My Roomate's Brother

Every year, my university would host an orientation weekend in the spring for high school seniors that would be attending the school the following year. It so happened that, my best friend's (and roommate) brother, Josh, had just turned 18 and was a high school senior, enrolled to start the next year at our school. Their parents encouraged him to come down and spend the weekend with us.

Josh was a painfully shy, marching band president type of guy. He was tall and skinny and carried himself in a way that showed he had no confidence in himself. He was very nice, and when he did start to open up he was pretty witty and funny.

He got to our apartment on Friday afternoon, so Sara took him on a tour of some of the buildings he would have classes in, the union, and some of the dorm buildings. Later on I met them for dinner and we went back to our place.

Most Friday nights, a group of our friends would bring beer over, we would hang out, play stupid games, get drunk, and pass out. This Friday night really started out no different.

Among this particular group of friends, one ongoing game that always got played was truth or dare. Not sit in a circle and spin the bottle type, just walking up to a person and asking truth or dare. No one really came up with dares or questions that were too outrageous because payback would be a bitch, but you also never backed down, because punishment would be much, much worse!

As the night wore on, I found myself in the kitchen talking to Josh about the school. One of my drunk friends comes in and asks me truth or dare. I thought for a second and said dare, since id been pretty truth heavy most of the night. She got a wicked look on her face, and dared me and Josh to sleep naked in my bed that night.

I gave her the dirtiest look ive ever given someone, but couldnt back down because she definitely had some dirt on me she could spill. I looked at Josh and said you don't have to do this, but I can't say no. He looked at me and told me that he didn't want to be the reason that I backed out on a dare.

My friend, Josh, and I went up to my room. Josh and I got into my twin sized bed and pulled the covers all the way before stripping completely and handing her our clothes. She closed the door behind her on her way out and the two of us layed there in silence for a few minutes.

Finally, after a few minutes, I asked him how many girls he had been naked with, kind of already knowing the answer. He confirmed what I was thinking, that this was his first time, then he shocked me when he said he had only ever even kissed one girl, and that was a few months ago on a band trip.

The surprise must have showed on my face because he rolled over onto his back to try facing away from me. I apologized and told him it was ok, and slid just a touch closer. When he rolled back to face me, our bodies were touching, with my naked breasts pressed against his chest and his hard dick poking at my thigh.

I let our position sink in for him a little, then moved in and pressed my lips to his, letting my tongue part his lips and enter his mouth. His lips were soft, and the kiss was really nice. I pulled away and told him that since we were naked in bed anyway, I could help him gain a little experience if he wanted. He just nodded yes, and I told him that the only rule was that it was just one night, no getting attached since I already had a boyfriend at the time. He said he understood.

With that, I backed away from him a little and grabbed the top of the blankets. I slowly pulled them down to our waists, showing him the first real breasts he had ever seen. His eyes were focused on them, so I took his hand and placed it on one of them. He started off squeezing and grabbing, but I took his hand and showed him how to gently massage. As he did that, I felt myself starting to enjoy what he was doing, and starting to get wet myself. I gave him the tip that when the time feels right, he can lightly pinch and pull on the nipple, and showed him the way I liked that done. He went back to massaging it and gave just the slightest pull, sending a thrill through my body.

I thought he was ready for the next step, so I told him the next step involved kissing, and that he needed to place nice gentle kisses where I tell him to. I started with my lips, then guided him down my jaw line, then neck, then upper chest. I told him it was important not to go straight to sucking on a girl's nipple, but to work his way into getting there. As he moved down my chest, his kisses got softer, and more gentle. He worked down to my left nipple, while working the right one between his finger tips. My only response was to moan a little in pleasure as he was getting very good at what he was doing.

Without guidance, he slowly kissed his way over to my right breast and started working that one while playing with the left with his hand. He was doing such a great job I was disappointed when he stopped. I just leaned in and kissed him deeply on the lips in appreciation.

After gathering up my composure, I told him I was going to switch it up a little bit. I laid him down on his back and told him he should learn how to receive attention as well, and that showing appreciation and restraint is a real turn on as well.

Once he was on his back, I straddled his thighs, and leaned down to start kissing his neck and chest. I kissed down the side of his neck while letting my boobs rub all over his hard dick. I could feel the wetness starting on them from the precum he was leaking.

I kissed his chest, playing a little with his nipples with my tongue, before working my way down his stomach. When I got to his waist, I wrapped slowly dragged my fingertips up his inner thigh, across his balls, and up the shaft of his dick. I ran my hand back down and wrapped around the base, pointing it straight up to give the tip of his dick a little kiss. I didnt notice until now that while he wasn't huge, he was a good 2-3 inches longer than my boyfriend and thicker.

As I took the head of his dick in my mouth, I felt him start to tense up. I went slow, since I knew he wouldnt last long, the precum was leaking out all over his dick and my mouth at this point. I was only able to take about 3/4 in my mouth, but when he hit the back of my throat I felt the hot stream of his orgasm start. He bucked a little a couple times, causing some to dribble out of my mouth, but I was able to swallow a majority of the four or five hard streams he unloaded. When I sat up, the cum that came out of my mouth dripped down onto my chest.

I laid back down next to him and watched as he laid there on his back breathing heavily. I let him recover and asked if he was ready for more or if he was done for the night. He said he wanted more if I did, which of course, I was still left with a wet pussy and no relief yet.

I told him that I was going to get started, and when he was ready, he could help. I ran my hand down to my pussy and started slowly rubbing my clit, while massaging my left breast. As I started getting pretty warmed up, I asked if he was ready again, and he just nodded yes.

He moved his hand down to my pussy and at first just started feeling around, which I guess I expected. Then he started doing what most guys do and started sticking his finger in and out of my pussy, which felt good, but wasn't going to get me off like I was hoping. I reached down and guided his hand a little higher, and placed his middle finger on my clit. I then started moving his finger in a slow circle on it and told him to go faster or slower based on my body reaction, that he has to feel my body to know how to continue.

He started slow and then picked up his speed slowly. I talked him through a little, then gasped, as he hit the perfect pressure and speed. I reached up and started pulling at my left nipple as I started feeling the warmth flow through my body as my orgasm built. He picked up his speed a little, and I exploded in an orgasm that shocked him. He pulled his hand away quickly which brought me down quicker than I wanted but I was very impressed with his abilities.

Once I recovered again, I saw him looking at my body and slowly stroking his dick. He was turned on again after what just went on, pretty understandable I guess.

I laid and watched him stroke it for a few seconds and lightly ran my fingers over his chest. As he picked up speed a little, I pulled his hand off his dick and pushed him onto his back again. I straddled him along his waist and lifted my body up. I had made up my mind earlier that I wasn't going to take his virginity, but in that moment, I knew I wanted to be his first. I reached down and pointed his dick towards my pussy, and lowered myself to where just the tip was in. I watched his eyes widen as he realized what was going on, then felt as he pushed the rest of his length inside of me. It hurt a little at first, but as we got a rhythm going, the feel was amazing, knowing I was his first and him filling me more than I had been filled in awhile.

I slowly rode his dick, trying to let him feel my body and react to me, while he was definitely trying to hold back another orgasm. When I sat straight up and pulled his hands to my boobs as I grinded back and forth, I felt his body tighten, and unload inside of me.

I laid next to him and laid my head on his chest. We didnt speak the rest of the night, just fell asleep in that position.

When I woke up a few hours later, I saw his morning wood sticking up and saw he was still asleep. I slowly started stroking him until he woke up. I knew everyone else would be waking up soon, so I told him if he wanted one more round, he would have to be quick. I rolled onto my back and pulled him over on top of me. He entered my pussy and started going hard, filling me up quickly with his hard dick. He was definitely lasting longer this time and right as I started really getting into it, my friend that made the dare opened the door with our clothes and gave a little gasp at what she saw, Josh balls deep in my pussy and my head back, eyes closed in pleasure. Josh froze, and I just laughed a bit and told him to keep going. He started back up as my friend just shook her head, dropped our clothes, and said "for when you're done."

It took a few more minutes, but eventually he exploded inside me in another huge orgasm. We then got dressed and joined the others for breakfast in the kitchen.

I left to see my boyfriend that afternoon and ended up spending the night with him. I saw Josh right before he left and he he just got a red face and said thank you as he gave me a good bye hug.