I was always curious about what it would be like to be with another guy. I would always go to chat rooms talking to older men, telling them how badly I want to suck their cocks. Sometimes if I felt bold I would post on craigslist saying that I wanted to hook up with some stranger. I was always way to nervous to go through with it so I usually just left the men who responded to my ads hanging.
One day while looking through my email I found a response from someone close in age saying they would like to experiment too. For a few weeks we kept emailing each other back and forth talking about hooking up with each other. He told me that a big turn on would be if I was wearing women's clothes. I got excited by that idea because I always liked getting dressed up in my mother's or sister's clothes and acting like a little slut when no one was home.
We decide that we should exchange some naughty pictures of ourselves, to make sure we would be into each other. I sneaked into my sisters room and put on some of her underwear and a pair of fishnets I knew she had hidden in her closet. I took a few pics of myself in the mirror(not showing my face) and emailed them to him. He sends me a picture of his thick 7in(he told me how big it was) hard cock.
I was so turned on by his pictures that I asked if we could meet soon. He told me that he would have the house to himself tomorrow night and that would be the best time to meet. We realized that we only lived a few blocks away from each other, and agreed to meet on the golf course before going back to his house.
Throughout the night we decide to get to know each other a little better. He tells me his name is Tyler and says that he's lived on the island his whole life. I start running through all the people I know in my head but nothing is ringing any bells. He asks what my girl name is and I said I liked to be called Jessica.
The next day while my parents are at work I sneak into their room and raid my mothers underwear. My sister's clothes were way sexier but my mom did have a black lacy garter belt that I thought would look good. I then make my way over to my sisters room and take the black bra, panties and fishnets that I wore in the pictures. Along with that I grab a black skirt and some of her make-up.
At around ten at night I log on to my email and wait for him to email me saying we should meet up. While waiting I decide to get all dressed up. Thankfully since I've been dressing up for the past two years doing my own make-up has gotten pretty easy for me. I grab one of my white button downs from my closet and tie it a knot kind of like daisy duke. I take a look at myself in my mirror and damn do I look sexy.
After thirty minutes of waiting at my laptop watching porn, I get an email from him telling me to be on the golf course in ten minutes. I put on a pair of sweatpants and a hoodie so that no one can see what I'm wearing and start walking towards the golf course.
The whole way over there my hands are shaking, I'm incredibly nervous. Part of me wants to turn back, I mean what if I'm not really gay. As I get closer to the meeting spot I can see that he is already there and that he sees me. There's no turning back now.
I walk up to him and say, "Hi I'm Jessica." "What's up Jessica I'm Tyler." When I finally see his face it all clicks. Back when I was in middle school this guy would always make fun of me. He used to tell me that I was gay and if I was ever eating anything phallic shaped he would say I was imagining that it was a penis.
"Tyler... we went to middle school together, you used to bully me." "Oh shit James I barely recognized you. If you feel awkward about this we don't have to do it?" "I mean we are already here so why not try it out."
We start walking towards his house in complete silence. I think we both realize that his really awkward but neither one of use want to break the silence. That's when he says, "So are you wearing girl's clothes under your sweats?" "Yea I didn't want anyone seeing me wear this." After a few minutes we arrive right outside his house and he tells me to take off my sweats the moment we walk in his house.
I do exactly as he asks and he says, "Damn you went all out with those clothes." I giggle a little bit and then ask him where to go. He leads me up to his room and tells me to get on my knees. The moment I get on my knees he whips out his cock, without being told I start sucking on it.
I start to feel it get hard in my mouth and I begin to really enjoy myself. I never could have imagined that dick tasted this good. While I'm sucking his dick I start involuntarily moaning. He grabs the back of my head and shoves his cock as deep as he can down my throat.
While this is all going on I start taking off some of my clothes. "Do you wanna try going all the way?" "MHM." He takes his dick out of my mouth and tells me to get on all fours on his bed. While walking towards his bed I slide my panties and skirt off and kick them to the side.
While I am waiting on his bed I can hear him grab something off his dressed and then squirt something. He starts slapping his hard cock against my ass and tells me to take a deep breath.
I breath in deeply as I feel his penis touch the my asshole. He starts to slowly slide it and at first it's very painful. "Be gentle." I moan. He doesn't respond at all he just keeps pushing it in. I start letting out these loud moans, he pushes my head down and tells me to be quiet.
After he get's balls deep he starts getting really rough. Sliding his cock in and out as fast as he can. When I start getting a little to loud he slaps my ass hard and tells me to keep my mouth shut.
After around 15 minutes he pulls out and tells me to get on my knees. I quickly get on my knees and he bust a huge load in my mouth. "Alright you can get dressed I'll meet you downstairs."
He quickly runs downstairs before I have a chance to say anything. Before putting my clothes back on I take a look in his mirror to see if my make-up got fucked up. Surprisingly it stayed together nicely, my lip stick got a bit smeared but I still look good. While I'm putting on my clothes I start thinking about why he was so quick to run downstairs. I try not to give it much thought but I feel like he is up to something.
When I get to the door, I go to pick up my hoodie and sweatpants, only problem is that my sweatpants are missing. "Tyler, where are my pants?" "I'm gonna hold on to them, walk home like that." After a few minutes of arguing and a threat made by him I gave up on trying to get them back. I put my hoodie on and walked straight out the door.
Even though I only lived a couple blocks from his house, it was still a pretty long walk. I pull the hood over my head in hopes that it my disguise me a little better. My hands are shaking uncontrollably in fear that someone might see me like this.
I get halfway home and I start hearing a car engine coming from behind me. I start looking to see if there is any where I can quickly. Sadly all that are around me are fences I am completely fucked. I can hear the car getting closer and closer, at the same time though it sounds almost like it's slowing down. As the car is passing me the person driving honks and says, "Nice ass slut!" I look in the direction of the car and I don't even recognize the driver.
Thankfully for the rest of the walk back to my house not another car passes me. Everyone is still asleep in my house so no one will see me like this. I run to my room, lock the door and hop right back on to my laptop. There's an email waiting for me from Tyler saying, "That was fun we should do it again, also you should buy a wig."
