How I Became a Cross Dresser Prostitute

 

When I was younger, I was a typical dude, jacking off watching filth on the Internet, trying to bed down every girl I could find and so on.

Then suddenly I’m all grown up, a young adult, working nine to five, have a mortgage and the obligatory once a month lunch with the in-laws. My wife is a great catch; 24, blond, smart, caring, beautiful and great in bed. So far she hasn’t turned down any of my suggestions under the blanket (or outside, on the roof top, airplane’s bathroom, you name it).
But still, or maybe because of this, I needed something else, something to make me feel naughty and dirty. So, I began to dress up in her underwear. Ok, I admit it, make up too. I did a few cam2cam’s on messenger, but still I didn’t feel that naughtiness I was looking for.

Apart from sex, the other great interests I have are fast cars. In my garage, together with my daily driver 5-series BMW, is my race tuned, street legal, first model M3. My pride and joy. Unbelievably fast, but being almost a race car, it is vulnerable. That’s why I don’t use it daily on daily basis.
My wife had another overseas assignment of couple of days, and I had to stay home. I took her to the airport and drove back home. I opened the computer and began to look for porn. I wanked off for a while, but I grew increasingly horny. I went to her dresser, put on her white stalkings, bra and a real see-through g-string.
I opened her makeup kit and applied a bit of eye liner and lipstick. Then I got from my hunting rifle safe my most guarded secret: a long blond wig. Now my cock got really hard. I was all four knees in our living room, toughing my arse, but still I wanted more. Hmm…
An idea came to my mind, no, too sick, I.couldn’t. Bullshit, of course I can.
I put on my sneakers and opened the apartment door. Quick look around, no one there. Good,
I ran as quickly as I could to the staircase, couldn’t risk getting caught in the elevator and went to the garage.
One one there, good. Ran to the M3, the 5 series was parked outside. Just when I was looking for the key a car came into the garage. My heart nearly stopped. Here I am, Mr. Jones of 7B, dressed up as a hooker with a hard on, how do you do? I crouched as the car passed by. Huh… that was close. Now I noticed that my cock seemed to like all this, it was so hard it ached.
I quickly entered the M3, and started it up. Normally I let it warm up for a few minutes before driving it, to treat the race engine better, not now, I just took off. The rough idle and the booming sound always attracts attention and people come to chat. Normally I’d be flattered, but as you can imagine, now wasn’t the best time.

Got out of the garage and headed towards the freeway. I was cruising below the speed limit towards the local industrial park where there was always a good number of hookers at night. I was wanking off while driving there, making girly sounds. It turned me on big time. I really had to watch for not to cum yet.
Got to the industrial park and headed to where the transexuals normally hang around. I had never been with one, but they had recently started to turn me on more than anything. I had a slight tint on the windows so I was able to admire their bodies and the huge cocks while remaining hidden. I had my legs spread open and my throbbing cock in my hand. I kept on driving and wanking. I nearly hit a van, it’s not easy to get your foot back to the race clutch when jacking off in stalkings.
I went around the block and reached a street with no hookers on it and decided to give the car a bit of stick.
An amazing race car sound echoed between the buildings and then suddenly… the engine shut off. Clutch in and let the car roll, looking where to park it. Saw a parking place of some company and steered the car there.

Anger filled my mind, I knew exactly what had happened, the ECU had shut down, I told the mechanic to make sure to order the motorsport version, which of course he hadn’t and we had to put a standard ECU in, that idiot! It had to be reset with a tool, which I didn’t have on me. Great!
Took a deep breath, trying to calm down. Ok, have to come back for the car tomorrow and reset it.
Then it hit me like a sledgehammer. I’m sitting here in full slut wear, no cellular, no wallet, no money. Oh shit! Please no, shit!
I began to tremble, what the fuck am I going to do now?
I looked around. Suddenly my fellow Johns turned into predators and I into their fucking prey. What if I get raped or something? Now I really got scared.
Maybe I have my race suit in the trunk! Looked around, no one there. Jumped out, opened the trunk, hoping to see the suit. Empty. Shit! I closed the trunk.

I heard a car stopping. Too scared to turn around. Definitely the new M5, I could recognise that V10 anywhere.
A guy speaks:”Hi baby, you’re not trying to steal my buddy’s car are you?”
I didn’t answer, who the hell was this? Do I know him? My cock got hard again.
Guy continued:”That’s a famous M3 in our forum, can’t steal that one, everybody knows it.”
Good point, never had though about it like that.
“Come here baby, I’ll give you something better. 50 bucks, come on”
I did my best to imitate a girl and gave my first reply as a girl:”Fuck off!”
“You fucking whore!” and the car took off.
I was scared shitless. Only then I began to think that I have been called a lot of things, but never a whore before. Crap!
I really began to feel restless. Definitely standing next to my M3 wouldn’t help, so I decided to walk away from it. I could feel my g-string rubbing against my asshole, which got me even harder. My balls were all over the place and my cock pointing out of the panty. Really girlie sight…

As I was walking another car slowed down. I turned my head just enough to see. It was a Taurus. The window rolled down. A man of maybe 45 years of age smiled at me. He seemed cool.
He spoke to me:”Hi beautiful. How’s it hanging?”
Never better said… and that got me hard again.
“I have been better.” I replied truthfully.
“Wanna come closer? I want to see you better.”
I began to feel aroused more and more. I think it was how he wasn’t rude; he treated me like a lady. I walked to his car. He leaned towards the window.
“My name’s Jake”, he said, “what’s yours?”
My name? I had never thought about that. Can’t say Robert really. “Robin”, I replied.
“Can I touch your boobs Robin”, he asked.
Now my cock was so hard that I was worried about damaging his door. I surprised myself by answering.”Sure honey. Is that all you want to touch?” Can’t believe I just said that.
“How much for half an hour Robin?”
How do I know? Shit! I tried to remember how much I paid the last time. “100”, I replied.
“Sounds like a lot to me”
“80”, I said immediately. I can’t believe I’m negotiating a price for my ass. This slut talk got my cock dripping already.
“Done. Jump in baby.”
My heart began to pound, hard. I opened the door and sat on the front seat.
“Where do you park normally honey?” he asked.
How do I know? I haven’t ever been the payee. “Anywhere free”, I replied.
He drove the car to a spot between two warehouses.
Now my heart was close to exploding, as was my cock also. He turned off the engine.
He began to touch my bra and my legs. My hand went to touch his crotch. I could feel his hard cock. I opened his zipper.

His cock jumped out like a Jack-in-a-box. A girlie sound came out of my throat before I dove for his cock. I wanted it deep in my mouth. He moaned as I deep throated his cock.
Suddenly I felt how he wetted his middle finger on my saliva, spread open my ass cheeks and put his finger in my ass. I nearly cummed.
He kept on fingering my ass while I enjoyed his cock. I couldn’t stop sucking it.
After a few minutes he stopped and said:”Do you mind if we use my condoms?”
Condoms? I knew I forgot something. “Sure I answered.”
He gently guided me to the rear seat, where I went on four knees, spreading my ass as wide a possible. What am I doing? That though was shortlived as his cock started to push against my virgin ass. The pain mixed with pleasure. I had never felt so dirty in my life.
Suddenly my ass gave in and his cock entered my ass so deep that I cried out. He stopped, letting my ass to get used to the intruder. I began to move my hips, to get his cock moving in my ass. Drops of pre cum fell off my cock. He wiped them off and rubbed it into my face.
Now he started to fuck me. Oh god how good it felt. His cock felt hundred times bigger than it was. I was weeping in pain and pleasure. He squeezed my tits and wanked my cock, while pounding my virgin ass. I tried to spread my ass as open as possible, I wanted him deeper in my arse. I felt so humiliated having a cock inside me, but still at the same time so horny. My head was against the leather interior of his back seat, without even noticing, I was licking the leather and my saliva was all over the seat.

My first client, can’t believe this was happening to me, was pounding my ass. He leaned forward and licked my tongue with his. I cock was throbbing so hard now.
“I’m going to cum soon” said my client.
“Wanna cum on my face? 20 bucks more.”
“Yeah! Done!”
I pushed him out of my ass, which suddenly felt as empty as some organ had been removed and turned around. I pulled off the condom and pointed his milk gun to my face and began to stroke him with one hand while fingering his butt with the other. Soon he shot a very generous amount of cum on my face and chest. I began to rub it all over my body. I felt like a bitch. Well, technically I suppose I was one.
My client finally caught his breath and began to get dressed. Suddenly I noticed that I was covered in cum.
“Got any Kleenex?” I asked him and he handed over a box. “Keep it.” he said. I had a feeling I might need them all, I was so wet.
My first client pulled his wallet out and handed the 80 bucks we had agreed, which I took. Then he handed another 50 saying:”that’s for the bukkake and the experience. You were fantastic. You were so tight I thought it was our first time.”
“Thanks for the compliment.” I replied. How little did he know…
“Can I kiss you good night?” he asked.
I looked at him, pulled his head closer and gave him a long passionate tongue kiss. My cock got hard again.
“Where do you want me to drop you baby?” he asked.
That was a good question. I definitely should say home, or even better, somewhere near home. I could sneak home undetected. I surprised myself saying:”Here’s fine love.”

I got dressed and checked my make up. Still ok. I could smell his cum on my face, which got my cock hard again.
I stepped out of the car. I saw the other hookers walking up and down the streets and flashing their goods to the passing cars.
A car stopped in front of me, a Golf. A blond girl opened the window and looked at me, interested.
“You’re a CD, right.” she asked.
“Not interested.” I replied. What did I just say? That girl was gorgeous! But my Willy was soft as a cotton candy. What was happening to me? She took off. This was getting really weird.

I heard it coming from far away, a Harley Vrod. As it came closer I saw it was more specifically the Night Rod. The name reminded me of myself. Damn.
The guy riding the bike was about my age, probably around 25-28, seemed to have a nice body. He was wearing shorts and a hockey shirt, no helmet.
“What’s up girl?” he said. Well, I knew something that was up…
“I’m good. What can I do to please you?”
“Me nothing, but my buddy’s getting married in a week, and we’re throwing this thing for him. We got him a stripper but we wanted to shock him a bit also, you know, a joke.”
“Ok.”, I replied, not really sure how to deal with this.
“So, could you come and do a striptease and the girl, I mean a real one, would take it from there.”
“When? Where?” I asked.
“Now. The place is about 20 minutes from here. I’ll pay you 200.”
“300. A flat fee. Sex or not.” I hoped there would be so, my cock and ass wanted more.
“Done. No sex for you babe, the guy’s straight as a judge. Got your clothes?”
“Sorry, this is all I have.”
He looked at my slutwear and thought for a while. Then he removed his hockey shirt and handed it to me.
“Here, put this on. We’re going to a condo, got to look a bit more presentable.”
“Sure.” I replied.
Now I got to see this guy’s body. He had a lovely six pack for abs and a smooth tanned skin. My cock got hard again. I began to breath faster. I put my hand on his cock while touching his short hair with the other hand and asked:
“Wanna test drive me first?”
He gently pushed my hand off his cock and replied with a smile:”Barking at a wrong tree honey. Sorry.”
I wanted this guy so bad!

I jumped on his bike. He started the bike and we took off and headed to the freeway. It was a strange feeling to be a passenger on a bike, I have my own bike and I was always the one riding it. Also, not having anything except a g-string to stop the wind hitting my genitals was weird, but arousing also. Especially with the wind lifting the hockey shirt up and the whole world seeing my g-stringed ass. Luckily I always kept my legs and ass shaven, probably a habbit from my swimming days.
I kept on looking at this gorgeous guy sitting in front of me and his bare skin. I wanted to put my hands in his shorts and feel his cock. I restrained myself. But my cock was up.

Soon we turned off the freeway, went through a neighbourhood and got to a high rise condo building. We entered the underground parking. We finally parked the bike next to a Porsche 911 cabrio. So the kids have money, I thought.
He took my hand and took me to the elevator where used a key to take the elevator to the penthouse. Interesting.
“Ok, so when we get to the top, stay in the entrance. I’ll blindfold the guy and then you come out and do a little friction dance and strip. When he freaks out, we’ll bring the girl out and I’ll call you a cab home. Ok?”
“Ok.”
The elevator reached the penthouse and the door opened and rock music and smell of illegal substances filled the air. Party time. It sounded like there was at least 10 people in the party. I got aroused again; the idea of stripping in front of 10 young guys turned me on big time.
A big sheer was heard from the living room, as well as some cat calls. I began to touch myself and finger my butt, I was so horny.
Soon another guy appeared. He looked at me like if he had seen the most amazing thing.
“Oh shit! Look at you man! I mean, baby.” he exclaimed.
“I’m Mark by the way.”
“Robin.” I shook his hand.
“Shit, this is sick man! Love this! He’s gonna be so shocked. Can I see it?” He seemed all excited about what was going to happed.
I pulled my hard cock out of the G-string and stroked it.
He laughed excitedly and exclaimed:”Unreal! Fucking brilliant!”
“Come baby, do your thing!” he said when he took my hand and guided me to the living room.

The room went crazy. Everybody shouting and jumping. The guy who had picked me up brought the girl in at the same time. Everybody’s eyes were on me and on the prank.
Then I saw the target. I stopped on my track. On the sofa there was the most amazing black guy I have ever seen in my life. His body was undescribable. He wore only shorts, showing his muscles. He had a bold head, a gold chain around his neck and ear rings. My cock was going to explode.
People were sheering like crazy.
I saw a bottle of Vodka on the table, opened it and drank a good load, I’d need it. People loved it. Next I took off the hockey shirt and kicked off the sneakers.
I was left only with the bra, G-string and the stalkings.
I took the bottle and went on four knees on the floor. I approached the guy and kissed his stomach. He surprised at the contact. God how tight his abs were. His cock seemed to react also, it was huge. Mine was about to explode.
I kept on licking his skin and when I got to his right nipple, I gave it a bite. He moaned. People were going off the scale. A bright light of a video camera blinded me, great, I was being filmed. Just great. Actually I didn’t care, I was in the seventh heaven kissing and licking this guy. What I really wanted was that huge cock hidden in his pants.
I moved the bottle under his nose so that he could smell the Vodka.
“Vodka, yeah baby, give me some!” he said.
Now I noticed that the party had also tied his hands behind his back. Good.

I poured Vodka in my mouth and then slowly dripped it into his open mouth. I repeated it once more and when all the liquid was in his mouth, I kissed him. The party was yelling so loud that I was worried for my ears.
“Fucking yeah!” shouted the hero.
Suddenly the party began to shout:”Panty off! Panty off!”
I turned to face them and slowly removed the G-string, showing my rock hard cock. Everybody screamed, yelled and pointed at my cock.
I began to rub my ass against his naked skin. He seemed to like that. I looked down ans saw his huge cock bulging in his shorts. God how I wanted that thing in my mouth.
I stepped up on the sofa and pushed my ass against his face. He began to kiss and lick it. I pulled my balls and cock forward so he wouldn’t notice them. Few times his tongue touched my asshole, sending jolts through my body. I was dripping pre cum.

And that’s when somebody pulled off his blindfold.
“What the fuck!” he shouted when he saw my cock 4 inches from his face.
“Get this faggot off me!”
The party was laughing their butt off and the video camera got a good close up of a very shocked man.
“I’ll fucking beat you up!”, he shouted at me.
Now the girl stripper went to do her bit. drawing most of the attention.
The guy who had brought me there came to me still laughing:”Off the scale! That was awesome! Did you see his face?”
I was more worried about the party boy, he probably really wanted to beat the crap out of me.
“Just give me the money and I’ll be gone.”
“What? Oh yeah, hold on.” He opened his wallet and gave me the money. He also handed me the hockey shirt and said:”You keep it.”
“Thanks.”, I said, and opened the elevator.
I got in and selected to ground floor. I realized that nobody had called me a cab. I’d find one on my own, didn’t want to go back there to be beaten up.
The doors opened and I walked through the lobby and through the front door.

I just got outside when I heard somebody shouting from the rooftop, 30 floors up.
“Yo blondie, hold on!”
It was the party boy, shit. Oh, well. I was going to get whacked, probably deserved it. Since I forgot my sneakers upstairs in the panic, I couldn’t outrun him anyway. Take it like a man I thought.
The guy run out of the building and came to me.
“Yo!”
I took a defensive step back.
“It’s ok baby, I’m not gonna hurt you. You just shocked the shit out of me. I’m Chris.”, he said giving me his hand.
“Robin.” I shook his hand.
“Hey listen Robin, come up with us, ok? Stay and let’s have some pizza, few beers and forget about this ok? No hard feelings.”
Well, I still wanted to feel some hard of his but that was not going to happen.
“Yeah ok.” I replied.
“Right on!”
Together we went back to the elevator. Just then I noticed that we were both a bit drunk.
While standing the in the elevator, I looked at my naked feet and we I looked up I saw Chris looking at my reflection in the mirrored elevator. Was he checking me out?
“Crazy party, huh?” he said.
I was left with a doubt. Probably he was just staring at me, not believing what just happened to him.

We got back to the penthouse and went back to the party. The stripper seemed to want some extra cash, she was blowing two guys on the couch. Somebody was smoking God knows what in a semi stoned state under the table. Everybody seemed to be very drunk.
“What do you want to drink Robin?”, Chris asked.
“Tequila, lots of it.”
Chris looked to the living room and then said:”None there, come, there’s some in the kitchen.”
I followed him to the kitchen. Just when I was about to enter the kitchen a guy came out, very drunk, with a beer can on his hand.
“Heeeey! It’s the cock queen!”
“Yeah what ever.” I replied.
“Hey listen, you have the best looking ass in the world. Don’t tell anyone I said that, ok.” After saying that, he walked out and joined the party.
“Actually you have a great ass.” said Chris, smiling.
“Thanks.”
He poured me Tequila. And some for himself too.
We downed the drinks.
“Come on, do a real striptease!” he said and took me back to the living room.

Party was wild there, somebody was boning the stripper already and somebody had passed out behind the couch.
Chris lifted me on the dining table like if I was alittle girl, he was strong.
I was so drunk and horny that I stripper off my clothes and left only the stalkings on.
The stripper had finished with the guy and joined me on the table. Together we danced and rubbed each other.
I don’t know how long we had danced there, but I had to rest, the room seemed to spin.
I saw Chris sitting on the couch and crashed next to him. Without even thinking, I turned to cuddle him. To my surprise he pulled me closer.
“Do you always have that hard on?” he asked me.
Only then I noticed that my cock was hard again.
“Only when I want some cock.” I replied.
He looked into my eyes and then turned his head away when somebody else jumped on the table and began to breakdance on it.

Suddenly I felt someone touch my naked ass. Playing with my asshole with his finger. It was the gorgeous guy who had picked me up from the street. I moved my leg, opening my asshole more for him. He pushed his finger deep in my ass. I moaned, it felt so good. I put my hand on his cock, it was hard. I slipped my hand inside his shorts and felt his cock. It was wet and throbbing. He pulled his finger out of my ass and put it into my mouth. The taste of my own ass turned me on even more.
Just when I was about to turn to face him, Chris barked at him:”Fuck off! She’s mine!”.
I couldn’t believe what I just had heard. The other guy seemed to react to this sudden outburst and quickly stood up and went to harress the stripper.
I turned to look at Chris. He was drunk, but still he was definitely looking into my eyes.
I slowly gave him couple of soft kisses on his lips. He didn’t pull away.
I kissed his ear and whispered:”Chris, fuck me.”

He stood up. I was sure he was going to throw me out.
Instead, he took my hand and walked me to the bedroom. I saw my reflection on the mirror. I was naked except the stalkings. Chris looked so good that I almost cummed there and then.
We reached the bed. Without wasting time, I dropped on my knees and pulled his shorts down.
I wasn’t prepared for the monstrosity that jumped up. His cock was absolutely massive. As I was on knees, it seemed like the Statue of Liberty to me.
I crabbed it with both hands and shoved it into my mouth. It barely fit. I began to suck it, while touching his unbelievably fit body and finger his asshole.
He moaned and pushed his cock deeper into my mouth. My mouth was dripping saliva on my chest. I pulled his cock out of my mouth and began to lick the shaft. I couldn’t believe the size of that thing!
Now I stood up, crabbed his head and kissed him passionately. I felt our cocks touch.
He slapped my ass. It felt so good.
“Again!” I begged. Another slap.

I pushed him on the bed and pushed his knees to his chest. I went flat on the bed and began to french kiss his asshole. It was so warm and sweaty.
“You like that?” I asked Chris. He didn’t reply, just kept on moaning. I tried to open his hole wider but i was too tight, so I pushed a finger in instead. Now Chris really moaned.
I moved so I could keep on fingering him while sucking his cock.
Chris had his eyes closed, moaning and rocking his body.
He opened his eyes and sat up.
“Want to be fucked Robin?”
I got scared, how the hell can that thing fit my ass.
Without waiting for my answer, he flipped me around on my knees and moved behind me.
He spat on my asshole and soon I felt his massive cock touching my hole. He began to push his cock in. My ass resisted, the thing was monsterous. He pushed harder, it began to hurt. Suddenly I felt how his huge cock entered me. It felt like that thing could reach my lungs.
He began to ram me, faster and faster.
I couldn’t even move, my ass was stretched to its limits. I felt my stomach to go upside down, he entered me so deep. All I could do was to hold on to the bed sheets and enjoy.

I saw myself in the mirror and felt so ashamed, dirty and cheap. I loved it.
Chris kept on ramming like a machine.
After what seemed like an eternity, he whispered:”I’m gonna cum.”
I was so deep in the pleasure that I barely understood the words and didn’t even reach before he pushed his cock so deep in my ass that I cummed.
I haven’t ever cummed so hard in my life. The bed sheets were drenched in my cum.
At the same time Chris cummed in my ass. It felt like if someone was hosing my ass with a shower nozzle.
I felt his cock throbbing inside me.
Slowly he pulled his cock out of my devastated asshole and fell down next to me. He fell asleep or passed out, I wouldn’t know.

I looked at his amazing body. I took his now sleeping cock and began to lick and suck it clean. I touched my asshole, it was still open like an owen. Sperm was dripping out of it.
I looked for something to stick into it and found a mobile phone. I would never have even thought about trying a phone, but after the last hour or so, my rear door had reached totally new dimensions.
I began to slide it in and out, which was easy as my ass was still dripping cum. I began to suck Chris’ sleeping cock while phoneing my ass. Even when the monster was asleep, it was huge. I pushed it as far down my throat as I could. It didn’t take long for me to cum again. I sprayed the cum on the sheets, already wet from the stuff.

I saw there was a bathroom connected to the bedroom. I entered and saw myself in the mirror. What a mess. I was surprised the wig had stayed on. My make up looked like a racoon and my body was covered in sperm and sweat.
I took off the stalkings and took a long shower.

Next I went to see if I could borrom some clothes from Chris. As I opened the closet, I found out that it was full of women’s clothes, presumably Mrs Monster Cocks.
I found a pair of really low cut and tight jeans. I tried them on. They were seriously tight for me.
Next I found a top, which looked almost like a sports bra, it was that short. And a pair of sneakers.
I also found make up and retouched mine a bit.

I wrote a note to Chris saying that it had been the best fuck of my life, true, and left him a list of the clothes I had stolen. We don’t want the groom to get into trouble, do we.

Last look and I went out of the room. In the living room the party was still on, few people had passed out though. Nobody noticed when I walked to the elevator.

I pressed the button for ground floor and looked at myself in the mirror. I was a cross dresser hooker.