Latest Posts by sissymadison027 - Page 3

If like to emphasize again that you don't need to ask me first! Sending ME a dick pic is guaranteed to get a response! Big or small I love them all! 😍

Reblog if you are sissy boy and you dont mind receiving dick or sissy hypnosis videos

i do

Anybody else dig the "crossdresser mom" aestetic? Like I'm all for long evening gowns and stockings and heels or short skirts and thigh highs, but sometimes I just love Lulu Leggings, a halter top, and a messy bun too!

Just bought some shapewear to help give me that hourglass figure! Better yet: it's crotchless, which gives men easy access under my skirt... 😘

So I have an alternate profile on Facebook under a fake name where it's my sissy identity, and I'm on Facebook Dating just because.

Well one of my dad's classmates matched with me on it, and I'm kind of freaking out about what to do.

It's VERY clear on my dating profile that I'm a crossdresser, so I'm not worried about that. But part of me is so horny at the idea of him finding out I'm his old classmates sissy son.

The idea of him KNOWINGLY fucking and corrupting his old classmates child onto a sissy cum dumpster is so intoxicating...

The older, the fatter, the more of a slob, the better!

My sister and my aunt!

Reblog it! No need to be embarrassed 😍😘

Wow! So I've started using a breast pump to make me feel more feminine by going through things real women go through and by hopefully inducing lactation. I'm also hoping it increases my nipples or areola size too, because I'm kinda into that.

But I never expected how it would make me feel! It felt amazing and my nipples are so sore afterwards (in a good way!).

Definitely looking forward to doing this more to help my feminization! 🥰

Reblog and say it with me, out loud: I am a sissy, I submit to Allah

I need to start learning Arabic so I can exclusively speak it and forget how to speak English!

Islamic power !!!!

If I was a girl, I'd never use a condom

I agree! The dirtier and older and more unpleasant the man, the better!

My biggest fantasy is probably being kidnapped and mentally and physically abused and manipulated until stockholm syndrome sets in and I do anything for the dirty old man who stole me.

Like lock me in a tiny dark closet with no light and only come in to feed me once a day. Dont talk or even acknowledge me so after some time I would be begging and crawling after you for your attention. Make me your little broken babydoll😇😇😇

Anything, anytime!

Reblog this if it's okay to talk to you and be your friend and ask you various questions about your Tumblr pictures/ and fetishes

Bet