My Neighbour Is A Sissy free porn video

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I could not believe Danny my next door neighbour was a sissy just like me! I found his profile when I was looking for fellow fetishists around my home town on Fetlife, his profile name being Dani. At first I was unsure so with a sense of excitement I sent him a personal message and a friends invite. When he accepted my friends invite I got the chance to see more of his pictures including full face pictures and I knew it was him! With a sense of wonder I scanned through his pictures. He had a few maids dresses and some slutty ones just like me. I had always liked Danny he was easy to talk to and now that I think on it slight of build with fairly long hair, just like me. We generally passed the time of day when we met but were not close friends. His missus Marcy and mine Penny also had a similar relationship. I knew things were going to change quite a bit from now on. We started exchanging personal messages and I got to know more about him and he about me. Much like me his missus knew about his dressing up but did not play. After a while we came upon a plan to have a joint dress up session. My wife was going to be out for a long work day so we arranged the session at my place. His missus worked from home so I guessed the future meetings would be at my place. On the day Danny appeared at my door first thing so I nervously ushered him in. He worked in town so he normally walked to work which meant his missus did not notice anything different when he left for work. Since she was not awake when he left she had not notice the small luggage case he had. I was already dressed when he arrived in black patent leather stilettos, black fishnet stocking, the suspenders from my black and purple PVC corset holding them up. My new black PVC knickers hugged my bottom, my cock hot and turgid pocking through the hole at the front. Over this I had on my black PVC dress which flared at the skirt thanks to the froth of petticoats and swelled at the chest thanks to the fake tits! A white satin apron circled my waist and a maids cap finished my ensemble. He smiled when he saw me, a smile I returned shyly. I took him to the spare bedroom and left him to dress nervously mincing downstairs. When he came downstairs he was now she....Dani. She had picked her pink maids dress which was cut in a similar style to mine. We could in fact have been mistaken as twins, one in black one in pink. After admiring each other we took it in turn to take some pictures. It was strange to have someone behind the camera....well phone, it meant I could relax and enjoy the pose session. I did the same for her and then we set about cleaning the house. She grabbed the hoover and I did the dusting, she had her phone so caught me in some action poses as did I for her. Finally we sat down mid afternoon and downloaded all our pictures to my computer. My cock was rock hard at the sight of some of the shots she had caught of me and she seemed to feel the same. Taking my had she guided me to the bed and after placing her phone on a tripod facing us she sat beside me. Her phone had a Bluetooth fob connection so she could use it to take shots with. She sat beside me and I heard the camera click. My pulse was racing as I looked into her eyes and saw the longing there. She moved closer and her lips met mine. I gasped as I had never kissed a man before but her lips were plump and lush coated with pink lipstick. Mine too were coated with pink lipstick and I felt them slide across hers deliciously. Her tongue snaked into my mouth and I did not resist in fact my tongue reached out to slide against hers. In the background I could hear the camera clicking away immortalising our first kiss! She pulled back a wicked grin on her lips and slipped from the bed moving between my legs. She lifted my skirt to reveal my cock, rock hard and dribbling. I heard the camera click as her tongue snaked out to lick the pre-cum slick head. I gasped at this and shivered at its hot touch, it felt so good. Moving up she took the head of my cock in her mouth swirling her tongue around it causing me to moan with pleasure, she chuckled at my cry of pleasure. Barely maintaining my sanity and not shooting my load in seconds I reached for my phone. She looked up into my eyes as I took the first shot, luckily it had voice activation so I could use both hands to steady the shot. She then gave me such a look of lust as she took half my cock in her mouth that I once again nearly climaxed. I used the fact that I had to get a few good shots of her sucking my cock to help me from not shooting too soon but it was not long before I was, my spunk gushing into her mouth. I was surprised by how much I did actually shoot. She seemed to swallow it all but as my cock popped from her mouth she sat back opening it to reveal a mouth full of spunk. Seizing the chance I got a few good shots then she got to her feet. Leaning in she mashed her lips against mine and fed me my own spunk back in a passionate kiss. My cock throbbed with life at this perverted twist and her wicked chuckle. Once again we sat at the computer to download the pictures and drool at some of the great shots we had taken. She then grabbed my hand once gain pulling me to the bed. Knowing full well what she wanted I went to my knees between her legs a shy smile on my lips. She handed me the fob so I had control of her phone whilst she took mine. I lifted her skirt to find she was wearing skin tight pink PVC panties. Her cock was tenting them lewdly and I realised it was quite big! I reached up with shaking hands to pull them down revealing his pre-cum slick eight inch cock. The scent that hit my senses was also delicious, musky scented sweat, it had my mouth watering in seconds. I pressed the fob to take a few shots and then with a salacious smile on my lips licked the pearl of pre-cum from the tip. Gasping she took a few pictures of me worshipping her cock. My heart was beating like a drum, I had never done anything like this before, never sucked another mans cock.......but I wanted to so badly. Her cock was a good eight inches long so I knew there was no way I was going to take it all. In the back of my mind though I was already planning to train myself so I could. Much like she did I took her cock into my mouth and looked up into the camera as she took shot after shot before my ministrations had her throwing her head back in pleasure. The sensation was unbelievable, I had sucked on dildos before but this was a whole different world. The taste was musky, salty.......delicious, but it was the heat and the throbbing pulse that really set MY pulse racing. I felt it twitch and swell at my ministrations and this in turn gave me a warm glow. I wondered if she, much like me was trying hard to control her climax. She had certainly given up taking pictures for the moment her head thrown back, mewls of pleasure coming from her lips. Once she was completely slick with my saliva I started to caress the lower part of her cock as I sucked on the upper causing her to growl with pleasure. Then I really began to feel her swell and knew what was coming partly because she was crooning. "I'm.......I'm.......going to..........." Not really knowing what to expect although I had imagined this many time, written about it several times! My heart began to race. I think this was partly because I knew what pleasure I was giving, and my submissive nature revelled in this. The spunk when it came was hot......so hot, metallic.....sticky.......and yes delicious. I swallowed the first and second mouth full marvelling at the copious amount and then sensing her diminishing climax kept the rest in my mouth. With a satiated lop sided grin she picked up the camera and I knew what she wanted opening my mouth to reveal its contents. She took a couple of shots before leaning forward to mash her lips against mind so that we could share a salty kiss!. Once again we downloaded the pictures to the computer and marvelled at some of the exquisite shot we had captured! As it was getting close to the time of Penny getting home we reluctantly undressed. I let her choose what pictures she wanted from the day and dropped them onto a memory stick smiling a knowing smile because I was sure she much like me would be uploading many of them to Fetlife. The chance to dress again did not come for a little while, Penny was going to be away for a conference so would be back very late. I personal messaged Dani on Fetlife and was quite shocked at her reply.She replied stating that she was up for it and that I would be the maid.........and she would be the Mistress! She then detailed what I should be wearing when she arrived, my cock grew rock hard at the prospect!. So nervously I waited for her to arrive. She had instructed me to leave the front door open so that she could let herself in and stand in the middle of the living room. So I stood and waited as per her instructions. Black patent leather high heels.....the highest pair I had which made me quite wobbly and mincing when I walked! Black seamed stockings....so hard to get right, in fact I had laboured long and hard to get them straight! Black PVC leotard, a new addition to my wardrobe. It was tight fitting, riding high on my hips meaning it slid into my bottom crack and caressed my puckered hole. A hole that was filled with my largest butt plug! The heavy silver pink jewel tipped butt plug. Its weight tugged deliciously at my puckered hole. My fake tits, pushed against the PVC material the nipples thrust out prominently! As if to show my own excitement even though they too were fake. My cock as per instructions was locked into my new pink cock cage where it throbbed achingly and I knew it was going to be a long day. The keys were on the hook by the door ready for Mistress Dani to pick up when she arrived. Over the leotard I wore my purple and black PVC corset the suspenders holding up my stockings. The extra layer of PVC adding to my hot excited state! And finally over this another layer of PVC, my black maids dress, the hem raised by a froth of petticoats. The finishing touches being a white satin apron ironed smooth, tied with a bow at the back and my maids hat. I had on my pink bob style wig with the side buns that made me look so gurly. My makeup simple....in pink of course. Standing there waiting I thrilled at the thought of being a sub to a sissy Mistress of all things. I must admit it seemed to add an extra thrill because although I had been dominated by a female Mistress it had been a pro dom. I know that even though she knew my heart it was still a slightly stilted affair. I knew that Mistress Dani was just as thrilled as I was to play out this scenario, which made it all the more thrilling!. My heart leapt as I heard her arrive, I stood my head bowed my breath held as I heard her pause at the door. There was a chuckle and then she headed upstairs and once again I was left to wait although this time my pulse was racing knowing my dream scenario was about to be fulfilled. A short while later I heard her descend the stairs and click across the hall, the sound sending a thrill down my spine! Since my head was bowed all I could see was her legs to her thighs and what I saw thrilled me. Black shiny patent leather boots, with very high heals and fishnet stockings. Danny had a very well paid job so all of her wardrobe was high quality and it showed! I must admit I was a little jealous of some of the things she had! She walked around me, inspecting me no doubt. "Tsk...Tsk...Seams not straight...." she quipped. After all that effort I mused. "...and this bow is not even!" She lifted the hem of my skirt. "Mmmm petticoats not fluffed enough." "Sorry Mistress," I mewled. "You will be," she growled. "Hold this," she demanded, handing me a riding crop. I almost climaxed at the thought of its kiss.....my cock twitching painfully. With both hands free she lifted my skirt and petticoats at the back and then reaching between my legs pulled the zipper through allowing my caged cock to spring free and also revealing my butt plug. "And look at you all wet....simply wont do," she growled referring to my leaking caged cock. I felt a little aggrieved because I could not help being horny! I felt her fumbling with the plug and then a sharp pain as she eased it from my sissy pussy. "Good...nice and clean....at least you've done something right," she quipped. I blushed and sighed glad I had pleased her with something at last! "Now since I know what a little slut you are, always playing with your clit.......and stuffing your sissy pussy. I have decided to lock everything up, including your sissy pussy." I felt something cold and fat touch my pussy lips and then thanks to the previous butt plug slip inside with little pain. Then I felt Mistress turning the key and knew instantly that it was the locking butt plug. I had the strange sensation as it opened up inside me and then Mistress locked it in place. Since she now had both sets of keys she now had full control. I shivered at the thought of her taking them away with her when she left today. I would have to beg her for the simple act of going to the toilet! She then zipped both the plug and my caged cock back inside my PVC leotard before moving around in front of me. Taking the crop from my upturned palms she used it to lift my chin to meet her gaze. It was such a dominant look that I blushed and lowered my gaze slowly, allowing me the chance to get a good look at her as I did. She had on a skin tight black PVC basque. So tight in fact that her eight inch cock hard and turgid bulged, lewdly, unconsciously I licked my lips. I could even see the slight indentation of her belly button. She has such a feminine figure that the basque looked exquisite on her. The neck was plunging allowing a good view of her very realistic fake tits and the cut on the leg high to show a lot of pale thigh. Her makeup from the brief glance I got was severe, her hair pulled back in a tight bun. On her arms shoulder length shiny black PVC gloves......all in all my dream dominatrix!. "Makeup a little uneven and definitely not enough lipstick.......I want to see it on my cock when you worship it later!" she growled. I blushed at the further errors and the fact I was going to be her cock sucker......but of course I was! "So Davina how many errors....how many kisses from my crop," she crooned. I counted quickly. "Seams, bow, petticoats, wetness, makeup and lipstick....six Mistress," I mewled. "Well I can't fault you maths....six of the best!" She smirked swaying to the couch and sitting down. "Place my phone on the tripod and set it on the floor in front of us, set it to video, and make sure I am fully in frame, I want to get all the action." She smiled a wicked smile. "Yes Mistress." She patted her lap indicating I was to go over her knee.....I thrilled at the thought. After setting up the phone I laid across her lap. She of course arrange it so that my caged cock was between her legs. "Now we can't just crop this naught bottom can we Davina?....." she quipped. "No...no....Mistress," I replied not sure where this was leading. "No, I want you to think about the sting....wonder when it's going to come...." she chuckled. "However you can't unpunished for your sins so I think we will warm this pert little bottom up first." She placed her hand on my quivering bottom and I shivered making her chuckle. The palm raised....... ......... CLICK......the phone started recording.....I tensed but nothing happened....she chuckled. ..... I waited a quivering wreck. SLAP!. The thin PVC covering on my bottom did nothing to lessen the sting! So I yelped with shock. SLAP!......on the other cheek. She continued until my bottom was hot and stinging then set me on my feet. "What do you say?" she smirked. "Thank you Mistress." "Now go and get me a glass of wine." I curtsied and minced to the kitchen my bottom hot and stinging.....my cock rock hard, throbbing painfully in its confines. I had bought the wine she had asked for and brought it to her on a silver tray with some snacks. She made me wait balancing the tray on one hand whilst she uploaded the spanking video onto her laptop, she then watched the whole thing as did I over her shoulder. "Mmmm that's got me so horny!" she mused turning to face me....she pointed between her legs and I took my place, wincing as I sat on my tender bum! I could see her rock hard cock thrusting against the crotch of her basque and so much wanted to pleasure her. She winked and I knew instantly what to do. With shaking hands I reached up and slid down the crotch zip allowing her cock to spring free. It came away from her stomach with a slurp leaving a string of precum behind, testament to her excited state! Eagerly I moved past her turgid cock eliciting a mewl from her and lapped up the sticky juices coating her stomach savouring the musky taste.....sweat and precum! I moved my ministrations to her balls and up the shaft and she crooned her pleasure. Keeping eye contact I sucked in the head causing her to gasp with pleasure. "Slowly gurl...." she gasped obviously barely keeping control. "Suck my balls....I want to make this last," she commanded. So as commanded I sucked and licked her balls until she could take no more and demanded that I returned to sucking her cock. Once again I kissed up her rock hard straining cock. Then I took in a deep breath and winked at her causing her to frown in puzzlement. I then slowly salaciously took the whole length of her cock down to the balls. You see, unknown to her I had been practicing.......a lot. I could now take the ten inch dildo I had without a single tear! I watched her eyes widen as I swallowed inch after inch. "OOOHHHH MY GODDDD......I CUMMMMING!!!!" she growled. Since I had her fully down my throat there was nothing I could do but take her sticky spunk straight into my stomach. I regretted the fact I would not be savouring a mouth full of spunk but revelled in the shocking pleasure I was giving. Her cock throbbed and pulsed inside me and having shot three loads I pulled back allowing the last few drops to hit my tongue. "Well, well, we have been practicing....quite the cock slut," she growled a lopsided grin on her face. I blushed and felt pleasure and pride at having pleasured her so. Gaining a little composure she commanded me to go and clean the bathroom and then return when I had finished. As I made to put away her still hard cock she stopped me. "No I'm going to do some uploading to Fetlife....so I may play." She winked. I cleaned the bathroom, toilet, shower, sink....all spotless, so I thought. I even considered putting the various bottles into size order but thought that was too much and then returned to Mistress. She was looking at some of the new pictures on Sissy Zelda's profile when I returned and with a curtsy informed her I had finished. She bid me freshen her wine glass and then led me to the bathroom for inspection. It turned out the bathroom was not as spotless as I thought. There was soap suds on the underside of the hot tap, a spot of lime scale in the shower, a watermark on the toilet seat....which she made me lick clean, I knew the seat was hygienically clean but I shivered at the humiliation, my caged cock twitching! And finally the various bottles were not neatly in size order.....I cursed myself. "So lets make it an even six....." she quipped. "Over the toilet!" she commanded. I blushed at the humiliation of having to bend over the toilet to receive my punishment. She used the crop this time and I thrilled at its fiery kiss.....but was reliably informed that the stroke were only light. I then sweated the fact that they still stung like hell......what was full force going to feel like!. So I cleaned the rest of the house in this manor receiving more stripes for my efforts. The final room she made me clean was the spare bedroom, when it was finished I once more returned to her. "Finished Mistress," I simpered. "Good, now go back and take the quilt off the bed and fold it neatly, then position yourself on the bed on all fours," she commanded. I did as she bid and a short while later she joined me. As she entered I noticed she had released her cock from its PVC confines. It swung hot and turgid in front of her. I gasped and blushed at the sight of it assuming I would soon be sucking it again. "Head down on the bed!" she growled. She then moved around the room no doubt inspecting my work. "Good gurl....you seem to have got the idea of my exacting standards...." she chuckled. I blushed at her calling me a gurl and the fact I had finally appeased her. "But there is still the matter of the six proper stroke," she quipped. She moved to the bed and flipped my skirt and petticoats over my back exposing my somewhat tender bottom, I felt the crop rest against my bottom. "You will count them and you will thank me," she intoned. The crop left my bottom and I tensed............. SWISH........CRACK! The stroke was fiery and intense causing me to yelp and shuffle on the bed. "Hold still girl," she demanded. "One......Thank you Mistress......Please may I have another," I whimpered. She chuckled knowing full well I did not! How I lasted I was not sure but my bottom was on fire when she had finished. It seemed the earlier strokes had set my nerves on edge making the final six even more painful....in fact I was in tears when she had done. I felt her mount the bed behind me and then she unzipped me allowing my caged cock to spring free. "Well someone may be crying like a baby but her clit is saying she liked it!" she chuckled. She was in fact correct my cock....clit was hot and throbbing adding to my misery in the fact I could not stroke it. She peeled the edge of the PVC over my bum cheeks to assess her handy work. "Well someone is going to have stripe marks for a few weeks." I shivered and my clit twitched. I know the purists would say you should not mark your slave but I loved bruises.....crop stripes. My wife Penny once beat me with a shower brush....she was mortified at the bruising but I loved them. All week, every chance I got I would look at them and get horny! I was not worried about Penny seeing these marks since I was always beating myself during my dress up sessions. I felt Mistress using the key on my butt plug and slowly it closed inside me. It was strange since I had become accustomed to its size. She then removed it setting it aside and I wondered what she intended. I felt her full weight on the bed and knew exactly what she intended. I shivered wondering if I was really ready for this. Of course I was kidding myself....I was more than ready.....I was eager! I felt her cock nudge against my puckered hole and then she moved in closer sliding her cock up the crack as if to tease me...her words confirmed this! "What do you want Davina?" she queried and I could hear the mirth in her voice. "Oh please......please I want you to fuck me!" I mewled. "But you're not gay.....are you?" she chuckled. As she was talking she was sliding her cock.....all eight inches up and down my crack! "I....No......I....I'm......please!!!" I pleaded. I was pretty sure I was not gay, or was I. I must admit I was definitely bi curious....so getting fucked by her hot fat cock seemed natural.....to cure that curiosity I mused. She in answer to my pleading pulled back and placed the head of her cock against my puckered hole. I was wound up so tight it felt like she was not going to fit inside without hurting me. Sensing this she eased back. "Relax Davina.....I'm going to fuck your tight little hole....but I want you to enjoy it as well......so relax," she commanded. I took a deep breath and tried to still my beating heart.....I so much wanted her inside me. Sensing me relaxing she pushed again and the head popped inside with a slight spike of pain. She held there allowing me to become accustomed to this new intrusion but truth be told I wanted her deeper. Once again I found myself comparing other things I had thrust inside myself and once again they came up short. Her cock was so hot it seemed to burn......and the pulsing of the blood inside it felt exquisite! She held still and I itched to feel more, so I started wriggling eliciting a chuckle from her. "I knew I was right to lock up your pussy.....you are such a slut!" she quipped. But still she held still, causing me to mewl in frustration. "Want more?" she quipped. "Yes please Mistress......please fuck me!" I begged. "I love it when you beg." With that she slipped further inside. I loved the point where the head nudged my prostate and hearing my gasp of pleasure she stopped to nudge the tip backwards and forwards sending me insane! I wondered if I was going to experience the fabled sissygasm, but was not close enough yet. Just before she was almost in I began to wonder if I could take all eight inches, I had never had anything that big inside me before! The pain and pressure began to build causing me to moan. She slowed and began to gyrate her hips until with a strange pop she slid fully inside, I shuddered because the feeling was so intense, I felt full, felt used...in a nice way. I could hear her panting behind me and wondered if she was just as excited as I was, I also wondered if this was her first time. I guessed she was excited because she pulled out straight away and then thrust back inside causing me to squeal with pleasure. Soon she was fucking me with abandon and I was loving it! Humping back and begging her to fuck me harder. It was with a little spike of frustration I heard her scream her climax as she shot her spunk into me. I did however shudder with delight at the feeling of her hot sticky spunk filling me! She collapsed against me and I thrilled at having pleased her despite the fact I had not climaxed myself. In the back of my head I was hoping she was going to release me and let me play. Once she had recovered she ordered me to the bathroom where she had me clean her limp, sex slick cock with a sponge before she disappeared off to the spare bedroom. Danny emerged a short while later with a wicked grin on his lips. I looked at my watch and realised it was quite late and Penny would be home soon...much to my disappointment. "Poor Davina, I guess you're quite frustrated," he grinned. "Yes Master....please may I......." "Hush sissy.....no you can't have the key.....which means you don't get to cum!" he winked. "But...what about Penny....when will I get the key back?" I mewled. "No more mewling sissy!.......you will get it back when I decide," he growled as he left. I was left......very....very....frustrated! *********************************************************************** NOTE TO READERS. This story is a labour of love but it is a labour so if you enjoyed it please leave a comment. Critiques, no thank you this is not Pulitzer material. ***********************************************************************

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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...

2 years ago
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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...

3 years ago
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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...

2 years ago
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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...

4 years ago
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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
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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 ...

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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Neighbour Aunty Nude Bath Seduce

Hai friends, I am rajan from Pondicherry. I have earlier written my first sexual encounter with my aunty few months ago. I have received marvelous response from the readers. With that inspiration I am going to write another real incident which happened a year back and also continuing now. As stated in the previous encounter, I like much to see the women bathing which makes me more excited than even seeing them fucking. Now I and my wife are living in the town street (I don’t want to mention...

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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  • 42
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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
  • 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
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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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Neighbour asks a special favour

As I got home I heard chatting, from across the street and noticed my opposite neighbour was out on her balcony having lunch with a friend about the same age. I'd sometimes seen her coming and going, a woman a couple of years older than me, maybe late thirties, quite attractive and certainly with a body that looked younger and fitter than that. I'd often looked down from my 3rd floor window into her 2nd floor flat and wondered if I'd catch a glimpse of her in her undies or naked but sadly...

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...

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