Living my dream

by SissyBoi

9 Dec 2019 7176 readers Score 7.3 (29 votes) PDF Mobi ePub Txt


My long-awaited transformation

I broke up with my girlfriend nearly two months ago because she cheated on me for the second time, exactly like my girlfriend before her. Understandably, I want to stay away from girls for now so I decided to try something I have always wanted to try but never did because I wasnt brave enough. But I realized that this is what I wanted and so said FUCK IT and now I have a story I can share with you  ; ). 

But first about me:

I just turned 18 a few months ago and would describe myself as very open and quite feminine, but not just mentally. I am a bit over five and a half foot tall, not very muscular, in fact I am very slim, but I alway get compliments (or jokes) because of my  big butt. But even if they joke about it, I always get very excited when one of my co-workers (I work at a beverage market) talks about how my butt wiggles when I walk, sometimes they even give me a little slap or a squish on my asscheek. 

But its true, nature gave me a very feminine look. When I was 14, my mothers friend had mistaken me for a, quote: cute little girl. But it was not her fault, I mean I had longer hair back then and also my voice was quite high for a boys. Today, I have not quite shoulder long hair and a still very feminine voice. In school or in public I always talk deeper because I dont want to sound like a girl. 

And through my hobbys (Swimming and jogging) my already big ass got even bigger, and so did my legs, but my waist and belly became slim and flat. My arms have never been muscular and after half a year of failed exercising, I gave up and left them as girlish as they were and all in all, even without makeup, in the right clothes I could easily be mistaken for a girl.

I have just had sex with one girl in my entire life, the girl that cheated on me (the second one). Besides that, our relationship was quite exciting when it comes to bedroom activities. We had a variety of sex toys, which I used on her but we also played the other way around. I told her that I liked the feeling of something big inside of me, which is true, but whenever she pounded my asshole with one of our big dildos, I closed my eyes and imagined being fucked by a huge muscular guy with a gigantic cock. She even worked nearly both her fists inside of me one time. 

I never told her but I had (and still have) an own collection of dildos and other sex toys that I used on me when I wasnt with her (our toys were at her place). There were times I even went to school or work with a huge buttplug inside of me.

But now for my story.

Yesterday, a few weeks after I broke up with her, the weekend I had dreamed about the whole last week finally arrived. I live in a fairly large, but not too large city, quite landly. With a tiny bit more than 30.000 people living here we barely crossed the border for being called a city, under 30.000 we just would be a village.

We have two gay-bars in the city center, the Rouge and the Pallette, and I decided to visit Rouge, simply because it was much closer to my place, only fifteen minutes if I walk. It was a Friday, and as soon as I came home from school, I ran to my room, took out my buttplug (kept it in there since Sunday to get as horny as possible, I did not masturbate this week too) and immediately stripped down and sprinted to the shower. 

Shaving was always problematic... I prefer being completly shaved and smooth on every single spot on my body, it makes me feel kind of sexy because it matches my feminine body and my cute face. But my girlfriends always liked me hairy and masculine, so I only shaved down there once a month and let the rest grow. One time, I was so horny I shaved just a tiny spot, a few inches of my leg so I could feel my soft and smooth skin. Everytime my fingers touched this shaved spot on my leg warming shivers went down my spine to my cock and made me feel so sexy and horny.

So I went in the shower that Friday afternoon and shaved completely. Almost one hour later, my face, my armpits, my balls and my 6 inch (hard) cock, my ass, my legs were all clean and smooth, not a single hair was left. I even shaved these very bright hair on my arms so that I was smooth from top to toe.

After I gave myself a long warm enema, I needed to find some clothes for this night. So I waited until my sister went downstairs so I could sneak in her room fast and borrow me something sexy. I had to be fast so I went in, opened her closet quietly and grabbed the first thing I could see, a pile of fresh clothes. I decided it would be too obvious if I took the whole pile so I left one half there. 

I was on my way out already as I froze and turned around looking at the "make-up section" of my sisters room. I could choose from a huge variety of parfumes, eye-liners, sponges and god only knows what else. I quickly grabbed a handfull of tiny bottles and cases and with all my borrowed goods I went to my room.

I put on panties my ex-girlfriend forgot in my room and looked at what I had brought with me: A black top, a red, very wide and loose top, a black leggings and some socks. I put on the red top and the black leggings and looked at myself in the mirror. Even though my girlfriend had a fairly big ass, her panties were a little bit so small and you could see their outline on my asscheeks through the leggings. My red top already ended five inches above my navel but everything fitted perfectly. 

After I put on my shoes and watched a little tutorial on how to do make-up I looked in the mirror again and omg I looked soo sexy, I immediately got hard and began to stroke myself through my leggings. Everything fitted perfectly, my ass and legs looked so good, my face looked even cuter thanks to the makeup and my hair fell down almost past my shoulders, still a bit wet from the shower.

I decided to borrow some more and went to the bathroom, carefully so I didnt get caught by one of my sisters (one is 16 y/o the other one 11 btw), my parents would get home in a few hours so I had not to worry about them. I took some hairclips and other stuff and, after the fourth attempt, I made two decent ponytails, one left one right.

I looked kind of slutty, but that was my intention because I wanted to get fucked tonight and if everything goes well, maybe not just once. After I put on some parfume, I was ready to go.

My sister was in her room again so I could go downstairs and put on my shoes and my sisters tiny jacket to match my short top. I put on fresh lipstick and looked at myself in the mirror again and thought that I could easily go to a regular club because I really looked like a girl, not a single sign of man in the mirror. 

It was 6pm as I arrived at the bar. I was very, very nervous because its a different thing to fantasize about such things and actually doing them, but after a deep breath, I continued to walk towards the entrance. There stood men smoking cigarettes talking to a security guard. After a few horny looks from the men I showed my ID and went past them, dropping my wallet as I wanted to put it in my bag and bending over to give them a good look what could be theirs if they wanted. It took me so much courage to do this but it was worth it as I heard moans and "oh yeahs" from them. After pulling my leggings up and letting my full and juicy asscheeks bounce a few times, I went in, swinging my ass extra sexy and letting it wiggle with each step.

Hope you liked it so far, I'll continue this story very soon : ) . I will also continue to write down my experiences because I am 100% sure this was not the last one! If you have feedback or anything else I would really like to hear! Thanks for reading, have a great day ^^

by SissyBoi

Email: [email protected]

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