I was very against anal for years. I loved watching it in porn and I know other guys think it’s the bomb but I was always apprehensive on moral grounds. I just felt that I didn’t want to fuck a woman in an orifice that I also had because it was gay even though I would be performing it on a woman. I felt the pussy was enough. But my FwB/ex-girlfriend said I was being homophobic and besides, she always told me she wanted me to be the one to do her. She thought my cock was the perfect size and shape for her and she wanted me to be the one to deflower her rosebud. I resisted and told her why but of course she came at me with some logic, I hadn’t thought of (or at least hope she wouldn’t think of). She said, since I dont want to do her in an orifice that I also had, then she would stop giving me blow jobs since I also had a mouth. After that I relented. Still I couldn’t figure why anyone would want something up their ass. Then she showed me a video of porn actress Sara Jay explaining why anal feels so good. Apparently anal sex for women stimulates the G-spot from a different angle that’s even more intense than through the vagina. She had heard that it was intense from her girlfriends and really wanted to experience it and she kept at me for some time. So I’ve decided to do it.
Sheila lives about an hour and a half away so I packed a bag before work that Friday and during rush hour, I drove out to her house to stay for the weekend. The whole time while I was stuck in traffic, I was thinking about backing out. By the time I was halfway there to the point of no return, I started thinking of my game plan of how I would fuck her. Haha. Can you believe I was afraid of a sex act? It wasn’t like it was my asshole.
She and I dated on and off for several years and always remained close friends. Very rare for me indeed. Usually my girlfriends wash their hands of me once we’re through. I guess because sex between us was always dynamic, it was more beneficial for us to keep that part of our relationship intact. But every time we’ve tried to rekindle the romance part, we fall back into the same petty arguments so FwB is a much better arrangement for us.
When I got there, Sheila answered the door wearing my favorite outfit. It was a short and sexy white and blue-striped tennis dress that she knew drove me crazy whenever she wore it. Now my dick was harder than some chinese math. She had all kinds of sex toys and scented candles and stuff laid out. There was new age music on the stereo. Wine, tequila. Hors deoveurs. She really knew how to set a mood. It was good to see her. It had been at least a couple months since I’d been out there.
I could tell she just got out of the shower from scent of the rose fragrant shampoo in her chestnut brown hair. She said she gave herself an enema an hour before I got there. Still I was a little nervous and also worried about hurting her. After we embraced, kissed and made out for a couple minutes, I reached under her skirt and ran my fingers through her freshly-shaven pussy lips. They were drenched. My index finger pushed its way into her molten pussy, then a second finger followed. She moaned and squirmed, kissing and breathing her hot breath on my neck. I pulled my fingers out and put them in my mouth sucking the sticky, juicy treat off my digits. The taste of her pussy always made my eyes light up. We immediately got undressed and assumed our favorite foreplay position of 69.
I had it all planned out in my head how I would do it so she would be comfortable. Figured I’d ride her pussy for a while to get her primed and help me get ready mentally. But she had her own ideas. After we had eaten each other into sloppy wet readiness, she pulled out some lubricant and generously smothered my cock with it from my balls up to my cockhead. I told her to lay on the bed but she pushed me back down on my back and climbed on top of me, cowgirl style. She reached between her legs and guided me, not into her pussy but her already lubed asshole. She slowly lowered herself onto my cock which now felt like it was squeezing into a coke bottle-sized hole that soon stretched out. I thought we would go much slower but by the time she got halfway down my shaft, she eagerly slammed her ass all the way down on my cock. Once her ass was resting on the top of my thighs, she reached back and pulled her cheeks apart then started to gyrate her ass and hips to make sure I was all the way up in there. Damn, it felt good but I thought she’d be tighter for a ass virgin.