u/D3V1LzJester

My male borderlines cross dressing - for me.

He will wear skirt, tights, stockings, be sexy. Don’t reply if you aren’t comfortable with him dressing up. He will be called a female name. You will be pleasuring me, whilst I watch him be aroused over us - I like to watch him play with himself whilst dressed up.

We met at work, he wasn’t interested - I kept flirting and eventually we got sexual together. 2 years we’ve been going on as friends with benefits. He’s covered in tattoos, stoner, looks “hard” in a way. He’s got a satin fetish, PVC, latex.

We use satin penis sleeves, gloves, lingerie. We’ve gone shopping together out of our home area, for lingerie. He wears these sexy shiny undies/panties that show his bulge.

We were driving somewhere and I joked (but was serious) that he should wear stockings and dress up in a skirt for me and he laughed out loud.

Then he asked more about it when he had dropped me off and we had both gone home, he text me asking about it and it’s gone full blown from there and I am in love.

He’s now loving it, he wears tight shiny skirts, tights, stockings, he wants us matching in lingerie and I am falling in love HARD. How is this possible?

We want him to wear a wig (he’s bald). He loved it when I painted his toenails and did his make up. He loved kissing with lipstick on. He loves seeing me turned on even more and he said it makes him feel sexy when he can see I’m turned on.

What else can we explore please? I know I’m falling hard, he said “I think I love you” on text randomly whilst we were texting and I kind of ignored it as didn’t know what it meant. But aside from that, what else can we explore? He said he’s not ready for pegging or me having any sort of penis which I 100% understand. Please share any ideas you may have please! We’ve already chosen a name for “her” when he’s dressed up, he chose it himself. Thank you in advance for any ideas!