Coming of Age Pt. 01

Literotic asexstories – Coming of Age Pt. 01 by NerdySex,NerdySex
“My dad is having a party next Saturday, and he said I could invite a fiend. You interested in going?” the boss at my summer intern job asked.

I was surprised by the invitation. I was a new no-body. “Tell me about it.”

“He has a big house, I mean really big, with pool and everything. Mostly his parties are for heavy hitters in Vegas business. But this one is more social. It’s his way to get me to spend some time with him. Anyway, it’s always fun and some real eye candy.”

“Eye candy?”

“Dad is a mover in the Vegas community. Knows everyone and everyone that matters knows him. Plenty of good-looking women hang around. Who knows, you could get lucky!”

“Yeah, sure. OK, yeah, I’m interested.”

I asked around. His dad was the real thing. Everyone knew him or knew of him. My boss, Jim, was 24 or 25 and already moving up in the company. I was the kid, one week past my 18th birthday. Saturday arrived and he picked me up and headed into the mountains just outside Vegas. This was “the” area. Jim didn’t exaggerate, his house was a mansion.

“Hi, Jim, glad you could make it.” His dad, Mr. Hammon, was mid-40’s, handsome and tanned. “And this is the new guy, the summer intern?”

“Yeah, this is Jeff, our newest summer hire. He starts at U of M in the fall.”

Jim showed me around his dad’s place. It truly was fabulous. Some thirty or so other people had already arrived, some couples, some singles, including some absolute knockout women. I felt so totally out of place among this crowd. I supposed it showed as Jim took me around for some introductions.

Fortunately, a couple of drinks and I settled down a little.

“So, who do you know here?”

“Huh?”

“I said who do you know here?” one of the best-looking women I had ever seen was talking to me! “Everyone knows someone.”

“Ah, sorry, my mind was elsewhere. I work with Mr. Hammon’s son.”

“Cool. You seem much younger than the others.”

“Yeah, 18. Just graduated from high school and going to U of M in the fall.”

“Cool.” She led me out to the pool. “I’m Susan. What’s your girlfriend’s name?”

“Ah, don’t really have a girlfriend.”

“Still getting started, huh? I like that. So, tell me, does that make you a virgin?”

“Ah, does it show?”

“Not really but being so young I figured it was a possibility. And you do seem a bit shy. On the other hand, you are strikingly handsome in a pretty sort of way. I mean, I bet younger girls are quite attracted to you. Girls that aren’t, however, ready for sex. I wouldn’t mind robbing the cradle, honey.”

“Oh, there you are.” Jim’s dad, Mr. Hammon, approached, kissing Susan on the cheek. “Jeff is a friend of my son. I see it didn’t take you long to notice him.”

“He’s simply delectable, Gregory. I’m not the only one who noticed.”

“Well, you know how I always like to assess the talent.” Turning to me, he asked “Have you gotten the grand tour?”

“Jim showed me around a little.”

“There’s much more to see. Will you excuse us, Susan?

“On this level is the master bedroom suite, several other bedrooms, office, etc. Upstairs are more bedroom suites for guests that stay over. Follow me.”

The house was indeed most impressive. The master suite was unbelievable, bigger than my parents’ entire house.

“This is my favorite room for reasons I think you can guess. So, tell me a little about yourself.”

“I live with my parents and just graduated from high school. A friend knew your son and suggested I talk with him about a summer intern job. I started last week.”

“He said you did some modeling.”

“I did some magazine advertisements when I was younger. It was fun and the money was put in escrow for when I’m 21.

“And girls?”

“I wish. I seem to get really tongue tied around girls, especially pretty ones. They probably think I’m stupid. I mean, I have some friends who are girls but… well you know what I mean.”

“Jeff, don’t be so hard on yourself. It’s quite normal at your age to feel awkward around women. Well, nice talking with you. Glad you came.” He moved away to join other conversations.

****

“So, what did you think of the party?” Jim asked on Monday.

“It was very nice. But I felt out of place, much younger than everybody else. And everyone else knew someone. I’m not very good at starting a conversation.”

“You are very handsome but look even younger than your age. In five or six years all those women will be drooling over you, dragging you into their beds. What did you think of Susan?”

“Very good looking, sexy.”

“She knew my dad wanted to show you around but otherwise she would have seduced you.”

“Yeah, sure. Don’t give me that shit. You never said but I assume your dad is divorced?”

“Oh, yeah, twice. I don’t think he will ever do that again.”

“I noticed women keep their eyes on him.”

“He has all the pussy he could every desire. You know my dad really likes you. He wants us to come over next weekend. Dad has a thing for virgin ass.

“Oh? What do you mean?”

“Good looking young guys with tight asses, like you. You ever played around with another guy?”

“No, never something I considered. I’m not that way.”

“I just have a feeling you are more curious than you say. Lots of guys your age do some experimenting. It’s a normal part of learning about sex. Play along and see where it goes. You can always walk away. How would you like to fuck some girls? He can arrange that. A pussy virgin and an ass virgin, lots to look forward to. Dad knows how to reward.”

I don’t look at guys the same way as I look at cute girls. How do I really know what I really like? I think I prefer girls but so far I haven’t managed any strategy or initiative in that direction. My only sexual experience to date is my hand. I start college in less than three months as the most naïve freshman on campus.

“So what did you decide?” Jim asked the next day.

“I guess I’m willing to do some of that experimenting guys do.”

****

“Hi, Jeff. Come on in. Jim, how you doing? How about lunch?” Mr. Hammon greeted us.

“This is my personal recipe for Margaritas,” he commented as we sat on the spacious patio. They were delicious and quickly gave me a warm feeling in my stomach. Getting me drunk was undoubtedly part of his plan. I was so very nervous and didn’t mind.

“Want to try out the pool? No one can see us here so we don’t need suits.”

Jim and I horsed around as Mr. Hammon watched from pool edge. “Nice body,” Jim observed. “Slender, bubble butt, just what my dad likes. Just go with the flow and let it happen.”

“Jeff, come over here.” So this was it, decision time. I took the easy way. “You know why you’re here?” I nodded, staring at his hard cock. “Good, get ready to be fucked. Lay on this chase, ass up.”

My head was swimming from the drinks but very much aware what was about to happen. He pushed my legs apart and put something cold on my anus.

“Just try to relax, I won’t hurt you.”

I felt his finger push inside and move in and out. I remained still, letting him do whatever he wanted. I felt more cold and then pressure. He continued to press against me and suddenly my anus was stretched as his cock entered. I was being fucked and letting it happen.

“You doing ok?”

“Uh, huh. Your cock is in me?”

“About half way. Just relax.” He withdrew almost all the way, then slowly pushed back in. Back and forth, each time I could feel a tingle as he held my hips and increased his thrusting. I don’t know how long he fucked me. My anus must have stretched since he didn’t seem nearly as snug. With a final shove he pumped several spurts into me. As he pulled out Jim took his place. I guess I then fell asleep.

“You did great, Jeff. What did you think of your first fuck?” Mr. Hammon asked as I sat up and looked around.

“It was OK.” Actually, I didn’t think much of it at all and didn’t feel any different. I took a shower in one of the guest suites and rejoined them.

“How about we get dressed and go to Joel Robucohon for dinner. I’ll call for a reservation.”

This was the most expensive restaurant in Vegas. I had never been there, of course, but it had a great reputation for food and for people watching. I was certainly enjoying my stay with Jim’s dad.

“You need something else to wear, Jeff. Jim, show him the guest closet and see if there are things that fit.”

“This is one of the few places where a coat is required,” Jim explained as I tried on some slacks and jacket. It was obvious I wasn’t the first guy to need sprucing up.

I was getting used to the idea that Jim’s dad was a heavy hitter, a really heavy hitter. At the restaurant the maître de greeted him with enthusiasm and quickly seated us at a prime table.

“Did you have any trouble getting a reservation?”

Jim laughed. “He never does. It’s a mark of distinction if dad frequents a place.”

“Now that we have become acquainted, please call me Gregory. You have the perfect young-man body and tight ass that I like. I hope you don’t mind that we spend tonight in my bed.”

Back at the mansion I was again spread eagled, his cock pounding into me. I now knew what to expect and was more relaxed. Being fucked in the ass wasn’t nearly the big deal I had anticipated. I waited for him to finish.

“I have a proposal for you,” Gregory announced over breakfast. “I really like fucking you. I understand you still live at home with your parents. How about if you stay here for the remainder of the summer? I would pay you $1000 per week. And in exchange you have sex with me and Jim if he’s around, anytime we want.

“I also realize you are young and haven’t tried pussy yet. I will arrange for girls. When you start college, you will be one of the more experienced guys when it comes to sex. Of all kinds. Two and one-half months of pretty much non-stop sex, money, and pussy. Do you think you could handle that? Think it over and let me know after dinner. Talk with Jim.”

****

“Your dad is serious about his proposal?”

“Oh, yeah. You are definitely his type, barely legal, handsome, slender, pretty face. You are willing to try new things. In business or in pleasure when dad decides he wants something, he gets it.”

“I would have my own room? And make myself available whenever he wants to fuck me?

“Yeah.”

“And what about the girls?”

“Some of the sexiest girls in town, I’m sure.”

“Pros?”

“Escorts. High class pros. He pays the bills; you get top notch sex and an education. I need not tell you this is a rare and unusual opportunity.”

Given the promised benefits I decided that getting fucked in the ass was no big deal. It was only until school. That evening after a scrumptious catered dinner they both did me. Tomorrow afternoon some girl comes to take my pussy virginity. Can’t wait.

****

Jim left early the next morning and Gregory fucked me.

“The girl will be here about 1 pm.”

“What do I do?”

“I’ll make the introductions and the two of you can go out by the pool and get acquainted. I expect she will take the lead from that point. Don’t worry, she knows this is your first time.”

“Hi, I’m Amber. And you are Jeff?”

“Yeah,” my mouth was filled with marbles. This girl was much younger than I expected and absolutely gorgeous.

“You are very handsome. Very handsome. I’m really pleased to be your first. Of many, I’m sure.”

“Ah, yeah, ah, would you like to go out by the pool. And talk?”

“Sure. Don’t be nervous, honey. We are going to have a great time.”

This girl wasn’t anything like I imagined. She was young, my age, the girl next door with a dynamite body. We chatted for a few minutes. “Jeff, let’s go to your bedroom.”

Moments later I was looking at my first nude woman. “Here, let me help you,” Amber unbuttoned my shirt. My cock should have been hard as a rock but had somehow shriveled up. A couple of minutes, however, and she had it working.

“Very, very nice, honey. You are going to have lots of fun with those college girls. Handsome and a big cock, you are very lucky. Now leave everything to me.”

Over the next hour she sucked me off, played with me until my cock was ready again, and then mounted me. Her pussy felt so lovely and squishy and even though I had just come once, I only lasted two or three minutes.

We snuggled together, her hand squeezing my cock. “Very nice, Jeff, you bounce back really quickly. This time you fuck me. I’m going to lay on my tummy and you do me from behind.”

I lined up my renewed cock and rubbed up and down her slit. “That’s it, honey. Push in.”

For only the second time in my life I was now enjoying the extraordinary feeling of pussy and softness that enveloped the full length of my cock. Afterwards we lay side by side as the girl asked me about myself. “You aren’t one of Mr. Hammon’s sons, are you?”

“No, a friend of his son. We work together.”

“So very handsome. Are you and his son lovers?”

Our arrangement confidential. “No, just friends. You are my first ever for sex.”

“I hope we have another opportunity to get together, Jeff.” She kissed me on the cheek and left. I showered and returned to the main area.

“She is a really cute girl, huh? How many times did you cum?”

“Three times. First a blowjob, then she got on top. I didn’t last long either time. Then I fucked her from behind and did better. Thank you for arranging this.”

“Now that you have had us and had a taste of pussy, what do you say about my proposition? Totally confidential, I assure you.”

“OK, I’ll go along. What will happen next?”

“Well, right now I’m horny so come into my bedroom and you can suck my cock.”

I was driven back to my parents’ house to pick up some personal items. Gregory said not to bother with clothes, that he would arrange for everything new. My parents were a bit suspicious about me going off to a new job and place to live.

“I’ve arranged for the same girl to come tomorrow? That ok with you?”

“Yeah, great. Nice girl.”

****

Hi, Amber. I’m sure glad you could come.”

“Me too, Jeff. So now that we have that pesky virginity out of the way, how about we just have some fun? Want me to show you how to eat pussy?”

Something new. She coached me. I was afraid the taste would be awful but it was really very sexy. I must have done ok because she pulled my head to her crotch and humped against me.

“Oh, wow, honey, you did very well for your first time. You will have to fight off the girls once they find out about your talents.” I should be so lucky. She rolled on top, positioned my stiff cock at her hole and slowly lowered. Oh, my, pussy is so great. Afterwards we talked while she fondled my limp cock. “I start at U of M in two months.”

“Oh, me too! I’ve never met anyone like you. How old are you?”

“Eighteen, three months ago.

“You and I are virtually the same age and yet I’m an inexperienced dufus compared with you. Do you like doing this? How did you get started?”

“My sister. She’s two years older and when I turned legal she set me up with the agency. All very discrete and classy. I need the money for college and rent.”

“Do you fuck lots of guys?”

“That’s not a question you should ask a girl. I just started two months ago and still inexperienced. Guys really like that I’m young and look even younger but only high rollers can afford me. I now see sometimes three or four guys during the course of a week.”

“And how did Mr. Hammon contact you?”

“Through the agency. In his business he frequently needs escorts for clients. I worked for him once before, last month, and he asked specifically for me because I’m your age. I liked the idea of being your first. I had no idea you were such a nice guy and so handsome.”

“I’ll get to see you again?”

“No. Mr. Hammon booked someone else for other times.”

“Why? I like you.”

“His decision. I wish it were otherwise.”

The next two months were a mixture of sex with Gregory and Jim and frequent afternoons with different escorts. I would have preferred Amber but the variety was educational.

School started and our arrangement ended. I was a typical bewildered freshman making sense of college. A few weeks later several of my new buddies and I went to the student union to play cards. I did a double take, the girl at an adjacent table was Amber.

“Hi, Amber.”

She looked up, a look of concern on her face. “No, you have me mistaken for someone else. Sorry.”

I was confused. It was Amber, or her twin. “Sorry, you look like someone I used to know. My apologies.”

Her group left and I followed at a distance.

“Hold up. Please.”

“Hi, Jeff.”

“It is you. Why did you act that way?”

“Well, for one thing I’m not Amber. That’s my professional name. And I was very concerned that you would blurt out something inappropriate. None of my friends here know about my job.”

“I would never say anything.”

“I know but I couldn’t take the chance of an accident. By the way, my name is Janet. So how is school?”

“Doing fine, a bit bewildering at first but I’m setting in. Can we meet sometime?”

She gave me a long look. “I don’t think that would be a good idea. You were a client of mine, nothing more. Too much history, Jeff.”

“Look, I really don’t know anyone here, I mean girls. You are very pretty and I would love to go out with you. Just a date. No expectation of anything else.”

“OK, we go out but it’s not a date. Remember, you and I had was business. I was paid very well to have sex with you. You are a very nice boy and in other circumstance I would definitely be interested. But mixing paid sex and relationships will not work.”

In spite of her reluctance, we continued to see each other. Not dating, she insisted, but just friends spending time together. A month later we had a real date and a couple of weeks later we went to bed. She complemented me on my improved skills. Two months of fucking escorts made a difference.

“What are you doing for Christmas break?” I asked as December rolled around. “Would you like to meet my parents?”

“I’m going to New York.”

“Oh, really?”

“I’m going with a guy. He needs someone on his arm for receptions and such. We fly out on his jet Saturday morning. It’s a job, nothing more.”

“Oh. I didn’t realize you were still doing that now that school started.”

“First time since summer. He asked specifically for me so the agency got me a bigger fee. And in case you are wondering, yes, I will have sex with him. I’ll get back here well fucked. Is that what you wanted to hear?”

I was momentarily nonplused about her plans and especially her somewhat challenging retort.

“Sorry, it’s really none of my business. When you get back you can tell me all about your trip.”

“Oh? Everything?”

“Yeah. Tell me about receptions and parties. Tell me about the sex.”

She looked at me with a funny expression. “You want all the details? Size of his cock, how many times, what positions? Why?”

“I’m curious and to be frank it turns me on.”

“Yeah, sure, and then you will get all bent out of shape when you hear the details. I’m an escort, Jeff, and I fuck guys for money. I suck their cocks, they put their cocks in my tight, little pussy and fill me up with cum. They don’t make love to me, they fuck me. And you want details?”

****

“Welcome back. How was the trip?”

“Good. Traveling by private jet is the only way to go.”

“I ordered a pizza. And you can tell me more while we are in bed.”

“You really want to know, don’t you? You are really something else. OK, he runs a big hedge fund, lots of bucks. A limo picked me and an hour later we were headed to New York. There was a reception that evening, very classy, and I was told to hang onto his arm. Easy to do since he was oh so handsome. About 40, I would guess, so others could probably figure out I was just eye candy.

“Afterwards I sucked his cock. It was medium size, by the way, not as big as yours but easier to suck. Then he fucked me doggy. I had to fake a climax. We used the hot tub as I fondled him and then rode cowgirl style. This time my climax was real.