The Princess, The Pirate, The Witch

Literotic asexstories – The Princess, The Pirate, The Witch by TruthwithaTwist,TruthwithaTwist
This is my entry into the 2023 Halloween contest. I always like to reinforce that (like my author name say), all of the stories I tell here have a basis in truth and are always based on actual events from my life. That being said, I do like to add some twists & embellishments to keep them interesting for the readers.

Please remember, authors & our stories thrive on ratings. We get better with feedback, so PLEASE leave your comments on our stories. I also love when people guess in the comments what parts are “Truth” and what I added for “Twists”

Everyone in the story is 18 years of age or older.

——

My wife Sherri was the Assistant Principal at a private school that held an annual fundraising event every fall. The Fall Ball was when parents and donors would pay for tickets to attend a night of drinking, dancing, entertainment as well both silent and live auctions. Because the function was usually held a hotel, a lot of parents would book a room to avoid driving after an alcohol-fueled night. One year, the event was scheduled for the weekend before Halloween, so the PTA committee decided to make it a “Costume Ball” for the first time.

Part of Sherri’s job was to be the faculty representative on the PTA and as a result she was heavily involved in the planning. The rest of the committee consisted of volunteer parents, mostly mothers, who managed everything from donations to ticket sales to the event itself. Somewhere in the planning stages, the committee members decided it would be fun to do a “group themed costume” and their pick? Disney Princesses.

Sherri came home one night after a meeting and I was waiting with a glass of wine thanks to her text, “Holy Fuck. You better have wine ready for me after this meeting.” When she came in, she kicked off her work heels, fell into our cushioned sofa and started to recap the meeting for me.

“The problem is these women all need a hobby – besides this event” she started. “They debate EVERYTHING from the color of the cocktail napkins to whether we should have Sharpies or regular pens at the auction tables.”

She continued to talk about the meeting until she got to the crux of her story, “And then … we had to decide who was going to be which Princess. June immediately claimed Cinderella and said that we couldn’t have two of the same princesses. Kiley got upset and said that she is a NATURAL blonde, so she should get to be Cinderella and June could be Aurora. Well, that pissed off Marie who wants to be Aurora AND it pissed off June who didn’t like it being pointed out her hair isn’t natural.”

“Ha!” I interjected. “What happened from there?”

“Well, then Laurie said she was going to be Princess Leia and June told her that she’s not a Disney Princess.”

“Well, technically … Disney owns Star War…”

“Shut up, nerd. Let me finish. So THAT went on for a few minutes. At one point, I had a few grown women screaming at each other, two women crying and the rest of us wishing we had stayed home. Oh, and one very confused father who regretted volunteering to put together the slide show.”

“Poor Lenny. So how’d it end?”

“I ended up pulling rank and making the decision for everyone. Basically, I said it’s supposed to be a fun event and if there are two Cinderellas or ten Cinderellas it won’t matter.”

“Nice. So which princess are you going as?”

“I have an idea, but I’m not telling anyone, including you, yet!”

“C’mon! You can tell me! Slutty Snow White? Maybe a sexy Moan-ana? Dress up so I can Poka-your-hontas?”

My wife picked up her wine and heels and left the room shaking her head, “There’s something seriously wrong with you, you know that, right?”

———-

Weeks went by and on the day of the event, Sherri went to the hotel where it was taking place early in the day to help set-up. I followed later and checked us into our room that we had booked. (Our young daughter was spending the night at the house of one her friends.) In the time that had passed, I decided to stick with the Disney theme, but I went in a slightly different direction – Captain Jack Sparrow! I thought it was a fun costume, kept in the spirit of the night and would let me drink and stagger around, all in character.

I went down to the ballroom to check on the preparation for the event and saw all the volunteers bustling around setting up decorations and auction items on various tables. Sherri handed me the keys to her car and asked if I could grab her bags and bring them up to the room while she finished some last details. I unleaded her suitcase, a huge garment bag, plus a big box that held what I assumed was her costume. I was tempted to peek but decided to just follow instructions, then settle in to watch some college football until it was time to get ready.

The hotel room we booked was a small suite divided into two parts. When you entered, you stepped into a small living room area with a pull-out sofa-bed and a desk there was a little half-bath by the door. The bedroom and bathroom were through a separate door across from the sofa.

I was sitting on the sofa, with a beer I grabbed at the bar, when I heard voices outside the door. The electronic lock triggered, and I looked up to see Sherri entering with someone close behind.

“Hey Babe! You decent?” Sherri called out. “Grace is with me!”

I looked past Sherri and saw Grace walking in behind her. Sherri stood at 5’5″ and Grace seemed to stand a bit taller, but this may have also been an illusion caused by Grace’s mane of curly red hair. She was obviously of Irish decent with bright green eyes, pale skin and tendrils of dark red hair spilling down over her shoulders, nearly reaching the middle of her back. Grace had on a pair of skinny jeans and tight black top that clung to her, showing off her toned body. Her chest was small, but when she turned, I got a look at her solid filling out her jeans. She was a natural beauty who could always light up a room with her smile and laugh. She had on a pair of calf-high boots that women love to wear in Autumn and I gave her an appreciative look as she walked in dropping her bags on the nearby chair.

We had hung out with Grace and her husband, Andrew, a few times over the past few years. They were both easy to socialize with and the nights were always fun. Grace and I had a fun, flirty rapport that usually caused our spouses to roll their eyes at us. Unfortunately, in January, Sherri came home and told me that Grace and Andy had separated. Turns out, he had been hiding a gambling problem and had done some serious damage to their savings. It all came to a head over the holidays, and she threw him out. Since then, Grace had to get a job teaching at a different school just to keep her head above water. Her mother moved in with her to help with her son and the expenses.

“Hey Grace!” I called out as I stood. “What’s going on?”

“Not much, Jay! Thanks for letting me crash your suite.”

“I told Grace she could get changed here. That way she doesn’t have to drive all the way home and then come back.” Sherri added.

“Sure! No worries. I’m happy to help either or both of you into your costumes.” The comment earned me an eye roll from Sherri and a giggle from Grace. Her bright white teeth spread open in a big smile as her crimson mane followed her into the bedroom. My wife spoke up,

“You’re an idiot. Why don’t you really make yourself useful and go get Grace and me drinks at the bar.”

Again following instructions, I ran down to the hotel bar, grabbed a bottle of wine and a couple of glasses, and then returned to the room. The three of us sat and chatted since we had time before we had to get ready. After an hour or so, we realized it was time to start getting dressed, but adding a third person to the room caused some logistical issues.

“Babe, do you think you could get ready in here if Grace & I use the bedroom and bathroom?”

“Not a problem. Just being able to tell everyone that I had two hot MILFS getting naked in my hotel room is a story I’ll be telling for years.”

The door to the bedroom was closed firmly in my face telling me it was time to focus on my own costume. I spent nearly an hour getting into costume, adding a beard and eyeliner, fake tattoos and what seemed like a ton of accessories. By the time I finished, I was a passable substitute for Captain Jack. I was making final adjustments when the bedroom door cracked open, and Sherri’s head peeked out.

“Can you give me a hand with the last of the costume? Grace is finishing up in the bathroom.”

When we were first together, Sherri was a tall, thin blonde with small perky tits, tight ass and long lean legs. There was an old store, “bebe”, that Sherri could have been the perfect model for. But age and motherhood does change things. Over the years, she had filled out in a good way. Her breasts were now larger and fuller and were just as sensitive before which gave me more to grab, lick and touch. Sherri’s long blonde hair was gone, she now had a close-cropped platinum cut that was in style. Her ass was larger, too, but her workout schedule had it toned and looking full and sitting high on her frame.

Sherri opened the door and stepped into the room, encased in a long black gown with flowing sleeves and a low-cut neckline. There were purple details in the sleeves and around her neck and flashes of purple in the long slits up the sides of the gown. I was surprised at the way her breasts were supported and showcased especially for a school function. They were round and firm with protruding cleavage over the top of the dress. She had darkened the makeup around her eyes, had on long fake eyelashes, and had created some sinister angles at the corners with green and purple eye shadow. Lastly, her lips were coated in a deep red lipstick making them look wicked and sexy at the same time.

“Holy shit. You look amazing! Maleficent? That’s your princess?”

“Yup” she laughed. “I figured since the kids all think I’m evil and I had to yell at all the princesses, it would be the perfect choice!”

“And you look hot in that. You really going to wear that in front of everyone?”

“Sort of. That’s why I need your help.” She handed me a big black cloak with a purple collar designed to spread up and around her neck. I took the cape and helped her secure it around her neck. When it fell around her, I could still see the details of her gown, but she was much more covered, especially her breasts and cleavage. She pulled on a pair of black boots, then went back to the bedroom and brought out the horned headpiece that would complete her look.

“I like the evil you!” I said using a terrible Jack Sparrow accent. “Can’t wait to let you cast a spell on me later tonight, savvy?”

“Well, in that case, I’ll give you a quick peek at the hidden treasure.” She spread open her cloak and lifted her gown at one of the high side slits. As she did, I saw that her black stockings ended at her thighs and were being supported by garters connected to a lacy garter belt. A miniscule purple strip of shiny satin covered her shaved pussy leaving all but her slit visible.

Before I could say anything, we heard an awkward gasp from the bathroom door and saw Grace standing there, staring in our direction, a blush rising on her pale cheeks.

“Oh! I’m so sorry” she blurted trying to turn away. Even in the awkward moment, I saw Grace was wearing a perfectly suited costume to her looks. She was in a long, velvety, emerald green dress with long sleeves that covered her arms. There was a leather belt cinched around her waist that highlighted her figure. Her long red curls flowed around her face and over her shoulders to her exposed collar and chest. Slung over her shoulder and back she had a plastic bow, and quiver of arrows to complete the look: Merida from Brave.

Sherri dropped her gown and cloak and smiled back at Grace. “Don’t be embarrassed sweetie! I’m pretty sure you saw me pull them out of the bag earlier. You just got to see them on me, too!”

Grace smiled, but I could still the flush of embarrassment in her cheeks from unintentionally interrupting us. I helped Sherri secure the headpiece on her head and we all went to the party.

Without going into a ton of detail, the event was a great success. Everyone ate, drank, and bid in the auction. The Princesses all took a picture together, with the evil Maleficent in the middle of them all. The magician they hired was amazing and just cheeky enough to entertain the adult audience. Of course, with that many adults being out without their kids, we all took advantage of the bar. As the night started to end, we were all pretty tipsy, including Grace who was laughing and giggling with some of the other moms.

I checked out at the auction table and quickly found out that in my buzzed efforts to support the cause, I had purchased more than my share of prizes and baskets in the auction. I had to run to the lobby and ask one of the bellmen to bring a cart and transport it all up to the room for me. After close to 30 minutes, I stumbled (allegedly just in character) back into the ballroom to find that most of the guests were filtering out.

Sherri and Grace were sitting with some of the other parents as I sauntered over, taking a seat at the table.

“Avast wenches! Be there any room for Captain Jack Sparrow?”

“Only if he’s going to get us all a round of drinks”

“Aye. M’lady.” I went to the bar where I got one last round and brought them on a tray back to the table. After handing them out we all toasted a successful night.

“Drink up, me hearties, Yo Ho!”

The group started to break up when Sherri leaned over to me, “I don’t think Grace can drive.”

“Is she that gone?” I asked.

“Yeah. She’s been drinking quite a bit all night. What should we do?”

“Tell you what. Take her upstairs, since her stuff is up there, anyway. Let me talk to the desk and see if they have any rooms.”

“Babe. I’m not sure she can afford one.”

“Don’t worry about it. With what I spent tonight, one hotel room won’t break me.” I stood up and headed to the lobby.

“Wait! What do you mean ‘with what you spent’?'” she called after me.

15 minutes later, I was in the elevator feeling defeated. The hotel was completely sold out because of the events being hosted. I quickly realized that my night with an uber-sexy witch wasn’t happening with a guest sleeping in our room.

When I entered our room, I saw the pile of baskets and packages stacked against the far wall. Somehow, in my inebriated state, I had collected quite the array of prizes. Sherri and Grace were looking through my treasures with amused looks on their faces.

“What in the hell did you buy?” Sherri asked. “And did we really need a kids’ gardening basket?” Both women giggled as I joined them in looking though the pile of cellophane and tissue paper. As I opened one, my face lit up.

“Yo ho ho, and a bottle of rum!” I exclaimed as I pulled a bottle of expensive rum from one of the baskets. “Anyone want a nightcap?”

I poured us three glasses of the amber liquid over ice, then excused myself to the bathroom where I used some makeup remover to take off my fake beard and makeup. I removed the heavy accessories to my costume and went back out into the living room in just my baggy pirate pants and shirt.

Sherri and Grace had similarly removed some of their costumes. Sherri was sitting on the coach, still in the black and purple gown. Her boots were on the floor, and I could see her nylon-covered feet tucked under her. Grace was in a chair and had taken off her shoes, quiver and belt and was sitting with her big green dress tucked around her. I settled in next to Sherri on the couch and she leaned back to rest against me.

We all toasted and chatted about the event, the various people and all the gossip that came with an event like that. At some point, I refilled all our drinks and we continued to chat and relax. As expected, the conversation turned to Grace and her situation. She got emotional talking about what Andy had done and how much her son missed having his dad around. Sherri and I were very careful not to criticize nor comment and basically just listened. Whether it was the liquor or emotion or a combination of both, Grace eventually had a stream of tears streaking her cheeks as she talked about how lonely she was.

“I’m sorry.” she whimpered. “I didn’t mean to bring you guys down. I’ll be right back.” With that, she stood up, staggered a bit, and walked to the bathroom in the other part of the suite. Once the door closed, Sherri rolled slightly to her side so we could talk quietly.

“I feel so badly for her” she started. “Andy really fucked her over.”

“No shit. I had NO idea how much money he blew and how much he left her in the lurch.” As I spoke, I looked down to see that when she shifted, Sherri’s Maleficent gown had opened slightly up her extended leg. I could see the top of her black thigh highs and some of her exposed skin. I could see the curve of her thigh and her bare ass cheek peeking through the open slit of the dress.

Sherri must have felt me slightly harden at the sight of her because she slumped her head against my shoulder and half-whispered, “I’m so sorry babe. This isn’t what I had planned for tonight. But she has nowhere else to go and I feel so sorry for her.”

“I get it.” I replied. “It definitely sucks, but maybe you can save this outfit for when my birthday rolls around.” I shifted my hand slightly and ran my palm up and down her skin, opening her dress a little more.

Sherri nipped and nibbled at my neck, sensing my building arousal. “Up to you. I was going to go with sexy cheerleader for your birthday, but I can do evil witch instead.” She then leaned up and planted a kiss on me. Just as she started to pull away, we heard a sound from the door.

“Shit! Shit! Shit! I’m such an idiot.” Grace cried out. She had washed off her makeup, but her eyes were still red and puffy from crying. She was staring down at us and had a clear line of sight to my wife’s exposed thigh and ass and her long nylon-covered leg. Our body positions gave away our actions and there was awkward silence for a few seconds before she continued.

“You guys had a whole romantic thing planned and I ruined it because I got drunk and can’t drive! I’m so sorry.” Tears were now running down her face again. “I’ll get out of here and give you some privacy. I’m so sorry. Shit.”

Sherri stood up and moved toward Grace, “Grace, honey, it’s ok. You’re not going anywhere. You can’t drive and Jason checked already, there are no other rooms.”

“Fuck. It doesn’t matter. I couldn’t afford a room anyway. And if I go home, I’m sure my mother will give me lecture.” A humorless laugh left her mouth. “Fucking perfect. 36 years old, separated, single mother, and somehow still going to get scolded by my mommy.”

Sherri wrapped her up in her arms a bit tighter as she started to sob even more. “Bad enough I’ve fucked up my life, now I’m messing up yours. I’m so fucking cursed that even though I haven’t had sex in close to a year, now I’m taking it away from others. I’m like a black hole of romance.”

My wife continued to hug and stroke her friend’s back in their embrace, “Honey, it’s not your fault. Stop blaming yourself. You’ve been stronger than 90% of the women I know. Supporting yourself, digging out of debt, taking care of your son. You’re an amazing, strong woman.”

Grcace’s breath started to calm down as Sherri rubbed her back and started to stroke her long, red hair. I saw my wife glance over at me for a brief second before she continued with, “But not having sex? That’s unacceptable. Turn around.”

Grace pulled away with a confused look on her face, “What? Why?”

“Because the way I see it, you have two options. Lay out here and cry yourself to sleep on a pull-out sofa bed, or…” She turned her friend around and reached under her hair to the top of her zipper, “Let us show you just how attractive and sexy you are.”

Now, to interrupt my own story, Sherri and I had been together for close to 15 years at that point in time. Over that time span, we had dabbled in a handful of threesomes. The first time was with her friend Linda after a party early in our relationship, another time was with a former female neighbor of mine. There was a professional escort in Las Vegas on my 30th birthday, a drunken fling with my ex, Tara, and finally a second romp with Linda when Sherri was pregnant a decade before. Until that moment in the hotel room, I thought those days were long gone. But as I watched Sherri slowly start to pull the zipper down, revealing Grace’s nearly alabaster skin, my hopes and arousal were renewed.

“Sher…I don’t know. This isn’t right.” Grace was almost whispering as more of her ivory skin was revealed.

“Please. You and I both know how much you and Jay have flirted over the years. I know for a fact he thinks you’re hot. And I also know that you would bang him in a heartbeat if you had the chance. So, I’m using my powers to grant your evil wish of having sex with my husband.”

Sherri continued to unzip the dress to the base of Grace’s spine before reaching back up and pushing the collar and sleeves down her body. I watched as the dress fell to her hips and I got my first look at Grace’s small tits encased in a basic beige bra. Her waist was tiny, and I could see a pair of matching panties just showing above the deep green dress sitting at her hips.

“No. We can’t. It’s not right. You’re married and a woman. I can’t. It’s like a sin or evil or bad or something.”

Sherri then spun her back around by her shoulders, so the women were facing each other once again. Her red lips curled into a smile as she stared into the ginger’s eyes. “Evil? Well, if it’s evil, you can blame me, then. After all, I am the evil sorceress giving a princess to a pirate.”

With those words, she pushed the dress down over Grace’s full ass and let it puddle at her feet. Grace had on a pair of unappealing “granny panties” that matched her nondescript bra. Her body language showed her nervousness as she seemingly squirmed in shame.

“Sherri…I’m not sure. Should we?”

“That’s enough! Jay, get your ass in the bedroom. And you…” SMACK, my wife gave her friend a slap on the ass, “will do as the evil queen commands.”

I nearly leaped off the couch, stunned at what was happening but doing everything I could, not to fuck it up (especially mentioning to my wife that she was starting to mix up her evil Disney characters.) I went to the bathroom, quickly brushed my teeth and got a little blue pill out of my valise. I would sometimes use a “boost” when Sherri and I were away like this and thought this was the perfect situation to use one.

I went back into the bedroom to see my wife standing by the bed with Grace standing by her. “Unzip me, princess.” She directed.

Our friend did as she was told and unzipped my wife’s long black gown. The sound of the zipper seemed loud in the silence of the hotel room. Sherri shrugged the dress off her shoulders and arms to reveal a black push-up bra that showcased her tits. Grace continued to pull the tight garment down Sherri’s body until she had to pull it over her hips. The lace of the garter belt appeared for the second time that night and the dress fell to the ground to show the strip of purple and long black stockings.

I was stunned looking at the difference between the two women as they stood so closely together. Sherri stood tall with her sorceress makeup and black lingerie standing out against her skin. Her legs looked long and sultry in the stockings and her shaved pussy was evident in her miniscule panties. Her chest was pushed up in her lacy bra and her lips shone with glossy red lipstick.

Grace, alternatively, was less confident. She seemed to be slumping, attempting to hide her exposed body. Her underwear was beige, nondescript and almost blended into her skin tone. Her hair was long and curly but was now partially covering her face. Sherri turned to face her friend, then gently and caringly brushed the loose hairs from her face.

“Honey, it’s ok. We don’t have to do this. I don’t want you to do anything you don’t want to do. But, if anyone deserves a guilt-free night, it’s you. And..” she added with a smirk, “You can always say I put an evil spell on you. After all, you were the one who said you were cursed. Isn’t this how you break an evil witch’s curse?”

I watched Grace absorb what my wife had said, before she looked up with a spark in her eye. “Fuck it. It’s been a shit year. Literally can’t get any worse. So, why the fuck not? If nothing else I’ll know that for once, I’m having more fun than that dickhead Andy.”

“That’s the spirit” said Sherri, “Now, let’s see what you have under there. Turn around.” When her friend turned, Sherri unclasped the redhead’s bra and let it slide off. Grace turned back around to show her small, bare breasts, pert nipples and areola so pale and pink that they almost faded into her natural skin color. Without prompting, she reached down to her hips and slid her underwear down revealing a patch of red pubic hair that matched the flaming color on her head. Her bush was trimmed at the edges, but full and I found myself staring at my first view of a natural redhead. She saw me staring and moved to cover herself.

“I’m sorry … I haven’t exactly worried about … down there. Nobody really gets to see lately.”

“Oh, stop that crap.” Sherri said, pushing her hands aside. “He’s staring because he thinks it’s hot. Right babe?”

“Definitely. Holy fuck, Grace. Your body is amazing. Andy’s a moron. Just sayin’.”

I watched as my wife started to run her fingers through her friend’s lush pubic hair while her other hand started to caress one of her breasts. I heard Grace gasp when she felt fingers slide up and down her pussy lips as she shifted her hips to the sensations. Sherri’s hand continued to stroke her friend and she used her other one to turn Grace’s head toward her. She licked her friend’s pale lips with her tongue before giving her a gentle kiss. She continued to stroke and gently kiss her until finally her tongue was met with Grace’s. The two women kissed slowly and romantically, while Sherri’s fingers continued their dance. Grace was slowly spreading her legs giving my wife better access to her pussy. Her free hand seemed to be moving up and down Sherri’s body attempting to keep her balance. As her hand reached Sherri’s lace covered breast, she worked it into the cup attempting to release it. Sherri pulled back for moment, reached behind her back, and unsnapped her bra, wriggling out and letting it fall to the floor. Her tits fell out with a bounce showing us that her nipples were erect with arousal. Grace grabbed and lifted her friend’s breast feeling its heft and weight in her palm.

They pulled each other closer and I watched as their naked tits pressed against each other while they continued to kiss. Sherri worked her fingers back down to Grace’s ginger pussy and began to strum along her slit. Grace gyrated her pelvis against the fluttering fingers that were flicking her clit. My cock swelled as the two friends kissed harder and deeper and Sherri’s fingers pressed into her friend’s pussy. It didn’t take long before Grace’s head rolled back and she was gasping for air. She gripped Sherri’s wrist and held it in place against her pussy as an orgasm rolled over her. Her gasps and moans filled the quiet room as she bucked against the invading fingers.

When she finally stopped moving, I could see that her pale skin had flushed pink and beads of sweat had formed on her forehead. My wife pulled her fingers away and dipped one between her lips, licking Grace’s juices off.

“Now, let me grant you your next wish, and get you into bed so you and Jay can have some fun.”

As Grace gingerly climbed onto the bed, I stripped off my remaining clothes and settled my head on the pillows, while Sherri pulled down her panties and crawled in next to Grace. She was still clad in her black stockings and garter belt with her own pussy now exposed.

“He looks ready, but I’m thinking one of us should make sure. Do you want to get him even harder or should I?” my wife asked.

“You do it. I want to watch first.”

Sherri smiled up at us both and turned her body on the bed so that her head was level with my crotch. I watched in awe as her red lips slid over the head of my cock. She kept only my head sealed between her lips as her tongue swirled around the sensitive skin. She pulled up and licked around rim again before taking me back in her mouth. She started to suck this time while she coated my dick with saliva. As my cock swelled and pulsed in my wife’s mouth, I opened my eyes to see Grace’s eyes glued to the scene while she stroked up and down Sherri’s nylon covered legs.

Sherri opened her eyes and looked up at me with her mouth still full of my cock. I watched her give me a sensual wink and open her legs wider, inviting Grace to increase her motions. Her friend took the hint and shifted her body so that she could run her hands further up to Sherri’s bare thighs. I watched as she moved her hands higher and just as she made contact my wife’s shaved pussy, Sherri plunged her mouth down taking my entire cock into her mouth and throat. Her head bobbed up and down faster, sucking and licking me as her friend fingered her pussy. I felt my cock start to swell and I reached down to grip her short hair. Just when I thought I was going to explode, Sherri pulled off my cock with a wet “POP”.

“Mmmmmmm. I think you’re ready, but I don’t want you to come yet. I think Grace needs some of that, but not in her mouth.” Sherri shifted again on the bed giving Grace and me room to get closer to each other. “What’s your favorite position, honey? How do you want him?”

“I think I want him on top of me.” Grace replied. “But…are you sure this is ok? I mean…”

“We’re WAY past ok. Lay down now, princess.”

Grace settled into the pillows and spread her legs with her knees bent outward. I was still in shock, staring at this hot MILF, with her red hair spread over the pillows, her pink nipples standing hard from her pale skin and her deep red bush framing her wet pussy lips. As I moved over her, I felt my wife grab my shaft and start to run it up and down her friend’s slit coating me in her juices.

“Here. Let me help you. It’s the least I can do.”

She continued to lubricate my cock with Grace’s juices until she positioned my head at the entrance to her pussy. She lined me up and I pushed forward but Grace’s pussy, while wet, was incredibly tight. I felt her body jolt away and heard a small grunt.

“Go slow, babe. She hasn’t had anyone in her for a long time. And you” she added, looking at her friend, “just relax and enjoy.”

I slowly pushed forward and felt her pussy open a bit more for me. I stayed still before pulling back leaving only my head inside her, waited again, then pushed forward. Again, while still tight, her pussy was slowly opening up for me. I repeated the action until I felt her lips gripping the head of my cock and slid forward again. There was less resistance now and her juices were coating my shaft.

While I slowly fucked her friend, my wife had moved up and started licking her small tits and nipples. Grace had her hands pulling my wife’s mouth tighter against her breasts as I increased the tempo of my thrusting.

“How’s it feel, baby?” Sherri asked between licks.

“She’s so fucking tight. Holy shit.” I moaned back.

“I was talking to HER, but that’s good to know” she chuckled.

“Oh, shit, it feels so good. I feel so full. So good.” Grace added to the conversation.

My wife moved again and positioned herself so that her larger breasts hung over her friend’s mouth. She leaned down so that her nipple tickled her lips and kept brushing it back and forth.

“Sher? What are you doing? I’ve never…”

“It’s ok, honey, just do what you think would feel good. I just want to feel your tongue on my tits.” She leaned down a bit more and pressed her fleshy globe into Grace’s mouth. Instinctively, Grace took it in and began to lick and suck. My wife was gripping her own tits and kept swinging them back and forth into her friend’s mouth, getting her to lick and suck on alternating nipples.

Grace was thrashing trying to keep her mouth on Sherri’s tits while I pistoned my cock in and out of her pussy. I pulled myself up so I was kneeling which changed the angle of my penetration. She moaned at the new sensation and shifted one of her legs up and out. Sherri noticed the movement and linked her elbow under Grace’s knee and pulled her open more. The bed was now a contortion of limbs and flesh as all three of us tried to maintain our motion and contact.

I felt my balls slapping against Grace’s ass I fucked her harder. Her moans were muffled by my wife’s breast stuffed in her mouth as I felt her pussy start to grip me tighter. She used her free arm to push Sherri away as she started to shake and spasm against me.

“Fuck! I’m fucking coming. I’m coming!” Grace moaned as she rode her orgasm. The muscles of her pussy spasmed and tightened around my shaft as she shuddered through her climax. Sherri had gone back to gently licking her nipples, allowing her friend to enjoy the release. When she stopped moving, I pulled out of Grace and watched her juices leak out of her inflamed pussy lips. I was still rock hard as I watched her chest rise and fall attempting to get her breath back to normal. Even in the dim light, I could see her ivory skin covered in a sheen of sweat and her red bangs were plastered to her forehead. Her mound of red pubic hair was wet and matted against her skin while the mane on her head was wild and tousled on the pillow.

“Good to see you are still at full mast, baby. Now it’s my turn to get pillaged.” Sherri moved down on the bed and positioned herself on all fours with her ass up in the air and her torso hovering over Grace’s stomach. Her tits hung down as she spread her legs wider for me. I repositioned and slid easily into her pussy from behind.

My cock was still covered in Grace’s juices and Sherri was dripping, so I encountered no resistance as I slid and out of the familiar cunt. I watched as her bare pussy lips gripped my cock on every stroke and opened when I pushed forward. My wife’s body rocked back and forth, and she dropped down slightly so her nipples were brushing against her friend’s sweaty skin.

“That tickles!” Grace laughed. “Your boobs are brushing and tickling me!” We continued our motion with me gripping my wife’s hips allowing me to slam into her harder, her tits dancing on Grace’s stomach. I felt my balls start to tighten, preparing to release my load into my wife. She felt it too, because she pushed back and stopped my thrusting.

“I can tell you’re getting close, baby. But there’s something I want before you come.”

She shifted a bit and sunk down so that her face was level with Grace’s crimson snatch. Sherri took her tongue and licked her friend’s slit from her ass to her clit. A sharp gasp erupted from our fair Merida and she unconvincingly groaned, “No. Sherri! I’ve never had a woman do that! You can’t!”

Being the evil minx that she was, Maleficent ignored the pleas and simply buried her face into the awaiting pussy. Her tongue was buried in her friend’s tunnel and with every thrust of my hips, the pressure and depth increased. For her part, Grace’s head was thrashing back and forth as she pinched her own nipples. The sight of my wife’s cropped, platinum hair buried in the pussy of another woman, while her ass rippled with every thrust of my hips, combined with a second MILF building to her latest orgasm was too much for me.

I moaned and dug my fingers into my wife’s hips as my cock exploded into the depths of her pussy. Grace screamed out as she pulled Sherri’s face in tighter, releasing into her waiting mouth. I was shocked that between the banging of the bed and Grace’s screams, we didn’t get a knock on the wall or a call from the hotel for excessive noise. Fortunately, nobody bothered us as I fell to the side of the bed, soaked with sweat. My cum dripped out of Sherri’s cunt as she slithered her way out of Grace’s splayed legs, coming face to face with her. Grace’s eyes fluttered open to see a pair of deep blue eyes staring into her own green ones.

“Here” Sherri whispered. “Taste yourself on me.” With that she pulled our little innocent princess to her own mouth and wrestled with her tongue. Grace could only moan in compliance as she returned the passionate kiss. As we all calmed down, we each left the bed and went to restroom one-by-one. Sherri emerged with her evil sorceress makeup removed and her stockings gone. When Grace came out, she looked tired yet satisfied with her hair in a ponytail as she crawled over me to the middle of the bed. I was the last to leave and return to the bed, having cleaned up myself a bit. When I returned, both women were sleeping soundly, covered only by the white hotel sheet. I climbed into the bed and pulled the blanket up, drifting off myself.

Somewhere in the night, bodies had shifted, and my arms were wrapped around the warm skin of our guest. My cock was pressed against her full, fleshy ass and found its way between her cheeks as I subconsciously hardened. Grace started to grind against me in response and shifted until my dick was pressing against the entrance of her pussy. I moved forward and slid in, much more easily this time. We spooned as we rocked back and forth, a slower more determined fuck than previously in the night. Our motion eventually woke up my wife who rolled over to face her friend.

I couldn’t see what was happening, but I felt Sherri’s hand sliding over her friend’s clit and my shaft where we were joined.

“Naughty girl.” My wife whispered. “Fucking him while I was asleep?”

“I’m sorry. We just….”

“It’s ok, honey. Does it feel good? My husband’s dick in you?”

“Yes” she groaned. “Feels sooooo gooood.”

“Can he come inside you? Do you want to feel his cum in you?”

“Yes…yes…I want to feel it. Please Jay. Come in me.”

“Is it safe?” Sherri asked. “Can he fill your hot pussy with cum?”

“Yes. It’s safe. Please. Please fill me, Jay.”

For the second time that night, my cock released a load into a hot pussy. I felt wave after wave shoot into Grace and then my own cum sloshing around my cock as I kept thrusting. The combination of my climax and my wife’s fingers did the trick and Grace began to shake and shudder again. Her orgasm made the muscles of her pussy contract, squeeze around my cock, and milk the last of my seed from me. A long, low moan escaped her lips as her entire body stiffened, then went limp. I pulled out of her, allowing our juices to flow out to the sheets below. Sherri was gently stroking her friend’s sweaty forehead while her eyes fluttered in the aftershock of her climax. This time, there was no encore to our activity. We each dozed off covered in sweat and sex.

One thing about a late night/all night drinking and sex session is that morning always comes quickly. Also, no matter how well you think you’ve closed the curtains, it is guaranteed that the one burst of bright sunlight will hit you in the eyes as you attempt to stay in dreamland. This was the case as I woke up with a line of a sunbeam shining across my face. I noticed there was more room in the bed, and I could hear movement in the bathroom. Stirring slightly, I could see that Sherri was still curled up with her head under a pillow, which meant that Grace must have been the one in the bathroom. When she emerged, I saw that she was dressed back in her jeans and top from the day before. She was obviously trying to gather her various garments and costume pieces from around the room without waking us.

“Mmmmm….” I heard next to me in the bed. “Are you leaving already?”

“Yeah. I have to get home to Daniel and my mother. I texted her last night, but I’m sure she’s worried.”

“You ok? With everything?” my wife asked.

Grace sat on the corner of the bed as she answered, “OK? I’m great. I’ll be honest, I never thought I would do something like that, but yeah, it was definitely fun. I may have to hide an ice pack you know where though. I don’t think my puss has gotten that much action in years. But seriously … thank you both. You won’t …uh … tell anyone, right?”

“No, sorry.” Sherri replied. “I intend to get on the school announcement system tomorrow and tell everyone that my pirate husband and I put a spell on an innocent Disney Princess and fucked her in our bed until she passed out. I’m sure that would go over great!”

Everyone chuckled as Grace gathered the last of her belongings and slipped out the door, allowing Sherri and me to drift back to sleep for a few more hours.

———

Epilogue:

About a six weks later, I was flipping through the stack of holiday cards that had started to arrive at our house. I did a slight double-take when I saw the family Christmas picture of Grace, Daniel and Andy posed at a Christmas Tree farm complete with matching sweaters.

“Hey babe!” I called to the other room. “Did Grace and Andy get back together?”

“Yup. I guess so.” She replied coming into the kitchen. “But I haven’t really talked to her lately.”

“Really? What’s up with that?”

“No idea. But something tells me that our little after party freaked her out a bit. So, she got back with her husband, and everything is back to normal. She’s probably avoiding me because I’m just a reminder of that whole night.”

“Weird. Are you surprised at all?”

“Not really. When you think about it, it’s the perfect ending. The Princess escaped the clutches of the Wicked Sorceress and Naughty Pirate, got back her Prince Charming and lived happily ever after.”

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