Sissy Stepson: Part 6 - Caroline's Sissification free porn video

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Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I will show it to your father if you don't cooperate!" Mrs. Monet angrily demanded. "From now on your name is Caroline, when you father is home you may wear your boy clothes and act like Carl, but until then you will wear sissy attire after school and all weekend, is that understood fag boy!" "Yes, ma'am, can I change into something else?" Caroline meekly asked. "No, leave my cum stained clothes on, but I will let you wear something over underwear, follow me," she sternly said. Caroline followed her dominant stepmother to her room where she picked out a pink slip for her sissy to wear. Caroline slips into the slip and became hard again and Mrs. Monet began laughing at the pathetic sissy. "Look your sissy cream is staining the slip and your getting turned on again," she laughing said to her pathetic sissy boy. She sat on the edge of the bed and order sissy Caroline to unlace her shoes and as he did she berated him, "What a pathetic sissy, you're just happy to be dressed in sissy attire. Look how horny you're getting unlacing my shoes. I bet you would like to put on a tight fitting skirt and silky blouse, would you little pervert?" Caroline stammered, "Yes, mommy, please I love dressing like a sissy, I really want to try on a skirt and a blouse." "Hmm, if I let you wear a blouse and skirt you must be disciplined with the hairbrush!" she said sternly. "Oh, I know, I will have to be punished, but it's worth it," said Caroline in a girlish voice. After Caroline was finished with unlacing the shoes Mrs. Monet picked out a tight fitting knee length pink skirt and bright pink frilly lace see through blouse and gave it to the sissy. Caroline was in heaven as putting on the blouse and the skirt, he had to squeeze into the skirt. Caroline's stepmother next made her sit on her lap as she applied gaudy eye shadow, rosy rouge and ruby red lipstick to her stepson. She fixes the sissy's hair with hair spray and clips to flip it up. She looked like a feminized boy, almost a girl but not quite. She noticed his bulging skirt and commented, "That's not very lady like. I think you should get across my knee and take your punishment like a good sissy." Caroline laid across her mothers nylon clad legs and began receiving hard cracks with the hairbrush. "Take that you slut little bitch, wearing my nylons, heels, panties, bras and know my skirt and blouse with make up and a wig!" The sissy was wriggling with pleasure and began crying out, "I am such a slut, I am sorry I wore your things, I can't help it, make me your sissy stepson!" One more, whack and Caroline was once again over the edge shooting gobs of gooey sissy cream all over her stepmothers well stained pantyhose and bleeding through the panties slip and even the skirt. Mrs. Monet again pushed her faggot stepson to the floor and took more pictures. She then ordered the sissy to take off her cum covered clothes and put them in a pink sissy laundry hamper. She then orders Caroline to shower and shave all his hair off and then come to her bedroom before bed. Caroline goes naked to his stepmother's room where she hands the sissy a sheer pink silky see-through negligee and Caroline becomes hard immediately. Mrs. Monet is determined to milk her sissy of all desire to play with him self. Caroline's stepmother grabs a couple of packages of sheer knee high stockings and she lifts up the negligee and puts the knee high over Caroline's sissy stick and pathetic balls. The elastic of the knee high cause the sissy's balls and cock to swell. Caroline is shocked when his stepmother begins masturbating him and she begins humiliating him by saying, "Come on you pathetic sissy you are going to shoot your sissy cream in the knee high and then I am going to make you eat it." Caroline was aghast and excited at the prospect of eating sissy cream. Mrs. Monet rubbed the nylon cover cock and balls, first cupping the sissy balls and then rubbing the shaft. Caroline was once again entranced with being a sissy and she began cooing, "Oh, mommy I love this my sissy clit feels so good in your knee high, I want to shoot my sissy cream so badly, please make me eat it." With one more stroke of her soft hand Mrs. Monet sent here sissy stepson over the edge he came gobs into the end of the knee high. The sissy cream collected in the very end of the nylon and translucent girl juice seeped through the outside end of the nylon. Caroline's stepmother gentle squeezed the effeminized sissy's balls very gentle to extract the rest of the sissy cream. She gentle took the knee high off and gave it her sissy and said, "Go ahead, eat up there's a lot more of that, we are going to keep going until you are milked dry." Mrs. Monet then immediately put another knee high on the sissy's while Caroline slowly licked the girl cream out the nylon. "How does it taste?" asked Caroline's stepmother. "It tastes salty, warm and creamy. I would like to try more sissy cream." "No problem, I bet you would like to another sissy's stick or a real mans cock!" Mrs. Monet said. Sissy Caroline answered, "Ah, I guess, I would try with another sissy?" "Well for now, you can eat your own cum and I will get you a dildo to practice cock sucking," sly said Caroline's dominant stepmother. That night Caroline went through six knee high's before being totally milked and sent to her room to sleep. Mrs. Monet repeated this activity all weekend, forcing Caroline to be begged to be spanked. Caroline was usually spanked and came two or three times a day and then milked at night between four and eight times. She continued to get sissy cream all over her stepmother's stockings, shoes, panties, slips, dresses, skirts and negligees. Here hamper was rapidly filling up with sissy cream stained clothes. Everyday was a different outfit. During the school week Caroline was spanked and came only once but was milked and feed cum up to ten times at night. She began training for cock sucking on a 10 inch dildo that her mother purchased with a squirter that she used to put Caroline's cum into. When she sucked it well she got a mouthful of cum. Caroline was approaching another weekend with a surprise from Step mommy!

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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...

Incest
4 years ago
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Sissy School Part 3

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

2 years ago
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Sissy Teaches Me Part Two

“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...

Incest
3 years ago
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Sissy Prudence Part 2

Sissy 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...

1 year ago
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Sissy School Part 5

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....

3 years ago
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Sissy Prudence Part 3

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...

3 years ago
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Sissy School Part 2

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...

3 years ago
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Sissy School Part 6

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

3 years ago
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Sissy 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."...

4 years ago
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Sissy dannis birthday party

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...

3 years ago
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Sissy discovers Part 4

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...

3 years ago
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Sissy discovers Part 3

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...

3 years ago
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Sissy Prudence Part 5

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...

1 year ago
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Sissy Prudence Part 4

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...

1 year ago
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Sissy Biker Chick Part 2

Sissy Biker Chick Part 2 Jolene drove me to Gus's place not saying a word except when she dropped me off on the porch of a run down ranch house "Good luck....you're gunna need it!" was her parting remark smirking. I watched her drive off in a haze of dust and wondered what the next month would entail. Timidly I knocked on the door "Get in here bitch," was the shouted reply. I was not sure it the shout was at me or someone else so I knocked again "Dumb faggot quit banging and...

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