Sissy Stepson 10 Stepmother s Sissy
- 4 years ago
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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 gorgeous brunette girl met me with a smile.
"Hi, how can I help you?" she asked, welcomingly.
"I have a room booked," I replied nervously, admiring her feminine features and subtle makeup.
She took my name and started tapping away on her keyboard, clicking the buttons loudly as I stood apprehensively waiting for her. My hand gripped the suitcase as my heart began pounding in my chest. She had no idea what I was holding, hidden inside the bag.
Little did she know that in my hands was a collection of sexy lingerie, dresses, makeup items, and sex toys. Everything a sissy like me needed to transform herself into a sexy and naughty little slut.
She looked up at me inquisitively, making me blush at the dirty thoughts that were running around my head.
"You're in room 103, just down the end of the hall," she said, looking at me blankly. "If you need anything, just dial down to reception and we'll be right with you."
I smiled back and thanked her, before grabbing my keycard and heading down the hall. I was so relieved to find that my room was at the end of the hall. It meant that I didn't have to worry about the noises I might make during the night!
Giggling to myself as I opened the door, I swiped the keycard and entered the room excitedly. Looking around at my own room... my sissy sanctuary.
The room was fairly large with a king-sized bed, desk, chaise lounge in the corner, and my own shower room.
I slammed the bag onto the bed and immediately began to undress, stripping naked as I pulled out my wash bag and headed for the shower.
Diving into the shower, I began preparing. Cleaning myself all over, and making my skin silky smooth, appreciating the sensual feelings as I ran my fingers over my soft skin.
'I'm so fucking horny!' I thought to myself as I ran my hands over my body, pinching my nipples hard.
After a long shower, I wrapped a towel around my chest and tiptoed back into the main room, rummaging through my bag for the first of my newly purchased items.
I tore open the packaging to reveal a sheer suspender bodystocking. My cock grew hard as I carefully pulled it out of the plastic and held the material in my hands.
'Fuck these are so sexy,' I thought, rolling it up over my toes and sliding the material over my smooth legs. The stockings clung to my every curve, making my petite body look flattering in the dim lights.
'I can't believe I'm doing this! I'm such a fucking slut,' I thought as I admired the lingerie in the full-length mirror.
I wanted to start jerking my little cock right then and there and shoot cum all over the stockings but I knew I was only getting started! I had to be patient and try to control myself, there was much to do before that.
I returned to the suitcase, searching for my new pair of sparkly stripper heels, pulling them out and setting them aside.
'Only a real fucking slutty bitch would wear shoes like that!' I heard my inner voice say.
Continuing to search through my bag, I found the sexy wet look mini dress I had bought a few days earlier. Eagerly pulling it out of the packet and holding it up against my body, feeling the fabric cling to my slender frame.
I desperately wanted to flaunt myself and hurriedly slipped it on, stretching the new wet look material and hearing it crackle tight against my ass.
As I appreciated the feeling of the dress tightly rubbing against my body, I adorned my long brown curly wig and stared at myself in the mirror.
"Mmm look at you. You fucking nasty slut!" I said to myself, mouthing the words, "Fuck me," aloud.
I could feel the blood rushing to my penis, quickly turning me into a horny little slut as I rushed over to set up my camera. I carefully tiptoed around the room in my ridiculous heels as I erected the tripod and set the camera to self-timer.
Quickly, I moved the suitcase off the bed and sat down cross-legged on the edge, looking at myself in the mirror as I picked up my new heels. I couldn't wait any longer, slipping on the five-and-a-half inch high heels and fastening the straps around my ankles.
I stood up, feeling my whole posture change as I slowly became more effeminate. Confidently strutting around the room, taking pictures of myself in various slutty poses on the bed.
My tiny cock had become rock hard, pressing tightly against the sheer lace stocking under my dress.
"I wanna suck your cock," I moaned, reaching back inside the suitcase and pulling out a brand new eight-inch realistic cock with a suction cup. Quickly I jumped up, ran across the room, and changed the camera setting to record. If I was going to do this, I wanted to capture every moment.
Within seconds, it was stuck to the mirror as I began licking and kissing the head. I couldn't believe how wobbly and real it felt, sucking the tip and letting it spring back and smack me gently on the lips.
'You fucking slut!' I thought staring at my reflection, appreciating the stockings, heels, tight dress, and pretty girl I saw sucking cock in the mirror. 'Who wouldn't fuck her?!' I thought.
For several minutes I practiced my cock sucking abilities. Making sure not to use any teeth, just my mouth, lips, and plenty of tongue. Taking it as deep as I could, all the way to the back of my throat. Making me gag and choke as I bobbed my head over the cock while it dangled from the mirror.
My boy pussy was beginning to ache for something hard, reaching back for my six-inch vibrating cock and a bottle of lube. Thirstily soaking it in lubricant before switching it on and searching for my aching hole.
"Mmm," I moaned, "you're such a dirty little slut!" Squealing softly as the tip penetrated me and began vibrating against my g-spot.
Staring in the mirror at this filthy little whore, I was more turned on than ever! 'I fucking love this,' I thought to myself, continuing to suck the realistic cock and bouncing in my heels as I slowly rode my vibrator.
My moans became more frequent and precome began to drip from my tiny cock as it flapped between my legs. 'Mmm', I moaned like a girl.
The camera was still recording as I began to shudder and shake, feeling the beginnings of a sissygasm stirring deep inside my tiny balls.
'No, not yet!' I thought, stopping and stepping up as I wobbled in my heels and pulled the 8" cock off the mirror. My ass was gaping now and I knew I could take a bigger cock, laying down on the bed flirtatiously.
I slowly removed the vibrator, switching it off and leaving it on the side, shifting my position on top of the realistic cock while I searched for my boy pussy.
As I tried to take it in, I realized how big it actually was. Not just the length. But also the thickness. After a quick failed attempt, I grabbed the bottle of lube and applied a generous amount over the tip before lowering myself and trying again.
The lube helped make it slide in, as I lowered my whole weight onto the bed, feeling a few inches penetrate my boi pussy. I moaned girlishly as my body trembled.
"Fuck," I squealed. I couldn't believe how good this felt. Rocking my body onto the mattress and touching myself as I rode the eight-inch cock. I had just begun to build to an orgasm when I was disturbed.
A loud noise made me stop and freeze on the bed, the dildo still inside my ass as I paused to listen. Distracted by voices I quietly got off the bed. Carefully, creeping across the room trying not to make too much noise, and put my eye to the door.
Standing in my slutty five-and-a-half inch heels, dress halfway up my ass, I peered through the peephole. Less than three feet away, two businessmen walked loudly past my door.
'If only they knew how close they were to a tranny slut,' I thought, running my hands over my stockings and smiling to myself.
My whole body lusted for cock. I wanted to be used and degraded right then and there. If anyone had come into the room at that moment, I would have bent over and let them fuck me like the nasty little sissy slut that I was.
The thought instantly turned me on, making me jump back on the bed and ram the dildo back inside my hole. Pushing down harder onto the cock, I began bouncing faster, riding it deeper and deeper. I watched myself in the mirror, dressed like a slut, riding cock in a hotel room like a cheap prostitute.
I wanted to be fucked like a porn star, trying to take as much as I could. Before long I looked down, realizing I had taken every inch of cock! Now only able to see the realistic balls poking out between my legs I rocked back and forth.
'Fuck!' I thought. 'I can't believe I can take eight inches!'
Turned on more than ever, I started riding faster, lusting over every thrust. My hair swishing around as I brought myself ever closer to climaxing.
"Don't stop until you make me come, baby," I screamed, my whole body shaking uncontrollably as I continued riding the dildo. I could feel my orgasm about to blow, sliding the cock out of my ass and frantically shifting my position.
This was the closest I'd ever been to sex with a man and I wanted to make the experience feel as real as possible.
As I leaned over the bed, I jerked my tiny hard cock. My vision blurred, trying desperately to aim as I began shooting streams of thick come all over the dildo.
There was come was still pumping out of my throbbing penis as I quickly bent over to wrap my lips around the dildo. My tongue lashed around feeling every vein on the realistic cock, enjoying the taste of my own come in my mouth as I continued to leak from my clitty.
After a few intense orgasms shuddered through my body I began to feel normal again. The blurry haze had cleared from my mind and I now realized what I had just done. Looking ashamedly at my reflection I rushed to strip off and clean up my mess.
'What I am doing?' I thought. 'What kind of pathetic loser dresses up and does shit like this!'
I felt so degraded and ashamed, quickly removing my come soaked stockings and dress, racing back to the shower. I was all sweaty and felt super dirty both inside and out. I didn't understand this fetish or what drove me to do it.
Was I a freak? Was there something wrong with me? How could I stop doing this! Dozens of questions ran through my mind as I tried to wash away the feelings of guilt.
I finished my shower, dried off, and sat back down on the bed. I'd packed everything away and was considering throwing out all my sissy items first thing in the morning. For twenty minutes or so, I tried to distract myself, watching TV, and drinking wine from the mini-fridge.
But, as time went by, I began to think about all the other items just waiting inside my bag. Looking over, I noticed a suspender strap dangling through a gap in the zip, instantly feeling an overwhelming urge run through me.
That was all it took. Despite all my previous feelings of shame and remorse, I knew who I was and what I was going to do next.
'I was going to dress up again, wasn't I? Yeah,' I thought, 'I was going to dress slutty and then suck and fuck cock all night long because that's whats sissies do, and that's what I was.'
A naughty little sissy... all alone for the night.
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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...
(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...
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...
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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...
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...
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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...
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...
"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...
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...
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...
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...
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...
Julian spends a most interesting and eventful first day in Lake Orenda Village. 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 portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....
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...
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...
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...
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...
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...
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...
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...
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....
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...
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...