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The Pleasures of A Man: Chapter 18- His First Time
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The Pleasures of A Man: Chapter 18- His First Time We met on the internet. He was 19 and had never been with a man before. His name was Andy and his ad on the site had said he was looking for someone to answer the questions of his sexuality. We began e-mailing back and forth and Andy said while he had no problem finding girls and getting into their pants, he was questioning if he was gay or bi. Seems since he was in high school he was having thoughts about guys. He had enjoyed jerking off since he was a young boy and always wondered who it would feel to jerk off another guy, but never had the opportunity to do so when he was younger. He often found himself looking at gay porn on the internet and getting way harder and hotter then when he was looking at straight sex. Andy said he had started experimenting, first finger fucking himself, then fucking his ass with different things. He ordered a vibrator by e-mail and had been using it a couple times a week and enjoying it very much. When he turned 18 he finally decided to visit a porn shop but had chickened out after having a guy walk in on him as he was jerking off. After that he decided it was safe to stay home and play on the internet. However, the more he did the more he wanted to experience having sex with a man. After e-mailing back and forth for about a month Andy invited me over to his apartment. He wanted to give it another try, and felt safer in his own apartment. The next morning I went to his apartment. I knocked on the door and Andy greeted me in a pair of shorts and tee shirt. He said he was very nervous and wanted to take his time. He suggested that we sit on the couch and watch some porn and see what happened. So we sat down and he turned on the TV which was hooked up to his computer. We went to a gay porn site and began watching two guys make out and slowly undress each other. I could see by the bulge in Any’s pants that it really turned him on. Once the guys on the TV were naked they began sucking each other and Andy reached over and started rubbing my hard cock. I did the same and slowly slid my hand in his shorts to get a better grip on things. As my hand slid over his dick and caressed his balls he let out a moan and said “Oh God that feels good”. Before I knew it he was sliding down his pants and taking off his shirt and begging me to do the same. As we stood up and removed our clothes, he reached over and began playing with my cock and balls. As we stood there playing with each other I asked him what he would like to do next. To that he said teach me. So I told him to sit down and spread his legs. I then got down between his legs and began kissing and licking his super hard dick. This drove him wild and he moaned loudly all the while straining to push his dick up into my face. Our cocks were about the same size and shape and his dick fit nicely into my mouth as I slows engulfed it all the way down to his hairs. As I sucked his cock he began moaning an whimpering as it got super hard and exploded in my mouth after only a couple minutes of sucking. Andy got very defensive and began apologizing for cumming so soon. I told him not to worry because the fun was only starting. I explained that since he had cum we could play a lot longer now that he had cummed the first time. This eased is mind and he asked if he could suck my cock. I sat down and said help yourself. Before I knew it he was between my legs and sucking. Since I was the first cock he had ever sucked he started choking as he tried to take in all in his mouth. I told him to slow down and take a little at a time. Andy sucked my cock for about 15 minutes and finally got it all in his mouth. The more he sucked the more he enjoyed it so I suggested we go 69. I told him to get on top so he could fuck my mouth while he sucked my cock. This really turned him on and his dick got super hard again. We 69'ed each other for about 20 minutes, when I asked Andy if he would like to try some fucking? He hesitated for a minute, then said what the hell we have gone his far, mind as well go all the way. Since Andy never had a real cock up his ass or fucked a guy before, I decided to let him fuck me first. I took out a condom and put it in my mouth and rolled it over his cock. Then lubbed it up with some KY and got on all fours. Andy got behind me and started rubbing his cock head against my asshole. Then he slowly pushed the head of his rock hard dick into my ass. Since my ass was no stranger to having a cock in it, and his dick was hard as a rock, it slid in easy and I told him to push it in as far as it would go until his balls were touching mine. This he did and I began rocking back and forth on his cock making him moan. He began slowly pumping my ass and gave me one of the best ass fuckings I had had in a long while. After about ten minutes of fucking I felt him really stiffen up as he yelled on the top of his lungs he was cumming. I tighten up my ass around his cock and milked every drop of cum out his cock that I could. I told him to keep fucking until his cock turned soft, which after a coulple of minutes it did, and he slipped it out of my ass exhausted, but still wanting to play. Much to my surprise Andy said it’s your turn, I just got to experience a dick in my ass. Since it was his first time I told him to get on all fours and I lubbed up my fingers and began to finger fuck him to stretch him out. As I began finger fucking him he began moaning and trying to hump my finger deeper and deeper inside his ass. I then slipped on a condom and got behind him and asked if he was ready for my cock. Please fuck me I need it so bad, he said. I got behind him between his legs and began rubbing my lubbed cock against his glory hole. I began to try to penetrate his ass but he was very tense and tight so I told him to relax. This he did and I was able to push the head of my cock into his ass. He moaned and said it hurt but not to stop. I slowly pushed my cock all the way into his ass and then held it there for him to adjust. He said the pain was gone and I started to slowly pump his ass. We fucked slowly for about five minutes before he began asking me to fuck him harder and faster. I began fucking him harder and harder until I was fucking him as hard and fast as I could. I could feel my cum building. I told him I was close to cumming and he started to yell for me to fuck harder and cum in is ass. Finally after holding back as long as I could I exploded in one of the best orgasms I had ever had. I fucked him until my cock was soft and we both fell exhausted next to each other. I asked him how his first time with a man was and he said we simply have to do this again. He said he had never had such great sex with his girl friends and knew now that he was bi and wanted to try all kinds of other things. We have been meeting one or twice a month and the sex has been wild. |
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