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. He then remembered what the delivery man had said, “I think I like the mini-skirt and blouse the best”. Jesse picked up the black skirt and placed it on the floor with the blouse right above it. He went through his new variety of under garments and picked out a black lace bra, placing it under the blouse and then placed the implants into the bra. Next he grabbed the matching black garter belt and thigh-high stalkings, placing them below the skirt. Finally he placed the thong with special tether underneath the skirt.
“Holy Shit” Jesse thought, “That does look good!”
He grabbed the clothes and ran into the bedroom. He started with the panties, slowly pulling them up to his waist and over his ass. He tied down the tether and tucked his package back between his legs. He tested them out by spreading his legs and shaking his ass a bit in the mirror.
“I look like Miley “fuckin” Cyrus” he chuckled to himself.
Next he stepped into the garter belt and pulled it up to his waist. It fit perfectly on his girlish hips. Next were the stalkings. He bunched them up as he had seen many of his girlfriends do and worked them side to side as he pulled them up his legs. Each inch they traveled up his legs his heart rate would increase. Once at the top the anti-slip band grasped his thigh just below the cusp of his ass cheek.
“Oh boy!” he thought “These almost feel too good!”.
Jesse’s cock tried to spring to action but was quickly denied when the tether tightened up and kept it right in place.
He ran the other stalking up his leg and stood to enjoy the view. Standing in the mirror he clipped the garter belt to the stalkings and admired his new look. He turned his hips and twisted his head to get a good view of his ass. Just as he had seen with the girl online, his ass was perfectly framed in black lace and looked absolutely perfect.
“How could you not want to fuck that?” he said to himself.
He moved back to his bed and picked up the mini-skirt. He stepped into it and shimmed as he pulled it up to his waist. Not wanting to ruin the surprise he continued with the rest of the outfit. He picked up the bra and clasped it behind his chest.
“This thing is so much easier to get off then on” he thought.
Next came the fake implants. He picked them up and played with them for a bit before sliding them into the cups of the bra. He looked down and gave them a squeeze. He couldn’t believe how real they felt. He picked up the blouse and put it on, buttoning it up and leaving the top 3 buttons undone to expose his newly acquired tits. The shirt was short enough that he didn’t need to tuck it in; it actually exposed his slender tummy and belly button.
Lastly was the wig. It was shorter dark hair much like his natural color. It ran down to his shoulders and was straight with bobbed ends.
Feeling complete, he moved in front of the mirror to admire himself. His mouth dropped, he couldn’t believe his transformation. There was no recognizing Jesse anymore; he had finally become “Jessica”.
He spent the rest of the night pleasuring himself and trying on each garment, looking for the perfect look. He soon realized that the delivery man was right, the mini skirt and blouse looked the best. His mind started to wonder if the young man was actually coming on to him? He decided to take a risky chance and test not only his looks, but his desires.
Jesse went back online and found a toy he thought he might enjoy. He added to the cart a bottle of anal lube with natural relaxers and the crown jewel; a 10” realistic dildo with balls. He quickly checked out and this time included “next day delivery”. Jesse had decided to answer the door as “Jessica” hoping this young stud would be the one to deliver his package.
Nervous and excited Jesse ran to the pharmacy to pick up a waxing kit and some light pink lipstick that “shimmered”. Once back in the safety of his apartment he went to the bathroom and sat on the toilet, reading the directions on how to wax himself. Luckily, Jesse’s hair had grown back enough that he could easily wax it off. For the next hour Jesse meticulously removed each hair from his underside. He then jumped in the shower with his razor and shaved his legs and face til they were smooth to the touch. He stepped out and dried off enjoying the look and feel of his girly figure. He grabbed a bottle of lotion and moisturized his entire body from head to toe. He put on one of his new thongs and curled up in bed, dreaming of the day he hoped would come in the morning.
Jessica was quick to rise, eager with anticipation, like a kid on Christmas morning excited to get his hands on a new toy. She slowly and methodically dressed herself in the outfit the delivery man had liked so much. Once dressed, she realized it was only noon and the package would likely not be there for a few hours. To calm the nerves, Jessica decided to make a drink. Feeling girly, she made herself a pink margarita, which quickly disappeared, so she made another. It had been two hours now and Jessica was 6 drinks in and feeling pretty tipsy.
“Just what I need to boost my confidence” she thought.
Time came and went and Jessica was realizing that the young man might not come today. “Next day delivery” doesn’t always mean what it says. She moved to the mirror to look herself over and pouted her lips when she realized she hadn’t put on her lipstick. She tip-toed to the bathroom and leaned over the sink, moving close to the mirror and exposing her breasts. She pulled the cap and slowly ran the lipstick over her lips. Just then, the doorbell rang. Jessica’s heart stopped and her stomach sank.
“Holy shit! This is it, now or never”
She swallowed hard as she moved towards the door.
“What if it’s not him? What if he laughs and tells everyone what I am?” her mind raced.
She took one final breath and opened the door.
Standing in front of her was the same young stud that had delivered her package just a day earlier.
“Hello” Jessica said as she battered her eyes.
“Oh, wow” the young man replied.
“I don’t think we met last time, my name is Jessica” she said.
“I’m Jake” he said with a sultry smile. “I have another package for you, and I’m sorry to say that this one accidentally broke open as well, but no worries, it’s all still there”.
“Oh, thank goodness! My night wouldn’t have been complete without it!” Jessica replied.
She couldn’t believe this was actually happening, she had taken to the role so well and he was actually smiling at her!
“I made sure to deliver this package last, just in case you wanted to discuss the recent mishandling of your deliveries” Jake said
“You know what? I do! Would you like to come in and we can talk about it?”
“I would be happy to” Jake said with a big grin on his face.
Jessica turned and walked away as Jake followed her, running his eyes up and down her body, fixated on her ass as it shifted with each step.
“Can I fix you a drink Jake?” Jessica said with a sweet voice.
“I’d like that” he said, “Thanks”.
Jake walked in and closed the door behind him, the bulge growing tight in his shorts with each step that moved him further into Jessica’s apartment.
“Is a margarita ok? I already have a batch made up” Jessica said as she seductively twisted around on her toes and stopped, popping her hips out to the side.
“That’d be great, don’t forget to salt the rim” Jake replied
“I can’t wait til you salt my rim” Jessica muttered to herself quietly.
“I heard that!” Jake quickly said.
Jessica turned slightly and gave Jake a little smirk with a sad puppy dog eyes. He didn’t need her to say anything, the look said it all.
Jessica turned back to making the drink, while Jake sat himself down on the couch adjusting the bulge in his pants so it would be easily noticed.
“She’s so fuckin hot!” Jake thought to himself “I can’t believe this is actually happening”.
Meanwhile, Jessica was pouring their drinks, thinking the same exact thing. Her body was tingling, thinking of Jake’s hands maneuvering over her curves. The nervous pit in her stomach had moved up into her chest and along her spine. She began imagining what his cock would look like and how it would feel inside her. The feelings moved from her chest down her body and dispersed throughout her underside. Her hairless prick began to swell and pull tight on the tether, her asshole began to relax and she felt like a little girl, getting wet between her legs.
“How’s it comin over there” Jake spoke up, breaking her trance and bringing her back to reality.
“All ready” she said, picking up the drinks and walking towards him.
She made her way to the couch and walked right up to him, putting herself between him and the coffee table. Jake followed her with his eyes and looked up to meet her gaze. He reached out for his drink, but she quickly turned around putting her ass right in front of his face. She straightened her legs and bent over at the waist. As she lowered her body to place the drinks on the table, her skirt rose up ever so slowly and inch by inch exposed her legs and then the top of her stalkings and straps from her garter belt.
Jake’s mouth began to water and his hands began to rise up. Jessica noticed, snapped back up and quickly sat on the couch a few feet from him. She knew she had him, now she was gonna play the game that she had been the victim of so many times before. She loved having this power over a man and she wasn’t going to give it up within the first couple of minutes.
“Now, let’s examine this package you brought me” she said, looking down at the obvious bulge in his pants.
Jake followed her eyes and looked down at his cock outlined beneath his shorts. They both looked back up at each other with a sexy smile.
“Not that one” Jessica said
“Oh, right!” Jake said with embarrassment.
“It’s ok honey, I’ll open that one later” Jessica said with a smile.
She didn’t even look at him for a response, she just took her hand and gently ran it over his shaft as she moved forward to get the package from the table.
Her heart skipped a beat as her hand moved along his member and over his swollen tip. She had just touched her first cock, and it was exhilarating, she couldn’t wait until it was freed from its fabric prison.
She picked up the packed and placed it on her lap. She slowly pulled to tape off, meticulously opening the package trying to build up Jake’s anticipation. The box opened and inside was the bottle of lube and life-like dildo she had ordered. A big smile grew across Jake’s face and he looked up at Jessica for a sign of approval.
“Well it all seems to be in order” Jessica said as she pulled the lube from the box.
“Easy Anal lube with natural relaxers for extended pleasure and wetness” she read from the bottle.
“I’m so wet right now, that last part may be unnecessary” She quipped.
Jake’s mouth dropped and he looked down for any sign of the truth that may be visible between her legs. Jessica saw what he was doing and jokingly slapped his arm.
“Easy does it big boy!” Jessica said with a smile, thoroughly enjoying how excited she was making him.
“Now, for the main item” she said as she reached into the box and pulled out the dildo.
She closely inspected the toy and turned the package around to read the description on the back.
“Big John, the most realistic dildo ever made. Featuring life-like veins and balls, equipped with suction cup for easy attachment to most surfaces. The closest thing to the real deal that money can buy.”
Jessica read the description aloud and pulled the toy from its package, running her hands over the shaft in a jerking motion.
“It feels pretty real” she said looking at Jake. “But I wouldn’t know, I’ve never had a real cock before” giving Jake a pouty look with saddened eyes.
Jake took this opportunity to play along and placed his hand under the box on her upper thigh.
“I’m sorry, I can’t imagine a sexy girl like you would have a problem finding a nice cock like that though?” Jake said with an apologetic tone.
Jessica’s heart was racing, her cock was straining against the tether, trying to break free from its restraints. Her eyes were dead locked with Jake’s, revealing her desires without ever saying a word.
“Well you know….” Jake said looking down at his bulge, “You still have another package to open”.
Jessica looked at his thigh and saw his cock twitch from beneath. She looked back up at him and bit her lower lip, trying to control her lustful urges. The longer she waited the stronger her desires and excitement grew, but she was ready to burst at the seams and couldn’t hold back any longer.
She threw the package on the table and tossed the items into it. Standing up quickly in front of Jake she bent over and put her hands on his thighs, placing one hand directly on his cock.
She gave him a serious yet seductive look and said:
“I’m still a virgin Jake, if I give myself to you will you treat me right?”
Jake reached up and placed her blushing cheeks in his hand and pulled her face towards his, placing a romantic and sexy kiss on her shimmering lips. The warm embrace lasted for what seemed to be eternity as he slowly pulled away and looked into her eyes.
“I’ll be good to you baby, I’ll take you places you have only dreamed of and be right here when you come on back” Jake said with true sincerity.
Jessica couldn’t believe what was happening, she wasn’t only ready to fuck this guy, she was ready to make sweet love to him and it was going to be as Jessica. She had finally found her calling and was ready to answer.
The anxiety in Jessica’s stomach had subsided and now it was pure desire. She gripped his thighs and spread his legs. She fell to her knees, never taking her eyes away from Jake’s. She slowly ran her hands up his legs until they found the buckle of his belt. Without skipping a beat she pulled it back and undid the hook. Following the belt’s release, she unsnapped his button and slowly began working the zipper further and further down.
Jake’s chest was rising and falling as his breaths got deeper and deeper, trying to remain conscious as Jessica’s hands worked closer and closer to his member.
Once the pants were fully released she grabbed them by the side and began shimmying them down his legs. Jake picked up his butt as Jessica pulled them down to his ankles and off of his feet. To this point she had still not left Jake’s beautiful blue eyes, but then, Jake’s cock flexed and quickly drew her lustful eyes.
She could not believe she was so close to fulfilling her desires. There was only a thin piece of tight Tommy Hilfiger fabric between her and this gorgeous man’s wondrous prick.
She ran her hands up and down Jake’s shaft, enjoying the massive girth and impressive length before breaking it loose from its prison.
Jake’s head fell back and his eyes rolled into his head. Jessica was not the only one amazed with what was taking place on this wonderful day.
She grabbed Jake’s boxers by the waist band and ever so slowly pulled them down revealing his body to her virgin eyes.
His bush was well trimmed, sitting below a tanned and well defined muscular abdomen. Jake was the premier specimen of a man and his scent, filled with testosterone wafted up into Jessica’s nose. The smells sent endorphins running through Jessica’s body and drove her craving to an all new high.
She pulled his boxers further down revealing the base of his cock. Just like his groin, it was well manicured and completely shaven. She stared at his swollen member, fixated on the features as she pulled his boxers further down. A large vein running up the top side of his shaft split into two and continued towards the tip. As Jessica neared the end, she saw the base of his massive head and was delighted to see had been neatly circumcised. As the boxers made their last advancement over his cock, it sprang up, like a diver reaching the surface, gasping for air.
Jessica froze, lost in herself and in complete awe as before her stood the most beautiful thing she had ever seen. It rose nearly 10 inches from its base and was as thick around as her wrist.
Jake looked down at her with a smile and said:
“Mind pulling those off the rest of the way?”
“Oh….yeah, sorry” Jessica laughed as she broke from her dazed state.
She hurriedly pulled his boxers the rest of the way off and brought herself face to face with Jake’s beautiful member.
“Don’t be afraid, you can touch it, take as much time as you need baby”
Jessica couldn’t think of even a noise to make let alone any words. She just reached out and placed her warm slender fingers around his shaft. The skin was soft and warm to the touch. The massive vein was pulsing beneath her grip. With a light touch, she moved her hand up and down his shaft, tantalizing the nerves along the way. She knew how to make a man feel good, after all, she did have personal experience.
As she reached the top on her second stroke, Jake’s cock throbbed and its massive head swelled nearly doubling in size. Jessica knew what was next and eagerly watched in anticipation as pre-cum emerged from the slit and pooled up on the tip. Jessica came up on her knees as she licked her lips. She spread her sexy lips and placed them on the tip of Jake’s swollen head. She slowly brought them together enjoying both the feeling and the taste of his beautiful member in her mouth. Having never tasted cum before, she swirled her tongue around spreading his milky seed to each of her taste buds. Just like his masculine scent had done, her heart raced and wondrous feelings surged through her body.
The sight of Jessica’s mouth grasping his cock sent a shudder though Jake’s body and he let out a deep groan. Jessica took this as a sign of approval and looked up at Jake:
“Oh….this is gonna be good” she said as they both laughed.
The laughter quickly subsided and desire took back over. Jessica came back up and positioned herself over Jake’s erect prick. She worked up some saliva and let it roll off her lips onto the tip of his dick. She brought her hand up and worked her fist up and down his shaft making it glisten in the light. She licked her lips one last time and took a deep breath.
“This is it” she thought to herself.
Mouth open and tongue out Jessica brought her eager mouth onto Jake’s cock. Fitting this beast of a dick into her mouth was surprisingly easier than she had imagined. The tip moved flawlessly into her mouth and towards her throat. Jake watched in complete awe as Jessica worked his cock up and down, deeper and deeper into her throat. She soon had him bottomed out in the back of her throat, but knew exactly what to do from watching her previous girlfriends. She took a deep breath through her nose and swallowed hard, sucking the head of Jake’s cock down her throat. Jake shuddered and let out another moan of approval.
“Holy fuckin shit!” he said nearly stuttering
Jessica, now full of confidence, continued to swallow his rock hard member down her throat. She pulled it out only to catch a breath and then quickly slid it right back into her mouth. Inch by inch she worked him down her throat until she finally had the entire thing down her esophagus and nearly in her stomach. Her nose pressed firmly into his pubic bone as her protruding tongue curled up and licked his hairless balls. She held his cock in place and swallowed repeatedly messaging his member with her throat.
Jake looked down at her in complete amazement and said in a loving voice:
“Oh baby, I can’t believe how good you are at this! You make me wanna cum SOOOO BAD!!”
Jessica quickly pulled his slobbery dick from her throat and licked her lips.
“You’re not cumming in my throat!” She snapped, “I wanna be able to taste it! And besides, your first load is always the biggest, and I have a special place for that”
With those sexy words and her lustful smile, Jessica stood up and turned her back to Jake.
“Can you take my panties off for me baby? My head is spinning and I can’t think straight.” She said
She actually could think straight and knew exactly what she was doing. She knew the longer she kept his balls from releasing, the bigger and more powerful Jake’s orgasm would be, which directly correlated with one thing; more cum.
Jake moved himself the edge of the couch to get a close up view of Jessica’s perfect, perky ass. He ran his finger tips up the side of her thighs and underneath her skirt. He grabbed her thong and slowly pulled them down over her supple ass cheeks, careful not to ruin the surprise and expose them to his eager eyes quite yet. As he reached the mid thigh, he saw the tether that was restraining her cock. He gently removed it freeing her hairless prick and exposing a generous amount of cum that had been seeping from her tip and pooling in her panties and invading her ass cheeks.
“You’re so wet baby!” he said with amazement.
Jessica couldn’t answer, now her head really was spinning. Jake removed the panties from her legs and she stepped out of them, spreading her feet apart to expose herself to him just a little more.
Jake reached up and put pressure on the flat of her back with the palm of his hand, motioning for her to bend forward. His hands moved to her hips as his eyes worked their way up her slender legs to her beautiful ass. He shook his head in disbelief.
“I can’t believe this is actually happening to me” he thought to himself.
Biting his lower lip, Jake began caressing her bottom and kneading her ass enjoying its firmness and perky stature. Sliding a few fingers under her skirt, Jake worked his hands upward revealing the pale flawless skin of the most perfect ass he had ever laid his eyes on.
His mouth started to water as he brought his lips in and sensually kissed each cheek. His hands massaging her hips and his thumbs placed at the crease of her buttocks, Jake moved his lips back and forth kissing her bottom and driving her absolutely crazy.
Jake’s hands moved from Jessica’s hips and cupped her bottom. He squeezed her cheeks and spread them apart revealing the source of his soon to be orgasm.
Exposed and feeling Jake’s hot breath on her tight hole, Jessica’s heart was racing with anticipation of a wet kiss. She put her hands on the table and arched her back, perking her ass up into his face for a better view of her underside.
Jake took this as a hint and placed his pouting lips on her tender asshole with a wet kiss.
Jessica’s body shuddered and it was her this time that let out a moan of approval. Jake continued to kiss her eager asshole, swirling his tongue over her opening and sending lightning bolts down her body. To this point, Jessica had only tickled herself with her finger and could have never of imagined how spectacular this feeling could have been.
Kiss after kiss Jake continued to make out with her ass, eventually working his tongue into her hole as it finally relaxed. Jake knew she was ready and he needed not tell her that.
Once she felt his tongue slide into her opening, she knew she was ready for the rest of him.
Jessica stood up and turned around. Mouth hanging open and eyes glazed over, she opened her hands revealing the bottle of the newly acquired lubrication.
“I need you inside me” she said with a sense of urgency
Before Jake could say a word, Jessica had the top popped open and a steady stream of lube running over Jake’s cock and down his shaft. She threw the bottle on the couch and took his member in her hand, working her fist up and down covering every inch in a thick coat of slippery delight.
Jake’s body shuddered as her hands made their way to his balls, swirling her finger tips and massaging that sweet spot between his asshole and his sack.
“Fuck! For a virgin you’re awful good at this” Jake said
“I just know how to please a man” Jessica replied and winked.
She turned around and grabbed both their drinks in her hands. Thinking she was going to give him one, Jake was surprised to see her quickly down both drinks before slamming the glasses on the table.
Jake looked on in shock as Jessica said:
“If I’m gonna handle that” pointing to his cock, “I’m gonna need all the help I can get”
Without any hesitation Jessica pushed Jake’s body back against the couch. She reached forward and weaved her fingers between the buttons of his shirt. Jake looked down just in time to see her rip his shirt open like a wild animal. She admired his tan pecks and flawless body before leaning in and taking his nipple into her mouth. Sudden, but sexy, she twirled her tongue around his nipple and finished with a nibble before standing back up.
Wanting to be funny, Jake reach forward and grabbed Jessica’s shirt, ripping it open and exposing her black lace bra. She only smiled at him and pulled it off, throwing it to the floor. She grabbed her skirt and squirmed out of it, shaking her hips from side to side being as sexy as she could, which was incredibly so. Jessica now stood there, her long slender legs grasped only by her stalkings, held up by her garter belt.
Jake looked over her hairless prick and smooth balls enhanced by the perfectly shaped patch of hair which conveniently pointed right to her tiny cock. He reached forward to take her erect member in his mouth, but she stopped him with a hand on his head before he could indulge himself.
“This night is going to be a long one baby, you can save that little treat for later” she said to him.
Disappointed, but still excited, Jake leaned back on the couch and motioned for his beautiful new girl to come to him.
Jessica bit her lip and her eyes grew big as she moved towards Jake and straddled his lap. She reached back and pressed his lubed cock between her soaking wet cheeks. She slowly worked her hips, running the tip of Jake’s dick over her wanting opening.
Jake’s left hand moved to her ass and cupped her bottom, squeezing her cheek and spreading them apart. His right hand moved to her tiny breast and massaged it as Jessica rocked her hips over his raging cock. They both began to moan in sweet harmony as Jessica placed her left hand over Jake’s right hand and stared into each other’s eyes with a deep passion.
Not being able to take it any longer, Jessica brought her hips up and positioned Jake’s swollen tip at her opening. Jessica took a deep breath and then slowly released it as she relaxed her muscles and let Jake slide inside of her perfect little ass.
As the tip penetrated her opening her eyes widened and so did Jake’s as he felt her warm insides grasp his throbbing cock. As his massive head made its way past her tight hole, it popped into her velvety insides pulling in the top of his shaft.
Jessica yelped in pain and clenched down on him, nearly sending Jake into orgasm.
“Easy baby” Jake said holding her firm to keep himself from cumming.
“The first time always hurts. Just try and relax” Jake tried to calm her.
He brought his left hand to her hip to keep her from moving and moved his right hand to her neck, pulling her head down to his chest.
Jessica rested her head on his warm chest and listened to his heart beat. She focused on the beats and as his heart slowed, her body began to relax. Her pulled her head up and looked into her eyes.
“It’s okay baby, I’m not going anywhere, just relax” he said while looking right into her beautiful eyes.
Jessica realized they weren’t actually fucking, they were making love. With that sweet realization Jessica’s body fully relaxed and her hips came down to meet Jake’s massive thighs. His wet cock slid into her luscious ass and rested with his balls snuggling tightly between her cheeks.
Jessica’s body was in complete shock from the massive rush of endorphins flowing through her body. Her eyes had never left Jake’s and she only broke their gaze to close them and lean forward for a kiss. Her supple lips met his and she wrapped her arms around his neck holding him close while they embraced each other’s body. As their tongues intertwined in one another’s mouth, Jessica’s hips rose and fell sliding her asshole along Jake’s glistening shaft.
With each pass, Jessica could feel his swollen head massaging her g-spot and milking her tiny prick from the inside. Stroke after stroke forced cum from her slit, dispensing it between her tummy and Jake’s rock hard abs.
Soon, her balls had produced a large collection of cum between her and Jake, lubricating her prick as it slid over Jake’s abs. Just like she had seen in so many movies, Jessica arched her back and extended her ass, working it up and down, back and forth over Jake’s shaft.
Jake placed his hands on her back and pressed his fingers along her spine running them down towards her ass in unison. Jessica threw her head back, still holding on around his neck, as Jake’s hands moved past the small of her back and down between her cheeks. They ran over her sopping wet opening before circling out and firmly grasping her ass. Jake gripped her as best he could with all the lube covering each cheek. Placing his fingers right at her opening, Jake squeezed and peeled her ass open like a juicy orange.
Jessica spoke for the first time since before Jake’s intrusion:
“Oh baaaaaaby, you treat me so good” she said looking deep into his eyes.
“I want it, baby. I need you to cum for me” Jessica said to her new lover.
“Will you cum with me?” she asked
Jake didn’t reply, he just looked back into her eyes and nodded.
He slowly repositioned himself on the couch, leaning forward closer to her body. He took his left hand and wrapped it around her back, grasping her side, right below her breast. His right hand crossed her ass and grabbed the opposite cheek, squeezing it firmly.
Jessica wrapped her arms tightly around Jake’s neck, pulling his head tight against her chest. Their bodies were now one. Jake’s breathing became deeper, Jessica feeling his chest rise and fall against her body. She arched her back as they both tightened their grip on one another. Then, as if a starting gun had just gone off, Jake’s body exploded into rhythm. With Jessica’s ass in the air, Jake thrust his hips into her, driving his cock deep into her wanting ass. His balls, covered in lube and sweet juices from her opening, slapped against her body creating an intoxicating sound of wondrous love making.
Jake’s cock, now frantically milking the insides of Jessica’s ass, was swelling up with an imminent orgasm. Jessica had finally reached the precipice of her desires and came to the most immaculate orgasm of her life. Her balls tensed and her asshole clenched Jake’s cock. As her body release stream after hot stream of cum between their sweaty bodies, her asshole pulsated around her lover’s shaft.
“I’m fuckin cumming baby” Jessica whimpered between breaths
Jake soon followed and his cock swelled, filling her ass with his throbbing member. Jessica felt the pressure building inside him and clenched her asshole harder around him. With one final thrust Jake erupted. His muscles tightened gripping Jessica’s body with immense force. Like a sexual geyser his cock spewed load upon load of steaming cum into her tight little fuck hole. Jake’s hot cream filled every nook of velvety cavern, coating her insides like a semen enema.
The feeling was euphoric for Jessica. They’re bodies intertwined with one another’s, covered in sweat and sharing this miraculous moment. Jessica’s brain released another massive rush of endorphins which flooded her senses and sent her back over the edge. As she collapsed in complete paralysis, her body convulsed with an uninhibited orgasm releasing more of her sexual seed onto Jake’s body.
Unable to move or speak, Jessica and Jake laid in each other’s arms.
“Oh….my….god….” Jake said between each gasp of air. “You alright baby?”
She only managed to say, “uuuuuggggghhhh…….uh huh…..”
They both chuckled as they knew they had just experienced the event of a lifetime.
Even with her body in a weakened state, Jessica knew she still wanted more. She clenched her asshole around Jake’s cock as she pulled her hips off of his lap. Their bodies were sticky with cum and sweat which clung to them like glue as they separated.
“What are you doing baby?” Jake asked
“I wanna see what love tastes like” she said as she looked up at him with sweet eyes
Jake only smiled as he knew she was right, “love” was the perfect word to describe what they just made.
Jessica tried to stand, but her knees just shook and she fell to floor between Jake’s legs. She placed her head every so sexily on his thigh, admiring her first cock and source of her best orgasm. Her finger tips ran up and down his cock, causing Jake to shudder when she brushed over his tip. She simply looked up at him and giggled.
“I fuckin love this girl” Jake thought to himself.
Jessica took his limp, but still semi-erect, cock in her hand and brought it to her face. She puckered her lips and gave it a kiss.
“Thank you Mr. Cock for the best sex a girl could ask for” Jessica said holding his dick close to her lips almost to whisper in its ear.
Jessica embraced Jake’s cum covered member in another kiss right below his sensitive head on the underside of his shaft. She continued to follow each kiss with another as she worked her way down towards his achy balls. With a light suck, she pulled his sack into her mouth and gently massaged his balls with her tongue. Enjoying not only the taste of his cum, but her ass as well, Jessica dragged her tongue up his shaft repeatedly, removing every drop of semen from his now flaccid member.
Jessica gave Jake a dirty look and he said to her:
“There’s a lot more of that still inside you”
“Oh I know, it feels so good inside me that I don’t wanna let it leave….kinda like you” she replied and winked.
Jake laughed as Jessica finally stood, just barely able to keep herself upright. She fell back into Jake’s arms and their lips met again for a passionate kiss. Their tongues swirled the wonderful flavors across their taste-buds. The kiss ended with a wet smack and they looked at each other in complete bliss. They both knew this day would be the start of many more to come.
If there are any good reviews I would be happy to continue, many more themes as well. Any lustful fantasies are always helpful for the creative mind. I hope you liked it as much as I did.