My first experience with anal [F19/M21] | 2016

These stories describe experiences I had in college. I just graduated, and I have never found a place to talk about what I went through. They all revolve around Kevin, an older student I met during my orientation week.

The day following my first time with him, we started texting. Following advice from some of my (quite new) friends on my floor, I didn't immediately give in to his texts to meet up, especially the ones sent late at night. We flirted back and forth via text and snapchat - he kept asking for nudes, but I kept just sending regular pictures.

Eventually, he texted at a somewhat reasonable hour, and I had been drinking in one of my floormate's room. I was just drunk enough to say yes - and headed over. After a bit of formality, we went up to his room and he had sex with me again, a replay of last time. I asked him to use a condom, but he said that he didn't want to and that he wouldn't cum inside me. With my panties around my ankles, I felt him pull out of me and finish all over my back - I had remembered to take my shirt off this time.

This became a regular occurrence. I was balancing my classes, meeting new friends in my building, and getting texts from Kevin, going over, and letting him have sex with me. Guys from his fraternity started to recognize me on campus, give me waves and talk to me - something which made me quite popular among my now growing group of friends. One of my roommate's friends started hooking up with one of the brothers at Kevin's house. I felt a sense of acceptance in a way I hadn't ever before.

At once or twice a week, it felt like a good situation - I got to socialize with people I never would. I started trying things to make Kevin's requests more frequent. He enjoyed dirty talk. Usually he would have sex with me from behind but sometimes halfway through I would stop and insist that I get on top. He would kiss my chest and thrust.

This had gone on for a month, and he texted me later than usual, on a Friday. I showed up and there were a few guys around, all drinking. Some of them I recognized and chatted with. Soon, Kevin and I were upstairs. Again, after a few minutes of making out and wandering hands, I felt his erection, unbuckled his belt and slowly began rubbing him. He unsnapped my jeans and slipped his hand down the front of my pants, roughly rubbing me.

He pushed me onto the bed and held me there. I felt his hands slip into the waistband of my jeans and pull them down to my knees, panties and all. He asked me what I felt like right now, and of course I answered what he wanted to hear - that I felt like a little slut. I felt his erection against me, and heard him spit. I'll never forget what he said after that.

"Then you should like this."

He pressed his erection into my ass. I had never felt pain like it. I cried out and he put his hand on my back. He felt enormous inside me, and all I could feel was tearing and stretching. He spit again, and I held my breath thinking that would make the pain less. Going slowly, he pulled out of me, I felt him add more spit, and then pushed in further than the first time. The pain was searing. The third thrust felt like it went in further than the second, and my eyes were clenched shut, hoping that it would end soon. I heard him asking if me if I liked it, and all I could do was gasp in. Wanting it to end so badly, I told him in the sexiest voice I could muster that I liked him fucking my tight little ass.

As usual, the dirty talk finally ended it. He pulled out, giving me some relief, but then pushed in fully, causing me to grip the sheets again - and grunted my name. I could feel him cumming inside me. My first thought was - well, at least no chance of pregnancy. After his orgasm subsided, he pulled out slowly.

I didn't stay that night. I pulled my pants back on and left. When I got home, I changed. There was a big wet spot on my underwear where his cum had leaked out of me. It took me a long time after that to text him again.