The first time with one of Kevin’s friends [F19/M21]

This one is short, because it actually was short. But it was the first time that I realized I had real power. We had now been fucking for a few months. He would text or I would text. My hall mates would give me looks, he could only show up when my roommate was out of town. I’m also pretty sure they could hear us each time. I tried to be quiet, but he wasn’t. He was laying in bed with me after a particularly long session and he asked point blank if I had ever thought about “branching out.”

I’ll never forget him calling it that, because it sounds like a word you use to describe taking a weird class in college or taking up pottery. By the end of the conversation, I’d agreed to help one of his fraternity brothers who had a lot of trouble with girls. It was simple, I would show up, talk to him for a while and then go upstairs. It wasn’t cheating, Kevin was okay with it – in fact, he said it turned him on.

The party was the following Thursday. During the week Kevin kept texting me – we had phone sex during the week. It was more of me talking dirty to him. I could hear the rhythmic stroking in the background until his breathing got heavy and he came all over himself.

***
I showed up to the party dressed exactly as he had told me, a particular red and black print dress, stockings and heels. I can’t remember the underwear but it was small and black I’m sure.

Seeing Kevin, I went over to him – he immediately directed me toward the back of the common room. People were drinking everywhere, but there was one guy, tall and lanky, in a cardigan. That was Tom, or Tommy as they called him. Kevin called out to him and he immediately looked me up and down.

He came over and the three of us chatted about nothing. Kevin walked away leaving me with Tommy. He asked me what classes I was taking, and commented that one of the professors was one he’d had. I could see he was a little nervous – he’d put his cup down and picked it up twice. His eye contact shifted between my face and my chest.

“Do you live in the house?” I asked. That was all it took. He offered to show me his room.

He was rougher than Kevin, which I didn’t necessarily mind. His hands wandered up and down my sides. He kissed my neck quite a lot, which felt nice. I couldn’t escape the fact that I was basically just an object for him. We fell onto the bed and continued making out. His hands had wandered down to the hem of my dress and were stroking my legs. I could feel his erection against me. I rubbed it a little, and this seemed to shift everything.

“Can you get on all fours?”

I did.

The sensation I remember most actually, is that of my underwear around my thighs, just above my knees. Why don’t boys remove it all the way? I could hear his belt unbuckling, the sloshing of fabric, and then the hot fleshiness of his cock, underneath my hitched up dress. I looked back at him and he smiled meekly as he drizzled a glob of spit into his hand and gingerly rubbed it over himself – circumcised, I noticed. He seemed Jewish. I thought about asking him to wear a condom, but I didn’t think it would go well with the flow.

He pressed himself in slowly, about halfway, and then pulled out. Then again. Twice. Then he shifted and for a second I thought he had stubbed his toe on the bed, because that’s what it sounded like. Then I realized what happened.

“Did you cum?” I asked. Looking back at him he was breathing heavily and looking at the ceiling. He pulled himself out of me – his cock was gleaming and drippy. I reached underneath and found that his cum had stained the front hem of my dress – there was a lot. I could feel it still coming out of my pussy, my hands slippery.

“Don’t tell anyone about this.” He said.

“I won’t, I’m sorry.” I genuinely was.

We went back to the party.

Source: reddit.com/r/gonewildstories/comments/52g9qs/the_first_time_with_one_of_kevins_friends_f19m21