Gary's Dressup Sissy free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One movie was all transvestite scenes. This shocked Gary but I found it a massive turn on. I'd been experimenting in wearing my sister’s clothes for a while. Gary could obviously see this, so suggested I dressup. We went up to his sister’s room and looked in her wardrobe. Gary immediately picked out her school uniform. She was a little younger than me, so when I slid into her grey pleated school skirt it was way above the knee. “Too short for school” Gary had commented.
This went on for a few days. I would go over when Gary was alone. He'd have me dress up in the schoolgirl outfit, skirt blouse, panties and ankle socks, and we'd either play games or watch movies.
Gary would tease me a little. But I could tell he liked me to dress up. Maybe he missed his girlfriend I thought.

One day in his bedroom, with me in my usual schoolgirl attire, there was a clothing catalogue lying around; a big thick book full of clothes, Gary had been shopping for new football boots from it. I began to flick through the pages, looking at the beautiful women.
Gary came and sat down beside me and closed the book, then opened at page one. We flicked through the catalogue together, commenting on the clothes, Gary would say how he thought I'd look good in certain outfits, making me blush, and I would choose ones that he should buy me. Eventually we arrived at the footwear section, again Gary picked out the shoes, always sky high heels. My cock began to stiffen, as I knew which catalogue section was next, as I'm sure did Gary, page 202, lingerie.

"mmmm" said Gary. I blushed. We flicked through the pages in silence. I waited for him to choose an item for me. He stopped at page 207. Black suspenders, panties bra and stockings. My cock twitched.
"I bet you'd fuckin’ love to wear that wouldn’t you, you little sissy" was Gary's response.
Although a little surprised by the manner of his comment I said "sure". I'd come this far, what was the point in being coy about it "I'd just love you to dress me like that"

Gary grinned a wicked grin. "Come on" he said, darting from the room. I followed him into his mother’s room. He went straight to her bedside table and opened the bottom drawer. It was full with lingerie. All colours. "I found this lot this morning" said Gary " sit down"
I sat on the bed as he picked through the knickers, "don't mess them up too much Gary" I said "she'll know we've been looking"
Gary quickly found a matching set of lingerie. Panties bra and suspenders, and also a pair of black lace topped stockings. He gathered them up in one hand and thrust them at me...."put them on" he ordered.

Slightly nervously I stood, stepping out of the schoolgirl skirt and removing the blouse. Gary handed me the suspender belt. I fastened it first, then stepped into it. Followed by the panties and then with Gary's help the bra. Gary then handed me the stockings, I slid them up my legs, they felt divine, my cock stiffened. I glanced at the rapidly growing bulge in the front of Gary's jeans and knew his cock was doing the same.
Gary then moved to his mom’s wardrobe....and picked out a pair of black high heels.
"Will these fit?" he said....I looked they were a size 6 and I was a 7, but I tried them. They fit although they were very tight. Gary was grinning from ear to ear.
"How do I look?" I asked...."hot" was his reply.
He picked up the schoolgirl outfit.....handed it back to me...."now this" he said
I put the blouse on and stepped into the short little schoolgirl’s skirt.
Gary grabbed me by the hand and led me back to his room. He sat me on his bed and went to his dressing table drawer. Taking out a Polaroid camera.
"Smile" he said as he shot off a couple of photos of me.
"Oh come on!" I said
"don't worry, they’re just for us to remember today ok?"
"Ok" I replied.
"Lie down he said, so I did.....he picked up his dressing gown from the floor, and removed the belt.
"Give me your hands" he said....again I did so.....I was so horny now I'd do anything he wished.
He tied my hands above my head to the wooden spindle of his headboard.
"Are you horny?" he asked
"oh god yes"
he stood up, took the camera and fired off two more pictures.
Then undid his belt and removed his jeans and pants...then his socks then shirt. He stood before me naked...I could see a long thread of precum dangle from the tip of his fully erect cock.

He climbed onto the bed with me. He straddled me before positioning his knees either side of my head, pinning me helplessly to his bed. He began to stoke his cock, right before my face. His cock looked fabulous. The precum dripping onto my lips. "You like this?" he asked....I nodded
as he continues to stroke.....I opened my mouth and licked his cock
"oh my god"....he exclaimed...."you filthy little sissy whore, I can’t believe you want to suck it!"
Again I nodded....He pushed the tip of it between my lips....I tasted him.....It tasted salty. God I was so hard.
Gary pushed his cock in and out of my mouth. Slowly at first. Then he got quicker. I closed my lips around it and tried to suck. I licked his cock head and shaft as best as I could. But as he speeded up I found it difficult. His hands grabbed my head and held it steady. All I could do was to keep my mouth open. He was now fucking my mouth. His cock was plunging in and out. His cock head was banging the back of my throat making me gag and cough. My eyes were stinging and slobber was going everywhere. I glanced up at Gary. He was red in the face and sweating. He was grunting and growling as he clearly enjoyed fucking my face.

He pulled it from my mouth and began to jerk off in earnest. I could tell he was close
"cum in my mouth Gary...” I pleaded..."over my face"
"don't worry slut....I’m gonna spray all fuckin over you"
With that his hips began to writhe on me....and the first spray of cum hit my face....I opened wide and he forced his cock into my gaping mouth. I eagerly gobbled up the rest of his load.....sucking him clean as he moaned in ecstasy.
Gary then wiped the initial spurt of his jizz from my brow and cheek into my mouth....I took it from his fingers.

He stood up...grinning he looked at me....the skirt had ridden up revealing my socking clad legs.
He untied me....I knelt up. Looking at him I said "can I cum?"
"Jerk off" he ordered....I hitched up the skirt and fumbled my stiff cock over the front of the panties
"Gary grabbed a glass from his bedside table and drank it's contents. handing it to me he said
"Cum in that, don’t get any on my sister's or mom’s clothes"
I positioned my cock into the glass....and with the other hand began to jerk off
"don't cum till I say so" he said....clearly getting off being the dominant male
I jerked off....stopping every minute or so to gather myself and so as not to cum.
he made me jerk off for maybe 10 or 15 minutes like that, occasionally taking my precum on his finger, before feeding it to me.
Eventually I begged to cum "please Gary...I can’t hold it any longer"
"ok slut....cum now....into your cum cup"
I spurted shot after shot into the glass. "Oh fuck" I screamed, as cum pumped from my cock, almost half filling the glass.
Spent, I looked at Gary
"Now drink up" he said "You need to get used to the taste of cum honey....coz you'll be sucking my cock every day from now on....otherwise everyone will get to see those Polaroids!"

I looked at him again. I could see he was clearly enjoying this. I glanced down and saw his cock was
Stiff... again! My stomach sank for a moment when I realised the position I was in. I was in my friends Bedroom, in an empty house, with no one due home for four hours. I was dressed like a slut in his mom’s sexy underwear. He had taken photos of me too. He had already fucked my mouth and spunked all over my face. He had just made me cum and he was still horny! What is more, I was loving every minute of it. Another thought crossed my mind. I thought back to the transsexual porno we had watched together. Trannies get fucked up the ass!

Gary picked up the cum filled glass and handed it to me. “Go on....slut....drink it all!” he ordered. His commanding voice sent a shiver up my spine. I lifted the glass to my lips, opened my mouth and poured the cum in. The salty cum slid into my mouth. The musky taste was nice and it must have showed on my face...”You filthy slut!.....you love it, don’t you!”

I nodded. I looked a Gary. His face was flushed and his cock was sticking up hard. He had that look in his eye again and he was not finished with me yet. “It doesn’t taste as nice as yours” I said. I put my finger in the glass and scooped up the last of the cum. I licked the finger and stared into his eyes.

Garry growled and then suddenly shouted “Hands...give me your hands!”. I held them out in front of me. He took the dressing gown belt and tied my wrists with one end. Next he pulled his bed away from the wall a bit and moved the mattress back too. “Lean over the side of the bed...sissy”. I moved on my knees, to the bed side and lay my body on the mattress. Gary took the other end of the belt and walked round to the other side of the bed. He then tied that end to the metal frame of the bed. I was going nowhere.

The Polaroid camera came out again and more photos were taken. A few of me in my tied position. He then moved his cock up towards my mouth. I opened my mouth while he photographed me licking and sucking his cock. The camera was empty, so he left me tied to the bed while he went for a fresh film cassette.
Gary came back into the bedroom, clutching the camera and a large jar. “What’s that...what are you doing?” I asked. “You!........That’s what I doing!....I’m going to fuck you!” He replied. Gary knelt on the floor behind me. He started to touch me. He ran his hands all over my ass, body and legs. His hands roamed all over me. I felt great! Up and down my stockinged legs and inside my knickers. He played with my suspenders and twanged them. Then, suddenly, he spanked my ass....hard. And again. And again. I turned my head round to look at him and shouted “owww!” “Shut up slut” was his reply.
Next he pulled my knickers slowly down. He continued to grope and spank my ass before he pulled then off all together. He took several photos as he was doing this.
Gary came up close behind. He forced my legs open with his knees, as he knelt right behind me. I could feel his cock against my bare ass for the first time. It was so hard! Gary rubbed and scratched my back gently. His hands slipped round the front and into my bra. His fingers tweaked and pinched groped my nipples as he groped my breasts. All the time, his hot hard cock was rubbing up and down the crack of my ass. I felt so slutty! He unclasped my bra and gave my back and front a good rub. His touch felt wonderful and his hardon was hot too.
“It’s time” he said. The big jar bounced on the bed next to me. The top was now open. It looked like Vaseline. I felt a finger exploring my asshole. Gary rubbed goo up and down my ass crack and he pushed it into my hot virgin hole.

And with that I felt a sharp pain in my ass as he forced his big cock into my virgin ass, I had never felt pain like it but I also kind of liked it. Gary kept forcing his cock deeper and deeper not pulling it back just pushing it in deeper until his full length was inside me then he pulled it all the way out and then plunged back in again. The pain was incredible! I screamed out loud! “Noooo....It Hurts! Gary ignored me He just kept on pushing his hard cock in and out of me. I was screaming in time with his thrusts. It felt like he was tearing my guts in two. Gary grabbed a handful of my hard and yanked my head back. His other hand forced my scrunched up knickers in my open mouth, and he pushed my head back down on the bed, forcing my face into the quilt. With one hand gripping my hair and the other hand in the middle of my back, Gary pounded my ass relentlessly. He banged me into the side of the bed. He fucked me like this for ages fucking hard and fast. His thrust moved the bed back to the wall and his continued assfucking was making the bed frame bang against the wall. My ass was still killing me and I was crying my eyes out. But I was just starting to enjoy the feeling. His legs rubbing my stockinged legs and his aggressive grunts and expletives made me feel all sissy and submissive. I felt a sharp pain and heard and loud slap, on one of my ass cheeks. This was followed by many more while he was still pounding his big cock inside my poor damaged ass.

He kept hold of my hair and he kept pulling me back on to his cock fucking me even harder and faster than before. I did not think I could take anymore when all of a sudden he thrust his cock deep inside me one more time and held it inside me. I felt his cock unload it's cum. My asshole could feel his cock twitch as he pumped me full. It felt that someone had turned a hose on inside my ass and it went all slippy. He did not seem to stop cumming for a couple of minutes.

His body collapsed on top of me. He was slippy with sweat and I could feel it dripping all over my body. Gary was panting and mumbling. He told me I was his sissy slut and he wanted to fuck me forever. It was quite a few minutes before I felt his cock slide out of my ass. I was so relieved but I also felt so empty not having him inside me.

We lay on the bed for about half an hour. I was drifting off to sleep when I felt Gary get up and untie my hands. He lifted me up onto the bed and lay down next to me. We locked each other in a passionate embrace and we kissed and caressed for ages. Gary gently wanked me off. I came on my tummy and Gary scooped it up and put it in my mouth. I licked it off his fingers. I lay back on the bed. I was flushed and spent.

Gary lifted my legs up and pushed a pillow under my bum. He wrapped my stocking covered legs around his waist and lay on top of me. And pressed me down into the bed with is weight. It felt fabulous. He French kissed and caressed me again. I surenederd to him. His hard cock was again bumping against my ass cheeks. I moaned with lust, as Gary French kissed me, and I felt his cock enter my ass again. This time there was no pain. I felt so open and slutty. Gary made love to me. I gave myself to him totally. His hot sweaty body on me as his hard cock filled my ass. He whispered lust into my ear as I promised him whatever he wanted. I looked at his face as he spunked deep into my body. The ecstasy and the release as he exploded. I knew then that He owned me, but I owned him too!

Same as Gary's Dressup Sissy Videos

2 years ago
  • 0
  • 6
  • 0

moms friend 2 dressup slut

so I had been visiting Linda for about 8 weeks. Every oportunity I got. My mom was none the wiser. I'd invented a girlfriend that I was seeing. Linda had backed up this story by telling mom that she had seen me with her.little did she know I was visiting her best friend to dress up as a whore every chance i got.Linda had had to lay down some ground rules. I had to dress in the outfit she had picked out for me as soon as I entered her house. She would watch me dress.Linda insisted I wear...

2 years ago
  • 0
  • 17
  • 0

Mommys Darling 2 Playing Dressup

Mommy's Darling 2: Playing Dress Up - By Billie Lovelace At twelve, I was deeply conflicted. On the one hand, I was a normal boy. At school I liked sports, roughhousing, and teasing girls. On the other hand, mother hated masculine aggressiveness. So at home I was more girlish. I played the piano, did housework, and spent hours with mother -- brushing her hair, polishing her nails, and helping her in and out of her high heels. It was so confusing. I wanted to be like other boys....

2 years ago
  • 0
  • 6
  • 0

Playing Dressup

My parents have a library. I was a very lucky girl growing up, not because of the collection of classics that they had in leather bound editions, or even the enormous number of new books that they seemed to add constantly from visits to the book store or from various book clubs that they belonged to. I liked a lot of those, but my favorite books in their collection weren't actually on the shelves in the spare room that we used as a library, they were in dusty boxes stacked in the garage and...

Straight Sex
3 years ago
  • 0
  • 16
  • 0

She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

3 years ago
  • 0
  • 20
  • 0

Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

3 years ago
  • 0
  • 23
  • 0

407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
  • 0
  • 13
  • 0

Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
  • 0
  • 19
  • 0

I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

1 year ago
  • 0
  • 11
  • 0

Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
  • 0
  • 23
  • 0

A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
  • 0
  • 9
  • 0

Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
  • 0
  • 8
  • 0

Saturday Morning Sissy

Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
  • 0
  • 18
  • 0

Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
  • 0
  • 10
  • 0

I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

3 years ago
  • 0
  • 11
  • 0

The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

1 year ago
  • 0
  • 25
  • 0

Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
  • 0
  • 17
  • 0

What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

1 year ago
  • 0
  • 17
  • 0

I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

2 years ago
  • 0
  • 9
  • 0

I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

1 year ago
  • 0
  • 14
  • 0

My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

3 years ago
  • 0
  • 14
  • 0

Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
  • 0
  • 9
  • 0

Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

2 years ago
  • 0
  • 7
  • 0

Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

1 year ago
  • 0
  • 9
  • 0

Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

1 year ago
  • 0
  • 11
  • 0

Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

2 years ago
  • 0
  • 10
  • 0

Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
  • 0
  • 9
  • 0

The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

1 year ago
  • 0
  • 14
  • 0

Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
  • 0
  • 9
  • 0

Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

1 year ago
  • 0
  • 15
  • 0

Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
  • 0
  • 8
  • 0

A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
  • 0
  • 7
  • 0

The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

2 years ago
  • 0
  • 8
  • 0

Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
  • 0
  • 8
  • 0

How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

3 years ago
  • 0
  • 7
  • 0

Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

3 years ago
  • 0
  • 12
  • 0

Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
  • 0
  • 8
  • 0

Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
  • 0
  • 11
  • 0

The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
  • 0
  • 8
  • 0

Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

3 years ago
  • 0
  • 11
  • 0

Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
  • 0
  • 8
  • 0

Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

1 year ago
  • 0
  • 11
  • 0

Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
  • 0
  • 6
  • 0

New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
  • 0
  • 17
  • 0

Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

3 years ago
  • 0
  • 25
  • 0

stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
  • 0
  • 16
  • 0

My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
  • 0
  • 11
  • 0

A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
  • 0
  • 31
  • 0

Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
  • 0
  • 31
  • 0

What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
  • 0
  • 13
  • 0

What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
  • 0
  • 14
  • 0

What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
  • 0
  • 9
  • 0

Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
  • 0
  • 21
  • 0

Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
  • 0
  • 35
  • 0

Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

1 year ago
  • 0
  • 14
  • 0

The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
  • 0
  • 22
  • 0

First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
  • 0
  • 16
  • 0

Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

1 year ago
  • 0
  • 7
  • 0

Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

Porn Trends