Only recently, I showed her a video on the internet of a man being butt fucked by a woman with a strap on dildo, and casually mentioned that I would be “willing” to try that if she was interested. Again to my surprise, she was open to it. We didn’t do anything about it for a while, and hadn’t bought a harness, but I had bought a couple of dildos for her, hoping she would use them to pleasure herself while I watched, bound and gagged, and locked in a chastity device. About the same time I bought an anal hook and expressed an interest in crossdessing. She was ok with that too and I soon began buying some women’s panties, stockings, and other things.Then one night she blind folded me and tied me face down across the coffee table and began to paddle me. The paddling was nothing new but soon I felt the new sensation of something slippery sliding between my ass cheeks. She was sticking a dildo in my ass! It hurt like hell at first but soon the pain went away and it actually started to feel. A slow song came on, and I asked Jennie to dance.I slid my hands under her jacket and rested them on her back right above her skirt. She put her hands around my neck."Thank you for tonight. I appreciate you being a gentleman." I was told that I had to be on my best behavior." I hope that wasn't on my account." No, I have gone through some girl related issues over the last few weeks. Tami wants me to go out and have fun without the pressure of a relationship." Are you saying you are not interested in me?"That one took me by surprise."To be honest, I hadn't thought about it." I could tell that was the wrong thing to say so I tried to recover. "It is not you ... that came out wrong and sounds horrible. Let's just tell it like it is. I am a 'stupid boy' at times and as such, I act like a jerk. Jennie, if I took two seconds to think about it, I would want to go out with you. As a matter of fact, I would love to see you again." Nice save. I ... shit."I felt someone tap me on the.
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