I Owe You OnebyBobcatPounce©
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.