I Felt Like A Sissy free porn video

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I felt like a Sissy Janet L. Stickney [email protected] I felt like a big sissy; from the ruffled panties to the cincher, pantyhose and dress, I looked like a little girl! I sat at mom's vanity doing my own makeup under her watchful eye, starting with foundation, then eyeshadow, eyeliner and mascara, followed by blusher and lipstick. She fastened the hairpiece on my head, brushing it out, then trimming my bangs. I clipped on the earrings, stepped into the short heels, and looked in the mirror. The very short pale blue dress was short sleeved, rolled over my small bustline, then tapered to my cinched waist only to flare out and end well above my knees. My dark brown hair curled around my ears, displaying my earrings perfectly. In my eyes, I was beautiful, I only hoped everyone else would think so too. "GOD! I never expected you to look like this!" mom said excitedly. "I figured maybe, but...." "Mooom... do I have to do this? I mean... look at me! I look like a sis...." "You look like a very nice young lady; now, no more of that whining, you'll ruin your makeup!" Taking me by the hand she led me out to the family room. There sat my father and the principal of my school! Both of them gawked when they saw me, but a smile did come to the Principals face. "I hope," mother said, "that you believe me when I say that I know how to tame boys who are out of control! In order to help him regain his status as a boy, I think that by spending the rest of the school year as a girl he will realize just how many privileges boys have. Is this going to be a problem madam?" "No, but we can't have him just show up like that, the other kids would crucify him! Especially the boys! If your son is to attend our school as a girl, then the best course would be to have him come in as a normally dressed female transfer student. I can arrange that of course, but there are certain requirements for the girls that he would have a hard time with, at least as he is right now." "How so?" asked mother. "Well, every girl must participate in a sport of some kind, which means showers. And of course, every girl is required to take classes to improve their skills as a homemaker. I don't see that one as a problem, the first however will." "Let me look into it. If I can find a solution, I'll implement it right away. If I can't...." "It is a requirement," the Principal said. "I'll do my best then." "Call me on Monday and let me know what the outcome is then?" "Of course." My father had just sat there like a lump while all that was going on; he had almost always defended my antics up until then, some of which had gotten me into some serious trouble, but when I had taken my mom's car for a joy ride, well, he went nuts. I didn't hit anything, didn't speed, or get caught, yet he was livid to say the least, and mom, well she went off the deep end. That's how I came to be dressed like a little girl. Mom simply told me to stay in the house, then went online to check a few things. Two hours later she called me into her bedroom. "Now you've done it! This time you have stepped over the line, and will have to pay the price. We did warn you the last time that if you continued doing these stunts that we would do something serious, and now, we have no choice but to do something. You are about to become a school girl in every way possible! I did find the items you'll need to attend school as a girl and get away with it, but it will be up to you to act like a girl at all times unless you want to be found out, and I'm sure that you don't want that! The items will be here tomorrow so you can try them on, and if they work as advertised, then you'll be starting school on Monday as a girl. Now then, so far I have made all the decisions, but I think it's time that you had some say. I'll let you pick a girls name to use. If you don't I will, and I promise that you won't like it. Okay?" She left the room, leaving me with no choices. If I did not pick a name, then I would end up with a name like Sissy, or Sassy, or some other stupid name! Looking in the mirror I saw a 14 year old girl, even if she was dressed like a ten year old. Not ugly, yet not quite pretty, the girl I was looking at was totally acceptable, except it was me that I was looking at. I went in my room to decide on a name; I had until dinner to make my choice. I knew that I did not want a name that sounded girly, like Mandy or Ashley or Suzie, and I had only a limited knowledge of girls names, so I went online. I found it. It was a girls name, yet not overly feminine. I chose a simple name, easy to remember, and easy to spell. Mary. That's the name I chose. "Well? Have you selected a name?" "Mary," I said. "Just Mary? What about a middle name? Everyone has one you know!" "Um....ah... Elizabeth?" I blurted out. "Mary Elizabeth! That's a very nice name dear!" The very next day the packages came to the house via special delivery, and I was dragged into my bedroom and told to strip. When I was down to the panties I hesitated, but mom made me take those off too, leaving me standing there naked and red faced. After she read the instructions, she smiled, and began by wiping my chest with a cleanser, then smearing something on my chest. After a momentary wait, she attached one, then the other, and voila! I had boobs! Boobs that looked like they were my own, but when she held out that panty for me to put on and I saw it, I almost fainted! "You'll have to push those things up into your body, then slip your member into that sleeve so the fit is right. Go ahead while I watch." There is nothing more embarrassing than to have your mother watch you as you tucked things away, believe me! I tried, but until she used the included lube, my member refused to be inserted into that sleeve, but when it did slide in and she pulled those panties up tight, well, you can imagine my shock. I looked exactly like a girl, from the top of my head down to my toes! No sign that I was ever a boy existed, but still, mom used that latex stick and her blow dryer to hide the thin seams, completing my transformation. "According to the instruction sheet, you'll have to use the same facilities just like all of the other girls, because from now on you'll eliminate like we do, sitting down. Also, in a few days, maybe a week, those packets I ordered installed will begin to work, and you'll start having periods, like the other girls! So, that means that you'll have to keep yourself clean like we do or risk smelling bad." "Periods! Mom!" "I know, maybe it is a bit over the top, but I want you to learn a lesson, and in order to do that you'll need to fit in! Since girls your age are starting to have periods, I thought that you should too! Now, quit moaning about it! It's done and there is nothing we can do about it. Just get dressed. A skirt and blouse will be fine." After she left I once again looked in the mirror, wanting to cry but I was unable to muster the tears. I grabbed my boobs and pushed them together creating cleavage, then I let my hand find my new lower parts. The thin line of hair that surrounded it was soft, and as I pushed, my finger went in. I figured that would happen because if I could have simulated periods, then it had to be deep enough for a tampon to go in. Silly me, the other uses didn't even cross my mind. I pulled on the panties, surprised at how much better they fit, and since I had rounder hips and a bigger butt, they hugged me like paint. The bra was harder to get on at first since I was not used to having breasts get in the way, but I managed, and soon appeared in a skirt and blouse. I felt weird in a lot of ways, yet the plain fact was that I was stuck. I had become what looked like a girl in the span of a few days, and there was zip that I could do about it. Getting angry and yelling would only make mom go off on another tangent, and probably make it worse, if that was possible, so I endured my shame in silence. Over dinner.... "We only want you to learn a lesson, not be made fun of, and since tomorrow is Saturday, you and I are going to spend time at my salon. You'll get your hair styled, nails and makeup done, then we're going shopping. You have so little to wear that you need almost everything! It'll be a fun day, I promise." The next morning mom got me up early, telling me to wear that same skirt and blouse, but tennies instead of the heels, and right after a bite to eat, we were off to see the wizards of the planet salon. I knew zero about what went on in a salon, but I got my first introduction when I was taken to the back, told to strip, and after I was on the table, I had my whole body waxed! You could easily say that was not the most fun thing I had ever done, especially as they ripped the arm from under my arms! Then I was taken to the sauna, baked a nice red just before I had the ice shower! After recovering from that thrill and when I was dressed, I was taken to the stylist. She washed my hair, then began cutting and trimming before she changed the color from mouse brown to luscious brown. After that came the rollers, a "soft perm," she said. Then, as I spent time under the dryer, another girl came over to do my nails. After cleaning them, she used acrylics to make them a bit longer and thicker before adding two coats of light red polish and a coating of clear. Back in the stylist chair, she brushed out my hair, then pierced each ear twice, adding small gold hoops before she spun the chair so I could see. I was speechless. I did not look like me in any way! "All we have to do now is get your makeup on and you'll be ready!" That took about twenty minutes, and once again I was in awe at how easily they had turned plain old me into a very pretty girl! "Mary? Are you done?" "I guess." "I'll pay the bill and we can get to some serious shopping!" By the time we got home I had what I thought was enough clothes for three girls, but mom assured me that I would need everything! Pants and shorts, swimsuits and bras, panties and skirts, dresses and jewelry, slips and shoes. The list seemed endless. On Monday morning, wearing a short pleated gray skirt and a simple white blouse with black flats, I made my debut at school. I was almost shaking in fear, afraid that someone, anyone, would recognize me, but to both my horror and delight, nobody did, not even my best friend Steven. I was entered into the rolls, and began my career as a high school girl. I felt scared and awkward, yet knew that I could pass any inspection, which only tempered my fear a little. My biggest hurdle came not when I had to join in playing volleyball, but when I had to take the mandatory shower. For a 14 year old boy, being in the girls showers is a wet dream; but in my case however, nada. No response at all! I looked just like they did, and none of them thought I was anything but a girl. It was sad in a way, but after that, I knew that nobody could ever say that I was a boy. Over time, without thinking about it, I began to use the same mannerisms the girls did, and also, like them, started to look at boys as something other than pests. I guess it was all that fluff and lace, or maybe the perfume. In any case, I found myself drawn into conversations with other girls about girl stuff, like boys, dresses, teen idols and boys, so it's no wonder that I slowly began to think of myself as a girl! Heather, one of the girls in our little circle, confided in us. "Me and Keith, well... I did him!" "You had sex?" asked Susan in a stunned tone. "NO! I gave him a BJ! It's safer. No pregnancy, no blood, no getting undressed and besides, it's not really sex!" After that, I knew that many, if not most of the girls that had boyfriends were probably taking care of their guys the same way. The very thought of doing that, while not an issue for me, wasn't that far removed from the possibility that I might, and that made me nervous. Ben had called me at home twice, and I knew that he was on the verge of asking me out, which made me not the last, but also not the first girl to be asked out that year. When he finally did ask me out, I was torn between knowing that I was a boy and my fervent desire to be accepted as a girl, and my struggle with being a girl won out. My very first date with anybody was to a show, then pizza. Ben was very attentive, and I liked him. Like me, he had also transferred in, so he had no idea that a boy had disappeared and a girl had arrived. When we were standing on the front porch, he took me by the hand, then leaned in and kissed me. It was quick, and I ran in the house after thanking him. I went in my room and got ready for bed, and was just slipping the nightgown over my head when mom came in. She shut the door. "Have you started your period yet?" "No, why?" "It's been almost six weeks, so I'm guessing that it'll start this week. You should make sure that you put two tampons in your purse every day. I have no idea how heavy the flow is going to be, so you should be prepared." "Okay." "How was your date?' "It was fine mom, why?" "You've become so... feminine in the last several weeks, and now that you're dating... this is not going the way we expected it to!" "What did I do!? I mean, I'm doing everything you told me to do!" "I know you are honey, it's just that... well, I guess we didn't expect you to date, that's all." "But if I don't I'll be on the out's with the other girls, and..." "I know how it is honey, I was a school girl at one time too." Mom sat here, then took me by the hand. What I mean is, you're so cute, and now Ben.... You seemed to be so happy, that's all. It's like you finally found yourself." "I... it's different, that's all, but now, well, I sort of like it!" "Like what honey." "I like the way I look mom. I like the clothes, and the makeup, and I like the way the other kids treat me, and I like the way the other girls have accepted me." "And Ben?" "I like the way Ben looks at me too, I guess." Then I started to cry, and mom held me in her arms, stroking my hair, until I slowed down a bit. "Lets not tell your father just yet. Lets let him figure it out by himself? This is just between us girls, okay?" I hugged her tightly, then lay back, afraid that I had ruined something. I had just admitted that I liked being a girl, dating boys, and maybe, that I might stay the way I am! I knew that my dad would never understand, and since I didn't either, I had no way to explain it to him. I slept better after I decided that I couldn't change anything, and by the morning, I was confident that I was doing the right thing. Just as I got up, it started, and I called out for mom. She ran in the room, saw what was happening, and led me into the bathroom. In my estimation, there is nothing more gross than the monthlies! You never know when it's going to strike, and you have to use obscene measures to control it. Mom told me to clean up, then showed me how to use the tampon, which in itself would be funny if it wasn't so serious. Once I had it inserted, I cleaned up again, then went to my room to get dressed. I was positive that I would feel that thing inside the panty move when I did, but it didn't. All I felt was a small pressure exerted against my skin, inside the panty. Having started what can only be described as the most feminine thing there is, I decided to be extra girlie, and wore my highest cut panties with the matching pale blue bra and a light blue slip. Then I pulled on a lightweight summer dress. It was well above my knees and was square cut at the neck with cap sleeves. White flats, some makeup, jewelry, and lipstick, and I was ready for school. When I went in the kitchen... "Hi daddy!" "Daddy?" "You are my dad aren't you?" "Yes, of course, what I meant was...." "That's enough of that. Eat!" I gave dad a kiss on the cheek as I ran out the door to catch the bus, knowing that he would be seriously confused by my burst of feminine behavior. Over the few weeks that I had assumed the role of a teenage girl, I had started to act and talk more like your average girl. It wasn't on purpose, it just happened; but as soon as I realized it, I knew that my salvation lie in being perfect in every way. I had to not only use those traits, they had to become second nature. Over the next few weeks Ben and I went out almost every weekend, and he began to get bolder when he kissed me. I let him get to second base, but that was all, and he gave me his class pin! Like so many other girls, I had a steady boyfriend, but when dad saw that pin, well, he freaked out. He knew what that meant, and knowing that I was his son, not his daughter, he assumed more than what there was. I did not help things at all either. I wasn't trying to flaunt anything, only wanting to be like the other girls. One Saturday I had planned on washing the car like dad told me, and wore my shortest shorts with a belly revealing crop top. He took one look and blew up. Up to that point he had only grudgingly accepted my total transformation, only commenting once in a while about how "girlie," I was getting. That day however.... "What the hell are you doing! That...that's obscene!" "What's obscene?" "Dammit! You look like a.... in a.... "A girl? Wearing shorts?" I said back. "Don't get smart with me! You know exactly what I mean!" I did get it, but after three months as a girl I knew in my heart that there was no way that I could be anything else, and dressed accordingly! My father however, wasn't to be deterred. "I want you to go in the house and change right this instant, and I do not mean into a skirt!" "A dress then?" I was being sarcastic of course. "Get in the house! Now!" I went back in the house with dad right on my heels. He dragged mom into the kitchen, then blew up. "I want him to change back into our son! Now. I've had enough of this girlie thing and I want it to stop right now! I do not want to see him in anything girlie from now on!" Mom, who was sitting at the table, calmly looked up at him and said one word. "No." "What the hell does that mean? No!" "You mean to tell me that you don't have a clue?" mom asked. "Mary has become a girl, and we can't change that! She has friends, even a boyfriend! She has better grades than before, and she's even started her...well, she has become a woman in every way, and I will NOT let you change any of that! Besides, she couldn't change if she wanted to. Those devices she has on are made to wear for a for very long duration, and she isn't even close to the end! Now, I want you to stop all this ranting and just accept the fact that we have a daughter rather than a son!" Turning to me... "And you, young lady. I want you to stop provoking your father!" "But I didn't do anything! All I did was get ready to wash the car, and he blew up!" "Go finish what you started Mary, your father and I have to talk." I have no idea what she said to him, but I'm willing to bet that she filled him in on several facts that fathers don't usually get but can assume. Like me having periods for example. Or why girls do certain things that baffle guys, especially fathers. Like talk on the phone for hours, and other inherently girl things. I know for sure that he never once figured out why I would wear clothes that were the least bit revealing, or act like a girl when I wasn't outside the house for example. For me, there was no middle ground; no halfway. It had to be all or none. I fought it at first, but found that being a girl wasn't all that different than being myself. I took almost all the same classes, wore just about everything the other girls did, and slowly, and finally, began to enjoy it. That's what mom was telling my dad. I went back outside and started washing the car. By the time I was finished, mom was done talking to dad, and came out for a heart to heart. "I've explained things to your father, and while he does not know the full extent of changes, he does know... well, I had to tell him that you suffer once a month like all the other girls. He was sufficiently shocked when I told him that, but he now understands that it's unlikely that you, as our son, will ever return." "Was he really mad? I mean, this just happened mom! I didn't do anything!" "I know, and I told him that. I told him that you had to fit in or be the class punching bag, and he understood that too, but he still has a very hard time understanding why any boy would want to be a girl, under any conditions! I reminded him that putting you in dresses was his idea as much as mine, and he simply had to accept the results of that decision! Now, as for you, you are just starting to figure out that men are clueless about women, something most girls know from early on, which is how we manipulate the men in our life. I want you to go in and change into something nice, and very feminine, then I want you to go talk to your father. You're the only one that can tell him that you can't go backwards, and convince him of it. Can you do that?" "I can try, but what if he gets mad?" "So? Let him. He won't hurt you, he would never do that, but you'll have to assure him that you love him, and trust him, and need him, even more, now that you're a girl. Girls need more attention, and you and he also need to get on track about your relationship. Okay?" "Okay mom." I went in my room, then showered. I very carefully selected what I was going to wear. Every single thing had to scream girl, yet still be tasteful. I wore a pushup bra with pink panties, and a half slip before I started my makeup. I used as little as possible, but enough to accent my natural beauty, then brushed out my hair. My hair had grown out to shoulder length, and was still a dark brown. I pulled on the pantyhose, and slipped the light green and white checked dress over my head. It was only a little bit tight across the bust and midsection, but flared out at the waist and stopped about two inches above my knees. I wore the low white heels and gold jewelry. I put on some perfume and took one last look in the mirror before I left the room to find my dad. It was time for me to confront him and tell the truth. I have great legs and a wonderful figure; I was down to 125 pounds, which was perfect for my height. As I walked out back to the patio, I was afraid, yet confident that I looked my very best. "Daddy?" "Come sit down... honey." As I sat... "Your mother tells me that you're more of a girl now I ever thought possible. She says that you can't go back to being our son. Is that true?" "I nodded my head yes, then... "Dad, this just happened! I didn't plan on it, but now that it has, I need you to... do you still love me? Is that it? You hate me now?" "OH god no! I don't hate you, I just cannot figure out why you would want to be a girl! What I mean is, boys.. men, have all of the advantages! Why would you willingly give up that birth right?!" "Men don't have all the say!" "Oh?" "You're here talking to me? And doesn't mom manage the house and tell you what to do? Oh, and does your secretary run your schedule? Women have been making men do what they wanted for a long time. Even little girls get their fathers to do stuff they don't want to do! So, no, I don't think I'm giving up anything! I might even be ahead!" "But you've become so... feminine!" "If I had to wear a dress to school, your idea by the way, you couldn't possibly think that I would do it as a clown did you? I would have been killed! I had to get this way to fit in, and now that I am accepted I just can't give it up I... I like being a girl!" There, I had said it. "I'll admit that you're pretty, and you certainly look and act like a girl, but...." "Daddy," I said softly, "I just need you to love me. I need you to accept the fact that you have a daughter now, and I really do need you." "I was scared honey. You have changed so much that I couldn't recognize you any more." "Dad, I'm the same person I always was, I only wear different clothes." "What about that boy Ben? Are you two doing..." "I'm not that kind of girl!" "I'm relieved about that, I was worried!" "That brought a giggle. "Dad! I only look like a girl! I can't get pregnant!" "Maybe, but you can try, I know that much at least!" "Maybe, but I won't confirm that, and even if I could, I wouldn't, not until the time is right, and when that day comes, you'll walk me down the aisle, right?" "It would be my pleasure honey." "OH daddy!" We hugged and wiped away mutual tears, the tension between us having been deflated. I was, finally, his daughter, and he was my daddy. As he hugged me I could feel the strength within him that it took to accept me the way I was, as well as his love for me. I knew from research on the Internet that love and affection were only dreams for many of my sisters. Hate and disgust were the norm, so I knew that I was the luckiest girl on the planet. We stayed out there for a while, then I went in to get something to drink. Ben stopped by, asking if I were free, and dad said it was okay for me to go, so Ben and I left in his car. We went to a show, then later, to our favorite spot in the park. Up to that point Ben had only touched my breasts through my blouse, but that day, everything changed when he slipped his hand into my bra. Both of us were on fire, lust and hormones taking over our common sense. When Ben took my hand and put it on him I wanted to recoil, but didn't; I rubbed him instead. It was at that point that I had an overwhelming desire to touch it, naked, but when he tried to unzipped his pants, I stopped him. "Kiss it," he said. "No!" "I'm clean, promise!" "No! But, maybe this?" I slipped out of my panties, let him bare his weapon, then used them to give him a hand job. Ben lay back moaning, as I rubbed him, realizing that I had to do it. It did not take long for Ben to erupt. I had crossed the line, if there was one, and any thought of going back, was out the window! He grinned, I grinned back, and after refreshing my makeup and stuffing those panties into my purse, I made him take us to the pizza place. I was not ashamed of what I had done, other girls were doing it for their guys, and I was no different. As time went on it became obvious, even to mom that I had to start taking hormones or risk having my body fill out in ways that I didn't want, so, almost six months after it all began, I entered into the program. It took less time than I imagined, but I began to sprout boobs of my own, and before I started my senior year the only device I wore was the panty. I had to wait, but eventually I became a female, met, and married a man that loves me dearly; oh, and my dad did walk me proudly down the aisle.

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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...

1 year ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

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 ...

2 years ago
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Raised a Sissy

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

2 years ago
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Curiosity Spanked the Sissy

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

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...

2 years ago
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Degraded Sissy

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

2 years ago
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How to Build a Better Sissy

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

3 years ago
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Checkerboard Sissy

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

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...

3 years ago
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New Little Sissy

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

2 years ago
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Its Hard For This Sissy

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

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...

1 year ago
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My Sisters Sissy

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

3 years ago
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A Nasty Daddy gets a Naughty Sissy

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

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

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

3 years ago
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What does it mean to be a sissy

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

1 year ago
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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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  • 30
  • 0

What does it mean to be a sissy

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

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

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

2 years ago
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The Misadventures of the Worlds Worst Sissy

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

2 years ago
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First time Sissy

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

Transsexual
2 years ago
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Im Not A Sissy

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

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...

2 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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