Sissy partner for first time?

[EBrand74]

Been fantasizing about being with a cd/trans for many years. I have dressed up privately and would love to share time with a like minded smooth sissy. I am a total virgin in this area, so must be understanding. Anyone else have this fantasy and it finally came true? How did it turn out?

[sissynancyboy]

Like many fantasies, some work out for us, some don't and some are best left as just that, fantasies. Many men like sleeping with sissy's and enjoy it, luckily for me. Most sissy's me included are sexually obsessed anyway and we often see sex with men as a way of demonstrating our femininity. Most sissy's are especially orally obsessed.
I have slept with other sissy's and it's been ok for me and hopefully it's been good for the sissy's I've slept with. But I'd much rather sleep with a man any day. I'm sure there are many sissy's out there that would enjoy pleasuring you, so give it a go. What's the worst that could happen, you might enjoy! One thing is for certain, you'll get a free blowjob

[Jizz_Jenny]

I ended up going home with two guys once, just curious to see how far I'd go.
I ended up jerking them off, inhaling the delicious scent of cock, but still too scared to taste.
One of the guys kept trying to finger my butthole. He certainly did not take no for an answer.

[johnnyys]

that's nice. Recently I found Cupid - Find Gay Singles site. I wasn’t sure what to expect at first, but it turned out great. I could connect with people near me effortlessly. The platform is straightforward, making it easy to arrange meetups. Everyone I’ve interacted with has been polite. I really enjoy using it for casual dating.

[Malate]

Not sure about sissy's but ladyboys I remember my first time. I was nervous and shy A little. Everything was just fine and you should indulge your fantasy. My first time was A working ladyboy so it was transactional. Was able to say what I wanted to try and what I was not interested in. Helped break the ice for me on this topic.


"love to share time with a like minded smooth sissy." My biggest ladyboy complaint in Asia is far to many of them are hairy dick and ass crack. Total turn off for me.