Jizz

I'm ready for our date daddy ;)

GoneWildCD, Sissies

Sissy first date!

Sissyperfection

Wishing I have a date for new years ?‍

FemBoys, Sissies

My lovely, perfect Lady Owner says I have a cock date today and She wanted me to look cute. But I have to stand for another three hours as punishment for tripping in my heels this morning.

Sissies

My date last night came with stockings and panties under his boy clothes. ?

Sissies

Sissy Maker - Interative Novel + Dating Futa Sim

futanari, NSFWgaming

what i wore for my most public appearance to date

FemBoys, GoneWildCD, Sissies

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

Sissies

Found on Grindr, wish me luck getting a date!

Sissies

My summer date outfit

FemBoys, Sissies

Ready for our date daddy

Sissies

Now i just need the date

traps, Sissies, Aoxxt

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

Sissies, BBCsissies, GoneWildCD

Hope you don't mind me wearing this out on a date!

GoneWildCD, Sissies, FemBoys

Tinder date just left and I'm still feeling horny :3

FemBoys, GuysFromBehind, Sissies, traps

Dressed up without a date on Valentine's...

TrapsUK, FemBoys, Sissies, Feminization, GoneWildCD, traps, SissyHeaven, sissyplace

Looking for valentines date ;)

SissyChastity, Sissies

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

Sissyperfection, sissycaptions, DegradedWhores

Hoping this is how our date will end.. ;)

GoneWildCD, Sissies, u_Brunk1874

Getting ready for a play date with my daddy ? He loves me in heavy makeup ?

Sissies, FemBoys

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

Date night for a sissy

Sissiesinaction

Does this outfit look good for a date?

Sissies

let's go on a date

traps, Sissies, FemBoys

Can I wear this outfit on our first date? ?

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Waiting on my dates can be fun... ;)

Sissies

When you leave work early to have your alpha male date take you shopping. I must say that stiletto heels are not only beautiful, but very functional too. They bring my ass to a comfortable height for my tall dates to fuck me standing up.

GoneWildCD, Sissies

Going on a Tinder date... Give me advice to groom my clitty before I lock it back up under my favorite panties ;)

Sissy_humiliation

Getting ready for date night.......?

GoneMildCD, Sissies, traps

Would you mind if I flashed you my cage during our date?

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Getting ready for our date tonight.. hope you're looking forward to it

GoneWildCD, Sissies, traps, u_trysexualcd, u_IGORIGORIGORIGOR420

EU: Sissy looking for a date

sissypersonals, Sissies

28 very dedicated CD looking for other sissies/CD to talk to ;) potentially date if it feels right. local to Southern CA but will talk to anyone as Im open to travel (after all this madness is over ofcourse)

sissypersonals, Sissies

Should we schedule a play date?

traps, Sissies, FemBoys

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

Sissies

I'm ready to go on that date daddy :3 (I wish)

Asiantraps, traps, Feminization, Sissies, FemBoys

Anyone want to take me on a date? :)

traps, Sissies

Prepping date outfits for after all this ?

traps, Sissies, FemBoys

Wanna go on a date and play 2ball pool together?

Sissies

Pretending I'm dressing up for a date and trying to be cute ?

FemBoys, Feminization, Sissies, sissypersonals

We get home from the lunch date and you see I wasn't wearing panties the whole time. What comes next?

GoneWildCD, Sissies, sissydressing, traps

Staying locked till my grindr date tomorrow night :).

Sissies

A date night with me always ends on all fours

traps, Sissies, trapsarentgay

what my date had for dessert

GoneWildCD, Sissies, trapsarentgay

Who wants to take me on a date? maybe fuck me after? ?

TransGoneWild, traps, GoneWildCD, Sissies, FemBoys

Ready for Date Night!

Sissies, sissypersonals, sissydressing, SissyChastity

a date night ..

traps, FemBoys, Sissies

Would you date me ?

Sissies

this would be fun date lingerie

u_sydneydommecd, Sissies, GoneWildCD, FemBoys, Sissy_hot, Sissydating

I can wear this under my date outfit for you if you like ;)

Sissydating, Sissy_hot, FemBoys, GoneWildCD, u_sydneydommecd, Sissies

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

Sissy_Positive

I'm ready for our date

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Stop dating your GF big bro

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Take me on a date ?

amateur_shemales, Sissies, trapsarentgay, trannyslut, FemBoys, GoneWildCD, sissyplace, u_ts_milk

This is how I'll look for our first date

SecretSassySissy, ForcedFeminization, GoneMildCD, sissydressing, Sissies

Ready for our date, babe

SecretSassySissy, Sissies, Feminization, sissydressing

Sissy first dates look a little bit different

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

I love guys who eat ass on the first date!

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