Been fun sharing these with you all, I’ve enjoyed sharing outfits more than I thought I would!
▲ 51 r/TrapCuties+2 crossposts

Been fun sharing these with you all, I’ve enjoyed sharing outfits more than I thought I would!

I’ve loved posting here lately, way more than I expected. Sharing my outfits has actually been really fun and I’m glad I started. What do you think of this one?

u/itsJessicaJayne — 4 hours ago

I like the red sweater top, but I’m stuck on the full look.

Unsure on this, does the full outfit work, or would you change something? I like the top but find it hard to match anything to it.

u/itsJessicaJayne — 1 day ago

Feeling bold in this one… is this outfit too much?

Went a bit bolder than I usually do with the gold skirt, fishnets, thigh high boots and leather top. Not sure if it’s too much, what do you think?

u/itsJessicaJayne — 2 days ago
▲ 65 r/TrapCuties+1 crossposts

Standard male clothing, trust me😅

Second time sharing on here, went for nothing fancy, just some regular boys clothes.

u/itsJessicaJayne — 4 days ago
▲ 41 r/TrapCuties+1 crossposts

Finally brave enough to post my first outfit💖

Hi everyone! This is my first time posting here.
I got the opportunity to dress up recently and it’s the happiest I’ve felt in a while!
What do you think of the outfit?

u/itsJessicaJayne — 6 days ago
▲ 18 r/Sissy

H! I'm new to the sissy lifestyle after years of private crossdressing, looking for similar experiences

Hi everyone,

I’ve been crossdressing privately for quite a few years now, but I’m still pretty new to the whole sissy lifestyle and a bit curious about it. I don’t think I’m very passable and I’m okay with that. I’m not really into guys, but I do find other girly/feminine types cute, as well as cis girls. All of my previous partners were women, but I have been kissed by men before.

Lately I’ve been thinking about sharing a bit more of this side of myself online. At the same time, I’m very protective of my privacy and I really don’t want my two lives to merge at all. I’m looking for ways to explore or connect without any risk of real life overlap. However, when I see other CD's, femboys or Sissies posting online I get a bit envious of their carefree nature and bravery to share themselves.

Has anyone else been in a similar spot? People who dressed privately for years, maybe aren’t super passable, aren’t primarily into men, and are now considering opening up online a little while keeping everything strictly separate? I’d love to hear how you handled it (or decided against it), what communities felt safe, or just any experiences that sound close to mine.

Thanks for reading. Appreciate any stories or advice you’re willing to share.

All the best,
Jess.

reddit.com
u/itsJessicaJayne — 14 days ago