A Night in Antwerp

Every year I spend a few days in Antwerp, Belgium around winter time for work. Usually a long weekend with Saturday night as really the only free time.

Most years I'm accompanied by a colleague, Dan, who also happens to be one of my closest friends so it always made for a fun trip. Dan was the best man at my wedding a couple of years ago, our wives also get on well with each other and us, so it all works nicely.

The journey and work conference could be a little tedious so we always looked forward to the Saturday night where we could let our hair down a little and enjoy a rare 'lads' night out away from the wives. We were both nearing forty so our wild nights out were long behind us in truth.

We both really liked the city of Antwerp. It's so multicultural and has the benefit of just about everyone speaking English along with two or three other languages, putting two men from England to shame.

Typically we'd find a nice steak restaurant for dinner followed by a quick drink in a bar if there was live music on.

We'd generally end the night wandering around the red light district. Rarely did we partake in any of the services on offer there, it was just an experience to wander around and see the women in the windows, some of which were truly stunning. Others not so much. There was definitely something here for most tastes.

Antwerp's red light district hides in the shadows of the famous Amsterdam red light district a couple of hours north, but is in many ways better. Amsterdam's has become a tourist attraction, an odd thing in itself but true. In the event you actually wanted a prostitute in Amsterdam you first have to navigate the bustling streets or know the area and best times well enough to avoid it. Then of course everyone is openly watching you entering and exiting the famous red doorways. Not exactly inconspicuous. It also means scams and getting ripped off are more likely.

Antwerp's red light area has almost as many windows, but is tucked away in the city and only really frequented by men looking for the obvious. They've added shops, sex shops, strip clubs, cafe's and other attractions to avoid it becoming a seedy dangerous zone. There's also a permanent Police presence.

Only once did I have sex with a prostitute there. I wanted to try it and see what is was like, my friend Dan would never go in but enjoyed looking. I paid fifty Euros and had sex with an extremely attractive petite woman with large fake breasts a few years back.

In truth I didn't enjoy it, it was very mechanical and not a turn on. I guess what turns me on is the mutual lust, exploring someone's body and taking their clothes off, the passion. All this is missing with a prostitute. But it was an experience I tried and found out.

Something that did secretly excite me at the thought of was the trans ladies in the windows.

I'd had fantasies of having sex with a trans woman for a while, I often watched trans porn, the girl fucking the guy. Giving anal sex didn't appeal to me.

I thought a prostitute would realistically be the only way to fulfil that fantasy. Part of me knew it would still have that mechanical element, but the excitement and thrill of something so new and out there would be a huge turn on.

Of course getting this opportunity was still so tricky, I would never tell Dan about this fantasy. I did secretly keep an eye out though for trans women in the windows to see what they looked like. I'd done the same a few years ago on a stag do in Amsterdam. They generally have blue lights or a little sign to let you know. Or they just grab their cocks to leave you in no doubt!

In truth I'd found them hard to find. The few I did see weren't attractive to me, often extremely masculine looking where as I preferred the idea of a beautiful female with a cock. I realised that perhaps I was experiencing the difference between a porn fantasy and reality, and maybe the reality didn't actually appeal that much.

This past year I found myself being sent alone on the annual conference without Dan. After the initial disappointment of expecting a tedious weekend ahead, I found that feeling quickly replaced by the opportunity of exploring the red light district alone, with the freedom to do as I please secretly.

I did some online research about what to do and where to go, it was a turn on just thinking about the possibility of doing it.

Saturday night came around soon enough. It was cold and windy so I dressed up warm with a big coat and scarf. Not exactly ideal conditions to go looking for sex.

After a brisk walk which helped warm me up I found myself back in the red light area.

It was busy, but not so much to be a problem. I decided to slowly walk around check out the windows. Secretly hoping to spot the blue light ones.

At first all I saw were beautiful women wearing very little beckoning me in. I'd done a complete lap and seen no blue lights. One woman stood out as she wore an elegant, tight red dress rather than just standing in her underwear. I always thought this might be a better way to secure custom, leaving more to the imagination. Maybe that's just me though and I digress.

On my second wander though I did finally spot where the blue lights were and actually there were a few of them all next to each other. They were at the end of street directly opposite one of the busiest areas and distinctly separate, deliberately so. Meaning if you wandered over there was no doubt what you were looking for. No one else was over there meaning I couldn't just blend in. Frankly I was scared.

I subtly looked over as best I could from across the street, there were several trans ladies, some in the windows and some outside chatting to each other. Generally they had two to a window. From afar they all seemed quite tall.

About three of them started waving wildly in the air in my direction and shouting, "Hey! Hello!"

I looked around me to see what was going on and they pointed at me, "Yes you! Come over here!"

I thought this was my excuse to finally go over there and at least get a good look. It wasn't far at all, a few seconds walk, but still away from the main crowd. I was shaking with nerves and the cold didn't help.

"Were you waving at me?" I asked trying to sound confident. At least five women gathered around me, three outside and two just inside an open door.

"What you looking for handsome?" one asked. They were confident, brash and all talking at once, no doubt trying to make a sale.

"He's so handsome!"

"Mmm yes please I like that ass"

"Want me to teach you something honey?"

Were just a few of lines I picked up in the background. They could tell I was nervous and clearly new to this.

"I'm not looking for anything." I lied, far too scared to say what I was after in front of them all.

One of the ladies in the open doorway was more astute than the others and picked up that the situation was probably a little intimidating.

"Step in here and talk, it's freezing out there." Giving me the excuse I needed to enter. She closed the door behind me and the curtain to avoid prying eyes. It was just me her and her friend inside a very small area with two little chairs. I knew from my previous experience this is where they negotiate and then take you out the back to a little room with a bed afterwards.

"I'm Tanya, this is Monique," she said gesturing to her smiling colleague.

Tanya was a little shorter than me, petite with a long black wig on that flowed down to her round ass. She had huge fake tits and was wearing very little. Basically just lingerie. Under her pants was the definite bulge of her cock. She was tanned with smooth long legs. She had a pretty face, with more clothes you wouldn't know she was transsexual. the voice gave her away though.

Monique was a little taller, slightly broader shoulders and shoulder length bright red hair. She had a leather mini skirt on and fishnet stockings. A little skimpy red lace bra covered her fake breasts. They weren't as big as Tanya's but very shapely and well done. Her face was a little more square jawed with a lot of make up and fake eyelashes but still attractive.

No doubt Tanya was my favourite of the group and reminded me of the trans porn I'd masturbated to. I was scared and turned on just at the thought I might do something. In truth I fully expected to still leave as I was so intimidated.

"I'll tell you what," Tanya began sensing I wasn't about to just come out and say what I wanted, "Why don't you give me fifty Euros and we'll go back here and just see what happens? No pressure."

"Okay," I replied nervously but secretly excited, this was perfect as I could ease myself into something or perhaps nothing. Either way it had already been a thrill way out of my comfort zone.

I paid Tanya the money and she grabbed my hand and led me back to her little room. It was small, dimly lit with just red strobe lighting. There was a bed surrounded by various sex toys, dildos, strap-ons and honestly a lot of things that I had no idea what they were. I could see through to a small room adjacent with a toilet, shower and sink.

"Just relax," she said soothingly sensing my tension. "Nothing will happened that you don't want, we'll just take things as they come. Start by taking off your clothes and lying down on the bed."

In truth that was already a big step, but I was reassured by her words and knew I would stop things if I wasn't comfortable.

I nervously took off my clothes down to just my boxer shorts and placed them on a nearby chair. I was already semi hard. As I did this I noticed Tanya taking off what few clothes she had on. I could see her big fake tits, they looked great. I'm normally not a fan as they can look so false, mis-matched, nipples pointing too high or oddly shaped. These were, whilst clearly fake, very natural and appealing.

She slipped off her underwear to reveal her cock. A wave of shock and excitement and nerves came over me as I realised I was really with a naked transsexual prostitute. I'd never looked at cock in this way before, in an appealing way. It was about average size, not completely flaccid though and she was shaved all over.

"Lie down on the bed." She instructed as she walked towards me, "Let's get these off too!" She said cheekily as she yanked down my boxers to reveal my semi erect penis.

"Mmm, someone's getting excited! Actually sit here,"

She said gesturing to the side of the bed.

I sat there naked with Tanya standing in front of me, just in between my legs.

She grabbed my right hand and placed it on her cock, guiding me to stroke it.

I slowly masturbated her up and down as she got harder, it was an odd sensation. Touching someone else cock and masturbating it in basically reverse from what I'm used to. It was also thrilling and a huge turn on. She was quickly fully hard and moaning a little. Feeling the firmness in my hand and having such a close view was all so new to me.

My left hand caressed her hip slightly and moved up to caress her tits, they were firm and didn't move much, I squeezed them harder.

"That's it baby." She encouraged me.

My cock was fully hard and sticking right up looking at her dripping in pre cum.

She had one hand on top of my head, scuffling my hair as I stroked her. She took her other hand and grabbed her own fully erect cock and guided it towards my mouth whilst pulling my head gently towards it.

I was petrified, 'Am I really going to do this?' I thought to myself.

I opened my mouth to accept it and she gently slid her cock into my drooling mouth. It was a thrilling but odd sensation. I could feel the warmth and firmness and the shape of her head on my tongue. It filled my mouth. She gently rocked it back and forwards as she moaned.

I wasn't really sure what to do, I'd never given a blow job before. Sure I'd received many, good and bad, but I had no idea how to give a good one. I reminded myself I was paying and this was for me to enjoy.

I sucked and licked her, moving my head and back and forwards to run my mouth up and down her shaft as I did so. I loved it. I was so turned on and hard, my cock dripping. My hands grabbed her round ass as I sucked her off. I wondered if she had fake implants in her ass as they seemed a little unnatural.

"That's so good baby," she encouragingly said. "Now get up on the bed on your knees and put your hands here."

She motioned for me hold the end of the bed rail facing it whilst resting on my knees, my ass sticking out.

She got up on the bed behind me, I was so nervous but excited. I wasn't sure I wanted to continue or whether I was ready for this but was so turned on I couldn't help myself.

She gently stroked her cock as she unwrapped a condom and rolled it on herself. I faced away from her at the end of the bed, there was a giant mirror on the wall where I could see her reflection behind me.

She squeezed out some lube on her hand and gently rubbed it around the outside of my anus. It was cold and tingly, a shock to the system and made me lurch a little.

"Just relax honey, I take it you're a virgin?" She asked.

"Well, I've never done this before, no." I answered.

I guess a professional like her has seen it all and can spot what a clients all about pretty quickly. She spotted I was new and wanted to take not give.

She pushed one finger, then two inside my ass and spread around the lube. Soon after I could feel the end of her cock pushing on the entrance to my ass as she removed her hand. I had a drool of pre cum extending from my cock to the bed.

She pushed a little and it hurt, I thought to myself there's just no way it would go in, it was just too big.

She pushed harder as I felt her head stretching me, I let out a moan of pain as I gripped the bed frame tighter.

She squeezed a large helping of extra lube onto her cock and around my ass and pushed so hard I screamed a loud "Aghhh!"

I felt the head of her cock break me in, my ass felt like it would tear in half.

She made gentle rocking motions to penetrate me more and allow the lube to spend inside me. Slowly I felt it pushing into my ass deeper.

I looked up into the mirror grimacing, in pain but incredibly aroused at the same time. I could now see her fucking motions getting bigger as she grabbed my hips and ass tightly and fucked me.

Her cock was fully inside my ass now, it was a completely new sensation. The realisation I was actually being fucked in the ass by someone with a cock hit me, I couldn't believe I was doing this, but I loved it.

She picked up her motion as her cock now slid in and out of me smoothly, she let out of moans of pleasure.

It still hurt like hell but my screams of pain were warping into screams of pleasure, or a mix of the two.

I watched in the mirror as she fucked me, staring at her tits and the motion of her hips pounding me in the ass. I started to push back a little and move my ass in time with her strokes.

I felt a tingling in my cock as I realised I was so excited that I was building to an orgasm without even touching myself. I didn't want to suddenly cum, as I was enjoying it so much. She'd likely end it there as a job done. I'd read they don't generally cum themselves as they service many clients in a night.

But if I did I did, there was nothing I could do to stop the building pleasure.

Tanya altered her position slightly and one hand pushed on the back of my head as started to really fuck me hard. She let out aggressive grunts with each thrust. I screamed in agony and ecstasy.

She was bent over me with her tits squashed against my back as her hips continued to thrust and destroy my ass. She licked my neck and ear as I moaned.

"You want my friend to come join us too?" She whispered in my ear in a tone that didn't really sound like I had an option.

I nodded and tried to let out an affirmative 'Mmm' in between my groans.

"Monique!" Tanya yelled. Monique quickly popped her head around the door. Someone else watching was even more of a turn on.

"He wants more cock!" Tanya continued laughing.

"Mmm okay!" Monique replied enthusiastically quickly removing all her clothes as she approached me. I was trying to watch her in the mirror but couldn't get a good view. The next I knew Monique was in front of me with a huge semi erect cock at my face. Much bigger than Tanya's.

Tanya continued to fuck me at a steady pace, "His virgin ass is so good, stick your dick in his mouth Monique, he sucks dick pretty good for a beginner."

Monique roughly grabbed my cheeks and rammed her cock at my closed mouth.

"Open your fucking mouth and suck it!" She aggressively ordered me.

I was glad I'd started with Tanya as Monique would have scared me off running.

I did as told and opened my mouth for a second even larger cock in one night. She grabbed my head with both hands and really roughly fucked my mouth. Her huge cock slamming into the back of my throat making me gag, choke and struggle to breath at times.

She was loud and grunting and shouting insults as she used my face for her pleasure.

Tanya joined in the pace and fucked me in my ass fast and hard. I was being roughly fucked from both ends as two cocks spit roasted me. At times their strokes were in rhythm, at other times one cock would slam in my ass followed by the other at the back of my throat. They high five'd each other loudly, maybe they were really enjoying it too? I felt like I was in another world things were so out of control.

The pleasure built so much I felt a pulsating in my balls, emanating from my ass and I knew I was going to cum.

As they slammed into me my whole body tightened up and my hands tightened on the bed post as I let out a huge "Ugghhh" and came all over the bed, ejaculating a big load of cum.

It was an orgasm like none I'd ever had, with no direct stimulation and a cock in your ass it changes the feeling.

"He just came, he's loving it," laughed Monique.

I nodded and relaxed expecting them to stop, after all I was done.

But they continued to fuck me even harder, moaning louder.

"I'm almost there," said Tanya in a tone of pure enjoyment as she let out moans of pleasure.

At that moment Monique grabbed my head even firmer and stopped thrusting. I felt her cock twitch hard in my mouth as large spirts of warm cum filled my mouth with each pulse. It hit the back of my throat and filled my mouth. It tasted salty, sticky and hot.

She let out a huge orgasmic groan as she came. As she removed her cock I let most of the cum dribble out down my chin, not really wanting to swallow it.

Tanya was clearly quickly building to an orgasm behind me, "Oh yes, yes!" she screamed in a heightening pitch as she reached climax.

She quickly withdrew her cock from my ass, that was a strange sensation, having been filled to suddenly be empty and gaping open.

She quickly ripped off the condom and came on my back and ass, letting out screams of delight as her hot cum sprayed all over me.

I slumped down on the bed as Tanya and Monique composed themselves.

I could feel the pool of my own cum on my belly along with cum in my mouth, cum dripping down my chin and all over my back and ass.

"Can I use the shower?" I asked timidly.

Tanya handed me some cheap looking paper towels to wipe myself with.

"I'm sorry the shower isn't for customers." She replied as she gathered her clothes.

Monique piped up, "Also it's an extra fifty euros for me." No doubt this was just a sales routine for them but I'd loved it, maybe after the adrenaline wore off I'd regret it, who knows.

"Of course," I replied as I reached into my wallet in my jeans and paid her.

I quickly put my clothes back on and left, aware anyone watching on the street would know exactly what I'd been doing.