Once I turned 18 I hopped on Grindr and started meeting up with older dudes (I have a huge daddy kink lol) I met this guy 50s good shape, great cock. Our first couple meet ups were pretty normal but the more we went he started giving me kinkier and kinkier things to do mostly revolving around wearing women’s clothes. First it was just thongs and sometimes a bra, stuff like that.
Anyway after a few more hookups he texted me and asked if I’d be open to a really special idea he had, of course I wanted to hear what it was. He sent me a picture of a wedding dress, turns out it was his ex wife’s (idk how he got it) he asked if I’d be willing to roleplay his wedding night where he and his wife had the best sex of their relationship. I wasn’t sure at first but came around.
I went over to his house put the dress on and waited in the living room while he set up the bedroom. Finally he came out and kissed me before taking my hand and leading me to the room. The lights were dim, some soft r and b was playing and some candles were lit, he called me by his wife’s name as we made out. He pushed me onto the bed and grinded on top of me before having me give him head. Still with the dress on he lifted the bottom up and slid his cock in and passionately fucked me while we made out.
It was kinda weird but looking back it was so hot, we begun role playing a lot of other wild stuff after that. I’d love to talk about if anyone is interested
Source: reddit.com/r/gonewildstories/comments/p53qoo/mm_my_kinkiest_grindr_experience_ever