Andrew The Unsuspecting Sissy Part III
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ANDREW THE UNSUSPECTING SISSY PART IV [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...
ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...
ANDREW THE UNSPUSPECTING SISSY PART II ANDREW'S SISSY EDUCATION BEGINS............ [email protected] Mother and daughter chatted while they ate their breakfast. Several sissies flitted about changing flowers and removing dirty dishes. "Mother," said Sarah. "How many sissies call the Manor their home these days?" "Hmmm," said Audrey as she placed her coffee cup in its saucer. I'd have to say with the school, the modeling agency, the internet dormitory, the domestic...
Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...
My thirty year old wife Ceras and I enjoy a fairly liberal sex policy. You can imagine she gets hit on a lot which leads to a lot of swinging opportunities. Ceras has an average looking short twenty-eight year old former co-worker friend named Andrew that has always had the hots for her. She would never do anything with him because they worked together plus he wasn't her type and as a rule we don't get involved with friends. He's a funny guy and I get along well with him and always found his...
SISSY 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...
Andrew James Wellington III, Esq. - Dead Beat Dad By Sirbosk1 ? sirbosk1 2009This story is a fantasy that contains scenes of Femdom, oral sex, rimming, cream pie eating, humiliation, blackmail, CBT, bondage, spanking, body modifications, and other erotic activities involving adults. If such subjects are offensive, uninteresting or if you are a minor, (i.e., child) please leave now. This story was written at the request of a sub fem friend of mine who’s husband recently walked out, leaving her...
Andrew by Grimbo Andrew slowly woke to the distant sound of a woman's voice. "Well sleepyhead," it said. "I'm glad you have finally awoken. You may be wondering were you are so I'll tell you. You're back inside Shannon's Boutique. You remember my store don't you? You came in here last week with your girlfriend and knocked a lot of the clothes off the rack. If my memory serves me, your comment was 'Let the staff pick them up. After all, that's what they get paid for.' Well,...
Andrew walked home from the party. No, he didn’t really walked, he stumbled and staggered, legs held as wide apart as he could, nursing an asshole that only a few hours earlier had been the virgin bud of a true stud, and was now gaping obscenely. Even as he walked he felt it throb and pulse… and he felt the warm liquid leaking down along his inner thighs – liquid that could only be Thomas’s cum. His mind kept going back to the party – a party to which he had been specially invited and to which,...
I met this guy Andrew on a website. He wanted to meet for coffee at the local coffee house. I agreed and met him at 2 in the afternoon. When I got there, he was conducting a meeting with some of his colleagues. I grabbed me an iced tea, then walked towards his table. Andrew pulled me to sit next to him on the booth bench.He wrapped up his meeting, then turned his attention to me. We sat close as we chatted about our likes and dislikes. His hands were all over my legs and arms. I didn't...
Andrew helps me put my stuff in my car, then he climbs in the drivers seat, to take me back to his house. Or so I thought. The man drove to the cute little boutique in town. "A Dream for Him" , Andrew lead me through the door with him holding my hand. An older woman built like a brick house stepped out from the back room. "Hi, Louise" Andrew said. Louise came over and kissed Andrew on the cheek and gave him a hug. Andrew introduced me to her and told me to go look around, as the two who...
Here's the 3rd part of my story, I hope I didn't make you guys wait toolong. Hope you enjoy, its best read one handed ;-)My Girlfriend Made Me a Sissy - Part 3-------------------------------------------------I lay on Jess' bed waiting for her and wondering what would happen forages. She was in another room getting ready for her new lover, I wasalready dressed up. Pale blue, see through panties and matching bra, ashort black skirt and a blue vest top. With my make up done to show off mypretty...
Three months after Andrew and I had had relations I was close to his house and decided to pay him a visit, knocking on his door he answered it and greeted me like a long lost friend. As I walked into the lounge there was a young Asian lad sat on the sofa, they were playing video games. As soon as I walked in Andrew said “This is Ansa” we nodded and said hello. I sat next to him.Andrew made me a coffee and turned the TV off, we made small talk and Ansa worked at the supermarket where Andrew...
Andrew Running (part 1 of Andrea's Stand) Chapter 1: Running I called my Aunt Clara from the bus station. She didn't seem that surprised to hear from me and when I explained why I was there she told me to walk a couple of blocks to the local diner and get myself a cup of coffee. She'd pick me up in about half an hour. I sat and sipped chocolate milk and tried to eat a pastry while I glanced nervously out of the window waiting for my father to show up and force me into his...
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...
Andrew always grew up feeling more then just a little different from the rest of the boys. He never felt sexually attracted to girl’s bodies but instead felt attraction for their clothes. He knew he was straight because he never liked guys so he just assumed he was straight. This began his seventh grade year and followed him into his senior year of high school. He started off by reading sissy literotica and watching sissy hypnosis. He then began experimenting by trying on his sister’s...
Hey guys this is my first story ....hope you all like it ...When I was 18, in spite of my shyness and not being in anyway incrediblyattractive, I somehow landed myself a girlfriend 2 years older than me. Iwas quite short for a boy then, around 5'7 and very slim having not yetdeveloped much muscle. I had shoulder length brown hair and bright greeneyes and I simply couldn't believe my luck in getting this girl. She wascalled Jess, a beautiful redhead with a body to die for and an appetite forsex...
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...
Chapter 2 I tried as best as I could to get comfortable curled up in the corner of the room. At first I kept squashing my tail which either caused the vibrations to start or pushed the plug further inside. I had eventually worked out the best position to lie in when Mistress appeared. "Time for bed Fifi," she said as she attached the pink lead to my collar. I was then led through the house and up to her bedroom. This was a strange feeling to enter her bedroom not in my usual maid's...
Larry and Andrew had been friends for about 9 to 12 months. Larry was black, 6 ft tall with dark skin. Andrew was white a little taller than Larry. Andrew was dating Jen, she was Asian probably 5’ 3” with long dark hair and a tight little body. Priya was Indian about the same height as Jen with brown skin, shoulder length black hair, and a very nice little body also. Jen was very much in love with Andrew but very flirty with Larry. Larry thought she was being nice and didn’t think too much...
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...
CHAPTER THREEMistress Jennifer and Mistress Susan's plans to create an entire"harem" of transformed men and boys continued apace. The lure ofTeasing Tammy (the transformation name of Susan's teen-agedbrother Tommy) proved quite effective. Each of the young men (theyoungest just 14, the oldest 22) the little tease brought back tothe home we all now shared was turned into a different kind offeminized sex-toy, all designed to please the Mistresses andtheir dominant friends.The little...
Introduction: This is my story for the CAW 10, it is also a true story about a dark part of my life that I am just starting to come to terms with and wanted to share. Please try to be constructive when giving criticism to my story. Thank you to my last minute proofreader and to you the reader for taking the time to actually read my story. Vicki x This is my first attempt at writing my story, I have decided to enter it in the CAW 10 also. Please give me constructive criticism and try not to be...
My 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...
Please give me constructive criticism and try not to be too harsh with me as it is my first story and a part of my life. Andrew I felt so lucky to have someone who loved and cherished me so much or so I thought. In my naivety, I gave him my virginity at the mere age of fifteen. It just didn't click that maybe he was using me for his own twisted pleasures. I always thought he truly loved and cared for me and my ambitions to go to art college. Everything was fine until I turned...
My name was, once upon a time, Andrew McKenna; now it's Ashleigh Barnes, and how that happened is a long story. I figure the best way to start is to tell you about the day I died. At least, I think I died! Even if I didn't die, though, I for sure went to heaven. I never in a billion years would have thought things would have turned out the way they did for me. Stick around and I'll tell you all about it. The day I died (maybe? anyway, let's just say died, because Andrew is totally...
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...
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...
Sharon’s Mistress throws a Sissy Party(Prior chapter is Sharon’s Sissy Saturday)The next morning Mistress was kind enough to let me sleep in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I...
My last "true life" story was about how I became Heidi's sissy crossdresser "Danni" - I only explained the initial experience of Heidi coming home to find me in one of her dresses - followed by spankings, punishment and eventually getting pegged by her wearing a strapon. Of course there is MUCH more to what happened next (like being taken out in public and going shopping, to hair salons, etc...), but I'd like to for now jump ahead to what happened to me on my 19th birthday. By then I...
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,...
My name is Andrew Lake. I am a junior at Brickton High School, even though I just turned 18 last month. I don't consider myself unhappy, just a little out of place. I'm a smart kid, but I'm not the brightest bulb in terms of social interaction. I only had a few friends, all of which in similar situations as me, and not a single girlfriend throughout my school career. Hense, my porn addiction. Romantic relationships aside, I had a pretty decent life, just not a perfect one. My life was,...
My name is Andrew Lake. I am a junior at Brickton High School, even though I just turned 18 last month. I don't consider myself unhappy, just a little out of place. I'm a smart kid, but I'm not the brightest bulb in terms of social interaction. I only had a few friends, all of which in similar situations as me, and not a single girlfriend throughout my school career. Hense, my porn addiction. Romantic relationships aside, I had a pretty decent life, just not a perfect one. My life was,...
My name is Andrew Lake. I am a junior at Brickton High School, even though I just turned 18 last month. I don't consider myself unhappy, just a little out of place. I'm a smart kid, but I'm not the brightest bulb in terms of social interaction. I only had a few friends, all of which in similar situations as me, and not a single girlfriend throughout my school career. Hense, my porn addiction. Romantic relationships aside, I had a pretty decent life, just not a perfect one. My life was,...
Introduction: Hey guys, this is my first story. Its based off of a dream I had, as will the sequels in this series. Please enjoy, like the story, and comment with any suggestions. My eyes hurt from staring at the small screen all night, but I couldnt bring myself to look away. I had been watching porn for what felt like ages, stroking myself to women on the internet doing unimaginable things to one another. I felt like a sick pervert inside, but I was far too busy to concern myself with such...
Introduction: And it happened again FFS. Made sure this account will not be deleted, enjoy the story and wait for more. I will be posting more I promise. Apologies for the technical difficulties ???? My eyes hurt from staring at the small screen all night, but I couldnt bring myself to look away. I had been watching porn for what felt like ages, stroking myself to women on the internet doing unimaginable things to one another. I felt like a sick pervert inside, but I was far too busy to concern...
Introduction: Hey guys, so my account was rejected by xnxx after I had posted this, so for the sake of simplicity I am re-uploading it here. I apologize for the confusion. Feel free to rate and comment again, and stay tuned for the next parts, assuming my account isnt denied again. My eyes hurt from staring at the small screen all night, but I couldnt bring myself to look away. I had been watching porn for what felt like ages, stroking myself to women on the internet doing unimaginable things...
AndrewCouple of weeks ago, we had been down our local having a drink and laugh with friends, Hubby had a few too many, and decided to get a cab home, but I was hungry, and wanted to eat, so I thought a takaway would be the answer, but again having drank a bit, the restaurant was a mile or two away, but my prayers were answered, when a son of our friends offered me a lift there to collect and return me to the pub, well though I was slightly pissed, I got some money out of hubby and said to chas...
I was in my front garden in shorts and T shirt when my neighbour Karen came walking towards me very quickly and agitated. “Oh Andrew, can you help me please I’ve got a leak in the kitchen and I’ve left Brooke holding a rag round it? I just don’t know what to do.”Karen, brunette and hot single mum, wearing a short skirt and T shirt was the object of my wildest fantasies and needed my help. I jumped up, eager to do my bit, “no problem Karen, let’s see what I can do”. I followed her to her house...
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...
SISSY SISTERS PARTY by Throne Bob Clump, the friendly retired guy at the end of the street, was taking advantage of the mild weather of late Spring. He was sitting on his front porch enjoying a fine cigar. Or at least a cigar. Those fine ones cost a lot more than what he smoked. As he sat there, a car pulled up across the street, in front of the house diagonal from his. In the dimming light of dusk he saw two figures emerge. The first was a woman, quite attractive in a slender,...
SISSY GIRL PARTY by Throne Danny felt so ashamed, standing there before his wife Melba in a pink and white party dress that would be appropriate for a nine year old girl, not a grown man like himself. He cringed inwardly and unconsciously took one of his short pigtails and wound it around his finger. His feet were shod in pretty ballet-type slippers, pink ones with little rhinestones on them. "You look so sweet, Dee Dee," she said with a smirk that he knew all too well. He had...
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...
My mum and I lived on the outskirts of a small Scottish village. John and his mother Beth were our neighbors, and he and I were best friends from an early age, sharing everything as we grew up. At Primary School and then Senior Secondary School, we were an inseparable pair, supporting each other through the good and bad times. This idyll came to an end when we had just turned sixteen. He and his mom moved away from the area to go look after a sick relative.The house was quickly re-occupied and...
CrossdressingMy wife and I were invited to some friends’ house on a beautiful estate in TX for a weekend party. While we were both well aware of the debauchery that could occur at the event, we had no idea how much participation we would both play. We were just getting off the plane to meet our driver when my wife handed me a slutty little maid outfit, and told me to go into the bathroom in the airport and change before we got out of the terminal. I did as she asked and then tried to walk out without anyone...
A 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...
'You want it again?' She said, as she climbed between my legs, spreading them with the force of her knee. 'Yes Mistress.' I said, turning my head to the side. Her gloved hand grabbed my chin and turned it towards her. 'You want to be my girly lesbian bitch?' She said, as she tweaked my puffy nipples with her other hand, the dry latex chafing me. 'Yes Mistress - I want to be your girly lesbian bitch,' I rubbed my horny cunt against her stocking clad leg, ignoring the pain, wanting, no, needing...
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...
The family – Sissy’s Babysitters Part-2Sarah had left, I heard the front door close and her car drive off.....I couldn’t believe what was happening. Sarah and me had done some things, had fun with others, but she had dressed and prepared me not for ‘our’ fun...to leave and let her parents use me, they obviously knew about ‘our’ pleasures....it was James & Helen the couple that I sat with, talked to before marrying their daughter...was it something they always knew, or something they had...
I 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...