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."
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?