Chapter 3
by Monalott
What's next?
I wait obediently for Mr Hollinhoe to return
I wait patiently perched on the edge of Mr Hollinhoes desk, completely naked with my legs spread and exposed to anyone who might walk in. This is easily the scariest thing I ever done, but the memory of what just happened and the excitement of what might yet happen quells the shame.
That doesn't stop me almost jumping out of my skin when the door opens and Mr Hollinhoe returns, but manage to stay on the desk.
"Don't worry it's only me. Everyone else has gone now." He tells me noticing the momentary panic on my face and doesn't bother closing the door behind him. "Put these on. I got them from the confiscated and the lost and found."
He places a pile of clothes on the desk behind me, giving me a kiss as he leans into me to put them down, and then he goes over to where my clothes and our underwear lie on the floor and starts stuffing them into my school bag.
I hop off the desk, my legs now more stable and pick up a red push up bra from the pile. I look at it for a moment before realising all the clothes are girls clothes. This bra will do the exact opposite of what my crop top does, it'll accenuate the cleavage that I've been trying to hide, that I've been trying to deny exists since I started growing breasts.
"It's just like your sports bra, but more comfortable." Mr Hollinhoe says coming up behind me and grabbing the bra. He slides it up my arms, pulling the straps over my shoulders and clasping it together on my back. The cups cup my pert little breasts and tries squeezing them together.
My big sister has been trying to get me to try on bras for years but I always refuse telling her that boys don't wear bras. She never pushes me after I say no, but that doesn't stop her trying again a day or two later.
Mr Hollinhoe is right, it is completely different to my restrictive crop top and feels nice and comfortable holding and supporting my breasts instead if trying to firce them back into my chest. I look down and admire my curvy cleavage for the first time as I run my hands over them and marvel at how firm tney feel in the bra.
I gawk at him when Mr Hollinhoe picks up a pair of black fishnet tights, like my big sister might wear as part of a costume on halloween, and he tells me to hop back up onto the desk.
"You found these in the lost and found?" I ask in disbelief as I perch up on the edge of his desk and lift one leg for him.
"The confiscated pile actually, just like your bra and thong." He says sliding the fishnet up my smooth slender leg until it reaches the bottom of my bum on the desk.
"You got me a thong too?" I ask shocked that they have these things in the school as I lift my other leg for him.
"Yeah, you'd be surprised what some of the little sluts will try wearing into school nowadays." He tells me sliding the other fishnet up my other leg until me sitting on the desk prevents him from pulling them any higher. I slide off and he grabs the waistband and pulls them up over my bum and hips, then slides a hand between my legs and pushes the gusset up to my crotch. They feel really strange but in a good way. The thread digs into my skin a little bit but makes my legs feel more sensitive, especially when his hands brush against them as I step into the red thong. He pulls them all the way up and the small patch of fabric is big enough to cover my tiny willy and testicles but not all of my pubic hair, then he pulls the tong up at the back so it and the fishnets slide into the cleft of my bum cheeks. It feels like a wedgie, but really nice.
Next he grabs a pair strappy platform shoes and kneels down to put them on my feet one at a time before strapping them up.
"There, try them. Walk to the end of the class and back. You want to place your next step exactly in front of or just the otherside of your last foot." He says shownig me with his feet. "Don't worry, they might take a little getting used to."
He's not wrong as just standing in them feels awkward with my heels postitioned higher than my toes. It almost feels like I am walking on tip toes, but not quite. I manage to walk down the classroom, concentrating so much on not stumbling that I forget that I am dressed just in a bra, fishnets and a thong. That is, until I notice Mr Holloinhoe staring at me hungrily, then I feel the movement of the air caressing my thighs, and the thong riding up between my swaying bum cheeks with every step I take. I stumble, but manage to catch myself becoming very self concious and blushing furiously as I try forcing myself to walk properly back to him.
Being intimate with and becoming one with Mr Hollinhoe while lost in the lust felt amazing, but parading about my classroom in front of my teacher wearing girls skimpy underwear, I am suddenly pulled out of my reverie and shame wells up in the pit of my bare belly.
"Come here Billy." Mr Hollinhoe instructs noticing me falter. I do as he says but can't help thinking of what we're doing without the fog of lust and am disgusted with myself. I just want out of these trashy garments and out of this classroom, this school and to crawl into my bed, curl up and cry.
I'm not gay, I can't be. I'm attracted to girls, not men. Looking at Mr Hollinhoe I don't find him attractive and feel some relief at that, until I reach him and he grabs me, pulling him against me with such authority that I feel a strange sensation unfamiliar to me.
I feel powerless to resist him and find myself not wanting to, as his arms wrap around me and hold me tightly against him. I look up at him to find him leaning down to kiss me. I part my lips remembering how he made me feel and wanting to feel that uncontrollable lust again as I take his tongue in my mouth and feel his lips rub mine.
I forget all about the shame even as it recedes away into nothingness and I melt in his embrace.
Suddenly he breaks the kiss and releases me fom the embrace leaving me breathless and wanting as he grabs a skirt and wraps it around my waist before buttoning it up. It is so short it barely covers my pert bum but I don't care and just want Mr Hollinhoe to take me.
He's not done dressing me though and next comes a short sleeved white blouse which I hold my arms out for as he slides it on me. The blouse is a size to small and when Mr Hollinhoe buttons up two of the buttons, it strains to confine my breasts and my bra can be seen through the gaps between the taut buttons. He leaves my new meager cleavage exposed and then ties the remainder of the blouse in a knot below my breasts leaving my flat belly bare.
"Nearly done, just your hair left to do." Mr Hollinhoe tells me grabbing a pair of red scrunchies before dividing my hair in two and using them to give me a pair if pigtails, one just behind and above each of my ears. "There all done."
He pushes me back a few steps with his hands on my shoulders and looks me up and down seemingly pleased with what he sees by the look on his face.
"Perfect. Come on. It's time for your first home schooling." He tells me putting an arm around my waist and pulling me next to him as he picks up my school bag and we walk out of the classroom. I slide my own arm around his waist and get excited when Mr Hollinhoes hand slides down over my bum before going under my skirt and cupping my bare bum cheek as we walk through the now empty hallways.
Oddly I feel really naughty and horny dressed like a slut with my teacher groping my bum and me enjoying it, so I reach across with my free hand and place it on Mr Hollinhoes crotch caressing his limp penis through his trousers. It swells to my touching and that excites me so that I don't stop even when we leave through the entrance and emerge outside.
I stumble as we descend the steps and it's only my arm around Mr Hollinhoes waist and his hand groping my bum that stops me falling when I see Simon and his mates still hanging around, apparently waiting for me. They look up at us and I blush so brightly that my cheeks burn and I prepare myself for the insults to start coming.
"First lesson baby, you don't stop rubbing my cock until I tell you, not even if there are people around to see." Mr Hollinhoe tells me and I hesitantly place my hand back on his bulge, turning my face away from them in hopes that they don't recognise me.
"Wow, Mr Hollinhoe has got himself some hot pussy." I hear Simon say not quietly to his mates as we walk past them. A thrill surges through me when I realise they not only don't recognise me, but think I'm hot also and I start rubbing Mr Hollinhoes bulge vigorously.
We continue on and I find myself wiggling my bum as we walk over to Mr Hollinhoes car. He opens the passenger door for me and I slide in, reluctantly letting go of his bulging crotch. I can't help but stare at it as he walks around the car and gets in the drivers seat.
"Here's your second lesson. Whenever we're in the car you're to pull out my cock and wank it off whenever you're not giving me a blowjob." Mr Hollinhoe tells me grabbinng my hand and placing it on his hard bulge.
I lean over and unzip his trousers, pulling out his hard penis as he pulls the car out of the school carpark and am captivated by it as I start wanking him off.
I have no idea where we are going as I don't take my eyes off his penis the whole time and don't stop stroking him until we pull up into a driveway lined by trees that mark the property line and a front garden filled fruit trees and lined by a high hedge that obscures the detached period house from the road and the neighbours.
Mr Hollinhoe gets out and comes around the car and opens the door for me with his penis still sticking out of his trousers. I grab it immediately and he puts an arm around me as he guides mes along the pathway with a hand up my skirt and cupping my bum cheek until we get to the front door of his house.
"Right, I think that's enough lessons for one day. You run off home now and come back tomorrow morning bright and early." He says suddenly and I look up at him only to recieve a passionate tongue filled kiss that makes me swoon.
Do you reluctantly head home or beg Mr Hollinhoe to let you stay?
What's next?
My life
The choices I wish I had after finishing school
Note - This story is told from a submissive sissy/femboy/tranny perspective and I try to write it so you, the reader, are the protagonist. So if you are more into being a top or domineering character, this probably won't be for you. Note - As always the way I write is rather erratic and I'll often return to and amend already published chapters to fit in with the direction a story arc has taken, so apologies for that. Note - please feel free to comment and message about anything. Prologue - Born to a pair of addicts I was a veritable crack baby addicted to the substances my parents abused. My early childhood was dire and dismal being 'brought up' in a home of neglectful and abusive parents. After my mum dies and my dad is turned into a vegetable from overdosing, I am taken in by my one time babysitter and adopted by her parents. She becomes my BFF and role model, grooming me to become her sister. Since my eleventh birthday she has secretly been feeding me a regiment of puberty blockers and female hormone therapy medication to ensure my transition but not make my development so obvious that it contributed to the bullying I already faced on a daily basis at school. For seven years I have publicly identified as a boy, with the last two years having to use restrictive undergarments and a permant exclusion from P.E lessons to hide the feminine characteristics that I am developing due to a rare genetic disorder that was caused by developing in my addled mothers womb and would be far more prominent if I was taking the meds that they've been feeding me, or so they tell me. Unbeknownst to me my emotional struggles stem from the fact that I am now more physically a girl who is masquerading as a boy and a boy still trying to deny he's mentally and emotionally a girl, but that's all about to come to a head.
Updated on Mar 1, 2024
by Monalott
Created on Sep 17, 2017
by Monalott
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