Moms New Sissy free porn video

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My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is involved.

I have to admit that I have always been bothered by my penis size. I've seen smaller dicks online by typing 'small penis' in google but mine is defiantly nothing to boost about at around five inches. I worry that girls are gonna laugh at me, which would be mean, or that I just won't be able to get them off and they won't be interested in sex with me.

I've never actually had sex yet. I just graduated high school a few days ago and I've never been a social butterfly. I had some close friends, Thomas for example; Thomas is a good friend of mine. He has short brown hair and a VERY prominent chin. He excels at computer stuff and loves reading. I read as well, but not nearly as much as he does. We play cards and World of Warcraft together all the time. As for females I've never had much luck, until recently that is. I've been dating this girl, Jennifer, and I think I am going to get lucky with her.

About a month ago she said to me, "Dan, I think that girls should make a boy wait at least six months before they fuck them. My mom told me so. It sure is a rough wait though!"

I blushed like a nervous ninny when she said that, but my dick got hard just from her hand touching my arm and saying that. We had been dating five months and I was sure she was telling me we would have sex soon. Jennifer was a big bookworm, but still popular by virtue of the fact that she was a gorgeous young woman.

So right now, at this moment, we are sitting in my room and it is Saturday night. We are laying side by side on the bed and I'm running my hand through her long dark hair. It's funny because she is doing the same to mine. I've had long hair my whole life. When I was little my mom thought it was cool to have a son with long hair just like hers and she had it cut that way. Since I got old enough to pick my own haircut I just went with it, long brown hair was part of what I saw in the mirror and if I cut it off it would be weird.

It has gotten me picked on some in school though, but I don't think cutting it would stop that. I get called a fag a lot just cause I'm a bit of a loner and the jock types think I look effeminate. It doesn't help that my butt is kind of big, which doesn't make sense to me because I'm skinny overall but fat seems to go to my ass instead of my stomach like most guys. One bully liked to compliment my ass to mock me, it was always, "Man you got a juicy rump," or "That ass is looking fine Danielle!" I'm not gay though just to clear that up. Metallica had long hair, they aren't gay.

I realized that this was the perfect moment as Jennifer snuggled her face into my neck, she had a long neck, with pale skin, should I start by kissing it? I felt myself getting short of breath. There were butterflies in my stomach and my legs began to tremble a little. 'Calm down Dan!' I thought. I had to act before I lost my nerve.

I shifted myself and lowered Jennifer's head to the pillow; I propped up on an elbow and looked into her eyes. She smiled at me and my legs quivered. I leaned in to kiss her while my hand squeezed her breast through her shirt. We had made out plenty of times before, and I had fondled her sometimes, so I wanted her to know I was going further then that and give her a chance to tell me no. I slid my hand down her chest and rubbed her stomach as our tongues danced inside my mouth.

I always start out by putting my tongue in her mouth, but somehow she always pushes me back into mine. She likes to bite my lips and hiss at me; sometimes she bites my neck painfully hard. My hand reached her pants and I slowly undid the button. When she didn't protest I lowered the zipper. Her hands went under my shirt on my back and scratched me hard, her nails digging into my skin as I pulled her pants off.

She had on cotton panties with blue and white stripes, tiny hippos were running along the lines. I rubbed my hand over her crotch, feeling the warmth and the moisture on the fabric. Jennifer pulled her mouth off mine.

"Those come off last bad boy." She breathed into my ear and then pushed her tongue inside. I giggled as she wiggled her tongue in my ear, it tickled. I got her shirt off, then her bra, and backed off a bit to take off my shirt and pants so that I was left in my boxers. Jennifer spread her legs and grabbed my arms, pulling me into her embrace and clamping her mouth on my neck again. I felt her tits pressed against my chest, the first time I had ever felt bare tits, my dick was hard and I wanted to fuck her bad but I didn't want to rush this. Jennifer bit me hard making me flinch then she kicked with her legs and rolled me over so she was on top. She sat up and looked at me with a wicked grin, licking her lips.

"You are so hot Jen!" I said, gazing at her round boobs. She looked down at them and pressed them together, then pushed them to my face.

"I know you want to worship my tits Dan." She said in a sultry voice.

"Oh yeah..." I gasped, running my lips along the lower curve of her tits, licking at her fingers as her hands squeezed her breast and shook them right in my face. The soft bouncy jugs drove me wild, I slurped loudly on her nipples which she offered me for a few seconds at a time, then moved her tits so I had to catch them. She slapped me with them a few times actually, not sure if that was intentional.

"Bite them." She whispered.

I took her nipples in my teeth and flicked my tongue over them.

"Harder!" she demanded.

I bit her with about half my strength and she moaned.

"Chew on my tits Dan! Hurt me!"

I left marks around her breast, they were covered in spit when I was done and had bruises from when I got really excited and she screamed at me,

"HURT ME! BITE ME HARDER! YES! OUCH! THAT DIDN'T MEAN STOP!"

Finally she pushed me down her strong hands on my shoulders. She lowered her face to my chest and proceeded to give my chest the same treatment. It felt great at first, her tongue electrified my nipples and it was like there was a straight connection from them to my dick, I was afraid I would soot in my briefs, but then she started biting the crap out of me and I whimpered. When I tried to push her back she slapped my hand away. I was afraid to turn her off, so I took it as best I could, emitting a combination of sighs when she licked gently around my chest, moans when she swirled her tongue around my nipples, and shrieks of pain when she sank her teeth into my flesh like she was going to tear out a chunk.

I was laughing as she licked the sides of my stomach on her way down, I was very sensitive there. Then the anxiety was back all of a sudden when I realized she was about to see my dick. What would she think? I looked down at her and tried not to show the worry on my face as she put her fingers into the waistband of my boxers and pulled. My five inch hard penis sprung free, and without batting an eyelash, she engulfed it with her mouth.

"Uhhhh!" I groaned and reached down to stroke the back of her head. The feeling was amazing, unlike anything I'd felt before. It was her breath and her tongue I think that really did it. I'd had wet towels before with hot water, and an awesome pocket pussy that was super soft... but they weren't alive like her mouth. Her nose let hot air flow out onto my crotch and goose bumps went down my legs, her tongue wiggled on the underside of my cock. She looked up at me as she bobbed her head on my dick, I felt my balls tightening up and the pleasure intensified. 'No not so soon!' I thought.

"Jennifer," I said, "I'm gonna, uhhh gonna, you know..."

She didn't stop or slow down; she just pumped my dick in and out of her mouth, staring up at me. I squeaked embarrassingly and came. My dick twitched in her mouth and poured cum onto her tongue. She held me in her mouth as I deflated. She kept a seal over my dick as she let it slide out her mouth, the wet head falling back onto my balls, and then she crawled up my body.

She opened her mouth and showed me then cum on her tongue, a grin on the corners of her mouth. I was horrified as she leaned in and stuck out her tongue. I turned my head away quickly. She closed her mouth and smiled then gulped audibly. She looked a little disappointed which I was sad about but seriously, what can a girl expect? I am not kissing her when her mouth is full of my cum. She lay next to me and started kissing my neck.

"My turn." She whispered in my ear, and flicked her tongue across it. I felt her hips wiggling next to mine as she pulled off her panties.

Jennifer sat up and crawled forward. She yanked the pillow from under my head and put a knee on either side of my head. I inhaled her scent and looked at her pussy. It was my first real look at one and I stared transfixed as she pushed it forward. She had shaved it to a landing strip over her clit. It was sexy as hell. My willing lips parted and I began to kiss around the lips of her juicy cunt. The taste was sweet and tangy, like a green apple, slick fluid filled my mouth.

"Oh yeah, eat me." Jennifer mumbled.

I did the best I could, probing her feminine parts with my tongue, exploring to see what made her respond. I pushed in as deep as I could, and lapped at the skin around the lips. I kissed her protruding slit and sucked on it, making it puff out a little more. Her fingers curled in my hair pulling my mouth tight against her. I loved her shoving my face into her wet slit, making it hard for me to catch my breath. My dick was standing up again.

"Do you like it?" Jennifer asked. I mumble my agreement as she shook, grinding her pussy over my mouth and nose. Her cunt-lips and pubic hair filled my vision. "Ohhh, suck my clit, suck my clit, suck it hard!" she squealed. I sucked her clit into my mouth and worked it with my tongue as she came.

Her body quivered as she came down off her orgasm and I licked her cunt-lips gently until she moved back off my face. She scooted back until she was astride me and lowered her pussy to my dick. I sighed as she took hold of my penis and lined it up with her vagina, lowering herself onto me easily. I shouldn't have been surprised that she wasn't a virgin, but part of me had hoped she was.

Her nails found my nipples and pinched me as she started to bounce on my dick. "You ate me good." She said, looking down at me. I tried to sit up but she pushed me back down. "You're gonna learn to do it even better." She licked her lips; I rubbed her thighs as her hot pussy gripped my dick with each stroke, her pussy juice splatting onto my balls and crotch.

"You feel so good!" I said.

"Don't you dare cum in me!" she shouted.

I managed to last a while that time, having just cum. Jennifer's tits were dripping sweet and she was breathing heavy when I finally announced I was close. Once I did she pulled off me and grabbed my dick. She jerked me hard and I spurted onto my stomach. Jennifer cooed and curled up next to me, putting her lips to mine. I could taste the saltiness of my cum on her lips, but I thought better then to refuse to kiss her now. She wrapped her arms around me and I just thought about how incredibly lucky I was.

***

My mom likes to stay out late. I had taken Jennifer home and kissed her goodnight, and was sitting in front of the computer wasting time browsing when her and her date stumbled in. I love my mom, and I don't mean to sound judgmental of her, but she is a bit ah... loose? Is that the word? I don't know I don't mean to say she is a slut she doesn't bang a bunch of guys and sleep around... but she always has a boyfriend and they never last more than six months. Although her current boyfriend breaks that trend actually, they have been dating for almost a year, his name is David and he is a pretty cool guy. He is laid back and has a twisted sense of humor.

Oh I don't know if I mentioned it but my mother raised me alone, my father ran off when I was little and my mom never heard from him again. I didn't have any issues with my mom's boyfriends about replacing my dad or anything, he was a prick, and my mom deserved to be happy. The only thing about the men she brought home that I didn't like, don't tell anybody this, was that I was jealous. My mom is really hot and sometimes I think about, you know. I've looked in her draws and sniffed her panties occasionally, which would get me hard instantly, especially the ones she left on the bathroom floor.

She didn't smell anything like Jennifer though, now that I thought about it. But I guess all women smell different. Anyway my mom has fantastic tits, bigger then Jen's. I heard music coming from my mom's room. She plays music to cover the sounds of her and her boyfriend's fucking; I figured that one out by like eleven. Sometimes I would creep up to the door and listen to the sounds under the music. I could hear slapping frequently, and that put dirty thoughts in my head of my mom being spanked.

In the morning I was sitting at the kitchen table when my mom came in and sat next to me. I was still waking up early because that's what I was used to from school. Soon I'll be sleeping until noon though. I was in my underwear. I walk around the house in my briefs all the time. My mom favors modest dresses at home, although I've seen her change into some revealing outfits to go out in. I was busy dwelling on the size of my dick. Did Jen like it well enough? She looked like she enjoyed riding me, but if she came it wasn't near as explosive as when I ate her.

"Are you okay honey?" My mom asked.

"Yeah..." I said.

"Is everything okay between you and Jen? I saw she wasn't here when I got home."

"Mom you got home at like midnight!" I told her.

"So? Your girlfriend can spend the night you know." She said, putting some breakfast bars and a magazine on the table.

"I don't think her parents would feel the same way." I said.

"Well you graduated high school you can do what you want. They can't keep her from growing up."

"Mom," I said hesitantly, "How big of like, dicks you think girls my age like?" I felt dumb for asking immediately.

My mom laughed and I looked down. "Oh I'm not laughing at you honey it's just that was out of nowhere. Really I don't know I only know what kinds of cocks I like, do you want to know about some of the best ones I've had?"

"No! Never mind mom that was a bad idea forget I said it." I had terribly embarrassed myself, why couldn't I just keep that to myself?

"It's okay honey. Are you worried you won't satisfy her?"

"Yeah." I admitted.

"Well, let me see it." She said.

"What? N-no way!"

"Don't be a baby you walk around me in your boxers all the time and I saw you naked all the time when you were younger it's okay."

I shouldn't have, but I shouldn't have brought it up. At this point I figured I might as well. So I slowly pulled down my boxers and show myself to my mom.

"Well you gotta get hard honey. There is a big difference between hard and soft."

"Ehhh," I blushed, "I don't think I can do that right now..."

Then I gasped as my mother reached over and touched my dick, she squeezed the base with her fingers and tugged on me. I was like a deer in the headlights but my mom just smiled at me casually. Slowly my dick came to life and stood out.

"Oh, that's not bad." My mom said. "It might be a little below average but so what. You think every girl needs ten inches to get off? You've been watching too much internet porn baby. Besides some woman is gonna love you just the way you are. You're a sweet young man now forget about that." She went back to her magazine and chewed on a fiber bar.

I was freaked out, but maybe a little relieved that I had told my mom about my fears. I was a little horny now too. I called Jennifer.

"Hey Jen, you ah, want to go out to the pool today."

"That sounds great... bring condoms."

'This is so awesome!' I thought as I got ready.

"Are you going out?" My mom yelled.

"Yes." I replied.

"Okay don't get her pregnant."

I'm too nervous to get condoms from the grocery so I stopped at the gas station and used the machine in the restroom. Jennifer came out of her house in her swimsuit and I watched her ass as she walked around to the passenger side and got in. When she sat down she put her hand in my lap and said, "Don't drive too close to any other cars."

I was super nervous as I drove, but I couldn't bring myself to push her head out my lap. It was the middle of the day and she was slurping on my cock as we drove down the highway. This girl had been waiting to open the floodgates!

***

That night when I got home David's car was in the driveway and I heard the bed creaking from my mom's room. I walked down the hall to my room and saw her door was cracked open. 'Holy cow.' I thought. 'You'd think she thought she lived alone!'

As I quietly crept past her door I couldn't help but look in. I saw my mom dressed like some cheap prostitute with bright red lips, a miniskirt, a strapless top that just covered her boobs, and thigh high pantyhose. David was naked and pulling her hair as he fucked her from behind. I even overheard them talking dirty.

"Uugh, fuck that hits the spot!" My mom said.

"You have such a tight asshole Rachel!" David hissed.

My mom was taking it in the ass! If Jennifer had not made me cum twice already, I would have pulled it out and started beating it. Fortunately I was sexually sated and so my higher thought processes weren't that impeded. I did stare for a long while though.

What I saw the next morning would change my life though.

As I walked past her room the door was wide open and I looked in. David was gone, and my mother was asleep on top the covers, naked. I peeked my head in and my eyes traveled down her body. 'Such nice tits! Even a hot belly button... wow she has a big bush... wait...' My mind failed to process for a moment. I imagine it was something like discovering you're in the matrix, the whole world didn't make sense! This was impossible! This was my mom, my mother, the women who gave birth to me, and she, how could she....

My mind reeled as I gazed at my mother's soft cock.

This couldn't be! She was a man, a man! My whole life she had lied to me! Her whole character took on a different light. All her boyfriends; I realized they were all fucking her in her ass! They were gay or just plain weird! My mom was a fucking fag!

I wanted to puke, I went in my room and closed the door, burying my face in the pillows and sobbing. I was sickened on so many levels, especially when I thought about all the sexual things that I myself had thought about her, those thoughts had been about a guy! My head was in pure turmoil, I must have lain there for hours by the time my mom came in.

"Son, baby? What's wrong?" She asked. She put a hand on my shoulder.

"Don't fucking touch me!" I screamed.

"Honey..." She tried to slip next to me on the bed.

"Don't get near me! You fucking faggot!" I screamed.

"Oh. Oh God Daniel I'm so sorry...." She tried to reach for me again.

"I said don't touch me you damn cock sucking sissy!" I was just so overcome with anger. I slapped her and shoved her off the bed. She looked up from the floor shocked and I glared at her. Tears started to well up in her eyes and she turned away. "We'll talk later..." She said slinking away.

I lay back on the bed and breathed out a sigh. I just couldn't believe it. I just wanted to avoid the issue. Jennifer would be with her family at her grandparent's today, so I called Thomas.

He showed up about thirty minutes later with some playing cards and we sat on my floor playing games. I tried to take my mind off my mom but it was hard, especially when Tomas made a comment, "So, your mom is she single right now?"

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Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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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...

4 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...

4 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...

4 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...

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,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

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,...

4 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...

4 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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  • 32
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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...

2 years ago
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moms new year gang bang

Every year my mom has a New Years eve party and every year she gets really drunk and I have to carry her to bed. But this year was different. I decided just to let her get drunk and see what happens. When the new year came she was really drunk and started to give every guy at the party a new year kiss. She was wear a tight black dress and I watched as she was walking around kissing all these men that her dress started to ride up a past her ass. Some of the men started to grab and slap her ass...

4 years ago
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mom made me her sissy

"Mom! I called out as I got home from baseball practice, "I'm home!""Hello Danny, we have to talk," she responded, while exiting my room.When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store."Please explain where these items came from."I should have told her I was sorry, and that it was just the one time,But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I...

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...

2 years 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
3 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....

2 years 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...

3 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...

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