Jizz

Will I disappoint my Craigslist date?

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

So you never did tell me which shoes you wanted for our date, daddy? Why?

Sissies, GoneWildCD

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

Sissies

Ready for date night in a new dress! Do you have plans for tonight? ?

Sissies

Found on Grindr, wish me luck getting a date!

Sissies

Ready for our date daddy

Sissies

Finally got nerve to make doublelist date. My 1st BJ. Any advice, What would please you? He chose the outfit. Or is enthusiasm all I need?

Sissies

my date didnt show, care to cum on my face and tongue?

Sissies, FemBoys, GoneWildCD, sydneydommecd, cumtributes

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

Sissies, BBCsissies, GoneWildCD

Date night part 2: Plugged and ready to get fucked whenever you want

GoneWildCD, Sissies

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

Sissies, FemBoys

Shaved for my date, but she got sick...

Sissies, sissypersonals

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

Sissies

Does this outfit look good for a date?

Sissies

Date fell through so I'm sharing some new outfits

traps, Sissies

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

Sissies

Would you use this on me before or after our date?

Sissies

Will you date me?

Sissies, traps, FemBoys

New wig, new (fake) tits, new lingerie, going to be a fun date this weekend

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

Should I give up on dating women?

Sissies

3rd date tonight, do I let him smash?

Sissies, FemBoys, GoneWildCD, trapsarentgay, sissykik, traps

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

Sissies, sissykik, SissyChastity, sissyplace, sissypersonals, traps

Planning a post-quarantine date outfit, would you smash?

Sissies, traps, FemBoys, sissykik

My favorite panties vs my date's

Sissies, men_in_panties

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

Sissies

Ready to go on a date... If you are want me?

Sissies

Dressed up? Check! Caged? Check! Plugged? Check! Grindr date? Canceled :/

Sissies

would you take me on a date?

Sissies, traps

Want me to sit on your lap the entire date before we go to your house? ; )

Sissies

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

Sissies

Staying locked till my grindr date tomorrow night :).

Sissies

Waiting in the hotel for my date to arrive

Sissies

Ready for Date Night!

Sissies, sissypersonals, sissydressing, SissyChastity

Would you date me ?

Sissies

Ready for our first date ?

Sissies, FemBoys

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

Sissy_Positive

My Valentine's date outfit

Sissies

I do anal on every date!

Sissies, Stupidsissyslutsclub, GoneWildCD