I have with Crossdressers. enjoyed it but one had hairy legs being a closeted dresser. Was a turn off for me. Need someone who is more Feminine.
Know someone who has Transitioned MTF. Would like to suck hers, and kiss, lick and caress her new Breasts. If she would give me the opportunity.
Yes I have. I am 71 years old now but often get hard thinking back 55 years or so to when I started out on my sexual journey. I had a friend of the same age and we used to mess about with each other in his bedroom. One time, he got dressed up in his sister's school uniform including her knickers. I ended up masturbating and shooting my load on the knickers. He pulled his prick out of the front of the knickers and I gave him a blow job. He came in my mouth. a week later we reversed roles. I have never done it since although I often fantasize about it while I masturbate.
Yes I have had plenty of cocks in my mouth. I love sucking cock, and yes I do swallow. I also like getting cum splashed on my face too.
I think it is the idea of being a little submissive on your knees sucking his cock, or letting him throat fuck you...yet at the same time I have the power to make him cum.