Sissy First Fuck Leads To Sluthood

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I could tell he wasn’t much into the more brutal aspects of BDSM by his delicate comportment. And upon dressing him, painting his face, and crowning him her with the wig, it was made more apparent. “I will call you Fannie.” She enjoyed humiliation even though she didn’t say so, I could read it. As if the cross-dressing weren’t humiliating enough, I took it a step further and decided some pegging would be in order and there were no qualms on the sissies part. I laid her on her back and looked into her doe-eyes. I worked it in slowly as if she were a tender virgin. I could tell it was her first time. “Do you enjoy having your pussy made love to?” “yes!” sighed out Fannie the sissy. “I am going to fuck you as if you were my

She enjoyed humiliation even though she didn’t say so, I could read it. As if the cross-dressing weren’t humiliating enough, I took it a step further and decided some pegging would be in order and there were no qualms on the sissies part. I laid her on her back and looked into her doe-eyes. I worked it in slowly as if she were a tender virgin. I could tell it was her first time. “Do you enjoy having your pussy made love to?” “yes!” sighed out Fannie the sissy.

“I am going to fuck you as if you were my girlfriend,” I said as I slowly, but firmly continued to thrust into her. She was getting into a headspace, truly believing herself to be a woman in that moment. She turned on her stomach and raised her ass up beckoning my strap-on. I thrust with more vigor, losing myself in the moment and she gasped in pain but arched her back challenging herself to take more of my dick. I flipped her sideways and threw her leg over my shoulder so she could look at herself in the mirror getting fucked as her mascara ran down her cheeks. A stream of cum flowed out of her sissy dick and came out so hard it got all on her face.

As Fannie gathered herself and got back into man-mode I asked him if he learned anything about himself? He said his intention when he came to see me was to feel like a woman for 90 minutes, but he knew in the back of his mind he was a man, a very important man with an authoritative position so the fact he was just in a wig and lingerie, getting his ass made love to like a young girl was ultimately humiliating, but it gave him this jittery feeling in his stomach. He left me a very generous gift so I gave him a butt plug. “Now that you are not a fragile virgin anymore, I expect to really be able to plow into you next time. Use this for practice.”

Miss Nikki

 

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