Becoming Marie Ch. 01

Story Info
How an 18-year-old starts to crossdress and cruise.
2k words
4.45
89.8k
26

Part 1 of the 4 part series

Updated 10/12/2022
Created 02/13/2010
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I'd had always liked dressing in women's undies from an early age. It was usually my older sister's panties and skirts whenever possible. When I finally left home at eighteen and moved into an apartment in the town center, it really took off. I had had a few encounters with a few guys, mainly glory hole fun in the local cottages. On a few occasions I found the odd pair of stockings behind a cistern also which I would take and wash and then wear myself while wanking off.

Eventually I got the courage up to go into the town and start buying my own lingerie and skirts. I soon built up a nice collection of stuff which I kept in the wardrobe for my wank off sessions. I'd not gotten a wig or even make up yet, as I was content in just dressing in undies and wanking at the time.

When visiting the local cottage near the cemetery, a guy told me about one in the center that might be worth trying. I got up late in the morning and was feeling especially horny. I thought I'd try the cottage later on in the day. I had a long hot bath and even though I don't have much body hair I shaved off what little I did have. I don't drive, so I cycle everywhere. I usually wear lycra shorts and use this excuse to shave my legs, if anyone asks. I decided to shave everywhere today just leaving a tuft of hair above my cock.

After my bath I fixed my enema attachment to the shower and went about the business of cleaning out my ass. I thought, well if nothing else happens I can always have a dildo session when I got back. I got my newest basque out of the wardrobe, a nice tight cream one I had bought the previous week and found a pair of see through pink panties to go with it. I then sat on the bed and rolled a brand new pair of white stockings up my smooth tanned legs. Just rolling them up my legs got my cock twitching. I put my baggy tracksuit on and at 4:45 set off into town to find the new cottage I had been told about.

I arrived a half hour later and entered the toilets casually. I saw a stall for pissing and three empty cubicles but not a single person in sight. I thought this is not going to be any good but I might as well wait for fifteen minutes. I entered the end cubicle and looked at the walls. There was a couple of messages on there asking for someone to suck their cocks and a little peephole at roughly eye level when sitting down. The main thing about the wall was where the toilet roll holder was supposed to be, someone had removed it and made a gloryhole into the next cubicle.

I sat down and undone my tracksuit pants and rolled them just to the top of my thighs, careful not to show anyone my stockings. It looked like I was doing a number two. I'd been waiting about five minutes, listening to a few people coming in, having a piss in the trough then going out. I was thinking what a waste of time this was, when the cubicle door next to me opened and then closed. I casually looked down at the glory hole and seen a nice pair of business style shoes then a pair of suit pants dropped round the guys ankles.

It was now 5:30 and I knew that these toilets would be closing at 6:00. I hoped for some action and thought, oh well if this guys no good. I'm going home to another wanking session. It was then I looked through the eyelevel peep hole and seen his eye looking through at the same time. I thought good sign so I slowly poked my finger through the glory hole to see if the guy was interested. I knew if he wasn't he'd probably pull his pants up and leave. I wasn't that worried of an attack by him so I just went for it. He in turn put his finger through the hole leaving the decision up to me if to go further.

I was just about to drop my tracksuit bottoms down to reveal my stocking clad legs when a note popped through the gloryhole wrapped around a pen.

"A,S,L" was wrote on the note meaning age, size and likes. I sat back down and wrote "18,7 inch, sub into undies," and passed it back through the hole. A minute later the note came back through the hole with "u dressed now," written on it. "Yes" I wrote back and passed it back again. I seen the guys eye appear at the gloryhole so I stood up turned away from him, undoing tracksuit top zip and then turned back round to show him what I was wearing.

He pulled away from the hole and I just stood there wondering is he going to leave, does he want me to put my cock through the hole, or is he going to put his cock through the hole. A minute later the note came back through. Written on it now was "I have a place to go right now if you fancy some fun. Just follow me out ok?" I quickly wrote on the note, "can I see your cock please," and passed it back. I sat back down and then sure enough the guy got on his knees and pushed his dick through the hole. I didn't touch it but it was about 6 inch long and already rock hard. He quickly pulled it back through, pulled up his trousers, flushed the chain and left the cubicle. I quickly done up my tracksuit, flushed and started to leave. The guy was waiting at the sinks and then left slowly to allow me to follow. I casually followed after him and he lead the way into the nearby multistory car park. We went up two flights of stairs and then he got to his car, got in and wound his window down. I walked past his car window and he said

"You coming to my place then?"

"Where would we be going?" I asked.

"To my office a couple of miles away. If you want?" he replied.

He was mid thirties, nice looking dark hair, good looking and looked nice in his business suit so I said

"ok," and got in the passenger side. On the drive to his office he told me his name was Kevin and he loved cross dressers. He asked me if I had a girlie name and I said I went by the name of Marie. I hadn't previously thought of a girly name but Marie was the first name that came into my head.

"Ok Marie, when we get to my office I'm going to go in first, check every ones left and you wait outside. When I switch the lights off and on twice, come in up the stairs and enter my office, but leave your shoes and tracksuit outside the door, right?."

"Right oh," I replied. Then two minutes later we pulled up outside an office block. He pointed out his office to me then we got out of car and he went into the building. After a few minutes the lights went off then on then off then on. I entered the building and went up the stairs. There was only one door so I took my tracksuit and shoes off and knocked on the door.

"Come in Marie," I heard through the door. I opened it and went into a big conference size room with a big table and chairs in the middle. Kevin was sat at one of the chairs completely naked with a cock ring round his ball sack.

"On your hands and knees and crawl to me Marie" he said. I immediately did as I felt the blood start to rush to my cock. When I got to his feet and looked up at his lovely smooth cock he grabbed hold of my head and started to shove his cock towards my mouth. I love masterful guys as it brings the slut out in me. I happily took his cock into my eager mouth. He didn't hold back and started shoving it down my throat forcing me to gag. I tried to pull back but he just kept pumping it into my throat. I thought I would puke but all I could do was keep slavering over his dick as he face fucked me hard. After five minutes of constantly being face fucked, my jaw was aching and his balls were covered in my saliva.

"Get on the table Marie," he said. He released my head from his hands and helped me get on the table as I caught my breath. I lay on the table in my lingerie and looked at his saliva covered dick and waited for his next instructions. He rolled me over onto my front and pulled my legs to the end of the table and then started feeling my pantie covered ass, before pulling them off my ass down my thighs and then fully off.

"Any lube Marie?" he asked.

"No, sorry," I replied. He went to his desk and came back with a tube of cream and squirted a big dollop onto my ass crack and began to work it into my hungry hole before inserting first one then two fingers. I murmured my lust for this and pushed back on his fingers.

"Mmmmm nice clean hole you have Marie," he said, taking his fingers from my ass.

"You ready for me, Honey," he said.

"Yes please sir," I replied. He again dragged my legs off the table and bent me over with my ass pushed out and my hands flat on the table. After the face fucking he had given me I was expecting a hard rough fuck but to my pleasant surprise he slowly entered my hole and gently worked the head in and out teasing my ass. He pushed half of his length up me before pulling practically all of his cock from my hole. He slowly picked up the pace till eventually I could hear his hips slapping against my ass cheeks as he fully fucked my hungry ass. I was loving being his slut and my dick was leaking pre-cum all over the side of his table as he increased his pace.

Suddenly he stopped thrusting and pulled his cock from my ass leaving me bent over the table. He came round and climbed on the table and told me to ride his cock. I got up on the table and slowly lowered my asshole to his rock hard dick in the reverse cowgirl position. I took the full length of his cock all the way in one smooth motion. He then placed his hands on my hips and lifted me till the head was just in my hole and then began to pump into my ass while i knelt over him. After five minutes of steady fucking he said

"I'm gonna shoot Marie. Where do you want it, Honey?" I immediately pulled myself off his cock and took his pulsing dick into my mouth.

"Oh God, you dirty slut, ass to mouth, you kinky bitch," he said as I wanked and sucked his cock till he shot four huge jets of spunk down my throat. I swallowed every last drop and then licked his cock and balls fully clean while he laid back with a huge smile on his face. After getting dressed up and getting my tracksuit and shoes from outside the office he took me back to my cycle and said

"You were fucking awesome. Here's my number. give me a ring anytime you fancy some more, Marie," I thanked him and got back to my apartment. Marie was born.

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AnonymousAnonymousover 2 years ago

Wonderfull men like this are good. I started wearing girls clothes when i was about fourteen i was lucky that i had three sisters so lots to borrow. My first suck and fuck was a friend in my room who i dressed for and i loved being a girl for him. Every now and again my sisters and Mum would have a clean out of clothes and bags of things would be left in our garage to go to charity shops and id pick items out and put them in the attic as nobody except me went up there because of spider or mice so i knew it was safe to put them there. I started really going further when i got a car as i had more freedom then and kept an outfit hidden in it so that if i needed to dress when out i had everything i wanted. I would go to places like parks with toilets and places i got to know had men wanting gurly fun and loved sucking cocks and having my bum fucked and man filling me with his sperm. One place which became my favourite was an overnight truck stop which had toilets and showers. I didnt have to dress as i just went in and got naked and had a shower and it was clear what i was there for as i was a fully shaved femboy and men loved sex there and some took me back to the sleeper in their truck to give me more. I loved guys who called me a dirty slut and cock socket and that made me feel hotter. I would go there every night if i had time as there are plenty of men wanting sex but i still like dressing up and having a man take me like i was a girl.

AnonymousAnonymousalmost 13 years ago
first time as a cd

liked the story very much. From my experience as a Crossdresser all the things certainly ring true. I started out with cruising the local truck parks and parks in general. When you find a guy that truly likes sex with crossdressers the experience is fantastic. When you get the cock in every hole from a total stranger you realize that you've truly become a cum bucket slut whore that will do whatever it takes to feel your pussy being fucked just like woman's cunt. As you start out you are very hesitant to go out in your shemale outfits but as things progress you accept the fact that you are now a bitch and proud of it. It's a great feeling.

jenniann469jenniann469about 14 years ago
I'm a CD too!!!

Great sexy stroy... I luv to be dominated also... Nothing better than a full ass and mouth... jen

AnonymousAnonymousabout 14 years ago
Hot Story!

Love cross-dressers as they are such dirty little slutty tramps, and you have certainly captured the genre. Keep it up!

AnonymousAnonymousabout 14 years ago
Hot!

Very nice... looking forward to more stories from you! I love the dress up!

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