Really, a first time sissy transformation stays with a sissy for the rest of his life. From that moment on, he always questions the idea of his manhood. I have to thank the patriarchy for that one. If men were allowed to show emotions and allowed moments of weakness without it being a threat to their manhood, then my first time sissy transformations would not be nearly so effective.
But as it is, they aren’t. So, transforming a nice big man into a femme sissy breaks something inside their brains permanently. I love it.
I always start a first time sissy transformation with body hair removal. We do the full range of body hair, too. I lather up his legs first, usually with a fruity Skintimate shave cream. I always point out the change. “Look at that delicate skin underneath,” I say as I pull back a razor full of hair. Once a patch has been completely removed, I point out how smooth it is, rubbing my hands all over it.
It often feels odd for the sissy, who has never shaved anything but his face. Some feel ticklish and others rub their legs over everything (fur is particularly nice). And after a moment, they realize the razor is still in my hand. Though they raise their faces, I turn them over to their backs or their bellies. Then, I shave their armpits. Hairless means hairless, I let them know. What sissy still has a hairy back?
Of course, the next step is the outfit. I always start with a g-string, something lacy they can feel over their cock. Since most of my first-time sissies aren’t big, this isn’t too much of an issue. Occasionally, I have had to adjust and tuck a sissy of mine. Size doesn’t matter when you’re a natural bottom femme.
We put those legs in pantyhose, because of how they feel against nice, shaved skin. I chose a nude match with my sissy’s skin, just so they can reinforce how shiny and hairless their legs look. I don’t go with thigh highs or garters right away, because I want that all-over smooth feeling. That’s easier to remember as a first time sissy transformation. Otherwise, there are too many other sensations and my sissies get overwhelmed.
Then, we put him in a tight pushup bra, one that gives him some cleavage. And then I drape him again, in something comfortable and soft rather than sexy. See, for me, it’s about the long-term change of the psyche in my first time sissy transformations. My sissies remember what it’s like to feel feminine and soft, hairless and pretty, and so I dress them in soft off-shoulder dresses that come down to about 4 inches above the knee. I have them lay in my lap for an hour or so while I pet their hair, letting them know how absolutely pretty they are.
No pet ever forgets their first time sissy transformation, I promise you that.
We finish this all with sissy makeup training. Want to see what that’s about?
Or if you’d rather be trained as a sissy yourself, call!
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I had a great time with my two beautiful and sexy ladies Carmen and Kayla. It has been a while since we played together. It was definitely worth the wait!
I had a great time with my two beautiful and sexy ladies Carmen and Kayla. It has been a while since we played together. It was definitely worth the wait!
Ariel is truly amazing. Her voice is seductive and she really knows how to bring out the dirtiest version of me, hehe!!
Aileen is hot as they cum. She really knows what she is doing and is always the most satisfying!
WOW, I had an absolutely wonderful and memorable call with Jade! She listened to the role play that I wanted to work through with her and she was beyond perfect. She was able to step into her role as my milf neighbor growing up and really made my phone sex fantasy come to life! I can’t wait till I am working out of town again and have another chance to call her as I have other role plays to do with her.
Joey OUTSHINES everybody!! She is the ABSOLUTE PERFECT combination of everything. Sweetness ✔️, Compassion ✔️, Sincerity ✔️, Intelligence ✔️. And her Sexiness. . . OMG!!! Joey makes my life AMAZING!!!
Bailee was super enthusiastic and rolled right into playing out the fantasy I had. She is phenomenal.
Amber is kind and understanding of my needs. She would make a good friend!
This was only my second call with Addison, and I am already addicted to her sexy voice. She knows exactly how to command and control me. Love the way she takes me all the way to the edge, before she gives me the hands off command. Looking forward to obeying her more often.
Vanessa is simply amazing. She can be so precious or be so fucking wicked. Her oral skills are insane. She will make your cock cum, cum and cum again. If you want a spicy and wicked good time, Call Vanessa!!
Had a super hot call with Gracie! Her voice sounds so innocent and seductive at the same time. She is so sexy and we always conclude with an explosive finish.
Brittany is Amaaaaaazing! I don’t think she has said no to any fantasy I have. She always plays roles I come up with to perfection and with realism, sexiness and intelligence. It feels organic, like it’s really happening. In addition, she is enjoyable to talk to casually about my life, hers, or miscellaneous stuff. I hope it is not naïve that I consider her to be my friend. I feel special and fulfilled with my conversations with her, not limited to but certainly including sexually. I believe that my life has become enriched through calling her. Please give her the highest possible praise.