Turn About is Fair Play

During my twenties I had a girlfriend who was very attractive and game for most things. Of course I was experimental too and we felt comfortable expressing a lot of desires to each other. I had talked about anal sex and we both did some reading. She was game to try it, although in hindsight, I believe she (Cindy) did it more to please me than out of her own enthusiasm. We did it one night with all the preamble as recommended by a few authors we had both read, Cindy was free of pain and very excited by the time I came and I went ahead and finished her off orally. Cindy was the type of woman who came very hard once and needed an extensive "refractory period" before not being too sensitive for further stimulation. Right after, Cindy was taking a shower and mentioned her ass felt "funny." According to the articles this seemed natural, as in the 'your asshole just got fucked.' There was no pain or anything the next day.

I the months following this she mentioned this several times. I was thinking it was a guilt trip inducing type behavior, so I did a little looking around since I enjoyed anal stimulation quite a bit. What I found was a selection of strap-on dildos at a progressive (for the time) kink store with male and female employees that were extremely helpful. The next time Cindy slid this into the conversation, I just send "Let's end this subject: I don't want to hear it any more. Do want to put the shoe on the other foot and get me back?" The way I said it took her back a bit, but I could tell I got her curious as to what I had in mind.

A few days later I just took Cindy to the store. She was very skeptical as the place sold BSDM and other role playing accessories, it did not help it was not in the nicest part of town. I eventually got Cindy into the store and was glad when a woman clerk came right over to her and was friendly, accommodating, articulate, everything needed for this situation. After explaining what we were looking into, I received the appropriate devilish smirk and grin and the two of them were ignoring me to examine the pluses and minuses of the various strap-ons. Of course Cindy picked the most expensive one, but a that point was actually getting a bit of an erection with all the stimulation in the store and just paid.

Cindy was pretty quiet on the way home, which I was thinking may be a little trouble for my ass. What had I unleashed? We made a "date" for the following Saturday night. Cindy was in a remarkably good mood for the next several days, so I was a little nervous going along with some building excitement. Preparing for the night Cindy shaved my neither regions up along with her own.

After a few drinks we were both naked and Cindy had already prepared adjusted the straps of the harness to her dimensions so the just quickly put it on and cinched. We always loved the foreplay, kissing and stroking, this time it included lubing and inserting some smaller toys to get my ass ready. Cindy stood up and stroked her "cock" as if she was jacking off while adding lube. She looked beautiful, hard, erect nipples, a look of desire in her eyes that was different than I had seen before. I could smell her desire, her breathing was already accelerated and audible.

I was much larger and taller than Cindy, but still let her push me down on the bed, laughing, maybe a little nervously. I got on my elbows and knees, Cindy was behind me in a flash. I could feel the dildo head at my opening, my clean shaven ass made it very sensitive and slick. She gently pushed in, past my sphincter making me gasp. We stay there for a minute until I was used to the size. Cindy began thrusting, it felt good, she was only going in a little bit. Cindy was too short to get the thrusting how she wanted, so we adjusted by me laying on my side and she got up behind me and inserted again. After several shallow thrusts Cindy stopped and was a little exasperated. We decided to move so that I was face down on the the bed with my legs on either side of the corner. Cindy stood behind me now, I felt her legs against mine and she thrust in harder this time. I was vulnerable to her and she went with it. Cindy seldom talked dirty, more of a moaner, and "that feels good" etc. Now she said "You like my hard cock, don't you. You want it fucking you." She was thrusting deeper and getting into a rhythm. I was being fucked, in the back of my mind I thought I should resist it somehow, but I let her take control. It felt good to give in. She said "This cock is rubbing on my clit." in a gruff husky voice. Cindy was into it. My cock was semi-hard as happens with anal, the other thing that happens is he intense prostate stimulation was getting me close to orgasm.

Cindy stopped thrusting, she pulled out with a little popping noise. At this point I felt empty, desiring to have the plastic cock thrusting in me with Cindy's nipples brushing my back again. I was panting, looking back, Cindy just looked at me with half closed eyes and said, "Turn over you slut, I need to see your face when I come." I obediently turned over and she ordered me to grab behind my knees, pull my legs up and apart as far as I could. Cindy hopped on and inserted and started thrusting in what seemed like one motion. Seeing her breasts bounce and the intense look in her eyes brought me to full erection. It snuck up on me and I started coming hard, grunting, toes curling, muscles clenching, jizz shooting all the way up to my chin. This triggered Cindy and she started thrusting fast and getting that familiar pink flushing on her face, neck, and shoulders, sweating. A long moan and arching of her back, stomach muscles clenched, one deep thrust. She pulled out and rolled onto her back, her glistening fake cock still standing away from her body as through the inanimate object was not finished. I was, happy and freshly fucked.