Ok so I guess I'm kind of lucky that I got into this lifestyle fairly early. A lot of other guys like me start in like their 40s or something.

When I got into this relationship with my girlfriend, right away we knew it wasn't going to be a normal one. She's almost 5 years older than me for one. She's taller than I am, stronger, more muscular. Shortly after we started having sex we got into kinky shit. She wanted me to dress up as a girl. I was always thin and effeminate to begin with (even my voice is androgynous) so this wasn't a huge deal, I didn't have many issues doing this.

I still identify as male, but she's transformed me so that I might as well call myself a woman anyway. I went on hormones for a short amount of time to grow (small) breasts, I've done corsetry and lots of different exercises for a feminine shape. I keep my hair long, wear makeup and women's clothes, etc. Everyone I meet assumes I'm a woman and I don't mind that.

Now, getting back into the reason I mention all this. I'm still with her, she's still my mistress. She keeps me locked in a chastity cage and ever since she found out that my balls won't explode or anything if I don't cum she only lets me out to tease me. I eat her out sometimes multiple times per day, and sometimes she puts my cage in her pussy to tease me.

About a year ago we started something else though. She'll invite guys over to fuck me while she watches. Usually more than one at a time. They'll show up and visit with her while I serve them food and drinks dressed as a maid, then one of them will usually push me onto my knees or something and they'll start fucking me. Recently with the stipulation that I stay locked up, I'm only allowed to cum from being fucked in the ass, and if I'm about to cum I have to ask for permission from one of the guys, and they're not necessarily inclined to say yes.

I'm pretty sure she's basically a lesbian since she's never been interested in men (except me, but I mean she basically turned me into a woman anyway)

I'm going to be clear. I have absolutely no problems with my life. I love being with her and all of the things she does to me. I'm glad I didn't have to wait until I was in my 40s to figure out I enjoyed this kind of thing.