Jizz

online dating works! [sissy] [gif]

xxxcaptions

Wanna go on a date with me? ;)

FemBoys, Sissies

Another date outfit? ;)

FemBoys, Sissies

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

GaybrosGoneWild, Sissies

My friend phil likes girls in white dresses. Well it took a while to come but :) when's the date?

GoneWildCD, Sissies

I had a great time yesterday after date

traps, Sissies

Waiting on my lunch date. I hope it goes well ;)

FemBoys, GoneWildCD, men_in_panties, Sissies

Would you ever date a guy with these feminine features ladies or am I destined for the sissy lifestyle?

ladybonersgw

got stood up for shopping date, so now just relaxing at home in this

FemBoys, Sissies, sydneydommecd, GoneWildCD, traps

NSFW-Day 36 and now I was told new release date is 3-1-2018

SissyChastity, Sissy_humiliation

Going on a date! ❤️

traps, Sissies, GoneWildCD, FemBoys

Dutch sissy. Make me so cockdrunk that I will finally take the next step by going on a date. Send me all your captions, hypnos and cocks. -Kelly_sissyNL

sissykik

My date liked my jewelry so much he asked me to keep wearing it until tomorrow morning ;)

GoneWildCD, Sissies

What inevitably happens on all dates as a sissy

bitchsissies

26 yrold. Experienced Chicago BBC Dom looking for white sissy for regular hook up and dating

sissypersonals

Waiting for my tinder date

twinks, FemBoys, traps, GaybrosGoneWild, GuysFromBehind, Sissies

NJ/NY Sissy SWITCH looking for boy/girl/sissy to have a fun date tomorrow night~

sissypersonals

Your Third Date as a Sissy... (gif)

Sissyperfection, sissyhypno, xxxcaptions, u_shaggyO1

Get ready for your date, sissy.

Sissyperfection

Sissy cd looking to talk. Just got home from a date

sissykik

Why would a model ever date you? [wholesome] [it cos the 3.4" u packin] [jk Im sure you have a huge dick] [unless ur one of the, like, 3 sissies who read these captions, in which, u got a tiny dick, slut.] [catering to the masses] [#contentcreator]

xxxcaptions

How our date would escalate :3

FemBoys, traps, Sissies, sissykik

Maybe if your date stood you up, would you... idk.. go out with me instead?

traps, GoneMildCD, Sissies, FemBoys, LGBTGoneWild, bigonewild, toolonglost, dykesgonewild, gonewild, UnderwearGW, cumtributes, CockTributes, NSFW_Tributes

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

26 M Hung Daddy/Dom in Connecticut looking for FWB and/or dating. Kik is MaFilmDom

sissypersonals, sissykik, Sissies

I want to be a good sissy and suck your cock under the table while you go on a date with my crush?

jobuds

Cute enough to date or hot enough to fuck?

traps, Sissies

I am a 24 yo sissy in Indiana looking for a dom daddy interested in dates and possible LTR. More details in comments

sissypersonals

It's been a really long time since I felt kinda cute. Now I just need a guy to take on a date. ?

traps, GoneMildCD, FemBoys, Sissies, LGBTGoneWild, AmIASexyQueer

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 need a date lol x

GoneWildCD, Crossdressing_xxx, TrapsUK, trapsgonewild, Sissies

Would it turn you on at the end of the date if you found out I was wearing a buttplug all along?

GoneWildCD, FemBoys, Sissies, u_suddenlypanties

Sissy speed dating

TFCaptions

Looking for a man or another sissy to date! Please be close to OC, CA! Dm me ❤️

Sissydating

got a invite to a roaring 20's themed new years, now I just need a date and a dress [Sydney] [T]

Sugardaddysiteranking, Crossdressing_xxx, ChubbySissy, GoneWildCD, Sissies, FemBoys, r4rSydneyXXX

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

I wanna sit under the table and slurp your cock while you date my friends... kik me same as here for their IGs and to chat about using my sissy ass in front of them?

jobuds

I'm dressed for our date but we maybe we should stay in ;) kik: sissy_bell

sissykik

36/sissy/NYC - I need an internet boyfriend. Our dates will consist of you watching me cum like a girl. Between dates, you'll post clips of it—the shameful moans, desperate facial expressions, embarrassing confessions. Make me feel used and humiliated lik

sissypersonals, u_bklynsis1983

❤️?❤️ Still looking for a Valentines date, babe? ❤️?❤️

FemBoys, Tgirls, GoneWildTrans, trapsarentgay, LGBTGoneWild, Sissies, Sissydating, Crossdressing_xxx, GoneWildCD, AmIASexyQueer, KINK

Date me: horny Austrian Sissy

sissykik, Sissydating

I put out on the first date

FemBoys, Sissies, trapsexuals, ChubbySissy

33 [T4F] - Any woman wanna date a sissy?

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West Hollywood guy looking for a sissy for a day date. Message me. Serious only

CaliSissies

Will you date with me? add me on OnlyFans BlondiBomb

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Ready for our date!

Tgirls, GoneWildCD, GoneWildTrans, BBCsissies, Sissies, FemBoys

I put out on the first date ?

FemBoys, Sissies, GoneWildCD, Gigi977

I'm ready for our date

SecretSassySissy, crossdressing, Asiantraps, Sissies, Feminization, sissydressing

My ex-Girlfriend caught me fully feminized at the high school prom on a date with her Brother. Now she knew how right she had been to break up with me, I was a sissy faggot

EffeminacyAndFaggotry

your face & my thighs have a date.

BlackOwnedSissies, SissyInspiration, BBCsissies, Sissies, trapsarentgay, TransDebauchery, Feminization, ForcedFeminization, dickgirls, Shemales, OnlyIfShesPackin, CDgonewild, FemBoys, ShemalesParadise, transporn, traps, GoneWildTrans, sissyplace, GoneWildCD

when you friends ask about your study-date with your androgynous goth classmate, you can show them this pic ?

FemBoys, Sissies, GoneWildCD

Its only her 1st date...

BreastEnvy, shavedpussies, CheatingCaptions, kirillwashere, nsfw_handpicked, gymgirls, Sissy_hot, bizarresex, fyiff, MatureLadies, wifeyworld, BondageStuff, FlaccidandErect, MeadowNymphs, Assgrab, nudemalecelebs, SummerHart, FatiVazquez, DanielleDerek

Its only her 1st date...

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33/sissy/NYC/online - I need a boyfriend for semi-reg cyber dates that end with you watching me cum like a girl on video

sissypersonals

How will our bathroom date end daddy?

BBCsissies, BlackOwnedSissies, FemBoys, Sissies

Both Ask You Out On A Date...Who Do You Choose? ?

FemBoys, Sissies, GoneWildCD

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

i'm gonna miss our study dates ?? can we still hang out, even though the semester is over?

FemBoys, Sissies, GoneWildCD

Your reward if you treat me right on our date?

FemBoys, Sissies, traps, GoneWildCD, YoungGuysGoneWild, GoneWildTrans

This "straight" boy wants to date a sissy, we end up here, and both get used and abused in a huge sloppy orgy. Let's RP, Kik GerFirl

Sissykik2