Cheryl has a plan – but it begins to look as if it may mis-fire – or should that be ‘miss-fire’?
As I entered Mistress Christina’s bedroom I was immediately struck by her beauty once more. She had let her hair down again and, as before, seemed all the more feminine. I knew this to be just an outward manifestation though.. Internally, this lady was made of the finest Swiss steel - and had a mind that matched the exactitude and precision of any watch ever devised in that country. She was sitting at a large antique desk, with what appeared to be some correspondence in front of her. A balloon glass of brandy was at her side. She took a sip from it, her eyes glittering like diamonds as I moved towards her.
"What took my little bride so long? I've been waiting and waiting for you," she said, pointing to another glass with a brandy already poured.
I stood stock still for a moment, amazed at this woman's insight.
"I had thought to surprise you mistress," I said, taking my nightgown at each side and dropping a curtsey.
She laughed. "Of all the sissy maids I ever have had, you amuse me more than any other."
"May I ask why Madam?" I asked pertly, somewhat offended by being reminded that I was not the only sissy maid she'd ever had, and somewhat by the fact that she found me 'amusing' when I had come to her bedroom in a very serious frame of mind – along with a plan!
"Come here girl!" she said firmly, pointing to an area on the floor just in front of her chair. Chastened by her tone, I walked slowly over to where she pointed.
"Now listen to me child. Tonight you are going to be my bride. I will relax with you – and you will relax with me. But your tone of voice there came very close to insolence. That I will not tolerate! Do you understand me?"
Again chastened by this powerful woman, I curtsied instinctively. "I am truly sorry Ma'am. I will not speak in such a manner again. I most humbly apologize."
"That's better my little frau. But a few things to keep in mind. Tonight? I am going to be the man in your bed. Yes?"
Shyly, blushing, I looked at the floor and nodded.
"Good! But wives do not curtsey to their husbands. So from now on, for the rest of this night, you will not curtsey to me again. I free you from this. Now I am going to be busy for a few minutes with some business that I do not wish to leave undone. Why don't you go over and sit at my dressing table while I am doing these things. You smell adorable, so you do not need any more perfume – but why don't you take a minute to touch up your hair? I just love to see little sissy boys sitting in front of a mirror and being sweet and girlish."
I went and sat at the mirror, and spent the next few minutes doing as she had suggested. Touched up my hair lightly with a comb. Carefully, went over my eyebrows with a pencil. Re-did the bows of my peignoir and checked my lipstick. I knew she was pleased with what I was doing as I managed to sneak some glances at her and found her watching me, smiling at my feminine antics, while she continued reading and signing documents.
To tell the truth, I got so engrossed in making myself prettier that I must have forgotten she was there at all. I actually jumped a little when I felt her hand fall softly on my shoulder and saw her reflection in the mirror, standing at my back, looking down at me. She inserted a finger between my neck and the collar of the negligee .
"Mmmm" she sighed, slowly exhaling. "How soft you are. How nice your hair smells. How pretty you are. Are your lips still waiting for mine?"
As she spoke, I felt the ribbon tie at my peignoir collar be untied and now her hand was slowly sliding down to land on my breast.
I sighed myself, and bent my head backwards, looking up at her. She leaned over and kissed me gently, her tongue making tiny contact with my lips, edging into my mouth, just a little way.
Both of her hands were now sliding down inside the front of my peignoir, now under the sleeve areas, pushing the garment down and off my shoulders. I could feel it sliding down, off my arms. She was whispering soft, soothing, sounds in my ears. I couldn't make out any distinct words – she could have been muttering Swiss endearments for all I knew. For some reason, I kept rolling my head in a circular motion as her mouth started kissing the area where my neck joins my shoulders, and giving me tiny bites there as she did so.
The bench where I sat had no back, and as I was leaning further and further backwards into her arms, it was no great surprise when I knew that she was lifting me, my flimsy negligee falling to the floor. One of my velvet slippers fell off as she was carrying me towards the bed. I waved my right arm weakly.
She stopped. "What is the matter liebchen?"
"My slipper, darling. I lost it." I whispered.
She released a little gurgle of laughter. "You won't be needing any slippers for a while dear." she said. With that, she laid me down on the bed. Tenderly, took my other slipper off my foot. Kissed my toes. "That feel better, my little Schatze? More 'balanced' now?"
"Oh my, yes!" I said appreciatively, and held both of my arms out towards her.
"Not just yet. Hold still a minute." She told me "What is that English saying? Hold your horses?"
I nodded, mute as she pulled pillows from the top of the bed and, lifting me up, positioned them at the back so that I was propped up somewhat. She then went a bedside table and opened up a leather container. Pondered the contents a minute, then made a selection. Went to desk where she'd been sitting and brought the two brandy glasses over and put on them on the same bedside table.
Then, I noticed what she's selected from the case – another dildo. Exactly the same as "my" lollipop only somewhat bigger I thought. She dipped the end of it in the brandy, then came to me. "Open up those pretty red lips Cheryl darling. Look what Mistress has got for you! Smile now!"
It was hard for me, but I tried to smile as best I could as gently pushed the tip into my mouth. I don't particularly care for brandy but it did help make the thing a bit more palatable.
"Push it in yourself dear – but don't make yourself uncomfortable." I was told. With that, she took her hand away and lifted mine up to hold it. I pushed it in about two more inches, then looked up at her enquiringly."
She nodded. "Comfy dear?"
"Fine!" she said happily. "I have to get something. So just suck on your new lollipop for a minute. Okay darling?"
Sucking hard, I watched her go to a dresser. She opened a drawer and took out a wand type thing. She then opened up a part of it and took out some batteries and replaced them. I heard a vague humming noise, then it stopped as she appeared to switch it off on her way back to the bed.
She put the thing, whatever it was, on top of the bed, then using one hand, took hold of my ankles and lifted them up off the bed. Then she used the other hand to lift the skirts of my nightdress and shove them up almost all the way to my waist. Now, still using the one hand, she gently tugged at my panties until they were down below my knees all the way down to my ankles, then off. She then let my legs back down on to the bed, but proceeded to bend them at the knees until I was now sitting semi-upright, my legs gaping apart and my groin easily visible.
In a kind of terror, I shut my eyes. I heard the quiet humming noise again and felt my mistress come closer to me. Seconds later, I felt the touch of something against my anus.
"Relax darling. Just relax. It won't hurt if you just relax," she said.
I tried to plead with her, but it just came out a mumble and, before I could think of anything else, the wand had penetrated me! Just a half inch or so, but there was a vibration to it – a sort of mild reciprocating movement – in out , in out, in out – very rapidly with a 'stroke that couldn't have exceeded a quarter inch. I took a deep breath and relaxed. It moved further inside me.
"Good Cheryl! That's a girl, just a little bit more – there!"
As I slowly surrendered, the wand kept working its way upwards. I was very uncomfortable to begin with, but gradually found out that, as I relaxed, it became a sort of thrilling vibration inside me. I started to feel my eyes rolling in my head. The mistress sensed this.
"Very GOOD Cheryl! Here, take the vibrator in one of your hands. That's a girl! Now, nice and slowly, start moving it in and out. Very good! "
Now her hand moved up to the one of mine that was holding the dildo and covered it. Started moving it in and out in conjunction with the hand that held the wand.
"Now keep doing that, just like that when I take my hand away. All right?" she said.
I nodded both my right and left hands in synchronized moves pushing things in and out of my body orifices.
She stood back and watched me, smiling. Then she clapped her hands happily. "Just a little while more Cheryl. Mistress wants to do something, so keep it up – just like that! Don't be losing control and coming now! I'll be very upset if you do!"
My hands working like those of a robot, I watched as she went to her closet and slid the door open. In a sense full of dull horror, I watched her take out a tripod with a cam-corder camera mounted on it. She moved it back into the room, opened up the tripod legs and set the camera, pointing it in my direction. Checked the focus, smiled. I saw the little red light come on that indicated it was now recording.
"Just as pretty as a picture Cheryl! Suck your lollipop a little harder, would you please? And would you splay your legs a little wider dear? Give the camera a good view of what you're doing down there! Yes! That's a girl! Move both hands a little faster please? Wonderful!"
She ran the camera for a few more minutes. Then stopped it. I started slowing down my arm movements.
"Did I give you permission to slow down, you naughty girl?" she admonished me.
I shook my head dumbly and started speeding up the 'stroke count' again.
"Yes. That's more like it. Now I want you to listen to me. I've stopped the camera because I want you to understand what I want you to do – and not record what I'm telling you. Understand?"
I didn't but did not want to chance upsetting her, so nodded.
"I'm going to turn the camera on and interview you." She smiled. "Just as if you were my own little starlet. The only thing is, I want you to be scrupulously honest. Understand?"
And? When you answer? You are allowed to take your lollipop out of your mouth, but as soon as you've finished speaking , I want it back in there – quickly! Just as if you were really hungry for it. Think you can do that? Understand?"
"Silly little sissy maid! You can talk now – so let us have a little practice. Do you understand what I have told you?"
I removed the dildo. "Yes mistress" I said, and hurriedly put it back in my mouth and re-commenced sucking.
She nodded. "Quite good Cheryl. But when you answer my questions? I want you to smile. Look happy! And try to project just how hungry you are to get your toy back into your mouth where it belongs. Look relieved – as if you were a hungry baby getting it's mother's teat in it's mouth. Want to try again?"
Again, I removed the dildo and smiled broadly. "Oh yes mistress!" then put the thing back in my mouth, trying as hard as I could to smile with my eyes.
"Very good! My, you do make a smart little actress. I can't wait until the next time my group plays Charades. But I'm turning the camera on again. Start these hands going again Cheryl!"
I saw the recording light go on again and did as she had instructed.
"Miss? What is your name and occupation?" she asked first.
I was confused for a split second, but took the toy out. "My name is Cheryl. I'm a maid."
"But you don't look altogether like a girl. Are you a sissy?"
"Yes mistress. I'm a sissy maid."
"You enjoy doing a woman's work? Dressing like a woman? Acting like one?"
"Right now? Are you enjoying what you are doing? Playing with yourself, using toys that only women use to satisfy their urges?"
I remembered what she'd about being honest. "Well, not really mistress. . ."
She quickly turned the camera off. "Didn't I tell you to tell the truth? Didn't I?"
“Yes Mistress - that’s why I said what...”
“I’m going to start the camera again. So make absolutely SURE that you answer all the questions truthfully. Okay, start playing with your toys again please.”
I started moving the dildo and vibrator into my orifices again, and she turned the camera on.
“You look like you’re enjoying your toy dildo. Playing with it like women do. Is that true Cheryl?”
I took it from my mouth and smiled widely. “Oh yes mistress! Thank you so very much for giving it to me.” Hurriedly, I pushed it back into my mouth, and started sucking voraciously on it.
She nodded approvingly. “That’s a very pretty nightgown Cheryl. Do you like it? Think it makes you look pretty?”
I nodded enthusiastically.
“But it’s white. Did you know that that color signifies virginity?”
“Are you telling me that you’re a virgin?”
I nodded my head up and down, blushing.
“Did you put your pretty nightgown on by yourself Cheryl? Without anyone forcing you to put it on?”
I removed the dildo from my mouth. “Yes mistress. All by myself.” and started to put it back in my mouth again. She held up her hand and stopped me.
“Then you came and knocked on my door. Didn’t you?”
“Then, while I was doing my correspondence you sat at the dressing table and made yourself pretty for me?”
“You know what I’m going to do to you? Make you act the woman’s part in lovemaking? Put that dildo inside you? Where you have your vibrator just now?”
I was so scared that I couldn’t speak. All I could do was nod at each and every question she was asking.
“This what you want me to do to you, my darling little sissy maid? Tell the truth now!”
“Yes mistress.” I whispered.
“A little louder, my wife to be. Please?”
I repeated myself, louder this time. She smiled radiantly, checked the camera to ensure it was locked in place. Then she came and sat on the bed beside me, faced into the camera and spoke.
“Cheryl is probably one of the nicest sissy maids I have ever had, She was given to me as a present by my three wonderful daughters just a few days ago. Without any previous experience she has shown a marvelous aptitude for being an obedient sissy maid. She has come to my bedroom tonight voluntarily, wearing what is the closest thing she has to a wedding gown.”
(I have seen the tape of what followed a number of times, and will never overcome the sense of shame as my mistress then proceeded to turn me into her woman.)
First of all, she warned me not to stop what I was doing with my hands. She then slid me, still on my back over to the side of the bed, so that I was now lying at right angles to my original position, repositioning the pillows until I was semi-upright once more.. “Don’t want to hide your pretty face when I mount you,” she said “Want the camera to catch all of your happiness. Turn your head now. Smile nicely for the camera now.”
As I followed her instructions, she took a hold of my hand that held the dildo and moved it away and down, positioning it to where I now held the vibrator in both hands. Smiling gently down on me, she took the dildo in her own hand, then removed it gently from my mouth. Still looking at me, she took the thing out of my sight and did some adjustments where I couldn’t see.
Then she came to the side of me that was farthest away from the camera, and started caressing my breasts. Soft, gentle caresses from her hands, then her mouth coming over and kissing my ear. I let out a small moan and instinctively raised my hand to caress her in return. She simply murmured “No, Cheryl” And put my hand back down on the vibrator again.
Her kisses became more demanding, and the caresses a little stronger. My mind was in a turmoil, the vibrations seeming to be the center of my whole being, while, at the same time, her hands and lips demanded my attention be given to where they were working on me. And now her lips were forcing onto mine, and her firm tongue poked its way deep into my mouth. Her hand slid in between my legs and took over control of the vibrator, nudging my hands to the side as she did so.
I sighed a little sigh and wrapped my arms up and around her neck when she moved silkily in between my widened thighs. For a second, I was aghast at the sight of a decided ‘bulge’ at the front of my lady when I caught a glimpse of her moving into the ‘center’ of operations so to speak, but lost all semblance of rationality seconds later..
“Lift my nightdress dear.” She whispered softly in my ear after a while. “See what Mistress Christina has for her sweet little Cheryl.”
As I followed her instructions obediently, she was using her hands, now at my shoulders, to bring me further down the bed, closer to the edge. Then a hand was at my anus, magically coated with something smooth feeling, and I knew I was being lubricated.
Minutes later, she took me the way a man takes a maid. What can I say? I acted, no differently from any other girl who is in two minds as to giving up her virginity – squealing and weeping with fright at one moment, demanding passionately the next.
I shuddered one second, thrust the next – squealed, whimpered, cried, laughed. I felt a true spasm of honest shame when I felt a condom being fitted to me – how DARE a woman think that I would be sexually aroused enough to ejaculate at being treated the way I was? But I did.
To make things worse? In the middle of the night I wound myself into and around the woman who had taken me. Pleaded girlishly for more! Kissed, sucked, whispered and tongued – until she made me a woman again. I was acting, but determined to make this woman want me – to lose any feelings she had for my competitor or her affections – Danielle!
I wakened to see her strong face looking down on me.
“Maid Cheryl? It’s morning! Time to do your morning chores. Up girl! Face the morning! Miss Brigitt will be here soon. Get you going on your corset training again. I have been most lax with you. She’ll give me trouble for spoiling you! Up now!”
Stultified with sleep, I slid out of bed, then realized just how sore I was when I bent to pick up my panties and peignoir from the floor where they had fallen. Quickly, I slid the panties on and up into position, then put the peignoir on, very conscious of Mistress Christina’s eyes focused on me. As daintily as I could, I slid my feet into my slippers. As I did so, she spoke to me.
“Cheryl? Come here girl.” And pointed to the side of the bed beside her.
My nightwear floating around me, I blushed and went to where she pointed.
“You’re my maid again dear. I expect you to curtsey me when I speak to you,” she said, but gently.
I blushed at the reprimand, but curtsied prettily . “I’m sorry mistress” I said.
She nodded. “That’s all right dear. Don’t forget again. If you do? I’ll notify Madame Directrice.” She paused and smiled . “ But you won’t make that mistake again will you? You’re such a clever little thing! SUCH a good girl!”
The question was obviously rhetorical, so I simply shook my head and curtsied again.
“You were surprisingly good in bed last night. I was very pleased with your performance. At the same time? I want you to understand that you are not to come to my bed chamber again without my specific invitation.”
My shock and hurt must have been immediately obvious. She continued in a more kindly tone. “Yes, I know I had told you to come – but that was to ensure that you were willing to give up your virginity. Now that you have? You’re just my little sissy maid again – available for sex when I wish it – not when YOU feel in the mood. Understand?”
Totally humiliated at the amused condescension she was addressing me with, I nodded.
“Good. Now when you get downstairs? I want you to notify Mistress Directrice that you didn’t curtsey me when I spoke – even after I’d warned you. You won’t forget, will you?”
“Oh no mistress! Please mistress? I’m sorry! Please mistress!” I was babbling and bobbing, curtseying and wringing my hands, all at the same time. She eyed me coldly and waved her hand in dismissal. Almost in tears with fright at my upcoming punishment from Madame Directrice, I curtseyed once more and left the room.
I knocked on Madame Directrice’s door and was told to enter. Before she spanked me, she had me help her to dress. She was a fine figure of a woman, extremely well formed and had beautiful skin. She didn’t make a big fuss about putting me over her knees, Just sat on a chair once she was ready, and pointed to her lap. Meekly I arranged myself over her knees.
She lifted the hems of my peignoir and nightgown and spanked me on my panties.
“You don’t have to pretend that you like this,” she said beforehand “so you don’t need to squeal and kick your legs if you don’t want to. This is NOT for my sexual pleasure, so you can be as natural as you like.”
I was very natural. Wept, writhed, squealed, moaned, pleaded, kicked prettily – and not so prettily. She must have spanked me at least a dozen or more times. Used only her hand, but how my backside stung.
My punishment was curtailed by help from an unexpected source.
“Stop that womanish squalling. Now!” Madame Directrice ordered, then called out. “Is that someone at my door?”
“Yes Esther. It’s me. Brigitt. May I come in?”
“Certainly my dear. Please do.”
From my prone position, I couldn’t see, but heard the door open and Miss Brigitt come into the room.
“Aha! Little Cheryl being naughty again?” she asked. Then, in a changed voice before Madame Directrice could answer. “White nightgown? White negligee? Does that signify what I think? And, was she found wanting in that regards?”
Madame Directrice laughed. “Yes, our little Cheryl was a bride last night. And from the lack of any other comments from Christina? It would appear that our little virgin was very satisfactory. I’m imagining that she just started trying to take advantage of her new position. Was disrespectful. I’m just in the process of reminding her of how to behave properly.”
“Don’t let me stop you.” Brigitt laughed. “I truly love to hear little sissies squealing.”
“No. I’m finished with her.” Madame Directrice said. “If you’re here to take over her corset training? She’s all yours.”
I sensed Miss Brigitt approaching my chair, but wasn’t ready for the cruel pincer-like grab on my ear. “Come ON sissy! Can’t be lollygagging around here all day! You’ll be needed to serve breakfast in a little while! UP!”
And, squealing and weeping again, I was pulled to my feet and led out into the hallway and down into my own room. There, Miss Brigitt settled down into one of my chairs and pointed to one directly across from her. She had a cruel smile on her face. “Sit there Cheryl. Lets have a little girl talk, shall we?”
Nervously I sat where she pointed, wincing a little at the pain in my backside. I rubbed my sore ear with my fingers – very gently. With my other hand, I carefully arranged my nightgown and peignoir to look as attractive as possible. Brigitt nodded approvingly.
“Like being Mutter’s girl? Was she gentle with you? Treat you like a lady? Come on. Tell me all about it. Don’t leave anything out!”
And, blushing and stammering, I admitted how I’d dressed all on my own, and presented myself to her mother. How I’d primped at the table. How I’d been ‘interviewed’ How I’d been ‘de-flowered’. How I’d initiated sex during the night. Why I’d been sent down for punishment my Madame Directrice.
Her eyes got a peculiar shine to them as I explained what had transpired and, about half way through my narrative, she got up from the chair and started walking around my room, searching for something, waving her hand at me to make sure I continued talking.
Like a rabbit hypnotized by a snake, I kept describing the events of the night as she found my little handbag and pulled out my ‘lollipop’. Holding it in one hand, she came to my chair and, held out her other hand invitingly to me.
Frightened, I took it, and she pulled me upright and back to where she’d sat. Then she lowered herself back into the chair and positioned me on her lap, kissing me hard on the mouth every so often, caressing my breasts with one hand, and very slowly, working the dildo up under my night clothes and into my anus. Very gently.
Practically transfixed with fear, I stammered on with my story as the dildo was worked, still gently, in and out of my body. Helplessly I was pulled further and further back into her arms, finally lying almost flat on my back, my legs raised, as she manhandled me.
“I think you’re ready for me. Are you Cheryl?” she whispered mockingly. “Going to be Brigitt’s girl now?”
“Please mistress? Please No!” I wept.
“You’re just being a silly girl Cheryl. Here. Help me get ready. Up now!”
Despite my rears and entreaties, she made me kneel in front of her and lift her skirt. Under it, she wore a peculiar harness type of thing. To my everlasting shame, I was forced to insert the dildo into it. Weeping the way I was, I couldn’t see too well and she impatiently shoved my hands out of the way and made the final adjustments herself.
It stood out from her body, like a man’s, her skirt draped around it. She then made me stand up and pulled me into her arms, then undulate my groin against hers like a woman in heat. Laughing now, she pushed me over to my bed, then made me kneel on top of it, My backside pointing over the edge. My nightgown and negligee were pushed up out of the way, her arms encircled me from the back – and she started to enter me, ignoring my squealed protests.
Just as she did, a knock came to the door. “Brigitt? May I talk to you a moment please?” It was Mistress Directrice.
“I’m busy Esther!” Brigitt snarled. “Can’t you tell?”
“I’m terribly sorry dear. But please let me interrupt?”
“Okay! Dammit! Come in!”
And, still kneeling, still impaled by the ivory shaft worn by the woman behind me, I was kept in the submissive position while Madame Directrice entered. Her eyes barely flickered in my direction, but no emotion of any kind showed on her face as she began to describe why she had interrupted my newest humiliation.
End of Chapter five