Sissy Friend Gets Himself Cornered While All Dolled Up

During a conversation at my place, my soon-to-be sissy friend drunkenly commented on how much easier girls have it than guys. He kept saying that all we needed was nice pair of legs and a smile and we could get anything we wanted and anywhere we wanted in life. I told him that it wasn’t that simple and that he wouldn’t last one day as a woman. When he assured me that he would, I called him on it and challenged him. We’d go to the mall together with him as a woman and see if he could get a guy to buy him a purse. He was hesitant but didn’t want to lose. I smirked when he shook my hand in agreement.

After a few hours, I have to admit that I was impressed at how convincing he was. Some make-up, pink pumps, fishnets, and my sluttiest club dress later, and he was totally passable. I dare say, even hot. It wasn’t until we were in the mall parking lot that the realness of the situation started setting in for him. The minute cold air hit his sissy, thonged ass cheeks, he started to panic and wanted out. But I told him that a deal was a deal. I locked my door, and refused to drive him home until he at least went inside one store. As he got used to walking in 6-inch heels, he realized that he was actually getting away with it. He passed two families who hadn’t noticed at all that he was a guy and that’s when things went to his head.

He started swaying his hips triumphantly at me as if he’d already won.

Unfortunately for him, I wasn’t the only one watching. He winked at a pack of guys he passed and, like a baby lamb skipping past a wolf den, I knew that his sissy ass was done for. It started out as harmless flirting as the four guys slowly surrounded him and copped the occasional feel. He was so in the moment that he didn’t realize that he was slowly being ushered down a dark alleyway. When the first cock popped out, that’s when he got scared. I had warned him that there was a subtle difference between flirting and ‘asking for it’ but he didn’t listen. And now the only way he was going to get out of this one was by sucking and cucking his way out. Did he really have it in him?

End of Part 1

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