Caught by My Bully and Exgf Ch. 01

Story Info
Sissy Cindy gets an unexpected visit by her ex and old bully.
2.1k words
4.39
83.7k
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Part 1 of the 2 part series

Updated 06/08/2023
Created 05/26/2017
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Dear readers, this my first erotic story, all of protagonists here are fictional consenting adults, I hope you enjoy reading it!

*****

I was 21 year old student with part-time job, living in a small flat in big city when this all happened. I broke up with my girlfriend Michelle, after seven month long relationship with her, because I received a video from my high school bully Jack, on which he stuffs his enormous cock down Michelle's throat before spraying a huge load all over her face!

I felt shocked and betrayed, but also turned on by the video, jerking myself off while watching it repeatedly and the strangest thing was, as I realized later, I was imagining being Michelle and how would my bully's mean cock feel and taste in my mouth. It was confusing for me, I have never considered myself gay or even bi-curious before, I dated many girls before and enjoyed sexual activities with them.

After the humiliation of being cheated by my beloved (ex)girlfriend something changed inside me. Michelle was about to have her 19th birthday before she cheated on me, so I had a gift for her already bought when we broke up. It was sexy pink lingerie set, consisting of sheer pink hold-up stockings with matching panties, bra and sheer pink babydoll.

I had always a thing for girls in sexy lingerie or costumes combined with sheer stockings or tights , but girls I had dated, hadn't been wearing such things at all. Since I was 18 I used to occasionally go into mum's drawers and try on her silky pantyhose for the nice feeling and looks it gave to my legs and tingling in my penis.

I tried to end this habit after I moved out and started dating Michelle, but now there I was, alone in a flat full of girlie stuff my cheating girlfriend left there. It was too much of temptation so I decided to have a bit fun pretending to be my ex whore. I unwrapped the gift (supposedly for her) and took off my boy clothes.

Luckily I had similar height, weight and foot size as Michelle, for a man I was quite short and slim, most people would think, I am still a teenager. My legs were nearby hairless as same as the rest of my body. I had just some light soft pubic hair above my dick, which got to its 4inch stiffness when I encased it in the pink panties. Then I rolled pink stockings over my legs, enjoying the divine feeling, then I put on the bra, which I stuffed with some socks to get nice fake B sized tits.

Finally I put on the pink babydoll and went to bathroom to check out my outfit in the mirror. Wow I sure looked hot! But something was missing yet. My face looked already girly with my small nose, plumpy lips, big blue eyes and no facial hair, but I decided to doll myself up with Michelle's make-up.

First, I done my long light brown hair in two cute pigtails, then applied some mascara on my eyelashes, dark blue eye shadow, dark pink blush on my cheeks and finally whorish red lipstick. For my first time make-up experience it wasn't bad, I looked a bit silly, but nearly passable. I couldn't believe it was me in the mirror! In the image I saw a sexy teen girl who I would love to have romance with.

Michelle also left sexy red high heels in my flat, so I slipped in them and started walking around. I felt so sexy, I wished I had a camera to film myself and add it to my spunk-bank. I turned on my computer and searched for some online porn compilations of chicks deep throating large cocks and rolled a blunt to get more into mood. When I had it rolled and smoked, in the high state I got more nasty thoughts.

I went to a secret drawer and pulled out Michelle's dildo, realistic model 9inch long and 2inch thick with many veins, with realistic balls and suction cup. I washed it with hot water and stuck the suction cup to tiles on the wall. I put my hands on it's balls and started licking the head. Soon I went deeper, rolled my tongue all over it, went under to lick those balls while the shaft rested on my forehead, before taking it to my mouth until it pressed on the entrance of my throat.

I enjoyed serving this dildo, pretending it to be the cock of my bully Jack and I was my nerdy ex. It was well lubed by my spit as I went deeper and deeper. One time I pushed so much, that the head slid into my throat. I held it there for a brief moment before I gagged it out and nearby puked.

Next time I went down on it, let it pop into my throat and slowly devoured more and more of it. When I gagged I tried again until I felt, those fake balls resting on my chin. After few seconds of having my throat fully stuffed I withdrew and huge spit fell to my knees, my throat felt sore, aching and used. My panties were soaked with precum and I haven't even touched my dick yet.

Since the dildo was so slimy, I got a nasty idea. I positioned my ass to it, pulled my panties aside and tried to stick the head into my sphincter. It was strange sensation for me, only thing I had in my ass yet, was Michelle's finger when we showered together and it was just for fun. I was too eager and pushed too much, making the head and inch of the shaft slip into my tight ass.

It hurt as hell and but I tried to relax and breathe deeply, letting my ass to accommodate the dildo. Slowly I stuck about half of it in my rectum and was lost in my perverted world of pleasure and pain. As my tight ass got used to the invader, I started fucking myself in fast pace, making loud feminine sounds, feeling climax building in my prostate.

Then I heard the door being opened! Fear overcame me and I tripped on high heels, fell to the floor with dildo still in my ass, which got stuck even deeper after my fall. I yelled in pain as I saw Michelle and my old bully, Jack, standing above me and laughing! I was frozen in fear as dildo fell out of my ass with loud "PLOP!"

"I knew you were sissy!" said Michelle, "that's why I had to find a real man who can satisfy my needs!"

She was mean but very well dressed this time, she wore short tight skirt, shiny tan pantyhose and high heels, decently made up face behind her glasses, brown hair made into "geisha style" bob and sheer red top showing her firm B/C sized breasts in lacy bra. Jack watched me with lusty and evil look in his eyes, I could clearly see bulging tent in his shorts!

"You fail as a man but you make a very sexy bitch." he said.

I was dumbed by the situation and weed I have smoked before so I answered:

"Thank you sir."

Ohh crap, my old bully is making fun of me again, but this time I look like a slut and I am being polite to this jerk! They both laughed again.

"You are such a slut Danny, I went here just to take my stuff and say goodbye to you, but after what I saw, you may keep my dildo, make-up, heels and clothes," said Michelle and asked: "What is your girl name sweetie?"

I answered with trembling high pitched voice: "M-my name is Cindy, Cindy Tightass."

Michele's eyes gleamed as she said: "Ok lets see how tight your ass really is, sit on the dildo now bitch!"

I obeyed her and took half a length in my ass while squatting on high heels.

"Good girl!" said Michelle and knelt next to me.

To my surprise, she took my head in her hands and gave me a french kiss. I tried to touch her tits while kissing but she slapped my hand and ordered me to put my hands behind my back. Jack took off his clothes meanwhile, revealing his tall muscled body with some tattoos and most of all, his hard 9inch veiny cock, pointing at my face, demanding attention.

I stared on it in awe, then I looked up to his eyes to see his self-conscious face. He was such an asshole, but he was well endowed alpha male and I was just a helpless weak sissy. Michelle held me by neck as he approached and put his dick on my face so his heavy shaven balls were on my lips, my nose smelling his overwhelming muscular scent.

Jack's cock felt heavy on my pretty dolled up face and I loved how it throbbed, getting even harder and thicker. He was slapping my face with his cock for a while, then Michelle held my nose so I had to open my mouth and his big cock slid in between my sensuous lips. It was much tastier then the dildo and I started to worship his erection more vigorously than the dildo before.

He took me by my pigtails and started fucking my face, while I still bounced on the dildo. Michelle was licking his balls while rubbing her pussy under short skirt through her pantyhose (she didn't wear panties).

Jack said mockingly: "You and Michelle are great pair afterall, good team to suck my cock, you sissy fag bitch whore and nerdy slut!"

He called me names, but I was actually happier then ever, kneeling next to the sexy girl I still loved, dressed as even more sexy girl, pleasing huge cock of the guy who used to make my life hard, now I made his cock hard and slippery. His swollen cock started invading my throat and Michelle held my head tight to help him get there.

After some resistance and gagging he finally slipped into my throat and in one slow motion my chin rested on his heavy balls while head of his cock must have been stuffed into my esophagus. Luckily for me, I have trained my throat on that big dildo before. My eyes were running with tears, smudging my make-up. I tried to push back to get some air but they held me there for what seemed like an eternity. When my vision started to blur and I felt like fainting, he took his cock out and smeared my spit and his pre-cum all over my face.

"Good messy bitch girl fuck yeah!" Jack grunted.

I felt kinda proud for taking such a monster down my throat. He started to fuck my mouth again, going fast and deep, my throat was now well stretched and I stopped nearly gagging. Michelle took my small hard cock and squeezed it, I wanted to yell but Jack's cock was lodged down my throat again. He felt like getting even harder and thicker, pulsing and massaging my throat from inside.

My tongue was licking his cum filled balls and I still sat on the dildo, which was now also deep balls in me. He fucked my throat as it was a pussy, his heavy balls slapping on my chin drove me crazy. Suddenly Jack gripped back of my head and neck, holding his cock all the way in my throat and started trash talking me:

"Ohh here it comes! Take my load you sissy bitch cocksucker!"

I was moaning like a schoolgirl, feeling him twitch in my throat as Michelle jerked my small dick. With savage manly roar my bully came straight into my stomach, nearby drowning me with all his jizz. He pulled back and few thick ropes of cum hit my face, while my small dick came too! Michelle smiled, scoping cum from my face and made me lick it from her hand. She still rubbed herself with the other hand and drained last bits of cum from Jack's softening cock.

"I love the taste of alpha male cum, I envy you for getting to drink his huge load Cindy!" she said.

I didn't know what to do next, I wished Jack would leave me alone so I could clean all the cum from me and speak with my beloved Michelle about all the stuff that just happened. But they had other plans for my tight sissy ass...

The end of part 1

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7 Comments
devinwhitegurldevinwhitegurlover 6 years ago
Great scenario! very Humiliating

Hit me up. I'd love to talk to you about commissioning a story from you. devinwhitegurl at g to the mail. I love your sissy scene :)

nullernulleralmost 7 years ago

I always like the bully - sissy stuff :) Good story.

cdCindy1cdCindy1almost 7 years ago
great start

My female name is also "Cindy" and I've been a CD for about 4 years. I haven't gone out in public yet but one of my female friends did catch me all dressed up just like in your story (she wasn't my ex but just one of my close friends). She was a bit shocked but not really surprised because she said she had always suspected that I was either gay or at least bisexual. I admitted that I'm probably "bi' because I'm still attracted to the female body but since I've been dressing up I really prefer being "gay" with men. I truly only want to dress up for men, make out with them, suck their cocks and then have the men fuck my man-pussy deep and hard. Yes, I'm a sissy faggot cocksucking CD slut -- AND I LOVE IT !!!! Please continue this story - I can't wait to read the next chapters.

AnonymousAnonymousalmost 7 years ago
OMG! I want one too.

So hot my panties are wet. I want my own bully someone to use and abuse my Sissy body than make me say "thank you Sir, please sir I want some more "

Thank you Candy Tightass.

LindaCrystal xx

300bowler300300bowler300almost 7 years ago
MORE PLEASE

GREAT JOB, WAITING FOR MORE OF THIS WONDERFUL STORY, HOPE IT GETS HERE REAL SOON...! BETTY jo xoxo

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