Sissy story "The Chalet Girl"

Another steamy sissy story from my slut Claire! Enjoy!

"The Chalet Girl" by Sissy Claire

When he stepped of the plane Alex was hit by a bitter wind. The journey had been good, thirty minutes ahead of schedule, but now he was waiting in a gentle fall of snow for the car to pick him up from the airport.

The sky was a very light grey and clearly full of snow which was now landing on Alex’s hat. A back car pulled up, a Rolls Royce and a man with a chauffer’s hat stepped out and opened the rear car door nearest the pavement. “Mr Dowler? Madame Kenoux is waiting for us in her chalet.” Alex stepped into the car and left the man to put his bag in the boot.

It was early January and Alex was taking a gap year before going to university. He’d signed up for a cleaning position and hoped to get out and learn to ski on the weekends. Madame Dominique Kenoux was a very wealthy woman who lived in the middle of a Swiss valley and was miles away from anywhere.

The car Journey took about three hours and Alex arrived at just past 17:00 local time. He was tired and shattered but the driver just dumped the case down and left him to commence the long trek up the driveway. Under the two inches of snow was a gravel path that led to the house about five hundred meters further. There were bushes that had once been trimmed into animals along the path but they had been overgrown and looked a mess now. The grounds had a twelve foot brick wall surrounding them and, with all the weeds and plants on them, they looked as over-grown as the bushes.

Dragging his case along, Alex began the walk to the house. It looked like something from a Victorian TV program. There were at least five rooms on the front wall on each floor. Four floors and a loft stood in front of him, causing Alex to feel rather small and tiny. He was used to London terrace houses, not Swiss chalets.

On the door was a brass knocker which was in an intricate pattern and it rested on a small heart of the same make. Alex banged the door three times and waited patiently. After a few moments the great oak door came swinging in and there stood the most exquisite woman Alex had ever laid eyes on. Her hair was tied back in a pony-tail and the light from the crystal chandelier made it shine and shimmer. She had a little button nose beneath two purple-blue eyes and above a pair of plump lips that had a bright red shade coated in gloss.

She wore a big and long white fur coat that trailed behind her. She held it close around her but the top of a black silk gown could be seen just above her bosom. The coat flared slightly at the end which put her black high-heels on display. They added a couple of inches but that meant that she was still about five foot seven.

“Alex? Pleasure to meet you! I’m Madame Dominique Kenoux and this is my humble abode!” She smiled and beckoned the freezing young man inside. She spoke perfect English but had a very thick and seductive French accent. The entrance hall was huge. There were three chandeliers hanging from the ceiling and a massive switch way staircase that allowed access to the balconies. “You’ve been chosen to be my assistant for the next few months really! It’s a big house and little old me can’t do it all on her own! If you’re willing, you’ll do whatever I say?” Alex nodded, trying to take in everything. “Good. So I guess we should get to know each other then!” and, without any warning or explanation, she through her arms around him and pulled him into a deep and long kiss. He was engulfed by her coat and felt warm and comfy between the fur and silk. She let him go and grinned. “Oh yes. You’ll do perfectly!” She slammed the door shut and then grabbed him again, this time forcing her tongue into his mouth. Both hands placed firmly on his cheeks. She walked towards the stairs and pulled him with her.

Dominique was the only one who spoke as they walked up the third flight of stairs. “I never get much company, the people who bring supplies and such aren’t around long enough so I decided I needed a young man to keep me company and amuse me. The cleaners come once a week to do the whole house, so you’ll keep me company the rest of the time. I looked at the questionnaire you filled in and decided we would get on very well!”

They ended up in a bedroom with a huge four poster bed. There was a white sheet atop the bed and a red velvet duvet cover. The rest of the room was scarcely furnished but for a mirror on one wall and a desk of drawers on the other. The window showed the front driveway of the house.

Alex stood in the doorway as Madame Kenoux lay on the bed and pulled the coat over her leg to reveal the long smooth skin beneath. Her black gown held lace at the top and the bottom but was slightly tighter around the bust so there was a very noticeable cleavage.

Her left hand travelled down to beneath the gown and slowly started to move. Alex looked startled but the bulge in his trousers betrayed any illusion he wasn’t enjoying this. “Come to bed darling.” She gasped as a finger was slipped inside her pussy. “I want to make love to you” The number of fingers increased as did the power and speed that they were being used. Mesmerized, Alex stepped forward until he was about a meter away. “Strip.” She said in a voice that suggested he shouldn’t refuse.

He did as was bid and went down to his boxers. “No. All the way.” She slipped off a shoe and traced a line down his leg with her toe. He nervously slipped off the boxers and was now naked. She sat on the bed and slid her gown up until it was around her waist. The lace and cotton knickers she was wearing were slid to the side. She used a finger to beckon the eighteen year old closer. Their lips were millimetres from each other and about to touch when two smooth silky hands were wrapped around Alex’s head and pushed it down towards the waiting pussy. “Stick out your tongue and take me to heaven!” He obliged and started licking at the warm moist hole that his head was being forced against. It tasted amazing.

Alex was of slight build and had modern stylish hair but he had an almost feminine look about him. He was a little shorted than Madame Kenoux and about the same size. He’d never been popular at school and had barely had a girlfriend let alone had sex. This was like heaven for him as well.

“Oh yes! We’re going to have a lot of fun this season!” She started thrusting herself towards him which made it even more intense. Her legs wrapped around his neck and she rolled over onto all fours and covered him in the fur coat. She sat up and saw the tongue eagerly trying to please. She pulled him closer and felt it go deeper and deeper. Groans and moans escaped Dominique’s lips as orgasm came closer and closer. As she reached the climax of the first of many orgasms, she collapsed onto his face, letting her neatly trimmed bush rub against his nose.

“Wow…you were definitely a good choice.” She rolled over, still gripping his face with her legs so that he could savour the scent, and began gaining her breath back. Alex was in shock at the introduction she’d awarded him. “Now on your application you put your sexual preference as bi-sexual. If that’s correct, then stick your tongue inside again.” He stuck his tongue in. “Good. Take it out now. Next, you said you experimented with cross-dressing. Did you and if you enjoyed it did you enjoy it? The enthusiasm that you lick my pussy will be the excitement you gained from dressing up as a sissy.” Alex wrapped his arms through her legs and buried his face between them licking and pushing himself inside of her. He kept going until she climaxed again. Her muscles went into spasm and Alex’s mouth and nose were enveloped between her perfect lips.

“Interesting.” She sighed “You clearly loved being a sissy! That’s good. Go over to that drawer there.” She pointed at the top drawer at the side. Alex opened it up and inside was a sexy set of black lingerie. Alex glanced back to the woman who was now tasting her own juices. “I want you to put those on and then come over here.” He did as he was told and let the fur trimmed black knickers graze against his hairless legs. The garter belt was put on next and then the stockings which clipped onto the belt. His cock was getting rock hard which caused a small damp patch of pre cum to appear. There was a bra that had two breast forms built into them that was the last thing to add. They felt real to touch through the material and the little nipples were made very hard so could be seen gently poking through.

“Oh very sexy. Do a little spin for me, that’s right, oh la la! I think you should come back to bed now!” She stood and took the coat off, hanging it on a bed post, then snuggled under the duvet with a smile. Alex tip toed in the stockings to the bed and got in with her. Dominique, being slightly taller, wrapped an arm around the chest of the lingerie wearing boy and gently guided his hand back down to her knickers. She guided them in a rubbing motion and then took her own hand and ran it under the fake breasts. She gently pinched at them with each hand and made them more sensitive whilst Alex’s hand continued rubbing. His middle finger pushed the material aside and slid inside. A quiet gasp escaped and Madame Kenoux started kissing at Alex’s neck. Various red lipstick marks began to appear. The single finger inside her found her spot and as it gently rubbed around spasms of pleasure shot through Madame’s body. She pulsed into him making the finger go deeper and cause more arousal.

They stayed like this for a while with Alex’s nipples getting more and more sensitive and Madame having orgasm after orgasm. When they were finished Madame pulled Alex onto his back and smiled as she straddled his chest, just beneath the breasts. She kissed him on each cheek and then once more, lightly, on the lips. “Now all of this wasn’t just fun and games for me. I wanted to give you a gift. I can see by the state of your cock you have enjoyed this but what I’m about to show you will be new to you I’m sure!” She patted the bulge that was behind her and turned to admire it. It wasn’t a small cock, probably about six inches when fully erect but it was by no means big either. She kissed the tip through the cotton and slid her hand under to pick up the pre cum with her hand. It was on her first and second fingers. She held it to his nose saying “Smell that delicious juice. Do you like it?” Alex nodded. “Good girl. Then eat it.” With that, the fingers were forced into the sissy’s mouth and were sucked clean with a great deal of enthusiasm. “Now for your gift!” Alex had thought that was his gift! He’d experimented with cum eating but had only ever had a whole load once but wanted to take it further.

Madame pulled of her gown to reveal her own, similar set of lingerie and undid her bra, letting her huge breasts fall free. They bounced slightly as Dominique leaned forward and kissed the cum layered lips. “Tastes like sissy juice. I do love a nice sissy! Now the nipple play earlier turned you on I’m sure but it was for a reason. I made them VERY sensitive which means when these forms are played with, they will feel like real boobs to you. Here let me show you.” She took her hands and gently caressed the plastic form’s. Alex suddenly shuddered. The feeling was like never ever experienced. It was like a miniature orgasm every time she squeezed at them or pushed them into him. Dominique slid down her knickers and was now naked as she lowered herself to the sissy’s cotton covered cock. She steered Alex’s hands to the forms and allowed him to start doing it himself.

She pulled down his knickers and slid his hard cock inside her soaking wet hole. She started bouncing watching this man in women’s sexy lingerie playing with two very sensitive nipples. She bounced up and down and started riding him like a toy. Alex moaned and groaned as he was brought close for the first time. As cum squirting was imminent, Dominique grabbed a wine glass and slid up and started working the dick with her hands. The combination of the nipple ecstasy and feeling his cock inside someone for the first time had greatly quickened the process. Using her hand, she angled his tip down and made him squirt the biggest load into the glass. After a brief recovery, he looked up, somewhat confused.

“Don’t worry, all will become apparent!” She went to lick the top of his head and as he gasped in anticipation she pulled away and planted a huge kiss on his cheek leaving a perfect lip mark. “For now, just hold me and sleep.” She lay down next to him, pulled up the covers and snuggled against the heavily breathing sissy. After a while they both fell asleep after a night of many orgasms. Three hours earlier, Alex had been stood at the front door of this house fully clothed and ready for a cleaning position and now he was lying in bed, in lingerie, with a beautiful woman.

He woke the next morning with his lips locked with Madame Kenoux’s. He wrapped his arms around her and they kissed and played for a while. As Alex started to get very aroused, he noticed his penis was straining against something. Under the covers he looked and saw his little limp cock was caged in pink plastic. “That’s just to make sure you don’t get overly excited. Don’t worry I’ll let you cum on a regular basis! I wouldn’t deprive you of that!” She kissed him again. “Time to get dressed I think! You can keep that lingerie on but I’m going to give you a uniform to wear.” She walked out of the room and signalled Alex to follow. They ended up on the second floor in a room that was effectively a huge wardrobe. The racks were filled with bright pink and red dresses, shoes along the bottom, silky dresses, gowns and so much more.

Dominique wandered over to a rack towards the back of the room and pulled out a black maid’s uniform. It had white frills around the hem and neck line. There was a white apron that went with it and a black fur head band. Madame then knelt down, her still bare breasts bouncing lightly, and picked out a pair of heels that were similar to hers. There were ankle clasps on them that had small padlocks connected.

She slid the dress over Alex’s head and arranged the shoulder straps just hanging slightly. The heels were slid on and Madame locked the ankle straps, ensuring her new toy would obey. She stepped back and observed her handy work. Excluding the face, it looked almost as if Alex was a sexy woman. They then travelled through a cupboard door at the side into another room that looked like a dressing room from a Hollywood film. There was a big mirror that had light bulbs around the side. Shelves and shelves of makeup were on either side and a comfy red leather chair was in front of the mirror. Madame gently led Alex to the chair and began doing his, well almost her, makeup. First came a very light foundation that worked well with the young man’s skin. After that, she worked on the eyes with some mascara and then some eye shadow. Eye-liner was next; all of this was either black or a bright pink, which gave a nice frame to his eyes. A little blusher was added which brought attention to his pretty little cheek bones. Finally, lips were the focus. Before she even started on them she straddled his lap and gave him a quick kiss, licking his lips afterwards sending tingles down his spine. She put a pretty bright pink lipstick on him and then topped it off with a small amount of gloss to perfect the made up face.

Madame wondered a moment and then left the room, commanding the sissy maid to wait patiently. Whilst she was gone Alex could feel the sissy stick straining against the plastic cage. He’d never wanted to jack it so much in his life. He waited for what felt like hours until Madame returned with a black wig. It was flared at the bottom but curved around above to frame his face nicely. She put it on and positioned it until satisfied. When he looked in the mirror, Alex couldn’t believe how girly he looked. It was as if Alex didn’t exist now and all that was left was a shell of a sissy waiting to be taught.

“Alex is far too masculine name for a sissy like you. How about Alectra? Yes, that suits you. Alectra, would you be a doll and walk a little so I can see the new you?” Alectra obliged and did a sexy cat walk for her new mistress. “Very sexy! You look almost as hot as I do!” the sissy came back and knelt submissively at the feet of Madame who was now sat in the leather chair. “There are many jobs I am going to get you to do for me. The tasks will range from picking out outfits with me and modelling clothes and costumes to pleasuring me with your tongue and giving me a massage if I’m tired. But first, I think you’ve been so good and you look so lovely, I’m going to unlock your cock and I want you to milk it for me. Really work that sissy stick for me.” They walked back to the bedroom from earlier and Madame sat Alectra down before unlocking the cage.

“Good girl. Now take a hand and lick it.” Alectra did as she was told and the little dick sprang to life as Madame Kenoux pushed her breasts together and breathed heavily against the tip. The moist hand was taken and wrapped around the base and started squeezing and moving up and down. Madame took her own hand, sat next to her new toy, and slid a hand to her own clit and started rubbing.

The sissy had never masturbated like this before. The breast forms bouncing as she thrust the cock into her hand whilst feeling the lace of the dress and the tight fit of the apron drove her crazy but the lubricated hand meant she would last longer.

Dominique kept spitting on the clitty so that it stayed smooth. This meant that she was able to reach climax several times before she saw Alectra getting close. Madame pulled the fingers causing her pleasure from her pussy and forced them inside Alectra’s mouth. With her other hand she pulled the glass with cum still in it from under the bed. Like the night before, the head was angled at the glass and another huge load was added. “Now before I lock you back up again, I want you to cum again. Quicker this time! GO!” Alectra eagerly started rubbing it again quicker and faster than last time. She was getting very close very quickly when Madame Kenoux pushed her back and sat just beneath her breasts so that she could pin her arms down. “Now before you cum, you’re going to drink this.” She held up the glass with the sissy cum in it. “Do you want to cum?” A vigorous nod. The glass was put to her lips and the cum poured into her waiting mouth. “Don’t swallow it yet! Savour the taste of your own juice. Now carry on jerking it.” With cum on her lips and in her mouth, Alectra continued to smack her cock head to balls. She was close again and Madame Kenoux pushed the stockinged legs up above her so that the sissy stick was in the sissy face. “Now when I get to one, you’re going to Jizz all over your own face. Three, two, one CUM!” The sissy milked the stick and sprayed the juice all over her own face. “Now swallow that milk in your mouth. Good sissy!” The taste was warm but very bitter. Alectra loved it though, she had no idea why, but she did. “Now lie down and leave that facial you’ve got for about ten minutes. Then we’ll have a movie day. I’ve been longing for a girlfriend to watch these chick flick films with!”

That’s how the days went for the first couple of weeks. The two of them would wake up and Alectra would bring Madame Kenoux to orgasm with the sissy mouth. Then she would be made to model different outfits. The uniforms were all sorts of colours from Red to black to purple. Then came the milking where Alectra shot a load into her mouth and drank it down like a little puppy. Each day she got better with aim and less was on her cheeks and more in her mouth. Then they would spend the afternoon watching films, doing hair or learning how to do nails properly.

The cleaning crew came once a week and was made up of mostly muscly men and a couple of very attractive women. They worked the house thoroughly and Alectra was tasked with tending to their food and drink requests. She received the occasional grope from the men and the odd gentle stroke on the bottom from the women.

One day Dominique was painting Alectra’s nails when the woman in charge of the cleaning crew came in and explained that there was a blizzard just hitting and they weren’t even able to get down the drive. Madame told her that they could stay in the guest quarters as long as they needed to. When she had been thanked and they were left alone Madame turned to Alectra “I have a brilliant idea! Wait here.” She skipped out the room and came back ten minutes later with four members of the cleaning crew. Two men and two women. “Come over here and kneel at their feet.”

Alectra was wearing a red mini-dress today. It had cotton and latex stripes but no straps, so the breast forms had increased in size to hold the dress up. The black wig was still in place but now pulled back in a pony-tail like her mistress’ because she wanted to try and be as beautiful as her. The four cleaners were all stripping off now as well. Alectra looked a little scared but Madame soon crouched next to her and whispered “It’s ok; this is what you’ve always wanted. Make me proud Alectra.” And with that suddenly there were four huge cocks around her head. The two women were actually shemales and both had bigger dicks than the men. The smallest was six inches flaccid but as soon as they started working them they all grew to at least eight inches long.

The first shemale was blonde and very tanned. She ran her hands through the sissy’s hair and started pulling her towards the waiting cock. The vein running down the side and the pre-cum already forming was very different to the usual dildo’s Madame had trained him on. The Goddess with the gorgeous cock guided the sissy lips around the head and then deeper almost to the base. Alectra had trained on various lengths and Madame had managed to get rid of the gag reflex which allowed her to take all ten inches of this cock without a problem. The juice was already being massaged into her throat.

Her dainty hand was taken by one of the men. He had a perfect physique, like a man from a magazine and he started her working up and down his shaft. Alectra took over and started playing with the balls as well. The other man who was less muscular but when she looked up from the cock she saw he was absolutely gorgeous. She gladly started working both man-cocks with her hands whilst running her tongue up and down the shaft of the she-cock all the way to the smooth hairless balls. Alectra had started to get really into this slutty position and at this point was now sucking on each ball and loving it.

The shemale behind her was more feminine in body than the blonde one and not as tanned. The breasts were bigger and the cock about an inch shorter. She knelt behind Alectra and started fondling the breasts through the latex strip around them. The hard cock could be felt through the bottom of the dress and the strong hands of the Brunette amazon slid the bottom of the dress up. She too rubbed the heads of the man-cocks and lubricated her own hard cock with their pre-cum. The tip slid inside the sissy’s ass to start with but was pulled out and then replaced as if to tease the slut. Eventually the cock was in to the base and the sissy ass was getting pounded.

Alectra’s pretty red nails had little flower details on them and they clinked together as her silky smooth hands worked the real man dicks. She continued to suck at the other shemale cock whilst she bounced up and down on the other cock. She had kept them all going for about thirty minutes now but kept teasing them further and further on.

Madame Kenoux had been sat in an armchair watching the events unfold and had resisted the urge to touch herself because she wanted to keep some respect with her cleaning staff. Besides, the video camera that was recording the whole event would provide countless hours of stimulation. She walked up behind her sissy, over the shemale who was thrusting into her ass, and gave a sharp tug on her pony tail so that the cocks slipped from her lips and dangled in front of her. “They’re all going to cum soon and I want you to be a good little pet and let them spunk all over your face.” She released her head and stepped back.

The ass pounding shemale eased out of the sissy hole and stood. She started stroking like the other three and they were all now stood in front of her. To think three weeks ago, Alex was knocking on this door expecting to be cleaning and now she was dressed in a sexy dress, four cocks in her face and craving the taste of the cum she was about to be rewarded.

The muscle man was the first to finish off. He shot a massive load directly into her mouth filling Alectra with the taste of sweet, sweet jizz. She didn’t swallow yet, she knew better than that, and waited as the second man finished off, leaving a little strand on her lips but mostly topping up her mouth. They both got dressed and just walked out. They were finished with the whore for now.

The shemales lasted a few minutes extra and watched as Alectra sat on her heels with a mouth full of cum waiting to be used some more. The strand of cum on her lip dripped onto the floor as the blonde shemale jerked her load into the mouth. Unlike the men, she knelt down and kissed each cheek and stuck her tongue down the cum-filled mouth. When she pulled out there was a little cum on the end and she smeared it all over the perfectly made up face.

The final shemale was all that remained. She flicked her hair to the side and rubbed the head of her cock on her cheeks, leaving a web of cum across Alectra’s face. Alectra had a proper look at the whole shape of the shemale. The balls seemed very large and full. When the final cum-shot erupted over her face, it looked like Alectra had just squirted moisturiser over herself. The biggest load she had ever seen was now coating her face. The shemale gave a little squeeze at the caged sissy clit and then walked out laughing.

Dominique walked over to the cum soaked sissy “Good girl! Now smile for the camera!” a few still photos were taken. “Now drink down those huge loads for me!” Alectra obliged lovingly and gulped down every drop in her mouth. Dominique smiled and then rubbed in the cum of the final blast across all of her face until it covered every inch of her face. “You’re going to wear that as a badge of sluttiness for the rest of the day my little cum-whore. That’s just the beginning; there are seventeen cleaners all with big eager cocks waiting for your mouth.” Dominique went to the door and flashed a wicked grin at Alectra.

Apply to serve Superior Goddess Veronica, 
sissy and slave training available:

goddessxveronica@gmail.com