Sissy the Redhead Making of a Slut Part I
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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 tight little baby tee that said Candy on it that showed off her tight, flat waist. The shorts she had on didnt hurt in the showing off department, either. They were jean shorts that were cut off no further than the crotch, and so tight they must have been left overs from when she was ten.
I sat on my screened in front porch sipping my sun tea, letting my fingers trail across my shirt, over my tits, feeling my nipples harden to tight little pebbles as I watched her. She was so tiny she had a hard time pushing that lawnmower, which made her sweat a great deal. Her shorts would ride up into the crack of her ass and shed have to pause to pull them out. Each time she did that, my breath caught in my throat.
Whenever shed pass the stoop leading up to her front door, shed stop for a drink out of her water bottle, rest with one hand on a thrust out little hip, and pull at a few long, red strands of hair that had stuck to her pretty face, all the time her breasts heaving from the labor.
I thought about what it might be like to peel those sweaty shorts off and slide them down her skinny legs. How her innocent little pussy would smell as I pulled apart the lips and licked her from her tight ass up to her hardening clit. I pictured my hands running over those pert tits and squeezing her nipples, making her moan and writhe under my experienced, womanly touch. Giving her her first real orgasm.
Before I knew it, my tea was forgotten and I had my hand shoved down the front of my shorts, three fingers jammed up into my cunt and a thumb on my clit. I was already close to cumming and was stunned at how fast these thoughts about a young girl were getting me there.
Then I began to imagine that my husband, Jim, was watching us. Watching me thrust my tongue into her small hole, hearing her girlish squeals increase until she would go stiff, and her fresh cum would pour out of her tight, young pussy and fill my mouth. When I pictured him seeing that, and shooting thick ropes of hot cum all over both of us, I went over the edge and exploded into my shorts. By the time the shuddering let off, and I pulled my sopping hand away, the chair I was sitting in had a big wet circle soaked into it and the redheaded girl had finished the lawn.
That night, after solitary dinner as my husband was away on business, I decided to take a hot bath and treat my pussy to a clean shave. As I relaxed in the soapy water, I wondered about the redhead girl and what her bush must be like at her tender age. I imagined it was lightly covered in a soft, downy fuzz, the same color as her hair. I finished shaving myself smooth, then brought myself off three times thinking about how that hair would feel on my lips. By the I toweled off and went to bed, I had made up my mind to talk to that girl the next day. No matter how irrational it was, no matter how wrong, I devised my plan, and would carry it out.
The next morning, I hussied myself up in a very short denim skirt, the kind that would show my baby-smooth pussy and pretty little asshole if I bent over at the waist. I put on a hot pair of elevated fuck-me sandals and tight white tank top, braless of course. I looked myself over in the mirror. Hot! Im only 31 years old, and look better than anyone I went to high school with. My husband says I have a Preying Mantis body. Long legs, a long, skinny stomach that climbs up forever before reaching a pair of high, tight small C sized tits. They are perfectly balanced with the rest of my body, and the little nipples sit high on the boobs, pointing slightly up with all the perkiness of a 20 year old college girl. My arms are as long, and slim as my legs, toped with the smooth, rounded shoulders models have. Add my dirty blond hair and big green eyes to the package, and its no wonder Ive been offered money in the thousands by men who wanted me.
Satisfied I would make even the straightest young girl consider what I was after, I walked across the street to put my plan in motion. I was hoping her parents were at work when I knocked, and I wasnt disappointed. even better, she must have just gotten out of the shower, because when she answered the door, she had nothing on but a towel. Not a full bath towel, but something about the size of a hand towel. Granted, she was small enough that it covered all the important parts, but god, I got wet just thinking about how easily it could slip off.
Hi, um, I live across the street? I was more nervous than I thought I was.
Uh huh. She was looking me over, her eyes lingering on my tits, which I knew without looking were sporting hard little nipples. That, I figured, was a good sign.
Well, I saw you mowing your lawn yesterday and I was wondering if youd like to make some money. You, know, mowing mine? There, that was easy.
She finally pulled her eyes off my chest and looked me in the eyes. She had a gorgeous face. Big blue eyes, a light dusting of freckles, just enough to accentuate her youth. And while my features were what youd call delicate, she had those high, strong cheek bones Irish girls always have, but they were still mostly concealed under an innocent layer of baby roundness. God, she was delicious.
How much, she said. Smart girl, I thought.
Hows $50. sound? Her eyes lit up. I knew that would at least get her over in my territory. It would be much easier to seduce her on my own turf.
Sure, Ill be there in fifteen minutes.
She was there in ten, wearing a different pair of cut-offs, these even shorter than the last, and a different baby tee, also tighter than yesterdays. This one said, Try Me over her tits.
Hi, I said when she pushed her lawn mower to a stop in front of my screen door. So, whats your name?
Sissy.
Nice to meet you Sissy, Im Charlotte.
Hi, she said. Up on my porch like that, I stood about a foot and a half higher than if we were on equal ground, which gave her an excellent view of my legs where my skirt ran out. In fact, if my skirt were to ride up, just a little, Id bet shed have a good look at my moist lips…
Just come onto the porch when you finish, Hun, I said. It took her a second to look away from my legs. Ill fix up some iced tea and well square up, okay?
Okay.
I sat back in my chair and watched bend over to pull the cord on her mower. I was in luck, because it took her a few tries to get it started, and from my angle, I could tell she wasnt wearing any panties under those shorts. With each yank, they would ride further and further up into her crotch until I could clearly see her puffy lips peeking around the edges. I already couldnt wait until she was finished.
After about an hour of me leering at her sweet little body heaving at the mower and soaking her tee shirt completely through, turning it almost see through and showing off her hard breasts and nipples, she shut off the mower, and came in.
Well, you look tired, I said. Why dont you sit down and Ill get you a drink.
Thanks, she said, and plopped down in a chair.
I went into the kitchen and came back out with the iced tea. I set it down on a low end table, and with my back to her, I bent down very slowly, with my legs slightly apart, and allowed my skirt to rise half way up my ass. I could feel her eyes glued to me, so I took my time arranging the glasses and pouring the tea. When I turned back around, I was pleased to see a sheen had formed over her eyes and her mouth was slightly open. I knew that look well–arousal. My plan was going quite smoothly.
So, Sissy, I said, in a soft, husky whisper as I handed her a glass. What do you like to do for fun?
Um, nothing much. Just hang out, I guess.
Do you have a boyfriend? I asked. She looked a little shy at the question. Its okay, its just between us girls. I threw my best seductive smile at her, complete with my irresistible glass-eyed bedroom gaze as I sat down across from her. I made sure my skirt rode up nice and high, and my legs were spread enough for her to get a good look at my bald, wet pussy.
Um, no, she giggled, looking down at my crotch.
Oh, I played coy. I suppose you arent old enough to like boys yet. I knew that wasnt true based on the outfits she wore, but I wanted to feel her out a bit before I made a move.
No, she sounded a little offended. Good. Im old enough. Im old enough for lots of things.
Oh, really? I leaned foreword, my smile teasing, my firm breasts bobbing close to the top of my tank top. What sorts of things?
She was staring down my shirt, the lust building in her eyes at this point. I had a feeling boys werent all she was old enough to like.
Um, was all she managed to answer.
I decided it was now or never, so I reached up, grabbed my own breast and started to slowly massage it, the whole time staring into her eyes. Maybe you like these sorts of things?
She nodded her head slowly.
Uh huh, she said, her own hand mirroring mine as she began touching herself.
Have you ever been with a boy? I asked.
No, not yet, she said, never taking her eyes off me. But I have fooled around with girls.
Really? I asked. I didnt even try to hide the excitement in my voice. You like fooling around with girls?
Yes, she said.
Do you want to go inside where its a little more private? I asked.
Uh huh.
I stood up and took her by the hand. I led her up to my bedroom and we sat on the edge of the bed. I couldnt believe this was going so smoothly. Just yesterday I was fantasizing about tasting this little girls fresh young pussy, and now she was sitting on my bed, her little chest heaving with passion as I ran my hands over her tits. When I leaned it to kiss her neck, she let out the tiniest sigh and began rubbing my tits. Oh yes. She had done this before.
Then I kissed her on the mouth. She opened up for me and met my tongue half way, both of our breathing speeding up, our hands frantic now, groping one another shamelessly. I couldnt take it anymore. I pushed her back onto the bed, perhaps a little roughly, but I didnt care. I was going to have this pretty young girl, and I was going to have her now.
I unbuttoned her shorts and pulled them to her knees, then I lifted her legs up, exposing that tight little pussy. Her fluff of hair was exactly as I imagined, but I didnt waste any more time looking, I leaned in and ran my flattened out tongue up her slit. She tasted a little like sweat, but she was soaking wet with her own juices, too. Those tasted sweeter than any I had ever tasted before.
I split her lips with the tip of my tongue, delving into the smooth entrance to her hole. When I did, even more wetness slipped out into my mouth. Form there I traveled up to her clit, flicking it back and forth, making her squirm. She started bucking her hips up into my face, rubbing her whole cunt along my nose and chin, allowing my tongue to dive into her tight little hole along the way. I decided to tease her a little, and I pulled away.
Then she kicked off her shorts and pulled off that soaked baby tee, and laid back, totally naked, exposed to me, and began fingering herself. I almost came right there, looking down at her small body. Thoughts of how wrong this all was, and how into it she was only made me hotter. I pulled my top off, but didnt bother with the skirt. I just hiked it up to my waist, turned around, and straddled her face. She wasted no time latching onto my hips and diving into my dripping pussy.
Oh my god! She had definitely had practice doing this. Within a minute I was screaming out, grinding my cunt down onto her pretty face, and filling her eager mouth with my cum. That good little girl drank every last drop.
Once my orgasm died down, I crawled off of her. She was still fingering herself, so I figured she might like to play with one of my toys. I reached into my nightstand and pulled out a small rubber vibrator. She cooed when she saw it.
Its not too big for you, is it? I asked.
No, I have one about the same size at home, she said. Only mine doesnt vibrate like that.
Well, you dirty little thing. Youre in for a treat.
I began with her clit, letting the toy bring her almost to the edge. She writhed and moaned. Her juices were flowing freely now, soaking the bed underneath her, filling the room with her spicy aroma. Then I slid it into her and began pumping it in and out, the whole time sucking and nibbling on her clit. Her moaning increased with each thrust, and I could tell she was close. Then she shocked the hell out of me.
Charlotte, God! Put it in my ass! Please!
Well, I wasnt one to deny a hot young girl what she asked for, so I placed the tip against her tiny back door, and began to work it in. Sissy, however, had other plans. She wanted it in her ass and she wanted it now. She thrust her hips foreword and the whole thing, all 5 inches of it, disappeared. With my mouth clamped down around her pussy, and because she was so small, I could feel it vibrate her whole lower half. She must have loved it, because within a minute, she tensed up and I felt the insides of her pussy push outwards. The next thing I knew she was squirting into my mouth, and screaming at the top of her lungs. And when I say squirting, thats what I mean. It was like she was peeing, only it was definitely girl cum, and about a pint of it shot down my throat, filled my mouth and ran down my chin, covering her and me and my bed.
We laid there for a while after we both came down, stroking each other. She wouldnt let me remove the toy from her ass right away, so the only sound was the muffled buzzing and our heavy breathing.
Will you teach me how to do it with a boy? She finally asked.
Sure, Sissy, I said. You can come over anytime you like, and Ill teach you anything you want to know.
What about your husband? She asked.
I smiled at her. Who do you think Im going to teach you on?
To be continued…
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Therese looked at the scene before her. Her father and brother naked, her grandfather’s cock sticking out of his trousers and her grandmother eating her mother’s cunt, both of us naked. Beth with the camera, filming. “God, the slut is only in the door and she’s gone sex mad.” she said referring to me. She went and sat on the arm of her father’s chair putting her arm around him and kissing him on the cheek. My father was now hard again. He pushed my mother out of the way and started to fuck me...
Well after getting fucked in the car park on the front of the limo by the driver my arse is ready to be fucked by my three black bulls.I have been waiting a long time for this and now I am ready for to be fucked like a slut my arse is Gunna get stretched to it's limits by these black studs cocks .The limo pulls up outside the apartment and my heart starts pounding so hard with excitement I can't wait .We go upstairs and as soon as we get in the door I'm sorounded by all the guys they are...
Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...
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...
Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...
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...
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...
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,...
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...
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....
The gist of this story’s prequel: I am Shakti, a sissy boy who used to try my sister’s clothes. My father fled when I was 4. Years later during college I was fucked by my father without even knowing. Please comment on this story and share it. Story Continues: “Who…who are you?” I asked trembling. “How could you not remember me? Shakti, I am your dad.” I was still in shock. “What are you saying?” I stammered and it was radio silence for a moment. Then without saying anything he went. I went...
Gay MaleI wake up to what seemed like a dream last night, but I'm still in the tight little panties, and have dried cum on my cheeks and lips. Was Pete serious... nah, he was just messing, its over, and maybe i can get some action with any spare women on the ship. I hop out of bed, slipping the panties off, and go to my closet. To my shock, hanging in the front is a cabin maids uniform... accompanied by a note saying to be wearing it, in the cabin at noon...and also a snap of my cum covered face with...
BisexualI 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...
'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...
Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...
One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...
One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...
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...
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...
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...
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...
MatureSISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...