How I lost my butt cherry

I had always fantasized about being with men, but it wasn't until college that I decided to do something about it. While home from school for a week, I decided to look into my curiosity of men. After everyone had gone to sleep I logged onto the internet and began looking at gay sites. Then I stumbled upon a gay chat room. As their were different chats I located one that was for the small town I attended school in. I expressed my curiosity and got several replies from men. One in particular caught my attention. He gave me his phone number and told me to call if I felt comfortable. He didn't pressure me. When I got to school I put off calling him for two weeks, mostly because of nerves. Then one night when my roommates had left for the bars, I decided to give Sean a call. At first he didn't know who I was, and asked me to call back since he was on the other line. 

I was shy, and almost didn't call back, but my curiosity and hornyness got the better of me. I called back an hour later. We talked about different things before he asked me if I wanted to meet. I agreed, but I thought it would look suspicious if he picked me up from my dorm room, so we decided to meet near a park not far from where I lived. I told him I'd be wearing a green jacket, which I wore. He drove up in a black pick-up truck. I got in the car and introduced myself. He was a tall muscular white guy with curly blonde hair about 6'2, 230 lbs. We drove back to his place and had small talk. I couldn't believe what I was about to do, but I figured there was no turning back now. He lived in an apartment just out of town. We sat on the couch and he fixed me a drink, then he popped in porno. It was the first gay porno I had ever seen, so it was kind of odd. I studied it, and he studied me. He put his hand on my inner thigh, and asked if I was ready. Before I could respond he was leading me into the bedroom. 

I don't know what came over me, but as soon as I got in I began to undress, Sean did the same. I left my tighty whities on and walked over to the bed, he did the same. He asked if I'd like a massage, and I responded yes. I lay down on the bed and soon Sean was on top of me massaging me with his strong hands. It was the best massage I'd ever had. I could feel his massive erection poking out of his underwear directly into the crack of my ass. I was extremely turned on by the feel of it poking against me. I wanted him to free it, pull down my draws and fuck me right then. I pulled off my underwear after the massage, and he got rid of his underwear. He began to give me handjob. I was in heaven, I grabbed his cock and began to do the same. It felt weird to be handling a cock other than my own. Especially his it was massive. I didn't know if I'd be able to take it, but I was willing to give it a shot. After the handjob I decided I wanted to give Sean head. I pulled out a condom and slid it on his dick, and then I began to go down on him. This didn't work well, the condom was non-flavored and the taste of latex was horrible. So I stopped. Sean was disappointed so I offered him my ass instead. He asked me if I was sure if that was what I wanted, I said I was sure. I only asked that he use a condom, and some lubricant, and that he take it easy on me since it was my first time. I laid on my stomach and prepared to be fucked. I felt Sean part my ass cheeks. He tongued my ass hole and it felt great. Then I felt the cold lubrication as he lathered up my asshole.

Next I felt a sharp sting of inexplicable pain as Sean's massive cock filled every inch of me. I screamed in pain and begged him to stop. He reassured me that the pain would pass. He asked me to take a deep breath and relax. Since I had no other alternative I did. He was right, after I began to relax it felt better. I was less tense nad the strokes began to feel good. He built up quite an intensity, and before I knew it he was drilling me like a jackhammer. I loved every moment of it. He was giving my ass a thorough fucking. I just let him have his way with me. He fucked me for what seemed like hours, before he let out a giant moan. I knew my butt would be sore from the buttfuck I had just received, but I didn't care I was happy at the moment, but still horny. It took some convincing, but Sean finally agreed to let me fuck him. By then I was so horny I thought I would die. I couldn't wait, after smearing his butt with globs of lubricant I jammed my cock up his ass. He let out a sharp moan, and pleaded for me to be more gentle. No such luck I fucked him hard until I blew my load. Then I collapsed onto the bed. Afterwards he drove me back to campus. He urged me to call him anytime I wanted to fuck. I thought about it many times, but I never did. I guess I was afraid of becoming a total butt slut. He was my first and only time with a man. Since then I've been with a number of women, but nothing will ever compare to that night. Who knows maybe I'll go for round two someday.