College First Time

My freshman year roommate and I were both from all-boys prep schools, both from strict families, and both with no sexual experience. I would jackoff privately in the shower, and I presumed he did the same. But when I would take the laundry downstairs, I couldn't help but notice that his underwear was often crusty with cum. I put that down to wet-dreams. Not a big deal between guys.

We threw really good dorm parties with the upperclassmen buying us beer. During one of these parties Bobby was making-out with a chick and disappeared from the party room to our bunk room. He got razzed for that for a couple of days - "What did you get...did she like it...was she wild in bed?"

But one night, Bobby said he had a personal medical problem and asked me to go to the social room with him and lock the door. (The social room was a two-man dorm room with couches on three sides and a big TV, nothing more.) Bobby said he was so embarrassed because he couldn't cum with the girl jerking him off. I said, "It's just like when you jerk yourself only she does it for you." I had no experience of this, but I thought that was how it worked.

Bobby explained with a lot of shame and hesitation that he had never jerked off. I couldn't believe this, since I had been jerking it since I was 12. He said he had a 'very different' way of achieving ejaculation. I asked - he showed. Bobby took his pants off and started to hump the couch.

I said, "Yeah I can do that, too. Why don't I show you how to stroke it." Bobby agreed and rolled over on his back, shirt still on, but naked from the waist down.

Right before I grabbed his hard cock, I said told him, "Here's how it works." Then I jacked him off. He started to breathe heavily, and then he said it tickles, and then he launched a huge cumload into my hand and onto his chest.

He was both shocked and relieved. He literally did not know that was how it works - and he was an 18-year-old college freshman. Then he asked me if he could do it to me. Of course I said yes.

I kept my shirt on and pulled my sweats and boxers down and let Bobby give his first handjob. Amazing feeling. And it was a bonding moment since we had just done it to each other.

But we couldn't stop. We started showering together and jerking each other.

Sophomore year arrived and we couldn't keep our hands off each other. And whereas in Freshman year our cum was a gross thing, by soph year we loved it. Eventually handjobs weren't enough. We started to do dick-on-dick humping and so we could cum and the same time. We could do that in the shower, on the floor, or on the couch (in a separate room so our roommates couldn't hear us).

Bobby and I got wilder and wilder. I visited his family's vacation house...and we got it on there. He visited my family's house...and the same thing.

But the final hurdle was hit on St. Patrick's Day (don't know why). Bobby had always liked to simulate doing me on all-fours. Well this night, in my own bed, in the guest house at my parents' place, Bobby and I were naked and making out and doing our thing, when he stood up, went to the bathroom, and walked back to the bed with a big smile, a bigger erection, and a jar of vaseline. He asked if I wanted to try it.

I said sure, let's go, and I know how you want to keep doing it - dog-style. Bobby lubed up his dick while I waited for the assault, but then he went in nice and slow, and only started pumping gently. But he got going and it started feeling good. Plus I knew I was going to do it to him. When I heard him getting ready, I looked under my legs and he came. When he pulled out, it was the biggest load I had ever seen him blow, and it went everywhere.

Bobby had to relax on the bed for a minute after his first experience. But then he grabbed me by the back of the head and kissed me and said it was my turn. That was our relationship - sometimes we kissed, sometimes we didn't. But this time he was in the mood.

Just as I knew he wanted me dog-style, Bobby knew I wanted him on his back so I could lick his nipples and eat-out his hairy armpits. He put his legs in the air and said go ahead. And then I had sex with my best friend and it was amazing. We kissed through most of it when we weren't breathing hard or moaning. And I came up his ass just like he came up my ass. Total bonding.

We slept together naked, as we usually did. And the next morning Bobby and I were horny again. He rolled over on his back and asked me to fuck him again. No problem. Then he fucked me up against the shower wall. Felt great to be able to do this with your best friend.