My Roomate's Brother

When I was in my junior year of college, I lived in an apartment with one roomate, Jen. We had been roomates since our time in the dorms, and were super close. We would go to dinner with each other's families, go home with each other on some weekends, and all sorts of other things.

One weekend, she let me know that her brother and one of his friends were going to stay with us as they toured the college. Both were seniors and 18 at the time. I knew her brother Ben somewhat well from my time knowing Jen (yeah, the rhyming names were a running joke for us), but I didn't know his friend Mark.

They showed up Friday afternoon, and we took them to dinner. We planned a night in with a couple friends coming over, drinks, snacks, and hanging out. Ben has always been super shy, he was a tall, skinny guy, dark mid length hair. Mark was more of an average build, sandy brown hair and blue eyes.

We were all sitting around drinking and we started off by telling embarrassing stories of Jen in front of her brother, which she started laughingly denying. Then one of the other girls hit her with a truth or dare, which turned into playing truth or dare as a group.

The game was mostly tame, but as it was getting later, the girls started asking both Ben and Mark about their sexual histories. Both turned out to be completely inexperienced, with Ben having kissed a girl once, that was it.

Around 2 am or so, it came to my turn, and I chose dare. I got dared to let Ben share my bed that night. Easy enough, I had had other guys share my bed, it didn't mean it had to be sexual. As everyone was getting tired, it was announced this was our last round. When it was Ben's turn, he tried going for truth again, which he had done all game, but the girl asking him convinced him to finally try a dare, so he agreed. She dared him that when he got in my bed, he had to strip naked and stay naked til morning. He got immediately red, and since I was already kinda drunk, I told him he didn't actually have to, but if he did it, I would do it too.

So, we got up to go to bed, and the two of us got into bed together. One of the other girls (obviously not Jen), came in and asked if he was gonna strip. He looked around, took a deep breath and started taking his clothes off. She smiled and pulled the blanket down while he did, and we both gasped when he pulled his underwear off. He had a rock hard, probably 9 inch dick. He apologized, and both of us told him he had NOTHING to apologize for.

She looked at me, smiled, said "have fun" and closed the door behind her. He still looked super embarrassed so I sat up next to him and told him he should be proud of that. He smiled, and looked down at my body a little, and I watched his dick twitched a little. I asked him, "do you want me to get naked as well?" He just nodded his head yes.

I stood up out of bed, pulled my shirt over my head, dropped my pants, then reached back to unhook my bra. I let it fall to the floor as I saw the first drops of precum forming at the tip of his dick. When I slid my panties down and presented myself, there was a steady stream dripping down the shaft.

I moved back into the bed, ran my finger up the length of his dick, cleaning the cum dripping down it and putting the finger in my mouth. His eyes got wide, and I asked if that was ok that I did that. He said it was, and that he liked it. I then asked if he wanted to kiss me, and he again said yes. I leaned in and kissed him, letting our tongues find each other. We made out for a few minutes and I could feel he wanted to touch me but was afraid to.

I reached out, and pulled his hand to my breast. He started squeezing it, obviously having no experience. I took my hand and guided his on how to properly massage a breast and play with a nipple. As he started getting it, I reached down, took his dick in my hand, and two strokes later, he shot his load all over my stomach and chest.

It had to have been the biggest load of cum I had ever seen. He apologized like he had done something wrong. I had to laugh, and told him he actually did something very right, then started stroking his semi hard dick.

He went back to kissing me, and I guided his head down to start sucking my breasts, while guiding his hand to my pussy, showing him how to properly work a clit.

He sucked on my nipples and played with my pussy and before long, his dick was rock hard again. I pulled him over on top of me, and guided him inside me. He pumped a few times and tensed up, unloading deep in my pussy.

He again apologized, and seemed to not know what to do. I let him roll off me, and told him to suck on my nipples again. He started sucking my nipples and I reached down and fingered myself to a pretty nice orgasm.

After that, we laid there and fell asleep.

I woke up to feeling the bed shaking a bit. When I looked, he was staring at my boobs and was stroking his dick. He saw me wake up and apologized (again), and said he didn't know when he would get the chance again to see a girl naked.

I told him to take advantage of it then, and pulled him back on top of me. He slid in and started thrusting. He lasted maybe 10 minutes before the door opened and in walked my other friend saying, "OK, times up, you can get dressed ag.. oh my god!! I'm so sorry!!" He freaked out but apparently that excitement got him because as he pulled out, he started cumming, shooting up to my neck and hitting everything in between. My Friend's eyes went from shocked to impressed as the cum covered my boobs and stomach. Once he finished, she slowly backed out.

I couldn't help but laugh, which made him turn red. I told him, "well, we better clean this up." I opened my door, yelled to Jen to stay in her room as Ben and I walked naked to the bathroom, passing a very wide eyed Mark on the way.

I let Ben clean my body in the shower, and I cleaned him, focusing on his dick. For good measure, I gave him a hand job in the shower using some body wash as lube, letting him cum one more time.

Part 2 will come shortly...