My first Anal Sex experience

Contributor: MacTheRipper MacTheRipper
My first experience with anal sex was when I was 14 years old, in southern California. It was summer of 87 and I was playing cards at a neighbors home who was 17 years old. She was a pretty girl, about 5'8 135lbs with the body of a 28 year old womana and was of German decent. At the time I was only 5'10" and weighed about at much as her. I would go to her place to play cards and pass the time laughing it up with her friends. One day we were playing war and after 8 hands we were even. She wanted to put a bet on the last hand and I agreed figured it would be something neither one of us would be losing much. She bet that if I lost I had to clean her car every other week until she went off to college the next year. I agreed and jokingly said that if I win we have sex. She laughed and I did too but was thrown off when she said ok. We played the hand and thank god I won. She asked me to come upstairs, so I followed and lead me to her bedroom. She went right to work, kissing me and rubbing my crotch. I was still in la la land, because I could not believe I was in her room about to have sex with her. Everyone in our neighborhood wanted her and here I am in her bedroom, with a hard on. We layer in her bed and the making out got heavy, so I reached in her pants and felt that she was wet. She took off her cloths and so did I when she asked me if I had a condom. This was a mood killer because I knew I didn't have one. I told her I didn't and she said that we can not have sex without one. Here we are both naked, hard and wet and with no condoms. I didn't want to leave her room because I feared that this was a once in a lifetime opportunity. So I began rubbing her vagina and kissing her neck. She started really getting into it and so I worked two fingers into her vagina. She whispered in my ear "I have an idea" she got up and went into her connecting bathroom and brought out a jar of vasoline. She got on all 4 on top of her bed and told me that I can stick it in her butt. I quickly got behind her and rubbed some vasoline on my penis and some in her anus. I lined up my boner to her anus and slowly got my head in before she backed up to get my whole penis inside her. She instructed me to go slow at first but after about 10 strokes she was bucking back and we were going full speed. It felt amazing to be in her round, juicy butt and could not take the excitement to long and I had an orgasm* that could be felt in space after moly pumping her butt 3 or 4 minutes. I didn't pull out and stayed still, in her, for about 5 minutes then I was ready to go again. The 2nd orgasm came after about 30 minutes. Afterwards we laid in bed and I was still in heaven. I became a fan of it and have tried to have anal sex with every woman I've been with. Me and her are still good friends and have had sex from time to time over the years before I got married. It's been 25 years since that hot summer day, and thinking about still gets me at full attention.
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Contributor: GingerAnn GingerAnn
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Contributor: dv8 dv8
No safe sex in 1987? Pregnancy is one issue but paranoia about HIV was prevalent and should still be.