Little Sissy Boy (written By Request For A Reader) free porn video

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This story is for one of my readers who made the request via my website www.6ixty9ine.org

It was only a matter of time before my wife discovered what I am, and I discovered her need to dominate and control me.

We worked different hours and I was often in the house alone which only encouraged my kinky tendencies. When she was away or had meetings she would get up and go to work early and I would stay home until it was time to go out. It began innocently enough I suppose with looking at things on the internet and whilst my wife is an incredibly sexy and curvaceous woman I knew I needed more.

I began to look through her drawers and her wardrobe to find the sexy and sluttish outfits to wear after she had left the house. I would get so excited as I tried on her stockings, heels, suspender belts, panties and bras, and even her nighties. I would dress up like a girl and often go online in chat rooms and sometimes even on camera. Then I would wank my rock hard throbbing cock before undressing, taking a hot shower and going to work.

I suppose I have been cross-dressing off and on since I was about 19. But I always have the desire to crossdress and I have always wanted to share that with my partner. And I have always wanted to be submissive about sex, and let my wife dominate me.

But of course it’s a secret I carry around and often I am forced to act like a dominant man during sex.

As time went on my lingerie longings increased and I began to dress everyday, so it was only a matter of time before I was caught by my wife and I wasn’t prepared for her reaction. I started getting sloppy about putting her clothes away and more than once she would ask me if I had seen a particular pair or panties, or a bra, or night gown.

One rainy morning, I fixed my wife’s breakfast, kissed her off to her job, and then went back to sleep for an hour. I woke up hard and began my usual routine of dressing up in the silk and lace of my pretty wife’s clothes like the secret sissy that I am. I picked out pink holdup stockings belt and white lace panties. The panties were always my favorite and I wore them almost everyday. I slipped on a pair of very slutty red high heels that my feet barely fitted in. Then I fastened a red lace bustier. To finish my ensemble, I placed a lace white silk teddy over my head that went down just past my bum. I went into the bathroom and put my hair in pig tails, applied eye shadow and white makeup to my face. And topped it all off with my wife’s deep red lipstick.

I looked at myself in the mirror and twirled around checking my arse out, making female sexy faces and sprayed some perfume on my neck. Then I walked back to the bedroom and lay down on the bed and began to log into a sex chat room. As the room logged in I saw that two of my favourite pervy guys were also in and said ‘Hi’!

Seconds later and suddenly I heard a noise just outside the bedroom and the door swung open. I just looked up in horror as my wife emerged through the doorway with a look of shock and upset on her face. I was panic stricken and as I was caught in the moment I couldn’t decide whether to crash the laptop in order that she wouldn’t see me putting on a sissy show for guys or running to the bathroom.

“I can explain!” I blurted out through my painted lips. “You see, I am working on a play at the acting group I am in and this is method acting. I am trying to get into the head of my co-star.” I begged my wife.

“You are caught you little sissy!” She almost spat the words out. “I caught you cross dressing in my clothes. You have been caught red handed wearing my clothes and by the look of your cock you really enjoy it!”.

“No, you don’t understand, I was just rehearsing for the play. Please believe me?” I pleaded.

“It’s bad enough that you have been stealing my lingerie and expensive sexy outfits to dress yourself in. You have been stretching them all out, forgetting to put them back in the proper place, and using all my fucking make up!” Her anger was rising as was her voice.

“Don’t lie to me on top of all that and say you are not secretly wearing my clothes, when it is obvious that you love to cross dress because you are a girly boy!”

This was the first time I had heard her use that phrase and my cock jerked involuntarily.
“Well? Isn’t that true you’re a little sissy slut?” She said as she glanced over at the laptop screen to see two men looking in through the camera.

I quickly closed the lid of the laptop.

I was speechless. I buried my head in the pillow and began to weep. It was true. I was a little sissy and had been caught cross dressing. I was so ashamed.

“You know Peter, when I met you; one of the reasons why I liked you was because you were such a sensitive man. A good listener, and had a very feminine side. I still love that about you very much. I have known about your desire to dress in woman’s clothes almost since the beginning. I was waiting for you to ask me to help you. But you never did. So, I had to resort to hiding and spying on you. This is not the first time I have done it. I have watched you prance around like a little girly boy several times. I must confess that at first I was concerned about it, but after telling all my girlfriends about you, I began to see the good side of it. And I began to realize that it turned me on.” I looked up and suddenly realised that she had a smile on her face now.

“It’s ok, sissy boy!” She crooned. “Mummy’s going to make it all better. I accept you and love you the way you are. Even if you are a panty slut. It’s the dishonestly that bothers me and I am going to have to punish you for it. Do you understand?”.

“Yes!” I sobbed. “I am so very sorry. Please forgive me. I love you very much and don’t want to lose you.”

“I want you to lay over my lap and stick that little sissy butt up in the air. Do it now.” She said.
I crawled like a slug across my girlfriends lap, she lifted up my lace teddy and exposed my bum in her white lace panties. She massaged my arse for a moment, then forcefully pulled down my panties and began to spank me many times. And as she slapped me hard she spoke.

“From now on you will always tell me when you want to wear my sissy clothes. Do you understand panty boy?” She said.

“Yes!”, I cried. “Yes, yes.”

“And you want cock too?” She suddenly asked.

“I’m not gay, if that is what you are thinking. I just like to dress up in women’s clothes. It’s a very liberating feeling. I still want to make love to you. I still want you, I still love you.” I said.

My wife kissed me and we lay down together as she stroked my cock in her panties until it was poking out of the top of the lace. I reached under her business suit and began to finger her swollen clit until she was moaning heavily in my ear.

“Are you my sweet sissy boy?” She asked.

“Yes, I will always be your sissy boy” I said.

“Make love to me now like the girly boy that you are.” She said.

My girlfriend took my hard cock out of my panties and slowly placed it in her wet pussy. She controlled my movement and I allowed her to do so.

“You are such a sweet and soft lover. From now on, when I leave for work, I am going to place your sissy clothes on the bed. You want that don’t you?” She asked.

“Yes, very much.” I replied.

“And when you get home at night, I am going to place different clothes for my sissy boyfriend to wear around the house. You want that too don’t you my panty slut? “ She said.

“Yes, I want that too.” I said.

“And from now on, you are going to be both my man, and lesbian lover aren’t you? You are going to fuck me like a man when I want, and fuck me like a girl too.” She said.

“Yes, oh yes” I cried.

My girlfriend began to climax and cum all over my pantied cock. The sound of my lace teddy against her business suit was too much and I exploded inside of her pussy and she came. We collapsed together and held each other tightly and kissed and hugged. It was wonderful.

The next day she did as she said she would and was home at lunchtime. I was dressed in a short skirt and no panties and a bra and holdups. As she entered the room she looked down at me lying on the bed.

“Strip me slut!” She said and I immediately began to remove her jacket and skirt followed by her blouse. Underneath she had a black latex bustier that was overflowing but it wasn’t until I released her skirt that I realised she had latex panties on too and I noticed some odd attachments at the front.

“What are these for?” I quizzed her and immediately.

She simply looked at me with a grin on her lips. “You love being able to be completely submissive to my wise and gentle hands don’t you?”

I nodded.

“And you are now my little play toy. My little sexy sissy that I get to do anything I want to don’t you? She continued and I nodded again.

“And I bet you know what I want to do most to my new sissy boy don’t you?” She asked.

“No! What?” I said innocently.

“Oh now stop lying to me sissy boy. We both know what sissy’s like most. You want to have your little sissy bum all full with Mummy’s large strap-on!” She said.

I gulped in fear but my cock was saying something completely differently as it started to harden again. “Yes!” I said submissively. “You are right. I want to feel your large strap-on buried deep in my sissy arse.”

Reaching down she fished her hand into her bag and pulled out a large strap-on dildo before attaching it to the front of her panties.

“This is to fuck you with slut boy!” She grinned.

Sitting alongside me on the bed she was an incredible sight with her overflowing breast flesh and this large rubber cock now fixed firmly on place over her pussy.

“Suck it!” She said and I felt her hand on the back of my neck forcing my face into her lap as I started to gag on her cock. “You need more lessons in that I think!” She laughed before instructing me to assume the position on my hands and knees. She began putting lube on the strap on and then in my arse as she worked it in with a finger.

“Are you ready bitch boy?” She said softly.

“Yes!” I agreed and trembled slightly.

Then she began slowly inching her cock into my arse and I began to moan in pain. Then the head popped in and she slowly slid the rubber monster deeper into me. She began to slowly work the large dildo back and forth as my bum muscles stretched for her more and more and the pain started to turn to pleasure as my cock was like a rock again.

“Now don’t cum just yet sissy. I want to fuck you in many positions first. I want to see you ride my cock like a good sissy every way you can before having an orgasm!” She said.

It was very difficult not to cum as I lay bent on my hands and knees taking her strap-on deep into my arse. Then I heard her moan and cum and and she turned me on my back.

“Now I want to see your face while I fill your sissy hole with my big man cock!”. She said.

She leant down and kissed me deeply as she thrust her dildo in and out. Her tongue gouged by entire mouth as I felt her rubber cock deep inside and her tits squashed against my chest. But then she pulled out and lay on her back with the rigid monster sticking up in the air.

“Climb on my cock and show me how well you can fuck it by yourself!” She said.

As I mounted her large strap-on, I began to bounce up and down on the cock while she looked deep into my eyes. Her hands rested on my shoulders and guided me up and down to a rhythm she enjoyed. She pulled my hands down and onto her breasts as she released them from the latex casing.

This just increased my excitement and I couldn’t take it anymore.
“I’m going to cum!” I gasped almost apologetically. And seconds later my rock hard cock was shooting out all over her huge breasts more than I had ever cum in my life as a huge orgasm racked through my body.

Still with her rubber cock in me I collapsed onto her and she held me still.

“We’re not finished yet baby!” She whispered and I looked up at her face as she pulled the strap-on out of me.

She stroked my hair and whispered nice and soft things into my ear as we held each other for awhile. Soon she led my mouth to her nipple and to suck on it slowly.

“Now little sissy, you have earned the right to fuck me. I want you to fuck me just like I just fucked you!” She grinned.

“I can’t get hard again!” I admitted with guilt. “Sorry!”

But she just grinned looking at me and I watched as she removed her latex panties with the strap-on cock attached. “I know sissy boy!” She smiled. “That’s why you’re going to put these on!”

She watched as I pushed my spent cock deep within the rubber panties and looked down at the rubber cock swaying in front of me wishing my real one was the same size as this monster.

Immediately she rolled me on top of her and I slipped the rubber dildo deep into her wet pussy. I kissed her deeply as I slowly began to fuck her to several orgasms with the strap-on and I could feel my cock now rock hard again but trapped within the panties. My wife reached around and put several of her fingers in my arse and felt my cock cum deep inside the panties as I continued to pump her with the dildo.

“Oh, and that’s the last time you fuck me with your cock Peter!” My wife said as she lay alongside me. “In future I’ll have the strap-on……………or other cocks and if you’re a good girl you can help me out with them!” ……………………………

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I knew I needed some choke back dicking hot saliva on my shaft and the thick spit from the back of the throat on the head of my hard cock.I found a panty boy online. We started texting dirty and depraved, she wanted to be treated like a mommy and breeded in her ass pussy. She had a tight rectal passage that boys liked to cum in but no ovaries, just the tight asshole and her dick and balls that she put in panties to try to seduce straight men and porno curious boys. I met her in her backyard...

2 years ago
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Sissy boy and a shave

It’s a Saturday night. I’ve been talking with this guy online for a while now trying to determine if he and I are the right fit…. and also work up the balls to meet up (…so my balls and much more can be worked over). We’d spoken about a whole bunch of things whilst chatting, his fetishes, mine, and what both of us would like to do to the other / have done to us. From this it all seemed pretty enticing so we teed up a night we were both free to dedicate to debauchery. Thankfully for me my...

3 years ago
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Forever Her Sissy Chapter 3

Forever Her Sissy - Chapter 3 This is a work of fiction for your enjoyment, all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. We were driving west, the sun was shining and the morning was warm without being hot. Although it was a...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

3 years ago
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Shemale on Male A boy cant outrun his fate of becoming a sissy

It had been about a week now since Nim had arrived at the Lunarfall Garrison in Shadowmoon Valley. It was the biggest choice he had made so far in his life to travel to the alternate Draenor, but it had been a relatively easy choice considering the life he was leaving behind. Nim had been gifted with quite the feminine body, so much so it had begun to get extremely tiring of constantly being mistaken for or picked on for being so lady-like. It was mostly from behind that his gender was...

1 year ago
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Transforme me to a little devot Sissy Slut

I dream of being trained by a dominate man or a bi couple to a sissy house and sex slave. im a bi boy and i want to be a devot good gurl. l want my little cock locked up permanent, servicing my alpha in all ways he likes it, i want lern take his big cock completey deepthroat whitout a gag and i want lern to cum like a gurl over the only way that is allowed anal ! I will not look at women any more unless I am ordered and i will never inside a pussy ! if I am trained by a bi couple then I would...

1 year ago
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Forced Sissy Wedding

Forced Sissy Wedding (Forced to be who I was meant to be) By: Missy Satinpanties I woke up feeling groggy, my head pounding, wondering what the hell had happened. My throat was raw and sore, and felt like someone had worked it over with sandpaper. The last thing I remembered was sitting with my father in his book-lined study, drinking my first glass of brandy with him to celebrate my 18th birthday. That I was with my father at all was rather rare, as my father was a very busy...

1 year ago
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Hotel Sissy Boy Bell Boy Fucked by Dominant Guest

I have a job as a bellboy in a small very exclusive hotel. I see many interesting people, especially attractive men. Almost always they are accompanied by attractive women or other attractive men. One weekend, a very attractive man checked in, alone. He is 6'3", around 225 pounds, with fierce blue eyes and jet-black hair. His trim waist and broad shoulders turned the head of almost everyone in the lobby. I almost knocked over the other bellboy to have the chance to carry his bags. As I escorted...

2 years ago
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Sissy Girl Forever part 2 and 3

Sissy Girl Forever Part two. No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies pants taking their place. Of course I have only had pretty panties and tight girdles for...

3 years ago
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Ladyboys Moving to Thailand and my first Ladyboy

After living in the Netherlands for 33 years I was ready for a big change. I had been toying withthe idea of moving to another country to get away from the stress of it all for a while.I had girlfriends in the Netherlands. Wives.I had one nighters and 2 nighters. I wasn't doing bad for myself.But, there was something missing on the girl side. I love variety. I think I've been withevery kind of girl I COULD be with in the Netherlands. I started thinking about other countries.Other girls. Other...

1 year ago
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The Making of a Sissy Boy Slut The Prequel

So this last time I was over there at about 7pm and they said they would definitely be back by 11pm and to help myself to whatever I fancied. Taking them at their word, within 5 minutes of their leaving, I was upstairs in their bedroom having a good rummage through Susan's underwear drawer. I always liked to pick out a pair of silky pink, black or red panties, depending on my mood, and rub those panties all over my hard little cock whilst imagining I was forcing it between those luscious...

4 years ago
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Forced to be a Sissy III

Forced to be a Sissy III By Cheryl Lynn This is a forced feminization fictional story and any resemblance to anyone living or dead or any other situation is purely accidental. If you do not like forced stories in which some pain is administered do not send negative commentary. Permission is granted to down load for personal pleasure. Down loads for any other purpose or for putting on pay sites is strictly forbidden. Forced to be a Sissy III Jacob stood before Mz. Nelson with...

2 years ago
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The Sissy Transformation Process

Phase 1: Softcore, then hardcore vanilla porn is discovered. Nowadays, it begins at an extremely early age thanks to the Internet (fortunately… or unfortunately)!Phase 2: Shemale porn is discovered by happenstance. Nowadays, the popularity of Shemale porn increases one’s chance of exposure to it. Traps (posted on 4chan /d/) influence the younger generation. At this stage, the fapper imagines himself strictly as a Top or perhaps a little “heteroflexible” (for Shemales and Traps only). After much...

1 year ago
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Transformation Pt3 The Sissy

The Sissy. I open my eyes and stare into the mirror. It is a male face but distinctly feminine. I am just applying the last touches to my makeup. Bright red glossy lipstick. I pucker my lips and think. "Beautiful cock sucker red lips." I notice the ever present band around my head with its glowing lights. My makeup is rather slutty, dark eye shadow, big eyelashes and my cheek bones rouged to accentuate them and of course the cock suck red lipstick. I can hear the boys getting...

2 years ago
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Forcibly transformed into a sissy

It was a warm summer?s day when it all began; I was a successful 34 year old, businessman man, with a large house, flash car, and a beautiful wife.As it was a Sunday I was out for any early morning walk, having just finished making love to my 27 year old wife Lorna, when suddenly a large black car screeched to a halt just before me.In a flash 4 burly men jumped out and I was unceremoniously shoved into the back.At the time I thought it may be some kind of kidnap attempt, little did I know...

3 years ago
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Sissy Femboy Chrissy in Drag at the Club

"Can you wear a dress tonight?""I can't crossdress in public, I'm not 'out' and don't want to be seen that way.""That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in.""Cool, but I'll have to change when we get there.""Awesome! See you tonight!"And that was my conversation with a new lover I just met on AdultFriendFinder. The guy is in his upper 60s, gray hair, wrinkles, very masculine, exactly what I am attracted to. He likes the fact that I am a...

1 year ago
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Forever Her Sissy Chapter 2

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 2 (By Purse Sissy) The drive home was uneventful and quiet, when we arrived I carried her bag in as usual...

2 years ago
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mommy sissy boy p2

ziiiiip taking his large cock out , not full hard but ye so bigger than my lil cockmy knees hot the floor, looking at him remove my tshirt, leaving me in the white panty, his fat cock in my hand my mouth opening , he took my back head and help me get it in''thats it , suck the cock sexy little sissy, ohhh yes make me hard with that mouth''i was sliding it in and out, just the head , feeling him get fully hard made me proud and i sucked on the nice black cock''your mom was so right about you,...

2 years ago
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SISSY BOY

Lori had James who had been her sissy boy for a long time. She loved to dress him like a girl and get him a date or a hook up with another gay guy. Tonight she stripped him naked and bent him over and used her thick strap on in his ass. Even though he was a sissy he had a great body. He had a nine inch thick cock and a great ass that he loved fucked. Lori fucked his ass hard as she jerked his cock and waited for him to cum in her hand so she could feed it to him. Then she pulled the cock from...

1 year ago
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Forced to be a Sissy II

Forced to be a Sissy II By Cheryl Lynn This is a work of fiction and contains forced feminization! So if you do not enjoy forced stories, please do not send negative commentary. Commentary on story line and grammar are appreciated. This story is down loadable for personal enjoyment only. Permission for other purposes or for pay sites is strictly prohibited. Forced to be a Sissy II Matilda entered his room without knocking and quickly reached his side where he had been writing...

4 years ago
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Are you a sissy Have you worn panties befor

I have known my masterbatrix lesbian dominate almost 6 years. All started in her pool one hot night. I shocker fingered her and made her convulse when she came. After waves of ecstasy pulsed through her, she grabbed my dick, pulled my trunks down and started laughing. I dont have a small cock, but it wasnt big enough for her. She led me into her bedroom, made me strip, opened up her top drawer of her dresser. Found a pair of nylon pettipanties and threw them at me, stared me in the eye and...

2 years ago
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Sissy Stepson 9 Forced to Suck

Part 9 - Forced to Suck "Get over her you bitch NOW!" screamed and angry Maryann. Caroline's aunt grabbed his limp red puny dick and put the knee high. "What's a matter limp dick sissy, can't get it up for a woman, maybe you need some perversion or more man cock" crowed Aunt Maryann. "Look sister, he's getting a little stiff, he must love to be degraded" said his stepmother wickedly. "Lay down in front of my feet and Phil put a knee high on your cock and start jacking off in front of...

1 year ago
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Little Miss Sissy Whore

Chapter 1 -- The Pick-up Every year I waited eagerly for the three days when PC-Expo was back in town. In the past, I was always able to find some willing and naive out-of-town female to pick up, "do the nasty," and say my hasty good-byes. Most of them were from some small hick town and were entranced with the Big Apple. In fact, that was both the nickname for the city, and for me. Most women just couldn't wait to sink their teeth into me. So there I was, looking for some love, on the last day...

3 years ago
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Forever Her Sissy Chapter 1

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 1 It was It was quite an opportunity to be on this special team dedicated to a multi-year market research...

3 years ago
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Sissy Girl Forever chapter 2

Sissy Girl Forever Part two. No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses soft pullovers and ladies pants taking there place. Of course I have only had pretty panties and tight girdles for...

2 years ago
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  • 8
  • 0

Sissy Boybreeder Whore

Sissy Boybreeder WhoreMistress likes Her sissy boys. The sweeter, the more submissive, the more obedient, …. the better. She thinks boys have been bad and need to atone. Atone by being girls, Women, Her women. And the first thing Her women must learn is submission. You have no choice. You must obey. Many women subdue their men through conflict. Not all relationship abuse, physical or otherwise, favors the men. The problem with just beating men down it that it takes time. It doesn’t scale if you...

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