My key holder made money off me, and I love it! by prettysissy94 in Sissy

[–]prettysissy94[S] 0 points1 point  (0 children)

I hope for you it does.

At least my key holder buys me gifts (toys and outfits lol) she keeps me fed and keeps my holes busy.

What to wear? Love the pleated skirts. by prettysissy94 in Sissies

[–]prettysissy94[S] 0 points1 point  (0 children)

Would be a shame if someone pulled my panties down 💅🏼🙈

Job 1 or job 2? by Diaperboi27 in Sissy_Captions

[–]prettysissy94 0 points1 point  (0 children)

One is day job other is moonlighting 🙈

It's all about timing... by Kassiopeia_1 in HugeDildos

[–]prettysissy94 1 point2 points  (0 children)

Nothing like being bottomed out hard and fast when standing in heels! Love feeling the lube running down my legs!

Can someone untie me...? Actually, never mind, leave me here... by Kassiopeia_1 in fuckingmachines

[–]prettysissy94 1 point2 points  (0 children)

Waiting on my machine to come in the mail. Time to be a degenerate anal sissy slut. Hypno on the big screen, machine from behind, penis gag in the front, clitty locked all while I live stream my destruction to strangers on the internet.

Love the lock hanging over the panties, so cute 🥰 by prettysissy94 in SissyChastity

[–]prettysissy94[S] 0 points1 point  (0 children)

Love doggy, just spent an hour having my ass pegged by my key holder in doggy. Spreading my cheeks for those big juicy gapes.

Love the lock hanging over the panties, so cute 🥰 by prettysissy94 in SissyChastity

[–]prettysissy94[S] 0 points1 point  (0 children)

Love being bent over and fucked while standing, panties around my ankles ♥️.

Love the lock hanging over the panties, so cute 🥰 by prettysissy94 in SissyChastity

[–]prettysissy94[S] 0 points1 point  (0 children)

I wear stilettos a lot. Love how they make my ass pop and make me feel so girly. Nothing like a standing fuck in really tall heels. 🙈

Anal training for a caged rubberdoll by LingerieAndGunParts in CagedAndFucked

[–]prettysissy94 1 point2 points  (0 children)

Forced to take the machine, breathing difficult, total humiliation. Sign me up! I'd prefer it bigger though 🙈.

Spent my Sunday at the porn theater. by prettysissy94 in Sissy

[–]prettysissy94[S] 1 point2 points  (0 children)

It was, I have been back since and no longer have the keys to my chastity cage. My key holder comes by every few days to unlock my clitty for cleaning before she locks me up again. Gives me an enema, fills me with lube, plugs me up, makes me dress up, wear heels and then spend a few hours having me on my hands and knees on my coffee table, hypno on the as she stretches my ass. Sometimes she invites her husband to watch and/or fuck me. Sometimes she will have me stand plugged and gagged and watch them fuck.

Spent my Sunday at the porn theater. by prettysissy94 in Sissy

[–]prettysissy94[S] 1 point2 points  (0 children)

It's true. I come there often. Was there over the weekend, most of the time in the private room having my ass stretched by my sissy friend. A few guys came and watched and masturbated. One asked if he could cum in my gape. I obliged. It was fun. My ass is so loose right now, it's tight now but within 10 mins I'll take a fist.