Friendzoned by a trans friend I’ve known since HS

This is a long one, but hopefully worth it. This is 100% true, barring shit I forgot, so ask me to clarify if you need it. :)

So for background, I (28m) had a crush on a tall, dorky underclassman twink in high school. After graduating, I didn’t see him again until I got on Grindr in my mid-20s. I hit him up and reconnected a little, a bit after… he disappeared, and I didn’t see him on Grindr again until he was mid-transition. And let me just say. Girl puberty hit her. Hard. In place of a flat twink chest were two C-cup breasts. She was just absolutely beautiful and despite being a gay sub, I was pretty whipped. I hit her up again, told her how pretty she looked, and eventually got her new snap. Nothing happened for a year after that, just being her friend, talking about men we’ve been with…etc. but then one day I invited her to go running with me. Something she was very much in favor of.

So the day comes and she cancels on me at the last minute to “help her dad with something”. However. About halfway through my run, she sends me a snap of her in bed with a stud. My heart started beating so fast I had to sit down by a lamp post and asked if she did that on purpose. She just replied “maybe 👀”. Boom. Seed planted.

I was so turned on and I didn’t even know why. Why was I, as a gay man, so turned on by my trans friend cancelling on me to get plowed? I started asking her to describe in great detail about her recent hookups and I’d get so hard hearing her describe the shredded twunks and hunks she’d been getting fucked by. Sometimes she’d even send me pics and I’d get a jealous aroused feeling in my chest seeing how much “more” these men were.

Eventually, she wasn’t having much luck getting a hookup one day so I offered her to come over to my place to play some video games and maybe fool around. Unlike last time, she actually made it to hang out. While we were on my bed, though, her phone was. Blowing. Up. So many dudes messaging her trying to hookup with her. She tried to apologize and put her phone away saying “no, I’m here for you” but I said it was okay and I didn’t mind if she replied to them.

Well, she took that permission and was texting them back pretty much the whole hangout. Until we decided to get going in the hookup side of things. Now, while I’m not small dick wise, my cock is super sensitive, so I had to stop her every couple of seconds from even touching it, or else I’d cum. me being a bottom who has never topped before, I was also in way over my head with her trying desperately to get me to “be the man,” but I just couldn’t muster it up. Plus, I was afraid of cumming the second I entered her ass.

She eventually settled into being the one “more in charge” and let me nurse on her tits for a while…but I could tell she was disappointed, and I was slightly embarrassed. I even apologized after saying, “I know it probably wasn’t her best hookup.”

And she said it was fine and not to worry.

Afterwards, I couldn’t stop thinking about all the guys that hit her up during and how she probably wished she was with an actual man that could pleasure her without cumming in 5 seconds lol. And get with someone she did.

 About a week later, she sent a pic of a dude that hit her up on Grindr, and he was absolutely shredded and apparently hung like a horse. At this point, I just had to say something. 

 I told her her “light cucking me was actually kinda hot” and asked if she was showing me all these men and talking about her hookups to try to get a rise out of me, and she said, “maybe…it’s hot seeing you get all worked up”. I then asked her if she’d be okay with me hitting up men on Grindr for her, and she said, “oh yeah, go for it.” 

  And I did. I’d find hot guys looking for trans women on Grindr and hype her up to them. I’d sometimes get a follow-up from her telling me all about the hookup I kinda set up for her. That’s where I am at this current moment in our friendship. She’s made no mention of wanting to hook up with me again, and honestly, I don’t blame her lol.

(Sorry if this doesn’t fit into this subreddit I tried researching what my feelings about this situation were and that led me here so)

TLDR: Had a crush on a hot boy in high school. Eventually, she transitioned and had a disappointing hookup with me. Now I find hot guys on Grindr for her, and she tells me all about it.