I originally posted this on r/TStories, thought I’d share it here too, who knows some might appreciate what I have to say.
Before I start I just want to make it clear that I don’t mean to show any disrespect to anyone from the trans community. I tagged this post as “fantasy” because that is just what it is, there’s no hidden meaning behind it and it does not reflect any hateful view or attitude that I have towards the trans community. If any part of my post comes off as offensive, it wasn’t my intention and you can DM me on which areas of my post should be corrected.
《MY FANTASY》
It’s been a long-time fantasy of mine to pick up one or two random ladyboy hookers (those who identify themselves as proper females and went through physical changes to look the part but have chosen to keep their male genitalias) off the street, maybe without making any prior arrangements for their services but just showing up to them unannounced, bring them to a nearby back alley and talk them into doing an impromptu “transaction”. The more “trashy” they are (heavy makeup, uncut cock, long thick pubes), the better for my “mission”.
If they agreed to my sudden offer, I’ll go straight into sucking off one of the two ladyboys with extreme force while the other watches. I have just one objective for my mission: to make her ejaculate prematurely. I’ll perform all the tricks I know of to escalate the intensity of pleasure on her until she reaches her tipping point, and I would refuse to let up when she needs a momentary “break” to stop herself from cumming at such a short time. My mission is a success if I manage to make her cock go from soft to cumming anywhere lesser than 3 minutes, otherwise I’ll switch from oral sex to an aggressive handjob while simultaneously pleasuring her in an attempt to milk her cock dry within the next 3 minutes. If during that 3+3 minutes she fails to ejaculate, I’ll proceed to hold up my end of the deal, pay her the agreed amount and politely send her off. I’ll then turn towards the other ladyboy hooker who’s been watching us closely and carry out the same set of actions too. So best case scenario is me successfully finishing two ladyboys in under 3 or 6 minutes each, the lesser desired scenario is for both ladyboys to walk away without cumming (and they’ll have to finish off without me since it’s the deal) but I will be coming by some time later to try my luck again to make them blow their load prematurely. End of the day, it’s nothing more than just a harmless game and they’re still getting rightfully paid either way.
I find that I’m attracted to ladyboys/transwomen who ejaculate quickly, and I enjoy the satisfaction from watching or making it happen because to me it means they are vulnerable under intense pleasure (I’m not saying they are weak or helpless, don’t get me wrong) and they should be treated with gentle care and deserve to be loved tenderly. She may feel flustered, embarrassed or insecure about herself for cumming prematurely, but I’ll assure her that everything is okay and it doesn’t bother me at all, in fact she’s now someone special to me because of it.
I hope my fantasy can one day become a reality and I hope it’ll happen somewhere in Asia. And when it starts to finally happen, I might come across my favourite one among them and maybe even settle with her as my lover.
Source: reddit.com/r/sexystories/comments/i70ajf/waiting_for_my_dream_to_finally_come_true