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Let me remind you how you came to be in this situation before you refuse.

I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy.

And what really turns me the fuck on is to take something precious and submissive and to transform it into my own little fuck toy. Remember when we met? You thought you were so manly and tough - but that first night you let me wrestle you to the ground and force myself on you. It got me so fucking hot that I dragged your shorts down, and started to suck you off as my hand snaked around to caress that sweet tight arse of yours. I fingered your arse hole with my spit-lubed finger until you came, writhing in bliss, in my mouth. I still masturbate and think about that time to this day.

But my desires couldn't be kept locked away for too long. You were such a sweet, innocent boy and I wanted so much you include you in my lesbian affairs. God, the times I fucked myself with the dildo imagining remaking you into my sweet little sissy. But when I thought about how I could go all the way and feminize you until you're a painted whore in slutty makeup taking my strapon up your arse - well, I came so hard I fainted the first time I pictured that.

I suppose it began with my latest conquest, a young student of about 21 who was a sweet little frightened deer until I met her. I taught her the delights of submission, and it wasn't long before she was doing anything I fucking wanted' and my imagination is rich and varied.

When the three of us went out to the bar, we made sure you'd be hooked. We'd got dressed together upstairs, sharing a bottle of wine while you sat downstairs. Both of us wore matching outfits - the red brocade corset with gold lace, matching satin French knickers and red-ruffled opaque black stockings. Our leather skirts were scandalously low, and our painted faces looked severe with arched eyebrows and cherry-red lipstick. While we were out drinking, you allowed her to apply some lipstick on you as I watched and laughed. That was our test, and you passed magnificently. I knew where that would lead.

After you invited us back to your place, I put more lipstick on you while she put two fingers in your mouth, telling you softly to suck. You were a born cocksucker, I could see that. Pure fucking sissy, and it made me so wet.

I noticed your erection and teased you a little about liking it - but I made sure I rubbed my hand across the bulge in your jeans as I did so. You gasped and then I explained we were going to dress you and fuck you until you begged us to stop.

At that point, her other hand had joined mine, rubbing you as you sucked. She asked if that was what you wanted - and you agreed.

We undressed you in front of a long mirror as we caressed and stroked your sweet and sexy boi body. She curled a leg around you and began to kiss you, your head clasped in her hands, your body shivering under her assault. I stroked your cock until it was even harder, as my other hand snaked around you to rub your cheeks.

We thought you'd come then, far too soon, and released you. She pulled out her makeup kit and began shaping your face to match ours. I took the outfit from my bag and started sliding heavenly red satin panties up your legs. I told you how good it would feel when you wore them - and let me slide them into place, giving your engorged dick a stroke as I smoothed them. I was soaking wet as I watched you submit to us. You had no idea what would happen next' but we did.

Your mouth looked so fuckable as she applied the heavy red lipstick and I wrapped the red brocade corset fringed with gold lace around your chest. As I pulled the strings and it tightened around you, shaping you and molding you, I saw your cock twitch in your panties. I commented on how excited your little girly clit was and breathlessly promised you even more pleasure.

She whispered filth to you as she put on fake lashes and arched your brows while I drew the stockings up your legs. You acted as though the ruffled tops were tiny kisses as I clipped the garter tabs to them.

You didn't even ask where she got the long blonde wig from as she carefully maneuvered it into place. When we were finished, we'd feminized you into our beautiful little sissy boislut. Looking at our reflections, you could see you were a perfect match for us in your corset, knickers and stockings. Your lipstick and eyebrows were startling against your pale-powdered face and the blusher only recreated the real heat behind your makeup. You were sexier than I'd ever imagined.

Any of my lesbian friends would have loved a girl like you, sheer fucking submission and open to just about anything. I could see it in your face. You felt beautiful, soft and feminine - I watched as the masculinity ebbed from you. I almost came there and then, but it was time for the reward we'd promised you if you'd play along with us and become our lesbian boislave.

I led you to the bed, pulling you on top of me. Your stiff cock rubbed inside your knickers, while they in turn rubbed across mine. I could only imagine how good it felt for you. I know it was starting to give me tiny mini-orgasms. I could smell the slutty perfume we'd sprayed on your neck.

She reached under us and guided your throbbing cock out of your knickers and into me. I gripped your arse with both hands and slid your length deep into me. As I felt your public bone rub over my clit, I couldn't stop it - I orgasmed. Slowly, so slowly, I began to rock your hips back and forth making sure you couldn't come.

You almost did as I sucked my finger, reached behind you and slid it into your arse. Your eyes lit up and you gasped, opening that painted whore's mouth wide.

Behind you, she strapped on a realistic dildo complete with balls. The very dildo I used when I masturbated thinking of this moment. She started smearing lube across your virgin arse, pumping her cock with her fist to spread the gel thickly over its surface. You moaned and struggled but I didn't let go of you, and wrapped my stockinged legs around you tightly.

I told you to relax and let it happen, that it would take you to a place you never dreamed of. She wasn't very patient, and you squealed as she put the head of the large strap on cock against your arse. I kept the slow rhythm of our fucking and stared straight into your bewitched face as she fucked you for the first time. She eased every inch of the cock into your arse as you grunted and whimpered and gasped around it. I knew it felt good, and you even admitted it when she asked you.

She withdrew slowly, and pushed back in as you wriggled and squirmed and filled me with your enflamed cock. Every time she thrust into you, I could feel your cockhead twitch as you plunged inside me. She picked up the pace, seeing you were comfortable with her now vibrating cock, and I began to orgasm again. It was too much for me - your cock inside me, my beautiful slutty boi fucking me even as you took it in the arse for the first time. What sent me into orbit was the look on your face. You fucking loved it. You could feel the buzzing intruder right through your body and it felt wonderful. Your painted face betrayed you, and I could see you were being delightfully violated. It was so fucking sexy groaning my orgasm out over your cock as I listened to your symphony of moans and begging.

I was so wet my clenching took you to the edge, and as I recovered from the first wave I felt your little sissy arse tighten with your impending climax.

But that wasn't enough for her. I'd taught her well, and she pulled out until just the head of the dildo was inside you. Her voice was seductive as she persuaded you to admit you loved it. She made you beg, and you'd become such a wanton, brazen little wench you did it. As you begged for her cock, she slid it deep inside you. Your frantic begging became incoherent as I started pulling you into me forcefully. All three bodies slapped together in a moment of pure depraved zen until I felt your arse cheeks grip the cock inside you. You squealed in abandonment as the cock violated you and my rippling cunt milked you as you fired into it.

So now, you lie there in your corset and stockings with your knickers full of cum, painted face dotted with sweat. Your stretched sphincter is full of warm lubrication and you're already missing the cock that fucked you until you begged it to stop. So I'll ask once more.

Will you be our full-time cross-dressing lesbian boislut?

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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...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

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