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.
