Acquaintances hook up post transition

Brandnewbuddy

Literotica Guru
Joined
Apr 19, 2021
Posts
718
So this is LOOSELY based on something that’s going on in my life right now. the real life situation is a bit more complicated but inspired this story idea so I figured I’d bring that up as opposed to just saying I pulled it out of my ass.

Two people used to be coworkers but as time went on they went their seperate ways and only occasionally met up. They finally meet back up regularly with a new friend group right around the time one of them comes out as trans and starts transitioning (MTF). Cis lead and the friend group are very supportive, they quickly adapt to her new name and she takes a noticeable improvement in her mental health as well as starts exploring other parts of herself, the biggest one being her sexuality. Before transitioning she didn’t have much of a sex drive but now that she’s more comfortable with her body she actually has quite a high one and really likes kinky stuff. Everyone is still supportive but friend group is little unsure of how to react to her being a lot more sexually open.

So one day, our trans lead makes a comment on a group chat after everyone is chatting about a hottie they saw, essentially fishing for some compliments. Friend group is pretty slow on responding so cis lead, throwing caution tells her that he thinks she’s hot as fuck and extremely sexy. This breaks the ice but friend group still stick to safe compliments (she’s pretty or cute). Afterwards our leads meet up and the two of them start flirting, almost playing chicken with each other to see who backs down first but after a few drinks and the two of them coming clean about their shared kinks, they wind up making out and fucking like mad.

I think it could be fun. Instead of a character being trans as a surprise, the cis lead knows from the get go and thematically I think it could be interesting as they couldn’t really get close until after the trans lead comes out as they didn’t really know the real side of each other.
 
I agree. This sounds like a good idea for a touching story. So a few personal thoughts, and then the story.

I consider myself 99% straight. I say 99% because I am not attracted to men, in any way. Zero interest in a masculine form. But a feminine form is another story. I have seen some beautiful, feminine trans-women who make me wonder if, once I got those panties off, whether a cock is a deal breaker. I suspect it is not. But, if I knew the her before her transition, as a man, that would be. I wouldn't be able to see Martha, without remembering Martin.

Having said that, I would have our MMC, joining a social group with a Martha. He knows she's trans and is open minded and supportive. And to his surprise he finds her attractive and fun. They really hit it off. Shared interests, meshing personalities and sense of humor. In every way, a perfect pairing. Except for ... ya know.

So at this point, make the story about his transition. Him moving mentally and emotionally away from "but she has a cock" to "so she has a cock, big deal". The understanding that he is wildly attracted to her and that her sexy bits don't change that. I'd make Martha, understanding and patient, knowing this part of both of their journeys and doesn't fall apart when he waffles a bit. That first kiss for instance. That would be a real eye opener for any straight guy.

But as I said, this is just my viewpoint. I think the OP should definitely write their version and I know I would read it.
 
I will admit I’m coming at it from the perspective of being bi so genitals have never been a barrier to me. If a woman has a dick or a guy has a vagina that’s all right with me, my tongue and fingers are not picky

I could see a good story in the lead learning to pleasure his new girlfriend’s dick. Like I don’t think kissing or making out would be a big barrier (not to mention sometimes the estrogen hits like crazy. Knew someone who went from being 6’1 and built like a brick shithouse to 5’10, curvy and they’re now rocking a c cup) but I could see actual sex taking a bit of time or the two them come up with a compromise that doesn’t really satisfy either of them but they’re both worried about things not working out if they ask for what they want. Like they only do doggy style or positions where they don’t face each other and lead always keeps his hands above the waist or on her butt.

But as time goes on he starts pleasuring her, like stroking her while he’s pounding her ass, or watching her play with herself while they fuck, and eventually they try other positions where he can even feel her cock rub against him. Never even has to get to the point of her fucking him but I think like a double stroke where one of them strokes both of their cocks at once would be pretty hot.
 
I think it sounds like a brilliant idea and would love to read it. Are you listening Mrs MacKenzie?
I've got a few notes in my ideas file about something along these lines but nothing significant. I'll have a think and see if I can come up with something.
 
Back
Top