After my first high school best friend dropped me, I didn't have any other friendships like that until adulthood. A couple got close, but not that close, and they were hopelessly straight at the time. In that pre-Internet age, I made do with industrial doses of magazines, videotapes, and solitary masturbation, including an increasing number of toys. I've had jobs for pocket money since I was 12, and as soon as I hit 18, a good chunk of that income went to the local adult bookstore for a slew of dildos, buttplugs, dolls, and more obscure implements, as well as a continued tide of printed porn.

 

After a college misfire, I ended up in the DADT-era Navy for a while, in much the same situation. However, in the places I was stationed, the places I went to get porn were places that carried more gay/trans material than I was used to, which I was fascinated by. I ended up going through a lot of relatively low-quality glossies of blondes with breast augmentation scars and small penises, etc., and older, badly written gay erotic novels, some of which had identical plots with the settings and names changed, and I do mean identical. Worked anyway, though.They also continued to have toys, and I continued to use them, albeit very carefully. By that time something resembling a non-straight sexual identity was coalescing, and I started my first furtive visits to gay bars, which didn't amount to anything at the time because I was too nervous.

 

At a peak of sexual frustration, met a pretty and very playful non-op black BBW MtF TS on hormones with a dick as big as mine; I was cute, young, fit, and desperately horny and she was cruising. The big reveal changed my life. I asked her to teach me what she knew! We hit it off, I topped for the first time (and bottomed as well!), and we had a grand old time all night, followed by a couple of months of dating. Then I got deployed to the Middle East (Desert Storm, dating myself here) and had to leave. Never saw that gurl again, but I still have a photo.