Crystal's StorySite


Holiday at Aunties

by Sissy Billie


It was still dark at 5.30 in the morning as Mistress Helen put my suitcase in the boot of the car, along with hers and Caroline's. I was ordered to sit in the back seat for the long ride to Auntie's house.

My travelling outfit was a skimpy white chiffon baby-doll nightie with fluffy marabou trim all around the hem. My ruffled white satin panties concealed the fact that I was severely restricted by a cruel metal chastity cage. White knee-socks and shiny white patent strappy sandals with 3-inch heels completed my sissy outfit.

My hair had been freshly permed and coloured the night before - this time it was a bright copper-red, short and tightly curled. I had spent the last thirty minutes applying my make-up, including pale pink lipstick, blue eye shadow, black eyeliner and long false lashes, according to Mistress Helen's instructions.

I sat apprehensively in the back seat of her car, clutching a small bunch of flowers, as my wife and her friend got in and we drove away. Mistress Helen and Caroline were going on a two-week Caribbean holiday, while I was to stay with Auntie. Mistress Helen had kept me locked in my chastity device and I had not been allowed any release for the past month as part of her preparations for my stay.

The sun rose as we drove along and Helen and Caroline discussed the tropical islands they would visit. Mistress Helen laughed and reminded Caroline of their plans to have holiday romances on every island they visited. All the while I thought of what was in store for me - two long weeks at Auntie's…

I was sure every driver that passed us took a double-take at the fluffy creature in the back seat of our car. Mistress Helen reminded me to sit up straight and not pay any attention to the other cars. My face was hot and flushed for the entire ride.

After what seemed an eternity, we arrived at Auntie's spacious country house. The garage door was open and we drove inside.

"Okay, Baby Doll!" Mistress Helen ordered. "Out you get!"

As she got out and took my big white suitcase out of the boot I nervously got out of the car. Caroline wound down her window, looked at me and laughed. I could see my breath in the chilly garage as Mistress Helen took my suitcase inside, instructing me to wait until she returned.

"You know what, little sissy boy?" Caroline smirked. "Your wife is going to get fucked by a real man on this holiday. Just think, while you're here being bossed around by your Auntie, some gorgeous black hunk will be pumping his hot load in your wife - over and over and over. Two solid weeks of proper fucking – that's what she needs!"

Mistress Helen returned and stood in front of me. Looking me straight in the eye, she gave her final instructions before departing.

"Remember everything I told you, Baby Doll. Give Auntie your bunch of flowers and the letter in your purse. You are to obey her as you obey me. Do everything she tells you or you know what will happen. I expect to get a good report from her when I return or you will be VERY sorry!"

"Yes Mistress," I blinked.

She gave me one last look up and down, and kissed me tenderly on the lips. She got back in the car with Caroline. As they backed out of the garage and sped off to the airport I could see her and Mistress Helen laughing.

I pressed the button to close the garage door, and nervously entered my Auntie's house - a fluffy little baby-doll, perched on high heels - feeling every bit like the little sissy I knew I was. I closed the door behind me, and stood alone in the hall, awaiting the woman who was to be in charge of my life for the next two weeks - my Aunt!

"Well! What have we here?"

I spun around on my heel to see Auntie enter the room. I felt my penis swell uselessly in its chastity cage.

Auntie was in her fifties, but had a body a woman of any age would die for. She had a shapely figure that still turned men's heads and her high cheek bones meant her face still carried an imperious beauty, enhanced by subtle makeup. Her golden hair was fluffed and teased into a chic bob.

She had obviously just returned from an early morning game of tennis and was still perspiring from the exertion. She wore a tight white top, which emphasised her well-shaped breasts, and a short pleated tennis skirt. Looking athletic and lightly tanned, she was magnificent - and incredibly sexy.

"Darling! It's so lovely to see you again - come on in. Leave your suitcase over there by the stairs – we'll settle you into your room later. Are those for me?" Auntie asked reaching over for the proffered bunch of flowers and kissing me on the cheek. "How sweet you are! Thank you my angel. You look absolutely gorgeous by the way – hasn't your Mistress dressed you beautifully? That baby-doll nightie – didn't I buy that for you when you were my little pet? With those long white socks you look so cute!"

As usual when faced with such effusive 'compliments' from Auntie I felt my face go red with embarrassment.

"Ohh – I've made you blush!" said Auntie, enjoying herself enormously. "You should be proud of the way you look my dear". With that she gave me another kiss and took me by the hand to lead me into the living room. "Let's have a cup of coffee, shall we? Come and sit with me on the sofa" she said patting the seat next to her. I sat primly on the edge of the seat in my flimsy nightie as Auntie relaxed next to me, her bare legs artfully crossed in her short tennis skirt only inches away. She reached across to the coffee table and rang a small bell.

No sooner had the sound of the bell died away than a beautiful young woman, dressed in a maid's uniform, appeared in the doorway! My jaw dropped in astonishment and surprise!

"Ah yes darling, this is Bobbie" The vision in the doorway smiled shyly and curtseyed. "You probably haven't heard about my new maid have you? Well, when you were living with me here I got used to having someone I could order about and who would put up with my little ways. So when you went off with your new Mistress – you heartless beast -" she teased, "I decided I needed someone to take your place. What do you think of her?"

"She's beautiful Auntie" I whispered hoarsely, taking in her slim figure and long blonde hair arranged in a chignon under the lacy cap of her uniform. Her face although heavily made-up, was extremely pretty.

"Say hello to my nephew, Bobbie" Auntie ordered.

"Pleased to meet you, sir" Bobbie said in a shy voice. "Hello Bobbie" I managed to reply, feeling all the more incongruous at being called 'sir', given my appearance. Bobbie however showed no sign of embarrassment. She smiled through lowered eyelids. "I hope you enjoy your stay here sir. If there is anything I can do for you please let me know". "Thank you Bobbie I will" I said, my mind reeling with the possibilities of having this beautiful maid at my command.

"Bobbie, get us two coffees and some biscuits please" Auntie ordered. The apparition in the doorway dipped another curtsey and was gone.

"Auntie – she's really beautiful!" I blurted out.

"I'm glad you like her because I'm very fond of her. I think the two of you could get along very well" she mused.

Then Auntie asked me for the letter from Mistress Helen. I fished about in my purse and brought out a sealed envelope. Auntie opened the envelope and took out the letter. She read for a couple of minutes, then felt inside the envelope again and brought out a tiny key. She held it up to me with a smile. "Do you know what this is, my cherub?" she asked.

"Yes Auntie, it's the key to my chastity cage" I answered, swallowing hard.

"That's right. Your Mistress has kindly given me this and told me to make sure that you know I have it for your stay here. She says here that you've gone for a whole month without any release down there – you poor boy! Well – if you are a very well-behaved sissy and do everything you are told, I might just allow you a little squirt as a special holiday treat! Would you like that?"

As she spoke I could feel my penis swell again inside the cruel confines of the chastity device. "Oh yes Auntie! That would be wonderful. I'll do anything you want, I promise". Auntie's eyes narrowed. "So you promise, do you? We'll see…" she said ominously.

The coffee arrived and was served with quiet efficiency by Bobbie, who then stood by the door, awaiting further orders. Auntie turned to the letter again as we drank our coffees. "There is a list of instructions here from your Mistress, about the routines she wants me to make sure you continue during your stay. Let me see… yes, bedtime is eight o'clock for you young man". There was a sound that could have been a cough from Bobbie over by the door. "-and earlier if you've misbehaved in any way. And she says here that you have a special hairbrush in your luggage that I'm to use on your bare bottom if you're especially naughty – is that right?"

"Yes Auntie" I replied miserably.

"And you have some special cream that you have to massage into your nipples for ten minutes every night before you go to bed. Now that sounds like fun – I might help you with that!" Auntie said with a gleam of excitement in her eyes. This was a fairly recent addition to my bedtime routine. Mistress Helen enjoyed playing with my nipples during our love-making, and had decided that she wanted them to be even more responsive to her caresses. One day a small jar of heavily fragranced cream has appeared in my room, and that night, after my bath, she had demonstrated how I was to sit at the dressing table, naked except for my chastity device, and rub the cream into my nipples. She also provided a small electronic timer to ensure that I did this for a full ten minutes. Whether there was some special ingredient in the cream, or whether it was just the effect of the prolonged rubbing, tweaking and stroking, but as well as ensuring that I went to bed every night swooning with delicious longings, it was becoming noticeable that over the course of the last few weeks my nipples were becoming larger, especially when aroused. They were also becoming more sensitive so that even touching the inside of my clothing could send them into a state of excitement.

After coffee Auntie ordered Bobbie to carry my suitcase upstairs to the guest room, and then left Bobbie to help me unpack, saying she needed to shower and change before a business meeting in town later that morning. She left us promising to be back for lunch.

The airy guest bedroom was decorated in delicate floral wallpaper with lace curtains over the large sash windows. A four-poster bed was covered in a pale cream satin coverlet, with a pile of embroidered cushions heaped at the head of the bed. An antique full length mirror stood in a corner of the room next to a pair of wardrobes and a dressing table.

"This is a lovely room" I said to Bobbie, "It's been redecorated recently, hasn't it? And I suppose you're in my old room - the one with the connecting door to Auntie's bedroom. Am I right?"

"Yes sir" Bobbie answered, blushing, "As I'm sure you know, Madam sometimes has things that need to be done urgently – even in the middle of the night" she added meaningfully.

Bobbie put the suitcase on the bed and opened it. "Oh sir, you have some lovely lingerie!" she exclaimed holding up a bra and panties set in pale blue silk on its own padded satin hanger.

This was a very strange experience for me: to be standing in a very feminine bedroom, dressed only in a flimsy baby doll nightie, while a very attractive young woman enthused about my collection of frilly underwear and pretty dresses!

"Bobbie-", I began nervously, "Are you not shocked by the way I'm dressed and the way I am treated by my Mistress and Auntie? You don't seem to be at all surprised."

"Sir, please don't have any concerns on my account. Your Aunt has told me all about your 'special' interests and I know that she loves you all the more for them. I've been looking forward to meeting you." She smiled and resumed unpacking and storing the contents of my suitcase, commenting and giggling over each item. Her enthusiasm and obvious delight in the finer points of my wardrobe gradually put me at my ease.

So when she held out my absolute favourite white satin party dress – an outrageously sissy confection covered in lace and bows - and said that she would love to see what I looked like in it, it seemed only natural to oblige her. I slipped off the baby doll and standing naked in front of her, allowed Bobbie to drop the dress over my head and zip it up at the back. The dress fitted tightly to my upper body and had short puffed sleeves and a high waistline from which flared a very short full skirt. Underneath an attached taffeta petticoat ensured that the skirt stood out and made delicious swishing noises. I stood in front of the mirror with Bobbie standing alongside as we both admired the exotic creature in the glass.

"Sir…" Bobbie whispered, standing very close and fussing with the numerous satin bows on the dress, "You look like an angel – you really do". She stroked my bare arm and then my cheek.

"Oh Bobbie" I replied, feeling my penis respond inside the chastity device. "It's wonderful that you can accept me like this…" I glanced over at my image in the mirror. "This is the real me. I didn't know it was until Auntie made me accept that I'm a – a sissy".

Bobbie moved closer still and kissed me softly on the lips. Then she pushed me gently backwards so that we both fell on to the bed. Her hands began to explore my body, stroking my nipples under the tight satin bodice and wandering slowly up my bare legs.

I moaned as the confines of the metal chastity cage became even more unbearable and my excitement grew. We kissed passionately and I placed my hand on her stocking-clad leg. Feeling very daring I slid my hand further up under her dress. Further and further, feeling the tops of her stockings and the taut suspenders that held them in place. My fingers felt the lace edge of her panties. Apart from the discomfort from my imprisoned penis I was in paradise! Bobbie was panting loudly in my ear – she seemed to be as excited as I was. I felt she was urging me on so taking a deep breath I slid my fingers into the warmth under the edge of her panties.

What I felt next made me scream out in shock! I could feel a hot, hard penis straining against the silky material of Bobbie's panties! I pulled my hand away as if it had been burnt.

"But…but…you're a boy!" I gasped.

Bobbie held on to me as I struggled. "Sshh…ssshh…ssshhh" she – or he – kept on repeating until I managed to calm down somewhat.

"Billie you're wrong – I'm not a boy, or at least I'm not an ordinary boy. I'm a sissy boy like you!"

"But you look like a girl" I said pathetically.

"That's thanks to your Auntie. She advertised for a sissy maid when you left. That was because she loved all the special games that she used to play with you. When she hired me I had short brown hair but she insisted that I grow it long and then she took me to the salon and had it dyed blonde. Did you think it was natural?"

Before I could answer the door of the bedroom opened and Auntie walked in! Bobbie and I both jumped to our feet and stood sheepishly at the end of the bed.

"Well I see you two sissies haven't wasted any time in getting to know each other properly! I was just about to leave the house when I heard you shout out. Do I take it that you've discovered Bobbie's little secret?" Auntie asked, her eyes narrowing.

"Auntie, yes – she's a boy! I can't believe it. She – he looks totally like a girl!" I said.

"Really Billie, you should know better than most that the difference between a boy and a girl is not always straight forward. You and Bobbie are both girly boys – that's the way you were made. Bobbie is just that little bit more girly than you, that's all"

Turning to her maid she said, "Bobbie you've been very naughty – I was planning to let Billie know about your, what shall we say, special equipment later on tonight, but you couldn't wait to jump on the poor boy could you? You've upset my darling I can tell.. Well you know how I deal with any disobedience – go to your room and prepare yourself for a severe spanking! Off you go – NOW!"

Bobbie's hair had become dishevelled during his tussle with me on the bed. His long blonde locks had fallen out of the chignon and hung around his face. His cheeks were flushed and his bottom lips seemed to quiver with emotion. "Yes Madam. I'm sorry Madam" he said in a quiet voice as he left the room.

As the door closed Auntie sat down on the bed and gestured for me to join her.

"My poor cherub. I imagine your feelings are all mixed up right now because of that naughty Bobbie. He will be punished properly I promise you. Now let Auntie give you a bid cuddle and you can tell her what's wrong"

"I just got a surprise Auntie. Bobbie is so beautiful and so convincing as a girl. I –I really fancied her – him, Auntie – but I'm not gay – I'm not, honestly!"

"There there my poppet", Auntie soothed, as she put her arms around me and pulled me to her perfumed bosom. "I know you're not gay, but I thought that might be what was upsetting you"

"Now listen to me carefully" she continued, "Bobbie answered my advert for a sissy maid after you went off with Mistress Helen. I had my pick of twenty very presentable young men who had some experience of being a maid. It was an eye-opening experience I can tell you! But I chose Bobbie because he has a good sense of fun and we get on very well together – and yes – he is very convincing as a girl. So it gives us the opportunity to play some other, very interesting games - which I'll tell you more about later."

"But what I want you to do during your stay with us is to make friends with Bobbie and to work alongside him as a maid. You used to love being my maid and I know you have to be a maid for Mistress Helen, so it shouldn't be too hard for you. I've got you some matching uniforms so you can dress identically. They are in that wardrobe over there. I will expect you to work hard during the day, and your Mistress wants you to be in bed by eight o'clock, but we can still have lots of fun – the three of us. How does that sound?"

"It sounds lovely Auntie. I just need a little time to get used to the idea that Bobbie is a boy…"

"Of course darling, and Bobbie and I will be very gentle with you. But now I have to go and punish that wicked sissy. He will be standing next to the bedroom chair in his underwear, holding out his special hairbrush in both hands, waiting for me to arrive. That's the way I've trained him - I used to do something similar with you I seem to remember."

"I want you to stay in here and finish unpacking you suitcase, and then change into one of the maid's uniforms from the wardrobe. You'll probably hear some squeals and crying coming from Bobbie's room in a few minutes – he is such a cry-baby! Wait ten minutes after his silly cries have stopped then come down to his room and take a peek in side – I'll leave the door open so you can come in quietly. Just watch from the door for as long as you want then you can come back here and I'll pop in and see you later". With that Auntie stood up and kissed me on the cheek. Then taking a deep breath she raised herself to her full height and marched down the corridor.

I only had a few items of lingerie to put away before I turned to the other wardrobe and threw open the door. Inside was a mass of maid's uniforms in a variety of pastel colours, plus several in black. Most were made of satin although I noticed with a thrill that one black outfit was of slippery latex rubber, complete with white frilly rubber apron.

I had just selected a pale blue satin uniform and was stepping into the dress, when I heard a wail coming from Bobbie's room. That sissy was now over Auntie's knee and having his bottom spanked! As the wailing continued and gradually built up in volume, I could not help picturing the scene and my penis strained against the confines of my chastity device. If only I could be released from the cruel cage! I would have dearly loved to relieve the pent-up sexual tension that my Mistress had imposed on me. Still, I was heartened by the fact that Auntie had a key for the device and had promised to allow me to have a 'squirt' if I was well-behaved. I made a mental resolution to be as co-operative as I could with any of Auntie's instructions.

Then I noticed that Bobbie's shrieking and tearful pleading had stopped. I had just ten minutes to finish getting dressed before reporting to the maid's bedroom – and I did not want to fail Auntie on her first command.

Quickly I zipped the dress and tied the lacy bib apron in an extravagant bow behind my back. I slipped my feet into the matching pale blue high heeled shoes and went over to the dressing table to run a hairbrush through my curly permed hair. I just had time to refresh my lipstick before the ten minutes were up, and I set off nervously down the corridor to Bobbie's room.

As Auntie had promised, the door was not shut. With heart pounding in anticipation as to what I was about to see, I pushed the door open.

The first thing I noticed in the dimly lit room was Auntie reclining comfortably on the upholstered bedroom chair. She gestured for me to come in. Only then did I notice that Bobbie was kneeling on the floor between her legs, dressed only in his underwear. His ruffled panties were round his ankles, exposing the red weals on his bottom. The hairbrush lay discarded on the floor nearby. Then I saw that Auntie was naked except for a voluminous pair of white Victorian style bloomers. She gestured down to them to draw my attention to the details of the scene before me.

It gradually dawned on me that there was something extraordinary about Auntie's panties - they appeared to have not two, but three legs, all richly trimmed with lace and ribbons. And Bobbie's head had been inserted into the third knicker leg and was confined there and held against Auntie's most private of places by a bow at the back of his neck! As my eyes became accustomed to the dim light I saw that a broad ribbon had also been used to tie Bobbie's hands behind his back.

Auntie held Bobbie's head through the satin and pressed the hapless sissy against her. Muffled slurping and groaning sounds could be heard from Bobbie as Auntie panted, looking over at me again through glassy eyes. She smiled at me distantly. Then she addressed the wriggling sissy contained in her panties. "Oh Bobbie, that's lovely. More of that… a little bit faster…yes, that's good. Now use your lips right on the tip…oooh yesss…Now back to licking…harder…harder!…" And in this way she directed her well-trained sissy to provide her with exactly the stimulation she needed from moment to moment.

I could only watch transfixed. My penis was ready to explode yet the chastity device made my erection into a painful distraction. All the while Auntie carried on with detailed instructions to Bobbie, her eyes now closed.

This carried on for perhaps twenty minutes. My legs were buckling with excitement and frustration and I leaned against the wall for support. Auntie seemed to have forgotten that I was there, and I felt I was intruding into some very intimate ritual between lovers – as indeed I was. Very gradually Auntie's commands became less specific and more frenzied.

"Oh god yes!...yes. Oh…oh…oh…yesssss!!" she screamed as she thrust herself against Bobbie's face and squeezed his head with her thighs.

I slipped out of the room and staggered back to my own bedroom. Collapsing on the bed with my penis still throbbing in its metal cage, I fell instantly into a disturbed sleep.

* * *

The End




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