Sissy Discovers (Part 3) free porn video

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part 3 of an original story

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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 look on and snicker as Tom is rubbing Vicky’s ass and she playfully pulls away.

Vicky coos “now behave Tom”

He whispers into her ear and she smiles and gives him a peck on the cheek.

The k**s are giggling and under the table Sissy is poking Brad with her foot.

Tom leaves the room, shortly followed by Vicky

On her way out she reminds the k**s to finish cleaning and asks if they want to watch a movie later.

Not me Sissy says – “I’m gong to go for a walk to the dock and look at the moon.”

The brother and sister are left in the now quite room.

Brad looks at her and asks, “a walk to look at the moon, really?”

Ignoring him Sissy picks up her plate and finishes loading the dishwasher.

She turns to Brad and asks , “What was up with Mom and Dad? Did you see how they took off out of here?”

“Huh?” Brad looks at her funny

She gets a mischievous look, and grabs Brad hand to pull him behind her. They slip trough the large open den and kitchen area out onto the porch. It is a long covered deck that runs the length of the back of the cottage and faces the water. It also goes past their parent’s bed room.

Sissy had noticed before that her parents did not always close the blinds when they were in there and she had seen them in some compromising positions by accident before. She had an idea of what mom and dad were up to.

Sissy edges to the window that is open and in the dusk of the evening the frogs are chirping at full sound, but a different kind of a****l noise was coming from the bedroom. Sissy kneels down and peers into the room with Brad, full of curiosity, leaning over her to peek in too.

Sounds of lovemaking drift out of the room.

Sissy turns and looks up at brad with a big grin. Brad looks down at her face and then his eyes drift a degree from her face to look down her top. She notices it, but turns away to see in the dim light her moms head in their father lap.

Vicky is kneeling at the end of the bed sucking on their father’s dick.

They watch with mouths agape – but they can’t turn away. Brad has never seen live sex before – and never thought it would be like this. Sissy is shocked too, because she has seen them scamper about in little or no clothes like k**s but did not expect to see her father’s dick being sucked up into their mom’s mouth.

Vicky knows what she is doing. The slurping sound is audible but she is not just going down on him, she is working her tongue over the top of his large head, and slowly pumping the large shaft with one hand while cupping his balls with the other. The tip of her tongue stops on his pee hole and flicks back and forth. Tom groans and sighs.

“You know I like that, but slow down or this old man is going to give you a surprise early” he whispers.

Sissy can see the male family resemblance. Tom’s dick is large. It is ever bit the size of Brad’s cock.

Vicky smiles and stands up. Her shirt is already open and her shorts are on the floor. She has a great body at 45 because of a religious commitment to workouts and yoga; she is tone and no hint of sag. She drops her shirt on the floor and undoes her bra to let out her nice 36 D-cup tits. Tom leans forward the give them a gentle squeeze then pulls her close to put one boob right into his open mouth.

Sissy and Brad wrinkle their face in disgust, and then giggle, then turn to stare in fascination as their parents are going at it.

Brad leans close for a better look and his dick in his shorts is rubbing on sissy’s back. She feels it but ignores him for the moment.

The couple in the room change positions and the k**s pulls back afraid they will be seen. Sissy uses this movement to “accidentally” brush Brad’s straining dick with her right boob. She can’t believe she just did that on purpose, but she is beginning to enjoy her game of teasing , and the pace of sexual thoughts from the past 24 hours is building up to something.

Brad moves to give her more room, but they both turn back to the show in the bedroom.

Vicky has moved Tom onto the ottoman at the end of the bed, and is giving him a kind of lap dance with her ass rubbing his large cock and sliding her ass up and down it without putting it in. It is a little difficult to see what is going on from their vantage point and the room is dimly lit. but the sounds are unmistakable and the k**s can tell it feels good to both parties.

Brad moves to one side to see better and Sissy gets behind him. She intentionally rubs her tits barely held inside her thin camisole on the back of Brad’s head. He pretends not to notice. As he is crouching, she can see the head of his dick peeking out of the shorts. Her hand on his shoulder as they watch the parent fuck slides down his arm absentmindedly. Brad is breathing hard. Sissy is breathing hard.

The parents have changed position again and are getting more animated, and a few giggles and shushes to be quite drift out of the room. Vicky is now straddling Tom and his large cock is sliding in her pussy. She is expertly lifting her self up and down on his shaft while rocking her ass. The k**s can see his big cock disappear inside Vicky’s pussy lips as they strain to wrap around the large shaft. Sissy notes that this is why they are on the ottoman so she could use her legs to control the pumping. She moves in a slow but steady unhurried pace. Damn they are good she thinks.

Sissy slides her hand to Brad’s leg. Brad leans back into her boobs more and his eyes become droopy. The parents are fucking

Sissy leans into whisper into Brads ear “This is crazy – look at them go!”

Brad, “yeah – it is crazy.” This is sick too he thinks, but he does not get up or look away.

“Are you getting horny?” She breathes into his ear – trying to make no more noise than the frogs.

“Damn Sissy – leave me alone” he says a little too loud. They pull back form the window and listen, but nothing in the room changes, and a feint creaking sound continues from the floorboards of the old cabin.

Brad and Sissy are facing each other, but Brad is standing and Sissy is crouched down. She looks up to his face and he has a sheepish look. She can see his pants are straining. “awe - look at your little wienie”

Brad rolls his eyes and quieter this time mouths “Fuck you”

“That’s OK. You have raging teenage hormones” – she teases
His cock is inches from her mouth; she imagines that it is leaking out some clear sweet pre cum. She resists the urge to reach out and touch him – she is not ready to cross that line, and she does not know what Brad would do anyway.

She looks in the room and Mom is stroking her dad’s dick. She has it pointed at her chest like a porn movie.

“Damn” Sissy mutters. Brad is speechless

Sissy makes a decision to follow her own a****l instincts and reaches up Brad’s leg and tentatively touches his dick through his shorts. He looks back at her with surprise. He is really speechless now. He starts to protest knowing this is wrong, but he has also dreamed of her touch a hundred times. How can he say no now?

She traces the outline of the long shaft and rubs along the ridge showing through the thick shorts. Then with a smile begins to match the pace of the stroking in the room with her fingernails sliding on the course fabric of his shorts.

Brad is frozen like a deer, he is nearly panting. Sissy has turned back to look into the room, but Brad has his back to the wall and dares not move for fear of stopping this unbelievable moment. He looks down at Sissy’s hand and then to her breasts heaving under the camisole top. It is still covering them completely, but in the dim light he can see the outline of her nipples that have grown into hard points under the fabric.

They hear more moaning in the room and turn back to see Tom getting ready to cum on his wife’s tits. Only Sissy is watching, with her mouth slightly open and air rushing over her teeth. She has not stopped with the stroking and is rubbing a little harder now through the shorts. If there had been more light she would have seen the wet spot growing on his shorts from the pre cum she imagined earlier.

Gaining some courage Brad reaches over to her shoulder the rubs it like he is giving her a massage. Sissy is relieved at this sign from him, because she was half expecting him to scream when she touched his dick and go running away from her. She looks up at him and gives him a knowing grin. He has not moved an inch. She rubs just a little harder, but not too hard. She has another idea.

New sounds come from the open window now and she looks back into the room to see several streams of cum spatter on her mom’s perfectly shaped tits. Even in the light from the table lamp across the room Sissy can see it is a lot of cum from the shinny reflection pools forming on the floor as it slides off of Vicky’s round breasts. Sissy gives Brads dick a healthy squeeze and they take the signal to go before they are found out, and scamper off to Brad’s room with Sissy in the lead and Brad in tow.




Sissy pulls Brad into his bedroom. It has pine paneled walls with a bookcase on one wall, and a large window looking into the woods on the other. Along with the bed is a small couch and low table in front of it. Every thing looks comfortable and well used.

They are holding hands laughing, when Sissy suddenly gives Brad a little kiss as they stand in the middle of the room. Then she kisses him again parting his lips with her tongue.

She playfully rubs his cock through the shorts with her fingernails. Brad is trying to believe what is happening at this moment. Fantasies never come true – but here he is with his sister who he has dreamed of and wacked-off in her panties a hundred times. Now that it is here, and she is touching his cock – he is not sure what he should do.

The kissing has an effect of calming him and he starts fumbling with her tits through her camisole. They feel just like he imagined, soft and yet somehow firm. Her nipples are pointing into his palms. He moves one hand down her back, grabbing her firm teen ass through soft shorts.

Sissy has not thought through what will happen next with her brother, but she has a bubbly feeling of excitement inside her as she decides to take control and moves Brad to the sofa. This is completely wrong, it is taboo in almost every culture in the world, and it makes her shiver with excitement.

Letting her more base instincts control her hands, she starts pulling down his shorts while pushing him down to sit. He is on the couch with shorts around his ankles looking uncomfortable and goofy with a tent in his underwear.

He stares up at her standing in front of him…..Sissy was gliding her hands over her body.

Brad mumbled, “Damn Sissy… what…” “Shush “ she cut him off

Sissy purrs, “I know you look at me … you horny baby. I’ve seen you peek.”
As she says this her hands stop on her breast and push them up nearly pushing them out of her camisole.

Brad looks away then looks back and smiles.

Sissy asks “ So how long have you have been jerking off on my panties?”

“What do you mean?” he asks out of reflex. He was embarrassed and never planed to ever tell anyone about his obsession with his sister……but as he looks at his sister, he sees she is not mad.

Ummm …you know about that huh?” sheepishly admitting he is caught

She walks over to Brad and rubs his head – “yeah that’s ok lil-brother… I saw you sneak out of my room Thursday night” Then teasing “ I also saw you make a mess of my blue polka-dot thong with that load of jizz.” She is intentionally talking dirty to him.

His head hung muttering “oh god”

“Awe, don’t worry.” She lifted his chin with her finger. “I liked it.

“I was watching from the door, and I saw that monster you’ve been hiding.”

As she talks she kneels down facing him on the couch and straddles him as she ruffles his blond head of hair. She is close, her chest is only inches from his face and the smell of soap from her shower is drifting around him.

As she sits in his lap, his aching cock is trapped by her crotch. He may just explode right now, but he is too frightened by all this and how wrong it is to have his sister sitting on his dick….. he can’t move….

As he looks down he can see her shorts are stretched up and her thinly covered pussy is sitting right on his bent down throbbing tool. Wow he thinks this is a dream come true or a nightmare.

“You know … I played with myself while you where whacking off…. you’re the cutest brother …..and I can’t believe how much your little baby dick has grown.

He groaned at his sister’s joke, but noticed that as she said this she started to move her hips and grind her pussy on his cock.


She continued “I was surprised how hot it made me and then … and well seeing what we just saw” I’mmmmm just getting very horny from all this.”

“I mean aren’t you?” she asks

“Ummm well …. Sure I guess” , Brad answers, still unsure how to react to what is happening.

She pulls his head to her chest, flattening her tits with his face and says “Poor thing. I bet you are.”

Her grinding increases. And they both began to breathe a little harder.

Breaking out of his spell of culturally learned inhabitation – Brad’s hands move to his sisters hips and urged her movements on. Slowly he slid them up under her camisole and cupped a soft fragrant boob in each hand.

“Mmmm” she murmured. “I think you need a girl’s touch… let me help you baby.”

She dropped her hands into their touching crotches and slid them around his shaft, as she was rubbing her hips slowly back and forth. As she sits up his shorts were all twisted and the head of his dick is sliding out of the fly of his boxers. She pulls his shorts back so his cock is fully exposed.

She cooed in a baby voice “hi there fella’ … come out and play” She looked at the large swelling member between her legs. It bobbed up and down from the pulses of blood flowing into his dick, the head not quite touching her crotch. Brad tensed his dick muscles and his dick slapped her right in the pussy. They laughed at his skill.

Seeing how hard he was she got an idea to slow it down a little. So she got up from her brothers lap and sat down on the coffee table directly in facing him.

“Grab your cock for me baby” she ordered.

Reflexively Brad began stroking his dick. It was thick with blue veins in wandering paths up to his head that was glossy from the stretched skin.

Sissy stared at it. It was even larger up-close, must have been an inch longer than her largest lover she had had in her young and short sex life. 9 or 10 inches? It was nearly as long as her forearm. Damn she thought. What a beautiful cock.

Then out loud – “what a beautiful cock.”

Brad now fully into the moment says “Show me your tits” nodding at her chest.

Without hesitation – Sissy pulled her top over her head. Her soft straight blonde bob falls back around her face – and her lovely full breasts are staring right back at Brad’s large eyes.

He had never been this close to and staring at real tits. Always just a nip slip or down-blouse lucky glimpse. Of course he saw his mom’s boobs just fifteen minutes ago, but that was so shocking a scene it had hardly registered.

Brand says “ what beautiful tits.” With a smile at his little joke

Sissy leaned back on one arm and pulled her shorts to one side so Brad can see her light blue panties as she began to rub her swollen pussy lips and hunt for her clit with a stiff finger following a back and forth pattern she knew very well.

They are both are so horny she knows it will only be moments before they cum.
He looks like he is going to cum before her and she says “Not yet Brad. If you cum now I’m leaving and I won’t come back” with a smile.

“Let go of it baby – just watch me” Brad slows down the strokes and then moves his hands to his thighs. The cock is at attention and bobbing.

She pulled down her shorts, and staring directly at his dick and began to urgently rub her pussy right through panties. Her breath became ragged. She looked at his dick right when a thin gossamer filament of precum slowly lowered from the hole in the tip to the floor. Oh wow she thought.

She pulls her panties to one side now and exposes her pink shaved lips to him. A wet sticky sound began to rise like a snare drum beat from her hands hard work.

Brad is fascinated and leans forward.

“Rub my legs” she said huskily and stretched them over to his lap. Her feet just resting on either side of his throbbing dick. Brad began at her calfs and was soon leaning forward and rubbing inside her thighs while her hand was a blur.

He wanted to jerk off , but, he mostly wanted this not to end. So he waited to see what she would tell him next.

“Touch my tits” while she plays with herself, then she says “suck them” and Brad moves from squeezing them to licking and sucking them.

Sissy now has her brother leaning over her sucking her tit as she is about to rub herself to orgasm. His massive cock is pointing down and is so long that it is bent on her leg and he is rubbing it back and forth ignoring her earlier order to leave “it” alone.

Brad now has a nipple in his mouth for the first time since he was a baby. It is magic. Her boob is soft and slides out of his mouth because of his slobber, but booth of his hands are busy rubbing legs and holding him up. He hunts the hard fleshy bump with is tongue and begins to flick it up and down.

Sissy moans at this – so he continues keeping pace with her hand he can just see. She can feel the flood begin in her body. She keeps up the pace on her hard clit. It is burning now with the heat of blood in her pussy lips.

It comes over her in an instant, and wave after wave of heat heaves over her as she spasms and her body shakes several times so hard that Brad is startled and pulls back.

Man that was great and then out loud “ oh god. That was mmmmmm great baby….”

She rests back on her elbows and lets her head flop back for a moment. Brad sees her fingers are wet, then looks at her tits again and bends down again and sucks her nipple into his mouth.

Now on his knees if front of her on the coffee table, she reaches out and grabs his nude cock for the first time, and says” hmmmm let me see this big boy.”

He is still massively hard and so excited Sissy guesses he is about three strokes from an explosion of cum.

When she touches him, Brad feels a tingle move up from inside his dick trough his stomach and up his spine. It is electric.

She pushes him back sitting on the couch and kneels down in front of him.

She is gentle, forming a ring with her thumb and forefinger like an OK sign she starts at the base of his dick and slowly pulls all the way to the ridge of his head then tightening as she gets to the end and slowly pops her fingers over his head. A dribble of clear liquid oozes out of his dick and flows onto her hand.

As she moves her hand up and down on the shaft Brand’s face screwed up with an attempt to hold back the orgasm that was about to erupt out of the cock. She wants to play with him more but knows she can’t keep him from coming. She thinks about taking the head of his cock in her mouth, but maybe she thinks this is too weird already for a brother and sister. A little masturbation is not too back but blow jobs may be crossing the line.

His stomach muscles tense and sweat is beading up on his forehead. She stops for a moment. Waiting for him to calm a little, then gives him another stroke. The shaft of his dick is so large she can just get her fingers all the way around it. The skin pulls up over his head even though he is circumcised. She lets go of her grip and with her fingers traces the outline rim of his head and rubs the pre cum from his pee hole over the top of his dick.

She leans forward and pulls the cock toward her and then rubs his head on her right tit circling around until she zeros in on her nipple. Then she moves it to the other side and lingers on her nipple right below his pee hole in the cleft of his head. It is too much for Brad and she can feel spasms in the massive cock.

The cum bubbles out of his dick in white clumps that cover her nipple, then with out warning a massive steam of cum shoots up her breast laying a trail over her shoulder, then again this time rocketing off of her throat. She turns her head just in time to miss another shot that lands in her short cropped hair and cheek.

He has covered her in cum and he is still jerking with orgasms as a few more little spurts drop onto her chest. A laugh erupts out of her at the joy of controlling him and making him have such a large orgasm.

“Holy molly baby, that is a load!”

His body finally stopped shaking as he the last of his cum dribbled out. The loads, lumpy and thick, start to slide down her tits and left a series spots on her belly, blue panties and legs, the excess running down the sides of her boobs onto the floor.

Damn he thought – he had never cum so hard and so large a load…. Out loud he said “ god damn” His balls felt empty, and he knees were shaking.

Sissy is a mess, but reality of the moment and what they are doing drops like a cloud over the room. They look at each other and force a shaky grin at each other.

They untangle and check the door to be sure they are still alone. Sounds of a movie drift from the den. They look at each other standing in the room. Sissy wipes the runs of cum off her and blots the dark wet stains on her blue panties.

Sissy says again, “Wow – that was fun huh?” “Are you OK?”

Brad looks down at the floor – “It feels pretty strange.” “ Ummm but I really liked it”

She reaches to his limp dick and begins to fondle it.

He opens his mouth to say something, but she leans over to kiss him on the cheek and whispers in his ear.

“It’s alright. You need some experience. Just a little hand job”

“Sure” he replies and gently touches her nipples again as they stand facing each other in the center of the room.

Sissy smiles and says, “I have some limits though – we can’t fuck “

He grins and his young cock is already hard again and pressing against her leg.

She pushes him away with a smile and says “That’s enough education for now big boy….we have to get ready for the lake tomorrow.

She looks at him sternly, “Really, will you be OK? We can’t freak out on this…. I mean…. or tell anyone, right?

Brad nods and mumbles “No way s*s. I’m OK …. Just a little fool’n around right? Nothing too bad, but I mean I won’t say anything.”

She says “ and I want my polka dot panties back.” Laughing as she pulls her top on and walks out of the room.

Brad exhales staring at the empty space his sister has left in the room and mutters “ holy shit.”

to be continued...

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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."...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven 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 Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - 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...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sissy gets a black master

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

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm 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 Doctor Shirley Williams. 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 Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

2 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl 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, fictional fantasy work. No references...

1 year ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

3 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve 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....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

2 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...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

3 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

3 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - 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; Doctor Shirley Williams: 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...

3 years ago
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Sissy Tammy

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...

2 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...

1 year 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....

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...

2 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....

3 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....

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