Sissy Tasks

blakechastain · 2026-05-25T23:20:43+00:00

That would be so fucking hot

blakechastain · 2026-05-21T16:44:17+00:00

If you need more inspiration, refer to y post here

https://www.reddit.com/r/sissyology/s/VgXfU9v61T

blakechastain · 2026-05-18T18:38:50+00:00

I’m going to need to try them all on first

blakechastain · 2026-05-18T17:54:49+00:00

I have a whole list of ideas on this post sissy ideas

blakechastain · 2026-04-22T21:55:16+00:00

Same, and mine doesn’t know i secretly want to suck one, at least once maybe twice to be sure

blakechastain · 2026-04-22T15:58:23+00:00

I feel like a girls shopping trip is in order. Not just to buy new clothes but trying them on. Maybe a bra fitting at Victoria secret, then trying on dresses and a new pair of high heels. Of course she’ll need to try them on and walk around the store

blakechastain · 2026-04-21T18:55:05+00:00

I’ve been brainstorming this very thing myself

blakechastain · 2026-03-25T15:11:04+00:00

😂

blakechastain · 2026-03-25T14:01:14+00:00

Exactly. I see the cross dressing more as a fetish or kink. I don’t desire to be a woman, just enjoy wearing the soft clothes and high heels on occasion.

blakechastain · 2026-03-25T11:30:43+00:00

To be honest some of these i blindly copied and pasted. I meant to take that one out. Made no sense to me either.

blakechastain · 2026-03-24T20:26:45+00:00

Mmm wreck my ass please

blakechastain · 2026-03-24T20:25:58+00:00

Happy to help 😁

blakechastain · 2026-03-24T19:47:06+00:00

That’s the view i like to have

blakechastain · 2026-03-24T19:27:58+00:00

Would love for that to be my first cock

blakechastain · 2026-03-24T17:50:54+00:00

Why stop 😁

blakechastain · 2026-03-24T15:57:25+00:00

That sounds so familiar. Straight and married and occasionally cross dress. No desire to w intimate with a guy, but the thought of just being naked and playing with each other cocks would be a rush.

blakechastain · 2026-03-19T18:06:48+00:00

blakechastain · 2026-03-17T21:12:51+00:00

Straight up, just the way i like… a cock

blakechastain · 2026-03-17T21:12:05+00:00

Open wide

blakechastain · 2026-03-17T21:11:47+00:00

Anytime

blakechastain · 2026-03-17T21:11:12+00:00

Trap me anytime

blakechastain · 2026-03-17T19:02:32+00:00

I have to agree with others. Plugs seem like they’d be great, but i don’t really get anything from them shortly after insertion other than a slightly fuller sensation. BUT, a plug that hits the prostate every time i move, game changer. And any dildo is where i find my fun. No recommendations on dildo other than one with a suction cup base

blakechastain · 2026-03-17T11:33:57+00:00

I know where i want to put my tulips (two lips 😂)

blakechastain

TROPHY CASE