TIGHTY TIGHT SISSY free porn video

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POLLY GLOSS HOOKS UP WITH TWO UNHAPPILY MARRIED MEN FOR TIGHTS/LYCRA FETISH FUN

I met Pat and Len via a fetish forum for lovers of crossdressers and tights enthusiasts. We shared saucy messages and pics. It was fortunate that they lived nearby, as I had told them in no uncertain terms, that I wanted them both. My hungry eyes behind my shiny stocking mask longed for their hard mature cocks in their tights, in my mouth and, naturally, up my arsehole. The fact that they had wives only deepened the thrill. Indeed the thrill of cheating is even more intense and tender when dressed for the occasion. Len was a retired barrister and Pat was a building labourer. Both of them were tall, strapping hunks, in comparison to my curvy body, slender legs and sissy ways. Len owned a few properties in the city, which he often rented out to students and tourists. He kept one room free, for perverted escapades like ours.

As soon as Len buzzed me into the apartment block, I paused outside the door, smiled and slowly stretched a thick glossy tight black stocking over my face. I smoothed my hands over my silky compressed features. ‘Tights,’ I whispered, placing my bag in the hall.

The hunks were waiting for me, as I swayed into the living room, with a hand on my hip, in my black polo neck sweater and form fitting, over the knee skintight purple lycra shorts, layered over my double layered tan/silver metallic tights; giving my crotch, arse and legs a brilliant gloss finish. My silver heeled sandals really gave my legs and arse a lift. Fuck, I was so aroused, as I pranced and minced for them. I paraded up and down the room, casting them looks of disgust. ‘What’s the matter, never seen someone in Lycra and heels before? I was supposed to meet two unhappily married perverts here? Have I got the right place?’

In the middle of the room was a free standing mirror, where I knelt down on all fours, and slowly kissed my nylon reflection, knowing they were watching. ‘Ooh, what do we have here? I believe we’ve met before. My name is Polly and your name is Polly.’
I’d move my arse from left to right, feeling their eyes piercing the sheen hugging my curvy arse, as I pecked my stocking reflection. ‘Oh me, oh my!’ I gasped in sissy voice.

After some moments, enjoying my own company, I climbed onto the arm of the thick cushioned chair, opposite the men, giving them a right eyeful of my amazing arse, as I rubbed, humped writhed and said how I love lycra and tights, letting them get a good eyeful of the tight sheen of curvy arse. Len was filming me on his phone. My lycra shorts were so tight they must have revealed the pantyline of my leotard underneath. I humped and groaned with as much abandon, as if no-one was watching me. It was a regular activity I usually did at home in front of my video camera, whenever I bought a new outfit, or thought about a person I fancied. I’d hump and call their names, as I was doing now, when I yelled, ‘Oh Len! Pat! Ooh, tights!’
‘No-one wears lycra tights like you,’ Pat leered, as he undid his belt and dropped his jeans, revealing his muscular legs and hard cock in high shine mahogany tights.
Still on the thick arm rest, I looked over my shoulder.
‘Ooh do you think! With a cock like that, I could say the same about you,’ I cooed, as I rubbed and ground my arse on the armrest.
‘I’m wearing my wife’s tights, I am,’ said Pat, in a rather simple way.
‘Good for you,’ I said with indifference, as I glanced at Len, who was already wanking himself off in, presumably his wife’s black tights. He’d put the phone away and was studying me carefully.
I smirked, as I climbed off the arm rest, knowing that Len was fixated on how my arse curved and gave off a shimmer. I pranced over to the sofa and curled up to Pat, and caressed his gleaming hard cock through his tights. ‘Oh I love shiny tights,’ Pat grinned, smoothing his hands over his thighs and reaching over to cup my arse. ‘What is your missus doing this evening?’ I asked playfully, putting my hands on his shoulders, looking up at him demurely.
‘Daft bitch is into that psychic reading over the phone,’ he scoffed.
I put a hand over my mouth and gave a short, fake sissy laugh, which made me sound like such a dumbass bitch.
‘Does she know you wear her tights while you wank yourself off to my pics?’ I said.
‘I couldn’t give a shit,’ he said.
‘Neither can I,’ I replied, as I leant in and we kissed deeply as my nylon mask allowed. I massaged his cock through his shiny hose and felt his hands smoothing my arse. I even felt his finger prodding against my covered arsehole.
After about ten minutes of this luxurious petting, we paused.
‘Will you do that thing for me, you said you would?’ he said.
‘Did you bring her picture?’ I giggled.
Pat reached into his jacket and produced his wife’s photo. I studied the capture, the worn face and the weird short back and sides hairstyle many women strangely go for when they hit 55. ‘You weren’t wrong. Oh you poor bastard,’ I pouted, jerking him hard. ‘Imagine looking at that every day, never mind waking up next to it. Do you like this? Do you like me wanking you off while I insult your wife? Huh, you like me dressed like this for you, as I insult that dragon?’
‘Oh Polly!’ he gasped, as my hand clasped his nylon shaft and vigorously jerked his hard cock, as I looked in his face.
‘Okay stand up!’
Pat stood tall, as I squatted before him, exposing the skintight sheen of my curvy arse to Len. I placed the photo of his wife under my arse, looked at Len angrily, screwed my face up and rasped a loud one over the photo. I sucked Pat through his tights, clamping my nylon lips over his shaft.
‘You dirty bitch,’ said Len, wanking himself harder.
‘That’s what I think of your wife,’ I said, gazing up at Pat, as I placed both hands on my arse and felt the shiny sheen of my pantyline, as I sucked him with no hands. While I was doing this, I’d look at Len, with my mouth bulging with Pat’s pantyhose cock, knowingly, as if my real sights were on him. Again and again I thundered a loud one on his ugly wife’s image, as I released his cock and shoved it under my mask in my mouth. I deep throated him, making gagging noises, making my cheeks bulge, before I released his cock, right at the moment his jet of hot spunk splashed over my nylon face.
After he recovered Pat emptied a bag of smelly tights all over me. I grabbed a few pairs and sniffed and dangled them on my head and shoulders. ‘Ooh tights, tights, I love tights!’ I then stepped around the room in my heels, swaying and swinging the tights around, caressing my nylon face with them and wrapping them around my shoulders. Len looked at me with a deep, cock-straining disgust. The self-satisfied beam stretched my stained, stocking mask. ‘Ooh, ooh, I’m a tighty, tighty sissy, a tighty, tighty sissy!’ I pranced and posed and minced around, until I paused before Pat and placed my hands on his shoulders.
‘You know what I really want, Pat? You really know. I want to hear you say it, for sweet, little me,’ I pouted.
‘Shag me,’ he said quietly.
‘Huh?’
‘Shag me. Shag me in my tights! Bugger me!’ he cried.

‘Now that’s what I like to hear dear,’ I said, as I pulled my sweater off and slid my lycra shorts down, revealing my body in a red leotard. I rescued a few pairs of screwed up tights I’d been writhing around in, off the floor and stretched them over Pat’s head. Real tight. With the other pairs over my shoulders, I stuffed them inside the back of my leotard, which formed a strange looking compressed bulge, which must have looked disgusting from the back. Another daring look passed between me and Len, as I took my place behind Pat.
Pat bent over, making his tights stretch against his arse. I parted my high shine legs slightly, propped up on my silver heels and dry humped him in my red leotard, bulging with my hard cock. This was so fucking easy.
‘Do you know how long I’ve waited for this, you fucking b**st!’ I panted, as I felt my hard cock straining in my leotard, at the friction of his nylon on my lycra. I grabbed his nylon hips and angrily humped him. ‘Does that ugly cow have any idea how many times you’ve milked your cock over my pics?’ I seethed.
‘No, but it’s hundreds of times!’
‘Only hundreds! Not good enough. Maybe I should stop sending you my smelly tights in the post!’
‘Please don’t Polly, sniffing and wearing them is one of my few pleasures!’ Pat wailed. ‘My sweet Polly. It’s you I want. I hate my wife. I’m going to leave her, get my own place, put all your sexy used tights in my special drawer, and put framed pictures of you all over the place,’ said Pat, pressing his knees together and poking his arse against my thrusts. ‘Then I’ll wear your tights, put a pair on my head as well, and call your name as I look at you! I only hope your tights are smelly!’ he cried out, as the sound of my hips slapping against his arse, echoed through the apartment.
I felt my teeth clench as I humped him harder. ‘Oh yeah! Uh, uh! Oh yeah!’ I shouted.
I noticed Len frantically wanking himself off. I gave him a cheeky smile and a wink.
‘Tell Len what we fucking did in the bedroom you share with your wife when she was out?’
‘You fisted me.’
‘That’s right. And what did you have on your head?’
‘Your silky smelly red panties!’ he cried.
The sensation and friction made me flood the crotch of my leotard. Pat put his clothes back on, while I went out to freshen up and prepare for Len.

I squeezed into my pair of black silky panties and high gloss black tights. On my top I fixed a satin corset. I smiled as applied more makeup and dropped a red copper wig on my head, cut into a bobbed style. I stepped into a high waist pleated purple tartan skirt and heeled buckle shoes. I stepped back into to the lounge.
‘Where’s Pat?’ I said, resting a hand high on my waist, and arching my leg.
‘I locked him out on the balcony,’ admitted Len.
I smiled. ‘It’s freezing outside,’ I said, taking out a pair of my old suntan tights and pulling them tightly over Len’s face.
‘So what?’ he said.

He took my purple lycra shorts and, with a long swish, eased them over his hunky nylon legs. They were super skintight and form fitting. I leered at him and said, ‘Hope they feel as good as they look on you.’
Pat was watching and wanking from the window. My heels clicked on the flooring as I smiled and slowly stepped over to the balcony door. I bit my lip coyly as I paused on my side of the glass, considering whether to let poor Pat in. I parted my heavily glossed lips seductively and playfully before I sharply pulled the curtains closed, and returned to Len. I placed my arms around him, as he took me by the waist.
‘Pat may have big cock but he’s so fucking boring,’ I said. I looked at Len solemnly. ‘If there’s one cock that I want to be plunged up my tight arsehole tonight, it’s going to be yours,’ I said, before we fell into a passionate kiss, which made my wig slide to one side. We paused. I straightened my wig. I noticed the music. We gently danced for a while. I smiled serenely over his shoulder, so privileged to be in the arms of this hunky mature man, and dressed for him like this. Inside my knickers and tights, I could sense my arsehole twitching for the sensation of his thick cock.
‘We should leave that poor prick on the balcony all night,’ I suggested, a flash of glee in my eyes, as we rocked to the romantic music. I could feel Len’s massive cock pressing against my nylon thigh. I closed my eyes, as I imagined it filling my mouth. I leant to his ear and whispered, ‘Because I’m in a charitable mood, I might even open the curtain slightly, so poor Pat can see what he’s missing,’ I added. This knowledge prompted another strong kiss. My hands smoothed and gripped his arse.

After the music finished we sat down on the sofa with our wine. I carefully crossed my leg with the swish of mesh, giving him a good eyeful of my glimmering thigh. I asked him if he had remembered to bring his barrister wig. He reached for a box on the table and took it out. I looked at it with fascination, as I caressed it. ‘Very classy,’ I said. ‘May I?’ I carefully fixed it over his head. ‘Oh my. How masterful and dignified it makes you look,’ I smiled.
We made small talk for a little while about his former career as a barrister. I found it intriguing. I tucked my nylon legs under my arse on the sofa, as he regaled me with some tales of his former occupation. My eyes were wide with interest and my panties were moist, in the presence of this hunk whose legs and arse were packed into my purple lycra shorts over his black tights. I giggled flirtatiously in all the right places, sometimes letting my hand fall on his lycra thigh.
‘I have to know something,’ I said delicately, taking his hand. ‘Did you ever, you know, get someone sent down who didn’t deserve it, just because you didn’t like them?’
Len’s smile stretched his stocking mask.
‘Oh go on,’ I teased. ‘Please tell me!’
‘But that would go against professional ethics,’ he said.
I shifted my legs from under me and carefully put the glass on the coffee table. I crossed my legs and smoothed my glossy thigh.
‘Oh darling, do you really think when your cock’s in my mouth, that I give a hot shit about professional ethics? The last thing that’ll be on my mind, when I get home and I’m wringing out my knickers after you’ve drenched in your hot cum all over them, will be some loser in the slammer,’ I said as my smile transformed into a look of calculated lust.
‘You really are a dirty bitch,’ he said.
‘You should prosecute me for being a panty pervert,’ I said. ‘Sentence me to sit on your mouth, three fucking times a week, for twenty years!’
I looked at him with a daring smirk on my lips.
We fell into a passion kiss. My glossy lips parted his nylon mouth, as his hands went up my skirt and smoothed and stroked my tight panties.
‘Oh my Len!’ I panted.
He pushed me onto my back, as I smoothed and gripped his arse in his lycra.
‘You dirty cow, you would do it as well. You’d really do it,’ he seethed.
‘And more, so much more!’ I panted. ‘Oh Len, I really have to hump your arse!’
I jumped up, took my skirt off, as Len lay on his front. His arse shimmered in the tight lycra. I positioned myself on top of him, in my tights and panties, and expertly ground my hard cock into his encased arse. My arse bobbed frantically up and down, as I breathed heavily in his ear. ‘Oh yeah, leave your wife for me and I will dutifully sit on your face any time you fucking want. There won’t be a day that I won’t wear immaculate tights and panties for you, that I won’t lie in your arms and kiss the hours away, or that your hard cock won’t stir my arsehole red raw! Do you understand?’
The friction between my nylon crotch on his lycra arse was fucking unreal! Ooh I could feel the stretch of my tight knickers under my glossy tights. My determined thrusts were also making my wig slip over my eyes. My eyes darted with wild lust. ‘There won’t be a day where your nose goes without my arsehole, where you won’t wake up and see me greeting you in my incandescent lycra leggings and aerobics leotard. There won’t be a day that goes by without you flooding my mouth with your cum. There won’t be a man on our street who won’t want to give me the fucking I so richly deserve, that I already get from you. Every fucking night! In tights, Len. In tights! In tights! And get this, there won’t be a minute that I won’t yearn to suck your big cock through the tights I make you wear! Now do you understand how I really feel about you, my darling!’
Len shifted under me. We changed positions, and he got on top of me, pinning me on my front. I gasped as I felt his rock hard cock in his lycra pumping my arse in my knickers.
‘You dirty, little slut!’ he seethed. ‘As soon as my back was turned you’d be offering your tight arse to every pervert out there!’
‘Not every pervert!’ I panted.
‘I know what you’re like, I’ve seen the way you relish all those men wanking over you on xhamster,’ he said.
‘Only the ones who dress in lycra and encase themselves in shiny pantyhose! I block all those miserable flaccid cock profiles,’ I confessed.
‘And I bet that gives you a thrill, does it?’
‘Absolutely. Honestly, you should see me, curled up in my leotard and tights on the sofa, yawning at the boring chancers, as I fart for my own pleasure!’ I giggled
Len’s thrusts were more violent. I can’t tell you how liberating it was, feeling the weight of this man on my back, with his hard cock pumping my arse through my panties, listening to my vicious and kinky truths. I couldn’t wait to tell my followers this story, hoping they would gush in their wives’ tights.
‘Aren’t you even ashamed of the way you dress and act, for strange men to jerk themselves off over you?’ seethed Len.
‘I’m only sorry that their wives’ aren’t aware of their husbands secret late night desires. I just know they’d be envious that their hard cocks were for me! Speaking of which…I need your hard cock! I need it now! In my mouth, Len!’ I scrambled off the sofa and went to the balcony doors, where I opened the curtain.
‘What are you doing?’ said Len, as he got to his feet, his hard cock bulging in his lycra shorts.
‘I really need to show poor Pat how I feel about you.’
I squatted down, surely giving Pat a good eyeful of how my black tights hugged my silky black panties. ‘Oh, Len, darling. Let’s swap wigs.’
Len exchanged my copper wig for his barrister wig. My slutty face in makeup, framed by the barrister wig seemed to make him harder. I looked up at him as I traced my tongue over his huge lycra shaft. Sometimes I’d look around at Pat, as I kissed Len’s lycra compressed balls. ‘Imagine I’m the barrister and you’re the smooth criminal. Ooh, and you’ve done very, very naughty things,’ I said, as I placed kisses on his shaft and pressed my nose under his balls, to sniff. ‘Oh I’ve read the case notes, and the bad things you did. I creamed my panties over you.’ I sniffed again. ‘Fuck, your lycra is sweaty,’ I grinned.

Knowing that Pat could see this, as well as the view of my shapely arse packed into my gleaming knickers and tights, gave me a thrill. By now I had whipped Len’s stiff prick out of his lycra and was on it, deeply sucking him, as I looked at him with devotion. I briefly turned round and glanced at Pat, my mouth full of cock. I then knelt down, resting my arse on the back of my heels, as I took Len’s prick in my hands and worked his prick in and out of my mouth making om, om, om sounds. I couldn’t take it anymore. I needed him up my arse. I got up, and pulled my tights and knickers to my ankles, and poked my arse out. I pouted, as Len eased his prick up my smooth arsehole. Within seconds, he was expertly shafting me. What a sight I must have looked. There I was, my knees pressed together, my arse sticking out, knickers down to my ankles, and my hysterical expressions, under the barrister wig! And behind me, gripping my hips, getting into a sweat, in a copper wig and black stocking mask, was this hunky, mature man, buggering me senseless.
‘Shag me, shag me, Len! Oh yes, give it to me! I’m your tighty tight sissy, tighty tighty sissy!’ I heard my heels sc**** the floor, as he shagged me with more determination. Few things could beat the feeling of being dressed like this for a man’s hard cock. I never tired of it, never got bored of this desire. The moment Len and I found each other, I knew there was only one way it would go. The fact was, ever since I first saw him, I longed for him to see my panties and tights stretched to the limit. What’s more I wanted to sit on his face like that, and for him to drench my tight arse with his naked lust. I quickly drew away and asked him to lie down.

‘I have to cum, Polly. I must cum!’ he cried, as he watched me pulling my tights and panties up.
‘You will, darling. I promise you will cum like you’ve never cum before. There’s something I need to do first,’ I gasped, as I lowered my encased arse on his stocking face. Len didn’t hesitate in sniffing me. ‘Sniff, sniff!’ I cried. Pat wasn’t only watching but he was wanking more frantically. I smiled self-assuredly, as I heard the sound of my silky swish grinding, on Len’s nose. After about twenty minutes, I swivelled around and straddled his cock. ‘I need to look in your eyes, as you drench my tights,’ I said. I rode and ground my arse against him, as my eyes penetrated his nylon mask to look at him. ‘I love you,’ I said. ‘You know this is what you’ve always wanted,’ I declared. Within seconds, not only did my wig tumble off my head, but Len violently flooded my tight panties with a tidal wave of spunk. It was so strong that I’m sure it must have penetrated the layers of silk and nylon. I fell into his comforting arms and relaxed my head on his chest, to recover. I curled into him and smiled serenely.
‘Never in my life have I met someone as filthy as you. Never have I cum like that, or have been so hard,’ he panted. ‘I think I love you too,’ he said. After some minutes, resting, we became aware of someone knocking on the window.
‘Pat!’ I smiled. ‘He’s still out there.’
‘I’ll tell him to go,’ said Len.
‘I need a shower,’ I said, as I got up and carefully took off my tights and knickers.. I held the sopping nylon between my fingers. ‘Give these to Pat, as a parting gift,’ I said, before taking a shower.
In the shower I sang. I felt so pleased with myself. When I finished I put a fresh pair of suntan tights and white ankle socks, with my buckle shoes. I put a short blue skirt on and my black sweater. Len was still in the purple, but stained, lycra shorts when I came in. He had taken his mask and wig off. We exchanged smiles, as I packed my bag. ‘I’ll drive you to the station,’ he said.
‘Thanks.’
‘We have to do this again,’ he said.
I fixed my copper wig on and posed with a hand on my hip.
‘Absolutely. I was yours from the moment you looked at me.’

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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 ...

3 years ago
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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...

2 years ago
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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...

2 years ago
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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...

3 years ago
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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
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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,...

2 years ago
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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
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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...

2 years ago
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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
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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
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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...

3 years ago
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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
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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...

4 years ago
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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...

4 years ago
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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
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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
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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
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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...

4 years ago
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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
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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...

2 years ago
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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...

4 years ago
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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
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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,...

4 years ago
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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...

2 years ago
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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
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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,...

4 years ago
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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...

4 years ago
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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
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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
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  • 38
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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
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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
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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...

2 years ago
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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...

2 years ago
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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
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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
3 years ago
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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....

2 years ago
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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...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

3 years ago
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Tightie Whitie Party

"You gotta come, Man!" Roger begged over the phone. The invitationrested in one hand while I held my cell phone in the other. "Half the guysfrom the gym will be there." "And I've fucked most of them, probably," I sighed. Our gym wasnot a gay gym, but it was notorious for the gay sex that occurred in theshowers and steam room. Those of us into man-to-man sex were discreteabout it. If we didn't know the guy walking into the shower room or thesteam room, we stopped whatever sex act we were in...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

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