I grew up with my best friend Jerry. Through middle and high school we did everything together. But after I got a girlfriend as a sophomore we didn't spend too much time together. I had always suspected he was gay but we never really talked about it. My girlfriend and never fucked but kissed and fondled each other a lot. I didn't really know a lot about sex at that age. Anyway, on the night of the school dances I would walk to his house and on the nights he parents were gone we would drink their beer and get to the dance a little drunk.

When I was a junior I was to meet my girlfriend at the dance. I walked to Jerry's house and his parents were gone. We each had three beers and I was pretty drunk by the time we got to the dance. By the time the dance was over I was only about half drunk. I kissed my girl goodbye and decided to walk home with Jerry. When we got to his house his parents were home but asleep. He invited me to his bedroom for a bit. He had stashed a six-pack under his bed and we each drank another three beers. That's when he told me he thought he was gay. I told him I didn't care if he was or not. I said I wasn't but I was still his friend. I was lounging on his bed and that's when he crawled on top of me and kissed me. I was pretty drunk and with my eyes closed I just pretended he was a girl. I felt my cock stir and didn't put up too much of a fight when he scooted down and unzipped my jeans. He pulled my smallish cock out and started sucking me. When I asked what he was doing he just ignored me and kept sucking. The longer he sucked the harder I got and found that a pair of lips on my cock was pretty good. Not even my girlfriend sucked my cock so this was my first blowjob. It only took about four minutes and I was ready to cum. I told him I was gonna cum and he just kept sucking. I filled his mouth to overflowing. He swallowed nearly every drop. Wow I thought. This was the best fucking feeling, even better than jerking off. If only Lisa, my girl would suck me like that. When He sucked every drop out of me he took his mouth off of my cock and said that this is what he wanted and needed and he would suck my cock whenever I wanted.

A couple weeks later I was over at his house on a Saturday afternoon and his parents had gone out for the afternoon. We were playing chess and he wanted to make a bet. If I beat him he would suck me but if he won I had to suck him. I hesitated but said okay. I won and he gave me a mind-blowing blowjob. Being drunk was one thing but sober I felt every suck or lick he gave me. I came in his mouth again and he swallowed every drop. Over the next couple of months we played a lot of chess and each time I won. Then came the day I lost. Fuck I thought. Now I have to suck him. I'd never even seen his cock let alone suck him and I'd never sucked a cock before. After the game he stood up and walked over to my side of the table. He unzipped and pulled his cock out. Wow I thought. It's much bigger than mine and had a foreskin. He stepped forward and told me a bet was a bet.

I leaned forward and gently took his cock in my mouth. He told me to push the hood back with my teeth. I did and his head popped out from the hood. He told me to take as much of it as I could. I got about four inches in my mouth but another two or three inches still stuck out. He started to mouth fuck me and said to just relax and enjoy it. I did. I closed my eyes and was getting lost in the experience. Then he put his hands on the back of my head and when he started cumming I couldn't pull my head away. He encouraged me to taste it and swallow. I did. This was actually one of the greatest things I ever did. He won the next game and I sucked him again. Then he lost a couple games in a row so I thought I was pretty much in control. Then he upped the ante. He bet me that whoever lost got ass fucked. I figured I would win so I said okay. He slaughtered me. His parents were gone and he ordered me to take my pants off and get on all fours. I was reluctant but knew if I didn't do it he would be really pissed and I would probably lose a friend. So I took my pants off and got on all fours. I felt him squirt some lube on and in my asshole, then I felt a cold wet hard cock against me. He slowly pushed in and I winced in pain. He said it would be okay in a minute. He was right. As he slowly fucked me it went from pain to pleasure. I found I really liked my asshole stretched by his big cock. That day he fucked me for about 10 minutes and pulled out in time to cum on my back. He cleaned me up with a towel. I won the next time and was oddly eager to fuck him. I didn't even think of it as a gay thing but as a winning thing. I fucked him and came inside him in a matter of minutes. I won the next week and fucked him again. Then he upped the ante once more. The loser had to suck the winner and swallow every drop and keep sucking him until he was hard enough to fuck the loser. I won that game and got sucked and fucked him all in one day. I won the next game and got the same.

Then He won. I had to suck him but kind of enjoyed it by now. I even took his entire load and was actually looking forward to having his cock in my ass. He won the next three games and I got a load of cum in my mouth and ass each time. Then he upped the ante once more. He said he had a friend with an eight inch cock and the loser would have to suck him and get fucked by him while sucking the winner. I agreed. He won. then he made a phone call. While we were waiting for his friend we both got undressed. I was kind of used to it by now. His friend was his cousin Jack. I knew Jack pretty well so It was a little uncomfortable at first, but Jerry explained that Jack was just another guy who liked getting his cock sucked. When he took his pants off I could see he had a massive cock. It was long and thick and when Jerry told me to start sucking I did. I was on the bed on my back and had Jack's cock in my mouth. He had the biggest load of cum I could imagine. I managed to swallow most of it but some ran down my cheeks. I kept sucking him until he was hard again. He pulled out and said it was time to switch. Jerry took his place at my head and shoved his cock in my mouth. Then I felt Jack's slippery huge cock at my asshole. He pushed in and slowly started to fuck me. I was pretty used to it by now so there wasn't any pain but just the pleasure of my asshole being stretched and the soothing rhythm of his cock sliding in and out. It was about 10 minutes and he said he was about to cum. He leaned into it and let if fly. I felt the warmth of his cum ooze out of my ass. I was still sucking Jerry's cock when Jack filled me up. I thought he was done but he said he could go again and continued to fuck me. He went a little soft but was quickly hard again, telling Jerry that he was right that I had the tightest boy cunt he would ever have. While he was fucking me the second time he reached up and started to play with my nipples. The was another new feeling. I was loving it with Jerry's cock in my mouth and Jack's in my ass. Playing with my nipples really got me going. Before I knew it my cock was rock hard and I was cumming. I barely noticed but when then both chuckled a little I realized what had just happened.

Jack finally came a second time shortly after Jerry filled my mouth with his load and we were done for the afternoon. After Jack pulled out of my ass he said he was going to give me the best advice I would ever have. He said that girls and women were afraid of cock and rarely swallowed and they would never let you fuck them in the ass or fuck you in the ass. He also I was better off with men than I was with women. Then he got dressed and left. Over the next year Jerry and I played a lot, both with each other and occasionally with one of his gay friends. I broke up with my girlfriend and after high school moved away to college. I got a girlfriend in my freshman year but she refused to swallow my cum and after a bit even refused to suck me and there was no way she would let me stick my cock in her ass. So we broke up. It was the same story with the next girlfriends and I finally realized that Jack was right. I would never experience anal play or a complete blowjob as long as I insisted on having girlfriends.

Then I met Teddy. He was about five inches taller than my six foot and about 50 pounds heavier. He had a really big cock, about the size of Jack's. He was cut but could suck cock like no woman and could fuck me like I'd never had. It's been 11 years since I graduated and Teddy and I are still together. I am still amazed at the size of his cock and the stamina he has when fucking me. A couple of months ago we got into the gay swinger lifestyle but I have yet to find a cock that can satisfy me like Teddy. We're both comfortable with each other playing and our love is stronger than ever. I guess Jack was right. Women don't treat the cock like men do. I'm glad I got that lesson early enough to avoid the mistake too many men make and choose a woman over a cock sucking man.