[TG] Becoming Jessica (Patreon)

Commissioned by Jessicatg24

Sick of striking out, Jason decides to try a drug that can turn him into a woman and experience sex from a new perspective and learns a few things about himself along the way.

~

Jason looked at the tiny message at the bottom of his phone screen.

‘Tanya521 has blocked you’

She was the fourth girl this month and it was only the 15th. As usual he scrolled through the previous messages, looking for something he said or did wrong and once again found nothing. With a scoff he chucked his phone down on the bed with a huff; women always said they wanted confidence but when he took charge he was ‘a creep’ and ‘too forceful’. Yet when he took things slow everything would fizzle out over the course of a week and the woman would use one of those lines like ;'we're just not right for each other’ or ‘you’re not confident enough’. He couldn’t win.

Frustrated he opened yet another beer; toasting the air to another Friday night spent alone with nothing but his hand to keep him company.

Was it so wrong to want to get a bit of tail now and then? It wasn’t like he was demanding anything much, no relationship, no extra strings. Yet no matter what he tried; from picking girls up at bars to Tinder to speed dating events, nothing worked. It had been months since he’d last had sex, and it hadn’t been great if he was honest. A drunken hook up at an old college mate's party. He’d been so sloshed he barely remembered it and he couldn't shake the feeling the only reason it happened was because his partner was in a similar state.

As much as he didn't want to admit it, perhaps he was just bad in bed? After a few minutes of frustration and feeling sorry for himself he flopped down on the bed and grabbed his phone again, closing the dating app and opening up google. Searching ‘how to have better sex’ made him feel even more pathetic but what else could he do?

He found all the usual advice, all the shit he already knew. Don’t skip foreplay, communicate, find the G-spot. Nothing even remotely useful. He started to dig deeper, reading through forum posts made by guys like him who were struggling to pick up. A lot of them actually made him feel better; even he wasn't quite as pathetic as the forty year old virgins and incels of the internet.

Then he saw a post that caught his eye; ‘understanding the female body gives you the best sex in the world!’

‘Bimbathryone gave me the best sex I have ever had. Seriously guys, it’s worth braving the dark web just to try it!’

“Bimbathyrone?” He mumbled, Jason had never tried drugs before but he had heard tales of sex on ecstasy and the likes.

The more he researched the drug the wider he felt his eyes grow. It seemed to have all sorts of effects depending on the dosage and who took it. Some women reported their sex drive going through the roof after taking it.

‘I had three guys in a single night and I still wasn’t satisfied!’

Men had some…different effects but they couldn’t possibly be true. Actually becoming a woman? That couldn’t possibly be real. Still, enough guys reported the same hallucination so there must have been something hormonal going on.

‘I don’t even need a woman anymore, just my hand. Bimbathryone orgasms are just the best!’

Jason’s stomach churned. He was actually tempted. He was sick of wanking by himself but if this could make it more enjoyable maybe he could get some actual satisfaction even if he couldn’t get a woman’s attention. If these rumours were true and it really did turn men into women…perhaps it could be worth it. A little experiment and it wasn’t as if anybody would know it was him. He could finally get laid and nobody would think any less of him for losing his masculinity. They were illegal though, the fact that he had to order them off the dark web alone should have warned him off.

He looked back at his phone, picturing the rejection messages in his mind. Horny and slightly drunk was a dangerous mix.

“Fuck it.” He sighed, getting to his feet and heading over to his computer; if anything it might make a good story.

~

Jason had to admit, there was a certain amount of thrill that came from ordering illicit drugs. He'd never been much of a rule breaker but here he was, waiting for his dark web order to arrive. His heart thumped every time somebody knocked on his door to deliver the mail; sure it was either his order or the police coming to arrest him. What would he do if he got caught? Was there a way he could spin this so that the police would believe it was an accident?

By the time a week had passed Jason was sure he'd made a mistake. Any day now the police were going to kick in his door and he’d be thrown in jail; all because he was horny. God he could just imagine the look on his coworkers faces! He was so worked up he didn't even see the package on his front step until it was almost under his foot.

His eyes went wide as he snatched it up, looking from right to left quickly to see if anybody saw before ducking back inside. He opened the box nervously, not really sure what to expect; there had been so many different varieties available so he had just picked one with a cheaper price.

Inside was a little bottle made to look like the sort you get medicine in from a pharmacy. A small note accompanied it in neat typed font.

‘Bimbathyrone - Five Day Activation, to prolong final effects simply take another pill. Effects will fade over a twenty four hour period after the last pill has been taken.’

He blinked in surprise; five days to get high? That might explain why so many people recommended taking it over a weekend so the effects could kick in while alone. It was Friday afternoon now, so perhaps he could take one now and hope the high kicked in by tomorrow morning? Hopefully enough to give some spice to his morning wank.

Then he could hit up the bar tomorrow night and if he struck out there was always the red light district downtown. Though resorting to prostitutes did make him feel a bit skeevy. Hopefully the drug took care of such inhibitions. With a shrug he downed the first pill dry and stood still for a few moments. Despite knowing it was slow acting Jason couldn’t help but feel slightly disappointed when nothing happened, save the chalky feeling in his throat.

~

When he woke the next morning the first thing Jason did was jack off. The stories of the amazing boost to his sex drive and strength of orgasm fuelling his hand as he pumped his cock and up and down before cumming. It was underwhelming; in fact, he barely came at all! A single tissue was enough to clean himself off and he got to his feet feeling wholly unsatisfied.

Jason grit his teeth; great, not only had he risked getting arrested by buying drugs on the dark web, they didn’t even work! Fucking scammers. With a huff he stood up and took a step towards the bathroom, hoping to drown his sorrows in the shower.

And promptly fell over.

He only just managed to catch himself on his hands and knees and blinked in confusion, glancing behind him to try and see what could have tripped him up. That’s when he realised his feet were looking rather…strange. They were a size too small and his ankles seemed to have shrunk as well.

Carefully he got to his feet, feeling the arches strain a little under his weight. They felt too small, making him wobble slightly and take smaller steps than usual that added an odd sway to his gait. The change was so subtle yet had affected his body so profoundly. Jason felt his heartbeat beginning to race in his chest; the bimbathyrone was real and it was working!

His cock twitched; perhaps that explained why his jacking off has been so unfulfilling, he was turning into a woman. Jason felt his brow furrow; that probably meant he wasn’t going to be able to get off until his cock and balls had fully transformed into a pussy and that could take almost three days!

The idea of having soft velvet folds actually sent a thrill through him. He’d never imagined what it would be like to be a woman before a few days ago and now the thought dominated him as he went about his morning routine. He felt so naughty; like he was hiding this massive secret and getting away with it.

He had never been the peak of masculinity but nobody would ever dare suspect he would willingly turn himself into a woman. Not only that he realised, but this new female persona could be anybody he wanted. She was a blank slate; he could reinvent himself as whoever he wanted! Any backstory, any personality, anything he wanted to!

It was freeing to think about. No matter how hard people might try, you couldn't really pretend to be somebody you were not; at least not by the time you were in your thirties. Everybody expected you to be a certain way and start all over again, in a new town where nobody knew you just wasn’t viable most of the time no matter how much you might wish for a breath of fresh air.

Here he was though, in the position to become a whole new person and even view his life from the outside. Again he thought about his plans to hit up a club or red light district and the idea was even less appealing than it had been last night. If he was going to have the best sex of his life as a woman he wanted the whole nine yards. He didn't want to pick up some stranger in a night club or worse, pay for company. A wicked idea formed in his head and Jason grabbed for his phone and scrolled through his contacts.

“Who to pick…who to pick…” He muttered under his breath, “Aha!”

Richard; he would be perfect.

Richard was an old friend from college; the sort everybody had. That one guy who through a combination of good looks, luck and charm managed to walk his way into a high paying job right out of school and was now at the top of the food chain. Jason only saw him every few months and he was beginning to think Richard only did it because he felt sorry for him.

‘Hey man! I know this is out of the blue but I was wondering if you could do me a favour? My distant cousin Jessica is coming into town in a few days and I have to work that night. I made dinner reservations before I realised and she is really excited to go out, do you think you could go with her?’

He waited a moment or two and to his delight Richard actually responded.

‘Hey dude, sure, I don’t have anything else on. Where is the reservation?’

Jason grinned ear to ear.

‘Basco’s, she’s really into wine and their menu is the best. Thank you so much man. I am so sad I can’t go. I have been saving for weeks just to afford a main and dessert!’

Basco’s was one of the most premium fine dining restaurants in the city. Jason had always wanted to go just to see what all the fuss was about but when it cost forty dollars just for an appetiser that was a lot easier said than done. Richard on the other hand, he had seen post several times on social media about how much he enjoyed they’re steak menu.

‘Yeah no problem, man. I have been looking for an excuse to go over there! Just give me the details and I will meet her.’

‘Thanks, you’re a lifesaver. I didn’t really trust anybody else not to act like a creep.’

Jason couldn’t have wiped the smile off his face even if he wanted to. Dating was exhausting; the flowers, the chasing, the giant holes in his wallet that didn't lead anywhere. It would be nice to be on the other side of things for a change, to be the one being wined and dined. He could even flirt with Richard a little and then ghost him once he turned back. Give the man a taste of what it was to fail once in a while, really knock the arrogant dick down a peg.

Of course, for any of this to happen he was going to have to finish his transformation and create Jessica. He would need to complete his transformation of course, then he would need an outfit and make up, not to mention a backstory and personality for his new persona. Maybe if he was lucky, he could get Richard interested enough to buy him a few presents, a necklace here, bracelet there, that he could sell once he turned back.

If this worked perhaps he could turn Jessica into a sort of side hustle, getting expensive gifts and dates with men, some amazing sex and then disappearing without any consequence. After all, who could like her to him?

Justin grinned at his reflection in the mirror, now able to see the slight rounding of his jawline. He’d decided to try this stuff just to get laid but it turned out he was more clever than he even gave himself credit for. This plan was full proof and he could not wait to get started.

~

The rest of his day was spent in quiet anticipation. Each time he felt a slightly shifting of his skin Jason was on high alert, taking in every single sensation with hard focus. He felt the hair on his chest, arms and legs slowly regress back under his skin, leaving it smooth and silky. He spent a good five minutes just running the soft pads of his fingers down the length of his thighs, revelling in just how sensual they felt.

He had to admit, he looked a little funny, with thick thighs and womanly hips sitting either side of his manhood. As the hours passed he watched as his butt slowly began to take on a more rounded, peachy appearance and his thighs grew to accommodate its new weight. He stood in front of the bathroom mirror, far enough back that he could see them and watched as they jiggled thanks to a press of his hands.

Everybody always talks about butts bouncing but nobody ever mentioned how thighs carried the movement on. He spent a good five minutes just experimenting, jumping, patting, slapping; watching how the skin wobbled like jelly yet still held firm in places. He wasn’t fat, only becoming curvy and Jason was here for it.

As he sat back, enjoying the newfound plumpness of his ass he began sketching out a persona to take on. Jessica would be everything Jason wished he could be; confident, flirtatious, gregarious. She would be the sort of woman who spoke her mind at all times and couldn’t care less if people disagreed. She didn’t need to worry about pleasing anybody; quite the other way around. She would be the sort of person people bent over backwards to try and please.

Jason pressed a finger to his lips, feeling them slowly filling and becoming more full over the next few minutes as he trawled through potential names. He already had a first name, Jessica was one he had always liked and wasn't too different to his actual name, but a last name had power. A Last name hinted at your background and he wanted Jessica to sound impressive.

In the end he settled on Dumas, a French name. Jessica may not be French but this hinted at a continental history and gave her a sophisticated air. Plus, with his now ever growing long lashes paired with his sharpening cheekbones he was taking on a sort of continental look.

By the end of the day Jason had everything planned out and his body was well on the way to being female. Not only did he have his now fabulous ass but his shoulders were starting to take on more of a slant, the slope made his neck look longer and more elegant and his facial features seemed to be softening and sharpening at the same time. His chin turned round while his cheekbones became more pronounced.

His eyes were his favourite feature so far. They had taken on a slightly more narrow shape, with long lashes and a slightly hooded appearance. He blinked them, admiring the shine of his iris. His eyes were still they same grey they had always been; but while he’d always thought they looked like dishwasher water before now they seemed cool and mysterious.

He ran his now fine nails through his hair; it had grown three inches over the course of the day and showed no signs of slowing down. The dark black locks seemed to be changing colour slightly too, going from dusty black to silky, jet black. There was even a slight wave to it which he hoped would only get stronger.

His lower stomach was hot; he was so turned on watching this happen it was unreal. And yet, he couldn't seem to get hard. A quick google online showed this was normal, his body was getting ready to replace his cock and balls so they were forced to stay soft despite his growing desire. All the forum posts talking about increased libido really were not kidding. One more sleep, some time tomorrow he would be fully transformed and able to complete his transformation into Jessica.

With one final wink and a quick kiss to his reflection Jason turned off the lights and called it a night. He was eager for tomorrow to come so he could wake up as a sexy woman and take the world by storm.

~

The next few days were some of the most exciting of his life. Yet, he never left the house. He was in limbo, body half female, half male. When he woke the second morning he found his hips were sore from sleeping on his side. Now they were sharp enough to dig into the mattress and he was forced to sleep on his stomach or back. Usually the latter as his chest was so sensitive he had taken to walking around his apartment topless most of the time.

His chest was still flat, for the most part, but each day his nipples grew pinker and more pronounced. He knew it was just a matter of time now until he had his very own set of tits. Would they be large? Pert? Stiff? Would they feel natural or hard like implants? He could not wait to find out.

Already his figure was starting to become more womanly, though right now it was more pear shaped than the hourglass figure he dreamed off. He was so bottom heavy with his bouncy butt and no boobs to counter balance it. Though his shoulders did slowly take on a more sloped look as the days went on.

“Hello, my name is Jessica.”

He stood before the mirror, smoothing a hand over the curve of his throat. He never expected his voice to change so quickly. Even though his facial features were softening, he still looked like a man, even if his hair was a bit shaggy. So itt felt distinctly odd to hear a very female voice coming from his lips.

He found himself liking it though; Jason kept waiting for the dysmorphia to kick in. The moment when he looked at himself in horror and felt totally wrong but if anything he felt more right the more he changed. This voice was no exception.

“I’m Jessica, the best lay in the world.” he whispered in a sultry tone, lowering his eyelids and shivering at the response his body had.

It was like an instant aphrodisiac. God, he wanted to get off so badly. It just wasn't worth it though and he knew it. He had no choice but to wait another night for the transformation to be complete.

~

Jason was thrust into wakefulness with a sharp gasp. Immediately he could feel something was different, as his chest filled with air he could feel a weight there that hadn’t been present before and for a moment he panicked; wasn't that what people said having a heart attack felt like. Then he realised there was no pain, quite the opposite. His whole body felt wonderful; especially the heaviness on his chest.

He threw back the blankets, hitting on his bedside lamp and gaping down at his body. Atop his chest were two small yet beautiful breasts. Round and pert with hard little nipples that pointed straight at the ceiling. The skin there was tingling and stretching as they continued to increase in size, starting as pert and swiftly turning huge and round.

“Oh f-fuuuuck that’s so nice.” He sighed, grabbing two handfuls of the soft skin and massaging them.

They felt better than any tits he’d ever touched and what’s more, they were still growing. He could feel them swelling beneath his fingers, growing more voluptuous by the second. His fingers found his nipples and pinched, causing his back to arch off the bed as his vision went white. He’d never know just how sensitive women’s nipples could be; how did they resist playing with them every second of the day?

He would have stayed that way for hours, maybe even indefinitely, were it not for the sudden sucking sensation between his legs.

“Ahhh! Oh…Ahhhh…M-my cock is-f-finaly!”

He struggled to sit up, leaning back on his hands and letting his new boobs rest against his chest as it heaved. He could feel his cock being pulled up inside his body, slowly disappearing into the hair around his crotch before leaving nothing in its place but a warm, wet hole. The pressure was building inside him as his organs seemed to rearrange themselves and he could do nothing but pant and watch, feeling a strange sense of pleasure build inside him.

“Hnnng! Ahhh, yes, more!”

He was filled with anticipation as he felt his pussy lips swell into being and a new clit bulged between his legs. The tiny nub was burning and the urge to plunge his finger down and rub it was strong but he managed to hold back. He wanted to wait until it was finished and perfect. His new, velvet passage quivered, begging to be filled and Jason shuddered, feeling the tingling sensation he’d come to associate with the change finally ended.

For a few moments, Jason simply laid there, letting the dawn rays slowly filter through his window to better illuminate his body. He could see the change in figure, the way his hips lifted slightly higher in the air thanks to his now bouncy butt. He stretched his toes, feeling the slight change in their shape. He could feel soft locks of hair brushing against his back and as he ran his now delicate fingers through it he marvelled at how soft it all felt.

“It really worked.” He breathed, “Holy shit.”

A gentle morning breeze wafted through his curtains and sent a shiver over his hot skin. His skin seemed to thrum with electricity and every movement seemed to send sparks dancing across it. Jason moved his hand from his hair back to his chest, sighing in bliss as the pleasure returned in full force from before.

Wetness slowly began to seep from his hole, coating his folds and soaking into his sheets. With feather light touch he moved his fingers away from his breast to rest between his legs. The intensity of the pleasure made his whole body jolt, despite the lightness of his touch.

With a groan Jason let himself fall back on the bed and began to rub furiously at that little nub. How could something so small create so much ecstasy? It felt ten times as good as having his cock touched and with every swirl he became more and more sure taking that pill had been a good decision.

After almost two days without any decent gratification he knew he wasn't going to last long; yet the swiftness and ferocity of his orgasm still took him by surprise. His vision went dark for a moment and he was hyper aware of every part of his body as pleasure made him writhe. If he had any brain power left he might have been embarrassed by the sounds he was making but he didn’t.

Gasping he fell back on the bed, taking a few long moments to bask in the feeling of utter gratification as he caught his breath. A wide smile split across his face as the day finally dawned. He could already tell this was going to be the best day of his life.

~

The best day of his life actually started out quite uncomfortable. Jason hadn't really thought through the fact that none of his clothing would fit properly. As a result he was wearing a pair of jeans that were too tight at the waist, yet too loose around his legs and a shirt that was too baggy to really show off his chest.

Still though, he could feel people staring as he walked through the shopping centre; without a bra there wasn’t a lot he could do to stop his boobs from jiggling with each step. He eyed off the various clothing stores available; there were stylish boutiques, giant discount stores and everything in between. He ignored the latter; Jessica was a classy lady, she wouldn’t be caught dead in sale items from Target.

Eventually he settled on what looked like a nice middle ground with plenty of options. Stepping inside felt like entering an alien world. Racks of dresses, skirts and shirts lined the walls, tables of shoes, counters full of earrings and make up; it was alien and exciting all at the same time. He sighed, fingers tapping against his chin as he pondered all the options available.

His gaze flitted from one hanger to another, evaluating each garment with a discerning eye. He dismissed the casual sundresses and jeans, knowing they wouldn't be suitable for the elegance of Basco's. A shame really, that tight fitting denim would look amazing hugging his new ass; but this occasion called for something special, something that exuded sophistication and grace. Something worthy of the newly christened Jessica.

His fingers delicately traced the silky fabric of a midnight blue dress, its shimmer catching the light. He held it against his body, studying his reflection in the full-length mirror. The dress would hug his new curves in all the right places, accentuating his figure without revealing too much. It was a contender to be sure but it almost seemed too conservative.

It was nice but he didn't want to look nice; he wanted to look spectacular. Jessica was the sort of woman who stood out in a crowd without even trying. He wanted all eyes in the restaurant tonight to be on him. His eyes drifted towards a rack of tailored suits, their patterns ranging from classic pinstripes to bold checks. A woman in a suit was quite a look; one that it took a certain level of class to really pull off, especially in a non-business setting.

It might give Richard the wrong idea though, that Jessica was some sort of workaholic. He wanted to strike a balance between power and femininity, to captivate his date without overshadowing his presence. The suits would have to wait for another occasion.

Returning his attention to the dresses, he continued to explore. Fingertips brushed against a soft, flowing gown in a rich burgundy hue. Its intricate lace detailing and plunging neckline added a touch of sensuality to its otherwise modest silhouette. As he held it against his body, she felt a surge of confidence.

But doubts began to creep into his mind once again. The lace did make it seem a bit old fashioned and the last thing he wanted was for Richard to think Jessica was some sort of prude, even with that lower neckline.

His eyes widened as they landed on a simple yet elegant option: a knee-length black dress. It was a timeless classic, the epitome of sophistication. The dress boasted clean lines and a tasteful neckline, offering an air of mystery that would undoubtedly pique her date's curiosity. The top was a halter neck, the thin straps creating a perfect oval that would draw the eye to his cleavage without being obvious about it. As he brushed his palm across the silky smooth fabric he felt a sense of connection.

Laying the dress carefully over his arm Jason made his way toward the change room, grabbing a few extra accessories on the way. He pulled the curtain closed and gave a little squeal of excitement, this was going to be so fun!

Eager to be rid of the ill fitting clothing, he stripped off till he was totally naked. He spent a few minutes admiring his naked reflection from all angles thanks to the mirrored walls of the cubicle before snapping back to attention. Changing, right.

As excited as he was for the sexy dress, what really made his heart race was the lacy strapless bra he’d picked up on the way. It was delicate, made from soft black fabric with a tiny pink bow sitting right between the cups. It was cute and sexy all at once. Gently he pressed the cups against his breasts before struggling to get the hooks done up one handed. Without straps to hold it in place it kept slipping down until an idea came to him.

Jason pressed his breasts up against the mirrored wall, trapping the bra against his chest and holding it in place while both his hands reached around to do up the hooks. His gentle breath fogged the glass and he felt the heat waft across his skin.

His lips were so full and pretty now, he couldn't help but stare. Perhaps it was vain to be distracted by his own reflection but he couldn’t help it; he was a ten out of ten hottie now after all! Who could blame him?

After the bra was finally in place he adjusted his breasts, making sure they were being pushed up by the slight padding at the bottom. It was amazing how such a tiny lift could improve his cleavage so much. Eagerly he grabbed the matching panties, brushing a finger over the bow at the front before pulling them up his legs. The lace around each of the holes scraped at his inner thighs and sent sparks shooting right up his legs and into his nethers. It was hard not to get wet; he didn't want to spoil his new underwear right after trying them on for the first time!

Finally, it was time for the main event, his dress! The soft fabric hugged his body as he pulled it down over his tits and ass. The skirt rested at his mid thigh and it was simple enough to clip the halter neck closed. As predicted the eye was immediately drawn to his impressive chest but what he hadn’t anticipated was just how fabulous his legs looked! The black dress somehow made them look even more long and smooth and he enjoyed stretching them out and posing in front of the mirror. There was no doubt in his mind; this was the perfect outfit.

It was very dark though; Jason picked up the pair of black pumps he’d grabbed and grimaced. He wanted to look sexy, not like he was going to a funeral! He walked out of the change room and placed them back on the display table before carefully examining each and every pair available.

Pink heels? Too girly. Purple boots? Too trashy. Red strappy heels? Perfect.

The buckles made them a little fiddly to put on but he loved the splash of colour. Jason had never been a foot person before but seeing how hot he looked in these red shoes gave him an idea of why the fetish was so popular.

The red really gave his skin a warm glow; eager for more he selected a pair of red disc earrings before paying for everything and walking right over to the piercing and tattoo place across the mall. Two pin pricks of pain later and the discs were in his ears looking fabulous.

As he strode out into the shopping centre again Jason couldn’t help but notice just what a difference his new look was making to how he held himself. It was more than the physical side of things; sure his hips naturally swayed now but his stride was longer too. He felt so much more confident and he realised he could get used to this.

As he walked past the salon the smell of hairspray and nail polish hit his nose making it wrinkle. Jason turned and saw the huge posters boasting women with luscious hair and ruby red lips looking down at home with sultry expressions. Unconsciously his finger came to rest against his plain, unpainted lips.

If he was doing this, he would go all the way so with a decisive nod he walked inside. A woman with a short bob cut smiled at him from the reception.

“Hair, nails or makeup?” She asked and Jason grinned.

“All of the above.”

He spent the next three hours in utter Heaven. As a man haircuts had always been cheap, fast and practical but as a woman there was so much more to enjoy.

The feeling of the hairdresser's fingers slowly working shampoo and conditioner into his long longs, untangling every knot and straightening it till it shined like a blanket of pure midnight from his shoulders.

The unique relaxation that came from having his nails manicured and pedicured before a rich lacquer of red was painted over each one. He even decided to splurge to get a little rhinestone attached to the pinky of each finger for a little extra flair.

Then there was the utter joy of picking out and having his makeup expertly applied. It was like art, only the canvas was his own face. He loved the feeling of the smooth lipstick coating his lips and his already dark lashes seemed to double in size thanks to the mascara. His beautiful, storm grey eyes seemed even more striking with a thin ring of eyeliner and his cheekbones shone prominently after his makeup artist did something called ‘contouring’.

By the time it was all finished, he was out more money than he’d expected but the results couldn’t be argued with. Jason looked and felt like a million dollars and as he walked back out into the mall he watched with joy as heads turned. It was official; Jessica had arrived.

~

Getting a cheap phone hadn't been a problem; he’d already spent hundreds of dollars getting Jessica ready for tonight. What was one bit more? With glee Jason put himself in the headspace of the women he had become and sent a message to Richard with the new phone.

‘Hi this is Jessica, Jason’s cousin. I just wanted to check if you were still alright to meet me at Basco’s tonight. I still can’t believe that loser ditched me lol.’

After a few slow minutes a reply appeared.

‘Yes not a problem, I actually love it there and I’m excited to have a reason to go! There are certainly worse ways to spend an evening.’

No defence for the ‘ditching me’ comment, he noted.

"Great, I am so looking forward to it. I hear their wine is superb. I do hope they have some actual champagne. I hate it when restaurants call sparkling wine champagne.’

He had decided Jessica was a connoisseur of sorts with very high tastes. He’d spent part of yesterday studying wine and learnt that ‘real’ champagne only came from one area in France (aptly named Champagne). Yet many less cultured people called any sparkling white champagne out of habit. He wondered if Richard was aware.

‘Yes! I feel exactly the same way!’

Jason grinned, this was almost too easy and the man hadn't even seen him yet. Charming his way into Richard’s bed was going to be easy. Not that he had any actual feelings for him, no, he just picked Richard because he was rich and if Jason was going to be a woman he may as well get the best possible treatment.

He had no doubt in his mind that Richard got laid on the regular because of his money. It was something he’d always been jealous of. Every time he saw pictures online of Richard out on the town with some woman on his arm he’d burned with jealousy. Not for the woman obviously but for Richard’s lifestyle. Yes, that was all.

‘It seems we are going to get along very well, I look forward to meeting you Richard. Tata for now.’

If Richard replied Jason didn’t see; he turned the phone off to avoid any temptation to keep talking. He needed Richard hungry for information, it was always best to leave a man wanting of that he was sure.

Jason opened up the compact he’d bought from the salon and adjusted his lipstick, making sure there was not a smudge or hair out of place as he got ready to call a taxi. It was time for the best date of his life.

~

It took all his self control not to order a limo to deliver him to Basco’s; he desperately wanted to make a scene with his entrance alone but decided that would be too…gouche. He made do with the way the taxi driver's eyes dipped as he opened the car door and Jason let one of his long legs stretch out as he stepped out of the car. He felt as though he were a princess stepping onto a red carpet.

He could feel eyes on him as he stepped into the restaurant and immediately he was taken aback by just how luxurious it was. The foyer greeted him with a soft glow emanating from crystal chandeliers, casting a warm golden light over the polished marble floors where they were not coated with plush yellow carpets. The air was filled with a delicate blend of tantalising aromas, red wine and beef and spices he couldn’t possibly name if he tried.

The maitre d', a distinguished gentleman with a crisp white jacket and a silver name tag that read "Edmund," approached Jason with a genial smile.

"Good evening, Miss." he said with a rich voice that sounded ever so slightly forced. "Welcome to Basco's. How may we assist you this evening?"

“I have a reservation under Jason, my cousin made it for me.” He answered coolly, resisting the urge to smooth over his dress, being in a place so expensive made him a little nervous.

His eyes darted to the fancy vases filled with flowers that lined the foyer and wondered just how much he would have to pay if he accidentally broke one. He grit his teeth before forcing himself to relax; Jessica wasn't a klutz, and tonight he was her, so there was nothing to worry about.

"Ah, yes. Right this way, please." Edmund led Jason through the restaurant, the soft glow of flickering candles illuminating the path.

Why did fancy restaurants insist on putting candles everywhere? Seemed like an odd choice now that he thought about it, especially in this day and age. Edmund stopped at a table situated near a large window overlooking a breathtaking cityscape.

"Here is your table, Miss," he announced, pulling out the chair for Jason. "Your server will be with you shortly to assist you with the menu and any other inquiries you may have. I believe you are waiting on somebody?"

“Yes, my date should be here any moment.” He nodded, “Thank you, that will be all.”

Edmund gave a little nod and Jason felt a thrill go through him as the man's eyes lingered on that oval shape in his dress. Nobody could resist looking at his body; Richard would be no different.

He settled into the plush seat and looked out at the panoramic view before him, his eyes twinkling with awe. It was amazing; he walked down this street all the time yet it looked so different from the inside surrounded by all this splendour.

Or perhaps it was simply his point of view changing the more he got used to this female body. He would almost be sad to say goodbye to it tomorrow. Then again, he did have a few more pills. He could prolong his time as Jessica if he really wanted to, call in sick and enjoy just one or two more days in this fabulous, sexy body. He had spent quite a bit of money outfitting himself, it would only make sense to make the most of it…

“Jessica?”

He had been so caught up in his thoughts Jason had totally zone out. He had wanted to plan his pose perfectly but that had gone straight out the window because standing before him was Richard. It had been a few months since last they saw each other, Richard had grown a short beard in that time. It suited him.

“Yes.” he smiled, “Thank you again so much for agreeing to keep me company. Dining alone, especially in a place like this is so…”

“Sad?”

“Yes.”

Richard took a seat and butterflies began to form in Jason’s stomach. Why was he nervous? He had this in the bag, he looked incredible enough that he was sure Richard was already undressing him in his mind. His tongue felt heavy in his mouth; he had planned so many clever and witty things to say. Jessica was never caught off guard and yet here he was sitting in awkward silence while Richard stared at him.

“You’re beautiful.” He said after a moment before quickly adding, “That probably sounded shallow, I just mean, it’s hard to believe you’re Jason’s cousin. Not that he’s ugly it’s just you’re…something else.”

Warmth bloomed across his cheeks and deep inside his chest. Somehow, he could tell Richard was being sincere and having somebody call him beautiful felt oddly nice. He’d been prepared for hot or sexy but strangely enough, not beautiful.

“Thank you, you’re quite the looker yourself.” Jason held back a nervous giggle, he hadn't meant to add that last part.

“Well, why don't you tell me about yourself.”

Ah, now this was a question he had a perfect answer prepared for.

“Oh there isn't much to tell, I flit from place to place, going where the wind takes me.” he said mysteriously, “I’d love to settle down one day but I can never seem to find somebody worth staying in one place for.”

“Oh, how interesting where have you been?”

Jason started listing the cosmopolitan cities he'd researched, saying each name with almost a slight trace of boredom as if living in twelve different countries was a normal, everyday thing. He could tell Richard was impressed and that made him happier than he thought it would. Of course the whole point of this was to experience the best sex of his life so impressing Richard was always part of the plan but…there was something more there. As they continued to talk Jason found himself slowly coming to the realisation that he actually wanted Richard to like him, not just want to sleep with him.

“I suggest having the lamb.” Richard said with a charming smile, “I always get it, every time I come here I tell myself I will try something else but I always end up back with the lamb. It’s addictive I swear.”

“I’ll take your word for it then.”

Truthfully, Jason was thankful to have the choice of food taken off his mind. His heart was racing and his body felt like it was starting to slowly heat all over. He could feel the short hem of his dress pressing into his thighs and the panties he bought were slowly starting to get moist. The bimbathyrone was humming in his veins and memories of that first orgasm were not helping him to stay focused and calm.

He had spent the whole day getting ready and now the moment was finally here. He almost wished he could skip the dinner entirely and go straight to having Richard for dessert.

“I have to admit,” Richard said after they ordered, “At first I was sad Jason wasn't asking me to come and hang out with him but seeing you now, I think I am rather lucky.”

“You want to hang out with me-with Jason?” He giggled, “You make his entire yearly salary in a month.”

“I don't see what that has to do with anything.” Richard’s face pinched slightly and Jason realised he looked genuinely offended, “How much money a person makes doesn’t affect how fun they are to be around.”

“I know I just…richer people tend to think that.” Jason replied awkwardly, his cool as a cucumber Jessica persona slowly slipping through his fingers, “Sorry. I am just a little nervous being here with somebody so…”

“Devilishly handsome?” Richard joked and Jason, to his horror, snorted in laughter.

“Oh my gosh I am so sorry that was gross.”

“No, no! I like it, that’s how I know it was a genuine laugh.” Richard said, leaning forward on the table, ignoring the man pouring their wine entirely, “And look at us, I’m already finishing your sentences. Looks like we’re a match made in Heaven.”

Jason’s pussy pulsed, another spurt of wetness coated his folds as we stared into Richard’s warm smile. His teeth were perfectly straight and white; he wondered what they would feel like running over his sensitive breasts. The thought was so overpowering it took all his self control just to keep his breathing even.

“Sorry, am I coming on too strong?” Richard winced, obviously taking Jason's silence as a bad sign. “This isn't even a date. Sorry you’re just really pretty and this place is so romantic my brain automatically sort of…”

“Assumed?” Jason finished for him with a wry but genuine smile. “Now who’s finishing who’s sentences?”

Richard chuckled.

“Is this a date now?” He asked, “I just need to know how hard to lay on the charm in the hopes that I can score another if it is.”

“Oh yes,” Jason lifted his wine glass and clinked it against Richard’s. “This is definitely a date.”

The wine warmed his blood and Jason could feel the facade he had spent so long carefully crafting starting to slip as the dinner continued. His body ached to be touched; his skin hypersensitive to each pit of fabric resting against it. He desperately wished it was Richard’s hands touching him instead.

As their meals arrived he couldn't resist resting the side of his foot up against Richard’s leg under the table cloth. As he cut into his lamb he watched with a small smile as the man tried to stay casual as he slipped off his shoe and continued to caress his leg.

As he lifted a piece of the lamb to his lips, the flavours unfolded on his palate. The meat, cooked to a perfect medium-rare, offered a harmony of textures—tender, yet with a slight resistance that showcased the skill of the chef. Each bite released a burst of richness and succulence, as the natural flavours of the lamb mingled with the subtle seasonings and herbs that adorned it. Normally, it would have his full attention but as it stood, his body was far hungrier for a man than food.

Richard leaned across the table as the meal went on, he had the most amazing talent to eat without ever looking at his plate. Jason could feel those eyes upon his skin and it made him shiver. It seems he was not the only one hungry.

“Would you like the desert menu?” Edmund asked as he cleared away their plates.

“No.” They responded in tandem, “Just the bill.”

“And a taxi.” Richard added, eyes never leaving Jason’s.

“Just one taxi, sire?” Edmund replied dryly.

“Yes.” Jason answered for him, “We will be leaving together.”

~

Jason had planned for his Jennifer persona to be cool on the surface but hot underneath. He’d wanted to be patient, to let Richard woo him and only right at the last moment give in and let the man ravish him. Furiously making out in the back of a taxi while it wove through traffic was certainly not what he’d had in mind and yet here he was.

His short skirt already bunched around his waist as Richard’s warm hands cupped his bare ass. He was straddling him as the taxi driver awkwardly cleared his throat. Jason paid him no mind, all he cared about was the bulge he could feel pressing against him and how lovely Richard’s lips felt against his own.

It really was different; being a woman. He felt as though he were on fire; Richard’s fingers trailing flames down his back as they stroked up and down his spine. The taxi driver cleared his throat three more times before they finally broke apart and Jason realised not only that they’d stopped moving but that he had no idea where they were.

“This is my apartment.” Richard whispered, “I hope that’s not presumptuous of me.”

“Not at all.” Jason breathed, reluctantly climbing off his lap and clambering out of the car.

Richard’s fingers threaded through his own and they entered the building; as soon as the elevator doors closed Richard was on him again and Jason couldn’t help the low moan that escaped him. This felt like a movie, making out in an elevator as time seemed to stand still. Richard’s hands slipped beneath the thin halter neckline of his dress and with a flick of his fingers, the top was falling down.

Jason didn't even have a chance to feel scandalised before the door opened revealing a huge penthouse suite. Normally, his heart would have ached with jealousy and bitterness but there was another part of him aching far more right now.

They practically fell into the room, elevator locking behind them as Richard hefted him up onto the island counter of his kitchen. The marble was cold but still Jason didn’t hesitate to let him slip off his panties as well as the dress, leaving him in nothing but his new, shiny bra.

Richard caressed the small bow between his breasts while Jason tried to catch his breath. His inner passage was so wet and wanting it was almost painful and for the first time he realised how on display he was. Spread across this counter, practically naked while Richard was still fully dressed. He would have to do something about that.

His hands went for the man’s fly, unzipping it easily and shoving his dress pants down. Richard needed no more encouragement , dragging them off and kicking them aside, finally revealing the object Jason's body was so craving. It was bigger than his old one; a true manhood and yet, Jason felt no envy, only desire.

Without any hesitation he wrapped his legs around Richard’s waist and pulled them together until the head rested against his hole. There was only a moment's hesitation; he had planned to savour this moment but now that it was here he couldn’t bring himself to wait a second longer. Richard’s arms wrapped around his back and pulled them together in one swift motion and all the air left Jason’s lungs.

In a single second he was fully impaled, filled completely by that hot length. He could feel it resting against some deep part of himself and a sense of pure bliss swept over him; it felt as though this was how he was supposed to be.

Then Richard pulled out and the sensation of his cock rubbing against his inner walls made Jason wail. His hips bucked and they came together one more, then again and again. All persona was gone, the only thing on his mind now was the pleasure and how he couldn't get enough. Each thrust felt better than the last, especially when Richard hit that bundle of nerves right at the back of his passage.

“Fuck! You feel incredible!”

“N-no talking, more fucking.” Jason breathed, the words taking far more brain power than usual, “Just k-keep–! Oh fuck yes…ahhhh…ahhhh…ahhhhh!”

The ecstasy just kept on building, surely he couldn't be far from cumming now. Yet every thrust seemed to just add on top of the previous one, taking him higher and higher without ever showing signs of crashing down. Thai was better than anything he had ever experienced and for a few seconds he was there; on the edge, teetering in nothing but pleasure until finally, orgasm washed over him like a crashing waterfall.

It wasn't like the orgasms he was used to, the intense burst of pleasure and brief tightening of his balls no, this filled his entire body and made it writhe out of his control. He clung to Richard for dear life and it kept going on and on until finally, he could breathe again and his partner threw back his head and grunted as he too finished.

Jason rested his head on Richard’s shoulder, both of them panting for breath. His pussy clenched around the softening cock inside him and he smiled feeling it begin to harden once more. Jason knew it would only be a matter of minutes before they were going again. He’d stay the night and then they'd fuck int he morning as well, then, after breakfast, he would go home and take another pill. He planned on staying Jessica for as long as he possibly could.