I’m My Wife’s Sissy free porn video

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I was online when l came across an article about dogging, when my wife came home from work l brought up the subject and suggested we try one of the local carpark which apparently was a meeting place. First Jolie thought me mad, but when we were in bed she said may be if we went for a drink before going to the carpark, then decided we would try dogging the following Friday evening.

Friday evening came l sat downstairs while Jolie dressed, l have to say she dressed to be noticed. Her top was a blue see through blouse that showed off the white uplifting bra underneath with a skirt just above the knee that had a split either side that ended about 9” below the waist band of her skirt, Jolie asked if she went to high with the splits, l nodded and remarked she looked fantastic and if l could have l would have fucked her there and then.

We drove to a little pub outside town for a drink there wasn’t a male head that didn’t turn to follow my wife from the entrance to the table which made her blush, but after a few wines Jolie became relaxed and even flirted a little when she went to the toilets before we left.

We arrived at the carpark and parked in one corner there were two cars next to each other, me and my wife both had butterflies. One of the cars put their indicators on, so l did the same, he came and parked my side of the car and asked if we were playing, l nervously explained it was our first time then realised what an idiot l must have sounded. The guy introduced himself as Martin, laughed and said “we all have to start somewhere” then got out of his car and went to Jolie’s window and l left them to chat as she seemed to be enjoying the attention.

Martin asked if he could feel her tits then slid his hand down her blouse, Jolie closed her eyes and sat back in her seat, soon her tits were out and he was leaning in the window sucking her nipples. Jolie didn’t need much persuasion to get out the car and when l got out she was in a passionate embrace with Martin kissing, his hand was now up her skirt and she was eagerly wanking his large thick shaft, Jolie glanced over at me and remarked “l’m going to get a real cock” and whispered something to Martin. He opened our car backdoor; Jolie climbed in and lay on her back then raised her skirt and wriggled out of her knickers, lifted her legs and Martin got into the back between Jolie’s spread legs and slid his shaft inside my wife’s pussy hole, the further he sunk his cock the louder Jolie’s cries became which were then muffled by Martin’s mouth on my wife’s mouth. I stood outside the car watching his buttocks lifting up and down every so often Jolie would let out a moan or groan telling Martin how good his cock felt wedged up inside her. He loudly declared he was going to deliver his hot sticky liquid, l heard Jolie gasp as he thrust downward the pair both whimpering and grunting as they stay locked together.

After another long passionate kiss Martin climbed from between my wife’s legs, he asked if l was going to now fuck her, before l could answer Jolie announced l didn’t have a cock it was more like a maggot then laughed adding a maggot was bigger, l could see Martin wanted to comment, but instead asked my wife when was she coming to the carpark again, Jolie answered soon and hoped Martin would be there they kissed and he said “thank you” before going back to his car. Jolie got into our car a lot less nervous than when she got out and we left for home.

We got home and l sat in the lounge my wife changed into her bathrobe then came into the lounge still quite merry from the wine and the fuck. She became quite abusive telling me l needed a cock to be a man then opened her robe, spread her legs and stretched her pussy lips to show me Martin’s creamy sticky load, Jolie’s inner pussy lips glistened from Martin’s spunk she even had cum over her pussy hairs, she accused me of being a sissy, her sissy and ordered l lick her pussy clean because that’s what sissy’s do. Jolie in a raised voice, shouted “come on, clean me!”, l slid from the armchair l was sitting in and crawled over to where she sat with her pussy spread, Jolie positioned herself on the edge of the sofa cushion and l put my head between her legs, l could smell the strong odour of Martin’s spunk and my wife’s juices on her pussy.

I ran my tongue between Jolie’s pussy, she let out a gasp it was the most excited l had got my wife in years so did it again this time harder, her clitoris became erect, l sucked her furiously she grasped the back of my head and pushed my whole face against her sticky pussy. Jolie had now began shouting “lick me sissy, lick me” then she did something Jolie had never done before she squirted straight into my mouth and face l couldn’t move because of the tight hold she had on the back of my head. I was ordered to carry on sucking as she raised her hips and wriggled on my tongue, the taste of Martin’s deposit in my wife wasn’t as bad as l imagined, l was enjoying myself hearing my wife have orgasm after orgasm.

All of a sudden Jolie let out one almighty cry and yelled “you bastard” as her orgasm exploded, she was panting, gasping trying to catch her breath, l kissed my way up to her tits she lifted my head and in no uncertain terms told me “that’s enough sissy get off me”, l was pushed to one side and told she was going to bed and it would be better if l slept in the spare-room till she needed me again. Jolie got from the sofa and left me kneeling on the floor in the lounge.

At breakfast l knew Jolie wasn’t herself she seemed to look down on me, l wasn’t asked l was told that she wanted the washing done and when l remarked what happened to ‘please and thank you’ she snapped l was her sissy and cockless sissy’s like me do as they’re told. I wasn’t scared, but she was more well-built them me and could give a hard wallop if she wanted, Jolie was 5 inches taller than me and that has always been the joke even when we first met, she would carry me over the fresh-hold because l’m not the athletic sort.

All that morning l was thinking of the previous night, Martin fucking my wife and me between her legs l was getting quite excited even my little maggot as Jolie calls it decided to appear all near one inch of him. I looked down at the wash basket and saw a pair of my wife’s knickers as for what happened next l really don’t know how it happened, l found myself going through Jolie’s knicker draw to find a pair of knickers to wear, next came a bra then l tried on an array of skirts, but found a dress which felt more comfortable, l spent the rest of the day dressed in Jolie’s clothes.

That evening we had our meal then Jolie had a bath and we sat watching telly, she had a few glasses of wine then at around 9.30pm Jolie announced she was going to bed, l asked if she wanted me to do anything, hinting at another tongue licking. Jolie gulp the last of the wine from her glass and informed me, she will tell her sissy when he is needed then gave me permission to wank myself off and crawly added, oh you need a cock to do that, she put her glass down and went to bed.

For about a week l had been changing into Jolie’s clothes and got on with the housework then one day the doorbell rang and without thinking l answered the door, it was Alice our neighbour, she was a pair shaped woman in her late 60s. I had forgotten all about being dressed in Jolie’s clothes it was only when her smile turned to a bewilderment that l realised, Alice handed me a letter saying the postman delivered it to her house by mistake then turned and almost ran down the path.

It was about 40 minutes later the bell rang again this time l asked who it was before opening the door, a soft whisper replied “me Alice” there was no point in me going to get changed, so l opened the door. Alice was clutching a bottle of wine, “can l come in” she asked, she followed me into the kitchen, we sat down and Alice opened the bottle, l put two glasses on the worktop which she then filled. We both took a sip l put my glass down and Alice came straight out and asked why do l wear women’s clothes, l decided to tell her about my sex problem and dressing up was how l now got my thrills, l could see she didn’t believe me about what the doctor called a male menopause that was when the questions started like why couldn’t l take hormone patches, so l explained male menopause wasn’t quite like a females and joked would she like to see my shrivelled balls and little cock to prove it, Alice giggled and declined my offer.

We had a few more wines and Alice declared if l was to dress like a woman then l needed her to show me how to sit and how to walk, the wine was going well. It was strange Alice had been a neighbour for 14 years and in all that time this was the first time that we had actually really spoken; l opened another bottle and our inhibition’s went out the window and the discussion got more frank.

Alice asked if l found knickers uncomfortable as the crutches wasn’t like boxers, l reminded her they would be if l had something there and gave her a quick flash under my dress, she put her glass down and said “show me” then egged me to show her. I was brave enough thanks to the wine l had drunk, so getting to my feet l lifted my dress and pulled down my knickers, Alice looked between my legs, “you’ve got no cock” she declared then pointed at my shrivelled ball sack and asked if she could touch it, l thrust my hips forward and said “go on then”, Alice cradled my balls in the palm of her hand and remarked how l felt warm and rubbery then gently slid her hand back and forth, the next thing l knew she had a very tiny amount of liquid in her hand, Alice smelt her palm and stated l had ejaculated, she put a finger into my spunk and began spreading it in her palm, l apologised and passed her a tissue.

I pulled my knickers up and sat down Alice wiped her hand and told me to sit correctly, l was to sit up not slouch then she got me to walk with her behind me and swing my bum like a pendulum, the sitting l found a lot easier than the walking. I was really enjoying having Alice teaching me how to be a woman, it felt nice being dressed in my wife’s clothes and feel another woman touching me and l think Alice felt the same.

Alice was showing me how to squat in a dress without showing off my knickers when she lost balance, l helped her up and she went to give me a kiss on the cheek to thank me, but l turned my head. I could feel Alice’s breath on my face, l shouldn’t have but l kissed her, she didn’t pull away, but then realised what we were doing a pulled away, l immediately said how l had over stepped the mark, Alice nervously blurted out she had to go as it was getting late, grabbed her cardigan and was gone.

I went into the kitchen rinsed out the wine glasses and put the bottles in the bin, it wasn’t that late and my wife Jolie wouldn’t be home till 5.30pm, so l could have a lie down, l lay on the bed thinking how l had messed it up with Alice, it wasn’t long before l drifted off to sleep.

I was woken by my wife Jolie screaming at me, l had fallen asleep still dressed in her clothes she was holding a black sack filled with my shirts, pants, socks and trousers, she was telling me if l wanted to wear her clothes then l can wear them, but she was throwing out all my clothes. My head was spinning, Jolie left the bedroom and l followed, she was in what used to be our bedroom putting knickers, bras skirts, tights, tops and dresses onto the bed, l was ordered to take the clothes and put them into the room l had been sleeping in then l was to meet her downstairs.

When l walked into the lounge Jolie was sat holding a glass of wine, l was about to sit down when she snapped “l didn’t tell you to sit down”, l stood there like a naughty boy, she took a sip of wine and asked “so you want to be a sissy”, and before l could answer she stated firmly, l was to be her sissy then hitched up her skirt and ordered l was to take down her knickers and clean her sticky hole as Graham a young doctor at the hospital had given her a good fucking in the back of his car before she came home.

Getting to my knees in front of her, l took hold of her knicker waist band and eased then down to her ankles then off, Jolie told me to lick the crutch, l held her knickers to my face and could smell the strong odour of seaman, “lick it” she screeched, l poked out my tongue and slid the crutch of her knickers down my tongue. The seaman taste sent a tingling through my whole body l felt my own watery spunk dribbling down my inner thigh, Jolie spread her legs and ordered l clean her, l got straight on with the job, burying my tongue between her sticky pussy lips, Jolie’s clitty started to swell, so l began sucking her clitty hard she yelled “don’t fucking stop, don’t you fucking dare” and pushed on the back of my head hard into her moist sticky pussy.

I gently bit on her clit this caused Jolie to cry out calling me a dirty whore, she thrust herself against my mouth and squirted, she had such a tight hold on my head l couldn’t move her gush squirted into my mouth, “drink me sissy, swallow it all” Jolie hissed.

Once she recovered from her orgasm Jolie got to her feet and said she was going for a bath and l was to clean up the wet patch on the sofa cushion and carpet because she was bringing a friend home the following evening and didn’t want the room smelling, before going for her bath Jolie informed me we were going shopping in the morning as she wasn’t sharing her clothes with a dirty little sissy, and left the room.

The next day we had breakfast then left for the shops l felt sick the closer we got to the shopping centre, my wife parked l got out the car and froze, she cruelly told me there was no point in hiding l had to go out sometime then announced that’s she couldn’t call me little sissy when we were out and asked if l liked the names Cloe, Rose or Cindy, l replied Cloe sounded nice Jolie nodded and said we were going to get me underwear first then scout a few charity shops for dresses, skirts and tops she turned and walked towards the centre as l followed l could feel the eyes burning into me.

Getting my underwear didn’t take long as my wife brought me plain simple bras and smart cotton knickers which l called Bridget Jones knickers, she gave me a glare and whispered “my sissy will wear what l say” then gave me a false smile before saying, Cloe l bet you can’t wait to get home and try your new undies on, well Jolie was half right l couldn’t wait to get home. She must have dragged me into every charity shop to buy all the old-fashioned clothes she could find, in one of the charity shops Jolie brought me a ginger wig to finish off my wardrobe then thankfully we went home.

When we got home, Jolie told me to change out of her clothes and warned me never wear her clothes again. I went to my room and redressed the bra l padded with loo roll and my knickers were a bit tight the white blouse and blue skirt fitted well, l looked at myself in the wardrobe mirror and fixed the ginger wig then l ventured downstairs dressed as my wife’s sissy Cloe.

Jolie was sat at the kitchen table, she told me to turn around for an inspection and explained the person coming for a drink was Martin the bloke we first met dogging. They had been meeting after work so he could fuck her, Jolie justified their fucking behind my back as my fault due to me having a tiny cock and not being able to produce a healthy load of cum.

Before Jolie’s guest arrived she put makeup on me then l had my orders for the evening which were basically l could be seen, but not heard. Jolie had drank almost a bottle of wine when the door-bell rang, so l went to let Martin in. I had forgotten how he was over 6ft with broad shouldered and l have to admit me being 5ft-6 with a slim frame l felt small standing in front of him. I showed Martin into the lounge and he commented on my dress, Jolie told him l was her sissy and she had named me Chloe, then added to be a man you need a cock and spunk filled balls and this sissy has neither, the pair laughed.

It wasn’t long before they were taking each other’s clothes off, l was sat in the corner every so often Jolie would meet my eye and make a sarcastic comment when wanking Martin by telling me it is a shame l never had a real cock like Martin’s then sucked his balls and with her mouthful Jolie would tell me how she couldn’t wait to get his steaming hot creamy spunk inside her.

They were both naked on the floor, Martin was propped up against the sofa and Jolie had her head between his legs wanking and sucking his cock, l could hear the slurping and sucking sound she was making. Martin had his head tilted back sighing and groaning as my wife worked on his hard shaft, l have to say l was beginning to find watching them was turning me on then Martin shouted “l’m cuming” and pushed my wife’s head downward so she had no option but to take his hot creamy sticky load straight down her throat, l also felt a warm dampness in the crutch of my knickers, it was my own tiny amount of cum there wasn’t enough to keep my wife or any woman happy, but l felt quite proud at shooting something.

After Martin shot his load down my wife’s throat she lay between his legs her hand firmly gripping his shaft to slowly wank him, Martin looked over at me then bushed his hand through Jolie’s hair and told her to work on his cock because he was going to give her a good fucking since her sissy husband couldn’t, Jolie took a sip of wine then l watch her lower her head and swallow up Martin’s shaft into her open mouth.

He put a hand either side of Jolie’s head and began slamming it downwards onto his cock then placed a hand onto her bum and rammed a finger into her arse hole, Jolie gave-out a little cry and worked her mouth faster on Martin’s shaft. He must have been near to emptying his balls once more because he yanked Jolie’s head up and she lay on her back with legs spread wide, Martin got into position between her legs clutching his hard cock and fed the whole shaft fully inside my wife’s eagerly waiting pussy. As they fucked each other all l could hear was their grunting and heavy breathing every so often Jolie would yell “harder baby, harder!”, Martin just let out “ugh, ugh yeses” as he rammed his thick rock-hard shaft deep into my wife’s hole.

Jolie was panting which got louder and louder, she was starting her orgasm; l knew this sound from when l’ve had to lay next to her in bed while she fucked herself with a rabbit.

From where l was sitting l got a good view of Martin’s thick shaft sliding in and out of my wife like a mechanical piston which all of a sudden increased it’s speed then her pussy swallowed the whole length and Martin yelled “oh baby, l’m gonna flood your tubes” and held his shaft firmly inserted between Jolie’s pussy lips filling her with his sticky love liquid, she dug her nails into his back leaving scratches like whip marks. Their panting and groaning subsided and they lay joined together in a sweaty heap, after a long kiss Martin lifted himself from between my wife’s legs and sat against the sofa the head of his cock had a covering of spunk.

Jolie lay on her back with her legs still spread, she half sat up and ordered l make myself useful and clean her dribbling sticky pussy, Martin had indeed filled my wife with a very full thick load, Jolie pulled my head into her hole and as l thirsted on Martin’s spunk she told me that Martin was now the man of the house, l finished cleaning my wife’s pussy and about to return to my seat when Jolie ordered that her lover would like to be cleaned and gave a little laugh, Martin held his cock and rolled his foreskin down. I crawled between his legs gripped his shaft and began licking his urethral opening, Jolie pushed the back of my head forcing Martin’s cock down my throat, “suck it!” she demanded. His cock tasted very salty, l found myself enjoying the flavour and the smoothness on my tongue, my wife ripped my head up and told me to go sit down.

They fucked each other another 4 time with me cleaning them both afterwards, l thought Martin might have stayed the night, but he had to get home to his wife. It was nearly midnight when he left in a taxi, my wife Jolie went to her room and l went to mine.

When l got up the next morning Jolie had gone to work there was a shopping list on the table, l told myself l had to go out sometime on my own and it wasn’t a big list so l could get what we needed at the minimart two roads away.

About 10am Alice knocked at the door as soon as l saw it was her l was about to apologise for the kiss we had, but she stopped me and explained why she dashed off, it was because Alice enjoyed us kissing, but felt guilty as she had only ever kissed her husband in such a sexual way. What she said sent cross messages to me, did Alice mean she wanted us to go further or just forget what happened, anyway for now l was happy she was still talking to me and we sat down to have a coffee. I was telling her that my wife Jolie had left me a shopping list,, but was nervus to go out, so Alice said she will come with me which was a great relief to hear.

The shopping trip with Alice wasn’t so bad as l imagined and we were really getting on, she kept reminding me to walk like a woman, when we returned Alice invited me into her house for a coffee, but that was replaced with a glass of wine.

Our conversation got around to my wife Jolie and what she thought of me as a woman, l don’t know why but l began telling Alice about Martin and Jolie, Alice put her hand on my knee and said she thought l looked wonderful then asked me to kiss her, her lips met mine our tongues entwined and we both sank back in the sofa.

I got my hand under her skirt and into Alice’s knickers, her pussy was very bushy, l whispered “l want to eat you”, she answered by opening her legs which spread her 60-year-old pussy lips, Alice’s clitoris had swollen and protruding from between her lips l gently rubbed my thumb over her clit she let out a gasp. I lowering myself into position and peeled down her knickers, put my mouth over Alice’s clit and started sucking her, she was pushing her crutch against my mouth whimpering, her love juices began to low like a babbling brook Alice was soaking me.

We moved to the floor l raised her legs and really wet to work on her pussy, she wriggled and squealed, l removed my knickers and we got into a scissor position the feeling was fantastic l rubbed my small dried-up wrinkled scrotum hard against Alice’s dribbling pussy even l started groaning, she began shacking and shrieked “oh yeses” then lay on the floor panting. When Alice caught her breath, she exhaled and confessed that was the first orgasm she had ever had as sex with her husband was once a month and anniversaries, it had been this way since they got married 42 years ago. That afternoon we taught each other many things and l don’t think Alice nor l had ever had such a wonderful few hours.

I had been dressing as a woman for 5 months, l didn’t need to wear wigs as my hair had grown and Alice’s training had helped me look more passable as a woman, my wife was bringing home different men, but Martin was her most regular.

One lunchtime Martin knocked at the door l explained my wife Jolie wasn’t home, but he still wanted to come in, so we went into the kitchen and l started to make us a drink when Martin grabbed me from behind turned me around and kissed me, l was powerless to do anything he was much stronger than me, Martin was over 6ft and broad shouldered compared to me at 5ft-6 with a thin frame. Next l was leant over the table and held in place by his large hand at the back of my neck, my skirt was wrenched up and my knickers ripped off, Martin declared he had never fucked a sissy.

I felt the warm head of his cock passing between my bum cheeks then my arse hole being stretched by the head of Martin’s cock, slowly his shaft sank further inside me the pain wasn’t unbearable, but extremely uncomfortable, my god Martin did have a thick hard cock.

When his hard rod was fully inside me he took hold of my hips, “ready sissy bitch” he asked and began fucking me hard and fast, l don’t know what happened, but the thrill of being fucked began to get me very aroused and l found myself pushing backwards to meet Martin’s forward thrusts. He must have been near to emptying his sticky load, l swear the head of his cock inflated just before he yelled “oh fuck yeah” and gave one hell of a thrust into my arse. I screamed with excitement as l felt Martin’s creamy hot stream of spunk flow from his urethral opening, once he delivered the payload he began giving little jerks into my hole then before sliding his cock from me Martin remarked “you’re nice and tight”, he slapped my bum and dressed where as l lay across the table well and truly fucked with a creampied arse hole, but l felt bloody good, it was about 20 minutes before l went to clean myself. I didn’t feel my wife Jolie needed to know about my visit from her lover as l knew Martin was going to make many more quick visits.

My wife Jolie came home and announced she was taking me to an Ipswich hospital to see a cosmetic surgeon, she wanted me to have breast implants and to get something done with my dried-up shrunken scrotum between my legs, it was made clear l didn’t have a say in the matter, but l didn’t really mind because l was enjoying my new life as my wife’s sissy.

It was a quiet drive to the hospital and the surgeon was a nice woman l didn’t do much talking as my wife basically told the doctor she wanted me to have breast and my balls removed. I was stripped and examined it was then the doctor declared she couldn’t give me the cut as my cock was to small so couldn’t insert it inside me to make a vagina, but she could shape my scrotum to look like vagina lips, but before any implants and operation l was put on hormone treatment.

I shall write how my hormone treatment went and what happened on the return visit to the Ipswich hospital.

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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...

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...

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...

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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Home Alone Sissy

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

3 years ago
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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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  • 19
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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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  • 17
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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...

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
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...

3 years ago
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The Lingerie Salesman Sissy

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

4 years ago
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son turned into moms sissy

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

3 years ago
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Cum Craved Sissy

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

2 years ago
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Born a Sissy

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

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