Michelle's Sissy Training free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
Michelle's Sissy Training By Wendae I'm an author and work at home which allows me to dress 24/7 as Michelle. My wife works at the state prison for women in administration. Today I had ordered out for pizza and flirted with the delivery boy. He had no clue! Anyway wife has said she's going to start my sissy training after my confession that the rape had left me fascinated with sucking cock and that the only pussy I was going to get was on my knees eating her cunt. She was running later today and I was wondering what was holding her up getting home. I made her a martini and placed it in the fridge so it would be perfect for her when she got home. An hour after her normal time she arrived and I met her at the door. "Michelle I brought you an appetizer for before dinner." So saying she kicked off her heels and sprawled on the couch. As I handed her the martini she lifted up her skirt and told me to kneel down between her legs. As I did so she said, "Pull down my panties and dive right in!" As I eased her panties off I noticed they were wet as I set them aside. The heat was rising up from her cunt as I placed my hands under her butt to lift her for easier access to her cunt and started running my tongue up the insides of her legs towards her cunt. It was really musky and cum was leaking out of it. As I started to pull back she grabbed the back of my head and said, "Lick it up sissy! I stopped off at your friend's on the way home and he filled it up for you. He is looking forward to you sucking him off in the future." I dove in and she ground her cunt on my face as I sucked and licked her clean. She had several explosive orgasms before stuffing her panties in my mouth. "Suck all the cum out Michelle. I'm going to check them over later. Now go get me my dinner and another martini." What she didn't know was that I had an orgasm as well. While the idea of sucking another mans cum out my wife cunt wasn't number one on my list of fantasies, when I actually did it I couldn't get enough. "You know Michelle, I've been slipping you hormone pills for over a year. I don't know if you noticed any changes to body hair or your breasts. Some times your dick starts to shrink. You'd love that wouldn't you?" I had noticed some changes but never gave it much thought. "Yes, Mistress, but I haven't noticed anything." "Well I never thought that would create a cocksucker. But, I guess it was you always wanted to be. A sissy faggot cocksucker! I can't understand how you enjoy being on your knees while some guy fucks your face and dumps a load down your throat. I never found any pleasure sucking your little sissy prick. I'd rather eat pussy! While I'm on the subject I remember you telling me you could suck your own dick at one time. I think it's time you get back in training and I'm gonna help. We'll start tonight." That night was the start of several months of stretching exercises and my Mistress helping me reach our goal until we were successful. I love sucking myself off. Once you learn how to breathe and are able to take it all the way down to your pubic hair and wrap you lips around the base you are in heaven. You can get off fast or make it last as long as you want. It's sort of like nursing. You just want to suck happily until you are ready to reach an orgasm. Some are so violent that you have to lock your arms behind your knees as your body tries to straighten out and bucks uncontrollably. The real reward is the flood of cum spurting down your throat and the spasms of that wiener on your lips. The feeling of the cum being sucked out is bliss. I love to lay there and suck on it once it's flaccid and sometimes it'll rise up for another session. "Your friend John is stopping by this evening. I want you to get all prettied up for him so I can show you off." This wasn't the news I was looking forward too. It was going to be hard to face him as Michelle. Mistress had me answer the door when the bell rang. My heart was thudding as I answered the door. John stood there staring for a long minute before coming in. I had on a white peasant blouse, black pencil skirt, black hose and black 5 inch heels. I also was wearing cocksucker red lipstick and nail polish. The little white maid's apron set it all off. Mistress stood there smiling. "Well John what do you think of your old friend?" "Geez, Mike is that you? She has been telling me about you but I would never have believed it until now!" "Come on in and sit while Michelle gets us some drinks." I served them drinks and stood off to the side while they chatted and John kept staring at me. "Okay , John it's time for a little demonstration of what you never knew you were missing from your friend. Michelle, you are up! It's time to show off your skills. Over here in front of John and on your knees." I froze and was unable to move. This was not how I wanted John to remember me. A jolt from the collar urged me forward and I dropped to my knees. "Well, I'm waiting you pansy ass. Get his zipper down and start sucking." I pulled down his zipper and pulled out his limp dick. I could see the shock in his eyes as I started sucking. As I got over my own shock and humiliation I got serious and decided I might as well enjoy myself. I didn't hurry and slurped up the juices as they flowed into my mouth. His breathing started to quicken as I increased the tempo. Finally with a groan he grabbed the back of my head and thrust it down my throat face fucking me frantically. He dumped quite a load down my throat and I sucked him until he shrank up. Leaning back and wiping my lips I smiled at him. He shook his head and said "My God Mike, Michelle, all these years I never knew. I wish I had of known you loved giving head. You could have sucked my dick anytime. I would have given you all you could handle as often as you wanted. You are fantastic. A man's dream girl. It's so much more enjoyable when the person blowing you is really enjoying what they are doing. The fact that you make a pretty girl adds to the pleasure." Mistress dismissed me to cleanup and serve more drinks as they sat and talked awhile .John left shortly there after. Before he left, he gave me a kiss on the cheek and told me he hoped to see me more often. "Michelle this is Clint. He is the owner of a bondage equipment store and has helped me bring home purchases he suggested for your sissification." Clint looked at me and shook his head to indicate I wasn't to recognize him. What a shock, I never knew that he had a store. After Clint left Mistress unpacked her purchases. There were latex catsuits, hoods, gags, butt plugs, a milking machine, sheaths, skirts, boots and a latex lined coffin. "Now, Michelle in order to remind you when you forget you are a sissy and need to act a lady or slut, as I desire, I've bought you this electronic dog collar. When you forget to use your fem voice or sit like a proper lady I will use this remote to jog your memory. Come over her and kneel in front of me."" Once I had settled in front of her she placed the collar around my neck and clicked the little padlock. "Here is a little demonstration of what you can expect." With that she pressed a button on the remote. The shock knocked me over backwards and left my head spinning. "There are lower settings but I wanted you to experience what I could do if you displease me. Here is and example of a gentle reminder." A small electric shock tingled my neck. "My God, I hope I never really piss her off!" I thought. "Also I got you some jewelry to wear when we go out to do girly things or shop. Two gold necklaces. One spells out COCKSUCKER and the other SISSY. I also got you a few cute pullovers with similar lettering on them so you can let everyone know what you are." My sissification was a continuing process of servitude, punishment and amusing her guests. True to her promise Mistress required that I eat her cunt everyday when she came home from work and each night at bed time. Sometimes I would be all in latex, bound, with my mouth pulled tightly into her crotch by a hood attached to the crotch of a pair of latex panties. The hood was belted around my neck. So I would eat until she told me to stop and start again, usually, in the morning for a wake up orgasm. These sessions would sometimes last for hours. For weekends there was the couch of oral pleasure where she could recline and I would be kneeling between her legs servicing her. Sometimes for most of the day. I would of course be incased in latex with my arms in sheath behind my back. Mistress came home early one after noon and found me blowing myself and flew into a rage. Next thing I knew I was laying on the floor as the collar knocked me on my ass. "Michelle I want you doing chores not sucking your dick. I know it is part of my sissification program but I want to tell you when you can suck yourself off. You'll only do it at my pleasure!" What she didn't know was that now that I was limber enough I indulged myself frequently throughout the day. I'll have to be more careful. It was Saturday night and the wife was having some girl friends over for a few drinks. I was all femmed up and wearing an apron with little hearts on it. I was serving and cleaning up like the maid I was supposed to be. On my neck was a electronic dog shock collar and a gold chain with "Cocksucker" spelled out on it. The girls were all having a great time making comments about me, pinching my ass and making lewd comments. "Hey girls", my wife chimed in, "Michelle is able to do something that most of you girls think is impossible for guys to do. He can suck his own dick!" (With my wife's help over a period of months I was once again able to suck myself off). Amid all the tittering my wife said, "Michelle give us girls a demonstration." I was horrified at the suggestion an hesitated which was the wrong thing to do. A reminder from the collar made me quickly remove my apron, drop my skirt and half slip and pull down my panties. Bending over and with a little coaxing I was able to start sucking on my growing prick. "Don't you dare swallow Michelle, I want you to show the girls a mouthful before I allow you to slurp it down." It wasn't long before I was able to get off. I straightened up and opened my mouth for all to see. The girls were all giggling and saying how wild that was. Wife gave me the nod to swallow and I pulled my clothes back on. Before I could go freshen up my make up, one of the girls asked if I could be allowed to do her. I looked at my wife and said "Mistress?" "It's ok Michelle. Go ahead." I dropped down between her friend's knees, lifted her skirt, and pulled down her panties only to be met by a tiny dick. As I went all the way down on "her" dick "she" gave a shudder and exploded into my mouth. I found I was a bit miffed and had hoped for a little longer session. Comments from the girls ranged from; "My she sure is enthusiastic!", "Look at her gobble that thing!", "A real cum slut!", "A born cocksucker!", "A man's dream girl!" "Does she eat pussy, too?" Mistress dismissed me to clean myself up and return to my duties. If I was a good girl my real rewards came at night as I prepared myself for bed. First I stripped down and powdered up my body, next I donned my latex catsuit, luxuriating in the coolness and silky feeling as I worked it up over my body. Next came long latex gloves that came up over my elbows followed by a latex hood with nose, mouth and eye holes. Once everything was adjusted I stepped into the coffin and worked my way into the 2 ply latex sheath. Before I slid my arms into the inner sleeves I attached the milking machine to my pecker and inserted the penis gag in my mouth. It had tubing attached to the milking machine to allow me to enjoy the results of it sucking me off. Using the inner zipper I closed the bag and worked my arms into the inner sleeves. There is a timer on the coffin so shortly there after the lid came down. A latex pad pressed down on my forehead and the sheath started filling up with air pressing against me tightly until I was unable to so much as wiggle. It is like being in a rubber womb. It was quiet, peaceful, warm and slippery. I was starting to doze when the milking machine came on slowly sucking. I lay the riding on waves of pleasure as it sucked and jerked me off. Finally there was a satisfying orgasm and my mouth was filled with cum. Warm, slippery and tasty. I sucked out the last drop a fell into a heavy sleep. Right on time (5a.m.) the milking machine came on awaking me to a warm breakfast in bed. Minutes later the bag deflated and the lid rose up allowing me to hurry out. I had to quickly clean up the latex wear, clean up, get femmed up and make Mistress her breakfast or she would be displeased. She didn't normally wake up in a good mood. If I was late or my makeup job was poor I was likely to get zapped. We had a full day of shopping. My Cocksucker necklace got a lot of snickers from men and women alike. After diner and I had cleaned up Mistress told me to get my purse and come with her. We drove for awhile until I noticed that were had arrived at the prison. The guard waved us through the gate. As we got out of the car Mistress grabbed my arms and handcuffed them behind me. "Come on cunt, I have a surprise for you!" She took me into her office and pressed a button on the wall. A panel slid back showing the interior of an elevator. We entered and went down several levels. The door opened on a long well lit hallway lined with doorways. "This is where we put prisoners in solitary confinement and this is your cell." So saying she punched in a code beside the door and led me inside. Before I could say anything a harness with a penis gag attached was slipped over my head and locked in place. I stood there in shock as she closed the door to the cell and silence closed in. The cell had a cot, toilet, and sink. I had fallen asleep on the cot when I felt a presence and opened my eyes to see a figure in hospital scrubs and a mask stick a needle in my arm. I opened my eyes to see a woman standing over me telling me to wake up. "Lets go Michelle! Wake up! Time to meet your new self. You've been asleep for awhile and while you were out we made a few changes. Let me help you up so you can see yourself in a mirror." As I stood I found I was pretty wobbly. When I finally looked in the mirror I was stunned to see a nude female form. Me!!! "Notice the 44C breasts, the cute little cunt and the hairless bod. You are now the girl you always wanted to be and your Mistress has some great plans for you. You've been here long enough to heal so you'll go home today where you will need at least a month to get back your strength. By the way you have some implants in your clit and breasts to heighten your pleasure during sex. Goodbye, and enjoy your new body." I was able to relax and recover from all the surgeries for a month. Mistress had someone come over to pierce my breasts with little gold rings and triple pierce my ears. During this time I was exploring my new body and found that I could now have multiple orgasms. I remember thinking that what a great toy women have. They can play with their cunt all day long and have numerous orgasms unlike men where you get one shot and that's it for several hours. "Michelle I just purchased a new toy for you. Strip down and stand with your legs apart." She then produced a harness with 2 dildos on it. One was longer then the other. She lubed them up and inserted them in me, locking the belt around my waist and at the sides of my legs. "What's neat about this is that each dildo has a vibrator inside. This remote has different settings, fast, slow, medium, random. They will also rotate, shrink and elongate. Let's try it out." With that she turned it on slow and the vibs titillated my sex. My nipples started to harden and my hips started to move. The medium setting soon had me panting and bucking trying to reach an elusive orgasm. With a smile mistress set it on high. A massive orgasm exploded in my brain and kept going on and on. Spasms rocked my body and I fell to the floor flopping around like a fish out of water. I was laughing and crying and pleading for Mistress to turn it off. As she gave a little giggle, her eyes rolled back in her head and she collapsed. Fortunately the remote fell out of her hand and landed where I was able to get it and turn it off. I crawled over and checked Mistress for a pulse and found none. I could try CPR or think it over. With that thought I got up and went down stairs where I made a stiff drink, turned the vibs back on low and let them hum happily away. Picking up the phone I called Clint to tell him that now we could be together.

Same as Michelle's Sissy Training Videos

2 years ago
  • 0
  • 27
  • 0

Sissy Julian Chapter IX Girlie Training

Sissy Julian - Chapter IX, Girlie Training by: sissystevie Calm before the storm as Julia learns womanly skills. But for whom? And as what? This is a transitional chapter that uncovers some of the mystery behind The Order and Miss Jane's recent activities. I included the section on The Order simply because it has been so long since it and many of the related characters were first presented in 'Dani's Story.' As always, this is a purely fanciful, fantasy fictional work....

3 years ago
  • 0
  • 53
  • 0

Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
  • 0
  • 24
  • 0

Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite...

3 years ago
  • 1
  • 24
  • 0

The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

3 years ago
  • 0
  • 20
  • 0

Michelles Continuing Affair Ch 2

When I got back to the house, Michelle was dressed in a pair of sweats and thin T-shirt, no bra. That didn’t surprise me, she’s been going without a bra at home more and more since she started seeing Mike. It still made me a little horny, seeing her so obviously braless in front of another guy, even if she had spent the night naked with him. I kind of suspected she wanted to get me alone, so she could ask about my night with Jacqui…and I was anxious to tell her, but it wasn’t to be for a while...

3 years ago
  • 0
  • 27
  • 0

Michelles Gift part 2

Siobahn and her boyfriend Brian have decided to give their friend Michelle a very special birthday gift. They’ve just returned from Michelle’s birthday party at the local bar to Michelle’s house. ‘Oh, someone’s been naughty tonight! Look, honey, she hasn’t beenwearing any panties,’ Siobahn said to her boyfriend Brian as she pushed up Michelle’s skirt. ‘Mmm and she’s’ very wet. Come taste.’ The tall black man was immediately on his knees between the legs of his girlfriend’s best friend. As...

4 years ago
  • 0
  • 25
  • 0

Michelles Gift part 1

‘I’m so glad you could make it!’ exclaimed Michelle when she saw Siobhan and Siobhan’s boyfriend walk into the bar. ‘Well, you didn’t think I’d miss your birthday, silly! Sorry we’re late.’ Siobhan gave a wry smile and then turned toward the tall, black man accompanying her. ‘Michelle, I want you to meet,’ ‘Brian,’ Michelle finished the introduction for her friend. ‘It is very nice to meet you, I’ve heard so much about you.’ ‘All good I hope,’ chuckled Brian. Basically the extent of what...

2 years ago
  • 0
  • 24
  • 0

Michelles Awakening

Michelle’s Awakening Ch 1 Finally, 4:30. Michelle could now leave work, and head to the gym. But she wasn’t going there to work out, like she told her husband, Greg. She was meeting Mike in the side parking lot. Mike was her lover. Their relationship had been going for almost 3 months. Michelle was bored in her marriage, and their sex life was routine, as well as infrequent. She longed for more. Michelle and Mike worked together, and had frequently met for lunch. The more they talked, the...

4 years ago
  • 0
  • 32
  • 0

Michelles Sexuality ReAwakened Ch 3

I was hoping that my imagination wasn’t outpacing what thereality would be. This could all turn out to be a big disappointment. The other possibility that was rolling around in the back of my brain was that Michelle would fall for Mike and then want him over me. Unfortunately, I was so obsessed with thinking about Michelle with another guy that the fear factor was relegated to the small part of my brain that was actually thinking clearly. But if I gave in to my fear, there probably wouldn’t...

4 years ago
  • 0
  • 21
  • 0

Michelles Continuing Affair Ch 1

After Michelle’s description of her weekend with Mike, I asked her to call him again and set up another date in our hometown, Pasco, Washington, as I wanted to actually see them together. Michelle told me that Mike was still in love with her from their affair sixteen years ago and the sex she described to me from the weekend was pretty fantastic. Michelle expressed her love for me above all else, but I have a burning need to actually see her and her lover together. And did I even want it to...

3 years ago
  • 0
  • 50
  • 0

2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
  • 0
  • 34
  • 0

Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
  • 0
  • 43
  • 0

Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
  • 0
  • 34
  • 0

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
  • 0
  • 34
  • 0

The SissyMaster

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...

4 years ago
  • 0
  • 34
  • 0

Michelles Sexuality ReAwakened Ch 1

Jan 1, 2014, a new year. Michelle and I were sitting at our dining room table playing a dice game with her parents after cleaning up the dinner dishes. After Michelle’s mom won the game by about three thousand points, I asked them if they would excuse us for a few minutes. I had been anxious all day, waiting for a few minutes of freedom from our company to show Michelle the story that had just been published, so I asked her if she would read something on the internet with me. Although I didn’t...

1 year ago
  • 0
  • 39
  • 0

Michelles AwakeningPart 2

PT 2 Ch 4 Life during the next week was difficult for Michelle. Seeing Mike at work and not being able to get close to him was maddening. In addition, Greg was expressing concern about their lackluster sex life. She knew that she shouldn’t ignore him, but try as she might, she just couldn’t get excited about having sex with him. Tuesday afternoon, Michelle was organizing her desk prior to heading for the gym, when Mike walked in, closing the door behind him. “Hi babe”. “Hi honey! I was just...

1 year ago
  • 0
  • 17
  • 0

Michelles Morning Surprise

Michelle squeezed the shower gel into her hand and started to cleanse her smooth skin. She lifted her leg and caressed from ankle to thigh, then over her flat tummy and up to the small swell of her breasts. She gave them a little squeeze and flicked innocently over her nipples with her fingers. Her mind was filled with images of Jason, a guy she’d met at a customer’s office earlier in the week. He was so fit and handsome and Michelle had noticed him looking her up and down, his eyes straying...

4 years ago
  • 0
  • 39
  • 0

Michelles Sexuality ReAwakened Ch 2

Michelle is thirty-eight now and still looks fantastic, I think evenmore so than before. She’s so much more mature than when we were first married. Her breasts have filled out very nicely, but otherwise her body stayed pretty much the same. She is 5’6 ”, 128 lbs, and has a figure to kill for, plus that beautiful face and personality! When she smiles, her entire face is radiant and can light up a whole room. Usually I only see her as my wife. But sometimes I look at her and don’t see my wife of...

3 years ago
  • 0
  • 22
  • 0

Michelles Continuing Affair Ch 3

Mike left for Seattle Sunday morning after breakfast. Shortly after he left, Michelle and I satdown to talk about the weekend. “Honey,” Michelle started, “I need to know, what are you really thinking about me and Mike?” I paused for some time, trying to think how to answer her question. “Babe, there hasn’t ever been anything hotter than watching you and Mike together, especially last night. I don’t know how to explain it more than we’ve already talked about, but I can’t get over the thrill of...

3 years ago
  • 0
  • 19
  • 0

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
  • 0
  • 30
  • 0

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
  • 0
  • 24
  • 0

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
  • 0
  • 21
  • 0

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...

1 year ago
  • 0
  • 26
  • 0

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
  • 0
  • 32
  • 0

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
  • 0
  • 25
  • 0

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
  • 0
  • 20
  • 0

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
  • 0
  • 30
  • 0

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
  • 0
  • 34
  • 0

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
  • 0
  • 28
  • 0

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
  • 0
  • 24
  • 0

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
  • 0
  • 36
  • 0

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
  • 0
  • 24
  • 0

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
  • 0
  • 22
  • 0

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
  • 0
  • 40
  • 0

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
  • 0
  • 25
  • 0

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
  • 0
  • 29
  • 0

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
  • 0
  • 19
  • 0

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
  • 0
  • 30
  • 0

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
  • 0
  • 34
  • 0

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
  • 0
  • 31
  • 0

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
  • 0
  • 24
  • 0

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
  • 0
  • 23
  • 0

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
  • 0
  • 25
  • 0

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
  • 0
  • 41
  • 0

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
  • 0
  • 45
  • 0

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
  • 0
  • 21
  • 0

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
  • 0
  • 24
  • 0

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
  • 0
  • 21
  • 0

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
  • 0
  • 23
  • 0

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
  • 0
  • 23
  • 0

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
  • 0
  • 28
  • 0

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
  • 0
  • 40
  • 0

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...

2 years ago
  • 0
  • 23
  • 0

A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
  • 0
  • 15
  • 0

Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
  • 0
  • 42
  • 0

Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
  • 0
  • 30
  • 0

I Now Own You Sissy

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

Porn Trends