Self-Sucking Sissy 3 free porn video

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My step-sister Avery was dancing around her bedroom in a red thong and a lacy red bra when I peeked in through her open door.  She checked herself out in the mirror, struck a few sexy poses, then danced around some more while looking into shopping bags and rummaging through one of her drawers.  Even though I just blew a huge load outside with her mom, I was more than ready to go again.  The only problem was that I was worried about how much of my dignity it would cost me along the way.

Avery was checking herself out in the mirror again.  She pulled the front of her thong up, causing it to wedge into the crease of her enticingly bald pussy.  Seeing her floss her cunt like that convinced me I was willing to pay whatever price she had in mind for any chance to play with her again.  I stepped into her room and cleared my throat.

“It’s about time, my sissy little brother.”  She fixed her thong, digging the moistened fabric out from between her pussy lips.  “So, bitch boy, did you enjoy sucking yourself off in front of your mommy?”

“Step-mom,” I uselessly corrected her, knowing it wouldn’t do any good to insist on that distinction.  “But, yeah, actually.  I liked it more than I thought I would.  Even though they’re fake, your mom has fantastic tits.”

“You mean the only man-made objects you can see from space?” she sneered as she laid out some delicate lingerie on her bed.

“Ha, yeah.  Also, did you know your mom is a big time squirter?”

She looked at me like I was a clueless idiot.  “There’s not a lot about my mom that I don’t know.”  Avery picked up a pair of blue panties, then came to me and held them up by my face.  “These go nicely with your eyes.”  Out of nowhere she slapped me across my cheek.  She wasn’t playing, either, it fucking stung.  “This is my playtime now, I don’t want to talk about your slutty whore of a step-mother anymore.”

“You brought her up,” I complained and nursed the side of my face.  The pain faded quickly when she turned and I got a good look at her pretty much perfect ass with nothing but a thin strip of red filling her cute butt crack.

“Get rid of those ugly shorts,” she ordered.  

I quickly did as she told me, happy to once again put my erection on display for my super sexy step-sister.  It’s funny how just having her seeing my dick was almost enough to get me off.

“Turn.”  She came up from behind and reached around me.  

I could smell her perfume all of the sudden, or maybe it was just her body wash – whatever it was, I loved it because it was her smell.  Her soft skin brushed against mine, causing my dick to flex with urgent desire.  I thought back to when she actually put me in her mouth.  I prayed she would do it again.

“Hold out your arms.”  She slipped the shoulder straps of a brand new, powder blue bra over each of my hands in turn.  This was what I was afraid of.  She settled the bra over my chest then fastened it in the back.  “Let me see.”

I turned around, feeling my cheeks grow warm with embarrassment.  

She fidgeted with the bra.  “Pretty good fit.”  Avery fussed with the front, reaching in and pinching each of my nipples really hard, then shifting the bra again.  “I thought you’d fill out those A-cups a little more.  I’ll have to talk to Mom about getting you on estrogen.”

I scoffed at that, but the serious look she gave me made me wonder if I should be more worried.

“Put these on, cum sucker.”  

I took the blue panties she handed me and put them on.  They were way too tight.  My balls were getting mashed mercilessly, and I had to try three times to get my hard-on to stay in and not pop out over the waistband.

“I think they’re too small,” I suggested.

“No, they’re perfect.”  She walked around behind me and pulled them up, giving me a wedgie.  

“These aren’t supposed to be a thong,” I pointed out, trying not to let the discomfort pitch my voice up too high.

“They are now.”  She smacked my ass before coming around in front of me, then standing back and looking me over.  She didn’t look happy.  “You really are quite disgusting, you know that?”  My evil step-sister made up her mind about something.  “Take everything off and follow me.”

I did as I was told and followed her into her bathroom.  I was once again jealous that she got the room with the private bath, while I had to use the one in the hallway.  She had me get wet in the shower, then she lathered me up with foam.  It felt nice, but I didn’t know what she was up to until she reached for the razor.

“Whoa, what’re going to do?”

“We’re getting rid of all that ugly hair.  I want my sissy bitch to be as smooth as the little girl that you are.”

I was going to protest, but she started right in on the faint signs of manliness I had on my chest.  Her hands on my body were enough for me to let her have her way.  It was only a little hair, after all.  It would grow back…eventually.

Avery quickly finished my chest, then did each of my legs.  My dick bounced, conspicuously inviting her to grab it, as she worked her way up.  Instead, she moved around to my backside and shaved my butt.  It was more than slightly humiliating when she pulled my cheeks apart to get in my butt crack, but I also kind of liked it.  After finishing, she came around and gripped my erection.  Yes!  It was handjob time!

“Stay still,” she warned and went for my pubes.

“Whoa, hold on!  I’m not letting you near my dick with a sharp blade.”

“You let me shave yours, and I’ll let you shave mine.”

It only took me a second and a half to do the risk-reward analysis on that deal.  “Okay, fine.”

She smiled, having known what my answer would be long before I did.  My gut clenched up as she began clearing away my sparse showing of curly pubes.  I relaxed a little as she worked.  She held my hard-on down out of the way, sometimes shifting it to the side when she needed access to a particular area.  I was doing my best not to blow my load, but there was a good chance I wasn’t going to be able to hold out.  That’s when she lifted my dick and my fear of spewing too soon went away in an instant.

The blade moved along the wrinkled skin of my scrotum and every part of me tensed up.  One wrong slip and I’d be bleeding from my nutsack.  The idea of the pain was bad enough, but the embarrassment of facing all those emergency room nurses would be even worse.  I held my breath as she rendered my testicles hairless one quick stroke at a time.  She wasn’t taking this nearly as seriously as she should be.  It was as if she didn’t even care if she accidentally sliced off my balls.  Or maybe that was her intention!

It seemed like forever before she was done, but in reality it couldn’t have been more than a few minutes.  She pushed my nuts around, feeling for any spots she missed.  It was weird, and scary, and amazing all together.  Avery grabbed my bald sack and squeezed.

“Smooth as a baby,” she said.  

I didn’t know if I should be turned on by that, or deeply disturbed.  She rinsed me, dried me, then yanked the panties back up into place.  Even with my cock half soft, it was still too tight.  She pulled them up into my ass crack again, and made sure my balls were fully crammed into the tiny garment proportioned to fit a pussy and allowed no space for a cock.

My step-sister led me by the hand back into her bedroom.  She sat me down at her vanity table.  With deft quickness she pulled my hair back and fastened it with a couple hair clips.  She surveyed my face with an appraising eye.  I wasn’t sure what she was up to until she plucked something from a drawer and began dabbing it on my face.

“What’s that?” I objected.

“It’s foundation, moron.  Now stop moving.”

“Cut it out!”

She pinched one of my nipples and twisted.  “Shut up and sit still, bitch.”

I did as she said.  I wasn’t happy about it, but I was banking on the payoff being worth whatever hell she was putting me through.  

Avery found a wedge-shaped sponge and began buffing the stuff she’d put on my face.  Her motions were quick and practiced.  I held still, my eyes cast down so I could admire her modest cleavage.  After getting off to her mom’s huge fake tits, it was a real turn on to see what I could of her small, natural titties.  

“If you want to be a sissy little slut, you’ve got to look like one,” she said as she applied some other cream under my eyes and to a few spots on my face.  This she buffed out using a big, round, soft brush.  

I couldn’t help but wonder how that brush would feel on my balls.  “What are you doing?”

“I’m making you pretty.”  She continued to work, then switched brushes and selected some kind of powder stuff.  “I only fuck hot chicks.  You should know that by now.”  

I let her pat the brush over up along my nose and across my forehead as I struggled to interpret what she meant by that last statement.  I hated the idea that she was putting makeup on me, but I had a breathless feeling in my chest that I didn’t want to go away.  Giving myself over to my evil step-sister was making me feel high in a way I never felt before.  I didn’t want it to end.  “I want to fuck you so bad,” I confessed out loud.

“No duh, dicktard.  Why wouldn’t you?  My pussy is fucking amazing.”

“Most guys would think it’s weird to want to fuck their own sister,” I responded lamely.

“Yeah, right,” she scoffed.  “Close your eyes.”  I felt another brush working lightly over my eyelid.  “My guess is that every brother wants to fuck his sister.  Every dad wants to fuck his daughter.  And every boy wants to fuck his mom.  Guys just want to fuck every female they know.  It’s disgusting, but that’s human nature, I suppose.”

“Girls are probably just as horny as guys, only they don’t want to admit it.”  I was expecting her to call me an idiot for that, but she didn’t make an argument against what I’d said.  “I mean, you want to fuck your brother.  And maybe your dad, too…”  I may have gone over the line with that.

She quietly tended to my other eyelid for a few long moments.  I felt a sudden jab of pain and realized she’d just plucked one of my eyebrows.  “Hold still, you sissy fuck face.”  She plucked a dozen more times, each one hurting as much as the last.  “It’s not so much that I want to fuck you.  It’s more just because I’m bored.”  She jabbed at my eyebrows with some kind of pencil.  “All the guys I usually fuck are too manly to let me dress them up and put makeup on them like a little bitch.”

I noticed that she didn’t deny wanting to fuck her dad, but I probably couldn’t get away with getting her to talk more about that.  Besides, I wanted her to be thinking about my dick, and no one else’s.

“Lips,” she said and nudged my chin up.  “How about a nice slutty red.”  She worked the lipstick around my mouth, then applied what appeared to be some kind of gloss over that.  

She sat back and assessed the results with a self-satisfied smirk.

“I’m guessing I make an ugly girl,” I said.

“I hate to say this, but you’re almost cute.  Take a look.”

With her permission, I turned and looked in the mirror.  I didn’t recognize myself.  It only took a little bit of makeup and ten minutes to transform me into something else…someone else.  It was freaky, but also weirdly exciting.  Although I didn’t dare say it out loud, I was one sexy bitch!

“Stand up,” Avery ordered.  She adjusted my thong again, squishing my balls and giving my shaft an encouraging pat.  “Now walk around for me.”

She leaned back and watched me do a circuit.  “No, all wrong.  I didn’t say tromp around like a retarded ape.  Walk like a girl.”

I did my best, but she still wasn’t happy.

“Hold on, I know what’s missing.”  She left the room and returned a minute later with a pair of her mother’s heels.

I should have protested, but I kind of wanted to see what it would be like.  It took some work to jam my feet into my step-mother’s high heels, but I managed it.  After a few teetering steps I found my balance.  I did an ungainly circuit, feeling less and less sexy by the second.  Avery gave me a few tips, and my next effort was better.

“Now you’re getting it.”  She watched me experiment some more.  “Nice, now get those hips into it.  Put some wiggle in that walk.”

I felt ridiculous, but the more I practiced the harder my cock became.  

“Ah, you like being a sissy girl, don’t you?” Avery taunted.  Strangely, there wasn’t that usual cruel edge to her teasing, but an undercurrent of arousal.  

Was this really turning her on?  I focused and made a real effort to be as feminine as I could.  I felt foolish, but at the same time it was freeing in a weird way.  I swished my hips, stuck out my butt, and pranced on the high heels as I moved around her room.  In my mind, it wasn’t just her there, it was a whole audience of people watching and cheering me on – all turned on by me, every one of them wanting to fuck me…the women and the men.  

It’s not like I’d turned gay or anything like that, but the lines felt like they were being blurred further than before.  I’d had a cock in my mouth – my own – but would it be much different if it was someone else’s?  I’d had my dick sucked and if felt amazing – but would it matter if that mouth belonged to a man or a woman?  My sister had pushed me to jam my finger in my butt hole, and even that turned out to feel pretty nice.  Did I really care what else got put up my ass, or by whom?  I stopped my parade, afraid of what I might be becoming.

“Very nice, sissy.  You have got to be about the biggest freak I’ve ever seen.”  

When I mustered up the courage to face her, I saw that Avery had her hand down the front of her red thong, her fingers working quickly beneath the thin fabric, and her other hand was up under her frilly bra.  My cock pulsed and burst out of the panties she had me in.  Instead of yelling at me she smiled and shifted her hand to the other titty.  

“You like this?” I asked as confidently as I could, cocking my hips to the side in what I thought would be a sexy girlish way.  

She nodded.  “Yes.”  She said it quietly, almost in a whisper, as if she didn’t really want to admit it out loud.  “I don’t know why, but I do.”  She moved to her bedside table, opened a drawer and pulled out a large, transparent rubber dildo.  It was shaped like a real dick, with balls and everything.  I watched with a racing heart as she pulled down her thong, fell onto her bed, and spread her legs.  “I like girls.”  She rubbed the tip of the bendy dildo along her wet slit.  “And I really like men.”  Avery nudged the head of the nearly invisible cock into her pussy hole.  “But I never thought I’d get so turned on by a sissy little bitch like you.  A boy and a girl all at once.”  She slowly fed the remaining length of the fake dick into her cunt.  Her face registered alternate looks of pain and pleasure as she forced it all the way in.  When it could go no deeper she shuddered and fixed me with a hungry look of lust.  No female had ever looked at me like that before, and I was pretty certain it would never happen again.  “Do something,” she said softly and pulled the disembodied cock all the way out of herself before inserting it again to the hilt.

“Do…what?” I replied lamely, knowing I had to come up with something or she’d scream at me to get the fuck out.

“Surprise me,” was all the help I got.

I minced around her room in a circle, my mind racing trying to come up with something to do that would turn her on.  I hit on something.  It wasn’t the best, but it was all I could come up with in the moment.  

With my back to my kinky step-sister, I hunched down and tucked my cock and balls between my legs.  It hurt some, but it didn’t matter…the show much go on.  I brought my legs tightly together and turned to face her.  Then, pulling down my panties, I displayed my “man-gina.”  It was like the psycho from that Jodie Foster movie.  With my dick all tucked away out of sight, it looked kind of like I had a pussy – a shaved one, at that.  Granted, it was more of a Playboy view of a pussy than anything else, but from what I saw in the mirror the effect was pretty convincing.

Avery sat up and made a face of disgust as she glared at me down there.  I’d obviously screwed up.  This was a bad idea.  I was about to undo the illusion when a smile broke across her classically beautiful California-girl face.  “That is so fucked up,” she stated in an almost reverent tone.  “If I didn’t know you were a boy, I would totally think you were a chick.  A very fuckable chick.  Don’t move.”

As she grabbed her phone and switched it into camera mode, I suddenly feared this secret would get out.  I’d never survive if people at school knew I was like this.  Not only was I done up like a sissy bitch, I was doing it if hopes of getting some kind of sex from my step-sister.  The words “Would you fuck me?  I’d fuck me.  I’d fuck me hard.” Bounced around in my head, drowning out my fear of being found out with the fear that I was more of a freak than even I realized.

Avery took a picture, the flash brought me back to reality – a reality that I barely recognized anymore.  “That’s it slut, turn to the side and show me some ass.”  I followed her direction without thinking.  What was she going to do with these pictures?  Use them to make fun of me?  Blackmail?  If I had pictures of her I’d be using them for jack off material.  There was no way she was going to masturbate to pictures of me done up like this…was there?

“That’s right,” she went on, leaving the dildo behind and taking on the role of a famous fashion photographer.  “Gimme a sexy look…almost…let me see sultry.”  She moved around me taking shot after shot.  The fact that she was naked and being so totally casual about it was keeping me rock hard.  My cock was going to spring out of hiding if she kept up with that.  “Here we go…give me a nipple…nice…pucker up, I want a pretty little kissy face…oh my God, this is too much…just a couple more with your dick out…let me see that sissy wittle wee-wee of yours.”

It was a big relief to release my hard-on and let it spring into its natural position.  I struck a few more poses – not even trying to act like a guy, instead using the kind of poses that women did in all the porn I’d ever seen.  I wanted to grab my cock and jack it like crazy right there, but I resisted and continued playing my sister’s game.  

I bent over and she moved in to get a close up of my ass.  On impulse I reached around and spread my cheeks.  I expected her to recoil and tell me to stop being gross, but she continued to snap away, making small grunting noises of approval after each shot she clicked.  She was really into this.  I leaned forward and put my hands on her nightstand to balance myself.  I went down into a half squat.  My balls were hanging loose and I thought this would give her a good view of them from behind.  From the faint grunts I was hearing, I was right.  That’s when I looked down into the drawer she had left open.

It was full of dildos and different sex toys.  It was a collection I might expect to find near at hand for a middle-aged sex addict, not for a popular high school girl.  When we started, she had admitted to having a couple vibrators, but this was far beyond that.  I guessed that maybe only two of them vibrated and the rest were dongs (big and small), or butt plugs, or…or whatever that thing was.

I had the sense that Avery was going to lose interest soon if I didn’t do something else, and a flash of perverse inspiration came upon me.  I grabbed one of the thinner ones – a long, bullet-shaped, pink vibrator with bumps around the shaft.  I didn’t know if it was one of the toys handed down to Avery.  Had this thing been in my step-mom’s cunt?  I put that thought aside, went for the nearly empty tube of lube, and quickly greased it up.

Before I had time to think through what I was doing, I reached around and poked it into my asshole.  This could be a huge mistake and end whatever was happening, but I was too horny to stop and consider it one way or the other.

“Oh, fuck…” I heard her say, sounding more incredulous that anything else.  “I was thinking of trying that on you myself, but I wasn’t sure you’d go for it.”  I glanced around just in time to see her lean in and take a picture.  “You aren’t fooling around, are you?  You’re all in.”

I guess I was.  I pushed the toy farther and it slid in almost effortlessly.  I was trying to relax everything back there, but couldn’t help clenching.  Even so, the lube did its job and before I knew it the whole thing was in my butt with just enough sticking out to hold onto with my fingertips.  Yeah, definitely all in.

“Go on,” she said behind me in a hushed voice.  “Go ahead and fuck yourself…I want to see you do your own ass…fuck your asshole, bitch.”

Once again, I did as I was told, unable to resist…not really wanting to.  It was humiliating, for sure, but more than that it felt good.  Not only did if feel good to fuck my own ass, but what made it better was to have my harshly judgmental sister watching me.  I looked back and saw her staring with slack-faced awe.  It may not have been honest-to-God awe, but I don’t know how else to describe it.  When her hand went back down between her legs and her fingers began working her pussy, I felt somehow honored in a strange way.

Not only was I turning her on, but she was more than willing to openly show it in front of me.  In that moment, I wasn’t her annoying step-brother that she couldn’t stand.  I was the object of her sexual desire.  Yes, I was nothing more than a plaything to her, but I was getting something out of it, too.  

“Shit,” I moaned.  “I think I’m going to cum.”  But that was impossible, I wasn’t even touching my dick.  My balls tingled in the way they only did when I was about to shoot my load.  “Oh…fuck…”  I had no idea what I should do.  Avery quickly came to my rescue.

“Don’t stop!  Keep fucking your ass just like that.  Turn around so you don’t cum all over everything, and keep fucking.”  By “everything” she meant her assortment of rubber cocks and plastic dicks that she masturbated with  (on what I could only assume was a nightly basis).

She messed around with her phone.  “Okay, video mode.  Don’t touch your cock!”

Pictures were bad enough, now video?  I wanted to tell her no, but I was too far gone to care.  “I’m fucking my ass,” I blurted out nonsensically.  It turned me on saying it, but it turned me on more hearing it.  So fucking weird.  “My sissy asshole is getting fucked by a cock.”  My voice sounded too high.  “My pretty little ass wants to get fucked with a big, hard cock!”  Yep, I was talking in a girl’s voice now, and I’d lost the ability to censor my words before saying them aloud.  “I want to suck a cock, and eat cum, and get fucked in the asshole like the horny little bitch that I am.”

Avery’s hand was moving faster between her legs.  She was humping her fingers as she stood with wobbling legs and filmed my shameless display of self-abasement.  I didn’t need her to tell me I was a perverted freak, I was doing it for her.  And she seemed to be loving every second of it.

“Ahhh…I want cock…!”  I cried out and began spewing semen.  I didn’t know how it was happening, but a steady stream of cum flowed out of my dick onto the floor of my sister’s bedroom as she filmed and ravaged her own cunt.

“Oh, fuck!  Oh, fucking fuck!  Fuck me, fuck me, fuck me!” she chanted and began to spasm.  Her whole body shook, but she didn’t take her eyes off the fountain of white jizz spilling from my pisshole.  I never let up on my ass the whole time, fucking myself as fast as I could and wishing I’d selected a thicker toy to shove up there.  “Ohhh, fuuuuck,” she sighed when her orgasm finally began to stall out.

After several orgasmic convulsions of my own, I stopped railing the vibrator into my asshole and tried to catch my breath.  Avery, stood in front of me, hand pressed to her side as if she had a cramp, and labored to catch her breath.

“What a mess,” she gasped with a slight giggle.  “There’s cum all over the tip of you dick.  Clean it off.”

I looked around for something to use to wipe up with and reached for the tissue box on her nightstand.

“No, no, no,” she scolded.  “With your tongue, perv boy.”

I nodded, feeling foolish for not picking up on the obvious.  She didn’t care about the mess, she just wanted to see me doing something nasty.  I began to get down on the floor so I could assume the position.

“No.”  Avery came to me, reachedTo continue reading this story you must be a member. Join for FREE here.

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I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

1 year ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

2 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

1 year ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

3 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

2 years ago
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Raised a Sissy

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...

1 year 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...

1 year 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...

2 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,...

1 year 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...

1 year ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

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...

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,...

3 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,...

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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  • 13
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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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  • 14
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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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