Jizz

Got stood up on my very first sissy date:( So I took these instead:)

Sissies

Sissy first date!

Sissyperfection

Would love to secretly wear this on a first date... :)

GaybrosGoneWild, Sissies

Nervous before my first craigslist date... but the look of a girl who truly knows her place. :)

Sissies

I do a lot more than kiss on the first date! ;) <3 As always, pms welcome, or kik me at sissyjessi2015!

Sissies, BBCsissies, GoneWildCD

Sissy First Date

Sissyperfection, sissycaptions, DegradedWhores

Started going out late at night all dressed up. Theres no better feeling than walk on high heels with a buttplug buried deep ;) Also i just created an account on a dating app;) my bff should be my first cock but i cant wait forever right ;)? Yes i'll buy

GoneWildCD, traps, Sissies

About to have my first Grindr "date", wish me luck x

Sissies, jobuds

I'm a crossdressing sissy slut and I had my very first Grindr "date" today x

jobuds, Sissies

Had my first Grindr date yesterday, just finished my second one already. Think I'm a lil bit addicted! x

Sissies

Can I wear this outfit on our first date? ?

bigonewild, Sissies, gonewild, AllGoneWildGifs, sissyplace, GoneWildCD, u_eceverici

Good girls go down on the first date, right?

Sissies

First time posting here but i'm done with dating apps. 26 y/o MA sissy seeking anything from online RP to a RL daddy?

sissypersonals

I'm a sissy going on a first date with my KeyHolder.. I want to dress for him, but I've never done it. (I'm fully shaved, in chastity, and panties 24 7) Help me out!!!

crossdressing

Home from my date :) My first time giving up my keys!

Sissies

I put out on the first date

FemBoys, Sissies, trapsexuals, ChubbySissy

Which panties should I wear for my first date night?!

Sissies

Ready for our first date ?

Sissies, FemBoys

I put out on the first date ?

FemBoys, Sissies, GoneWildCD, Gigi977

[25] NJ/online. Anyone want to be the very first sissy I date?

sissypersonals

Any positive vibes. First 10 registered at MAKE FAST DATE.com (makefastdate.com) get my 10 GB of nudes for free !

Sissy_Positive

Secretly I love BWC Im half black and I think about being a white alphas sissy bitch. First 10 registered at MAKE FAST DATE.com (makefastdate.com) get my 10 GB of nudes for free !

BlackSissies4BWC

Let me be your sissy fucktoy . First 10 registered at MAKE FAST DATE.com (makefastdate.com) get my 10 GB of nudes for free !

indianSissies

This is how I'll look for our first date

SecretSassySissy, ForcedFeminization, GoneMildCD, sissydressing, Sissies

22 Sissy looking for long time training/dating. Online at first and in person if we connect! WA state

sissypersonals

Sissy first dates look a little bit different

sissycaptions, SissyInspiration, u_Ilovedicpic, sissydressing, u_4everarake, u_Sissiboi95, u_closetlover

I'm a "straight" man, wanted to take a sissy on a first date, and this is where you picked for us. Kik is GerFirl let's tell each other what happens to our bodies.

Sissykik2

Would you me suck you off for a first date?

Sissies

I love guys who eat ass on the first date!

traps, FemBoys, Sissies, thiccfems, GoneWildTrans, GoneWildCD, BBCsissies, Rearcock, timmythicc, boypussy, trapsarentgay, ThiccBoiss, Slut, needysluts, assholegonewild, TrapCumTribute, NSFW_Tributes, Nudes, sissyplace, sissydressing, Feminization, thickwhitegirls