Sissy Transformation ♕

Sissy Transformation

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.

Home Alone

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.

What to Wear

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.

Pretty as a Picture

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.

Touch It All

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?”