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I had placed an ad on Craigslist while on vacation alone in another town. It said: "Submissive sissy bottom seeks older dominant top to service. Teach me how to be a bottom".

I wasn't even sure if I'd go through with it but I got a reply from an older man that got me kind of hot: "Older dom with 9" cock here. No kissing, no hugging, just looking for a sub bitch to service my cock. You provide the holes, the lube & the place; I provide the cock. I also decide when, where & how I cum & you will take it. If you don't want this, don't reply".

I had sent him pics of my ass & butthole. He sent me pics of his huge cock. Just looking at that thick, veiny shaft made my little dick hard so I responded and we set up a meeting. Ben told me to meet him at an adult bookstore in town in the gay section one night. He told me to wear short shorts, a girly shirt & be looking at large butt plugs at 8:00 so he'd know it was me.

I got there early & nervously looked at the butt plugs for 15 minutes, wondering if he was going to show. Finally, someone walked up behind me & said, a bit too loud, "I got something right here that'll plug your ass if that's what you're after" as he put his hand on my butt. I blushed, looked down at the floor, and stammered "so... you... want to uh, go to my... hotel room?".

"Not yet. A lot of you little bitches are all talk & flake on me when the moment arises. I need to know I'm not wasting my time here tonight. I've got a five day load of cum in my balls that needs to end up in someone's holes, either you or some other faggot."

"So... what does that mean?" I asked, nervously & blushing.

"Come to the video booths in the back with me. If you suck my cock to completion & swallow my cum, I'll go back to your hotel room, let you suck my cock some more & fuck you. You gonna do it or should I move on?" He asked, rubbing his crotch.

"Um... yeah, I... I guess."

"We'll see. Follow me back here in a minute; I'll be in the last booth on the left. Just come inside".

I waited for a couple of minutes, wondering what in the hell I was doing. Should I just leave? I mean, what was this guy going to do to me? But something made me stay, & I headed back to the video booths. There were other guys back there hanging around, watching, & I heard whimpers & groans in some of the booths. I found my way to the back booth & opened the door.

Ben was in there, a smile on his face. "Good girl," he grinned. I looked up at the video screen, & saw he was just starting a movie called "Faggot Cum Pigs". He stood there, watching me as the video started playing. A 19 year old guy was giving some older bear a blowjob as he knelt in a pair of pink panties that were around his ankles. Ben grabbed my hand & placed it on his crotch.

"Yeah, that's what you want, isn't it slut? Take care of this load for me & we'll have some real fun in your asshole later on. But I don't wear condoms. If you want this cock, you take my loads raw. And I don't fuck gently; I fuck little sissies like you however I want to fuck. You got that? If you're still interested, get down on your knees & make me cum with your mouth. If not, get the fuck out & I'll find another bitch to take my cock.

"No, I'll... I'll... do it" I stammered. Touching his cock, even through his pants, made me hungry for it.

"Good girl," he said, grinning. He knew that he had me when I said that & began to unfasten his pants as I stood before him, my eyes locked on his crotch. I gasped as he whipped out his bare cock. Even soft, it was huge."

"Now you strip for me, bitch. I like my bitches naked when they suck my cock to remind them of their place," he said.

Nervously, I began removing my clothes until I was completely naked before him, my tiny cock standing at attention.

"Looks like someone's little clit is hard, eh girl? I'll bet it won't stay hard once this cock is up your ass," he grinned, pinching my nipples & reaching around to fondle my bottom. I winced slightly as he slipped his middle finger into my asshole; he smiled in response. As he fingered my hole like a pussy, he made me look into his eyes. "Grab my cock girl. Feel it."

I reached out, finding his member and grasped it with my hand. Smiling again at my reaction, he said "this is going to be in your rectum later, bitch. After you swallow my cum, I'm going back to your hotel room with you. I'm going to bend you over, spread those ass cheeks open wide & fuck you like a girl until you squeal like a little girl. Feel my balls," he said. My hand moved down & I grasped his huge balls gently. "These balls are full of cum, slut. All of it is going to end up in you & on your face until my balls are drained. On your knees, bitch, let's see how bad you want this cock. Get down there & suck me. Show me what a good girl you are."

Never letting go of his cock, I got down onto my knees on the dirty floor & grasped his dick. I'd practiced on my dildo so many times & watched so much porn that I sort of knew what to do with his cock. I held it gently, stuck out my tongue & began to lick all over it, tasking his meaty member as I slobbered on it. When his whole shaft was glistening wet with my saliva, I opened my mouth & wrapped my lips around his cock. I did what I had seen girls do to guys' cocks on porn videos, massaging his balls with one hand while I worked the shaft with the other, my head bobbing up & down over his pole. He was moaning, so I knew that I was making his cock feel good.

He pulled it out of my mouth & wiped it all over my face, smearing it with spit & precum before jamming it back into my mouth. As I sucked him, I saw a flash & looked up to see him taking pics of me blowing him! I backed away for a second, terrified. "Wh... what are you doing???" I asked, horrified.

"Just some insurance to make sure that you do exactly what I want tonight. If you give me what I want, I'll delete the pics. If not..." he grinned. "Just be a good girl & suck me."

I picked up the pace, sucking him as hard & as fast as I could, really working his shaft. He was moaning louder now & his cock was rock hard. When his balls began to tighten against his body, I knew he was about to ejaculate.

"Fuck yeah, bitch, just like that, don't stop now. You're about to get a mouthful of cum. Do not take your mouth off of my cock until you've swallowed every drop, you got that? Fuck... get ready bitch... here it... cums..."

With that, Ben's thick cock began to throb in my mouth as it blasted gobs of cum inside. His load splashed against the roof of my mouth, my throat & onto my tongue as I sealed my lips around his convulsing shaft & struggled to swallow all of his load. Finally, his cock was done squirting & I began to milk him dry, sucking the last bit of cum out of his shaft until it was empty. I gasped for air & he chuckled.

"Yeah, now that's a good girl. You passed the test. Now we can go & haves some real fun. Let's get out of here. Get dressed," he said, "but leave your underwear here. Put these on" he said, handing me a pair of lacy pink panties. "I like fucking sissies in panties."

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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...

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...

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...

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...

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...

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...

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...

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...

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...

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