big sisters

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It’s not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All characters are over 18 and fictional. I may be persuaded to continue this story if there is demand.


The two men lounge back in the comfortable leather chairs sipping their drinks. One is fat with a ruddy complexion and wears loose shorts. Sweat dribbles down his bare chest despite the cooled air in the suite. Fat man owns the bar above which they are enjoying their drinks and chat, attended by a couple of lady boys. Both gurls are dressed in frilly pink satin sissy maid dresses. Under the dresses they wear pink corsets with garters holding up white seamed stockings and pushing up their pert little breasts. Frilly white aprons and caps adorn them and their heels are seven inches high. His guest is a well-built man with darker skin and a moustache. Bare chested, he is enjoying the cool air and the ministrations of the girly boys. He hails from a country of oppressive heat, oil, sand and immense wealth. Pretty maids such as these are unheard of in his land except in private harems.

His drink being empty, fat man clicks his fingers. One maid minces to the bar and returns quickly to replace both the empty glasses with full ones. The second maid brings a cool hand towel with which she wipes his sweaty chest. He feels his cock stirring in his shorts. Across the room a pair of lady boys, wearing only suspender belts, stockings and heels are sucking each other noisily in the sixty nine position.

“First one to cum will be punished extremely painfully,” fat man shouts out across the room.

“Have you received notice of that sissy to be auctioned shortly?” asks the fat man.

“Oh yes. I’ll have to bid on it. It’s absolutely stunning. I find it hard to believe that it is really eighteen. It is so small and innocent looking. It’s perfect. Did you check out those budding little titties and the bubble butt? I can see me spending many hours punishing those lovely globes and nipples. “

“Well the vendor is adamant that she has the paperwork and history that proves its age. I won’t be bidding as I know your resources are much greater than mine. I did enjoy the advertising material that arrived. I can’t stop watching the disk they sent. Just thinking about it is hardening me now. I have sent a deposit for a hand- on inspection. I’m really looking forward to some close up fun with it even though I won’t get to fuck it or have it suck me I will pay more for a cheeky slide and some kisses.”

“Yes, that scene on the rocking horse is amazing. I’ll have to demand that the horse is part of the deal. I just love the way it cleans its sissy cream from its panties after it cums. Once I’m finished with it I may pass it on to you my friend. I guess that will depend upon how well it can be repaired after I pop its cherry.”

“I’m ready for some release,” says the fat man “how about you?” the fat man giggles and snaps his fingers. The boy maids click over to them on their impossible heels.

“Oh yes I’m ready for some maid mouth.”

At that moment one of the pair on the other side of the room explodes into her companion’s mouth with much panting.

“The loser can wait in the corner. The winner will be rewarded later but for now, can go back to work.” Fat man says “Face away and bend over maids.”

The two turn away and bend forward forcing their dresses to rise and expose their panties. The backs of the panties have an open slit to allow easy access to their bottoms.

Fat man wanders over to the loser and leads her to a high backed chair over which he bends her. Quickly he binds her wrists and ankles to the arms and legs of the chair. After gagging her he walks behind and spanks her hard on each cheek until tears flow down her cheeks. Grabbing a handy tube of lube he squirts a liberal dose into her well used bottom.

“Very nice,” says the younger man as he slides his shorts down. The maids gasp and start to chat to each other in the local language.

“What are they babbling about?” the dark man asks.

“They like the look of your prick and are arguing over who gets to ride it” fat man answers.

His manhood is at least twelve inches long but not much wider than a regular prick. Reaching out he grabs one girl by the hand drags her to him and, putting a hand behind her neck, he forces her mouth onto the head of his penis. The maid sucks the head and then gradually works it into her throat. Although it is a challenge, she is well trained and manages to engulf the whole length.

Meanwhile, the fat man has forced the other maid onto his much more normal cock. She immediately engulfs his length.

The guest’s cock is now fully erect and the maid servicing him is sliding her mouth up and down his length and hoping that she will be shortly impaled.

“Enjoy the one over the chair. She is my gift to you. You will find her tighter than the maid” the fat man snickers.

Pushing the maid away, the guest leaps to his feet and positions himself behind the hapless girl. Puling he cheeks apart he places the head against her rose bud. Grasping her hips he forces himself into her. She is no virgin but has had less time than the other girls to fully open up so she squeals as she is entered. Soon her squeals turn into moans and then to panting as she enjoys the deep invasion.

Fat man lifts his maid onto his cock and lets her do the work as he watches the spectacle unfold. The guest rocks back and forth pulling almost all the way out and then driving back in as deep as he can. The girl is crying with pleasure by the time he explodes into her bowel. The maids look on with envy as he pulls back. There is a trace of blood mixed with his seed on the length of his tool.

“Clean him off” fat man says to the unoccupied maid. She does her best to lick the gooey mess from the massive length.

An hour later the two men are alone. Relaxed, they sip on their drinks. The well fucked girl has left and the maids are nearby in case they are needed.

“Thank you for your hospitality” says the guest

“It’s been my pleasure. I hope to visit you soon. Best of luck with the auction, I hope it goes well. I’ll be watching, wishing I could afford to compete.”

1. Suddenly I’m all grown up.

My name is Pansy and I’m a sissy. I live with my aunt and her twin daughters who are a few years older than me. I don’t remember my parents, as they died when I was very young. When I was very young aunty treated me as a boy until she discovered I preferred dolls to my boy toys and loved it when the girls dressed me in their old clothes. Aunty has brought me up, schooled me and helped me be a good sissy. I love my pink bed room where I spend most of my time with my dollies and my books. My room even has its own bathroom. In the corner is a beautiful rocking horse which I love to ride. There is a little bump in the saddle that rubs against my bottom which feels nice. I love to read about girls and their ponies. Sometimes there are boys in the stories but I prefer the ones with just the girls. I’ll explain more about my upbringing soon. For now I must tell you about the strange and exciting things that have happened over the last few weeks.

Something strange has been happening to my peepee. It keeps getting so stiff that it almost hurts. All my life it has gotten stiff occasionally but not so regularly as now. Aunty has forbidden me from touching it. I have always hated my little worm as the twins call it. I wish I was nice and smooth between my legs as they are. Oh, why can’t I have a cunny like them instead of my ugly peepee? Their cunnies are so pretty and taste nice too. As well as my stiff peepee I have noticed that my boobies are getting tender and more puffy than usual and my nipples tingle. Maybe all those special sissy tablets that I have been taking for years are starting to work. I have this overwhelming need to touch my little worm.

After breakfast and my bath I’m lying on my bed reading a story. Dressed in my day wear of very short satin dress, frilly panties, ankle socks and white Mary Janes I can feel my peepee growing against the smooth satin of my panties. Today the dress is pale yellow, high waisted with puffy sleeves and matches the bows in my pig tails. Feeling a little dampness on my tummy, I slip my hand under my dress. There is a drip of wetness at the tip of my peepee. Unconsciously I start to rub myself. Hearing a giggle, I look up and see one of my cousins staring at me. Running from the room I know she will tell on me for sure but I can’t drag my fingers away from the front of my panties.

Aunty rushes into the room, grabs my shoulder and stands me up. Clasping my hand she drags me out of my room and into the parlour. Without a word she hitches up her dress and sits on a straight backed chair. She roughly pulls my panties down to my ankles and throws me across her stockinged legs. My little peepee is pushed hard against her leg as she starts to spank me. This is the hardest spanking I have ever had and seems to go on forever as my sobs turn into cries and then screams. All the time I’m wriggling and squirming which makes my peepee rub against the smoothness of her stockings. Suddenly my little worm tingles and I gasp with pleasure as I spurt all over auntie’s leg. Oh, that feels so good.

“You dirty little faggot.” Aunty screams as she throws me onto the floor. Lying there I pant as I recover from my first ever squirt and the savage beating. Angrily aunty grabs my hair, pulls me back towards her and pushes my face down towards the mess on her leg.

“Lick it all up sissy.” She snarls. I hear the girls giggling from across the room.

I touch my tongue to it and recoil from the yucky taste. Aunty pushes me back down onto the goo forcing me to lick it up and swallow it. As I swallow it I feel it drying out my throat. I gag and almost throw up.

“Get used to it. All sissies have to get a taste for this stuff as it will become an important part of your diet for the rest of your life.”

Soon her leg is clean as is the floor where a few drips had fallen.

“Go to your room. I will talk to you later.”

I pull up my panties and scurry back to my bed where I lay sobbing and wondering what was happening to me. My throat is really dry and I needed to wee so I wandered to the bathroom where I drink water from my Barbie cup and then sit to pee. Feeling a little better I return to my bed and fall asleep waiting for Aunty.

The bed moves as aunty sits down. I awaken and sit next to her. She cuddles me which makes me feel a little better.

“Today is your eighteenth birthday. I have meant to talk to you about this before but you starting to spurt has leant some urgency to the matter. As you are now an adult and can spurt I will have to find a place for you in another household. This house is no place for an adult sissy like you. I am sure that you will fit in somewhere as a gentleman’s personal maid. Over the next month we will teach you the skills to perform for the most discerning lover of sissy maids. You will want to spurt every day and I know that I won’t be able to stop you. I will allow this but only under my supervision. Defy me on this and I will cane you.” She said severely. “Do you understand?”

“Yes Aunty” I replied meekly.

“From now on you will call me mistress.”

“Yes mistress.”

Mistress allows me to eat a light lunch and then leads me back to my room where she gives me a fresh pair of panties. These are very tight, made of stretch nylon. My peepee is clearly visible standing straight up in front. In the back of the panties there is a hole with frills sewn around it which aligns with my bottom hole. My rocking horse seems to have something sticking out of the saddle. The rocking horse is very realistic, carved out of timber and the size of a pony. Mistress leads me to the horse and I see that it is a peepee that is sticking up through the saddle. I remember that there used to be a plug in that part of the saddle. Mistress rocks the horse and I see the peepee, which is much larger than mine, move up and down out of the saddle. Mistress smears something oily onto the peepee and helps me to climb on. Slowly she forces me to sit down upon the peepee which stretches my little hole. I would jump up if I could but mistress forces me down until it fills me. After I settle mistress starts to rock the horse and I feel the peepee move in and out of me. Mistress allows me to rock on my own. Soon I find the sensation quite nice and my little worm stiffens. It feels especially good when the head of the peepee is just inside me. There seems to be a special spot there that feels extra good. I wish I could rub my hard peepee but I know that would invite a caning. The peepee in my bottom feels really nice now that I’m used to it. Soon I’m panting with pleasure and feel that I’m going to explode. Mistress senses that I’m close and gently rubs the back of her fingers along my nylon clad peepee. That is enough to have me squirting for a second time. The juice oozes through my panties and starts to run down the outside. Mistress takes my hand and uses it to scoop the goo up and pushes it towards my mouth. I lap it up. It still tastes awful but better than last time.

“You will ride this each day for as long as it takes to make you spurt. Every day we will put a slightly larger peepee on until you are stretched to my satisfaction. I will supervise your ride to make sure that you gobble down your sissy juice every time. Do you understand?”

“Yes mistress.” I answer.

Left alone I continue to ride, taking pleasure at the full feeling in my sissy bottom. Mistress returns with a book which she places on my desk.

“As part of your training I want you to read this book. It is more suitable for a sissy of your age than that childish stuff you usually read. I’m sure that you will learn lots from it. Get off that horse and stay off until I put you back on tomorrow.” She says as she drops the book on my little desk.

Fascinated I climb off reluctantly and go to the bathroom to wipe my slimy bottom. My panties are all sticky at the front so aunty tells me to take them off and to lick them clean. Sitting at the desk in my damp panties I find the book is entitled “Rich man’s toy an erotic romance.” Soon I am so engrossed with the tale that I’m still reading when I’m called to dinner. I have learnt so much about love, punishment and the sex act. Sex for girls and boys seems to involve mouths, peepees and cunnies usually after the girl is tied up and spanked. Girls really love the taste of spurts and get very excited by being spanked. They just love having big peepees pushed into their cunnies. I just can’t work out how this is at all relevant to me. After all I don’t have a cunny and I don’t think any girl would be interested with my little peepee.

After dinner I continue reading and discover that girls can learn to like having big peepees forced into their bottoms. They are usually reluctant at first because it hurts but soon they are addicted to it and like it as much as cunny sex. I guess this is how a sissy like me could have sex if any man wanted me. Is this why mistress wants to stretch my little bottom?

Finishing the book I do my evening bathroom stuff and change into my nightdress. It’s a pink short cotton baby doll which I wear with a pair of matching shorts. Exhausted after such an exciting day I am soon asleep.

Mistress wakes me early and sends me to the bathroom before I follow her through to the kitchen for breakfast. There are my usual three sissy tablets, two big tabs and one tiny. I swallow them with juice, eat some toast and have some herbal tea.

“Go to your bathroom, undress and wait for me kneeling in the bath” I am told.

I scamper away and soon I’m waiting on hands and knees in the bath when mistress enters carrying some odd items of hose and a rubber bag. She busies herself at the sink for a while and then turns carrying the now full bag with the hose attached. There is a strangely shaped plug on the end of the hose. After hanging the bag from a hook on the wall, she dons a rubber glove, squirts some clear gel on her fingers and pushes a finger into my bottom. Soon she replaces her finger with the plug which locks into my bottom. Turning to the bag she opens a little tap at the base and soon I feel warm liquid flooding into me. At first it feels good but soon I feel bloated and then start to feel very full and sore. I start to groan so mistress cuts off the flow, helps me move to the toilet, sits me down and pulls the plug. With relief I force a huge spurt of liquid out of me. Once I’m empty mistress shows me how to prepare what she calls an enema and helps me to fill up and void myself. She watches as I prepare another. Once she is satisfied that I know how to do it and that I am running clear she leaves me to shower with orders to clean myself out every morning before my shower.

Showered, I wander naked into my bedroom to find a new outfit laid out across my bed. There is a pink satin dress with a flared ruffled skirt and panties with a split bottom. Next to that are a pink coset, white stocking, frilly apron and a maid’s cap. On the floor is a pair of white Mary Janes with two inch heels. I have only worn one inch heels before as part of one of the twin’s games, and wonder how hard I will find these taller ones to walk in.

Mistress returns to help me dress. Firstly she wraps the corset around me and hooks the clips up the back together. It is very tight and squashes my waist giving me an hourglass look. The quarter cups push my little boobies up and leave my nipples exposed. Mistress shows me how to roll the white stockings up my legs, attach the garters and make sure the seams are straight. I slide the panties up my legs and settle them in place. I feel a little exposed with the opening at my bottom. Mistress tells me that the pants are called fukk pants. Slipping on the shoes I do up the straps and stand up. I am forced to walk back and forth across the room. I almost trip a few times but soon manage to walk elegantly.

“We will gradually increase the heel height until you are teetering around in seven inches with ease. I will have to hobble you until you take much shorter steps” she laughs.

The dress is placed over my head, my arms pushed into the puffy sleeves and settled into place. Cap and apron in place, mistress hangs a pink plastic spoon on a chain around my neck.

“That will help you clean up your messy spurts so that you won’t miss a yummy drop” she smirks as I grimace. “You will spend the morning learning how to do your makeup.” A pretty young woman wearing a white uniform and heels enters carrying a small case.

We sit next to each other at my dressing table while she teaches me how to apply various cosmetics. I’m a fast learner she tells me. I have had make up on before during a game that the twins used to play but that had been applied by aunty or the girls. By mornings end I am competent with several styles including: little girl, sweet teen, demure lady and slut hooker. She warns me that men can be quite particular about makeup styles and that I should sound him out before settling upon a particular look. The twins look on attentively throughout the demonstration. I think they are envious.

I go to lunch wearing the slut look. Pancake foundation, heavy glittering eye shadow, lots of blusher, glossy lipstick and lashings of mascara. Mistress and the twins mock me mercilessly.

“I have some special training planned for after lunch that will suit that make up perfectly. I want to test your gag reflex” mistress smirks. What does that mean I wonder?

The girls take my hands and lead me from the kitchen to the parlour where a strange high backed seat has been placed. I am soon seated, restrained at the ankles, wrists and around my tummy. My head is held in a clamp attached to the high top of the chair.

Mistress enters carrying a big rubber peepee. It is skin coloured and very lifelike. She pinches me hard on my arm so that I cry out. As soon as my mouth opens the peepee is quickly jammed into my mouth so far that I gag. When mistress pulls it back I bight down onto the soft rubber to stop it going back in. Mistress tries to push it back in but can’t. She smiles as I feel her reaching under my dress and grasping the little sack between my legs .Her fingers squeeze my sack, I scream and the peepee goes down my throat. As I feel the bile start to rise from my tummy, the tormenting rubber is pulled back. I barley manage to hold my lunch down. Mistress continues this game until I finally manage to get the thing down my throat without gagging. Pleased with this, mistress releases me and sends me to my horsy telling me to fix my make up on the way. I notice that a pair of video cameras have been set up at front and back of the pony when I return.

A slightly larger peepee has been fitted to the saddle and is already lubricated. Willingly I climb on and lower myself onto it. The slit panties come in handy for this. I find that I slip onto the thing quite easily and my little wormy responds by standing straight up. Mistress grabs my dress hem at the front and lifts it. She clips it to my collar. I hadn’t noticed that a little bra loop is fitted to the hem and a bra hook is sewn to the collar. She repeats this at the back so exposing my panty clad and peepee invaded bottom for all to see. I start to rock. The feeling is bliss as the rubber peepee invades my bottom making me pant with pleasure. My own peepee is dribbling in response. The twins are giggling. One of them reaches out and gives my little thing a long hard squeeze so that I cry out. They both laugh as it goes flat. Slowly the poor little thing recovers and becomes stiff again. Mistress reaches out and gently strokes me until I squirt.

Unclipping the baby spoon from around my neck she hands it to me ordering me to scoop up my sissy juice. The twins pull faces as they watch me gobble down my gooey mess. Although I’m starting to get used to the taste, it still dries my throat. Once the goo is off the outside of my panties, mistress orders me to dismount. Back on the floor I am led to my desk chair. Mistress pulls my panties down to my thighs and then makes me sit my bare bottom onto the chair. She carefully slides the wet panties down my legs to my ankles making sure that the wet bits don’t get near my stockings. One by one she carefully lifts each foot through the panty leg. The panties are now free of my legs. One of the girls is videoing me.

Mistress passes me the panties saying “use them to wipe yourself clean then lick it all off you dirty little faggot. Then you may put them back on. I hope you took note of how I removed them without dirtying your stockings as you will be expected to do this each time you spurt. If I see one drop on your stockings, shoes or floor you will be caned.”

Complying with her wishes I am soon sitting at my desk in my now clean but damp panties. I am left alone to read my book in which I’m soon engrossed. Reading the book has given me a wonderful insight into how even a sissy like me can have sex and maybe even find love. The book is finished just in time for me to have my evening meal. After the meal, mistress allows me to watch some DVDs on my television. All of them are pornographic covering both straight sex and various forms of bdsm. There is even a story about a sissy maid and her master which I really love. Eventually mistress undresses me and sends me to bed wearing a new translucent nylon baby doll in pink with a matching thong. I think I look very grown up and sexy in it. Knowing that I can’t touch my peepee I reach between my legs and tickle my bottom. I slide a finger inside and ease it back and forth. This feels really nice and I feel a little tingle in my peepee. My peepee slowly dribbles a little juice which feels lovely. I drift off to sleep dreaming of a handsome master pumping his big peepee into my tight bottom.

My days develop into a pattern of training. After my enema, mistress dresses me in a fresh sissy maid’s uniform. Gradually I get used to successively taller heels until I am comfortable in seven inch stilettos. As my ankles are hobbled together and I wear ribbons which must not touch the floor attaching my ankles to my wrists I am soon mincing well enough to satisfy mistress with short steps and my limp wrists held at shoulder height. I practice serving drinks on a tray and take over all washing duties for the household. I learn to curtsey whenever I provide a service or meet someone. Of course my sex practice continues. I spend lots of time practicing my oral skills on the dildo and stretching my bottom on horsy. My peepee spurts at least once a day and I am soon very good at removing my panties without soiling my stockings and cleaning them with my tongue. The taste of the spurts no longer worries me and I almost look forward to cleaning myself up. I am becoming obsessed with my bottom. The enema and time on horsey aren’t enough for me and I fall asleep each night with my finger in my bottom. Mistress tells me that soon I will be interviewed by some possible employers.

2. Before my spurts started.

I have no memory of life before aunty. Life has been mostly happy here with aunty and the two girls. Every day is like the one before but I don’t mind. My life has a great certainty to it.

Every morning I happily hop out of bed and go do toilet. I play with my baby dollies until aunty calls me to breakfast. I have to eat my special tablets with this meal. There are two big tablets and one small one. I asked aunty about them once and she explained.

“The two big pills are sissy pills to make your body soft and girl like. They will help you to have a nice rounded bottom, no body hair, cute little boobies and a layer of padding over your bones and muscles. The little pill is to stop you getting anxious. Sissies often get worried because they are not real boys any more but can’t quite be the girls that they want to be. The little pill will make you happy to be who you are and not what you might have been.”

After breakfast aunty bathes me and dresses me in a satin little girl dress a with high waist and puff sleeves, panties, matching ribbons in my hair, frilly ankle socks and white Mary Janes. It is then time for lessons until lunch time. Aunty has taught me to read and write and how to add up numbers. I practice reading my books aloud to her. If I make mistakes she puts me over her knee and spanks me until I cry. Once I have finished lunch I am sent to bed for a rest for an hour. The afternoon is spent riding my horsey, playing with my dolls or reading. Often I just gaze out of the window as the twins play in the yard where I am never allowed.

“Why can’t I play outside?” I ask Aunty.

“Sissies must not get sun on their skin. It will be very important for you in the future to have soft, creamy, unblemished skin. This is why you must never go outside.” She answers.

I feel happy with this explanation. All aunties’ lady friends comment on how pretty I look. I’ve been told that I’m short for my age and very lightly built. I have strawberry blond hair and creamy skin. The tablets must work as my body is just like aunty says it should be. I’m soft and rounded and very girl like with a lovely rounded bottom. If I had a cunny I would be perfect. I often wonder what it would be like to have friends to play with. The twins like to play with me but I never feel that I’m playing with them. I’m just a toy to fit into their games.

When we were all younger the girls used to dress me as a baby and pretend I was theirs. They would feed me bottles and soft food from a spoon. Sometimes I had to suckle on their little nipples for ages. They seemed to like that a lot. Tormenting my little peepee was a favourite game. Rubbing to make it stiff and then squeezing it until I cried was popular. Playing schools was also fun. One of them would be teacher while I and the other twin would be students. I was always the naughty one who had to be punished with a spanking. Aunty just used to laugh when I came crying to her. Sometimes I would get so upset that aunty would double my dose of happy pills for a few days.

As they got older the uses they found for me changed. Their developing boobies needed much more suckling than before and the girls didn’t bother with pretending I was a baby. Aunty had deemed that I was as well educated as I needed to be so the girls had all day between meals to use me for their pleasure. When I complained to aunty she just spanked me and explained that a young sissy’s roll in life was to serve girls and ladies in any way they pleased. Soon they had me cleaning their cunnies with my tongue for ages until they panted that they were happy. At least they had smooth hairless cunnies because one if my jobs was to shave them. I hated having to attend to aunts’ friends when she had a few over for afternoon tea. Occasionally aunty would have a lady stay the night with her. There were never any men in the house except tradesmen. On those occasions I was locked in my room.

Aunty was to have some friends to afternoon tea soon so the twins decided that they should have a beauty pageant to entertain them. They decided that I could be a contestant too. Aunty thought this was a great idea and took the girls out shopping for costumes. They promised to get me some outfits. Whenever they went out I was locked in my room, as aunty didn’t trust me to behave. I didn’t mind as I could read my books or play with my dollies.

After a few hours they returned with bags filled with clothes. The three had decided that we would each wear three costumes. There would be a competition where we would wear pretty party dresses, one for swimsuits and one for pretty night wear. My dress was really pretty in pink of course. The girls had one in silver and the other in white. We each had pretty sandals with one inch heels. My swimsuit and night dress were to be a secret while I got to see the pretty bikinis and night gowns that the girls got. I hoped mine would be just like theirs.

The following morning was spent with aunty as she did our hair and makeup. I even got to paint my finger and toe nails bright pink. My hair was curled into ringlets while my makeup was really more suitable for someone older. After lunch we put on our party dresses. Mine was so pretty and fitted perfectly. I thought I looked like a princess. The girls looked lovely too. We stayed in our rooms until the guests arrived.

Aunty called us and had us wait in the hall near the parlour. The twins were sent in one at a time to show off their dresses. When it was my turn I walked into the room to find that a space had been left between two rows of guests for us contestants to walk through. There were four women on either side. I sauntered along until I reached the end of the makeshift runway, turned and walked as daintily as possible back and out to the hall. There was polite clapping from the audience.

We were called back in together and informed that I had won the first part of the contest. I was surprised when the girls congratulated me as I expected them to hate me. Once I saw my swim suit I understood why they smirked with the congratulations. We changed to our swim suits in the hallway. They each had a very pretty bikini which fitted them perfectly. I, on the other hand had a nylon one piece at least one size too small. When I managed, with aunties help, to slide into it I discovered that my peepee was clearly outlined in the front. When aunty saw this she reached through the leg opening, grabbed my peepee and forced it between my legs. I looked ridiculous but at least my peepee wasn’t visible although walking was uncomfortable. I was sent in first and all the women pointed and laughed at me until I ran crying from the room. The girls each followed and were applauded. They were deemed to have tied for first in the swim suit competition.

For the sleep wear competition the girls had beautiful long satin night dresses. One was black while the other was white. They looked very grown up. I was given a pink baby doll that was very pretty but completely transparent. There were no panties so there was nowhere to tuck myself away. I burst into tears and refused to enter the parlour. Aunty slapped me and threatened a severe caning. I was scared enough to walk, crying into the room where the women called me horrible names and said they should punish me for being such a nasty little sissy who showed it’s peepee in front of ladies. Trying to run I was grabbed by a woman who threw me over her lap and proceeded to spank me while the two girls had their turn to show off.

That was the worst ordeal that the girls inflicted upon me. All in all I couldn’t complain too much with my upbringing. I was well fed, clothed and had plenty of toys. Mostly I enjoyed the girl’s games and was happy with my pampered life.

Interview time

My training continued. I could now mince easily in seven inch heels if they had a platform sole. Each day I spent half an hour trying to walk in eight inch ballet heels. After a week I am able to hobble around in these torture devices. My calves are left burning after each session. Mistress tells me that it is important to learn to walk in them as I will be more employable if I can. My makeup skills were adequate and I only needed help to do up my corset. Aunty deemed that my bottom was stretched enough for most men to find me a nice tight fit without doing too much damage. I had learned how to carry drinks on a tray without spillage and how to iron a man’s pants and shirt just in case I really was going to be a maid.

My first interview was scheduled for two o’clock so I had the morning to prepare. By the time he arrived I was clean inside and out, with my bottom plugged for safety and wearing my French maid outfit over my corset and white seamed stockings. Seven inch white heels completed the outfit. My makeup was modest as would befit an innocent young woman and my hair was tied in pig tails.

As ordered I waited in the hall near the front door so that when the bell rang I was able to immediately answer it. Before me stood a very fat and sweaty old man wearing baggy shorts, sandals and a Hawaiian shirt. I truly hoped that he was not going to employ me. Curtseying I stepped back to allow him in and closed the door behind him.

“Please follow me sir” I said and minced along the hall into the parlour. I could hear him puffing as he followed me. After he was seated on a two seat lounge I ask “may I get you a drink sir?”

“Yes please. A beer will be nice. Call me Daddy” he leered at me as he says this.

Mincing across to the bar I took a bottle from the refrigerator opened it and poured the contents into a tall chilled glass. Tottering on my heels I carried the glass on a tray to Daddy and placed it on a side table next to him. After curtseying I returned the tray and stood with bowed head waiting for instruction.

“Come here and stand in front of me” he ordered “and clip your skirt up at front and back.

Quickly I complied.


I did and soon felt his hands massaging my bottom before he slipped a couple of fingers through the hole in the back of my panties and ran them up and down through my crease. I gasped initially with shock which turned to pleasure as he pushed against my plugged bottom. I could feel my peepee stiffen. He soon tired of this, removed his fingers and ordered me to turn and kneel in front of him. After dipping a finger into his beer he offered it to my mouth. Being a well-trained sissy, I sucked the drink from his finger and continued sucking vigorously until he pulled his finger away.

“Sit on my knee” he ordered. So I stood and gently eased my bottom onto his lap. Wrapping one arm around me he used his other to pull my face to his and then passionately kissed me. Yuk. I hated it but my training was such that I kissed him back and pretended to enjoy. While he held me in his embrace he slipped his other hand down my front and massaged my peepee through my sheer panties. Soon I was panting while the pressure built inside me. With a gasp I exploded.

Daddy took my spoon from my neck chain, scooped up my escaping sissy juice and fed me every drop that went through the fine material.

Pushing me away he said “clean yourself.”

Standing, I eased my panties down my legs squatting to get them past my shoes. I used the skimpy garment to wipe my peepee and tummy clean and then my tongue to clean the panties which I then slipped back on. The panties, although sheer were very tight and hugged my bottom tightly pushing my cheeks hard together.

Daddy said nothing as he lifted his bottom to allow him to slide his shorts down his legs. I could see his big peepee outlined in his underpants. Pulling me down onto the seat next to him, he took my hand and placed it upon his rapidly stiffening peepee which was now sticking out of his pants. My duty as a well-trained sissy was clear so I started to stroke it. This evoked a groan from Daddy. Soon he was panting and his peepee was rock hard.

Daddy pushed me to the floor making me think he would force me to suck him. Instead he climbed off the lounge, positioned me kneeling over one of the cushions and knelt behind me. I felt his peepee pushing through the split in my panties and being forced into the crack between my rounded cheeks. Daddy would dearly have loved to push into my bottom but had to make do with rubbing back and forth, trapped between my buttocks and the tight panties. His breathing rasped with excitement as he pumped back and forth enjoying what I would later discover was called a cheeky slide. His thrusting soon sped up and he started to moan. I wasn’t sure if I liked this although my peepee did as it hardened up again and started to dribble. Suddenly he stopped and held me tight. He groaned and I felt wetness between the round globes of my bottom. Once his breathing slowed he slid out of my panties, wiped his peepee on my bottom, pulled on his shorts and just walked off and left the house. I felt disappointed that I hadn’t even received a thank you. Was this how a sissy is treated? Aunty walked in and told me to go my bathroom and clean myself.

Each afternoon that week a different man interviewed me. Most were old and ugly and used me in much the same way as the first. There was one who was younger and quite handsome. He was very nice to me. I enjoyed kissing him and thought he would make a lovely employer especially after he sucked my peepee until I spurted.

The following day Aunty took me aside and explained that several men were interested in employing me. She had decided that the fair way to choose would be to auction me to the highest bidder. That way she would recoup some of her expenses incurred while training me to be a good little maid.

“Would the men pay me for my work?” I asked.

Mistress laughed “That would be highly unlikely. They will be purchasing you from me and will use you as they please. You may be put to work as a maid or just used as a sex slave. Most of the men will value you so that you will only be punished if you are naughty. They are all rich and have a reputation of looking after their slaves keeping them in luxurious quarters and providing them with lavish gifts and clothes. Today and tomorrow we will prepare for the auction which will take place in two days’ time. “

I burst into tears. I was to become a slave. Maybe even a sex slave. Although I looked forward to having a man inside me I was hoping for more than just sex. My dreams were falling apart. Mistress slapped me and sent me to my room.

After lunch I was ordered to do some clothes washing. Mistress set up a video camera on a tripod and gave me some specific instructions. Dressed in my maids outfit I pulled various items of lingerie out of a basket. As instructed, I pushed the gusset of each pair of panties to my nose and sniffed. After a deep breath I would put the panty into the washing machine and smile while licking my lips. Amongst the delicate panties and other lingerie I discovered a pair of men’s boxers which were stiff and stained around the area of the fly. I sniffed, smiled and licked the dry spurt that had been deposited before reluctantly dropping them into the machine. While the machine did its work I ironed a man’s dress shirt and a pair of pants. I guess this was to show both my domesticity and my obsession with sexy smells and tastes.

After being videoed hanging the washing on a clothes line set up in a shaded courtyard mistress ordered me to pour a glass of wine and deliver it to her in the parlour. One of the twins filmed me pouring the wine and carrying it on a tray to mistress. I placed the glass on her side table, curtseyed and retreated to a corner where I waited with bowed head for further instruction. During the rest of the afternoon more video was shot of horse riding, squirting, cleaning up my juicy panties and deep throating a rubber dildo. Finally a long session walking, standing in ballet heels and receiving a mild spanking was recorded. I was exhausted and had very sore legs and bottom by the time I settled down after dinner to read some more erotic fiction and then to sleep. I dreamt of being spanked whilst wearing a beautiful wedding dress by a tall dark haired gentleman in a dinner suit.

Next morning I was videoed showering, shaving, cleaning the inner and outer sissy and dressing in a variety of outfits. The afternoon was free for me to read and relax after another hour of ballet training. During the night I dreamt that I was tied over a vaulting horse wearing the tattered remains of my wedding dress servicing an endless line of filthy smelly men with my mouth and bottom.

My big day.

Awakened early I had breakfast and then did all my bathroom duties. Freshly clean both in and out I dressed in my usual underwear of pale pink corset with quarter cups, matching panties, seamed white stockings and my seven inch heels. Mistress had instructed me to apply a nice girly style of makeup and to put my hair in pig tails. I then watched as Mistress and the girls packed all my clothes into a large case. As the auction was to start soon Mistress told me to remove my panties and shoes. She then helped me into my ballet heels and applied rouge to my exposed nipples. I was to be very much on display for the bidders. After locking a pink dog collar around my neck she led me slowly hobbling into the parlour with a light chain attached to the collar.

I was led up onto a raised round platform with a pole in the centre where Mistress attached the chain to a hook on the pole above my reach height. I could move around the platform, even kneel on the floor, but was stopped from leaving it by the chain. Mistress placed a small bud microphone in my ear, telling me to listen for and obey instructions. I noticed several cameras set up on tripods pointed towards me. There were no bidders in the room. From my position I could see a large television screen on which was playing videos of my daily activities. Now I understood why I had been filmed so much lately. I guessed that this would be an internet auction. Suddenly I was flooded with bright light from spotlights and the platform started to revolve. I heard a voice in my ear telling me to bend over and to spread my cheeks. Doing this I had to be careful not to fall over in my crazy shoes. Then I was told to push a finger into my bottom. As soon as I did this my little peepee stood up and started to dribble a little juice. The voice told me to stand upright which exposed my dribbling little worm to the gaze of the cameras and bidders. Soon I spurted and managed to catch most of the juice in my hand which I licked up as instructed. A couple of drops had landed on the floor which I cleaned up after the stuff in my hand was finished.

After about twenty minutes the platform and lights stopped. I guessed that I was now a slave to hopefully a kind owner. Mistress unhooked my chain and led me back to my room.

“Change your shoes, put the ballet shoes in your suitcase and put your panties back on.” Mistress said. As I complied she continued. “You have been purchased by a very rich man. I hear he is quite handsome and not terribly old. If you are a good little sissy I’m sure you will be treated well. Rumour has it that his cock is magnificent which I’m sure will suit your new found obsession with having a well filled bottom.” Kissing my forehead and unclipping the chain she stepped back. “Wait here. Your master is sending someone to collect you and deliver you to him.” A little tear stained my cheek as she dragged my case from my room and left me alone. Looking around I noticed that my horsey was no longer in the room.

Soon a tall woman walked into the room. She was dressed in a voluminous white hooded dress which covered her from head to foot. She was even wearing white gloves with a veil clipped to the hood covering her face. Pulling the veil aside to expose her very pretty pale face she spoke.

“My name is Jasmine. Our master has sent me to fetch you.” Passing me a carry bag; she said” dress in this.”

There was a dress identical to Jasmine’s in the bag which she helped me into. I hoped that I wouldn’t have to dress this way all the time. I would miss my frilly satin dresses.

Jasmine must have read my mind as she said “Don’t worry; the sack is only for the trip to our master. We must be modest in public but you will wear all your pretty stuff for him in private. Follow me.” She walked from the room after clipping both our veils into place. I had difficulty keeping up as she strode along on her long legs while I minced along in my usual sissy style. In the hallway our heels clicked on the timber floor as we made our way to the front door, down the steps and into a waiting limousine. And so I had my first ever car ride. I was amazed at all the sites I saw during the one hour trip through the city. Finally the car stopped at a wharf where there was an enormous ship tied up. Jasmine led me from the car to a gang plank which we climbed onto the deck. I saw a couple of rough looking dark skinned men coiling ropes nearby. They ignored us as I was led through a doorway along a corridor and into a sumptuous cabin. Soon my case was delivered by a uniformed steward.

Once he left, Jasmine quickly removed her sack. “It’s so good to be out of that ugly thing. Take yours off. You won’t need it again in here. We must wear these whenever we are off this deck or in public. The religion forces me to wear it as I’m a woman. You will wear it for modesty as we don’t want the crew to get excited. Any one on this deck will be safe to see us.” Pointing to a door she said “that is your dressing room, robe and bathroom through there. Mine is on this side. We have to share the bed.” Indicating the queen sized bed. Her lingerie was similar to mine but black rather than my pink. She was blond and blue eyed with long shapely legs. Taller than me with well-defined arm muscles I knew that she would have no trouble controlling me. Her lovely firm breasts were completely exposed as her corset had no bra cups and was just shaped under each globe. I wished I had boobies like those. Jasmine smiled as she saw me looking at them.

“If you please Master he might give you a pair just like these” she said with a giggle. “Unpack your clothes and I will take you to him.”

Through the door I found a dressing room with vanity and mirror with lights. To the right was a walk in robe with plenty of hanging room, shoe storage and drawers. To the left was a bathroom with bath shower stall, toilet and basin. It was all beautifully appointed. While I unpacked Jasmine spoke.

“When we enter the Princes chamber we drop to our knees and place our foreheads to the floor. If he wants us we must crawl to him keeping our eyes averted. We are not allowed to look at his face unless he requests us to do so. Once we are close he will present each of us in turn a foot to kiss. He may then allow us to sit back on our heels while he inspects us. Don’t look at his face unless you want a whipping. Now take off your panties and we will go.” Jasmine removed hers at the same time exposing her hairless cunny. We left the room through yet another door with me trying to emulate the way her beautifully rounded bottom swayed seductively. I noticed that there was a strange mark that seemed to be branded into her left buttock.

Meeting Master.

Through the door we found a parlour with comfortable furniture and a well-stocked bar in a corner. Our heels tapped as we crossed the timber floor. My horsy was set up against one wall. At the far end was another door which Jasmine knocked upon.

“Enter” a deep voice boomed out.

Jasmine opened the door and dropped to her knees. I followed and glimpsed a tall handsome man sitting at the far end of the room as I kneeled.


Keeping my head down, I crawled behind Jasmine until she stopped and rested her forehead on the floor. I crawled next to her and pressed my head to the floor. In front of my face was one of master’s feet which he tapped against my head. I lifted my head to allow him to push the foot under my face so that I could kiss it. I did so, not stopping until he removed the foot.


We did. Pointing at me he said “turn slowly.” I turned.

“Hmm. You are a plump little thing. We will need to watch your diet. I like my sissies rounded but not fat. That bottom looks perfect for my purposes. Is it clean inside.”

“Yes master.” I whispered.

“Do you need to pee?”

“No master.”

“Good. I don’t want my floor wet when I punish you for glimpsing me as you entered this room. Jasmine take her to the room.”

She led me through a side door and into a dimly lit room. The decor was all red and black with dark timber and strange leather covered equipment. Jasmine bent me over a leather topped vaulting horse and secured my wrists and ankles with leather cuffs. My ankles were pulled well apart so that my buttocks were spread exposing my little bud. Even though I was expecting a punishment, I was excited. My little peepee dribbled as I heard master pad across the room and walk around to my front. He was naked; all I could see were his muscular legs and his exceptionally long penis hanging between them. Wow. Slowly I saw his hands lowered into view holding a whippy cane between them. Gasp.

He moved out of my sight and I heard him pad around behind me. It seemed forever before I heard the cane whooshing through the air and felt its burn across my buttocks. I screamed and struggled against my bonds. A second swoosh and my bottom was on fire. Crying, screaming and begging for mercy was my world for the next few minutes as the cane struck another eight times. Suddenly he stopped. My bottom was on fire as I slumped there sobbing as he padded around in front of me again. Grabbing my hair he pulled my head up and pushed the head of his penis into my gasping open mouth. Through my tears I could see his cruel but handsome face.

“Suck” he commanded.

My open mouth was full as I tried to get control of my breathing and concentrate upon my training. Soon I was suckling hard on the head which was like velvet on my tongue with a salty taste. Slowly he began to force himself into my throat. I managed not to gag as more and more length was forced into me. Just as I thought I must suffocate he pulled back to allow a breath before assaulting my throat again. Amazingly, during this oral rape a strange feeling overcame me. A warm tingling flutter invaded my lower belly and my little peepee hardened and the dribble of sissy juice increased. Had my mouth and throat not been full I would have been gasping with pleasure. My little bottom bud twitched with anticipation or fear. Although very long his member was only a little thicker than the peepee on the pony’s saddle making me think that it may not hurt too much.

I lost track of time as I contemplated my total subjugation and strange physical response to it. Suddenly he pulled back so that only the head was in my mouth. He was panting and I realized he must be ready to squirt. I sucked as he exploded in my mouth. There was much more juice than I had ever squirted but I managed to swallow every drop. Pulling out he squeezed the head to expel a few more drops which I gratefully lapped up with my waiting tongue. His juice tasted a little stronger than mine. Yummy.


“Yes master.”

“Clean up here, take it to your room, treat its bottom, start it on the new hormone mix and feed it. Bed it, flush its insides and yours. I want both of you to serve dinner tonight so be dressed correctly and attend to me at seven.” With that said he padded out of the room.

Jasmine undid my bonds. Then told me to lick up the dribbles I had deposited on the floor. Once clean I followed her back to our room. The ship must have left the wharf as I could feel some movement through the deck.

“Lie on your stomach on the bed.”

As I relaxed on the bed jasmine rubbed a soothing cream onto my punished bottom which made me feel much better. She walked away and returned a few seconds later. I felt a cool wipe across a little patch and then a sting of a hypodermic.

“A few weeks of this should get those boobies growing. If not, I’m sure he’ll give you implants. He likes his girls and sissies a bit busty as you will see when lunch is delivered.”

A quick k nock on the door was followed by the door swinging open to allow a trolley loaded with food to be pushed into the room. The creature with the food was naked, six foot plus tall, fat with a bald head, crazy make up and enormous breasts. Between its legs was a small peepee but no sack of marbles. It was grotesque in the extreme and spoke with a high squeaky voice. Thinking back on the busty comment that Jasmine had made, I hoped I wouldn’t end up with a pair like that. It left us with the tray.

As we tucked into the salads and fruit Jasmine explained about eunuchs. By the end of that discussion I was very happy with my life so far compared to what that poor creature had lived through.

Having eaten we stripped, snuggled up head to tail and sucked each other to climax together on the bed. I was dreaming of master’s massive member when Jasmine woke me. The ship was rolling a little more.

“Does master have sex with you?” I asked.

“Oh yes. He uses all my holes but prefers my bottom as it is the only one he can get fully deep.” We spent the next two hours preparing ourselves for the prince as instructed.

By six forty five I was ready to serve my master and was tingling with anticipation. My insides were squeaky clean, lubricated and my bottom was plugged. My uniform was a frilly black maid’s dress that barely covered my bottom and was an inch above my seamed black stocking tops. There was a satin apron and cap to complete the dress and seven inch pumps connected together with a short hobble chain which would shorten my step. Under the uniform I wore a pink under bust corset with suspenders to hold the stockings and a pair of pink fuck panties. My make-up was over the top slutty with too much of everything. I had a little shoulder bag with extra make up. Jasmine wore an identical uniform. We had a lot of fun helping each other to prepare.

Jasmine led me to the dining saloon where we found a table set for two. There was a bar in one corner and a door with a small glass window which I guessed led to the kitchen. We waited side by side with head bowed near the bar. Soon the door opened to allow or master to enter. We dropped to our knees and bowed our heads to the floor.


We stood. With Master was a tall muscular Negro in a sailor’s uniform. Following Jasmine’s lead I pulled back the sailor’s chair while she looked after Master. Once we had them seated I placed a napkin on the black man’s lap.

“Beers for both of us Pansy” master demanded. I minced to the bar to prepare them while jasmine served anti pasta. We then stood back with heads bowed. We served two more courses with wine and later coffee. Jasmine bumped a wine glass during the meal, spilling a drop on the cloth.

Master stood “get a cane slave” pointing at Jasmine who scampered to the bar where there was supply of canes.

“Assume the position.” Master flexed the cane between his hands.

Jasmine slid her panties down to her ankles and grasped her ankles, presenting her magnificent bottom to Master. Before the first stroke he slid the cane between the folds of her cunny. I heard a gasp that sounded like pleasure and was sure I could see moisture on the cane as it was pulled back and slashed across her bottom. There was no cry from jasmine just a sigh replaced by panting as once again the cane rubbed across her slit. The cane slashed again. Jasmine was now panting loudly as her moisture dribbled down her inside thighs to stain her stocking tops. With each slash and rub she was louder and wetter until, on the tenth stroke she cried out in ecstasy as she came. Wow.

Master threw the cane to me and returned to his seat to finish the meal. “Clean it and put it away” he snarled at me. I licked the lovely juice from the cane and placed it back in the bar.

The captain sat slack jawed and then asked “was that real or does she fake it?”

“It’s real. I have owned her from birth and she has been trained by the best bed slave trainers to cum to pain stimulus. She will cum even more strongly if pleasure is combined with pain. Pleasure alone is much more difficult for her. She is a true pain slut who begs for release, as you will see after dinner.”

Once they had finished their meal, they led us to the room where I was orally raped earlier. I was told to stand in a corner where I could see what would happen.

“Remove those panties” master ordered Jasmine.

“Lie on the bench.” Jasmine climbed on to leather covered bench which had a set of gynaecological inspection stirrups set at one end.

Jasmine was now on her back with her feet held high, wide and pulled towards her shoulders. Her cunny and little bottom bud were totally exposed. Master was flexing a long whippy cane between his hands. Standing back a little master slashed the cane down upon the hapless slave’s tender parts. Rather than a scream jasmine gasped out a sigh. Time and again the cane whistled through the air to strike the delicate flesh until Jasmine’s orgasm rippled through her. Her red striped cunny and bottom were slick with her juices as she writhed in pleasure. Eventually she calmed down.

“Now that she is tender and moist, please feel free to use her for your pleasure” master said to the captain who wasted no time in freeing his thick member from his trousers. Although not as long as masters’ penis, the captain’s was at least twice the girth. I wondered how it would fit into Jasmine’s cunny which looked quite small. I hoped that I wouldn’t be forced to accommodate such a monster.

I was surprised at how easily that thick member slipped into the girl. Obviously a cunny could stretch much more than my bottom.

Master led me to another bench and lifted me easily onto it lying on my back. There were no stirrups so master just grabbed my ankles and placed them on his shoulders. Reaching through the access hole in my panties he roughly pulled the plug from my bottom. The lubricant that we had put there earlier seeped out, making my panties damp. I tried not to look at Master by looking to one side. Grabbing my face he forced me to gaze upon his cruel but handsome visage.

September 2018
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