Leslie and I take the Next Step

On our third date, Leslie started dropping hints about anal sex. She told me how she loved the movie Swept Away, and told me that her previous boyfriend loved to fantasize about her ass. She called herself the Wild Woman of Borneo; I was not sure what that meant but she seemed ready for anything. Could this beautiful, slim woman really want me to sodomize her? I had not tried anal since college with my dear friend Nancy; it had hurt her and vowed to be super careful and gentle should the opportunity ever arise again.

It seemed improbable that such a beautiful woman as Leslie would want anal and her ass was tiny; I could not imagine how my thick cock would fit into her tiny, cute little derriere. Anyway, I decided to see how far I could get. I lay flat on her bed and asked to hop onto my cock which she readily did and started to ride me up and down. Then I took a finger, reached around and rubbed her anus as my cock was in her pussy. She immediately had a thunderous, noisy orgasm. I then got on top, entered her pussy with my cock and slid a lubed finger into ass. She went wild again. Then she asked me if I wanted to make love to her ass!

Wow, I said yes, of course, but said we needed some lube. We then had a mad scramble to find something, anything, to use and finally found some coconut-scented suntan lotion (to this day, the scent of that stuff turns me on).

We had no idea what the best position was so I decided we would try it on our sides. I got behind her and lubed her ass and my steel hard cock. Anal (successful anal) was new to me, and I was hot as a firecracker and my cock was rock hard; however, I knew I had to go slow and control myself.

I put the lubed head of my cock at her ass and applied gentle pressure. Then I very slowly and carefully worked the head back and forth at her entrance. The head of my cock gradually pushed inside her. She was panting, as was I.

Eventually the head of my cock slowly slide inside her. I asked if she was OK. She moaned yes and shocked me by pushing back against my cock and burying it halfway into her ass. She wanted my cock there so bad! What an amazing feeling. Then I slowly worked my cock in the rest of the way until I bottomed out. I pulled out a half and inch to let her get used to my girth until she gave me the OK (the outstroke is more comfortable), and then I slowly worked my cock back and forth until I came and came and came deep in her ass.

Before our next date, we needed to find a good lube and made an embarrassing/erotic trip to the drug store to get a big tube of KY jelly. Of course, we had to try it out and could not wait; we quickly retired to her apartment and stripped. We made love in the usual passionate way with lots of licking, sucking, and fucking. I was in a sexual haze, intoxicated by the scent / taste of her pussy and anticipation of what was to come. She orgasmed a number of times, especially when I rubbed her ass when my cock was in her pussy.

Then it was time for The Main Event. For anal sex she suggested a different position that elevated our passion to a new level. She lay face down with her ass wiggling up at me. I suspected, well actually I knew, that she had a deep fantasy about being doubly penetrated (in her ass and pussy at the same time) so I climbed on her back and worked my cock into her soaked pussy. Then I reached for the KY jelly, lubed her ass and worked a slippery finger in her ass. I could feel my cock in her pussy going back and forth. She was going wild. Then I worked my thumb in her ass to stretch her out a bit more and then it was time.

I pulled out and lubed my cock with the cold KY jelly (it would not be cold for long I thought!). I was rock hard as placed the head of my cock against the entrance to her ass and slowly rock back and forth. We both moaned as the head slowly slide in, and I held still until she started squirming. Then I slowly worked my cock deep into her ass and bottomed out. Then I pulled out a half and inch and waited until she was ready. She was ready! She started squirming and panting and carrying on. When she gave me the OK, I slowly started to fuck her up the ass. She gave a squeal of delight every time I bottomed out. I don't remember how much time I spent fucking her ass, but it could not have been that long.

She was pushing back on my cock on every stroke, increasing the friction. I could not last much longer and came deep inside her clutching ass.

Then the most amazing thing happened. She had the most thunderous orgasm imaginable with thrashing and screaming and pounding the bed with her fists but neither of us touched her clit. She had cum just from being ass fucked! Eventually my spent cock slipped from her ass and she moaned in disappointment at losing her instrument for such pleasure....but I would be back.

And so it went. She was hesitant to get her ass fucked every date because she was worried that her plumbing could not handle it; she asked her gyn about it, and he said it was fine, so that is what we did. Every time was as hot as the first with me climaxing deep in her clutching ass as she orgasmed at the same time.

Every time we had sex, we both knew that I would end up deep in her ass. We would start with the usual preliminaries until she could not take the sexual tension anymore said these magical words:

"Take me away!"

That was the signal. I would pull out, she would roll onto her tummy, and I would reach for the KY. Then ecstasy and bliss.