I saw someone begin a “diary” of their experiences as a sissy on here recently and it inspired me to give it a shot myself. The following will be true stories from my past starting from the first time I ever hooked up with a Tranny / Cross dresser / Sissy.
First things first, I consider myself to be a straight male; despite having had sex with all of the above. I am not attracted to men, rather the idea of complete submission; I see Trans, CD’s, and Sissies as a fetish, an object if you will (I suppose if it makes you, the reader more comfortable we can say I am bi). If this offends you, please do not read any further.
I have always been an avid porn watcher for as long as I can remember; as my love for porn grew so did my sexual spectrum. I found myself coming across new genres and fetishes that I never imagined I would be turned on by; I stumbled across a Trans pornstar named “Kimber James” and I couldn’t believe my eyes. She looked like every other big tit blonde bimbo I had seen before except she had a cock between her legs.
I was confused and borderline disgusted but slightly aroused; something convinced me to dig deeper. This led me to the sexual underworld of cross dressers, sissies, fembois, and so on. This was never my “go to” when I’d sit down and masturbate but every now and again, it would certainly get me going.
A few years later I ended up leaving my relatively small city and moved to Los Angeles; upon arriving I downloaded a dating app to meet women in the area and quickly realized there were far more CD’s and tranny’s in LA than there were where I was from. I only partially knew one trans person in my previous city and while I would flirt with her at parties, I never had any intention of actually hooking up with her or going any further.
Only a few weeks after living in LA I met a girl and that quickly turned into my first very serious, yearlong relationship. After a year, my girlfriend had cheated on me and our relationship went up in flames; a few months later we started dating again but we weren’t “officially” together again and we could both tell that it didn’t feel right. I stayed on dating apps and kept my options open as I knew my ex was doing the same; it was during this time that I came across a semi-instagram famous tranny (she had about 100 thousand followers at the time).
Out of respect for her, I’ll call her “L.”
Truthfully when I saw her online profile I wasn’t even aware that she was trans; she was a very tiny girl and had a gorgeous face. I shot her a text and figured what the hell, at the least I’ll just flirt around a bit; again with no intention of ever meeting up with her in real life. She turned out to be a genuinely interesting person and her social status piqued my interest to say the least; we chatted back and forth for a couple weeks and she would invite me to grab a bite to eat every now and again and I’d find an excuse not to meet up with her.
Besides, that wasn’t exactly what I was looking for. I didn’t want to date a tranny; I didn’t want to date anyone except my ex, even though that wasn’t working out. But, L was very persuasive; with her I found out just how flattering transgirls were when it came to men. I’m very fit and I work out constantly, so naturally I post gym selfies on social media; L would always message me to compliment me on my body and even go as far as telling me she wanted me to fuck her. Admittedly this was a bit uncomfortable at first.
I remember the night I agreed to finally meet her very vividly; it was December 23rd and I was alone while my ex (who I was still dating at the time) was celebrating Christmas with her family. Needless to say, when I got the invite from L to come over, I took it a bit more seriously than I ever had before.