Sissy Stepson Part 3 Caught in the Trap
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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...
Part 8 - Milking Caroline "Our sissy is going to get ready for milking, I have enough knee highs for everyone to participate" said Mrs. Monet excitedly. She gave everyone three knee high's, sissy Caroline was going to get the milking of her life! Caroline came back to the group with here outfit on and was instructed to sit next to Regina for milking. Regina encased the Caroline's sissy stick with the nylon and instead of using her hand. She took off her high heel and stuck the toe...
Part 9 - Forced to Suck "Get over her you bitch NOW!" screamed and angry Maryann. Caroline's aunt grabbed his limp red puny dick and put the knee high. "What's a matter limp dick sissy, can't get it up for a woman, maybe you need some perversion or more man cock" crowed Aunt Maryann. "Look sister, he's getting a little stiff, he must love to be degraded" said his stepmother wickedly. "Lay down in front of my feet and Phil put a knee high on your cock and start jacking off in front of...
Part 5 - Pantied and Punished Carl begged his stepmother not to spank him and he pleaded, "I'll be good, I will never try your things on again, please!" "To late, you can't be trusted and must be properly punished, but first I want the truth about why you did this. If you don't tell me the truth I will make sure your father knows, his family, your friends and everyone at school!" Carl shook with fear and started to cry. "Please I couldn't help it, I am attracted to your sexy...
Sissy Stepson Part 2 ? Sissy Heaven Carl knew she was going shopping, so he feigned being sick to stay home. He saw that his stepmother wasn't wearing her stilettos and this excited him. They would be his to explore and touch. She bitched at him, "You're not sick!" "Yes, I am, I feel sick to my stomach." plead Carl. "Well, I am still going shopping, I am not waiting on you today, you're on your own!" bellowed Mrs. Monet. "No problem, I just...
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 Trap Everything had went so terribly wrong from my long anticipated shopping experience. I had been a lifelong cross dresser not remembering my first actual endeavor into slipping into my mothers or sisters lingerie drawers. Over the years I had kept this well hidden from my family and friends and had even ceased dressing for 6 years during my ill fated marriage. When my marriage ended I found myself with the passion, time and means to fulfill these long hidden desires. In no...
Introduction: I finally get a test of my stepmothers milk. My father remarried a few years after divorcing my mom. He literally ran into another woman on his way out of the court house. Depressed and in need of company, he invited the woman out for coffee the next morning. I didnt get to see Pamela for a few months. I knew my father was going out with her, but she never really came around the house. They always went out. After returning home one drunken night my father confided in me that he...
Chapter Five: I realize I needed to understand Robert's motivation and desires betterIt happens again the next morning.I arose early, slipped out of bed without waking Robert. Silently, I went into the bathroom. I turned the water on, giving the hot water time to work its way through the pipes for my warm shower. While waiting for the water to warm up, I stared into the mirror and assessed my thirty nine year old body. Objectively speaking, I was in excellent shape. My breasts were firm and...
TabooHi Y’all,Well the week could have been better but it’s ended well. This past week we had a little bit of ice and snow Wednesday night causing for a not so fun Thursday morning of getting the k**s off to school and driving for Uber. My bad Thursday morning started off as I was driving home after dropping the k**s at school and hit an ice patch on a downhill road. The car in front of me hit their brakes as soon as they hit the ice and they started sliding, I hit my brakes too and joined in the...
Foreword – This story though of a familiar genre was inspired by a letter to Dear Abby that contained the line My husbands son – Ill call him Duncan – came to visit The Sneaky Stepson By rutger5 (An original story- copyright 2012) Dont misunderstand me honey, Im not dismissing your concerns but I believe youre overreacting a little is all&hellip, Overreacting? I dont think so Paul. If it was the shoe on the other foot you wouldnt feel the same Im sure Tara Ferguson replied to her husband....
Hello.. I want to tell you about how i started to breastfeed my stepson and start to have new lovely bond with him till now. Before let me introduce myself. Myself riya and i am my husband’s second wife. His first wife was actually my elder sister who had meet with an accident and expired so later on my family made me marry my sister’s husband only. He has teenage child shreyas who was now also my son. Days passed on and i gave birth to a baby boy. My relationship with my step son was not good....
IncestMy 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...
John, a straight forty-year-old, takes his eighteen-year-old gay stepson's virginity. To please his wife and bond with his stepson, John asks Aaron if he wants to learn some mechanics with him. As they have a nice moment together, John discovers something he had never felt before, a need hidden deep inside him. He's going to breed the young gay boy. New message from Sandra — Don’t forget what we talked about! Go talk to Aaron. Luv you. I read the text message from my wife and put...
GayMy 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...
... New message from Sandra — Don’t forget what we talked about! Go talk to Aaron. Luv you....I read the text message from my wife and put back the phone in my pocket. Aaron was her son. After living with his father for a few years when he was a teenager, he came back to his mom’s at the beginning of the summer, as we were living closer to his college.I never had children with my first wife, so kids were not my specialty. Well, he was eighteen, so not really a kid anymore, but still, we barely...
Gay MaleHi Y’allMany people have commented on my last story of an amazing random cock I sucked while on vacation. The main private comments I received were wondering if my stepson tried anything with me while I was in Utah and he was joining us from 29 Palms where he is stationed. I’ve been reluctant to say anything but have to admit we did have a little fun. The first time something happened during the trip we were sitting in a cabin we had rented outside of Capitol Reef National Park. I was in the...
I’ve been married to my husband nearly three years now, I’m 28 and he is 45, I was probably the cause of his marriage break up with being his secretary. He has a son and daughter 17 and 15 from his first marriage, which we often see, and I get along fine with.Four months back my husband suffered a stroke; he was paralysed from the waist down and needs a lot of help all the time. Jake my stepson came and stopped with us to help look after his father. Jake is used to having girls stop over at his...
A few days after Peggy broke the taboo ice by fucking her new stepson, she was anxious to share the event with Wanda, her college girlfriend. Wanda was the one person she could tell anything to and would not get any condemnation from. In fact, it was quite the opposite. She and Wanda had an unspoken competition between them. Each wanted to outdo the other with the dirtiest stories and nastiest desires. There was always a hazy line between what was real and what was fiction between these two....
“Can we do it again soon Sarah? I would love to have your man and you could have mine,” Lara whispered as I escorted her and her man to the car park. “Would love to soon, very soon,” I whispered back as we kissed goodbye. “And perhaps just you and one of you girlfriends one day soon?” You can read all about that encounter in my story SARAH WATCHES ANOTHER MAN HAVE HER MAN. Three weeks later while my man is away, and by coincidence hers, Lara has invited me to her condo to meet Joyce at two...
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...
This story is a work of fiction. Jack off and enjoy!My stepson Bobby jacked off a lot. And I mean a lot! Even for a boy his age.I had been married to his mother for about two years and had watched him mature and grow. Of course he was at the horny stage and although he hid it well I knew he never had sex far from his mind. Nobody at that age ever does.And I knew why Bobby was spending so much time in the bathroom and in his bedroom in the afternoons. I knew what was going on. I did the same...
I was putting all my stuff into big cardboard boxes, when I heard the doorbell. I grabbed a towel and wiped all the sweat off my face, and then headed to open the door. “Hi,” the young man standing in front of me said, “Mandy,” he finished, calling me by my name. It was my stepson, Johnny. He never called me mom or stepmom. For him, I was just a woman his dad fucked a couple of times and then decided to get married. I married his dad seven months earlier, but I met Johnny ten months earlier. He...
TabooIt was a hot afternoon and after finishing all the housework, I was watching TV in the living room. My husband, Robert, was at work, and I was all alone in the house. My stepson, Edward, lived in the hostel since he was ten years old. The last time he came to meet us was at his nineteenth birthday, which was two months earlier. A year earlier, when I married Edward’s dad, I started noticing that Edward had some dirty feeling about me. He never accepted me as his mother, but I guessed he wanted...
TabooSTEPSON BECOMES MOMMY’S MAIDJeanette Stewart was a very beautiful, big & sexy woman. She oozed sex from every pore & men all but dribbled in her presence when they gazed longingly at her tall, curvy frame. She had large, firm breast that she liked to show off in all those low-cut tops she always seemed to wear. Her slim waist tapered into sexily curving hips, her bottom was full & round with meaty cheeks that squirmed as she walked under those tight skirts. Her legs was long &...
I awoke last Friday morning to the sound of my dogs barking to be let out, I laid in bed thinking that my husband would let them out as today was my 50th birthday and he had promised me a sleep in and something special as a present. After what seemed forever the dogs were still barking so I angrily threw off the covers and not bothering to put on my house coat wandered through the house in just the long t-shirt that I always wear to sleep, not finding my husband I let the dogs out and went to...
My Stepson, My Slave- My Stepson, My Slave- Beth had thought about it for the almost six straight weeks since her husband told her that he was being sent overseas to help launch his companies operations in Mongolia. He was an MBA-trained geologist who often had to travel abroad to survey the rocks and minerals that were his company's livelihood. What was different this time was that he would be gone a year and that the place he was going to was so remote and barren that it really...
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...
My name, by the way, is Kimberly and I am the reporter for this story. This story is based what was told to me by the son and his stepmother. There is another story about when I come into the picture and that is when the stepson, Randy later on wants to marry me. Then I have do decide whether I am willing to marry someone who wants to retain his sexual relationship with his stepmother. Of course, I was shocked when Randy told me about his unnatural relationship with his stepmother. ...
“Dane, wake up, or you are going to be late for your classes,” I said calling my eighteen-year-old son from the kitchen. “And Jenny, hurry up, honey, Megan just called for you again,” I said to my twenty-year-old daughter who was in shower from past twenty minutes. I guess she was masturbating in shower. Dane was my stepson while Jenny was my real daughter. I married Dan’s dad two years ago. I married him because had same life, same choices but he was full of money too, and I thought for me and...
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...
This is my second marraige and my husband and I always fantasized about somebody watching us fool around. I had never really thought about showing my body off in the past years but my husband prompted me to do something one night recently that really got me started and already i find myself wearing sexier clothes to work and shopping. My husband was married before and has a 22 year stepson from his first wife. Things weren't going well for him since the company he worked for closed down and...
ExhibitionismPeggy was now in full MILF Slut mode. A week or so back she broke all norms by seducing and then fucking her stepson, Steve. It happened innocently enough, she thought to herself, but it would never have happened if she had been more careful. If she had just made sure her bedroom door was closed during her morning ritual of masturbating on her bed, then Steve would not have innocently seen her playing with herself. Events then took a new course and she ended up with his lovely young erection...
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...
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...
Stepson losing virginity to step mum. Pt1 I had just finished dinner with my step mom gale, as my father was still away on a work trip. Dad had just met her a year ago and they quickly got married. Gale was 40, 5-11 brunette with brown eyes and a voluptuous figure. Her ass was round and plump with a slim waist and flat belly, she worked out a lot. Then the tits omg her tits made me so hard, two huge double d's. Ohh how she must of caught me looking every time we talk. She has these beautiful...
I'm susan,35, pretty and i have a very nice body for a 35 year old. I am married to john,50. It was my first marriage and his second. we've been married for just 2 years now. John and his first wife are divorced. john has a beautiful son,Greg, who is 18 years old. he's tall and slightly built. He's a football player and a very active boy. he also loves motorbike racing.I have always wanted to fuck a 18 year old. Young studs got a lot of stamina and unlike my weak 50 year old hubby, they can...
Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...
How I came to meet my GF, and eventually her Daughter and Stepson......who now live with meMy situation began when after a divorce, I was in need of a place to live for a while. On the suggestion of a mutual aquaintance I spoke with a lady under his employ, who might be able to accomodate me for a while. We talked briefly and she offered to let me stay at her place, as her two c***dren were at friends for the summer in Baltimore MD. I followed her home after she finished work and she welcomed...
I am Saroja, 35, pretty and I have a very nice body for a 35 year old. I am married to my husband, businessman aged 44. We have been married for 10 years now. We have two daughters and both have been put in a convent hostel for their better studies. Last year, my elder sister’s son came to stay with us on his job for a short period. Sathish, who is 24 years old, is tall and slightly built. He’s a football player and a very active boy. He also loves motorbike racing…Of late I got likening to get...
IncestAfter the incident of the face painting orgy on the basketball court by her stepson and his buddies, Peggy had to take a break from the boys for a day or two. It had been a surreal, totally spontaneous, and wonderfully sordid event. She loved the eroticism but felt it would be awkward to be around them so soon after it happened. So, Peggy called Wanda. She just had to meet up and tell her partner in ‘Prurient Interests’ her recent tales about the boys. Wanda was a friend from college, who...
After the incident of the face painting orgy on the basketball court by her stepson and his buddies, Peggy had to take a break from the boys for a day or two. It had been a surreal, totally spontaneous, and erotic event. She loved the eroticism but felt it would be awkward to be around them so soon after it happened, so Peggy called Wanda. She just had to meet up and tell her partner in ‘Prurient Interests’ her latest tales about the boys. Wanda was a friend from college, who never married,...
Note : This story is completely fictional! I'm susan,35, pretty and i have a very nice body for a 35 year old. I am married to john,50. It was my first marriage and his second. we've been married for just 2 years now. John and his first wife are divorced. john has a beautiful son,Greg, who is 18 years old. he's tall and slightly built. He's a football player and a very active boy. he also loves motorbike racing. I have always wanted to fuck a 18 year old. Young studs got a lot of stamina and...
IncestPart 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...
It was . It was an arranged marriage. Things happened so quickly that we didn’t even get much time to get introduced to each other, leave alone knowing about my horny stepson. We got engaged the same day we first met and got married in two weeks. I didn’t want to have sex with him that night. But he was in a real mood. He didn’t even listen to me. He just ripped my saree, pinned me against the wall. He drilled my pussy for 30 minutes and sprayed his creamy juice all over my ass. I went to the...
IncestSISSY 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...
“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...
IncestSissy Prudence (Part 2) (by Sissy Caroline 22 December 2006) Section 1 "Prudence. Come here at once." Dressed in his maid's uniform, Prudence walked obediently into the room and then knelt down before his mother, his eyes lowered to her feet. He knew he was in trouble because she had called him Prudence. "I have just been talking to Mrs. Smithton, who tells me that she is increasingly concerned about the quality of your work when you are supposed to be performing maid duties...
SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....
Sissy Prudence (Part 3) (by Sissy Caroline) Section 1 "That's our Sissy Prudence in the garden. Isn't he a delight?" Bridget looked out the window and, despite the fact that boys were not really her interest, she found the sight presented to her was quite exciting. She had never thought that a boy in a dress could be such an erotic fantasy. Prue was working in the garden, which was something he now really enjoyed as a break from his duties inside the house. Not that he was...
SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...
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...
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."...
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...
the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...
part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...
Sissy Prudence (Part 5) (by Sissy Caroline) Section 1 It had to be measured perfectly accurately and it was. The two halves slipped together easily and the joins were virtually invisible. About a half inch wide and a quarter inch thick, the collar now fastened permanently around the sissy's neck was gold in appearance and as difficult to cut and remove as the collar that had been fastened around his scrotum some time ago. A small silver panel glued to the front was engraved...
Sissy Prudence (Part 4) (by Sissy Caroline) Section 1 "Control, discipline and dependence are all very closely linked Jennifer. Ultimately we want him to be totally dependent on us and we use discipline and other means of control to help us achieve that state of dependence. Although you should be very pleased with progress, he is a long way yet from where he could be as we have discussed previously." "I know that you're right Janice. I love the way he has responded so far but...