The Making Of A Sissy (Part 3: The Obsession) free porn video

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As I laid in bed the next morning, I was overcome by the painful soreness and tingling sensations emanating from my tight freshly used hole. I could still feel his seed dripping out and leaking down the sides of my ass cheeks. I was lying there naked in bed, my long feminine legs spread out underneath the sheets. I felt like I had been hit by a train, but the previous night was the most satisfying experience I had ever had in my life. As I rolled near the edge of the bed, my eyes caught a glimpse of the panties I had been wearing. They were still laying on the floor by the side of my bed. My heart started racing as my eyes wandered around the room as if I were checking to see if anyone, like my mom, was around. Hopefully she hadn't come in before I woke up and seen them laying there. Surely she would have picked them up or said something to me. Suddenly I was completely awake and a bit nervous. I picked up the cute little pink and black lace bikini off of the floor and walked over to my closet where I shoved them inside of the pocket of one of my coats. As I walked across the room my little clit sized cock bounced around above my balls. Standing in front of the mirror, I examined myself again. Looking up and down at my feminine figure, I knew that I was changing and that there would be no going back. Sam had buried his seed deep inside me, but with it he had also buried (or perhaps uncovered) a secret that was much deeper.

As I felt his man juice lingering inside me, I began to wonder where all this would be headed. What did we have between us, and what did this make us? Was I gay? Suddenly I heard footsteps from upstairs, so I headed into the bathroom. I turned on the shower to let it warm up, and then I sat down to use the bathroom. As I looked down at my little cock and my long skinny legs I felt so feminine. My tight little swollen hole was still sore, reminding me of the big black cock that had exploded inside of me. It was happening again. I couldn't stop thinking about his massive cock, his muscular manly body, and how he took control of me and made me his sissy.

Nothing had ever turned me on this much, and as I stepped into the warm shower my little cock was getting hard again. As the shampoo and soap suds dripped and started sliding down my body, I gently rubbed on my cock. My eyes were closed as I was thinking about Sam, the way he made me feel, and how much I was attracted to him. When he laid his cock on top of mine, it looked easily twice the size. I couldn't stop picturing that and thinking about how much it made me feel like I was his girl. My fingers slipped around my thin little erection, and around my little balls. Before I knew it they were sliding even further down, and I pressed one of my soapy fingers between my ass. Circling around my tight swollen hole, I bit my lip and pressed firmly against it. My finger suddenly slipped inside my warm cum-stained boy pussy. There was that feeling again! My cock kind of went from being fully erect to semi hard. I started fingering myself harder, letting out girlish moans as my little cock flopped up and down as I rode my hand. With my other hand I reached down and started rubbing my little clit with my thumb and a couple of fingers. Just gently massaging the tip while I focused on moving my other fingers into my ass. I had two fingers inside of myself, working on the third, but it was just too tight. Before I knew it I started to climax. My cock stiffened up and let out a couple of little spurts of cum. My hand was cupped around the tip, so I managed to catch every little drop. With two fingers still inside myself, I pressed my other hand up to my lips and started licking up my girly little load. It tasted nothing like Sam's. His cum had a much stronger taste, and was much thicker and abundant. As my fingers slid out of my tight hole, I wrapped my lips around them trying to hopefully taste some of the remains of his seed. It tasted so yummy, and I felt like such a dirty slut.

After I got dressed and began my day, I walked upstairs to find an empty house. I wandered into my mom's room, and my nose was sniffing the air trying to catch a whiff of the sex smell that Sam had left behind. She had made up her bed, and her room was very tidy as usual. Curiosity started getting the best of me again as I made my way to her dresser. Opening up the top drawer my eyes were lit up by a huge assortment of panties. Nervously I tried to look around without disturbing the order in which they had been put away. Then I spotted a pair that I couldn't leave without. It was a silky purple thong with little bows mounted up around the hips. The tiny piece of string that connected the back side would certainly make my ass look good for Sam. I stuffed them into my pocked and went downstairs to try them on. I couldn't wait to slide my pants off and check myself out in these. As I slid my legs inside, and pulled this new skimpy sexy thong up my thighs I felt the tiny little string wedge inside of the crack of my ass. The front piece was so thin it barely covered my little clit. My small little cock was pressed tightly against them, and it was well defined through the fabric. The cute little bows made a nice touch. Happy with the way they looked, I slid my pants on and decided to wear them all day.

Later that evening, Sam and my mom came home after a night out together. I suddenly realized how happy I was that they had hooked up and that things were working out between them. Then I wondered if maybe I was the reason he kept coming back. Certainly that was wishful thinking. I giggled to myself and began to blush. As I walked around with panties underneath my pants, pressed into my ass and around my little cock, every step made me feel like a woman. My mom caught me in the kitchen, and she told me she wanted me to go out tonight.

"Honey, Sam and I need some alone time tonight. Can you maybe go out to the movies with a friend tonight or something? It's just that we would like a night to ourselves" she said.

So many feelings immediately went through my mind. I'm sure the expressions on my face were changing rapidly, and my face was probably turning red. I was actually furious! Before I could open my mouth, Sam came around the corner.

"Ummm...Okay, I suppose" I responded. I couldn't tell if I was sad, mad, or just plain jealous. She just thanked me and smiled.

Shortly afterward, I called up my best friend, Eric, and told him I needed to get out of the house. After these past few days I had totally forgotten about my guy friends. There was no way I could tell him what had been happening. We agreed to hang out and go to a movie. As I walked upstairs to say my goodbyes, my mom said "Okay thanks honey, let me get you some money."

When she had left the room, Sam and I exchanged eye contact. I was studying his face to see if I could read anything out of him. He just sort of plainly looked at me. Then I thought of something! I reached down and grabbed the waistline of my pants and slid them down around my backside, exposing my new purple thong to him. His eyes kind of lit up, and he smiled back at me and gently nodded. The sense of approval in the way he looked at me had made me feel so much better about the whole situation. My mom came back with some cash and sent me on my way.

On the way to the theater, and throughout the whole night I couldn't help but imagine all the things he was going to be doing to her. She was so lucky! Then I started questioning things and wondering if it was his idea to have me leave the house. Either way he knew I was still wearing panties for him, and surely he planned on getting back inside them. During the movie I barely paid attention, and afterwards my conversations with Eric were limited. It was like I wasn't even there, my mind was in a totally different place. The evening dragged on, and it felt like forever.

I ended up making it back home at about a quarter til midnight. As I walked into the kitchen I noticed quite a few empty glasses, and several empty beer bottles. Either they had thrown some sort of party or they had gotten hammered. I didn't think much of it, but disappointed that I had missed out on the fun, I walked downstairs to my room. The house was completely silent. As I gently pushed my bedroom door open I gasped in shock as I spotted someone laying in my bed. It was Sam, and he was looking right at me. He smiled and said, "I've been waiting on you baby."

Tears of joy almost came to my eyes as I rushed over to him. He wrapped his arms around me, and his hand gently caressed my face. Pulling me closer into him, I could feel his massive bulge pressed up against me. He leaned in and gently kissed my lips, then moved his lips to my neck. I could smell the alcohol on his breath. By this point his hands were working my pants undone, and I helped him wriggle them off my hips. As they lid down to my ankles, his big warm hands were climbing underneath my shirt. I lifted my arms up so the could pull it off. Suddenly there I was, standing in front of the man I couldn't get off my mind, wearing nothing but a tiny little thong.

He admired my body as he unbuttoned his pants. As he slid them off, his huge cock was set free, bouncing and swinging before me. Without missing a beat, I suddenly fell to my knees. I knew this was my place, kneeling before a strong black man. He pressed the big mushroom shaped head up against my lips, and I wrapped my mouth around his thick manhood. As I took each inch deeper into my mouth I could feel his cock getting harder and harder. I also felt my little clit pressing against my tight thong, and the string between my ass made me feel like such a girl for him. I looked up and caught him admiring my booty as I arched my back to show it off. He put his hands around my head and pulled me into him deeper and harder. Then he pulled it out and let me catch my breath while a mixture of his juices and my slobber rolled down my chin onto my chest. Before I knew it he slammed his cock back into my mouth and held it there with his hands pulling the back of my head. I began to gag and choke as everything dripped down his balls and my chin. He gave me a firm slap across the face with his hand.

"Take it bitch!" he ordered.

As I caught my breath, he pushed it right back into my mouth. Tears were welling up in my eyes as he reached the back of my throat.

"Good girl," he said while I struggled to manage his cock. "You love Daddy's dick don't you baby girl?"

"Mhmmm" I mumbled with my mouth full of his cock.

He slapped me again. "What did you say?" he demanded.

"Y..Yes Sir!" I responded with my voice muffled by his cock.

"You goin' to let Daddy breed that little pussy again?" he asked as he pulled his cock away from my mouth.

"Yes Daddy!" I said as I caught my breath.

He grabbed my hands and pulled me up from my knees and got behind me. His hands wrapped around my body, working their way around my waist and my tummy. He slid his fingers between my thong moving them back and forth around the waistline as his hands passed over the cute little bows. His warm hand slid down around my throbbing cock. It felt so amazing when he touched it, like it and everything else of mine belonged to him.

"You're always horny for this big black dick aren't you Brianna?" he whispered into my ear.

"Oooh yes Daddy," I moaned.

"Too bad you missed our little party earlier," he said in laughter.

I still wasn't sure what he was talking about, but he pushed me down onto the bed. He was still behind me, and I was down on all fours. My tight sexy little ass was exposed with only a thin piece of thong hiding my hole. He pulled my panties around my hips and down between my knees. I heard him spit, lubricating his fingers, and he rubbed them between my ass around my tight reluctant little hole. One finger then penetrated my boy pussy as I let out a soft moan. Looking back I saw him with his other hand stroking his hard cock. Then I closed my eyes as I felt the head of his massive cock press up against my hole, begging to be let inside. I was still a little sore from the night before, but with persistence his cock managed to convince the muscles to relax and take it. As the head of his huge penis popped inside of me, I felt my cock oozing out with girly pre-cum, dripping out onto the bed.

He started humping me harder and harder with each thrust while my little cock was swinging back and forth. With this position he was able to reach deeper inside me. His cock filled my hole completely. As I let out moans that began to grow louder and louder, he pressed my face down into the pillow to keep me quiet. His cock felt so amazing, and his hands were sliding around my back, my hips, moving around my tummy all while he kept making me take him deeper and deeper. I loved the way he touched me. Then he slapped my ass firmly a few times, leaving his hand prints behind and calling me his little slut. It felt amazing, being taken and talked to like this. He completed me!

Eventually he was ready for another position, so he slid his throbbing cock out of me. My hole tightened up as his head exited my boy pussy. Then he laid down on his back and motioned with his hands for me to come to him. I slid my panties off completely and climbed on top of him and moved closer. As he held his cock up in front of me, his erection reached up and pressed against my tummy. His hand grabbed my little rock hard boy clit, and he pressed his massive manly cock up against mine. Holding our cocks together he stroked up and down with his hand. My body started shaking as I was growing close to orgasm. Right before I climaxed he let go, denying my orgasm. My little balls had to be turning several shades of blue by this point. He pulled my hips closer toward him, and I lifted myself up, mounting his huge cock. I reached down and guided his long hard dick into position as I sat down on it, feeling my hole relax again.

His cock pushed up inside me as I rode him. His hands were around my waist as I gently rocked the bed back and forth, trying to let each inch of his cock get deeper inside me. More pre-cum was oozing off my cock, and drops were landing right above his dick onto his pelvis. As he grabbed me, he started humping harder and harder. Meanwhile I was riding him as hard as I could. His cock was buried so far deep inside me I could feel it in my tummy filling up my sissy womb. I looked down and my little cock was flopping up and down as I rode his massive shaft. His balls were slapping against my ass as he pushed deeper and harder. He put his hands on my tummy as I was playing with my nipples, then he pulled me closer to him and started going faster and harder. I felt his huge manhood grow rock hard as it stiffened up. We were both about to climax at the same time. My little cock was sliding and rubbing against his pelvis, under his stomach all covered in pre-cum. He firmly gripped my hips and let out the most intense orgasm, moaning loudly as he buried his cock inside me. While I felt his load flooding my pussy, my cock exploded letting out a couple of spurts that climbed half way across his stomach. He continued to let out loud moans, while he pumped more and more of his sperm deeper into me, breeding my little ass pussy. We laid there for a minute while we tried to slow down our movement.

As I climbed off of his big pole, gobs of cum leaked out of my tight little hole, which now felt like it was gaping. Thick white seed oozed down around his shaft and his balls.

"You know what to do," he said looking down at his soaked cock.

I gently nodded and got my face down there where it belonged. I began licking the cum off of his long dick as it laid there semi erect extending up to his stomach. I could taste his potent seed, and my ass as I took his cock into my mouth, sucking it all clean. My tongue moved back and forth on the shaft and I even sucked up the little load that I had blown on his stomach as well. He held my head there, and as his cock had started getting cleaned up, and he moved my mouth down to his balls. I had each of his balls in my mouth, one at a time, licking them clean as well. Then he kept moving me lower, until my tongue reached his asshole.

"That's it baby," he moaned.

Obediently, I kept licking up all the juices as my tongue circled around his ass. It was so humiliating, but I loved serving him so much. Once I had finished, I went to the bathroom to clean up before bed. When I stepped back out, my room was empty, but on my bed I noticed something laying there, but couldn't tell what it was. As I approached the bed, I noticed it was a pair of black thigh high stockings, and another pair of matching panties. As I picked them up, I could tell that they had a strong sexual odor lingering on them.

"You don't even have to tell me...I know what to do with these!" I smiled to myself.

TO BE CONTINUED!

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Blackmailed Sissy Whore Part one

Blackmailed Sissy Whore Part 1 It's amazing how quickly life can spiral out of control. One moment your enjoying what you think is just a little harmless indulgence in your submissive crossdressing fantasy life when, out of nowhere, your life is turned upside down. It was a Saturday morning in February, 2020. I was a single guy, living the dream. I had a really good job and was living in a 2 bedroom apartment in an upscale complex a few miles South of Pittsburgh. I had transformed...

4 years ago
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The Making of a Sissy Part Twelve

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as she pulled her indoors.“Well, you’ve certainly impressed Mr Roberts, and it’s nice to see you with your clothes on again. We are quite the little harlot now aren’t we? We’ll soon have you back down to...

4 years ago
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Maid to Measure or Sissy Slave by Design Part Two

Maid to Measure, or Sissy Slave by Design, Part Two By Mistress Kathrine The room was very bright. It hurt to open his eyes so he tried to cover them with his hand but found he couldn't move it. He started going over carefully the last things he could remember. He was in a beautiful home, Kathrine? No Mistress? Oh if only he could wake up and remember what happened? As his mind began to clear he could start to see more clearly. It looked like he was in a...

1 year ago
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Becoming a Sissy Part 10

Apologies for the delay. This is the final part of "becoming a sissy". Obviously, I have packed a lot more into this story, and I apologise if it got complicated with too many characters. I'm thinking of writing another story which will take up from where we are now, but I will make it more focused on one or two characters. It's my first story, so I guess lessons.Over the next five days a plan formulated in Tom's mind. As he thought about it he would have three submissive sluts vying for his...

2 years ago
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Andrew The Unsuspecting Sissy Part VII

ANDREW THE UNSUSPECTING SISSY PART VII [email protected] *** A NOTE TO ANDREWS' FANS: I DON'T GET VERY MUCH FEEDBACK, PERHAPS 4 OR 5 PEOPLE WITH EACH CHAPTER. WHILE I APPRECIATE THE SUPPORT FROM THOSE THAT ENJOY THE STORY, I CAN'T SEE CONTINUING THE TALE IF SEEMINGLY VERY FEW PEOPLE ARE INTERESTED. SO, IF YOU ENJOY THE STORY, OR DON'T, PLEASE LET ME KNOW! MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN...

3 years ago
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Maid to Measure or Sissy Slave by Deesign Part 3

With Kind Proofing by Vickie Tern Maid to Measure, or Sissy Slave by Design, Part 3 By Mistress Kathrine The morning after Kathrine let Nikki sleep in the Master bedroom with her, she lay thinking about the things she still needed to train her pretty Sissy. Sissy Nikki didn't know anything about Kathrine's plans to marry her, and have a child with her, not yet. She decided it was time to wake her Sissy and get at least the wedding...

1 year ago
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A sissy called Jezebel Part XX

A sissy called Jezebel Part XX - Jezebel and hir entire family next attend a family wedding, where the bride is a sissy (of course.) What sexy, submissive traditions prepare the beautiful blushing bride for hir big day? Will our bride vow to love, cherish and (especially) obey, all orders, whims, without any hesitation, from hir goddess/wife/mistress and to her complete and utter satisfaction? There is non-stop teasing in the car about the bridesmaid dress. Everyone knows I adore...

4 years ago
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The Making of a Sissy Boy Slut Part 2

If you have not already done so, it may be best to read part 1 first. Your comments and ratings are always welcome. I hope you enjoy the series. M ------------------------------------------------------------------------------------------------------ The next morning, as I gradually awoke from a restful sleep, I became aware of atightness in my groin. With a start, the previous evening’s events flooded back to me as I reached down to find the thick elastic band still stretched around my...

1 year ago
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My Sissy Life Part 17

My Sissy Life Part 17 I fixed my make up and went back to cleaning, I didn't want to get into trouble because my chores weren't done. I don't know how I would explain that, 'I'm sorry mother I couldn't finish dusting because I was too busy sucking Jake's cock.'. That is not a conversation I wanted to have. I wasn't sure what was going to happen when Jake babysat me for the weekend. I had an idea that there would be a repeat of what just happened. The rest of the night. I served...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

3 years ago
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Mein erstes Mal als Sissy Part 10

Fortsetzung von:https://de.xhamster.com/stories/mein-erstes-mal-als-sissy-part-9-708712„Hallo meine kleine Schlampe“, begrüßt er mich nachdem er mich ein Zeit lang mehr oder weniger ignorierte. „Nun kommen wir zu meinem persönlichen Höhepunkt des Wochenendes“, er führt mich nochmal ins Bad und legt mir Dessous in Rot bereit, dazu ein rotes Negligees, die blonde Perücke lasse ich auf und er bittet mich, dass ich mich ganz nuttig für ihn zu Recht mache. Ich freue mich darauf endlich wieder von...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
3 years ago
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Rubber Sissy Panties Part 2

Rubber Sissy Panties Part II Clark woke up at work. He was dressed in the same clothes as in the previous day, shaven and the clothes were clean and ironed to perfection. He looked at the clock on his computer, and it was 7am, way earlier than anyone else would be hanging around. He raised himself off his chair and walked to the W/C, ready to relieve his full bladder. Not noticing his own behavior, he lowers his pants and sits down on the toilet, and points his sissy clitty...

4 years ago
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Blackmailed Sissy Whore Part Three

Blackmailed Sissy Whore Part 3 I did manage to get a little sleep. After Tiffany finally zonked out, and the continual grinding on my thigh and the relentless playing with my nipple rings stopped, I couldn't keep my eyes open any longer. Friday night was the last full night's sleep I had gotten since Marcus took over my computer, and my life. I woke up before my alarm went off, which was a good thing. I was tangled up in limbs so securely, it took me several minutes to snake my way...

2 years ago
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Lockdown Sissy part 1

Author's Note: Thanks to those who have reached out to me with story ideas. It's been difficult to get any writing done these past few months, but hopefully my head is finally back in writing mode. I hope you enjoy this nasty little fantasy. Please let me know if you have any thoughts or ideas--either here in the comments or directly at [email protected] xoxox Emshoninque Lockdown Sissy- part 1 I made a resolution to become a better sissy in 2020. It's something that has...

3 years ago
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The Making of a Sissy Boy Slut Part 4

--------------------------------------------------------------------------------------------------------------------------------------------- I spent the next hour on my own, cleaning myself up and tidying away the training equipment in the kitchen, until my attention was drawn to preparing my cum meal for the following evening. Miss Marsh had left me with a small Tupperware container, complete with lid so as it could be transported easily during my journey the following night, though I had...

3 years ago
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Becoming a Sissy Maid for Mark and Rebecca Part Three Ms Rebecca Shares Her Sexual Research of Sissies

Becoming a Sissy Maid for Mark & Rebecca, Part Three - Ms. Rebecca Begins Sharing Her Sexual Research NOTE to Review Writers: Thank you so much for the incredibly positive feedback. It is definitely motivating me to write more and write faster. Now to part three of our story. "Tell me what you know about males who are feminized so completely they are transformed into a sissy, changed from the less than manly person she had been before coming under the control of a strict...

2 years ago
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I Want To Be A Sissy Part 4

After my intense and strangely satisfying lipstick application initiation, all the women and young girls and the male pharmacist drifted off, allowing Judy to take control of her cute little pansy customer once again. I was dumbfounded that the woman I first saw coming towards me with what I thought was disgust in her eyes, was really a rougher, blunted extension of my darling wife, my Mistress Claire. Judy seemed perfectly happy to take command of me and my sissy needs. She proved...

3 years ago
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Andrew The Unsuspecting Sissy Part II

ANDREW THE UNSPUSPECTING SISSY PART II ANDREW'S SISSY EDUCATION BEGINS............ [email protected] Mother and daughter chatted while they ate their breakfast. Several sissies flitted about changing flowers and removing dirty dishes. "Mother," said Sarah. "How many sissies call the Manor their home these days?" "Hmmm," said Audrey as she placed her coffee cup in its saucer. I'd have to say with the school, the modeling agency, the internet dormitory, the domestic...

3 years ago
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Sissy Prudence Part 2

Sissy Prudence (Part 2) (by Sissy Caroline 22 December 2006) Section 1 "Prudence. Come here at once." Dressed in his maid's uniform, Prudence walked obediently into the room and then knelt down before his mother, his eyes lowered to her feet. He knew he was in trouble because she had called him Prudence. "I have just been talking to Mrs. Smithton, who tells me that she is increasingly concerned about the quality of your work when you are supposed to be performing maid duties...

2 years ago
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My Sissy Life Part 3

My Sissy Life Part 3 When I got to my room I saw the Hello Kitty dry erase board on my door. There was a note from my brother that said 'Sissy, I need my jock strap clean by Friday morning.' Oh good, I get to hand wash my brothers jock strap again. Is it Christmas already? Almost every day there is a note on the board from someone telling me that they want me to do something. I walked in my room. I still can't believe how ultra girlie my...

1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Mommys Dirty Sissy Slut part 2

Mommy's Dirty Sissy Slut part 2 by dirteesissy Please read part 1 before enjoying this instalment. Chapter 5. After I had finished cleaning Lisa's toilet with my tongue, she had me brush my teeth, as she finished her bath. I dried her with a fluffy white towel before helping her dress. Kneeling in front of her as she stepped into a pair of darling lacy pink thong panties, she bade me to pull them up. I obeyed and was overjoyed to serve her in such an intimate way. A pink...

4 years ago
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Becoming A Sissy Slut part 2

I awoke Sunday morning alone in Kassy’s bed, still in the tight mini skirt, my ass was deliciously sore bringing back a flood of memories from last night. I had spent the evening in full drag dressed as a slut and serving my mistress’s rubber cock followed by swallowing my own cum. It was hands down the best night of my life, I had never came so hard, and the rush I felt while serving her was a high that I’d never known. I rolled out of bed and stood up, my wig had fallen off in the night...

4 years ago
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A sissy called Jezebel Part VII

A sissy called Jezebel Part VII - Jezebel has finished hir tour with the Head Mistress into the secretive dungeon/reform school below the fair walls of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. But is the Head Mistress entirely done with Jezebel? Additionally, what ever does one learn in a 'sissy life skills' class? I require the gurls in my harem to crawl on the floor at home and in private at the office. So get on...

3 years ago
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Sissy Prudence Part 3

Sissy Prudence (Part 3) (by Sissy Caroline) Section 1 "That's our Sissy Prudence in the garden. Isn't he a delight?" Bridget looked out the window and, despite the fact that boys were not really her interest, she found the sight presented to her was quite exciting. She had never thought that a boy in a dress could be such an erotic fantasy. Prue was working in the garden, which was something he now really enjoyed as a break from his duties inside the house. Not that he was...

3 years ago
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Americas Next Top Sissy part 3

After waking up, Jim finds himself in a feminine bedroom with the 11 other naked men. When the Nurse from the previous night enters the room dressed in a leather cat suit and introduces herself as Ms J, she wakes the men wake up and they soon learn to behaviour or implants in their bodies will make them. Now forced to wear ultra feminine clothes and wait holding each others hand for the looming elimination! Part 3 Jim is standing in the middle of the bedroom waiting for Ms J...

2 years ago
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A sissy called Jezebel Part VI

A sissy called Jezebel Part VI - Jezebel's inspection has been completed at the Head Mistress's office of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. Jezebel is taken by the Head Mistress into the secretive dungeon/reform school below the fair walls of Templeton. All sorts of secrets and surprises are revealed. Headmistress Saxon looks at me. "What class did you just miss?" "Deportment, Headmistress." Forty five minutes...

2 years ago
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Sharons Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party(Prior chapter is Sharon’s Sissy Saturday)The next morning Mistress was kind enough to let me sleep in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I...

2 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

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