u/Significant-Dog-7636

So.... ive only done some light crossdressing, heels, stockings, panties, and a few blouses, but it has always been alone and in private. There's been a few times when I have been in a sexual scenario with cis women where I would wear their panties and top them, but thats as far as it went.

I have been with a few trans "providers" and have bottomed for them, and it was always a great time. I discovered i have a mild degradation kink, and have been curious if that would be expanded on if I were to bottom while dressed. I dont want it to seem like a fetish, amd theres not really a good way for me to explain it, but I would like to live out a fantasy where I am topped while dressed as the opposite sex.

I am in no way passable, and have never been with another male, so if I were to do it, I think it will be with another trans provider. However, I am not entirely sure how to go about asking for such a request. Is it something I am straight forward with, or something that is best eased into?

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Ive been meeting with trans escorts since I was 18, the first time I met up with one, she was very polite and I was clearly unsure about what I wanted. At that point in my life, I had only been sexually active with cis women, but I was curious after discovering trans porn. So meeting up the first time, I was nervous, but luckily she took charge and took me through a little of everything. She let me suck her cock and get comfortable around her, and then gave me a massage. About 25 minutes of a massage, she climbed on my back and slid her cock into me. That was thr first time ive ever had anyone other than me insert something there. She took her time and let me get used to the feeling, then she started going faster and harder. All in all, it was an amazing experience for my first time. I visited her several times throughout the years and became a sort of regular of hers. Once or twice she filmed our sessions for her onlyfans, and that was a big excitement for me.

I travel a lot for work, so I am always in a new city, and o occasionally look through the classifieds for another trans escort. Ive hooked up with several, but it was never as good as it was with my first.

Last week, after not bottoming or seeing an escort for 3 years, I decided to browse the classifieds, and I found a girl that checked all the boxes.

It was a quick session and right to the point, but she was fun and easy to talk to.

All in all, it was a great experience, but it didnt come close to my first time