In my previous story I mentioned how I had an itch inside me which did not need to be scratched, but *wanted* to be scratched badly. However, my path to BDSM was not a straight line. First, I figured if I were to do anything anal again I’d want it to be with a woman. Second, I was apprehensive about looking for older men I didn’t know to scratch that itch. So, the best option I could find was finding a woman to peg me.
My search started by finding **MANY** Femdom personals. All of which required payment, and all of which seemed like a business transaction. No connection. No heart. This was *not* what I was looking for. With this I took the plunge, made an email specifically for this able to be nuked if this didn’t work out, and made a personals ad on CraigsList, way back when it was easy to do this.
The ad was pretty straightforward: “22 M Curious about being pegged”, and in it I laid out my preferences and limits. Essentially I was looking for someone 40 and under, who could host, and was comfortable with a first timer and not jumping into things. I did specify I wasn’t looking to pay for anything as well. Hitting “Post” made me realize I was holding my breath, and was far more nervous than I fully understood.