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Anal sex - pics gifs and confessions

I love all things Anal.

My obsession started young and entirely by accident. In my last year of high school, my then girlfriend and I (both 18) were just exploring sex for the first time. She was a virgin and I had just recently lost my v-card and was by no means experienced. She wanted to keep her virginity, she wasn't sure if she was waiting for marriage or not, but we were so horny. One night after we had exhausted our oral skills and were still unfulfilled I suggested we try anal, something I had only seen in old Hustler magazines I had found (this was right as the internet was becoming popular).

For whatever reason she said "Yes". We didn't have any lube so we used a large amount of saliva and pussy juice, I eased my rock-hard cock into her slippery hole. She had a medium-tight asshole, as I've learned since, everyone is built a little different. Some are tighter and others are more willing, and these natural variations get modified by how much preparation you do before penetration. If we think of initial tightness as a one-ten scale with a one being very open and a ten being super-tight, my first anal partner was about a seven, tight enough to cause some initial difficulties getting inside, but easy enough one it slipped in for the first time.

Now my cock isn't huge, but it's long enough and plenty thick. Think just a little bigger than the cardboard tube in a toilet paper roll, with a nice big head that's made even thicker when my foreskin is up. The point is, if it's in your ass you're gonna know about it.

So my girlfriend's -we'll call her Seven- butthole was getting a real workout, but she took it like a champ and after a few seconds pause for her to get used to being filled we started to fuck. I predictably didn't last long, emptying my young balls deep into Seven's colon. She didn't come, we didn't know it at the time but she wound up having great difficulties having orgasms no matter the type of sex or partner, but told me she really enjoyed the experience. We wound up falling asleep together with our limbs entwined and my softening cock in her ass. Seven and I wound up having anal-only sex for several moths, being teens we didn't have places of our own that were reliably private, so we wound up having a lot of our sex outside or in cars (some other things I have come to love).

Being young and dumb, I wound up cheating on Seven with... Nine. (if you got that reference punch yourself for being a big fat nerd).

Nine was another high-school friend of mine, but while my previous girlfriend was an innocent, girl-next-door type, Nine was exotic. She was an artist, and openly Bi, and living in NYC. She introduced me to drugs, atterall and cannabis. And in return I fucked her brains out. We had our first anal experience in a blisteringly hot NYC dorm apartment, high as kites, she asked me if I wanted to after we had already been having sex for what felt like hours. Of course I eagerly agreed and again, not having real lube, used liberal amounts of saliva to ease my finger into her anus. Nine was as tight as her name implies, and could barely take my cockhead. We probably had to wait five minutes for her sphincter to relax enough for me to continue. Again I came quickly, but unlike Seven, Nine used her hand to rub her clit until she too had come.

Me and Nine would have anal sex occasionally for the rest of our relationship, one of my hottest memories is hearing her in the bathroom after we had buttsex, farting my cum out.

I've had some other fun partners, Two was the horniest woman I've ever met, she could have orgasms like most people can laugh. Anything sensual would get her off. She was my first partner who had had an orgasm due to my dick being inside their ass, and she's the only partner I've ever had anal without using any lube, she was always just ready to go.

Eight loved ass-play, she could barely come if she wasn't getting some sort of backdoor stimulation, but anal with me was too much for her and therefore no fun for either of us.

My current partner is Ten (of course she is!) and our anal sex journey has been long and rewarding. She was a virgin when we met, and relatively innocent, so we had pretty vanilla sex for the first few years of our relationship, but we would talk about everything, so she knew I liked anal and would want to take her ass at some point. By this point in my life I had learned to keep lube on hand, and I purchased a sizeable collection of butt plugs for preparation duty, so by the time we got around to trying full anal-sex it was a much more civilized affair. I was very gentle, easing my fat cock into her waiting orifice over the course of several minutes. Once all the way in I gave her even more time to get used to the sensations before I started to fuck her. We went on for quite a while, switching positions several times. We ended with doggy style, and by then she was screaming for me to fuck her harder. When I was done her asshole was actually gaping, you could have dropped a ping-pong ball into her with ease. She was crying with the force of multiple orgasms that she described as being the most intense in her life.

We do butt-stuff on a weekly basis, maybe next time I'll tell you all about the fun we have using toys on each other...
 
Anal is incredibly taboo, sexy, and rewarding extremely. Taking a rock hard dick up my ass drives me wild. A cock is so big and rigid, my hole so tight and gripping, I love being fucked. I am a male.
 
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