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.
Suddenly Jolene began to giggle and asked Will, “Would you fuck my sister? She needs to have one good fuck before she gets married.”
Will, who was bringing more drinks to the table, was so shocked by what she asked him that he almost dropped the tray.
“Ah…ah…yes I would, but she would have to be willing,” Will told her, figuring the subject would then be dropped because there was no way in hell she would agree to that.
To his surprise, Hilda struggled to her feet, her hands going to the buttons on the front of her dress, fumbling to open them. Soon she had the buttons open after her fumbling caused a couple of them popped off and rolled across the floor in her hurry to expose her breasts. Will tried not to stare at her breasts, bound in a sensible white cotton bra that was unable to completely hide the promise of the hidden flesh inside. Her hard nipples were prominently pushing against the cups making Will’s cock jump to attention as he imagined his lips around them. And her cleavage…why it was just begging to be used as a fuck tool; he could just feel them clenching him tightly as he came all over her face and chest.
‘Damn, this ridiculous. I cannot believe I am getting hard over an older woman who is about to marry a preacher. I wonder if she is a virgin,’ Will thought to himself.
Out of the blue, it hit him that she was a bit tipsy and probably would not normally exhibit such behavior although he could imagine her sister doing it. He decided that out of respect for her tipsy condition he would not make the first move although his cock was telling him differently.
“Will, what do you think of my cousin’s tits? Did it give you a boner?” asked Sherry
“Come over here and show me,” Jolene told him.
As he walked around the table, he tried to turn his mind to non-sexual things hoping his hard-on would dissipate but no such luck.
“I’ll be damn sis; you did give him a boner. Wonder if you can do that to George?”
All of them started to laugh when suddenly Jolene stood up and removed her dress, leaving her standing there in a pale blue cotton bra and matching panties.
“Oh hell,” Mindy said, “let’s all get buck naked and fuck Will silly. You are the bride, so your pussy gets his cock first Hilda and Jolene, he can eat you out.”
Will just stood there, not sure what was going to happen but soon dresses, shoes, panties, and bras were being taken off and dropped to the floor until all ladies were naked. Will looked from one to the other, amazed at the various sizes of breasts and nipples and general body shapes. Hilda’s breasts were at least a 38C while her sisters had to be at least a 40D. Mindy had the smallest breasts but big areolas. Her sister Sherry was just a little bigger with smaller nipples.
“Well hell, there is no bed here so guess we will have to do it on the floor,” Sherry said as she grabbed the drink tray from Will and piled the empty glasses on it and carried it over to the bar to put it down. Grabbing the table cloth, she spread it out on the carpet.
“On your back Will,” Jolene said pointing to the table cloth.
By now Will was rock hard and did not try to hide it. He was not sure after he came how long it would take him to recover and if he would be able to fuck all four. It seemed as if his worst nightmare was about to come true…the inability to man up and fuck all four women. Undoing his pouch, he tossed it on the table after he removed a condom and covered his cock.
Will then laid down as he was told and motioned for Hilda to come to him. As she knelt down beside him, Will said, “Straddle me and let me have those luscious tits of yours. As she did as he said he grabbed one of her nipples, rolling it between his fingers while he sucked the other one into his mouth, his other hand stretching down to rub between her folds.
Hilda let out a soft moan as she started to feel things her ex-husband had never instilled in her. Will then switched, sucking hard on the other nipple while his fingers worked their magic on the other. Suddenly Hilda gave out a little squeal as his thumb brushed against her little nub. Will continued until she was on the edge and then he stopped, pushing gently on her sides to indicate that he wanted her to ride him.
“Kneel on either side of me and let me guide my cock in you and then you just move up and down,” he instructed. “Jolene, bring me that pussy of yours over here…now.”
She did not need a second invitation as she squatted over his face. Once Will felt Hilda sliding down his cock, he reached up, putting his hands on Jolene’s hips to pull her down toward his face. Spreading her lips Will ran his tongue up and down her slit, pulling her clit between his lips, sucking on it gently. Hilda began to slowly move up and down on his cock, hoping she was doing it right. Instinctively her pussy gripped him tight causing him to moan into Jolene’s pussy.
As he sucked her clit, he used two, and then three fingers deep inside her pussy to finger fuck her as he blindly reached down toward Hilda looking for her opening. With a little searching, he managed to find her clit. Soon both women were moaning as he brought them closer and closer to an orgasm. Suddenly he could feel both women tense up, their juices covering his face and cock, their bodies twitching and shaking as he sent them over the edge together.
Both were gasping for breath as Jolene moved off and sat down on the floor above his head. Will grabbed Hilda by the hips moving her onto her back as he started to fuck her hard and deep, reaching for his own release. Grabbing her legs, he bent her forward so he could get in deeper. Giving out a small cry as he came, filling the condom full of his seed and setting off another orgasm in Hilda. He laid there for a few moments and then slowly eased his way out so the condom did not dislodge from his cock. Sitting back on his heels, he slowly removed the condom and tied it off. Getting up he took it over to the trash can to dispose of it.
As he turned around to address Sherry and Mindy, he saw them all sitting on the table cloth or near it on the carpet.
“Ladies, give me a few minutes to recuperate and then it will be your turn if you want it,” Will assured them.
Mindy laid back and stated, “I am les-bi, and all I want is my pussy ate but not your cock.” When she saw Will looking down at her with a puzzled look, she quickly explained, “I have a female lover and I am not into men’s cock in me but love to have a man eat me out.”
“In that case,” he began as he got down on the floor, gently pushing her back and spreading her legs, leaning down to nip at her lips and then started to drag his tongue from the tip of her pussy to the bottom. Will gave a little jerk as he felt a tongue licking his balls, and then his balls were sucked gently into a mouth, one at a time. A hand soon encircled his cock, lightly stroking him.
Will continued to lick and suck at Mindy’s clit and pussy bringing her closer and closer to the edge. The hand around his cock gripped him tighter and continued to stroke with long sensual strokes. Although he had just cum, whoever was stroking him knew what they were doing. He was shocked at how fast his cock was recuperating. The stroking and licking of his balls were bringing him closer and closer to the edge. He knew it would not be much longer until he shot his load. Mindy reached down, grabbing him by the hair with both fists, pulling him closer to her pussy, her body starting to twitch and wiggle as she neared the edge. Will changed his tactics and began to suck harder on her clit until she screamed and squirted her juices in his face and down his chest.
Suddenly he felt himself being rolled off Mindy and onto his back as Sherry moved her mouth from his balls to his cock taking him deep into her mouth, her tongue grazing the head. Squeezing his balls, she began to take him farther in her throat and then back to the tip.
“If you do not want me to cum down your throat Sherry you had better stop and let me shoot on your chest,” Will warned her
Sherry continued and began to deep throat him causing him to breathe heavier and faster, his balls starting to tighten. Fighting back a scream Will shot his load down her throat. She continued to suck until she drained him dry.
As he struggled to a sitting position, he saw that Hilda and Jolene had already redressed and were trying to make themselves presentable by looking in the mirror behind the small bar.
“You two had better get dressed. Our cab will be here in thirty minutes,” Jolene told the other two.
Both struggled to their feet and quickly dressed, leaving Will sitting on the floor. He slowly got to his feet and as they made their way to the door, each one kissed him goodbye. Once they were gone, Will quickly cleaned the room and then made his way to the employee’s locker room. He took a quick shower, put his pouch back on, and went up to the door to sign back in, collecting his tip envelope and putting it in his pouch.
Finding Diego, he walked up to him and said, “I am back. Which tables need my attention?”
Diego pointed them out and went to tend to his own. As he walked up to his tables, he saw Ann and Beth sitting at one of them.
“Evening ladies, do you want your usual?” he asked smiling.
Touching his cock, Ann said softly, “Hope that still works because I expect an explosive orgasm or two…and maybe a little bondage,”
“We will have the usual Will,” Beth told him
As he turned to go away, Beth smacked him on the ass, leaving a light handprint. He went to the bar and got their drinks, taking them back to them. As he waited on his tables, each time he passed their table they took the opportunity to touch him or pinch his ass. By the time the club closed, Will was exhausted and all he wanted was to get home and go to bed so he could recharge for the party with Ann.
He went to see Doug to get his tip envelope. When he walked into the locker room, he flopped down on the hard bench in from the lockers, exhaling a loud sigh.
“You sound like you are tired Will. Did your group wear you out?” asked Diego smiling as he sat beside him
“Unfortunately they did,” he admitted, as he struggled to get to his feet and open his locker. After getting dressed, he emptied his pouch and stuffed the wad of bills in the front pocket of his jeans. “Hey Diego, did the server who worked my tables get their tip?”
“Yeah, I did,” he answered.
“Thanks, buddy,” Will said. “I will see you on Monday.”
“Make sure you rest your cock,” Diego teased him. “And don’t jack off before going to her party. She is insatiable and so is Beth if she shows up.”
“Thanks for the warning,” he said as he headed toward the employee entrance, opening his tip check on the way.
Suddenly he stopped dead in his tracks, his mouth dropping open when he saw a check for five hundred dollars…along with Jolene’s phone number. As Will headed for his car, a smile crossed his face, wondering if it was allowed to see clients out of the club.
