tagBDSMTraining of a New Sissy Ch. 01

Training of a New Sissy Ch. 01


I'm not sure who was more surprised at my reaction to the surprise party. Certainly She expected that I would enjoy my time, She is very considerate like that. But I think it took even Her by surprise at how much I, for lack of a better word, gushed like an excited teenager when telling Her about the experience. I think that's partly why She insisted I write my feelings down, chronicled my time as a sissy, what I enjoyed, what I didn't. I get the feeling that She plans to share my story, though I do not know with whom. Until I arrived at the party I hadn't realised that She even knew anyone else into this kind of kink, not around where we live, anyway. The internet transcends mere geographical boundaries, so I always expected She'd be in contact with others. For all I never saw anyone else at the party, there was clearly quite a few people there!

Nevertheless, I couldn't hide my excitement from the night, even if I tried - which to be fair, I wasn't trying to do. It was weeks ago, but still fresh in my mind. Partly because She enjoyed the swift erection I got every time I was reminded of it, and partly because She continued to hint that it wasn't a one-off. We continued to play, my having to wear some fairly simple single items of lingerie, like stockings. I kept hoping it would lead to me, that She would insist I shaved, or wore a proper dress. Her hints kept the hope alive, but, if I'm honest, I was disappointed that nothing seemed to be happening. Don't get me wrong, our sex and play is always fantastic. I mean *really* fantastic, I just couldn't shake the feeling that She wasn't really into the sissification.

The weeks grew into months, the hints became less frequent. I still, literally, dreamed about that one night but concluded it was a me-kink, rather than a Her-kink or an us-kink. I should have known better than to think She was unaware of my thoughts. After all, She organised my party invitation in the first place! I am slightly ashamed to say that I had concluded She didn't really care.

Winter gave way to spring and with it, brought us to Her annual trip to visit Her parents. Each year She flies to them to spend two weeks with Her family. Her siblings often travel as well, making it a regular catch up for the entire family. Typically I am left behind, with a list of chores to complete. Some regular around-the-house maintenance and some much more interestingly kinky. In order to achieve the list I also take the two weeks off work, freeing my time entirely for devotion to Her. I never know what is on the list ahead of time. There is often obvious things, like some painting that needs doing, or fence that needs mending, but I find the full list pinned to the board in the hallway when I get home from work on the Friday.

It's exciting, and a little nerve-wracking, coming home that evening. I'm not always confident I can achieve everything on the list - though I always have so far - so there's a touch of shake in my hand as I unlock the door, step inside and make my way to the list. She's cute, this year the list is rolled up like a scroll, tied with a silk ribbon, the loop hung over a pin. Unfurling what is to be my focus for the next 14 days, I can feel my heart in my throat - the paper is blank at the top. Blank in the middle! At the bottom I find some actual words, and release my breath with a sigh of relief. I had feared She was upset, had left me with nothing to do.

A frown crosses my face as I read the single instruction:

"This year you will be helping a friend of mine with her household. Report to the address below at 9am on Monday. Do not be late, I have assured her that you are responsible, reliable, punctual and obedient, with no task too dirty. Her name is Mary Jane, and you are to treat her as if she were Me. She will be reporting on your performance throughout your time there. Make Me proud, and you will be rewarded."

I could hear her quiet voice in my head adding "Disappoint me and there will be consequences."

Checking both sides of the scroll I confirm the only writing is at the bottom. It would seem that this break is entirely new!

Monday rolls around, and I leave what I thought would be my home for the next two weeks early. No point in risking starting off on the wrong foot by being late. Throwing my bag on the passenger seat, I start the car, and wait for the satnav to boot up. Entering my new address I pull out onto the road, wondering why I'd never heard of Mary Jane before.

An hour later I pull up to her address, crossing my fingers it's the right thing to do, I idle up the long gravel driveway and come to a stop under her carport. Bag in hand I check the car clock: 8:56. Nailed it. Stepping up to her door I hear my car beep as it locks behind me. A deep breath, let slowly out and I ring the doorbell. Here we go...

The wait is short. The door opens to reveal a smiling lady around my height, slim and athletic. "Hello" she says "I am Mary Jane and your timing is excellent. This is a very promising start."

She steps to one side, waving me through. Looking around I can see a hallway extend before me. Some pictures are on the walls, and all the doors I can see are shut. I jump slightly as I feel a hand on my shoulder.

She laughs at my surprise "Relax. We don't bite! Here, let me take your bag for you."

I start to protest, but stop as I see a frown developing on her brow. I recognise the look - it wasn't a request, I am to surrender my bag. "Thank you." I reply as my bag is, slightly curiously, placed in a hallway closet. Of greater surprise is the key she uses to lock the closet, dropping it into her pocket as she starts off down the hallway.

"Come now," she instructs. I follow her down the hallway, listening as she continues "This is my house, and you will follow my rules." Pausing at a door, which she unlocks with another key, she pushes it open and gestures inside "This is your room. You will sit on the bed and wait, quietly."

I nod as I step past her into, apparently, my room. Looking around it strikes me that it is very pink. Pink walls, pink curtains, pink ceiling. Even the bedding is various shades of pink. I turn to ask her about my bag to find the door clicking shut, the unmistakable clunk of a lock closing is quickly followed by the equally unmistakable sound of a key sliding out of a lock. This is not at all what I was expecting!

'Make Her proud' stampedes across my thoughts and I dutifully sit on the edge of the bed and wait. And wait. Examining my surroundings I notice other curious things: there is no clock; the curtains frame windows that do not open, and which show only trees; there is a mirror surrounded by lights, as you might see backstage at a theatre; more pink furniture, drawers, chairs, there's even a pink rug! The room is quite large, the four-post-bed which would easily be a king-size, taking up only a fraction of the floor space.

Just as I consider standing to see what, if anything, is in the drawers I hear a key clicking into place in the door lock. Again the bolt slides, then the door opens and I can see two people who promptly walk in.

Mary Jane is again smiling. It's a very distracting smile, the edges of her mouth curving deliciously. I start to wonder what her kiss is like, how those soft lips would feel against mine. Her voice snaps me back to reality and I blush slightly. I'm here for her, not for me.

"This is Alexandra. We are in charge, and you will do as you are told without question or hesitation." Alexandra stands quietly, also smiling. They both seem quite pleased to have me here. I nod in agreement, though Mary Jane is no longer looking at me, but has her gaze on Alexandra.

"Would you like to select her first panties, Mother?" she asks. Alexandra nods and turns to the pink drawers, sliding the top one open. Mary Jane's attention is back on me "Strip." she commands.

My mind is racing even as my hands start the methodical removal of my clothes. I'm used to instructions, that's easy. But who is this third 'her'? Why are they selecting her some panties? How does my being naked help? I blush again as I realise I am stripping off for two complete strangers. Not the first time I've been naked in front of others, but usually we've at least met first. Well, apart from that party I got taken too. As usual, thinking back on the party my cock hardens. The pleasant ache interrupts my thoughts and my focus returns to the room, and the two women standing looking at me. Again I blush, I'm not usually easily embarrassed, but for some reason the intensity of their gaze unnerves me.

I realise that Alexandra is now standing in front of me, a pair of red silk panties in her outstretched hand. As she offers them to me I hear Mary Jane's voice again

"Put those on." she commands. I take them from Alexandra's hand and step into them. They're a nice fit, aside from my still hard cock pushing against them. Alexandra steps back after picking up the underwear I had been wearing.

"Now, get dressed. You will only wear suitably girlie panties from now on. The bag you brought has been repacked for you, but you shall only wear clothes from it during the day, and after you have been given permission to dress. Additional attire can be found in the wardrobe and drawers here in your room. If you have been out during the day you will return here and redress each evening. You are a pretty girl and we expect you to dress accordingly every evening, and for the entire weekend."

By this stage I am again dressed, though my cock is still hard as I realise this is what the hints had been leading to. She had never forgotten, merely bided her time until Her annual trip, when I would be handed over to these two for whatever they have in mind.

Alexandra has taken over with my instruction "We know you crave to release the girl inside, even with the thin veil of denial, the mistaken belief that you are actually a man. So we will help you with your transition." she puts an emphasis on 'help' in a way that makes me slightly uneasy "To this end you are to pee as a Lady should, while seated. If we find any toilet seats lifted up you will be punished. You are to masturbate as often as possible, such that it doesn't interfere with your other duties. As you climax you will whisper our names, honouring us as your useless semen is expelled from your body."

I blink a little, trying to take this all in.

Alexandra continues, asking Mary Jane "Shall we give her a name? Something she can use to refer to herself as she learns?"

"I think she should just use 'sissy'."

Alexandra nods in agreement, looking back to me to reiterate "From now on you shall call yourself 'sissy'." A brief pause then she asks "Do you have any questions? Anything you feel wasn't clear?"

I consider a moment, everything seems clear. I am sissy. I will try to dress like the pretty girl I really am. They will help me, and I will honour them in return by whispering only their names as I orgasm. I nod, slowly, saying "I believe it was clear, thank you."

They both smile again, that seems to have been the right answer.

"One last thing," Mary Jane tells me, "Before you go outside and mow the lawn, I want you to masturbate for us, show us how you honour our names, cover those silk panties in your seed, so you are reminded constantly while outside, of your place."

Yet again I blush, undoing my jeans and letting them fall to my ankles. I can hear them laugh as they see the wet patch on the panties, my cock has been dripping, proof positive that they are right.

I've always loved the feel of satin against my skin, so I stroke the length of my cock through the panties, an involuntary gasp of delight as my fingertips brush against the wet tip. My eyes meet Mary Jane's and she holds my gaze unwaveringly. My heart thumps in my chest, I hadn't initially realised how excited these two women had made me. The delicious feel of the satin rubbing against my skin causes more precum to soak the fabric. I concentrate on the head of my cock, stroking just the top of the shaft, the slickness making it feel oh so good. I can hear my own breathing, getting heavier, louder. Still Mary Jane holds my attention.

A soft groan, my hand curling around my ever more aching cock, stroking the full length, the satin and precum making a sticky sticky mess in my palm. I can feel my orgasm building, a slow link as the excitement rises. My cock feels good in my grasp, warm, yielding, pleasurable. My thumb moves to the middle, sliding up the shaft and over the head, stimulating that oh-so-sensitive spot where shaft meets head.

I can feel more than an orgasm, white hot pleasure focussing in my balls and slowly rising along my deliciously aching cock, the climax approaching, hitting the point of no return I start whispering over and over "For you Mary Jane, for you Alexandra."

My eyes flutter shut, lips still moving in silent homage to the two and cum fills the front of the panties, spilling down inside them, coating my shaft and balls, leaking through the satin onto my hand.

Finally, I release my cock, eyes opening again, breath heavy. I look to the door, to my audience, but I am alone. The door is open, of course, I'm to mow the lawns. I can feel my cum still sliding down inside the panties pooling under my balls. Wiping my hand off on the bottom of my tshirt I pull my jeans back up and tighten the belt. This is all very new, doing chores in panties soaked in my own cum. I head out the door and down the hallway, hoping the wetness isn't going to chafe. Out the front door I pause to let my eyes adjust to the sun.

Suddenly I realise my car has gone. They're not keen on me doing anything without permission, clearly. Still, She trusts them enough to send me to them for two weeks. I trust Her enough to accept what will happen. It's going to be an interesting fortnight, that's for sure!

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by Anonymous

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by Anonymous05/24/18


Why do I get a feeling that the sequel is going to fall into the Incest/Taboo category?

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by Anonymous05/22/18


Let me get this right. You mean to tell me that both the wife and the mother in law are into feminizing hubby? Both of them? That's hot, man.
My mother in law would never do that. Not that I'd have themore...

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