Young Chrissy Dresses and SucksbyCrossdressingChrissy©
I'm a recent college graduate at home for a bit while I look for work. I'm 21 years old. People don't know about this side of me at all, which makes all this even naughtier. I identify as being straight to everyone, but I was very curious about guys my whole life. However, I was always also curious about crossdressing. As a kid I loved to go into my mom's panty drawer and try on her clothes. I've also always felt kind of feminine, not sure about whether I should really be a guy.
When I got to college, I began to explore my bi side more. The only way I have ever done this is through Craigslist, though. So I started off by just putting ads up to get blown every once in a while because I wasn't getting any action from girls. I quickly became curious about doing more so I began sucking guys. I became really addicted to this. Some weeks I would post every night of the week looking for guys to suck. I would meet them in the parking garage near my dorm, get in their car, and suck them till they shot their cum down my throat. By my senior year this wasn't enough anymore, and I really wanted to try getting fucked.
One time when I was home from college I finally got the courage to meet a guy and let him fuck me. We swapped head, he rimmed me (my first time getting rimmed), and then fucked me. I was in heaven. He took it nice and slow and made sure I was comfortable. After that I let a few more guys fuck me, always from Craigslist posts. They are always older guys, and dads are my favorite. One time a guy asked if I wanted to try dressing up and being his girl, so I said yes. I felt so hot wearing a top and panties and lipstick. He bent me over and pulled the panties to the side and fucked me. I never felt so naughty.
I decided that I wanted to get my own clothes recently. So I got the courage together and bought a lingerie set of a sexy red thong and a red bra with lacy white around the edges. I also bought some lipstick, and then met with guys from Craigslist a couple times and sucked them off. This set of panties and a bra weren't enough, though. I want to try to become passable and to go out in public comfortably. So for the next step, I went to Macy's and bought myself a black skirt, some brown tights, and a white top that has a lacy front showing some of the bra underneath throw.
After I got these clothes I posted on Craigslist again. This is when I met Sam (what I call him in this story, I never actually got his name).
I posted on Craigslist:
"i am looking to suck your cock until you cum on my face or down my throat. i'd also love to cd for you if you'd like me to wear my girly clothes."
Ya, I know what you're thinking, slutty post, but that's what I'm into. I love being a dad's little girl who services his cock. So Sam responded to the post and we exchanged a few emails, deciding that we would meet in the Dunkin Donuts parking lot, and I would get in his car to smoke a joint and give him road head. His stats were 53 years old, 6'4"m a 240 pounds. He turned out to be much taller and stronger than me. I am about 175 pounds with an average body and not much muscle. Perfect, we would meet in 30 min.
So I shaved, because I hadn't met anybody in a while in my outfit I hadn't shaved, and then showered. I walked through my house with my normal clothes on so that my parents would just think I was leaving. I had my girl clothes in my coat, though, and put them on in the garage before I left. I put on my panties, slide on the tights, hooked the bra, put on the shirt, and finally applied lipstick. I was ready to go. I got in the car and drove to the Dunkin Donuts. I pulled in, turned the lights off, and when I did so, Sam pulled up in his car. So I got in his car and we greeted each other. We drove out of the parking lot and he offered me the joint he had rolled. As we smoked it, we were rubbing each other's legs and getting a little turned on. He told me that he was really horny and wanted to go to his friend's garage instead of doing road head. He told me it was a few minutes away, and I agreed I would go there. So we kept rubbing each other as we drove to the garage.
We pulled into the garage, closed the garage, and turned off the garage light, leaving just the car light off. As we stood in the garage, we started kissing. Wow, I thought to myself that all we were going to do was have me suck him, but I was really horny too and kissed him back. We kissed passionately using our tongues as much as possible. We kept rubbing each other, now starting to play with each other's cocks. He pulled my skirt up and played with my balls. Then Sam turned me around and kissed me on the neck while he reached around stroked my cock. Man it felt so good.
I reached behind me and started rubbing his cock. When he was really hard I asked him if he wanted me to suck him. So I got down on my knees and took his nice cock in my mouth. He was 7 inches and thick, but it tasted so good. I took it all in right away, sucking all the way up and down while he grabbed my head and pumped his hips into my face slightly. He kept holding my head down on it while I swiveled my tongue all around his tip. I could taste some of his precum.
Then Sam took my head away and sat down on the steps by the door to the house. I walked over and he pulled my thong to the side, grabbing my cock and rubbing it. He had a great firm grip and steadily rubbed it. Then he took my whole cock in his mouth. I am thick and about 7.5 inches and he had no problem taking it all in his mouth. I'm usually a quick cummer, so he sucked me for about a minute all the way up and down, taking it deep.
Then he popped it out of his mouth and turned me around. He said sit back and I sat back on him on the steps. I didn't actually sit on him but rather did a little dance, rubbing my ass on his cock while he sat down. Since Sam was a big guy I could rest my back against him and my neck on his shoulder while I grinded my ass against his cock. He then took his fingers and started rubbing my ass. I was nervous that he was going to try to fuck me, even though we hadn't agreed to it. (I know I have fucked before but this night I was just in the mood for sucking.) But he just took his dick out and rubbed it against my butt. Then he lifted my skirt again, and pushed my panties to the side while he slid his tip back and forth between my ass cheeks.
Then Sam turned me around and told me to suck him. I got down on my knees and slid his cock in my mouth. I took it deep each time, sliding it in as far as it goes. He loved to grab my head and pull me in. Finally, he pulled me in hard and wouldn't let me off while he shot load after load after load in my throat. I love having it shoot in my throat because you just automatically swallow it all. His cum tasted so delicious. After this, we got up and walked to the car. I pulled my skirt down and got in the car. I was so horny because he had sucked me before but not to completion. On the ride back to my car, he kept rubbing my leg while he talked to me. He told me to pull up my skirt again, so I did and he grabbed my cock. I loved the way he jerked my dick. A nice firm solid grip and a constant up and down. I pushed my hips into his hand each thrust, wanted to cum so bad now. Finally, after 3 or 4 more minutes I couldn't take it anymore and shot my jizz all over my pretty skirt and shirt.
We got to my car and I got in. Wow, I thought to myself, that was so hot, as I felt a mess. On the drive home I jerked off again thinking about how hot it was and how I want to do it again. I emailed him back while writing this story to ask if he wants to meet again. This happened last night.