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Sissy the Redhead Mammas Home Pt III

Introduction: If you dont like stories that involve incest, I suggest you stop here. The rest of these chapters will have increasing amounts of it. If you like that sort of thing, its only getting started. Sissy the Redhead: Mammas Home Pt III I couldnt wait to get out of the car when I pulled in out driveway. A six hour drive home from picking up my sixteen year old son from his fathers, and the whole time I felt his eyes on my legs and chest. Granted, I was wearing a hot leather mini-skirt,...

Sissy Night at Brucy s

• We moved into auntie’s place, who is desperate for sexual relief, she being single. Dad discovers me dressed in auntie’s clothes and makes me fuck the neighbor and more. I am still in college and have friends who think outside the box.• This happens on a Friday morning and I stay home for the weekend to pleasure Harry our neighbor, who loves my dressing and looking gurly. Daddy thought my long blonde hair to my waist was sexy, and with my plump butt, skinny by some opinions, was perfect hand...

Sissy the Redhead Mamma s Price Pt VI

My kids had been on their “walk” for a couple of hours now. Of course I knew better. I was sure they were across the street involved in some sort of hot, sticky, depraved and illegal sex act with either one or both of my “classy” neighbors. I didn’t mind. They were my kids, after all, and were bound to be at least as horny as I was. The only problem was, I was feeling left out. Fucking my sixteen year old son, Luke, was a pleasure I had only enjoyed once, yesterday. And I...

Sissy Downfall 2

Sissy Downfall 2 * My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress, hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really lucky the young mistress would have me lick her to orgasm. She had the most fragrant tasty pussy that I had ever experienced. Sometimes she would alloy me to play with my clit as I served her and if really...

sissy Meets her New Daddy Ch 1

So I took the plunge and put out an ad on Craig’s List. I was travelling in a city about 120 miles from home and figured this was far enough to not be found and close enough to go back if I had success meeting a fuck buddy that could be longer term. I got myself all primped and wore a tight print dress, matching bra panty set subtle yet slutty makeup and my fave long blonde wig. The ad attracted immediate attention and I was sure to mention I was a sissy who wanted to be treated like a girl. I...

Sissy Downfall 2

Sissy Downfall 2*My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress; hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really lucky the young mistress would have me lick her to orgasm. She had the most fragrant tasty pussy that I had ever experienced. Sometimes she would alloy me to play with my clit as I served her and if really...

Sissy Downfall Ch 02

My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress; hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really lucky the young mistress would have me lick her to orgasm. She had the most fragrant tasty pussy that I had ever experienced. Sometimes she would alloy me to play with my clit as I served her and if really lucky I was allowed...

sissy fucked by two big men until i was sore and m

I got to know these two guys at work, they were sporty and worked out. I used to listen to there talk on a Monday about the girls they had fucked over the weekend. I thought they were a couple of macho strait guys into girls and that was it. All the time, under my trousers and shirt and tie, I was wearing stockings, pink satin sissy panties and a lacy bra. Im a sissy! What more can I say, when I get home I take off my trousers and horrible black socks and shoes and put on my blue satin Alice in...

Sissy picked up in hotel

...you are having a drink at the hotel lobby bar, another night in a hotel working away, sipping your drink thinking how you are becoming sick of the same boring hotel routine and looking around at the people checking in and out, the bar is relatively quiet for this time of night. A girl walks up to the bar next to you and asks for a drink, you glance over and the first think you notice is her bobbed blonde hair, down to just below her jaw line, she catches your eye and you become more...

Sissy discovers part 1

This is an original fictional story, where a young woman finds that she has an admirer at home, and unexpectedly decides that she likes the attention. I'll post more parts of the story over time if there is interest so please comment.Outwardly Sissy looks like your average pre-college teen with a wholesome family. Cute and sexy she has a special effect on all that meet her that creates lusty thoughts in her fiends, and as she will find out, particularly her younger brother. When Sissy finds...

Sissy Emma is Turned Chapter 5

After that they let me go home.Everything had been removed other than the cage which they said should remain on throughout the week to ensure my mind was attuned to being a sissy. Once home I showered myself completely and fell into a deep exhausted sleep.The following day I went to work and tried to act as normal as I could despite the fact that I was wearing stockings and panties underneath as instructed, not to mention having a butt plug stuffed up me and my 'sissy clitty' in a cage. All day...

Sissy Sabrina Goes Out On The Town

Sissy Sabrina Goes Out On The Town ? by: Sweet Sabrina Chapter 1. It all started with the email Mistress sent me. Okay I guess technically it all started when I began to serve her via email. She had a website and for a small monthly fee she would give assignments to her sissy slaves. I had done all the assignments on her website and had now graduated to receiving personal emails with instructions on what she expected me to do next. Of course being email she couldn't tell if I...

Sissy to Be Chapter Six

Sissy To Be, Chapter Six - By: Beverly Taff List of Characters: Me: Robert, now Rosie; Wendy: My twin sister; Angela: Our younger half-sister from mother's second boyfriend; Doris: My drippy mother who lets everybody walk all over her; Aunty Janet: My mother's pushy domineering sister; Harriet: Our friend from the next farm; Aunty Margaret: Harriet's Mother; Jessica: Harriet's older sister. Sissy To Be...

Sissy to Be Chapter Eight

Sissy to Be ? Chapter 8 ? By: Beverly Taff List of Characters. Me Robert, now called Rosie! Wendy My twin sister. Angela Our younger half sister by my mother?s second boyfriend. Doris My sad working mother who lets everybody walk all over her. Aunty Janet My mother?s pushy domineering sister. Harriet Our friend from the next farm. Aunty Margaret Harriet?s Mother Jessica Harriet?s older sister Charlie My New found clubbing friend Sally Charlie?s...

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...

Sissy Husband Gets Punished

SISSY HUSBAND GETS PUNISHED by Throne "Well, well," said Sara. "Looks like my sissy husband has gotten himself in trouble again." "B... but, I just wanted to try your new shade of lipstick," Bobby explained nervously. "Don't you have your own make-up? Didn't I give you some stuff I didn't want anymore? And buy you some other things at the dollar store?" "Yes. It's just..." Bobby was standing in front of the mirror on the medicine cabinet in their bathroom. He had on...

Sissy Sierra

SISSY SIERRA by Throne Connie called out from the den, "Sierra, the girls and I are waiting for you." In the hallway, her husband stood still, hugging himself. The last thing Seymour wanted to do was go in there and have his wife and her three friends see him. It was bad enough that, several months ago, she had made him legally change his given name from Steven to Seymour, just because she thought the new one was funny. After that she had begun sissifying him in earnest. First...

Sissy Of The Lamp Part 1

Saarleena licked his heavy balls savouring the musky taste, sensing the potent seed within, her tongue gliding onto the hot ridged shaft. Half way up the hard eighteen inch pole she paused and took a deep breath. "Please lord release me.....I have been in bondage to the lamp for centuries," she begged. The demon lord looked down at her a knowing smile on his face. "Saarleena you know as do I that I cannot grant that request." She sighed and returned to licking his hot shaft much...

Sissy gets unexpected surprise from wife mistres

Me and my wife get dressed and head out to what I assumed was a ordinary date night. As we are driving, she tells me that we need to make a stop somewhere. She directs me where to go and we arrive to a building. We go to a room and you knock on the door. This well built and athletic black guy opens up the door and says what’s up to you and me. I’m confused, but I go with it. He invites us in and points us to another room and as we walk in, you turn and tell me to go in the bathroom, clean...

Sissy 101

Wanting more and never being satisfied,I began exploring other avenues to achieve orgasmic pleasure. One day I came across a paperback book, "Pretty boys in panties." I had never been so aroused. The more I read, the more stiff my little prick became. At one point,all I did was touch myself and I erupted in my shorts. I had to find some panties of my own. Living with my Grandparents and my sister,I searched the hamper and found two pairs, one satin the other white cotton with little pink...

Sissy Is as Sissy Does

A tiny black skirt hugs her tight rump; black garters set off her milky thighs; seamed stockings veil her long legs like smoke. Her sheer silk blouse is buttoned demurely to her throat, but her rosy nipples are stiff beneath it; her hair is pulled back primly, but her lips are lush and blood red. If heaven had a librarian, this is what she would look like. Had I spotted this creature in a bar, I would gladly have bought her champagne all night for just a single glance from the sultry eyes...

Sissy Julian Chapter XI Trap Shooting

Sissy Julian - Chapter XI, Trap Shooting by: sissystevie Julia plays the trap for W. Badford Milhous III's really bad day. Dominica rules, and Julia's Jock fitting is coming as the next and penultimate chapter. Caution: Heavy XXX BDSM at the end. As always, this is a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. Sissy Julian ...

Sissy s stroke story for Deebsflo Part one

Cast: Dee (The Master), Jennifer James (The Movie starlet) The Sissies: Mika, 5’11”, light brown long hair. Sammie, 5’9”, peroxide blonde, with a fringe. Bobbi, 5’7”, brown curly shoulder length hair.. Glenda, 5’4” brunette, bob-cut style, Toni, 6’, leggy peroxide blonde, long hair. Terri, 5’8” Brunette with a fringe and Alexi, 5’9” natural blonde with long platted hair.Part one In all his years, Dee could not recall seeing such a look of desperation and desire as he did now with Mika....

Sissy wife for a Turkish man

Confessions of a girl slut 8Sissy ‘wife’ to a TurkI mentioned in a previous confession - where I first had sex with a black stud in Berlin - that I had been seeing an Arab guy so now I want to set that down too on record!I moved to Berlin fifteen years ago, partly for the culture - great music and opera and cheap! - and partly for the sex scene. I thought that as a sissy if there was so much going on, then there must be a lot of sex for sissies. If there was, I found it difficult to source....

sissy wants to be black man s slut

Hi Sweeties! Guess what? Well, adult arcade sissy, Miss Terilyn Bardot, got her ass whipped but good the other night. It happen at an adult video arcade in Providence, RI.One of the reasons Terilyn likes going there is because they could care less what kind of sex goes on in those preview booths. in fact they installed larger booths that hold up to 6 occupants. A lot of the adult bookstores, mainly the ones in Massachusetts, have signs posted to the effect of no sexual behavior allowed, or, one...

Sissy Headhunters

SISSY HEADHUNTERS by Kimmie Holland and Meeah Mackenzie **One** Andy tried not to be obvious about it: but it was hard not to notice that there wasn't another white person in the entire restaurant. He'd let Mr. Asad pick the place of their lunch meeting. Maybe that was a mistake. But he wanted to make sure everything was to the black man's liking. Andy hadn't landed an account in months so when he'd been contacted by a corporate...

Sissy Social Work

Sissy Social Work I couldn't help myself. Wearing tight, sheer panties all day at work, or thongs with a string up my ass. Or pantyhose against my ass and cock, feeling them rub against me every move I made, leaking constantly. Or even garters with a belt if I was feeling particularly daring. I shaved nearly every day, everything below the waist. Practice makes perfect and I was able to get to everything, even around my ass, with strategically placed mirrors. I even managed to avoid...

Sissy Story Chapter 01

Mom and Dad and I were a family. My first memories were of three of us, Mom and Dad and me. We lived in wonderful big house with a pool and a maid to help with the cleaning, and men who came by to do the yard and the pool. I didn’t see it as privileged, rather as reality, but we had a lot of money. Dad left when I was six, in the summer after first grade. I cried, but it didn’t help, he left anyway. At least the yelling stopped at home. Instead, there commenced a time of Mom crying...

Sissy the Redhead Her First Cock Pt II

Introduction: They wil continue to bet better and better Sissy the Redhead: Her First Cock Pt. II I couldnt believe my plan had worked so well. That hot housewife across the street was even more game than I had thought. I had dressed as slutty as I could, digging out clothes from three years ago when I was only ten years old, squeezing into them, and flaunting my tight little thirteen year old body all over the yard pushing the lawn mower. It only took twice before she came over an made her...

SISSY

SISSY Looking at me now, one will have an extremely difficult time believing this story. But let me assure you that every word is true. It started late one spring afternoon. The weather was typical spring weather, windy, wet and cold. I was walking home from high school, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was very small, looked 16 and feminine. If you’re thinking...

SISSY KNOWS THIS WILL ONLY END IN HUMILIATION BY

SISSY KNOWS THIS WILL ONLY END IN HUMILIATION BY BBC_ But will it be from what i suggest or will it be from him being absolutely disgusted and angry at me for even thinking he might enjoy this.And let alone stupid enough to ask such a real man like him something only a sissy faggot would want .So my newest sissy items i ordered had arived so i decide to get real high and get real dirty and i wanted to make myself feel really pathetic and humiliated so i dicided to go to the local store and...

Sissy Hotwife Spa Story

I have booked us a room at a nudist spa just off outside London for a couple of nights.Before we go there we do some shopping, you choose some stockings, knickers and a little mini skirt but they are not for you, they are for me. We also bought a dildo, lube and condoms.We go into the spa and are showed to our room and drop our gear. We strip off and make our way down to the spa. We go out into the wet area and start with a swim and splash around naked for a while. Then we go to the steam room...

sissy maker 2

Its became so clear he was going to keep me as his secret sissythe next morning i had clear instruction waking up dizzy still plugged and the buzzing waking me up my phone ringing daddy texting me''morning cindy , daddy is working until 17 after that i want you getting dinner done as i relax''''i want you to go get your order at this store before you come home''i never felt so shyhe finished by sending a pict of me in panty ass up taking his bbc''never forget who is your daddy''i felt like a...

Sissy Staycation

The Sissy Staycation Dennis was so close to cumming he couldn’t see straight.The vibrator up his ass hummed against his prostate. His meager dick was slick with precum, with the head just popping out over the top of a pair of lacy panties.He planted his feet on the coffee table in front of the couch, spreading his legs. He caressed his aching balls through the panties with one hand while the other hand toyed with his nipples under the thin, lace babydoll that covered his top. He watched the two...

Sissy Teaches Me Part One

Okay, I’ll admit it. I am still a virgin. There, I said it. There is nothing wrong with being a virgin. I am actually quite happy being one. After all, I am sixteen. Yeah, yeah, I know, most sixteen year olds have lost there virginity by now, but my hymen is still intact. Well, from the normal way, that is. I guess one reason why I am still a virgin is because of being a little sister and seeing my older eighteen year old sister pretty much give hers away. I cannot count on my hands how many...

Incest

sissy love daddies bbc

Its so nice and fun to walk in skirt at night, dress up and waiting at the park where there not enough lights,my little polka dot white string keeping the buzzing plug in place, in my wet horny sissy boy pussyall it needs is one of these factory worker to see me and ill be sucking a bbc in no time, like it happens to sissy like me all the time when we go out dress like slutsmy hearth starts to beat when i saw these 3 daddies walking toward the parking lots near the parkmy sissy nature in full...

Sissy Fantasy Part 1

Part 1:I walk into a seedy motel in LA. Old woman at the counter gives me a slip with a key card in it. When I unfold the slip, there’s a note. All it says is…“10-day load, sissy”I’m immediately aroused. I walk to the room, trying not to be seen, and I feel my heart racing. I key into the door. The lights are dim, but bright enough to see.He’s standing there, tall and lean, wearing business dress attire and his V for Vendetta mask. “Take off your sweatshirt,” he says. “And get on your knees.”I...

Sissy Becomes a Slut

So by this time I was a sissy with two lovers Peter and David the brothers next door. They were quiet different from each other, Peter tended to be the gentler of the two. When he fucked me, he would carress my sissy body, lick my nipples and toy with my boi clitty. When we had the house to ourselves we would make a date out of it. We would kiss on the couch and explore each others bodies, he would take me upstairs to the bedroom, I wouold suck his fabulous cock and he would then hike my legs...

Sissy cuckold husband

Like many husbands, I've wanted to see my wife fuck other men. I like the idea of being a cuckold. I had thought my wife Pam had been fucking a man but I had never seen it. One afternoon a friend of ours came over while my wife was at work. His name was Marcus. Marcus was a big young black man, very nice looking. He was wearing jogging pants and I could see his dick moving in his pant leg. Swinging back and forth. He told me that he had been fucking Pam for over 2 months. He planned on...

Sissy fate

For a long time I have known that I was not like other guys. My first gym shower showed me that, the black guys cocks the size of grown men at age of 17. I sat and watched, trying not to stare as they walked past me cocks swinging from side to side huge balls, my God huge fucking balls mine looked nothing like these cocks. My first contact came by accident I was playing basketball with a couple of black guys, trying to guard this guy he dunked on me his big dick smacked me in the face as the...

Sissy Boy Slave and His NEW Playmate Sadie

sharleesisterboyYes, Sadie, I am a 'Lil Slave Bitch' for My Big 'brother's Cock use, when He and His friends get in the Mood for Young Sissy Boy meat to strip and abuse on the livingroom floor, inside the 'Big House'! I'm f******n and have been His Secret Sissy, Piss-Whore Slave since He traded for me five years ago when I was Nine! He KEEPS Me Locked Up in a rusty, smelly old trailer, parked inside a dark, Old Red Barn. I'm Locked up inside and I sleep on an old, Urine Smelling, Stained...

Sissy Bitch

I removed my bra slowly, letting the straps fall off my shoulders, then finally revealing my breasts. The boy stood before me, as ordered, and stared. I looked down to see a bulge forming in his pants. Maybe he is a virgin - I thought to myself - most of my boys are not so fast to respond. I let the lace bra fall to the floor, then made a motion toward my nipple. He didn't react... clearly a virgin. I snickered a little at how innocent this boy really was and decided verbal cues would be...

Sissy slaveboy gets trapped blackmailed Pt 2

When Empress had finished taking pics and videos and collecting enough evidence to ruin an army, let alone one guy she sat at her laptop and downloaded all the images onto her hotmail account and sent a copy to Mistress Saskia who was sat with her."There sissy, now they are safe in our hands and there is NO WAY you can get to them or more importantly, get rid of them. You are one fucked little whore boi"Her words echoed in my head... she was right... i was screwed over...Empress rose to her...

Sissy Crissi Chapter 4 The Morning After

Chapter 4 - The Morning After I awoke to the sound of Erika's voice. "Come on sleepy head. We've got a lot to do today." I opened my eyes and peered through thick waves of my hair to see Erika standing next to my bed. She had one knee on the mattress and was leaning over and shaking me. She had obviously not been up long. Her hair was tussled and her makeup a mess. Dressed in only an oversized t- shirt, I'm guessing one of Leroy's, her shape was largely concealed, but still...

Sissy Subjugation

Randi Michelle's Sissy Subjugation To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. It would start through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. While this is just a possible scenario, I believe that it's entirely possible that it can be turned into reality by the right Master with the means and wherewithal to...

Sissy Emma is Turned Chapter 2

Sissy Emma is Turned chapter 2 At that point I was allowed to go back upstairs and remove everything and go home. As I was walking out towards the door, John said he would see me the next week. Not if I can help it I thought. Once I got home, I quickly got into the shower and washed away the thoughts of what had happened to me and was soon in bed and fast asleep. Over the next few days, I began to forget of my ordeal and resolved to keep away from any of the chat rooms. I hoped I...

Sissy B

SISSY by Sissy Property of: __________________ (part 2) Mistress hands Master an envelope which He stuffs inside His coat and leaves. Standing in front of Mistress, She then places a heavy steel collar around my neck, locking it. Introducing Herself, Mistress tells me about my new life. "Your name is now sissy. I'm Mistress Catherine. And this is my personal slave susan. I have just purchased you from you former Master. You will accept the fact that I now own you totally. First...

Sissy Situation

Sissy Situation By Ellen (It has been a long time since my last contribution to Fictionmania - I hope this helps give you readers something very erotic to read.) Her arms were up against the doorway as she stood staring at me as I was dressed in my silky pink bra, panties, garter belt, stockings, and high heels. My long blonde hair wig cascading over my shoulders, with a touch of make-up, the usual lipstick, blush and eye shadow. When training with Mistress, I am not given...

Sissy Outed part 2 Alice finds out

As I had no other clothes to change into, I realised that I would have to walk home in a skirt. I went into the ladies toilet to check my appearance and then checked that I had my keys and credit cards in my handbag. Then I left the office and set off home, trying to look confident even though my heart was pounding. This was the first time I had been out in the street on my own in girls' clothes. I was aware of being looked at, mainly by men and boys, but not in a way that suggested...

Sissy Outed part 4 Gerald finds out

The story continues from two different points of view. Didi carries on his narrative, but we also hear from Gerald. DIDI: You probably won't be surprised to learn that I haven't worn trousers in the office for a few weeks now. In fact, I spend much of my time in girl mode. The rest of the time (that is, when I'm with Alice) she keeps me aware that I'm not a girl, but that I'm her sissy boyfriend wearing girls' clothes. She often wears trousers when we go out and she likes to look...

Sissy Denise s nightmare is her Mistress sweet dream

I dreamed I had Denise absolutely at my fingertips. I know I couldn't do that in reality to her, but it was a dream. After a long foreplay I had her finally tied with her belly down and her ass up. But she was curiously tied. Not hands and feet, firmly in leather and chains in an X over the bed. Her legs, from feet to knees were firmly tied and her breasts also, with big broader leather straps. Denise couldn't move those parts. Her head was free to move so I guess I could kiss her. But her...

Sissy diary episode 2 crossing the border

Dresden 10/21/17I’m sitting in front of my computer and trying to decide on what to write in my Sissy Diary. It’s been a while since my last post and a lot has happened since then. My entire life is entirely different now. I have so much to share.So, what’s changed? Let’s talk about the simple things first: My English has gotten so much better with every day, there is a soccer match currently on air and I’m not even tempted to have the TV on for background noise, for the first time in five...

Sissy to Be Chapter Seven

Sissy to Be ? Chapter 7 ? By: Beverly Taff List of Characters Me Robert, now called Rosie! Wendy My twin sister. Angela Our younger half sister by my mother's second boyfriend. Doris My sad working mother who lets everybody walk all over her. Aunty Janet My mother's pushy domineering sister. Harriet Our friend from the next farm. Aunty Margaret Harriet's Mother Jessica Harriet's older sister Charlie My New found clubbing friend Sally Charlie's...

Sissy Love

I opened the door. She was there, wearing her chocolate-colored long raincoat, pearl choker and earrings with brunette curly wig, made up and right in front of me. I smiled like the cat who had the cream (and I was hoping to have that soon!) and stood back as walked in. I was in my sheer pink nightgown with red bra and panties, stockers and garters, tottering in shiny black heels. "My own sissy!" I said to Regina and we kissed, our lips slithering against each other, smearing our...

Sissy Therapy

My advertisement read: MEN Interested in sex with other men but don't know how to proceed? Looking for a safe, friendly way to find out if this is for you? Obsessed by online bi/gay/sissy/crossdressing porn but frightened to meet someone? Is your marriage at risk because of your desires? I can help! One four-hour sexual therapy session will help you to decide if this is right for you, and will help you to understand your desires. Don't suffer alone, I can...

Sissy rules

SISSIFICATION RULES OF OUR HOUSEYou will NEVER NEVER use the word NO.You will be trained to dress properly in a french maid’s outfit, dressed, latex or Lingerie and monitored by phone and email, if not in our presence.You will be forced to wear make up at all times: foundation, blush, lipstick, lipliner, mascara, eyeliner, loose face powder, and body and face glitter.You will be taught to stand correctly at attention, bosom thrust out, belly in, …You will be trained in walking on high heels.You...

Sissy Story Chapter 04

Black silk shirt, short black leather skirt, black hose, black garter belt, black panties, black bra, black patent leather 5-inch heels and black onyx disks for earrings were, I thought, the perfect outfit for Campbell’s Happy Hour. Campbell’s was the most popular bar downtown and its happy hour was legendary, not for the prices, but for the customers. I’d been there before, and knew a couple of the staff, including the manager. He liked good-looking clientele--they dressed up the place,...

Sissy the Redhead Mamma s Home Pt III

I couldn’t wait to get out of the car when I pulled in out driveway. A six hour drive home from picking up my sixteen year old son from his father’s, and the whole time I felt his eyes on my legs and chest. Granted, I was wearing a hot leather mini-skirt, and a halter top that showed off my flat stomach and huge double d tits, and it’s not like it didn’t enjoy the attention, it’s just that six hours of having a hot, wet pussy I couldn’t touch made me really cranky. Especially since my...

Sissy the Redhead Her First Cock Pt II

I couldn’t believe my plan had worked so well. That hot housewife across the street was even more game than I had thought. I had dressed as slutty as I could, digging out clothes from three years ago when I was only ten years old, squeezing into them, and flaunting my tight little thirteen year old body all over the yard pushing the lawn mower. It only took twice before she came over an made her move. And, my god, what a move. I’ve never cum so hard. Even when Mom and I fool around....

Sissy the Redhead Making of a Slut Part I

Introduction: I have many more chapters to come–each increasing in dirtiness, variety, and taboo. Sissy the Redhead: The Making of a Slut Part I She was out mowing the lawn again. That little red head across the street. She was probably thirteen or so. Maybe fourteen, and she had long thick curls of deep red hair. The kind that looks dyed, but isnt. Her titties were just coming in, but they were coming fast. She must be pushing a B cup by now, only she wasnt wearing a bra that day, just a...

sissy s first party part 1

It had been a long 2 weeks since i moved in with my tv mistress Kate and not what i expected. I wasn't allowed to share her bed despite me proving myself a good little cocksucker and had to reside in the spare room.Kate had immediately put me in chastity on day one with little clitty locked tight in a small bright pink chastity cage, and i was introduced to my new wardrobe immediately which largely consisted of skimpy frilly pink lingerie and short pink slutty dresses and high pink shoes.i was...

SISSY

SISSY Looking at me now, one will have an extremely difficult timebelieving this story. But let me assure you that every word istrue. It started late one spring afternoon. The weather was typicalspring weather, windy, wet and cold. I was walking home from highschool, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was...

Sissy Finds Black Cock Bliss

Sissy Finds Black Cock Bliss byfrezrevup©Gina had a dangerous smile on her face as I walked in the house covered in red clay matted to my body with sweat from a long thankless day at the office. My gorgeous petite wife walked up in a flirty barely there dress that showed off her big breasts and curvy hips and it did nothing to improve my mood. It added to my depression. Gina was so pretty a dozen times a year some idiot would bump into her car just to get to talk to her. Cops incessantly pulled...

Sissy Emma is Turned chapter 2

At that point I was allowed to go back upstairs and remove everything and go home. As I was walking out towards the door, John said he would see me the next week. Not if I can help it I thought.Once I got home, I quickly got into the shower and washed away the thoughts of what had happened to me and was soon in bed and fast asleep.Over the next few days, I began to forget of my ordeal and resolved to keep away from any of the chat rooms. I hoped I had learned my lesson.That was before I...

Sissy Mission 6 Poodle Skirt Sissy

Sissy Mission 6: Poodle Skirt Sissy By Cheryl Alison I sat on the bench assessing my surroundings. It was a well-kept small town, with a cobblestone main street and nicely maintained historic buildings. Banners and awnings in the front of shops fluttered in the breeze, advertising everything from antiques to hardware. Since it was a town located on a large lake with lots of recreation opportunities, it was busy on this early June day. People strolled up...

Sissy fulfilled on business trip

"MMMH! You'll do nicely," I heard as I felt a finger traced the waistband of my lacy panties. "Stand up sissy." Horrified, I stood and turned around from the weight machine I was adjusting and stared at the shoulders of a very fit black man. I wear lingerie 24/7 so didn't even think about my panties showing above my gray fleece capri workout pants as I was working out at the Albany hotel I was staying at for business. Looking up at his face his eyes fixed on mine and said, "What...

Sissy Farm Chapter Twenty Nine

Sissy Farm - Chapter Twenty-Nine - 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 Bev's brother.); James,...

Sissy Samplings

SISSY SAMPLINGS by Throne "Richard," my wife said, "you are such a pansy." "I am not," I responded, biting my lower lip and trying not to start crying. It was hard for me to stand up for myself, dressed as I was. Vonda had picked out an especially shameful outfit for me that day. There was a red thong that resembled the bottom of a bikini, and it showed off the tiny bump made by my endowment. Attached to that and fitted over my narrow shoulders were loudly colored suspenders. On...

Sissy Puppy Fifi

Chapter One I had prepared myself for my new life; my body was completely devoid of all hair, which included my head. I entered my room and the smell of rubber filled my senses. Immediately my cock got hard. This was however a major problem and very painful. I had been fitted into a new and very unusual chastity device by Mistress. It consisted of a bright pink rubber ball about four inches round. Into this both my cock and my balls had been pushed with quite a struggle. The ball was...

Sissy Downfall

This story is about my conversion from a cross dressing sissy to submissive transformed slut owned by Mistress Rebecca George. Having been to the beautician for a full body and face wax I check into the hotel to prepare. The suite consists of a large living room and a comfortable bedroom with a large bathroom. The bedroom has a nice dressing table with mirror and stool. A full length mirror is adjacent. The king size bed is of an older style with metal barred head and framed foot. The living...

Sissy Stepdad

Sissy StepdadChapter IDaaadddeeeee!" the shrill voice of my stepdaughter called. "Get your sissy ass up here! I have a clean-up job for you!"Shit. As if having to clean the house while wearing a red lace panty and bra set with six inch stiletto heels, and a butt plug shoved up my ass wasn't bad enough. I knew she was in her bedroom with some boy, and also knew exactly what the "clean-up job" would be. Just like all the other times. She'd just been laid, and I was going to lick the cum out...

Sissy Cuckold Rebecca Lynn

By: Rebecca Lynn Sissy Rebecca Lynn Cuckold Rebecca got married to a very understanding woman who was fine with her crossdressing - but eventually, she needed a real man. My wife knew I was bisexual when we married; we agreed early on that any 'extra-curricular' play had to be talked about, no secrets. We're both very submissive, but we connected on a lot of levels, and we've been happy for several years. I'm hung very small, so our sex life usually consisted of me giving her...

Sissy Dick Johnson

Sissy Dick Johnson by Throne He was really annoying. Dick Johnson was a wimpy guy. Short, unathletic, with his brown hair falling over his forehead and ears. At 21 he had no significant experience with females. And he was smitten with Angel Giovanni. She was stunning. Short and buxom, with her jet-black locks streaming halfway down her back. At 24 she had confidence born of being a sex bomb. And she was irritated by Dick Johnson. Since he had moved into her apartment...

Sissy Kristy Gets Drilled in the Lowe s Parki

Another true story of one of my many sex-capades:Late one night (more like early one morning) I met a trucker on Kik that was passing through my area. For me, nothing is hotter than getting plowed by a truck driver in the sleeper cab of his truck, so I had to make this hook up work! The problem was that I was horny now, but he wasn't going to be in my town for another couple of hours. So, I decided to hook-up with another guy from Kik. (A decision I would totally regret later on.) You can read...

Sissy Slut for Master S Finale

In the last month I had agonized over confronting Penny with the revelation that I was a bitch to Master S and ask her if she was as well but could never get up the nerve to do so. If she was Master's bitch she definitely had a mean poker face. So when I had got the text from Master to be his bitch once more I eagerly jumped at the chance. Since I was still in chastity I desperately needed relief. So here I was once again in the hotel room having endured the scorn of the receptionist....

Sissy the Redhead The College Plan Pt VII The Finale

Introduction: the last, unless you want a prequel Sissy the Redhead: The College Plan Pt VII: The Finale The last few weeks have been unreal. That night after my mom confronted Charlotte about everything, Jim had come home. Charlotte and Mom sat him down and explained that he was basically going to be providing for all of us now, but there were two tradeoffs. First, he and his wife wouldnt have to go jail, and second, he had three women to choose from whenever he wanted them. Sure, he would...

Sissy for Sister In Law

“Oh! excuse me,” Tiffany said in a startled tone, shocking me awake from my intoxicating stupor as I enveloped the aroma of the decadent delicate I’d discovered in my exploration of her dirty laundry. I had been caught red handed, standing in her room holding a precious pair of her purple panties to my face in one hand while my other depressed at the distending underwear, bulging from my open fly. I fumbled around foolishly, nearly falling over, as I watched her turn and storm off down the...

SISSY BOY

Lori had James who had been her sissy boy for a long time. She loved to dress him like a girl and get him a date or a hook up with another gay guy. Tonight she stripped him naked and bent him over and used her thick strap on in his ass. Even though he was a sissy he had a great body. He had a nine inch thick cock and a great ass that he loved fucked. Lori fucked his ass hard as she jerked his cock and waited for him to cum in her hand so she could feed it to him. Then she pulled the cock from...

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...

Sissy For a Year 6

A few days later, Achref told me he had to return to Egypt to tend to some urgent, serious family matters. He looked worried, and out of love I was worried too. But something He did really showed me how much He cared for me: following on my oath of sissiness, He knew I needed to be at the service of a man who could be my guide, my Beacon of Light in developing my female persona. So I was told, during His absence, I would be serving another man, whose task would be to watch over my honour...

Sissy Alone for the Night

As I pulled into the car park outside the hotel, switching the engine off and stopping for a second to catch my breath, my heart beat with excitement.After a few deep breaths, I looked around, making sure I didn't recognize anyone before stepping outside to make my way to the trunk. My hands were trembling as I reached inside for my suitcase, pulling out my bag and trying to hide the guilty look painted all over my face.I composed myself, then walked inside and approached the front desk where a...

Toys

Hypnosissy

Hypnosissy By Margaret Jeanette Paul Peters was awake at midnight again. He had gone to bed at his usual time which was 10 P.M. For about the last two weeks he was sleeping every other night. The other nights he would lie awake in bed wondering why he coulldn't fall asleep. He tried sleep aids from the drug store and they seemed to work in reverse keeping him awake all night. At work he discussed his problem with Sid Werner. Sid told him he had once had a strong aversion to...

Sissy Story Chapter 05 Finale

All the stuff, some dishes, the leash, the collar, the toys, a chew bone and a ball with a bell in it, a couple of bags of training reward dog treats, and some dry dog food, were ready the next day. His dog tag and dishes with his name on them would take a couple of weeks, but I thought that was way too long for the first time in a chastity belt. I wanted him fired up, not frantic and thinking of ways out. I felt like it was most important to start having fun. Mom agreed, so I sent off...

Sissy the Redhead Making of a Slut Part I

Part I She was out mowing the lawn again. That little red head across the street. She was probably thirteen or so. Maybe fourteen, and she had long thick curls of deep red hair. The kind that looks dyed, but isn’t. Her titties were just coming in, but they were coming fast. She must be pushing a B cup by now, only she wasn’t wearing a bra that day, just a tight little baby tee that said “Candy” on it that showed off her tight, flat waist. The shorts she had on didn’t hurt in...

Sissy

Well. That was interesting, wasn’t it? We’ll play with your little titties again tomorrow. For now, just close your eyes and rest. Did you have a good nappy? Do you need to go potty? Ok. But remember to catch the little dribbles with a tissue. You wouldn’t want to stain those cute little pink panties. Now that you’re back, I think it’s time we did something about that little tiny – it’s too small to call it a cock, don’t you agree? It’s not even a dick. Dicklet. A dicklet. That’s all it is. Not...

Sissy Experience Episode 3 Neighbourhood Uncle

Hello All,Hope you’re all doing well!Hey Guys and Girls if you have not read my previous episodes I recommend you read those and come back to this one.In the previous episode I told you guys how the sissy part of me was evolving. I was now dressing like a complete girl whilst fingering my ass pussy and pinching my titties. My ass would get wet and my dick hard when I would dress like a girl. Whenever I was home alone I would look for sexy clothes either in my Mom’s or Sister’s cupboard and put...

Sissy masturbation and light exhibitionism

This is the backstory of the gallery "Sissy masturbation". I would like to share the thoughts and sensations behind the pictures and videos I took. Today my brother had classes in the morning and my mom was driving dad to work. I knew I had an hour to satisfy myself. I took a shower before my family left, don't want to get my last set of underwear dirty. I then retrieved the set of underwear from my secret stash. The sports bra was tight and I struggled into them. The cotton panties were so...

Sissy Fucked In Adult Book Store True Story

100% True Story.I was 19 years old and working 3rd shift at a department store and taking classes during the daytime. I had visited an Adult Bookstore about 15 minutes away a few months back and went back into the video booths. It was the first time I had even been in an adult video arcade and wasn’t really that impressed. There was a strip club next door and I had heard stories of hookers giving guys head at the bookstore video booths. I realized that turned out not to be true. I was pretty...

Sissy all dressed up at a rest area

Sissy all dressed up at a rest areaSo, i had a bit of a scary encounter recently. But it was totally worth it =]. I was driving from my home town to the town where i go to school. It is a windy little road that goes right through a big slice of nowhere, with very minimal cell service. And it was night time. I had been all dressed up and hoping to find someone at a local wildlife area that is an OK place to find guy sometimes, but no dice. I am pretty shy, and don't go to places like that much,...

Sissy Lucy meets her daddy

I’m in my late 20’s and manage a local restaurant/bar. I am 5ft 8 and slim with quite feminine features. To most people I’m just Tom, a regular guy who has occasional girlfriends, likes a beer and watching the football. To my closest friends I’m Lucy, a sissy slut who loves cock. Recently I’d found a ‘daddy’ online. He was an older more experienced man. We started off chatting and I sent him some naughty photos and video clips of Lucy playing. As we talked I revealed that I like to be...

SISSY

Looking at me now, one will have an extremely difficult timebelieving this story. But let me assure you that every word istrue. It started late one spring afternoon. The weather was typicalspring weather, windy, wet and cold. I was walking home from highschool, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was very small, looked 16 and feminine. If you're thinking that's normal...

Sissy Slave

Joanne, my wife, has for many years insisted that I wear lingerie and girly things under my male clothes when at work as part of my sissy training. At home I am a sissy slave.“Sally” she said “Today we are going to make you feel more aware of the pretty things you wear”. After years of taking hormones my breasts are a nice 38C with dark brown shades round my nipples and Joanne had arranged for me have my balls and sac removed when we went to Thailand one year. Despite this and though my cock...

Sissy Downfall

Sissy DownfallThis story is about my conversion from a cross dressing sissy to submissive transformed slut owned by Mistress Rebecca George. All characters are over 18.Having been to the beautician for a full body and face wax I check into the hotel to prepare. The suite consists of a large living room and a comfortable bedroom with a large bathroom. The bedroom has a nice dressing table with mirror and stool. A full length mirror is adjacent. The king size bed is of an older style with metal...

Sissy boy and a shave

It’s a Saturday night. I’ve been talking with this guy online for a while now trying to determine if he and I are the right fit…. and also work up the balls to meet up (…so my balls and much more can be worked over). We’d spoken about a whole bunch of things whilst chatting, his fetishes, mine, and what both of us would like to do to the other / have done to us. From this it all seemed pretty enticing so we teed up a night we were both free to dedicate to debauchery. Thankfully for me my...

Sissy

Well. That was interesting, wasn’t it? We’ll play with your little titties again tomorrow. For now, just close your eyes and rest. Did you have a good nappy? Do you need to go potty? Ok. But remember to catch the little dribbles with a tissue. You wouldn’t want to stain those cute little pink panties. Now that you’re back, I think it’s time we did something about that little tiny – it’s too small to call it a cock, don’t you agree? It’s not even a dick. Dicklet. A dicklet. That’s all it is. Not...

Fetish

Sissy Tranny Annie Slutty Fantasy

I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me. My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved...

sissy for mum and friends p4

I reluctantly sat between Ali and Nick. As I sat down I took care to keep my legs together so not to show my panties and I crossed my legs to try and sit like a lady. I realized I did both of these things naturally, god im starting to think like a girl, I thought to myself. I glanced across the room to where Greg and Chris were sitting, I realized they were quite drunk and they were both almost leering at me. I found myself blushing a little and my cock twitched in my panties. "God you...

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