The evolution of what's considered a "Sissy"

JennaChaste JennaChaste
533 0 10

Riding his cock felt so good I wanna go permanent and never jerk off again (OC)

Riding his cock felt so good I wanna go permanent and never jerk off again (OC)

There's nothing better than getting fucked in the ass while my useless clit is locked in chastity

There's nothing better than getting fucked in the ass while my useless clit is locked in chastity

What do you think ‘bout my most recent upgrade?

What do you think ‘bout my most recent upgrade?

I was mistaken for my girlfriend! 💞

I was mistaken for my girlfriend! 💞

By request AMA with mistress and me

By request AMA with mistress and me

Had my eye on this toy for months, can’t wait to try it out tonight! Anyone have any experience with it?

Had my eye on this toy for months, can’t wait to try it out tonight! Anyone have any experience with it?

I bought it at the heat of the moment and HE'll be my first. Any advice? (I'm a bit scared now)

I bought it at the heat of the moment and HE'll be my first. Any advice? (I'm a bit scared now)

Crossdresser people are not crazy or should be "healed". They are just human beings expressing their sexuality🥰

Crossdresser people are not crazy or should be "healed". They are just human beings expressing their sexuality🥰

Love to be Caged, it's a gooood feeling, but I want to be able to have a sissygasm. Someone to help me with that?

Love to be Caged, it's a gooood feeling, but I want to be able to have a sissygasm. Someone to help me with that?

💜Men’s Jeans, Never Again💜

💜Men’s Jeans, Never Again💜

Love my new cage

Love my new cage

Oh i would love to be her getting fucked

Oh i would love to be her getting fucked

Went out and grabbed a pizza with these under my sweatpants last Friday night. Stopped off on the way on a residential road, whipped off my bottoms and took a risky, slutty walk around the car. Got caught by headlights 🤭

Went out and grabbed a pizza with these under my sweatpants last Friday night. Stopped off on the way on a residential road, whipped off my bottoms and took a risky, slutty walk around the car. Got caught by headlights 🤭

Just shaved all my legs today;) what do you think?

Just shaved all my legs today;) what do you think?

5 rules for sissy cocksuckers - agree?

5 rules for sissy cocksuckers - agree?

First Pic, First profile

First Pic, First profile

Ask me questions about makeup? 😊💖

Ask me questions about makeup? 😊💖

From my old tumblr, thought it might be appreciated here too.

From my old tumblr, thought it might be appreciated here too.

Did my own makeup for the first time ☺️

Did my own makeup for the first time ☺️

I made a flowchart for sissies wondering what physical changes they can make. This is just a draft, feedback is GREATLY appreciated!

I made a flowchart for sissies wondering what physical changes they can make. This is just a draft, feedback is GREATLY appreciated!

This is it. The holy grail. Buy Natalie Mars' latest scene on Legalporno.com NOW to make more professional porn like this possible in the near future!!!

This is it. The holy grail. Buy Natalie Mars' latest scene on Legalporno.com NOW to make more professional porn like this possible in the near future!!!

When did I become SUCH A FAGGOT?

When did I become SUCH A FAGGOT?

Adjusting her heels

Adjusting her heels