I was in my early 20s and I was prone to long dry streaks because women my age at the time in NYC expect you to have an apartment and car despite how expensive both of those are in nyc. So I was would browse Craigslist personals…wouldn’t get any replies on w4m but some posts on t4m were quite intriguing. T4m was my go to for stroking off to how hot the posts sounded or if I had the balls to meet irl which I rarely did because of my fear of STDs and getting robbed as I often saw people post horror stories.
So I saw a post close to my school about a trans woman at a gloryhole but wouldn’t reveal their face because of fears which I was ok with because (1. I was so fucking horny, 2.it worked perfectly with my schedule to blow a load early in the morning so I wouldn’t be pressed for time, 3. I wanted them to feel comfortable and safe as I did). I replied with pics of my cock and we exchanged numbers and they sent their address. I was extremely nervous as I often am entering apartment building for cl meetups.