Dec 26, 2006

More about Stephanie

There's a missing chapter here. After getting away from Sally Strumpet, I went on with my life but still had an urge to Dominate. Likewise, my itch for a male experience wasn't scratched. That's when I was lucky enough to find Stephanie. I can't even recall where or how we met, I do remember that we went out to dinner fairly early on in our relationship. I think that that helped build a lot of trust with her.

I was to be her Dom and she my sub, though we knew that it would be an occasional and non-exclusive thing. Both of us are sluts, it seems.

Stephanie is very much into pain and bondage. She's one of those people that will actually test the bonds that she's placed in and will try to escape, meaning that you'd better tie her properly! And, for pain, she could take what Sally could take plus more. She's the kind of girl that makes a person switch from using their hand to a paddle.

We met at her friend's apartment. It was a nice little hideaway. She was a very patient girl, helping me know when knots weren't tight enough and when I wasn't hitting her hard. She wasn't topping from the bottom as much as just being friendly and trying to put me at ease. It took a while before I felt comfortable hurting her and using her pretty mouth to give me pleasure. I found the most fun part to be her tied up and blindfolded with her legs spread and my hand upon her cock and mine, both of ours in my hands next to one another and rubbing, masturbating the both of us. And, while I had engaged in anal sex before, she was the first person I had ever been with that begged for it. I was more than happy to oblige.

We met at this apartment several times. Each time I felt more at ease. She helped me feel more comfortable administering pain and taught me some fun bondage tricks such as mummifying with cling wrap. Stephanie was always more extreme in her tastes than I was comfortable going. I think that the only time I managed to get to her level was the day when I introduced the "pain and pleasure gloves." These were a pair of leather golfing gloves. They were incredibly soft and smooth when I bought them. However, I modified one glove by turning it inside out and putting as many thumbtacks through the surface as I could before turning it back to its right way. Now I had one glove of soft leather and one glove of metal spikes...

Bound and over my knee, she never knew which glove would be used on her next. Soft or spikey. Grabbing onto her cock with the spikes proved to be very fun. And the spanking I administered... it actually drew blood. While this freaked me out a bit, I think it satisfied her.

During one of our online conversations, Stephanie mentioned switching in the past. This perked my ears and I felt out her out a bit. It would be a few months before this was brought up again but, when it was, she asked if I would like to be topped by her. With the agreement that we would engage in some roleplay it was decided.

Stephanie and I had done a lot of roleplaying; usually she was my errant daughter and I was the corrective father. This time she would be the horny aunt and I would be the naive nephew. This became our regular fantasy for the next few times we played together. It was even more fun serving her than it was topping her. I think that, of everyone I play with, I often feel most comfortable with her. I think that's because we think a lot alike and have very similar needs. We've been going back and forth via email recently and I hope that my next time with Stephanie happens soon...

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