" ... But I'm Also Ashley " - (Ch1 of My Steamy Autobiography) (Patreon)

So, I’ve been asked my story so often over the years, I figured instead of continuing to piece meal it together via tweets or Tumblr posts, I would write it out, in full, in the same way that I would write any of my other fiction pieces… the catch of course is: this time, it isn’t fiction.

You’ll notice a lot of similarities to my other fiction stories from the past but, I mean. That makes sense — where do you think a lot of those ideas came from? ;) And just like my other stories, yes, it gets pretty erotic. If you think this is gonna just be some boring autobiography - don’t worry, I’m writing this like I would write any of my erotic stories - the build up and tension is worth it for the release.

So strap in, and enjoy. Hopefully this will be as much of a ride for you, as it was for me.

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"... But I'm Also Ashley." - Chapter 1

Admittedly, gender bending always fascinated me growing up. It wasn’t something that was on my mind all the time, but it definitely peaked my interest whenever I ran across it. The long outdated idea of “OMG, that attractive woman was actually a man?” often seen in media always caught my attention and always got me thinking: “Was that actually possible? Is that some kind of film trick?”

Often, yeah, it was - bring in a female actress for the setup and then ultimately the butt of some joke or the punchline came back around to: “Haha - isn’t it gross that the main character (and you) thought that the attractive woman was actually a DUDE? How silly and gross.”

Thankfully, a lot (but not nearly enough) has changed since then, and my fascination when I ran across this kind of material as a kid was something I also used to shame myself about in my own head — “WHY would you find that interesting? WHAT about it even interests you? Can’t you see it’s silly and gross? That’s what they say it should be… what would even interest you outside of that anyway?”

To be honest, I pretty much forgot about these kinds of feelings as I grew up - becoming a teenager changes a lot. And I changed a lot. I grew up fast — too fast. So fast it gave me a hormonal imbalance, and a slight case of gynecomastia (excessive breast growth for a male) The funniest thing is, it’s not until years later, in hindsight, that I even realize how much that should have concerned me as a kid. As far as the doctors told me, it was a normal thing to happen, and it was never treated as silly, or gross like the media told me gender bending was - so why would I even attach it to any level of the subject that fascinated me or made me feel any shame about how “femme” that was. It quickly became unencumbered from my mind. Especially once I picked up football as a hobby — and was good at it. Nobody questions your masculinity when you’re good at a sport, and nobody makes fun of your body when you’re a foot taller than everyone in your early teens and can catch a ball.

Besides - I had other things to worry about than what a hormonal imbalance might mean. One of them being - girls. Hot girls everywhere, and here I was, tall for my age, built pretty well, and with features I was often reminded did a pretty decent job of reeling them in — features I never connected to being softer and more androgynous due to that imbalance. All I knew was the girls called me cute, and I was all about it.

Everything about a woman I found hot - the curves and all those feminine assets were especially appealing to me in tight clothing, or even better - sexy lingerie. Nudity is great, but hidden curves can be just as hot, if not more so. And I couldn’t get enough of it. I had no direction in college, so what was there really to do outside of that but experience the rest o f”college life” to it’s full potential?

Now, I’m not trying to do some masculine bro douchebag bragging here (how can I when I literally look the way I do now - seems silly doesn’t it?) but I definitely got around in college. I became fairly well known as the dude you invite to your place to make drinks for your party (it’s no wonder I became a bartender later) and that meant a lot of chatting up women without having to break the ice. The game was easy: Make decent drinks, get a number, get a date later that week. Word of advice, never hook up with someone at a party, you’re all gonna have a bad time. As someone who weirdly didn’t like drinking much, and also speaking from experience (from the view behind a makeshift bar table), there was way too much vomit involved out there.

A compliment that often came up during my early college days (according to women around campus) was that I was the bartender with the great butt. The first time I heard this, I honestly didn’t know what they meant by this. Was it a compliment? What about it was great? I mean, I did have an ass. Hell, I remember at least one of my male friends growing up asking me once if I realized I had a woman’s ass - I never took this at face value, and always assumed it was some kind of ridiculous insult… but what exactly did that mean?

Looking back now, I still think that if I had never ran into my Ex Girlfriend, I would probably be in a very different place today. I would probably be in some office job somewhere, using my business degree on some desk job in a cubicle, while bartending at night - and what you’re reading now wouldn’t even exist… but who knows. Maybe I was always destined to end up in sexy bras and panties. I maybe I was supposed to be one of the Seattle Tech Bros you see being way too loud at stop lights in their sporty car.

When I met my ex, my streak of “womanizing” had definitely slowed to a crawl, I was striking out more often than not, and I truly didn’t know where it came from. I do now. It was pretty obvious from the outside that the specific hot women I pursued wanted the masculine guy I thought I was… but I was never self aware enough to realize I was far more androgynous than I ever was masculine - especially after I grew out of my “growth” stage and settled into the body and face nature had determined I would be as an adult… or at least what nature thought it had determined. All I knew was, at the time, it was frustrating, and a pretty big blow to my ego. Of course, had I been able to accept this, maybe I would have realized there were plenty of women out there looking for an androgynous pretty boy, not some masculine douchebag I seemed to think I was.

When I met my ex I was already feeling out of sorts, so when she came into my life, it was honestly great - initially. Things progressed quickly and my slightly bruised ego was flourishing again. But ultimately, as we became a bigger part of each other’s lives - I settled on the idea of maybe settling down, finally retiring my “douche bartender womanizer” persona and locking in my life - “Growing up” basically. And I was about to start growing up… just not in the way the masculine side of myself would have preferred.

We were about a year into our relationship and living together, when she began cheating on me - it was bizarrely straight forward when it was finally revealed. I didn’t catch her, she didn’t show any hints at it - she just came forward one day and told me that the ex-boyfriend she had been seeing before me wanted her back in his life, and that was what she wanted, and had been doing for the last couple of months. Her emotional disconnection from what hearing all that might do to me was really the most shocking part for me. I begrudge her nothing now, and wish her well - but at the time, I was devastated.

She left that night, gathering whatever she could from our apartment in a couple hours, and then pretty much disappeared from my life like she had never existed - only that couldn’t be true, because she left plenty of crap behind.

I hit a pretty heavy depression. And drank to cope - for about a month… which was stupid. Whenever I wasn’t drinking, I was working the bar wishing I could, and whenever I wasn’t doing that I was going out, trying to find anyone who might be up to have some fun and make me forget my pain. But at that point, most of my college friends had gone about their separate ways in life and all the friends I had made that were connected to my ex were unbearable to be around - they reminded me of what I had lost.

It was at about week 6 of feeling bad for myself that I got a little too messed up on rum one night at my place. I had the weekend off and couldn’t psych my ego up enough to try going out alone to strike out again - so I hit the rum pretty hard… But this time I hit it in celebration, I figured that ultimately I was pretty lucky to have my own place, my own job, and be reliant on myself - and that was nothing to be sad about.

In all honesty, that night is still a haze in my mind, but there are definitely certain aspects that I can remember pretty vividly.

For one, the rum hit me good, and I actually was starting to feel like maybe I was at the crossing point of the depression threshold - and that put me in a pretty good and goofy mood. So it was with that mindset that I ran across the large stack of my ex’s clothing in my guest bedroom. I had pretty much tossed it all in one gross pile after she left, and hadn’t really returned to the room since. I’m pretty sure I went in there to start throwing some of it away, as some kind of silly symbolic first step in pulling myself back up. I remember a very drunk me teetering around the room and trying not to fall over as my hands dug through clothing, makeup, shoes, toiletries, suitcases, several giant mirrors, college assignments, papers, and artwork from the walls - one giant soup of an ex relationship.

I don’t even know how the memory came flooding back so strongly into my mind (likely from the rum), but as I dug through some of her stuff, I ran across a pair of her panties. And it made me stop and recall a past event. Something about seeing them made me remember what she had told me once while dating. She used to joke that my ass was better than hers, and that she was “jealous” of it. It made me start thinking about all the times people had complimented me on my ass over the years… my supposedly very feminine ass.

I can’t fully explain what really compelled me to put them on. I think honestly, that part of my drunken mind wanted to see if she was right. I think another part of my mind just found the idea hot. I mean, panties are sexy, they look amazing on a woman, and these especially used to look amazing on her. They were stripped, sexy cheeky panties from Victoria’s Secret, with black lace around the edge… my ex did love to wear sexy stuff, it was a big part of my attraction to her. So I was curious - would it look like a woman was wearing them if I put them on? My drunken state decided to let me explore that.

I bring this moment up a lot when people ask “How did you get started dressing?” The quick answer is “My ex left stuff behind, I got drunk and tried them on.” The full backstory kinda shows you though - I was kinda doomed to eventually reach this point. The strong, masculine side of my brain that wanted to drink, fuck, and take power, was silenced by the rum that night, and I don’t think he will ever forgive me for that… because it allowed this little dormant feminine persona through the door… and as soon as that happened - it started the cycle.

Because here’s the thing: When you find soft feminine curves extremely hot in lingerie and tight sexy little outfits - the masculine side of your brain demands and craves seeing it and getting off to it if they have access to it. And if you ever dress up and take notice that your feminine side actually looks soft, and curvy, and hot in lingerie - that means the feminine side of your persona can actually fulfill your masculine sides desires. And you suddenly realize you can be your masculine sides personal dress up doll… And then — you can’t escape the cycle. He wants more of that hot chick to get off too, and that hot chick tries hard to look good for him - otherwise the illusion breaks…

But I didn’t know any of that yet. All I knew was that my ass actually did look extremely femme and girly in those panties… even without shaving, even without trying… and it was simultaneously both incredibly thrilling and horribly terrifying. And my drunken mind had no idea how to handle it. How could I find my own ass hot… what was even happening here?

Even in my drunken clumsy state I took them back off fairly quickly… I remember barely being able to stumble out of that room and make it back to my bed… but escaping that room didn’t really matter. The seed had already been planted. I had already seen what I could pull off with minimal effort… what would happen if I actually tried?

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Yup, end of Chapter One… How does an autobiography even have a cliffhanger? Because it’s more fun that way. Hopefully you enjoyed it! It will probably be a while before I add more to this, but that just means you can wait in anticipation I suppose 😝