Chapter 88
by
SimonLF
What's next?
Some self attention
Part of your mind feels ashamed. You're a cross-dressing man in another man's office trying to pleasure yourself. Shouldn't you just push this down until you were in a more private location... preferably in less feminine clothing?
But the urges are surging through your body, and you've been spending the last few days in the company of a man who has rarely held back in satisfying his sexual needs. It's just not fair. You're not some doll made for someone else's pleasure, whatever you're wearing. You are a man with your own needs! You push the heel of your palm back into your crotch and a surge of pleasure spreads out.
You start kneading that area, pushing through the shiny material of the dress. You can feel the pressure building as you push harder. Recklessly, you reach down to the hem of your dress, pulling it higher and higher.
To heck with this, you think, and stand up on the heels, pulling the entire dress over your head once again, and casting it down on the floor. You look down to see your bright red bra holding an ample pair of boobs. The sensation of this mixes with the arousal you already have and you sit down. You reach down to your crotch and are reminded you aren't wearing any panties. Less to get in the way you suppose.
There in the office chair, wearing nothing but black heeled boots, a red bra and a black choker, you begin in earnest.
Pushing down, kneading, trying from the side. You good remain trapped, but they keep responding. In some way the tease makes it all the more exciting, but you just want this volcano to erupt. You press harder and harder, sending wave and wave through you. You drum your fingers, press, knead and after a moment of hesitation, you find the opening in the prosthetic. Pushing your fingers up its self lubricating channel and finding them in much closer contact with your penis.
It's feels good, you dig deeper, again and again.
You're getting into a rhythm. The crescendos are mounting. You close your eyes in bliss.
There's a knock on door.
You're beating heart almost has an attack. Who's outside? Ray wouldn't knock. Didn't matter, nobody should see you like this!
You slide off the chair and behind the mahogany desk onto the carpet, just as you hear the door open.
"Ray?" You definitely don't know that voice.
"He's not here," a second voice slightly younger voice, as footsteps enter the room.
"Neither is that new secretary of his. I think we can take a good guess of what he's doing now."
"We'll give him five minutes," and you hear the slightly older person sit on the couch.
"Hopefully that's all he'll need," the voice is getting closer. You cautiously crawl back on your hands and knees into the footwell of the desk, nervous he'll see your head if he gets closer to the desk.
"Must you really be so gauche with this?"
"Me? We're talking about a guy who's screwing his secretary and you're saying I'm inappropriate for pointing it out?"
"Ray does a lot of good work for this company, his weakness for the ladies notwithstanding. And while I admit his latest hire is quit the looker, you can never be certain of these things."
"Oh I am certain. I've access to business expenses. Last night he booked a suite at a fancy hotel at very much short notice, and a few drinks at the hotel bar to boot." You gulp, was Ray really this reckless? Charging his company card?
The person on the couch took a moment to respond. "I... well that is pretty damning, but it's not proof..."
Another knock on the door, and it opens with the assent of the two men.
"Hello?" Wendy's voice, with an air of uncertainty, "I was told to bring... this bag up here?"
"Just leave it in the corner," the couch voice replied curtly
You hear a plastic bag being put on the ground at the back of the room. After Wendy confirms the men don't want here for anything else, she leaves the room. And with her goes any chance of that bag being brought closer. You seethe in frustration. If the men weren't here you could dash out, get clothed, and be in a better position to plan your next move.
"You know, I've a feeling..." You hold your breath as you hear the person near the desk walk back and hear the plastic bag ruffle "Pumps, stockings, work dress. You were saying I didn't have proof?"
The couch man coughs in response, but doesn't say anything. The 'investigator' continues.
"Wherever the secretary is, she definitely isn't wearing work appropriate clothing right now, if she's wearing anything at all." You grit your teeth. You never want this guy to discover how right he is.
"You may be right, but still be cautious of how you talk about Ray."
"Hey, I'm not trying to criticise the guy. I'd love to be in the position he's in. A hot secretary who's always at my beck and call. Company comping me for hotel nights with here where we talk 'business'. Having someone who could keep me company on business trips. Who wouldn't want that?" You frown, while you'd normally empathise with the guy's point, this this case 'that' was referring to you!
There was a chuckle from the couch voice. "There's an attraction to it to be sure, but it comes with drawbacks. For instance, right now Ray hasn't shown up for the meeting. Now if we knew he was as diligent as he is a lot of the time, we'd understand that there was probably a good reason. But if we suspect he puts pleasure before work, and this week he happened to hire exactly the *wrong* sort of secretary for keeping him focused..."
The door burst open. "Ah you're here already," Ray's unmistakable voice, and confident stride.
"Glad you hadn't forgotten about us!" Older one said.
"Never shall Damian! And Peter!" there was shuffling as hands were being shook and with the couch guy (Damian?) now standing up. "We've a lot to discuss."
"Certainly. Oh and by the way, will your new secretary be joining us?" Peter asked, semi-mischievously.
"Jane?" Ray queried, "Oh she's..." there was a momentary falter in Ray's voice, probably wondering where you were, "...busy at the moment."
Damian spoke up, "Peter was worried you'd find her a bit distracting."
Ray gave a laugh with a slight edge to it. "Well Jane may be easy on the eyes but right now this meeting is top priority."
You freeze, as you hear Ray's confident steps towards the desk. You'd miscalculated. Ray's business meeting wasn't taking place in some meeting room somewhere, it was taking place right here in his office!
You're on your hands and knees on the soft carpet, practically naked with a red bra holding in your hanging tits and backed into the footwell of a mahogany desk. Smooth hard wood was above, to the side, and behind you. The only way out was in front of you where you could see the office chair suddenly moved back as Ray's hand gripped it.
"So be rest assured," Ray said, as he settled into the chair in front of you, his crotch level with your head, "the matter in front of me will have my full attention."
What's next?
Disable your Ad Blocker! Thanks :)
The Chronicles of Miss-chief
An anthology featuring stories about gender bending adventures!
An anthology featuring stories about gender bending adventures!
Updated on Jul 25, 2025
by BHCP2
Created on Feb 21, 2020
by vanillathunder
- 6,620 Likes
- 1,308,545 Views
- 705 Favorites
- 573 Bookmarks
- 469 Chapters
- 110 Chapters Deep
- All Comments
- Chapter Comments
