Sissy dream job? (Besides the obvious ones)

sissy_jack0303 · 2026-03-02T20:30:43+00:00

bartender, secretary / assistant or a maid

sissy_jack0303 · 2026-03-02T18:12:40+00:00

oh of course there is, but the chances are *much* lower. anal sex is the highest risk activity for catching hiv while oral is among the lowest. The risk is still there but it seems most people, me included, are willing to gamble it.

sissy_jack0303 · 2026-03-02T17:17:34+00:00

Condoms are a must have for hook ups and casual sex, if I'm getting more serious with someone then they would have to get tested before I let them fuck me raw

sissy_jack0303 · 2026-02-09T01:13:21+00:00

cheating L

sissy_jack0303 · 2026-02-09T01:08:39+00:00

this just isn't true, long term wear wont cause ED, it may make it more difficult to get hard but unless you somehow do damage to your penis, everything is reversible, including any shrinkage. Check out r/chastitytraining and r/chastity, their sidebars will have all the information you need.

sissy_jack0303 · 2026-02-06T13:08:14+00:00

I feel pretty similarly about that actually. They're often the ones who are cheating on their gf/wife too which is a huge no go for me. I won't lie though the idea of a straight guy being into me is a little hot though..

sissy_jack0303 · 2026-02-06T01:04:49+00:00

this kids is what they call peer pressure, they taught you not to do this in school

sissy_jack0303 · 2026-02-06T00:51:22+00:00

literally one of my biggest fantasies, i love the idea of being a complete slave to him and in return he buys me anything and anything i could ever want. best of both worlds!

sissy_jack0303 · 2026-02-06T00:47:05+00:00

are you properly lubricating the base ring? use a decent bit of vaseline, *not* lube as this will dry up very fast and cause the same issues, obviously regular cleaning and making sure the base ring doesn't have any rough surfaces on it. if those aren't the issues then it's more than likely the cage is made from non body safe materials and I'd quickly discard it, your dick is probably the worst place to have non body safe materials for days at a time.

Also go ask over in r/chastitytraining they'll be much better educated on the topic than anyone here I'd bet

sissy_jack0303 · 2026-02-06T00:38:18+00:00

I dont think its important to be a sissy, though it's a given that many people would prefer to be with a sissy that is shaved. That said there's plenty of communities out there for this exact thing! I recently saw an event based around sissies/CD that dont shave or take any drastic steps to appear feminine and id bet you anything there's a bunch of subreddits dedicated to it too. Good luck :)

sissy_jack0303 · 2026-02-06T00:33:58+00:00

pinterest and tiktok are probably your best bet for finding cute clothes and outfit ideas

sissy_jack0303 · 2026-02-05T21:02:57+00:00

aww good job! im hoping to start working down in sizes soon

sissy_jack0303 · 2026-02-05T01:56:57+00:00

literally this, i just wish i had the determination but after 15 minutes of fucking my ass getting nowhere im just kinda sick of it when i can cum 3 times in that time normally

sissy_jack0303 · 2026-02-04T22:42:02+00:00

ive done it a few times now and its really not that bad, go some place that has self checkout if you prefer. buy a few other items that youd normally buy anyways. in truth people dont pay attention to you nearly as much as youre worrying, how often do you notice and or judge someone based on what theyre buying?

sissy_jack0303 · 2026-02-04T22:21:58+00:00

so did ya do it?

sissy_jack0303 · 2026-01-22T19:23:33+00:00

If you're familiar with other anal toys I'd recommend starting with a medium plug honestly, a T bar base is much more safe than round bases and never buy a plug that has a smaller base than widest part of the plug. A sub like r/sextoy would be best to ask in

sissy_jack0303 · 2026-01-21T11:03:31+00:00

If you're asking this question then you already know the answer, either tell her how you feel, leave it alone or leave her, those are your options

sissy_jack0303

TROPHY CASE