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A Re-education
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Ever since I was young, I would sneak any chance I got to try on my mother's tights and clothes. I began with tights and was instantly aroused by the right, clinging feeling of them against my body. I knew this was wrong but couldn't help myself in going back time and again. The shame of this desire was always superceded by the uncontrollable want to do it.
As the months went by my bravery increased and I graduated to tights and maybe a skirt and blouse over them. Following this, high heels were a revelation. Painful to wear and hard to walk in but they made me feel so sexy it was never long before I wanked myself to completion, very careful not to get a drop on the forbidden clothes.
I would always replace them exactly as I found them and felt like I'd gotten away with something every time afterwards. This was a shameful and confusing thing to do but it was just my little secret so there was no one to judge me.
As I got braver and had the house to myself I would risk a little lipstick and maybe tie a towel around my head to give the impression of long hair.
Next I would steal one of my mother's cigarettes and pretend to smoke it while dressed. I wouldn't dare light it for fear of covering the clothes in the smell and giving the game away. I was also afraid to in case I liked it and I definitely didn't want to become a smoker.
One day, around Halloween, my mother announced that she would be going out for the evening to a work dinner and wouldn't be home until very late. I was thrilled at the news. I had never gotten so long a period of time to myself alone in the house and I knew exactly what I wanted to do to fill it.
This would be the night I went further than I ever had before.
The day of the work party finally came after what seemed an eternity since the big announcement. I was sick with nerves and excitement. My plan had been laid out in my head and I could barely believe in just a few short hours it would commence. As it turned out those hours felt like days and more than once my nerves had me abandon it completely and just watch TV for the night. Finally however seven O clock came and my mother appeared in the sitting room door.
"How do I look?" She asked.
"Great" I said. It was just the two of us and she rarely took the opportunity to get done up and have a night out to herself. Despite my selfish reasons for wanting her to go out, she deserved it.
"Don't stay up, I probably won't be home before midnight" she told me and I couldn't have been more excited.
I heard the door close behind her and it was time to get to work. |
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I rushed up to her bedroom, checking the window to make sure she hadn't forgotten anything and was on the way back. Coast clear I pulled out a silky pair of panties and matching bra. Sliding them up my legs and feeling their smoothness against my skin I was hard already. That would have to wait though as I wasn't wasting this opportunity for a cheap wank. This one was to be earned.
Next I put on the matching bra and fumbled with the catch, eventually having to turn it around and do it from the front. With this done I turned it into place and filled each cup with a bulky pair of sports socks. Completely amateur but running my hands over the filled outer cups made my penis twitch.
I picked the shiniest pair of tights I could find from the drawer and slowly slid them up my legs. I was going to take my time and enjoy this.
With them in place and any bunching taken care of, I then took a look in the mirror. A skinny young man in women's underwear and tights with a massive bulge in the crotch area.
It felt so wrong but so right at the same time.
I had chosen a silk blouse and carefully put it on and buttoned it up, It felt so delicate and I didn't want to damage it. For reasons of not being caught but also because the garment felt like it demanded a gentle touch.
Over this I ran a figure hugging pencil skirt up my legs and it clung to my figure, the restriction of my legs reminding me how much effort women go to to look attractive and sexy. I was more than willing to put up with it.
From the closet I chose a pair of shiny white heels and clicked my feet into place in them. Despite the contorting of my foot, it felt right. My ankles went a few times walking to the bathroom but practice makes perfect.
In the bathroom I switched on the light above the mirror and pulled out my mothers make up bag. I wasn't going to put on too much as I was afraid of getting it off.
Besides, a dark red lipstick overdrawn on my already generous lips was nearly enough for the effect.
I dared try a little mascara and thrilled at how much of a difference it made to my eyes.
Too much blush on the cheeks next and I was ready to tie the towel around my head. A black one, so as to look vaguely like black hair.
The effort was beyond crude but I could see the makings of something in it.
I was slight with food bone structure and my terrible make up job did enough to suggest that I might make for a very good looking woman indeed.
Ready to go, it was downstairs for the next part of my plan.
I nearly toppled on the stairs in my heels and images flashed in my head of my mother finding me lying at the bottom and me waking up in hospital dressed like this. It wasn't enough to make me go back and change but definitely enough to have me grab the bannister with both hands.
Successfully downstairs, I had planned to go a little further than I had gone before. I was going to finally light a cigarette while dressed.
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I knew from my mother's smoking that if I opened a window all traces would be gone in about twenty minutes. I could have my epic wank, race upstairs and change and go back down and watch TV, having pulled off the perfect crime, and myself.
I had no intention of starting smoking, it was a filthy habit and the only girls I knew who did it in school were the bad ones. That was the turn on fro me. I was going to be one of those bad girls and give myself the greatest orgasm anyone ever had.
I took out the pilfered cigarette and picked up one of the myriad lighters strewn about the house. My heart was racing and my cock strained against the restrictive trio of panties, tights and pencil skirt. I thought I was going to faint with excitement as I lit the lighter and brought the flame to the tip of the cigarette, dangling from my painted red lips. It caught and I sucked in, as I knew you do, the smoke hitting the back of my throat in a very pleasing way and my head feeling a rush that made my muscles melt.
I had read that you suck on the cigarette like a straw then breathe in.
Doing this made me cough as I'd never smoked a cigarette before but behind the cough was a very high and relaxing feeling. "Hmm" I thought to myself, "I can finally see why people do this."
The feeling given by the smoke and the though of being a bad girl for doing it had me reaching for my swollen cock.
I struggled to get it out from beneath the layers it was encased under but there was no chance of it staying there.
It sprang out from under my blouse and instantly I was stroking it. The stroking became furious as I pulled on the cigarette at the same time, the back of the throat hit complimenting the self given pleasure in my groin.
Within seconds I could feel myself cumming and took a super strong drag which added to the most powerful orgasm I'd ever felt. I squirted a torrent of cum everywhere, more than I ever had before. I couldn't stop rubbing my cock up and down, long after the cum had stopped flowing and the cigarette now dangling hands free from my mouth, me still pulling away at it without even thinking. If this is being a bad girl, I want in.
My entire body was feeling waves of pleasure and as I finally slowed down on the stroking and puffing, like a train slowing down well before the station, I heard behind me the front door slam. |
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It took about two seconds for the sound of the door slamming to go from my ears to my brain. It took a lot less time for the feeling of sublime pleasure, the likes of which I'd never felt before, to turn to abject terror, the likes of which I'd never felt before.
The next five seconds slowed down to feel like five minutes, like someone falling from a great height going over their entire life to see if there was something there to save them in their predicament. The life flashing before your eyes effect.
If I ran out the back door, I would be caught for smoking but could perhaps avoid being caught for crossdressing.
There was no getting away from the smoke filled kitchen. It was thick from how hard I was puffing while wanking myself to completion.
However if I did run out the back I was bound to be seen by a neighbour and if not, where the hell would I go?
As my escape plans cancelled themselves out one by one, at the very least I managed to put my cock back where it came from. I would be caught in my mother's clothes, smoking her cigarettes, but at least I wouldn't be caught wanking as I did it.
My mother opened the kitchen door and surveyed the scene.
She whispered to herself "what the hell?" As she looked upon me in her best work clothes, cigarette with long inflicted ash dangling from my painted red lips. As for the third embrassment, I didn't get away with that either as she spotted the pools of cum on the floor tiles and her eye line moved from them to my bulging crotch, which had saw fit to find just enough cum left in me to seep out to the front of her expensive pencil skirt, leaving an unmistakable stain in the front.
We stood looking at each other for what felt like forever, neither breaking the silence. It was me who broke it when the smoke from the cigarette in my mouth found its way into my eyes, stinging them painfully and causing me to spit it out.
"I'm sorry " I said, "I don't smoke, this was only a bit of fun," as if that was all that needed explaining.
I was mortified to be found dressed like this. Mortified to be caught smoking on my first attempt, boys these days don't smoke, only girls, and bad ones at that.
Eventually my mother said "I forgot my phone" and went over to where it was on the sideboard. She took it and said, "I'll see you later" and once again left the house.
This was nearly worse than her giving out to me as I had no idea what she was thinking. I quickly scrambled to get undressed, scrub the make up off, clean the tiles and throw the skirt into the washing machine.
All of that done I went and hid in my bed. Not that I could get any sleep with the fear and adrenaline coursing through my veins.
I lay awake for hours and at some point heard her arrive home.
She pottered about downstairs for about a minute then went straight to her bedroom.
She did not make any attempt to talk to me. |
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The next few days were excruciating.
My mother didn't address what she saw which was worse than if she had gone mental over it. She didn't seem mad however, instead she appeared lost in thought. We spoke little and when we did it was polite and small talk.
The stress was killing me. My appetite had gone and I couldn't sleep.
After two weeks she got a phone call from the school headmaster to say I wasn't paying attention and kept falling asleep in class. I had turned 18 but still had exams to do and at this rate hadn't a hope of passing them. The phone call from the school finally made her act.
That evening when I went home she called me into the kitchen where she was sitting at the table, smoking.
She must have been there a while and gone through a few cigarettes as the air was thick with smoke and hard to breathe. "Cigarette" she offered and all of a sudden my stomach lurched.
"But I don't smoke Mom" I said.
"I know, but I think it would relax you and me both, just take one."
What was I to do. The offer brought back the intense memories of the wonderful night two weeks previous but also the immense shame. I also had to admit to myself I was dying to try another cigarette.
"Take one, we need to talk" she said in a sterner voice and my hand trembled as I reached for the open pack.
I could barely keep my hand still as I put it to my lips and attempted to flick the lighter. Bringing the flame to my lips the smoke hit the back of my throat again and for the first time in two weeks I felt sweet relief of any kind. Better yet, the sweet relief that this amazing experience brought me.
"Now" she said, "I've had a call from your headmaster about your performance in school this past few weeks. You're not paying attention and are falling asleep in class. It's alright, I understand you have been worried about...that night, but you don't have to be. I assured the headmaster that you have been under stress lately and that I would take you out for two weeks for a respite."
"What kind of respite?" I asked.
"I've arranged somewhere for you to go to deal with...all of this, and re-evaluate things. Also to get some rest.
That's all you need to know. I want you to go to bed early and we'll be off in the morning."
I finished my cigarette and felt the better for it.
"Thank you Mom" I said.
"You're welcome sweetly" she replied.
"How was your cigarette?"
"Very nice, but I don't smoke, you know that right?"
"Of course I do, tell you what, take one more then head to bed."
"Ok" I said, secretly thrilled as I wanted another, though I had no intention of becoming a smoker. |
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The next morning came and my mother handed me what I thought a very light bag for a two week holiday.
As much as I enjoyed smoking in front of her, In the cold light of day I was embarrassed about it and also didn't want to get addicted so I decided there and then there would be no more smoking for me. When she got into the car and motioned towards her pack, saying to light us up one each, I replied "No thanks, I'm not a smoker" and felt good in my resolve.
"I know that sweety," she said as she fumbled with her phone, "Tell ya what, light me one as I text this person back."
This seemed reasonable so I took one of her extra long 120 length cigarettes out of its pack. I felt a bit embarrassed realising I was in public, albeit in a car, lighting one of these super long, feminine cigarettes but it was only to pass to her.
The flame hit the cigarette and I took a pull to make sure it caught and once again that hit at the back of my throat sent me into a tizzy. I would miss that feeling but it's not worth it for all the downsides of smoking.
"Shit, I forgot my purse" my Mother said and rushed back into the house to get it.
She hadn't taken the cigarette off of me and I sat there with the smoke drifting upwards, the smell reminding me of how good they felt. She had been inside for a minute or two and the ash was getting longer. What the hell I thought, I might as well take another pull until she gets back, and did so.
This one felt even better. Still no sign of her, I took another and another until the cigarette was completely smoked. About two minutes after that she finally reappeared and getting into the car said "Light me a cigarette will you?" With no mention of the one I had smoked completely.
The journey lasted hours, deep into the countryside. She wouldn't tell me where we were going. We stopped at a service station for something to eat and after she lit herself a cigarette before hitting the road again. She didn't offer me one this time and my stomach felt a little jolt as it would have been very satisfying to smoke one after the meal. For the rest of the drive she lit herself three more cigarettes and at this stage, being trapped in the car with her as she smoked and I didn't, I was positively ravenous for one.
As the daylight began to fade and I was felling somewhat cranky from the long drive and teasing smoke, we finally arrived at a set of gates in the countryside. My mother gave our names to a crackly voice over the intercom and we entered.
Little did I know what awaited me when I reached the main house. |
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Upon the gates opening I had thought thank God, were finally here, but the road to the house seemed to go on forever. There were trees either side so you couldn't see beyond but this was clearly a large estate. After about two minutes of driving up the winding road lights finally appeared in the distance and soon after the house came into view.
You couldn't get a full look at it in the now dark but it was clearly enormous. Whoever lived here had money. Was it some kind of spa resort? Was I going to get massages and play golf for two weeks to help me relax and get back to myself? I would soon find out I would be getting back to something but it was far from myself.
We pulled up outside the enormous front door with pillars either side and I took my bag from the back seat. My mother had packed it for me and placed it in the car and if I felt it look light, it seemed practically empty on lifting it. Walking over the gravel crunching underfoot we climbed the steps to the front door and pulled an old fashioned bell. I heard it ring deep inside the house and a moment later a door opened.
A very tall and very attractive woman opened the door and greeted us. She was wearing a full length black dress and had her hair tied up severely. Despite this her smile was warm and welcoming.
She confirmed our identities and asked us to follow through to an office underneath a grand staircase which split two ways after the first ten steps or so. The foyer was large enough to play football in and I started to feel a little excited to go with my curiosity about staying here for two weeks.
The tall woman led us into a dimly lit office with a fire blazing.
The walls seemed black but were probably some kind of dark brown wood.
There was a tone of red decor tastefully decking out the office. Red leather chairs, red banners. It was very comfortable. My mother was directed to one of two large leather armchairs set in front of a large wooden desk, behind which was a darkened window with the curtains opened. By the lack of lights outside we seemed to be the only building for miles. I was directed to sit on a three legged stool with no back between the two armchairs which I felt was odd, could I not sit on the other chair? I did as I was told however and the tall woman made to leave, telling us Mistress Clea would be with us shortly.
Mistress? |
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Alas no, the story was a few parts further ahead on the other site but got deleted by mods.
I have no idea why and asked for feedback but didn't get any so I don't know what I did for it to be deleted.
Therefore reluctant to continue here. |
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