Losing my (other) virginity

When I was in my twenties, many men tried to fuck me in the ass. This usually happened in the heat of a passionate, headboard-banging doggie-style fucking. He might start fingering my anus, and then I would feel him pull out and put his cockhead right on the tip of my virgin asshole. I just couldn't do it. I would always say no, then slide forward so he couldn't do it.

Don't get me wrong, I loved it when a more prepared and sophisticated lover would whip out the KY or Astroglide and finger my anus while he licked me or fucked me. He might reach around and do it while I rode him. A couple were dexterous enough have one finger in my anus, another caressing my perineum and a cock inside me. The orgasms were always very intense. My perineum is very sensitive and I love it when a man touches me there. But, still, I was afraid of anal intercourse.

Maybe some of this was my repressed upbringing, but I had always been turned on by breaking those boundaries. I think one element was that I had taken some large cocks, starting with the drunken football player who fucked me at the frat house way back in college. Some of these monsters had made me feel like I was being split open, at first, but usually my pussy relaxed and accommodated them quite nicely, and I loved that filled up feeling. But I knew my anus was not built to expand that way. And I always wanted pleasure, not pain.

I finally crossed the threshold with my future (and later ex) husband. Like the best of my lovers, he was very playful, uninhibited, always horny, inventive and, at just the right times, gentle. He also had what seemed to me a perfect cock: about average length, but with a nicely thick shaft and a beautiful head. It's still the most beautiful cock I've ever seen. At work and at home, I could fantasize about that cock in my ass. We did a lot of buildup, with fingering and rimming. He was on fire from the moment I said, "I want you to fuck me in the ass."

He did his usual long, magical foreplay...lots of kissing, holding, caressing, leg licking...cunnilingus. I had already had one orgasm. I fucked him on top, and he fucked me missionary, then with my legs up under his arms. Finally, I was on my knees, my ass high in the air, my head down on the mattress. He told me how beautiful I looked as he slowly fucked my pussy from behind. He opened the KY and fingered my ass, then slipped in one finger. He finger fucked my anus as he cock-fucked my pussy. He told me what an amazing feeling it was to feel both going in and out. (And he had been very careful to trim his fingernails; hint to you gentlemen). Then he started fucking me with two fingers. It felt good.

Then I felt his cock on my anus and he gently slid it in. It had been well slathered with KY, too. Wow...I could feel it. A very different feeling from a cock in my pussy. I adjusted my pelvis and back, and it felt better. He was all the way in and started to very gently fuck me. I liked it. Liked the fullness, the sense of ultimate surrender. Then it just really started to hurt, and as turned on as I was, I moaned "hurting..." and he pulled out. As I say, he was a gentleman. A hood might have just taken me and fucked me anyway. Would I have liked that or not? Anyway, that was my first time.

About a week later he was fucking me hard from behind, fingering my ass with one KY'd finger -- though he often did this. He was moaning himself, I was screaming...and suddenly I felt his cock slide right into my anus as he came. I couldn't feel him shooting inside me the same way I can when a man comes in my pussy. But it felt very forbidden and nasty and I came again myself. As he often did, he stayed hard and just gently fucked my ass for a few minutes. It felt great. My anal virginity was gone, semen was in my anus and I could hear and feel it sloppily running out as he fucked me.

New horizons were ahead.