Sissy Discovers (Part 5) free porn video

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Part 5 of the story about Sissy and her sexual awakening

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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 stared at the huge house. Lisa’s dad had owned a few businesses over the years and sold the last one for a fortune, and she can see where some of that money went. Stone columns hold up a large deck that went the whole width of the house. Behind the deck is a wall of glass that stretched up into the high roof and a warm glow of lights inside spilled out into the dusk. Under the deck was a patio in front of the basement recreation-room and home theater.

Lisa had on the dock lights and a row of small lights lit up the path to the house, and she stepped out of the basement and waved to them to come up.

“How the fuck are you two” she gave her usual greeting while hugging Sissy and then Brad.

They walk into the basement that has a pool table and bar, were Lisa grabs a beer for Brad. She is drinking a blood red frozen drink and she pours one for Sissy out of a large pitcher. “Follow me – I’ve got some great new movies here.”

She leads them into another room with a giant wrap around sofa facing a huge movie screen. The lights are dimly glowing around the ceiling edge and music is coming from hidden speakers. Even with the music there is a hush of a room that is full of sound deadening and you have the sense you have been transported to Hollywood directors private screen room.

Brad sweeps his eyes around the room and says ‘daaaaaamn” this is great. Lisa is telling them about the movie choices as they plop down on the couch three in a row with Brad in the middle.

Lisa picks up a remote the size of an iPad and begins pushing buttons. The music stops and the sound of groaning and panting fill the room. Sissy looks up with a surprised look on her face and Lisa begins laughing and both crack up at the unmistakable sounds of some serious fucking coming through the speaker system at concert level.

“Holy shit” What the fuck is this?” Lisa says as the screen warms up and the image of a blonde face fills the screen. Her head is rocking back and forth from the pounding she is getting outside of the camera’s view. Then she looks off camera and smiles and opens her mouth as a dick comes in from the side and slides onto her waiting tongue. The image fades and then starts over a gain in a loop and she notices the menu at the bottom of the screen for the DVD and the title “Co-ed Cock Lovers.”

“My fuck-nut brother.. He left this in here” Lisa yells and she turns down the volume some. “ he was up here last week with his buddies and must have left this in the player . What a num nuts!’ He is lucky I found this and not Mom – she would have a shit fuck of a time if she saw this!”

“Mmmmm let’s see here” Lisa navigates the menu to the scene selections that are all animated with videos of various girls getting a cock in various ways.

“What do you say Brad – see any girls here you like?”

Slow to take the bait… he says something about liking blondes.

“Good answer buddy – you’ve got two hot blondes here already tonight!” Lisa laughing at her joke.

She picks one scene to play and says “Let’s have a quick look at the competition Sissy – see how we stack up to sexy little co-eds”

The screen goes black and then comes into focus in a dorm room with a blonde sitting at desk, writing a paper with a pencil, wearing a tank top, panties and calf high socks.

“Hey shit head, buy a computer “Lisa tells the girl on the screen. This action is slow so Lisa fasts forward to when boy has come into the room and has pulled the girls top off and she is keeling down in front of the boy.

“OK this is what your good at – not writing the English paper” jokes Lisa.

Sissy is laughing, and looking at the large cock the boy has. Brads is bigger. The girl is actually very pretty and her boobs are only a little bit on the large side. She glances over at Brad who has clamped his legs together and holding his beer in his lap. Ohoh she thinks. He is getting a boner from this.

Lisa stand up in front of the huge screen, and mouths like she is giving the blow job to the dick that is the size of her head. Sissy notices that Lisa has on a tight tank top like the girl and short shorts and socks. She narrows her eyes and wonders how much of an accident this was.

Lisa stops the blow job mime and pirouettes for Brad but turns to Sissy and asks her – “So am I as hot as miss big tits?”

Brad downs his beer.

Sissy says” well mmmmm” she acts like she has to think about it, “Let me see your ass” she orders Lisa, going along with the fun.

Lisa complies and turns her butt toward Brad and arches her back into the classic swimsuit model pose with her ass pointed right at Brads face. The tank top pulls up showing her smooth flat belly, and the shorts are softie style rolled over at the waist so they are ridding up her crack.

She slowly bends over at her waist using her dancer skills and grabs are ankles. Her short shorts ride up her butt cheeks that slowly emerge and her pink panties start to peek out of each side of the crotch. Brad is mesmerized.

Sissy has to admit that Lisa’s skinny little body looks pretty good. She says with authority – “your ass is way better than the slut on the screen.”

Lisa almost falls on her head laughing and hops up and grabs her drink. She runs into the bar and gets Brad another beer and drinks for the girls. They are all looking now as the guy has the co-ed sitting on the desk and is eating out the girls pussy.

Lisa pauses the video on a close up of the pussy and the guy’s tongue just flicking on her clit. It is really big on the screen and detailed

“Now listen to me young Brad, see that?” Pointing at the 3 foot high pussy on the screen. That is a skill you should master – and you’ll get all the girls you could ever want!”

“OK” – says Brad – then trying to play along “so how do I practice that?”

Lisa and Sissy squeal laughter at his cleverness. And Lisa takes the bait to play along.

“Well you have to know a few girls who can let you practice on them” and teach you all the right moves” First you need to know the basics. You can’t start right off on the pussy baby!!!!

She stands up in front of him again and runs her hands over her body – “you have to warm up a girl you know.”

She pauses with her hands on the little points on her chest and then gives then a vigorous rub.

Sissy laughs at the show, but Brad is all eyes and he is leaning forward. She notices he has moved his beer and hands out of his lap and a tent is definitely visible.

Lisa then slides her hand to her crotch and says, “you have you earn your way down here boy” with a husky growl. They all laugh at this and the tension of the room easies a little.

Lisa says I’ll be right back – got to pee like a damn filly”

She does not stop the porn and the girl is getting a serious fucking from the guy now on the bed.

Brad looks away – and Sissy jokes, Looks like last night eeehh?” Brad laughs and he looks at his sisters tits in the dim light and sees her nipples are poking through the white scoop neck shirt she is wearing.

Sissy reaches into his lap - forgetting for a moment that she was trying to set him up with Lisa , and runs her hand on his bulging pants and says “getting a little fired up tiger?”

He says “yeah – I’d like to go soon,” and lifts his eye brow in a sly way. She is surprised to hear this. He wants to fool around with me and not Lisa! She will have to work on that….

“Nah we just got here baby – lets have some more fun with Lisa – we can watch the movie, umm the real movie”

Lisa returns with yet another round of drinks for everyone. They are getting a bit drunk.

“Now where were we?” She asks – “Oh yeah. “How to get a girl hot.”

“Well kissing is very important.” Let me show you… ummm on Sissy here.”

Sissy say’s “whaaat ?”

But Lisa commands her to stand and they face each other. Lisa continues “ Your hands are very important.” “They have to naturally wander to the right places.”

As she says this she pulls Sissy over to her and gives her a little peck on the lips. “see slow at first”

Then Lisa puts a hand in the small of Sissy’s back and one behind her head ad gives her a long passionate wet open mouth kiss, and slides her hand up to her breast in a slow deliberate motion, and gives her boob a good squeeze.

Sissy is giggling and then lets out a loud moan to show Brad how good that was.

Inside her heart is pounding and the drinks have her head swimming with the kiss. Brad is all eyes and his shorts have a large bulge. Sissy thinks her may not be so eager to leave at this point.

Lisa turns to Brad and says the predictable thing, “OK, now your turn – show me what you have big boy.”

Brad hesitates and then stands up in front of Lisa. He gives her the peck on the lips, then pulls back.

“OK – good, now part two.”

He wraps his arms around her waist. Lisa pulls him tight to her thin body and closes her eyes to receive her kiss. Sissy can feel the heat in her panties from watching this as Brad gives Lisa a full French kiss and their head tilt and mouths part. Lisa does not let go of Brad and she takes one of his hands and guides it to her ass, and then the other she pulls up onto her hard puffy tit that is only covered by the thinnest t-shirt material.

Brad seems to like this. Lisa finally lets him come up for air and smiles, “ well that was not too bad was it Sissy?”

“Yep grade A” says Sissy

“That was a pretty god-damn hot-ass-fucking kiss, boy.” Lisa grades him.

His hand is still on her ass and tit. And Lisa says – OK you got that pretty good, now for the next lesson.” And she gently moves his hands and lowers him onto the couch. She looks at his crotch and sees the massive bulge….She has just realized that Brad must have a giant cock.

They all take a drink, and Lisa turns to Sissy and says “ I need my assistant again. “ “Now Brad - this may be a little strange, but you have to know that you can’t go straight for the puss with a girl, you have to work your way down.”

She turns to Sissy and gives her a kiss on the neck, and rubs her back with her hands. Then to Sissy’s surprise her mouth lowers down her neck to her chest just between her boobs in the scoop top and kisses her cleavage.

She is not surprised at this until Lisa’s hand move to her tits and she pushes them together so she can kiss them and nuzzles past the shirt to take her left nipple right into her mouth. “mmmmmm” coos Lisa. Sissy is not sure what to do. Brad has seen her tits, but Lisa does not know that. She wants to keep going but she is afraid Lisa will wonder why she would do this in front of her brother with out a fuss.

She grabs Lisa’s hands and says “whoa there.”

Lisa smiles at her and says, “To much for baby brother?”

Brad interrupts her and says – “Hey don’t stop because of me, I’m OK – I need to learn this stuff” he says with a fake goofy sounding voice to keep the girls going.

Lisa laughs and winks at Sissy, who gives her a look back like “why not?”

Lisa – “That’s my boy, and grabs the bottom of Sissy’s shirt and pulls it up over tits now covered by a thin bra. She pulls the bra to one side and says – you have to give the nipples just the right amount of attention.

Both the girls sink down onto the couch right next to brad who is watching like he may miss something. Lisa has pulled off Sissy’s top and bra and is now giving each breast a solid sucking and licking. She then says “you know you have to give her a little something to look at too” and then to make her point she pulls off her top and her lemon sized puffy tits are in full view for Brad for the second time today. She kisses Sissy on the lips again and fondles her boobs. Sissy is getting very hot now and is grinding her leg into Lisa’s shorts.

Brad has moved over so he can see better and has dropped his hand onto his cock and is absently stoking it through his shorts.

Lisa glances down at the large outline in his pants and lifts her head from Sissy’s tits with a big exhale “whheeeew.”

She rubs Sissy’s crotch through her shorts and is thinking if she can eat out sissy in front of her brother. She decides this is too weird but she wants to get Brad’s pants off. She moves over between Sissy’s legs and leans back on her like a chair with her back on Sissy’s chest.

And announces “ Now for the final lesson.”

Brad is not sure what is going to happen, but his dick is hard as a rock and he is dizzy with the excitement of the show. Sissy has reached her hands around Lisa’s waist and is moving up over her small tits and rubbing them gently.

Lisa points her legs straight into the air and slides her shorts off exposing her pink panties that he can see have a damp spot on them already.

Lisa commands him to get on his knees in front of her. “Now this is a pussy” she says with the voice of an instruction video. “It is a beautiful instrument of sex and must be treated with respect.” The girls are laughing and Brad has a large grin. She pulls his hands to her panties and slowly helps him rub her lips through the thin fabric. Brad is in heaven.

Sissy is in heaven too – she can’t believe Lisa is going for it.

As he rubs her, he notices a small protrusion – like a bump right at the top of her pussy. She guides his finger to it and shows him how to gently make a circle motion over it.

In her instruction voice she continues “This is the main Female sex organ for pleasure, the Clitoris, and it is the secrete to achieving the female orgasm.”

“Now this example is particularly lovely and large…. On some poor girls you can hardly find it.”

Sissy is looking over Lisa’s shoulder at her brothers hand rubbing the clit through the panties. As he is kneeling in front of Lisa his shorts have pulled tight on one side and his cock has made a small wet spot at the end of his head. She is rubbing Lisa’s tits during the instruction and thinking what could possibly come next that will not be embarrassing and yet hot as hell?

Lisa say to Brad, “Kiss it boy.”

He obeys and his lips pucker-up and he gives the bump in her panties a tentative kiss. She puts her hands on his head and keeps his lips on her clit as she helps him move back and forth over the damp pick cloth. “meemmmmmmememm” she coos and tells him to use his tongue.

She pulls the panties to one side and he now see the pink little clit – and he thinks it looks almost like a penis with a hoodie on it’s shoulder. The end of the clit is shiny, smooth and just below the folds of skin is a darker shade of pink and wet with juice. They open up to a dark opening that is her pussy.

She says “ there try that’ and her dives down again onto her clit and pussy. Is it musty and smells like nothing her has smelled before. No hint of the fish smell his buddies always joke about. It is magic. He is not sure if he is drunk but the sounds of the room recede and everything around him gets soft and glowing in the dim light. He is only aware of his stiff tongue lapping up the wetness in her pussy as he drives it in as deep as he can. He can feel the soft skin and flesh give way as he probes and pushes his tongue trough every part of Lisa’s wetness. When he reaches her clit again it is harder and longer than before and remembering her instructions work over it with care and purpose.

“Oh yeah baby that …. that is it. Keep it there for a minute ummm yeah” she instructs him.

Her hips begin to gyrate and squirm uncontrollably, and Sissy is relentless on her nipples. She can feel a rush a pleasure coming over her, but she has another plan. She grabs his head and pulls him up. She wants to see his cock.

“OK – I think you have the idea.” That was really very good. Was that really your first pussy eating?”

“Um yeah” he says

She pushes him upright on his knees and runs her hand on his cock through his shorts. Aawwww baby – look at you. That is not fair is it?”

She unsnaps his short and pulls them down with his underwear and his massive hard cock springs into the room.

Sissy give an “ohhh my” whisper into Lisa’s ear.

Lisa lets out a whistle and exclaims “holy mother of fucking cocks!” Look at that beauty. “

“Take off those shorts boy.”

Brad stands and pulls them off, and Lisa leans forward to examine his cock now even with her face. She takes it in her hands and gently rubs her fingers over the large head and down the hard shaft, tracing the bumpy path of blue veins. She has never seen a cock this large in person.

“God damn, this is as large as my arm.” She bends it up against Brads stomach and it passes his belly button. She holds her arm up with her elbow at his balls and his head is even with her wrist. “That must be 11 inches, and look; it is the size of my wrist!!”

Sissy is giggling now as her plan is working perfectly and Lisa’s surprise is all she had hopped for. Brad is smiling like the proud parent now instead of the embarrassment his dick has always brought him in the past.

Lisa starts to stroke the long shaft and looks at his large pee hole. The black opening is nearly the size of a pencil but is perfect proportion with the rest of his enormous head. The ridge around the head is smooth and sharply defined with all the blood pulling his skin tight, and the cleft from the hole to under his head blends smoothly into the shaft. It is a thing of beauty.

Lisa leans forward and with her tongue pointed flicks the end of his dick while giving him a tight tug on the shaft working from the base all the way out to the ridge like milking a cow. A bubble of clear liquid syrup forms at the end of his pee hole and a large droplet grows at the end that she lets fall on her tongue. She slurps it up and then for the first time slides her lips around his head and takes the large gland into her mouth.

Brad wants to look but he closes his eyes to focus on the feeling her has dreamed about for so long. He looks down again and Lisa has her mouth stretched open to fit his head in and she is trying to slide more of his dick into her mouth. She works it in and out slowly as she tries to get use to the enormous proportions of his dick. And after a few moments she has about four inches in her mouth as she strokes his shaft and balls with her other hand.

Sissy is still sitting behind her and can only see Lisa’s head moving in and out. Brad is in heaven his face is alternating in smooth open mouth sighs and furrowed brow as waves of tingles move through his young body.

Sissy slides to one side to see the action and slides her hand into her shorts and begins to rub herself in a hurried back and forth movement. Her pussy is sopping wet and she can hear it in unison with the slurping sound of her friend’s mouth on her brother’s dick.

She can see the hard cock sliding into Lisa’s mouth. Her jaw is stretched open and her tongue is flattened under his dick as she tries to take more and more of the cock into her mouth. Sissy imagines Lisa’s throat is actually bulging as she is getting almost half of Brad’s dick into her. She gags and strings of saliva are poring from her bottom lip. She pulls off his dick and strokes it and a tear rolls down her face.

“God damn” she says for the fourth time. That is the largest cock I’ve ever tried to suck.”

Sissy is looking at the dripping cock and thinking she has ever had a cock that large either – “I know she says.” As Lisa turns her head to slide her lips down the side of the shaft and faces Sissy.

She stops and grins and says to Sissy, “You need to help me.”

Sissy says “Oh no I’m just here to watch… “ but she is thinking she would love to suck on her brothers hard dick. She can’t bring herself to do it in front of her friend.

Lisa says “hey it.” is just a little suckky nothing too serious.” Lisa pulls Sissy’s hand out of her short and puts it on Brad’s dick.

“You don’t mind do you Brad?’ Brad is in such a state what he mumbles the girls don’t understand.

“See? It’s OK with him”


Sissy is stroking the damp cock for the second time in two days. Lisa’s other two hand rides up and down with hers. They still do not cover his entire dick with three hands. Lisa slurps on his head and then runs her tongue round and round the ridge and then his pee hole.

Lisa is looking up at him as she does this and sees Brad’s face is screwing up like he is not going to hold back much longer.

She pulls off of him and let’s go of his cock and grabs his head in the palm of her hand and gives him a tight squeeze.

“OK boy time to slow down, I want to try one more thing.”

She motions Sissy to move back behind again like a couch pillow and leans back pulling her long slender legs high into the air. Her pussy is shinny with wetness and pointed right at Brad standing between her legs.

His dick is bouncing in anticipation. She commands him to get on his knees, and takes his dick into her hand again.

Sissy is looking over her shoulder and can see Lisa’s hard erect clit facing off against the Brads massive tool. Brads head looks impossibly large, like a fist on the end of a baseball bat.

Lisa pulls him closer and rubs the end of his dick around her mounds and then slides it up to her clit. The black dot of the opening in the end is rubbing against her clit.

She rubs around the pee hole with her clit then forces the clit into the hole in the end of his dick. It fits in with a little effort and she begins to rock her hips. Sissy can’t believe what she is seeing. Lisa is fucking Brad’s dick with her clit.

Lisa moans and coos about how good this feels. Brad is not sure if this is good for him or not but likes the look on Lisa’s face. The clit slides in and stretches the hole like a pussy getting a large dick. Her clit disappears into the hole pushing the hood and folds of skin out of the way. She is rocking her hips now and panting as she fucks his dick with her clit. She speeds up the motion and she can feel the nerves in the pussy scream as her body racks with spasms and she lets out a laugh as she cums from the feeling on her clit.


Brad is standing there looking a little uncertain about what to do as Lisa lets go of his dick and roles her head back on Sissy’s shoulder.


Lisa looks up at him smiling and says, “ that was fucking awesome Brad.” Your cock is a dream. Now put it in me.”

Brad can’t believe this but is does not hesitate.

Lisa sits back, letting go of the control she has exerted on the party from the moment Brad and Sissy walked into the house that night.

Brad looks down at his hard cock, and takes it in his hand at the base and rubs her camel toe lips with his shaft like he has seen in porn movies. He does not try to put it in yet. He pushes forward and slides his dick on top of her belly. As the bottom of the shaft reaches her clit and his balls are on her pussy lips the head of his dick is nearly up to her tits.

She says “That’s right baby, take it slow.”

He slides his dick back down the slit of her pussy he can feel her still hard clit pushing on the bottom side of his dick. Sissy is watching this intently still in a little bit of shock at the click fucking. He makes a few more slides with his dick then pulls it down further and rubs his head around her pussy, pushing the folds of silky skin around with the head of his cock like a k** playing with his diner.

Lisa’s hands slide down on either side of her pussy and pulls open the mounds of skin and lips so her swollen pussy is open wide like a black cavern.

“Put it in me, “ She begins to plead.

Brad slowly moves his throbbing head to the dark opening between her fingers. Even with her spreading hands, his large head still has to force the flesh aside. The tip disappears and the lips strain open and wrap over the rest of his glands, the pussy lips sliding tight around the ridge of his head. Lisa lets out a moan. Sissy snakes her hand into her pants again whishing she had pulled them off earlier.

She is looking at the shaft slowly slide into her friends pussy and it looks impossible that it will all fit in. Only a inch or so has slide in and it occurs to Sissy that from this point of view it is like her brother is fucking her. She looks at the pussy and tries to imagine that large cock sliding into her. Lisa’s large clit is rubbing on the shaft of the cock and Sissy takes her free hand and reaches down to rub the clit against Brad’s dick.

He pulls back a little and then slides more in. He slowly begins to pump in a gentle rhythm going a little deeper each stroke. Lisa is really gasping for breath and letting out sighs and moans at every plunge.

“ Oh yeas that is good, damn”

Sissy watches the inside of Lisa’s pussy lips pull out of her every time Brad’s cock slides back, the wet slime on his cock marking how far inside her before going back into the wet hole.

Lisa stiffens a little as about ¾ of his dick is in her. “Oooohh” she says. Her body is having trouble finding room for this mass of stiff flesh. He feels the pressure and slows the pumping and does not go deeper for a few strokes. Lisa’s face is serious and with her eyes narrow she looks at Brad and says “it’s ok… don’t stop…. put it in… please fuck me.”

Brad pumping gets a little more intense and he is working his dick further and further into Lisa’s body. Her legs are splayed out one foot on the coffee table behind Brad and the other on the floor. She slides down a little to make her body flatter in the direction of Brads thrusting.

Sissy’s hand is cramping in her shorts trying to satisfy her own craving with the weight of Lisa’s body on her. The thrusting is sliding Lisa back and forth on Sissy and it is strange sensation of being fucked through her friend. Sissy moves the cushion form behind her and both girls lean back more. Sissy rotated her pussy up into Lisa’s back and the bony hips and butt are rubbing her now every time that Brad pushes into Lisa. Damn Sissy thinks – he is practically fucking me.

Brad is nearly all the way into Lisa, only a about an inch is still dry. She reaches up and grabs Brad’s ass with her hands stops the thrusting, then slowly pulls him closer to her body. His stiff cock slides deeper and goes all the way in until his thin fuzzy pubic patch is grinding into her clit and pussy mounds. She has him buried in her body. She lets out a thin crying sound and through her teeth tell Brad…. “FUCK ME”

Brad follows the order the begins to pound her pussy with his hips. Sissy feels her orgasm coming and is helping the motion above her with her hands on Lisa’s hips. Her knees pointed so her pussy is rubbing right on Lisa’s back. She cums in fits of spasms.

Lisa feels her friend’s body rack behind her and it pushes her own body give up another orgasm and both girls are laughing as Brad is fucking them silly.

Lisa can see that Brad’s face is screwed up into a knot and his muscles are tense as he is about to let go.

She comes up with one final command,

” Shoot it all over us Brad!” Cum on my tits.”

The sultry command must have been all that Brad needed and he pulled out his cock and without even one stroke with his hand a lump of cum boiled out of the black hole onto her stomach. Lisa is surprised that that is all that came out. Then Brad lets out his breath and his dick jumps again and again as three large spurts shoot out of his cock like jets of white lava.

The first shot lays down a trail of white cream that did go right over Lisa’s right boob just missing her nipple and stopping someplace over shoulder. The second was a bulls eye for Lisa’s chin and cheek, and the third went wide and just did miss Sissy’s face, grazing her shoulder. The cum continued to pump out of his dick for a few more spasms making puddles on her stomach, the sticky streams simply oozing out leaving strings from the tip of his dick to her belly button.

Brads fell back onto the carpet and let his arms fall out on either side of him.

Lisa lets out a loud “HOLY FUCK, that was awesome Brad!!!”

The girls laugh again the tension of the session completely drained from them and Sissy give her friend a big hug.

Lisa – Circles her finger in the large thick puddles of cum on her belly and traces the stream over her breast. Sissy reaches over with her finger and sc****s off the dangling white drops off of Lisa’s chin. And Lisa grabs her hand and sucks the sticky cream off of her fingers. “Mmmmm – I love the taste of warm jizz.” Want some?” Sissy scrunches up her face, “nah” Thinking she still wants to look like she is not a creepy brother fucker…. Maybe not eating his cum will help.

They look at Brad on the floor, his cock is finally drooping a little. His eyes are closed and he is not even looking at the girls.

The surrounding slowly creep back into their consciousness and the screen is back on the main menu of the DVD, looping to the girl turning her head to get the giant cock, and the honky-tonk music playing. The video finished while the three of them were making a sex scene as hot as any ever filmed.

More to come .....

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SISSY SISTERS PARTY by Throne Bob Clump, the friendly retired guy at the end of the street, was taking advantage of the mild weather of late Spring. He was sitting on his front porch enjoying a fine cigar. Or at least a cigar. Those fine ones cost a lot more than what he smoked. As he sat there, a car pulled up across the street, in front of the house diagonal from his. In the dimming light of dusk he saw two figures emerge. The first was a woman, quite attractive in a slender,...

3 years ago
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Sissy Girl Party

SISSY GIRL PARTY by Throne Danny felt so ashamed, standing there before his wife Melba in a pink and white party dress that would be appropriate for a nine year old girl, not a grown man like himself. He cringed inwardly and unconsciously took one of his short pigtails and wound it around his finger. His feet were shod in pretty ballet-type slippers, pink ones with little rhinestones on them. "You look so sweet, Dee Dee," she said with a smirk that he knew all too well. He had...

3 years ago
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Sissy Bachelorette Party

'You want it again?' She said, as she climbed between my legs, spreading them with the force of her knee. 'Yes Mistress.' I said, turning my head to the side. Her gloved hand grabbed my chin and turned it towards her. 'You want to be my girly lesbian bitch?' She said, as she tweaked my puffy nipples with her other hand, the dry latex chafing me. 'Yes Mistress - I want to be your girly lesbian bitch,' I rubbed my horny cunt against her stocking clad leg, ignoring the pain, wanting, no, needing...

1 year ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

3 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...

1 year ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
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...

2 years ago
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Sissy Slumber Party

Sissy Slumber Party I was on my way to the slumber party and I was so excited that my panties were getting wet. As I felt the moisture between my legs I blushed and giggled. My high heels clicked on the sidewalk as I went and my full skirts and petticoats swooshed around my baby smooth nyloned legs. I wiggled down the street and my long curly hair and bangle earrings swung from side to side as I walked. Some men in a passing car whistled at me and I just smiled. But my panties...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 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 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."...

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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