Jason woke up because someone was sucking his cock.
Actually, sucking is probably inaccurate. There was a lot of licking and squeezing and stroking going on, but not a whole lot of sucking. Still, it had Jason rock hard and it felt good.
The “someone” part of it is more accurate. Jason could tell that the tongue and the lips and the fingertips didn’t belong to his business partner and girlfriend Dylan. And that was more than a bit disconcerting.
The room was dark and his eyes were still adjusting as he scanned for familiar objects. It sure seemed like the hotel room he and Dylan had been in for more than a week but he couldn’t be sure given the circumstances.
The person giving attention to his cock was currently under the top sheet so he couldn’t see who it was. Jason put his hands under the sheet and on the head below.
The hair was short, but it wasn’t Dylan’s short hair. By feel alone he couldn’t recognize the person giving him pleasure. His mind was saying “what the fuck” but no sound reached his lips. He decided it was best to sort things out before speaking.
The world was coming more into focus, though an alcohol-induced fuzziness still hung in his head. Jason heard a buzzing sound start up. That sound he recognized. It was Dylan’s bullet vibrator and its location was about 5 feet ahead and to his left. He squinted in that direction hoping to see more and he did, making out Dylan’s figure in a chaise lounge.
Yes. It was their hotel room. His eyes continued to adjust. Dylan looked to be wearing her leopard camisole with matching collar. She was watching the scene unfold in the bed. Her legs were spread apart. Her right hand slowly moved in circles above her pussy. The buzzing sound of the vibrator changed, getting lower and slower as she pressed it more firmly against her lips. The whole scene made Jason harder.
Jason closed his eyes and tried to remember exactly how he ended up in this situation. He and Dylan had just enjoyed a hell of an evening out.
It was the last night of a long business trip. The night started early, somewhere around 3:30pm, if Jason remembered correctly. Too early for happy hour except that Dylan had a knack for getting bartenders to bend the rules for her.
She suggested a “reverse evening” by starting with really good single malt scotch. They usually reserved that for the end of the night but Dylan was selling Jason on a Mad Men-type experience. That’s how they ended up sitting at the bar of the oldest, classiest hotel in town in the late afternoon.
It was everything you’d expect from a bar in a hotel with nearly 100 years of history — lots of big wood and red leather and drinks made the same way they were made decades ago. The bartender looked like he could have been there on opening day. Barely a hair on the top of his head but plenty of white along the sides, wire rim glasses, a neatly squared bow-tie over a sharply pressed white shirt, and the bartender’s vest to complete the picture.
Dylan got his attention and cheerfully chatted him up about getting happy hour pricing a bit early. That’s how she ended up with a generous pour of Macallan 12 and Jason an equally generous glass of Lagavulin 16. Both neat and both at a tidy discount thanks to Dylan’s negotiating skills.
Dylan and Jason had frequented this bar on previous trips. Several memorable evenings followed, including a visit to the penthouse ballroom shortly after 1am for some very hot sex.
On this particular day there was some sort of medical instrument conference in the hotel. An encore performance in the ballroom would probably not go over well with the vendors. Still, the conversation about that past sexual romp led to reminiscing about other adventures. Jason remembered getting very horny and hot and unable to do anything about it at the time.
The time was 4pm or close to it. More patrons made their way in to the bar and a waitress showed up to handle the seating around the perimeter of the room. Dylan noticed her first. Jason noticed her only after he saw that the waitress had caught Dylan’s eye. She looked to be about five and half feet, maybe an inch shorter. She looked fit, especially wearing the standard black slacks, white shirt, and yes, bartender’s vest. The vest fit her snugly and well.
But it was the hair that made her stand out. It was dark brown and short — a nice crop that highlighted her facial features. It wasn’t butch. It was sexy. It was a haircut that belonged on 23 year-old fashion magazine model in Manhattan, except that this women, who was probably in her mid-30s, owned it.
When it comes to fashioning a cute look, no one compares to Dylan. Her hair is short too. It’s a pixie cut with sexy little spikes. And it’s a sensual, sexy red with bright accents.
On this day, Dylan was wearing a vintage 1960s paisley cocktail dress with calf-high cowboy boots complemented by a deep tan she picked up in Florida a week earlier. It was an astonishing look, one that no one else could make work.
It means something when Dylan takes notice and she was noticing this new waitress. So much so that she dropped out mid-conversation with Jason to watch her carry drinks across the room.
“Someone like her,” Jason said.
“What? I’m sorry,” Dylan replied. “I was lost in thought.” Dylan paused as Jason’s statement began to register. When they shared fantasies, they often talked about what a threesome would be like. It was understood that it was just fantasy talk, and it often occurred when Dylan was using her vibe.
She would be lying on her back, the bullet gliding over her clit with Jason on his knees up by her face.
First she would watch as he stroked his cock. Then she would turn her head slightly and open her mouth. Jason would ease his cock to her lips and slowly start to slide in and out. Sometimes that’s all it took for her to start coming. The pace was more leisurely at other times. And when Jason sensed that Dylan needed a bit of encouragement, he would describe how what they were doing at the moment could evolve into a threesome. It almost always worked, bringing Dylan to a full, intense orgasm.
Jason’s words during sex play painted pictures in Dylan’s mind of that perfect threesome partner, even though he never actually described what the other girl. He left that up to Dylan’s imagination and once asked her what their fantasy threesome partner was like.
“Like me,” Dylan replied, “Short with sexy hair and a body that fits well with mine.”
They had never seen that girl before today, even though Jason occasionally pointed out possible matches. Dylan composed herself and focused her gaze on Jason. “Yes. Someone like her.”
Over in the chaise, Dylan was beginning to moan. The vibrator buzzed angrily, trying to keep up its speed as she pushed it even harder against her pussy. Jason pulled the cover sheet away and verified what he had just figured out. The short-haired cocktail waitress had his thick cock in her mouth. She looked up and their eyes met. Hers were smiling. His had a look somewhere between bliss and panic.
This was not part of the threesome fantasy. In fact, Dylan made it very clear on several occasions that her fantasy was girl-on-girl in front of Jason and that Dylan, not the other girl, got all of the cock and cum.
That meant the current situation was a mix of potentially bad and good news. The potentially bad news, at least in the context of his long-term relationship with Dylan, was that the other girl was getting his cock. The good news, at least for the moment, was that he wasn’t about to come.
In fact, Jason wasn’t close to coming. It occurred to him that waking up to a blow job from a complete, and sexy, stranger while his girlfriend was five feet away giving her pussy a high-speed vibe workout should cause him to come fast and hard. That he wasn’t close to coming could only mean one thing; he had already come and fairly recently at that.
Dylan and Jason left the bar after their first drink. Jason offered to buy since Dylan negotiated the deal for early happy hour prices on non-happy hour scotch. Dylan refused, insisting on paying for the first round of their night. Jason used the time while she was waiting for the credit card receipt to hit the restroom. Dylan took her turn when he came back.
The next stop was a more traditional happy hour, with bar snacks for a buck and half priced drinks. They spent a few hours talking over work and summer plans. They checked out online reviews for a few new dinner places before settling on an old favorite up towards the university area.
It wasn’t until dinner was over and they were drinking the last sips of a good bottle of Grenache that the waitress came up in conversation. It was Dylan who brought it up, but it a way that made it seem like Jason’s topic.
“So I’ve noticed you haven’t said another word about the waitress,” she said, “Anything up with that?
“It’s a bit awkward,” Jason replied. “I’m not sure what to make of your reaction. You seemed a bit mesmerized. ”
Dylan smiled and replied, “Yet you’ve said nothing about girl-on-girl with her.”
“Um, well I’m not sure what to think except we usually don’t talk fantasy sex over dinner out.”
She pressed on, “Or maybe you don’t want to bring it up because she looked like someone you’d like to have.”
“Now that’s not fair.” Jason said with forcefulness. “You have me so completely satisfied. We have the best sex ever and I don’t need anything or anyone else.”
“Come on Jason. She was hot. If you had the chance…”
Jason kept protesting. “I’m not looking for the chance.”
“Even if I said it was okay?” asked Dylan.
Was this okay? It seemed that sex had been had at least once already tonight. The waitress was feasting on Jason. Over in the chaise, Dylan seemed close to coming. And no one was complaining. Was this round two for this threesome?
The blowjob was getting more intense with the waitress deep-throating Jason’s cock. Her heading was bobbing with long, steady strokes. Her mouth stopped at the tip of his cock each time and she circled it with her tongue before going down again.
That caused Dylan to moan even louder. She stared at the bed and cranked up the speed on the bullet one more level. Jason started to feel like he could come again, in part because of the sucking and licking, but mostly because he felt like this was a taboo being broken. Dylan was watching another girl go down on him. Buried in the middle of these great sensations was also a strong feeling that he could still end up in trouble.
Their hypothetical argument about the waitress carried on as they left the restaurant with Jason refusing to budge on his position and Dylan pressing the issue further.
“How come,” she asked, “it is okay for me to say I would have sex with someone else but not you? How come you get to talk about it out loud when you and I are having sex? How come if I try to take the conversation there, you take the fifth?”
“Because,” Jason answered, “you said our fantasies involve girl on girl only and because you come big when I talk about it during sex.”
“I’ve tried to bring the topic up before,” she said. “Remember when I asked if you would want to fuck the girl? You were so adamant that you wouldn’t that I almost didn’t believe it. And then there was the time we were making love, it was really intense, and I had just come. You were still going strong and I started talking about another girl and I going down on you at the same time. The words were barely out of my mouth before you came and it was huge.”
Dylan grabbed Jason’s wrist, spun him so he was facing her, and let her hand find his crotch.
“Oh my God,” she gasped. “You are as hard as granite.”
She pulled him closer, rubbed his cock through his khakis, gave him a deep kiss, and whispered in his ear.
“The waitress came up to me when you were in the restroom. I told her that her hair was cute and she was too. She said she hoped my boyfriend appreciated having a girlfriend with sexy short hair. I told her you did, and that you liked her look too.”
“We’re supposed to go back for one more drink, at her table, if we want to hang out with her tonight. Her name is…”
Damn. Jason could not remember her name. It was an important detail that he failed to retain as the meaning of Dylan’s words sunk in. She had negotiated a threesome in the space of less than five minutes. That explained why the waitress was in the hotel room. It did not explain how the night evolved to the point that she was going down on him with Dylan watching, and masturbating, close by.
Dylan and Jason found a table in the corner and sat on the same side, backs to the wall, looking at the rest of the bar. Both were a bit jittery to be there, not knowing what would happen next. It added to the excitement of the moment.
The waitress was there in a flash and asked, “What’s your pleasure this evening?”
Jason managed to get out the words, “Good scotch.” Dylan added, “Good company.” The waitress replied she could help with both, the scotch right away and the company shortly after 11. That was about 30 minutes away.
The time passed quickly as the waitress came to check on them with increasing frequency. It was flirting and it was directed mostly towards Dylan. There were compliments on haircuts, and hair color, and fashion. Tips on shopping and hair care were exchanged. And, in the last 10 minutes, a flurry of comments laced with sexual innuendo.
The innuendo peaked with Dylan saying that the boys must like her body and the waitress speculating that girls would like it better. The deal was done. Dylan and Jason were actually going to be part of a threesome. The only question is whether it would live up to the fantasy.
If the night hadn’t already matched the fantasy, it was sure seemed it was about to. Jason could tell Dylan was going to come any second now. He could tell by the sounds of her moans and her quickening breaths. He could tell from the sound of her bullet vibrator. It was at full speed and oscillating as Dylan rubbed it hard against her pussy in small circles. But the giveaway was her panting out, “Oh God, I’m so close to coming. I’m coming.” The waitress paused her blowjob to watch but kept stroking Jason’s cock. It must have been quite a sight for Dylan. Her eyes were fixed on his rod pointing straight at the ceiling as an unfamiliar hand worked slowly up and down his shaft.
Dylan moaned and bucked, slowly at first and then a little faster. The whole process took nearly a minute. The vibrator clicked off. Dylan let out a few sighs and a long “whew” before saying, “Okay. That was awesome.”
She got out of the chaise, came over to the bed, and planted a deep kiss on Jason’s mouth.
“Welcome back to the world of the living, baby,” she said. “We’ve been waiting for you to rest, reload, and join us again.”
Jason started to speak but Dylan stuck her left index finger in his mouth. It was covered with tasty juices from Dylan’s pussy. Jason sucked it and licked it until it was clean. Then Dylan pulled her finger out of his mouth and placed the pad of that finger on his lips.
“This is no time for talk,” she said. “It is time to play again.”
So they really did have sex already. Jason had come and both girls were still going strong. The haze was lifting a bit more. Jason was beginning to remember.
They had finished their drinks and met the waitress in front of the hotel shortly after 11. The waitress thanked Dylan and Jason for coming back. She was pretty giddy about going out on the town and even offered to buy the first round because the tips had been pretty good for that shift.
Her story was pretty simple. A bad marriage right out of high school. No kids. She left after 10 years and had been putting a new life together over the last five years. She was an assistant chef at one of the better known places for business breakfasts and lunch and a part time cocktail waitress some evenings. She was saving her money to start a small cafe and wasn’t in a hurry to hitch up with anyone. Tonight was a rare night out and, she said, Dylan and Jason seemed like fun. So Dylan and Jason got the hospitality workers’ tour of late night city life and it was a blast. They ended up at a few new places with good drinks and even got a few perks from bartenders who knew the waitress.
The innuendo continued to fly. Dylan and the waitress did a lot of touching while talking. Everyone was pretty buzzed and when they left the last bar at 2am, Dylan and the waitress were arm-in-arm walking down the street.
Jason was looking for a cab. Finding one at this time of night was no easy feat. He had the girls wait at a corner while he went down part way down the block to see if any cabs were camped in front of a chain hotel there.
When he came back, Dylan and the waitress were lip-locked. The waitress had both hands on Dylan’s head. Dylan’s right hand was palming the waitress’ ass.
Jason walked slowly towards the pair not wanting to break up the scene. He was a hundred or so feet away when the headlights hit the girls, lighting them up in full splendor. Jason had to reach down and adjust his cock in his pants. Things had gotten quite tight down there.
The headlights belonged to the cab Jason flagged at the hotel. The cabbie pulled over and the gang piled in. Not a word was spoken but there was a lot of giggling in the back seat. And the girls were still feeling each other up.
The cab driver was of Middle Eastern descent. It was pretty clear he did not approve of what he saw. All for the good, Jason thought. This was probably better than some guy who found the whole thing exciting.
Jason was glad he had already told the cabbie their destination. That way he didn’t have to say anything at all.
It took about 10 minutes to get to Dylan and Jason’s hotel. Dylan and the waitress were barely in the elevator before they were kissing again. Jason was starting to feel left out even though he knew his threesome deal with Dylan was girl-on-girl only. His mind understood that Dylan would take care of him at some point, perhaps even with the waitress watching. His cock and balls, however, were aching to get in the game.
Once in the room, Dylan got a little more focused. She poured a drink for Jason, walked him over to the chaise, patted the cushion, and told him to sit down. Once seated, she straddled Jason and ground her crotch against his cock. She began to unbutton his shirt.
“You, my dear,” Dylan said loud enough for the waitress to hear. “You get to watch. I’d suggest keeping your cock tucked inside those pants for a while so you don’t come too fast. I’ll be back for you in a bit.”
Jason could see the waitress over his shoulder. She was busy getting undressed as Dylan was giving Jason his instructions. By the time Dylan was done talking, the waitress was standing naked behind her. The body that looked fit in a waiter’s outfit looked even better without it. Nothing was out of proportion. Her breasts weren’t overly large but they stood out against her smallish frame. She wasn’t skinny and she wasn’t buff. She just looked healthy and a little younger than her years thanks to the short haircut. Like Dylan, she had a perfectly shaved pussy. And she looked comfortable in her own skin.
Dylan rose from the chaise and turned to see. She looked back at Jason and smiled. “Thank you for giving me this opportunity,” Dylan cooed. “I owe you one.”
The waitress pulled Dylan closer and kissed again. Dylan’s hands were all over the waitress’ body. First, a trip back to her ass and then up, to play with her breasts and to pull on perfectly erect nipples.
It didn’t take long before Dylan bent down and started to lick those nipples. The waitress put her hands on Dylan’s head, cradling it against her breast. Dylan started to nibble and suck harder. The waitress tilted her head back, letting out and let out a long, pleasurable sigh.
Jason took a long drink from his glass. He was drunk enough that he really didn’t need any more alcohol but since he was forbidden from even touching himself, there wasn’t much else do with his hands. So he simply watched as Dylan shifted her attention from one breast to another, no more than four feet in front of him.
The waitress was lost in the moment, enjoying the pleasure of Dylan’s lips and tongue on her chest. Jason smiled at the sight and at the thought of living this fantasy. So far, it was good.
Dylan eventually worked her way back up to kissing the waitress and, in return, the waitress started sliding her hand up the back of Dylan’s dress. They kissed and felt each other in front of Jason, moaning and swaying a new lover’s dance as they learned to make their bodies fit.
It looked to Jason as if the waitress was leading this dance and, sure enough, the girls found their way to the foot of the bed. It was so graceful that it didn’t appear to be intentional. But in a fluid motion Dylan was sitting on the edge of the bed and the waitress had Dylan’s dress in her hand having lifted it over Dylan’s head. As Dylan unlatched and removed her bra, the waitress went down on her knees.
It was at that moment Jason realized Dylan was still wearing her cowboy boots. But instead of being an obstacle, they simply became part of the swirl of arms and legs and beautiful bodies in front of him.
A guy trying to take off a girl’s cowboy boots in these circumstances ends up feeling clumsy and lame. Two girls on the other hand, at least these two girls, made it look like ballet. The boots and Dylan’s panties were quickly on the floor.
There was Dylan, sitting in front of Jason, in all her splendor, full tan, and a shaved pussy. And also in front of him, the waitress with a body to fit Dylan’s. Just like hers. Just like Dylan wanted. Dylan told the waitress she wanted to finish what she started in front of Jason. The two climbed on the bed, kneeling at first while kissing and feeling each other’s breasts. Eventually they tumbled down. The waitress was on her back and Dylan stretched out on top of her, kissing her, feeling her, rubbing her pussy against the waitress’ crotch. Jason started to rub his cock through his pants as he watched Dylan play the role of the aggressor. It reminded him of the first time they had sex.
Jason was so horny for Dylan that everything was moving forward — his head, his lips, his tongue, his hands, his cock. He swarmed her. It wasn’t forceful. In fact, Dylan was very receptive, yielding in some places and moving her body to meet his in others.
He saw the same thing happening in front of him right now. Dylan swarming forward and the waitress yielding, receiving, and embracing. Dylan’s right hand slid between their legs.
The waitress let out a loud moan as Dylan’s fingers penetrated her pussy. Her hand underneath her and firmly in place, Dylan moved her hips as though they were fucking. The waitress clamped Dylan’s ass with both hands to make Dylan’s pump faster.
Dylan broke the position after a couple of minutes. She quickly slid to the foot of the bed and threw open the waitress’ legs. It didn’t take long for Dylan to lick her way up into the waitress’ crotch.
Jason had always wanted to watch Dylan go down on another girl. Dylan liked the taste of her own pussy. She would lick her fingers, his fingers, and even his cock if there were fresh pussy juices to be had. And she was so passionate when sucking his cock that he thought she would have the same passion for going down on girls.
Jason stood up to get a better view and when he did, he saw Dylan’s tongue probing the waitress’ pink lips. Moans from the waitress caused Dylan to give more attention to some areas than others. Every so often, Dylan would pause, lick her lips and even swallow some of the juices. She was clearly enjoying the moment. And that made Jason want to fuck her.
Over time, Dylan began probing the waitress’ pussy less, instead concentrating on the most sensitive areas. The waitress moaned even more. And although the waitress was starting to guide Dylan’s head to the best places, she didn’t have to put out much effort. Dylan knew. She knew from her tongue probes on the waitress and she knew from the spots where she liked to be licked by Jason. Jason stood next to the bed with his shirt open and his pants bulging. He was under strict orders to not come. Dylan had suggested he keep his cock in his pants as well, but that wasn’t going to work much longer. He was aching to get out so he undid his belt and dropped his pants and shorts as quickly as possible. His cock was already its full 7 inches. And it was as hard as it gets. The veins looked like they were about to burst and his helmet had a deep purple color.
Jason slowly ran his left hand from the tip down to his balls. A loud “holy shit” drew his attention back to the bed. The waitress was staring right at his cock.
“I’ve never seen a shaved one!” she exclaimed. “It’s so fucking… nice.” Dylan looked up for a moment, rolled her eyes at Jason, smirked a little, and then when back down on the waitress. It didn’t seem like she was mad that he had his cock out. The look was more “Oh, well” than “I’m pissed.” Jason figured she was enjoying herself too much to make a big deal out of it.
Jason slowly stroked himself as Dylan homed in on the most pleasurable spot of the waitress’ clit. The waitress started pushing her crotch up towards Dylan’s face. And she alternated watching Dylan licking her pussy and Jason handling his cock and balls. The waitress’ body started to tense up and she started telling Dylan over and over that she “licked pussy so good.” It wasn’t really yelling. It was more like enthusiastic panting interspersed with the occasional “Don’t stop. Keep licking me.”
The waitress’ body was taut on the bed and it jerked wildly as she came. She put her hands on Dylan’s head. Dylan held her tongue firmly in one place as the waitress fucked her face. Dylan’s eyes were wide open as she watched the woman in front of her come again and again. Jason also watched in amazement. He had even stopped stroking his cock. Dylan nuzzled her face into the waitress’ crotch and inner thighs as she came down from the intense orgasms. Dylan licked up all the pussy juices she could find and then slid up into the arms of this new lover. They embraced and kissed. It dawned on Jason the Dylan must have this woman’s essence all over her. And the waitress was enjoying tasting herself on Dylan.
His cock was in dire need of attention at this point. He was good so far on the promise to not come until Dylan was ready for it. But now he was feeling it was his turn. Dylan cut him off as he started to speak. “Ladies before gentlemen,” see declared. “And this lady is ready to go.”
The waitress took her cue and gave Dylan one last deep mouth kiss before kissing and licking her way down to Dylan’s pussy. She stopped at Dylan’s breasts, spending some time sucking and biting on her nipples. Jason liked to do that too. He couldn’t get enough of having them in his mouth.
It didn’t take long for the waitress to have her face between Dylan’s legs. And once there, it wasn’t long before the waitress looked up and told her, “I love the way you taste. This is heaven.”
Dylan closed her eyes and moaned. Her head went back. Her lips parted and her breathing started getting heavier. The waitress seemed very adventurous. She alternated between working her tongue deep into Dylan’s pussy and lightly licking Dylan’s clit with the tip of her tongue. Every so often, she would use a finger or two to rub a sensitive area or penetrate Dylan’s pussy. Jason had tried some of these techniques with some success, but the waitress had a girl’s touch and Dylan’s moans made it clear she was enjoying it all.
Jason could stand by no longer. He climbed on the bed, leaned over Dylan and started sucking on her right nipple. He had the left one between his finger and thumb. Dylan squirmed at his first touch. It surprised her but then she readjusted her body to better accommodate the girl between her legs and Jason’s probing mouth.
Dylan’s body was exploding with pleasure. Both breasts. Both nipples. Inside and outside of her pussy. She turned her head to the left, only to see Jason’s cock just a few inches from her face. She wanted it.
“Jason,” she whispered. “Your cock.”
He knew what that meant. He readjusted his position on the bed so his cock was hovering over Dylan’s face. Her head was turned to the side and her mouth opened. Jason lowered himself to an “all fours” position so his body was draped over her head. He slowly pushed his hips forward and watched as his cock entered Dylan’s mouth.
The waitress was watching as she licked Dylan’s pussy. She started to concentrate on the areas of greatest pleasure for Dylan and Dylan helped out by guiding the waitress’ head with her hands. All this was going on as Jason’s cock slid slowly back and forth in Dylan’s mouth.
Jason decided it was time to talk.
“This is it Dylan,” he whispered. “This is our fantasy. This is the moment that makes you come so big, a cute girl licking your pussy and my cock in your mouth.”
Dylan began to moan even more. It was a moan of deep pleasure mixed with a tiny bit of panic. Jason had heard this before. She wasn’t afraid. She was at that edge of pleasure so great and so strong that it almost hurts.
“Dylan.” Jason said. “I want you to come. I want you to come big. I think I’m going to come soon. Where do you want me to come? In your mouth? On your face?”
The waitress was licking Dylan hard and trying to finger her own clit at the same time. She was beginning to make noises of pleasure too. Dylan moans became more constant. And while they weren’t getting louder, they were muffled by the cock in her mouth, they had a greater sense of urgency.
Just when Jason started pumping his cock faster, Dylan put a hand on his chest. This was the signal to stop. Dylan had about five inches of Jason in her mouth. Her shorter, urgent moans turned into that familiar long, slow moan that meant she was coming. Her whole body convulsed as the orgasm hit. The waitress buried her face deeper into Dylan’s pussy. Dylan opened her mouth a bit wider and Jason withdrew. “Oh God,” Dylan gasped for air. “I’m still coming. I’m still coming.”
Her body convulsed again and she pushed the waitress away from her pussy. Jason knew what had to come next. It’s what they almost always did when Dylan used her vibrator to come while Jason fucked her mouth. Jason grabbed the waitress by the arm and helped her up all the way up on the bed. She lay next to Dylan and watched as Jason positioned himself between Dylan’s legs. His cock was huge next to her swollen pussy. Dylan reached down and guided it as Jason pushed forward.
Jason practically came watching his cock separate her pussy lips and disappear inside her. But somehow he controlled the impulse. Dylan started to come again as Jason entered her. The waitress started kissing Dylan and playing with her own pussy.
Jason pumped slowly at first. This usually gave Dylan a very intense second orgasm. Sometimes it was more intense than the first and it looked to Jason like that’s what was happening now. He pumped faster after Dylan’s second wave of pleasure began to subside.
He was trying to get her to a third orgasm but he wasn’t sure he was going to last that long. That’s when Dylan asked to lay on her side.
Jason obliged by pulling out. Dylan and the waitress each turned on their right sides. Dylan embraced the waitress, putting her arm over her hip and her fingers on her clit. Dylan kissed the back of her neck as the two of them stroked the waitress’ pussy.
Jason took up position on the other side of Dylan and slid his cock into her pussy from behind. It had reached the point that Jason couldn’t go slow any longer. He sped up as he pumped and his weight shifted until he was practically on top of Dylan, who was on top of the waitress, but with her hand in the waitress’ pussy.
They were all moving at Jason’s speed when the waitress started to come. It was all very new and different and odd. Jason felt his cock in Dylan’s pussy but he heard someone else coming.
That was it for Jason. He started to moan as the pent up energy released itself. Jason thrust his cock as deep as he could into Dylan and held it there as wave after wave of cum shot through his thick rod and deep into her body.
Then every muscle relaxed. Jason fell back onto the bed, spent and drunk and tired. The room was spinning. He heard Dylan.
“Thank you, baby, for a perfect night of fun. I owe you one. But get some sleep and reload first.”
Jason passed out.
That was then.
Apparently, he was rested and reloaded now. At least the girls thought so. And apparently, when Dylan said she “owed him one” she meant the girl-on-girl only rule was not in effect. That explains how he woke to the waitress was sucking his cock. But Dylan had just gotten off with her toy and Jason wasn’t sure what was next. He certainly wasn’t sure if he was supposed to take the lead on anything. Fortunately, he didn’t have to.
“Our friend Claire here has never had a chance to play with a properly shaved man before,” Dylan said. “How do you like it so far?”
So that was her name. Claire! Well, Jason thought, it’s never too late to learn.
“Most fun I’ve had sucking a cock,” said Claire.
“It’s even better on the inside,” said Dylan. “Why don’t you climb on?”
Holy shit, Jason thought. Dylan is telling another girl to climb on my cock.
“Only one rule,” Dylan said. “You get the cock. I get the cum.”
Claire didn’t hesitate. “I can live with that.”
And with that Claire straddled Jason and lowered herself on his cock. Jason wanted to close his eyes and just feel the moment but cutting off one of his senses didn’t seem like a very good idea at that moment.
The body was experiencing pleasure. The mind was a little scrambled. Claire let out little noises of pleasure as she wiggled and adjusted to get all of Jason inside her.
Jason felt her wet pussy on the shaved skin around his cock. He loved that feeling with Dylan. This was the same, but somehow different. Claire wiggled even more, grinding her pussy against Jason’s smooth skin.
“Ooooh. I like that,” she said. “Not sure I can ever go back after this.”
Dylan smiled. Jason hadn’t shaved before he met her. She had often told Jason that he’d never go back to unshaven once he tried it and she was right. What he didn’t understand until this moment was that Dylan never wanted him to go back either. Not a problem.
Dylan stood next to the couple on the bed and watched for a moment as Jason clutched Claire’s ass and started to pump her. It didn’t take long for Dylan to reassert her control over things.
“Claire,” she said. “Grab his wrists and pin him to the bed.”
As Claire complied, Dylan reached for her bullet vibrator and turned it on. Jason felt the bullet touch his balls sending wild shocks of pleasure through his body. When it wasn’t touching him, it was touching Claire and she started to tremble with pleasure. Claire slowly moved up and down on Jason’s cock while Dylan explored their pleasure zones with her vibrating probe. It wasn’t long before Jason felt Dylan’s fingers on his balls too. He could feel the cum starting to boil up inside of him. “I can feel your balls moving Jason,” Dylan said. “Don’t come until Claire comes. Save your cum for me.”
Claire responded first. “I come best when I can touch myself too.”
Dylan instructed Claire to sit straight up but to stay firmly planted on Jason’s cock. As Claire released her grip on Jason’s wrists, Dylan got on the bed behind her. She straddled Jason’s legs and wrapped her arms around Claire.
“I think what you’re saying is that you come best when you’re touched,” Dylan said. “But I’m guessing that you don’t have to be the one doing all the touching.”
The vibrator clicked on again. Dylan’s left hand reached around from behind Claire and grabbed a breast. Her right hand reached around with the bullet and found its way to Claire’s pussy.
Claire gasped and threw her head back against Dylan, exposing even more of her pussy to Dylan’s reach and Jason’s eyes. Though it seemed impossible, he felt his cock grow harder. Claire seemed to notice it too. She simultaneously started to ride up and down on Jason’s cock and guide Dylan’s hand to the best places. Dylan followed Claire’s lead on location and pressure. Jason watched as their fingers found their way to the very top of Claire’s pussy lips. Their hands stayed there as Dylan fondled Claire’s breasts and kissed her neck. It was quite a sight, Dylan decked out in her leopard camisole and collar, wrapped around Claire’s body and Claire completely lost in so many sensations — the wetness of Dylan’s lips on her neck, the pressure of Dylan’s fingers squeezing her nipple, the heat and girth of Jason’s cock filling her pussy, and the shock waves emanating from Dylan’s bullet vibe on her clit.
Jason trying to take it all in and, at the same time, trying to on not come. He was close to releasing his load and the combination of a two girls and a vibrator was making it a tough battle.
Jason’s stamina paid off a few minutes later when Claire came hard again. Dylan held her tight to keep her from separating from Jason’s cock. Dylan loosened her hold as Claire relaxed and fell forward on to Jason. Dylan was soon next to the two of them.
“Claire,” she said. “Still one more thing to do.” Claire rolled off Jason and came to rest along his side. Dylan slid down to the foot of the bed and took Jason’s still hard cock in her mouth. It tasted of Claire and Dylan was happy about that. Claire looked Jason, kissed him and said, “Excuse me, but I can’t miss out on some of this.”
The next thing Jason knew, his cock was engulfed by Dylan’s mouth and his balls were getting a good cleaning from Claire’s tongue. He propped himself up on his elbows to watch but the feelings were too intense to stay upright for long. After catching a hungry glance from Claire and a loving glance from Dylan he laid back and got lost in the pleasure. Jason could tell that they were taking turns — one sucked his cock while the other licked his balls. Claire was good on his cock, but not nearly as good as Dylan. Every once in a while he would feel them both in the same area. Two tongues running up his shaft or one on each nut. Dylan was deep-throating him when he felt the finger near his ass. He didn’t know who was doing it, but it only took a tiny bit of penetration before the cum swelled up and raced through his cock. Jason leaned up a bit and put his hands on Dylan’s head, as he had so many times before. He was coming huge. It felt like forever.
And yet Dylan stayed on him, taking in every last drop. The cum was hers, just as she said it must be. But once she got it all, she grabbed Claire’s head and gave her a deep passionate kiss. Jason watched as small amounts of his cum leaked from their mouths.
When they finally parted Dylan said, “I hope you don’t mind that I decided to share.”
No one was sucking Jason’s cock the next time he woke up. The sun was streaming through the window. Dylan was propped up in bed next to him, still in her camisole but minus the collar. She was reading something on her smart phone. The clock radio showed it was just after 8:30am. Jason moaned, but it wasn’t from sexual pleasure. “I have a hangover,” he said. “A Bloody Mary can fix that right up,” Dylan replied.
“I think it’s a sex hangover.”
“Like I said… well, maybe not… never mind.”
“Where’s Claire?” Jason asked.
“She left about an hour ago.”
Jason paused for a moment and then commented, “I always wondered how threesomes were supposed to end. They never show that in porn. They just cut to the next scene. Now I know it ends with a sex hangover.”
“I think you have to explain ‘sex hangover’ to me,” Dylan said.
“I know I had a great time,” Jason said. “But my entire body is aching and tired. I don’t think I could even get up for another threesome right now.”
“And that’s a good thing,” said Dylan. “You know how I said ‘I owe you one?’ Well, I really meant one. That was a once in a lifetime treat for both of us. Once. Lifetime. I hope you’re not disappointed.”
“Not at all,” Jason said. “We have better sex in a week, any week, than most people have in a year. I’ll take that anytime.”
“Good,” Dylan answered.
She was about to say more when the text alert beeped from her phone. Dylan looked at the screen and smiled. “Then again…” she said as she showed Jason the screen.
It was a text from Claire.
It said, “Thanks.”
And, “I owe you one.”