Introduced Her To Anal

I had been dating this woman for a few weeks when we shared New Years Eve together. Since she lived a long drive from my place, and the NYE party lasted well into the early AM, she invited me to spend the night at her place. We had sort of agreed I would anyway, since we were already intimate.
Anyway, we came home and made love to celebrate the new year. It was nice and she was a wonderful lover with a terrific, curvy body and voluptuous breasts. We went to sleep and woke up with the sun shining into her bedroom. She looked lovely half asleep.
I asked her to roll over onto her stomach and offered her a gentle backrub. Soon she was purring with relaxed pleasure. I loved looking at her beautiful behind as I massaged her.
I gradually worked my way downward, until I was massaging her cheeks. I gently spread them, exposing her small opening. I noticed a slight shift in her hips and interpreted it as curiosity. So, I laid against her back and started kissing down her spine. By the time I got to the base of her spine, I could hear her breathing more heavily. I kissed on each cheek; then with the tip of my tongue, I flicked lightly down, towards her anal opening. She raised her hips slightly, showing she wanted more.
"Have you ever done anal sex?" I asked
"No I haven't, but I've always wanted to try it." She replied
I asked her not to move and went looking for some lube. All I could find was hair gel. Brought it back and put a dollop on my fingertip, and started gently stimulating the outside of her anus. I whispered for her to relax and not be afraid. Slowly and gently, I inserted my finger into her, letting her relax as I went deeper. I asked her if she felt OK, and she said yes, she liked what I was doing. I told her I needed to put two fingers in to open her a little more, and that this might feel a little uncomfortable. Again, I whispered for her to relax and try to draw my fingers in.
When I felt her opening relax, I slathered the hair gel on my penis and positioned myself over her hips. I told her to relax and anticipate the pleasure. I placed the tip against her relaxed anal opening and pushed ever so gently. She was very relaxed and breathing heavily with anticipation. I whispered how it would be fun to be at a party and look across the room at her and have her know I wanted to take her home and be inside her ***.
When I about had the head in, I told her to push back, like she was going to the bathroom. While she did, I exerted gentle pressure, and could feel my penis moving in deeper, past the inner ring - the one that usually hurts. I asked her if she was OK, and she said it felt wonderful. When my penis was halfway in, I stopped and let her get used to it. Then I started slowly thrusting, very slowly.
After a few minutes, she started moving her hips back to meet my thrusts. She told me it felt really good, and to move harder and deeper. She asked me to push myself completely into her. When I did, she told me she wanted me to deposit my ***** there, deep inside her. She asked me to **** her hard, and I did; coming forcefully deep inside her hips. After a minute of heaven, we collapsed in exhaustion.
I withdrew and went for a shower, while she made coffee. When I came out, she laughed and said "Well I have a lot more respect for hair gel now!". She also smiled and told me she didn't think my *** was going to come out for a week, it felt so deep. Nice compliment for my manhood.
Anyway, I finally had to leave. She walked me to my car, gave me a sweet kiss and said "Can we do that again soon?" I said sure, she said she couldn't wait.
Alas, that was the last time I saw her. I moved away. Hope you enjoyed my story; I've wanted to tell it for years.
IMBillw IMBillw
56-60, M
2 Responses Dec 12, 2012

Too bad you had to move. A woman giving her *** and taking your ***** deep inside is yours much more than one just sharing her ****.

Great story thanks for sharing.