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Josephine's First Night Out Dressed

"An exciting adventure into the unknown that didn't turn out as planned."

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1.4k words 1.4k words

Author's Notes

"This is my true story and experience. The photo is from my first night out."

After I moved from my home country to Scotland at seventeen years old and started working at a high street retailer. I soon found myself attracted to the lingerie department, especially panties. I would secretly try some on as I really loved how I felt. This obsession carried on through my life, including my failed marriages. I was never caught, but I had a few close calls. Fast forward to 2020, my last marriage failed, and I am now living on my own in a shared house. I have a large furnished en-suite room and only share the kitchen.

I am not sure how it started, but after a short while, I found myself buying some panties and wearing them under my jeans when I went out. I then progressed to buying some bras. This carried on until I had a few different sets of lingerie that I would wear to bed. Then the urge to buy stockings and suspender belts came over me followed by getting some dresses a wig and shoes. I would dress most evenings when indoors and loved how I felt. but something still was missing. I wanted to go out dressed but didn't have the nerve to. I would get dressed without any idea where I wanted to go but would change my mind at the last minute. This went on for a few weeks until one evening I googled crossdressing/trans clubs in London, (I live an hour's drive from there), and I found one that had recently reopened after lockdown on Saturday nights. I decided that the following Saturday I would go there no matter what.

Come the Saturday evening, and I am dressed in and, in my car. I am wearing a Burgandy lace dress, sexy red lingerie complete with a suspender belt with sheer stockings and three-inch chunky heels red shoes. It was such a thrill driving when dressed, I was feeling so excited by the whole thing, and cursing myself for not doing this earlier.

I found the multi-story car park around the corner from the club parked and set off. This was my first experience of being in public dressed as Josephine and I was extremely nervous. Now I had to walk along the pavement and mix with other people and just wasn't sure what would happen.

I eventually got to the club after a fifteen-minute walk, and no one had said anything to me on the way, which was a relief. However, as I hadn't read the information on the club's website correctly, I missed the part where it said it only opened every other weekend and that it was closed.

I felt devastated as I walked back to the car park and really upset. My feet were hurting slightly in the shoes as they were new which added to my discomfort. Back in the car park, there was more trouble, as the payment machine was broken which meant I had to join a queue of people at the office to pay. My head was all over the place at this point, but as it turned out I was worrying unnecessary, as the reality was that no one actually cared how I was dressed. Though I was very happy when a couple of different people passed comments on how nice I looked, and this helped boost my confidence a lot.

Now back in the car wondering what to do, I googled once again for trans clubs and found one a fifteen-minute drive from where I was, so I headed there. Still very nervous. I found the place and parked on the street nearby, and once again I was walking with other people on the street. When I went into the reception the hostess was there and she could spot I was nervous and when I said this was my first night out dressed as Josephine she came round and gave me a big hug, then showed me around the club, where the different play areas were and such like. She really made me feel very welcome and comfortable. I was with people who didn't judge me but accepted me as Josephine.

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After chatting to a few other girls there I ventured upstairs to where the dark room and cubicles were. there were quite a few guys and girls just walking around and I got chatting to one of the young guys,) and he put his arm around my back and started to rub my bum. I felt scared at first, but I soon started to enjoy the sensations that passed through me, and I found myself moving closer to him. He turned me around to face him and gave me a long deep kiss, and then asked if I would join him in one of the cubicles. He called me Josephine, and it sounded so natural.

Paul was his name, and he took my hand, led me into the cubicle turned and locked the door. I sat on the edge of the bed, my mind racing with the thought I was been treated as a girl for the first time. Paul guided me to the edge of the bed, and we sat there kissing and cuddling for a while, (I didn't have makeup on so no worry about messing it up). Paul then stood up and as he turned to face me, he dropped his pants and he had such a lovely hard uncut smooth cock, which was facing my mouth. I was feeling very slutty on my first night out and now I was going to suck someone's cock.

After a while when he was good and hard, he pulled out and pushed me back onto the bed, reached under my skirt, and pulled my thong off and threw them at my face. He then put a condom on then lifted my legs in the air and applied some lube before putting his hard cock against my tight hole. My senses were all over the place, and I realised that this was what I craved, to be treated as a girl by a strong guy.

I had never felt anything like this before, and it hurt slightly at first, but Paul was gentle and slow with me. I was in heaven feeling him inside me. He kept this slow pace for a few minutes but then started to get faster and harder, I was moaning out so loud and not caring who heard me, I just wanted what was happening so badly.

After quite a while of this I could sense a change in him, his breathing got faster, and he was going really quick and hard, I could feel his cock start to throb in me. He then pulled out ripped the condom off and pulled my head towards him and stuck his cock in my mouth just as he started to squirt his lovely warm cum into me, I sucked and swallowed greedily every last drop, until he got soft and pulled out.

We lay together on the bed for a while, then got ourselves presentable, (Josephine with a glow on her face), and went to the bar for a drink. As I sat with my drink, I realised this was what I was meant to be, a sissy slut, to be used as Josephine by either girls or guys. I drove back home that night with a glow and a lovely warm feeling inside.

It is now fifteen months later, and I have visited that club nearly every Saturday night. Josephine has made some wonderful friends who support and help her expand her experiences. I have gone to a lady's day at the races and visited a motorway service dressed, and also gone to a big trans night out in a north of England city.

It has been said that Josephine's outfits are getting more daring and revealing and she is really coming out of her shell, and I now have an extensive range of clothes lingerie shoes and makeup. Who would believe how much has happened in a relatively short space of time? Now looking forward to more adventures as time goes on.

Thank you for reading this. xxx

Published 
Written by jocuk
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