The Transformation of Jesse

This is only the third story I have ever written so please only helpful criticism. I hope you enjoy.

Jesse was like every other guy he knew. He liked sports, hanging out with friends, getting drunk and the company of a good looking girl. He was a sophomore in college and constantly in the company of beautiful women, both in and out of the bedroom. He lived alone in his own apartment which made it very easy to bring home a cute piece of ass from the local bar or house party. As the number of girls coming and going increased, Jesse began to get bored with the typical sexcapades that took place in his life. He soon found himself searching the web for new and exciting thrills to get him off. He had never been interested in men, or so he thought, until a night of surfing the web set off a chain of events that would change his life forever.

“What is this?” Jesse thought as a pop-up appeared on his screen.

Jesse clicked on it and a window popped-up. There was a gorgeous girl wearing black thigh-high stalkings with a garter belt and thong. She had dark brown hair that fell over her chest and covered the nipples of her bare breasts. Intrigued, Jesse scrolled down. The next picture had her nipples exposed and her hips turned to the side showing off her beautiful curves.

“Damn, she’s hot!” Jesse thought as he continued to scroll down, eager to see the next pic.

The next pic revealed even more of her sultry body. Her long tan legs grasped tightly by the stalkings which ended at the cusp of her buttocks perfectly framing her beautiful ass in black lace. Jesse quickly removed his dick and began stroking. Pre-cum had already seeped from his tip, lubing his fist as it moved up and down his shaft.

As the pictures continued this goddess of a woman began pulling down her panties. Soon she was bent over straight legged with her panties at her ankles exposing her hairless underside.

“What the fuck!?” Jesse said out loud as he saw a perfect ass and beautiful asshole seamlessly united with a hanging set of cock and balls.

Jesse instantly got an anxious feeling in his stomach and his heart started racing. His dick twitched is his hand and he got really excited. He had known that there were girls with penises, but had never ventured to look at any online. Now that it was in his face, he couldn’t help but look in awe at this beautiful woman with a gorgeous dick hanging between her legs. Jesse licked his lips as he continued to scroll down the screen seeing more of this girl exposed with each continuing picture. He was soon pumping his fist up and down on his member as he landed on the final picture. She had her legs spread wide, hand on her cock which had erupted and released a massive load of creamy cum that was running down the underside of her shaft, over her balls and onto her puckered asshole. Jesse could take no more and quickly followed suit, erupting deep from his balls with one of the most exhilarating orgasms he had ever given himself.

“Holy shit” Jesse muttered as his head finally stopped spinning and he regained composure.

Her sexy curves and erotic surprise continue to occupy his thoughts for the rest of the night and well into his dreams. He awoke the next morning with healthy dose of morning wood. He imagined her sexy body as he stroked his dick. He played through a scenario in his head where he had her in his bed enjoying all of sexy curves and eventually her hardened prick. New desires began to form is his mind and he was soon imagining her dick, glistening in the light as it slid between his eager lips. His mouth started salivating as he thought of her swollen head slide past his lips and down his throat. It was the single thought that brought his morning session to and early conclusion and some sticky sheets.

He arose from bed and wearily made his way to the bathroom.

“Did I really just cum to the thought of sucking a cock?” Jesse thought to himself.

He walked into the bathroom and stood in front of the mirror.

“How is it possible that a guy can look so much like a girl? And a fucking gorgeous girl at that!?” he thought.

As he stood there looking at his naked body in the mirror he began to inspect himself. He wasn’t a buff guy, with big broad shoulders or beefy thighs. He had a flat tummy but no real muscle definition. His arms and legs were long and slender while his butt was plump and perky.

“Kinda like a girl” he thought.

He ran his finger tips from his chest down his stomach ending at his limp dick. It wasn’t a huge piece and his balls were rather small and held tight to his body, almost like they had never dropped. He ran his open hand from his groin over his prick and and balls pushing them down between his thighs. He tucked them back and brought his thighs together to keep them in place. He looked himself over and thought:

“Fuck, I could probably look like that, minus the tits of course”

The longer he stood in front of the mirror the longer the thought ripened in his mind.

“First, this hair would have to go”

Jesse wasn’t a hairy guy. His chest, back, stomach and ass were hairless to begin with, but his face, groin, cock, balls and asshole were a little furry. With a nervous pit of excitement in his stomach, he grabbed his razor and shaving cream from the counter and began lathering himself up. He drew the razor down the shaft of his cock starting from the tip and working his way to the base. He then worked his balls with the razor until all the hair was removed and they were as soft as the day he was born. He grabbed a hand mirror from his vanity and placed it on the floor. He squatted down over it and for the first time saw his own asshole. He lathered it up with the shaving cream and slowly moved to razor between his cheeks, removing all the hair and careful not to cut himself. Once done he gazed at his perfect little hole in the mirror and lightly ran his finger tips over his opening. His body shuddered as pleasure raced through his body and the pit is in stomach dissipated for a split second.

“Well, now I know how to cure that anxious feeling” he thought to himself.

He stood up and examined the last bit of hair left on his body, the bushy little patch that sat above his member. He imagined all the girls he had been with and tried to think of what he had enjoyed the most.

“I don’t like the Amazonian jungle look” he thought.

So he took his beard trimmer and thinned it out.

“Still too much” he thought to himself.

So he spread on some shaving cream and shaved off the sides at an angle. Now it looked like an arrow pointing right down to his hairless prick.

“Perfect!” he thought.

He ran his fingers over his now hairless underside and loved the way it felt. The feeling of his hairless ass how his cheeks touched skin to skin with nothing to obstruct the contact and the way his balls seemed to have a million more nerve endings running through them, was overwhelming.

“No wonder girls keep their pussies hairless, this feels amazing” he thought.

It was at that point that he remembered that he had a g-string that his last fling had forgotten in his bedroom. He quickly raced to his room and found them sitting on his dresser. He picked them up and smelled the sweet aroma of her pussy as he brought them to his nose. Once more his heart started racing and he lowered them down to his shins and stepped though them. He slowly pulled them up, enjoying the feeling of the lace material as it tickled his skin. As he brought them to his waist the string slipped between his hairless cheeks and nestled right up against his puckered asshole. He ran his thumbs down the sides of the front and spread the material over his dick and balls. He spread his thighs and pressed his manhood between his legs, tucking them back and hiding them from view. He turned to look in the mirror and loved what he saw. His idol hands uncontrollably ran over his stomach and back to his ass. They cupped his cheeks and squeezed them, spreading them apart and seating the string even closer to his hole. His mind went wild and his cock swelled, popping out from between his thighs and pressing firmly against the fabric begging to break loose.

Full of excitement, Jesse ran to his computer and found a video of a sexy shemale making love to hung stud until both her and her suitor climaxed in ecstasy. Jesse stroked his raging hard on, tugging at the thong, grinding the string tight against his body until he finally came to orgasm. As his body tensed and balls clenched, the thong snapped and Jesse released a hot stream of cum from his swollen tip. He lay there, panting heavily, head spinning and then he realized what he had done.

“Oh no!” he muttered. “What have I done?”

Jesse’s heart sank as he realized he had just destroyed a new source of desire and excitement. He then realized that he could just buy a new pair online.

He found a website he had seen on TV, “Adam & Eve”. He searched the site to find a new pair of panties. He scrolled through the options and soon realized he could get an entire outfit, not just panties. He clicked through page upon page selecting items for his cart. He went to the checkout and realized he had over 15 items. There were thongs, stalkings, bras, garter belts, fake implants, skirts, blouses, dresses, tube tops, even a wig and a set of panties that had a tether that allowed him to properly secure his dick between his legs. His heart was racing with excitement as he imagined himself wearing all these items. He quickly ordered them and put a rush on the delivery.

Jesse was distraught with anticipation as he tried to go about his daily routine, having drinks with his buddies and continuing with his studies. Finally the day came when his much anticipated package was finally supposed to arrive. He skipped school and even shut off his phone so nobody could interrupt his special day. He sat on the couch waiting for his package to arrive when the doorbell finally rang. He ran to the door and quickly opened it to find a young delivery man standing in his doorway. He was tall and cute. Even under his brown uniform you could tell he had a nice body. His shoulders were broad and his arms were big, filling the sleeves of his shirt.

“I have a package for the lady of the house” the young delivery man said.

“I’m the only one who lives here” Jesse replied.

The delivery man smirked and gave Jesse a once over from head to toe.

“Oh” he said “The package accidentally broke open during delivery here, but I checked the packing slip and made sure it was all still there, so you should be good to go”

Jesse’s face went pale once he realized the extent of the situation. The young man handed Jesse the package and said:

“Should look cute on you, I think I like the mini-skirt and blouse the best”

Jesse just stood there in complete shock as the delivery man winked at him and walked away.

“OH NO, OH NO, OH NO, OH NO!!!” Jesse stammered as he closed the door behind him.

“Wait, did he just say what I think he said” Jesse thought.

He raced to the window and peeled back the shades to see the delivery man walking to his truck. The man looked up before he got in and smiled. Jesse quickly hopped back from the window hoping he hadn’t been seen. He ran to the box and examined it before opening it. The items were in disarray and the package had clearly been opened.

“Shit!!” Jesse said as he thought to himself “What am I gonna do? He knows what was in there! Why did I say I live alone!?”

Then Jesse’s mind went back to what the man had said, “Should look cute on you”.

“Was he coming on to me?” Jesse thought.

His mind was racing with worry, but his excitement for the package was enough to block the thought from his head, for now.
He pulled each item from the box and unwrapped them all, placing them neatly on display so he could examine each one.