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Showing a Sissy his True Nature Through Humiliation

Sometimes a sissy just doesn’t know they are a sissy, or they know but they just can’t face it quite yet and I have to step in and show them their true nature. This happened one night, with a friend of mine, we’ll call him Steve. He was built more like a girl than a guy, slim hips and long legs, delicate hands, graceful fingers; a full soft mouth and he even wore his hair a little longer than most guys. Steve was the most obvious sissy ever to me and my girlfriends, but he just kept insisting he was only hanging out with us, because like all the other men he was totally into us and was interested in having me for his girlfriend.

Sissy Intervention

First of all, I don’t date men with little dicks, which I could tell he had and secondly, I don’t date sissies. It just turns into a fight over clothes and mirror time and really who needs that! So, we decided an intervention was in order to show Steve who and what he really was and of course turn him into Stephanie. So, I called him up and invited him over, using my sexiest voice and the promise of a Sex in the City marathon! I knew it would work and he showed up prompt and prepared to have a night of movie watching, that he kept referring to as “a date”. I smiled and let him as he arrived, instructing my friends to hide in the back until we were ready for them, I knew I could handle everything but the big reveal on my own!

He settled into the sofa with me and as we watched, I brought up shopping and some new clothes I’d gotten. He was very interested in hearing all about them of course, especially when I told him about one certain dress I’d seen him lusting after in the department store. He laughed and said he was thinking how good it would look on me and I teased him saying, “Don’t lie! I know you want that sexy little number for yourself.” He demurred and then asked if he could see it! This was going even smoother than I’d hoped and I nodded, leading him into the bedroom with my full length mirrors.

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Tempting the Sissy

I’d prepared the room ahead of time, high heels lying about and the sexy dress on the bed with some silky panties and a padded bra. I knew that we were about the same size, I told you he’s not built like a man, but that everything would be just a little too tight on him, giving him a super slutty look. He opened his mouth in awe as we walked in and forgetting all about me headed over to the shoes! “Just admit it! You want to try those heels on.” I told him and he protested a bit, then said...”Well, maybe. I mean what’s it hurt to try them on?” I knew I had him and things only got easier from there.

He picked them up and I pointed out that stockings were required as I wasn’t about to have him ruining my heels. He laughed and said okay. Getting him to take his pants off took a little bit of doing, since he wasn’t wearing underwear (“Those briefs are soooo ultra uncomfortable!” he explained) and was worried I’d get all turned on and want to touch his cock. That was so NOT going to happen, but I tossed him a pair of silky pink panties and some stockings and promised to close my eyes until he had them on. It didn’t take long at all and I knew he’d been practicing.

Are you Gonna Be My Girl?

I smiled and told him how pretty he looked and that he must have done this before since it was quick. He said it came naturally and almost giggled. So I picked up the short pink dress and dangled it in front of him, teasing him and encouraging him to put it on. He made me promise again not to tell as he slipped into it and then blushing and giggling twirled in front of the mirror.

“I look almost as pretty as you!” he said and picked up a tube of lipstick. “Now I just need a date!” He said and then paused. “I mean…I wouldn’t want a date, but it looks like I am going out and…” I just nodded and smiled. “Don’t worry Stephanie; I’ve got that covered too!” I told him and before he could protest the new name, our friends walked in, all of our friends, male and female. He started to blush then one of the guys; his favorite walked over and put an arm over Stephanie’s shoulders. “So, I hear you need a date!”