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Chapter 5
by Cdslavejessie
What happens the next week at work?
Tyler’s drive home and new wardrobe
Tyler sat in the back of the car, relishing the Xanax coursing through his veins so he didn’t panic. He had gotten out of that spa and out of the hands of that…. That…. Woman who did this to him! What the hell did she mean he asked for this? And what was all that about a conversation? Tyler had basically fall asleep immediately on the massage table and barely remembered speaking to that bitch. There must have been a mix up in his paperwork. Yeah, that must be it, cause there’s no way he’d ask for all of…. This! He’ll sue the place and end up owning it by the end of the week!
But he could fix this. None of this was permanent. His hair would grow back, eventually! The ear piercings would heal. And the filler would disappear after a few weeks, or so all his ex girlfriends said when they complained about how often they needed touch ups.
Feeling a little better from his ordeal, he was brought back to reality by the shoulder strap of his bra digging into his skin. The tightness of the feminine garment on his chest was very noticeable. But…. It did feel… kinda nice? He touched his chest through the shirt and the soft satin of his pink bra on his nipples felt electric. He continued to rub his nipples loving the feeling. And the tightness of the bra felt comforting in a way. The same went for the garter belt and stockings. For some reason, the tight construction felt…. Good. And the silk stockings on his legs felt amazing, no denying that one. He couldn’t stop rubbing his legs together. And even the panties and their satin fabric felt amazing, even with his dick tucked back between his legs.
Tyler didn’t love this new revelation about his girly underwear and needed to relax. It wasn’t like he could just strip down in front of this driver, who was eyeing him quite a bit in the rear view mirror. Fuck, was he just watching my touch my nipples?? He can’t see through my shirt can he? What was he some sort of queer? Was he gay and wanting to fuck him? That’s disgusting, I’m a guy dude!
Needing to relax, he slipped in his ear buds and put on his meditation, feeling like he needed it more and more with every crazy day. The crashing of waves and soft feminine voice filled his ears as he closed his eyes….
The next thing he knew, he was walking away from his penthouse door. Stopping in his tracks, Tyler did a look around trying to figure out what the hell just happened. Damn that Xanax is no joke. I don’t even remember getting home. He looked down and saw he was holding the broken down boxes that were in his apartment this morning. “Huh, that’s weird? I don’t remember opening them up? Xanax is wild” he said aloud.
But then he noticed he had changed clothes. Instead of the white t-shirt, he was wearing a tight fitting light blue work out tank top with thin straps. The bottom hem didn’t come down to his waist, so a few inches of his toned stomach poked out underneath. He’d gotten it to work out in during the summer awhile back but saw how fruity he looked in it and never wore it again. The ruffles from his bra straps (not his bra damnit! This isn’t mine!) were clearly visible poking out of the thin straps. It was so tight you could see the ruffles of the bra through the tight top.
He’d changed also changed into tight compression leggings, normally worn under his running shorts during cold weather. The shiny black leggings were very tight, showing all the details of his legs, especially the garters still attached! But the front where he’d normally have a bulge was flat from his tuck. They were capri style, showing off several inches of ankle and he wore no socks so his pink toe nails were on display!
Tyler panicked, being out in the open dressed like some twink! He rushed over to the garbage chute to get rid of the boxes and then ran back inside his apartment before someone else could see! Breathing heavy leaning against the door, Tyler wondered what the fuck just happened. Clearly the Xanax had gotten to him, that’s the only explanation. And from all the girly shit hed been through that day, his brain must’ve short circuited and put this on. Yeah, that’s it! It’s gotta be. But much more clear minded, Tyler was determined to masculinize himself again.
Going to his bed room, Tyler threw off the baby blue tank, exposing his girly pink and white bra with ruffles and lace. Struggling to get the tight compression leggings off him, he finally was able to with a huff. Standing in the mirror in just his white and pink lingerie, Tyler looked at himself. The white stockings made his legs look extremely feminine, and combined with the garter belt look more sexy than cute. His pink panties with the white lace on the edges and white bows looked so girly, especially with his flat front from his tucked cock. He turned around and looked over his shoulder, seeing his hairless butt covered in satin and lace framed by the garter straps looking even more perky than normal. The garter belt gave this “cute” bra and panties set that extra bit that made it into a sexy lingerie set. The pink and white motifs giving a cute innocent vibe but with a side of slut when combined together. His bra, while unlined and providing no padding, outlined where breasts would be, giving the impression he had a small pair. The bows and frills and ruffles were so girly he wanted to puke. The earrings and arched brows gave his pretty boy face a much prettier foundation. With the filler in his cheeks and lips, he was on the verge of girl/guy with his pink lingerie.
His brain saw a faggy twink and railed against that reality. He was a very successful business man and an alpha dog. He fucked women and left them, just like he did to the businesses he acquired. He wasn’t some pretty boy twink! But for some reason, his body enjoyed what he was seeing. Not that he wanted to fuck someone who looked like this. His body liked that HIS body looked like this. And his body let him know that from the sudden tightness in his panties as he dick tried to get out of its tuck. He felt his nipples harden and a tingly feeling inside him.
Out of their own accord, he felt his hands go up to his satin bra cups and gently rub his hard nipples. He lightly gasped as he made contact, the soft satin brushing his hard nipples. His mouth was slightly parted as he gasped, his newly plump lips looking like so many of the girls he fucked as he did the same to them. He closed his eyes as He moved one hand down to his panties, feeling the smooth skin of his hairless torso on the way down, and gently rubbed his tucked cock through his panties. Electricity shot through his fingers into his cock entering deep inside him as he rubbed, causing him to moan.
He opened his eyes and saw a slutty feminine figure in the mirror touching themselves. He saw a wet spot form in the gusset of his panties. He snapped back to reality at that moment, realizing what he was doing. His hands snapped away like they’d been shocked from his intimate areas as he began taking off the lingerie. He struggled with the bra and the garter belt and stockings, but ultimately was able to get them off in his mad haste to return to masculinity.
Finally, with his girly finery off his body, he was naked in his bedroom panting for air. “What. The. FUCK. Was that?!?!!” He said aloud to himself. Shaking his head, he stepped over to his big black dresser to get some normal underwear on. But when he opened his drawer, typically filled with dark and neutral colored boxer briefs, he was assaulted by a rainbow of colors, all in silk and satin and lace. His drawer was filled with panties of all different kinds. And not Hanes 5-pack cotton panties either. High end boutique style all made of silk or satin or lace. Some were even leather and latex! All varieties ranging from somewhat modest boy shorts (with lace edging so there’s no mistaking it for girly panties) to tiny little g strings with just a piece of floss for a back! There were some that were confusing contraptions of straps and and strings that would be incredibly sexy when worn but confusing to look at on its own.
Tyler opened the next drawer and saw where his undershirts used to be were all the matching bras for his panties. Some were unlined for AA cups like the one he was wearing earlier, but others were padded with lots of push up. One he held up with a leopard print and rhine stone straps and lots of padding said it was a 32 DD! Others, like the panties, had straps and buckles that dangled from the cups that would look enticing when worn. There was even a black bra with leather cups but with a sheer lace that covered the upper chest that went into a high collar choker. There was a heart shaped ring attached to the choker in the front with a lock on the back of it. Tyler shivered thinking about wearing that and being locked into it.
And of course his next drawer that was his sock drawer he knew what he’d find. Instead of his men’s socks there were dozens of stockings, all incredibly expensive stockings or all sorts. From rather modest office type stockings to ones with a sexy back seam to slutty fishnets a hooker or stripper might wear. Some were hold ups with a thin silicon ring along the welt to grip to your thigh, but most needed garters, which Tyler now had plenty. Some were simple, but sexy, garter belts meant to hold up the stockings. Others were higher waisted with laces in the back to cinch in your waist. Some were garter skirts, form fitting over your hips and down your thighs before connecting to your stockings. There were a couple pairs of “socks” but all were incredibly girly. Some were knee or even thigh high socks with bands of pink at the top. Others were ankle socks with a ruffle of lace at the top.
And a final drawer had corsets and nighties and teddies. Some were pretty, designed for lingerie and to be seen and not as waist cinching. But the majority had full boning, meant to cinch your waist and train it to remain an hour glass figure. Full cups and half cups corsets. Waist cinchers and waist trainers. Most with a single base color with a decorative black floral design over it. There was even some leather and latex corsets of black and pink and red. Some of them had locks on the back. There were baby doll nighties of all colors, some with a poof of fur around the bodice and bottom hems. There were lacy teddies and body suits. Leather and latex ones as well. Several camisole sets of silk and satin to be worn underneath blouses, or so he believed. There were even several pairs of elbow and arm length gloves of various fabrics.
Tyler was dumbfounded. How did this happen? Where did this come from? And why was it in his drawers? He looked around his room and couldn’t find his normal underwear or shirts or socks anywhere in his room. Where were his normal clothes?? He needed to figure this out but couldn’t do it naked.
He went to go put on a pair of gym shorts without underwear, but suddenly the thought of going commando disgusted him. He’d never had the issue before, but now He couldn’t bring himself to do it. So begrudgingly he rifled through his panty drawer and found the least offensive looking panties. They were a satin pair of royal blue boy shorts with just hints of light blue lace along the waist band and leg holes and light blue bow above the crotch. He stepped into the panties, hating himself but also loving the satin feeling on his skin as he pulled them up. He adjust the panties, finding they fit decently well like a pair of trunk boxer briefs, except they left a bit of the bottom of his butt cheeks out and was just a bit tight in the front. Completely unwilling to tuck his dick, he let it ride with a bulge in the front.
Seeing the panties he willingly put on humiliated him so he pulled on a pair of gym shorts to cover his shameful underwear. He opened his walk in closet, thankful to see it still held his suits and more casual mens wear in there, and grabbed a t-shirt and threw it on. He looked down and saw his pink painted toe nails and needed to cover those up too, so he begrudgingly put on a pair of white knee high socks with pink bands at the top.
Covering the majority of his feminine appearance, he went over to his home office and booted up his computer. He had security cameras installed in his apartment awhile back. While he’d never had an issue with security, they did serve as a nice home recording for his escapades in the bed room. Did the sluts he bring home need to know about the cameras? Absolutely not but he wasn’t a monster. If they asked he would tell them about it, he just didn’t openly let them know before hand.
Tyler rewound the footage back to when he entered the apartment from his doorbell camera. From there, he watched himself walk up and open the door, humming a little tune to himself. His outfit looked a little different on him. It looks like he hiked up his tight joggers so the crotch and ass were tight against the fabric. And his white T-shirt was tied in a knot in the front, showing off more of his stomach and much tighter too, clearly showing the bra he was wearing. He didn’t remember the shirt being tied up or his pants being so tight.
He followed himself on the cameras walking in and noticed he was walking differently. His elbows were tight at his sides with his arms slightly out and wrists turned outward. His hips rolled with each step, rolling his butt from side to side. He looked like a gay sissy flaunting himself.
The Tyler on screen saw the packages next to the door and did a girly screech, clapping his hands together and jumping up and down. He watched as he grabbed a hand full of boxes and carried them into the bed room, making several trips. Once all the packages were in, he saw the Tyler on screen open his dresser drawers and shove all of his boxers and socks and shirts into plastic bags and setting them aside. He then stripped down to his pink lingerie and preen in the mirror like some Instagram lingerie model. Posing with his hip cocked or bent over or looking over his shoulder at his panty covered butt blowing kisses to the mirror.
Then he saw himself open each pink box and pull out the lingerie lying within. He couldn’t believe it was him pulling out each piece, oooo-ing and ahhh-ing them, holding them up against himself. The Tyler in the video didn’t say much, just mostly girly sounds of excitement. He saw him look at his phone to check the time after holding out a dark green “teddy” made of straps and lace that had more holes in it than fabric, shake his head and put it in the drawer. “Next time” he heard himself say, but much higher pitched, sounding like one of those drag fags on the show.
Tyler fast forwarded, not able to watch the flamboyantly feminine figure gush over the lingerie before carefully placing it in the empty drawers. It must’ve taken at least an hour for all them to be unboxed. Once complete, he watched himself grab the leggings and tight tank top from his closet and slip them on, sighing contentedly once they were on. He grabbed the trash bags full of his guy underwear and take them out the door and to the garbage chute! Wiping his hands clean, he returned to the apartment, same hip swaying arms out motion, and come back with the boxes broken down.
But then, mid step, he saw himself stop and shake his head. That must’ve been when he came to and realized what he was doing!
Tyler closed the laptop and leaned back in his chair. How did this happen? It must’ve been the Xanax and that Jillian bitch’s weird feminization that fucked up his head. That’s the only explanation for why he looked and acted like a sissy. He needed to get this out of his system and decided to head to bed.
He remembered that Jillian said he could have severe side effects if he didnt take care of his skin after his treatments. Sighing in exasperation, he went over and grabbed the instructions and products Jillian gave him. Not one against using products to better his skin as he used quite a few already, he just hadn’t really used any on his body. Tyler stripped out of his clothes, including his panties. Reading the instructions, he lathered up his hairless skin with two different oils to add some vitamins and other essentials to keep his skin Healthy and soft. Followed up with a gentle moisturizer, he rubbed it all over his body, giving his skin a gleam to it especially on his legs. With his legs looking like a women’s razor commercial shining and gleaming, he moved on to his face. Adding oils and acids to keep his skin healthy and hydrated. Followed up with a hydrating night mask. Applying some anesthetic to his piercings and a lip mask to his now plumper lips, Tyler saw that it had taken him a good 45 minutes to get everything done. “Damn this is gunna be annoying every night!” He said aloud.
Tyler normally slept in a t shirt and boxers in bed. But with his underwear now gone and unwilling to sleep naked, Tyler slid back on his silky boy short panties and put on a loose fitting t shirt. With the loose fit shirt and tight boy shorts, Tyler looked in the mirror and saw he looked more like a girlfriend borrowing her boyfriend’s shirt than he did a man. Humiliated by the view in the mirror, he slid into bed and turned off the lights. But not before having his relaxation playlist playing on his bedroom speaker….
The next week at work…
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Blank Spaces
A ruthless business man has some blank spots in his memory
Tyler Matthew’s is a cutthroat business man who always gets what he wants, no matter who is left behind. But he starts having holes in his memory, and when he wakes up, there’s changes to his life. Very feminine changes
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- Femboy, lingerie, sissy, trans, make over, mind control, hypnosis, gay, crossdressing, humiliation, panties, feminization, bimbo, high heels, crossdresser
Updated on May 7, 2024
by Cdslavejessie
Created on Mar 15, 2024
by Cdslavejessie
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