Years ago I was looking for a roommate and a good friend of mine told me that his coworker (straight) had just moved into town and was looking for a place to stay. My roommate had just left so this was perfect. When I first met him I was floored. He was a bit taller than me, was well dressed, great head of a hair. Anyways, after a few weeks we started to become close and hung out quite a bit. One morning after a late night of partying we got up and hung out in our living room. Both of us were in our underwear and watching TV. He was lying on the couch and I could just focus on his massive bulge in these small pink briefs. After that one day we started getting more comfortable with each other and started just wearing our underwear around the house. He was lean and smooth with hairy legs.
I started doing this thing where I would go to bed naked and leave my door open and partially expose myself. My room was near the bathroom so I know he would see me when he would come in after going out.
One night he came into my room ‘drunk’ and jumped into my bed and started to tickle me. This night I wasn’t naked (unfortunately) and I grabbed him and pinned him down. He really liked it and it became a bit of a joke between us.
Years went by and he stayed over at my house while visiting friends in the city. In the morning I popped in the guess room and crawled into his bed. I told him to move over and started to cuddle him. He was shirtless and I was rubbing his smooth chest. His nipples started to get hard and he told me it felt good. So we chatted a bit and I was rubbing further and further down until I hit the band of his shorts. This is where I felt the tip of his hard cock tucked just under the elastic band of his shorts. I turned over to be little spoon and he couldn’t figure out where to put his hand. He had rested it on my hip and then pulled away. So we went back to the original position of being on our backs and rubbing his chest and ‘accidentally’ hitting the top of the elastic. Be never repositioned or moved away so I could tell he liked it. He kept saying that it felt nice. I could hear one of our other friends waking up from the couch and making their way down to the guest room. So I got up grabbed his cock with my hand and smiled at him. He smiled back and that was the end of it. From time to time he will text and flirt with me but I know we are both waiting for the next time he sleeps over again so we can go into round two.