Tyler’s first day at the office

…. Tyler blinked his eyes open a few times, trying to get his bearings. Last thing he remembered was laying down on his bed listening to his meditation tapes. But now he saw he was near the elevators right outside of his office door!! He looked around and saw himself in the mirror, wearing the same outfit from earlier! His hair was still brushed and plumped for volume and his hair was over his ears showing off his double ear piercings! His face still looked his own, but much more pretty since the procedures and the light make up. His eyes looked wider and lashes more full and his lips plump with a light shine.

He was still wearing his powder blue suit, the cut of the jacket showing off his compressed midsection from the corset that was definitely still on and providing an illusion of a bigger chest. The button down, well more a blouse, looked fine at first glance but looking more closely you saw the shiny satiny material and the buttons on the wrong side. But the floppy black silk ribbon bow tie was a dead giveaway of a women’s suit.

Thankfully the jacket covered most of his butt and groin, as it looked decidedly lady like at the moment. The pants there were skin tight, showing off every curve and digging under and between his cheeks. And with his dick and balls still tucked between his legs with that tape, no bulge could be seen. He could feel the garter straps still tight on his thighs under the pants holding up his black stockings. The pants were tight to the thigh and then flared out at the knee, giving off a decidedly feminine cut to his legs. On his feet were the three inch heeled work shoes, thankfully the loose pants covered the heel. Slung across his shoulder wasn’t his normal briefcase but a brown leather tote bag with gold embellishments across it.

He quickly tried to move his hair to cover his earrings, trying to do something to cover his feminine appearance. He was able to cover his lobes, but He tried to mess with his hair to get a more masculine look, but there must’ve been hair spray used and it kept springing back into a femmy cut.

Sighing in exasperation, he moved to take the girly string bow tie off but heard footsteps coming into the elevator bank. The sound of Peterson talking on the phone brought on panic for the femininely dressed executive. He couldn’t let his rival see him dressed like some poof!! Panicking, Tyler briskly walked to his office door and hid inside.

Closing the door with a bang behind him, he turned around and saw Charlotte typing diligently at the computer.

“Good morning, ma’am. Mr Matthew’s isn’t in yet. Do you have an appointment?” She said almost reflexively as she continued to type. Her hair was in a very cute up do, a twisting and braiding of hair around the base of her ponytail that was curled as the end giving it a little flip. Two bangs hung loose on the front framing her face. She wore thick rimmed glasses, more for the blue light than needed to see, over a neutral shimmery eyeshadow and her long lash extensions. Beautifully contoured make up gave her skin a sun kissed bronze look. Her matte red lipstick, overdrawn just a tad but perfectly done, gave her look a bit of color and a bit of sluttiness that was “highly encouraged” for assistants.

She wore a black top where the torso was a tight thin silky material with rows of black buttons down the middle. It had a solid black color with several buttons undone showing off quite a bit of her cleavage and a bit of the black lace of her push up bra that would be inappropriate at most workplaces, but not here. The sleeves were a poofy sheer chiffon down to the wrist ending in a white ruffle with white black polka dots throughout showing off her toned arms.

Tyler stood there looking at her not sure what to say. “Ma’am? Do you have an appointment? We’re very busy today.” She said as she looked up from her computer. Her eyes went from cold corporate gaze to wide eyed when she saw who was standing in front of her.

“Oh! OH! Oh Mr Matthew’s i-i didn’t realize it was you. You look… different! New erm… suit I see?” Charlotte’s eyes looked him up and down, taking in the whole look. While the color immediately stood out, the cut really caught her eye.

“It, um, yeah, errmm, trying out a new look. New boy-um girlfriend thought it would look good! Wanted to shake things up a bit. Thought it would um, keep me on my toes for the next project ya know?” Tyler stammered out his lame excuse, trying to cover his flat groin more with his jacket but only looked like a shy girl with her hands clasped together caught in a lie.

Charlotte stifled a giggle at her boss’s new look, “Um yeah, it looks good on you! That boy-I mean girlfriend of yours has some taste! *giggle*. Makes sense you want to be on your toes to finish up this Spade Corp project” Charlotte looked at Tyler’s footwear, seeing the high heel in the back. “Um, any way. Peterson needs to see you first thing. I think he’s on his way over right now. He didn’t sound happy”

Tyler’s eyes went wide as Peterson was in the hallway outside right now! “Don’t let him in! Tell him I’m busy with another call!” He frantically ordered as he went to his office and slammed the door behind him, hearing Charlotte break out into a fit of belly laughter. What he didn’t realize was the girly wiggle to his walk the combination of the corset and heels did to him, making his butt sway back and forth.

Tyler went to his desk and started up his computer before moving to sit down heavily, stressed and already exhausted but it felt like he’d just woken up. But when he sat down, he felt intense pressure and pain coming from his butt, along with immense pleasure. A girly moan escaped his plump lips as the intense feeling crashed over him. He stood up, shaking slightly from the feeling, and looked down thinking he sat on something but nothing was there. But then he felt the fullness inside him as his ass clenched involuntarily around the object lodged inside him. Did he have a dildo or something inside him!! He felt back there between his cheeks over his tight pants and felt a hard heart shaped object stuck between. He’d been with kinky girls before and knew that it was a butt plug! How the hell did it get in there? Did Antonio come back and put this inside him?? He’d never ever do that willingly, would he??

As he was feeling his butt and his new plug through his pants, his face getting hot and blushing from the weird yet erotic feeling, wondering if he should take the plug out in his office, he heard voices outside.

“Mr Peterson, he’s on a call. Can you please wait outside”

“Bullshit, Charlotte. We both known he’s dodging me again. I’m not playing these games with him”

Fear hit Tyler as he heard the door start to open, not wanting his rival seeing him dressed in this fruity outfit with a corset and lingerie on underneath and a plug in his butt! He took his hand off his plug and turned to the door, face still hot and blushing underneath the minimal make up he had on.

Darius Peterson strode in with his usual confident swagger, wearing a clean cut grey suit with a black tie and pocket square. The suit was tailored to use big physique, his broad shoulders tapering down to his trim waistline. His close cropped beard faded into the short fade on his head. His face had the same angry look that many running backs and quarterbacks saw before they were tackled to the ground. “Matthews! Enough is enough! We need to figure out the Spade corp….”

His sentence trailed off and that face changed seeing Tyler in his colorful and feminine new suit. He went from angry to surprised to humorous all in the matter of a few seconds. A smile spread across his face seeing his bitter rival, usually so cocky and clean cut masculine, standing there in his feminine suit with a floppy little string bow tie, blushing and shyly looking down with his hands clasped in front of him. And, to be honest, the suit fit him really well. He knew Tyler was a smaller guy but he was pretty fit, never showing off any thing feminine. But the suit seemed to accentuate his slender small frame. His waist was small, like very small. And his legs didn’t look like a man’s legs in those tight pants. He could see thick thighs and a rather large butt and hips for a guy, even more so from the tightness of his pants. They looked like they would be Charlotte’s legs rather than her boss’s.

“That-that is a, uh… new look for you Matthews. *chuckle*” Peterson tried to hide his amusement as a professional but this was such a shock and so funny to him that he barely hid it. Did he lose a bet or something? Why was he wearing such a feminine outfit?

“Oh uh yeah, new uh girlfriend got me a new suit. Thought I’d uh, try it out. You know how it is with women” Tyler lamely attempted to excuse his girly outfit, reflexively brushing his hair over ear as he wasn’t used to how it lay at the moment.

“Yeah, sure. What you do for love. I don’t know if I’d do THAT. Don’t think it fits my body shape, or really my look. Did she get your ears pierced too, Matthews?” Darius asked with a smirk and slight chuckle seeing the dual shiny piercings on his ear.

Tyler blushed even more, frantically brushing his hair back over his ear to cover the effeminate piercings. “Uh yeah! Anyway, um what can I help you with, Peterson?” Tyler tried to move past his appearance and move on to a different topic.

Darius smirked again but with a darker look to his face “Don’t you remember what we talked about last week, Matthews? Let’s keep things professional. Call me Mr Peterson.” Darius purposely left off the honorific when addressing Tyler.

Tyler, all thrown off from his hectic morning, squirmed a bit at being talked down to and meekly nodded his head, eyes down. “Yes, of course, um, Mr Peterson. Please, have a seat”

Darius liked this cowered and unconfident Tyler much more than the pompous asshole. This new girlfriend must’ve really gotten to her hooks in him, bad. His anger from Tyler’s cut throat tactics with Spade Corps had dissipated. He was going to try the angry technique to try and get him to work with him to save Spade Corp, but Seeing this cowardly effeminate man in front of him, he decided to change tactics.

Darius sat down in the chair in front of his, casually crossing his leg over the other. Tyler sat as well, slowly this time from fear of the plug and also because the corset restricted him bending. But he still felt the plug pressing deeper inside him as he settled in. He quivered, closed his eyes, and bit his plump lip try to stifle the moan that was begging to escape. Once settled he let out a sigh, trying to take a deep breath but the corset not letting him, and opened his eyes seeing Darius looking at him quizzically.

“Uh had a big leg work out yesterday. Still trying to get past the um, soreness” another lame excuse from Tyler but Darius seemed to accept it. Its not like Darius would put two and two together that Tyler was wearing a powder blue corset and a butt plug to work!

“Oh I understand. Leg days can be tough the next couple days. But the hard work seems to be paying off for you, Matthews. Your legs look very…. Toned” Darius complimented him, trying a nicer approach.

Tyler blushed again at the compliment. Was he admiring my legs?? It’s these damn pants they’re too tight! But why am I not grossed out by the compliment? Why did I get butterflies in my stomach from this?? He shook his head, his longish hair flaring out a bit from the shake.

“Yeah I, uh, have been working out a bit so um, thank you for the compliment, Mr Peterson”

Darius grinned his perfect smile using his charm on the young man before him. If he likes being praised and that makes him more malleable, so be it. Darius wasn’t a stranger to flattery in his business dealings.

“That’s good to hear, Matthews. Maybe we can work out some time, have you show me a few things. Been neglecting leg day a bit, old football injuries you know, focusing on my upper body more.”

Tyler could see Darius biceps through his jacket and saw he wasn’t kidding about working out. His pecs looked massive and rock solid in his white button down. Tyler was jealous of course as he never was able to bulk on muscle like that, but a new feeling crept in, the same feeling he felt when Antonio held him in his big strong arms. A warmth and tingly feeling deep inside him. But now he felt his tucked dick twitch between his legs and his sphincter tighten down on the base of the plug. He squirmed in his seat, never taking his eyes off Darius’s bulging muscles.

Darius could see Tyler not making eye contact and staring at his chest and arms as his face blushed even more. He had this affect on women in the past, and even some gay men, he knew he was a good looking man. But he never took Tyler as gay before today. He was always bragging about the girls he was with. But maybe he was just closeted this whole time. This changed things for Darius, and he was going to use it to his advantage.

Leaning slightly forward with his arms slightly bent to show off his biceps, he pressed his advantage. “Anyway, Matthews, I think we got off to the wrong foot on this Spade Corp deal. I think we can work together on this. It’s a big undertaking for just one man. How about we COUPLE up and do this thing together? I can handle some of the filings if you send it over to me. What do you say?”

Tyler was mesmerized by the big muscles wanting to bulge out of Darius’s jacket and shirt when he suddenly came to realizing what Darius was recommending. No way was he letting Darius near this deal! He’d try to save Spade Corp’s failing business and cut into his profits from the take over.

Just as he was about to tell Darius off, a vibration kicked in inside his plugged ass. The plug started vibrating on a high setting, sending vibrations through Tyler’s prostate and waves of pleasure through his body.

“YES! YES!” Tyler practically screamed, gripping the edge of his desk hard with his shiny manicured nails. The sudden vibration stopped and Tyler had to work to not start panting in front of Darius.

Darius was taken aback by the sudden acceptance but he knew better than to look a gift horse in the mouth. “That’s great, Matthews. I’ll talk to Charlotte outside and let her know to send over the filings. I’m glad we can come to a compromise here and look forward to working with you in the future”

Tyler needed to get Darius out of his office and away from him. His mind was a mess trying to figure out what the hell was going on and he needed space and quiet. He stood up and started walking around his desk to escort Darius out of the office. “Yes of course, I um, look forward to it too, sir. I mean, Mr Peterson!”

But Tyler was still a novice in his new heeled shoes and as he was rounding the desk he tripped, beginning to fall forward into Darius! But two strong arms grabbed him under the arms before he hit the ground, lifting him up with ease and planting him on his feet but not letting go. Tyler felt those strong hands slide slowly down his sides, stopping briefly at his waist. Did he feel my corset? It was a brief touch maybe he didn’t. God I hope he didn’t!

With his hands now gripping Tyler’s arms Darius grinned even more at the effeminate man in front of him. He looked into Tyler’s eyes, seeing his mascara plumped lashes, the light make up softening his face, the plump glossy lips. He had felt the tight boning of the corset under Tyler’s shirt and everything was starting to click. He might not know the why of Tyler’s new outfit, but he was definitely understanding that this wasn’t just some new outfit from a girlfriend. This was something much more.

“Don’t worry, I got you, Tyler.” He spoke softly but with the bass in his voice of a dominant masculine man. “And did you call me sir? I like that. Let’s keep it that way shall we?”

Tyler meekly nodded his head, so humiliated at the moment that he had to rush Darius out of there. If he had to call him sir so he could be alone, so be it.

Opening the door and letting Darius out, Tyler responded. “Yes um…. Sir. Charlotte can get you sorted out. Charlotte give Mr Peterson here the files for the Spade Corp deal. He knows which ones. ” Tyler saw Charlotte eyes widen in surprise hearing Tyler call him sir and widened even farther hearing that he was giving him the Spade Corp files. He’d been fighting Darius on that for weeks and now after a five minute meeting he was allowing Darius in? Something was definitely up with her boss, and not just his new wardrobe. His little ribbon bow tie was cute though. She’ll have to look into getting one for herself.

Tyler turned on his heel, which Charlotte saw was an actual heel at that, and returned to his office, locking the door behind him. Breathing heavily, he went to his desk and sat down gingerly, not wanting a repeat of earlier. He had to figure out what the hell was happening to him! But the stress of the moment was too much he needed to relax. He pulled out his bag, more a purse, and rifled through it. Besides his phone and keys and wallet, there was mascara and lip gloss and a small compact, as well as a few condoms. Sneering in disgust that this was in his bag, he rifled through some more before finding his bottle of Xanax. Taking two pills and dry swallowing them, he pulled out his head phones and set the meditation to start. He had felt a craving for it, almost like an addiction like cigarettes or something, and needed to melt into his relaxing world once again.

As the soft waves crashed over him, he closed his eyes, faintly hearing the female voice in the background…..