Reality Slut Ch. 02

And that was that.

I spent the following months working, dressing and reliving my first male experience.

Around this time, a good friend moved in with me. We drifted our way across the hazy, summer city, drinking cider with ice, chatting up hot women and trying to bring them back to my apartment to play. The fact I like to suck cock whilst dressed as a woman has very little bearing on my attraction to women whilst living as a man. Maybe I only want to get myself as close to true femininity as I can or maybe I am just a red-blooded male after all. Whatever way, it's fine: I just cannot get enough of hot kissing, slow teasing, wet pussies, hard cocks, making people come and coming myself. It probably sounds a little narcissistic, but I never feel more powerful than in the moment after I have given a person the gift of an orgasm. It's one of life's rarely discovered treasures.

It was in that frame of mind and moved by that kind of sultry, city heat, that I drifted into a stormy relationship with a stunning Spanish cocktail waitress. She had small breasts which were firm and high, masses of lightly curled black hair, a heart faced shape with olive eyes, classical cheekbones dusted with freckles and full, soft lips. And even though she was only 5ft 5" tall, her smooth, taut legs seemed to go on forever - until they came to a stop, that is, at the cutest, firmest, most caressable arse it has even been my pleasure to know, fondle, lick, finger and fuck. It would be remiss of me not to tell you that I was always getting a little more out of that arse than she ever really knew - the only thing more nutritious for my sexual soul than the sight of such a wonderful, naked bottom, openly presented just for me was the sight of it framed in the most exquisite lingerie London had to offer. What I wouldn't do to have an arse like that myself!

Whenever she was working, I'd go to her bar in the city. She would watch me watching her as she flirted with customers, offering them eyefuls of her perfect rear, liquid but muscular beneath her tight skirt as now she stretches to reach a bottle from one of the higher shelves and now she pushes her breasts up and out as she lifts her hair to cool her neck, damp from the heat of the lights. After closing time, we'd drink with her colleagues until the ache in her pussy and the throb in my cock became too much for either of us to bear and we'd rush back to fuck until the small hours.

But, as I say, it was stormy.

Whilst we fucked like tigers, we fought like dogs: where I wanted refinement and luxury for our tour of France, she wanted parties and hostels; when she wanted crystal and linen, I wanted to finger her pussy under the table of a cheap bar as she made eye contact with the men who craved her. But, through all the craziness, we stuck it out for a year - and what a year it was.

When it came to sex, she liked to be controlled. It didn't matter if I tied her up or held her down, she just wanted me to show her some aggression. In fact, it wasn't long until she asked me to start slapping her across the face as she sucked my cock. Soon, I was choking her when she was coming and after that it got very crazy very quickly - I was verging on giving her the hardest beatings I had ever given anyone in my life (ok, I'm not a fighter, but it was pretty rough) and the only outcome would be a sopping wet cunt and mind-blowing orgasms for both of us.

My suggestions of wearing her panties every now and then were met with little interest, so I didn't press the point and just kept on giving her what she needed and taking what I desired.

Anal play was something we took to early on. In France, we purchased a toolbox of toys. Before I knew what had become of us, I would have her face jammed down into the carpet of our 5-star hotel (sometimes she bent to my will), a vibrator in her pussy, my cock in her arse and a buttplug up my own.

And then there were the public shows.

One time, we fucked on some steps in London as a crowd of about 30 looked on. Another time, we put on a show for a taxi driver whilst coming home from a bowling alley. He enjoyed watching her suck my cock in the rearview mirror, but probably not as much as he enjoyed the eye contact she made with him, inches from his face, as she arched over the passenger seat when she came into my hand from the muscular fingering I was giving her.

Before long, I confided in her that I wanted to play with a cock. We talked a lot about it when we fucked, but nothing really came of it.

Then, one night, I was one of two dinner guests at a friend's house. The other guest was a gay man. The dinner itself was entirely forgettable, but with the wine flowing I started to wonder whether he would like to play. Having worked up the courage, I put my hand on his leg under the table as we waited for dessert. My attentions weren't misplaced and whenever our host left the room we would quickly kiss and fondle each other.

As it happened, we were both staying over that night and we made an arrangement that after everyone had gone to bed he would come to find me. And so he did, but we were drunk and whilst we did manage to suck each other off it was functional more than sexy.

Despite that, I got extremely turned on as I told my girlfriend about it the next time we met. But she didn't share my enthusiasm and, in fact, it put her into a jealous rage. It seemed she couldn't handle the fact I had been with anyone else. Eventually our interest in each other started to wane: I was 29 to her 20, and before long she moved away to Italy.

The end of our relationship coincided with my friend also moving abroad and so I found myself once again alone in London.

And that's when I decided to abandon myself to my desires and let the slut in me come rushing to the fore.

I broke open my stash of panties which I had kept hidden from my girlfriend and got back into the pleasure of dressing and coming.

At that time, internet shopping was really taking off and broadband had just started to arrive. Taking advantage of both, I built on my collection of panties with a corset and a basque, some black patent high heel shoes, a pair of thigh high leather boots, a range of different hold up stockings, a plaid school girl skirt, a PVC micro mini, a fitted tight white shirt, mascara, lipsticks, eyeshadows, foundation, false eyelashes and nails, a pair of silicone breasts and a long brunette wig. Then there came more anal toys and even some bottles of poppers. The whole lot. And you can imagine that I soon became pretty deft at making up my face and getting myself dressed to kill, even if I was only killing myself!

I started to cruise hook-up sites, looking at pictures of hot women and imagining I was them. I settled on one site, created a profile and uploaded a series of hot photos of me dressed in lingerie showing of my fairly well sized cock and, in one photo, my hairless arsehole, puckered against the thing string of a black thong.

Surprisingly, the response was underwhelming. I couldn't understand why my profile wasn't drawing any men. And that's when I hit the message boards. I posted a couple of ads letting the entire internet know what I wanted to have done to me and the messages started flooding in. Cutting through all the crap of fat bellies hanging down over wildly hairy cocks, I started to work up a couple of decent leads.

One man really stuck out. He was sensitive and intelligent and he knew all the right things to say in his messages to get me playing with my rock-hard cock and fingering my gaping hole. After a week of nightly messages, I couldn't take anymore and asked him if we could meet. That was on Thursday and we agreed to meet the following evening.

I was nervous as hell and suggested to him that we meet first in our normal lives and, if we wanted to pursue anything further, we could do it that night. We picked a pub and agreed on a way to identify each other. I even told him that I would be wearing panties under my business suit and would try to give him a glimpse of the waistband in the pub if circumstances allowed.

The next day, I wore a tiny little sheer black thong to the office. It rode against my arsehole all day and I was so distracted by the plan to meet up that I made a couple of crucial errors in my work. My boss was not exactly diplomatic and at one point in the day he had me standing in his office as he shouted at me for my sloppy work.

Professionally, I was annoyed but sexually, I felt like a naughty little school girl being chastised for wearing slutty panties to class - and the sense of humiliation was overwhelming. Once my boss had vented, I went off to the toilets to masturbate furiously. Fearing that I would disappoint my date if I didn't have piles of thick come for him, I stopped myself right at the edge and was barely able to hold it in. I went back to my desk with my heart in my mouth.

The end of the day couldn't come soon enough. But it did and I made my way to the appointed pub. I worked in the West End at that point and pubs on a Friday night were always busy. As per the plan, I went inside, got myself a pint and went and sat outside on a table where I spread out a copy of the Evening Standard. It was late autumn then and the air was pretty cold. I sat there and I drank and I read. But no-one came. I was afraid that maybe I wasn't obvious enough - but I was the only person outside with a yellow tie reading the newspaper and drinking alone. I got another pint and continued to read. But still no-one came. After 90 minutes, I concluded that his feet had gone cold so I folded up my newspaper and I headed home barely able to move under the weight of the crushing disappointment.

Putting this one down to experience, I flipped open my laptop and logged into the dating site.

At the top of my inbox was a message.

From him.

It started off with an apology: he had cycled past the pub and saw me sitting there, but he had chickened out. It went on to say how much he regretted wasting my time like that and wondered if we could arrange to meet again. It ended with his hopes that I would understand and a plea for me to get back in touch with him.

I felt my cock twitch at the prospect that this wasn't over. I hastily stripped off my work clothes, and threw on my black basque with pink satin ribbon details and a pair of stockings. I fired off a couple of shots of myself on my digital camera, uploaded them to the site and sent him a message back. Keeping my burning desire in check, I explained to him that I was disappointed that he had bailed and I pointed out to him what he was missing by uploading the fresh shots. I started to sign off by saying that if we were going to get together he had better come up with some alternative suggestions pretty quickly - but then I deleted that text and replaced with something much more appropriate: "If you really want to get into my panties, it's tonight or not at all". My chest heaving within the constraints of my basque and my cock pushing against my little black panties, I hit send and went to the kitchen to grab a glass of wine, my hands shaking as I poured it out.

Within minutes, a message had come back consisting only of his address and the words "Please come". I replied straight away to say I would be around at 10pm. It was only 7 o'clock then, but I wanted to be prepared.

I went straight to the bathroom and douched out my arse a couple of times: I was crazy to get fucked for the first time in my life and wanted it to be as straightforward as possible.

Next, I slathered hair removal cream into my armpits, up my legs, over my belly and all around my cock, buttocks and pussy. Giving it enough time to work its magic, I jumped in the shower and scraped at and washed away the stubble that had grown back since I last did it. Once I had dried off and moisturised my newly smooth skin I lubed up my pussy and slid in my buttplug so that I would start to get nice and open for him. Resisting the urge to masturbate, I went to the kitchen and made myself a light meal.

I hastily assembled a bag of goodies: my basque, stockings, a tight black dress emblazoned with the playboy logo in various shades of hot pink sequins, my thigh high boots, make-up, wig and breasts.

To keep me in the mood I wanted to be in, I decided to travel with my buttplug up my arse, so I slipped it out, re-lubed, and popped it back into my nicely yielding hole.

I pulled on the lacy panties which matched the basque, straightened them over the plug and threw on a pair of jeans, a T-shirt and a jumper. For good measure, I chucked the lube into my bag and headed to the Underground station.

The journey was going to be about 30 minutes as I lived the other side of the city. Where I lived, there wasn't much going on, so the train was empty for the first few stops, but as this was a Friday night in London, it soon began to fill up. A range of men and women ready for a night out got onto the train and I couldn't keep my eyes of the women. They were all beautifully made up and dressed in a range of clothes from classically elegant to hot and slutty.

The smell of perfume in the air, the sight of these beautiful women who were doubtless wearing gorgeous underwear in case they got lucky, the looks the other men were giving them and the bumps and lurches of the carriage sending wonderful sensations through my buttplug and into my cock all produced the incredible sense of erotic anticipation which was pumping through my veins.

And there, on the floor between my legs, was my leather gym bag. A thin layer of material separating the world from my deepest, most secret, most powerful desires.

It wasn't exactly my focus as I let the train rock me in my seat, but in the back of my mind was a sense of fear at taking public transport whilst wearing panties and a buttplug and ferrying a bag of lingerie to meet the man I was hoping would treat me like the slut I wanted to be. I was sure I wouldn't be found out, but the ramifications were unthinkable.

In time, the revellers left the train as it passed through central London and by the time I had reached my destination, there were only a few shop-weary workers heading home to families or empty apartments.

It was only a short walk from the station to his apartment. When I arrived, I didn't give myself time to think and pressed my finger against the door buzzer. It was a modern apartment block with a CCTV entry system. I heard the line open.

He spoke my name, as a question.

"Yes," I replied.

"First floor," he said and the electronic door lock released. I pushed the door and took the stairs. At the top, I turned to the right and saw an open door. I walked in, and closed it gently behind me.

There was soft music playing. I walked the length of the corridor and came to his open plan living room and kitchen. He was stood, leaning his back against the kitchen counter top.

I am not particularly attracted to men, but I noted that he was around 6ft 2" tall, muscularly built and dressed in jeans and a blue polo shirt. The short, tight sleeves accentuated his biceps. I could have done worse, I thought.

"Would you like a glass of wine?" he asked. He was well-spoken - clearly from a well-to-do background, doubtless privately educated. I noticed he wore a signet ring on his little finger: a tell-tale sign of his privileged upbringing.

"Yes, please," I said.

I watched, mesmerised, as the muscles in his forearm flexed when lifted the bottle and poured two glasses of white wine. I started to think about the power he would have as he held me down and did whatever it was he wanted to do...

He went and sat on his sofa. Cream leather, I remember thinking. I sat down at the other end, we touched glasses and I took a welcome a gulp of wine. It was cold and crisp as I swallowed it - an incredible contrast to the heat rising in my face, groin and arse.

"I'm sorry about earlier..." he started, but I cut him off.

"It's ok," I said and relaxed back into the sofa.

Various bits of small talk followed about our courses in life but soon we came to the point where it felt like we were saying things just to avoid talking about the purpose of my visit. I reached up to run my hands through my hair and as I did so I felt my jumper and T-shirt ride up over my flat stomach. He glanced down at my bare skin and a smile slowly spread across his face.

"Mmmm...so those are the panties you wanted to show me, are they?" he asked.

I looked down and saw that my thong had ridden up above my jeans.

My heart skipped a beat and my cock twitched.

"Yes," I replied coyly. I bit my lower lip. "Can I use your bathroom?" I asked.

"Sure," he answered. He stood up to show me the way. I grabbed my bag and went into the bathroom.

"I'll be a few minutes," I said, as I closed the door.

I pulled off my clothes and unzipped the bag. My heart was racing and I couldn't control the shake in my hands as I pulled out my clothes and accessories. I worked fast - panties off, stockings on, step into basque, fasten suspender straps, buttplug out, more lube, buttplug back in and panties over the top. By this time, I had started to get into character and I began to move slowly and sensuously. I took a few breaths and started to apply my make-up. I wasn't long and I was soon fitting the wig over my closely cropped head. I slipped my breasts into the basque and made an assessment of my efforts in the mirror.

I looked hot!

Pink lips, black mascara, a hint of blusher on my cheeks and long flowing hair. My breasts were full and the lingerie was beautiful against my smooth and hairless skin. I stepped into my dress and pulled it slowly up over my stockings to hear the whisper of the two fabrics brushing together. Then it was a quick step into my thigh high boots, a tug of the zips and I was ready to go. I gave a girlish little giggle as I looked down and saw my hard cock pressing through the dress - well, I wasn't going to pretend I wasn't aroused!

I opened the door and walked as effeminately as I could back into the living room. I could feel my arse sway as I walked and I let my hips roll from side to side as I went.

He was sitting on the sofa again, looking over at me. I went over and sat down next to him. I crossed my legs and felt my dress ride up and expose my stocking tops and suspenders.

"Wow," he whispered.

I took a sip of wine and licked my lips.

"What do you think?" I asked.

"You look...hot," he answered.

Having put my glass back on the table, I placed my hand on his thigh and leaned into him. He leaned towards me and we started to kiss. After a few gentle nips at each other's lips, our tongues started to get involved and soon we were slowly and passionately French kissing.

My mind was galloping and my cock felt like it was getting harder and harder. Then I felt his hand on my own thigh. I moaned softly into his mouth as he started to slide it up my leg, pushing my dress higher as he went.

We kissed faster and faster now and all I could imagine was how hot we must have looked - a slut and her man, making out on the sofa. I felt his finger hook under one of the suspender straps and pull it taut - and then he let it go and it smacked against my smooth thigh with a little slap. I gasped and recoiled from him slightly, but he grabbed my hand to pull me back in and thrust it against his crotch.

That was it. I started to rub his cock through his jeans and force my tongue into his mouth. I was murmuring gently - not only from the pleasure it was giving me to imagine myself as a slut working for her man but also from the length of his cock and the heat it radiated through his jeans. His breathing started to get deeper as he relaxed into the sensation I was giving him but suddenly he broke away.

"Stand up," he ordered.

I stood up slowly and stood at 90 degrees to him not sure what was going on.