Kaylie knows her boyfriend Jessie is a closeted sissy. He may look all alpha on the outside, but his fragile feminine side comes out whenever he thinks no one is around. He never leads during sex, he likes being pegged, and Kaylie has even caught him trying on her panties and stockings on more than one occasion. She knows Jessie secretly wants to be transformed into a girl and Kaylie has plans to make that sissy transformation permanent.
Jessie steps out of the shower and towels himself off. He’s smiling from ear to ear because he knows his girlfriend Kaylie will be out tonight. This means he will be all alone. On nights like these, he takes full advantage, sniffing Kaylie’s perfumes, trying on her shoes, and caressing the satiny fabrics on all her clothes. It’s not that he is obsessed with Kaylie. Don’t get me wrong, he loves her immensely, but what he really wants is to BE Kaylie.
Jessie loves the way she walks, talks, and even giggles. He even thinks the way she chews her food is adorable! What he would give to have her hot figure and wear all those sexy clothes! If only there was a way to make that type of sissy transformation! Jessie would take that opportunity without hesitation.
Jessie, fully dried, places the towel on the bed and immediately heads for the closet. What to wear was always an exciting question on nights like this. He picks out one dress at a time and holds it up against himself in front of the mirror. They are all so lovely! How would he choose?
Jessie finally decides on a light lavender slip dress with tiny white flowers. He lays it carefully on the bed and then heads to Kaylie’s dresser drawer where she keeps her stockings and panties. He finds the perfect pair of white thigh-high stockings, lavender panties, and a matching bra. “This should make my sissy transformation complete!” Jessie grinned.
Jessie completes the outfit with a pair of white heels. He stands in front of the full-length mirror admiring his ensemble. “This truly is beautiful, but it would look so much better on Kaylie. She’s the one with the perfect body!” Jessie says a little deflated.
But his words weren’t the only thing a little flat. Jessie starts to feel a tingling sensation in his chest and groin area. It’s a sexually arousing stimulation. Jessie is swept away in the feeling, He closes his eyes and in mere moments, he has a full-blown orgasm.
When he opens his eyes he sees a beautiful woman standing in the mirror before him. He doesn’t recognize his reflection at all. Jessie is now a woman with full, voluptuous breasts, long flowing hair, and very nice curves!
“I must have gone through some sort of sissy transformation with that orgasm”, Jessie says in a very feminine voice. He can’t believe what has happened.
Jessie wants to see everything that has changed. She strips out of her dress, pulls a chair closer to the mirror, kneels in it, and pulls her panties down slowly. “Holy shit! I have a pussy! ….. And it’s wet!”
Jessies starts masturbating in front of the mirror. Touching herself feels so good, but watching this gorgeous woman in the mirror makes it even hotter. Jessie is close to climaxing, fingering her pussy.
Just then Kaylie appears in the doorway. “Don’t stop on my account! I want to watch.”
Jessie should feel embarrassed or shocked, but somehow having Kaylie there while Jessie explores her new, sexy body just feels right. This makes Jessie cum hard and fast, over and over again. Jessie, not knowing it was possible, squirts on the mirror during her last orgasm. She finally stops when she is out of breath.
“I knew you’d love being a woman. I just didn’t realize how much! Damn!” Kaylie says. “I bet you’re wondering how I pulled off a complete sissy transformation, aren’t you?”
I made Clint my sissy bitch! Clint has always been different re... Read More
Kiss My Ass I’ll Do Yours If You Do Mine You Sexy Thing K... Read More
My secret sissy boyfriend! I’m often asked whether I prefer... Read More
Are you looking for someone who accepts you as you are? If so,... Read More
Pantyhose Fetish Jack had a stockings and pantyhose fetish for years a... Read More
Panty licker knickers sniffer… I know you do it. You ca... Read More
I Didn’t Know He Wanted Some Neighbor Pegging Sex See I h... Read More
He became a Partition Propositioner before my eyes… Hello... Read More
Universe Alpha Centauri –Dance under the rule and era of your Go... Read More
Showing off the goods The door opened and Jim was greeted by an... Read More
Turning Gay For Mistress – Could It Happen? Hello, bloggi... Read More
As I looked at my new sissy slave, all dressed up in the sluttiest out... Read More
Tremendous customer service and professionalism. Aileen took the time and interest to start getting to know me. Just a delight to have a conversation with, aside from her sexy voice.
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.