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Pegging my Sissy Boyfriend

Ratings:
34 pages33 minutes

Summary

On an otherwise normal late afternoon, Carly comes home to find her boyfriend crossdressing, in her clothes! Rather than being upset, she finds the whole ordeal to be a little exciting. The young man, a thin and lanky fellow who isn't much larger than her, actually fits into her wardrobe pretty well. With a little extra help, she decides to teach him a few lessons on how to be a proper sissy!

Word Count: 9,100

This erotic short story features adult content, including gender bending characters, feminization, themes of submission and domination, and the use of a phallic-shaped toy on a man. For mature audiences only. All characters over 18.

Excerpt:

Naturally, my next question was probably what any girl would have asked to inquire about her boyfriend's sexual inclinations. "Do you like wearing girl's clothes? Because if you do, I'm sure I can help you pick out an entire wardrobe for yourself." I strutted up to the bed and tossed my athletic bag onto the mattress.

"No. I swear," he was quick to say. I'm pretty sure I saw him trembling as I drew in on him closer. "It was just a one-time thing! I really don't know what came over me. I was an idiot for trying on your clothes because I knew you'd be back. I don't know why I thought this would be a good idea."

"I don't know either." Once I was all but a foot away from Jonathan, it was obvious that he was quite intimidated by my presence. It didn't surprise me; after all, I had accidently come across him when he was living out what I could only assume was one of his secret fantasies. I'd never known a boy in real life to love dressing in women's clothing, but I knew they were out there, mainly due to the internet and television. So, in essence, it wasn't a total shock to me, since Jonathan was already way more feminine than most men, even as going so far to get his hair treated in a professional salon.

"Are you mad at me?"

"A little," I lied. Actually it kind of excited me. "Have you always had a desire to wear women's clothing? Are you one of those sissies, or whatever they're called?"

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