(This post has been deleted on r/sissy because my account wasn’t 15 days old but anyway there’s some update)

Hey there 👋 I recently made a post about my situation that I’ve been wearing chastity and wanted to hookup with a man. Well I didn’t want to use Grindr at first but, I did, I made a profile where I say I’m a crossdresser and wanted to do my first time with a man. Shortly after another crossdresser (don’t know if he define himself as a sissy tho) reached out to me, we chatted for a bit, and we decided to meet next monday. So now I’m waiting for the day, I will bring some of my girl clothing, but, anyone have an idea of how I should prepare? This guy seems really cool so I’m not scared, just a little stressed out 😅. For now I’ll just continue to chat with him and see what could happen ^^

And now there is the update to the post. So as I said we chatted more and when I asked him "what can I bring ? Female clothes ?) He said “Yeah you can bring that, I also have some things to try on you: Collar, Chastity, Sextoys”

As I said before I was a little bit stressed out, but now I’m even more stressed 🤣. I really want to meet him, and try all those things, I know I will love it, just need some tips to calm down, because I’m stressed and excited at the same time. (And I dont want to say no to try the things he mentioned because it will just be even better).

Thanks for reading me

You are viewing a single thread.
View all comments View context
2 points

He’s very understanding and seems like a chill dude, I feel like if there’s something I don’t like or don’t want to try he’ll be “Yeah ok I understand that”. I’m very happy that I found someone like him but still as it’ll be my first time, I’m nervous, but right now I don’t think about it too much, because I know it’ll be great ^^. I will post update tomorrow, hopefully it will be great, and if it does I’d be happy to meet him again in the future !

permalink
report
parent
reply

Sissy

!sissy@lemmynsfw.com

Create post

A safe place for sissies and those interested in sissy culture to talk about all things sissy!

18+ Only

c/sissy is a safe place for sissies and those curious about sissy culture to talk about all things sissy!

Ask questions or discuss about anything sissy related :)


Sister subs:

for sissy captions !sissycaptions@lemmynsfw.com

for sissy hypnos !sissyhypno@lemmynsfw.com

for sissies to share pictures of themselves !sissies@lemmynsfw.com

for sissies to make hookup requests !sissypersonals@lemmynsfw.com

for pictures of sissies in chastity !sissychastity@lemmynsfw.com


Rules:


1. 18+ only

2. Be kind

  • Please contribute to the community in a positive manner. Avoid using things like hate speech or bringing up politics unnecessarily

3. No blackmail or lost bets or anything that has any potential to be without consent.

4. No selling, spam, “upvote if” posts/comments of any kind.

  • All selling or spam type posts will be banned permanently.

5. No advertising unless mod approved. Read description for how to get approved.

  • Unless you get an advertisement approved, no advertising is allowed, including directing users to your profile

  • If you have something that you think is relevant to the sissy community (meaning support, help getting started, resources, etc.) message the mods before posting to request a mod approved advertisement. (Currently there is no modmail so just message one of the mods directly)

  • After reviewing the mods will approve or deny your request.

6. No personal information of any kind

7. No Task/DM Requests,

8. All interactions have to be in English

  • We want everyone to be able to read and take part in the conversations. So please write English!

Community stats

  • 27

    Monthly active users

  • 69

    Posts

  • 239

    Comments