Choosing My Strap On

I love the idea of choosing the strapon I will be fucked with. If I were to look back and think seriously, I’m still not sure I could tell you when my desire to be fucked with a strap on began. It goes back so far that it almost seems like I’ve always wanted to be a bitch for a Mistress, but that can’t be entirely true. There had to be some point in time where I became aware of strap on Femdommes and what they did exactly. But it was so long ago that I can’t even pinpoint that moment in time anymore.

Despite the fact that being strap on fucked has been a long-running fantasy of mine, it took many years before I was ever able to indulge it. I’d married young, just out of high school, and my wife wasn’t into that sort of thing. As often happens in these kinds of marriages, we eventually realized we weren’t compatible (sexually or otherwise) and went our separate ways. So I found myself in my early 30s, single, and horny as hell.

I drifted around, having sex with quite a few different women and trying to meet a Strap On Femdom Mistress who could give me the chance to submit–the chance I’d been waiting for for years.

It was slow going at first. It’s been said that there are ten submissive men for every one dominant woman out there, and I believe it. Actually, I wouldn’t be surprised if the ratio were even higher than that once you take out all the Nigerian scammers and so forth on the BDSM dating sites.

Eventually, I Did Find My Strap On Femdom Mistress

I could tell you horror stories that’d curl your toes, but that’s a story for another time. I’ll just suffice it to say that I persevered until I finally found my lovely Mistress. We hit it off immediately, both sexually and otherwise, and things moved pretty quickly.

We did a lot of exploring in the bedroom. It turned out I enjoyed being submissive even more than I thought I would, and since she doesn’t have a switch bone in her body, that worked out well for us! Mistress had me confess to her what my biggest fantasy was one night. I had to share with her that I wanted to be fucked with a strap on.

I was a little embarrassed, but she didn’t seem to be at all surprised. I don’t know if it’s because strap on fantasies are common among male submissives or because she knew how much I enjoyed all the anal play we’d been doing. She just smiled a little, seemingly to herself, and told me that we’d just have to find a way to make my fantasy come true. I was kind of nervous after I saw that smile.

A Little Humiliation And A Big Surprise

One day, Mistress told me that we were going to the adult toy store in town. I was surprised because Mistress normally buys her toys online. Then, she told me that she was taking me so that I could pick out the perfect strap on dildo for her to fuck me with. I caught on quickly: Not only was this an exercise in selecting the right one, but it was also an exercise in erotic humiliation.

The store was actually crowded when we got there on Saturday evening. Of course, Mistress had picked the time when they were most likely to be busy to take me there. She made a big deal out of looking at nearly every dildo in the store and asking me what I thought. She always spoke just a touch too loud when she asked, “Do you think this will fit in my strap on harness?”

It was worth all the humiliation, though, because when we got home, I was more turned on than I’d ever been in my life. Apparently, she was, too, because she ordered me to the bedroom. I helped her get undressed and get into her strap on harness. Then, she washed off the new toy, stuck it in her harness, bent me over the bed, and started slowly working it inside me.

It felt so good. I also loved it when she taunted me about how the people in the store looked at me while we were shopping. “Do you think they knew this dildo was going to be buried in your ass within 15 minutes of us leaving?” she asked.

And that was when I discovered that I love strap on humiliation as well. But that, too, is a story for another time….