Sissy Sierra free porn video

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SISSY SIERRA by Throne Connie called out from the den, "Sierra, the girls and I are waiting for you." In the hallway, her husband stood still, hugging himself. The last thing Seymour wanted to do was go in there and have his wife and her three friends see him. It was bad enough that, several months ago, she had made him legally change his given name from Steven to Seymour, just because she thought the new one was funny. After that she had begun sissifying him in earnest. First she had made him have all his body hair removed. It wasn't until after it was done that she casually mentioned that the process was permanent. Then she had started making him wear lingerie around the house, and under this clothes when he went to work. It was so humiliating to have her see him in lacy panties and filmy, short nighties. All day in the office he was aware that, unseen by others, he had on bikini-cut panties and stay-up stockings. Now, however, he was naked. His wife had made him put blush on his cheeks and apply bright pink lipstick to his mouth, along with using mascara on his lashes and liner around his eyes. He hated having to look so unmanly. But Connie, with her cute face and sexy figure, was domineering and took real pleasure in controlling him. He had tried to reason with her recently and she surprised him by saying she would consider his grievances. But now she wanted him to expose himself to her likeminded friends. Seymour knew that hesitating too long would only make his situation worse. He pulled back his narrow shoulders, sucked in his soft belly, and tried to look less scared than he felt. As he entered the room he saw the other women sitting there, two on the sofa and one on the recliner. They laughed and clapped at the sight of him. His limited resolve melted away and he automatically assumed the body language and gait his bride preferred. As they watched, he put his arms out slightly to the sides, wrists limp. His steps grew short and mincing. He even remembered to raise his chin a bit and push out his lower lip. The two females on the sofa were Rona and Arlene. Over on the recliner was Trish. Rona pointed at his undersized penis and chortled. Arlene imitated his limp-wristed look without rising. Trish sat there and rocked her hips side to side to mirror his way of walking. They each had a glass of wine by their side, and there were several bottles present, all of them half empty or more. Seymour shuddered inside. Connie was standing at the far end of the room. With a smirk on her pretty features she said, "There he is. My big strong man, Steven. I mean Seymour. Except that he's such a pansy that now I have to call him Sierra. But you know, girls, I think he secretly likes it." "Yeah," said Rona. "He couldn't make it as a man, so now he wants to be a sissy." "Agreed," Arlene seconded. "With that tiny dick he could never satisfy you, Connie." "Or any woman," added Trish. Connie took her stemmed glass in hand. She raised it and the others did the same. Seymour's wife said, "To the man of the house, who sure isn't any kind of a man." She sat herself in an armchair across from the sofa. The beleaguered husband turned awkwardly one way and another but in any direction he was still mortifyingly exposed. "So, Sierra," Connie told him, "I said I was going to think about your endless complaints. And I did. I also consulted my friends here to help me come up with some solutions. I think our ideas will make you happy. Are you excited to find out what we're going to do for you?" He looked neither happy or excited. Even so, not wanting to upset her, he nodded mutely. She gave him a big wink. "First of all," his bride went on, "you fussed about not having anything on your bottom. Or should I say, your cute, soft, girly bottom?" She smiled. "Well, Rona came up with the solution to that." He watched unhappily as Rona moved to a wooden chair, taking her copious shoulder bag with her. She reached inside and produced a wooden, sorority-initiation-type paddle. Seymour bit his lips and tasted fruit- flavored lipstick. She summoned him over with a wagging index finger. He went reluctantly and then had to stretch himself over her warm lap. It made him uneasy to have his hips across her firm thighs. Connie didn't allow him intercourse and only occasionally permitted him to ejaculate, making sure it was under shameful circumstances. Seymour was perpetually horny. He lay there with his bare bottom upturned. Rona raised the paddle and brought it down hard. Seymour let out a high-pitched wail. She didn't hold back and soon had him thrashing and crying. It was easy for her to keep him in place with one hand on the small of his back. The others watched avidly as his backside turned rosy and then red. She didn't stop until it was starting to swell. Then she made him get up, walk around the room -- again taking dainty steps, although they were stiffer from the pain in his rump -- and show each of the seated women what an effective job she had done. "There you go," Connie announced. "Now you have something on your bottom. A cheery glow. So let's move on to your next gripe. You keep telling me how I shouldn't make fun of your itty bitty dicky. Don't mock the half-a- cock. Fine. Arlene found a simple fix for that. Why don't you go over to her so she can give you what you want?" He put himself in front of Arlene, fearing the worst. She reached into her smaller bag and came out with -- oh no -- he knew what it was -- a chastity device. It was a short pink tube made of plastic, with the accompanying ring and a small red padlock in the shape of a heart. She took her time donning gloves of thin latex, letting him suffer anticipation of what was to come. Then she fitted the ring over his genitals, working each of his testicles through it one at a time. When it was in place she next worked the tube onto his penis. Even as short and slender as his organ was, this was still a snug fit. Then she held up the lock for him to get a good look at. He couldn't suppress a whimper. She got the lock in place. "Now I want you to participate. After all, you're the one who wants that little bugger covered up. So give the lock a squeeze and close it. Let me hear it click shut." He did it. The females were all silent so that they got to hear the sound that signaled his penile imprisonment. Arlene reached up to fiddle with his nipples. It felt strange with her fingertips encased in the thin rubber. He shifted his feet and moaned. His confined male part tried in vain to erect. And his bottom still burned. The pain and stimulation and frustration all got mixed together in his mind, a preview of what he could expect if his wife made a regular practice of punishing and teasing him while he was locked. Seymour fully expected her to do that. "Now, Sierra," Arlene said, using that sissy name he disliked so much, "I'll just give the key to your lovely wife, who I'm sure will take very good care of it. This way she'll have it whenever she's in the mood to unlock you. Which I'm sure she'll want to do all the time. So you two can have sex. Or did she tell us all that the only sex you have is with your face between her thighs? Oops. At least that will save her the bother of using the key. Maybe she can just wear it on a slim chain around her neck, so you'll see it every time you admire her cleavage. Or would you rather she hang it on an ankle bracelet? Maybe if it was down there, you'd develop a fun foot fetish. Isn't you life exciting?" He could only stand there, biting his lips and sniffling, wondering what came next. Without being told to, he turned toward Trish. She looked at Connie and asked, "What was Sierra's other grumble?" "The poor thing didn't want to have to make herself pretty with cosmetics. Isn't that ridiculous for a sissy to dislike?" "You know, it can be time consuming. So no problem. We all want to make her life easier." Like the others she had something for him in her bag. "That's why I got this." Out came a rubber mask, a full-head one that zipped up the back. The face was exaggeratedly female, with wide, overly decorated eyes, a pert nose, and plumped-up lips. He saw that the pupils of the blue eyes were small holes, as were the nostrils. The mouth was slightly open as well. Trish stood and adjusted it over his head. He smelled the rubber as she smoothed it down. Then she zipped the back closed, being careful not to catch his hair. It even covered his neck. In seconds his face was getting hot, starting to perspire. "Isn't that adorable?" Trish wanted to know. "And now you can't forget all that bothersome make-up. Swish around the room and give everyone a close-up look, Sierra. Go on, sweet cheeks." The pain in his bottom penetrated more deeply. His nipples still tingled from being teased. His cock was cramped in its pink plastic penis prison. He felt his balls begin to throb. He was already blinking from sweat that got into his eyes. Seymour groaned miserably. Following Trish's order, he went to each of the ladies. At every stop they had him bend forward, supposedly so they could get a better view of his new face, but actually so they could finger his receptive nipples. He wriggled with nervous energy as he circled the room several times. They felt his rear end, marveling at how warm it still was. Rona gave it a few nasty pinches. Arlene caressed his scrotum in her still-gloved hand. Trish directed several air kisses to the mask's perpetually puckered lips. She stuck her index finger through the mouth hole and made him suck it, then used the wet tip to stimulate each of his nipples. "There you go," summarized Connie. "All of your gripes have been dealt with. You must be thrilled, Sienna. Aren't you?" From behind the artificial lips, his voice slightly muffled, he answered, "Yes, dear." Just to be safe he added. "Thank you, Connie." Looking at the others he added, "Thank you all." "But," his wife went on, "I didn't want to be the only one without a gift for you. After all, you're my personal, all-purpose sissy. I'm having so much fun with your ongoing makeover. I get excited each time you become less male and more wimpy, wispy and womanly. So let's see what I have in this side table at the end of the sofa. What could it be? Hmmm?" She opened the drawer, reached in, and came out with -- oh no! -- a glittery silver tiara. It was metal but covered with some sort of cheap fake gemstones that caught and reflected the light. Connie forced it on above his eyes. The sparkly headpiece was much too tight. It squeezed the sides of his skull uncomfortably, pressed against his forehead like some medieval punishment device. She chuckled and patted him on top of his rubber-covered head. He peered at her through the tiny vision holes, his eyes stinging from sweat, vision distorted to make her appear fiendish. His nose started to run. Connie squeezed the soft flesh on either side of his hairless chest. "You know," she said thoughtfully, "the next logical step might be to get my Sierra some perky little breasts. Nothing too showy. She could hide them under her boy clothes at work. Or maybe wear a training bra every day. How would you feel about that, my yummy sissy missy?" "I... don't want boobies," he protested ineffectually, the rubber pressing against his lips and deforming the words. "Did you hear that, girls?" Connie said gleefully. "My squishy sissy husband wants bubbies. I knew that once I pushed him far enough he'd discover his true pansy personality and understand that whatever I want for him is what he wants, too." She cupped his chin in her hand and made sure he was staring at her when she went on, "And that tiara isn't just a pretty gift, darling. It's also to help you remember your new name. You didn't like what I was calling you so, instead of Sierra, from now on you'll answer to 'Tiara'. I know you're delighted by that. Aren't you, honey buns?" "I... I'm... so happy with my new name. I want to be called Tiara all the time. Thank you, dearest. And I'm sure you'll think of plenty more to do to me. Or rather, to do for me." "Oh yes," she said with confidence. "I'm sure I'll never run out of ideas for what to do to my sissy husband Tiara. Never ever. You can be certain of that." ********* (Just a quick little something I couldn't resist writing. Hope you liked it.)

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Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

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...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

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

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

1 year 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
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....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. 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 portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Gets A Black Master

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

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

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...

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