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. I stripped down to my bra and panties, put on some lipstick, squirted some lube under my tongue, hit play on the computer, and laid down next to him.
I immediately began rubbing all over his body for a few minutes. He would wrap one of his big arms around me, and firmly grip one of my ass cheeks through my panties, and squeeze it over and over again. After rubbing all over his chest and belly, my hand would make it down to his flaccid cock. The minute I touched it, he would exhale loudly. I would squeeze it gently, caress his balls, run my hands along his inner thighs, then start kissing my way down his body. I would start at his nipples, and shimmy down until his cock was staring me in the face.
Another great blow job tip I learned from that tutorial was to utilize your tongue on the head, and particularly on the underside of the head, which I gladly did on Reggie. Then I took the head of his cock into my mouth, and began kissing and licking it. I put the whole head in between my lips, while running nonstop circles around it with my tongue. He was grunting in delight, and after a minute or so of that, I took the whole cock into my mouth. This is when the growth really starts to accelerate. I locked down on his entire cock, swirling my tongue nonstop, and my nose was buried in his balls.
He started to moan loudly as his cock reached full growth, and I reached up and put my finger over his lips telling him to be quiet. He took my finger into his mouth and sucked it like a cock, as I began to pick up the pace on sucking his actual cock. He let me suck it for another minute or two, but he made me stop, because he wanted to fuck me and didn’t want to blow his load. I was in full agreement with him on this, because for as much as I love sucking cock, the main thing it does for me is get me really horny to take that cock in my pussy.
I told him to have a seat in the chair, and he did as I requested. I walked around him, bent over the desk and grabbed the lube and rubber. He grabbed 2 big handfuls of ass and started squeezing them mercilessly.
“I’m fixing to pull your panties to the side and you gonna take this young hard dick,” he said, which made my heart race.
I put my satin draped ass on his cock, held on to the desk, and started swishing from side to side on him. He was holding his dick at the base, and started slapping my ass with it as I swayed. He told me to stop, and he pulled my panties to the right side of my ass, spit on his fingers, and began sticking his digits inside of me. He started with the middle finger, sticking it as far up my pussy as he could get it, and swirling it around the walls as he did so. He added another finger, then another, and had all 3 of them swirling around in circles inside of me. It felt wonderful.
I took a big hit of poppers and as I exhaled, he pulled his fingers out one by one, then out of nowhere, he grabbed his cock and tried to insert it inside of me. He knew my head was high from the poppers, and I guess he thought I might not notice, but I did. A thick daddy cock doesn’t feel like a finger, ya know? I pulled up from him, and looked back at him to over my shoulder to let him know that I knew better, and wasn’t going to be taking his dick unwrapped, which made him smile.
“Let me just start like that, baby,” he said, “you know it feels so much better raw.”
While I did know that raw felt better than wrapped, I also knew that Reggie was pretty much a stranger to me, and he never answered questions when I would ask him about his status, so I knew I had to wrap that salamander. I learned another trick from watching porn, where you put the rubber between your lips, and work it down over the shaft, and Reggie fucking loved when I would do that. I put the rubber in my lips, turned around to him, got on my knees, and proceeded to work it over the pulsating head of his cock, and began to shimmy it down his shaft until I had reached the base.
I grabbed the lube, squirted it liberally into my hand, and jacked his shaft a few times through the rubber to make him stand at full attention. I took what was left of the lube on my hand and rubbed it between my pussy lips, then turned around to face away from him so that I could sit on his cock and ride it. I took a few deep hits of poppers, and began to back up and center my pussy right over his cock. I was angling it so that he could stick it inside of me with ease from that angle, but for some reason, it wasn’t aligning properly.
I tried to back up and reposition myself so that it could go inside of me easier, but again, we weren’t lined up and I was missing again. I tried a third time, but not for long, before he told me to sit still until he told me to come down on it. I did what I was told, but he also couldn’t get things align. He kept getting the tip in, but as soon as he would try to go further, it would plop out, frustrating both of us really badly. He was done with trying and told me to get up so he could get up, which I did, and he took control.
“Kneel on the chair, and hold on to the back of it,” he said, handing me the bottle of poppers.
I knelt on the chair as I was told, and immediately took 2 deep hits of poppers, holding the last one in my lungs as long as I possibly could. I felt him digging around my pussy with his cock. I felt him pulling my left ass cheek wide, so I reached around and pulled my right cheek wide to help him with his cause. The second I exhaled, he plunged inside of me. He didn’t ease it in like usual, he put it all the way inside of me. I yelped audibly, and like a smart ass, he told me to be quiet. He pretty much got his whole cock inside my pussy, and held it there for a minute.
I hurriedly unscrewed the poppers bottle and took 3 long sniffs. I was holding it in, and as soon as I screwed the cap back onto the bottle, he began pulling out and sticking it back in at a slow pace. As soon as I exhaled, he must have felt my pussy lips loosen up, and he started going to town on me, rapidly fucking my hole, so much so that I felt the legs of the chair coming off of the ground. I tried to quietly tell him that I felt like he was going to knock the chair over, and he told me to relax.
“Don’t worry about it, boo,” he said, as he was pounding in and out of me, “I got you, and wouldn’t ever let you fall, so you need to relax and just take this dick.”
I did what I was told, and took a few more hits of poppers before closing the bottle, closing my eyes, and letting my man take control of the situation. The legs of the chair were coming off of the ground, but lost in the moment of everything by me was the fact that he had his hands firmly on my shoulders, and partially around my neck. He was using his hands to push and pull me back and forth on his cock. In essence, he was manually forcing me to ride his cock, and it began to feel really good.
He was grunting and breathing heavy, thrusting his cock in and out of me for several minutes, all the while, whispering dirty talk to me about being his slut, and telling me what a dirty little sissy bitch I was. I was loving every minute of it, especially the feeling that I was almost floating in the air, as 2 of the chair legs were totally in the air. I felt a little spurt come out of my clit cock that was flopping like a fish as he was infiltrating my pussy hole. After a few more minutes, he wanted to get into a different position.
“Now, you gonna get on your hands and knees on the blanket,” he said, “and put your knees as close together as you can, understand?”
All I could do was nod to let him know that I understood him, and I got off of the chair and wobbled over to the blanket. I put my elbows on the pillow that was there, and stuck my pussy up in the air as far as I could. I could hear him breathing heavy, and walking towards me. As he knelt down behind me, he grabbed my thighs with his big, burly hands, forced my legs closer together than I had made them for him, and told me to keep them there. He grabbed more lube at my request, and put a big gob of it inside of my quivering pussy hole. I took 2 big sniffs of poppers, and prepared to be gloriously violated.
As I exhaled, he entered me again, and once again, went as far inside of me as he could go. I felt his balls slapping me between the legs, right where my pussy should have been when I was born. Initially, it was equal parts pleasure and pain, which quickly translated into equal parts euphoria and ecstasy. It’s impossible to describe the feelings that run throughout your body to anyone who has never felt the power that accompanies giving yourself to someone else in complete sexual submission like a woman. It’s the most liberating and stimulating feeling that can be achieved sexually.
As he was fucking me, I could feel sweat dripping all over my back from his body and his face. He told me to lay on my stomach but keep my legs together, so I shimmied down to the floor with him still inside of me, and put the pillow under my head and face so that I could lay flat. Turns out, I needed that pillow to muffle my moaning and yelping, because he began going to town on my pussy. His thrusts intensified, and he kept barely pulling his cock all the way out of my pussy, before ramming it back in as hard as he could with every thrust.
He put his entire body weight on me, and had his mouth right up to my ear when he started saying things like, “this my pussy, that’s your dick, take that big dick, sissy bitch, take daddy’s big dick.” It was seriously hot, and also somewhat threatening, which was oddly a turn on as well. I was covered in his sweat. He quit whispering in my ear, and started kissing my shoulders, and licking the creases between my arms and my back, all while furiously pumping his cock inside of me.
It was so intense that I didn’t even realize how much he had made me cum until everything was over, and that was several minutes later, because when he reached the point of cumming, he pulled out of me and told me to turn around so that he could cum on my face and down my throat. I did what I was told, despite the fact that my legs were shaking and I was completely disoriented. I turned to face him, and held one of my legs up in the air, and took my other hand directly to dilated pussy and started running circles around my sugar walls while looking at him.
He was breathing heavily, chest heaving, struggling to get the rubber off, and his cock was completely engorged. It was much more swollen and plump than it was after I sucked it earlier, and it was really big and fat then as well. I took my leg down and reached over to help him, gently using my nails to get under the thin cock jacket, and started to roll it off for him. The minute I got it off, I gripped his cock tightly and started stroking it for him, which made him moan audibly, and look down at me in amazement.
I was in awe, to be honest. It was totally rock hard and throbbing, and I instinctually went to it with my lips and kissed it as I continued to stroke it. He told me to stroke it harder, and I did what I was told. As I was doing so, I began subconsciously talking about it and him in a low voice, anxious to milk him until he came, and that really turned him on. I gripped my hand around it and started stroking it towards my face. My eyes were locked in on his cock, totally fixated on this slippery, throbbing vein that was inflating more and more as I did so.
“Oh, baby, you’re such a fucking stud,” I said, “Give me that hot load from your fucking meat, you fucking stud.”
This must have really pushed his buttons, because when I pulled my eyes away from his cock to look up at him, he was staring down at me, his eyes and mouth were both wide open. Sensing his pleasure, I smiled, blew him a kiss, and looked him right in the eyes as I continued stroking his cock. I put both hands around it and picked up the pace. I leaned into it and put my lips on the tip of it, running my tongue in circles around it, all the while smiling and looking him right in the eyes.
He pushed my hands off of him, grabbed his cock, and with two quick pumps, cum began shooting out of him in a projectile manner. He groaned as it did so. The first spurt came out like a rocket, hitting me right in the eyes, disorienting me, and before I could recover from it, a second, third, and fourth blast hit me in rapid fire. I had my mouth open and managed to catch a lot of it like that, but he was spurting so heavily that it was still plastering my cheeks, forehead, and hair.
When I sensed that he had finished shooting blasts of cum, I put his cock back in my mouth and rifled it all the way down my throat, moaning as I did so. His body pretty much fell forward on me at that point, and he grabbed onto a wall to keep himself up. He was drenched in sweat, which meant I was drenched in his and my own sweat, and his chest was still heaving as he was trying to regain his composure and catch his breath. I began to realize that our time together was coming to an end, so I let his still raging hard cock loose from my lips, and stroked it a few times for good measure.
My panties were dangling from my right ankle, so I pulled them up, and maneuvered my way out from under him to crawl away. My entire libido was tingling, I had cum on my face, and was still savoring the taste of it as I crawled on my hands and knees like a cat who had just been hit by a car. I crawled a few feet from him, when I felt something grab my ankle. I could barely turn around to look before Reggie had his other hand on my other ankle, and pulled me to the ground. I started to say that the floor was painful and scratched my legs and belly when he pulled me down, but he was having none of it.
“Shhh, sweet little bitch, be quiet,” he said, “Daddy’s not done with you yet, just give me a few more minutes.”
I put up a half ass protest, before just giving in and abandoning my resistance. He mounted me from behind, but didn’t pull my panties down. He began dry fucking me outside of my panties, and muttering filthy talk into my ear. I could feel him sliding on my body, and drenching me with even more sweat.
“You took that 25 year old dick like a good sissy bitch. You loved it and want it every day. Tell me you want it every day. Tell me you want that dick up in your fine ass pussy holy every day,” he said, as he thrust his cock hard and fast between my ass cheeks and over my panties.
“I want that dick every day, daddy,” I said, in between thrusts and breaths, “Give me that dick daddy. Give it HARD to me.”
I have to admit, it was pretty hot, despite no penetration. He had put his big hands on both of my petite shoulders, and was rocking my ass back into his cock repeatedly for 2-3 minutes, before announcing that he was about to cum again.
“I’m putting this one on your back, bitch,” he said to me, as he pulled himself up and immediately started spurting ropes of warm cum on my back.
I think a lot of girls probably find it degrading to have a man cum on their backs, but not this sissy bitch. I love that feeling. He was grunting and straining as hard as he could, and slapping his cock down on my ass cheeks as he was stroking and draining it. He picked some cum up with his fingers and put it up to my face. I put his fingers into my mouth and sucked them dry.
He got another couple of fingers drenched in cum, then stuck his hand down the back of my panties, sticking his fingers directly into my sissy cunt and moving them around in a circular motion, which somehow began to make me cum again.
He fell on top of me again and began whispering in my ear.
“I’m sorry if you didn’t want that to happen. I just wanted to make sure I gave you all that my dick could give, and I wanted to make sure I snatched your soul, baby.”
What can I say? It turned me on.
He chuckled and kissed on my ear a bit, pretending to be biting on it, and sticking his tongue down in it. We hadn’t ever really done much kissing. The very first time he fucked me, he had me in missionary position, and he leaned forward and gave me deep kisses before he started cumming, but that was it, and this was probably our 4th or 5th time to fuck at this point. As soon as he heard me cooing and chuckling at him, he got up off of me and started looking for his things.
I handed him a towel that he immediately drenched, and put his clothes back on. He excused himself to go to the bathroom, then informed me that he was leaving right after that. I blew him a kiss, he blew one back, and tipped on out the door. I remained on the floor, on my back, and immediately began fingering my wet, creamy pussy, imagining the next time we would do it again.