Who're For The Homeless

Story Info
A sissy gets completely blackmailed and pimped!
2k words
4.18
38k
34

Part 1 of the 4 part series

Updated 06/10/2023
Created 03/24/2021
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I'm SOOO afraid of Mr. Johnson! Everything I do revolves around whether or not I think my Daddy will be ok with it! For days leading up to Friday, I was anxiously dreading what he might do to me!

I picked up a dark blue short skater dress at the resale shop hoping it would be cute or sexy enough to satisfy Daddy. I was hoping black undies would be good enough this time. Because to tell you the truth, I didn't want to stand for who knows how long in the back alley in anything reflective. Being it's my own neighborhood!

The dreaded day arrived and I was a bucket of nerves! I started getting ready at eight o'clock and by ten pm I was standing in the alley behind my house in my skater dress, black stockings and garter belt, black panties and bra with black high heel pumps!

I had curled my hair and did my make up to the best of my ability. I am actually nervous as I am awaiting Daddy's arrival! Am I pretty enough? Are my garters straight? Is my hair holding curl? Just like a nervous little girl waiting for her date, here I am, a sissy crossdresser waiting for her Daddy.

I see a shadow at the end of the alley! This alley is used by lots of my neighbors too! I step into the shadow of my fence and watch with wide Bambi eyes as the shadow makes its way down the alleyway! My heart is racing! At one point I almost go back in my back yard because I'm afraid it may be my neighbor!!

Thank goodness I stayed put as it turned out to be Daddy! He motioned with his fingers a circle. I knew he wanted me to spin around. So like last time I turned around slowly, feeling his eyes inspect me.

He then took my hand like a child and walked me out of the alley! He was walking a normal gait, but because of his height and my heels, I was walking a much quicker pace to keep up! Which, to my horror, made my high heels echo off the houses like I was stomping!! If ANY of my neighbors are out they will no doubt see us!! Daddy didn't care though as he held my hand and proudly walked his little pretty sissy through the streets!

After a couple of blocks I figured we would go through the park. But instead he began walking me toward the school!

I couldn't tell if my heart had stopped or if it was racing so hard I was feeling hyperventilated! THERE'S A FOOTBALL GAME GOING ON TONIGHT!!

Every game night there is ALWAYS kids out cruising the main drag and Daddy seems to be walking me straight to Main St.!!!

As we approach the last street we can turn on before Main St. I try to slow and just so slightly, so as not to anger Daddy, try to veer us down that street. But Daddy had nothing to do with it as he pulls me closer and puts his arm around me! I dare not challenge him! But I know my face has GOT to be red!!

As we turn the corner I see many cars that are more than likely my schoolmates out cruising!! Just as I think, "Well, at least we are walking fast." Daddy slows down, a lot! I bow my head in an attempt to shield my face with my long hair, but Daddy is keen to my desperation, "HEAD UP!" He commands in a scary voice that makes me jump and jerk my head up!

He's literally showing me off! The cars notice too! Some slow down and gawk, maybe holler "HEY BABY!" or whistle!

I can only pray that no one recognizes me as we somberly walk through the bright lights lining the schools main drag!!

It's obvious that he is proud of having me on his arm! I have so many mixed feelings as my schoolmates whistle and gawk at me!

Scared someone will notice me, embarrassed that I'm dressed this way and even a little surprised that I'm regarded as sexy!

By the time we reach the other end of school grounds I've relaxed and even started swaying my hips. Honestly... For more attention! Daddy noticed anyhow, "Good girl." He said as he continued walking me down town!

He started walking faster again and I noticed that if I kept the sway, it was easier to keep up with him.

In the store windows I saw our reflection and I was mesmerized by my feminine figure! Almost hypnotized!! He turned me down a street that ran along the tracks for a couple blocks. Which, at the end, he led me onto the tracks where I struggled to keep up and didn't notice how far he had taken me. All I knew is suddenly there was a box car off the side of the tracks!

As we approached the dark eerie looking lonesome car, I was actually a little scared and gripping Daddies arm! He led us to the open door and turned me around with my back to the car. He stepped back and looked at me as if he were waiting for something.

Suddenly a pair of hands grabbed my hair and hoisted me inside the car!! I was so startled I think I pee'd a little!! This stranger held me as Daddy climbed in.

Daddy took me from this shadow person and led me to the far wall, into absolute darkness, then let me go and stepped away!

I was SOOO SCARED!! I had no idea what was going on!!

Then suddenly, lights!! LOTS of lights!! The kind that studio photographers use!! I looked around and there were white sheets hung up and on the floor with a single stool!!

"SIT", Daddy commanded!

Sitting on the short stool made me show a lot of leg! Before me was a video camera sitting on a tri-pod and this stranger taking pictures of me non-stop!

"If I see anything less than a flirty smile for your pictures, I WILL see to it that you regret it!" Daddy threatened! Which immediately wiped the stunned look from my face and replaced it with a sexy, flirty smile. Fake, but none the less, it was all I was going to portray!

Daddy held up some que cards and said, "Read this off and make the camera believe it." My heart dropped as he held up the stack of cards for me to read.

The stranger started the video and Daddy said, "ACTION!"

"Hello, my name is Rob Chandler, but I prefer to be called Sissy Krissy. Because I LOVE to dress up in sexy clothes just so I can get more dick! I LOVE man meat SOOO much! I wish I could have dick to suck all day, everyday!! Call me...."

They stopped the video and took my stool. Then re-starting the video Daddy said, "Take off your dress like a stripper and get on your knees!"

I looked right into the camera as I swayed to imaginary music and stripped out of my dress. Then, crawling down to my knees still looking in the camera, I sat in my lingerie as commanded.

They stopped the video again as Daddy walked up behind me and squatted down to take my face in his giant hand! He covered my mouth and nose, stopping my breathing completely!

I didn't know what to think! Was he going to KILL ME!!?? I started panicking for breath, but still Daddy held on!

I was just about to start fighting for my life when Daddy uncovered one nostril and shoved a small brown bottle under it!!

I sucked in breath after breath, desperate for air! I had no idea what was in the bottle, but whatever it was, it made my mind grow VERY fuzzy! It was like I was drunk almost! I lost focus of where I was and who was in the room!

All I knew is there was a hard dick in my face and I did what any empty minded faggot would do! I began licking and kissing, sucking and deep throating that beautiful dick! My ONLY focus was giving this phallus the proper attention it deserved no matter how long it took! My inner slut was suddenly set free and my male ego's humiliation was forgotten!! I was a cocksucker on fire!!

The whole time I pleasured Daddy's dick that photographer guy kept videoing and taking pictures! But I didn't care!! My world was this magnificent cock!! When Daddy finally reach his orgasm he pulled out and came ALL OVER my face with video and pictures to prove it!!

Daddy stepped back and put his dick away. As I was catching my breath I finally looked around and was TOTALLY FREAKED OUT!! THERE WERE SOOO MANY MEN IN THE CAR WATCHING!!! Daddy noticed that I suddenly got self conscience so he grabbed my face again, smothering me! I knew what he was going to do when he placed the bottle back under my nostril. I couldn't have stopped him if I wanted to anyway!

I went black and when I awoke I was sucking dick again, but this time there were dicks EVERYWHERE!! ALL AROUND ME!!

Sucking dick for hours and every time I started getting clear headed that brown bottle was put back under my nose to make me a cock hungry faggot again!

I have no idea how many men I sucked off that night or how many times I sucked them off?! But every single one of them came on my face or body. Never in my mouth! AND it ALL got recorded!!

Just a couple of hours before sunrise the last man blew his load in my hair which was already dowsed with cum! My entire body was too! My stockings, panties, bra, my arms and even my back! Daddy was no where to be seen and the photographer just packed up and left.

I quietly stepped over a few men, probably homeless, and crawled out the door so as not to wake any. My jaw hurt from devouring cock all night!

Now I had to walk home even FURTHER than the first night I met Daddy! At least I'm wearing all black lingerie this time!

I walked the tracks closer to the grocery store and made my way through the dark neighborhoods to the highway. Luckily it was early and there was virtually no one out so I scurried across the highway to the park.

It was uneventful until I got close to home. I guess Ronnie Ledbetter was up getting ready to go somewhere. Well, he saw me!!

We locked eyes and I ducked behind a row of hedges and rushed behind them into an unknown backyard!

I could see Ronnie looking for me! I stayed quiet as he kept getting closer!!

"I saw you, come on out little girl, I just wanna play with you, don't be afraid." I WAS afraid!! VERY AFRAID!! RONNIE LEDBETTER IS MY CHILDHOOD BULLY!!!

Just when I knew he was going to find me I heard someone else yelling at him. He rushed away, leaving me still hidden and panicking!!

I was so afraid to move but the sun is LITERALLY coming up!! I waited to hear Ronnie's truck drive away then came precariously out of my hiding place. I rushed down the street and by the time I reach my block the sun was up!!

As I turned the corner into my back alley way I saw Daddy there waiting at my gate!!

I was so scared as I approached him!! He shoved me against the fence, "Pull down your panties faggot." He commanded

He kneeled down and started messing with my little sissy clitty! He pulled and pushed, hurting me a few times. Then I heard a 'click' and Daddy stood up and walked away giggling.

I looked down to see a chastity cage on my clitty!!

I stood there for just awhile staring at the metal contraption locking my penis away until I remembered where I was and how I was dressed!!

I pulled up my panties in haste as I scurried into my back yard and through my bedroom window.

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4 Comments
ApanderApanderalmost 2 years ago

Such a wonderful story! MORE PLEASE!!!

nikkicd_tvnikkicd_tvabout 3 years ago

I loved the story! I could feel the tension, and being dressed in public always has that fear of being recognized. Well done, and I loved the tease about the bully!

AnonymousAnonymousabout 3 years ago

Who are for the homeless

AnonymousAnonymousabout 3 years ago

We need more!! I love the chasity!!!!

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