4:07am Sissy free porn video

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My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled with cum and a big blob of creamy semen dripping from my nose. My face was clearly visible, but just in case there was any confusion, my name, address, phone number and email were written across my forehead under the words "Sissy Cum Dump Sean." Fuck! I was immediately jolted wide-awake. I cautiously typed out my reply. "Good morning," I said. "Please don't share that picture." The reply was immediate. "Don't you worry your sissy head about what I will do with this picture," it said. "Just do what I say and I'll keep your secret safe. Disobey me and I'll send this picture off to your friends and family." I meant to think, "fuck," but what I typed was "Yes, Master." Okay. Please allow me to back up a bit. Yes, I was something of a weekend sissy. I love running home from work on Friday night, jumping in the tub to do an all-over body shave. Then I painted my nails, put on an extra thick coat of long-lasting lipstick and eyeliner and then I started my sissy weekend adventure. A couple of drinks later and I'd be on Craigslist posting an ad for some guys to come by my apartment and use me like a full-on sissy slut. My little sissy stick would swell to full staff, so I'd usually have to tape myself up so that my penis and balls were tucked away until late-Sunday night. I looooove being so hot and bothered after spending a weekend servicing several horny men that I'd finally earn my sissy release on Sunday night; jacking myself off while some anonymous stud fucks me one last time before I hit the shower to say farewell to my sissy weekend adventure. With that in mind, this past weekend I'd met a man online named John. He seemed nice, but he practically came in his pants when he stopped by my apartment a few hours after we'd exchanged some online messages. It was a bit odd, as I am a bit older, and not the most passable sissy out there. John didn't care. He came in and shoved his cock down my throat. It only took a few strokes before he filled my mouth with his seed. That was a no-no. He had promised to play "Safe and sane" with me. He lied. It turns out that I was so happy that he lied. He wasn't done using me yet. Before I knew what was happening, John pulled out some handcuffs and locked my hands behind my back. I started to protest, but a ball gag was quickly locked into place. It was followed by a blindfold and nipple clamps. I already had a butt plug in place (I like to be nice and stretched out before somebody stops by) but John pulled it out and replaced it with a much larger model. John dragged me into my bathroom and sat me down in the tub, cross-legged so that all of my weight pressed the butt plug ever further into my ass. He locked my handcuffs to the faucet. He used some duct tape to secure my legs and then I heard the first tale-tell camera CLICK of the weekend. CLICK. I tried to protest, but I was tied up and gagged. Making matters worse, my sissy stick was as hard as it can get while remaining in its tucked position. CLICK, and then he left me for a moment to worry about how my weekend sissy habit had finally gone too far. He returned a bit later and pushed me forward, I felt something hard pressing against my thumb, and knew that he had found my iPhone and was using my fingerprints to unlock it. After that I heard him chuckle and proceed to put his contact information into my phone. He said, "I hope you don't mind, but I'm going to download a file to your phone." Personal information. I was still blindfolded, so I didn't quite know what was happening, but I knew that I was pretty much screwed. John laughed and then left me, saying, "Don't go anywhere, sissy." He pushed some ear buds into my ears and taped them down. He played a music file that had strange voices underneath. He then left me tied up in the bathroom, wondering what was coming next, and finding myself oddly compelled to listen to the audio file. I'm not sure how long I was tied up in the tub, listening to the music, but I did try to get free (the handcuffs were solidly locked in place) and eventually I ended up falling asleep from exhaustion. I woke to hear the sound of two male voices entering my bathroom as they removed the ear buds. A strange voice said, "Fuck yeah," and then unseen hands unlocked my ball gag. I started to say something, but my mouth was immediately filled with cock. It wasn't going to be a quick face fuck this time. At one point I heard the stranger tell John to slide out of the way. I opened my mouth to allow his cock to enter me, but was surprised to have it filled with a stream of piss instead. I started to spit it out, but I was stopped by a hard slap across my face. "Keep that mouth open, Sean" he said and I gulped hard when I realized that he had learned my real name. The two men drenched me with their piss before heading to my living room. I heard the TV come on and they opened some beers. John and his friend watched the football game, stopping by the bathroom every twenty minutes or so to fill my mouth with their piss. Scared about what was going to happen next, I swallowed as much of it as I could. Somewhere in there, the ear buds went back in. I didn't quite know why at the time, but the music made my cock spring to life as I fantasized about a never-ending parade of cocks filling me full of yummy cummy. My whole body was shaking with frustration by the time the football game ended. John and his friend took pity on me. The turned on the shower to wash away the smell of piss. Then they dragged me, naked and wet out into the living room. They re-wrote my personal information on my forehead with a Sharpie and then John fucked my face while his friend took pictures. Then they swapped places for more pictures. I ended the night being spit-roasted and filled with cum on both ends. CLICK, CLICK, CLICK went the camera as I was used like the sissy cum dump that I had claimed in my ad that I wanted to be. And then it was over. John and the mystery man unlocked the cuffs and left my apartment with nothing more than a "We'll have to do this again real soon." They put the ear buds in my ears and pushed play on the phone. It felt right to go to sleep listening to the music file filling my ears, and I collapsed and fell asleep right there on the living room floor. Sometime around midnight I woke up and stumbled to the shower. I removed my makeup and fingernail varnish, cleaned myself off and mentally vowed to take a break from my sissy weekend adventures. Things had gone way too far, although I did notice that my sissy clit was still throbbing and calling out to me. This was, after all, my sissy fantasy finally come to life, although I swore to myself to not allow it to happen ever again. Boy, was I wrong. My new life as a sissy slut started at 4:07am. The text message and the picture came, followed by a list showing the emails of my friends and family members. My mother's email address was the last straw. I typed back, "Yes, Sir. What would you like me to do?" By 4:10am I was back in my bathroom, with my enema bottle flowing into my ass. "Master John," as I was instructed to call him from now on explained that I would wake every morning at 4am and clean myself out so that I would be ready to serve Master and his friends. Master John explained that I should text him a picture each morning to prove that I was being an obedient sissy slut. I replied, "Yes, Sir." What else could I have done? And as he instructed, I chanted my sissy mantra while I douched myself out in anticipation for the day to come. "I am a cock-hungry sissy slut," I repeated, not quite sure how I had memorized this sissy mantra. "I live to suck cock and be fucked like the sissy cum dump I am. I want nothing more than to spend my days being fucked and filled full of hard cocks and cum. I need to be filled every single day, like a good sissy slut, so I will obey Master John and beg him to make me into the sissy whore I want to become." I repeated this ten times and then emptied my bowels. I texted Master to tell him that I had done as I had been instructed. I felt a surge of pride, knowing that I was being a good sissy slut. Master replied and told me to go check out the Craigslist's T4M section. I found an ad right up at the top entitled "Sissy Slut Needs Daily Training." The ad explained that Master John was training a new sissy slut, and that I needed men to stop by my apartment every morning before work, every day during my lunch break, and again late at night in order to help turn me into a full-fledged sissy slut. All Master John asked in return was a picture every time the men splattered me with their cum. He explained that he would provide me with a "Word of the Day" that I would write on a Post-It note along side of the date. It must be visible every day in the pictures. Master would expect at least five such pictures each and every day, which is why he was looking for an ongoing series of cocks for his new sissy slut to practice upon. My picture was posted with the ad, although my contact info had been blurred out. It ran alongside of some pictures of tied-up sissies with captions like "I need to be fucked every day," "A good sissy always swallows" and "You're the one who asked to be trained. Nobody said becoming a sissy slut would be easy." I could almost hear Master laughing in my head as he sent his next text message. "You asked for this," he said. "I'm going to make all of your sissy cum dump dreams come true." Five minutes later, as per Master's instructions, I had my butt plug back in place, was wearing my bra, panties and stockings and kneeling while blindfolded and gagged in my living room with my front door unlocked. A piece of pink duct tape had been stuck to the doorknob to help my new practice cocks know that they had arrived at the right place. I put my headphones on and pushed play on the file labeled "Sissy slut training 1." I couldn't really make out the words. In the back of my mind, I figured out that it was something like a sissy hypnosis-training file. I knew that I was foolish to listen to it. I couldn't help myself. I pushed play and set the music file to play on repeat. I stayed on my knees for the next hour or so, listening to the strange music. Sometime around 6am another new Master, Julian came in and fucked my mouth. He put his contact info into my phone, along with a picture of my face stuffed full of his cock as the profile picture. From that point on, every time he called me, that picture flashed across my screen. Just before 7am, yet another new Master, Dave also stopped by and shot his load deep into my ass. I was happy to see that he used a condom, although he did tip it over and make me swallow his cum before he left. Both men used my phone to take a picture of me in full sissy-slut mode along with a post it note that read "Sissy 1" along with the day's date. Sometime around 7:30 Master texted me to say that I was free to shower and go to work. He warned me to be sure to be "pantied, plugged, shaved and in stocking from this day on." I couldn't dream of disobeying his commands. Sure enough, Master texted me at work just after 9am, demanding a picture to prove that I was being a good sissy slut. I practically ran to the restroom so that I could comply with his demand, lest he send an incriminating picture to my boss. For some reason, I put my ear buds back in and listened to the sissy file while I worked. I couldn't help myself, it was just something I "had" to do, and it would be something I did everyday from that time onward. Just before 11am, Master sent me a text saying that I would have a visitor coming to my apartment at lunch, and that I should not keep him waiting. I sped home and as per instructions, I was naked and waiting on my knees in my living room by 11:55am with my front door unlocked. Another new Master, Joel came over and fucked me for 20 minutes straight. He turned on my webcam so that people could watch me being a complete sissy slut. 15 people logged on to watch my first day of sissy lunch service. They offered suggestions, so I was spanked like a bad gurl while anonymous men watched me being degraded over my webcam. Then it was back to work. Master John demanded another picture to prove that I was still plugged so that the lunch cum wasn't leaking out of me and spoiling my panties. I complied with his demand and then put my ear buds back in. Sometime around 3p, Master sent me a text explaining what my evening schedule would be. I was to leave my car at work and instead go home with Master Stewart, the mystery man who had fucked me last night, who would pick me up at work at 5pm exactly. The receptionist called at 4:58 to tell me that I had a visitor. I put away my things and went to the lobby. To my utter humiliation, Master Stewart grabbed me by the groin and dragged me out into the parking lot. He popped open his trunk and pushed me inside, instructing to strip and then tie myself up with the roll of duct tape that he tossed into the truck. Like a good sissy slut, I did what I was told. I felt compelled to obey him. He was a man, after all, and he had a cock full of yummy cummy. I really wanted to obey him just in case he would allow the honor of sucking his cock later on. As he drove away I obeyed his command and stripped naked and proceeded to use the duct tape to secure my ankles and knees. I wrapped the tape around my genitals, knowing full well that it would hurt like hell to remove the tape. Then I used my mouth to wrap and tear the tape around my wrists. It wasn't a great job, but Master Stewart stopped after a few miles. He popped the trunk and threw my "ugly boy clothes" to the curb. He then wrapped my wrists up tightly, slammed the trunk shut and drove off. He smiled and said, "Good sissy," and I was thrilled to think that I was being a good sissy slut. My only disappointment was that I couldn't listen to that sissy hypnosis file while I waited in the trunk of Master Stewart's car. It turns out that the Craigslist ad was a hit. More than 20 men had responded. Master John chose the 10 with the biggest cocks. I spent the night being driven to one house after another. I would be dragged into the house, shoved roughly to my knees and then filled full of cock. In the back of my mind, I knew that this was far more than I had wanted. But the sissy hypnosis files were in full effect and I was thrilled to know that if I was a good sissy, Master someday would make me into a real girl. Master Stewart joined in the fun at the first house He mounted me from behind while I sucked off the man in front of me. I heard the ominous CLICKS as round one of my sissy service was documented. Yay! He came quickly, so I was being a good sissy slut. Hmm? Why did I think that? Then I was dragged back to the car and thrown in the trunk. We drove to another address and the scene was repeated. The difference this time around was that I was given a sissy mantra to repeat while I was being fucked. "My name is sissy slut Sean. I love being a cum dump for hard and horny men. I will suck any cock of any man who wants to use me like the cum dump I am." I then repeated my real boy name, my email, phone number and address in between the horny thrusts that pounded into me from behind. Of course it was all recorded. More blackmail to keep me on my knees like the obedient sissy slut I was finally becoming. That was unnecessary. By this time I truly believed everything I was saying and longed to become my fantasy sissy slut for real, 24/7. This went on all night. By 2am I had been dropped off and forced to suck off 10 horny men. Every time I thanked them for allowing me the honor of serving them and swallowing their delicious cum. Every time I gave them my home address, phone number and begged them to stop by and use me anytime they got the urge to fill a sissy cum dump like me full of cock and cum. Every time they promised that they would be stopping by on a regular basis. I got back to my apartment sometime around 2am and found Master John waiting for me. He had a copy made of my door key, so when Master Stewart dragged me inside, I was greeted by the sight of Master John sitting on my couch, watching TV while some strange woman slowly and sensuously licked his cock. He smiled when he saw me. "Hello Sissy," he said and directed me to get on my knees and join in the cock service. Then directing his comments to Master Stewart, he asked, "I got the pictures. Looks like she was a good slut." Master Stewart agreed, although he sounded disappointed. Master John laughed. "Don't worry," he said. She'll fuck up sooner or later, and then we'll make her into a real sissy cum dump." The comment caused me to stop what I was doing and shudder in fear. I felt a sharp sting on my ass, and the mystery woman roughly forced my head up and down on Masters cock. "I fucked up too," she hissed into my ears. "Best mistake I ever made." That was day one. I had serviced sixteen men and had been fucked and had sucked my two new Masters off twice each. I wasn't hungry as my stomach was full of all that yummy cum. I was, however, exhausted, but I couldn't stop until Master was satisfied. At 3:00am I was finished for the day and led to my hall closet. I would be sleeping in a tiny closet for the rest of my life, because a sissy slut doesn't deserve to sleep in a bed. I didn't shower, because I wanted to feel and smell the dried cum that was on me. It made me feel happy; proof I was being a good sissy slut. Master smiled and said, "Good sissy," as he closed the door. I put my ear buds in and pushed play on my sissy hypnosis file. I had a huge smile on my face. I had proved that I was a good sissy. I had sucked and swallowed cocks all day long. My jaw was sore and my stomach was full, but I felt good because I had obeyed Master's commands. I didn't really have a choice. "Good sissy cum dump," he said as I closed my eyes. Maybe tomorrow, I thought, I would be a bad sissy. Not so much that I would disobey Master, but just enough that he would punish me and help make me be a better sissy slut. What would he do? Ohh, maybe he'd tattoo me? Or get me pierced? I knew that deep down, in my heart of hearts I absolutely needed to be pierced and tattooed and then locked in a chastity device so I could never, ever come again. Cum was yummy, but my sissy cum would be icky and gross. I should never ever cum again and a chastity device would keep me safe until Master did me the favor of chopping my clitty and balls off. That wouldn't happen until I grew breasts and had makeup tattooed onto my face. Maybe, if I was a good sissy tomorrow, he would take me to a tattoo parlor. Maybe, if I was a bad gurl, he would take me there as punishment. I kind of wanted to be punished. I didn't know what to do. And then it hit me. Be a good sissy. Always obey Master. But tomorrow I would beg him to punish me anyway and take me to the tattoo parlor and have me marked as his sissy slut forever. With that happy thought, I pushed play on the hypnosis file and drifted off to sleep, repeating my sissy mantra in my head. "I am a cock-hungry sissy slut," I said as I drifted off to sleep. "I live to suck cock and be fucked like the sissy cum dump I am. I want nothing more than to spend my days being fucked and filled full of hard cocks and cum. I need to be filled every single day, like a good sissy slut, so I will obey Master John and beg him to make me into the sissy whore I want to be." My phone buzzed at 4:07am. I didn't hesitate. I stood up and got out of the closet. I filled my enema bag and cleaned myself out for another day of being a good sissy slut. I repeated my mantra ten times, and then another ten just to make sure I was good and clean. I sent Master a text picture to prove that I was being a good sissy, and then, on a whim, I decided to paint my fingernails a bright red. I had a bottle of polish remover in my cupboard. I poured it all down the toilet. I decided to go to work today in full sissy mode. In fact, I couldn't wait any longer to prove that I was a good sissy slut. I went to my closet and threw all of my boy clothes into a trash bag. I walked out, completely naked and put my clothes into the trash dumpster. Today was garbage day, so my yucky boy clothes would soon be gone forever. It was the right thing to do. I went back into my apartment and knelt down, waiting for the first cock of the day to stop by. I put my ear buds back in and started chanting. "I am a cock-hungry sissy slut..." I was on autopilot when the first man stopped by. I attacked his cock like a bitch in heat. I begged him to take my picture and send it to my boss. I begged him to make me into a sissy slut for real. He laughed and said that would be coming soon enough. I heard the garbage truck stop by while he fucked me, and I shuddered in pleasure knowing that I was being a good sissy. Master John was making all of my sissy dreams come true. I would do whatever he wanted, and fuck and suck whomever he wanted. Sixteen cocks yesterday suddenly seemed like I hadn't lived up to my full sissy potential. Maybe if I got myself fired at work today, I would have more time to get that number up closer to thirty. Thirty cocks! That sounded like a good starting point for a sissy slut in training like me. Just before 7am, Master John texted me and told me to get ready for work. I replied that I intended to go to work today dressed as sissy slut Michelle. Makeup, fingernails, wig and slutty dress that would surely get me fired. If that didn't work, I would beg my boss to let me suck him off. Ooh, how great would it be to become the company's sissy slut, spending my days answering phones while sitting on a dildo in the front office and then running off at a moment's notice to suck the cocks of all of our sales staff. Yes, that was what I would do as soon as I got to work, because I was finally becoming a good sissy cum dump. I put on my makeup, thinking that it would look better if it was tattooed on. I used the semi-permanent lipstick and mascara. I started to put on my wig. On a whim I decided to shave my head bald and then used the medical adhesive that I used on my breast forms to attach the wig to my head. I glued the breast forms to my chest and then sprayed the glue on my sissy clit and then secured it back between my ass checks. Panties, stockings and garters and then a short skirt and low cut blouse came next. I looked in the mirror and saw a sissy slut that screamed sex. I knew I was ready and started out the door, off to work. Just as I was about to leave, my front door opened and a man stepped inside. "Sorry, I'm running late," he said. I assured him that it was no problem as I sank to my knees and immediately devoured his cock. Another nasty thought filled my head. I begged him to cum on my face, and he was more than happy to comply with my request. I didn't clean it off, and it was still wet and dripping as I drove to work. There was an audible gasp from the receptionist as I stepped into work. I just smiled and announced that; "I am sissy slut Sean. I belong to Master John and hope that he makes me into a real sissy whore. I can't wait until he chops off my ugly clitty and balls. In the meantime, I will be in my office and will suck the cock of any man who wants to stop by and use me like the sissy cum dump I am." I swiped my key card and headed to my office. I put my ear buds in and pressed play, stripping off my clothes and desperately hoping that I would get to suck a few yummy cocks from sales before security escorted me from the building. If I was really lucky, I would even get to be a sissy slut for my boss, but either way, I knew that I was finally living out my sissy slut fantasies for real!

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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

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

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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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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  • 37
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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...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

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

4 years ago
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son turned into moms sissy

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

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...

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...

3 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...

3 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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