What made you try anal the first time?

For me, it was always a form of self pleasure. I started slowly but worked my way into it :)

Now I will sometimes beg for it.
 
Thanks for the replies.
Ok so it would seem the first step is an enema if I don't want to find any nasty surprises. So no one does it spontaneously then?
 
I really didn't like the idea of going back there but my then-fuckbuddy asked me to try it and once I got inside her and felt how tight it was and how crazy she got as I was fucking her back there, I was hooked. She acted like she was having an exorcism and it was such a turn-on getting her hot like that.
 
I've posted this story before but for the sake of answering this question here is a shortened version.

I was 18 and working in retail. My boss hit on me constantly. I always turned him down because I was afraid everyone would find out. Well, one day the only road that took me home was closed. It was only he and I closing the department. He offered his place for me to stay. I agreed.

We get to his place and sit back and watch some tv. He says, "I've been wanting to do something but afraid you will smack me." I say, "Go ahead and do it." So he takes my pants down and starts sucking my dick. It felt fabulous. He did that for a bit then suggested we go to his bedroom to continue. He was pretty well hung. Biggest cock I had ever seen. Probably 9-10 inches. I was on top of him and we were making out. He was rubbing his cock against my asshole. I kinda liked it. He says, "Can I put it in?" I said, "Yes. Pls do." So I got on my hands and knees. He lubed his cock and eased it in. He got the head in and it did hurt. He stopped and said he would wait till it went away. Then he pushed a bit more. Didn't hurt as much. He waited. Then pushed more. Then waited. I asked how much he had in. He said all of it. He put more lube on his cock. Slowly fucked me. It stopped hurting. The more he fucked me the better it felt. The sexiest part was he didn't warn me before he busted his nut. I could feel his cock throbbing as he emptied his load.

We laid on our sides. He spooned me with his cock still in me. I woke up early that next morning. I was ready for more. I sucked his dick hard and he woke up with me on top of him balls deep.
 
I was gingerly instructed. This older more experienced woman said the most erotic words, "just slip it in."

It was a point of no return ever since.
 
Did the experience improve for you after that or do you not enjoy it?

Yes, I tried it again with my other ex and he was great, it definitely pleasured me. But he said my pussy was tighter, so he preferred that.
 
Just happened...

I had a few drinks in a bar, got picked up by a very seductive and influencial guy and let myself get caught up in the moment. First time ever that i let myself lose control and it was wonderful to feel him inside me. Yes i would do it again someday :)
 
Yes, I tried it again with my other ex and he was great, it definitely pleasured me. But he said my pussy was tighter, so he preferred that.

Pussy is always best, but ass is naughty ;-)

I'm glad you enjoy it now and that bad experience didn't ruin it for you.
 
Nice, what's your favorite position?


I like prone.

For some reason, me on my stomach, facing away from him and his cock pounding away inside of me makes me feel like a slut. Facing away implies we're not talking so he has no interest in my mind. So he's simply using my body as a fuck toy for his own pleasure. Like I said ... slut. :)
 
I like prone.

For some reason, me on my stomach, facing away from him and his cock pounding away inside of me makes me feel like a slut. Facing away implies we're not talking so he has no interest in my mind. So he's simply using my body as a fuck toy for his own pleasure. Like I said ... slut. :)

Prone is a great formation, one of my favorites.
 
I had lots of wine, my kids were away for the weekend, I watched a Lady Gaga concert and that woman turns me on SO much....then we went to bed and we put "porn" (Cinemax) on to be goofy....but the moaning and panting turned us on even more. I was lying on my stomach while my husband, fiancé at the time, entered me from behind and I was so wet it almost slipped into my ass...and he said, "sorry"...I said "don't be sorry....you can do it..." And it was hot as hell!!
 
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