My Little Toy Sissy-boi - Ch 1 free porn video

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My Little Toy Sissy-boi

Chapter 1

By CDJackie


I was standing at the sink with my lingerie about half done when I heard the door bell ring. I didn’t care for the interruption but thought what could I do so I went to the door figuring I’d just send away whoever it was. When I opened the door my young lover was standing there and it ticked me off, when I talked to her earlier on the phone I had told her to come over to see me but to not arrive for at least 2 hours since I was going to be busy.

I let her in and as she moved past me in to the living room my eyes dropped to the sway of her tight little ass. When I closed the door and she turned to face me I gazed up and down her body admiring how she had dressed for me. I had said I wanted her to look girlie for me today and she had followed my instructions. She had on tight hip hugging black women’s jeans which bulged a bit in front from her little dick, a pale yellow see though blouse, a black bra showing through which was obviously filled with her breast forms. She had her hair combed out, it was now shoulder length since she stared growing it out for me, and pinned back behind her right ear with a yellow flower clip that matched her blouse. She had applied her make-up carefully, even including bright red bitch-whore lipstick.

“Do I look like you wanted me to, Jackie,” she asked hopefully, standing demurely in front of me with her small purse dangling from her hands clasped in front of her.

“Yes, my little toy, you look very sexy. You did well. But…”

“But what?” her voice was nervous when she replied.

“But…” I said as I moved to stand closely and directly in front of her. “Just what the fuck are you doing here this early? I told you I had things to do and you’re not supposed to be here for about another hour.”

“I couldn’t wait to see you and be with you,” she replied softly with her head bent and eyes downcast. “I didn’t think you would mind.”

“Listen to me,” I said, placing my fingers under her chin and raising her head then sternly and raising my voice, “When I give you a time to be here don’t you ever ignore that and come early. Understand? I told you I had things to do. Suppose I had a friend over and we were having sex, do you think I would want to be interrupted? Huh?”

“What’s that?” I said firmly. She had answered me but I could barely hear her reply.

“I said no,” her voice was quivering a bit from my reprimand.

“Good,” I dropped my fingers from her chin. “Don’t forget it. I wasn’t having sex but I’m in the middle of washing my lingerie. Now you sit in here and watch TV or read or whatever you want to do but leave me alone for now. I’ll let you know when I’m done and we’ll go on from there. Understand?’

“Yes,” again she answered softly and I could hear hurt and disappointment in her voice. “I’m sorry, Jackie. I really am.”

“Hmmphff,” I snorted and shook my head. “I’m going to go finish and…” I leaned forward and in a louder voice “…I don’t want to be disturbed. Got that?”

She nodded her head and sat down as I went back to my lingerie. But she hadn’t ‘got it’ as she indicated. It wasn’t but about 20 minutes later when I heard her coming up behind me in the bathroom.

“Yes, what is it?” I said with exasperation as I looked at her in the mirror.

“I…I…I just wanted to tell you how sorry I am at making you upset. And I’ll do exactly what you tell me and not disobey any more.”

“That’s fine,” I said as I turned around. “But you could have told me that later. I told you I did not want to be disturbed and yet here you are, disturbing me.” My voice was rising. “Now get out and go back to the living room before you make me mad. You don’t want me to get mad at you, do you? You’ve never seen me get real mad but let me warn you little one, I am a true bitch when that happens. Now,” I waved my fingers in a backward brushing off manner, “get out of here before you piss me off.”

“Yes, ma’am”, she cowed as I turned away from her.

Hmm, I pondered as I went back to finishing rinsing out my things. “Yes ma’am” she had replied. I kind of liked that. Maybe I just ought to teach my little fuck toy to be more submissive and subservient when she fucks-up and doesn’t obey. But considering how submissive and willing she already was I probably wouldn’t have to push it too much further. We’ll see. I went back to my rinsing.

Then. Then. She was back.

“What the fuck is this!” I hollered, slamming my hands on the sink counter and turning around.

“I just wanted to see how much longer before you’re finished,” it was almost a whimper as she saw the fire in my eyes.

“I’ll finish when I finish,” I sharply replied. “But you, you disobedient little slut, you are finished right now. I told you to LEAVE ME ALONE.” I dried my hands, stormed past her, grabbed her by the wrist and tugged her behind me to the bedroom. In the bedroom I half tossed her toward the bed but she fell against the side on to the floor.

“Get up on the bed,” I said harshly as I continued walking toward the armoire in the corner of the room. I fumbled around inside and when I found what I wanted turned to find her curled on the bed in an almost fetal position. Then I strode over and looked down at her, my hands behind my back so she couldn’t see what I had gotten.

“I told you, I warned you. Don’t piss me off. But you just couldn’t seem to listen or understand huh?” I was leaning over and looking down, she had a look of fear on her face as she shook her head. “And now I am pissed. And you force me to teach you a lesson. Now Strip! I don’t want to see a thing on you except bare skin. When you’re naked, lie on her belly. You’ve got 30 seconds.”

It was obvious she was aware of my anger and was a vision of almost blurs as she removed her blouse, bra, jeans and panties and lay face down on the bed.

“Good girl. Now spread your legs wide and reach back and pull your cheeks open.”

She immediately did as she was told and in just seconds her crinkly brown rose was wide open to me. And without her being able to see, I pulled a 1 ½” thick, 12” long life-like vibrating dildo complete with veins and balls from behind my back, spurted a line of lube along its length, and without any warning shoved it up her boi-pussy. I heard her let out a gasp and a grunt as it disappeared up her fuck tube and I slapped the back of her head with a warning to be quiet.

“Now, turn over,” I commanded sharply. “And spread your arms and legs wide apart. Like a big X. Understand.”

She complied without even the slightest sound, and looked on with surprise as I secured her hands and feet to the bed posts with fur lined restraints. “So I guess this answers the question you asked me before about why I have a 4 poster bed and what those little silver rings in each post is for, doesn’t it. Don’t answer, just lie there quiet. We’re not quite done yet.”

I went back to the armoire, picked out what I felt most appropriate and went back to the bed. Leaning over her body I reached down to her crotch, grasped her little flaccid dick by the tip with the fingers of one hand while I positioned a locking cock cage around her shaft. The inside was formed like a cock to hold her somewhat comfortably and it was curved downward, but it was just tight and short enough to prevent her from getting an erection.

“There we go,” I gave her a wicked smile, “comfy?”

She seemed somewhat surprised at what I had done and almost seemed speechless but I did see she looked to be enjoy being restrained. I then reached down to the control for the vibrator built inside the dildo, flicked the on switch and set the speed to a medium-low with an intermittent pulse. She gasped in surprise and I saw her hips rise as it began to stimulate her.

“Well, if you couldn’t manage to keep yourself occupied and out of my hair like I asked, I guess this solves my problem. Now lie there and be quite or I might have to do something to be sure you keep quiet.” I walked over to the armoire again, pulled out a ball gag harness and held it out for her to see. “Believe me, I won’t hesitate to strap this on your head if need be. Understand?”

“Yes, ma’am,” she answered meekly.

I went back to the bathroom to finish my lingerie, smiling smugly to myself. Now I would have the peace and uninterrupted quiet to finish what I had started long ago. After about 5 minutes I peeked in the bedroom to see how she was doing and it was somewhat arousing. I could hear the faint buzz of the vibrator working away up her fuck tube and she was squirming and writhing on the bed from the sensations, her face a bit red and her nipples hard from arousal while she softly moaned. I found it kind of stimulating and my dick was getting hard from the watching the gyrations of her naked body, but returned to finish rinsing my things. It was about 20 minutes later when I returned to the bedroom.

“Well, my little sissy, having fun?” I asked as I sat on the side of the bed. “Do you like my little toys?”

“Ohhh, Jackie,” she panted, “I am so turned on from that dildo. I want to cum but I can’t, my boi-clittie can’t get stiff and I can’t touch myself any where to help.”

She was almost in a sexual frenzy from the non-stop vibrations inside her, circling and humping her pelvis in a continuous fucking motion, her back and ass rising off the bed, her face red and covered in a light sheen of perspiration. Wanting to climax and relieve the sexual tension pent up inside her.

“Well, it’s something you brought on yourself. I warned you about not bothering me and making me mad but you wouldn’t listen to me. You were disobedient so this is your punishment. Do you think you learned enough to pay attention to what I tell you from now on?”

“Yes, oh yes, I promise. Just make it stop,” she pleaded. “I don’t think I can take it much more.”

I reached down and turned off the dildo. “Better?”

“Thank you,” she sighed with relief.

“That’s okay, sweetie. You look like you are absolutely ready to explode.”

“Oh, I am. Can you please release my boi-clittie so I can cum?”

“Not so fast little one. You know, seeing you like this has gotten me all horny too. See,” I stood up, pulled my t-shirt off then removed my shorts to let her eye my hard cock bulging against my panties. “I just love seeing my little toy all fired up and ready for a good fuck.” I reached down and shook the cock cage then trailed my fingers up her belly to her tits and pinched her hard nipples. “My, oh, my. You really are hot aren’t you?”

She shook her head.

I released my thumb and finger from her nipple and cupped my hand under the fleshy pad of her tit. “Hmm, these little titties are getting nice. It looks like those female hormones I’ve been getting for you are certainly working. What size are you now?”

“I’m 32A, almost a B.”

“You’re getting there.” I leaned over her a little and placed the palms of both of my hands on her tits and rubbed them in circles, occasionally squeezing the soft pads. “They feel so nice. But I wish they were bigger. What do you think if you had a nice set of full sized tits like mine,” I hefted my boobs with my hands. “Not big mommas, but cute perky breasts, yet still big enough for me to tittie fuck. All your own so you wouldn’t have to wear those forms anymore. Hmmm?”

I leaned my face to hers and kissed her. She met my open mouth with hers and our tongues stabbed and danced together. I could feel her squirming, trying to, if possible, bring her hands to wrap around me, but they were held tight by the restraints. Instead, I placed my hands on the sides of her head while we kissed, long and passionately. I thought briefly about unfastening her, I was so horny, but decided to leave her like that for a bit longer. But I needed release. The sight of her naked body and feeling her growing tits, along with the image of them being fuller, had me totally aroused. I broke our kiss, took off my panties and crawled on to the bed.

“I’m not going to let you cum right now but I need to cum,” I said as I straddled her shoulders. “And since your boi-pussy is still filled I’m just gong to use your mouth. What do think of that? Wanna give me head?”

“Please, Jackie, put your cock in my mouth. Let me suck your beautiful cock.”

It looked like her mouth was watering as I scooted forward, sliding the length of my shaft up over her lips until the tip was just below her eye, then grasped it and lightly slapping it up and down on her face, as her tongue snaked out to lick at my balls and as much of my shaft as she could.

“Please, Jackie, please. Put it in my mouth,” she whimpered as she thrashed her head side to side trying to wiggle her mouth to capture my dick.

“Okay, little one. Here you go.” I slid backward, dragging my cock down her face until the bulb on the end plopped into her mouth. Her lips immediately closed around the meat stick she desired so badly as she began sucking.

“Yes, that feels so nice. Now take it all down.” I leaned forward, bringing my pelvis over her head and stabbed forward, shoving my cock all the way in and into the opening of her throat, then started face fucking her.

“Mmphh,” she moaned around my shaft.

I fucked her face and throat for a minute or so but it was a bit awkward so I sat back, pulling myself all the way out.

“Jackieee,” she moaned. “Don’t stop. Pleeaassee.”

“Shhh,” I touched my finger to her lips then reached over to the restraints holding her hands, one after the other, and released them. Then I scooted back onto her legs to give her room to bend forward then got on my knees. “Now sit up and suck my dick.”

“Yesss,” she hissed and dived her head forward, engulfing the entire length of my stiff pole in her warm mouth, taking it all the way until her nose poked my groin. “Mmm,” she moaned.

“That’s it baby, that’s it,” I put my hands on her head and stroked her hair. “Suck your lady’s dick.”

She attacked my cock in a frenzy; holding it in her hand as her puffy soft lips glided on my shaft as her head bobbed up and down. Sometimes stopping a moment to hold my dick in her mouth while her tongue swirled around it, other times diving down and deep throating me; all the while her hands in my crotch and playing with my balls.

She feasted on my dick for a few minutes then let if fall from her mouth on a back stroke and pushed her face into my crotch. She still had her hand on my shaft and stroked me as she extended her tongue to lick all around my balls and along the underside of my shaft then going back down to lick and suck on my balls.

“Thaatt’s nice, baby,” I pulled my hand from her head and reached beneath her to play with the gentle swells of her growing breasts and tweak her nipples. “Keep it up. I’ll give you a treat soon.”

“Oh yes, Jackie. Please. I want your cum in my mouth.”

She returned to sucking me and I loved it. Watching her lips on my flesh, leaving a coating of wetness along the shaft as her head moved back. The suction of her mouth like it was trying to draw my cum out. Sucking, bobbing, and taking it out, a trail of spittle connecting my dick to her lips as she momentarily licked up and down my length. Then back in for her sweet sucking motions.

She drove me nuts. It was probably one of the better blow jobs she had ever given me. I let her have her way with my dick, she knew what she wanted and I wanted to let her have her pleasure. But it wasn’t long before I felt my orgasm coming on and I didn’t want to cum in that position. Grabbing the sides of her head I lifted it off my shaft and stood up on the floor at the end of the bed. She whined and chased after my cock with her face, her mouth in a circle, wanting more of that meat.

“Get up on your knees,” I told her as I unfastened her ankles, “at the end of the bed.”

As soon as she was in position I thrust my hips forward to meet her face and drove my dick back into her mouth.

“Suck me, little toy. I’m getting ready to cum.”

She reached her hands around to grab my ass cheeks to hold on as she sucked and bobbed while I made gentle fucking motions into her mouth. As I watched her consuming my cock her eyes were looking up, never leaving mine, a look of uncontrolled passion, maybe almost a loving look, as she slobbered all over my tool. Working for and seeking her reward of the treat of a mouthful of warm, creamy cum.

“Oh, shit,” I groaned as I felt myself ready to release. “Here you go baby, I’m cuummimg!” and started squirting in her mouth. Spurt after spurt I unloaded, watching her cheeks puff in and out and her throat muscles move as she swallowed my cum. It was intense and after my third spurt I had to grab her head for stability as I threw my head back and closed my eyes in orgasmic bliss. She sucked and swallowed until I was empty, then continued to hold my cock in her mouth and gently suckle it.

“Oh, honey, you have to be one of the best cocksuckers in the world,” I praised her as I bent down to kiss the top of her head. I drifted my hand to her cheek and lightly cupped it as I withdrew and stood back.

“Okay. I’m going to go out and sit down. You can take that cage off your boi-clittie but I want you to leave that dildo in your boi-pussy. Then come out and join me.”

“Yes, ma’am. And Jackie, thank you. I really like sucking your dick and love the taste of your cum. And I knew you did what you did because I acted badly.”

“Good girl,” I leaned forward and kissed her lightly on the lips. “If you want to take a few minutes to massage your wrists and ankles that’ll be fine. But don’t take too long. And don’t even think about touching your boi-clittie. Understand?”

She smiled and nodded as I left the room.

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THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. 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 Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

2 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

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