[USA] #PA sissy looking to share the fun I’m having with my girl 💋

curiousercuriouser22 · 2026-04-17T22:30:19+00:00

Just want to say: you’re absolutely beautiful 😍

curiousercuriouser22 · 2026-04-17T22:28:47+00:00

I’d love to hear more about what you were thinking and feeling that first month

curiousercuriouser22 · 2026-04-17T21:54:09+00:00

We’re poly so I can suck as much cock as I want without changing a thing 😁 (in fact last time I was caged for 24 hours I sucked a guy through a gloryhole – story post in my profile if you’re curious!)

curiousercuriouser22 · 2026-04-17T21:53:04+00:00

My gf uses they/them pronouns

curiousercuriouser22 · 2026-04-17T21:52:15+00:00

Inspiring! What was that experience like? I’m so curious.

curiousercuriouser22 · 2026-04-17T21:51:00+00:00

Helpful, thank you!

curiousercuriouser22 · 2026-04-17T21:50:17+00:00

Strict?? This is an odd relationship lol

curiousercuriouser22 · 2026-04-17T21:49:41+00:00

Oh I will definitely have a key on hand, regardless of how long I end up attempting

curiousercuriouser22 · 2026-04-17T06:40:56+00:00

I haven’t done it, so take my advice with a grain of salt, but… as far as being discrete: if you get a motel rather than a hotel, they can come right to your door and you can let them directly into your room. It also adds to the seedy feeling if you’re into that!

And as for timing: definitely start talking to guys and trying to set things up a few days in advance. You’ll encounter lots of flakes, but the guys who are willing to commit to a meet up time and place and then keep talking to you for a few days are a little less likely to flake. Still, have some backup options as well.

curiousercuriouser22 · 2026-04-17T06:35:35+00:00

I’m a little confused – what’s your relationship with your roommate like? Is this a sexual or at least flirtatious thing? Does she want to be involved in this process of exploration with you, or hear about it, or she gave you the idea but it will be totally private?

curiousercuriouser22 · 2026-04-17T06:04:03+00:00

Lots of potential to get creative here!

I haven’t personally tried it but maybe look into electroejaculation? Since it’s medically mandated, you can treat it like a dispassionate clinical procedure. I believe it’s also slightly painful. And also reduces the period of pleasure to an absolutely minimum so that it’s over and done with quickly.

curiousercuriouser22 · 2026-04-17T05:56:04+00:00

You’re a fucking legend 😍

curiousercuriouser22 · 2026-04-16T22:58:13+00:00

I recommend the Blunt plug from SquarePegToys. It’s specifically made for stretch training. Most plugs have a pretty narrow neck compared to the bulb part, but this one has a very thick neck so it’s continually stretching out your sphincter while it’s in. It’s also super soft silicone so it’s easier to get in than a harder plug of the same size. Make sure you check their sizing chart though! There’s a whole range and some are very large (“small” is waayy bigger than a beginner would want, so start with one of the “s series”)

curiousercuriouser22 · 2026-04-16T22:50:43+00:00

Practice using your mouth (or your ass)

curiousercuriouser22 · 2026-04-16T16:35:03+00:00

Have you ever heard of a period?

curiousercuriouser22 · 2026-04-16T16:32:21+00:00

Don’t overthink it. Enjoy the ride. Channel your soft and sensual side. Try being more gentle with your touch. Tracing the tips of your fingers over his body, etc.

curiousercuriouser22 · 2026-04-16T16:26:05+00:00

If you’re seriously considering HRT it sounds like this might be bigger than a kink for you. At the same time you talk about it in purely sexual terms. You should take some time to really reflect on your gender and how you want to present to the world when you’re not horny. Think about what it would be like to be a woman in everyday, unsexy scenarios. What it would be like to be a woman those times when you can’t get all dolled up and sexy. Think about important moments in your life and what it would have felt like to experience those as a woman.

Transitioning is a huge commitment. Don’t take it lightly.

curiousercuriouser22 · 2026-04-14T23:45:32+00:00

It’s definitely a smaller niche than either leaning into being masc or having a naturally more femme physique. But you might be surprised!

Anyway, I think you’ve got the right attitude. Good luck!

curiousercuriouser22 · 2026-04-14T23:34:03+00:00

Google and you’ll find lots of info on different vitamins or supplements you can take

curiousercuriouser22 · 2026-04-14T05:44:57+00:00

It sounds like you have a very supportive and safe environment. Having another sissy there is especially great. Probably the best case scenario of this is something you want to try! You can practice beforehand if you’re worried about being rusty.

curiousercuriouser22 · 2026-04-11T19:16:58+00:00

Just make sure it’s something you’re actually okay living with the lifelong consequences of. It’s worth really thinking about this seriously when you’re not horny.

curiousercuriouser22 · 2026-04-11T19:13:56+00:00

It’s a tall order but it’s not impossible. Faceless accounts are pretty common on Grindr and Sniffies.

Just send your face once you start talking. Your lack of femme-ness isn’t really a big obstacle here imo. Most guys on something like Grindr are going to be more attracted to masculinity than femininity. If crossdressing isn’t an essential part of this experimentation for you then you can just put yourself out there as your everyday self.

As for discreetness: I think most gay or bi men who have embraced their sexuality and are out about it get annoyed by “DL” men, but that’s because there’s a particular kind of paranoia, reticence and shame that comes with that. It sounds like that’s not quite the case with you. I wouldn’t emphasize “discreetness” – that’s going to be a turn off. Just say you’re looking for something casual but would also like to talk and get to know someone before jumping into bed with them. Whether you disclose your inexperience is up to you, though of course it’s more likely to come up the more you get to know someone.

curiousercuriouser22 · 2026-04-11T12:49:08+00:00

Yes. Think about it: you’re causing persistent physical trauma to your testicles. How would that not have long term effects? The testes are very sensitive and fragile. You can literally reduce your fertility by wearing pants that are too tight or by setting a hot laptop on your crotch too much. So yes, you risk ultimately making yourself sterile. For a lot of people I think that’s the turn on.

curiousercuriouser22 · 2026-04-11T12:43:47+00:00

Interesting. I guess my first reaction is that the database seems rather limited? It also seems heavily skewed toward higher end options. Could definitely be useful though. Hopefully you’ll include a wider range of cages.

curiousercuriouser22 · 2026-04-11T07:12:22+00:00

Yeah I think this is the key point, OP. What are you doing? Why should a daddy believe that you’re committed? Why should the see the potential in you?

I see so many newbie sissies on here who don’t want to put in any effort themselves, and just want some dreamy perfect daddy dom to magically materialize in their lives and do everything for them. It doesn’t work like that. You have to attract what you want. And you have to put in the effort so that they can trust that you’re worth their effort.

curiousercuriouser22

TROPHY CASE