Wanting to go farther... - Sex Stories

Wanting to go farther...

... of course added to the feminizing effect. The panties were so small that they did not reach over my butt, but instead barely gripped on. My butt crack stood out, which was hot especially since it was smooth. I looked in the mirror and the sight took my breath away. The shaving and the panties had done the trick, this wasn't the butt of some hairy dude. This was the butt of a sexy women. Rotund, smooth, and accentuated by the extremely tight pink panties that clutched the skin. I couldn't wait for Jon to see this. But then again they were my friends so I put them back with guilt and shame. But I needed to get some, and I needed to be prepared for next time. He would want to stick his cock in me again and I needed to be prepared for it. The thought, "maybe I should just refuse this painful and degrading act" never even entered my mind. I ended up by getting a polka dot pair of boy shorts, that also gripped the ass from the laundry in my apartment. For some reason, from the laundry and not my friend felt better, although I am not sure it was a better act in hindsight. Now I needed be prepared. My asshole was sooo tight and painful but I at least had to try to prepare for what he inevitably would do (stick his dick up my ass) and what I new I would submit too, no matter how painful. So my thought was a toy of some kind to try and prepare. For weeks I would look at the sex shop and be too scared to walk in. "What if someone saw me? They would definitely know I was a fag ...

... then?" But I finally built up the courage thinking, "so what, a lot of people do this." I walked in the sex shop and to my chagrin a very attractive and young woman was at the counter. "Why couldn't it be an old woman or an old man???" I had never debased myself purposely in a front of a young attractive woman. My heart beat and I felt so much guilt and shame. I walked around aimlessly looking at the toys and dvds, trying desperately not to look at anything "too gay." Finally, my lust overcame my shame. I picked up a medium butt plug and tried to steel myself and walk up to the counter. I put the butt plug on the counter and hoped that the transaction would be quick. Instead, it felt like it took ages. She glanced slowly, painstaking at the butt plug, looked me straight in the eyes for what felt like a long time and then slowly rang up the shiny purple butt plug. I felt my face flush and my eyes downcast. I had never revealed so much weakness in front of a young attractive woman. I knew when our eyes had met that her assumption of me had changed. Not in a mean way, but in a reassessing way. When I walked in, I might have looked like a tall competitive guy. Maybe even an alpha that she would consider fucking. After that glance in the eyes I knew she saw me as a confirmed beta... I knew that she now knew that I take other men's cocks in my ass. Other men fuck me for their pleasure, not only was I gay, but I was the bottom, the pleaser. Now she looked at me different, but it felt ...