Richard the Sissy gets Caught by Sis
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I led Jaime from the garage to my master bedroom in the back of the house and told him to get in the Waiting Position as he had done before and to remain silent until he was told he could talk. I smiled when he nodded his head up and down for yes since he had just been denied the right of speech. Perhaps he may just become as valuable as he appears on first glance, but that was rarely the case and each sissy was a reflection of the woman who transitioned him from his maleness. He was merely...
FemdomSISSY SEX THERAPIST by Throne "But honey," Darren said in a whining tone. "You can't mean that. How could I be a... a sex therapist?" His wife Kelly smirked at him and said, "You have to understand, Darla, that a sissy like you could be very valuable in helping some men to deal with issues they have in their sex lives. For instance, the new guy I just started dating, Brad. He doesn't understand the whole sissy mindset, and how useful a weak feminized husband like you can be in...
Part 4 - Stepmother's Test She crossed her legs and began dangling her high heel again and Carl became excited. His sissy stick started to stick up as he watch the dangling show and fashion models prancing on the run way. He had no where to escape and his stepmother noticed her panties bulging with his sissy cock. She nonchalantly let the shoe fall on the carpet and said, "Well, missy are you going to pick my shoe up and place back on my toes or can't you get up!" "Yes, ma'am, I...
Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...
Heather's SissyMy husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.I'm not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it...
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...
Community Service: Chapter OneBy Posing SomdomiteBANG. BANG. BANG. "Sharon, get your lazy ass out of bed," Margo yelled between forceful knocks on the dorm room door. The fact she even had to go through this little charade agitated the young red head beyond words. There was no way in hell Sharon was still asleep, Margo was pounding loud enough to wake a corpse. The Blackberry in her back pocket started to vibrate, indicating a text message was received. Margo cursed very softly as she...
Sissy Stepmother A Pantyboy Profile INTRODUCTION Cheryl here. You remember me. The 20-year-old pantyboy extraordinaire. Every man's naughty, secret, wet dream. Raconteur without equal. In "Service" and "Test Driven," I told you about Amy and Judy, two of my lovely roommates, fellow pantyboys and like me, covergirls for "Panty Boy," the only publication worth buying, besides some of those Spermco comic books about us "special boygirls" and the "Sunday New York Times." And Panty...
BANG. BANG. BANG. "Sharon, get your lazy ass out of bed," Margo yelled between forceful knocks on the dorm room door. The fact she even had to go through this little charade agitated the young red head beyond words. There was no way in hell Sharon was still asleep, Margo was pounding loud enough to wake a corpse. The Blackberry in her back pocket started to vibrate, indicating a text message was received. Margo cursed very softly as she fished the phone out of her designer jeans. sorry. sick....
InterracialKeith Spencer looked up at the clock on the wall and sighed. The crew-cut eighteen-year-old couldn't believe that only thirty minutes had passed of the eight hours he was required to put in at the Roosevelt Park Tri-County Help Center. For perhaps the hundredth time this month alone, he asked himself how he had gotten into this fix. A few years back, the local school board had passed a requirement that every student have a hundred hours of community service in order to graduate. While it did...
“Did you finish the agency report Jack? I want a simple yes-or-no answer.” asked the old man angrily, looking at the handsome young intern through his bifocals.“No sir, but –” stuttered Jack knowing that he had really screwed up this time, and the boss was not going to let him off lightly.“So you sat at your desk doing nothing all week knowing fully well that I needed that agency report this morning. I am at a loss of words at your lackadaisical attitude Jack!” the old man was shaking with...
The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 4: Southern Belle Sissy By Cheryl Alison Mistress believes in community service. So when she dropped the ad on my desk at home, I knew that I would be a faithful community servant within a short while. The ad read: Southern Belles Needed The Ladies' Auxiliary needs...
It was a warm summers evening as sissy rode around the indoor school on her masters favourite mare her tight white jods were clinging to her as she gripped tightly with her legs urging the mare on with a gentle kick .The mare was proving to be a difficult ride and gave a few playful bucks sissy gripped tighter with her legs and found that she was getting a hard on from the vibration coming through the saddle instead of correcting the mare with her crop she lent foward pushing her cock against...
My advertisement read: MEN Interested in sex with other men but don't know how to proceed? Looking for a safe, friendly way to find out if this is for you? Obsessed by online bi/gay/sissy/crossdressing porn but frightened to meet someone? Is your marriage at risk because of your desires? I can help! One four-hour sexual therapy session will help you to decide if this is right for you, and will help you to understand your desires. Don't suffer alone, I can...
Richard arrived in a taxi at his friend Aaron’s family home, a huge mansion like house for the mid-winter party at the same time as an elegant looking lady with silver grey streaks in a stylish expensive coiffeur cut to just below her ears. She was very fashionably dressed wearing white tailored cut satin slacks that shows her ass nicely. She was also dressed in a designer black faux-fur vest, black soft leather gloves with a small designer leather bandolier strap i-phone wallet hanging from...
Margaret arrived to do the cleaning on Friday and she knew that she would be returning to the house again that evening to spend another night with Richard. She had still not made up her mind whether the caning that Richard desired would be administered on this day or whether she would postpone it until another time.Richard was determined to keep the caning at the forefront of Margaret's mind and she smiled to herself when she found a magazine opened on a page showing a young man bent over and...
SpankingMy Stepmothers Sissy Daughter By Malissa Madison The dream was so real, she was being chased by some evil thing that thirsted for her blood. She was cornered with nowhere to hide. She felt its hot breath on her as she tried feebly to squeeze through a hole too tiny to fit. The hot breath as it pushed its nose against her bottom. It felt hot and wet, Wet? She woke with a start in full panic unable to stem the flow. All she could do was lay there and cry in silence. She'd had this...
Richard has never understood himself when It came to love. He just wasn’t ready for it. But, in one of trips home he found love. He found love in a girl names Jeanette. Jeanette was a pretty girl, something Richard was not to used to. She was about 5’ 3” tall, no more than 120 lbs, and a nice B size chest. Not overly top heavy, but enough to make him happy. She has soft blonde hair that goes just past her shoulders, with bangs that hang just past her eyebrows. Blue eyes that can just cut...
Richard showed Margaret his (skeletal) house and described what he hoped to do. She told of her school in Brisbane – St. Margaret’s – and how she had worked in the new school library. “It seemed like a fine way to spend time: surrounded by knowledge and both preserving and disbursing it.” Richard told her about the Agricultural College and his two years at Lamorbey. “My folks live in Warwick! That’s only an hour from Gatton!” “And only double that to Southport, where my parents...
Richard invited his parents to the graduation ceremony and they drove to Gatton on Thursday, 1 December. The ceremony ran from about 10 to 11, before it became really hot. Andy and Sybil then helped Richard load his accumulated detritus into their (new) Ford Falcon and a few things into the (rusting) Jeep. “It’s done well over these three years,” Andy remarked. “Yes. I’ve had no major problems: plugs, belts, shocks, tyres, wiper blades, but nothing large.” “Well, it’s little over two hours...
"You do have a choice Richard. You don't have to do it, but life will be so much easier for you if you do. If you do it nothing changes except that you will never sleep in my bed again. Although I'm going to be taking on the role of CEO you will still be president of the company, you will still have your country club membership and you can even keep your bimbo. If you don't do it you are out of a job, homeless, probably not able to buy your little blond slut a cup of coffee and the only way...
Lamorbey Station seemed to comprise a sprawling house, a second, smaller house, a pair of barracks-like buildings, and a number of barns and sheds. At first it seemed more extensive than College, but fewer people. Richard had been introduced to the Millers and several other people at dinner, but he recalled none of them. He’d slept in his swag on the floor of Ferd’s room. They were up at six, washed, and outside to join a group of about forty, half of whom were aborigines, to hear the day’s...
The year ended. Richard drove west and north, arriving at Lamorbey on schedule. He was welcomed by Janey with an exuberant night of sex. In the morning he was welcomed back by the foreman and many of the crew. Ferd was in Emerald on a “shopping trip.” Ferd turned up in mid-afternoon. He’d been purchasing ammunition: .30- .30 and .30-06 cartridges and a box of slugs for the 12-gauge shotgun, which Richard had never seen. The “hunting party” was to be made up of Ferd, Richard, Janey, Al, and...
Lamorbey Station seemed far away when Richard pulled onto campus early on Monday. He’d spent Friday night in his Jeep, near Tambo, an hour past Blackall. He’d lunched and dined out of the esky. The next night he’d spent in a motel in Roma, where he’d enjoyed a shower. Last night he stayed at the Royal, an older hotel in Gatton, and so was well-rested. He was also in a good mood. He’d opened the “pay envelope” and discovered ten five pound notes – far more than he’d expected for just under...
Richard asked for the Christmas to New Year’s Day week off and drove to Southport in two harrowing days, with extremely high temperatures. He was welcomed by his parents with the news that “Cat’s on a cruise to Auckland.” After unloading the Jeep he showered and re-dressed. It was a luxury to have real hot water on tap. “How are things?” Andy asked him. “Well, I’ve worked hard for two months and I think I’ve learned a lot. I’ve been talking to one of our Aboriginal drovers and learned from...
One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...
“It’s actually just under 30,000 acres,” Richard was told about two weeks later. “Can you explain?” “Of course. First of all, it’s unclear to me whether the property is within the bounds of Womalilla or of Mungallala. Most likely Mungallala’s too far west. I don’t think Brisbane’ll have to adjudicate. But the land itself extends south of where that two creeks you crossed join to an unnamed east-west road. The land is lightly wooded in the east and shrubby in the west. Because of the...
Richard drove to Mitchell on the 28th, taking a room in the nearly-empty Richard’s Hotel. He ate dinner, washed up and slept. It had taken nearly nine hours to cover the 400 miles from Southport to Mitchell. But he felt invigorated in the morning. After a hearty breakfast, he drove to the store, and bought a 600’ coil of 1/4” manila, a small sledge, a bright orange grease marker and a 40’ measuring tape; he also bought ten pounds of sugar, two bricks of chewing tobacco and a tin of pipe...
Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...
Time flies, they say. Richard knew from school that Ovid wrote “omnia mutantur, nihil interit” (everything changes, nothing perishes Metamorphoses XV), where he later refers to “tempus edax rerum” (time the consumer of things). But what eats up the days, the weeks, the months? One of the Greeks wrote that everything flows. 1962 certainly flowed away. Like water or sand through your hands. Jenna was pregnant again. Joyce would have a sibling before she was three. Ferd was married, but was...
As with any relationship, things change. The suprising thing that happened between me and Martin was at the begining he was a bit soft and I was the dominant person. It could have been that he was new at college and a bit shy. But as the summer went on he bacame a member of the Football, Tennis and Hocky teams. All the better as far as I was concerned as he had three different kits for me to sniff and lick after he had been playing. Blue top,shorts and socks for football, white t shirt shorts...
Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...
NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...
sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...
My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...
I have been doing some community service due to a DUI.It is my first, and I didn't have to do any jail time, but I did however get sentenced to 300 hours of community service.That is a lot of spare time.One thing that this has given me is a lot of contact with young studs that are doing the same thing.I have been able to look over quite a few of them and while cleaning up the road sides, I have had to use mother natures rest room along with a few of them. I can visually check them out and I can...
I had got a DWI and had to do eighty hours of community service. The first 48 hours I worked picking up trash off the side of the road and other stuff like that. The last 32 hours I ended up working with this group cleaning up trails that go thru the woods. My first day I showed up and there was another guy who had to do community service and a old man, I would guess in his 70's. Three women that must have been around that age were also there. They were peppy and ready to work. The women went...
Richard had little use for his wife anymore. He couldn?t even remember why he had married her, aside from it being a naïve college sweetheart thing. He had been a bright young ROTC cadet, on his way to a commission in the Army, while she had been an ambitious marketing major, seeking a career in advertising. Well, Uncle Sam had dragged him around the world in 19 years of service. He had no choice in where he was stationed. This was something that Lacey had never grasped. She had constantly...
hello richard my name is wendy but you can call me maam welcome to boys fat camp are you ready to do whatever it takes to loose weight ?yes maam my method works but you have to do everything i tell you no argueing no questioning me if you can't do that then leave now i have to loose weight maam i'm fed up being the fat boy , now i'm 19 it really can't be passed off as puppy fat anymoreok strip and get on the scales lets see what we are dealing with um everything ?of course naked come on don't...
It was only when her husband Richard promised to ensure her anonymity that Nikki agreed to go out with him and dance in wild fashion and wear the party dress he picked out for her. The club in Tribeca was a long ways from where they lived, but it was one of the hotter clubs and everyone there was in their late twenties or early thirties and looked hot. And going there for the third time now, Richard had got them a hotel so they would not be in their own community to satisfy Nikki’s fears of...
Group SexA sissy and four brothers -What is it like? Mother is very strict about separating me from 'the boys' but they've never experienced a 'sister' in the house before so there seems to be a lot of snooping around. A few of my readers have asked me for some additional information about farm life and living as a sissy with four brothers, and I'll respond to the question about seeing Jack again. Jack's mother called me and told me that I'd done wonders about boosting his self-esteem and she...
Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...
Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...
Richard the III Janet L. Stickney [email protected] Richard left on the Crusades, leaving his maiden alone, longing for his return. She cried out went he left, telling of her love for him, hoping, pleading, that he would not go. Richard, with but a single glance back at her, rode off on his quest. The maiden, her eyes filled with tears sank to the floor in despair, her gown draped around her as her impending loneliness descended on her. The curtain fell to the resounding...
It was a little before sunrise and he was lying in bed, wearing only his boxers, as usual, when his bedroom door opened. There was his daughter. She was sixteen, and developing beautifully. Her firm breasts were beautiful mounds topped with her stiff little nipples. They showed through the thin nightshirt she was wearing. He had seen her in that nightshirt before, and he had wondered if her mother would have permitted her to walk about the house wearing only that. Her mother had passed away...
IncestMy stepson Richard was a very nice quiet boy. Very shy. He was 18 years old but looked much younger. His mother was a bit of a slut and I loved her for that. However, she never really liked Richard and he came to me for love and attention.She told me that he was a fucking looser, never be a real man and was in summer school so he could finally graduate from high school. He would come home from summer school and give me a big hug and kiss. I loved his kisses. I guess I should mention that I...
Bound at the wrists, Richard was draped over a sawhorse in Dietrich's basement, much to the delight of several of his wide-eyed friends. The sexy, bearded German, whom the victim had met over the internet, was giving a small demostration of his leather skills to the appreciative gathering, who sat in abject silence as Dietrich began probing the prostrate man with an irrigation bulb. Richard winced as the hot liquid was injected into his anus, instantly clenching his sphincter closed, more by...
GayI love dressing up whenever possible, which is not often enough. But, what I love even more is dressing up as a hot and wanton sissy slut cocksucker and then going to the local adult theater for some great XXX fun. I am not totally passable, but have been told my legs are fantastic and my ass is nice and tight with a hot tramp stamp just above my ass. Most guys say it's sexy as hell while they are fucking me. Fortunately, my wife had to go out of town for a few days and thereby giving...
My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...
Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...
Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...
CrossdressingPart Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....
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...
One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...
One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...
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...
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...
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...