Home Alone Sissy free porn video

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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 patterned line up the back which makes putting them on a chore but well worth it for the effect. They are held up by garter straps from a wickedly tight black silken corset. Well black with pink piping and lacy edges at thighs and breasts. Two medium sized breast forms fill out the cups and give the black PVC high collar maids dress I am wearing that feminine shape. My tiny cock is encased snugly in full black panties that are ruffled with pink lace. No cock cage today I wanted to luxuriate in the touch of silk against my rock hard but still tiny cock. The caress would drive me wild as I worked making for a very pleasurable frotting session later. The finishing touch is a maids cap perched on the candy pink curly wig I am wearing. The makeup is light, the only exception being the bright pink glossy lips. I love glossy lips. I spend the first part of the day posing and taking a few pictures. I then log onto Fetlife and upload them along with a message that there will be more to come. I know I will be able to play long into the evening because my wife Penny has a long meeting today, she told me as she was leaving after breakfast that she would not be home until ten. Knowing this I mince downstairs to wash the breakfast things, my first chore of the day. As I turned into the hall to head for the kitchen I came face to face with a strange man wearing a ski mask. "What the fuck......" he exclaimed. "Who are you?......" I exclaimed. At the same time he realizes I am the owner of the house, and I realize he is a burglar! I turn to run but only get a few mincing steps before he tackles me and we land in a heap on the floor. My breath is knocked out of me so for a few seconds I am unable to struggle. I feel and hear him fumbling with something so I draw in breath to shout for help. As I open my mouth to do so he thrusts a sweaty glove into my mouth effectively gagging me. He then grapples one of my arms behind my back and presses upwards, the pain is intense! "Stop struggling or I'll break your arm," he growls. I comply due to the pain and after more fumbling he has both arms behind my back. He shuffles a little keeping his weight fully on me and then I feel him binding my wrists with what feels like his belt. Once I am secured he stands and then takes a couple of Penny's scarves from the hat stand by the door. Quickly he binds my legs at the knees and ankles with them. He steps in front of me and crouches down. "Well what do we have here....a mincing fag..." he snickers. "Well I was just going to rob the place but it looks like I get to have some fun as well," he chuckled. Leaving me to contemplate my fate he headed upstairs. To my horror I realized all my girly things were on display on the bed, as was my box of bondage gear and sex toys! I also realized the computer was on and logged into my Fetlife profile! I heard his gasp of surprise and knew he had found my sissy things, I blushed at the thought of what he was finding out about me. It was quiet for quite a while then my phone chimed and I heard him moving again. He returned shortly after and to my horror I saw he was carrying my box of bondage gear and toys. He lifted me with ease and threw me over his shoulder then he headed to the kitchen. He dropped me onto a kitchen chair and then retrieved the toy box he had left in the hall. When he returned I noticed the smug grin on his face, he brandished my mobile phone before me. In a falsetto voice he read the text that had just arrived. "Hi honey, the meeting is going to run into the early hours so I've booked a hotel room. I will be home tomorrow morning....." He chuckled as he looked into my shocked face. "It seems we have all night to play........" He placed the box on the table and then winked at me as he started to rummage. I blushed bright red knowing the pervy contents of the box. "Perfect," he smirked pulling out a pair of handcuffs. He moved behind my chair and replaced the temporary bindings with the inescapable handcuffs making a show of putting the keys in his pocket before going back to his search. "What the hell!" he exclaimed as he pulled out my candy pink cock cage. "Do you lock your dick up in this!" he snickered. Blushing bright red I nodded. Once again he moved to me and lifted my skirt. It was at this point he got to see how submissive I was because my tiny cock was tenting my knickers! I blushed even redder as he laughed uproariously. "Hell, this is making you hard," he snickered. Once again I nodded my cock twitching in my panties at this humiliation. To turn the screw he snickered. "Well it's hard but not really big.......more like a clit," he cajoled. He stood and moved to the fridge freezer where after a little searching he found a bag of frozen peas. With a leer on his face he pulled my panties down and dropped the bag of peas into my crotch. I gasped around the glove gag. He then started to play with the cage working out how it worked. By the time he had my tiny cock was completely frozen and shrunken almost to nothing. He snickered as he placed the first ring around the root of my clit. "Damn this is one tiny clit," he smirked as he clicked the tiny heart shaped padlock into place securing my cock as it started to get hard again despite ......or because of my predicament. Once again he pocketed the keys but this time I was not so concerned because I had a key squirreled away. He went back to the box, this time he picked out ankle cuffs attached with a short length of chain. He knelt with a grin and fitted them to me before removing the scarves. The next thing he picked out made me blush and drop my gaze. It was the largest of my butt plugs, candy pink and six inches long. My caged clit throbbed painfully at the thought of how it felt inside me. "I suppose this goes in your sissy arse!" I just nodded my head not daring to look him in the eyes. I heard him rummaging then came the command. "Stand." With some effort I got to my feet, he then placed the well lubricated butt plug on the seat behind me. "Sit," he commanded. Carefully I started to sit feeling the cold tip of the plug against my puckered hole. I adjusted my position slightly to allow it to slip inside slowing my descent as it reached the widest part. He was having none of this and grabbing my shoulders he pushed me down. I yelped as the widest part stretched me painfully then the plug popped inside filling me deliciously. I wiggled my bum enjoying the new full sensation, then I noticed he was watching me and blushed. "I can see you're enjoying yourself.....now it's time for me to have some fun," he growled. He stood and headed for the living room. "Follow me," he commanded over his shoulder. I struggled to my feet and hobbled after him the butt plug making its presence felt deliciously and causing my locked up clit to drip into my panties. In the living room I found him sitting in the chair facing the TV.....my seat. He pointed to the floor before him and then laughed as I struggled to do as he bid, bound as I was. I looked up at him submissively and blushed at the wicked grin on his lip. "Now I am going to remove the gag.... if you shout..... I mean whimper...." he snickered. "I will use the pink ball gag and then beat you bloody," he threatened. Despite the threat, and to my shame the thought of him gagging me had me wiggling on the butt plug. "I think it's time you showed me just how good you are at sucking cock. After all you've written plenty of stories about it." He winked salaciously. I blushed knowing that he had been on my computer....and on my Fetlife account! He unbuckled his belt and then wriggled out of his jeans revealing a semi hard eight in cock, my eyes bulged at the sight of it making him chuckle. "Well I guess you've never seen a cock this big before.....well." He pointed at his cock. Bound as I was I had to shuffle forwards and then lean in my face buried in his crotch. He opened his legs slightly to allow me access and them squeezed them around me so I was now bound by the soft flesh of his legs, a fact that made my clit throb! As I was doing this he pulled out his phone and began to record my ministrations. Immediately I was hit with the scent of him, musky.....manly, it made my mouth water and my clit throb. My heart was beating like a drum as I realize that I was going to suck my first cock. I have fantasized about it so many times and now it was going to happen. Here I was being made to suck another man's cock against my will......but then I realized not entirely against my will! Tentatively I licked his balls, they were salty and the taste matched the manly scent. I relished the taste and lapped avidly at his balls causing him to chuckle. "You're as good as your stories say you are," he snickered, but there was a touch of lust in there. My heart jumped at the fact I was pleasuring him. My submissive nature reveled in this and my clit throbbed painfully. I blushed in response and kissed up the shaft watching it rise to its fully engorged ten inches! At the bulbous head I noticed a tear of pre- cum. Tentatively I stuck out my tongue and tasted him. It was salty and metallic.....and very, very manly. I shivered at the taste giving myself to the submissive cravings knowing full well that he was capturing my every emotion. The butt plug throbbing in my sissy pussy did nothing to calm my submissive cravings in fact it doubled them! "Well that seals the deal....." And with that he removed the ski mask. He was quite handsome with a rugged look thanks to a stubble beard. He grinned down at me obviously enjoying his domination over me! "Since I have all your contacts from your phone and video of you WORSHIPPING my cock...." he laughed. I nodded my head and blushed knowing full well what this meant. "I guess you're going to be my sissy bitch for the night....... and maybe longer....." He laughed at my shocked expression. "Well what do you say sissy bitch?" I wracked my brain wondering what he wanted me to say. "Thank you Master..." Then added, "Please may I suck you magnificent cock," in a simpering voice. He laughed uproariously at my response. "Master.....I like that.....and yes you can cock sucker," he smirked. I blushed bright red at this humiliation but my clit loved the fact I was now his bitch. Eagerly I sucked the head of his cock into my mouth eliciting a contented sigh from him. It was hot and spongy and the taste of his pre-cum overwhelmed my senses. It was hard to take him further into my mouth tied as I was and he seemed to realize this but allowed me to struggle for a while a wicked grin on his lips. Did he realize I wanted to pleasure him, take the whole of his cock..... and yes... yes... taste his spunk! With a knowing smirk he pushed me away fishing in the pocket of his jeans and then reaching round he released me from the handcuffs. As I sat back the butt plug was thrust deeper into my sissy pussy and I wriggled on it unconsciously releasing a moan of pleasure from my lips. "You like having something up your arse...." he growled. "Yes Master," I confessed submissively. "Or should I say boy cunt.......no sissy pussy," he laughed at his inventive name. "Yes Master." I blushed profusely at this humiliation, but knew he was completely right. He sat back and this time I took hold of his cock guiding it into my mouth, eager to taste him again. In my hand it felt so big and I knew I was not going to take all of him. I managed half before the gag reflex kicked in. He said nothing and did not force me so I started to bob up and down on the length I could take, and with my free hand I caressed his balls. My ministrations soon had the desired effect as his breathing quickened. It was not long before his breathing became ragged under my ministrations and my heart beat faster knowing what was about to happen. A submissive thrilled suffused my body knowing I was about to drink another man's spunk. I felt the shift in his body and amazingly his cock swelled even bigger in my mouth! Then he shot his first hot sticky load into my eager submissive mouth. I swallowed it down trying to savor the taste and sensation but a second load followed, then a third and fourth! I barely managed to swallow his massive load. In the back of my head I was comparing his copious load to my pathetic squirt. I shivered realizing just how pathetic I was compared to this man. I truly belonged on my knees at his feet, his sissy bitch to do with as he pleased. This thought and the overwhelming salty, metallic taste of his spunk had my cage clit weeping into my panties. I licked the last few drops from his cock reveling in the manly taste and allowed him to rest, as he did I sucked and kissed his balls knowing his cock would be hyper sensitive at the moment. Regaining his senses he grinned down at me. "Fuck that was good......go get me a beer," he commanded. I got to my feet and performed a low curtsy eliciting a laugh from him. I then hobbled to the kitchen the butt plug sending me into fits of submissive passion, my clit dripping. I served him his beer on a tray with some snacks. He pointed between his legs and I returned to my rightful position. I sucked and caressed his balls whilst he drank his beer, surfing the TV channels until he found a football game. Slowly and to my pleasure/shame I brought him back to full hardness allowing me to once again kiss and lick up his rock hard cock. He seemed to want something because he downed most of his beer in one, burped loudly and commanded. "Stand up." He then unchained my feet leaving the cuffs in place which I am sure was on purpose to show I was still in bondage, this thought made me shiver. He then ordered me to fetch the tube of lubricant he had seen in the box. With a racing heart I headed for the kitchen after once again performing a low curtsy. I knew exactly what was coming and I wanted it, wanted him to take me and make me his bitch completely. I returned to the living room to find that he had stripped completely, I paused in the doorway making him smirk. He was a god, his body was toned and muscled and compared to mine he was all man..... I was a wimp, I sank lower into submission at the sight of him! I moved in front of him and knelt presenting the tube of lubricant to him as if it was an offering to a god, which with my submissive nature he was. He looked down at me a wicked grin on his lips...... and he turned the screw. "Get me nice and slippery, time to make you my sissy bitch!" he growled. I took a large hand full of lubricant and smothered his monster cock with it, as I did I realized how fat it was! I could barely wrap my hand around it and I wondered what it would feel like inside me, I worried it was going to be painful. He interrupted my musings with another command, laced with a sneer. "I know you're enjoying playing with my cock, time to get your sissy pussy ready." With a blush I reached round and pulled the nagging butt plug from my throbbing sissy pussy. It felt good coming out but there was that feeling of loss at its absence much to my shame. I took more lubricant and easily slipped two fingers into my sissy pussy, eager to get it ready for Masters cock. "Enough frotting yourself..... my turn." He had me move into the centre of the room head down ass up. Moving behind me he lowered my panties to mid thigh which I was sure he did on purpose to remind me how pathetic I was. He then slid his monster cock into my ass crack. It felt so big and hot, I could feel it throbbing with life which in turn made my caged clit throb. He moved back and the monster cock slid back until it was resting against my pussy lips. Then with gentle pressure he pushed, there was some resistance so I relaxed and thanks to the butt plug he popped inside without too much pain. There was a burning sting but overriding this was the fact that I was being taken like a girl. The thought filled my head, made me shiver with humiliation......but deep down I loved the thought and my clit twitched in response. All that remained now was for him to fill me with his manly spunk and I would truly be his bitch! He paused allowing me to become accustomed to his girth before slowly filling me inch by inch with his monster cock until I could feel his spunk filled balls resting against my sissy cherries. He paused there not moving, I wondered if he was savouring my hot tight sissy pussy. After a while I started to crave the fucking, I wiggled slightly on his cock eliciting a chuckle from him. "What do you say sissy bitch?" I could hear the smirk in his voice and without hesitation I replied. "Please....oh please Master.....please fuck me.....please fill me with your manly spunk.....please make me your sissy bitch!" I mewled. He slowly pulled out and I groaned with pleasure, then he pushed back in a little faster causing me to yelp as his cock head nudged my prostate. The burning sting was still there but as his tempo increased it subsided replaced with the pleasure of getting fucked. I revelled in the humiliating act, here I was getting fucked by a complete stranger and loving it. I was bucking and humping his cock, begging him to fuck me harder. I was completely lost in sub space but not only that my own orgasm was building. I had used dildos on myself numerous time to try and achieve a sissygasm and here I was about to have one thanks to my new Master. It sent me to a new level of devotion and submission and I begged for him to...... "FUCK MEEEEEE!!!!!" My enthusiasm seemed to spur him on and much to my disappointment he bellowed his own orgasm filling me with his hot sticky cum, I could feel it flooding my sissy pussy. Unfortunately having cum his tempo slowed and so my orgasm subsided. I so much wanted to cum so I wiggled my ass trying to spur him on and keep him inside me. He chuckled, slapped my ass and pulled his semi hard cock from my well fucked pussy. "There is plenty of time sissy bitch..... we have all night." "Yes Master," I mewled. Sensing my disappointment he added, "Besides you're now my bitch so you will be getting plenty of cock." He laughed. I heard him return to the chair but I remained in position hoping he would come and fuck me again. I realized that with just one fuck I had become a sissy cock whore, I blushed at the thought and my clit throbbed..... I just wanted to cum! "Get me another beer," he ordered. Reluctantly I stood and started to pull up my knickers. "No leave them there," he chuckled making me blush. Completely humiliated I curtsied and scurried off to the kitchen his spunk oozing from my sissy pussy with every wiggle of my ass. When I returned he was on the phone. He took the beer and pointed to his sex slimed cock. I knew exactly what he wanted and to my shame my mouth watered. Between his legs again my tongue snaked out licking his balls clean of his spunk and my pussy juice... "Hey dad how you doing?....listen I'm on a job and I need you to come over and help...." He winked at me as my eyes popped open with shock. Not only was I going to be humiliated by this stranger... my Master, now he was going to invite another.....his father, surely I was not going to become his bitch as well! The thought made my submissive self revel with pleasure. My rational side however assumed that he was getting help to rob the place. Since he had spent most of the night using me he would need someone else to finish the robbery. I listened as he gave my address to his father. "Oh and when you get here don't bother sneaking round the back, just ring the door bell..." he laughed. "Yes for real........see you soon." He sighed as I continued to clean his cock, in fact it was now clean and I was working on getting it hard again. He sipped his beer and watched football, but I could see my ministrations were having an effect. When the doorbell rang I jumped and my heart started pumping, I realized I was about to be humiliated even further. "Go answer the door.....but pull up your knickers first!" He winked. Nervously I headed to the door realizing it could be anyone and I was answering it enfemme! I opened the door to an older man but I could see the resemblance in his face, he was also just as physically well built as his son. To my shame my eyes wondered to his crotch as he exclaimed. "WHAT THE FUCK!" I heard a laugh from the living room. "In here dad," called my new Master. He stepped inside looked me up and down incredulously and then headed to the living room shaking his head as he went. I followed meekly blushing with humiliation, my cock throbbing and Masters spunk oozing into my frilly panties. When I entered the room I found that Master had put on his boxer shorts and was lounging on the couch explaining the situation, he paused in his story to command. "Get dad a beer bitch." I scurried back to the kitchen having first curtsied making them both laugh uproariously and me blush. I return served Masters father his beer and as ordered knelt. However not at his feet but at his fathers, I of course knelt submissively my clit throbbing painfully at this new humiliation. Master cocked an eyebrow at me and I immediately knew what he wanted me to do. Much to my shame I eagerly begged. "Please may I suck your cock Master." He immediately began unbuckling his jean a broad grin on his lips. "Shit the last time someone sucked my cock I had to pay for it," he smirked. "Trust me dad she gives better head than any whore," came the ribald remark from Master. He quickly wiggled out of his jeans his semi hard cock springing up before me making my mouth water. If anything it was longer than Masters at about twelve inches long although it was not as thick. This was the second cock I was going to suck and I was relishing the thought. It seemed the non consensual sex had awakened something inside me. I had always been bi-curious now I realized I loved cock as much as I did pussy. It made me blush at the thought but I knew it was the fact I was giving pleasure, I was born to serve, born to pleasure others be they female or male. Eagerly I moved closer and immediately got the scent of him, it was musky, but stronger than Master. My tongue snaked out and tasted his balls, they were salty and the muskiness soon filled my mouth and senses. He looked down at me and I could see the complete look of lust on his face. I kissed and sucked up his cock and then took the bulbous head in my mouth never breaking eye contact. "Shiiiiiit she is good.......definitely better than a whore," he growled squeezing his eyes shut with pleasure. As I started to take as much of his cock as I could I felt Master moving behind me and with a shiver of submissive bliss realized I was about to be spit roasted. I felt the tip of Masters cock against my pussy lips for the second time. This time he did not thrust it inside but waited, I knew what he wanted and with a blush and a throbbing clit I thrust back onto his cock impaling myself. Because he had recently fucked me he easily slipped inside and was buried balls deep. But I could not stop there and began to move backwards and forwards thrilling at the feel of his cock. "She even humps like a whore," laughed Master slapping my backside very hard. This had the effect of re-igniting my climax and I began to hump Masters cock faster whilst sucking on his father's monster cock. Master was soon eager to take control and began to fuck me hard which had me groaning with joy, my climax was coming like a train! I began to shudder and buck as the sissygasm overwhelmed me. It was sweet and painfully as my caged clit swelled in its confines spurting my sissy juices all over the floor. As my sissygasm washed over me I thought I heard the tinkle of Penny's laughter. Through climax clouded pleasure I thought it could not be, Penny was at work, then Master spoke. "You were right your hubby is a fag, you won't believe how easy it was to get her sucking my cock!" he chuckled. I opened my eyes to see my wife Penny standing in the doorway a Cheshire cat grin on her face. I was about to plead my innocence...... claim rape..... and then it clicked, this had been a setup and not a robbery after all, Penny knew my new Master! When she made eye contact she winked and said, "I told you she was Darrel...... but who is the hunk with the...... mmmmm very big cock!" she exclaimed. "Penny, meet my father Paul." "Pleasure to meet you.....or it will be if you don't mind me filling you sissy hubby with my spunk," growled Master Paul. "Oh don't let me stop you," quipped Penny, she moved into the room taking a seat on the couch to watch my debasement. This both thrilled and shocked me causing my just pleasured clit to once more rise to hardness painfully. The sheer bizarreness of the situation sent Master Paul over the edge and soon he was filling me with spunk which much to my shame I eagerly guzzled down, reinforcing my fag status with my wife. As both cocks slipped from my well fucked body she spoke. "Get me a glass of wine sissy," she commanded. I rose and curtseyed and once again headed for the kitchen. My head was in a whirl, what did this mean? Was Penny going to fulfill a lifelong dream and become my Mistress, it certainly seemed so. I returned with Mistress Penny's drink to find her sat between my two new Masters, she was caressing Master Paul's cock which was once more hard again! "I believe you have some cleaning up to do," she smirked pointing at Master Darrel's cock. Obediently I got between his legs and began licking his spunk and my sissy juice from his quickly hardening cock. I could not believe he was getting hard again, I could barely achieve one orgasm and he was ready for his fourth, it reminded me how inferior I was. "That's it get him hard again so he can fuck MY pussy this time," snickered Mistress Penny. She stood and taking hold of both Masters cocks pulled them after her to the bedroom, over her shoulder she quipped. "Lick up the mess you made on the floor, then you can sleep in the spare bedroom...oh and be up early to prepare breakfast......I'm sure the boys will be hungry "she giggled. I slurped my cold sissy juice from the floor and then headed to the spare bedroom where all my sissy clothes were, already I could hear Mistress Penny screaming in pleasure. As I slipped into the spare bed the sounds of their ecstatic cries filled my ears, I fell asleep to Mistress Penny's ecstatic screams! The following day I was up and dressed as I felt I should be in my pink maids uniform, Mistress Penny seemed to approve as I served them breakfast. Mistress even allowed Master Paul to take me to the spare bedroom, now my room and fuck me in my sissy pussy. To my shame I screamed as much as she did the night before. As I was cleaning away the breakfast pots after the Masters had left Mistress had me kneel before her. "So since your true faggot personality has come to life you will now be my sissy maid. You will only pleasure my pussy with your tongue from now on. You will sleep in the spare bedroom, because most nights I will be getting fucked in ours......after all I need to make up for the pleasure I never got from you..." she snickered. I blushed and lowered my gaze because of course she was right, how could I pleasure anyone with such a small cock. "You will only get pleasure from getting fucked in you sissy pussy.....and don't worry about temptation." She grinned mischievously pulling out a chain that hung around her neck to reveal a key. With a shock I realized it was the other key to my chastity device! "Yes that's right, Master Darrel and I now control your orgasms.......just think how eager you will be to please after a couple of months in chastity." I shivered at the thought but my clit dribbled in my panties. "So what do you say sissy........Davina?" "Thank you Mistress...... oh thank you." I kissed her feet and reveled in the fact I was about to embark on my dream life. Mistress left me kneeling and headed for work.

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

3 years ago
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What is a Sissy

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

1 year ago
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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...

2 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...

1 year 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...

3 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 ...

2 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...

1 year 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...

1 year 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...

2 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,...

1 year 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...

1 year 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...

2 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...

3 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...

3 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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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...

1 year 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...

3 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,...

3 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...

1 year 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,...

3 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...

3 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...

1 year ago
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  • 15
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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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  • 14
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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...

1 year 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...

1 year 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
2 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....

1 year 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...

2 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...

2 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...

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...

2 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

2 years ago
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Irsquom my Wifersquos Sissy

My story starts 2yrs ago when l retired early from work, also at that time l was having trouble with my sex life, so went to see a doctor who informed me l was going through what he described as a male menopause which l never knew existed. My scrotum had shrunk and looked like a shrivelled ping-pong ball, my penis had retreated into my balls and could only be seen if l got an erection which measured almost an inch and with a cock that size l was finding it impossible to please my wife Jolie, so...

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