Sissy School - Part 1 free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
SCHOOL FOR SISSIES By Missy Crystal I was sitting at the table eating my cornflakes and drinking a glass or orange juice when I suddenly began to feel woozy. It was hard to keep my head up and I couldn't seem to focus. "Mmmmommm," I slurred. "Immmmm feeeel funnnny." Mom was standing at the sink. She turned around. "Of course you feel funny. I put a big dose of tranquilliser in your orange juice. I warned you what would happen if you didn't mend your ways. You were already on probation and the call I got from the principal telling me you were expelled was the last straw. It's off to boarding school for you. "Pleezzzeee Mommmm," I pleaded with her. "Noooo. I'lllll beee gooo...." I was losing my concentration. "Gooodddd," I managed to finish. She looked at me sternly. "I've heard that too many times before. Since your father walked out and left me to raise his brat son, I have had no peace. The neighbours, the police, your school. No more promises and no more chances. I have already made arrangements for you to be placed in a special academy for incorrigible boys like you. The drug is to make sure you don't give me any trouble getting you there." Mom came around to where I was sitting and lifted me to me feet. I was completely limp. I had always been small and people usually thought I was much younger than fourteen. Mom had no trouble lifting me up and dragging me out to the car. She laid me down on the back seat. She got in and headed out of the garage. I couldn't see where we were going and time just flowed as I drifted semi-conscious during the trip. Finally, the car stopped. I heard the door open and a woman's loud voice. "Ahh, he gave you no trouble I see. Yes, Yes. Much easier this way. It makes it easier for us to get them settled into their new life too." Mom must have been speaking more softly, because I only heard the woman's part of the conversation. "Visit him? Oh, no, no, no. Once you leave him here, he is no longer your son or your problem. You do understand? Good." The door opened and I managed to look up. There was a very large woman dressed in a shiny black skirt and blouse. She had shoulder length blonde hair and exotic looking makeup. Dark lipstick and dark eye shadow. She reached in and pulled me towards her. Then she easily picked me up in her arms like a baby and carried me into the house. As we went in, I heard the car drive off. As soon as we went in, I heard what sounded like a bunch of giggling girls. What kind of school is this, I wondered dreamily? Then I heard funny voices. "Oh, Mithtrith Mary, Oh, Oh. She'th so scrumpthus, I could'th justh eath her awlll upth. Another high pitched voice asked, "Can'th weh pleath pway with her? Then another voice, "Pwetty pleath?" The voices were all so sing song and lispy, I was sure that there drug must have done something to my hearing. "Now, now girls," the woman scolded them. "You know you silly heads must be patient. Your new sister must be properly prepared before she can play sissy games with you. Now, run along and get the special chair ready. Hurry, hurry." I heard footsteps as the girls headed off. My groggy thinking was that Mistress Mary, as the girls called her, must be the Headmistress of the school. Maybe it wasn't going to be so bad after all, if there were girls here. And they thought I was cute. I wondered if they were pretty and then I thought that it really didn't matter, because I had been trying to get laid since I first found out that my wiener got hard and spurted if I played with it. None of the girls I knew wanted anything to do with a little runt who had a bad reputation. Whether the girls were pretty or not, maybe I was going to get lucky. Mistress Mary turned into a doorway. I had been in the principal's office enough times to know what it looked like. There was the usual desk, chairs and filing cabinets. She walked over to a leather covered table with metal pieces at the end and laid me down. It looked like something you'd see in a doctor's office. Well, maybe the school nurse used the office too, I guessed. Then she started to take off my shirt. What the heck? I made a made a feeble effort to stop her. Even at full strength I wouldn't have been a match for her. She looked down at me and then moved away. Mistress Mary, picked up something from the desk and walked back. She held it up for me to see. It was a black leather paddle about a foot long. "There is only one rule here," she said sternly, "complete and total submission. Any disobedience or even the slightest resistance will be severely punished." She swished the paddle back and forth for emphasis. "You have already earned yourself three strokes," but since you are a new student, I will suspend your discipline this once. However, if you give me further cause, then it will be doubled." From the look in her eyes, I knew she meant business. She put down the paddle and again started to unbutton my shirt. Maybe she was a nurse too and was going to give me a school physical. I thought about trying to jump up and escape, but then what? I had no idea where I was and I was still too weak to make much of an effort. I decided that for now I would play along and wait for my chance. Besides, I wanted to get a shot at the girls. After all, I though confidently, what's the worst that they can do to me. A spanking? How bad could that be? After all, there are laws, I reassured myself. After she had my shirt off, she reached down and pulled my undershirt over my head. I expected her to start doing the pushing and poking that usually happened during a physical. Instead, she went back to her desk and returned with a strange looking belt. It was about an inch wide and had metal rings to which some type of bands was attached. She reached under me with it and fastened it around my waist. Then she took one of my wrists and put the band over it. I heard a click as it snapped shut. Before I realized what was going on, she snapped the cuff on my other wrist. This was getting really weird. Now I had my arms pinned to my sides. I looked up at her. She smiled back at me. Once I was restrained, she removed my shoes and socks, then unsnapped my jeans and started to unzip them. I tried to sit up, but with the effect of the drug and my hands useless, I barely managed to lift up my head. She turned to look at me with one eyebrow raised, just waiting to see whether I would be foolish enough to provoke her. I started to speak and she put her finger to her lips. I immediately put my head back down. She went back to undressing me. Finally, I was in nothing but my underpants. She pulled them down and I was naked. Then, to my surprise, she lifted me off the table and stood me up. The drug had pretty much worn off, but I was still unsteady and she held me up. "Let's go," she said. "It's time for your initiation to our school." Mistress Mary, directed me towards the door. It struck me that she intended to parade me out for the whole school to see naked. I hesitated. She looked down at me with a frown. "I warned you," she said sternly. Together with your three suspended strokes, that is now six. I gave her my 'I'm really sorry' look. "Neither pleading nor promises will get you any mercy. The punishment will be carried out. However, the girls are waiting for your initiation and I don't want to disappoint them. Therefore, it will be postponed until later." She paused. "Make no mistake and take no comfort," she warned me. "It will be just as painful. Only a more convenient time for you to have a blistered bottom." With that she began again to move me towards the door. This time I had no choice and I let her guide me out into the corridor. I looked nervously around, sure that I would be gawked at by the students and teachers. To my surprise, the corridor was empty and all I heard were the giggling voices of the girls. We moved into a large room. I got my first good look at them. Each of them was a knockout. Beautiful long hair, elaborately styled into cascading curls; lots of makeup, bubble gum pink lipstick and pastel eye shadow with long, sensuous lashes; and the hands that they were waiving about had matching pink nail polish. What was really strange, was the way they were dressed. It must have been some kid of school uniform, because I had never seen girls wearing that type of outfit before. Each of them wore what looked like a baby's dress in soft pastel colour, covered with frilly lace and ruffles and puffed out with frothy white petticoats, so short that your could see their matching ruffled panties. Their legs were bare and each wore they same lacy white ruffled ankle socks and incredibly high heeled shoes with a strap across their ankles. I had to look twice to make sure I wasn't hallucinating from being drugged. They were all doing something in the centre of the room. I couldn't see what it was, because they had their backs to me and as they bent forward their dresses rode up even further exposing even more of their frilly panties. "Girls," Mistress Mary announced, "your guest of honour is here." With that they all turned around and started towards me with the most peculiar walk. Their hips swivelled and their bottoms wiggled, making their short dresses flounce around. There hands were held out in front of them with limp wrists and swished back to and fro as they sashayed their way across the room. The strange thing was that it didn't seem to think anything of a bound, naked boy standing in front of them. From their comments, you'd have thought it was something they saw every day. "Ohhh, Mithtrith Mary, he'th soo adorable," gushed one in that same high pitched lispy voice I heard when I first came in. "I couldt jutht eat him awlll up." The other girls clustered about us and were equally enthusiastic about getting their hands on me. "Now girls," said Mistress Mary, "there will be plenty of time for all of that. Right now, you need to show our new student to his seat." That sent all of the girls into a fit of giggles. "Yeth, yeth," they said enthusiastically, as two of them took hold of me under my arms. They just about swept me off me feet as they guided me back to where they had been gathered before we came in. The girls stopped in front of a chair. It had a straight back and flat seat. I was puzzled what this initiation was all about and then I looked closer at the chair. The seat had a shaft sticking up in the middle, maybe four inches high, and it was covered with what looked like a piece of slippery rubber. It took me a second and then I recognized it from health class. A condom. It didn't take a genius to figure out what they had in mind for me. What the hell kind of school was this? I was supposed to be scoring with the girls. Not the other way around. Before I could do anything to stop them, the spun me around and two of the girls grabbed my legs, pulling them out from under me. Then the two holding me under the arms lifted me up and positioned me over the tip of the shaft. I pleaded with them. "Please, don't do this to me. I don't want that in me. Please stop." It did not do any good, as I felt the tip beginning to press against my puckered virgin rosebud. I looked up for Mistress Mary, hoping that she would intervene. She had a big smile, obviously enjoying my humiliation. One of the girls holding me moved her lips to my ear. She started licking and nuzzling it, distracting me. Then she whispered seductively, "Pweeth, my darling, don't stwuggle. Ith will only make ith painful and you wilth hurt your delithious little heiney." Then the girl on the other side of me started to lick and nuzzle me other ear. By now the shaft was deep inside me. "Relaxth, sweet cheekth," she whispered to me. Finally, the shaft was all the way in and my butt was hard against the seat. The two girls kept pressure on my shoulders while the two girls holding my legs spread them in the air, making sure that I got the full penetration. Then I heard a click and the shaft started vibrating and slowly moving up, then it started to withdraw, then it thrust up. The girls were all smiles and giggles as it went up and down inside me. The shock and surprise of the reaming I was getting made me gasp. The two girls holding me down must have taken the sound as encouragement, because they returned to licking and nuzzling on my ears, kissing and nibbling their way down my face to my neck while using their free hands to rub and pinch my nipples. I thought that only girls got off on having their nipples played with, but it felt really good as they moved their mouths down to lick and gently bite them. I closed my eyes and a wave of pleasure washed over me. "All right, Sissy Heather, your turn," I heard Mistress Mary say. I opened my eyes and saw a girl getting down on her knees while the two girls holding my legs kept them spread apart, so that I was fully exposed. Of course, between the sensuous attention being paid to my nipples and the vibrating shaft going up and down in my butt, my little soldier was at full attention. Sissy Heather wasted no time, using her pink painted fingernails to tickle and tease the shaft while fondling my balls with her other hand. I don't know how she learned the tricks she was using, caressing, squeezing, massaging, but I was about ready to explode. Then she bent forward, opened her pink-coated lips and began to gently kiss the tip. I saw her coax out a dribble of pre-cum, but instead of being turned off, she licked it off and then closed her mouth over the head while pumping the shaft. I was ready to blow my load and tried to warn her, "Ahhh, Ahhh, I'mm comminggggg," but she kept her lips wrapped around the head and continued to suck and stroke. I would get myself off looking at girls in their bras and panties in Mom's catalogs, but I only got a couple of globs of cum. I never knew I had that much in me as spasm after spasm spurted into Sissy Heather's eager mouth. I was sure she was going to choke, but she kept on sucking and pumping, coaxing out the last drop. I was exhausted and slumped back in the chair, not even noticing the moving shaft I was still sitting on until I heard the click and felt it stop. As Sissy Heather got up, I could see a little drops of my cum on her lips. "Okay, Sissy Tammi, your turn," Mistress Mary announced. One of the girls, who had been holding my legs went over to Sissy Heather, got down her knees, arched backwards and opened her mouth. Sissy Heather swished her mouth like you'd do with mouthwash and then bent over and drooled a load of cum mixed with her saliva into Sissy Tammi's mouth. "Okay, Sissy Cindi," Mistress Mary called out. Sissy Tammi got up and the other girl who had been holding my legs took her place. The cum swapping continued from girl to girl with Sissy Danni and Sissy Nicole taking their turns. The last girl holding a mouthful of drooled cum walked towards me. Before I knew what was going on, she straddled my lap and sat down facing me, provocatively wiggling her butt, so that the ruffles on her frilly panties were sliding back and forth over my still sensitive penis. I was so distracted that it wasn't until she moved her mouth towards mine that I realized that she wanted to feed me my own cum. No way, I thought, clenching my teeth. She gave me a pretty smile, which let little dribbles of frothy cum bubble out of the corners of her mouth, then quickly reached behind me with her right hand, grabbing my hair and forcing my head back. With her other hand, she pinched my nose shut. I had to me open my mouth to breathe and when I did, she quickly spit what was in her mouth into mine. To the great amusement of the other girls, I sputtered and choked, dribbling most of the salty white fluid down my chin. After giving me a big, sloppy wet kiss with her cummy lips and using her tongue to lick my face and neck clean, she climbed off. Mistress Mary came over. "It seems like you've taken quite a liking to our initiation chair," she commented, as I was still impaled on the shaft, "but its time to get up. Girls, I am sure our new student appreciates the way you welcomed him to our school. Now you may have playtime." To my astonishment, the girls immediately paired up and began making love to one another without any shame, passionately kissing, hugging, sliding their hands into each other's panties, moaning with delight. "Come along," said Mistress Mary as if nothing was happening. TO BE CONTINUED

Same as Sissy School - Part 1 Videos

4 years ago
  • 0
  • 39
  • 0

Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
  • 0
  • 39
  • 0

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...

2 years ago
  • 0
  • 28
  • 0

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
  • 0
  • 24
  • 0

Sissy School

Chapter 1: Welcum to Sissy SchoolDear Diary, My name is Aaron Antony, 18 year old bi curious male. For the past month I have been seeing another man, his name was Geroge but he preferred that I call him Daddy. I never thought of myself as being completely Gay, because I would still find girls attractive, and Daddy knew this which was fine by him. But one day at the beginning of summer time Daddy suggested I should go to a special school for 4 months, a place where other boys confused about...

4 years ago
  • 0
  • 37
  • 0

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
  • 0
  • 40
  • 0

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."...

1 year ago
  • 0
  • 24
  • 0

Sissy Puppy Fifi Part2

Chapter 2 I tried as best as I could to get comfortable curled up in the corner of the room. At first I kept squashing my tail which either caused the vibrations to start or pushed the plug further inside. I had eventually worked out the best position to lie in when Mistress appeared. "Time for bed Fifi," she said as she attached the pink lead to my collar. I was then led through the house and up to her bedroom. This was a strange feeling to enter her bedroom not in my usual maid's...

3 years ago
  • 0
  • 31
  • 0

SISSY DANI PART3

CHAPTER THREEMistress Jennifer and Mistress Susan's plans to create an entire"harem" of transformed men and boys continued apace. The lure ofTeasing Tammy (the transformation name of Susan's teen-agedbrother Tommy) proved quite effective. Each of the young men (theyoungest just 14, the oldest 22) the little tease brought back tothe home we all now shared was turned into a different kind offeminized sex-toy, all designed to please the Mistresses andtheir dominant friends.The little...

4 years ago
  • 0
  • 63
  • 0

Sissy dannis birthday party

My last "true life" story was about how I became Heidi's sissy crossdresser "Danni" - I only explained the initial experience of Heidi coming home to find me in one of her dresses - followed by spankings, punishment and eventually getting pegged by her wearing a strapon. Of course there is MUCH more to what happened next (like being taken out in public and going shopping, to hair salons, etc...), but I'd like to for now jump ahead to what happened to me on my 19th birthday. By then I...

2 years ago
  • 0
  • 38
  • 0

Sissy Sisters Party

SISSY SISTERS PARTY by Throne Bob Clump, the friendly retired guy at the end of the street, was taking advantage of the mild weather of late Spring. He was sitting on his front porch enjoying a fine cigar. Or at least a cigar. Those fine ones cost a lot more than what he smoked. As he sat there, a car pulled up across the street, in front of the house diagonal from his. In the dimming light of dusk he saw two figures emerge. The first was a woman, quite attractive in a slender,...

4 years ago
  • 0
  • 26
  • 0

Sissy Girl Party

SISSY GIRL PARTY by Throne Danny felt so ashamed, standing there before his wife Melba in a pink and white party dress that would be appropriate for a nine year old girl, not a grown man like himself. He cringed inwardly and unconsciously took one of his short pigtails and wound it around his finger. His feet were shod in pretty ballet-type slippers, pink ones with little rhinestones on them. "You look so sweet, Dee Dee," she said with a smirk that he knew all too well. He had...

4 years ago
  • 0
  • 29
  • 0

sissy schoolgirl and her black daddy

I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning...It was summer time. As always I spent my summers hanging out and occasionally mowing neighbors lawns for some extra cash. Although I wasn't exactly the big high school jock who all the girls saw mowing the lawn shirtless and fawned over, I...

3 years ago
  • 0
  • 39
  • 0

Sissy Bachelorette Party

'You want it again?' She said, as she climbed between my legs, spreading them with the force of her knee. 'Yes Mistress.' I said, turning my head to the side. Her gloved hand grabbed my chin and turned it towards her. 'You want to be my girly lesbian bitch?' She said, as she tweaked my puffy nipples with her other hand, the dry latex chafing me. 'Yes Mistress - I want to be your girly lesbian bitch,' I rubbed my horny cunt against her stocking clad leg, ignoring the pain, wanting, no, needing...

2 years ago
  • 0
  • 43
  • 0

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
  • 0
  • 40
  • 0

Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

1 year ago
  • 0
  • 29
  • 0

Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
  • 0
  • 31
  • 0

Sissy Slumber Party

Sissy Slumber Party I was on my way to the slumber party and I was so excited that my panties were getting wet. As I felt the moisture between my legs I blushed and giggled. My high heels clicked on the sidewalk as I went and my full skirts and petticoats swooshed around my baby smooth nyloned legs. I wiggled down the street and my long curly hair and bangle earrings swung from side to side as I walked. Some men in a passing car whistled at me and I just smiled. But my panties...

3 years ago
  • 0
  • 43
  • 0

Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
  • 0
  • 53
  • 0

Sissy Farm Chapter Eleven

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

2 years ago
  • 0
  • 56
  • 0

Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

4 years ago
  • 0
  • 36
  • 0

Sissy Farm Chapter Eighteen

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

2 years ago
  • 0
  • 35
  • 0

Sissy Hypnosis Fun

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

2 years ago
  • 0
  • 51
  • 0

Sissy gets a black master

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

3 years ago
  • 0
  • 34
  • 0

Sissy Training at Last

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

3 years ago
  • 0
  • 36
  • 0

Sissy Farm 20

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

2 years ago
  • 0
  • 40
  • 0

Sissy Farm Chapter Fourteen

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

4 years ago
  • 0
  • 30
  • 0

Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
  • 0
  • 59
  • 0

Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
  • 0
  • 40
  • 0

Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
  • 0
  • 44
  • 0

Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

2 years ago
  • 0
  • 40
  • 0

Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
  • 0
  • 52
  • 0

Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
  • 0
  • 33
  • 0

Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
  • 0
  • 49
  • 0

Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
  • 0
  • 36
  • 0

Sissy Farm Chapter Twelve

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

4 years ago
  • 0
  • 29
  • 0

Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

3 years ago
  • 0
  • 38
  • 0

Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

2 years ago
  • 0
  • 34
  • 0

Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
  • 0
  • 32
  • 0

Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

2 years ago
  • 0
  • 40
  • 0

sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
  • 0
  • 33
  • 0

Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
  • 0
  • 29
  • 0

Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

4 years ago
  • 0
  • 54
  • 0

Sissy Farm Chapter TwentyOne

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

3 years ago
  • 0
  • 29
  • 0

Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
  • 0
  • 32
  • 0

Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
  • 0
  • 32
  • 0

Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
  • 0
  • 35
  • 0

Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
  • 0
  • 30
  • 0

Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

4 years ago
  • 0
  • 32
  • 0

Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
  • 0
  • 40
  • 0

Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
  • 0
  • 40
  • 0

SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
  • 0
  • 46
  • 0

Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
  • 0
  • 39
  • 0

Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
  • 0
  • 31
  • 0

Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
  • 0
  • 32
  • 0

Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

3 years ago
  • 0
  • 62
  • 0

Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
  • 0
  • 36
  • 0

Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
  • 0
  • 34
  • 0

Sissy Farm Chapter Eight

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

Porn Trends