How I Lost My Anal Cherry

John worked at the corner store/gas station next to where I worked. I would often stop there and put gas in my car or buy stuff. He was what I would call a "Man's Man" in the context of gay sexual preferences. That is to say he was very masculine (though he was quite short) and very well-built and he was only interested in masculine men (like me). He also made no secret about being gay or that I was to his liking. He knew I was attached to a woman but always dropped hints about how interested he was in me.

My girlfriend thought it was really sweet the way he would almost be drooling over me whenever he would see me. She even jokingly suggested that I should spend a night with him because he was such a nice guy and it would make him so happy.

Over the course of time I kept running into him and he was always interested in talking to me. One day he even gave me his phone number under some pretext. I never let on my occasional bisexual side because if I did it would have been tantamount to saying, "Let's fool around."

Sometimes I talked to him when would take a cigarette break behind the store. He was a nice guy and I enjoyed talking to him even if I knew that he just wanted to pull off my clothes and jump into bed with me.

On one occasion we were talking about weightlifting. I worked out and had a good build. John, of course, would often comment how good I looked. He was quite a few years older than me but in good shape. He told me about his previous weightlifting experiences and mentioned some photos that he could show me sometime. I said sure and that was that. Of course all this hanging around with John started to get me horny. Thinking about just how much he desired me turned me on and one day I decided I should take the plunge.

The next time I saw him I brought up weightlifting and he brought up the pictures. I said I would like to see them sometime. He told me he would be finished work soon and I could stop by his place a few blocks away if I wanted to. I said, "Sure, I'll give you a call."

Time ticked by very slowly as I thought about how excited I was getting by the thought of an encounter with this man who desired me so much. Finally the time came and I called him and he said come on over. I got there pretty fast!

I knocked on the door and he let me in. I sat down on his couch and he offered me a beer. He sat down next to me on the couch and showed me some photos which were quite impressive but honestly I wasn't there for the photos. He sat quite close to me, so close that his legs were next to mine, barely touching. I could have cut the sexual tension with a knife!

My heart was beating fast when I turned and faced him and said, "You know, John, sometimes I fool around with guys."

He looked at me with very big eyes and asked if I would like to fool around with him. I answered with one word. "Definitely", I said, gulping slightly.

He put his hand on my crotch. and then I put mine on his. We started to rub each other through our pants. I quickly removed my jeans and so did he. He kneeled down in front of me and started rubbing my cock through my underwear. He peeled them down and my six and a half inches was standing at attention. Just like that he put it in his mouth and softly sucked me. Like a lot of gay men he was very good at deepthroating. He deepthroated me and made me moan softly as I throbbed inside his mouth. after a few minutes I suggested we go to his bed.

I told him to lie back and I got between his legs. I blew on his cock softly through his boxers. I rubbed up and down and took his underwear-clad shaft between my lips. That cock felt quite big.

I could not wait any longer. I pulled down his underwear and saw a very impressive cock, a good 9 inches and fairly thick too. it was not a monster but it was a nice big juicy cock. I wrapped my hand around the base and jerked it slowly. I lay it against his belly and licked up the shaft. I nibbled on it. I kissed it. I licked it. I rubbed it on my face. In short I made love to his cock with my mouth, lips and tongue. I did all the things I would fantasize about doing with a nice hard cock.

He said I gave good head for a straight guy. I told him when I suck cock I'm really horny for it because I don't do it much. With that I took him in my mouth and started to suck on him like a horny slut. I sucked on the first five inches with my mouth while my hand jerked the bottom four inches. Essentially I was masturbating him into my hot mouth.

After a few minutes of pleasuring him I got up and, with his head against the headboard on a pillow, I started fucking his mouth while holding his head with my hands. I thrust in and out using his mouth as a fuck hole. He couldn't really move his head so I could push all the way down his throat and hold it in deep. I took it out and tapped it on his face and put it back in. He allowed me to use him anyway I wanted. I told him how hot it was to fuck his mouth. I told him, "I am fucking your mouth just like I would fuck a hot pussy. I am using it like a soaking wet cunt".

After a few minutes I took my cock out of his mouth and went back to work sucking that gorgeous 9 inches of meat. After fucking his mouth I felt so slutty that I sucked his cock like I was a whore and he told me how much he enjoyed it which just made me even hornier for his cock.

Then he sat up and put his mouth on mine and I did something I had never done with a guy before. I started making out with him. I mean we were really making out. Our tongues were probing each other's mouths. I kissed him long and deep. I lay on my back while he lay on top of me, our mouths locked together in a passionate embrace. Our crotches rubbed against each other and our cocks frotted together. I almost came right then and there it was so hot! I grabbed his ass and pulled him tightly against me. I licked his neck and ran my hands up and down his body. I had never been this passionate with a man before. I had sucked cock and had my cock sucked and even frotted. I had explored men's bodies a little bit but it was always a bit tentative. It was always like I was just experimenting, fooling around. Not this time. I wanted to make love to him like I had done with women. I stopped kissing him just long enough to tell him something.

I said, "John, I have been with men before and it has mostly been about the cock. I think of man-to-man encounters as kinky sex. But this is the first time I have really wanted to have GAY SEX."

Just telling him that made me even hornier. I then went back to making out with him passionately and rubbing his body against mine while trying not to come from the hot sensation of our cocks rubbing together.

We made out like that for a long time and then he asked me if I liked having my ass eaten out. This also was something I had discovered not long before. Another guy had eaten my ass out and I enjoyed it. I said I would love it.. I turned over and lay on my belly. I felt his tongue probe my asshole. I moaned while he licked me passionately. He poked it softly and remarked what a tight little ass I had. He asked me if I had ever been fucked. I told him I'd been fucked once by a woman wearing a strap-on dildo. He asked me if I would like to be fucked and I said his big cock could never fit in my tight little virgin ass.

He squirted some lube on a finger and gingerly penetrated me with it. He continued to expertly lick and finger fuck me slowly. I enjoyed the sensations and the worship he was giving to my ass. After a while I could feel two fingers probing me again very softly and gently, giving me lots of time to relax and get used to them.

I told him he could rub his cock up and down my ass crack. He squirted some more lube, straddled my legs and started frotting between my ass cheeks. I could feel the heat of his horny cock. It turned me on and I slid my hand under my crotch to play with myself while he rode my cheeks.

Then I felt something new. He was probing my hole with his cock. I told him it would never fit but did not resist either. He kept gently probing. After five minutes of poking softly he told me the head was inside. I couldn't believe it but I was so excited by the feeling that I told him to keep going. Slowly he pushed and kept pushing a millimetre at a time. I could feel his big cock filling me up. It was much better than a strapon. For one, it was hot and throbbing. The warmth against the walls of my anus was unlile anything I had felt before. Also, unlike a strapon, his cock was attached to a hot man that lusted after my sexy ass. I had often wondered why gay men liked being fucked. I thought all the pleasure was for the one doing the fucking. Now I understood why they liked taking it up the ass.

This was a completely different sensation from doing the fucking. I had to really relax and let it happen. Luckily for me he was an expert and knew exactly how to get me to relax, when to push and when not to push. a few minutes later he said he was completely in. I couldn't believe it. Like I said his cock must have been a good 9 inches and it was not skinny either. I turned my head to look as best I could and it was true. There he was, balls deep in my asshole. I was definitely no longer an anal virgin.

With his cock fully inside me he started to pump me gently. The feeling was so much different than I was used to feeling during sex. It was a strange mixture of discomfort and pleasure but I definitely did not want him to stop. After a bit he pulled his cock out slowly and removed it from me completely. My sphincter tightened and then relaxed. He reinserted his cock into me, penetrating me anew and a gasped with pleasure. Again he pushed it all the way in balls deep, held it there and pumped me a few times, then stopped and slowly pulled it out all the way again. He repeated this sequence over and over. I noticed that every time he would put it back in me I would gasp and it would go in a little easier than before. We got into a good rhythm of penetrate, pump, remove, repeat.

After a while I realized I was relaxing more and more and his cock was going in and out of me fairly easily. It actually started to feel like my ass was just like a tight pussy: A tight pussy that was discovering how good it felt to be fucked.

Soon he was pumping me more seriously, still being gentle but concentrating a little more on his own pleasure. His hot horny cock went in and out while his hands spread my cheeks so he could fuck me deeply. I really got into it and let myself go. My hands were above my head and I just lay on my stomach while this sexy man fucked me. I ground my pelvis on the bed and my inner ass slut came out. "Fuck me, John, yeah, fuck me good. Give me that beautiful cock of yours. Right up my tight little virgin ass!"

Between the ass fucking, the dirty words coming out of my mouth and my cock rubbing against the bed I could feel an orgasm building slowly. "Keep fucking me just like that", I said, "Oh fuck, I'm coming. Awwwwww........"

With that I shot a huge load all over his bed sheets. My ass clamped down on his cock. He just patiently kept pumping me until I was completely finished. Then pulled it out and jerked it all over my ass. Load after load of hot come splashed over my ass cheeks.

He wiped his sperm of my ass and collapsed next to me. I put my arms around him and held him. We made out tenderly while rubbing our bodies together....