Anal With Anne

As mentioned in a previous story, my former girlfriend Carolyn was open to a lot sexually, but not anal. My next girlfriend and future wife, Anne, was different. From the start she liked the feel of my hands on her big, soft ass cheeks. Her favorite way to start foreplay was to ask me to play with her ass. She would lay on her stomach while I would straddle her thighs and massage her butt. She loved me rubbing the sides of her hips and thighs, and squeezing her cheeks. It always got a reaction when I tickled the top of her ass crack and ran a finger all the way down to her pussy. Although she wasn’t interested in hand spanking she did like and often request that I spank her with my cock, both on her ass and pussy. One day I asked if she wanted me to slide a finger in and she slightly reluctantly said okay. I got my finger wet with her pussy juice and dripped spit onto her asshole, then slowly pressed  my fingertip in. She started breathing heavy and told me to move it a little. After a bit she told me to stop and rolled over so I could fuck her.

The next development came when She was on her hands and knees and I was fucking her from behind. My hands were holding her hips, which she liked, and I couldn’t stop looking down at her asshole. I stuck one thumb in my mouth and got it wet, then reached down and eased it into her ass. I loved that my thumb could feel my cock sliding in her through the flesh between her ass and pussy. She liked it too and it became standard procedure when doing it doggy style.

One day when she was sucking my cock, she reached down and pressed her finger into my ass, which made me come quite quickly. She became fond of playing with my ass and probing me. She would be the first to admit she enjoyed butt play. When she would suck my cock she would kneel next to me and I liked to reach over and play with her ass, sometimes slipping a finger in.

She knew of my previous relationship with Carolyn and felt a little jealous how many sexual firsts I had experienced with her while all of Anne’s firsts were with me. One day after we finished fucking we were talking and it came up that I had never fucked Carolyn in the ass. I had never done it before and Anne asked if I wanted to do it with her. Of course I said yes. I got some lotion to use as a lube and she got on her hands and knees. I rubbed some on my cock and her ass, pushing my finger into her anus. She told me to use my finger for a little bit, which I did. When she said she was ready, I moved up behind her. Since I had just come in her pussy a few minutes before, my cock wasn’t fully erect, which was probably good for our first time, but it was hard enough to press slowly into her anus. I paused once my head was inside and asked if it was okay. She said it was but to take it easy. I slowly and gently thrust back and forth into her, going in barely past the head of my cock. It felt better than I had fantasized and was very little time before I came inside her.

It didn’t become a routine thing, but on special occasions she’d let me fuck her ass. Luckily she could handle my cock in her butt at full hardness because that was its condition when it knew it was going in her ass. We tried doing anal with her facing me but couldn’t make it work which disappointed me because the thought of fucking her in the ass while looking into her eyes really turned me on. While I loved fucking her and coming in her pussy, sometimes I would get in a mood where I wanted to come in her somewhere else and she often preferred I come in her ass rather than her mouth. I never slid my cock all the way in, concerned it would hurt or turn her off, but the feeling of my cock head sliding back and forth in her asshole felt so great I didn’t miss going deeper. I considered myself a lucky man to have the wife I did.