I am a 39 year old professional. I’m unmarried (by choice) and have no kids. I’ve been very successful in my career. I don’t say that to brag, only to point out that money isn’t a big concern for me.
About two years ago, I’m out with some friends at a bar when I see this smoking hot girl. I went and chatted her up. “Jenny” (not her real name) was younger (24) and clearly attracted to me. We wound up making out for a while in an Uber, during which she was also stroking my cock through my pants. We made plans to hang out a few nights later, which ended with her giving me a brain-melting blowjob. Honestly, best I’d ever had.
The next time we hung out, I was fully expecting to fuck her. And, sure enough, we were going down that path at my place, when she stopped and, looking sorta embarrassed, gave me the “I’m not like most other girls…” talk. And dropped the bomb that this girl… had a dick.
Now, a thing you should understand here is that Jenny was fucking hot. You wouldn’t have picked her as a guy in a million years. Her “breasts” were pretty small, but not abnormally so. She had a thick, round ass that was just begging to be spanked. So this whole thing was a shock. But… Jenny was cool, extremely feminine, I was very attracted to her, and, uh, I was horny. So I went with it. I ended up fucking her soon thereafter.
And it was amazing.
From then on, things got physical real fast. Jenny did not like me touching her “clit” (dick). Often she would, but she didn’t ejaculate very much even when she came. She loved to service me, though. Her “pussy” felt incredible. She gave the best blowjobs I’ve ever had. She loved to act super slutty for me – cooking for me in just a skimpy little silk robe, happy to drop to her knees to drain my balls at any time. It was like having a “normal” girlfriend, except she was always super horny and no shark week.
Jenny had been on hormones for several years but hadn’t had any surgery because she couldn’t afford it. She worked as an assistant at some art gallery (lived 100% as a girl), made very little money, lived with a bunch of roommates and spent tons of her disposable income on hormone therapy.
After two or three months, Jenny started sleeping over at my place a few nights a week. My place was *much* nicer than hers, as well as private. I also started giving her some money. It wasn’t much, just a few hundred bucks a week, but it made a huge difference in her life. She upgraded her cosmetics, nails, wardrobe. Got some pretty amazing lingerie. It all made her even hotter. And I didn’t mind being her sugar daddy one bit. We both thought it was actually sorta hot.
So eventually, Jenny was accepted into grad school across the country. It sucked, but we agreed she had to go – it was a great opportunity. She was leaving that summer, so for Christmas, I got her a present: breast augmentation surgery. She’d always wanted it, but it cost way more money (nearly $10k, all-in) than she’d ever have. I called around to a bunch of regional clinics, talked to some doctors, figured out what she’d need, set up what I could. When I told her about it, she actually broke down into tears, she was so happy.
After the surgery, it took about 6 weeks before she was ready to show off to me. 8 before she’d let me play with them. And I did. She got a really spectacular pair of C cups, and they made her 1,000% hotter. She got a whole new wardrobe to show them off, and I picked out lingerie for her to wear. They bounced beautifully when I fucked her. She loved titty fucking me now. She’d send me nudes and teasing videos when I traveled.
Then she left for grad school, where she’s had a great time. I’m happy for her. She still sends me nudes every now and then, and when she comes back to town occasionally, she sometimes sleeps at my place so she can get her fill of my cock.
Source: reddit.com/r/gonewildstories/comments/g00x5l/i_dated_this_girl_discovered_she_was_trans_went