I went online, and started on some chat rooms. I regularly went into chat rooms to flirt, and find guys for some fun phone sessions. This time I wanted more. I started talking to one guy who seemed like he could be a good fit. He was friendly, and made me really comfortable right away. We talked for quite a while, until finally, he asked if I’d like to come up to his place. I was hesitant. I had not done this often, and I wasn’t sure how far I would be willing to go. But I said “yes.”
I got myself all dolled up for him. I put on a sexy thong, and bra, garter, black stockings, five inch heels, a sexy blue dress, and I did my makeup and nails as sexy as can be. I put on some sexy Victoria’s Secret perfume, and I walked to my car completely dressed and confident. I drove up to his place, wondering what was going to happen. Would I be able to go all the way?
He came to the door as I pulled into his driveway. I got out of the car, and I could see him smiling as my heels clicked against the pavement on the way to his door. He opened it. “Hello, Vanessa, nice to meet you,” he said and kissed me on the cheek. We hugged and he led me to his living room. He sat on a chair, and I sat on his couch on the other side of the room. I asked him for a drink, so he got us a couple of beers.
As we drank, we exchanged some small talk, both knowing what was on our minds. He finally came over and sat next to me. As we talked, he put his hand on my leg, and started rubbing it. He asked if I liked it, which I replied that I did. Then, he stood up and pulled his pants off, and took out his cock. It was already pretty stiff, but I reached out and started stroking it. It was an odd feeling since it was only the second time I felt another penis in my hand, but I liked it. I liked the way he reacted to me touching it. I liked the feeling of it getting harder in my hand, and the way I could tell how much he wanted me while I pleasured his stiff cock.
He moaned enjoying my hand working his rod. I was seated, already at about the right level, so I decided it was time to taste my first cock. I put it in my mouth and started sucking it, bobbing my head up and down on his hot cock. I took it deep into my throat, and then licked it up and down. I played with the head with my tongue, and then swallowed it down my throat again. This was my first time and it was a long time in the waiting so I was going to enjoy every inch of that dick. I wasn’t sure what to do, but it somehow felt instinctual. His moans told me that I was doing it right, so I just enjoyed the soft flesh against my lips and tongue. I deep throated him again, letting all that practice on my dildo pay off, and he let out a loud moan.
After a few more minutes of sucking his hard cock, I decided that I wasn’t going to make the same mistake as my last encounter, where I knew I wanted to go further and didn’t. I laid back on the couch, kind of on my stomach and my side, and I pulled up my skirt. I pulled my thong over, and spread myself open for him. He quickly understood that it was time for my virginity to become history.
He got his cock lubed up, and slowly began to work it inside my tight hole. I couldn’t believe the feeling of it sliding into me. I had used my dildo a hundred times before, but it doesn’t prepare you for the feeling of a real cock. As he fucked me, I couldn’t believe I was finally doing it. I finally had my first man, and I finally felt the pleasures of being fucked as a woman. I squeezed his cock with my hole, wanting him to feel fully pleasured by me. It seemed that was all he could take. He asked me if I wanted him to pull out, but I decided that I wanted to experience it all. I told him to cum inside me, so he did. It felt so wonderful, as his dick spasmed inside me, filling me with his load.
We talked some more, and I decided it was time to get home. He walked me out, and I got into my car and started home. I felt like a new woman.
Via: https://www.lushstories.com/stories/cross-dressing/vanessa-goes-all-the-way