Saturday Morning Sissy free porn video

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Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red dye. If that wasn't enough, my toenails and fingernails were painted a cherry red and I was wearing a jet-black baby doll nightie, a pair of crotchless panties and there was something lodged securely up my ass. Something big lodged securely up my ass. It was obviously not a typical Saturday morning. There was a post it stuck to my phone that simply read, "Check your voice mail." My heart skipped a beat as I picked up my phone and pushed play. "Hello Sean, or perhaps Sissy Michelle is more appropriate." It was an unfamiliar voice greeting me from the tiny speakers. "You probably don't remember me, but we had a very revealing conversation last night." "My name is Marcus, but you should call me Master from now on. After all, you practically begged me to make you into my own personal sissy slut last night. If you don't believe me, check the photos on your phone." I pushed pause and flipped to the Photo Album app, even though I was pretty sure what I'd find there. I was still shocked to find that there were 97 new photos waiting in an album titled "Sissy Michelle night 1." 97 pictures! In each one I was on my knees in a bathroom stall with a glazed look on my face and a cock shoved down my throat. Or it was a picture of me from behind with a cock plowing in and out of my ass. Every single picture had a good shot of my face, usually glazed with cum and a look of half- drunken lust. The different sizes and skin tones of the cocks revealed that I had been used by at least ten different men last night. In fact, one of them had me on my knees surrounded ten cocks in the one picture. All of them looked like they were ready to pop. These were pictures that could easily destroy me, especially as most of them were labeled with the email addresses of my family, friends and co- workers. They were shocking, but also pictures that made my cock stand up straight, bobbing in anticipation of a repeat performance. "I hope you like the photo shoot," the voicemail continued. "I know that I had a lot of fun taking the pictures and finding all sorts of total strangers to come by and make you over into a total sissy slut. I had so much fun that I think I'll do it again tonight. And every night from here on out." My cock was throbbing with the thought. In my heart of hearts I knew that this was it. My darkest fantasies had finally been exposed. I knew that I had met a man who would make all of my sissy dreams come true. I was scared to death. I couldn't wait. I still don't remember a lot about that night, but I do recall a few bits and pieces. I went to a club with a group of friends after work. Somehow I ended up at the bar with a very tall man who started buying me drinks. I couldn't recall his face, but I remembered his eyes. They were a piercing blue and seemed to bore right into my soul. Those eyes were stern, yet full of promise. When my soon-to-be Master asked me about my deepest fantasies, those eyes demanded that I bare my soul for his amusement. I did just that with only a few shots in me. I told him that I longed to be a full-fledged sissy slut. That I longed to belong to a man who would take me and make me over into a complete shemale. That I was looking for somebody who would train me, and force me to service a never-ending parade of hard cocks. Somebody who would lock me in a chastity, start me on female hormones and then start turning me into the perfect sissy cocksucker. While I admitted these fantasies of mine, this strange man with the intense blue eyes kept demanding that I take one shot after another. I was totally trashed before midnight when he had me post my first ad on Craigslist. I've since printed it out to remind me where I started. "I am a sissy slut in training," my ad read. "I require several men who will allow me the honor of sucking their cocks on a daily basis if I am ever to become a good enough sissy to please my new Master. If you are interested in helping to train me, please respond to this ad. Tell me how often you can stop by and feed me a creamy sissy treat, what time of the day you are free to stop by, whether you're okay with using me while other men line up for sloppy seconds, and if there are any other kinky activities you'd like to force me to try. I am interested in it all." "Please be prepared to take pictures of me servicing your cock," the ad continued, "as my new Master will require proof that I am becoming a good and constantly-horny sissy slut through lots and lots of practice." The ad was illuminated by one picture. A picture of me with a large cock shoved down my throat with the word "Sissy Slut" and my cell phone number and personal email written across my forehead in dark black ink. The ad had obviously attracted plenty of attention. In addition to the 97 photos from last night, I had scores of voicemail messages and emails waiting on my phone. So this was it. My life as an average, everyday working stiff was over. I'd gotten drunk and revealed my darkest fantasies to a man who seemed determined to make them all come true. I was scared to death, but also thrilled beyond belief. I was also quite horny, and while I desperately wanted to grab my cock and get some relief, deep down I knew that I shouldn't do so without my new Master's permission. Back to the voice mail. "We had fun last night, and I intend to have fun with you on a regular basis. That being said, you were quite drunk last night, so I'm not quite sure if you're serious or not. If you truly want to become my sissy slut, I will make you into the most depraved slut in town. I will keep you in the sexiest clothes and tallest stiletto heels. You can expect to spend your days with your ass filled with cock--either a butt plug or the real thing, 24/7. I will start you on hormones immediately and will take you in for breast implants as soon as your titties have grown big enough to accommodate them. If fact, I will personally shove the needle in your ass tonight while I'm fucking you." There was a dark, dangerous laugh on the message. "If you look over on your nightstand, you will see a chastity and a padlock. Notice that there is no key. This is how you will prove your devotion to me. If you truly want to be my sissy slut, you will lock it on, snap the padlock closed and send me a picture of your cock locked away for good. Do not be fooled. If you put on the chastity, I will not unlock it for at least one month, and only then if you've been a good sissy slut the entire time." "You will be given sissy goals. We'll start out some simple tasks. You will suck 10 cocks every week, loose 5lbs each week, dress in full sissy mode every night after work and start a journal where you expose your slutiest fantasies for the entire world to read. We will post these fantasies online, along with plenty of photos of you acting them out. We will also be posting your contact info along with the stories, so that any horny man can track you down if he really wants to do so." There was a long pause in the message. My heart was pounding in my head. Somehow this man knew exactly what I wanted to hear. "If that's what you want to have happen, lock the chastity around that little thing you call your cock, take a picture and text it to me. You'll find my number in your phone under the heading of Master." "Then you will have 15 minutes to prepare yourself for your new Master. That means your should be gagged and blindfolded, stuffed at both ends and totally immobilized while you wait for Master to come whore you out. I'll give you more instructions on this in the future, but for now you should leave the butt plug in, then go to your garage and get a roll of duct tape and start binding yourself up tight. I expect to see you completely wrapped up from your nipples down when I show up." "Leave the chastity sticking out, as I'll want easy access to torment your tiny clitty." Be sure to save some of the duct tape so you can stick a rag in your mouth and tape it in place. I generously left a dirty rag by your bed that should give you a preview of what you'll be tasting from here on out." "Tape the rag in place--enjoy the taste. Go to your voice-recording app on your iPhone and push play. It's a recording of you begging for my cock and getting fucked last night. Make sure you put it on a repeat loop. Then use some of the tape to tape your eyes closed and handcuff your wrists to the furniture so you can't change your mind." "Then wait." There was another long pause. "Wait for as long as it takes for me to come by. It could be minutes. It could be days. Either way, you won't be going into work on Monday." "So what do you say sissy? Do you have the balls to make your fantasies come true? Be aware that if you do have the balls, I will probably be cutting them off in the near future. But until then, I promise to make all of your sissy slut fantasies come true. I will break you and then remake you into the world's biggest sissy slut. There will be full body- transformation, lots of humiliation and a career in fetish porn in your near future. That's if you're willing to lock yourself in the chastity and give yourself over to me." "Personally, I don't think you will do it. But I hope you do. It's been five years since I last made a sissy slut, and I have lots of new ideas to try out. Lock yourself up and send me the picture and I will make it all come true." "Or don't and I'll leave you alone. Of course you'll have to figure out how to explain the nail polish and writing on your forehead. I'm sure that the sissy slut words will wash off your face in a week or two. I used a permanent marker and wrote it out several times so that it will be there for quite a few days." "But it's your call. Take the picture and I'll change your life. Or chicken out and go back to being some nobody with all these unfulfilled fantasies. I hope to hear from you very soon, but I'm not going to stay up all night waiting." What to do? This was exactly my fantasy come true. I'd dreamed of having a Master who would turn me into the perfect sissy slut. Somebody who was demanding and who would fully own me. The porn career thing was a new twist, but it was one that set the gears in my head turning. Could I do it? Could I give in? The tone on the voice mail and the memory of those blue eyes made me feel that this was no joke. If I locked the chastity around my cock, I knew that I'd be changed forever. I had a good job, lots of friends and a loving family. I would loose all of this. How could I give that up? Especially for a man I'd only known after one drunken night of slutdom. Perhaps he'd be willing to ease me in, I thought and then immediately dismissed the idea. This was a man who wanted a total sissy. Nothing else would do. I was torn, unable to make a decision. But then I noticed that in my revere I'd gotten up and moved to the garage. The duct tape was in one hand while my throbbing cock was in the other. I was on sissy autopilot. My cock was too hard to fit in the chastity, but a couple of ice cubes shrunk me down, banishing my hard-ons for the foreseeable future, maybe forever. Before I could stop myself, the ring of the chastity device was tightly nestled behind my balls, the cage was slipping over my cock (quickly, before it got hard again) and the padlock was slipped into place. This was it. One click and my life would be changed forever. Click. My cock was throbbing so much that I could see the chastity rise and fall. I immediately loved the feeling of being so hard yet unable to touch myself. I hoped that it would be this way from now on, even if that meant that I would never come again. I went to the bathroom and covered myself in shaving cream. I had been shaved last night, but there were a few places that Master had missed. I quickly made sure that I was smooth all over then took a quick shower to clean myself up. The butt plug came out just long enough for an enema before it went back in. The butt plug was huge, much bigger than anything I'd ever used before. It took a while to get it seated back into place. It finally popped in as I was thinking that it probably wasn't the biggest plug I'd ever have to wear. The sharpie was still sitting on the counter. I carefully re-wrote the message on my forehead, although very little of it had faded from my shower. I added my real name to go along with my phone number and email. Then I took a red sharpie and gave myself some lipstick. I checked the front door. It was unlocked. As was the back door. I was ready. I laid myself down on the couch and began to tie myself up. The duct tape was amazingly secure. I wrapped it as tightly as I could around my legs, being sure to wrap extra around my ankles. It was unnecessary. There was no way that I was ever going to break free. It suddenly dawned on me that one roll wouldn't be enough. I hopped awkwardly to the garage and collected two more rolls. The first one became a makeshift corset. It was difficult, but the next roll covered my arms all the way to my wrists. I would have done the hands, but I was afraid that I wouldn't be able to get the handcuffs locked on if I did. There was still more tape. "In for a penny, in for a pound," I thought and started to wrap it around my head. This was going to pull my hair out in the morning. I kind of liked the idea of being a bald sissy slut. When I was finished, there was only a little skin showing around my eyes, mouth, cock and hands. I was sweating already, but horny beyond belief. I took out my phone and took my first sissy selfie. It was off to my Master in no time along with the message, "Please come make me your whore." I pushed play on the voicemail file and turned the volume up to full. It was loud, but not so loud that I couldn't hear the click of the handcuffs being ratcheted down on my wrists. Then I waited. My phone pinged after a few minutes. It was either a voicemail, an email or a text message. Either way it was probably somebody looking for a kinky sissy slut. I wished I could answer him, but I couldn't get to the phone with my hands handcuffed and locked around the arm of my couch. I don't know how long I waited. My phone never stopped pinging and ringing. Each time my cock jumped in frustration. The voice recording continued to play. Over and over I heard myself say; "I am nothing but a sissy slut. I live to suck cock and be fucked, each and every day. I spend my days dreaming about cocks and cum and feel empty when there's not a hard cock filling my sissy pussy." "Please Master, fill me full of cum and then make me into your perfect sissy slut. I will do anything and everything you say, if you'll just turn me into your si..." My words were interrupted by the sound of something being shoved in my mouth. The taste from my gag gave me a good idea of what it had been. The rest of the file was nothing but grunts, slapping sounds and high- pitched squeals as I heard myself being fucked over and over again. There were two men grunting on the recording, so I was obviously being plugged from both ends. God, I wished that I was being plugged from both ends again right then. But no. I was just a horny sissy, tied up tight and dreaming of cock. The recording ended and started with the sound of Master's deep chuckle, and then it started up again. "I am nothing but a sissy slut. I live to suck cock and be fucked..." Over and over again until I had the mantra memorized. Hours later, when my phone's battery ran dead, I was still repeating my words in my mind as I drifted off to sleep. "I am nothing but a sissy slut. I live to suck cock and be fucked..." I woke to the sound of a deep male chuckle and the feeling of hands pulling and twisting my chastity cage. "Wakey, wakey, slut. Master is here to claim you." I groaned in anticipation. "Good girl," Master continued. I wasn't sure if you'd slut yourself out for me or not. You went above and beyond what I asked for. Who knows, you might just earn an orgasm in a month or two after all." Suddenly he pulled by chastity straight up in the air, practically lifting me up by my balls. "But probably not. Your days of cumming are over." Master went to the kitchen and I heard him rummaging around in the drawers for a knife. I'm shamed to admit that I was afraid he was about to murder me. But he came back and sliced a hole in my gag and then fished the rag out. My mouth was completely dry and my jaw was very sore. Master didn't care. He shoved his cock in and started fucking my throat. He only stopped once to tell me "If I feel your teeth again, I'll have a dentist friend of mine pull them out for good." I opened my mouth and throat as wide as I could while Master pounded into me. It only took a moment before I felt his cock swell up and then spurt after spurt went right into my stomach. I moaned and swallowed, then licked him clean as best I could. "Not bad for a new sissy," he told me. "Don't worry, you'll get batter with practice." Then he undid my handcuffs and stood me up. But instead of unwrapping me, He pulled my arms behind my back, took out another role of duct tape and proceeded to completely mummify me. I thought I was immobile before, but now I couldn't even wiggle as Master wrapped me even tighter. There was only a slit left for my mouth, a few holes for my nose, the opening where my chastity poked out and with another scary slice, a hole that would give horny cocks access to my sissy pussy. There was one new hole to be added. It was a tiny prick of a needle that went straight into my ass. Master made good on his promise and gave me my first dose of sissy hormones. Master then went to the kitchen and came back with some water. I felt a straw being pushed into my mouth. I greedily sucked down the liquid. Then Master picked up my phone and noted that it was dead. "No worry," he said, "you should have memorized your lines by now." Without hesitation, I started to repeat the only words I would say for the next two months. Non-stop, I repeated my sissy prayer. "I am nothing but a sissy slut. I live to suck cock and be fucked, each and every day. I spend my days dreaming about cocks and cum and feel empty when there's not a hard cock filling my sissy pussy." "Please Master, fill me full of cum and then make me into your perfect sissy slut. I will do anything and everything you say, if you'll just turn me into your sissy gurl." While I repeated this, Master logged on to my computer and started responding to the men who had responded to my ad. "Damn gurl," he said, laughing. "We're going to be here all night before you take care of all these horny men." And so it started. I heard Master call or email one man after another. He gave each and everyone of them my real name and address. I heard my webcam turn on as Master set out to prove that I was indeed a sissy slut, waiting all tied up for men to come fill me up with their cum. It didn't take long before they started showing up. At first they would fuck me while I was still mummified. After a while there were more than a few men waiting to use me, but I was tied up so tightly with the tape that I couldn't hold my body in a position that would allow me to suck their cocks while being fucked. I heard somebody say, "Fuck this" and they started unwrapping me. I would have screamed in pain, but my mouth was stuffed with cock and I remembered Master's warning that he would pull my teeth if I ever bit down. As you might guess, ripping the tape off my head was the worst. Enough hair was pulled off that Master dragged me to the bathroom and immediately shaved me bald. "This was a good idea, slut," he said as he dragged the razor across my head. "More exposed skin for the tattoos." Master never took the tape off my eyes, so I couldn't see the look on his face. Well, I could still see his eyes in my mind, and that was all I needed to keep me in full sissy-slut mode. I spent the next several hours on my knees with one cock pounding my ass with another shoved down my throat. I frequently had two more cocks twitching in each hand while I did my best to service a never-ending parade of horny men. They never stopped coming. It was one cock after another, and I never saw a single one of the faces that was attached to those spurting monsters. At a certain point, Master noticed that I was shaking in physical exhaustion, so he called off the assault. He was almost tender as he ran his hand over my bald head. "This is going to work out just fine," he said before taking me to my bed. He flipped me over, fucked me quickly, and then left me dripping with cum. "See you tomorrow, slut" he said as he left. I immediately fell asleep dreaming of what was coming next. I woke up the next morning, exhausted and sore all over. Angry red marks striped my skin from where the duct tape had been. Everything was sore, but I looked at it like a badge of honor, and couldn't keep my hands off myself as I stood underneath the hot shower. If I could have reached my cock, I would have jerked off immediately, but it was locked away in its cage, so I had to rely on one hand rubbing across my skin while the other hand snaked a finger into my ass. I was completely lost in myself when I heard somebody rummaging around in my living room. The bathroom door opened and Master's voice told me to get out of the shower. He put a blindfold and a pair of handcuffs on the sink counter and told me to blindfold myself and lock my hands behind my back before coming out. I jumped out of the shower, dried myself and then dropped to my knees. The blindfold went on, the hands were locked behind my back and then I crawled as best I could out to meet Master. "I told you this one was a keeper," I heard Master say, and then a strangely familiar voice chimed in, "I always had a feeling about this slut." Fuck! I knew that voice. It was my boss, Don Peterson. I was supposed to be working right now, instead I found myself on my knees while Mr. Peterson fucked me roughly from behind. He slapped my ass and laughed, "things are going to be much different at work from now on, Sean, or should I say sissy slut." I was pretty much in shock from that point on. Mr. Peterson fucked me, bred me, and then turned me back over to my Master. I heard him ask Master if he could buy me after the transformation was finished. I never heard Master's response. I fell asleep with my sissy mantra repeating in my head. "I am nothing but a sissy slut. I live to suck cock and be fucked, each and every day..." A few hours later I was tied up and shoved into the trunk of Master's car. We drove around the city for a while, and I was able to sneak in a quick nap. It was very late at night when the truck was finally opened and I was dragged out. I was untied, slammed down across the trunk and immediately filled full of a very large cock. I could tell that I was being fucked by a huge man; somebody who could break me with his bare hands if he wanted to do so. I wasn't tied up, although I was still blindfolded and caged. Still, I didn't dare move. I sat there and allowed this man to fill me full of his seed. He grunted and said "Not bad." There was a pause before he said "fifty fucks, plus I get to film her and post it online." Master agreed with a grunt and the huge man dragged me inside his building. We were at a tattoo parlor. It was closed, but the man, Dogg, had agreed to stay open all night to work on me. By the time the sun rose in the morning, I had been permanently marked as a sissy slut. Dogg didn't say much to me all night long as he pierced and marked me as a slut. He seldom tied me down, preferring instead to just push me around and have his way with me. I never even contemplated resisting. I simply repeated my sissy mantra. "I am nothing but a sissy slut. I live to suck cock and be fucked, each and every day. I spend my days dreaming about cocks and cum and feel empty when there's not a hard cock filling my sissy pussy." "Please Master, fill me full of cum and then make me into your sissy slut. I will do anything and everything you say, if you'll just turn me into your perfect sissy." Dogg began by tattooing my nipples a dark red. That hurt like hell, but at least I was numb by the time he pierced each nipple with a heavy gold hoop and then clamped them closed. I was flipped over and he gave me a tramp stamp that was actually quite beautiful. It consisted of a series of silhouettes of women sucking cocks and being fucked. "Sissy Slut" was spelled out in fine cursive just above my ass crack. Two arrows were added to my butt cheeks--each one pointing to my gaping ass hole. Dogg took this opportunity to shove several fingers up my ass while he tattooed the oversized arrows that would guide men for years to come. Next up was my cock. This hurt as well. Master had given Dogg the key to my chastity, so I was finally freed, but not before I was tied down to the bench for safekeeping. I was so horny that I came almost as soon as Dogg fished my cock out of its cage. He immediately slapped me hard across the face. "You'll pay for that, slut," he said as he started the tattoo gun buzzing while scooping my cum back into my mouth with his free hand. My cock was eventually covered in delicate flower tattoos and stylized warning signs. "Out of Order," "Keep Away" and "Do Not Touch!" were etched permanently into my sissy clit. At some point I must have been crying out in pain so loudly that Dogg gagged me so that he could continue his work without distraction. I passed out at some point. While I was asleep I had three rings put into my cock and shaft and another one embedded deeply just in front of my ass. This would allow Master to lock my cock back between my cheeks some years in the future when I finally earned a release from my chastity. I came back to consciousness when Dogg split some smelling salts under my nose. "Suck me off before I work on your face," he grunted and then rammed his cock down my throat. His cock was as big as he was, but by this time I was so sore and abused that I had no trouble taking it down my throat. He smelled terrible, but there was a musky scent that actually turned me on. He came after just a few minutes of face fucking me. Then he started in on my face. He gave me permanent makeup. My lips were lined and then filled in with a dark red. They were so swollen and plumped up after the tattoos that I couldn't feel them for days after that. I must admit that I hated loosing my cocksucker lips a few days later, and eventually went in for collagen injections just so I could recreate the feeling. Dogg also did my eyeliner in coal black, and then wrote "sissy" and "slut" across the ridge of each ear in a surprisingly delicate script." My nose, belly button and tongue were pierced and then I was given a slave identification number on my upper shoulder. I was in such a haze that I didn't even see the brand until it was too late. There was a searing pain as Master's brand was seared into my flesh. I passed out once again. I woke up some hours later, asleep in my own bed and covered with sterile gauze pads. I wasn't tied up, but a steel cage had replaced the plastic chastity device and the end of my cock was now tethered securely to the bottom of the chastity device thanks to my new piercing. I hurt all over. I dragged myself out of bed and went to the bathroom. I looked like hell. My face was swollen from the tattoos and I looked physically beaten down. I burst into tears as I sat to take a pee. What had I done? There was no going back from any of this? Was this really what I wanted? Yes. This was exactly what I had asked for. I'd never had the guts to go for it before, but thanks to my Master it was now all completely real. My tears of anguish turned to tears of gratitude. I started to repeat my sissy mantra. It calmed me and also caused my cock to twitch in its cage. Eventually I dragged myself back to bed and fell back to a much- needed sleep. I woke to feel a cock pushing into my mouth and hands roughly holding my eyes closed. It was Master, taking his time as he slowly plunged his cock in and out of my mouth. He faced-fucked me for a long time. I'm not sure how long, but what else did I have to do that day. I licked and sucked him until I felt him tense up and deposit another load of cum down my throat. It wasn't much of a surprise when I heard Mr. Peterson unzip his pants and shove his cock down my throat. "Don't worry, Sean," he said between strokes. I've arranged it with human resources. You've got three weeks of stored up sick leave before we have to fire you. But by then you'll be able to get a job as my new sissy slut secretary. I foresee locts of 'dick-tation' in your future." With that he grunted and filled my mouth with his cum. I heard Master tell him, " Only if you can afford her. Sluts aren't cheap." The two men laughed and left me alone to savor the taste of their cum. I wondered what they were discussing, but only briefly. My mind was soon filled with my never-ending sissy mantra that kept me grounded in my new reality. "I am nothing but a sissy slut..." A bit later Master returned and dragged me to my feet. "You're in no condition to be seen in public," he informed me, "but no worries. I know a place that's perfect for a slut like you." He took a minute to change my bandages, then I was dragged out to his car and shoved into the trunk. I was surprised that I hadn't been tied up, but then I noticed that there were several pairs of handcuffs rattling around in the trunk with me. I knew what Master expected. I handcuffed my feet together and then handcuffed the end of my chastity to the chain between my feet. I took the last pair of cuffs and locked my hands behind my back, making sure to link the chains so I was locked in a rather painful hogtie. We drove off into the night. I had no idea where we were headed, but I didn't care. I had found my place in the world. "I am nothing but a sissy slut," I told myself, and shuddered in ecstasy as I wondered what was coming next. Author's postscript: I hope you enjoyed the first part of this story. Heaven knows I had a lot of fun writing it. I realized that our sissy heroine's character isn't overly developed, but I'm writing this story for the man who once told me that good sissies don't think so much as just submit and trust that their Master will take care of them. That's what I'm hoping to accomplish in this tale. There will be more submission and trust in part two, which is still being formulated in my head. I'm certainly open to suggestions. Once again, I hope you enjoy my literary fantasies.

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It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Becoming a Sissy

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

3 years ago
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What is a Sissy

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

2 years 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...

3 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...

2 years 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...

4 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 ...

3 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...

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...

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...

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