From Novice To Experienced, We All Go Through It

I can only suppose that everyone has his day. My day came during a church mission trip to Costa Rica. There were seven boys and nine girls and the chaperones. I was 15 and horny as hell and masturbated quite a lot. The boy who shared a room with me told on me and the chaperone had to talk to me about it. First time ever talking about masturbation with an adult.

That night, after everyone was asleep he came to my room and sat on my bed to see if I was all right. The boy on the other bed was fast asleep and he rubbed my behind while he spoke in whispers, about how every boy had this happen, we just needed to learn to control it. Laying on my stomach my dick was hard and the more he rubbed my behind the harder I got. I started to hump the bed under me, his hand slipped under the covers and into my pjs, his finger laid right down my crack while he massaged my anus, matching my thrusting on the bed. I came, shot the bed. He leaned over and kissed my cheek and told me that now I could go to sleep.

After that all I could think of was having something in my anus, a finger, a dick, a stick, anything. It was later on during a swim meet that I met a boy, same age mind you, from another school and his dick sprung out of his wet bathing suit when he was going to take a piss. His dick was hard and he had to bend it down to piss in the urinal. I went into action and reached over and held his hard dick down for him. He pissed hard and when he was done I leaned over and put his dick in my mouth. My first blowjob attempt. He liked it and I liked it and we agreed to meet later. We agreed that the equipment room was a good place to meet.

Not only did I suck him down as much as I wanted, he was hard and stayed hard and I bent over and he poked around pushing his dick against my anus. I had to spread wide before he got his dick in. Like most naturally born tops once in he shoved and I got my first fuck. I loved it. But it wasn't like on my church mission trip, feeling the warmth over me, feeling him kiss me. That's what I wanted, not just a dick in an equipment room.

Fucking with him never felt just right. He was rough and fast and wanted nothing more than to fuck and cum and then leave. I won't say I felt used, but I was used. Nothing in it for me, all for him. In my freshman year of college I got along well with the History professor, a man in his forties, gentle man with hair on his arms and chest. He had magic fingers, I told him I liked having my anus massaged and he massaged my anus, helping me cum into the sheets. His dick was large enough and he was uncut and pulling his foreskin down to suck on his knob was such a good feeling. He fucked me by laying on my back, long slow fucks, in and out, gently fucking me, kissing my neck, mouth and face. I loved fucking with him. He was very oral too, and taught me how to kiss and about nipple play and rimming.

Once I graduated from being with him I went out into the wide, wide world looking for the right man. I met him at work, he was in his early thirties, obviously gay and very much a top. Not quite as experienced as my History professor so I had to teach him. Still to this day having a man massage my anus and kiss my neck and mouth before mounting me is one of my favorite forms of getting ready for him.