Adventures after Dark Ch. 01

-Author's note-

I started crossdressing in my teens, but coming from conservative South-east Asia, it was definitely my darkest secret for many years. I would often dress in my mother's dresses, and put on her makeup when I was home alone, but I stopped crossdressing when I moved away to start college.

When I won a scholarship to study in the UK, I did not expect to go back to old habits, as at that time I've almost all but forgotten those days and thrills.

Needless to say, I found my old passion, as was more daring that I would have been, being in a different country and all.

I'll probably write more about my (mostly true) crossdressing adventures in the UK if this is well-received, but meanwhile, do enjoy my first story ever here on Literotica.

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My housemates had left for the winter holidays, and I had the house to myself for two whole weeks. Being so far from home, I could not go back home during the Christmas holidays as the flights were unbelievably expensive. Regardless, I looked forward to these two weeks.

Now, as, I'm sure, most of us crossdressers do, I planned and schemed for an adventure almost immediately after learning that my housemates were leaving, about a month before.

I had just moved to Southampton about 3 months back, and had never ventured out dressed here. I was not familiar with the surroundings. It took a bit getting used to, but after 3 months, I knew where the dark corners in the streets were, which roads were deserted, and what time my neighbours would turn off the lights.

We stayed in a 3-bedroom house not far from Southampton Commons, a beautiful park just north of the city, and luckily for me, I discovered over the last three months, that it was quite deserted after dark. I knew this was the perfect opportunity to go the full mile to dress up fully for a stroll in the night. My anticipation grew so quickly after I started planning that I decided to go out the very first night I would be home alone!

I waited for the last of my housemates to leave for her 9pm flight on the last Friday before Christmas. A peck on her cheek, a wave goodbye, and after I shut the door behind her, I quickly rushed to bathroom, drew a bath, and then went upstairs to my room to open my locked suitcase above my wardrobe.

Now, at this point I had stayed in the UK for over two years, and had a substantial collection of dresses, wigs, makeup kits, shoes, the whole shebang.

A bit of myself: I am about 5'7", dark hair and eyes, quite fair, with a nice round ass and some fat around my boobs. Not too much that they stick out, but with the right bra, padding, and tape, I could squeeze out a realistic and decent cleavage. I had a slim waist as I do sit-ups quite often, so I had a quite convincing figure.

I took out my pink blouse and a black flared skirt which I bought after seeing a picture of Brenda Song at the 2013 Pink Party ( do a google image search ^^). I bought them online, so while the blouse was a good fit, the skirt was actually quite a bit higher than mid-thigh. It was the right amount of slutty, but this meant that the laces of my black stockings were visible.

Next, I picked a lovely pair of black high heels, about 3 inches high. I rummaged a little and took out my favourite winter jacket. It was red, with a fur lining, and zipped up front, if I wanted to close it.

My bath was almost ready; I took my special grooming kit from the suitcase, which I had not used for quite some time.

Due to my heritage and age I had no facial hair and only a bit of leg hair. I knew to be thorough, I would need to shave them off, and also pluck out stray eyebrows. I shaved my armpits and pubic hair as well, then soaked in the luxurious bath for as long as I could. It was heavenly, lying in the hot bath, while feeling up my hairless body. I cummed at the end, after letting my imagination go wild.

After I dried myself, it was already 9.30pm. I called for pizza delivery, which I knew would usually take an hour or so, then started putting on my selected wear. First, I tucked male parts into my body to hide them, followed by a nude-coloured waist shapewear. Then, I put on a pair of seethrough red panties, followed by a pair of black sheer thigh-high stockings with frilly lace on top which were held on by silicon bands.

I then put on a pink lacey bra, which was at least an inch smaller that my actual size, but its tight pull enabled me to have a cleavage, which was a plus. I adjusted the bra, shifted my breasts around and inserted the silicon pads beneath, therefore creating the illusion of cleavage. These took about 15 minutes to get right, but the hardest was to come.

Makeup. The bane of any crossdresser. I always start with foundation, then the lipstick, a bit of blush, then the eyes. I love the smoky eyes look, and it definitely looks the best on orients, especially with our eyelids. It took me the best part of 30 minutes just to perfect the look. I had a couple of paste-on diamonnd earrings, which I stuck to my earlobes.

Lastly, I put on my black shoulder-length wig, and finally felt ready. I looked in the mirror, saw a different person who was about to get dressed.

I put on the blouse and skirt, saw the amount of exposed skin just below the skirt hemline and chest, and felt pleased. I was doing the final touches to the face when the pizza delivery guy came.

The ultimate test! I went downstairs with my 10 pound note while trying out my high pitched voice, and opened the door.

The cool air rushed in, and I gave an involuntary gasp. The delivery guy was stared at me, then gave me a smile. I knew then I was convincing, and I quickly thanked him, gave him his money and shut the door.

I quickly had a couple of slices, followed by a few cans of beer, all this time urging myself to go through it. I wondered around at home while taking photos around the house.

At 11pm, I wore my lucky pendant (another story for another day), then drank another can of beer just to warm myself up. I grabbed my handbag, which had only my house key, a mirror and some cash, and left everything else that could identify me at home, including my phone. An afterthought made me put a vibrator into the bag. I put on my coat, then the heels, which lifted my ass higher, making me shapelier. I had a last look in the mirror, knew this was as womanly as I would get. This was it.

It was now or never. I switched off all the lights in the house, and went outside, and quickly shut the door behind me. The cold winter air hit me, and i felt a breeze under my skirt, a feeling I loved so much. I felt so exposed.

I had a quick look around, no one in the area, and I quickly crossed the road to the alley opposite.

I walked the half-mile to the commons, all the while hiding in shadows. It was a cold night, and few people were out in the streets. Among them was a group of drunk guys and girls. My jacket was zipped up, and while I was warm waistup, my exposed legs were feeling cold. I saw that the girls were wearing jeans, and I felt a surge of pride knowing I was more sexily dressed than girls that night.

That gave me some newfound courage, and I unzipped my coat, showing off my cleavage. The roads were pretty empty, but a taxi driver drove past, and slowed down quite noticeably, hopefully to check me out.

I took a couple of right turns, and as I almost got to the commons, I met 3 white guys, all in their mid-20s, taller than me even with my heels. They walked past me, and they made no effort to stop staring at me as I walked past.

A few moments later, one of the guys said, quite loudly "Look at those legs and ass!" Another said something quite quietly, and they all laughed. I turned my head, and saw that they were still looking. I hastily walked down the next turn, feeling embarrassed, and at the same time, exhilarated from the experience. I waited a while, and when there were no cars around, crossed into the Commons.

There are a few benches near the entrance I went through, so the first thing I did was sit down. My legs were tired from the walk; heels aren't the best of things to walk in. I checked my clothing to see if anything wrong was showing, padding, wig off the mark, but everything seemed OK.

It was probably a good 15 minutes for me to get here, so I decided to stay a while. I was feeling quite cold at this point. I walked deeper into the Commons. It was quite an experience, dressed in women's clothes, and walking in the park on a cold evening. I began to feel quite cold after a while, probably due to the alcohol wearing off. After about 10 minutes, I started walking back home.

As I walked towards the entrance, I noticed a group of guys on one of the benches near the entrance. It was the same 3 guys earlier! They had a carton of beer, and it seemed like they just started. Just then, one of the guys saw me, and waved for me to come over.

I panicked a little, but seeing that I couldn't outrun them in heels anyway, I just walked towards them, hoping that they would be decent guys and just let me walk through. The other alternative was to go the other way, and that would bring me to the other exits which meant another half-hour's walk.

I got closer, and they quiet down a bit. One of the guys (James, I would find out later) asked me if I would like a beer, and without thinking, I answer back in my normal voice, no thanks.

The initial shock wore off quickly, as another just said, go on, have one anyway, it's cold. I pulled my coat closer, and said in my high-pitched voice, "Alright, just one." No point arguing when drunk, I thought. They seemed all right anyway, and were quite accepting.

I sat on the bench under the lamppost opposite their bench, lighting up my pale skin. I crossed my legs in a girly manner. We started talking, and they asked me questions about crossdressing, like how long have I done it, why, who did my makeup etc. I answered their questions, and all the while having a few more beers.

I noticed them staring at me and my legs, although they made some effort to hide it, I felt thrilled that they were interested. I felt quite drunk, and had less inhibitions. I started crossing and uncrossing my legs, each time the skirt hiked higher. I noticed that James and Dave who were standing up started to adjust their jeans, which made me feel more excited.

I decided to tease them a bit more, and took off my coat. I no longer felt the cold. This time, they just stared. The last guy, Jim, said, "Wow, you're hot."

I smiled and said thanks. We resumed drinking and talking, and after another can, I asked Jim what he whispered earlier when he saw me. He looked embarrassed, but told me that he said to the others that he would 'bang her like the slut she was.'

I started feeling quite aroused and uncrossed my legs. The skirt was hiked up so much now that it showed my pale flesh above the stockings. I pretended not to notice, and asked them to pass me another beer.

James and Dave sat next to me at that point, and started chatting me up, in a joking way. They were using lines like, "you know you have beautiful lips", and "your tits look real." I looked at them, and reminded them that I was a guy, and said that I wasn't gay.

They laughed and said they knew it, they were just complimenting me. They started touching me, at first quite subtly, a quick pat on the back, a brush on my thigh, but after a while, without me noticing, my blouse was off my right shoulder.

Just then, Jim said out loud that I had shaved my armpits. I replied, "That isn't the only place I shaved."

And being drunk, I asked if they wanted to see it.

They laughed and said, "Why not."

I opened my legs, and lifted my skirt, pulled the shapewear aside and showed them my shaved V. With my tucked away penis, which wasn't very aroused, partially from a mixture of cold, alcohol, and a bit of fear, it must have looked like a real pussy.

Jim stood up and said "Fuck it", whipped his cock out and started jerking off.

There I was, sitting on a lit bench, not far from the entrance to Southampton Commons, two guys on each side, and a guy standing in front of me wanking. It was surreal.

I said, "Guys, it's too open, someone might see us.."

Jim picked up my coat from the bench, and threw it behind a tree near the bench. It was hidden away from view. James and Dave started feeling up my legs, and with their arms around my back and legs, lifted me up, with my legs wide open. I put my arms around them, suddenly conscious that I may be in trouble.

They put me down gently on my coat, then James said to me, "Look, just say stop if you're uncomfortable and we will."

I looked at him, felt a surge of comfort, and said, "It's all right, we're all having fun, that's all! Just no fucking, ok?"

My clit was getting hard, and it popped out from my panties. I squatted in front of them in anticipation, as they took their cocks out and start masturbating. I stared at their cocks, which were at least 6 to 8 inches long; mine was shorter, just partially erect, making it look small compared to theirs.

I opened my handbag, and took out the vibrator. I sucked on it, putting on a show, then inserted it into my ass, while moaning and feeling my erection.

I felt bold, and beckoned James to come closer. Then, for the first time in my life, i held someone else's dick in my hand. I started jerking him off, but as I stared at it, I knew I had to play my full part, and I started sucking it. At first I was clumsy and didn't know how, but the smell was so intoxicating, and my drunk self had abandoned all morals, that I started using my tongue more, and giving proper head like those girls in porn. My left hand on the vibrator, my right hand and mouth servicing James, I never felt more like a slut.

Soon, one of the other guys pushed me forward, and I got into kneeling position. He took my vibrator and continued fucking me with it, freeing my other hand. I used both hands to grab James' hips, and started deep-throating him.

They then took turns with my mouth, all the while someone played with my ass and clit while I serviced the others. They also slapped my face with their dicks whenever I stopped, the glistening cum mixed with saliva on their dicks splattered over my face.

One of them said he was gonna cum, I think it was Jim, so I smiled and asked them to give me their seed on my face. I started jerking off my semi-erect clit.

As they cummed over my face, I cummed too. I took my fingers to my mouth and sucked on my own cum, then scooped theirs from my face and put them in my mouth. I rolled it in my mouth, opened it for them to see, then swallowed.

I laid down on my coat, tired, their cum on my face. They sat down on the benches, tucking their cocks into their jeans again.

After a while, I got up, picked up my coat, and said that I had to go.

They asked me when I could see them again, and I said "Perhaps another time." Jim then apologised for getting my coat wet and dirty. I said it was OK.

He took out a twenty-pound note and said, "Here, take this to cover cleaning costs." I refused it. The others then took out their wallets and pulled another twenty each. They insisted I take it, and to use it to buy more clothes if I wanted to.

Against all judgement, I took the money, and asked for their phone numbers. Dave wrote his number on the beer box and tore it out. I put everything in my purse.

"I'll call you this coming week, if you are all around," I said. I turned and hurried home.

It was already nearly 1am as I walked home with cum on my face, and sixty pounds in my handbag for services rendered, I felt more happy than I ever was, a true slut and cockwhore.

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Hope you enjoyed it :D