From Beta Male To Woman – A Sissy Feminization Story [M23/F26] [Sissy] [Feminization] [CrossDressing]

It feels like it all happened at least an eternity ago and roughly twenty year old me was studying at the university. To get myself some spending money, I worked part time on the weekends: Serving drinks in a bar. It was then when I met her, a woman, a few years older than me, definitely a top, and a hardcore lesbian.

I might have had a little crush on her, totally knowing that nothing would ever come out of me, because she as mentioned before, she was in into woman, and because who would date a beta male like was. A beta male that wasn’t even seen by most woman, and that was not much respected by male human beings either.

During that time I was living in a shared apartment, with three other men, where the only way to get some privacy was looking yourself into your room late at night. So I really struggled to find the time to give in to a secret desire of mine, to put on some nice panties, to fuck myself up my as while watching some nice sissy porn.

I’d loved to devote more time into that hobby of mine – it really wasn’t much more back then, just a slightly kinky hobby of mine to relief some sexual tension, because I had no luck at all with women – but I just hadn’t enough alone time to do so, because when sharing a place with three other people, you are never home alone.

And I really needed to be careful, because my roommates catching me in the act, them seeing me in my early female form, it just was too dangerous. Because they weren’t that kind of men that would just join in and fuck me senseless, they were the ones that would laugh at me, tell everyone about it, and that would be the end for me who was attending a technical university with mostly male students.

So I kept on studying, I kept on working in the bar until something else came up: An engineer’s office was hiring part time, and they were looking for someone that was good in crunching numbers. I applied, I got the job and it happening did more than good. It gave me some self esteem, and it gave me the funds to eventually look for a different place to live in. Maybe something small on my own, or a bigger place with one, two roommate maximum.

I was in about a year after I had stopped working at the bar, I still was looking for a new place for me to stay in, I meanwhile had been looking at many places, meeting up with many possible future roommates, that I came over an add on an online platform that really caught my eye.

And surprise, it was my former coworker, the die hard lesbian barkeeper I had crush on and got along with more than well that had put the add online. I immediately contacted her, to my own surprise she remembered me, something that very rarely happened back then, and two days later I was sitting with her in her living room, having a nice conversation over a glass of water after she had given me the grand tour of her place.

A few weeks later I moved in with her. Rent was affordable, the place was in an awesome part of town, the apartment itself had a living room, her room, my room, a more than decent sized kitchen, a broom closet, some hallway, a bathroom and a toilet. It looked like I had found a place to stay for the foreseeable future.

My roommate and me got along more than well. When she told me that she picked a male roommate because she had enough of the roommate falling for her roommate drama when living together with a woman, I totally fully understood, and told her that I woman that were into woman only like her totally did nothing for me. What was a lie, but it was what she wanted to hear.

We then kept on living with each other, or next to each other. Because she was mostly working in the evenings, sometimes into the early morning hours while I was mostly out during the day: Attending classes at university or crunching numbers in the engineering office.

So we didn’t really see each other a lot, and her not being home when I was home, and that all being totally plan able, it gave me plenty of home alone time. Time I used to dive deeper and deeper into my biggest hobby, maybe even live goal: Turning myself into a hot woman, because as a man, despite having some success, I still mostly was nothing but a failure.

It shouldn’t take long and I began to fully shave my whole body. I got myself more and more female underwear, some sexy lingerie too, and my toy collection grew. I spent most of my home alone evenings, I had at least five of them in almost every week in about the following way back then.

After coming home from work, or university, of both of them I mostly always made myself something to eat, my roommate almost always was already at work, at least during weekdays from Tuesday to Friday, then I enjoyed my meal before having a long and relaxing shower where I made sure that my whole body was nice and smooth afterwards.

Once I was done showering, I did my hair – I was letting it grow out back then, in a way that I could style it in a female and a male way – then I put on some makeup. I had to use mine, because my roommate didn’t owned something like that. She didn’t care about such things, and despite not prettying herself, she was drowning in hookup or even marriage offers from men that she served drinks too. She really was an attractive one.

Then, after I was done with my makeup, it took me a long time to get something passable done when I moved into the place I had been living in back then, but with time I got faster, and the results got better and better: I began to look more and more pretty every week. I really began to love feminine me.

Before leaving the bathroom I put on some lingerie, then I mostly always went to prepare my backdoor before I ended up in my room, where my toys, and a computer filled with sissy transgender female domination porn were already waiting for me. It shouldn’t take long and horny me was in full swing.

I always began with a smaller toy, and I always used plenty of lube when fucking myself. I started to give it to me gentle, slowly, to built some tension, to relax, to prepare my body for more while watching porn on a relatively big screen on full volume. I doubt that any of the neighbors were able to hear anything, because I rarely ever was hearing them.

The sensation of my toy going in and out of my asshole, the images on the screen, the moaning coming out of the speakers, it shouldn’t take long and I was gone, and I was in my happy place where all that mattered for me was putting something more kinky on the screen, and shoving a bigger toy up my ass. My dick already stayed untouched, but also unlocked back then.

After drowning a bigger toy in lube it went up my ass, and I fucked myself with it a little bit harder, maybe a little bit deeper, which made me feel even better. From time to time I took break to take a selfie, back then mostly for me, but sometimes also for some men from the online world.

For some kinky conversations, and to maybe get a compliment on my feminine looks from time to time. To make me feel good, to make me feel approved, to fill out a hole that was there, deep down inside me. I loved those home alone evening, and I also loved the people I met online back then, that mostly encouraged me to take things one step further.

To maybe slide an even bigger toy up my ass, to ride it – suction cups are awesome – while sucking on another toy. To make me feel even better, to make me moan out even louder, to turn my brain off even further and turn me into a next to perfect cock craving cum and cock hungry slut.

I long had lost track of time, track of my surrounding, track of everything but the more than pleasant sensation of riding, of fucking a more than decent sized toy with my meanwhile limp, but pre cum leaking dick bouncing up and down with every thrust I gave myself. It shouldn’t take long, and I would come.

Coming like a woman, coming from anal only – it took me some time to get there – with my dick and my balls not having been touched in a sexual way at all. I was gone, I was out, the porn on screen had turned into blur, the moaning from the speakers was overwhelmed by my own while my body went up and down on the more than well lubed suction cup dildo I was sitting on.

Then an incredible heat built up inside me, sweat began to run down my body, fuck it felt so good, just one more up and down, one more in and out, then another one, then the next one, and then all of a sudden, meanwhile on almost every evening, I finally came.

My whole body trembled while my cum leaked out through my meanwhile fully limp dick. A few last very loud moans escaped my body while it happened, the dildo was as deep in my ass as anyhow possible while I came more than good, while I came from anal, from penetration only.

When I returned into my body, after enjoying that more than awesome post orgasm sensation, after regaining myself, I mostly always found myself laying on the floor, next to the more than decent sized suction cup dildo that had given me more than just some pleasure. What a great way to end my day.

Once I was done fucking myself, it was cleanup time. Time for a quick shower, time to remove the towels I was fucking myself on, time to go to bed. Always hoping that it wasn’t that late, and that my roommate hadn’t returned home yet.

And yes, looking back from now, it really was just a matter of when she would catch me in the act, and not if she would catch me in the act. But some time should pass by until it would finally happen, until my roommate would see me in my female form for the first time ever.