Leaving work and a workout at home

Hi girlies and boys!!! Sorry for the delay in writing! Was on vacation enjoying the sunshine! But now I’m back :) the chapter got away from me again (what a surprise, Jessica got wrapped up in writing about outfits again) but the next chapter will accelerate the timeline a bit so more dramatic changes can happen to our corporate bimbo :)

Love you and missed you all :)

Mwah!!

-Jessicaxoxoxoxxxx

Tyler’s first day flew by in the blink of an eye, at least it seemed that way to Tyler. Suddenly, it was 5 pm but it felt like he had just arrived at the office. Blaming it on the stress of the last few days, Tyler surprisingly took it in stride, not realizing his conscious thoughts were being manipulated to be more accepting of his blank spaces. He walked out of his office into the secretary office. Well, walk wasn’t the best way to describe it. Tyler more wiggled, due to his heeled shoes, tight waist cincher, and plug still lodged in his butt.

Charlotte was once again shocked at her boss’s appearance and body movements. He had messaged her saying he was to be left alone for the rest of the day right after Peterson had left and to cancel the rest of his day. His voice sounded odd on the intercom, a little higher pitched and a little… gay? He had also called her honey as he signed off. Odd. Everything was odd. While it wasn’t unusual for him to cancel his day as Tyler would normally do that when he wanted to go golf with his fellow finance bros, but he just stayed locked in his office all day. She had forwarded him several emails and messages with no response, so as normal Charlotte handled it. Charlotte was a competent business woman so all these items were no problem for her to handle.

But seeing Tyler come out of his office, the shock of his outfit was crazy. His powder blue suit was more a pant suit than a man’s suit. To be honest, it was a pretty cute outfit. And he was definitely wearing heeled shoes. While he was a shorter guy, it never bothered him before. Maybe his shortness finally got to him? Or this new girlfriend was taller than him or something? And the way he holds himself now was just… kinda effeminate. His shoulders were pulled back, pushing out his chest and his hips pushed back really making his butt pop. He did have a nice butt too, even mostly covered by that jacket. His elbows were tight to his side with one hand on the strap of his “man bag” that was clearly a woman’s tote bag and the other hand held out from his body, wrist turned out and going forward and back. His face totally different too. He clearly got some work done, which was really really well done. She only noticed cause she wasn’t afraid of a little Botox and filler herself. But his cheeks were much fuller, giving an apple cheeked look especially with some blush on them. And his lips were bigger too. And was that gloss on them? His lashes were long and full, clearly from mascara. She didn’t know what was going on, but Tyler was definitely going through something.

“Um, I’m leaving for the day Charlotte. You get home soon too. You’ve worked hard today and you deserve it. Thank you so much for all your work”

Charlotte wasn’t unused to compliments from her boss, but they were normally on her outfit or how great her legs looked not on the quality of her work. And she hardly ever let her leave early.

“Th-thank you Mr Matthews. I-I appreciate it. Um, are you alright?”

Tyler did a nervous smile, clearly uncomfortable with the question. “Yeah, I’m, like, fine. Just a month, ya know? The new outfit is a lot but I think I’ll let my girl know it’s not really my look. Have a good night, Charlotte”

Charlotte was relieved that the outfits weren’t going to stay. While he did look surprisingly good in it, it was more of an appreciation for how a woman looks in a suit than a man. She didn’t think it would work well in this testosterone filled company.

“Thanks, Mr Matthew’s. You too. Oh, I do love your tie btw. It’s very cute”

Tyler blushed, making his pink cheeks even pinker as he wiggled out of the office without a response. Charlotte just shook her head before packing up her stuff for the night.

Tyler got into his car and drove. He was so confused about his day and his outfit. He had to get some new suits so he started driving to Antonio’s. Realizing what he was doing, there was no way he could see Antonio after last night. Even though his cock was swelling pressing up against the tuck kit, he shook his head to get rid of the thoughts. No, absolutely not. Not again. He changed the GPS to a local high end department store instead. He’d get a couple cheaper suits, no Italian high end suits this time, just to get him through the week.

His mind felt like it was in a fog as he drove. The jumbled emotions and thoughts of the past few days hidden in a shroud of smoke. Pulling up his meditation playlist, he let the waves crash over him….

…. Tyler’s eyes fluttered open. He’s standing in his living room, panting for breath. On the TV in front of him is a YouTube video for “Big Booty Workout” where a white gym bunny type brunette was going through a cool down exercise. Tyler looked at the time at the bottom and saw the video was an hour in.

Looking down at himself, another groan of despair hit as he saw another humiliating outfit. His legs were encased in a skin tight pair of shiny black yoga pants. The waist band was high waisted on the hips but cut down in a V at his navel, showing off most of his toned abs. Or it would be showing off his toned abs if it wasn’t for the black workout waist trainer tightly cinched around his stomach. While not as dramatic as the corset from earlier, it still gave his stomach a slight hour glass, constricting his breath. His crotch was completely flat, and by the right constricting feeling on his groin he still had his dick taped between his legs with his balls pushed up inside him. The back was a similar V shape with high waist on the hips, showing off his back dimples. The shiny material of the pants shined in the light, showing off the shadows of his thick thighs and toned calves. Three neon pink stripes wrapped around his thighs, giving the work out pants a “thigh high athletic sock” look to them. The pink giving an even girlier, bimbo type feel to the look. On his feet were white and pink work out shoes, but by the feeling of the arch in his foot and how thick the back sole was they were definitely heeled sneakers!

His butt looked like it was transformed in these pants though! The back was a ruched scrunch butt, with the seam going deep between his cheeks separating the two. There was a lighter black design that outlined his butt, drawing attention to it while making it look bigger. The material was so skin tight that it confined around the bottom curve of his cheeks, accentuating the apple bottom shape. He moved his legs a little bit and saw his butt jiggle even after he stopped moving! Thankfully, it didn’t feel like the butt plug was still inside him, but his hole did still ache and felt a bit stretched out from the infernal toy.

What was worse, but not by much, was his top. Well not a top, it was a sport bra! The neon pink shiny spandex material covered his chest with two triangular shaped padded push up cups. While he didn’t have much flesh there, or so he thought, it took what skin was there and pushed it up and together into a definitely there cleavage. And the padding gave him full A cups, if not a small B cup! Two thin black straps went over his shoulders before crisscrossing his back, connecting to a slightly wider pink back/band strap. Tyler grabbed the two cups with his slightly shiny manicured hands, feeling the silicone gel padding that gave them some weight and realistic feeling. Gripping them up before letting them drop, He was shocked to see his chest jiggle a bit!

Tyler walked over to the full length mirror next to his TV, the one he used to watch him getting blown by some bimbo or fucking them from behind while doing muscle poses, and saw a pink gym bunny staring back at him! His skin was gleaming and dripping with sweat from the hour long work out. Sweat beaded down his face, onto his chest and into the cleft of his new cleavage. His legs in the full length mirror looked magnificent, if they were attached to a girl and not him! He didn’t realize how feminine his legs were and the work out pants definitely showed that. And his butt in these ruched leggings looked incredible, he couldn’t deny that as much as he wanted to. His rigorous work out schedule must’ve laid the foundation for the pants to paint a girly masterpiece!

His still girly hair was pushed back with a pink hair band with a twist in the middle. The hair band kept the hair off his face but allowed it to fall down to the sides to his neck and back of his neck. His earrings were on display, gleaming in the light. Even through all the sweat, Tyler could see he was still wearing make up that hadn’t streaked. His skin tone was just a tad too perfect without some make up, his cheek bones too defined and his cheeks too rosy to just be from the work out. His eyelashes were much longer, darker, and fuller from mascara. And his plumper lips too shiny and pink from lipgloss.

Tyler tried dumbly to explain his sudden girly appearance. He must’ve zoned out from the Xanax and came home. The gym was a sanctuary for him so it made sense to want to work out. But with all his male work out clothes gone, he had to wear a girly outfit to work out in. Yeah that’s gotta be it! Why he chose to wear a sports bra and touched up his make up he couldn’t fully explain, but he felt a little better with some semblance of an explanation, even though it was a weak one.

Tyler realized several minutes had gone by as he was thinking and saw that he had been preening and posing in the mirror, checking out his girly looking body. At the moment he had right leg bent slightly in front of him with his toes touching but heel off the ground, his body twisted showing off the side of his right butt. His hands were clasped in front of him, arms straight with his upper arms pressing together his chest to accentuate his cleavage even more. His mouth was pouting as his head was tilted slightly down so he looked up through his lashes, giving a flirty bimbo type look to his reflection. He did look pretty cute in this outfit….

Snapping out of it, he shook his head causing his hair to flair out a bit. He lightly slapped his face to knock some sense into him. Heading to his bathroom, he stripped himself of the waist trainer first, taking forever to get the little busks to unclasp. Breathing deeply he saw the lines of the waist trainer dug into his sweaty skin and that his waist seemed to maintain a bit of that hourglass shape.

Next he stripped off the bra, the spandex get stuck to his sweaty torso as he pulled it off him. Finally free of the ultra feminine garment, Tyler looked at his naked torso. While it was still a male torso, the corset and waist training use had brought a little bit of curve to his thin athletic frame. The indents from the waist trainer and the bra didn’t help his masculine image at all, as the cup indents outlined his chest to look like he had small breasts still. And his nipples looked even larger than before, and were poking out a bit. Must be the damn bra making them sensitive, Tyler lamely reasoned. When he touched one of them and a bolt of pleasure shot into his chest down to his groin, he pulled his hand away quickly, not wanting a repeat of the night before.

Tyler took off the heeled sneakers, sighing as his feet touched flat for the first time that day. Looking down at his pink toes, he remembered he was supposed to get polish remover but forgot again. Putting his fingers into the high waistband of his leggings, he slowly shimmied them down his legs, leaving him in just a pink seamless microfiber thong. The sight of his flat front humiliated him as he looked nothing like a man in his cute little thong. Stripping out of that too, exposing his heart shaped pubes, he saw the damn tape covering his manhood. He tried to rip it off but the pain was so bad that he couldn’t do it.

Thinking a shower would help loosen the adhesive, he started his multiple head with waterfall shower head shower and stepped into the warm water. The water did help loosen it after awhile and finally his cock was free and hanging where it was supposed to be. As he soaped it up to clean it, he tried bringing himself to orgasm as he’d been so horny all damn day, especially after the brief encounter with his nipples. But try as he might, his dick stayed soft as a cooked noodle, even with him massaging his newly sensitive nipples. Sure he felt horny as hell, but he never felt a build up of cum and his dick stay disappointingly soft.

Grunting in frustration, he stopped his efforts and stepped out of the shower. Next he did his new multi step skin care routine since he really didn’t want to go to the doctor as he was right now. Exfoliating and lotioning, oils and serums dropped and spread from his face to his toes. His face glowed with renewed vigor, looking years younger than his 28 years would suggest, especially with the lack of facial hair. He could pull off 21 or even 20 at this point. His body gleamed from the exfoliation and oils, his arms glistening with healthy moisture. But his legs with the leg oil looked like a lady’s razor model, shining and gleaming more than anything else.

What surprised Tyler was next to his skincare stuff was a high end make up set. Just a few brushes that Tyler had no idea what they were for, some eyeliner and mascara, a few tubes of lip gloss and even a couple nude lipsticks, one was more pink than nude! And then some containers of foundation and concealer and highlighter and a contour stick As well as a couple shades of pink blush. Antonio must have brought it last night, since he apparently loved femming up Tyler so much, what a queer. But the thought of Antonio and his touch did bring a warm tingling feeling to his groin and surprisingly his butt. Tyler didn’t remember seeing that this morning but the morning was so crazy that wasn’t surprising. He didn’t need this shit though, he already had enough girly shit in his life so he took it all and put it in the bathroom trash. What he didn’t see in the trash can was a receipt from the department store he was planning on going to with a time stamp of this afternoon with his signature on it.

Tyler walked out naked into his bedroom, unconsciously walking on the tip toes and swaying his butt back and forth. He caught the sight of him sashaying in the mirror and immediately dropped to his flat feet and tried to walk like a man again. But flat footed, his arch and Achilles felt a dull pain, like a strain or something. It wasn’t anything too bad that he couldn’t handle at the moment.

Opening his drawers, he sighed again at the dizzying array of colorful panties in his underwear drawer. He looked around the apartment and didn’t see any new men’s clothes that he would have gotten at the department store, so he assumed he just didn’t go. As much as he hated the frilly panties, the thought of going commando disgusted him. So rifiling through, he tried to find a some what normal pair of panties to wear to bed. The feeling of the thong between his cheeks from his workout didn’t seem appealing for bed, so he settled on a red bikini panty. The front and gusset was a crimson satin, but the thin straps were a see through lace, as was the back showing off the skin of his cheeks through the red lacy motif. He didn’t tuck his dick back, letting it bulge through the shiny crimson satin. Thankfully, his heart shaped pubes were covered so he didn’t have to look at the fruity pubic artwork anymore. He really needed to just shave it smooth at this point….

His mind drifted away as he realized he wasn’t paying attention to what he was grabbing for pajamas. The soft flutter of satin and silk settling over his torso snapped him out of his day dream. Looking down, he saw he had grabbed the matching camisole top to his panties, and realizing he mentally called them “his” panties angered him more than wearing a silky girly camisole.

The silk red satin gleamed with shine as it covered his torso. The cami fell loose down his stomach as it came to just above his waistline, showing off a bit of his toned stomach if he lifted his arms at all. The thin red spaghetti straps were tight on his shoulders, pressing the heart shaped cups with lace trim against his chest and nipples. There was some light padding, making his chest look bigger than it was.

Tyler moved his hands to his chest to pull off the girly top, but his hands brushed against his nipples. His fingers pressing the soft satin into his newly sensitive nipples caused him to involuntarily moan. His eyes rolled back slightly as he bit his lip lightly brushing his now hard nipples through the fabric. A warm pleasure coursed through him, centering low in his stomach. The girly gasp that came out as he lightly pinched his right nipple snapped him out of it, his hands shooting away from his chest like his chest was a hot frying pan.

“Holy fuck! That felt… amazing! Maybe these types of shirts aren’t that bad. It’s basically a tank top….. But don’t do that again, Tyler. Not in this girly get up.” Tyler admonished himself.

Seeing himself standing there like someone’s girlfriend in matching panties and a camisole, Tyler riffled through the drawer again grabbing the matching red pajama shorts. They looked normal enough to Tyler, maybe a bit too much lace for his liking around the leg holes but they’re just shorts. But pulling them up his waist, he realized the legs were higher cut than normal shorts. The waist band rose high on his hips, exposing a lot of his thighs as well as a bit of his butt cheeks hanging out the lace trimmed bottoms. Tyler groaned seeing how slutty they looked but at this point he was too tired to look again.

Tyler settled into his satin sheets, luxuriating in the sensation of his hairless legs and skin on the expensive fabric. Putting his phone to his blue tooth speakers in his bedroom, he put on his meditation and drifted off into the crashing waves…. A faint but distinct female voice saying “sleeeeep, princess…. Sleeeeep”…….