r/Sissy • u/emily_sissy07 • 16h ago
Need Help / Advice How do i encourage my gf to letting me play? NSFW
What do i even do?
A bit of story time incoming because i need a honest opinion and there is background needed.
So I (M19) have introduced my gf (F19) to chastity a couple months ago from now and after some honest chats she started getting more playful with it and a better keyholder overtime, i hope it is not going to stop like that. As currently it is locktober i’m ofc locked but she likes to play with my cock so i will probably get unlocked for her to play. I’m not really aroused by penetrative sex or getting blown although i enjoy it slightly I can’t cum like this, i can only cum while masturbating with my hand.
I was sharing with her lately about my state of mind and the fact that i like the whole crossdressing thing and also i feel great pleasure from playing with my ass. Basically through the chat about it (mainly the crossdressing thing because she thought that the ass thing was not a big deal) she was being very negatively affected bc she immediately started associating it with the fact that i want to be a woman. I don’t, i just like to crossdress bc i feel very submissive and pretty and i like to play with my ass bc it gives me straight pleasure and i also am bi but that’s another level of it that i’m not trying to introduce as i don’t think that she is ready to talk about it. She was clearly mad about it and encouraged me to throw out my outfits and toys. Even tho i tried to explain to her that i absolutely do not want to be a woman she still stayed worried about it.
So my question basically is, how do i encourage her to accept the things i do like to do sexually or maybe even introduce them to our mutual sex life? i really enjoy being in chastity with her, she even lately started teasing me by sitting on my cage and humping it or kissing it and sending me much more spicy pics than normally. I enjoy it but am definitely not even close to fulfill my sissy desires or feel pleasure from this side of me. What do i even do to get those things to be real?