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.