My First Anal

Many years ago, I was having sex with my girlfriend, Lynn. Lynn was the first woman I had ever eaten. I enjoyed making her squirm with my tongue. Bringing her to orgasm, or just to the brink and then filling her with my cock. One of my favorite positions for this was to lie on my back and have her kneel over my face. This let her control the pace of our session. She would support herself by holding onto the headboard.

How sweet, to see her beautiful pussy lower to my face. My tongue extending to lightly catch her clit as early as I could... she, rocking back and forth, offering me first her clit, then her vagina.

One night, as we played in this way, I began massaging her ass, pulling her to my mouth or spreading her cheeks. While licking her clit, I finger fucked her, turned on by her wetness. Then, I moved my index finger, wet with her juices, back to her asshole and gently teased it. I did not press, simply held it there, making tight circles on her sphincter. As I continued to eat her, she began to press herself backwards onto my finger. Very slowly, often stopping or withdrawing a little. I let her have the freedom to decide if she liked it and wanted more. We did not speak, but eventually, after maybe twenty minutes, she had my whole finger in her ass and was wriggling her hips, clearly enjoying this intruder. She came, and again I let her control the pace, leaving my finger in her ass until she slowly pulled herself off of it. I had found it all highly stimulating but did not expect anything more. At least not that night!

But she surprised me as we lay cuddling, by telling me that she would like to try to take my cock in her butt. My heart was pounding! I had never done this before, but it had been a fantasy of mine, and here was Lynn asking me to try it.

I don't remember what, if anything, we used for lubrication. But I remember her getting onto her hands and knees on the edge of the bed, ass in the air, as I stood behind her and stepped forward. Her ass was very tight, and it hurt her, so I don't think I even got the whole head of my cock into her that first time. When I had my finger in her, I had been licking her clit, so she reached between her legs to play with herself in an effort to relax. This helped, and her pain went away. But any motion of my cock brought her pain anew, and I do not like to cause pain. So, I held still, enjoying what we had already achieved, and came in her ass just due to the excitement over what we were doing and how it looked to see her asshole stretched around the head of my cock.

Over time, Lynn became more and more anally aware, though I was never able to truly fuck her ass. But she found that she liked smaller things in her butt. Like a small vibrator. We bought a small butt plug for her that she liked. She liked me to finger her ass when I ate her, or when I fucked her from behind. Mostly she liked having something in her ass, rather than something moving in and out. She said she liked the "full" feeling it gave her. I think her favorite was to have the small butt plug in her behind as I fucked her doggie style. I think she really enjoyed the little nudge the plug was given every time my hips struck her ass. Reminding her that it was there and how naughty she was being.

It is a topic I still enjoy exploring.