Sissy Cuckold Humiliation Stories

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by SissyTwinkleToes
on Dec 24, 2019

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Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life.
8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...

I'd spent what seemed like forever locked away in my cock cage, looking at and downloading porn for Mistress while she slept. I felt like the slightest touch to my cock would cause me to explode. I had tried and tried to touch myself the whole time but the cage more than served it and Mistresses purposes. I was only able to get so hard and my balls ached. I...

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried.
She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...

My Mistress was entertaining her sister Lady Brandi and her friend Lady Alexis in the living room and watching a Mistress dominate and humiliate a couple of her sissy slut males on DVD. The ladies were drinking wine as I was attending to the dishes after serving them dinner. I was wearing a French maid's uniform with black patent leather pumps and fishnet st...

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her.
The e-mail read:
"Hello, sissy slut,
I have decided I wish to go...

To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real.
I've spen...

My wife/Mistress, Heather and I had over the years developed a large repetoire of ways of playing together, with me, of course, always in a submissive role. One of our favorites was her as Mommy and me as her obedient little sissy boy. What a delightful combination of humiliation and safety it created in me.
However, as frequently was the case, she had deci...

I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door open...

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it.
Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...

I would never say that life was routine with Mistress Monica. She kept me on my toes—or, more literally, on my heels—at least around the house. On days when I got home from my law office before she got home from her corporate job, I would immediately take off my suit and tie and put on one of the frilly aprons Mistress preferred me to wear at home, and a pai...

I excitedly pull my tight red lacy panties up over my small, limp penis. They feel so nice. Tight, but soft, containing the perfect amount of room to hold my little package. My penis does not attempt to get hard despite the pleasure, if anything it seems to shrink a bit in order to fit more comfortably. This was my first time seeing Princess T without her in...

Chapter Three: More Fun and a Deeper Push into a Reality.
[10:15pm]
My phone rings, I look to see who is calling me and I see it is Master Camron. I dutifully answer the call, "Hello, Master, sissy Chantel at your service."
"Hey sissy, I need you tomorrow morning, that will not be a problem I suppose?" He asks.
I reply, "Oh no sir working afternoons or...

After Viv's stimulation it took me a few moments to recover. By the time I looked around Viv was sat on the couch sipping at her almost empty wine glass. A slight smile on her lips and a satisfied look on her face. Our eyes met for a moment before hers wandered down to her pink lace fronted panties I was wearing.
A wave of awareness swept over me as I sudde...

I faded in and out of consciousness.
My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

Here is the third installment of a story of loving spouses, the husband a sissy submissive to his Mistress/Mommy. She has invited over a girlfriend to witness and perhaps participate in his humiliation and degradation. At the end of Part II, the women were on the couch and the little sissy was on the floor. He obeys his wife's command to beg.
*
"Oh, please...

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy.
*****
Chapter One: The Journey Starts.
Well another night and here I sit dressed in m...

I spent a tension filled week on edge. I was easily distracted from even the simplest of tasks as the memories of my adventures in the parking lot with Those People continued to haunt me. I fluctuated between arousal and disgust as visions of my performance played over in my dreams both waking and while a sleep. I had become nerve rattled, jumping at every s...

Lloyd squirmed at the pole in a strange blend of discomfort and sexual euphoria, on an image flickering to life upon the screen before him, his mind fast reclaiming its lucidity from the waning drug. He fought with his own conscience as that lucidity only served to heighten his arousal, his boning cock betraying the undeniable pleasure that had been awoken b...

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Miss Sarah's party finally gets underway.
Husband cuckolded side by side with his wife.
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Michelle's long night continues, but he learns her lesson.
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Cuckold Erotica
This post was modified 3 years ago by JoeMontagna
Until last year, I was the only man that my wife, Julia, had ever slept with. We met in college, She was a freshman, just out of high school, and I was a senior. We met at the library. I accidentally bumped her table when I passed by. She was petite with small breasts and Asian facial features. She looked up at me with her dark eyes and smiled. I smiled back, and I was hooked on her from that day forward.
After a few years of marriage, kids, and jobs, the initial love struck feeling in our relationship had faded, although we were still in love with each other. One night, after an exhausting day, we lay in bed talking about where that love-struck feeling disappeared to and how to get it back. For some reason, we got on the topic of her former boyfriends and why she never had sex with them.
“To be honest," she told me, "I was afraid."
She paused before she answered. She looked into my eyes and smiled. Then, without taking her eyes from mine, she slid her hands into my pajamas and touched my soft cock. She started stroking me lightly as she spoke, "Well, it's complicated, really....See, I know I told you I was a virgin when we met, and that was not a lie....However, I did not tell you how much I loved giving head to my boyfriends. In fact, I had a bit of a reputation for that in high school. I didn't want that to happen in college, so I never told you. You don't really want to know about that, do you?"
Still staring into her eyes, I could feel my cock growing with her light touches. This was a side of my wife I had not known about in all of our years of being married. The fact that she had kept it secret all these years surprised me. "Yes," I replied. My mouth felt dry as I spoke quietly, "Yes, I do want to know."
She slid my pajama bottoms off, leaving me completely naked in the bed while she kept her nightshirt and panties on. Her long black hair brushed against my leg before she swept it to one side of her head. She grabbed a hair tie off the nightstand and twisted it into her hair, forming a ponytail. She looked into my eyes again and smiled, placing her hand back on my cock.
"Oh, my! This conversation seems to be making your cock so hard." She continued to stroke my cock.
"So you had a little more fun in high school than you let on. I thought I was the only one. So what made you afraid of sex?" I suggested as I felt her soft hand stroke the sides of my cock, then the head, back down to the base.
"Oh, you were the first one I had actual sex with. My boyfriends....well.... there's no good way to say this....They were all bigger than you, and I was worried that I'd never be able to fit them inside me. I was afraid it would hurt. Does that bother you?" She asked before quickly adding, "This is exactly how I sucked their cocks," she continued before placing her lips on my cock.
I could feel her tongue circle the head of my cock each time she pulled out to the tip. She then plunged me back into her warm, wet mouth. Her hand worked up and down along my shaft with her lips. Her hand twisted slightly with each stroke. The overall effect was undoubtedly making me aroused and approaching orgasm. I suggested she stop so I could slip inside her.
"Shhh." She told me. "I'm enjoying this. Just listen. So one night, my boyfriend really wanted more than a blowjob from me. His cock was enormous. Well, at least I had not seen one that size before. It seemed almost as long as my forearm. In fact, I had to use both of my hands, sort of like I am with you now. I could not fit him all inside my throat. I mean, I don't usually need to use my hand with you like this since I can fit all of you in my mouth." She paused again to take my cock inside her mouth once more.
As she moaned, I couldn't help but wonder who's cock she was thinking about mine or her ex-boyfriends. I had my answer a moment later when she continued, "I mean, your cock I was so tiny and cute even when it got hard, how could I not want to give it a try? His cock was so huge...Hmmmm....Scary huge." She made a slurping sound as she took me back into her mouth again then pulled her lips off me as she sucked. "Oh, his cock hit the back of my throat and caused me to gag. I tried so hard to get the whole thing inside, but it just wasn't possible." She stroked my cock.
"Is this still OK? Are you sure you want to hear more?" She asked.
"Unh, huh," was all I managed to get out in agreement.
"It took me a lot of practice before I was able to take most of it down my throat without gagging." She continued. She touched my cock head with her palm then drew her fingers up the sides of the shaft until they met at the tip. Then she slid her fingers back down the head to the shaft again. She looked into my eyes once again, bent down, and whispered in my ear, "His cock was so big, I was too scared it would hurt if I tried to take him inside my pussy, not at all like your cute little cock that fit inside me easily."
Her whisper sent shivers through my body. Her fingers stroked me quickly, firmly, and I shuddered in orgasmic bliss. I was so excited that my cum shot against my forehead and hair. Julia noticed and commented, "Oh my! Someone was very excited!"
From that point on, our dirty talk in bed often involved her recounting of her old boyfriends or even fantasies about our current friends. We never thought we would act on those fantasies until, in the act of revenge for a minor prank I played on her during a Bahama vacation, she ended up having a week-long fling with a single, much younger man named Beck. At first, she thought she was just pranking me back, flirting with him, pretending that she would have sex with him. She planned to make me jealous of her attention to Beck's muscled body, but things went a little too far. Her desires took control of her, and suddenly, I was a real cuckold. My wife experienced the thrill of new cock and, through my acceptance of her actions, a renewed realization of her love towards me.
She kept in touch with Beck ever since that day and now, was visiting him in Colorado while I remained at home going to work each morning and caring for the kids each evening. She was gone just over 24 hours of her one week trip before I got her first text.

         "Glad you made it safe."

         "Wow, is that the view."

"Yes. Only a couple hours away from ski areas."

          "But you're not skiing, are you?"

"Umm. No. But I know how much you like to ski."

"Only hot cocoa, warm fires, and red wine for this girl."

          "That sounds about right."

          "Wait. Text me again soon. I miss you."
In the weeks leading up to that visit, Breck insisted that Julia keep my cock locked away in a cock cage. From time to time, Breck had Julia send him photos of my locked cage at random times to be satisfied I was locked. I was forbidden from touching Julia whenever she was nude, and Julia discovered the freedom of remaining naked in our bedroom for prolonged periods. If Breck's rules were not followed, he would not allow Julia to visit him. Furthermore, I worried about the photos Breck had of Julia and I. Although he always promised to keep them safe, I still had a slight worry that others might one day see those photos. Most importantly, Breck also had the key to the chastity cage. If Julia did not go out there and convince him to give her the key, I would remain locked.
A few hours later, I received a single text from Julia's phone.
I spent the night wondering what Julia and Breck were up to. I lay in bed and had a hard time falling asleep. Well, I knew what they were up to. They were fucking. My cock grew hard in its cage at the thought of it. They were fucking, and I haven't even gotten a full hard-on in a month. I wanted just a little sexual relief. I needed to jerk off. Instead, I humped the bed mindlessly until I realized that I was not going to be able to cum like that and only frustrated myself further.
At 2am, I received another text from Julia's phone.
I opened the video. What I saw was my wife in the back hall of a club. She had obviously been drinking and was staggering a bit, but appeared happy and was laughing. She held a cup in her left hand. Someone was using her phone to record the video. She kept pointing at something and saying, "Oh my god! I can't believe you..here? Now?" She handed her cup to someone nearby and got on her knees on the dirty club floor. Then her hands wrapped around a big cock.
"That's right, baby girl...tell me you want Daddy's big cock" It was Beck's voice.
"I want your big cock," came Julia's reply, followed by a giggle.
Julia gave a puzzled look before adding, "Daddy?"
People circled around her and Breck, providing a little cover from the rest of the club. The video showed Julia, my wife, take hold of Breck's cock, put it into her mouth, and close her eyes. Then the video stopped, and I suddenly realized how painfully tight the cage had become. I grabbed a washcloth, wet it, and placed it on my groin. The cool cloth soothed the aching that I felt, and my erection quickly went down. As I sat there with the cloth on my cock, I heard my phone buzz again with another text.
"Show me yours." Came from Julia's phone

         "Show you my what?"

          [Caged cock photo]

"Ha, Ha. That's what we wanted to see."

"Surprise! They all think your caged cock looks cute."

          "I don't like surprises. :("
I turned off my phone and went back to bed. I was embarrassed and angry at myself. Not only had my wife given a blowjob in a crowded club, but everyone with her saw that I was her locked-up cuck. I was also jealous that Breck was there, with my wife. What did I let happen? Why did I let this happen? I realized how much I still loved her and wanted her here with me. Tears formed in my eyes as I was powerless to do anything about it and could only trust that my wife would return to me at the end of the week.
Buzzzzzz. I was at work the next time the phone buzzed with a text from Julia.

           "I'm at work."

            "Oh, OK, I guess."

            "Miss you too."

"He made me go down on him in the club for it."

            "You did that for me?"

            "I love you."

            "You know, I do."

[photo of bare breast pulled out of bra cup.]

             "Isn't that the lingerie set I bought you for your birthday?"

             "The one you haven't worn for me?"

             "Don't tell me you are wearing boots and stockings too."

             "That is so not fair."

             "Wear those boots for me when you get home?"
The next couple of days was the same routine for me. I got up, sent the kids to school, and went to work. Julia sent me texts, some naughty photos. I sent her back pictures of my cage to show I was still locked. She called the images her "Random Check." Taking and sending the photos made me realize just how much I was at her mercy, how much I trusted her, and
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