So with 2017 on the cusp of ending, I figure I buckle down and type out my stories from it, as it was a very critical year for my sissification and self discovery. Let me start from the beginning i suppose, it will be abbreviated to get to the point of the story. My first memories of cross dressing were very innocent, as many people who delve into this brand of lifestyle does. I was about 7, and I tried on a pair of my aunts satin, lavender panties. And it was absolutely exhilarating, as you could imagine. After making this discovery it became a childhood obsession. I loved finding new clothes to wear, that weren't for boys like me. It felt wrong from the get go, but that was definitely because of the type of house I grew up in. Follow the path of least resistance, and hope you don't have to make too much of a fuss. Needless to say, when my dad found the copious amount of bras, panties, and night gowns I had been hoarding, it made quite the fuss. Nothing too extreme ever happened, my folks chalked it up to childhood curiosity. Then I got my first laptop. A beaten up Toshiba that was passed down to me by my mom, who had recently gotten an upgrade. This single piece of shit computer would be the catalyst for my future sexual desires and tendencies. I found sites like "GetDare" and "The Experience Project" where people shared ideas and stories based around a concept that I previously believed I was alone in. I felt scared and welcomed all at the same time. My heart beat 1000 miles a minute and I could hardly contain my excitement. But I had to. All throughout middle school, and the majority of high school. I kept silent and progressed in my online exploration.

So that's my start, my background and foundation. It could easily be expanded to it's own chapter, but as for now I would like to share an experience that happened over the summer. It was late June and I was staying with my uncle in Dallas. I recently got a grindr, and was up late looking for some fun, when someone out of the blue messaged me asking for a meetup. I said yes i'm interested but at this time I was very high maintenance. I had no car with me, and my uncle couldn't know that I had left, or else i'd be doing a lot of explaining. When I got back. Thankfully, he (I use he loosely) was willing to work with me. He explains that he too is a sissy looking for some fun, and I explain my situation. To which he replies "It's okay, my friend can pick you up and drop you off when we are done" That's right, I was in for a threesome. Now may be a good time to point out that this would be my first meetup ever. We exchange social media's and I feel comfortable enough with meeting. A lot of risk involved, believe me my mind thought of all the worst possible outcomes. But I decided to swallow them and march outside at about 11 o' clock after my Uncle had gone to sleep, clad in skin tight black pj pants and a black tank top. Oh, and of course 5 inch black heels and an assless/crotchless baby doll underneath. I wanted to be discrete, but not sexless. As I hop into the friends truck, I am immediately aware who would be the top for the night. In the driver's seat beside me sits a ripped black man, whom I can only accurately describe as "Luke Cage esc." We made light conversation on the way to the apartment where the deed would be done, and halfway through the car ride he grabs my thigh, and I learned the meaning behind all those posts about "every girls' weakness". Once to the apartment I begin to have a bit of anxiety. I walk in confident enough, but my stress must have shone through because as soon as I sit down on the bed, Sasha (the "he" from earlier) begins to get therapeutic with me. She is wearing a school girl type outfit, and is about the same as my body type (see previous posts for reference). She tells me her interests, and i tell her mine, and she cues up some sissy hypno. The cut black man who picked me up ( i never go the name) has been waiting in the kitchen while me and Sasha were talking on her bed. After our chat, she leads me to her wardrobe and I strip out of my pj's revealing my lingerie. I give a twirl, and she slaps my ass on the way around. After that she approves, and walks me out to the bed, where now the real man in the house lays. I look at him, then at Sasha. The hypno is blaring throughout the dimly lit room, and it's clear what I am to do next. I look him in the eyes and crawl on top of him, grabbing is junk on my way to his lips. I kiss him, and he pushes me off playfully. I do a little pout and he curls his finger at me. "c'mere" Is all he says, and he leads me into the kitchen and shuts Sasha in her room. I'm his toy. He pushes on my shoulders and my knees buckle, forcing me to the floor. He takes his cock out. Now I have met up with about 10 people total, and he is still the biggest cock I have ever been face to face with. A lot of girls would have seen it as a pain, but a good, well trained sissy slut like me saw it as a blessing. I worship it. I lick it up and down and take the entire length of it down my throat. I had been training with dildos for years prior to this, so I knew what I was doing for sure. He pulls me up by my shoulder straps and pushes me back toward the bedroom. I spin around and brush my ass across his cock, tauntingly wagging it all the way to the bedroom door. Sasha sits watching on her bed and gets up to move. As she does this, the man pushes me hard onto the bed. Now this was a moment of ecstasy. And I don't mean that in just a sexual way. I mean my head literally exploded in dopamine, because sure. I was INCREDIBLY aroused. But more importantly I was wanted. Not as a man, but as a sissy. I was all dressed up, lipstick smeared, legs spread, and wanted. It was the first moment I was one hundred percent comfortable with my sexual preferences. All the backlash from my family, and the purges of my sissy stashes melted away as soon as the tip of his cock touched my smooth asshole. I took it all. I took in his dick and I took in the feeling of being me. Jenna. I was fucked for the first time by a real cock. Warm, beating, and clean. It was eye opening, empowering, and solidifying. Once he finished, my job wasn't done though. Now that the epiphanies of self discovery and acceptance are out of the way, it was time for me to serve Sasha. Turns out she was more dominant than I had gauged, and she ended up fucking me too. By the end of the night I had laughed, cried, squealed and moaned my way to a better me. So to anyone out there who sees this sub-reddit, or a tumblr post, or a caption, and thinks "Well thats fuckin weird", I just want you to know that it means a lot more than the surface will tell you. To anyone who says that it's just a phase, or it isn't for me; you very well could be right. It's not for everyone, but I encourage your exploration. To my family, who as I was growing up, stumbled across my internet history on the regular, I don't really want you to understand, just stay outta my stuff god damn it! Let a girl live! To my loving girlfriend and mistress, thank you for supporting me, doming me, and loving me for who I am, and what i'm all about And last, but not least, to this sub-reddit and others like it, thank you for being my first support system in this journey. You were a critical part in my growth, and I don't think I would have made it this far without you.

This concludes Chapter 1. If you would like to see anymore, all feedback is appreciated. -Jenna Annabelle