Sissy Wife Stories

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Sissy Wife Stories

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I married my wife, she was 18 and I was 20. We were married only one year then I noticed I was growing b**** and my skin was getting soft, hair on my body was light as I'm a blonde,my ass was getting bigger while hips were getting wide and I noticed I had curvey body like my wife. I asked if could see her sister that was OB. She made the appointment. I went in nurse handed me a cup said to pee in the cup and get into the cown and climb onto to exam table nurse put my feet in the stripups and said doctor will be in about five minutes but I needed to sign a paper agreeing for treatment. My sister in law walked in and asked if I still wanted and I said yes not knowing what wife and her had planned. She washed my ball area, wife shaved it before we went to the appointment, doctor applied this numbing agent in my b**** area and castrated me. Said this will help in the changes and her husband has me scheduled for surgery in a month to finish my transsation. When got home wife said she fixed up the guest room up for me said she bought me new clothes for me to wear. She said sense I was a girl I needed to dress the part. I was told to change throw away the clothes. She told me I'm Cassidy from now on. She explained that since I had 4" c*** and couldn't get her pregnant and she couldn't divorce me because I soon get my money from grandfather's will. And she showed me all the papers I signed stating I wanted to become a woman, all my friends they knew I transgender because the way I looked and was dressing.


Sounds fake, but I Shure wished it were true. This would be most sissy males' dream!


You're a disgusting freak... You probably gobble man sausage like a pathetic f***** .


I’m married to a gorgeous blonde and she’s been having an affair. I’ve watched my b**** shrink over the years, but they’re the smallest they’ve ever been now. He breeds her regularly while I stay at home. We experimented years ago with me wearing lingerie while we had s** and she knows I was with some men in my younger days. I’m talking recently, she said we would be best friends if we were divorced...that I could REALLY pursue my interests. I asked her what she meant by that and she said she knew me better than anybody and she knows how I would like to live. I waited a couple of days and this AM, after she came back full of c** and I went down on her, I asked her if we were getting back together. She said probably like not but that we were going to be BFFs. I jokingly said you want to sit around and do makeup together snd paint nails with me while you keep your lover around. She cocked her head and said, “that’s exactly what you want to!” Then she just stared at me...I finally broke down and said ok, so if I give you up, you will help me learn to do makeup and help me pick out lingerie and etc? She said, yeah, and in fact I will also set up dates for you with my lover and other guys. You can clean us up anytime we have s** and get all the c** you want and we’ll even get you a s** machine to use so you can be in the room while we are together. She said she could also get me estrogen supplements and her liver already said he would pay to have my b**** permanently removed! I finally caved in all the way and said I would love that arrangement. And with that she let me clean her up and suck every delicious drop of c** out of her p**** . After we finished she helped me order just over $500 in lingerie and the s** machine. My life as a sissy cuckold is just beginning...


Wish one of my wives had offered to do this for me.. i mean to me!!!


Wow my wife would like to due that to me


Nice dream, but I very much doubt you wen't talked to by the doctor to confirm the treatment. Never have I ever seen that not happen. If it were that easy I would have been done like that years ago.


Ah such a dream of a middle aged man


Your story sounds fake as h*** , but If what you are saying is true, why not persue legal actions. Otherwise I just don't believe you. In order for your body to progress to the level it did, as you say, and you sat around as if things were normal makes you sound crazy. It's people like you that still believe in magic!! LOL!!

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I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door.
He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down.
I felt a chill of fear, but tottered down the stairs in my high heels. Lucy tittered as she slapped my bum through my pink nightie. 'Have fun,' she whispered with a mocking edge to her voice, and walked upstairs.
I stood there for a second. I heard laughter from her lover, Pablo, upstairs, a decade younger than me and now invited into my house nightly. He must have pulled her to him as I heard him say, 'Fuck I love your big tits.'
I don't know how I had ended up agreeing to Lucy 'having a boyfriend', or that he could live in our house. Did I know that I would end up so turned on, as I heard her screams of pleasure every night?
I don't know why, in the days after 'Pablo' first appeared, I had confessed to Lucy that I wanted to dress as a girl and give pleasure to a man.
She had helped me, buying outrageously sissy clothes for me online. She never wanted to see me in them, though, but moved directly to contacting men on a forum, saying that I wanted to wear sissy lingerie and be a 'sissy wife' for older men.
I think all her 'help' was guilt after I walked into the kitchen and saw Pablo pawing at her G-cup boobs through her blouse, with an obvious erection pushing into her. He had laughed and said, 'Oh hi Rob,' with an edge to his voice that told me Lucy had told him all about my fantasies.
I heard a deep voice from the living room say, 'Come in...'
He was quite a bit older than me, tall, bearded and muscular, wearing a three-piece suit. I suddenly felt terribly vulnerable wearing my pink baby-doll nightie and white stockings and panties.
He chuckled when he saw me, 'Well you ARE quite the sissy, aren't you? What's your name?'
I started, 'I'm Rob...' and he burst out laughing, saying, 'You don't look like a 'Rob', do you, standing there in your nighty? What is your sissy name?'
I stumbled, 'I'm Chloe,' in a high-pitched voice. My panties suddenly tented as I felt a surge of desire for this strong, masculine man. He must have been mid-Fifties, looked wealthy, and had an air of confidence that I immediately liked.
He smiled and said, 'I'm Hamish,' patting the sofa to show that I should sit down next to him. 'And you're in luck. I love sissies like you. I particularly like to help men who've been pretending all their lives, pretending that they're real men. Is that like you... 'Rob'?
I was feeling flustered already. He knew exactly what he was doing. I sat down next to him and his strong arm went round my silk-clad shoulder.
'I suppose it is, Hamish,' I sputtered, as his fingers began stroking my shoulder through my sheer pink babydoll nightie.
'And what is it you want, Chloe, he said,' chuckling again. 'Do you just want a man to tell you who you are... or do you want a boyfriend... or a husband? Do you want to be a sissy wife?'
I was suddenly rock hard. I felt like I might actually faint from desire after the words, 'Sissy wife.' I felt a desire far stronger than anything I'd felt in years of passionless heaving away on top of my wife, being told to hurry up and finish because I couldn't make her come, too intimidated even to touch her huge, flopping boobs.
``I can see you're a little overcome, Chloe,' Hamish said. 'Is it the idea of being my sissy wife? Why don't you show me what a sissy wife might do for her husband?'
As he said it, his hand moved mine to his crotch, and I felt that he was already semi-hard... and huge. I was so excited myself I thought I would faint, my cock rock-hard in my panties.
I moved to unzip him, but he said, 'I think we should go upstairs, don't you?' Breathing heavily I nodded, and tottered back to my feet.
We climbed the two flights up the stairs. When we passed Lucy's door, I heard her saying to Pablo, 'Yes fuck me, fuck me, my darling.'
To my horror, Hamish knocked on the door and said, 'I'm just going upstairs with, ah, Chloe, and we'll see you later.'
Pablo shouted through the door, 'Make sure you've got Vaseline, sissy!' and to my horror I heard Lucy laughing with him.
Hamish patted my pantied bottom and whispered to me, 'What a silly boy your wife has chosen. You're lucky, Chloe, I'm not a boy... I'm a man.'
I felt a rush of affection for him, and a strange excitement, even among all my humiliation. When we reached the attic room, he sat on the bed and said, 'OK Chloe, so you want to be my sissy wife, do you? To wear dresses, to be my woman?'
I blushed again, and said, in a small voice, 'Yes.'
He said, 'OK Sissy Chloe, do a twirl for me,'
Blushing, I stood in front of him and twirled round. His two strong hands stopped me with my back facing him, and I felt his hands running down from my shoulders, over my satin bra, and down to my satin panties.
He said, 'You are a pretty sissy aren't you Chloe. Now why don't you show me how good a sissy you can be.'
I felt his hands pushing me to my knees. I felt panic. It was all happening too quickly! But I turned myself round and moved my hands to his crotch, where he was sitting on the edge of the bed.
'You've wanted this for a long time, haven't you, sissy Chloe,' he said, 'All those years of pretending to be a man. Look at your hairless arms, your long fingernails. Look at your pink nightie, your lipstick, that blonde wig. Just do what comes naturally, Chloe.'
I shivered in excitement, feeling my cock surge with blood. I was harder than I'd ever been in years of ogling my wife's boobs, wanting (but failing) to take her to bed.
Shivering I slowly unzipped his fly, and pulled his suit trousers and boxer shorts down.
'Here's a treat for you, sissy,' said Hamish, as I bent my head down and took his semi-erect cock into my mouth. I was happier than I'd ever been, suddenly, knowing that this was what I was meant to do, and that I was making this big, manly man happy.
'That's it, Chloe,' he said, 'Gently now, my little cocksucker.'
He stood up and started removing his shirt, as I knelt in front of him, working on his growing cock. His whole body was hairy, unlike mine, and I found myself cupping his balls and licking up and down his circumcised cock as it grew in my mouth.
'You will make someone a lovely sissy wife, I think,' he purred, as his cock began to push against the back of my mouth. I was delirious with excitement when I heard Lucy screaming from downstairs, 'Yes, Pablo, YES.'
Hamish chuckled and said, 'So Chloe, do you want to be down there, or up here?'
I was panting helplessly as I licked his cock and my erection was painfully hard. He knew very well what the answer was. I was gulping at this big man's cock desperately, hungry to make him cum.
He patted the bed and said, 'Come, Chloe. Time to see just how much of a sissy you are. Will you let me fuck you, as that boy makes your wife come downstairs?'
I felt this delicious weakness as I crept onto the bed, and Hamish pushed down on me, kissing me passionately.
It was more intense than any sexual experience I'd ever had, this big, muscular bearded man pushing me down with all his strength, his hands pulling down my panties, his smell everywhere.
Suddenly I felt his hands pushing my legs up, and something wet on my bottom.
I was so intoxicated by desire, I half-wanted to say, 'Wait,' but said instead, 'Fuck me, Hamish, fuck me, please.'
I felt his hardness pushing into me, then this sudden, breathtaking pressure, almost choking me. 'Shhhh, sissy Chloe, shh,' Hamish said gently, then started pushing into me.
I was in pain, but I was still harder than I'd ever been, and he started thrusting into me harder, and harder.
I wrapped his arms around him, like I really was a beautiful, willowy woman and this hairy, masculine man was taking her roughly on her wedding night.
He was pounding into me, and I almost felt like I was having an out of body experience as I felt my cum spraying onto me from my erect cock. I had come without even being touched, just from my man's big cock.
'You really are a sissy, aren't you,' growled Hamish, still pounding into me, 'A sissygasm, I wasn't sure if you'd be able to do it. That's what I want from my sissy wife.' As he said it, I watched his face grimace, as he shot his sperm deep inside me. I was soaked in sweat, utterly spent, and so swept up with desire I suddenly wanted to dress as a woman full time, to go on holiday with him, to live with him...
'God, Chloe, that was great,' grunted Hamish. 'But there are a few more things I need from my sissy wife...'
Quick progression, we almost don't get how the couple's lives were before she got a bf and he dressed up.
You covered his scottish lover really well (although I couldn't shake the image of count Dankula from my head, I'm sorry... That was cracking me up whole story).
But I think you missed a chance to cover how Chloe got ready for her big night and how humiliating this was in front of his wife and boyfriend.
But I think you got a nice story going, curious about the continuation
This is so many of sissies dreams. I have wanted to become a mans wife as my wife finds a woman's pleasure in the bed beside us or in the next room. Feel his strong arms holding me as he kisses me making me feel so safe then to feel his hardness entering me and taking me for his own as my wife feels her mans hard cock giving her what she needs. her. 4yourpleasureiam
i love it, i love the sissy wife to a real man husband plot !!!
please continue you're so gifted !!!
I love this story every time I read it. I too am a sissy husband who would love to be a sissy wife for a hot well-hung man, while my female wife gets fucked by her bull boyfriend.
please tell us more stories like this one. It's fantastic !!!
Your writing is sensory and hits a combination of my own fantasies that I've been meaning to write about--the women's clothing, the first time mlm encounter, the cuckolding. You made me horny for sure. Can't wait for the sequel.
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It is a privilege to be owned by Miss J and I commit to being her Sissy boy. 

I am a Sissy, and I want it to be known that I formally consent to my role.

I am proud to be a Sissy. This might be an insult to many people, but to me it is a dream. I am privileged to have you in my life as a loving partner, and I unequivocally consent to being owned by you. You are the only one for me, and I will always be loyal to you. Your role is much harder than mine, and I promise to try my best to help and assist you. This requires my complete honesty, loss of ego and self-inhibition. Although I still have a long way to go before I become the Sissy-gurl I want to be, I look forward to the road ahead. 

I look forward to wrapping my legs around you as you make love to me,I look forward to feeling you from behind and giving myself to you.

I look forward to kneeling before you as you grind into my face until you cum, I look forward to masturbating at your feet, I look forward to you fingering my pussy while I read this Pledge. 

To be a Sissy is a privilege. I like to wear cute panties and bras, I like to where feminine dresses,I like to look sexy and pose for photos. But with this privilege comes responsibilities and expectations. I pledge that I will respect wearing heels and I will respect wearing make-up; this is a Sissy's rewards, not a right. I am not Woman like you. I am a small-dicked boy who gets excited to where new outfits, who likes to be spat on, spanked, pissed on, cummed on, written on, exposed and helped to remove any masculine or egotistical thoughts. I pledge that I will show my appreciation for what you have accepted me to be, and from here on in, if I am playing the role of a Woman, I will drop to my knees, give you my pledge, and ask to show you my commitment. I will lovingly look you in the eyes as you stand above me and tell you how much I want this. I will moan and show you my eagerness to be your Siss
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