Neighborhood Harem by Toro1,Toro1

Neighborhood Harem

A man loses his wife and after recovering from grief, goes on a journey of sexual discovery with help of his daughter. All characters in this story are 18 or over.

This is a complete story on its own. After I wrote Neighborhood Moms and Daughters, I had a lot of feedback suggesting that include the main character’s daughter in the action. I tried, but couldn’t figure out a way to write her into the story that didn’t feel contrived or phony. In the end, I continued the series without getting there.

The following story is similar in scope to Neighborhood Moms and Daughters, but focusses much more on a relationship that develops with his daughter after his wife’s passing. I think it works well and provides a lot of unique ideas, as their relationship develops.

The story takes some time to build, as I develop the characters and their background. When the action starts, it is frequent and I tried to be creative. I hope you enjoy.

Lastly, I hope it will showcase how I have developed as a writer. It has been a year since I wrote my first story and with your feedback and help of a great editor Kenjisato, I have improved. If you see improvements I can make to get better, please leave a comment.

Be prepared for a complete story. The build is slower. The sex goes from conventional to kinky in the end. It includes lesbian sex, a lot of anal sex, group sex, mild BDSM, and eventually incest. If these themes don’t interest you, please move on.

As is customary with my stories, I listed a porn star who approximates the physical image of the character. This is listed at the end of the story, as many readers may want to use their own imagination.

This is fantasy and I have taken liberties in ignoring STD, birth control. All characters are at least 18 years of age in this story.

As always, I appreciate your feedback, favorites, and followers. Seeing people read and enjoy a story is the motivation I need to keep writing. Feel free to be constructive and/or positive. Know that I have poured many hours into writing this.

Chapter 1

I was beset with loss. My wife, Susie, of twenty years, had just passed away after a short brutal fight with cancer. We had a great life until six months ago, when she had received her diagnosis. We had just dropped off our only daughter, Jordan, at UCLA to start her degree in psychology.

The past six months flew by in a flash, with us taking increasingly desperate measures to look for a miracle that never came. In the end, Susie was the pragmatic one and called an end to the extraordinary lengths we were going to, so she could spend her last weeks at home with Jordan and me.

Susie was clear in her advice to both of us, in her final days. “Don’t sulk for years in misery at my passing,” she said. “Go back to living your best lives and remember that I support this.

“Jordan, you need to go back to school. Excel there and become the woman I know you can be. We are already so proud of you. You are only twenty years old and have your whole life ahead of you. Don’t let my passing change your life’s trajectory.

“Rob, you have been the love of my life. After I pass, you need to find a new love. I know it will be difficult. For your own sake, don’t drown in sorrow. Remember me fondly, and know that I support you finding someone.

“Don’t jump too quickly for the first woman that shows interest. Take a while to get your head straight and then carefully choose what you want.”

“Mom, we are going to miss you so much,” cried Jordan. “I can’t imagine going back to school.”

“You must go back,” Susie said, with conviction. “School will help you move forward and be a positive focus.”

“What about dad?” Jordan said. “He will be lost without you.”

“Dad has our mutual friends to help,” Susie responded. “He will have to adjust and that will be easier without you. Your future is as an independent woman. That journey started when you left for school. Dad can’t go back to caring for you every day because that isn’t who you are anymore.”

Jordan and I put on a brave face and promised Susie that we would try to follow her advice.

The end for Susie came a week later, when she passed quietly in her sleep.

The funeral was later that week, with a brief service at the funeral home and it was followed with a wake at our house. The neighbors all pitched in by helping with food and drinks. Over one hundred people came.

I saw many old friends from my past, that I didn’t expect.

My best friends, Kenji and Jess, were there. Kenji and I had been best friends since we were six years old, and I had introduced Jess to him many years ago.

Jess was outgoing to a fault and both Kenji and her had no filter. They called everything like they saw it, no matter how inappropriate it was.

Jess came up to me and said, “Rob, look at what the cat dragged in. There are female sharks swimming everywhere here, and they think you are the chum.”

“What do you mean, Jess?” I asked.

“Rob, you are now a hot prospect and many of the women here are sizing you up,” Jess said.

“At the wake for Susie?” I asked, with incredulity.

“I have spotted at least five women who are interested,” said Jess.

“How would they be interested in a guy at his wife’s funeral?” I asked.

“Well, you are a good catch,” Jess said.

“I don’t see it,” I said.

“Then you are blind,” retorted Jess. “Let me lay it out for you.

“Physically, you are tall with a full head of blond hair, and still very athletic from years of rowing. You are the best-looking guy in this room right now, but that isn’t the only thing you have going for you.

“You are successful and have an executive job with an engineering company. Don’t underestimate that woman will find that very attractive. It isn’t necessarily about the money; it is that they see you as a confident leader.

“On the social side, you are outgoing, funny, and have a large circle of friends who all admire you and want to spend time with you. Again, this signals success to women who are looking for a mate.

“On the emotional side, there are those that feel sorry for you and want to comfort you.

“Lastly, many have seen your close relationship with Susie, and want the same for themselves. They see a loyal caring man and hope that they can replace Susie.”

“Wow, that is what you see here?” I said.

“I just call it like I see it,” Jess said. For instance, isn’t that your old girlfriend, Abby, from university? I don’t see her with anyone here and she keeps glancing your way.”

“We stayed in touch through Facebook, and she saw the obit and came by to offer her respects,” I suggested.

“She is offering you more than her respects with that low-cut dress and that push-up bra,” Jess suggested, with a grin. “How about Jenn over there, with those CFM pumps over there?”

“Jenn is married to Rick,” I said, as I nodded towards where Rick was talking to a couple of his buddies.

“Jenn might be currently married,” Jess said. “Her body language says she is on the prowl with those shoes and push-up bra. She wants to upgrade, just like a lot of other frustrated wives here. I will bet that she will be over with a casserole within a week.”

Kenji came and joined us putting an arm around Jess and said, “What are you two being all catty about?”

“I’m making observations on the women looking to snag Rob,” Jess responded.

“I think Jess’s imagination is getting the better of her,” I said to Kenji.

“She does have a dirty mind,” Kenji said, with a smile. “I do believe that she’s right, though, on this.”

Jordan came over and said, “Dad, you should mingle a bit, just to show people that you are all right.”

“I will, honey,” I said. “I just had to get Jess’s and Kenji’s minds out of the gutter.”

Jess gave me a push to go mingle, and grabbed Jordan and whispered something in her ear.

Jordan smiled and just nodded her head.

I was inclined to go back and join them, but was then set upon by people who had come to pay their respects and tell their favorite stories about Susie, or recount times that we were together.

Jordan and I cleaned up the house after the last guests left. After we finished, we both had a beer on the patio by the pool.

“Dad, I have been thinking about what mom said and wanted,” Jordan said. “I am going to go back to school. It’s only a month until I finish my year and I will be back for the summer.”

“That’s great,” I said, with enthusiasm. “I thought you had a job lined up in San Diego this summer. Why are you going to come back here?”

“Well, I have two reasons,” Jordan said. “First, is that your friend, Andrew, offered me a summer internship at his marketing company which will be a great experience, and second is so that we can spend the summer together.”

“Don’t come back for me,” I said. “I will be okay.”

“I know that you both want me to move forward with my life and know that I will,” Jordan said. “Don’t worry that I won’t go back in the fall. Together, we will both heal and have a great summer.”

“That will make for a great summer,” I said.

Chapter 2

Jordan departed for UCLA the next day. She was clearly loving her college life in LA. “I will be back in a month,” she said, at the airport. “Don’t get into any trouble while I am away.”

“How is that even possible,” I asked.

“Jess was pointing out all the cougars who are stalking you,” Jordan replied. “Don’t let them sink their claws into you, for at least a little while.”

“I think that you are both delusional,” I said.

“Track the number of casseroles and dinner invitations you get over the next month from single women and frustrated wives,” Jordan suggested. “I think you will be surprised.”

I headed home to an empty house. The quiet was deafening and this was the worst part of being alone.

Much to my chagrin, however, the casserole dishes started arriving. Many were from well-meaning friends and neighbors. I dutifully kept track of those who sent them and followed up to say thank you to all of them.

There was a subsection of these casserole ladies, that were clearly checking me out. Some would arrive dressed to the nines, while others wanted to see if I needed company.

Jess had been right about two of the ladies. Abby followed up her wake visit, with a casserole and suggestion that we get together. I rebuffed her advance, saying that I wasn’t ready yet and had plans to spend the summer with Jordan.

Abby was disappointed, but suggested that we talk in the fall.

The second advance was by Jenn. She also delivered a meal while dressed in tight yoga clothing. She suggested joining me for dinner. I asked if Rick was going to come as well.

A frustrated look came over Jenn’s face and she said, “Rick has gone fishing with the boys for the week and left me alone. I thought we could spend some time together.”

I rebuffed her like I had done to Abby. I left the possibility of doing something in the fall.

Others tried similar tactics and met with the same results. I wasn’t ready to start dating yet.

After the first wave of casserole dishes died down, a second wave started. These were women that I didn’t know but were friends of friends. My friends were now trying to set me up. Again, I persisted in rebuffing until the end of summer.

While Jordan was away, I focused on work. It had slid a bit with all the time I had put in with Susie’s decline. My boss was happy to see I was back, and my results were stellar.

On the personal side, I kept up with a senior rowing club where I rowed three mornings a week, and did a few workouts in the evenings. After a month of intense workouts, I was back in fighting shape with a lean build.

Jordan returned for the summer, which provided a great distraction from the female attention I was getting. I might have succumbed to temptation and gone on a date if I didn’t have this to focus on.

We had a great time on her return.

After our first dinner at home, she said, “Dad I noticed all the casserole dishes in the freezer. You have enough food there to feed an army.”

“You and Jess were right about the casserole brigade,” I relented. “They just don’t stop. I get invites to go out all the time, but have rebuffed them so far. When you head back to college, I may relent as it is lonely here when I am just on my own.”

“Dad, that is a healthy attitude,” said Jordan. “I know you miss mom, but we must move on. It is what mom would have wanted us to do.”

“I know,” I responded. “I just don’t know if I can find someone who compares.”

“Well, you can at least have some fun trying,” Jordan said, with a laugh. “Just don’t settle for someone who you don’t connect completely with.”

I blushed red at the implication that Jordan had made and then realized that she was clearly fine with me exploring, as long as I made smart choices. Our interactions were evolving to becoming friends, instead of a parent/child relationship.

_____

The next night after dinner, Jordan asked who all the casseroles were from.

Instead of trying to remember, I excused myself and got my laptop to show her the tracking sheet I had created.

“Clearly, Jess and you were correct on the cougar hunt,” I said, with resignation.

“Dad, you are such an engineer,” Jordan exclaimed. “You have never seen a problem that couldn’t be fixed with a good spreadsheet.”

Jordan scanned the data and said, “Wow dad, there was a lot of interest.”

“I know,” I said. “Some were from people who are just friends, but many had additional motivation. I’m glad that Jess and you prepared me for the onslaught.”

“This spreadsheet is a good start,” Jordan said, while looking through the entries. “We are going to need more details, though, if we want to use this to make decisions with.”

Jordan added columns to the spreadsheet and started making notes while quizzing me.

She focused on the women who were interested in me and started making notes to the side.

“I know a number of these women,” Jordan said. “I’ll do some research on them for you and maybe get Jess to help me out. It will be my little side project this summer.”

“You are going to pimp out your dad?” I asked, with a smile.

“I am just going to ensure that you are selective in the qualities you are looking for.”

_____

A week later, Jordan came back with the spreadsheet with additional questions like last names, physical characteristics, job titles, and even marital status.

I had arranged to meet Kenji and Jess at their cottage later in the summer. “Can Jordan join us?” I asked Jess, when we were discussing details.

“That’d be great!” Jess said, enthusiastically. “Then I won’t only hear boring stories of Kenji’s glory years in high school.”

_____

We joined them the next Friday, and had a great outdoor dinner on the lake.

“Rob, how did you fend off all the ladies fighting to ask you out,” Kenji asked, in a joking fashion.

“Kenji, he has had over twenty-five women who showed real interest,” Jordan shot back.

Kenji’s jaw dropped and he said, “I thought you would get a few callers, but I can’t imagine twenty-five. Did you have to beat them off your porch with a broom?”

“I told you, Rob,” Jess said, knowingly. “A young widower is a hot commodity. Let us live vicariously through you and tell us about them, as long as Jordan doesn’t mind.”

I laughed out loud and said, “Jordan clearly doesn’t mind. She’s created a spreadsheet with notes on each of the prospects.”

“This I have to see,” said Kenji. “Get your laptop and we can Chromecast it to the main television.”

Jordan jumped up, and ran to the car to grab it. They were all loving this.

Kenji made a round of drinks and we all grabbed a cozy seat, while Jordan pulled up her spreadsheet.

When it came up, I was shocked. There was a lot more information about each of my pursuers. Jordan had added photos, links to Facebook, Instagram, and LinkedIn. She had detailed notes summarizing what she found.

“Jordan, how did you get any work done this week?” I asked. “This is very extensive.”

“I did it during the evenings,” Jordan said, with a smile. “It didn’t take that long, and I loved doing it. It is a good combination of data science and psychology, which I am studying.”

As Jordan scrolled down, Kenji and Jess commented frequently, sometimes lewdly.

Jess spouted additional details and commentary which Jordan added to each profile.

“Who do you think he should contact first, after I leave this fall?” Jordan asked.

Kenji suggested a few women and after he named a fourth, Jess said, “Are you just basing these picks on bra size?”

“You have to use something to make a decision,” said Kenji, with a laugh.

Jess gave it some actual thought. “Definitely not the old girlfriend,” she said. “If it didn’t work out when he was younger, it won’t work out now.”

“Rob had quite the way with the ladies in his youth,” Kenji added. “All of his old girlfriends took it hard when he broke up with them, and many showed signs of pining after him for years.”

“My friend, Aria, who was dating your dad, when he introduced me to Kenji, was smitten as well,” Jess added. “Your dad told Kenji that he was going to break up with her and Kenji leaked that information to me. When Aria found out that I knew ahead of time and didn’t warn her, she got mad at me and still doesn’t forgive me.”

“Dad, what was your magic?” Jordan asked.

“I have no idea,” I said, with conviction.

Kenji laughed and said, “The only thing I can attribute it to is that many of the guys on the basketball team talked about your dad’s size. And I don’t mean his height.”

I blushed due to Jordan hearing this. It was common for Kenji to make inappropriate comments, I just found it embarrassing in front of my daughter.

Jordan broke the ice by saying, “So, who should we enslave to dad next? I was thinking about Heather. She was an old classmate and looks stunning.”

“I am not sure,” said Jess. “She has never been married and may be too prim and proper for our Rob. His first date should be someone sexy. He isn’t looking for an immediate long-term relationship.”

“That is a good suggestion,” said Jordan. “How about Erin or Jenn?”

“Jenn is married,” said Jess. “Although your story of her comments suggests she is unhappy. She is very good looking and exudes confidence at parties.

“Erin is a good choice, as well. She is single and I have inside knowledge that she is quite the player. Our boy, Rob, would have a wild time with her.”

“I know both of their daughters,” Jordan said. “I went to high school with them, and I believe that they are both in town. I may invite them over to our pool to pump them for additional information and do some initial marketing for dad.”

“That’s great,” Jess said. “I will do some quiet asking, as well.

Rob, you have to keep us up to speed on the progression. We all are invested in your future and want to help you.”

“Jordan, it would be helpful if you could share that file, as well,” Kenji suggested.

“You just want it for your own dirty imagination,” Jess said, with a grin.

“A man can dream, can’t he,” Kenji said.

“They just shouldn’t all be wet dreams,” Jess said, with a laugh.

Kenji laughed sheepishly and then winked at Jordan while pointing at her computer to ensure that she shared the file. What a horn dog Kenji was.

_____

I hung out with Kenji through much of the next day.

Jordan and Jess were poring over the file again. They came up with secondary options for me to pursue.

Over dinner that night, I was teasing the girls about their research.

“Oh, we aren’t done yet,” said Jess. “Jordan has instructions on how we are going to market you. She is going to take you shopping and make you buy some decent clothes and then get professional pictures to use on possible dating apps. You need some tighter fitting clothes to display the muscles that I see when you go swimming.”

Jordan nodded agreement with Jess, and gave me a pleading look. “Please say yes, daddy. It will be a great father/daughter bonding experience. I will really get to know you better.”

I sighed and relented. A father could not refuse his daughter, even if she was trying to set me up.

_____

The next week we arranged to go shopping for a couple of evenings. Jordan made me buy a few suits, new jeans, shoes, shorts, and a bathing suit. They were all tight fitting which I thought would be uncomfortable. I was wrong, as most of the clothing had stretch to it which made it much more forgiving.

By the end of our shopping excursions, Jordan added two new names to her prospect list. It seems that a couple of the sales ladies had been interested and asked Jordan about me after they found out that she was my daughter.

Chapter 3

The following weekend, Jordan invited Samantha and Hannah over to our house to spend some time around the pool. Samantha was Jenn’s daughter, who had turned eighteen and graduated from high school. Hannah was Erin’s nineteen-year-old daughter and in her first year of college.

They arrived on Saturday afternoon, and immediately decamped to the backyard after offering me condolences. They all stripped down to swimsuits. All three were gorgeous.

Samantha had long dark hair in contrast to her mother’s blonde locks. She had a tall lithe body with muscle definition from her years of dance. One of her best features was her face with watery-blue eyes and naturally full, pouty lips.

Hannah was a shorter and had a tight, lean body, with pixie-cut red hair and freckles that lightly dusted her nose and shoulders. She exuded sex with a strut in her step and how she pushed out her chest with firm, medium-sized breasts.

Jordan, I should mention, was also stunning with her tall figure and tanned skin.

After they got settled around the pool, I went out with some snacks and asked if anyone wanted a drink.

Hannah suggested a beer and then Jordan suggested that I do a round of G&Ts.

“I am fine with a few drinks, but have one demand,” I said. “Whoever drove here must surrender her keys. I will happily drive you all home, but don’t want any chance of anyone getting hurt by being impaired.”

“Wow, you are a pretty cool dad,” Samantha gushed, as she threw me her keys. “My dad is so square. He would have gotten all up tight and probably told us all to go home.”

“That is a fair trade for me,” Hannah said, and threw her keys as well.

I deftly caught the keys rings. “One round of G&T specials coming up,” I said, as I headed into the kitchen.

G&Ts were my specialty. I used Hendrick’s gin and fresh, hand-squeezed limes.

I returned with drinks which were appreciated by all.

“What a gentleman,” Samantha gushed, as she took a sip and raised her eyebrows in appreciation.

As I left the pool area, I could hear Samantha ask, “How is your dad doing? Is he considering dating yet?”

Jordan started responding, but I passed out of earshot and didn’t catch any more of the conversation.

Jordan came in and found me in my study doing work.

“How is your get-together going?” I asked.

“Oh, we’re having a great time,” Jordan responded. “The drinks got us all relaxed and we have been having a great time gossiping. We are getting hungry, and I was wondering if you could work a bit of your magic on the grill.”

“No problem,” I replied, and headed downstairs.

I pulled out some chicken wings and shrimp. I went out on the patio where Samantha and Hannah were talking and said, “Jordan says you ladies are going to join us for dinner. I assume shrimp and chicken wings will be good.”

“That sounds awesome,” Hannah exclaimed.

I fired up the grill and started prepping the chicken wings with a spicy rub and shrimp with Old Bay seasoning. “Would you be open to another round of G&Ts?” I asked.

I was greeted with nods all around and headed back to the kitchen.

“Can I learn how you make them,” Samantha asked, in a bubbly voice.

“Sure, they really aren’t that hard to do,” I said. “You just need to use quality gin and fresh limes. My only real secret is to actually squeeze the limes into the drink, so it isn’t just a garnish and really adds to the flavor.”

I demonstrated as Samantha looked on.

“Jordan was mentioning to us that you might try dating soon,” Samantha said. “I think that’s healthy. Some might say that it is too soon, but there is no sense in waiting based on what other people think.

“My mom and dad are splitting up, and I would bet that mom would be open to a call. She was a good friend and always thought the world of you.”

“I am sorry to hear that,” I said, with empathy.

“I am actually happy that they are breaking up,” Samantha said. “Dad has been ignoring her for years, letting himself go, and always goes off to do his own thing. She was a bit bossy, but is generally a good person.”

“How are you doing through all this?” I asked.

“I am fine,” said Samantha with a sigh. “I’m going to a local college for business and will be living at home. I was hoping to go away, but I think my folks’ finances won’t support it.”

“If you ever need any help with anything, please give me a call,” I said.

“That means so much to me,” said Samantha, as she touched my arm to add emphasis.

I went back out to the grill with the fresh drinks and started the cooking.

Hannah came over to check out my work and display her tight body to me and said, “Those shrimp and wings look great.”

“How was your first year at college?” I asked, to make small talk.

“Oh, it was great,” Hannah replied. “I learned so much and expanded my horizons in so many ways.”

“What was your favorite part of the year,” I asked.

“I learned a lot at school, but also learned about myself, as well,” Hannah said, provocatively. “I experimented a lot with different relationships.”

“And what did you find that you wanted?” I asked, as I flipped the wings. I shifted a bit as Hannah’s provocative talk was getting me excited.

“I always thought that I wanted to be in control,” Hannah said. “I was wrong. I like exactly the opposite. I want others to be dominant and order me to do things.”

“Well, I have an order for you,” I said, with authority.

“I can’t wait,” said Hannah, in a breathy voice.

“I want you to go in and bring out the plates and condiments,” I said, with a laugh and broke the tension.

Hannah laughed back and as she headed to the kitchen, I gave her a quick hit of the spatula on her ass and said, “Make it snappy.”

“Yes, sir,” Hannah replied, with mirth.

She came back out with the condiments and said, “I was hoping that sausage was on the menu tonight, but it seems I will have to come back for that.”

As Hannah put the plates down, she noticed the bulge in my shorts and shot me a quick glance and said, “And here I thought that my teasing wasn’t having any effect.”

As she said this, she reached out and gave the front of my shorts a quick pat which had her exclaim, “Oh my, Rob, you are packing something special down there.”

I didn’t know what to say at this point, and she just laughed and said, “This was fun, but I can see that I won’t get anywhere tonight. You should, however, give my mom a call. I think she might be even wilder than I am.”

I grabbed the food and we headed to the table to join Jordan and Samantha.

“Thanks, daddy,” Jordan gushed, and gave me a hug from her chair.

I hadn’t yet deflated, and I could feel Jordan’s arm across my member.

Jordan gave a little jump and then recovered by starting to serve.

“What were Hannah and you talking about?” Jordan asked.

“She was telling me about all that she learned at school,” I said, innocently. “She likes the freedom that it offers, but sometimes misses the discipline that was set in her high school.”

Hannah just gave a little giggle and started helping herself to food.

We all dug in and had a good dinner.

After we finished, I drove them both home with Jordan. We promised to drop their cars off early in the morning so they wouldn’t be missed.

Both girls thanked Jordan and I profusely for the afternoon.

On the way back home, Jordan started quizzing me.

“Was Hannah flirting with you tonight?” Jordan asked.

“Yes, she was,” I said. “You know she had an effect on me when you gave that hug. I think that it was innocent. She was probably just having some fun trying to push my buttons.”

“Well, by what I felt, she was certainly doing that,” Jordan said, with a smile.

“Both of them suggested that I contact their mothers,” I said. “You must have been dropping hints.”

“You came up in discussion,” Jordan said, with a grin. “I think they both find you attractive but understand that it would be very awkward with the age difference and that they are my friends. They both suggested their mothers as possibilities.

I am sure they will work it into their conversations over the next week,” Jordan said. “So, who are going to ask out first?”

“I am leaning towards Jenn,” I responded. “By all accounts, Erin is wild, and I am not sure that I am ready for that.”

“Okay,” Jordan said. “Just make sure you experience some wild before you get locked into a full-time relationship. You shouldn’t settle for anything that you don’t want.

“Dad, I think you are ready to take the next step and go on a date. I know that it will feel strange going on your first date in twenty years, but the first step is the hardest. I know you are ready and want you to do this.”

“Jordan, I will do it,” I said. “It feels strange getting all this advice from my own daughter on something so intimate. I have to say, it has been a fun project and we’ve grown closer by doing this together. I love you and will miss you dearly when you go back to school.”

“The project is only starting,” said Jordan. “I expect frequent updates and you aren’t gonna hold out on any of the details.”

I blanched at the idea of having to share sex details with my daughter. “I am not sure how much detail I’ll provide,” I said, with trepidation.

“Oh, you are going to spill your guts to me,” said Jordan, with a grin. “Moms and daughters share this kind of detail all the time. You are just holding onto your old sexist stereotypes in not wanting to share with me.”

“You have me there,” I said, with a smile. “You may have to work at breaking those down over time.”

When we got home, Jordan went to the mail pile and pulled out the invite to the Smiths’ engagement party for their daughter.

“You are going to this,” Jordan said. “Jenn will be there, and you can have a flirty conversation with her.”

“What if Erin is there?” I asked.

“Then you should have a flirty conversation with her, as well,” Jordan said, with confidence. “They will both see that as attractive in you, and creating a bit of healthy competition for your attention won’t hurt.”

_____

As the week wore on, I became more nervous about my upcoming goal.

Jordan kept coaching me on keeping the conversation focused on the person I was talking to. “Make sure you listen and ask follow-up questions based on what they say,” Jordan suggested. “It demonstrates interest and shows them that you are listening to what they are saying.”

“I wish I had you there with me,” I bemoaned.

“I will be, in spirit,” Jordan said. “My flight is on Friday, so I can’t be there with you in person. I will be thinking of you and know that you can do this.”

I took Jordan to the airport, and on the way, she gave me a last bit of advice, “Dad, you are going to go on a number of dates and many of them will end with you having sex. Everything I read about older relationships suggests that this happens far more quickly than in your youth. Everyone knows that they want it, and so it happens. Be confident in telling your partner what you want, and ensure you understand what they want.”

“I will try,” I said, with some doubt in my voice.

“I know that you and mom had a great sex life until she got sick,” Jordan said, with a sheepish grin. “I could hear you from my room. Be creative and try some new things.”

We hugged at the curb, and she whispered in my ear, “Have fun!”

Chapter 4

The next day was the party. I took time getting ready, and wore one of my new suits along with a white shirt. I figured that if I started sweating from nerves, the white shirt wouldn’t show the sweat as badly.

I arrived at the party and reintroduced myself to friends. Everyone was happy to see me out socializing again.

I saw Jenn across the lawn and when she spotted me, she made a beeline to talk to me.

“Rob, so good to see you,” Jenn purred, as she touched my arm. “My, you look dashing in that suit. I didn’t think engineers usually wore suits and especially not such well-tailored ones.”

“Jordan is to blame,” I said. “She has been working to get me to improve my game this summer. I must say that you look ravishing tonight, as well. I love the black dress and if I may be so bold, the plunging neckline.”

Jenn blushed at the comment and said, “I think Jordan must have been giving you charm lessons, as well.”

“She did,” I said, truthfully, “are my charms working so far?”

“Oh yes,” Jenn said, as she reached out and touched my elbow. “What else did you learn this summer?”

“Well, I did hear about Rick and you,” I said. “I was sorry to hear, but not really that sorry, if you know what I mean.”

Jenn blushed again.

We were then interrupted by the Smiths, who were happy to see us both.

As we talked with them, others joined the conversation.

I took the opportunity to excuse myself and get a drink at the bar.

As I was standing waiting for the bartender to mix me a Bloody Mary, I felt a hand on my back and looked to see Erin standing next to me and she said, “Hello, stranger. I haven’t seen you out at any events this summer.”

“Jordan has occupied most of my time this summer,” I said. “She left to go back to school yesterday, so here I am.”

“Yes, here you are,” said Erin. “And you look amazing. That suit is hip, and I like that you let your hair grow a bit longer. Makes you look a bit like a taller Bradley Cooper.”

“Well, I don’t think anyone is noticing how I look, when you are standing here, wearing this intriguing wispy outfit,” I said.

Erin was wearing a semi-transparent shirt that revealed her black bra. She had her hair up in a messy bun, and had a thin black strap around her neck. Erin had red hair like her daughter, and dusting of freckles across her toned shoulders.

I reached out and touched the silk strap around her neck and said, “I haven’t noticed this fashion statement before.”

Erin smiled and said with one eyebrow raised, “It is more of a lifestyle choice than a fashion statement. I have been getting some coaching of my own, from my daughter this summer and realized that we have a lot in common.”

“Your daughter was interesting to talk to when she was over at my place,” I said. “Very provocative and forward and maybe in need of some discipline.”

“Oh, we could both use more discipline in our lives,” Erin said, as she licked her lips and kept her hand on my back. “Just let me know when you are ready to dispense justice and I will be there.”

Others came up behind us at the bar, so we had to give the flirting a break.

I turned and could see Jenn giving us a glare.

I grabbed my drink and excused myself, to head back to talk to her.

“I see Erin is trying to get her claws into you,” Jenn said. “She certainly plays the field.”

Jenn wasn’t frustrated with me, as much as she was frustrated with Erin who was her friend.

Jordan was right. A little jealousy wasn’t a bad thing.

The afternoon party wore on with Jenn sticking close to me to mark out her territory.

When she excused herself to go to the bathroom, Erin swooped in.

“I see Jenn is on you like white on rice,” Erin said. “When you are done with the secondhand burger meat, give me a call for some tenderloin.”

“I will, Erin,” I said. “We have much to discuss about your naughty behavior.”

Erin turned with a coy smile and said, “I will be awaiting your call, master.”

Erin was going to be wild. She exuded sex and wanted everyone to see it.

I have to admit I was still intimidated by her, but also had to admit that I was intrigued, as well.

As the afternoon party was winding down, Jenn suggested that we go grab some dinner at a local restaurant. She wasn’t wasting any time in moving forward.

We both drove to her place to drop her car.

The place I had suggested was a hole-in-the-wall Thai restaurant. The food was simple and delicious. As we sat on the patio eating slices of oranges and sipping green tea, we talked about our recent experiences.

Jenn talked about leaving Rick. “Rick had no passion for our relationship,” Jenn complained. “I think he purposefully took up hobbies that I had no interest in and would take him away from us. On top of that, he let himself go physically.”

I nodded politely and agreed with her. “What did you get interested in, to fill the time?” I asked.

“I have been doing yoga and spin classes,” Jenn said.

“I love the results,” I said, indicating what great shape she was in.

“Are you still doing the rowing?” Jenn asked. “You look cut beneath that suit.”

“Rowing has been a good way to channel my time since Susie’s passing,” I agreed. “My other occupation has been spending time with Jordan.”

“Tell me more about the coaching she has done with you.” Jenn asked.

“At first, Jordan wanted me to wait to start dating, so I could get my head straight after Susie’s passing,” I said. “She was worried that I wouldn’t be a good judge of character in my fragile state.

“Then she helped me evaluate all the women who had shown interest and came up with a short list of women that she thought would be good for me.

“Lastly, she polished me up with some new clothes.”

“Well, she did great work,” Jenn said. “Maybe I should reach out and thank her for pointing you towards me. Who else is on your short list?”

I smiled and said, “I don’t think that is something that I am comfortable sharing. Do know that you are the first person I have been out with.”

“I am flattered,” Jenn said. “I hope to make it memorable.”

“I hope it will be for both of us,” I responded.

I picked up the check for dinner and walked back to the car with Jenn on my arm. I leaned in for a quick kiss, as I opened the door for her.

We headed back to her place in relative silence. I was nervous about the next step that I was anticipating, and I suspected that Jenn was, as well.

As we approached her house, Jenn said with some nervousness, “I hope that you are coming in.”

“I am great to do that, as long as you are comfortable moving ahead quickly,” I responded.

“Rob, I am an adult and know what I want,” Jenn said. “I want you to come in and spend the night. I have been neglected by Rick for a long time, and am looking forward to this. You are a great guy and I think we will have a lot of fun. There is no pressure to make this serious right away.”

Jordan was right again. This was going to move quickly.

We went in and she grabbed us both a drink, which we had in her living room.

“Is Samantha around tonight?” I asked.

“She is out with friends and won’t be home until late,” Jenn responded.

“Well then, I won’t have to worry about her seeing this,” I said, and leaned in for a kiss, as I held Jenn’s face and pushed back her long blonde hair.

Jenn responded by forcefully pushing back and opening her mouth.

My other hand was on her shoulder, and I pulled her closer as we extended the kiss.

Jenn had a hand on my chest and another on my side, which she was using to pull my shirt tails out with.

I responded in kind, and ran a hand over her breasts. I could feel her stiff nipples through the dress, and I gave one a quick squeeze. It was soft and full. Jenn had a nice pair of D-cup breasts.

Jenn gave a little yelp, and I was worried that I had done something wrong.

“Let’s take this to my room,” Jenn suggested.

I just stood and reached to help her off the couch.

We hurried upstairs like teenagers and closed the door to her master bedroom, and immediately started ripping clothes off each other. There was a trail of a shirt, pants, and a dress leading to her bed.

We were both lying on top of her covers, dressed only in our underwear.

I caressed her soft, round breasts which were encased in a lacy white bra. In between the lace, I could see the darkness of her erect nipples.

Jenn was rubbing my engorged cock through my underwear. “Oh my,” she said. “This is much bigger than Rick’s. It is going to feel so good when you put it inside me.”

I ran a hand behind her back and released her bra, and then pushed Jenn onto her back. I was up on one elbow and pulled the bra from her and said, “Your breasts are beautiful.”

I then leaned down and put a nipple gently into my mouth, moving my tongue around the outside.

With my free hand, I pushed down her panties which she kicked away. I ran my hand briefly over her pussy and dipped one finger to run along her slit. I felt the moisture which made her pubic hair wet.

Jenn let out a moan, as I kissed my way down her belly. She spread her legs, but I didn’t take the immediate invitation to dive into her pussy. Building anticipation had always been important. I kept kissing down her legs to her feet, which I massaged and licked her toes.

I repositioned myself at the bottom of the bed and then started kissing my way up between her legs. With my hands, I pushed Jenn’s legs apart and back which exposed her pussy wide to me. I nibbled on her inner thigh and then brushed my nose up her slit. This elicited a frustrated moan from Jenn.

I gave her a long, slow lick then from the bottom of her pussy up to her clit. She was wet and pulsing with anticipation.

I licked a finger, and then pushed it into her pussy while giving periodic licks to her pussy without pushing too hard on her clit, as I sensed that would push her over the edge. I pushed a second finger into her sopping pussy while giving her clit a bit more pressure. Jenn started her first orgasm, which I felt as she contracted on my fingers and leaked her girl cum into my mouth.

I didn’t make a move to go up, but let her orgasm pass and then started my oral play again.

At first, she made motions for me to rise and then just gave into the pleasure of the oral attention. I didn’t take as much time on my second pass, and was aggressively licking her while I held her legs behind the knees.

Jenn screamed out her second orgasm and pulled my head into her honeypot to apply pressure to her needy cunt.

I rose with a glistening face and went to give her a kiss.

Jenn recoiled a bit and reached over to her nightstand for a tissue to wipe off my face.

“Rob, that was awesome,” she cooed. “Rick rarely did oral and never that good or for that long.”

Jenn reached down to pull down my underwear. I helped her by raising my bum from the bed. She grasped my member and said, “This is going to feel so good. You have warmed me up and now you are going to fuck me so well with this big dick.”

She swung a leg over my torso and guided me into her juicy hole.

As she descended my shaft, she kept making little grunts, and said how amazing it felt. Once I was fully sheathed in her pussy, she slowly started to rise and descend. I tried to meet her strokes to get maximum penetration. It felt great, but I must admit, that I was used to more control and wasn’t sure I could get off this way.

To get her closer, I cupped both of her butt cheeks with my hands, to help guide her down my shaft.

Once we got a rhythm, I chose to spice it up a bit and let a hand wander to the crack of her ass and ran my fingers over her anus. On the second pass, I put a finger into her ass up to the first knuckle. It was something Susie had loved, and I thought Jenn might appreciate it as well.

I felt her orgasm start as her passage contracted on my cock and she yelled out again. After she came down, she pushed my hand that was on her ass away.

I pulled Jenn close and rolled Jenn onto her back while staying lodged in her pussy. I gave her a kiss and then started flexing my hips to pump my cock into her.

“You are insatiable,” said Jenn, in a husky voice.

I picked up my pace. Jenn screamed out once again in orgasm, and this finally sent me over the edge. I groaned and relaxed and slipped out of Jenn.

On my side, I draped an arm across her belly and caressed her breast.

“That was the best sex I have ever had,” Jenn said. “With Rick, it was fifty-fifty if I would even have one orgasm. I just had four.”

“This is just the half-time show,” I said, as I moved my hand to her breast.

“Rob, I am not sure that I am up for a second half tonight,” she said, with regret. “You are so much bigger and I am a bit sore after that pounding.”

“There are other things we can do that don’t involve my cock in your vagina,” I said, as I stroked her breast.

“Oh, Rob,” said Jenn, as she turned away to her side. “Just go to sleep like every other guy.”

I said under my breath, “I am not like every other guy.”

_____

When I woke up in the morning, Jenn was up and just coming out of her ensuite bathroom with a towel around her head and nothing else on. She had a great body.

“How are you this morning, Mr. Big,” Jenn asked, with a smile.

I lifted the sheets and made a show of looking down and said, “Still pretty big.”

Jenn was now by the bed and laughing.

I reached out and grabbed her waist and pulled her onto the bed as she squealed.

“Yes, I am still big, and we are going to have to do something about that,” I said, as I pinned her down on her back. “But before we deal with that, I think I need some breakfast. I had a fine meal last night, and believe there might still be leftovers.”

I gave her a quick kiss and then moved down her body, stopping briefly at her breasts for some oral attention. I then made my way to her pussy. Her pubic hair was still damp from the shower and was now getting damper with expectation.

I dove in and Jenn’s giggles turned quickly to gasps, as I ran my tongue around her outer labia.

Jenn spread her legs wide and grasped them behind her knees to give me similar access to last night. I ran my tongue from her rosebud up to her clit coating it all with a heavy layer of spit. I put my index finger in my mouth and then pressed it to her ass.

I had thought that she secretly liked this, as it had sent her into an orgasm last night. She had also sent the signal that didn’t want it by pushing my hand away.

I looked up, and she raised her eyebrows in question, with my finger applying gentle pressure. She shook her head in refusal, so I moved it up to her vagina and kept up my oral intensity. When she was close, I pulled my face back and stopped moving my finger.

Jenn let out a frustrated moan, as I smiled at her. She tried to grab my head, but I was able to dodge.

I then blew lightly across her pussy lips which made her shudder. I then slowly resumed licking until I brought her to an orgasm, as I had my mouth clamped to her pussy.

“Oh, my fucking god, that is amazing!” she yelled.

I crawled back up next to her with my glistening face.

Jenn took the damp towel from her head and gave my face a wipe before giving me a kiss. As she kissed me, she reached down and grasped my cock and started to stroke me.

I laid back with the expectation that she would now give me a blowjob.

That didn’t seem to be happening, as she just continued to stroke me.

My hand was on her back and applied a little bit of pressure to indicate what I wanted.

She then, hesitantly, moved down lower on the bed and used the towel to give my cock a quick wipe. I suppose she didn’t want to deal with any residue from last night. This wasn’t something that had bothered Susie, but I had to respect differences.

Jenn then resumed her stroking and would give a quick, tentative lick to the head.

It had been so long since I had sex other than last night, I was still not going to last long.

Jenn got a bit bolder and put the head of my cock in her mouth as she kept stroking. It felt great and the sight of her doing it, started my orgasm.

As my first stream shot into her mouth, she instantly recoiled from my cock with the second stream hitting her from nose to chin. She opened her mouth and spat out the cum in it and looked up at me with venom and said, “What the fuck was that?”

“What do you think it is?” I said, with disbelief. “You are an adult and have to know the basics of how a male orgasm works.”

“But you just came in my mouth!” Jenn yelled. “That is so disgusting. You are supposed to let me know so I can get it out before you cum.”

“Jenn, I am sorry,” I said. “I didn’t know that was your expectation. You have to realize that this is the first time I have had sex with another woman in over twenty years.”

“Well, that isn’t happening again, ever,” Jenn said, as she wiped her face with the towel.

I stewed for about a minute and then thought fuck it. No sense stewing on this, time to get it out on the table.

“Jenn, I think you have a bit of a double standard,” I said.

“How do you mean, Rob,” she said, with some anger in her voice.

“Between last night and this morning, I have gone down on you twice which resulted in you cumming in my mouth three times,” I retorted. “You even pulled my head into your pussy as you orgasmed.

“Now don’t get me wrong, I loved it and I loved giving pleasure to you. I had no problem with it. I just don’t see how it should be so different when the roles are reversed.”

“It is totally different,” she said, unreasonably. “Good girls don’t swallow.”

“Well, I think that is an outdated idea,” I said. “I guess that maybe I am not looking for a ‘good girl'”

“Yes, maybe you should go and take your perverted ideas with you,” Jenn said. “I hope you find your cum-swallowing anal slut.”

I laughed at her attempt at a carve and said, “I hope I do, too. Since you brought up your disgust for anal, you might want to remember what set you off on your orgasm when you rode me last night. Your mouth said no, but your body was saying yes.

“Think about that when you find a guy who just shoots his load and rolls over.

“Oh wait, you won’t have to think too hard imagining that, as that is the person you just left.”

I got up and started pulling on my clothes, as Jenn was fuming on the bed.

As I finished getting dressed, I went over to her and sat on the bed. “I am sorry that this isn’t working out,” I said. “I went into this with every hope that it would. I hope you know that I have not tried to deceive you in any way.”

Jenn still didn’t say anything.

I got up and said, “I am sorry again. You are a beautiful lady and clearly, we just aren’t compatible in bed right now.”

I got up and went to her bedroom door where I heard footsteps just outside.

I let myself out of the bedroom and headed downstairs to find Samantha in her pajamas in the kitchen. She looked up and gave me a smile which was probably half genuine and half out of guilt for eavesdropping on us.

“Hey, Samantha,” I said.

“Hey, Mr. Smith, do you want some breakfast?” Samantha offered.

“Call me Rob, and thanks for the offer, but I think I should go,” I said.

“Too bad it didn’t work out,” Samantha said, quietly.

“Yes, it is too bad,” I agreed. “We are both adults who don’t want to go down a path where neither of us will be happy in the end.”

“I understand,” said Samantha. “Good luck on your search. You are a nice man, and you’re going to make someone very happy. Say hi to Jordan and ask her to give me a call when she gets a chance. I enjoyed spending time with her this summer.”

I took my leave and headed home.

I checked my phone when I got in and saw a few messages from Jordan. She was looking for an update on how the date went.

I texted back: “We had dinner after the party which went well. The after-dinner stuff didn’t go as well.”

My phone dinged with a reply in seconds, “You are going to give me a LOT more details.”

A video call from Jordan then came up. It was time to face the music with my daughter.

“Dad, well done on going on a date!” Jordan gushed. “You are not getting away without describing the juicy parts, though.”

“I am not sure that I am comfortable sharing that and especially with my daughter,” I said.

“Dad, get over it,” Jordan said. “I am an adult and fully aware of all aspects of relationships. Hell, it is what I am studying.”

“Yes, but you are my daughter, not my therapist,” I argued back. “Intimate details shouldn’t be discussed with your children.”

“Dad, that is so old school,” Jordan said. “And I have news for you. My old bedroom at home shares a wall with yours, so I have been aware of all your intimate details for years.”

“You listened in on mom and me?” I said, with shock.

“All the time,” Jordan said. “And I will say it was very sexy. When I was old enough, mom and I would talk about it after you left for work. You had a great thing going and made me very liberated about sex in my own life. So don’t think that anything you are going to describe will shock me.”

“That is a lot to process,” I said.

“Okay, we don’t have to get to juicy bits right away,” Jordan said, with patience and a knowing smile. “Tell me about the party and dinner and then you can spill your guts about the rest of the evening.”

I told her about the party and how Jenn had latched onto me right away. I also told her about my brief conversations with Erin and her blatant propositioning.

“Erin is clearly a wild one,” Jordan commented. “We knew this, but her submissive gestures in public are eye opening. You know that the silk band that she was wearing denotes her submissiveness. Touching it would have been a big turn-on for her.”

I moved on to talk about the dinner and the open conversation that we had about me staying over.

“That is a good conversation to have while you are dating,” Jordan said. “You want to set clear expectations and ensure that you aren’t misinterpreting her signals. So now we are at the meaty part. Time to give me real details.”

I described our making out on the couch and then our quick move to the bedroom. “I was really enjoying myself and I think Jenn was getting a lot of pleasure,” I said. “The issue was that the pleasure was not reciprocated.”

Jordan pressed for real details, and I finally relented and described her ending the lovemaking in the evening, and her hesitation to provide oral and her subsequent disgust, “…with me blowing in her mouth.”

“Dad, you did the right thing by expressing your disappointment with her,” Jordan said, sympathetically. “Life is too short to put up with selfish lovers and bad oral. I do have one question. I know that you and mom did some bum stuff. Did you try that with Jenn?”

I relented all the details about that with Jordan. I really had no secrets left with her.

“I think that Jenn is just stuck in an old way of thinking,” Jordan said. “She might come around, but I don’t think you should go on that journey with her. Let’s move on to your next prospect.”

“So soon?” I asked.

“No time like the present,” Jordan said, with confidence. “You have to get back on that horse and ride. Your first date wasn’t that bad, it just wasn’t perfect and isn’t going to result in a longer-term relationship. To find someone good, you need a larger sample size to choose from.

I want you to message Erin and Heather by end of day tomorrow. It is time to get a couple of balls in the air now that you are back in the game.”

“Yes ma’am,” I said, as I saluted my new taskmaster.

“I have messages from Jess and Samantha,” Jordan said. “Am I okay to talk to them? I will reveal some details to Jess. She deserves some juicy stories for all the work she put into this. Samantha is probably disappointed, and I will talk to her. She has had a rough time with her parents’ break up.”

“I am fine with that,” I responded. “I will never hear the end of it from Kenji. He’ll be relentless in his ribbing.”

“Dad, you did well yesterday,” Jordan said, with enthusiasm. “I think you will have a wild time with Erin and you should learn more about Heather. Let yourself go and don’t be afraid to try different things. Your bum obsession is no longer frowned upon. It has gone mainstream, and most people are into it… I know I am. Go forth and prosper and don’t forget to share the details.”

“I will,” I said, with confidence. “I am not sure if I am ready to hear your intimate details yet.”

“Give it time, dad,” Jordan said. “It will become normal, just like it was between mom and me.”

We signed off and I headed to my bedroom to take a shower, do a workout, and then a dip in the pool. Jordan’s pep talks and the workout cleared my head and by the afternoon, I approached the future with a new sense of optimism.

I sent three texts that afternoon.

The first was to Jenn, thanking her for the evening and saying sorry that our needs didn’t match.

She responded with a brief acknowledgement, and finished with an apology of her own for being a bitch.

The second was to Heather, an old friend from school who had never been married. She was successful and had a killer body. I suspected that she had never found someone due to her lack of confidence. I suggested that we get together for a coffee.

Lastly, I took some time composing a message to Erin. She had indicated that she was submissive and had even made reference to me as ‘master’. I messaged, “Time for you to get some prime rib. The secondhand burger meat was a bit rancid. You will come to my place for six tomorrow night. Dress appropriately and include the collar.”

Erin responded in second with a “Yes sir! Should I bring an overnight bag?”

“I am disappointed that you don’t know the answer to that question already,” I replied. “You should bring anything you may need to be satisfied.”

“I will come fully equipped. See you at six.” Erin responded in seconds.

I copied the text exchange and set it to Jordan who responded with, “I love your assertiveness. It is what she wants, so play it up to the max.”

I spent the afternoon buying some groceries to make a dinner for tomorrow. I also went to my bedroom and got out some of Susie’s toys and fixed some restraints to the post of the bed and made sure I had a supply of lube. I had been a scout in my youth and always believed in being prepared. Getting set up had gotten me excited, but I held off indulging myself as I was going to need stamina for tomorrow.

Chapter 5

I took off early from work and prepared a seafood dinner. At exactly six, the doorbell rang.

I opened the door to find Erin dressed in a kimono. She had her red hair pulled back in a tight ponytail and she had a leather collar around her neck with a metal ring on the front.

“I am here to deliver the prime rib you requested. It hasn’t been cooked yet, so you may want to put a leash on it,” Erin said, as she handed me a black leather leash.

She stepped into the front hall, and I took the leash and her duffle bag.

I knew I had a role to play here, which was not natural to me, but was very intriguing. I walked around her and wasn’t able to discern too much about her outfit, as the kimono hid much. As I got back in front of her, I reached around her back and grabbed the ponytail and pulled her head back. This exposed her neck, and I deftly clipped the leash to the ring on her collar.

“The meat needs to be more exposed,” I said, as I pulled the bow apart on her kimono. I pushed it off her slender shoulders and fell to the ground around her feet.

What was inside, was spectacular. Erin was much slighter than Jenn, with elfin-like features. Erin had a matching set of black lingerie that left little to the imagination. Her pink puffy nipples sat atop firm B-cup breasts and were straining at her lacy bra which was semi-transparent. Like her daughter, she had a dusting of freckles on her face and shoulders. Her skin was alabaster white, other than the freckles. She had a garter belt on, to hold up her silk stockings.

I did note that her black lingerie panties were over top of the garters which would allow me to remove them without having to take off her stockings. Very thoughtful.

“You are finely dressed,” I said, with appreciation. “Let’s have a bit of dinner prior to the main event.”

“Thank you for your compliments, sir,” Erin said, as she licked her lips. “I hear the appreciation in your voice and see it in your eyes. You look ravishing as well, in that tight black t-shirt. I can see your rippling abs and those pants don’t leave much to the imagination. My daughter alerted me to your endowment.”

“She is a little minx, as well,” I said. “She teased me when she was over visiting my daughter with Samantha.”

“The apple doesn’t fall far from the tree with her,” Erin stated. “She is having a wild time at college, and I have been envious.”

“Let’s ensure that we make her jealous,” I said.

We sat down and I served up a seafood stir fry over rice accompanied by white wine.

“Rob, you have suddenly come out of your shell,” Erin said. “You showed up at that party like a breath of fresh air, after being absent all summer. What happened?”

“Obviously, it took time for me to get over Susie’s passing,” I said. “In addition to time, I have been getting coaching from Jordan this summer. She has been encouraging me to get out there and explore.”

“Jordan is a good daughter,” Erin said. “Did she guide you into going on a date with Jenn first?”

“She did,” I responded. “Don’t be offended. Jess and Jordan had heard about your wild side and didn’t want to throw me to the wolves on my first date. They thought that it would be more traditional and ease me back into it.”

“So, how did it go?” Erin asked.

“I would describe it as being too traditional for my tastes,” I said.

“Jenn called me yesterday and indicated that it had not gone well and that she didn’t meet your expectations,” Erin added. “She is starting to regret some of her behavior. Her loss may be my gain, so I won’t complain. She is a friend, but our mutual interest in you may put a wrench into that.”

“That would be too bad,” I added. “I don’t hate her. We just didn’t connect over a few things.”

“You mean her aversion to performing blowjobs,” Erin said, with a knowing smile.

“Wow, you women really do talk a lot,” I said. “My daughter beat that information out of me and clearly you’ve had a candid conversation with Jenn.

“Did any of Jenn’s revelations about me give you pause in coming here, tonight?”

“On the contrary,” Erin said, as she provocatively licked her lips again. “I am excited about tonight and have high expectations.”

We had finished our meal and were sipping wine.

“I think it is time for dessert,” I said. “We should retire to the bedroom to commence.”

I got up from the table and went around to Erin. “Are you ready for dessert?” I asked, forcefully.

“I am so ready,” Erin purred.

I grabbed the leash and guided her out of the dining room. I picked up her bag on our way through the hall and we ascended the stairs.

When we reached the landing at the top of the stairs, I said, “For the entrance to the bedroom, you should proceed by crawling to the bed.”

I went ahead of her while loosening my pants. I dropped them to the floor and sat on the edge of the bed in my boxers, as Erin did her sexy crawl to me.

I spread my legs and Erin crawled right in between.

“I have been visualizing this since Hannah indicated her discovery,” Erin said, in a sultry voice.

Erin reached slowly and put her hand in my boxers and pulled out my very hard cock. “Oh, this is going to be great. I can’t even get my hand around the base. You are going to stretch me in so many ways.”

I put my hand on the back of her head and she looked up at me and gave me a subtle nod, and then opened her mouth to engulf my cock. Initially, Erin darted her tongue around my head.

I steadily applied pressure forcing more of my cock into her mouth. I felt the head of my cock touch the entrance to her throat. I kept it there for a second, until I applied more pressure and pushed my hips forward to quickly enter her throat. Her small mouth was now stretched around the base, and her eyes were watering. There was no gagging which impressed me.

I released her and Erin came up for air. “I have never had anything that deep down my gullet,” Erin exclaimed, and then started feeding herself again.

I pulled her off my cock and said, “Erin, that is so awesome, I have never had anyone take me to the root. However, if you keep that up, I am going to blow my load right now.”

“And how is that a problem?” Erin asked.

“We are going to take it slow tonight, and I have to pace myself,” I said. “I am not just a one-shot cowboy, but there are limits to my endurance.”

Erin put on an exaggerated pout.

“Now get up on the bed on all fours,” I ordered.

Erin quickly complied and arched her back making her ass look rounder.

I got up and went to the two posts at the head of the bed and pulled out ties that I had affixed there yesterday. I gently tied each of her hands so that they pointed out to each corner. She now had her chest on the bed with her bum pointed up.

Once she was secured, I got up and went over to her duffle bag and put it down next to her. “What surprises are stored inside here?” I asked.

Erin smiled and said, “I guess you will have to open it and find out.”

“Hmm,” I said, as I pulled open the zipper.

The first item was a pair of handcuffs. “I won’t be needing these tonight,” I said, as I tossed them over my shoulder.

Next up were some dildos, a butt plug, and a bottle of lube. I looked at the dildos and shook my head and said, “So small.” One of the dildos had what looked like a mouth guard attached at the base. I held it up to Erin and said, “Can you explain this?”

“Simple,” she said, “it allows someone to control the dildo with their mouth, getting an up-close experience to the penetration.”

A strap-on dildo came out next. “You won’t be using that on me,” I said.

“Don’t knock it until you try it,” Erin said. “I also thought I might need it if your daughter was here,” she added, with an evil grin.

“You are a dirty one,” I said.

“Rob, you have no idea of the depths of depravity I am willing to go to,” Erin said, with sincerity. “Tell me your darkest, most perverted fantasy and I will love making it happen for you.”

I thought for a second and said, “I want to fuck your daughter’s ass on the edge of her bed until I unload in it. As I withdraw from her ass, you will clean my cock with your mouth. I will then lower her bum so that her gaping asshole is directly over your mouth and you will felch my cum as it oozes out. You will take that cum and drool it into her mouth so she can then swallow it.

“That is the dirtiest fantasy that I can think of on the spot, but if you give me some time, I am sure that I can dream up many more.”

I looked over at Erin and she had her mouth agape in surprise. “Rob, that is the nastiest scenario I have ever heard. It combines anal, lesbian incest, cum eating, and ass to mouth. I love the creativity by involving my daughter. No guarantees, but I will try and if I can’t get her, maybe Jenn could be a substitute.”

I was now rock hard again with those thoughts. I kept digging through the bag and found a blindfold and a ball gag. “Do I need to use this on you?” I asked. “Are you going to scream like a banshee when I plunder you?”

“I can make no guarantee,” Erin said, with a smile.

“I am going to allow you to talk tonight,” I said. “It will help me to better understand your needs. If those needs require me to gag you, I will. I want you to tell me what you like and what you don’t, tonight. I might listen.”

“I am loving the start of our evening,” Erin said. “Your control of me is perfect and you are doing a great job of building anticipation.”

I reached out and caressed her face. “I am trying to take the control that you want,” I said. “I am new to this, and you have to let me know if I go too far. All good relationships are based on good communication, even if there is a dominant person and a submissive one.”

“I will let you know,” Erin said. “If you are new to this, I would recommend that you proceed aggressively. It is what I want.”

I ran my hand from her cheek to her chin and grasped her chin while inserting my thumb into her mouth, holding her jaw down.

Erin was playfully running her tongue around my thumb.

I moved my hand behind her head and grasped her ponytail tightly and pulled her head back. “It this why you came with a ponytail tonight?” I asked. “So I could use it to pull you onto my cock as I enter you from behind.”

“Yes, master,” Erin said, with a shudder. “Or use it to direct my mouth when you face-fuck me.”

I let go of her hair and undid the clasp on her bra which rose above her breasts. Erin’s breasts were firm mounds and had erect, puffy, pink nipples. I reached under her and ran my hands over her breasts and then gave each nipple a firm twist, which elicited a moan from Erin.

I went around her back side where Erin had her ass pointed in the air with her knees spread apart. I ran my hands over her firm white buttocks and touched a wet spot on her panties. “Someone is excited,” I said, as I pulled the panties aside to sink a finger in her shaved, sopping pussy.

Erin pushed back on my finger in desperation.

I removed my finger which was covered in her juices. “Look at this mess,” I said. “This won’t do.” I moved my hand up and put the wet finger in her mouth which she sucked on like a baby.

“So, you like the taste of pussy,” I stated. “We will have to see where that leads to.”

I pulled my hand back and pulled down her panties which were over top of her garter belt. As I ran them down her legs, I noticed something between the alabaster cheeks of her ass. It was a pink plastic disc.

“You went through dinner with this in your ass?” I asked.

“You said to come prepared tonight,” Erin said. “Jenn told me about your fascination with her asshole. I thought I should demonstrate my willingness in this area and to have myself prepared for the coming sodomy.”

“Very thoughtful,” I said. “I appreciate creativity and initiative in my partners.”

I gave her alabaster ass cheek a quick slap which elicited another moan from Erin.

“You like having your ass slapped?” I asked.

“I do, sir,” Erin said. “It heightens the pleasure and anticipation.”

I then got up and pulled my shirt off and dropped my boxers while appreciating the sight in front of me. Erin had her hands spread out with her chest down to the mattress. Her ass, with the butt plug in it, rose above her knees and was perfectly accentuated by the garter belt and silk stockings.

An idea came to me, and I grabbed my phone and took a couple of pics.

Erin didn’t say anything, but had a look of need in her eyes.

“Jordan had demanded all the details of my dates,” I said. “I am going to send her a visual to get those started.”

“That is so kinky,” Erin said. “I have never been much of an exhibitionist, but that is great. Keep your phone close and do some more selfies through the evening. I am fine with pics as long as they aren’t for public use.”

“I am not so sure of showing images of me doing things to you,” I said. “That might be crossing a line with my daughter.”

“Rob, get over it,” Erin said. “You described a fantasy where you violated my daughter. You have already crossed that line. Own it and enjoy it, and never be unsure.”

Erin was right. I sent an image to Jordan with the caption, “Date is going well!” It was from the Erin’s rear quarter and showed her tied to the bed and you could clearly see the butt plug. I took the phone with me and was going to place it on the nightstand when it dinged with a message.

I read it out loud, “Dad, that is awesome. I want you to fill all her holes tonight. Don’t hold back and send more pics.”

“You heard your daughter,” Erin said with a smile, as she wiggled her ass. “Time to get to work, big boy.”

I put the phone down and grabbed a breast and while twisting a nipple, I said, “Not so quickly, my little hussy. Good things will come to those who wait.”

I went behind Erin and ran my hands over her bum. I could see the handprint where I had spanked her. I bent down and gave it a gentle kiss.

I ran my hand from the disk of the plug down across Erin’s pussy which was freely leaking now. “It is so wet,” I said. “I think we may need to do a bit more cleaning.”

I bent further down and kept a hand of each of butt cheeks and inserted my tongue into her leaking gash. I pressed my chin into her mons and moved my jaw up and down to provide stimulation to her clit while I tongue-fucked her pussy.

Erin started orgasming in less than thirty seconds, which sent a new flood of juices onto my face as her pussy contracted around my tongue.

“Hmmm,” I said, “that just seemed to worsen the problem. Maybe I should try to plug the hole to stop this leaking.”

“Impale me with your fuck-stick, sir,” Erin pleaded.

I could have cut diamonds with my cock at that moment, and rose to kneel behind her.

I ran the head of my cock up and down her slit.

Erin tried to push herself back on my cock, but I withdrew my hips, and gave her other cheek a spank.

Erin held still as I again ran my cock up and down her pussy getting it lubricated with her juices. I tapped the disc with it and mused, “Maybe I should claim this hole first.”

“Either one is available and ready,” Erin said, in a needy voice.

I moved my cock down to entrance to her pussy. I was intrigued at how it would feel with the plug in her ass. I slowly pushed in which elicited a grunt from Erin.

It was a tight fit, with the plug taking up some of the room. I could feel where the maximum girth of the plug was, and it was easier going in penetrating Erin from there. I continued to push until I felt my cock touch the top of her tunnel. I had it all in with only a half inch showing outside her pussy.

The view of her spread pussy and narrow hips was great. She had taken me like a champ. I did one slow first stroke and when I touched the end of her tunnel again, Erin let out with a scream.

I waited for her spasms to stop and then started stroking into her, trying to maximize the distance I pulled out and then roughly pushed back in. Erin was incoherent and was cumming again.

I didn’t stop this time and kept pounding her like an animal, as I was approaching my own climax.

I pushed in with one last stroke and then sent my seed directly at her cervix which caused her to spasm some more.

I left myself sheathed in her, to allow all of my cum to drain into her.

Erin looked back at me over her shoulder and had a big sloppy grin.

“Did you like that?” I asked.

“You don’t have to ask me that,” Erin scolded. “I had multiple orgasms on your righteous cock.”

“Then a simple ‘yes, sir,’ will suffice,” I said, and gave her ass a spank.

I pulled out of Erin and went around and untied her hands. She had to be getting sore from being in the same position for so long.

As I finished untying her other hand, she rolled onto her side and grabbed my now-limp cock and eagerly put it into her mouth.

“Master must be clean before he gets dirty again,” Erin said.

I grabbed my phone a took a quick picture as my cock regained its hardness in Erin’s mouth. She saw what I was doing and said, “Send her two pictures. One with just the head of your cock in my mouth and a second one with you lodged in my throat.”

I complied with her idea and while Erin kept up with her oral attention. I thought about the message I would send and knew that I was crossing a line no matter what Erin said.

The message read. “Clearly no issue here with oral pleasure after taking her pussy. Ass is next.”

I hit send and crossed that line. I hoped that I wouldn’t regret this.

An immediate reply came back, and I read it out loud to Erin, “So hot, dad. Push that monster into her asshole and show her who is boss. Pull out of her ass when you cum and feed it into her mouth to complete the trifecta.”

My cock instantly got harder, which Erin could feel. She pulled back and said, “I think you like her plan, and so do I. Your daughter is a revelation and nasty piece of work. This is going to be so much fun.”

I manhandled Erin to lay on her back with her ass extended over the edge of the bed while she held her knees close her chest.

I ran two fingers into her pussy to get her warmed up, before I slowly pulled out the butt plug. Erin had prepared herself well, as I could feel the lube on the plug. This reminded me to apply lube to my cock, as well.

I ran a bead down my shaft and Erin rubbed it in and then placed the head of my cock at the entrance to her asshole.

I took a quick pic for the before image. I put the phone down and then nodded to Erin as I pushed into her ass.

As I passed her outer ring, Erin let out a scream. She had sweat on her brow and said, “Oh my fucking god. It feels like you are shoving a telephone pole up there.”

I held my position to let her get used to it and took another quick pic. When I put the phone down Erin looked up to me and nodded.

I kept pushing in until I was about halfway in.

“I don’t think I can take any more tonight,” Erin exclaimed. “I will have to do a better job of prepping for the next time.”

I took a quick pic again, as I held steady and applied more lube to let her get used to my penetration.

I looked up at her face and asked, “Are you ready?”

Erin nodded, and I pulled back slowly. When I had my cock head just in front of her anal ring, I applied some more lube to my shaft and then slowly pushed in, to halfway again.

Erin still had sweat on her brow and an intense expression on her face. She grunted when I stopped and said, “Okay, that was better. You can start stroking me to that depth.”

I complied and slowly built my rhythm.

After a couple of minutes, Erin was moaning and then suddenly her muscles contracted in orgasm which put incredible pressure on my cock.

She screamed out, “Ah, ah, ah, that is my first anal orgasm.”

I let her spasms pass and then continued to stroke her never going past the halfway point. I was getting close and said, “Are you ready for the finale?”

“Grab your phone and make it a video,” Erin suggested, with a naughty grin.

I did as suggested and scrolled to the video setting.

The distraction of doing this meant that I had to build my rhythm again. I quickly got close again as I watched my phone screen of my cock sliding in out of Erin’s ass. I looked up at Erin and nodded.

I pulled back and out of her now-gaping asshole.

Erin pushed herself up with her hands and then slid down to the floor and had her head directly in front of my cock.

I used my other hand to grasp Erin’s ponytail and guided my slimy cock to her mouth. As my cock approached her mouth, Erin opened her mouth wide and extended her tongue.

I guided her head and let her lewdly lick the head of my cock. I then pushed steadily into her mouth and put my cock all the way down her throat.

I pulled back and Erin gasped in air and started stroking my shaft with her hand.

My first stream exploded from my tip and hit her upper lip and dripped down into her open mouth. The second went across her cheek. I closed the gap and reinserted my cock into Erin’s mouth and continued to spasm into her mouth.

I withdrew my cock from Erin’s mouth and pulled her head back and said, “Open your mouth and show us.”

Erin opened wide and used her tongue to swirl around the cum in her mouth.

“Now, swallow that load and show me what a cum-slut you are,” I ordered.

Erin made a show of gulping the cum down and then used her finger to scrape the cum from her face and then lick it off her fingers.

The display was so erotic, I felt my cock responding again. I didn’t think I had a third round in me, but it wasn’t out of the question based the eroticism of Erin’s actions combined with the involvement of Jordan.

After I stopped the video, I reached down and drew Erin up and said, “That was the hottest thing I have ever done.”

“Me too,” said Erin, with enthusiasm. “I have more ideas and I am sure you do as well. I am open to it all.”

We collapsed on the bed and Erin snuggled into my side and stroked my chest. I grabbed the phone and hit play on the video, and we watched it together.

“Next time, I will be better prepared to take you balls deep in my ass,” said Erin. “I may not be able to walk afterwards, but it will be worth it.”

I pulled up the conversation with Jordan and first sent the before the pic with me at Erin’s asshole. Next was the pic of me buried halfway into her narrow hips. Lastly, I sent the video.

“Erin, you are my new hero,” Jordan replied.

What came next from Jordan, I was not prepared for.

“You have both inspired me as I have seen what you have done,” Jordan texted.

An image then came across with a smiling Jordan holding a large pink dildo next to her face.

The next image was Jordan laying on her bed with her skirt hiked up and wearing no underwear. The view was from the bottom of her bed. She clearly had the ability to take the pic remotely, or there was someone else there to take it. Jordan, like Erin, was completely shaved in her pubic area.

The next image had her with the dildo being shoved in her pussy. Her other hand was under her bum, and she was inserting a finger in her ass.

The last text was a video. I wasn’t sure I wanted to open it and see this.

Erin sensed my hesitation and said, “Rob, you crossed the Rubicon earlier tonight, she is just reciprocating in style. You would be disrespecting her by not opening that.

“By the way, you are showing your actual excitement down below.

“Lastly, if you don’t open it, I’ll take your phone and do it. This is hot as hell, and I can’t wait to see what she sent.”

“You are right,” I said. “It has been a big night and I hope you understand.”

“Rob, I do understand,” Erin sympathized. “I only wish I had this level of trust with my daughter. In reflection, you will realize that this is very special.”

I hit play on the video.

Jordan was now on her knees with her bum raised like Erin’s was. She was pumping the pink dildo in and out of her ass while her other hand had two fingers pumping her pussy in time with the dildo.

I realized there was audio and turned it up to hear my baby daughter grunting and then screaming in orgasm. She rolled over with the dildo still inserted in her ass.

Jordan withdrew the dildo and looked at the camera and said, “Erin, if you can do it, so can I.” She then pushed the dildo into her mouth and down her throat. Jordan gagged a bit and pulled the dildo out with a gasp and said with watery eyes and drool falling from her lips, “Daddy, I can’t wait to get home for Thanksgiving for a front-row seat.”

I was now rock hard again and looked at Erin.

Erin looked back at me as she was stroking my cock and said, “Jordan might just want to see us do it, but I think that she may want direct involvement.”

I just nodded, as Erin descended to insert my cock in her mouth. She aggressively deepthroated me, and I could see her neck expanding as my cock went down her throat.

I was so turned on by Jordan’s video that I was about to cum for the third time after only a few bobs by Erin.

I grabbed her ponytail and held her head down on my cock, as I shot my last load of the night directly into her throat.

After that intense final session of the evening, we cuddled again and watched Jordan’s video a second time.

I tapped out a simple reply saying, “We can’t wait.”

_____

I had work in the morning and was dead asleep when the alarm went off. I quickly got up and showered. When I came out of the bathroom, Erin was just waking up.

“Erin, I am really sorry, but I have to get to work,” I said. “Please don’t take my quick departure as an insult. Last night was very special and I want to continue seeing you whenever you have the time.”

“Rob, you are so sweet,” Erin said, with a smile. “I am open next week. Call me and we can make a plan. It just better include us spending the night together.”

I gave Erin a deep kiss and hugged her before excusing myself to go. “I will call you later today.”

As I was leaving, Erin asked, “Can you please send me those pics and video. I want to review, and it will tide me over until we fuck again.”

I agreed and then quickly headed out to work.

After settling at work, I sent Erin the media. I had only been on one date but had to trust her, as she trusted me.

I left for lunch and gave Jordan a call on my way. I was in Boston and was three hours ahead of her in LA. She greeted me with a cheery voice and when she determined that I was alone, she said, “Daddy, that was so hot last night. I really appreciated your trust in me in sharing those details. I hope you liked how I reciprocated.”

“Jordan, involving you in this journey has been the best decision I have ever made,” I said, sincerely. “I hope I didn’t cross a line last night that will hurt our relationship.”

“Daddy, I am closer to you now than ever,” Jordan said. “There is no going back, and I am excited about what you have in store.”

“I feel the same, honey,” I said.

“I have some new information for you, by the way,” Jordan added. “I have been in contact with Samantha. She has total understanding of what went down with Jenn. She admitted to walking into the house early on the evening you were with Jenn.

“Samantha stood outside her mom’s bedroom and heard you first eat her mom to a screaming orgasm and then fuck her brains out. She was flabbergasted when her mom refused to carry on that night.

“Samantha resumed her spying the next morning when you repeated your oral skills and then heard the subsequent argument when Jenn was reluctant to reciprocate. Again, she was shocked by her mom’s attitude.

“Samantha commented that you had every right to dump her. She added that Jenn is having a lot of second thoughts about her behavior and had even talked to Erin about the evening.

“You probably know much of this, but I think you will find her last comment interesting.

“Samantha said that if she would do anything for a person who wasn’t a ‘wham bam, thank you ma’am’ kind of guy and someone who would get her off multiple times in an evening.”

“I hope I haven’t put a wedge between her and her mom,” I said. “I never wanted to cause either of them pain.”

“I don’t think their relationship is in your control, or something you should be worried about,” Jordan said.

“Then why are you telling me this?” I asked.

“I will bet dollars to donuts that Samantha may be interested in you,” Jordan said. “I am going to add her to the list.”

“That is ludicrous,” I said. “I am a forty-two-year-old man and could literally be her father.”

“Yes, you are,” said Jordan. “She won’t see you as a father figure anymore. You are a confident, accomplished older lover who can meet her needs, which are very real. She broke up with her boyfriend who was everything you are not.”

“With respect to the list,” I said. “Aren’t we done with evaluating new prospects after last night.”

“No, we are not,” said Jordan, emphatically. “One night does not make you exclusive with Erin. You still need to continue to date and experience others so you will know what you want.”

“I want you to go on that date with Heather,” Jordan said. “And I want you to be open if Samantha approaches you. Adding the experience of age differential will help you figure out what you want. You should also consider asking out one of those sales ladies we met at the clothing store. They are women you don’t know at all, and that would be a new experience, as well.”

“How do I explain that to Erin?” I asked.

“Erin has been playing the field for years,” Jordan said. “I believe that she is very attracted to you, but I doubt that you are her exclusive now. Ask yourself why she isn’t seeing you until next week?”

“So, you’re saying that I should continue fucking with abandon,” I said.

“Absolutely,” Jordan said. “If I read the tea leaves correctly with Erin, I doubt that she would be disappointed. She might want to join you, and have you recount stories of your conquests, just like I do.”

“Wow, you are going to have me worn out,” I said.

“Dad, you are in the best shape of your life,” Jordan said. “Own the challenge. You are up to the task.”

“Yes ma’am,” I said, with confidence. “Talk to you soon.”

We said goodbye and I promised to keep her up to date. I thought about my way forward over lunch and sent two texts.

The first was to Erin. “I know the advice is to not immediately contact a date, but I never follow pop culture on dating. Let me know when you are free next week so we can come up with a plan.”

The second was to Heather: “Looking forward to seeing you for coffee after work tomorrow.”

Erin responded that she would come up with a plan for the following Tuesday and she would take care of the preparation.

My next text wasn’t from Heather as expected, it was from Samantha. She wanted to meet me and talk about her mom. I suggested Thursday at my place after work, as I had the date with Heather on Wednesday.

_____

I met Heather at the coffee shop. She was dressed professionally and looked great.

Heather was the picture of confidence until you started to talk to her. She was still unsure of what she wanted in her career, or from a relationship. Her career had gone well so far and was probably driven by her intelligence and looks, but held back by her indecision.

Heather expressed empathy at Susie’s passing, but did not show that much interest in exploring a relationship. I could have pushed it, but decided not to, as I that indecisive quality about her would never go away and she would live her life with regrets. It wasn’t what I wanted.

After getting back in my car, I called Jordan.

I let Jordan know of my developments with Heather.

“I understand your decision with Heather,” Jordan replied by text. “I have traded a few messages with Samantha and have some details we should discuss.”

I called Jordan and she immediately picked up.

“You said you had some more info on Samantha,” I said.

“She is clearly hot for you and is using the excuse of talking about her mom as way to engage with you,” Jordan said. “She was quizzing me on what you have been up to and things that you like. I mentioned that you were exploring new relationships and that you liked women who are decisive and yet submissive.”

“Jordan don’t lead her on,” I implored. “I don’t want her to get hurt or to destroy her relationship with her mom.”

“Dad, she is an adult,” Jordan said. “She isn’t the kid that you knew when I was growing up. She is eighteen and has firm grasp on who she is, and is not inexperienced.

“Don’t concern yourself with her mom. That is water under the bridge.

“Rocking Samantha’s world, would open her up to understanding what a positive sexual relationship can be. If it doesn’t work, she will forever have the gift of understanding what a confident, capable lover can do for her.”

“I should talk to you more,” I said. “I always come out of it feeling better about myself.”

“You should feel better, daddy,” Jordan said. “You deserve love more than most.”

_____

Thursday arrived, and I was home from work and had just finished dinner when the doorbell rang.

Samantha was there and dressed in an athletic skirt and a tight, sleeveless top that showed her model-like qualities. She was tall and athletic, with long toned legs, tight abs, and medium-sized breasts. Her long dark hair was tied back in a ponytail, and this accentuated her full lips and large blue eyes.

I offered her something to drink and she said she would have whatever I was having. “It is a weeknight, so I am just drinking water,” I said. “I hope that’s okay.”

We grabbed glasses and headed to the patio.

“You look nice tonight, Mr. Smith,” Samantha said. “You have really come out of your shell since the summer.”

“I had a lot going on both with the estate and with Jordan home,” I said.

“My mom was surprised when you showed up to that party,” Samantha added. “I think she had been stalking you for a while.”

“We had a nice evening, which obviously went on longer than the party,” I said.

Samantha took a big breath and said, “I know that things didn’t end well between you two. If I am being honest, I heard most of what happened. Personally, I was horrified with mom’s behavior. She was so selfish and inconsiderate with you.”

“I am sorry that you were caught up in it, at all,” I said. “You have had to deal with your parents’ divorce, and you now feel involved with your mom’s relationships.”

“That was a choice I made,” Samantha responded, “Just like Jordan, who I understand, has helped you figure things out.”

“That is very mature of you,” I said. “How are you helping Jenn, now?”

“I have been giving her some tough love,” Samantha said. “I’ve called out her behavior with you and suggested that she is an idiot for not respecting your needs and at least reciprocating.”

“How did that go over?” I asked.

“She refuses to acknowledge her own issues,” Samantha said. “She doesn’t blame you, which is a start, but is still blind to her shortcomings.”

“How can I help?” I asked.

“I don’t think there is anything you can do for her,” Samantha said. “I do have something you can do to help me, however.”

“What is that?” I asked.

Samantha looked up at me with those big eyes and reached out to put a hand on mine and said, “I want to experience what you and my mom did. I have never heard lovemaking that lasted that long, or ended in such a vocal crescendo. I would promise to reciprocate and would be open to doing anything you desire.

“I have talked to all my friends, and they have never described themselves as having experienced anything like that, or have they heard of anyone who has.

“I’ve laid awake every night since you were over, and imagined myself in my mom’s place. I want you to eat me to orgasm and I’ll suck your cock until you blow your seed in my mouth so I can swallow it. I want you to fuck me repeatedly and not just once a night. Lastly, I know you like anal and would be honored to give you that cherry.”

“Wow, Samantha,” I responded. “That is quite an offer. I want to discuss some aspects of this, though. How would this affect your relationship with your parents when they find out? How will this affect your standing in the community, when neighbors find out?”

“The neighbors and my parents don’t have to know,” Samantha suggested.

“They always find out,” I said, with confidence. “Nothing is ever a secret after two people know about it. I am not saying that I would go and crow about it, but my experience is that everyone eventually learns about it.

“Look at what happened with your mother. You know, Jordan knows, and Erin knows. Soon, the information will be widespread. What is your mom likely to do and what will your dad think? Your friends will treat you differently and say you’re perving on a sugar daddy.

“You really need to think about all those implications, as do I.”

“I hadn’t considered all those scenarios,” Samantha said.

“I want you to take a couple of days to consider it,” I asked. “I want you to tell your mother, if you want to do this. I will give it consideration, as well. You are a beautiful and bright woman, but I don’t want you to act impulsively with these implications.

“Jordan alerted me of your interest, and I rejected the idea initially, until she convinced me to consider it. She said how mature you were.

“Let’s meet on Saturday and we can discuss this further. I am not saying no, but I am not saying yes, either.”

“That is very fair, Rob,” Samantha said. “I’ll think about the issues and confront my mother if I want to try this.”

We said goodbye and I gave her a brief hug that she wanted to extend. “See you Saturday afternoon,” I said.

I called Jordan that night and told her about my developments with Samantha.

“Dad, get ready for action on Saturday,” Jordan exclaimed. “You were insightful and reasonable at articulating the issues, but they are nothing in comparison to the fucking that she is expecting.”

“You think so?” I asked. “There are real risks for her.”

“All of that will be overcome by lust,” Jordan predicted. “Samantha wants to scream out like her mother, and try to possess what her mother couldn’t. You will give in to a young, willing girl who has a model-like body, and a desire to learn and do anything.

“I expect that you will share details again. Hopefully, in a similar manner.”

_____

Saturday came quickly and Samantha arrived on my doorstep ten minutes early, with a spring in her step and an overnight bag on her shoulder. Jordan was right again.

Samantha came in and wanted to go directly upstairs.

“Not so fast,” I said. “I think I know your answer, but I want to discuss it further.”

“Can’t we do that upstairs,” Samantha said, with an eagerness which was endearing.

I ushered her to the kitchen, for two weak G&Ts. We went out on the deck and took seats.

“Samantha, I know you are excited,” I said. “I want to ensure that you understand what you are doing and what my expectations are. I want to be completely transparent so there are no hurt feelings or misunderstandings.

“Tell me how the discussion with your parents went?”

“I tried to talk to my mom again,” Samantha described. “I told her that I had heard the whole argument and her screams of joy during your lovemaking and that I disagreed with her decision, but respected it. I continued to tell her how intoxicated I was at what I had heard and discerned.

“I told her that I wanted to experience that, as well.

“Mom said, ‘good luck with that. There aren’t many guys out there who will bring you there.’

“I said that there was clearly one guy like that in our neighborhood and he might show me.

“Mom scoffed and wouldn’t listen to me after that.

“With respect to my dad, I haven’t spoken to him in months. He pulled a full disappearing act, so I don’t owe him anything.”

“Good on you for trying with Jenn,” I complimented her. “You realize the other implications with people you know, as well?”

“I do,” said Samantha, sincerely, “And I don’t care what others think of me. That is mom’s gig; I am going to pursue what is best for me and not worry about what other people think.”

“You seem to have this straight on your side,” I suggested. “I want to be fully transparent with you about me and the possible relationship we might have.”

“I am all ears,” said Samantha, with a smile.

“As you are aware, I am in frequent contact with Jordan,” I said. “We share everything now. I would be sharing details of our relationship with her, even pictures.”

“I’m cool with that,” said Samantha. “We’re good friends and I see how close you are with her. Frankly, I am jealous of that and wish I could be that way with my folks.”

“The second area is around exclusivity,” I said. “I obviously went on a date with your mother, and I have been on dates with others. For now, I would continue to date others and that will likely involve intimate moments.”

“So, you’re going to keep fucking Erin while you fuck me,” Samantha said, with a smile.

I almost did a spit take with my drink but held it in, and took a second before I said with a smile, “You paraphrased that well.”

“You wanted full transparency, so I thought I would put it bluntly,” Samantha said.

“My last question is less of a deal-breaker,” I said, carefully. “How adventurous are you, and would you consider a threesome with another woman?”

“Let me paraphrase again,” said Samantha. “If Erin shows up one night, am I willing to share and possibly do lesbian acts with her.”

“Jordan said you were perceptive and bright,” I said. “That is a reasonable way of putting it.”

“Rob, I am probably open to anything if it brings me to orgasm or if it is something you want,” Samantha said, with sincerity. “I am a submissive person by nature, and here I am choosing to let you direct me. I trust that you will have my pleasure in mind. I have done a few things like this already, with my dance partner. I liked it, but eventually realized that I like men more.”

I reached across the table and put my hand on her cheek and drew her to me for a kiss.

“I am so excited that this is going to happen,” Samantha gushed.

“We are going to start pretty slow,” I suggested. “There is no rush in any of this, and we have the whole afternoon and evening.”

“As you can tell, I’m impatient and raring to go,” Samantha said, and rubbed her hard nipples through her shirt.

“Maybe we should get a quick one to settle you down,” I said.

Samantha jumped up and let out a little squeal of joy. “I can hardly wait,” she said.

“Let’s go to my bedroom,” I said, as I stood up.

Samantha came in a gave me full body hug. She was almost six feet tall, so she was close to my face and looked up and pulled me down for another kiss.

We went hand in hand up the stairs and went into my bedroom.

Samantha started taking off her shirt and I grabbed her hand and said, “Allow your partner to undress you, it adds to the anticipation.

“You are a stunning woman and I love your intelligence and candor. Always tell me what feels good and if you are ever uncomfortable with anything. I will direct you, but don’t want to push you into anything you will regret.”

As I spoke, I started unbuttoning her shirt. I leaned in and nibbled on her ear while completing the unbuttoning.

I stood back and slowly peeled the shirt from her narrow shoulders. Below her shirt, she had on a black sports bra which contained her apple-sized breasts.

I ran my hands over her shoulders and let one hand glance off her covered breast and let it descend to now unbutton the top of her skirt.

I was just wearing a t-shirt which Samantha pulled from my shorts. As her skirt fell to the floor, I raised my arms so she could remove the shirt.

“Rob, you are in better shape than most of the boys on our football team,” Samantha complimented. “I love the lean muscle.”

As Samantha unbuckled my belt, I ran my hands up her side. As my pants dropped down, I pulled up her sports bra to liberate her breasts. They were firm and capped with rose-colored nipples with hard, pencil eraser-like points to them.

I guided Samantha to lay on the bed and I followed her onto it. I ran my mouth from her neck to one of her breasts, which I tenderly took into my mouth.

With my other hand, I ran down her flat, toned belly to grab the waistband of her panties. Normally, I would go slower, but she was making urgent sounds to proceed. I intended to make her cum once, and then go slowly.

Samantha, on her own accord, grabbed the sides of her panties and pulled them off.

I ran a hand over her smooth mons which elicited a brief moan.

I raised my head to look at what had been uncovered. Like Erin and Jordan, she was completely shaved. “I appreciate a shaved woman,” I said. “It makes everything more visible and cleaner.”

Samantha glowed with appreciation.

I kissed my way down from her breasts and she clearly wanted me to enter her triangle, but I wasn’t going to go that quickly.

I gave the top of her mons a quick kiss, and then made my way down her long legs and grasped her slender feet. I put a toe in my mouth and looked up to see that Samantha was dripping juice from her slit.

I slowly kissed my way north, as I spread her legs. I gave her slit a quick lick and then rested my chin on her lower belly and smiled at her.

Samantha’s brow was furrowed, and she clearly wanted me to focus on her pussy.

“Are you ready?” I asked.

“Oh, yes,” Samantha said, in a husky voice.

I raised my head up a bit and pursed my lips to blow first on her belly and then on exposed pussy. I could feel the shiver run through her body.

I kissed her outer lips, but did not touch her clit or penetrate her.

I finally used a hand to spread her pussy lips and then firmly put my tongue on her spread vagina. I slowly moved my head and taking long, slow, languid licks.

Samantha was moaning now.

I stopped short of her button, and when she tried use her hand to stimulate it, I pushed it away.

I inserted a finger in her tight pussy and kept the pressure up, just above her opening, with my tongue. I slowly inserted a second finger and then started to time my finger insertions with the strokes of my tongue.

Samantha was rolling her hips to try to get more pressure and to move my mouth onto her clit. My fingers were all the way in her and I moved my mouth to her clit to comply with her desire. She started orgasming in seconds and let out a mewling-like sound, as I felt her pussy spasm around my fingers.

Samantha thought I was done and made movements to encourage me to rise to her.

Instead, I waited until her orgasm passed and then slowly kept pumping her with my fingers and then applying my tongue to bring her to a second climax.

After she came down from that one, I pulled my juicy fingers out and brought them to her mouth.

Samantha grabbed my hand and started fellating my fingers. She had no hesitation in tasting herself.

I pushed back her legs to expose her ass and proceeded to put a well-lubricated finger into her anus, just up to the first knuckle. I reapplied my mouth to her pussy and brought her to her third screaming orgasm.

“No more,” she said, after coming down. “I need time to recover.”

I relented and crawled up next to her.

Samantha held my face that was covered in her juice and first kissed me and then licked her juices off of my face.

“That was incredible,” Samantha said. “I have rarely had one orgasm when I have had sex with boys. You have given me three and I haven’t even seen your cock yet.”

Samantha reached down for my cock and pulled it out of my boxers. Her slender hand was just able to encircle it and she raised her eyebrows. “Hannah wasn’t kidding when she said you packing a cannon,” Samantha said. “How big is it,” she asked.

“About eight inches,” I responded.

“Is it going to fit in my tiny pussy and tight asshole,” she asked, with a smile.

“Yes, it is,” I said. “We are going to make sure you are well lubricated and prepared before we attempt that.”

“I know one place that doesn’t need any lubrication right now,” and with that, Samantha quickly started kissing down my chest. She quickly stopped to lick my nipples but clearly wanted to insert my cock in her mouth.

She approached my cock, held it vertical, and looked all around it before leaning in for a kiss on the head.

While doing this, she kept up a steady stroke with her hand.

Next, she opened her mouth and sucked the head in. I was warm and I could feel her tongue roam around. She popped it out and looked up at me and asked, “Are you going to direct me?”

I smiled and said, “That will come later. Your first experience should be one of self-discovery.”

Samantha smiled back, and then proceeded to lick down the shaft and started to lick my balls. I have to admit that this never did that much for me, but I appreciated her efforts.

Samantha returned to the crown and engulfed it again with her mouth. This time, she tried to push more of my cock into her mouth until I touched her tonsils which caused her to briefly gag.

“How much did I get in?” Samantha asked.

“About half,” I said.

“How far can Erin go?” Samantha asked.

“All the way to the root,” I responded.

Samantha looked with shock at my cock, and said, “I clearly need some lessons from her.”

“Practice will be needed,” I said. “Taking a man’s cock into your throat is an enormous turn-on for most men, including me.”

“I will practice,” Samantha said. “I want to be a deepthroat queen, and have you shoot your spunk directly into my gullet.”

“It helps to get your throat aligned with my cock,” I suggested. “Then you won’t be pushing on the back of your throat so hard.”

Samantha scooted around to have her bum close to my head and proceeded with her attempt of putting me in throat again. She got the head past her tonsils and then started to gag and retch.

I stoked her head and said, “That was a good start. Give it a break, or you are going to throw up on my stomach.

“How should I get you off, then?” Samantha asked.

“Grasp my shaft in the middle,” I suggested. “Then, put your mouth over the end. Move your mouth up and down in time with your stroking hand. Apply pressure with your lips and dart you tongue at the bundle of nerves on the underside, just below the head of my cock.”

Samantha was a quick learner and did exactly what I suggested.

I was going to cum soon and said, “I’m almost there. When I cum, keep a lip lock and allow me to completely finish in your mouth. I want you to swallow it all. That is another turn-on for me and was key failing of your mother. She spit out the cum I delivered and got mad at me for blowing in her mouth.”

Samantha lifted her head off my cock and said, “Fill my mouth with your seed any time you want. I won’t spill a drop.”

With that said, she put her mouth back to work and it was only a few more strokes before I let go and sent a big load into her mouth. Samantha was good to her word and gobbled it all. She even showed me her empty mouth after finishing.

“Good girl,” I said, and gave her a kiss. I didn’t really want to taste myself but there wasn’t any real taste left by the time we kissed. It seemed only fair after she had licked her juices off my face.

“Are you going to fuck me now?” Samantha asked, with eagerness in her voice.

“I am going to need time to recharge,” I said. There is no hurry. I can’t orgasm as many times as you, so I’ll pace myself.”

“Are you going to try and claim all of my holes with your seed?” Samantha asked.

“I don’t think that I will be able to ass fuck you, tonight,” I said. “Your asshole needs a lot of loosening before it’ll be able to accommodate me.”

“How do I loosen it up?” Samantha asked.

“The primary way is with butt plugs,” I said. “They will get your sphincter used to being stretched and make some room in your anal cavity.”

“Do you have any here?” Samantha asked.

I went to dresser and pulled out the one that Susie had used. I grabbed a bottle of lube and returned to the bed. “You should start with the small one first and then graduate to a big boy and leave it in until I replace it with my cock. For tonight, just stick with the small one.”

“Okay,” Samantha said. “Put the small one in now. It’ll be a good test.”

I thought her eagerness would dissipate after three orgasms and blowing me. I was wrong.

I got her to kneel on the bed and started applying lube to her asshole with a finger. I then lubed up a finger and pushed it in, to the second knuckle.”

“It feels funny and there is some burning at first,” Samantha said, as I started pump the finger in and out. “Now it feels better.”

I kept adding lube and drove my finger deeper which had Samantha starting to moan. I pulled out my finger, applied lube to the smaller plug and then started to push it in. There was some discomfort on her face when the widest part expanded her anal ring. It dissipated as the plug went all the way in.

“It is in now,” I said.

“It feels good, but I want to do more,” Samantha said, with desire.

I shrugged, got up and grabbed a selection of dildos from the same drawer. “I can fuck you with one of these and you can experience your first double penetration.”

“That sounds great,” Samantha said, as she rolled onto her back.

I selected a smaller dildo and Samantha spread her legs.

“Wait, I have an idea,” Samantha said, and pulled her legs up and was able to put her arms on her thighs which then had her feet behind her head. It lifted her bum a bit off the bed and had her pussy completely exposed with the butt plug visible just below.

“Where did you learn that?” I said, with wonder.

“Twelve years of dance has made me very flexible,” Samantha responded.

I leaned down and gave her pussy a quick lick and then spat on it and used two fingers to lubricate her already-moist lips.

I put the dildo at the entrance to her pussy and looked up at her.

“Push it all the way in,” Samantha said.

I shrugged my shoulders and put the dildo all the way in, as I spread her pussy lips with my fingers. I lowered my head again and licked her clit as I pushed the phallus in and out.

I remembered my commitment to Jordan and took a moment to quickly get up and grab my phone for a picture.

Samantha had taken over with the dildo and asked, “Are you going to send that to Jordan?”

“I am,” I said. “I have never seen someone so flexible and widely splayed. I think she will find it very sexy.”

Samantha posed for a few shots and said, “Sending pics to your daughter is so twisted. I love it.” She then started orgasming again, and I got a great shot with her mouth open wide in pleasure.

I went to put down the phone, but Samantha suggested I take a couple of more shots. She pulled the juicy dildo from her bald pussy and made a show out of sucking it.

I laid down next to her with my phone and showed her the pictures I had taken.

I reached out to her and pulled her in for a kiss.

“I had no idea what a dirty mind you have,” I said. “I recall a line from the song ‘Bang a Gong’ which went: ‘You’re dirty, sweet and you’re my girl.’ I think it describes you perfectly.”

“Your dirty, sweet girl isn’t done yet.”

“No, you are not,” I said. “But we should take a break for some dinner to get our energy back.”

“I do need some fluids,” Samantha suggested. “I have cum four times already and don’t want my pussy to become dehydrated. We need to keep it lubricated for the main event.”

We both got up and I put on a pair of shorts and Samantha put on my t-shirt.

We went to the kitchen, and I poured her a large glass of water and said, “Here’s to keeping you hydrated.”

I joined her with some water and started boiling water for pasta. “Carbs will help us after that workout as well.”

“Normally, I would avoid them to keep my dancer bod,” Samantha said, with a smile. “I think I have earned them tonight and will need the energy.”

I pulled up a few of pictures of Samantha and put them into a message to Jordan titled ‘Afternoon Delight’.

Jordan responded quickly with, “I knew that Samantha would make this decision. Ask ‘flexy’ what other tricks she has?”

I read the message to Samantha, and she thought for a second and then lifted one leg that she was able to hug to her body. Given that she was only wearing a t-shirt, I exposed her pussy and plugged ass to me as I took a photo.

Samantha grabbed my phone and typed a caption for the picture, “This is to allow easier access from a standing position.”

“Enjoy your evening with the ballerina,” Jordan wrote. “I am jealous.”

“If I sent that pic to mom, saying that she wouldn’t respond positively is an understatement,” Samantha said.

“Keep taking steps with your mom,” I suggested. “It took a lot of coaxing from Jordan to get me to be so open.”

We talked over a glass of wine and then plowed into dinner.

“Rob, you really are the whole package,” Samantha said. “You are an amazing lover, you’re handsome, in great shape, you cook, and are easy to talk to. What faults do you have?”

“I am sleeping with multiple women and have started a voyeuristic picture exchange with my only daughter,” I responded.

“I don’t see those so-called faults as negatives,” Samantha said. “You have been transparent with me, and I’m sure you will be with your other lovers. With your daughter, you have a close, caring relationship that I am envious of. Yes, it isn’t traditional, but you are both making it work to become closer. How can that be a fault?”

“Samantha, you are so sweet,” I said. “Thanks for your compliments and support.”

“You forgot about the dirty part that goes with that sweetness,” Samantha said, as she put the tip of her finger in her mouth and gave me a pouty look.

“We are getting back to dirty soon ‘Miss Insatiable’,” I said.

We cleared the plates to the kitchen. As I was loading the dishwasher, Samantha jumped up on the counter with her legs spread on either side of top rack of the washer.

“There is something else that needs cleaning,” Samantha said, as she drew up her t-shirt and pushed her bum closer to edge of the counter.

“Did I spill something on the stove?” I asked, in mock concern.

“No, it is something on the counter,” Samantha said, with a grin as she put hand on top of her pussy and ran a finger down each side of her slit to spread her dripping pussy open.

“Oh, I see the spot,” I said, again in mock recognition, and grabbed a cloth and wiped the drop of liquid that had escaped her pussy. “How messy of you, Samantha,” I teased. “If I clean up your mess, you will have to clean me up later tonight.”

“That isn’t a chore,” said Samantha, with eagerness. “I like the taste of my pussy juice and the combination with your cum should be heavenly.”

I closed the dishwasher and put my hands on Samantha’s thighs, and ran my tongue from the plug to her clit. I stood up and pushed Samantha to lie on the counter and then descended to lick her a second time.

I grabbed the end of the plug and pulled it out and then pushed it back in. “Do you like the feeling in your ass?” I asked.

“I am used to it now and enjoyed what you just did,” Samantha said.

“You’re still very tight back there,” I said. There is no way that I will get my cock in there tonight. You will have some work to do to get it ready.”

“As I have demonstrated, I am very flexible,” Samantha said. “I’ll just apply the same principles to my ass. I am just going to need some larger plugs to work with. People might say I am stuck up little bitch and they would be right.”

Her easy commitment to getting ready to take me in her teen ass had me hard as nails. I dove down on her, and aggressively tongued her hole, while rubbing her clit with my thumb.

Samantha grabbed my head and pulled me into her pussy. “That is so good,” she exclaimed between gasps, and then climaxed, sending a flood of juices into my mouth.

I stood up and pulled Samantha to a sitting position on the counter and then bent down and lifted the lithe teen dancer over my shoulder, and carried her to my bedroom holding her legs.

“I think I have woken the beast,” Samantha said, from my back side. “Are you finally going plunder my tight teen pussy with your cock?”

I just growled and tossed her on the bed and pulled down my shorts to expose my raging hard-on.

“How do you want me?” Samantha asked. “Do you want me to ride you like a cowgirl or do you want to fuck me like a dog.”

“I want you on the edge of the bed with your feet behind your head again,” I said. “You will be spread wide for my first entry, and we will both have a front-row seat.”

Samantha immediately started to move to end of the bed and then took a quick detour to grab her phone. “I think we will want to share that front-row seat with Jordan,” she said, with a wicked smile.

As Samantha got in place and bent like a pretzel, with her arms on her the back of her thighs. She ran a finger up and down her moist slit and then lewdly put it in her mouth.

I grabbed the lube and applied it to my cock and then approached her.

Samantha had a look of wanton lust on her face, and I am sure that I matched her.

I put the head of my cock at the entrance to her splayed-out pussy.