Jizz

Sissy Date pics

Sissy first date!

Sissy first date!

Sissyperfection

Wanna go on a date with me? ;)

Wanna go on a date with me? ;)

FemBoys, Sissies

a real sissy dating site

a real sissy dating site

sissyhypno

Another date outfit? ;)

Another date outfit? ;)

FemBoys, Sissies

a real sissy dating site

a real sissy dating site

sissyhypno

a real sissy dating site

a real sissy dating site

sissyhypno

My friend phil likes girls in white dresses. Well it took a while to come but :)

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

I had a great time yesterday after date

traps, Sissies

Sissy Maker - Interative Novel + Dating Futa Sim

Sissy Maker - Interative Novel + Dating Futa Sim

futanari, NSFWgaming

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

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

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

SissyChastity, Sissy_humiliation

Going on a date! ❤️

Going on a date! ❤️

traps, Sissies, GoneWildCD, FemBoys

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

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

sissykik

Sissy veronica, 29 yo. Rehoboth. I'll be visiting in a few weeks and I'd love to

Sissy veronica, 29 yo. Rehoboth. I'll be visiting in a few weeks and I'd love to find a date. I want a man to treat me like a lady in the street and...you know ;)

sissypersonals

Sissy First Date

Sissy First Date

Sissyperfection, sissycaptions, DegradedWhores

How our date would escalate :3

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?

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

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

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

sissypersonals, sissykik, Sissies

Date night for a sissy

Date night for a sissy

Sissiesinaction

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

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

I need a date lol x

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

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

Sissy speed dating

TFCaptions

Nothing like BBC to get you goin in the morning

Nothing like BBC to get you goin in the morning

bbcpersonals, ChurchOfTheBBC, BBCsissies, blackmale, u_BlaqMeat, sissykik, Threesome_Dating_Site, Sissydating, Sissies, CrossdressersOnKik

got a invite to a roaring 20's themed new years, now I just need a date and a dress

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

36/sissy/NYC - I need an internet boyfriend. Our dates will consist of you watching

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? ❤️?❤️

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

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

Date me: horny Austrian Sissy

Date me: horny Austrian Sissy

sissykik, Sissydating

I put out on the first date

I put out on the first date

FemBoys, Sissies, trapsexuals, ChubbySissy

Creativity in sissy dating

Creativity in sissy dating

sissycaptions

Will you date with me? add me on OnlyFans BlondiBomb

Will you date with me? add me on OnlyFans BlondiBomb

Pegging, RuinedOrgasms, chastity, WomenLookingDown, girlswearingstrapons, littlespace, sexybunnies, furryfemdom, feetish, simps, PerfectPussies, Cuckold, Sissies, CuckoldPregnancy

Ready for our date!

Ready for our date!

Tgirls, GoneWildCD, GoneWildTrans, BBCsissies, Sissies, FemBoys

Your ex girlfriend dresses you for your sissy dates now

Your ex girlfriend dresses you for your sissy dates now

futanari

your face & my thighs have a date.

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,

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...

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...

Its only her 1st date...

resonantfrequency, nakedinthekitchen, FlannelGetsMeHot, WhyWouldYouFuckThat, ArabelleRaphael, desixchick, AikaYumeno, ChelNSFW, Sissy_Positive, Brazzers4U, FreakyPuss, NSFWasianbabygirls

How will our bathroom date end daddy?

How will our bathroom date end daddy?

BBCsissies, BlackOwnedSissies, FemBoys, Sissies

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

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

FemBoys, Sissies, GoneWildCD

Sissy first dates look a little bit different

Sissy first dates look a little bit different

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

Your reward if you treat me right on our date?

Your reward if you treat me right on our date?

FemBoys, Sissies, traps, GoneWildCD, YoungGuysGoneWild, GoneWildTrans