The First time made me a Slut

Introduction:

A story of a cross dressing young man who’ first outing was more than he bargained for.

True story of my first time..

The first time i went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to pull it down as cars were whizzing by. I walked or should  I say wobbled the half block to the door. I opened the door and walked towards an older man behind the counter who had put down his book and was smiling at me.

What can I get you beautiful”  He asked?  I blushed at the compliment and his smile got wider. I pulled a five dollar bill from my purse and asked for tokens. There were four men scattered in the store and all had turned to watch me come in and walk to the counter, and when I asked for tokens three of the men headed through the arch that  said arcade before me. The man behind the counter told me :Have fun and if you need anything just ask me. I blushed again and headed for the arcade as he chuckled and everybody there heard my five inch heels coming,

They watched me walk into the arcade. There were no doors on the booths and there seemed to be about twenty men looking at me with big smiles on their faces, a couple of them whistled. I darted into the first doorway without a light above it.

I took money from my purse and fed it into the slot and just as the video started a man walked in, lifted my skirt and gave me a hard swat on the ass. “That is for teasing us” he said. so there i am standing there with my ass cheek burning, but not in a bad way, in a kind of daze when he says “Well what do you have to say for yourself girl”

I take my first real look at him and he is big so big and hard looking, it scares me. I say “Im sorry” but it only comes out as a squeek and I try to squeeze past him to get out of there. “Not good enough” he says and stops me by grabbing my arm and spins me around, he lifts my skirt again and pulls my panties down and slaps my ass again and says “Count”. I could not think and again he spanks me and says count. there is a lot of other men outside the booth and I am so embarrassed, he slaps my ass again and I cry out “one”.

I hear laughing from the men outside. he keeps slapping my quickly reddening ass, and head turned away from the men outside the booth I count.when I get to twenty he stops. I have tears in my eyes. he says good girl really soft puts an arm around me turns me around and starts kissin me, forcing his tongue into me and I let him.

I feel his whole body pressed up against me.He feels so solid and I can feel his cock, it is hard and pulsing against my belly button, a lot bigger than my teeny thing and I am so turned on I started moaning into our kiss and pulling myself against him harder. He sticks a finger in my mouth and says “get it wet”

. I suck on his finger like I had his tongue his other hand on my ass spreading my cheeks. he takes his wet finger and pushes it all the way inside me, I muffle a scream into his shoulder when i hear a man say “Oh she really likes that”.  and I remember all the men watching, so embarrassed then so incredibly turned on  by the looks of lust on their faces and how much they wanted me. I looked out at them while wiggling my ass on his finger smiled and said “yes i do”.

I felt like such a slut, it was fantastic. my man turned me towards the wall and bent me at the waist so it was put my hands against the wall or fall. then a bottle of lube was squirted against my ass and then one hand pulled behind me and put on his oh so warm and hard cock him telling me to “put it in”. as his other hand raised my skirt again. I put his hard , hot cock against my hole and started pushing back but it wouldn’t go in just kept slipping. then another man was holding a little brown bottle up to my face, when I looked at him he smiled and told me to “breathe it in through your nose honey. it will help”

I started breathing it in and felt that incredible rush of heat traveling down to my hole and I pushed back hard and he was deep in me. the man who gave me my first poppers started kissing me and I was so glad after the way he was making me feel with that little bottle. my blouse and skirt pulled over my head, panties around my ankles in garter stockings and heels a mans cock so deep inside me another mans tongue down my throat then someone crawling between our legs and taking my peenie in his mouth and a whole group of men watching this happen to me and waiting to do even more to me.And in my ass the man was thrusting harder and deeper and the stuff the man kept putting under my nose to sniff had me so turned on my ass was moving back to meet him. I was coming into the mouth of the man underneath me. the pain in my ass had become such an intense pleasure that my legs were just shaking. And I was moaning so loud that the man with the poppers said “put my cock in your mouth and moan on that”.

He pushed my head down right on it and said “open up slut” right then the man behind me thrust so hard my mouth opened and the cock was thrust to the back of my throat making me choke up some phlegm and man said that’s right baby get it nice and wet I tried to push off with my hand but the man behind me grabbed them and pulled them behind me using them to get even further up inside me and the man in my mouth he started forcing his cock down my throat it completely blocked my Airway and I could not breathe at all I am trying to scream and he just says “slut stick your tongue out lick my balls when I go that deep”.

He pulls out I get one breath before he’s thrusting back in again. and there’s a couple sharp smacks on my ass and The Man Behind Me says got to keep it pink he’s pulling his cock all the way out of me and ramming it all the way back in. I catch a quick glimpse of a lot of the men watching me and they are all breathing hard stroking their cocks, and I wonder how many are going to fuck me before I can get out of there and I couldn’t help the wiggle my ass.

. The man in my mouth thrust deep into my throat and held my head, his cock started swelling and he was shooting his cum down my throat I tried to back up so I can taste it but he held me there after about five squirts he pushed my head off and handed me the bottle saying “you’re going to need this girl”.

He moved away then there was another cock in front of me and it was huge I took three quick hits off the bottle then looked up at the man the cock belong to.  He saw the look of fear in my eyes and said “darling you ain’t got to take it all but get it good and wet because I’m going to have that pretty little ass when your other gentleman caller pulls out.” And he chuckled again seeing my eyes go wide. I took another quick sniff off the bottle and tried to get the cock head into my mouth but my lips would not stretch wide enough he had his hand on the back of my head and with a little push he got the head of his cock in my mouth.  He had to be as big around as a soda can my teeth were raking him,  causing him pain cuz I could not open my jaws any wider so I pulled my mouth off his cock as the man behind me pulled hard on my hips and his cock started pulsing inside me The man in front of me saying “better hurry darling or you are going to get it dry”

I grab his cock and start getting as much spit as I could on it. The men watching started laughing and saying “look at Her Go”. I kept stroking his cock real fast with my hand hoping I could get him to come, meanwhile the guy inside me was filling me with his cum it felt like a lot. I was glad, it was going to be extra lube for when this other man tried shoving his Monster in. The man behind me pulls his cock out and I feel a cool breeze rush in for a second and some cum seeping out.

He pulls up his pants, slaps my ass again and says “hope to see you again in here.” and the man that I would never forget the man who took my ass cherry, walked out the door and was gone. I wanted to race after him, He had opened up a world for me that I had only been looking at from the outside, and for that I owed him all he could ask of me. But before I could even straighten the man with the big cock moved around behind me grabs a cheek in each hand spread me wide he said “little girl that does look pretty tight and I will say sorry before hand”

. I told him “no you can’t do this”. and he just chuckled and said “girl when you came up here in them panties and swinging that upturned ass with them heels you gave up all right to say no” and took three of his fingers and shoved them into the second knuckle I screamed and I heard all the men start laughing again . and the big cocked man Bent down his hands behind my knees and lifted and spread my legs in one motion. my back against his hard chest his mouth next to my ear he whispered “you ready girl?”

I said “no” his cock head forced its way in. I screamed and he said “that was the hard part “. my ass so full and in so much pain was trying to force him out it just kept convulsing and causing me more pain. and despite my ass trying to force him out he started sliding in. I think that’s when I passed out the first time. when I came to he was pistoning his cock in and out of me. my cock was standing up hard and leaking all over strings of come going this way and that as I shook as he fucked me. I had never hurt so much and felt so much pleasure at the same time . and I think I passed out again for a little while.

I heard whispering in my ear again, he was saying “hey little darling wake up this isn’t over by a long shot”. I was no longer feeling pain but so much pleasure I could not process it all. while I was out of it more lube must have been used because the rawness was gone and it felt silky smooth and the stretching feeling still there but welcome now. I grabbed the biggest of three cocks in front of me and pulled it to my mouth, he pushed as it went in and it bent right down my throat. I looked up at him in surprise, but he did not see, his head was thrown back.

He sure felt my mouth pulling off though because his hand shot out to the back of my head and slammed his cock down my throat again and held me till spit bubbles came out my nose. they matched rhythms and crushed me between them on every thrust and I struggled to breathe. they both came 3 or 4 minutes later. The man in my mouth pulling out and shooting the first jerks on my face, some in my eye where it burned and I tried wiping it out. but I only saw fogged Images through my eyes after that.

Behind me my hips gripped hard enough to see bruises the next day. he filled me up inside alot spilling out when he pulled free. another cock in my mouth I could not tell who was on me now. from that point the only thing I remember is someone giving me a soda in a paper cup and a couple paper towells that I tried to clean my eyes, the cum was dry and little came off.

{ woke up in the back seat of my car, my blouse and skirt lying over the top of me, stuffed bra, panties, one stocking and my heels gone, cum dried all over me, could not spread the fingers on right hand at first, my ass i’m sure was bleeding my knees torn and swollen, my lips the same. and despite all the pain I could not stop smiling. I had found my true calling. SLUT!!!  Hope you liked that little piece of my life, I know I did. it was raw and real and went by in a blur but was the most defining moment in my life.