The Clothes Make The Sissy free porn video

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I don’t know what happened to my clothes. It seemed like they just kept disappearing. Amy’s solution was always for me to wear her clothes, and I must admit that they made me feel really sexy. I’d worn women’s clothes before here and there, but it was always for a party or some special function where it was expected or at least accepted.

My feminine build always gets lots of attention from guys, and it’s not hard to understand why. I’m a petite boy with a big ass, lips, and chest, and a small waist, shoulders, and cock. I’m not gay, but I’ve always enjoyed inflaming the raw, animal sexuality of men. It gave me a sense of power that was always a turn on, even if sex with guys isn’t what I was after. Some people play chess; I play horny studs.

It was a weekday afternoon, and I was busy cleaning the house and getting it ready for Joe, my one-time high school bully who was going to be moving in with us. I still wasn’t quite sure why. I had asked my wife Amy, who had arranged the whole thing, but she was vague about it.

I had asked her once. We were lying in bed spooning, and I was the little spoon as usual, even though we’re basically the same size. I was naked and she was still dressed from work in her white blouse, black pencil skirt, and black pumps. We had been silently cuddling for awhile when I spoke.

“Why is Joe moving in with us?” I said with a pout that was audible in my voice.

“Aww sweetie,” said Amy, chuckling softly. She kissed my neck and reached around and started caressing my left nipple. As she started sucking on my earlobe, I whimpered and instinctively ground my ass into her crotch. My little dicklet ached.

“This is going to be so good for us, baby,” she said.

“But he bullies me,” I whined. “He has since high school.”

“Mmm hmm…” she said as she moved her hand to my ass. She started massaging it as she kissed the top of my back and my shoulders.

“He treats me like a girl… ohh ahh,” I said, as she started caressing my puckering asshole.

“Everyone treats you like a girl, my dear,” she said as she started to work her finger into my boi pussy.

“Unnhgg hngg… yeah but it’s… ahh… you don’t understand,” I said. Her finger felt so good I could barely get the words out.

“It’s gonna be fine, honey. Just remember you need to get the house ready this week.”

I dozed off and woke up to Amy rolling me over on my back. I opened my eyes to see her skirt hiked up around her waist and wearing a giant red strap-on. She pushed my knees up and apart as she lay down between my quivering legs. As she leaned down to kiss me, I pulled her in and devoured her pouty lips and slinky tongue. I was whimpering and moaning as I sucked her tongue like a tiny cock. My asshole trembled and puckered, each time sending a warm jolt of electricity up my abodmen.

“Mmm hngg unnh please… ungh please fuck me… hngg,” I mewled.

She reached over me for a bottle of lube on the nightstand, her tits dangling in front of my face. I took a nipple in my mouth and started to suck and lightly bite it. She paused to moan and I imagined someone doing the same for me. Instead she stood up on her knees and began coating the dildo and stroking it. I lay there, legs splayed, nipples red and puffy, girly cocklet leaking precum, my boi pussy begging to be wrecked.

She started prodding the entrance to my tight little twat before falling on me and driving it home in one thrust. I screamed and moaned as she pushed my legs back, propping herself up and putting my ankles on her shoulders. She pounded me harder and faster and deeper than she ever had. Before long, my hips were bucking, and I was shaking and shivering as my little cock exploded all over my stomach.

She collapsed on top of me and kissed me as I whimpered into her mouth, the aftershocks of orgasm still rippling through my body. I fell asleep and woke up after she’d gone to work.

I spent the next day cleaning, naked except for a frilly apron. It barely covered anything. I got the chills thinking about how every time I bent over, I was leaving myself open to someone walking in and taking me. I was home alone, and that prospect was very unlikely, but it excited me more than I wanted to admit.

Some time in the late afternoon, the doorbell rang.

“Just a minute!” I said.

I went in the bedroom and scrambled to find something to put on. All I could find was a big old t-shirt, so I threw it on. It almost covered all of my ass, and the  neck hole was so big, it slid off my right shoulder. I quickly pulled my hair into a ponytail, and as I did so I realized that I’d be giving whoever was at the door a cheap thrill if I raised my arms at all. Oh well, I thought. What’s the worst that could happen?

I opened the door, and three burly men with moving boxes stood there.

“Hi, can I help you?” I said.

The one closest to the door looked me up and down, licking his lips.

“Are you the lady of the house?”

“I um… I… well… umm.. yeah, that’s me.” My nipples stiffened and my cheeks turned red. I could feel the blood rushing to my clitty.

“We’ve got deliveries for Mr. Russo.”

“Oh, okay.. umm, come on in?”

They came in without another word and went right to the master bedroom. I was confused. I assumed Joe would be staying in the guest room, but I figured they knew what they were doing.

They moved a few more boxes in and then left. About an hour later, Amy came home from work. She was wearing a grey pant suit and heels, her hair held together in a bun with chopsticks. She looked tall, powerful, put together. I was a small, sweaty, horny, thrown-together mess.

“So these moving guys put Joe’s stuff in our bedroom?” I said.

“Yeah,” she said. “Was that a question?”

“Well should we move it to the guest room?”

Amy smiled and bit her bottom lip. She ripped off her jacked and undid her hair, shaking it out so it fell around her face. She walked briskly over to me, backing me against a wall. She grabbed my hips and pulled me in for a wet, hungry kiss. I put my arms around her neck and melted into her.

After a minute or so, she broke the kiss. She gazed into my eyes, caressing my cheek.

“You’re the sweetest thing I’ve ever known,” she said. She kissed my forehead and turned around and walked to where she’d dropped her jacket. She spoke with her back to me.

“Joe thinks it’s best if you take the guest room,” she said. She looked over her shoulder at me. I must have looked confused. “He’s way too big for that bed, and it’s too big for both of us. So one of us has to sleep with Joe in the master bedroom. Do you want it to be you?”

She looked at me with her eyebrows raised. I swallowed hard and my cheeks flushed as I imagined crawling in bed naked next to a naked Joe. A shiver ran up my spine. Amy smiled.

“I didn’t think so. It’ll be fine babe.”

She walked into the the bedroom to get changed, and I leaned against the wall, sliding down till I was sitting on the floor.

Did I want to share a bed with Joe? All I could think about was his cock twitching in his pants, his intoxicating aroma, his commanding presence that I found irresistible. I couldn’t think straight. Joe had decided our sleeping arrangements, and there simply wasn’t room in my head to imagine anything else. Pleasing him crowded out every other thought. I felt dizzy.

Amy came out of the bedroom wearing yoga pants and a t-shirt, her hair up in a pony tail.

“Also Joe has requested a certain amount of modesty from you, which I think is reasonable,” she said.

“But I… I mean I’m modest! I just… my clothes… I just haven’t had a chance to go shopping,” I said.

“That’s not really the problem,” she said, sitting down next to me. “He wants you to wear a bra.”

I groaned in embarrassment and covered my face with my hands. My whole body throbbed in shame.

“That’s so ridiculous,” I said with less conviction than I’ve ever said anything. “Why?”

She smirked and grabbed a handful of my right breast.

“Gee, I wonder?” she said.

“They’re A cups! I shouldn’t need a bra.”

“Baby girl, these are not A cups,” she said. “And you can’t just wear my clothes the rest of your life, can you? We’ll go shopping tomorrow.”

I got up suddenly and ran into the master bathroom, locking the door behind me. I rifled through the drawers till I found Amy’s large suction cup dildo. I pushed it into the floor of the tub, took my shirt off, and climbed on top of it. I slowly lowered myself on it, shivering and shuddering as I went, and soon I was bouncing on it with fervor. I grabbed a nipple with my left hand as I sucked the thumb on my right, bouncing faster and grunting and whimpering in a higher and higher pitch.

“Hnngh unhh unngh, Oh Joe, fuck me harder!” I was screaming now. I didn’t care who heard me. All I could think about was wrecking my juicy ass on Joe’s massive cock. Every inch of my body was hot and tingly. I grabbed both breasts now, my tongue lolling out, my chest covered in sweat and drool.

I sat all the way down on the dildo, bottoming out and feel it scrape my insides. I ground my ass in a circular fashion on it as I imagined grinding on Joe’s cock, his muscular arms squeezing the breath out of me as he grunted and bit and sucked my tits. I imagined prancing around the house in slutty, girly clothes, driving him to distraction. As I ground my ass back and forth, I whimpered and groaned and my aching little cock exploded, sending convulsions up my spine and down through my legs.

I raised myself off the rubber cock and collapsed in the tub, my breath ragged and heavy, sweaty hair matted to my forehead. I was spent but not satisfied. I knew what I needed and it wasn’t a rubber cocking stuck to a cold bath tub.

I laid there until I caught my breath, at which point I got up and got in the shower. The hot water relaxed me as I washed my long hair, the hot, soapy water flowing down my back and between my ass cheeks, soothing my tender rosebud. I sighed as I washed my breasts, my little cock hard, aching, useless. I was starting to get a bit of stubble on my legs and naughty bits, so I lathered my body up with shaving cream and went at them with my lady shaver. The cold razor caressed every inch of me, leaving my skin smooth and soft.

I dried myself off and walked out of the bathroom. Amy was already asleep in bed, so without getting dressed, I sauntered naked down the hallway to the guest bedroom. When I got there and turned the light on, I was struck by how girly the room was. Lots of pink and lace, with a daybed against one wall. It wasn’t creepy or anything-- no psychotic dolls or cuckoo clocks-- but everything about it was feminine. Our master bedroom had a feminine touch, but it was much more neutral. Had the guest room always been like this? I couldn’t remember. I guess it had. I’d never really paid attention to it, but I always felt very warm and cozy in this room. It was like a little pink womb protecting me from the world.

I slid my naked, freshly shaved body between the silk sheets of the bed, sighing contentedly as I rubbed myself against the slinky material. I woke up to the sound of Amy’s voice the next morning.

“Wake up, angel. It’s time to dress you.”

I stirred and groaned, rolling over to face the wall, my back now to her. She grabbed the covers and yanked them off me. I whined and pouted.

“Mmm mm mmm,” Amy said. “Seems like a crime to cover up such a prime cut of triple-A fuck meat with clothes. But rules are rules. Come on.”

She grabbed my hand dragged me out of bed. I was pouting and rubbing my eyes as she led me into our bedroom.

“Today we’re gonna keep it simple,” she said. “You’re a blank canvas.”

She handed me some baggy grey sweatpants and a white t-shirt.

“What about underwear?” I said.

“You won’t need it.”

“But what if I, umm… you know, the friction might, uh…”

“Just think about baseball players,” she said. I breathed hard and started blushing. She smirked. “Okay, softball players then.”

I put the clothes on. The shirt was tight and exposed a bit of midriff. The contrast with the bagginess of the pants was hot. My nipples hardened.

“This is why we’re getting you some unmentionables, my dear,” said Amy. “It’s not fair to walk around and give every red blooded man you see an aneurysm.”

I smiled and tongued my upper lip as I looked at myself in the mirror.

“You’re so boring,” I said. Amy rolled her eyes.

“Never did I think I’d marry a bigger ho than me.”

When we got to the mall, Amy took me by the hand and led me straight to Victoria’s Secret. I asked her why.

“I can’t do anything about what a slut you are,” she said. “But maybe we can make you a classy slut.”

I felt incredibly awkward as we walked in. Amy approached a saleswoman and started talking to her. I hung back, out of earshot. I saw the saleswoman smile and approach me.

“Hi Bobbie, I’m Jane,” she said. “Let’s get you to a fitting a room.”

The three of us walked to back of the store to a large fitting room.

“Don’t we need some clothes first?” I asked as Jane shut the door behind us.

“No, we need to get your measurements first,” Jane said.

I swallowed hard.

“I’ll need you to disrobe please,” she said.

“Do I have to?” I said, looking at Amy and pleading. “Can’t I just get a few A-cup bras and get out of here?”

Amy and Jane looked at each other and laughed. Jane put her hands on my shoulders and looked me right in the eye.

“Trying squeezing those things into an A-cup, and you’ll get five marriage proposals between here and the parking lot. Denial ain’t just a river in Egypt, honey.”

I blushed as I kicked off my pink Adidas and took off my shirt. I pulled down my grey pants, and to my extreme chagrin, my hard cocklet sprung up and slapped my abdomen as I did so.

I stood there with one arm covering my boobs and the other hand covering my crotch.

“I’m sorry, I uh… I don’t know…”

“Sweetie, it’s okay,” said Jane. “It’s actually better for our purposes if you’re fully hard. But this bashfulness will not stand! Let’s see that sexy body.”

She walked up to me and gently but firmly pulled my arms away from my body, lifting them up in the air.

“Ya know, the challenge of this job is making women feel sexy,” she said. “And sometimes I’m in the position of being a miracle worker, which is a challenge I’m more than equal to. But I can see that’s not going to be the case here. You, my dear, are a work of art.”

I stood there, naked, arms upraised, my hard little clitty sticking straight out, blushing profusely, as two beautiful women admired me like a sculpture. The female gaze--the straight female gaze, I should say--is very different from the male gaze. It’s serene, appreciative, there’s no desire or possessiveness in it. It always made me feel awkward. In some ways I’m more comfortable being leered at by slobbering men. At least I know I can control them, lead them around by the dick, so to speak. These ladies were not slaves to their desire for me, so I had no leverage. I felt meek and powerless. And embarrassed, hence my arousal.

“Okay, let’s see here,” said Jane. She approached me and pulled the measuring tape from around her neck. She measured my bust.

“37 inches.”

She moved the tape just below my breasts.

“32 inches. 37 minus 32 is 5, which makes you a DD.”

My eyes got as big as dinner plates. I looked over at Amy. She was impassive.

“Princess, you’re the only one in the world that would be shocked by that information,” she said. Jane laughed softly. I guess I really was in denial. What else was I in denial about?

Jane measured my waist next.

“24 inches.”

And then my hips.

“35 inches. Well well well. It seems the measuring tape agrees with my assessment. A masterpiece!”

“Really?” I said.

“Baby girl,” Jane said, “if I had those measurements, I’d quit this job and lounge on the beach somewhere, making millions from posting bikini pics on Instagram. You could probably live comfortably just selling your used socks.”

“I don’t know what to say…” I was well and truly stunned.

“Oh, almost forgot,” said Jane. “One more measurement.” My eyes got wide again. She grabbed my cock and squeezed it.

“Well it certainly makes up in spirit what it lacks in size,” she said. I was hard as a steel post. She pressed the measuring tape into my pubic bone and stretched to the end of my dicklet.

“2 inches.”

“Ha!” said Amy. “Bobbie always tells everyone it’s 3.”

“Anything else you need to come to terms with Bobbie? Sounds like you’ve got some trouble accepting yourself,” said Jane.

“Let’s not open that can of worms,” said Amy.

“Of course. Didn’t mean to pry. I’ll go get some things for you to try on.”

When she left, I put my arms down and slumped down on a bench. I burst into tears.

“Why am I like this?” I sobbed.

“Aww honey,” Amy said. She sat down beside me and hugged me and stroked my head. “I love the way you are. Sure, it’s pretty clear that Mother Nature was on acid when she made you, but I wouldn’t have you any other way. Neither would that mall cop we passed on the way in.” This last part made me laugh through a sniffle.

“Oh shut up,” I said.

“I saw you look at him, you randy minx. Think you could find his cash and prizes under all those fat rolls?” I made a fake vomiting sound.

Jane returned. She had an armful of bras and panties.

“I thought I was just getting bras here?” I said.

“Well, honey, um… why don’t you give these a try? You know you really liked wearing mine the other day.”

I lost my breath momentarily as I remembered Joe staring at my meaty, thong-clad ass as it hung out of my pants.

“Yeah, um, okay, I guess.”

I tried on so many bras and panties that day, and we left with bags full. I wore a pink set out of the store, and while it was certainly more comfortable, I felt significantly less slutty, which was a let-down. I mean, I always figured that if I was obsessed with sex, everyone around me should be too. But then I remembered that this is what Joe had decided, and suddenly the bra and panties felt like sexy restraints, like he had manipulated me into tying myself up for him. That thought made me lick my lips and think about his strong legs and huge cock. I really hoped my new wardrobe would please him.

In addition to the unmentionables, we also bought regular clothes. Seemed like it was mostly booty shorts, yoga pants, leggings, high-waisted jorts, half shirt and tank tops. All of which made sense, since it was summer after all. We hadn’t planned it that way, and at first I tried on men’s clothes, but none of them fit right, which was nothing new. Maybe it was the bra and panties softening my resolve, but somehow I let Amy convince me to try on some women’s stuff, and I couldn’t deny that it all looked and felt better. Besides, it was mostly the same kinda stuff, just cut differently, which made sense for my body. We even got me a hand bag because none of the clothes I got had proper pockets.

The next few days, I felt a lot more confident wearing my new clothes. Of course, I didn’t wear them much at home. I was busy cleaning and getting things organized for Joe, and I still wore nothing but an apron while doing my chores. I figured I might as well enjoy it for a few more days, since I’d have to wear clothes when Joe moved in.

Of course, even at home, my contempt for clothes could get me in trouble.

One day, I was sunbathing nude out by the pool when I heard the gate open. I was lying face down and looked over my shoulder to see the pool boy Zeke walking across the lawn to the pool. I thought about covering up, but I figured, what the hell, he’s seen what he’s gonna see. May as well stay here and relax.

“Hi Zeke,” I said to him, wearing nothing but sunglasses and a wicked smile.

“Hi,” he said. He was clearly uncomfortable. This was going to be fun.

“I wasn’t expecting you,” I said.

“Yeah, um, I’m a little early.”

“Mmm such an eager beaver…”

“Haha, yeah, umm…” he said, swallowing hard.

“Is it hard?” I said.

“What?!?”

“Is it hard?”

“Is what hard??”

“Your job. Is it hard?”

“Oh, haha, umm.. I thought you meant… I mean, yeah, I mean… no, it’s not hard.”

“What did you think I meant?”

“I um…”

“Did you think I was talking about your cock?”

“Oh umm… aahhh… no, that’s not what I thought.”

The boy was clumsy and awkward and skinnier than I usually like them, but I was having fun.

“If I wanted to know about your cock, I’d ask.”

“That’s good to know…”

His back was turned. The deal was all but sealed.

“Zeke can you do me a favor?”

“Sure, what do you need?”

“Can you rub some lotion on my back?”

“Sure!”

He hastily stumbled over to the lawn chair I was laying on. When got there, I quickly rolled over on my back and spread my legs, pulling my knees up to my chest. He was wearing shorts but no t-shirt, his torso a golden bronze.

I reached a foot up and pressed into his crotch. He was frozen to the spot.

“You didn’t really think that’s what I wanted, did you? What, did you think this was a porno or something?”

“Well, I uh…”

“Get out of those shorts and give me your cock.”

He pulled down his trunks. The skin underneath was a milky white contrast to his tanned torso and legs. His cock was big and angry. I licked my lips.

“Damn Zeke, you’re gonna hurt somebody with that thing.”

He sort of fell on top of me. I guided his cock into my asshole, and he started jackhammering me. I grunted and whimpered.

“Oh yeah, fuck me you stud, give it to me.” He pounded away at me, clawing my tits and chewing on my mouth. It wasn’t the best I’d had, but ever since that day with Joe, I couldn’t get his cock out of my mind. Plus the shopping trip had made me feel some kind of way. I just needed some dick and this kid had plenty.

Thinking about Joe was like turning the voltage in my body up to 11, and my eyes rolled back as Zeke pummeled me furiously. My toes curled and spilled my seed all over my stomach as Zeke’s hot cum splashed my insides as I wrapped my legs around him and dug my nails into his back. He grunted and spasmed a few more times before collapsing on top of me.

“Okay buddy, back to work!” I said, running out of breath as his weight forced the air out of my lungs.

He went back to cleaning the pool and I went inside to take a shower. Tonight was going to be Joe’s first night living with us and I need to get ready. I washed everything twice, and shaved even though I probably didn’t need to, but I wanted to feel clean and sexy for him. I put on some high-waisted jorts and a green halter top. It was a slightly rebellious choice, since I wasn’t wearing a bra, but Amy’d said that I’d be fine if I was wearing a top that didn’t need a bra. Plus she had been sending him pics during our shopping trip, so I knew he’d approved.

Truth be told, I wanted to be waiting for him naked and bent over the back of the couch, but I knew that wouldn’t fly, and I couldn’t fathom defying him. It just seemed like a physical impossibility, like breaking a law of nature.

Amy and I had agreed that I would play hostess for Joe and his buddies that were helping him move, since she was gone on a business trip. And really he didn’t have much. Just a few more boxes. Most of his stuff was going in storage, and some of it was already here.

I had just finished pulling some cookies out of the oven and pouring iced tea for everyone when I heard the front door open. I went to the entryway, and Joe and three of his beefcake friends were walking through the door with boxes. I had a college crew flashback and had to remind myself that these guys weren’t here for a gang bang, as disappointing as that was.

Somehow Joe was even hotter than I’d remembered him, and it’d only been a week or two.

“Hi Joe!” I said. I bounced over to him and gave him a hug, trying to suppress my greedy thoughts. It wasn’t easy. He pulled close and I melted into him. I was sweaty and breathless.

“Hi baby girl,” he said. His friends snickered. “These are the guys. Guys, Bobbie.”

“Hi all!” I said, cheerful as can be. I gave them all hugs. They were studs, but none of them had that aura that Joe had. I couldn’t explain it.

I offered them some tea, which they declined. I was a little disappointed. I think they were health freaks or something because they didn’t want my cookies either. The guys moved a few boxes in then said their goodbyes. Joe and I sat at the kitchen table.

He was reclined, his legs outstretched, drumming the table with his fingers. He was wearing short jogging shorts and a tank top. I was leaning forward, my arms crossed under my breasts, pushing them together.

“So what’s for dinner?” he asked.

“What do you want?” I said.

“Something with meat,” he said.

“Mmm, I could go for some meat myself,” I said.

“I thought you were a vegetarian?”

“Well, you know… Everyone can be tempted…”

He smirked.

“So whaddya got?” he said.

“I’ll probably have to go to the store. You wanna come?”

“Nah,” he said.

“Okay, well I’ll be back before long,” I said. “Oh, and Amy said to ask you if I need some money?”

“Yeah?”

“Well um, can I have some?”

“How much do you need?”

“I’m not sure.”

“Okay, just put it on your credit card and we’ll talk when you get home.”

I went to the garage, got in my Prius and went to the store. When I got back, he wasn’t in the kitchen. I put the groceries away and went to my bedroom to change clothes before cooking.

When I opened the door to my room, I stopped dead in my tracks. My heart jumped into my throat and started thumping like mad. There on my frilly little daybed was Joe, asleep, naked as the day he was born, his glorious cock on display. It was bigger and more beautiful than I’d imagined. A million questions raced through my mind. Had Amy not told him he was sleeping in the master bedroom? But that was his idea. Was he drunk? Was he really asleep? Why was he naked?

I didn’t know what to do, so I figured I’d just change in a hurry and then go make dinner. I stripped out of my clothes and put on some booty shorts and a loose-fitting t-shirt. I started to tiptoe out of the room when he spoke.

“You didn’t put on a bra,” he said.

I instinctively covered my chest and looked over my shoulder at him. He was sitting straight up on the bed, his hard cock point straight out.

“I, uhh… I thought you were… umm…” I swallowed hard.

“You know the rules. Come here.”

I walked over to him in a trance.

“Take off your shirt.”

My heart was beating out of my chest. I obeyed. As soon as my torso was naked, he grabbed my arm and pulled me over his lap. He pulled my shorts down smoothly, gently, then raised his hand and gave me three hard slaps on my juicy buns.

“You will obey the rules.” Slap slap slap! I moaned and whimpered, writing around on his lap. I could feel his hard cock throbbing under my bare stomach. My little clitty was spilling precum. He kept spanking and my ass jiggled with every stroke. My whole body felt like one giant clit and every smack was orgasmic.

After my bottom was sufficiently warmed, he pushed me off of him. I fell to the floor on my knees. My naked body surged with desire with every heartbeat. I instinctively crawled between his legs and reached for his cock. It was hard and heavy. I slowly worked my mouth around the massive head and started bobbing up and down on it. After a bit, he pulled it out and started slapping my face with it. I was in heaven. Then he stood up, grabbed the back of my head, and shoved his cock down my throat and started fucking my face without mercy.

I choked and gagged and held onto his ass for dear life. My throat was his cocksleeve, and he brutalized it such that I thought my cocklet would literally burst. I can’t remember ever being more aroused. Pretty soon his whole body tensed and he flooded me with a firehose of hot jizz. He pulled his leviathan cock out of me and exploded all over my face and chest as my little dicklet exploded all over my abdomen.

After he was done he walked over to where his pants lay and pulled out his wallet. He pulled out a wad of bills and set them on the nightstand.

“Thanks, baby girl,” he said.

My body flushed with shame. Not only had he used me like a piece of meat, he’d paid me for it. I was so hot for him I could have gone a hundred more times, but no such luck.

But hey, if I’m getting paid, it’s not gay, right? Is just paying bills.

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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

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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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
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Saturday Morning Sissy

Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
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Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

2 years ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

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...

2 years 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...

3 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...

2 years 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...

4 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 ...

3 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...

2 years ago
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Curiosity Spanked the Sissy

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

2 years ago
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Tweak Chapter Three Birth of a Sissy

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

3 years ago
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Beth and Sissy

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

2 years ago
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The 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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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...

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...

2 years 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....

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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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...

4 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,...

4 years ago
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stepson becomes moms sissy

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

2 years 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,...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 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...

2 years ago
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  • 38
  • 0

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...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

2 years ago
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Theater sissy

This is a true story. No exaggeration, no BS. Hope you enjoy it.My ex girlfriend Tori and I had lived together for sometime. Our schedules were such that we had one day off together and one day off alone. I loved our together days but my alone days were porn days. And I LOOOVE porn.I would grab my case of beer, pack of smokes, a towel and head for the computer room. I would look up pics, vids, hop in and out of chat rooms. The whole nine. I was really getting into crossdresser vids at this...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

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