My Road So Far

Hi, I'm Jacquelyn! I've realized that I'm a sissy and I always have been around 2 years ago and those 2 years were quite the roller coaster.. So, the following will basically be my journey to now. Enjoy

The Beginning
As a kid, I can recall the desire to sneak into my moms room and try on her panties/bras just to see what it felt like. I would always think "Why couldn't I have just been born a girl so I could wear the things I want?". I would sometimes press my clitty inside of me in hopes that it would just stay there so I could be a real women. I would let my sisters dress me up in princess outfits and pretend like I hated it but actually loved it! I don't know what happened, but somewhere down the line I lost touch of that woman inside me and it didn't come back until around 2017.

2017-2018: Marriage
This was around the time I began having thoughts about how amazing it must be to be a woman. Maybe it was the girly things/clothes/panties/makeup around the house from my ex-wife? I'm not sure. But one thing let to another and I stumbled upon sissy hypnosis. It took control of my life. I would listen to it on the way to work, on break, in the bathroom at home, whenever my wife wasn't home, I couldn't stop. Eventually I began wearing my ex-wifes panties when she wasn't home. I LOVED IT. Eventually one night we were both drinking and she wanted to do my makeup. Of course I let her! After that I jokingly said "I might as well put a dress on!" She thought it'd be funny so she told me to do it. I put one of her dresses on and she jokingly said "Awhh what a pretty girl you are!" I can't tell you how good that made me feel even though she was teasing me and didn't know I loved it. A little longer goes by and I somehow started the conversation of me experimenting with guys just so I could know if I liked it or not. She said that she would support me if I wanted to try but I had to let her see other men too if I was going to be doing this. I said okay, but eventually my jealousy got the best of me and we stopped. A few nights later she fucked me with a dildo and was surprised how eager I was so she whispered to me "you're a little faggot aren't you? You love being fucked in the ass". After that I was obsessed. I started going on grindr trying to find someone to hook up with and try my first real cock and eventually I found someone. I snuck some of her lingerie to work and after work I met him at a motel. He even bought me a wig to wear! I began sucking his cock and being the paranoid person I am, thought my ex-wife would be suspicious if I came home late. So I stopped, got dressed, apologized, and left. A few months pass and my ex-wife is getting suspicious about how submissive I was getting. She didn't like it because she didn't like being dominant. So, things had to change. I went back to being the more dominant one in bed and had to put my fantasy away for a little while.

2019: Divorce
We moved to a new state (Florida) and started over. One day we started dabbling in bondage and I asked if I could be tied up one night. That was the moment my submissive nature came back. My urge to be feminine came right back. I began listening to hypnos again, wearing her lingerie, all in secret until one day she just couldn't be with me anymore. I changed too much and she didn't like who I was. We barely had sex because she hated being the dominant one, so eventually we get a divorce.

2019: I realize I'm a sissy
Once we got divorced I realized how much freedom I had. I could do whatever I wanted without the fear of being caught or stopped. She left a lot of her clothes at the apartment when she moved because she just didn't want them so I began wearing them. I wore her panties that went with some lingerie that she forgot and eventually began purchasing my own. I went all out. I bought probably around 20 pairs of panties, a few bras, wigs, makeup, dresses, lingerie, breast forms, heels, collars, buttplugs, dildos. and eventually, a chastity cage. This was a big one for me. I bought it and didn't know what to do because I had such little control over myself with how horny I was from all these new exciting things I was doing. So I found myself a local Mistress (I now realize she wasn't the best Mistress). She took only took 1 of the 2 keys from me and would unlock me when she came to see me and would make me pleasure her dressed in full girl mode. (Fuck, oral, kiss her feet, etc.). She'd then leave me with one key and me having little control would end up unlocking myself a couple days later. Eventually that ended because of things going on in her life. I began listening to Bambi Sleep and let me tell you, it works. I was skeptical but eventually I began doing things differently. I needed cock to survive. I began fucking myself ever chance I had, practicing sucking cock on m dildo constantly, until I started going back onto grindr and fetlife. I found a couple that wanted to sleep with a sissy so I reluctantly went to see them. I got there and immediately began sucking his cock while she watched. They brought me to their bed and made me suck his cock more while she fucked me with a dildo. Then they moved me up and made me take his cock in my ass. This was the first cock I ever had inside me and it was incredible. I only wish he came inside me but he was wearing a condom. Eventually I left and the drive home was an emotional roller coaster. I called my friend (who is an online findomme who I know in real life so I thought she'd understand) and confessed what I've been doing. She was so supportive. She even taught me how to apply my makeup! Now that I had my first real cock, I was even more addicted. I slept with ever guy I could find (Not every, but the hottest one that would message me that day hehe). This kept up until around February 2020 when I started talking to an old friend I had liked a long time ago. Long story short, I stopped dressing, purged all my sissy things, and moved back home where she was in New York.

2020: New York
I was living with my grandparents at this time around August/September. My first few months there I didn't think of any of my sissy thoughts up until my heart was broken. The girl I moved there for decided she didn't want a relationship. So I went back to my old habits. I bought all of my things back. Each time I went back to my sissy ways, the urges would get stronger. So, this time, I found an online dom who forced me to send pictures throughout the day to him to prove I was wearing my panties and chastity. He even had me melt my keys into wax and send a picture everyday to prove I did not tamper with them. This went on for a couple months until I found a Mistress who was even more sadistic. She found out who I was in real life and in a way, began blackmailing me to enforce my feminization and didn't make it about money as she did not ask for anything (Kind of). It was incredible at first. At this point, I couldn't say no to anything she said. She forced me to listen to Bambi Sleep files before bed and as soon as I woke up. She forced me to take over the counter MtF hormones (Puereria Mirifica, DHT Blocker, Estrogen Boosters, etc) to make me more feminine and they actually worked. My breasts began to bud, my skin was smoother, and my libido went down (More on this later). She had me wear a butt plug at all times (Of course keeping it sanitary and washing it often, but as soon as I cleaned it, it went right back in). She made me bury my keys in a park over the winter so I wouldn't be able to get them back for months until the snow had melted. Eventually things started to get almost too real for me. She forced me to make an onlyfans and myfreecams account and forced me to live cam every night and upload a specific amount of photos/videos a day. These accounts were linked to her bank account but other than that, she did not request money from me. I didn't mind the fact that she had complete control, but eventually it got tiring. It became a chore after a while and the fear of missing a day terrified me because of how much power she had over me. She eventually began enforcing weekly hookups. I was required to have sex with multiple men a week so I had more content/more interesting content for my onlyfans. This was especially difficult because men are very camera shy which I completely respected. She understood this but still required me to take before and after photos of myself when I would have sex with these men. She eventually brought up the idea of escorting. She wanted to get me so feminine to the point of no return and had plans for me to move to California away from all friends and family to become a full time escort. She was going to make me begin real hormones that would be stronger and more effective. She would allow me to keep my earnings so I could survive and wouldn't be struggling but was going to enforce a fee almost as if she was going to be a manager. I realized she was pampering me and trying to perfect my feminine image to become her whore and she would become my pimp. Everything was getting so real and I felt myself turning into a prostitute it seemed. She even began to arrange hookups for me sometimes that I wasn't allowed to say no to. The moment I realized I may be in trouble was the moment my breasts began to bud. The realization that I was permanently changing my body almost terrified me and made me feel as though I might not have been ready. Thoughts of "What is my family going to think? My friends? What if I end up stopping this again and want a real job? How would they react to seeing someone with breasts everyday?" I thought "What if I go so deep that I have no choice but to dress feminine because dressing as a man would look weird?" This all terrified me and it scared me away. Eventually I told her how I was feeling and she was completely understanding. She let me go and told me she was never going to actually blackmail me, she just thought it was exciting to think about. At this point I'm stuck I purge my things but Im still stuck in the chastity cage until the snow melts so I wait. I get my keys, I take it off, and I cried. I didn't know what I was doing.

Now
I left my hometown and moved back to Florida to get my old job back. My body (Breasts) went back to normal for the most part. They weren't tender from the growth, my nipples went back to a normal size, but the actual breasts are still about the same as when I left which is a not so quite A Cup. I'm currently living with friends but have had the urges continue to emerge. Never actually acting on these urges, but they're there. I meet a girl who I really like and those urges go away but eventually just as before, the relationship ends. She wasn't ready for a relationship because of multiple factors that didn't involve me, mainly family and health. Needless to say, I was a bit heart broken. I still am in fact and the thoughts and urges are back and stronger than ever. I'm moving out of my friends in a couple weeks and all I can do is think of how much freedom I'll have again and how strong this is going to be. It'll be my first time living by myself since 2019 and I'll be free to be the biggest sissy ever. I'll get over my fear of rejection from friends and family and I'll go see a therapist to start my transition. I'll get my feminine items back, and who knows, maybe this will be the actual moment I'll become my true self.

 

This was going to become my bio but decided its way too long lol