My Stay in Amsterdam

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Crossdresser Mimi tries prostitution in Amsterdam.
2.1k words
4.34
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Part 1 of the 8 part series

Updated 06/10/2023
Created 07/28/2021
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One cold wet Thursday afternoon near the Walletjes...

For various reasons I was in Amsterdam for a few weeks. I had decided to take the opportunity to explore the sex scene for crossdressers and my first adventure was to work as a window prostitute for a few days. I ran into Petra who worked in the Bloedstraat normally but wanted a couple of weeks off to visit her family after her father had died, but was reluctant to give up her window, which was well-equipped and favourably located. She had arranged for her colleague Ricca to help me with the ins and outs of being a working gurl in Amsterdam.

I decided to take her up on the offer and go ahead which was why I was sitting here behind a glass door in filmy lingerie, suspender belt and stockings at two in the afternoon looking out over a very grey Amsterdam.

I had followed Ricca's advice and got a spray tan, been waxed, and gone to a dressing service to be made up earlier. I had also been to a STD clinic and had had full blood tests and been prescribed a month's PrEP, just in case I was exposed to HIV during my adventures.

I had butterflies in my tummy and my red lacquered platforms felt like lead weights on my feet.

A face looked into my window and I forced a smile onto my lips. The face had one of those stubbly designer beards.

It disappeared, and then there was a shadow and a voice "'Ow much pretty?"

I straightened up. And went to the door.

It disappeared, and then there was a shadow and a voice "'Ow much pretty?".

I straightened up. And went to the door.

I'd been told to keep the chain on the door until matters like this were agreed. I opened it with the chain on.

"Transvestite" I said, as had been drummed into me. "Fuck and suck € 50".

The body belonging to the voice smelled of sweat and onions.

It wafted in through the crack in the door.

"Can you take me luvvy?" the voice asked. "I'm quite large".

"Transvestite okay".

"Of course okay, what about it?"

"€ 50 fuck and suck".

"Okay"

I slipped off the chain and let him in.

I'd been told to be very friendly when the punter first came in, so I burbled.

"Cold outside? Visiting are you? Have you had lunch yet?"

I pulled the curtain shut and then "What's your name luvvy?"

"Call me John, what's your's?"

"I'm Mimi, dear! I moved closer brushing myself against him.

"Come on John then, let's go upstairs!"

I led the way making sure "John" got an eyeful of my wiggle and a peek under my skirt as we climbed the stairs. I felt him grab a piece of the action and I pushed back, before playfully slapping his hand away.

"Business first, John!"

We arrived in my work room. Red and blue lights, a mirror next to the bed, with the mattress just at crotch height. A mirror ball in the ceiling sent odd flashes of light into the corners of the room. Fake greenery completed the decor. I turned the heater on.

"€ 50 euros please", I said, holding my hand out.

"Yeah, yeah," said John, digging a bulging wallet out from his back trouser pocket.

He handed me a € 50 euro flap, which I immediately went and tucked away in the little secret place next to the chest of drawers on which my make-up lay.

"Why don't you undress" I said to John. Who was standing in the centre of the room looking a bit uncertain. "You can put your clothes over that chair." I said pointing to a chair in the corner of the room away from the door.

John stripped off, although he kept his socks on, flinging his clothes into an untidy heap on the chair.

He turned towards me with his hands over his cock.

"Oh John, I've seen a cock before! You don't have to hide it away from me sweetie!"

I approached him, patted him on his flabby bum, and grabbing him by his semi-tumescent cock under the well-filled stomach I marched him over to the wash basin.

"Let's have a little clean up, heh?" He really did stink of onions, and sweat, and stale cigarettes, and beer.

I held his cock over the washbasin and poured some soap into my hand. With the tap on I ran lukewarm water over, his penis which slowly swelled while I was washing it.

"Don't make me come yet, Mimi!" he said nervously, wafting his beery breath over me. It was true, his uncircumcised cock was now a knob and the tip was a fiery red.

"Like that?" I said, pulling back the foreskin and sluiced a little more water over it. "Some boys just come here to have me wank them off in the sink!" (Where do I get it from). Then after briefly drying him off I propelled his large and wobbly frame towards the bed.

He sat on the edge with his knob jutting out in front of him.

In the meantime I pranced and twirled in front of him tearing open a condom and put it ready on the pillow, together with the poppers inhaler and the lube.

I moved in close, making sure he could smell my perfume. "Well just sit here darling, and open your legs so and lean back on those cushions and make yourself comfortable John."

I ducked back out of his aura of onions and grease and pulled up a padded bench to kneel on. I then lowered my painted lips over his cock. He quickly grew in my mouth and as advised by Ricca I made noises of pleasure while I was slurping on him.

"What a lovely cock" I said insincerely, between mouthfuls, "Not had one this big for some time".

He liked that and I felt him stiffen and moan. Then as I'd been warned was likely, he asked, "Can I suck you?".

"Cost you extra" I said.

"How much?"

I thought 50 but said "30" and "Give it to me now".

He stood up, picked up his wallet and gave me a twenty and a ten.

I tucked the money away and then took my knickers off.

I decided a bit of domination was in order and told him to kneel on the floor and picked up the riding crop from next to the chest of drawers.

He obeyed, and opened his lips as I stuck my flaccid penis into his maw.

"Suck harder, John" I ordered and flicked my crop over his buttocks.

He started sucking and whirling his tongue over the head of my willy, which was altogether quite stimulating.

I let myself grow to my maximum size before grabbing the back of his head -- his hair was horribly greasy and I regretted not wearing mittens -- roughly shoving myself into his throat so that he almost gagged.

I withdrew slightly and repeated the operation. Again he almost gagged.

So I picked up the poppers inhaler and laid the tube in his left nostril and held his right nostril shut for a second or two. While laying the crop over his buttocks again.

I then started fucking his face properly.

I kept up the commentary, "Faster, good, that's right slut. Suck me deep". And lo, now that his head was spinning from the poppers he had no trouble with taking me deeper.

I went on fucking his face until the poppers wore off.

Crestfallen he looked up at me, "I didn't make you come".

"Oh John dear", I giggled, "You are quite a sweetie aren't you?" and chucked him under the chin.

John was trying to get something said, and finally got the words over his lips, "Could you fuck ME, Mimi, please? You're such a nice girl".

"Oh John, what a naughty thing to say!" I tapped him on the bottom with the crop. "Is that what you came here for?" "Well yes of course I could, but can you afford it? Cos it will cost you a 100 extra."

He didn't blink, and I gave him a hand to steady him as he clambered to his feet, and braving his pong, I slipped my arm around his waist and fondled his tool to make it stiff again.

He handed me the 100 note, which I put with the rest of my earnings.

"Are you clean inside?" I asked. He looked a bit puzzled as if he hadn't thought of that before. "No, not sure?" Better give you a quick douche then.

I bent him over the bed, lubed his hole up and pushed the neck of the douche bag up his bottom.

"I'm going to squeeze it empty now and you've got to hold the water up until you get onto the toilet" and if there's any spills you can clean it up yourself with your tongue."

I slowly squeezed the bag empty and removed it. Holding his hole shut with a piece of kitchen roll I steered him to the toilet, where he blew everything out.

"Stay there" I commanded, "Give me the douche!"

I quickly refilled it and told him to douche himself this time, just to make sure.

Afterwards I cleaned him up with kitchen roll and made him kneel on the bed, with his face in a cushion. I made him spread his legs and put a cushion under his belly so that his hole was easily accessible. I crawled up behind him and made my prick stiff again. I slipped the condom on and after lubing his bum pushed into him.

I thrust a few times and started massaging his cock, which fortunately stiffened up. No way though was I going to let myself come fucking this lump of lard. So after a couple of minutes I pulled out and picked up a long flat-based dildo. I poured some lube into my left hand and reached for his cock. With my other hand I passed him the poppers and then smeared more lube into his hole. My left hand him already made good and stiff and he was moaning in pleasure.

"Ready!" I said "This is a dildo and it's a bit bigger than my cock."

The end of the dildo went in quite nicely and he started working himself against it.

I was thrusting on the dildo with hips and now I had a hand free, I reached under him again, to work on his cock. It was still good and stiff and then I told him "Sweetie, took a good snort of the poppers now!"

He obeyed and then various things happened at once.

The dildo went right into the base.

He cock started squirting like a hose.

He let out a huge groan.

He jerked back repeatedly against me trying to get more dildo inside as his orgasm spasms lasted.

I let him calm down and said, after slowly withdrawing the dildo, "John you just lie there for a minute while you recover, and I clean up."

I stood up, pulled off the condom and chucked it into the bin. Took the kitchen roll and started cleaning around his hole. I retrieved my knicks and pulled them back on. I really wanted a cigarette, but refused to give into the craving as I'd given up several years before.

After making sure that everything was neat and tidy again. I helped John straighten up. Fortunately all his spunk had landed on the towel, so there was no mess to worry about.

John came back to life. "Here time to get dressed." I said holding his pants out to him.

Now he wanted to do the grateful thing, "Oh, Mimi, that was lovely. You really did a good job. Thank you."

I hung back just in case he got the idea of kissing me.

I chivvied him and finally he was dressed and going down the stairs.

"Bye, bye Mimi", he called as went out the door.

"Bye John" I waved back, and sotto voce "Smelly git".

I looked at the clock. € 180... not bad for 50 minutes.

My mentor then popped her head round the partition.

"My, my Mimi, you handled him well! You're off to a good start. I wouldn't have bothered with the douche because it takes up so much time and there's the chance of a mess."

"Yes." I said, "But there's no way I was going to stick my cock up his smelly hole without first cleaning him out."

Ricca pulled her head back, "I think you've got somebody else" she said nodding to the door.

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