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first time anal

General Sex Stories (Written By MEN)

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Old 02-21-2011, 11:49 AM   #1
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Default first time anal

Senior year of high school, I had tried a lit of things with my girlfriend, but she had never been willing to try anal. Gaby was short and curvy with browh hair and brown eyes, big breasts and an ass that looked really good in jeans. One night i was feeling particularly horny while I was over at her house watching a movie, and I asked if we could try it. She was reluctant and nervous, especially because her mom was home at the time, cooking upstairs. But she said yes anyway. We were too inexperienced to know much about lube, but she did find some lip balm and smear it onto the tip of my erection, making me really anxious and aroused. She shyly moved onto her knees in the dark, and I rolled her pants and underwear down around her thighs. I'll never forget the sight of her big, pale rump as she laid there so submissively, waiting to take me in. Leaning into her, I pressed the head of my penis against her anus. It was tight, but slowly her ass relaxed, and in what was pretty much one slow smooth motion I watched the warm white globes of her butt swallow my entire shaft. The first time was amazing... she was gasping and flushed with the feeling of having me so deep in such a personal place, and I was blown away at how erotic it was and how tight and smooth she really felt. I didn't last too long... draping myself over her, I felt a frantic feeling of needing release. I lurched in and out of her a handful of times, drove my erection deep into her anus, and as we both grunted quietly, I filled her rump with my wet pleasure in one of the strongest climaxes of my life. We waited just for a moment to feel our interlocked bodies slicked with the cum, then quickly put our clothes back on. It wasn't a moment too soon, because a couple of minutes later her mom came downstairs to check on the laundry! She hadn't heard a thing, so we sat there like everything was normal, but I couldn't help but think of Gaby sitting there with her butt still full of cum for the first time as her unsuspecting mom did chores a few feet away! Luckily for me, she found the experience enjoyable enough that we repeated it often, but the first time was like no other.
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Old 02-21-2011, 05:02 PM   #2
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Wow that was hot. My first anal was actually with my girlfriends best friend. We were young and my girlfriend was a tiny girl. Sex of the normal type took some care with lube and warming her up. I asked about anal more than afew times as I had some friends that talked about it and how amazing it felt. Finally one night when we were drinking in her friends basement my girlfriend brought up anal sex. Her friend said she never had it either but was open to it. My girl said she thought it would be too painful since she was so small, only about 5foot 1 or 2. I am 6 foot 1. Anyways my girl asked her friend if she would consider having anal with me. I had no idea she was going to ask this. My girl explained she thought I would stop asking her if I did it once. We were drunk enough the other girl agreed. We did it right there in her basement with my girl watching. It did feel amazing and I didn't last too long. But what a feeling cumming in this girls ass while my girl watched. The funny thing is I never saw this girl naked really. She hd just bent over and pulled her pants and underwear down enough for me to enter plus the basement was a little dark. We never did it again since she was my girls best friend and I never asked for anal again from my girl. But the feeling and then having that between us was really something.
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Old 09-05-2011, 12:55 AM   #3
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Thumbs up hot

That was sooo hot. I brings a lot of goood memories.-----Ann
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