I began hooking up with a young man who lived in close proximity to my office, and together we pushed the boundaries of what an “office romance” could be. I’ve written about him before (The Office Chair)

Reggie is significantly younger than me. I would say he’s at least 20 years younger, and we met on a hookup site. His profile said very little. It said he was 24, black, had an 8inch cock, he was a top, and liked the “trans fetish.” He checked all of my boxes, but I didn’t think he would be into me. I struck up a conversation with him, and he was really receptive to me. He said he liked “boys who want to be girls” because they try harder and fuck better than anyone else out there. Knowing my own history, I couldn’t disagree.

I have a white collar job, and am surrounded by other business professionals, and Reggie was definitely not one of those types of people. He is rugged, blue collar, stocky, his hair is a mess, and he often dressed like a video game street pimp. He came to see me one night in a shiny white faux leather trench coat, coupled with black Adidas sweatpants, and with a pick sticking out of the back of his unkempt hair. He had charm, but anyone seeing him in a professional office setting like the one I work in would think he was lost.

I kept a stash of stockings, panties, bras, makeup, wigs, and nighties along with various butt plugs, vibrators, and dildos in a drawer in my office. I have a business partner who has no idea about my alternative life, and I can only get wild if he isn’t around, which thankfully has been pretty regularly lately. He took off around 3pm one day, and I went online right away to hit up Reggie. I sent a few messages and got no response, but about an hour later, he popped up and said he could come see me in 15 minutes.

That’s very little time to get ready, and it was during business hours, so I couldn’t wear makeup, and would have to parade him through the office building while people were still around and working. On the off chance that we would get to meet up and fuck, I had been prepping quietly all day. I douched once in the morning and again in the afternoon to make sure I was all cleaned out.

After the second douche, I inserted a vibrating butt plug into my boi pussy, and worked with it inside of me for the better part of the afternoon. The control to the vibrating mechanism was a single button on the end of the plug. It had 3 speeds, and I can grind my pussy into a chair and make them change up, which is fun to do.

I asked Reggie to dress somewhat regular, but all he kept replying with were things like, “You need this dick in you,” or, “You gonna take control of this dick or it will take control of you.” Those were hot messages, and got me excited, but they also let me know that he wasn’t listening to a word I was saying, and was fully focused on fucking me soon. He didn’t like it when other people were in the office building, because it meant we had to be quiet, and Reggie likes to be verbal when he is fucking me. When something feels good to him, he likes to moan loudly, or give me direction.

I actually kind of like the fact that we had to be quiet sometimes. It heightened the level of intimacy to me, and allowed for more nonverbal communication, and looking into each other’s eyes. Those are things that sissies really enjoy doing when they’re being fucked, but it bothered him. I only have one immediate neighbor in the office, and it was a real estate firm. Most agents were out in the field, but their secretary was in there, and would definitely be able to hear if people were audibly fucking on the other side of a paper thin wall.

I was drinking warm water nonstop, so my mouth could be welcoming and cozy for his cock to be harnessed in. I watched a YouTube tutorial on how to give great blow jobs, and that was one of the tips. Another was to squirt a little bit of lube under your tongue right before you start sucking cock. Both of these are great tips, by the way. I stood out on the deck of my office building, with my butt plug at top speed, and watching amateur interracial sissy vids to keep me turned on and horny.

I sent a message asking where he was, and he said, “Turning the corner right now.” Then from around the corner, I see Reggie, wearing a lime green jacket, red track suit pants, and untied Air Jordan’s. He stood out like a goddamn Christmas ornament. I immediately came down from the deck and met him at the door to walk him in. I had a manila folder with “Tax Documents” written on it that I handed to him, to make it look like he was here on business. He looked at it, looked at me, then chuckled, and followed me inside.

As we walked up the stairs to my office, he reached out and put his hand on my ass and squeezed it, which excited me, but also made me nervous, and I picked up the pace to try and get away from him. I opened the office door and let him enter first. I had a nice blanket that I folded twice over, and a pillow on the floor. I was burning 2 candles, the lights were off except for a lamp in the corner, and had my sissy playlist queued up on the computer. I put rubbers, lube, and poppers under a towel on the end of my desk, and had laid a towel over my office chair for him to sit in, so that I could recreate the last time I rode his cock in the chair.

Every time he came over to fuck, he would walk in the room, immediately get fully nude, and lay down on the blanket, not saying a word. His dick was always soft to start, which honestly, I kind of love. I get turned on making a dick go from totally soft to rock hard and throbbing with my mouth and tongue.