It's All About Reputation

The three friends sat around Jim’s living room. The three amigos’, as they called themselves, were as unlikely a group of friends that can be imagined.

There was Paul, the son the town’s richest man. He was a freshman at the state university, and had pledged at his father’s old fraternity. He drove a brand-new BMW and had a wardrobe right out of Brooks Brothers. Despite all his advantages in life he was the epitome of the term geek, all the money in the world would never change that. All through school he spent his Friday and Saturday nights studying. He took every advanced course his school offered. He graduated as class Valedictorian. All this was done at the sacrifice of a social life. After four years of high school, he had never even had a date. His only friends were Jim and Kate. they were really tight out of necessity as the group had been rejected by every clique in the school.

Then there was Jim, academically the exact opposite. There was never a school book he liked. It was only through Paul’s help he got through school. His family lived from one welfare check to the next. Out of necessity he had an after-school job, the only one a lad his size could get was at the town’s only boutique, where he was the janitor and handyman. He was a petite young man, who had grown up with the stigma of being the smallest boy in his class. As a young adult, he topped out at only 5’ 4’’ and weighed only 120 pounds. Surprisingly, he didn’t mind it at all.

Then there was Kate, a woman known for her Rubenesque figure. As a result of her experience with her father, she had never shown any interest in acquiring boyfriends. She was turned off of men in general being a product of a broken home with an abusive father. That and the fact she had been carrying a torch for Paul since she reached puberty.

Her face was pockmarked with acne scars, makeup could easily cover, yet she showed no interest in her appearance. Her blonde hair was long and unkempt and always looked like it needed to be washed, so the other boys made a point of staying away from her like she had the plague.

She was also Jim’s protector during school. During elementary school, she had pounded more than one unsuspected boy for picking on her friend. Today she was the same height as Jim but outweighed him buy a good 50 pounds. She was also stronger than her two friends.

@ @ @ @

Kate had always been the leader of their small group so it was no surprise she was the one to bring up the reason for their gathering, “Alright Paul, tell us why you called us all together.”

Paul swallowed twice then explained his problem. “My father picked my university, his alma mater, as well as my major. Business Administration. He insisted I join his fraternity. He said the contacts I make will serve me long after I graduate.

"I pledged the fraternity, but was accepted only because I am a legacy. I am afraid they aren’t my kind of people, I don’t fit in. I am not a typical Alpha Delta Omega. This chapter consisted of jocks, mixed in with serious students, combined with a good mix of races and creeds. The one thing they all have in common is that they are ‘players’ with the ladies. It has been made clear to me I have to prove I fit into that crowd.”

Jim, was curious, “How can we help you?”

“I need to show up with a girlfriend, not just any girl, she has to be hot. A real looker.”

Kate snickered, “Well that leaves me out! I don’t even know any girls like that. I bet there are some ‘ladies’ you can hire for a night, or even the hour.”

“No! I thought about hiring a professional escort, but there is a chance she might be recognized as a working girl by one of the other guys. That would get me blackballed. I need your help to come up with an alternative.”

There was almost 20 minutes of silence as everyone was racking their brains for a solution. They all knew how important this was to Paul.

Finally, Jim made a life altering decision, and spoke up, “I have an idea, but it is really an out of the box solution. Are you ready for something way out there?”

“Sure, I’m open to anything at this stage.”

Jim picked out a movie ‘Tootsie’ and slipped it into the player. “Alright, guys don’t go anywhere I’ll be back as soon as I can with my solution.”

Kate and Paul sat back and watched the movie and waited for Jim’s return.

The ending credits were running when there was a knock on the door.

“Who is it?” Paul hollered.

“It’s me Jim.”

“Well, come in the doors open.”

The door swung open and they turned to see what Jim had brought. In unison, both of their jaws dropped.

There was no sign of their friend Jim. Instead, a young busty redhead woman with dramatic makeup wearing a figure-hugging black dress and 5’’ stilettos walked through the door.

The stranger spoke, in Jim’s voice, “Well what do you think? I could be your date I have been told I make a very pretty woman?”

It took Paul a few minutes to get over his astonishment. “Jim is that really you?”

“Actually, this is Jasmine, Jim’s alter ego. Sorry I have kept this from you two, there was never a right time, until now to introduce you guys to her. I have been dressing as a woman since I was 12.”

Kate jumped up and circled her friend looking for possible problems.

“You know Paul, Jim does make a believable woman, not quite the gorgeous babe you need. I think with a few modifications like a professional makeover he might fill the bill.”

“Jim, how is your feminine voice?”

“Sorry, I have tried but never had any success sounding like a lady. If you take me as your date, I will just have to keep my mouth shut.”

Kate sat back down and rubbed her chin. “Paul your goal is to convince your Neanderthal fraternity brothers that you are the second coming of Casanova. Right?”

“Exactly!”

“I have a plan that will work, it will be expensive is that alright?”

Paul handed her his credit card and said, “Spend whatever is necessary.”

@ @ @ @

THE PLAN

Two weeks later, the Omega’s were having a small party and all the pledges were told to bring an appropriate date. Chauvinistically, the pledges would be judged by the quality of their companions.

Jim had just left the transformation studio. His makeup was dramatic and appropriate for a formal evening, his wig styled and combed out so soft curls rested on his bare shoulders. His eyebrows had been plucked to almost extinction. Jim, looking at his reflection, couldn’t believe such a thing could make such a dramatic change in his appearance.

Kate had gone all out and bought a breastplate that gave Jasmine a fantastic feminine shape. Combined with his lowcut dress, it displayed an almost indecent amount of cleavage, even an in-depth inspection would show Jasmine to be all woman.

Kate had found the perfect jewelry to compliment his outfit. A few bangle bracelets, dangling earrings, a feminine watch, a chocker neckless that matched his earrings. In her opinion he looked like a fashion model.

As Jim walked to the door, the tight skirt forced him to take mincing steps. His realistic breasts moved as if they had a mind of their own.

He turned to Kate, “Honey, don’t you think the G cup is a bit too much? They sure are heavy and even this bra doesn’t seem capable of controlling them.”

“Nonsense, they are perfect for the part you’ll be playing tonight. They are the most realistic faux boobs on the market. Come on Jasmine. We have to get you home. Paul will be picking you up in only a few minutes. I can’t wait to see what he thinks of his arm candy for the night.”

Paul was right on time. Kate answered the door and invited him in and called out, “Jasmine, your date's here!”

As she walked into the room. Paul’s eyes bulged out. He couldn’t believe the vision before him. Was this vision of beauty really his lifelong buddy Jim?

“Jasmine, if you are ready to leave your coach awaits you.”

“Let me grab my purse, then we can go.”

Paul turned to Kate, “I’ll have the window in my room open and waiting for you at 10.”

“Okay, I’ll be there. Have fun you two lovebirds.”

The car pulled up to the front of the fraternity house. Even from the street, they could hear the music blaring. Paul offered Jasmine his arm and walked her to the front door. He opened it and allowed his date to go first. Paul watched with amazement as Jasmine walked, his butt swishing from side to side as if he had been walking in heels his entire life.

As they entered, it seemed like all eyes turned to evaluate the newcomers. It was obvious that Jasmine had made a good first impression. A half a dozen young men rushed to offer Jasmine a drink. The two mingled and found a seat in the back room. They sat on the settee. Jasmine snuggled up close to her date. Paul put his arm around her shoulder and pulled her close to him. The music was so loud that conversation was impossible, which suited Jim just fine, he still hadn’t mastered a feminine tenor to his voice. The two just sat there sipping their cocktails that seemed to magically appear every time their cups emptied.

At 9:50, Paul took Jasmine’s hand and led her to his first-floor room. They entered, with all eyes on them. Paul insisted Jasmine take off her bra, which he hung on the outside doorknob of his door. The universally accepted single some hanky-panky was going on in the room.

Paul opened his window and helped Kate climb through. The three settled down and waited for the party to settle down, before they could put the rest of their plan into action.

Around midnight the house was quiet. Paul pushed his bed so the headboard touched the wall.

He climbed on the bed and starting to hump like he was making love. The headboard was banging against the wall in the rhythm of vigorous intercourse. Kat went to the wall and started in on her part. As the bed banged against the wall, Kate went into her best Meg Ryan impression from ‘When Harry Met Sally.’

She was screaming it until she was hoarse. Everyone in the house had to have heard. Some must have thought there was a revival meeting going on with all the “My god, sweet Jesus, Glory be!” Being tossed around.

Kate left no doubt that her fucking was the best she ever had. She yelled Paul’s name and said such things as, “You are a total stud with the largest cock in the northern hemisphere.”

Paul waited about 15 minutes and went back to the living room to find it full of stunned partygoers.

“Sorry to disturb you folks, I just came out to get a bottle, I need to replenish my fluids for round two.”

With the bottle in hand, Paul returned and passed it around. Kate took several long pulls on the bottle to help built her nerve for what she hoped to do. She stripped her clothes off and climbed on the bed with her ass facing away from the wall. She turned to Paul looking over her shoddier, “Come on Paul, let’s get act two started.”

Paul was surprised, “But you are on the bed.”

“I know, no acting this time. I want to be a full participant.”

“Are you sure?”

“Get your ass up here, I am positive. I have never wanted anything more in my life.”

Paul hopped up and crawled toward his target, his erect penis pointing the way. With great trepidation, he eventually achieved a successful docking with her sopping pussy. It was the most glorious thing he had ever felt. He humped away to joyous cries of Kate. This time, his own sounds were added to the interesting harmonic content of ecstasy coming from the two lovers.

The two lovers lost their virginity together and verbally celebrated. The walls reverberated from their cries. Jim sat off in the corner with total lack of inhibition he frantically masturbated watching the show. The two lovers eventually collapsed in exhaustion and laid together.

About an hour later Kate realized she would have to sneak out before it got light. She decided there was just time for one more act. She woke up her partner, “Get up sleepyhead.”

She got up and in a loud voice announced, “What you want to go again? Alright sexy show me what you got. Wait a minute, you are at the wrong hole. You animal, you want to fuck my ass? You are so big you will rip me apart.”

That started another round of oh no’s that changed to oh, yeses. That culminated in a screaming faux climax. At the end, a satisfied Kate climbed back out the window and headed home for a well-deserved rest.

Back in the bedroom, a sleepy Paul woke up with a glorious feeling emanating from his crotch. Looking down he saw the head of Jasmine bobbing up and down in his groin.

He reached down and with his hands on each side of her head he stopped the blowjob.

“Jim what are you doing?”

“If you have to ask, I must be doing something wrong. Don’t you like it?”

“Oh god yes, it is unbelievable.”

“Then let me get back to it. I have spent the night watching you and Kate having all the fun. Now it’s my turn.”

With that, Jasmine went back to her task. Now it was Paul’s turn to be vocal, his moans only served to spur Jasmine on. Eventually she was rewarded with a mouthful of Paul’s, manly essence. She swallowed it with a sense of satisfaction.

It was time to go, Paul got up and got dressed. He handed Jasmine her dress which she rejected.

She put on her panties, stockings and heels, the asked Paul for one of his dress shirts. She put that on and only secured one button down low, leaving her massive breasts free. It was just long enough to cover her panties. A brush threw her hair and a coat of lipstick from her purse and she led Paul out of the room for her walk of shame.

What she got was a standing ovation as the two made their way to Paul’s car.

Paul drove Jim to his apartment. Their timing was unfortunate, the area was swarming with students moving between classes. They were stopped at a stoplight surrounded by gawking students. Jasmine decided to have a little fun, she laid her head into Paul’s lap, then bobbed her head up and down, simulating oral sex. As her eyes cleared the side window, she noticed they had acquired a significant audience. The light changed and the car behind them was honking its horn.

EPILOGUE

After that night, Jim took it upon himself to work with Kate and taught her how to be a woman. Through diet, exercise, and makeup lessons, Kate was ready for her unveiling by the time of the fraternity’s Christmas dance. Jasmine took her to her beauty salon for a full makeover. With the aid of some serious shaping articles and strategic padding, Kate was turned into a hottie. Paul showed up at the dance with two beautiful women, one on each arm. It only elevated his reputation.

During the next two years, Jasmine kept turning up anytime there was a fancy celebration where Paul needed some eye candy. In between those times, the sexy Kate and Paul became an item.

Paul’s reputation as a lady’s man eventually propelled him to the fraternity presidency. Upon graduation, Paul took over his father’s company and he and Kate were married, with Jasmine as the maid of honor.