Sissy's Journey: The Cocktail Party

Brett was an attractive boy with a swimmer's build in his late twenties with short dirty blonde hair, clean cut in appearance with soft features and a chiseled, toned but slender body. He had been busting his ass since high school trying to make a name for himself as a musician, but as more time had passed without landing that elusive record deal, he began to grow discouraged. When his parents finally forced him to move out from under their roof, he became determined to never have to rely on their support again, no matter how much he had to struggle for self-sufficiency. He simply couldn't go crawling back to his parents for help now, it would be too embarrassing.

The moment had finally arrived, it was at last time to put the finishing touches on his grooming ritual and await his ride to his first gig as a private party waiter. Times had been tough for Brett for longer than he could even remember. Ever since he'd been living out on his own, he'd been scrapping for every dollar he could manage to get his hands on, feeling lucky each month he could afford to make rent. He was determined to make ends meet one way or another, whether that meant delivering pizzas for tips, bar tending for local events, or the occasional catering job that happened to come his way. He'd been on a downward spiral ever since dropping out of college, and had earned the judging scrutiny of his parents in the process.

Brett decided he'd do whatever it took to make it on his own, and when he saw an ad on Craigslist advertising $5000 for a single cocktail waiter gig, perhaps he should've seen the writing on the wall that it was too good to be true. However, once he saw what the job paid, he pushed aside his doubts and decided he had to reply.

He typed up a well-written response to the ad and attached his resume, then got in the shower to wash the smell of pizza and sweat from his freshly groomed skin. He didn't hear the beep of his phone, but when he exited the shower to dry off, he heard the sound of a missed call. The voicemail was very matter of fact and the caller spoke with an almost cold detachment.

"Mr. Williams, I have your resume here in front of me and I was hoping to speak with you about the bar service required for tomorrow's party. Please call me back at your earliest convenience so I can inform you of the unique requirements requested for this particular position, thanks!"

Brett's excitement level spiked and he hurriedly dialed the number. The voice from the message greeted him and he could scarcely hide his eagerness. "Um...hi, hello this is Brett, I just emailed my resume in response to the ad for bar service for tomorrow's party..." He verbally stumbled through his response and he heard a silence on the other end of the line. "Hello?"

"Hello Mr. Williams, glad to hear from you," answered the voice on the other end of the phone. "We normally don't reach out last minute like this, but our regular girl cancelled and we need to find someone to fill her position immediately..." The payment will be deposited into your account following the party, but my team will need to work with you prior, so we will require that you arrive early tomorrow afternoon to prepare.

Brett's mind was racing considering how much of a godsend $5000 would be to his current situation that he barely heard half of what the man said. It wasn't until he realized he'd been asked a question that his mind snapped momentarily back to reality."

"Is that acceptable Mr. Williams?"

Brett hesitated, realizing he'd accidentally tuned out the conversation. "Uh...yes sir, that all sounds good to me, I just need to know where and when to arrive tomorrow."

"We will send a car for you tomorrow at 3:00 p.m. and the party will start at 10:00 p.m. It will be a late night, but I assume the agreed upon rate will cover any inconvenience" the voice on the other end of the phone replied.

"Thank you Sir, that all sounds great! How many people are expected if I might ask?" As he finished his question he heard silence on the other end and realized the man had already hung up.

Well that was certainly short and to the point he thought, but he quickly breathed a sigh of relief and climbed into bed to be sure he got enough sleep for the next evening. It wasn't until he awoke the next morning that he considered the fact that he would be picked up seven hours prior to the party. "What kind of party requires that much prep time?" he wondered to himself, but quickly dismissed the question by recalling the wage he stood to earn in one easy night of pouring drinks for a group of privileged yuppies.

As Brett got dressed in his well worn tuxedo and fed his Great Dane he called Duke, he left and waited downstairs in the parking lot for his chauffeur. As he waited, he felt his phone vibrate and reached into his pocket to answer.

"Hello? This is Brett..."

He barely got the words out of his mouth before he heard a subdued voice on the line instructing him to look for a black Mercedes. He was informed to get in the back seat and to tell the driver that he was the server for the evening, and say nothing more.

Brett thought the instructions were a little strange, but he brushed off the thought by simply assuming the party must be very discrete for some reason or another. "I suppose that's why the pay is so good" he thought. "They don't want anyone blabbing about the lifestyles of the rich in this town.

After twenty minutes or so in the car, they finally began to slow and Brett could see they were turning into what seemed like a vast and rolling estate. They pulled up to an iron gate and the driver mumbled something to the speaker box as the gate slowly began to open for them. After traversing a long and winding driveway, they pulled up to a sprawling mansion and the driver instructed Brett to enter through what he referred to as the servants' entrance off the attached garage.

As soon as he walked hesitantly through the entryway, he was greeted by an intimidating woman in her forties who addressed him as if in a hurry, "You must be Brett, the man of the house insists upon perfection for his parties, so we have a lot of work to do to get you ready, come with me please."

She turned on her heels and walked through a corridor leading into a gargantuan bathroom. "Lay down on that table there," she said motioning to what appeared to be a massage table. "We must get started right away!"

Brett was beginning to wonder what he'd gotten himself into, but once again pushed those thoughts to the side as he considered his generous compensation. As he began to lay down on the table she stopped him.

"No no no," she said. "Remove your clothes first please, we need to make you presentable for our guests Mr, Williams."

At this he stopped, confused as to what she was implying. "I thought this was a bar service job, I already showered and got dressed accordingly Miss...sorry what was your name again?"

"No time for formalities Mr. Williams," she replied. "We need to get you ready. We only have six hours before guests will begin arriving."

Apprehensively, Brett began to disrobe and laid himself on the table face down to conceal his nakedness as much as possible. However, before he could fully process what was taking place, he felt a warm sticky substance being spread along his legs. Before he could even begin to protest, the woman had ripped the first waxing strip in one fluid agonizing motion from his calf.

"FUCK!!" "Ouch that hurts! What the hell???" he exclaimed. "What are you doing?"

"We are waxing your body dear," said the woman. "We have to make sure you're entirely smooth in the outfit you wear tonight. Our guests won't be satisfied with a stubbly bar girl."

"I'm...uh...not a girl," Brett replied, confused by what was going on. "I'm just hear to serve drinks."

"You're free to leave at any time Mr. Williams, but I have a job to do, and that job is to turn you into a presentable bar girl in time for the party, and I will NOT disappoint. You would be wise to simply comply and take the generous payment you've been given."

Brett knew it was a mistake to take payment before the service was rendered, but it was too late now. How could he give the money back now? He'd already spent it all on past due bills and rent. Besides, he'd look like a mutant with one leg waxed and nothing else. So he decided to go ahead and let her finish her waxing, no matter how it hurt.

An hour later and he was as smooth as silk from head to toe, and somewhat in awe of how soft he felt all over. "I could actually get used to this no body hair thing" he thought to himself. However, before he had time to process his new look, she instructed him to shower again.

When he exited the shower, Brett saw two other girls enter the bathroom and motion to follow them into the guest dressing room. It housed a walk-in closet sporting every conceivable type of lingerie imaginable, and some he had never even seen before. He gulped as he began to realize what the plan was...

A short time later, and following numerous giggles and humiliations from the girls as he tried and failed to dress himself sufficiently, he finally swallowed his pride and asked for their help. They laughed and agreed as they began to pick out the perfect lingerie to compliment his shapely ass and newly waxed legs. They had even fitted him in small heels to "help show off his ass" as they had said.

Realizing he'd be paid eye candy for a party was a shock at first, but as the girls did his makeup, fitted him with a nice blonde wig, and attached fake earrings, breast forms, and a few other accessories, he began to not even recognize himself as a boy when he looked in the mirror. He saw a cute young girl, dressed in a pink lacy thong and stockings that had lace in just the right places. He turned around and noticed that the heels really did show off his soft and round yet well-toned ass. He could no longer recognize his former self, and he began to blush at the thought that he was about to be seen by men looking as he did.

They had just finished when a bell chimed on the wall clock signifying there was only one hour remaining before guests would begin to arrive. His excitement turned to nervousness as Brett started realizing he was actually going to go through with this. "$5000" he kept repeating in his head. "A few hours of bar service in lingerie for $5000, I can do this" he reassured himself.

The woman in charge who had greeted him initially and ripped the masculine hair from his body reappeared with a tapered piece of rubber in her hand, and before he could protest she said, "This is a butt plug, it will help you remain in a feminine stature throughout the evening as you walk around to serve the men." And without so much as a warning, she walked behind him, pulled his lacy pink panties down, and slid the lubed up plug inside him as he yelped in surprise.

"Is this really necessary?" Brett asked in shock. Her only reply was, "You'll thank me later," as she turned and walked out of the room.

(One hour later)

Brett waited in the dressing room until he was summoned by the woman once again. "Quickly, guests are arriving, come with me so I can show you how the bar service is expected to be performed."

Brett followed the woman to the bar overlooking a sunken living room with multiple fireplaces, crystal decor everywhere, and black leather furniture of all shapes and forms. There was even a fucking sex swing hanging down in the middle of the room.

"Now Brett, the last order of business is your name. Obviously, since you're now a pretty little girl, you can't go by that name. Tonight you will answer to whatever name the men call you, but if asked, your name is Brynna. You are at no time to acknowledge yourself as a male this evening, is that clear?

"Yes Miss," Brett replied with uneasiness. "But I'm confused, aren't I just here to serve drinks?"

"You are here to provide drinks in part Brynna, but in actuality, you're simply here to serve."

With that, she once again turned and left the room. Brett was at a loss, but he had little time to consider his options before the guests began arriving out front and filling up the living room.

"Oh my god," he thought to himself. "I can't believe I'm about to present myself this way in front of god knows how many men." If he was being honest, it excited him a little to be this exposed, but it also terrified him of what he might be compelled to do in "service" to the attendees.

Hours passed and the men were scattered about the first floor including outside in the pool, the hot tub, or drinking on the deck. Brett had done far more walking than he thought he'd have to in order to keep all the men well supplied with drinks. It hadn't really been what he feared, other than the occasional slap on his ass, or crude comment, it'd been sort of a normal party (aside from being done up like a girl). The only strange things were the fact that the party's attendees were ALL men, no women. The only women here were apparently working the party in some fashion, most of which I only saw when I was being waxed and dressed. They had seemingly disappeared.

As the party flowed it started to become easier for Brett to walk with the butt plug inside, but he was constantly aware of how it stretched his ass. At first it had been uncomfortable, but the longer he wore it, the more his body seemed to get used to the feeling.

Brett began to grow tired as the men began filtering back into the house one by one. He had poured so many drinks he finally walked over to the bar and sat down to make one for himself finally. As he mixed his potent concoction and began to chug to get his buzz on quickly, the lady of the house appeared behind him.

"You've been a splendid sport tonight, Brynna. All of the men have been pleased with your service. Only a few more hours and the men will all be spent and start to filter out back to their wives."

"How do you know they all have wives Miss? Do you..."

The woman of the house cut him off mid-sentence. "The same way I know you're a desperate college dropout behind on his rent and willing to humiliate himself and sacrifice his entire masculinity...for the right price," she said, shocking Brett into speechlessness.

"I have to go now honey," she replied laughing at his deer in the headlights face. "Enjoy the rest of the party." She winked as she walked away from him which caused Brett to begin wondering what the hell she was on about.

As the men began congregating in the living room, he was once again beckoned by the lady of the house. "It's your turn to be the life of the party now Brynna, its time to be initiated into the mansion properly."

She led him out to the bar and tapped the microphone to ensure it worked. As he stood staring at the 50-60 men gathered with their eyes burning into him, he heard the lady introduce "Brynna, tonight's full-service bar girl, here to indulge each and every pleasure of the guests." He gulped at that, but managed to smile and meet the eyes of the various hungry looking men.

What was going on? What had he gotten himself into? No sooner had he thought this than the lights dimmed and the men began to gather in a circle around him. They slowly joined in chanting "sissies serve, sissies serve," over and over like some Gregorian verse.

His eyes met those of the woman who had tricked him who beckoned him to stand in front of the fireplace facing the men. He did so nervously, and slowly raised his head to take in the scene. All of the men began clinking their glasses and the man of the house stepped up in front of Brett with a magicians hat in hand.

As always, we will draw the name of our guest of honor from the hat, at which time I will hand over control of the night's proceedings to him. He drew the name and read it aloud to thundering applause as a man in his mid 50s stood and approached Brett.

"Hello sissy," he said addressing Brett, and before Brett could say anything in reply, the older black man guided Brett to his knees and lowered his pants revealing the largest cock Brett had ever seen.

He wasn't gay or even bi, so his shock and realization took a moment to register. The man approached him with his cock glistening with pre-cum, and before Brett could protest, he felt the man grab him by the back of the neck forcefully and guide his girthy black cock into his mouth.

Brett couldn't believe this was happening. The crowd of party goers cheered as the man began to thrust down his throat and choke him. All he could do was try to open his throat and allow the desecration of his virgin mouth to unfold as he watched in horror. Some men were laughing, some looking upon the scene in lust, and to his eternal shame, he began to give in to being used, just waiting for the man to have his fun and let him get back to serving drinks.

No such luck existed though, as the man suddenly grabbed a hold of Brett's head and forced his cock further down his throat as he let go of a guttural moan. The man pulled out after a few thrusts and began spurting stream after hot stream of salty cum onto his tongue, then he pushed his cock slowly back into the waiting mouth to force every drop of cum directly down his throat. He had to either swallow or choke to death, so he chose the former and gulped down each warm spurt of shame he knew he could never take back. After what seemed an eternity, Brett tried to catch his breath as the man pulled out of his mouth and left trails of sticky cum dripping from his lips.

Brett couldn't believe what was happening, but just as the first man had finished, there appeared three more men around him who picked him up and carried him to the sex swing mounted in the middle of the living room.

They clasped his wrists and ankles into the locking cuffs of the chair and effectively immobilized every bit of his remaining pride along with his ability to protest further. Then the man who had just seeded his throat with the load of cum he could still taste spoke up.

"Alright boys, lets show this little slut what she's gotten herself into tonight!"

With that, all 50-60 men rose almost in unison and made a close circle around him in the swing. Almost as if it were a ritual sacrifice, the men began brandishing their erections and slowly inched toward the swing.

Brett knew now there was no escaping his situation. He noticed the faint red light of several different cameras in the room and then noticed many of the men with cell phones out to film the event as well. The first group of men approached him as he sat helpless in the swing. One man removed the butt plug and tossed it aside as he spit on his hand and lubed his enormous cock. Two others approached from the sides and beckoned his mouth and hands. He was just getting used to the idea of sucking one man off when he was forced take another cock deep in his throat.

"Man this slut has some soft lips and a velvet throat," one man said.

"How is his ass?" one of the other men asked.

"Let's find out," the man with his cock poking his ass said as he plunged all 9" of himself deep inside Brett's tight asshole in one quick thrust.

"I think we've got ourselves a virgin here boys," the man exclaimed as he began to pound in and out of Brett's virgin hole.

Things quickly turned into a blur as Brett tried not to focus on the burning pain in his asshole and the knowledge he was about to be fucked like a real girly slut.

"Ruin that sissy pussy!" one of the other men cheered as his virtue was ripped away and all that was left was the realization that there was no turning back from this now. As soon as one man came in his mouth, there was another stepping up to take his place, and he had already lost count of how many men had spent themselves deep inside his ruined throbbing boy pussy.

He yelped each time a new man entered his cum filled ass and began pumping him like some two-cent whore, but as the cum dripped slowly down his face coating his entire chest and onto his lingerie, he began to feel a semblance of pleasure coursing through his core. The scent of the men's mingling cum entered his nostrils, and without warning, he was thrown into a frenzy of carnal lust. He threw his head back and took another waiting cock into his mouth and one in each hand as he surrendered to the newfound rush of becoming such an emasculated sissy slut. He would never recover from this, never be the same, never be a real man. It was too late for that, and he gave in.