My Step-Sissy free porn video

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The Step-Sissy

I attached the brand-new leash on her thin, pale neck. The word "Slut" in fake diamonds adorned the front. My sissy was on all fours, wearing her favorite pink wig and a leopard body stocking. Her shapely little ass beautifully complementing the outfit. Between the cheeks and beneath the leopardskin, is the visible outline of a small dildo inside. Done up in full make-up, flat-chested, with her fake thick-rimmed glasses on. My nerdy sissy girl. She liked being walked around the house with her toy in her hole before we fuck. I gripped her leash and guided her towards the upstairs bedroom for her daily dicking.

I always tried to instill manly values in my son. I tried taking him out to baseball games, to wresting matches and all that...But he never took to any of it. He just spent all his time sitting on his ass on the computer. I always thought he was a nerd. A nice, smart boy sure, but still nerdy. He had a skinny, even feminine body, I thought it was pretty sad at first. I'm 36 now, 220 and fit like an ox. Never have had a better period in my life. My step-son is 22 now. I married his Ma about 6 years ago. Met her at a hot nightclub in the city. Figured she was slutty from square one, turns out she fell for me hard and she was. She loved anal, got dripping wet from it. We're divorced now and the k** is living with me now. Has been for 4 months.

My son always had the vibe of being a pushover, sort of a weak k**. But he was socially active and sometimes had friends over. I was fine with that. Until he started smoking weed in the goddamn house. After I divorced his mom, I got a little harder on the k**. I didn't want to hit him when he fucked up, but I wanted to discipline the stupid twerp properly. So I took to doing to him what my dear old dad would do to me when I fucked up. The next time I caught him and his friend smoking in the bathroom, I kicked his stupid nerd friend out and threw him on the couch.

"You're a fucking immature k**, so you're going to get it"

"Dad, you can't throw me like that! That's abuse"

"And you're doing d**gs in the house"

I pulled down at the waistband on his pants hard, he grunted in pain but I didn't give a fuck.

"Dad, what the shit"

Now this stupid asshole is cursing in my house. I pulled off his little undies and pushed his back down, completely in control even if the skinny k** struggled. I slapped his right cheek with excessive force.

"Agh!"

Then the other little white cheek. Harder this time.

"You still want to curse and do d**gs in my house you little shit? I'm tired of this."

Whap. Whap. His pale ass started to turn real pink and he even stopped struggling. Started crying into the pillow on the couch.

Four more even slaps on each cheek and I ceased. He got the point. He didn't sit right the whole next day.

He straightened up for awhile after that, he wasn't allowed to have anyone over and I was done with that smoking shit. Of course he fucked up as teenagers do and whenever he did I spanked him harder. He may have turned into a good boy all of a sudden, however I noticed he never hung out with any girls. Not even a date.

And he has been locking himself in the room, almost all of the time...

The next morning he was off to class, so I decided to check out the search history on his computer. Turned it on, got on his browser and then...I found some freaky shit. I said the searches in my head. "2 BBC fuck white boy" "Sissy gapes" "Sissy gangbang black" "Big black daddy fucks white boy" "Daddy fists sissy boy" "Daddy son anal".

I feared that my son was in fact turning into me at that age...Because I was a pretty slutty k** back then, I was always playing with myself and trying to find things to use as sex toys around the house. Was too shy to buy a dildo. I was always bisexual, however I found a exhilaration in being with other men even from an early age. I couldn't resist the temptation after I found a tape of Leather Hunks 3 among the straight porn in my father's stash. My first encounter was with my high-school coach. The guy was a balding 40-something. He was a total bear. I was in the 11th grade at the time, hadn't done anything with girls yet. I was just like the k**. Watched a lot of gay videotapes at home, got some real crazy ideas that swam around in my young promiscuous brain.

I had a fight with another k** in gym. Some jock guy who bullied me sometimes. Had to stand up for myself, the coach even said so. Then he said that I should let him know if he could do anything to help me take the edge off. Looking at me up and down the whole time as I sat in his office. I caught on to his signals and before I knew it, I walked over to coach and smiled at him, when got up from his seat and smiled back, I knew what I got myself into. Before I knew it I had coach's 9 inch jammed in my mouth. Even let him blow his load on my face like in the movies. Loved that shit. There were still 10 minutes left in class, he was giving me some tissues when he said "Lemme get you off, baby, get on your front, stick that beautiful butt at me."

I was worried we would get caught, but I obediently did as told. On all fours with my stiff young cock throbbing madly. I could feel the precum leak like a faucet. I could feel him gently lick my ultra-sensitive cockhead. He took his grasp on my cock even further by pulling it backward between my legs. "Are you flexible?" He asked. I gave him a sultry "mmm-hmm". He pulled it back slightly and started stroking downward, my first milking. I let out gasps and light moans as he expertly and rhythmically pumped my cock. Just as I felt I was going to reach my limit, I felt, for the first time, a tongue encircling my virgin pink hole. It tickled, I let out a little femmy giggle like, "What are you doing?" But he kept at it, pumping me while practically making out with my asshole. His tongue started going deeper. I realized this was starting to feel really fucking good and started getting loud with my moans.

"Shhh, baby we gotta go, you're gonna cum now okay?"
"Awhh, mmm, okay sir."

He pumped my shaft harder and faster, my cock was completely on edge when suddenly he said,

"Shoot in my hole, put it in boy"

I stood up without saying anything, I never, ever, did this before. He was bent over his desk now, his athletic thighs spread like he was getting searched. His tan skin contasted his paler, finer smooth butt. I rubbed my leaking boycock on his asscheek, guiding it toward his brown manhole. I spit on my cock like I learned in the pornos, he fingered with three fingers, spreading his entrance. It went in easy. He grunted as I put one inch and another up his tight sexy butt. Then I pulled and pushed his warm hole loose. I was closer than ever and didn't want to stop but before I could ease up, I shot hard. Pushing even deeper, with my coach who I saw everyday, grunting and moaning like an a****l. His asshole tightening as I went deeper, almost seeing how far I get my load up his sexy ass. He turned backward and grabbed my neck. Kissing me hard and wet, our tongues practically dancing. My cock flopped out of his butt, my cum followed. He was limp on his desk, still bent over. He pulled his cheeks apart, presenting. Now every stud I fucked had to take my load up his ass.

It was late at night, the door was cracked...Which I found to be very strange. When I looked in, his eyes were closed, legs spread in my very direction, his right hand working his stiffy while he rubbed his asshole with the left.

I thought back to my method of discipline I had relied on for so long...

I remember when I caught him smoking in my bathroom, door open, not even trying to mask the smell. First fuck up in months. Pulled his pants down to find a rounder, shapely butt underneath. I hesitated and had flashbacks to the twinks and the sissy boys who I watched in my pornos. His ass was pretty sexy like theirs. Then I shook myself out of my daze and laid the hammer down. He stuck his face in the pillow, didn't scream or flinch as the blows landed on his cheeks. They were a brighter red than they have ever been and yet I could feel his ass push up against my hand, I could recall a slight moan beneath the pillows as I rubbed his baby-soft bottom to relieve some of the pain.

I decided to figure out for myself at last.

He left the door open, again. This time I knew exactly what my son had transformed into. It was 1:00am. On a school night and I hear some creaking upstairs in the guest room. I could see that the light was on. I crawled on my hands and knees so that he wouldn't see me. Got right up to the door and peeked ever-so-slightly. There he was.

He had a shiny ebony big black dong, attached to the bed via a suction cup. He was on all fours, wearing a blue bra and panties. His mother's I know. And a blonde wig...I continued watching to my own confusion. His computer was open in front of him. Recording. He guided the exceptionally long dildo into his entrance and with surprising expertise, sank the cock deep into his hole in less than a second. Then he pumped forwards and backwards. Over and over. I was shocked. I watched with a massive hard-on. I had always known that I secretly enjoyed spanking him but...He was my step-son. I figured, whatever, he isn't my blood and that boy has gone completely sissy.

I pushed the door open slowly. He looked up faster than a deer in headlights. He slid away from his sex toy and it popped swiftly out of his bottom.

"Oh my fucking god dad!"

He said in an obvious feminine voice. He was caked in make-up. I was startled at how passable my boy turned out to be. He even stuffed the bra to make his "tits" look huge.

"I'm so sorry dad, please"

Like magic I turned into my young self again, forgetting all about my step-son. Only seeing the slender, shapely sissy girl in front of me.

"Get on your fours, stick your ass up, girl. I know you want to be spanked you little sissy slut!"

I had this delicious butt all to myself. On all fours, his ass was particularly round, both cheeks had smooth dainty white skin. His boypussy was shaven bald, he laid still but his hole seemed to be energetic enough. Lube flowed lightly from his velvety pink hole as he continually winked his asshole. Whap. Whap. Whap. I slapped him so hard he let out little tiny yelps, just like the sexiest sissy boys do. He was really getting me hard and passionate. Another last smack, the cheek stopped jiggling. I grabbed his big black cock toy and shoved the head right in his butt.

"Mmmmmm, Daddyyy, please stretch it, stretch it daddy"

His sissy voice needed work but he would be taught soon enough. I gave me another inch, then another. He groaned as it sank deeper and deeper inside. I could feel his asswalls tighten, his prostate pushing my efforts back.

"Loosen up. You're my toy now, get this dildo."

He continually pushed. Smacked his stupid ass and pushed in harder.

"Ogh, mmmm fuck, daddy! That hurts.."

"Shut up bitch..You were taking that big black cock like a pro when I was watching."

"yes..sir...hmmm...oohh..."

He didn't like it.

"Fine, push it out boy, push it."

Bit by bit the toy slid out. Then it stopped, I saw his pussy pucker and tighten over the cock. It went in slightly and then out slightly as he pushed. An inch inside then out, the end of the dildo bounced and wiggled around until it slid out completely. Shiny with juice. My son's fuckhole was sloppy with lube. His cheeks were recovering already from his spanking, turning it a faint pink now. All this time, obediently remaining on his fours with his slender feminine back arched perfectly. He shook his ass, presenting to me.

I put my face right up to his shiny white ass, took a hot breath on his super-smooth pussyhole. He let out a light prissy moan. I immediately dove in as deep as I could with my thick tongue. His asswalls were hard to reach after that toying, but I found everytime I licked them, he let out the softest and the sexiest little noises.

I grasped his soft cheeks in each hand, his ass ever-so-slightly wiggled on my face, as I was nose-deep in his crack. Without words, I separated myself, turned him around on his back and moved his panties out of the way. I buried my face between his legs, his big sagging boyballs resting on the bridge of my nose. Gave his thigh a smack while I licked. I was hooked on his moans everytime I went deeper, licked his rim and spit on his pussy.

Got a grasp on his cock, felt the pulse inside as it throbbed hard. Leaking tons of sweet cum. Had to separate myself from his sweet asshole to give my tranny boy's big dick some attention.

"You got a big dick, boy. Real big balls for a sissy, babe."

"I play with them too much."

"Fuckin' right you do."

Hot breaths on his pink stiff cockhead then I went to work giving this boy his reward. k** couldn't keep his mouth shut moaning like a slut. Loved that. Reached underneath his bra and pinched his little nips. Rubbed his skinny shaven body. Took his pulsing dick out of there, then gave his super tight hole a lick from the end of his crack to the tip of his dick.

Cum leaked out of his beating sissy cock. I pumped it while I sucked. From base to head. Long slow sucking, like I wanted to suck the cum out myself.

"Mmhmm, mmhmm"

I took it out of my mouth.

"Gonna shoot?"

"Yesss, oh my god sir, you make me feel so pretty and sexy. Please make me shoot"

After about a minute of stoking his now shiny penis, licking his nips, cradling him in my arm as I use the other to get him off. He's breathing hard now and I feel the cock pulse harder, I pulled the skin down and he spurted all over his jaw, neck and chest. He gasped as if he was going to have a heart attack, real dramatic. Again and again, his cock pushing hard after every shot. I could feel him go soft, he moaned femininely and sucked on my neck.

I looked at him in his glitter lipstick, thick makeup and purple eyeliner. His fair skin was shiny and wet with his own load. I looked in his eyes after he separated himself from sucking on my neck and I gave him a wet kiss on his little girly lips. Then a sloppy kiss. Licking everywhere, cleaned his jaw of his load. He pumped my big curved cock then he stopped kissing and used his mouth for awhile, sucked it like a pro. He probably practiced on that giant toy the way he deepthroated my steel-hard dick. I was on edge already, I was about ready to spurt in this little bitch boy's mouth.

He tried to mouth something so I pulled out, threads of wet saliva with it.

"Cum inside my mouth." He pleaded, with half-closed eyes and a still wide-open mouth. His mouth was almost indistinguishable from his ass, because this boy was fucking excellent. Way too sexy to hold this load in any more, so I spared him his gagging for a moment so I could pull slightly, giving him just 3-4 inches of my cock before blasting my sperm down his throat. "MMMMM, MMMMMMMM" Was all the noise the pretty slut could make. He sucked hard at the head of my dick and took it alright at first, but eventually had to spit. He and I needed to clean up.

Took a shower together, couldn't take my hands off his body even without the sissy get-up. He hugged me, rubbed my body and touching my package with his. We had a laugh about it after, considering he told me he was bisexual and had wanted to fuck me since I started spanking him. He really liked being spanked, made him feel like a disobedient girly boy he said. Apparently the way I spanked him kinda, sorta gave away the fact that I actually enjoyed it. So he looked forward to it. Oh well. Told me he had been wearing girl's clothes since he was 10.

A year later now. It's close to Christmas and my boy, or rather I should say girl, has really come around. I've never been a more fit top, I make myself hard sometimes. I'm leading a more active sexual life than ever. But my favorite time is at home with her. She's home from her college class now and as we do every day at 5, she dresses up in her pink wig and leopard bodysuit, ready to be walked. We're up in the bedroom now, I'm rubbing my face in her bulge, smelling the sweet strawberry lotion on her skin. I work my way up to her neck. She has two hickeys now from this but that's why she's my sissy. I suck on her neck and stick my thumb in her mouth to suck. The dildo is still in her asspussy, I feel the end through the outfit and push it in and out. We're going to fuck like we do every night. Or so she thinks, because my new black friend with a massive floppy dick is about to meet her acquaintance.

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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

2 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

3 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

3 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

3 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

1 year ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

1 year ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

1 year ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

2 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

2 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

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