My first time with a guy [M/M] | 2016

This all started my senior year of high school. I had always been into girls but I was always curious when it came to sex. While watching porn I wondered what it felt like to have a cock in me. So I started to steal my mom's dildo when she wasn't home. The thought of a man having his way with me was so erotic. I started watching alot of porn and masturbating with a dildo. Soon I got my own that I could suction cup to my shower.

Eventually I grew tired of using a dildo. I started to order sexy outfits and thongs/panties. Being dressed so feminine was such a turn on. One night I was scrolling through craigslist at the causal encounters page. I just planned on reading ads and jerking off but one caught my eye. It was by an older guy named James that was looking for someone younger and new to this scene. We started messaging back and forth. I told him how I liked to wear skirts and panties. James told me that was weird and not normal. He said I was a sissy and a slut. This didn't turn me away from him but it turned me on.

After a few days of texting James asked me to come over and join him in his hot tub. I was nervous and hesitant but he was very overpowering and dominant with his words. I agreed to dress up and meet up with him. So I put on this little gold skirt and top with a black lace thong. I put on sweat pants and a hoodie over it and left. I walked to his house debating if i should back out or not. I got to his house and stood outside his door for what seemed like hours. I eventually knocked and he let me in.

I was nervous and shy. He asked me a few questions. He then pulled down his pants and asked me if I wanted to touch his cock. I was apprehensive at first. My cock was about average girth and 7 inches long. James dick was about 8 inches long and really fat. He took my hand and placed it on his cock. I played with it for a few seconds completely mesmerized at it. Then something came over me and I got down on my knees and took him slowly in my mouth. I was so hungry for his cock.

I never really thought much about sucking cock but once I did it I loved it. He just sat back while I happily engulfed as much of his dick as I could. After 10 mins or so he told me to take off the sweat pants and hoodie. He was surprised to see the outfit I had on underneath. I eagerly told him I wanted him inside me. He led me to a big bean bag chair bent me over, lifted my skirt up, and pull my thong to the side. He noticed that I lubed my ass up before I came and he called me a little where. I just wiggled my ass. I felt the tip of his cock press against my ass. My mind begin to whirl with thoughts of regret. I knew once that cock was in me there was no return.

I had only used small dildos, so it was a struggle trying to take his cock in my ass. It was very painful but such a turn on. He finally got it all the way in. He started to make long slow strokes. After about 10 minutes of slowly fuck my ass it started to feel so good. My ass had fully accepted James cock. I thrust my ass back towards him as a sign I wanted him to pick up the pace. He then started to fuck me harder and faster. He was going so deep and I was lost in ecstasy. He pulled out and sat back on the bean bag. I turned around and slowly sat down on his cock. It was so hard as I slid all the way down it. I bounced on his dick like my life depended on it.

I got tired of being on top so he led me to a bar stool and had me sit down facing forward. He adjusted the height of the stool so my ass was even with his dick. He grabbed my be the hips and pulled my ass to the edge. He then pushed his dick against worn out hole and my ass swallowed it. He preceded to fuck me relentlessly. All I could do was sit there and enjoy this pure bliss. For the next 15-20 minutes I just moan like a little slut while he fucked me like a whore.

Finally he asked me if I was ready for his cum. Instinctively I told him to cum in my ass. He gave me a couple more powerful thrusts and then I felt a rush of his cum spray into my ass. After we cleaned up and I got dressed James asked me if getting fucked was what I expected. I told I was in love with the feeling of a cock fucking me. James told me he would give me a ride home and I was thankful because it got alot colder since I walked over. On the drive back to my house I asked if I could give him road head on the way back. He just laughed and pulled down his short and said you're a cock hungry slut. I said I couldn't deny that as I inhaled his dick. He had to circle around my block so he could cum. He pulled next to my house and I got out and told him thanks for the night. James said hopefully we could do it again waved and left. I went into my house. My mom asked what I've been doing. I told her just hanging out with a friend. She asked how it was. I told her I had a amazing time as I felt James cum dripping out of my ass and down my thigh as I went to take a shower.