It was just a little past noon when Will finally started to stir. As he slowly opened his eyes, Will realized that he had fallen asleep on the couch sitting up. Every muscle in his body was protesting as he stretched and slowly made his way to his feet. “Fuck,” he moaned as he started for the bathroom, hoping a hot shower would ease the tightness of his muscles and the slight ache in his cock from all the attention it had received last night.
Turning the water on as hot as he could stand it, Will stepped into the shower, turning his back to the water letting it cascade down his back as he rotated his shoulders and neck to ease the tightness. After a few minutes, he turned around to let the water hit the front of his body. Bracing his hands flat against the shower wall he stuck his head in the water. Grabbing the shampoo, he quickly washed his hair, and then rinsed it.
He had no idea when he walked into that small office that his entire life was about to be turned upside down and that his body would become a hot commodity. He had never been one to workout religiously but did try to keep fit. As he stood there his thoughts turned to the hot sex he and Jasmine had along with all the other hands, lips, and tongues that had touched his cock and balls.
All these thoughts seemed to hit the ‘need to cum’ button as his cock began to harden and twitch. Reaching for his body wash Will squirted a little on his hand to make stroking easier. Picturing Jasmine’s mouth on his cock Will began to slowly stroke himself with his fingertips. His head tipped back as his mouth opened slightly, taking in deep, shallow breaths as his hand tightened around his cock. Slowly his hand moved up and down his cock, pulling out his cum. Getting to the edge, Will forced himself to stop from shooting against the shower wall.
After giving his cock time to soften some, Will restarted by lightly running his fingertips up and down the underside while his other hand started squeezing his balls. “Oh fuck,” he moaned as he gripped his cock tight in long deep strokes. Getting closer to the edge his movements increased as he continued to moan, “Oh fuck…suck me off Jasmine. Make me cum. Swallow my load,” as he unloaded, splashing against the shower wall and down the drain.
Will slowly regained his equilibrium, his shaky legs barely holding him up. As the water cooled, he turned it off and climbed out, grabbing a towel and semi-drying himself off. Dropping the towel on the bathroom floor, he headed naked into the kitchen for a glass of sweet tea and a sandwich. He now felt he could handle all the attention he was sure to get that night without worrying about a hair trigger.
When he walked into the club at three thirty, his mind was all awhirl, wondering what the night would bring. To his surprise, he was not asked to go upstairs nor was his services requested for the next three weeks. As he continually worked on the club floor, he started to wonder just what he had done wrong. He saw Ms. Jasmine Jameson every weekend, but she did not initiate any more upstairs visits although she was always sitting in his section. Finally, he had enough, so he arrived at work early, planning to go see Ann and ask her if he had done something wrong. But that all changed when he got to work that Friday night and saw a note taped to his locker door.
‘Schedule changes: Friday Bachelorette party of four at 7:00 pm, Saturday initiation party.’
Diego saw him looking at the note with a puzzled look on his face, so he said, “Party on Saturday is with Ms. Ann.”
“Ms. Ann?” he asked, “Is that normal?”
”Yeah, she always has an initiation party for new servers after they have worked here about a month. Sometimes Ms. Beth even joins in. It is nothing to be worried about. We all had to go through it and believe me; it was really fun. You will also get paid for having fun.”
“That sounds very interesting. Ms. Ann is a foxy lady. I love women with some junk in their trunk and full figured. When you fuck them, it offers you some cushioning and doesn’t feel like you are fucking a bundle of sticks.” Will comment as he stripped off and put his clothes in his locker, strapping on his little pouch.
What he was unaware of was that Ann had been passing by the open locker room when Will made his bold statement about her. After hearing from her other best friend Jasmine about the great orgasms he had given her Ann did not want to wait her customary month before having him in her bed but forced herself to wait. She didn’t want to show partiality to any of her servers and cause problems among them. Ann kept telling herself that waiting would make it all that much sweeter and hotter. Tomorrow night she would find out if Jasmine was right and she could hardly wait. Just thinking about it made her thong wet.
For the first couple hours he and Diego worked the floor alone, but around six o’clock the other four servers showed up. As Will gave the bartender the order from the table, he was waiting on, Doug came up to him, saying, “Your bachelorette party of four is here. Let someone know and come sign out. They have reserved five hours.”
“Sure,” Will said. “Give me five minutes.”
Once he delivered the drinks and made sure the ladies were taken care of he went in search of Diego.
“Hey Diego, my bachelorette party is here and have reserved five hours,” Will said, “Whoever takes my tables tell them to take a hundred dollars out of the tips.”
Diego nodded in agreement and waved Will away. Will went up to the Doug and signed out, then asked, “Where are they?”
“They are in the convention room and there is a self-contained bar in the room. Do you know how to make drinks or do you need a bartender?”
“I know how to make the basic drinks, so hopefully I can manage. If not, is there some way I can let you know?”
“There is a buzzer under the bar so if you need help, just push it and help will be sent and don’t worry; we have all used it before,” Doug told him. “Room is down the right hallway.”
Will nodded and took a deep breath, heading down a side hallway to the convention room. When he was out of sight of everyone he gave a fist pump in the air. He was finally being asked for his services off the floor and he wanted to make a great impression on them and Ann so his services would be requested more often. All he knew were that there four ladies and while he liked to fuck he was not sure he could cum that many times if they leaned that way, especially if any of them were like Jasmine.
He knocked and slowly opened the door, stepping just inside the room, not sure what to expect. What he saw made him stop and take a second look, wondering if the guys were playing a trick on the new server. Across the room he heard a bunch of ooh’s and ahh’s from the ladies in the room when they saw his nude body. It was easy to spot the bride as she was wearing a veil and looked to be in her fifties. The other ladies in the room were also in their forties and fifties.
Once he assessed the situation, he started to feel less stressed about performing. Considering their age and the conservative way they were dressed he was a bit shocked that they would even consider having a bachelorette party there. They seemed more like a nice quiet event in one of their homes. This was probably the only shocking thing they had done in their entire life. ‘Wonder who the wild woman is in this party to book it here’ Will wondered to himself.
Suddenly he realized all eyes were focused on him and that he had been standing in just inside the room for at least five minutes. “Welcome to The Cougar Lounge ladies,” Will said gathering his wits about him as he shut the door behind him. “What would you ladies like to drink?”
Will took their drink orders and went behind the bar to fix them. As he set the drink in front of the bride, he was surprised to feel her hand reach out and wrap around his cock, giving him a squeeze.
“Wow, you are so big,” she commented. “I hope George is at least half that big.”
“I get the next drink and feel,” said the woman sitting next to the bride. “It has been a while since I had my hand wrapped around a cock not to mention in my pussy.”
“Jolene Marie,” scolded the bride, “that is too much information. We do not want to hear about your scandalous love life.”
“Then plug your ears sis,” Jolene said sticking her tongue at her sister
Will worked hard to suppress a laugh but could not help the smile that appeared across his face. Jolene Marie was as round as she was tall and he could just imagine how she would feel underneath him. ‘Will, she is old enough to be your momma. You should not be thinking about fucking her,’ he scolded himself.
As he set the drink in front of her, Jolene’s fingernails grazed his semi-erection and then she leaned down and licked her tongue across the head. When she sat up, she started laughing at the redness of her sister’s face.
“He sure tastes good. Why don’t you have a taste,” Jolene said to her sister. “It will probably be your last opportunity to go wild since you are marrying our pastor Sunday after church. After that, it will be in the dark and missionary position. Wham, bam, thank you, mam,”
“That is enough Jolene. I should have known better than to leave you in charge of my bachelorette party,”
“Well I have to make sure that my sister has one wild fling and you did reach out and squeeze him first,” her sister argued back.
At this time Will was wondering what Ann had gotten him into and if he was going to be called in to break up a fight between the two sisters as he delivered the other two drinks, both of them copping a feel.
Suddenly the image of the two sisters wrestling around in a swimming pool of Jell-O sent shivers up and down his spine. Normally the idea of seeing two women in bikini’s wrestling in Jell-O would be a turn on, but the thought of Jolene and her sister was not.
“Will,” said the bride breaking into his thoughts, “I am Hilda and getting married Sunday as she said. Jolene is my younger and only sister. These two other ladies are sisters and our cousins, Mindy and Sherry.”
Hilda was almost a carbon copy of her sister, but she was a bit taller and a little slimmer. Both of the other two ladies were tall with an athletic build and judging by appearance Mindy was the youngest. Will just stood there waiting for them to tell him what type of entertainment they wanted.
“Will, what kind of entertainment is included for our bachelorette party? Mindy asked smiling.
Not exactly sure how to answer them he just stood there for a minute trying to formulate an answer, finally saying, “It is up to you ladies to decide what type of entertainment you want,” hoping it was the right answer.
“Just you being eye candy and letting us cop a feel is enough,” Hilda said quickly before her sister could suggest something wild and out of her comfort zone. “I will have another drink though.”
“Anyone else need a refill?”
The rest of them requested a refill and for the next hour, all the ladies did was drink and cop a feel of his cock. By this time Will was fighting the urge to clock-watch, trying to will the clock to move forward faster. He had the feeling that nothing sexual was going to happen and the tip, if any, was not even going to cover what he was paying the one taking care of his tables.