First Anal Play

My balls were swollen. My gf and I were on a temporary break and I hadn’t had sexual contact in a month. This may not seem like a long time but we had been fucking 3-4 times a day for a year and a half. She was just as insatiable as I was. Draining my cock to porn was not enough to quench my sexual appetite.

One summer evening I was alone in my apartment with several bottles of wine. Upon finishing the first bottle I browsed the newspaper. In those days the classified section offered ads to various escort services. My curiosity got the better of me and before I knew it I had arranged an incall to arrive within the hour.

I pulled out the sofa bed, lit some candles and incense, poured a couple of glasses of red and waited for her arrival. When I greeted the knock at the door, I was taken aback. This woman was stunning. Mid-40s, petite athletic body with small firm breasts, medium black hair in a ponytail and a sexy little black dress stocking and heels. I brought her into the living room and we drank and talked for a bit as I explained I was just looking for oral, not full sex.

Quite the conversationalist, she offered me a first-timer special: we would relax, drink and chat. Only when we began the encounter would my one-hour session begin. I was worried the agency might charge me for going over the time limit but she assured me she was an independent and could do as she pleased.

When we got down to business she had me lay on the bed while she did a sexy striptease. Her body was tight and almost perfect, with a completely shaved pussy. She began with a brief light massage then began teasing my cock to full hardness. Once achieved she put a condom in her mouth and rolled it down my shaft using only her mouth no hands.

For the next twenty minutes, I was treated to what should have been the best blowjob of my life. She licked and sucked me in ways I’d never experienced. Despite her efforts the alcohol and condom had a numbing effect until I came up with an idea.

I had her open another condom and put it on her index finger. She began teasing my asshole with her covered finger while continuing to suck my cock like a woman possessed. I was in heaven and then it happened.

She slowly slid her finger into my virgin asshole. I had experimented with my ass by myself but this was the first time another person did it for me. She slid her finger up to the knuckle and paused for me to adjust to the feeling. When I relaxed she resumed sucking my dick and began massaging my prostate with a come hither motion. Every now and then she would swallow my cock to the base and lick my shaved balls with her extended tongue.

After about forty minutes of her tireless cocksucking skills my world began to spin. I felt my orgasm coming on from miles away, slowly creeping over my entire body. She sensed it and began finger fucking my ass hard and fast while bobbing her sexy mouth up and down on my throbbing member. With one final push into me she squeezed her finger tightly against my prostate and I began cumming with the force of a thousand suns. I filled the condom with more sperm than I thought I could ever produce as her mouth and tongue continued to milk me. 

As I basked in the afterglow, she removed her finger from my core, slipped the lipstick-stained condom off and tied it up. She told me to keep it as a souvenir, and if I ever get back together with my girlfriend to remember this experience when we are fucking and sucking each other.

After cleaning herself up, we had some more wine and she went on her way, leaving my balls and my soul satisfied.