Possibly a great beginning

I started chatting with a guy on Grindr today that is closer to my house than I realized. Not close enough to walk to but definitely close enough for a short drive.

Somehow he's been playful and forward without being pushy and demanding. He knows I'm looking for someone to take a little time to get comfortable with to start exploring my sissy side and I get the impression he knows if he plays his cards right he'll bring out the little cock slut in me for him.

For the first time I have been thinking this might be the guy that I really want to show off for and learn how to please and not just a guy in my head during fantasies.

He shared a couple pictures of his cock and while it looks a little intimidating it definitely looks very hot. Definitely above average, thick enough to not be too worried about, and a very defined head that I love.

We'll see what ends up happening between us but I'm actually thinking, for the first time, how much fun it would be to show off myself in some sexy lingerie for him and want to learn to please him.

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u/sarcasticallysarah69 — 8 days ago
▲ 9 r/u_sarcasticallysarah69+3 crossposts

Would you like to have a friend like me....

Would you like to have a friend like me knowing I'm wearing something like this for you under my regular clothes whenever we hang out?

u/sarcasticallysarah69 — 3 months ago
▲ 4 r/TransMarylandDMV+1 crossposts

T4M Sissy/CD in HARCO

I'm looking for someone, preferably in HARCO, that is interested in exploring having a sissy friend. Maybe someone that wants to go have a drink somewhere or hangout sometime and can appreciate knowing I'm wearing something sexy underneath my regular clothes. Maybe you'd enjoy pushing me to show you what I'm wearing when no one is watching or see if I can make giving me a ride home worth your time.

If you are married I would prefer everyone is on the same page and not keeping secrets from each other. Drama free just makes things better.

u/sarcasticallysarah69 — 3 months ago