Time with Antonio, waking up with a new outfit

Tyler’s breath quickened as he heard the footsteps approach the door. He wanted to run, to hide, to cover himself up, but he couldn’t move. He laid on the bed, torso propped up on his elbows with his silky smooth legs crossed over one another to try and hide his raging hard dick straining his silky red panties.

Antonio stepped into the door wearing a white button down with far too many buttons undone showing off his manly chiseled pecs covered in a tuft of chest hair. His shirt was tucked into a pair of tight fitting grey trousers that showed off his muscular bottom half, as well as his clearly well endowed bulge. His brown hair was long and wavy, looking soft and full with the carefully applied gel and mousse giving it a carefree look. His chiseled jaw turned to a smile as he saw Tyler laying out before him in slutty red lingerie. Tyler didn’t realize how he was positioned looked like he was waiting for Antonio and presenting his feminine body for him like a lingerie model.

Antonio looked from Tyler’s pretty painted toes up his shiny smooth legs that looked so soft to the touch. The red boy shorts were silky and just as inviting as his legs. He couldn’t see the bulge in the front but he assumed Tyler was playing it coy with him, the little minx. The red bustier brought in his waist just a bit giving him an even more feminine figure. He knew from earlier Tyler didn’t have much in the way of breasts, even with his nipples looking much more feminine than a man’s, but the bustier made it look like he had a little something there, even making a small cleavage. But his beautifully made up face, even with just this light make up, brought him from pretty boy to very attractive “girl”. There was still boy in there but not much.

“Well well well, hello Bella!! Did you do this all for me? Did you get your friend to help you look all pretty for me?? Good girl” Antonio sauntered towards Tyler, looking like a jungle cat about to pounce on its prey. Tyler tried to scoot back away on his bed but Antonio grabbed his hands in a soft but firm grip, pulling him up to standing next to the tall Italian man. “Holy shit he’s strong!” Tyler thought as he was suddenly standing and looking up at the handsome man.

“Antonio it’s not what it looks like! Britney was here to *gasp*….. mmmmmHhhhnmnnnnm!” Tyler tried to protest but Antonio had pulled him in close with his strong hand firmly gripping his panty covered butt. His other hand grabbed the back of his neck and pulled his face towards his own and kissed him! Tyler tried to protest and push away but it was like pushing a steel wall of hard muscle. He tried to speak but that just allowed Antonio’s tongue into his mouth, dancing with his own. Tyler’s protests melted away as the kiss was… good? Really good. The kiss was such a stark contrast for him as Antonio had taken control And left him as the submissive. The stubble on Antonio’s cheeks was so different when experienced from the other side, but also thrilling. Feeling how powerful and masculine Antonio felt was a whole new experience for Tyler and made him feel so small and emasculated. Plus, the feeling of his lingerie, the big strong hand massaging his butt, felt so good but humiliating at the same time. Tyler hated kissing this man, but his body couldn’t get enough. So much so that when Antonio pulled away, Tyler found himself trying to lean forward with puckered lips trying to kiss him again. He opened his eyes and realized what he was doing, shaking his head to get a grip on the situation but the and horniness was making it extremely difficult.

“Mmmmm your lips taste even better with lipstick on Bella. And I can tell that that little blonde bimbo didn’t just help you get dressed. I can still taste her on your lips. That’s alright with me if you like to have some fun on both sides, bellisima. We can still be together and have some fun on the side mi amor. But I can see that a real man is more your taste” Antonio smirked as he looked down at the wet tent in Tyler’s panties. Tyler was about to say something but quickly forgot it as Antonio’s big hand engulfed Tyler’s pantied cock with his palm, gently rubbing in slow circles.

“MmmmmMmmmmMMMM uunnngghhhh oh my god” Tyler moaned in a much high pitched voice than normal.

“Mmmm that’s right. You need a strong man like me to make you feel good, not some girly girl. You are the girly girl. And you want to be pretty and feminine and submissive. Tell me, Bella. Say it to me, Tara”

Antonio kept rubbing with soft but firm pressure over his silk covered dick. Tyler grabbed a hold of Antonio’s big strong arms for fear of his legs collapsing from the pleasure. He bit his lip and closed his eyes, trying to hold back the moans and pants Antonio was trying to get from him. But when his hand went from circles to sliding his fingers slowly up from his panty covered balls all the way up his shaft and slowly rubbing circles along his head, Tyler gasped and moaned opening his eyes wide looking up at his Italian clothier.

“Mmmmmmm unnghhhh!…… yes” Tyler moaned and softly answered unable to stop himself.

“Mmmm no louder, sissy girl. Say it louder and with meaning.” Antonio ordered moving his hand up to Tyler’s bra covered chest and massaging it.

The silk rubbing against his newly sensitive nipples made him moan even louder, making him bit his crimson covered lip.

“Yesssss! Mmmmmm! Omg yes. I’m-I’m a girl…” Tyler moaned not able to stop the humiliating words coming out of his mouth. The booze and horniness were getting to be too much and he was losing control of his body.

“Louder Tara! Say it with pride mi bellisimo!” Antonio slipped his hand under the cup of his bra and started toying with his sensitive nipples as he gripped Tyler’s cock for the first time.

“Aiiiiieeeee!!!! Yes! I’m a pretty sissy girl! I’m your sissy girl omg omg omg!!” Tyler’s eyes went wide and his mouth into an O as he was so close to cumming but Antonio slowed his ministrations. He grabbed Tyler’s manicured hand and brought it to the large bulge straining the front of his tight grey slacks. Tyler’s hand lightly gripped the massive bulge from habit in his drunken and horny state. “Holy fuck he’s huge! That’s gotta be fake no way that’s real” he thought to himself. He began moving his hand around exploring and trying to figure out just how Antonio was so big down there, thinking there must be padding or stuffing down there somewhere.

“Mmmm that’s right, my Tara. Good girl. I know you want my cock so bad. You were very descriptive in my store just how bad you wanted it. But you have to work for it sissy Bella. You must work for Daddy’s cock, and I don’t think you’ve earned it yet.”

Tyler realized what he was doing listening to Antonio and quickly pulled his hand away from groping this guys dick. But Antonio took that as Tyler being an obedient girl and smirked.

“But, with all the effort you went through today, I think you’ve earned some relief, even though you were a little lesbian slut. Lay down, bellisima.”

Antonio put his hand gently between the cups of Tyler’s bustier, right on the bow, and firmly pushed him back onto the bed. Tyler’s brain was no match for it and fell back with his arms above his head. He looked down his body and saw the small swell the bustier made on his chest, as well as the much larger swell in the red silk panties. He looked up at Antonio with a mix of fear and lust as Antonio smiled before putting one knee on the bed between Tyler’s spread legs and returning to massaging Tyler’s swollen member.

Tyler moaned and squirmed in the bed but Antonio’s free hand held his hips preventing him from moving away.

“That’s it girl. You’ve been such a good girl for Daddy. I’m going to make all your dreams come true, just like you told me in the store. You’re gunna be my pretty feminine sissy girl. You’ll wear all the most beautiful clothes to show off this tight little body. Hair done like a model. And you’ll be on my arm as I show off that tight little ass of yours” Tyler squirmed hating what he was saying but the firm and incessant rubbing of the silk on his cock was getting him close.

“That macho attitude of yours will be gone and all that will remain is a little sissy submissive girl. That’s what want isn’t it? That’s what you told me in the store. Tell me again and I’ll let you cum baby girl”

Tyler had no idea what he was talking about but he was too far gone. The silky fabric of the panties was delightful. He had brought a hand down to his nipple and was furiously rubbing and pinching it, sending electricity through his chest. Antonio’s hand on his panty covered cock was incredible, better than any pussy he’d ever had. He looked into Antonio’s eyes and tried to bite his lip to stop the words from coming but they came anyway.

“Yes! YES! Please! Anything! I’ll be your sissy girl! I’ll wear pretty outfits and show off for you! Just let me cum please!”

Antonio smirked “Good girl. Cum for your Daddy”

And that’s all it took. Tyler’s back arched leaving just his shoulders and but touching the bed. His hand was pinching his nipple hard. And his cock exploded cum into his panties. Wave after wave of euphoria crashed through him as he let out a scream that would put a porn star to shame. His cum flooded his panties, soaking the fabric. His cock head poked out of the top and the last few spurts shot out so powerfully that the covered his bra covered chest. One even landed on his crimson lips, a dramatic contrast between the red and white.

Finally, his orgasm began to subside and his body collapsed to the bed, leaving Tyler gasping for air. He opened his eyes and saw Antonio’s handsome face above his own before he leaned in and gently kissed him on his cum covered lips.

“Good girl, Tara. That’s what happens when you’re a good girl for your man.”

Tyler’s eyes started to flutter closed, unable to stay awake any longer. The last thing he remembered was Antonio saying “don’t worry, Bella. I’ll put your new suits up and take care of your old suits. Tomorrow starts your new life, sissy, just like you asked for.”

And then darkness……

….. Tyler came to with his eyes fluttering. He found himself standing in his kitchen pouring a coffee and his coffee mug was overfilling and spilling over the counter. “Shit shit!” He yelled in a high pitched voice, stepping away from the liquid mess on the counter.

He instinctively looked down to make sure he didn’t get anything on himself and saw he was wearing a light blue suit. Light blue would be an understatement as it was almost powder blue in its color. He didn’t have any powder blue suits? He also didn’t remember getting dressed that morning at all.

He quickly cleaned up the spill and saw he had oat milk no sugar creamer and no sugar caramel syrup on the counter next to the coffee. He always took his coffee black, what was this fruity shit on his counter? He started walking to his bedroom and His feet made a click clack noise and he looked down and saw shiny patent leather shoes on his feet. Not anything very out of the ordinary, but he didn’t recognize them and the style was odd. He kicked his leg back and saw the heel was a good 2-3 inches of Cuban block heel, much too high for a man to wear. He also saw that his pant leg was much too wide cut at the opening before getting skin tight at the thigh. Tyler hurried his step, being careful with his new found height in heels taking smaller steps, into his bedroom.

Standing in front of the mirror, Tyler couldn’t believe what he was seeing. His normally masculine hair wasnt slicked back with gel like he normally had it. It was combed and fluffed into a very femmy yet somewhat androgynous hair do with sweeping bangs and the back and sides just barely missing the base of his neck. The two studs in each ear were on display, adding to his feminine look. While his face didn’t look much different, well besides the bigger lips and fuller cheeks and manicured eyebrows, it was leaning much more femme than androgynous, let alone masculine. He thought something looked a little off and looked closer, seeing that his eyelashes were fuller and darker probably from mascara. His cheeks just a touch too rosy from blush. And his fuller lips were slightly shiny from gloss. And did his nose look smaller? Was that contour on it?

While that wasn’t too bad, his outfit really rocked him. He was wearing a powder blue suit that looked more like a woman’s power suit than anything a man would wear. Besides the color, the jacket was cut differently, tailored tight around the waist giving the illusion of a larger chest and hips that only had a single button at the navel. The jacket was long coming to just above the bottom of his butt cheeks, but just not the style for a mans jacket. Underneath he had on a white button down tailored the same at the waist as his jacket but the buttons were on the wrong side. The material was silky and had some shine to it. It was buttoned to the neck but instead of a usual tie he wore a long string silk bow tie. The bow drooped down his chest, with the ends of the silk tie falling around nipple level.

His pants were the same powder blue with a wide cuff at the ankle, covering most of the 3 inch heel when standing still. At the thighs the fabric became skin tight, showing off all the curves of his thighs and especially his butt. The material seemed to form around his butt, showing off every curve of the two globes, even wedging itself between the two for added definition. Thankfully the jacket covered the tight pants in the back, mostly. There was no zipper in the front, only a side zipper, and also no pockets on the front or back. Clearly these were women’s pants! What made it even worse was the flatness in front where normally he would have a bulge!

Tyler lifted his leg and saw what might be socks underneath but was just slightly too sheer and shiny. He had felt the silky smooth sensation on his legs of what he feared but he had to make sure. Lifting his pant leg he saw not socks but almost opaque black stockings on his legs. He tried to unbutton his pants in the front like normal but there was nothing to unbutton so he unzipped the side zipper and peeled the tight fabric down his thick thighs and butt.

Removing his pants to his knees he saw he was wearing a silky powder blue thong underneath, matching his suit. The waist band was seamless, apparently to hide panty lines, with a lace detailing on the front covering what would have been his bulge if one was there! He lifted the front of the thong to look under and saw his heart shaped pubic hair but under that there was just a flesh covered tape. Following the tape down, it went under and between his legs, holding back his tucked cock with his balls pushed inside of him. The tuck tape had given him a flat girly front!

Letting go of his thong with fright of his newfound undercarriage, the silk thong snapped against his skin. Next to his thong with six garter straps attaching to the lace welt of his stockings on his thighs. He couldn’t see what the stockings were attached to, but his difficulty breathing gave him a clue. He struggled with the wrong sided buttons on his shirt before pulling them apart, revealing a powder blue corset!

The corset was underbust, stopping just below his chest, but was rounded underneath to provide support to his tits, if he had any. The panels were powder blue with a white lace detailing throughout. The metal busks were heavy duty, as well as the boning underneath. Turning around he saw the corset was pulled very tight in the back, the two sides almost touching. But what was worse was the laces were tied in a bow that was just out of his reach! Try as he might, with how tight the corset was he couldn’t quite reach the laces to remove the damn thing! After struggling for a few minutes, he gave up and sat down on the bed panting for air from his exertion.

He had taken off his shirt jacket and pants trying to undo this damn corset so he sat on the bed huffing and puffing in just the corset, thong, and stockings with his heeled shoes on. Looking down, it was hard to imagine his body wasn’t some flat chested girls. Even his nipples looked feminine and puffy, larger too. The corset brought in his waist, accentuating the difference between his chest and hips and waist, making a more prominent hourglass. With his thong presenting a flat front, his legs encased in shiny black stockings, he had to admit he looked hot.

“Fuckkk this is too much! Antonio must have did this after I passed out! No way I would have dressed like some fag and wear this lingerie!” But the memory of him begging Britney the night before to wear lingerie came to him, as well as all the pleasurable feelings of her and Antonio. He shook his head and stood up on his heeled feet, wobbling a bit for a moment.

“I gotta get out of this stupid shit. At least get one of my normal suits on.” He clicked over to his walk in closet, unconsciously rolling his hips due to the heels, and opened the door. Instead of the normal black, greys, blues, and neutral colors that normally awaited him, a barrage of bright colors assaulted him. In place of his normal Armani and other high end suits were an array of feminine looking suits, each more feminine than the last! Pinks and salmons, powder blues and purples, white and even red suits, all with varying differences in their femininity. There were even a few with pencil skirts rather than pants! On hangars were various dress shirts that changed to straight up blouses with ruffles and pussybow neckties. Some were low cut, very low cut that would be attention grabbing with the right chest size. Others high necked but with sheer cut outs on the chest. Ruffles on shoulders and sleeves, bows and lace were everywhere. All screamed femininity and corporate slut.

On the wall opposite where his dress shoes used to be, all Italian leather, stood feminine dress shoes like the ones he was wearing and all of them had at least a 3 inch heel! Someone weren’t even pretending to be men’s shoes, but straight up women’s heels! Pointed and rounded toes with stilleto heels 4 inches tall or higher, all in different colors as well.

He remembered vaguely Antonio saying he would put up his new suits and take care of his old ones. This must’ve been what he meant!

Tyler backed away from what used to be a bastion of gentlemanly masculinity and was now a businesswoman’s power suit treasure trove, Tyler slammed the door closed on it. Breathing heavily he clicked over to the bathroom, carefully mincing with his faster pace and swung open the medicine cabinet. He could feel himself having a panic attack and dry swallowed two Xanax to curb it. Mincing over to his headphones, he slipped them on, needing to meditate and relax and figure out his next move.

He closed his eyes and breathed deeply, or as deeply as his corset would allow, listening to the crashing waves and soft music. He thought he could hear a soft voice amidst the wind and waves, but he couldn’t make out what they were saying…..