[TG] Transformed and Entranced (Patreon)

Commissioned by Serious Sentence.

When Bradley’s girlfriend Viv wants to try dressing him up as a woman as foreplay, he isn’t sure; but soon he finds himself addicted to it.

~

Months ago, when Bradley finally studied and saved up enough to move to an Ivy League college in the city, away from his hick hometown he had made himself a promise. He would be successful; so much so that he would never need to see those cows and cornfields again and the first two decades of his life could basically be wiped away. So when he arrived at college he set about ensuring he had the perfect image. He pledged to the best fraternity in order to make connections, he made friends with the sons of senators and businessmen, he took great care to ensure his appearance was classy and most importantly, manly. He had a strict gym schedule to maintain his physique; not overly muscular but enough to be attractive and give him a leg up with the ladies. That is where Vivienne came in. If he was going to be the perfect, successful man, having a hot chick on his arm was practically essential. Vivienne was the only daughter of some cosmetic magnate and everything he needed. So when she agreed to go out on a date he was ecstatic. He wined and dined her enough that soon they were going steady and he was the envy of every man on campus; he finally had it made.

Or so he thought.

The icing on the cake that came with dating Viv, was that she was kinky as hell. He’d heard rumours from past boyfriends of course and had planned accordingly, when she bought out the handcuffs he hadn't even blinked. He had discovered that he quite enjoyed it. Being so dominating, exerting his manhood, it made his blood rush and his orgasms even harder. After several months he was ready to declare his life perfect and on the right trajectory to have the life he’d always dreamed of.

And then Viv had bought out a blonde wig.

“You want me to wear that?” He blinked, staring at the long tangles of wavy blonde synthetic hair.

“Yeah.” She pouted, “I want to reverse the rolls a little, and have you as my submissive girlfriend.”

Bradley’s stomach did a flip. Kinky stuff was one thing, hell, he was open to being a bit submissive behind closed doors so long as nobody found out about it but this…this was too much.

“I don’t think I can.” He grimaced, “I mean, I wouldn't even know the first thing about acting like a woman.”

“No, I suppose not.” Viv pouted, “Such a manly man, it would be your polar opposite, acting like a horny bimbo.”

She looked so sad; her large brown eyes met his and he swore for a second, there was a strange flicker of colour there. It must have been a trick of the light though as it was gone a second later. He didn't dwell on it though, his guilt was suddenly tenfold and he shifted uncomfortably on the bed.

“I suppose, maybe I could try it. Just with you…but I don't think it’ll be any fun for either of us.”

“Oh it will!” Viv beamed, leaning in close so that those pretty eyes were an inch from his face, “Aren’t you curious to feel what it’s like on the other side?”

Not really…then again. He’d never really thought about it. The gears in his head began to turn and to his surprise, the idea was sounding less and less strange. People did weird shit in the bedroom all the time right? And it wasn't as if anybody important would find out. It was just a wig, there was no harm.

“I guess I’m a little curious…” He mumbled, taking the wig and putting it on.

It moulded to his head perfectly, like it was made for him. He had expected it to itch or sit awkwardly atop his short cropped black hair but instead it was actually quite comfortable and with a little adjustment, you couldn't even tell it wasn't real. This must have been some sort of high end wig made by Viv’s father’s company.

“Oh my gosh you look so cute.”

Bradley flushed, instantly regretting it.

“That’s not really a compliment for guys, Viv.”

“But you’re not a guy right now, you’re my bimbo girlfriend.”

They were roleplaying right now? What did he even say? He felt tongue tied and humiliated.

“Uh yeah that’s me…like….totally?”

He sounded like an awkward robot. The mood was anything but sexy and Viv pouted.

“Maybe you need some practice before we dive into this.” She sighed. “Come over here.”

She pulled him over to the bathroom and pulled open her makeup drawer. Bradley watched with growing dread as she gathered multicoloured tubes and powders from the pile and placed them on the bench. Surely she didn't expect him to wear that?

“Here, this peachy pink will go great with your complexion.” She smiled, uncapping the tube and moving it toward his lips.

Bradley took a firm step back.

“No, sorry Viv. This is too much for me.” He took off the wig, “I don't get off on being a woman, let’s just do our regular stuff, okay?”

Viv pouted.

“Aw, but that’s so vanilla. I thought you were exciting, Bradley. A real man would do anything to please his woman sexually, don't you think?”

Having girls talk about how great he was in the sack was one of his goals. But if it got out that he let his girlfriend turn him into her little doll, that would ruin all the hard work he’d put into his image.

“You enjoy our usual sex though, don’t you?” He was suddenly filled with self doubt which only compounded as Viv hummed awkwardly.

“Yeah I guess, but I’d cum so much harder if you did this for me, Bradley.”

She was looking right into his eyes as she said it, there was such honesty there. He instantly knew this was the only way he would ever truly and totally satisfy her and…he wanted to do that, right? Pleasing Viv was very important to him. The longer he looked at those big, pleading eyes the more he knew it to be true. But then he remembered the lipstick and wig and shook his head.

“I’m sorry Viv. I just can’t.”

She sighed, placing the items away with a disappointed look on her face that hurt harder than any slap.

“I guess I will just have to learn to live without it.”

~

Days passed since he’d dismissed her new sexual roleplay and with each sunrise, Bradley became more tense. Sex became robotic, neither of them fully satisfied and there was an awkwardness to the air. All of that he could deal with but the day dreams; that was what really got to him. Every time his focus slipped from studies or fun a mental image of himself in that blonde wig, with shiny pink lips greeted him. At first it was awkward but then, to his horror, it started to make him aroused. He remembered how wanton and hot Viv looked writhing under him when they first started dating, how submitting to his touch made her cry out in pleasure. Then he would imagine himself in her place, blonde hair splayed around his head like a platinum halo as his full lips formed an O.

Such images got conjured up more and more until finally, one night in the shower he couldn’t take it anymore. He gripped his cock and pumped, less than a minute later he was cumming, the vision of himself as a helpless bimbo still front and centre in his mind. Shame burned under his skin but…it was the best orgasm he’d had in weeks. Maybe he could indulge Viv just once with this little fetish of hers.

Just once.

~

“Oh Bradley! Yes, let’s get started right now!” She flung her arms around him, kissing him deeply before pulling back and holding a hand against his cheek, “You make me so happy.” She sighed.

Bradley couldn’t help but grin, a warm wave of affection passing over him as he looked at his girlfriend. She was so pretty, and if she was happy, he was happy. Once again he let her place that wig on his head and lead him to the bedroom. Surprised when she asked him to sit down to do his makeup.

“Should I get undressed?”

“No, I think we’ll keep it simple for this one.”

He opened his mouth to ask what she meant but the light caught in her eyes once more and he found himself momentarily dazzled and the question forgotten as she slowly painted gloss onto his lips. It was funny, as she applied the gloss Bradley was sure she must have been looking at his lips, how else could she properly apply it? But from his point of view, it felt like she was staring him down intensely. The gaze made something stir within him, with each pass over his lips the gloss felt more sensual and arousal began to build. Part of him was still utterly humiliated, being turned on by something as girly as putting on lipstick but as she finished up Viv put the lipstick down and pressed her hand into his crotch.

“Oh fu-!”

He hadn't even realised he was hard already and the pleasure hit him hard. He didn't have time to finish his sentence because Viv’s lips were covering his and she swallowed what sounds escaped him. They kissed with more passion than they ever had, tongues intertwining, teeth scraping against lips until the sweet, artificial taste of strawberry gloss permeated his mouth. Viv’s spare hand raked through his blonde wig and he swore he could feel the tug of roots at his skull. It felt so good. A moment later there was weight on his hips as she sat in his lap, still palming him through his jeans until all of a sudden, his balls were tightening. He tried to pull back to warn her but it was too late. They broke apart just as he shuddered, hot seed spilling out and soaking his boxers enough that a wet patch was soon visible on his front.

Bradley had never been so embarrassed in his entire life; not only had he cum in his pants like a teenager, after some light petting no less but he’d done it dressed like…this. He’d never felt less manly in his entire life.

“Oh God, I am so sorry Viv, I-I just got carried away-”

“Shhhh, it’s alright.” She cooed, “That was so hot. We’ll try again tomorrow, huh?”

He felt ashamed at the bolt of excitement that went through him when she suggested it.

“Just promise you won't ever tell anybody we’re doing this?” He begged and she patted his head gently.

“It’ll be our little secret.”

~

Slowly but surely, Bradley started to become more comfortable with their little sessions. Each time Viv would introduce a new element; high heels, sexy panties, stuffed bras. Each time Bradley planned to put his foot down but she would beg and pout with that sexy look on her face he would acquiesce, promising himself it would just be the one time. But then she would pleasure him and it would taste so sweet. He felt himself starting to get addicted to the pleasure dressing as a woman bought. He wanted to fight it but between his increasing need to make Viv happy and the addictive nature of the pleasure she gave him his will power was steadily shrinking. Which led to his current situation. In front of a mirror, wearing nothing but a skirt, stuffed bra and his wig while Vv jacked him off. He could see the skirt flapping in the breeze, see his own face twisting in pleasure as she pumped. It was just like the fantasies that had originally bought him here; a literal dream come true.

He was so embarrassed at his behaviour but he couldn't stop moaning. Making breathy, high pitched sounds that almost sounded like an actual woman’s as he got close. He desperately wanted not to like it, for something to be the one step too far and turned him off. He didn't want to cum like this…like a blonde bimbo who couldn't look away from her own face in the mirror as she crested.

“It’s okay to like it.” Linda whispered in his ears, “Being my little bimbo makes you feel good doesn't it.”

“Y-yesssss!”

“Then cum for me, girlie.”

The order was all it took, he fell over the edge and cum stained the front of the frilly skirt. He watched the moisture drip from the lace fringe as he gasped for air.

“Are you imagining what that stain would be like if it were pussy juice?” Viv asked, he almost choked.

“How did you know?”

She stroked his hair, gently wiping him clean with such care that his whole body shivered; he’d never felt so loved.

“I know you darling, that’s all.”

“Did you want me to…?”

“No, watching you is enough.” She purred, “In fact, I think you’re ready to go all the way?”

“What do you mean?”

She laid a kiss at his temple.

“You’ll see.”

~

Bradley’s thoughts were constantly filled with thoughts of Viv and their next rendezvous. Nothing strange really, a young man obsessed with his hot girlfriend, certainly nothing to be concerned about. As a result, he got sloppy. It was late, he was sure the rest of his fraternity were asleep by this point and he was still tossing and turning. There was an odd ache deep inside him, a sort of deep need he had no idea how to satisfy. He had been horny before but this felt…different somehow. He tired quietly jerking off but found he couldn’t cum. Not even when imagining his reflection in that mirror. Laying there naked in his all too male body was ruining the experience. His mind wandered to the box under his bed, the one Viv had carefully packed and gifted to him several days prior in case they ever decided to go at it over at his fraternity. He knew what was inside, surely just one little look couldn't hurt.

He sprung out of bed and grabbed it, opening the discrete package with his heart racing. Inside was a skirt; pink and slightly poofy with a crinoline underneath for extra volume. A pair of pink heels that wouldn’t look out of place on a barbie doll and a tube of hot pink lipstick to match. Instantly, his cock began to harden. The girlier, the better. Without any hesitation he slipped the skirt up his legs, sighing in contentment as the lace scratched at his inner thighs and made him shiver.

Just as he snapped the elastic around his hips he was hit with the strongest feeling that somebody was watching. He looked around the room, ears pricked for any sounds of footsteps outside in the hall. Nothing. He was getting paranoid. Dismissing it quickly he did up the straps on his heels, effortlessly standing afterwards. Viv had been so kind, helping him learn how to walk in similar shoes. She’d made him strut around the house many times, learning how to sway his hips to keep his balance.

“I just don't want you to fall and twist an ankle.” She insisted, “Better get in the practice now so you’re confident during our escapades later.”

She was so thoughtful.

The only thing left was the lipstick but to his horror, he realised that he had no mirror. He was going to have to go down to the shared bathroom down the hall. Bradley bit his lip; without the lipstick his look would not be complete but…he couldn’t walk out wearing this. If one of his frat brothers got up for a midnight snack and saw him, God he didn’t even want to think about it. But on the other hand, even if he took the hells and skirt off, he wouldn't walk back up the hall from the bathroom wearing lipstick for the same reason. If it were a less flamboyant colour maybe he could lie and say he’d been making out with Viv but to have it so perfectly applied would be an obvious giveaway.

He was rock hard already, maybe he could skip the lipstick this time. His dick had already lifted the skirt fabric and he could feel precum dripping down the shaft. He knelt in the middle of the rug and began to pump, groaning with satisfaction. Finally; he had been right about wearing his outfits, the gratification had finally returned. It wouldn’t take much now; he started to let out his breathy female moans. He didn't even have to try anymore, it was just the sound he made in response to the bliss. He was getting close when all of a sudden there was the sound of footfalls outside and his door slammed open.

“Bradley’s got a girl ov-WHAT?!”

He was right on the edge; even as his eyes widened in horror at the sight of his brothers at the door Bradley couldn’t hold back his orgasm. Humiliation flooded his system as he knelt on the floor, knees apart with a hand still gripped around his cock, hidden from view beneath his thick skirt.

“What the fuck, dude?” Sam gaped.

“I…I…It’s a thing for Viv.” he croaked, “She has this fetish I…I’m making her a video! I don’t actually get off on this! I swear!”

“Looks like you just did dude, holy shit.” Ben gaped before turning around.

He pleaded with them, tried to insist his phone had been set up to record and he’d just forgotten it. Some said they believed him, most didn’t. Bradley felt his manly persona, all his dreams slowly slipping through his fingers. He’d made a complete fool of himself in front of all his future connections; nobody was going to give a leg up to a sissy boy like him now.

~

He threw the outfit away. None of his fraternity brothers were treating him normally anymore, some teased him sure but for the most part everybody just stepped around him. Like that one awkward kid in grade school the rest of the class just decides to ignore. He felt like he was walking on eggshells and could do nothing right; if he did anything even slightly effeminate everybody glared. He’d not realised just how much of his girly persona he’d let slip into daily life. When he giggled, covering his lips with the tips of his fingers in an effort to laugh things off everybody had gaped; including himself. But acting macho got him nowhere, each time he asked one of his fellows to join him on a run or go to the gym they looked at him with this strange expression; as if to say ‘c’mon man, you’re not fooling anybody’. He was stuck between a rock and a hard place. He’d come to this college to reinvent himself and he'd succeed; but instead of the successful, respected man he’d dreamed of…he was now the sissy frat boy with a feminization fetish.

After three days he’d had enough. He walked over to Viv’s apartment off campus fully intending to break off this little game. If he had any chance of regaining the respect of the other men around, he had to go cold turkey and get over this new obsession. Fortunately, his girlfriend was home.

“Hey, Viv, can we talk?”

She took him by the hand and led him to the couch where the whole affair spilled out; he told her about being discovered and how he needed to stop this little game right here and there. To his surprise, Viv took it well and by the time his story was done she was holding his face in her hands, a look of love and even slight concern on her face.

“That must have been hard,” She cooed, “But I think you need to look on the bright side. Don't give up.”

“What do you mean?”

“Now that everybody knows there is no reason to hide.” She hushed, he wanted to argue but that strange light was in her eyes again and her words started to make sense.

“Now you can be who you really are.” She whispered.

“A…bimbo?”

“Yes.”

Arousal washed over him like a wave. No! No he didn't want to get turned on by this. He had to resist-! He was already hard, Viv’s gentle hands divesting him of his clothing had him shivering in anticipation; he’d stop in just a moment, any second now he swore. Then she reached behind the couch to reveal his beloved blonde wig. Oh how he’d missed it!

‘Stop! Stop!’ He mentally begged himself but it was like he was in a trance, driven by lust he placed the wig on his head and sighed in relief.

There was a strange pressure, almost like the hair of the wig pressing into his skull for a moment before disappearing. He raised a hand to itch at the hair and…the wig was gone. In shock he tugged at the blonde hair; it was real! He wanted to yell but no sound came out as his jaw dropped in shock. His eyes flew to Viv but she just smiled with those twinkling eyes.

“I'm going to make you just perfect.”

Oh. Oh he liked that idea. It would make Viv happy and Viv must always be happy. It gave him pleasure to know he pleased her. And what gave him even more was the sight of a full, DD bra that appeared in her hands. It had forms inside it to simulate breasts and his heart began to race. He didn't even see where she grabbed it from but he eagerly held out his arms and let her hook it up. He looked down with glee, watching the breast forms jiggle as he moved. Curiously he pressed against them, unable to even see the seam where skin met silicone and was surprised to find he could feel them. Just like real tits!

“And I have one that’s even better.” Viv announced, producing a strange pair of panties.

They were flesh coloured and thicker in the front, he realised with a start that the front was made of silicone just like the breast forms; shaped into a pussy. If he put this on, his cock would be squashed against his body to the point that he would be female all over. He didn't want to be turned on but…it was just too alluring. He had to try it. Getting his erection flat against himself in order to pull the panties on was difficult but eventually he managed it and with a moan, he felt a strange sort of suction as the silicone seemed to merge with his skin. He found he couldn't even feel it anymore, what he could feel was that same dull ache inside him, that need he didn't know how to satisfy.

He wanted to tell Viv about it but he didn't have the words, she seemed to understand though, taking his hand and leading him to the bedroom. As they walked he couldn't help but quiver; with each step his legs rubbed together and a warm slickness began to drip down his legs. Instead of the bed, Viv led him to the mirror and ordered him to sit. She sat behind him in turn, reaching around to his front to cup those heavy tits.

Bradley looked at himself in the mirror and felt a strange mix of confusion and arousal. His reflection wasn't there; in his place was a sexy blonde, wearing nothing but a black bra. Her full lips were parted, his pale skin flushed with blood as she grew more and more aroused. It was only when he saw Viv’s hands moving in time with the lovely feeling at his chest that he realised the reflection really was him. His eyes drifted downwards and stared in shock; somehow that pair of panties had disappeared, the fake pussy on the front was real! It was glistening with wetness and before he could come to terms with it all, Viv’s finger was parting those folds further to circle his new clit.

“You love this so much.” She whispered, their eyes locking in the mirror, “You want to stay this way forever.”

Yes. Yes he did! God he wanted it so bad. The pleasure between his legs was so intense he was shaking. He could only nod his head and moan, already the muscles in his torso were tightening, the pleasure going beyond complete as he came with Viv’s name on his lips. His embarrassment at the fraternity was long forgotten now; his mind was filled with nothing but pleasure and the sight of Viv’s beautiful, glowing eyes.