Normally I never would have entertained the idea of sleeping with a co-worker but when I saw my boss’s son for the first time, that idea quickly went out the window. It wasn't like I didn't think about fucking my co-workers,

I did… in fact, I would leave work some days leaking with precum from the various exchanges I had and my mind running wild there are so many private spots that I would love to take advantage of with the right person but let us leave those fantasies for another story…

This situation was different. The fact he started flirting with me almost right away just made the whole idea of hooking up with him even more enticing. It’s not like I was lonely, but my situation as a trans woman in the office sometimes made me have to make sure things were kept on the down low. I wear tight figure-hugging dresses and skirts every day, I didn't need everyone to find out that hidden in my stockings was also an eight-inch uncut cock.   

It was easy to get him to come over to my place with a simple after-work invitation. And I knew right away that this time the seduction part was going to be easy to accomplish. So many guys were into trans women but of course, the seduction process was sometimes complicated, however pressing up against me more than once in the office, I knew he was well-hung already and that was something I couldn’t wait to experience sliding into my ass. In my dreams, I pictured myself opening up his pants and seeing a delicious long shaft hard and ready for me to devour. 

The day before at work I’d invited him back to my place after he flirted with me in the lunchroom and he’d eagerly accepted. There was so much unspoken between us, but the one thing I knew was that he wanted me. 

Flirting at work was one thing and was always a bit risky. Thankfully he was the boss’s son and was part of the ownership group, so there was no way I was about to get an HR violation by flirting back. But there was really no be coy at all in my own home. I wanted to see his nice thick cock just like I had been dreaming about. 

Sexual harassment? Not if I was willing. And I knew because I was a very sexy trans woman, I’d been flirted with and hit on a lot during my career. Normally demure, now it was time to open up because frankly, he was sexy, virile and I could tell from how he was so damned cocky that he’d fuck me into oblivion. All good qualities for me to enjoy.  

Now that we were alone, it was easy to let myself be seduced. He was smart enough to make the first move and kiss me, and then as we made out all I had to do was make sure he was okay with everything by moving his hand over my hard cock. When he squeezed it and moaned into my mouth I knew it was all good to go. 

I told him I would be right back and strutted into the bedroom, where I changed into a tight back stocking dress. When I walked out, my cock was encased in my panties but was nice and hard. He’d taken off his shirt and as we kissed again and he eagerly squeezed my ass, I knew exactly what I wanted to do. Give him a blowjob he’d never forget. He cupped my erection through my panties and I could tell he was eager to explore and be explored. 

I knelt down and slowly took him out. When I did it was a pleasant surprise. He was rock hard, nicely groomed and clean and looked delicious. It was easy to lick his shaft and then take his lovely throbbing dick into my lips, sucking gently. He encouraged me the entire time with gentle groans but wasn’t lewd about it. The flavour was slightly sharp as if he’d just come from the gym and had a light sheen of sweat on his body. Or maybe he was just nervous.

Taking it out and looking at his bare shaft, the veins formed little ridges I could slide my tongue around and his spongy head was engorged fully, almost purple with his obvious desire. 

My tongue ran up the underside and then I teased his head with my lips, swirling around the bulb because I knew how sensitive it was. Taking his thickness in my mouth I sucked gently, then eased off and teased the head again. It wasn’t long before he took a grip on my hair and forced his dick into my lips, making sure that I wasn’t going to tease him anymore. Now it was time to suck him off properly. 

His dick was nice and long, easily reaching the back of my throat as I took him deep and almost cut off my breath. Pulling off, I spat across his length, making him slick with my saliva and then stroking his entire length to make sure he was good and lubed up. There was no way I wasn’t letting him fuck my ass today. But for now, it was all about enjoying his length and making sure he was enjoying me. 

So I decided to take my time, going up and down the length of his shaft and then liberally applying spit to it, stroking the base. I slipped his balls into my mouth while I stroked him, enjoying his groan of pleasure and the way his cock flexed in my hand as I gently sucked the sack between his legs. It was hard to resist sliding a finger into his ass, but that could be for next time. After a few minutes of deliberate slowness and coating his cock thoroughly, I was ready for him. 

Normally my men would suck my cock as well a bit, depending on the dynamic, but I knew that this was all about him enjoying his new transgender lover. Younger guys were also always eager to get my clothes off and just get inside my tight hole, which was fine with me in this case. I had been thinking about and craving a nice big cock in my ass all week and ever since I’d offered for him to come over.

His shaft was just so delicious and musky flexing in my mouth I decided to hold him off for a bit, making sure that he was definitely ready. After all, we were finally alone with time to enjoy each other. His moans started to get lower and faster, and I made sure to reach down and squeeze his shaft to back him off before taking him deeply again. It wasn’t long before he grabbed my arms and pulled me to my feet. 

Standing me up, I knew it was time and slipped my panties down, finally letting my own hard cock spring free. I didn’t even want to head to the bedroom, instead turning around and placing myself on the couch in front of me. My legs were spread and my dress was around my hips as he spanked my ass once sharply. Then I felt him step forward and his sexy cock pushed against my eager asshole while his hand slipped between my legs and stroked my dick a few times. 

He was well lubed up, so he slipped in quickly and his thick head spread me wide right away with a gasp. Inch after inch slid inside, and then he pulled out and thrust in again, making my own cock sway with the force of his thrusts and the moans that came from behind me. Within a few movements, he was buried deep in my ass, the fullness making my whole body feel like it was singing with pleasure. As he moved, my cock swayed between my legs. 

Moans filled the air around us, his cock filling me perfectly while his hands gripped my hips and continued to fill me up. The slap of his balls against my own was intensely hot as we swayed back and forth, easily moving into a rhythm of sexual pleasure that we both had been craving for so long. 

His hand reached around my hips as my cock swayed between us and he took a hold of it, jerking me slowly at the same time as his wonderful cock fucked my ass. I couldn’t wait to feel what it might be like if the tables were turned, but for our first time together I was happy to be his bottom. Every thrust inside felt like fire to my insides. 

Placing myself on the couch on my knees, it was an easy adjustment to push back into him now that I had some support underneath me. His lovely dick moved easily inside me, picking up intensity. I knew that my tight asshole could milk the cum out of his cock in no time, but I wanted our sexual fun to last and last.  

I could tell he was close when he started pulling out after every few thrusts, slapping his hard dick on my bare ass, then sliding it back in to repeat a few times. But there was no way I wanted him to stop. I wanted to feel his sexy cock spurt cum all over me. Inside me, filling my tight hole with his cream and feeling it leak out of me.  

Both of us were moaning loudly, finally, I could feel his dick pull out and he began to stroke his cock hard with a gasp. Then the glorious sensation of his cum spurted into my ass cheeks. His hand massaged my cheeks as he drained his cock, using his softening dick to rub the cum into my skin. 

All we could hear was the hard breathing until he let out a sigh of satisfaction. His hands massaged my ass cheeks and he sighed as his hands rubbed the sticky cum onto my skin finally I knew that he had been satisfied. It was great, for the first time.  

Turning around, I leaned in and kissed him again, feeling our bodies rub together. Even though he hadn’t gotten me off, I didn’t care. For a first-time experience, we both could tell there was going to be another. And another. 

After all, there was an entire office to enjoy. And I also needed to shower off. It was time to put his oral skills to the test. I couldn’t wait to feel that sexy young mouth wrapped around my cock and then turn the tables so that I could enjoy his sexy ass.