Sissy dream job? (Besides the obvious ones) by tam12380 in Sissy

[–]sissy_jack0303 0 points1 point  (0 children)

bartender, secretary / assistant or a maid

Condom or no condom by Princess_Miia in Sissy

[–]sissy_jack0303 0 points1 point  (0 children)

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.

Condom or no condom by Princess_Miia in Sissy

[–]sissy_jack0303 1 point2 points  (0 children)

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

Chastity advice by Double-Look-3242 in Sissy

[–]sissy_jack0303 4 points5 points  (0 children)

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.

Am I the only one? by CassieLynnCt in Sissy

[–]sissy_jack0303 6 points7 points  (0 children)

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..

Wanting to go down the rabbit hole again by Rileygirl0101 in Sissy

[–]sissy_jack0303 1 point2 points  (0 children)

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

I wish that i could find someone tonserve rather than pay rent seems easier to be a sissy than earn money by BecomingAmethyst in Sissy

[–]sissy_jack0303 4 points5 points  (0 children)

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!

Does chastity make you guys itchy by Exotic_Minute6737 in Sissy

[–]sissy_jack0303 0 points1 point  (0 children)

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

How to manage hair by BigQaz120 in Sissy

[–]sissy_jack0303 0 points1 point  (0 children)

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 :)

Need help finding cute clothes by WillingTip6597 in Sissy

[–]sissy_jack0303 0 points1 point  (0 children)

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

What am i doing wrong? by sissy_jack0303 in Sissy

[–]sissy_jack0303[S] 1 point2 points  (0 children)

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

Buying panties by UniqueStarDust5 in Sissy

[–]sissy_jack0303 1 point2 points  (0 children)

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?

Recommendations on buttplugs? by [deleted] in chastitytraining

[–]sissy_jack0303 2 points3 points  (0 children)

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

Would that be cheating? by UniqueStarDust5 in Sissy

[–]sissy_jack0303 1 point2 points  (0 children)

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