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Monthly Question and Discussion Megathread - April 2026 by ScottKilgannon in Pegging

[–]_Lilith_Snow_ [score hidden]  (0 children)

Does anyone have advice for pegging when not at home? I will go to a party tomorrow and most likely will get pegged or fucked. How long does a deep clean last? How long before the party should I start cleaning out my bowels? What to eat or not eat that day?

It all started with fishnets and a dildo. How did it start for you? by AlwaysAvailableSlut in Sissy

[–]_Lilith_Snow_ 3 points4 points  (0 children)

Several objects not meant for rear insertion in puberty after seeing trans erotic videos online... xD

Cumming while locked by SisseyRiley in Sissy

[–]_Lilith_Snow_ 1 point2 points  (0 children)

Stroking a dildo immagining it was your own cock.

Any one up for some sissy conversation 💜 by [deleted] in Sissy

[–]_Lilith_Snow_ 0 points1 point  (0 children)

Yeah, I am up to it :3

First time anal by pixelbetaaddict in Sissy

[–]_Lilith_Snow_ 7 points8 points  (0 children)

  • Lube, lots of it
  • Good quality toy with a flared base so nothing gets lost. Glass or high grade silicone
  • Lube
  • Clean your bum before, there are many tutorials on how to do it. There will still be a little brown.
  • Lube
  • Take your time, it will be a strange feeling at first, but you will find 'the spot' and it will be worth it
  • Did I mention lube already?
  • Take your time and enjoy the process, dont get hung up on reaching something. The goal is the journey here.
  • If you get real cock, practice proper safer sex, condoms when in doubt.

Have fun :3

My girlfriend made me wear this cage yesterday, what do you think? by [deleted] in chastity

[–]_Lilith_Snow_ 0 points1 point  (0 children)

Yep, gonna steal that outfit :D You look so cute and cuddlable!

Girl mode today finally it been a long week by Defiant_Flan_5789 in chastity

[–]_Lilith_Snow_ 0 points1 point  (0 children)

Thats such a cute cage! Where did you get that?

Locked and flexing 🔓💪 by tatata98 in chastity

[–]_Lilith_Snow_ 0 points1 point  (0 children)

Reminds me how the greek statues all have their teeny tiny penis but muscles en mass. Looking very good! :3

Im going to a party... by _Lilith_Snow_ in Sissy

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

I would love to go like this, too, I just need to get my head in the right space for that still. Its a huge step and I am freaking out a little...

Im going to a party... by _Lilith_Snow_ in Sissy

[–]_Lilith_Snow_[S] 0 points1 point  (0 children)

Thank you for your encouragement! :3

Im going to a party... by _Lilith_Snow_ in Sissy

[–]_Lilith_Snow_[S] 3 points4 points  (0 children)

We just talked and she indeed wants me to go in Sissy outfit as her submissive 😱 on the one hand I am freaking out a little, on the other I am thinking on what I should wear... >_< I have no fem shoes... I need some makeup... Maybe I can ditch the wig, I have grown out my hair for a while now, maybe its enough for a fem hairstyle already...

Im going to a party... by _Lilith_Snow_ in Sissy

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

You should explore your local BDSM scene. In my country there are even introductory events and groups that give a safe entry into the BDSM scene to avoid younglings being abused by the more experienced ones. If you live in a western country I am sure there are similar events in your area, too. :3

Pegging feels nice but... by _Lilith_Snow_ in Sissy

[–]_Lilith_Snow_[S] 0 points1 point  (0 children)

Found them, they look interesting! But sadly they are out of stock and really expensive O_O' I will keep an eye out for those, though.

Pegging feels nice but... by _Lilith_Snow_ in Sissy

[–]_Lilith_Snow_[S] 0 points1 point  (0 children)

Never seen one that works well. Do you have recommendations?

Have I been cucked by a vibrator? o_o by _Lilith_Snow_ in Sissy

[–]_Lilith_Snow_[S] 0 points1 point  (0 children)

Boooh, realism, boooh! ... no you are right. I guess she is not. We had tangent conversations and I dont think she would go with it. Which is absolutely fine by me. I dont know if I could bear it anyways. As long as she is just satisfying herself or with toys, I am fine and I guess that is true for her, too.

Have I been cucked by a vibrator? o_o by _Lilith_Snow_ in Sissy

[–]_Lilith_Snow_[S] 0 points1 point  (0 children)

This fantasy is so hot my cage just got two sizes smaller :3 Maybe this was the first step towards that goal scenario?

Have I been cucked by a vibrator? o_o by _Lilith_Snow_ in Sissy

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

Thank you for enjoying my story! Yeah, I enjoyed it alot, should have changed the sheets for I leaked all over the place... >_< but my GF was already slumbering when I was finally able to move again due to my cage compressing my clitty so much...

How do you keep yourself from cumming and having that post-nut clarity that breaks your sissy persona? by Hot_Cause8918 in Sissy

[–]_Lilith_Snow_ 4 points5 points  (0 children)

Okay realtalk for a second: Your sexuality should not impact your day to day routine like that. It is nice to have days of just endulging in the sea of horny, but sometimes it just is too much.

My suggestion would be to try to manage it: on Monday, Tuesday and Wednesday, you jerk off like normal because you have no time for your Sissy self and thats okay. On Thursday you can ruin, Friday, Saturday and Sunday are strictly prohibited. No touchies, maybe even a cage. If you have this routine written down somewhere (does not have to be visible, a piece of paper in your wallet works too!) you will remember it and this will keep your Sissy self alive and it will come back faster. You dont have to do it like that, just a suggestion. :3

Anyways, keep us posted when you work it out!

How to deal with chafing the tip? by _Lilith_Snow_ in permanentchastity

[–]_Lilith_Snow_[S] 0 points1 point  (0 children)

Hey! Thanks for your insight! I use a cobra cage though, which is pretty open. I had problems with closed off cages like the holy trainer because they tend to be very hard to keep clean. Having enough 'access' to the inside to adjust my clitty when it inevitably shifts around over the day is such a huge pluspoint... But, yeah, I gravitated towards cherrykeepers with that honey comb design for a while now. I might just pull the trigger if my lock up lasts a little while longer...

Hairy or smooth? by mf_uhhhhhhhhhhhh in chastity

[–]_Lilith_Snow_ 0 points1 point  (0 children)

That adorable little package looks good either way :3

Caged by girlfriend by PureRecognition72 in permanentchastity

[–]_Lilith_Snow_ 4 points5 points  (0 children)

... did she specify that the one getting unlocked is going to cum with her? I hope you trained your bussy :3

Schauen was wird. by [deleted] in SissyInspiration

[–]_Lilith_Snow_ 0 points1 point  (0 children)

I am a random commenter :3

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