[TG, M->Feminized Male]

[CW: Non-con, Deception, Drugging, Bondage/Stuck]

Oliver woke up to his clothes still missing. Not that he was surprised, given that the night before Gabrielle had ominously told him that the fun was ‘just beginning’. He sighed, debating between staying in bed, or dealing with more of whatever Gabrielle had planned. Ultimately, there were things he wanted to get done today, so it made no sense to waste the day.

Glancing at the pile of yesterday’s clothes, Oliver sighed. What was going on? Why was Gabrielle doing this? He shimmied his hips into the booty shorts and then tugged on the t-shirt. He glanced at the sandals, shaking his head. Not today.

Oliver walked to the bedroom door, about to open it when crashing through it came his girlfriend. They both stared at each other, taking in the sight. Slowly, Gabrielle offered the mug in her hand to Oliver, and he accepted it. Morning tea, complete with that same strange taste as the day before. If anything, it was stronger today. It took everything Oliver had not to spit it out, but he made the effort so that he wouldn’t offend Gabrielle and the effort she put into it.

Gabrielle, for her part though, was shaking her head. “Nope, this won’t do,” she stated, with a gentle sigh.

“What won’t do? Aren’t you happy that I’m wearing this again for you?” Oliver asked, sipping his tea.

“Well, yes, but you can’t wear the same thing two days in a row.”

“Why not? You can’t tell me you have even more girly clothes for me to wear?”

Gabrielle did a gesture that seemed to be halfway between a shrug and nod. “Look, it’s just not proper to wear the same clothes two days in a row.” Oliver raised an eyebrow as he took a long sip of his tea. Clearly, he didn’t get what Gabrielle meant by that. She sighed. “It’s not ladylike.”

With a chuckle, Oliver set down his mug; somehow, he’d already drunk the whole cup. “Well, not a problem there, then. I’m not a lady, so I don’t have to act ‘ladylike’. I don’t get what you’re up to with this, but you’re not turning me into a girl.”

Gabrielle’s hand flew through the air, smacking Oliver’s cheek. She made sure it wasn’t hitting him that hard, just enough to startle him. Oliver stared at her, mouth agape as he rubbed the tender pink spot on the side of his face. The normal anger he would typically feel flooded through his body, though it quickly dissipated. Instead, a soft whine left his parted lips and tears formed in his eyes.

“Today’s outfit is going to be worse because of that outburst,” Gabrielle promised, her tone cold and stern. “Now, get undressed.”

Oliver quickly obeyed. Once again, he found himself compelled to do as Gabrielle was telling him to do, as though the idea of resisting was foreign and inaccessible to him. Within seconds, the pair of garments were off his body, and he stood in front of Gabrielle completely naked. From within a pocket of her dress she pulled out a pack of razors, handing them over to Oliver. He stared at them, befuddled.

“You’re going to take a shower, and you’re going to shave. Completely.”

“Come on, Gab--”

“No, Oliver, listen. You agreed to our arrangement. You can either move out, or do what I tell you. Besides, are you scared to shave some body hair?” Oliver shook his head, taking the razors and turning to go into the master bathroom.

Oliver started by shaving his face, trying to delay the inevitable. That didn’t take long, especially with the brand new sharp blades in the razor Gabrielle had handed him. He looked off to the side and saw Gabrielle watching him. He felt uncomfortable, mostly embarrassed, as he made eye contact with his girlfriend. For what came next, he needed privacy.

Shutting and locking the door behind himself, Oliver weighed the best ways to go about this. He vaguely remembered reading or hearing somewhere that women shave their legs in the shower, so he figured he would try that. Hopping in and running the water hot, Oliver sighed. Why had Gabrielle smacked him? More importantly, why was he about to cry from it?

Oliver dragged the razor along a patch of his calf, watching the hair curl off it. Satisfied that it seemed to be working easily for him, he resigned himself to removing all his body hair while he thought about his situation.

‘Submissive’ was never a term that Oliver thought applied to himself, but here he was, doing everything that was told to him. Nor would he ever call his normally-demure girlfriend ‘dominant’, but that confident stare and powerful pose she’d been doing? Yeah, ‘dominant’ seemed the only way to describe what was happening there.

And the sex yesterday? Oliver shivered as the memory rolled over him. Could it even be called sex, if no one finished? It was too intimate though to be anything else. He wasn’t used to being out of control like that, but he hadn’t been able to get it out of his head. Oliver bit his lip as he thought about it, feeling himself getting turned on. He shook his head, surveying the progress on his body.

Normally, standing in the shower with water running over his body hair darkened the already brown hair to a dark black. Now, with it missing, it felt like he was looking at an entirely different person. Oliver set the razor down, taking a moment to run his fingers over his body. From the neck down, he was as smooth as a baby. With the warm water still hitting his skin, it felt like touching silk. It felt…

Like touching a girl.

Oliver recoiled at the thought, standing horrified by the revelation. He quickly turned off the water, and hopped out of the shower. He stole a look back at the razor, taunting him with its glossy pink sheen that he hadn’t even noticed. The cold air rushed to hit his body, and his anatomy shriveled up in response. He’d always been more of a grower than a shower, but right now he hoped to look like a man in the mirror. Instead, he looked petite and slender without the body hair creating texture or extra depth to his appearance.

Turning from side to side, he stared at his reflection. On a whim, Oliver covered his chest and his crotch with his arms. He winced at the sight. While it didn’t look outright female, it certainly wasn’t doing any favors. At least this way, his throbbing nipples were hidden from view. Gently Oliver rubbed them with his hands while looking down at them. They seemed swollen, and tender to the touch. Very uncomfortable, and very distracting.

Still, the deed was done. Gabrielle had threatened - or perhaps promised? - that today’s outfit would be ‘worse’ than yesterday’s. What could be worse than girls’ clothes, Oliver mused. Did he really want to go out there and face whatever she had planned? Did he want her to see him shaved like this?

After a moment, the decision was made. There wasn’t much he could do, and certainly he couldn’t live in the bathroom until his hair grew back. Boldly, he opened the bathroom door back to the bedroom, only to find the room empty. Well, not entirely empty. A bundle of clothes sat on the bed, positioned perfectly to be noticed by Oliver as he entered the room. No sign of Gabrielle, though.

Cautiously - as though it were a coiled snake ready to strike - Oliver inched toward the bed. He gently nudged the stack of fabric onto its side, looking at the contents. Oliver groaned, shaking his head.

This was definitely worse than yesterday.

Other than the shoes - which Oliver brushed aside for last - everything could just be described as 'tubes' of fabric. Sadly, he was familiar with each piece of fabric, as Gabrielle had worn similar items before, though only when going out partying.

Oliver sighed, grabbing the two identical lengths of clothes - a pair of stockings. His fingers slipped into the opening of one of them, and his thumb ran over the surface of the material. It was smooth, with little friction. With a frown, Oliver forced himself to sit on the bed and raise a foot, pushing his toes into the opening of a stocking.

It didn't go well. His toes caught and snagged on the material every inch or so, and it was a struggle to keep readjusting the opening to allow the nylon to slide up his leg easier. Getting frustrated, he took off the stocking and stared at it. It occurred to him - after much thought, since, as a guy, he had never pondered this before - that if he could put his foot into the foot area of the stocking directly, the rest should slide up his legs with ease.

Bunching up the material, Oliver cautiously stuck his foot in. Success! His toes found their home at the end of the stocking. He pulled and tugged the material up his leg and grinned. Overwhelmed by the triumphant success he was feeling, he marveled at the sight of the dark blue nylon gracefully coating one of his legs.

Then it came time for the second one. This was a much easier process, especially with Oliver being more cautious in how he rolled up the length of the stocking. Slowly and cautiously he unrolled the fabric up his calf and then his thigh, dwelling on the sensations. His smooth, hairless legs made it feel heavenly to have the ultra-silky nylons running against them.

Oliver stood upon completing the task, putting his feet together and twisting his legs. The effect was immediate: his legs ground and slid against each other, causing the faintest of friction between them. Oliver was left panting, biting his lower lips. It made sense now why women felt sexy wearing these. The sensations would drive anyone wild, it seemed.

Next up was an easy one, a mini skirt. It seemed to be a similar dark blue to match the stockings, and as Oliver slid them up and over his hips, he noticed an interesting effect. It seemed as though his blue legs disappeared into the tight skirt that teased midway down his thighs, like the blooming of an umbrella around his waist.

All that was of the clothing left was the top. It was a simple tube top, a bright green. Presumably, Gabrielle thought this would give a pop of color to his outfit, though Oliver wasn’t sure about it. If anything, it seemed too vibrant to go with anything, but then he realized that an outfit like this, with its bright colors and revealed skin was themed more around clubbing. Oliver just hoped it didn’t mean they’d be going out. The top clung to his body, a sad sight given the lack of curves it would normally be stretched over. Instead, Oliver positioned it to rest across his chest just below his armpits, stretching down to just above his navel. Blushing, he realized his hard nipples now poked through the thin fabric, leaving little to the imagination.

The shoes he had pushed aside were all that was left. While the wedge sandals from yesterday had a heel on them, it was more that the entire soles of the shoes were stretched and made taller. These shoes were definitively high heeled. Oliver strapped them on and tightened them, cautiously standing up. The heel - a good few inches of narrow plastic - sunk into the carpet a bit, and Oliver took his first timid steps forward.

The sandals yesterday had proved to be great practice for these higher heels, leaving him able to walk more confidently than he would have without the training. As Oliver paced around the room, he noticed his reflection in the large vanity mirror. He gasped, hands lifting to his sides in slight panic.

He was hot.

He definitely didn’t look like a girl, but more like a feminine tomboy. He realized that his longish hair, shaved body, and feminine clothes were all coming together to make him look far more girlish than he would have thought possible. And he liked it, as evidenced by the rapidly swelling bulge lifting his skirt up. Oliver couldn’t process why he liked it, though. He whined softly and sniffled as he tried to hold back the sobbing he knew was coming. This look was destroying his mental image of himself as a guy, and instead of getting mad he was nearing a breakdown.

As if on cue, Gabrielle swooped through the door, jumping at the sight of Oliver. He turned away from the mirror to face her, tears in his eyes. “I… Look at me… I’m such a freak,” he whimpered, looking to her for support.

Gabrielle rushed forward, pulling Oliver into her arms. Normally the pair stood at the same height, but the heels pushed him up above her. “Darling, no, you’re not a freak!”

“Look at me! I… I think I look good like this, even! What does that mean?”

“Hun, listen--”

Oliver cut her off, a spark of anger in his voice. “You! Why are you doing this to me?!” He exclaimed, tears starting to flow down his face.

Gabrielle put her finger to his lips, and watched as Oliver quieted himself down. He was still crying, but softly now. “Hun, you are coming together so perfectly. You’re not a freak. I think you’re beautiful, whether you’re wearing guy clothes or girl clothes.” As if to punctuate her statement, Gabrielle rose up on her toes and pushed a kiss onto Oliver’s lips. The two made out for a long while, and by the end of it, Oliver wasn’t even sure why he’d been crying. Everything seemed to be okay at least for now.

 ===

Oliver woke up the next morning, looking around at the empty bedroom. Beside him on the nightstand was his morning tea. It seemed Gabrielle had gotten up early to get ready for work, and made it for him.

Work. The thought made Oliver shrivel up on the inside. He glanced at the laundry basket where yesterday’s outfit lay trapped inside. He sipped his tea and winced. No way could he go to work like that. He got up - taking the mug of tea with him - and started to wander through the house naked to find Gabrielle. The air was cold, licking against his shaved skin and giving him chills. Oliver hadn’t valued how much his body hair was keeping him warm, but now that it was gone it was sorely missed.

Finding Gabrielle wasn’t too difficult - she was in the kitchen, making up food. She was dressed in business casual attire, perfect for her job at the salon. She glanced at her nude boyfriend as he walked into the room. Setting down the mug, he covered himself up, electing only to hide his lower genitalia. Gabrielle couldn’t help but to giggle to herself as she stared at her boyfriend’s swollen and puffy nipples, causing Oliver to blush and whine softly.

“Hey babe…” he started, trailing off. He looked around sheepishly, before finding the resolve to continue once more. “I have work today. So… I was wondering if you could tell me where my clothes are?”

Gabrielle grinned and chuckled at him, shaking her head. “Nuh-uh. We’re not done yet.”

For the briefest of seconds, Oliver felt like he was going to get angry. After all that was his usual response to situations like this one. But it never came, instead, panic set in. The look on Oliver’s face was drastic, as he became crestfallen. “I-I can’t go to work like this!” He exclaimed, looking panicked. “They’re going to think I’m a freak!”

Gabrielle walked over, kissing her boyfriend on the lips. “Not a freak, hun. You’re perfect. Besides, don’t you have some vacation time? Take the day off if you don’t want to go in.” Oliver nodded, considering it. “Just remember,” Gabrielle added, “if you stay home while I’m at work at the salon, you still need to follow my rules.”

Oliver paced a little bit, weighing his options. This seemed like the perfect time for their 'game' to stop, in his opinion, but it wasn't. If anything Gabrielle seemed to want this to continue without an end in sight. He walked over to where his phone was charging on the counter, and made the call. It was a simple enough act - feigning the need for a little rest and recovery after a long weekend - but the implications were huge. He was giving in to her wishes yet again, and not even the need to go to work would stop that from happening.

Turning to her, Gabrielle was able to see the stress on his face. She rushed over and held him, silently rocking back and forth. After a few minutes of this quiet consolation, she took him by the hand and led him upstairs to the bedroom, where she opened a drawer in the dresser.

"Here's your outfit for today, hun. I'll help you get dressed."

True to her word, Oliver hardly had to lift a finger in putting on his clothes. He felt pampered, being spoiled by his girlfriend. She delicately rolled up a pair of tights, and - after pushing him to sit on the bed - delicately slid them up his still-smooth legs. The tights had a compressing effect on Oliver's lower half, though it was most noticeable at his crotch. It was so extreme that when the panties slipped up over his hips, his manhood had completely disappeared and was more or less smooth. The skirt that came down to his knees was a nice change of pace from the day before's extremely short selection, even if it was a plain off-white color.

The strangest part, though, was the bra that Gabrielle insisted that Oliver wear. Fishing his arms through the straps wasn't too bad, though he wasn't sure how he would have fastened it had Gabrielle not been helping him. The strangest part was that, once fully seated on his chest, the cups were full. Oliver frowned, tentatively squeezing his chest while unaware that Gabrielle was hungrily watching him. In the end, he rationalized that the bra had to be padded, but that still didn't explain why the bra rubbing on his nipples felt so stimulating and good. It didn't help that the light blue blouse Gabrielle put on him was designed to accent the wearer's bust, making it looked like Oliver had a modest curvature on his torso.

"Shit!" Gabrielle called out, rushing toward the door. "That was too much fun, I'm running late!" She doubled back, giving Oliver a strong kiss on the lips while running her hand through his hair. While making out, Oliver was puzzled by how far she was able to drag her fingers against his hair, as though it were longer than he remembered it being.

"Remember," Oliver's girlfriend warned, "you need to follow the rules. That means staying dressed like that all day. And don't get carried away!" Gabrielle grabbed at Oliver's compressed crotch, making him whimper softly in pleasure before she sprinted away out the door with a giggle.

Oliver looked around the room, and back into the dresser drawer. There was something tucked in the back, that both of them had missed. It was a pair of high heeled shoes, constructed entirely of leather. The ankle strap was slightly thicker, and had unlocked padlocks around them. Oliver teetered back and forth on the balls of his feet, sighing. He walked around the room, feeling the carpet through his nylons. It was intense, and his toes curled automatically as he paced. After a few laps around, the stimulation of fabric on fabric was too much to handle. Oliver grabbed the shoes, and slipped them on.

The only way to actually fasten the straps was to engage the locks. One for each foot, they dangled there, taunting him. He knew Gabrielle would want them fully on. He even wondered if this was her testing him. Shaking his head, he let go of that train of thought. He had to trust her, and right now, he had to trust her to have the keys. He snapped the locks shut, sighing from the pent up stress of the decision.

Walking on what felt like his tiptoes, Oliver made his way out to the kitchen and grabbed his phone again. He took a picture of the shoes on his feet, and after triple checking who he was sending it to, delivered it to Gabrielle. Her response was immediate.

Gab: I thought we missed something!

Gab: Show me the whole outfit!

Oliver gulped, propping his phone up on the counter to record himself. Backing up, he found enough space to be fully in frame and then on a whim did a slow spin in place. The skirt he was wearing was especially twirly, and he couldn't help but to giggle as it fluttered up and around his legs. He teetered back over to the phone and stopped the recording, hitting send.

Gab: Perfect! You look beautiful!

At first, Oliver blushed at the compliment, then he was mortified. What was he doing? Why was he doing this? Panic set in as Oliver played back the video. Fuck, he looked so girly. It was humiliating but also... strangely arousing. That part scared Oliver the most. He pressed his hand against his member, but despite being turned on, nothing was happening down there. He pulled down the skirt, the tights, and the panties, only to find himself completely soft. If anything, he was a little wet with precum.

That was too much for Oliver to handle. He couldn't wear these clothes any longer, consequences be damned. He pulled off the blouse and shucked the bra off over his head, and slid off the skirt. But then, a problem. He wouldn't be able to get his tights off without removing his heels, and those were locked on. He thought about cutting the straps of the shoes, but the risk of accidentally hurting himself was too high.

"Fuck," Oliver whispered, looking down at himself. He didn't have many options. He pulled his tights back up and laid down on the couch. From the hips down, he looked entirely feminine. It didn't help that his nipples were still swollen. This wasn't going to work, he decided. He needed a distraction until Gabrielle came home. Then he'd straighten this all out.

 ===

The front door silently opened a few hours later, shortly after what would have been lunch time. Gabrielle creeped in through the entry hall, looking into the living room to find her boyfriend sitting on the couch playing video games. Well, 'playing' wasn't exactly the right turn of phrase, since the game was paused, and one of his hands was idly playing with his nipples while he breathed heavily while the other was rubbing the layers of fabric between his legs.

"The slut..." Gabrielle muttered to herself, upset at seeing her half-naked boyfriend clearly disregarding both of the rules of the day. She dropped her shopping bags, the sound alerting Oliver as she stormed into the room.

"What do you think you're doing?!" She snapped, standing in front of him.

To his credit, Oliver immediately stopped playing with himself, fumbling around for long moments as he reached for his game controller before stopping himself. He sat awkwardly, covering both his crotch and his chest.

"I ought to kick you out right now! Who do you think you are, not following my rules?" Gabrielle stormed over, scooping the discarded bra and blouse from the floor and throwing them onto the couch next to Oliver.

"I... I just... I can't..." Oliver stammered, struggling to find his words.

Gabrielle stood in front of him, arms folded. "Explain yourself to me." Her voice shook Oliver to his core. She didn't even say it with anger or any other emotion, and that was what unnerved him the most. It was calm, demanding, and insistent. She was in control, and they both knew it.

Oliver bit his lip, looking over Gabrielle and then himself. How would he tell her that he was liking this, perhaps a little too much? Or that he found himself hot? Or that he was getting aroused by himself, and aroused like a girl at that? A part of Oliver, the old hyper-masculine part that had to be right and macho and in charge, rebelled. All of this was Gabrielle's fault. If they had just done what he wanted that night, none of this would have happened. His anger built up like a fire inside him, swelling and preparing to consume his emotions like kindling...

And then, it was gone. Like a house of cards that fell apart, his emotions tumbled away. He was left feeling vacant and empty, before, rushing in, came sorrow. Oliver let out a whimper, tears forming in his eyes. Within moments the dam burst, and he was reduced to a sobbing mess in front of his girlfriend.

Gabrielle watched, stunned. She felt terrible for having broken him down like this. Kneeling on the couch beside him, she pulled him close and stroked his hair. She let his face get smothered in her own chest, muffling the sounds of his tears.

"It's okay hun, I know a lot has been going on," she whispered, patting his back. "Don't worry, we're going to get through this. Since you had an issue today, and didn't do what I told you, we'll be spending the rest of the week together. You're gonna come to work with me at the salon, and we'll bond and become closer than ever."

Oliver lifted his head up, sniffling. His eyes were large and doe-like, lip quivering. "Fuck... why am I crying?" He said to himself. "Are... are you mad at me still?" His voice trembled as he asked.

With a shake of her head and a soft smile, Gabrielle gently replied, "Of course not. Now, I'll stay home the rest of the day. Let's get some food into our bellies!"