Who're for the Homeless Pt. 03

Story Info
Continuation of a crossdresser's blackmail.
1.1k words
3.69
15.6k
17

Part 4 of the 4 part series

Updated 06/10/2023
Created 03/24/2021
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I couldn't sleep that night. I kept imagining that nasty, scary man lingering outside my window! A few days later I was helping my mom carry in the groceries and he was walking by our house real slow! Our eyes met and he grinned and said hi to my mom!

Who, being the sweet natured lady she is said hi back and actually made small talk with him!! I grabbed some bags and took them in the house. When i got back he was gone, but my mom said that he was such a nice gentleman and that maybe they would hire him as a handyman soon!

OMG!! Can this get any worse??

I couldn't concentrate at school, all I could think about was Mr. Johnson getting open access to my whole house!!?? OH PLEASE don't let that happen!!

That night around 8ish, I was in my room doing my homework when I was startled by metallic tapping on my window! I knew who it was and I SOOO just wanted to shut off my light and pretend I wasn't there! But there was no telling how long he had been watching me and I was still afraid of him! So I reluctantly opened my window.

"Come out here bitch" He said while quickly looking me over. "Put on something sexy first and hurry." He demanded.

I went to my secret sissy stash and pulled out some pantyhose and cotton daisy dukes, a bra stuffed with socks and a tube top, my high heels and painted my lips red and quickly got back to the window!

"BITCH, why it take you so long!?" He complained as he helped me out to the ground.

"I tried to be as fa..." POW!! He SLAPPED ME!! HARD!!

Tears filled my eyes as the familiar fear for this man returned to my now racing heart!

"C'mon", He said pointing toward the back alley. Our fence and all our neighbors fences are 8 ft. privacy fences with an alley running behind.

Once the back gate closed behind us, he grabbed my long hair by the back of my head and slammed me against the fence pretty hard! I am TOTALLY afraid of him!!

He was giving me this look... I wasn't sure if he was going to hurt me or not!! Time definitely stood still as he stared into my eyes making sure he instilled solid fear in me!

It wasn't until I was visibly shaking and crying that he finally broke his stare with a VERY forceful kiss! His tongue took possession of mine as he pulled my hair until I reciprocated!

His tongue was so deep sometimes that it made me gag!

He broke our kiss and demanded I remove my shorts and as soon as he realized I wasn't wearing panties he made it clear that that was NEVER to happen again!!

"WHERE'S YOUR PANTIES FAGGOT?!" he demanded, scaring me into more cowering and crying!

"I... I... I just thought..." is all I got out when he took my shorts away from me and demanded I open my mouth. To which he stuffed my cotton shorts in!

Then, spinning me around he said, "You put your faggot hands on that fence and don't you move them till I say you can. cause if you do, I promise you I will not stop till I see blood!

I nodded in absolute fear of what he was about to do! But I didn't see the switch!! I thought he was going to use his hand again!

When the first strike landed on my pantyhose covered ass it took my breath away!! He was on his third swing by the time my breath came back for a healthy scream. I swear if it weren't for my cotton shorts I would have had the attention of all my neighbors in an eight block radius!!

The next breath was the same except it brought desperate cry's!

He chewed me out as he punished my poor sissy ass!

"Don't you EVER go without wearing panties again! You understand me faggot!! Sissies like you supposed to wear panties every fuckin day of the week! In fact, you best be wearing panties from now on, cause you don't know where I might find you and check your panties!! You understand me faggot?! EVERY!! FUCKIN!! DAY!!" He demanded as he had me trying to dance away from the brutal switch!

When he stopped, he unzipped his slacks and pulled out his massive dick. I was too afraid to turn around! I was holding the fence for dear life and desperately trying to breath through my shorts because my nose was filled with snot!

"GET ON THIS BITCH!" He demanded.

I knew what to do! I spit out my shorts, hit my knees and started being the best cocksucking faggot I could be!

I was still crying on his dick as he started fucking my mouth, taking my head in his possession and fucking my mouth in earnest! Soon my spit and snot were mixed up and smeared all over my face!

I cried the whole time he skull fucked me because my ass REALLY HURT!!

"You learn, sooner or later you'll learn to be a good faggot for your daddy!" He said as he continued to saw his monster dick in and out of my mouth! Sometimes only mouth deep, but others he would plunge in to the hilt cutting off my air supply. Then he would saw what felt like at least 5 or 6 inches in my esophagus!!

I held onto his thighs praying it would all be over soon as he started pumping in a steady rhythm! I felt his cock swell in my throat and I knew he was about to cum!!

When he did he pulled out and coated my face with blast after blast of hot sticky cum!

I sat there dazed catching my breath as he put his dick away. Then he kneeled down and started scooping up his cum with a finger and said, "Open".

He fed me his cum as he gave me instruction.

"You get yourself prettied up for your daddy next Friday night. Wear some sexy lingerie and a pretty dress. Don't disappoint me now. cause if you do you know what you gonna get.

So you be ready for your daddy right here in this spot next Friday at 10 pm. understand me faggot?"

I nodded in agreement as he fed me more of his thick cum!

Then he just left me there! A sobbing cum covered crossdressing sissy in the alley right behind my OWN HOUSE!! When I finally pulled my head together and realized my predicament I made my way back to my room hastily!! Once there I sought my full length mirror to check my poor sissy ass!

OMG!! HE LITERALLY SHREDDED MY PANTYHOSE!!

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3 Comments
AnonymousAnonymousalmost 2 years ago

Why so many exclamation marks? It's exorbitant... It seems too affected, like a cliché about Sissy

AnonymousAnonymousabout 3 years ago

Love this, can’t wait for more

dieter40sndieter40snabout 3 years ago

Geile story, bitte schreib weiter

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