Roy Taes My Cherry

I remember the first time I ever thought of being of receiving anal. It was 1973 and I was laying in bed with my girlfriend at the time. We had just had sex and I asked her about having anal sex. She laughed and asked me how I would feel about having someone shove a big cock up my ass. I told her that I didn't think that anyone would be interested in fucking my ass and she blurted out that Roy probably would.

Roy was Karen's brother, 18 years old and what would best be described as a nerd. In the days of long hair and beards Roy looked like he had just stepped out of a 1950's farm calendar. As much as I knew him quite well I had never considered him as a potential sex partner. As the weeks went by each time we met I began to wonder about him and about being fucked. The more I wondered the more I wanted to try it.

Roy lived just north or Dartmouth and it was customary that he would drop by my apartment from time to time on his way home. We would have a few beers, talk about girls and watch some television. On his next visit I left out some porn magazines that had a lot of pictures of girls sucking cock and getting fucked in the ass. As we sipped on our beers and talked, Roy started to thumb through the magazines in front of him. He soon turned the conversation around to sex.

What surprised me the most was that he was specific in asking about me and his sister. Did she suck my cock or take it in the ass? I explained that she gagged each time I tried to put my cock in her mouth and might take it in the ass sometime in the future. As we talked about her I could see his cock hardening in his jeans. I started to describe her great tits and how she liked fucking and noticed his cock grow rock hard. He told me that he jerked off a lot but had never had any sex with anyone yet.

I then asked if he would like a blow job from the girl in the magazine, moving closer to him so I could point out the picture to him. When he said he would take it from anyone I decided to make a move. I pointedly rubbed my own hard cock and told him how glad I was his sister was coming over that evening, then moved my hand over and asked him what he was going to do as I squeezed the hard lump in his pants.

Roy tensed and sat straight up. At first I thought he was going to bolt for the door or take a swing at me but as I continued to squeeze his cock he leaned back on the couch and then turn slightly pointing his cock in my direction.

Staring at him I rhetorically asked how bad can it be to suck a cock, some girls seem to love it. I went on to tell him that I had tasted cum before and it wasn't bad. I could see the shocked look on his face and went on to explain that some girls love to get eaten after they are fucked and I like to do that for them. His sister loved it all the time. Roy seemed content to just lie back there and let me rub his cock at that point, enjoying the feel of my hand on his crotch.

As I pulled the zipper down on his jeans and opened the button I asked if he would like to have his cock sucked. Rather than answer he just lifted his hips, pushing his cock towards me. I open his pants and pulled his underwear down over his cock, 6" of fat meat, wet and slimy with precum slid into my hand. I really enjoyed hearing his groan as I stroked his cock and then leaned over to take the head into my mouth. He lifted his hips and drove his cock into my mouth, making me swallow most of it. I pushed his hips back down and started sucking his cock quickly. In a matter of a few minutes I could feel the head swell, the shaft grow thicker and harder and the vein start to pulse and taste his cum blast into my mouth. For the first time it was more cum than I could handle and as much as I swallowed more dripped out of my mouth and onto my beard. I kept sucking his cock until I could feel his body collapse back into the cushions.

Roy didn't move as I got up to wash the cum from my face and beard and was still laying there, eyes closed as I returned and started to wash up his cock and balls. When he finally open his eyes I asked if he was ok. He said he was great and had loved it and asked if I liked sucking his cock. I told him that yes I really liked it too and would do it again whenever he felt like it, if he felt like it. As he sat up he pointed to some cum that had dripped onto my shirt and said he would love to have me blow him again.

I stripped off my shirt and went to get another. As I returned to the living room Roy was still sitting on the couch, leafing through another magazine, pants still around his ankles, underwear pulled down and his cock out. He asked me not to put my shirt on and that I take my pants off too. Once stripped down I sat beside him as he leafed through the magazine. At first he just absently started stroking my cock slowly, rubbing his thumb over my head as he did. His own cock started to swell and jerk back to life so I started to stroke him as he stroked me. He kept reading his magazine, concentrating on pictures of men taking cocks up the ass as he did. Finally I asked if he wanted another blow job or to try something else. My heart was pounding in my chest as he asked if we could try this, showing me a picture of two guys fucking.

This was what I had wanted all along but at the same time I was worried about how badly it would hurt and if I would really enjoy it at all. I hesitated a little than told him we could try, but slowly at first and he would have to stop anytime it became to uncomfortable for me. I could feel his cock jerk hard in my hand at that and knew he was excited by the idea of fucking my ass. I then went into the bathroom and lubed my ass with vaseline then went out and greased up his hard cock. Explaining that I wanted to see his face I lay on the floor with my legs up waiting for him.

I held my legs up as Roy started to rub the head of his cock against my ass, spreading the lube out. The look on his face was amazing, hot pure lust. Slowly I could feel him press down against me and the head of his cock force its way into me. The pain I had expected was not there, just a feeling of being full and I told him to go on, sink his cock into me.

It felt like a baseball bat sliding into my ass, how did 6" of cock feel like it was sliding up my ass and out of my mouth. It seemed forever before I felt his balls slide into mine. My ass felt like it was going to explode. Roy asked how I felt and I told him ok but don't hold back, cum as soon as he could. Ray slowly started moving his cock a little at a time in and out of my ass. There was no real pain but a uncomfortable pressure. Slowly he started moving more until he was slowly pulling his cock almost out of my ass and then sinking back into me filling me up with his fat cock.

As I got used to his steady fucking I looked up into his face. He stared into my eyes and started to pick up speed, thrusting faster and harder into my ass. I told him how big his cock felt, how he was filling me up till I felt like I was going to burst. I could feel my ass heat up with the friction of his cock and see the dazed look in his eyes as he really started to fuck me hard. His excitement excited me, I wanted him to take me, fuck me, use me. I beg him to fuck me, cum in me, fill me up.

He slammed his cock deep into my burning ass and started groaning, I could feel his cock get harder, swell in my ass and then start jerking and pulsing. I wrapped my legs around him and pulled him deeper into me, holding him as he shot his cum up my ass. I could feel the burning being soothed as he came, coating my ass with sperm. Then he started bucking hard, fucking me as he finished cumming in me.

After cleaning up we discussed our day and agreed that we both really enjoyed it and wanted to continue. This was to become a weekly event, sucking Roy's cock and getting fucked and would lead to my most exciting adventure ever.