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Part 1 - Lessons in Femininity.
This story was written by Billy Blaze. If you have any comments I would love to hear from you. Email me at. [email protected]
This is a story of an extremely unusual experience I had when I was 16, even now looking back all these years it still seems amazingly unreal, but it's all true. This is what happened.
When I was 16 years old I had a sort of crush on my teacher, Miss Granger.
She must have been in her mid thirties, short strawberry blonde hair, glasses, she was quite pretty in a 'Motherly' sort of way. She didn't have 'model' looks, but I was strangely drawn to her, she had a sort of power over me that made me instantly do whatever she asked.
On my way out of the school one day, one of my friends came over to me and told me that he'd found out where Miss Granger lived, so a little while later after I had got home and got changed I met my friend and we cycled across town to where she lived. It was a nice house, a small garden in the front, the living room windows faced the street and had those typical 'eighties' style vertical blinds in the windows. It was quite a large house, apparently Miss Granger had a 17 year old daughter from a previous marriage and the two of them continued to live in the house after her husband had left. After we had had a good look we went off on our bikes to the nearby woods and spent the rest of the day scrambling.
Up until this point my life was pretty normal, I was a typical 16 year old boy, out on my bike every day, sometimes the whole weekend, only popping home for a bite to eat before going out again. My parents pretty much left me to my own devises, I loved getting dirty (much to my mother's annoyance), I was always playing in the rivers and making camps in the woods, but now something else had grabbed my attention, and I found myself compelled to go round and look at Miss Grangers house. I would cycle up and down outside wondering if she was there, sometimes I would sit on the pavement across the road and look over, seeing her sometimes through the blinds or at an upstairs window. Looking back now it seems obsessive, but at the time I think I was just fascinated, seeing my favourite teacher away from school, doing normal everyday things, seeing her in a totally different environment, I didn't know it at the time, but my life was about to radically change forever.
One day during one of my visits to her house, Miss granger caught me. She asked me what I was doing and why I was constantly around her house. I was struck dumb for a moment, stumbling and babbling I replied that I wasn't doing anything, at which she took me by the hand and led me into the house, saying that if I hadn't anything to do she would find me something. Moments later I was standing at her kitchen sink doing her washing up, Miss Granger stood behind me and informed me that after the washing up I was to do the dusting in the living room. I couldn't believe what I was doing. Here I was at nine O'clock on a beautiful Saturday morning, doing various cleaning chores in my teacher's house instead of out playing on my bike. I had just started the dusting in the living room when Miss Granger called me into the dining room, she was standing on a stepladder to change a light bulb in the ceiling, she asked me to stand on the bottom rung and steady it for her, I did as I was told and stood there at the bottom. I then did something that was to have a fundamental effect on my whole life. This one moment in time changed my life forever. I looked up.
I was staring up her short skirt, she was wearing a pair of silky white knickers, her legs looked so soft and smooth, and her knickers were shiny and had little lace edges, it was an amazing site, I was transfixed, I'd never really noticed women's knickers before, certainly not sexy ones like these. It wasn't long before my chores were done and I was on my way home with strict instructions to return the next day.
The next day came and the image of the day before was still fresh in my head. I turned into Miss Granger's quiet little estate on the edge of town, freewheeled down the hill towards her house, wondering if I would get another chance to see her skimpy knickers. As I walked up to the front door my heart was jumping, I nervously rang the bell. Miss Granger opened the door to let me in.
"Now young man," She said as she closed the door behind me.
"We'll start upstairs today." And she led me up the stairs and over to a door, which had a sign on it saying, 'KIRSTY'S ROOM DO NOT ENTER!!' We went in and she instructed me to sit on the bed. I sat there looking around, it was a pretty cool room, posters of sexy girl bands on the walls, a dressing table which was covered in beads, makeup, perfume bottles etc. Then Miss Granger turned to me and said, "Right then Sam, I couldn't help noticing that while I was on the stepladder yesterday you took the opportunity to have a very long look up my skirt at my underwear!" I suddenly felt the blood rush to my face.
"No I didn't Miss," I said shakily.
"Yes you did Sam!" She said smiling, "I saw your reflection in the patio doors. I saw everything, as did you I imagine." My face turned a shade of purple and my heart was pounding in my chest. Then Miss Granger got up and walked over to a chest of drawers, and rummaging around in one of them said, " I don't mind if you want to stare at my knickers Sam, but I've got a better idea." She turned round holding a pair of pretty white panties and said, "Instead of just looking at my knickers, I'm going to make you wear a pair." I sat there in total shock, it hit me like a slap in the face, and before I had time to react she placed the panties on the bed and told me to put them on.
"Now Miss?" I said, as I sat there looking at them.
"Yes Sam, now please." She replied, her face deadly serious. Shakily I started to undress, conscious of her watching my every move. When I had taken everything off except my underwear I paused, "Come on Sam, hurry up!" She snapped, "I want you to know what it's like to be stared at wearing silky knickers, now put them on and don't be so silly!" Taking a deep breath I quickly pulled my own pants down, picked up the knickers and slipped them on over my feet and pulled them up. They were tiny, and felt really silky against my skin, they had really narrow sides that were made of lace and there was a small pink bow on the front. Miss Granger looked at me admiringly, "They suit you Sam, much nicer than your boys pants," She said as she turned me around to have a good long look at me, "So I think you should wear these for the rest of the day while you do your chores." And she opened the door and ushered me out of the room, patting my silky bottom as I walked past.
"Can't I put my jeans back on Miss?" I asked.
"No Sam, you can do your chores in just your knickers today." And with that she led me downstairs and instructed me to start in the living room.
So I spent the rest of the morning doing housework dressed only in a pair of skimpy knickers, It felt really unusual wearing women's underwear, but strangely I wasn't that embarrassed, I just got on with my chores, and I must admit they did feel really comfortable. I'd never worn anything but cotton underwear all my life, but these felt great. I found myself constantly touching them and looking at myself in the mirror, I loved the feel of silk against my skin, the way it sort of slid against my skin as I moved. But there was one other thing that was strange, and that was Miss Granger's attitude towards me. She now seemed much nicer, and gentler. After a while she called me into the kitchen to have some lunch, I padded into the kitchen, the lino floor was cold against my bare feet and I took a seat at the breakfast bar. Miss granger put some lunch on the table, looked at me and noticed that I had goose bumps.
"Oh you're cold," she said, giving my bare legs a rub.
"Let's get you some more clothes to wear." And she led me out of the kitchen and took me back up to Kirsty's room, sat me on the bed and proceeded to get out some clothes from the wardrobe. I couldn't believe my eyes when she took out a denim mini skirt and a pink long sleeve top.
"There," She said, putting them on the bed next to me.
"Put these on, Kirsty won't mind, she's away at her father's house this weekend." I sat there quite shocked not knowing what to say or do. Then she said, "Better be quick or lunch will be getting cold." Then she left the room and went down to the kitchen. I took the clothes and proceeded to put them on, it felt so strange to be wearing girl's clothes but I didn't want to be told off for letting my lunch go cold. Before I left the room I took a quick look at myself in the mirror, I hadn't noticed it until then, but I had quite a feminine look about me, my hair was blonde and shoulder length, and my face was smooth and almost pretty. I hadn't developed any body hair yet so my skin was quite smooth. As I walked into the kitchen Miss Granger looked at me and smiled, she told me that I looked really pretty and that if I wanted to I could wear these clothes again tomorrow. My mind was spinning around like a washing machine, the situation was so unusual, but I was really enjoying the attention. I lived in a cold house emotionally, both my parents didn't really take any notice of me and had never shown me any affection, and although it was weird wearing girl's clothes I suddenly felt wanted. As I cycled home that day I couldn't get the days events out of my head, it had certainly been the weirdest day of my life, and I put it down to the fact that Miss Granger was obviously missing her daughter and I was her temporary substitute, but I also realized that deep down I secretly longed to wear those clothes again.
By nine o'clock the next morning I was already on my way across town to Miss Granger's house, having gulped my breakfast down and ran out the door telling my Mum that I was off to a friends house for the day. When I arrived at Miss Granger's house, she told me that because I had looked so nice as a girl the day before I was to be dressed as a girl again. So I had to go up to Kirsty's room, put on the clothes she had got out for me and return to the living room. Nervously I went up to the room and entered, on the bed was another pair of white silk panties, the pink top I had on yesterday, a white mini skirt and a pair of sparkly high heel sandals. After I had dressed, I went back down to the living room, Miss Granger was sitting on the sofa, she got up, walked over to me and kissed me on the cheek.
"You look very pretty," She said as she adjusted my skirt and looked me up and down, my face glowing red with embarrassment.
"You have the perfect legs for little short skirts. How do you find the sandals?" She asked.
"Can you walk in them ok?"
"Yes Miss, I like them, but I'm a little wobbly still." I said. Then she led me over to the sofa and sat me down next to her.
"Now, I have something to say and I want you to listen carefully," She said.
"Do you like coming over to see me?"
"Yes Miss," I replied.
"Good." She said.
"Because from now on I want you to come over every weekend ok?"
"Yes Miss, that would be nice," I said.
"And from now on whenever you're here you're going to be a girl. You'll be dressed as a girl and treated like a girl understand?"
"Yes Miss," I said, my heart pounding in my chest.
"Your name will be Samantha, and you will remain a girl until I say you can go home, you can share Kirsty's clothes for the moment, we can look through some catalogues today and you can choose some clothes of your own." I sat there in total silence not really believing what was happening.
"Now you will be required to do some of the housework," She continued.
"But I want you to treat this house like it's your home, and sometimes if you like, I will let you stay here over night providing your parent's agree, ok?"
"Yes thank you Miss," I replied.
By mid morning I had finished my chores, Miss Granger beckoned me over to the sofa. She had a large selection of catalogues, which she had piled on the floor by her feet.
"Now then young lady," She said, opening one of them, "Let's get you some nice new clothes." We spent ages looking through them, she asked me to pick out a few items that I liked, I picked some little skirts and tops before we came to the lingerie section, there we had great fun picking out lots of pretty silky knickers for me to wear, and I suddenly became aware that my cock had risen up hard inside my panties. On the next page there were lots of sexier lingerie, there were pictures of women in stockings and suspenders and basques etc.
"I like those Miss," I said, pointing to a woman in white stockings.
"I don't think your old enough to wear stockings and suspenders yet young lady," Said Miss Granger smiling, "Maybe when you're a little older." But I couldn't get those images out of my head, the way those stockings hugged that woman's beautiful legs.
After we had finished flicking through the catalogues, Miss Granger turned to me and said, "Samantha there's something else I want to say to you." She took my hand and in a gentle voice said, "Now from time to time I will feel the need to establish my authority over you." I looked at her blankly, "What do you mean Miss," I said.
"Well despite whether you've been naughty or not, I will want to spank you," She said. My heart began to pound again, "Spank me Miss?" I said, surprised, my voice shaking slightly.
"Yes," she replied.
"From time to time I will put you across my knee and spank you, just to remind you of my authority." She smiled at my nervousness and said, "Don't worry, it doesn't hurt that much, I spank Kirsty every once in a while, she's used to it now." Then she put her hand on my knee and said, "Have you ever been spanked before?"
"No Miss," I replied softly. There was a pause and then she said, "Would you like me to spank you now?" I sat there not knowing what to say.
"I don't know Miss," I said meekly. I didn't want to, but at the same time I knew that she wanted to spank me and I didn't want to say no to her.
"I think perhaps it would be best if I did," She said, and she got up from the sofa and held out her hand towards me, nervously I took her hand and she led me out of the living room and into her study. My heart was beating hard at the thought of what was to come. Miss Granger closed the door behind me and placed a chair in the middle of the room, before sitting down on it.
She took my hands in hers and pulled me closer to her, my whole body was shaking as I approached her, the heels on my sandals clicking on the wooden floor.
"Now don't forget," She continued, "I'm not spanking you for being naughty, I'm not cross with you, I'm just doing it to maintain my authority over you, ok?"
"Yes Miss." I said, not knowing where to look.
"Ok then." She said. And with an heir of authority told me to lay across her lap. I took a step towards her and leaned forward, arms outstretched. I placed my hands onto the edge of the chair to stop myself from falling forward and slowly and awkwardly lowered myself onto her waiting lap. I wriggled around embarrassingly trying to get comfortable. I felt very exposed and vulnerable as I lay there. I was totally in her power which was exactly her reason for doing it, to confirm her power over me. My heart was pounding harder than ever as Miss Granger reached under the hem of my mini skirt, slipped her fingers under the lacy top of my panties and slowly and deliberately began to pull them down over my bottom. My sense of vulnerability grew stronger as I felt my panties gently being pulled down over my bottom and down my legs to my ankles. Then she pulled my mini skirt up exposing my bottom to the air, I felt my face glow red with embarrassment at the thought of being in such a position. Miss Granger then placed an arm across my back to hold me down. I screwed my eyes tight shut waiting for the first strike. I didn't have long to wait, within seconds she began to spank me, hard stinging slaps reigned down on me, the sound echoing around the room. I started to squirm and wriggle as the pain intensified. Miss Granger tightened her hold on me and continued. The feelings and emotions I was experiencing grew more intense with each slap, deep humiliation, vulnerability, shame, and total domination. Being undressed, held down and spanked, also made me feel violated. There didn't seem to be an end to it all, Miss Granger was spanking me harder and harder, It all became too much to take and I started to cry.
"No Miss, please." I cried, tears running down my face, my body wriggling and writhing on her lap, my white silk panties wrapping themselves around my high heel sandals as my legs kicked out in pain.
Then at last the spanking stopped, Miss granger then began to rub some cream onto my sore bottom, it felt cold against my skin, her touch was gentle and soothing as she slowly rubbed it in, then she pulled my knickers back up and adjusted my mini skirt before sitting me up on her lap. Partly due to the relief and partly all the emotions I was feeling, I threw my arms around her and, burying my face in her neck cried long and hard. Miss granger hugged me and comforted me, telling me I was a good girl and that I could do what ever I wanted for the rest of the day. As I sat there on her lap, with my arms around her, crying, I felt somehow secure in her presence, that despite the spanking I'd received it had been for my own good, she was looking after me, protecting me. Maybe it had something to do with the little amount of love that I had received at home, and the only way that Miss Granger could show me she loved me was to spank me. The strange thing was, the experience had actually made the bond between us stronger, the feeling of master and servant had been re-established, she'd always had a power over me but now it was different, I felt very submissive towards her, a kind of respect that wasn't there before the spanking.
The following week went like a blur, I'd slipped into the usual routine, school, home, play, but every now and again I would think about the coming weekend, spending my weekends as a girl at Miss Grangers house was what I looked forward to most of all, completely the opposite from what I was doing before. I had gone from playing in the mud and dirt with my bike, to dressing in up in girls clothes and doing household chores, a situation I look back on now as totally bizarre, but back then it seemed more natural, like taking up a new hobby.
Saturday came at last and as I cycled up to Miss Granger's house I saw a girl on the front drive, she looked at me and smiled as I got off my bike.
"Hello," I said, "You must be kirsty. And then it suddenly dawned on me did she know about my 'special' weekends? For a split second a horrible thought came to me, what if I wouldn't be aloud to carry on with my secret life now that she was home. But my secret was out, Kirsty looked at me with a sly grin and said, "You must be Sam, or is it Samantha?" I immediately went red in the face.
Although it seemed that my weekends would continue, I wondered how Kirsty would react. But she saw that I was a bit embarrassed and put me immediately at my ease by taking my hand and telling me that she was looking forward to sharing her weekends with me, and that her Mum had told her all about me and that she was pleased to have a sister to spend time with. As we went in, Miss Granger was standing in the doorway, "Mum, can I take Samantha upstairs and help her get dressed?" Asked Kirsty excitedly.
"Ok," She replied, "But be quick, I want the living room tidied up before you two can spend time together understand?" Kirsty literally dragged me up to her bedroom and I just caught Miss Granger shouting the words, WORK BEFORE PLAY! as the bedroom door shut behind me.
Although I was pleased that Kirsty knew of my dressing up, I was still a little embarrassed to get dressed in front of her. Kirsty sensed this and sat on the bed next to me.
"Don't be shy Sam," She said, taking my hand, "When Mum told me all about you I was really excited, I'm an only child, I've always wanted a sister, I don't care if you're really a boy," She let out a cute little giggle as she said, "And lets face it, you don't exactly look like one do you?"
"How do you mean?" I said, smiling back.
"Well, look at your face, so smooth and soft, you only have to do your hair the other way and you look just like a girl anyway without the clothes." I leaned over to look at my face in the dressing table mirror.
"And your legs," She continued, "They're the same shape as mine." She ran her hands across my leg and said, "And not a sign of any hair." She went over to her wardrobe and took out a really short beige Mini skirt, "Here, try this on," She said, "Show off those gorgeous legs." I picked it up and held it up in front of me. It was made of a stiff fabric like combat trousers, and was the shortest skirt I had ever seen, "Wow! It's really short, are you sure it's ok?" I said, as I slipped off my shorts.
"Sure." She said. Suddenly all my fears and doubts faded away, Kirsty let me choose a nice pair of her knickers to wear with it, and a pretty blue top.
Then we heard Miss Granger call us from downstairs, and I quickly got dressed, leaving the room cluttered with discarded clothes.
During the course of the weekend, Kirsty and I became really good friends.
We just seemed to hit it off straight away. We would sit in her room after we'd done our chores and listen to music, chat and play games. I lived for the weekends. My parents didn't seem to mind me going off all day every day, but that had always been the case. During the week at school, Miss Granger never mentioned my other life, nor did she treat me any differently.
On the next weekend the clothes arrived that Miss Granger had ordered for me from the catalogue. Kirsty and I had great fun sorting through it all. It was nice having my own clothes to wear. They were put away neatly in the spare room, which had more or less become my bedroom. Kirsty also had some new clothes, and we spent the whole morning trying on our new things. My favourite outfit was a tiny pair of pink satin panties with lace edges and ribbons that tied the sides, a very short denim mini skirt, a lavender long sleeved top and sparkly high- heeled sandals.
"Wow!" Said Kirsty as I walked into her room, "You look great!"
"Thanks." I replied. I was on cloud nine, and I suddenly realized that I felt the happiest I'de ever felt. As I sat on Kirsty's bed, I looked jealously over at her as she was putting on her makeup, I really wanted to wear some but I was too shy to ask. Kirsty caught site of me staring at her as she was putting on her lipstick, and I turned away embarrassed.
"What is it Sam?" She said inquisitively.
"Nothing." I replied shyly. Kirsty smiled at me and squinted her eyes trying to read my thoughts.
"Why have you gone red? What's up?" I sat there unable to reply.
"Come on Sam," She said.
"You're my sister, you can tell me anything." She took hold of my hand and gave me a reassuring smile. I felt my face glowing redder as I said, "Can I wear some of your makeup later, after we've done our chores?" Kirsty's face lit up with a huge smile, "Of course!!" She replied excitedly, Kirsty noticed the look of relief on my face and threw her arms around me and hugged me, "We'll come back up here and I'll do your makeup for you, and then I'll teach you how to put it on yourself, I'll even do your hair and nails if you like!!" After we had done all our chores, Kirsty took me upstairs to her bedroom, there we spent the entire afternoon trying on different makeup styles, she sat me in front of her dressing table and plied me with lipsticks and eye shadows, she put mascara and eye liner on me and even curled my eye lashes.
I had no idea that there was so much choice, and so many ways to look pretty.
"I think this colour suits you best." She said as she reached for a bright pink lipstick. She untwisted it and handed it to me and showed me how to put it on. I leaned close to the mirror and pursed my lips like I'd been shown and gently touched the lipstick to my lips and applied a liberal amount to them. I looked at my face and it was almost unrecognisable. I had long black curly eyelashes, smoky black eyes and soft glossy pink lips. Kirsty looked at me and gasped, "Wow!" She said, "You look gorgeous!" I felt myself blushing, "Come on" She said excitedly, "Let's go and show Mum." She took my hand and literally dragged me down the stairs and into the living room.
When Miss Granger saw me she was amazed and told me that I looked really pretty. They both made a real fuss of me, telling me how pretty I looked and how they liked having another girl in the house, I felt on top of the world, I'd never had this much love and attention before and it made me feel really special.
My relationship with Kirsty was growing everyday, we had become really close, but something happened that next Saturday that took it to another level. When I arrived at the house Miss Granger told me to get dressed into my girls clothes and come straight down stairs and do some housework.
"Where's Kirsty?" I asked.
"She's in her room." Replied Miss Granger, "You can go up and see her when you've finished." This seemed rather odd because Kirsty always did the housework with me but I didn't say anything. After I had finished I went up to see her, she was lying on her bed reading a magazine, I could see that she'd been crying, she had black streaks on her face where her mascara had run. She told me that she had had a spanking before I had turned up that morning.
"Did it hurt?" I asked, placing my hand on her shoulder.
"Yeah, but I'm ok now thanks." She replied. I sat there in silence for a while, and then she said, "Has Mum spanked you yet?" I told her that I had and that it had been my first time, "It's a strange thing to do," I said, "But I don't mind, I'm ok with it."
"You're really brave." She said, her big pretty eyes looking up at me. She looked really cute as she sat there forlornly on her bed, thin black streaks on her cheeks. Without really thinking about it I leant forward and planted a kiss on her lips. She looked at me for a second and then kissed me back.
We gently rolled over on the bed our lips locked together, our arms around each other. Kirsty's soft tongue gently slipped into my mouth as we lay on the bed together, I felt my cock stiffen and rise up, pushing it's way out of the tiny satin panties I was wearing, (which wasn't difficult considering how skimpy they were). Without a doubt, being dressed as a girl certainly made me feel sexier than I'd ever felt before. To anybody else, we must have looked like two lesbians as we rolled around on the bed.
We continued kissing for quite a while, I felt incredibly horny and really wanted to go further, but the thought of Miss Granger coming in and seeing us put me off a bit. We lay there together on the bed and smiled at each other, Kirsty's mouth was smeared with little pink sparkles from the lipstick I was wearing. Despite the fact that she had responded to my kiss my mind was in a spin, it was a very strange situation. I really fancied her but did she feel the same? Did she fancy me as a girl or a boy? And if she did like me as a girl, did this mean that she only liked girls? All these things were whirling around inside my head. Kirsty, noticing that I was deep in thought said, "Are you ok Sweetie?"
"Yeah I'm fine," I replied, as I ran my fingers through her hair.
"I'm the happiest I've ever felt, but I'm also a little confused."
"About this situation." Kirsty looked at me blankly.
"I mean, I really fancy you, and I hope you feel the same, but. well." I began to stutter, unable to get the words out. Kirsty placed her hand on my knee.
"You want to know if I like you as a boy or as a girl right?" She said, her whole face smiling.
"Yeah." I said with a big sigh of relief.
"Listen silly!" she said, grinning at me like a Cheshire cat.
"I'm cool with it, I really like you. You have a great personality. Most boy's are too complicated, I don't care if you're in touch with your feminine side, I don't know, maybe there's a bit of lesbian in me, but I really fancy you dressed as a girl."
"Really?" I said, my heart beating wildly in my chest.
"Are you kidding? She said.
"When I did your makeup for you last weekend, and you were wearing that tiny miniskirt, and this pink sparkly lipstick, you looked gorgeous! I wanted to kiss you there and then." Right then a huge wave of relief and happiness washed over me. I went over to the dressing table, took the lipstick and, looking at Kirsty, slowly and deliberately applied a fresh coat to my lips before sitting back on the bed.
"Well what are you waiting for?" I said cheekily. Kirsty smiled wickedly, and pushed me down onto the bed, climbed on top of me and started kissing me with a passion. I threw my arms around her waist as her soft warm tongue slipped into my mouth. I felt my cock stiffen again, straining against the satin of my knickers. She moaned gently as she pushed her tongue deeper into my mouth, swirling it around like a sweet tasting eel. I gave myself up to her, letting her take control of me. I began to softly moan with pleasure as she slowly slid her hand up my leg, her lips and tongue kissing me with a hunger. Her hand slipped further up my leg and under my mini skirt to my panties, I gasped as she began to caress my cock through the satin. Then suddenly she pulled away.
"You're wearing your favourite panties aren't you?" She said, still with her hand up my skirt, and she gave my cock another squeeze. I nodded, unable to speak. She reached down, unfastened the button on my miniskirt and took it off me, leaving my pink satin panties in full view. Then she took my lipstick, twisted it open and coated her lips with it, making them pink and sparkly. She then reached down and took hold of the ribbon ties of my panties and slowly pulled them undone. I looked down to see her gently take my throbbing cock in her hand and slide her mouth over it.
Those next few months were the best weeks of my life. Up until then I hadn't had many girlfriends, and I certainly wasn't that sexually aware. Kirsty and I were inseparable. It didn't take long for Miss Granger to work out that we were together, and she was really cool about it, even giving us some space now and again. At first I only wore girls clothes in the house, if we went out anywhere I would wear jeans but would always wear a pretty pair of knickers underneath them. Kirsty would be forever slipping her hand down my jeans to find out which ones I was wearing. One time, we went to the cinema and I had on my favourite satin ones with the pink ribbon ties, which were quite long and would tickle against my legs when I walked. Kirsty slipped her hand down my jeans in the queue and pulled one of them undone, giggling loudly. As soon as the lights went down, she unbuttoned my jeans and tied it up again but insisted that I leave my jeans open so she could touch my knickers while we watched the film. We both loved the feel of satin against our skin, so smooth and sexy. Kirsty didn't mind me wearing boy's clothes when we went out, but gradually as the weeks went by I got more and more brave, and with Kirsty's encouragement started to go out as a girl.
I remember the first time I left the house as a girl, I felt incredibly nervous but also really excited like I was doing something naughty. I wasn't brave enough to wear a skirt so I wore a pair of white combat trousers that were pretty much see-through, with a pretty white g-string that you could clearly see underneath if you looked closely. Kirsty gave me a short crop top to wear that came down just above my navel, and I wore just a little make-up, some eye shadow and a bit of lip-gloss. Kirsty took my hand and we left the house and made our way to the bus stop. I remember looking around nervously in case I bumped into anyone I knew, but as the afternoon went on that didn't happen and I started to relax. We had a great time around the mall, laughing, shopping and generally having fun. Kirsty's wicked streak and zest for life soon became too much for her control and she whisked me off into a department store and headed for the changing rooms, where she managed to convince me to swap clothes with her. Excitedly I put on her short skirt and applied some more make-up before leaving the store looking nervous and feeling that all eyes were upon me. As the weeks went by I became more and more comfortable going out dressed as a girl, we would have great fun together. Sometimes we would go shopping for clothes and end up snogging in the changing rooms. Kirsty was a tease, she would grab me and start kissing me, which would give me a huge hard-on, and then it would be impossible for me to leave the changing room because of it showing under my miniskirt. We'd eventually come out with smudged make-up and see a long queue of disgruntled women waiting to try things on.
A few weeks into July, Miss Granger invited me along on holiday with her and Kirsty. My excitement at spending a couple of weeks away with them reached fever pitch a few days before we left. I just couldn't wait. My parents said yes as usual, they never did care what I got up to which was fine by me. We were due to leave for The Canary Islands on the Monday, but I was allowed to come round to stay on the Friday which happened to be my birthday. All that week, Kirsty had been telling me that she couldn't wait to see me in my birthday present she had got for me, which gave me a tingle of expectation. When the evening came I was led into the living room and presented with two cards and a neatly wrapped box. The cards said 'HAPPY BIRTHDAY SAMANTHA' on them. Kirsty was excited and kept telling me to open the box first. When I did I had the surprise of my life, inside was a selection of white lingerie, including a white suspender belt and stockings, just like the ones I had seen in the catalogue all those weeks ago. I just had time to kiss Miss Granger on the cheek before Kirsty had grabbed me and taken me upstairs to dress me up. Firstly, before I had a chance to try anything on, she ran me a bath and insisted that I get in and soak for a while. She ushered me into the bathroom and told me to stay there until she called me. I sank under the bubbles letting the warmth envelope me, the sweet scented water lapping at my neck making me feel relaxed and drowsy. A little while later Kirsty came in with a towel and a pair of tiny white silk panties and told me to come to her room when I was ready. I quickly dried myself off, slipped the panties on and tentatively entered her room. My eyes nearly popped out of my head when I saw what she was wearing. She had on a school shirt and tie, which was unbuttoned down to her ample cleavage, a very short grey school skirt, which was so short I could see she was wearing white stockings and suspenders. I stood there for a moment, my jaw felt like it had hit the floor. Kirsty came over, took my hand and led me over to the bed which had all my birthday lingerie laid out on it. She sat me down and told me to sit still while she did my makeup. My cock began to stir with anticipation as she carefully began to put makeup on me, eye shadow and eyeliner, lots of mascara, and my favourite pink shimmery lipstick. That done she picked up the white suspender belt and hooked it in place around my waist, then she took the white stockings and slowly and carefully rolled them up my legs, stretching them all the way up to my thighs before clipping them to the suspenders. The sheer nylon hugged my legs like a second skin.
Then she went to her wardrobe and got out a school shirt and tie, and a short grey school skirt just like hers and put them on me. When she had finished dressing me, she stood me up in front of the mirror. Kirsty cheekily lifted the hem of my skirt revealing my stocking tops and suspenders.
"Do you like your presents Samantha?" She cooed as she teasingly adjusted my stockings by giving them a gentle pull.
"Very much." I replied. My body was trembling and my cock felt like it would burst with the tension. Kirsty pulled me closer and very slowly inched her lips towards mine, her pink glossy lipstick shining in the light. She kissed me so gently that I hardly felt it.
"You look gorgeous!" She whispered as she kissed me again.
"And Mum has gone out tonight and won't be back for hours!" Then she took my hand, led me out of her room and into Miss Granger's bedroom and stood me by the bed.
Then she went over, closed the door and walked back towards me with hunger in her eyes.
"Your legs look so sexy in stockings," She continued. She put her arms around me, her face inches from mine. I went to kiss her but she pulled away teasingly, kissing my ear. She ran her fingers over my stocking tops, "Tell me how they feel on you." She whispered. I stood there, my whole body aching with lust, unable to speak.
"Tell me what it feels like to be wearing pretty stockings on your legs." She said, as she kissed my neck and slipped her hands up my skirt. My heart was pounding so hard I could feel it shake my whole body. Kirsty continued kissing my neck and whispered, "You like being dressed as a girl don't you? You feel sexy wearing these pretty silky knickers don't you Samantha?" I couldn't answer, I felt my knees almost give way as she slipped her fingers under my panties.
"Your so pretty," She continued.
"I want you so much!" She kissed me full on the lips. I reached under her skirt and squeezed her bottom as she slipped her tongue into my mouth. We stood there for a moment, our hands all over each other, kissing feverishly. Kirsty reached round and unzipped my mini skirt letting it fall to the floor. Then she began to kiss me with a passion I'd never experienced before, she was insatiable, slipping her tongue in and out of my mouth, moaning and sighing with lust, her hands caressing my bottom and legs as she continued her seduction. Within minutes her own skirt was off and she was pushing me down onto the huge bed, we rolled around on it, our bodies and lips locked together.
It all seemed like a dream, the sensations I was feeling were so erotic.
Kirsty laid me down on the bed, pulled my knickers down to the tops of my stockings, then she climbed up onto the bed and squatted over me, gently lowering herself onto me in a sitting position, my cock slowly slipping deep inside her. She then produced a lipstick from her top pocket and told me to paint my lips while she fucked me. With shaking hands I untwisted it and pressed it to my lips and gave them a coat, Kirsty then began to gently fuck my throbbing cock.
"Don't stop." She said, "Keep putting it on until I say you can stop. And do it slowly." She added, her eyes bearing down on me. I coated my lips once more as she slowly continued to thrust up and down on top of me. I was getting seriously turned on, without thinking I dropped the lipstick on the bed and slipped my hands around her bottom. Kirsty stopped, picked up the lipstick and handed it back to me, "Samantha?" She said.
"If you stop, I stop!" I moaned with frustration, took the lipstick and placed it to my lips once more.
The bed started to squeak as she slowly and rhythmically fucked me, her breasts swaying up and down, her pretty face looking down at me. My frustration at not being aloud to touch her was intense, Kirsty liked to be in control, she ordered me not to cum, and to continue painting my lips.
"God you look gorgeous!" She said, as I added yet another layer of shiny pink lipstick.
"I might have to kiss all that off in a minute." She said teasingly, "And your legs look dead sexy in white stockings, so smooth and shiny, I'll have to keep you in them all the time from now on, you can wear them under your jeans when we go out tomorrow." Then suddenly, sensing that I was about to cum, she pulled off of me, pushed me down onto the bed again and planted her lips against mine. She gave a little gasp as I pushed my tongue into her mouth and at the same time slipped my fingers into her wet pussy. We kissed long and hard while I frigged her, my fingers quickly becoming wet with her juices. Then she pulled away from me and began to kiss my neck, then my chest, and then down to my cock. She took it in her mouth, slowly sliding her lips over the tip and down the shaft, masturbating me with her hand while sucking and licking with her mouth, and bringing me to an explosive orgasm. Kirsty crawled towards me on all fours like a cat, until her face was just inches from mine, and stuck out her tongue towards my mouth for me to suck. Hot cum was dripping from it as I eagerly slipped my mouth over it sucking at it like a lollypop. She pushed it deep into my mouth and threw her arms around me as we rolled onto the bed.
It must have been close to midnight when we eventually woke up. We quietly returned to Kirsty's room before Miss Granger came back, and snuggled up together in Kirsty's bed.
The next day was spent buying clothes for the holiday. Miss Granger took us into town in her car. Kirsty had insisted that I wear stockings and suspenders again, and kept teasingly raising the hem of my mini skirt to look at them. I jokingly warned her that if she kept doing it I would take them off and never wear them again, which stopped her immediately. We spent ages looking at all the nice summery clothes in the stores and trying on a few items in the changing rooms. Then she spied a shop that seemed to specialise in bikinis and dragged me in for a closer look.
"Ooh, you'd look great in this!" She said, holding up a shiny pink bikini.
It was very skimpy, and sparkled in the lights of the shop.
"It matches your favourite lipstick." She said with a sly grin, and cheekily slipped her hand up my mini skirt.
"But how can I wear them without a skirt, I mean. people will see I'm not a girl." I replied, looking at them enviously.
"Oh but you can silly." She said smiling at me.
"Mum's villa has a private beach, we'll have it all to ourselves, so no one will see you except me." She gently kissed me on the lips and whispered, "And when I see you in them, you won't be wearing them for long anyway." When we got back to the house, we went up to Kirsty's room and spread all the clothes out on the bed to see what we had bought. Then we sat and chatted about the holiday, Kirsty told me all about the villa, and how wonderful it was going to be. Then suddenly the bedroom door opened and Miss Granger came in and sat next to me on the bed.
"You girls getting your clothes ready?" She said. looking at the mountain of clothes scattered around.
"Oh we can't wait Mum." Said Kirsty, literally bursting with excitement.
Then Miss Granger turned to me and said, "Now Samantha, I know you need to start packing but I was wondering, it's been quite a while since I spanked you last hasn't it?" My heart leapt up into my mouth at the sound of those words.
"Yes Miss." I said shakily, looking down at my feet.
"Mmm, well I think it's about time I spanked you again don't you think?" She said, placing a hand on my leg.
"Yes Miss." I replied. My head bowed in shame as Miss Granger held out her hand towards me.
"Come with me then young lady." She said. Then she took my hand in hers and led me down the stairs and into the study. Miss Granger placed a chair in the middle of the room and sat down on it, she then told me to go over and close the door and come back and stand by her chair. My legs were shaking as I slowly walked back to her, my high heels clicking loudly on the wooden floor. Then she told me to take off my top, I took it off feeling her eyes boring into me, then she reached around behind me and unzipped my skirt, letting it fall to the floor. I felt my face glow red with embarrassment as I stood there in just a frilly white suspender belt, white stockings and tiny white g-string.
"You look very pretty Samantha." She said, and gave my suspender belt a little pull. Then she turned me around to look at my bottom.
"And as you're wearing a g-string, I'll let you wear them while I spank you."
"Thank you Miss." I said. Miss Granger then turned me back round to face her, took my hands and gently pulled me over and across her lap. I felt the blood rush to my head as I wriggled around trying to get comfortable. Miss Granger ran her fingers up and down my stockings, telling me how nice they looked on me, and how silky smooth my legs were. The tension was mounting by the second. It was as if she was teasing me by not spanking me straight away, prolonging it, making me wait.
"These are pretty." She said. As she 'twanged' the sides of my g-string, "They show off your lovely bottom." She pulled my g-string up really tight, and then gave my bottom a good squeeze. I felt my cock start to stir and swell against her legs, as she continued to fiddle and adjust my underwear.
"Now remember," She continued.
"I'm not spanking you for being naughty, I'm just re-establishing my authority over you, ok?"
"Yes Miss." I replied, my heart pounding harder and harder. Then she placed a hand on my back and began to spank me.
The first slap was a shock, I hadn't reckoned on being spanked that hard.
Sharp stinging slaps rained down on my bottom, making me wriggle and squirm as I lay on her lap, the pain quickly intensifying as she continued to spank me. Her grip on me tightened as I began to writhe and kick my legs, the pain becoming too much to bare, tears ran down my face as I started to cry.
When it was all over, Miss Granger gently smoothed some cold cream all around my sore bottom.
"Sshh." She said softly, as I continued to cry.
"It's all over now, don't cry." Then she pulled me up and sat me on her lap. I threw my arms around her, buried my face in her neck and sobbed uncontrollably.
The holiday was probably one of the best times of my young life. It was the first time I'd been on a plane, I had to wear boys clothes on the day we left because of my passport, but Kirsty made sure I was wearing my favourite satin panties underneath my jeans. As soon as we arrived at the villa we got changed into our bikinis and went down to the little private beach. Kirsty took my hand and led me down the stone steps, which wound their way down to a small crescent shaped beach. I remember feeling a little self-conscious wearing my tiny pink bikini, but to my joy the little beach was completely deserted. It was very sandy, and had quite high cliffs on each side, and being that the only property around was our villa, there was no danger of anyone seeing us.
We spent our days playing on the beach, or in the swimming pool, there was a tennis court and a games room. It was so nice being able to remain a girl the whole time, without having to get dressed as a boy and go home. Some evenings we would all go out for a meal in the local town, and I got more and more comfortable going out dressed as a girl, and Miss Granger and kirsty liked it too. It really was the best two weeks of my life. I didn't even mind when one morning Miss Granger said that she wanted to spank me.
Kirsty had had a spanking the day before while we were playing tennis, miss Granger had interrupted our game and took kirsty up into the master bedroom, I could hear the slaps and cries from the poolside. I sat there and imagined kirsty sprawled across Miss Granger's lap, bikini bottoms round her ankles kicking her legs in pain, and I suddenly realized that I was becoming aroused, and also. jealous. Its sounds totally bizarre now, but I was jealous that kirsty was being spanked and not me. So the next day while we were lying on sun loungers by the pool, and Miss Granger came out of the house and told me it was time for my spanking, I actually couldn't wait. We walked hand in hand into the house and up to the master bedroom. Then she sat down on a chair and pulled me closer to her, reached forward and gingerly untied my bikini bottoms, letting them fall to the floor exposing my erect cock.
"Looks like you're starting to enjoy your spankings a bit too much Samantha." She said, giving my rock hard cock a little stroke.
"I'll have to make your spankings a little more uncomfortable won't I?"
"Yes Miss." I replied, looking down at the floor. Miss Granger then got up, leaving me standing by the chair completely naked, and walked over to a chest of drawers and began to rummage around in one of them. When she returned she had something in her hand but I couldn't make out what it was, she sat back on the chair and placed the item on the floor, then she took my hands and pulled me across her lap. I wriggled around trying to get comfortable and gripped the chair legs with my hands. I could feel my stiff cock squashed against her legs as I lay there exposed. Miss Granger then slipped her hand into a clear plastic disposable glove and began to smear some gel or cream around my bottom. Then she parted my bum cheeks wide and smeared it all around my hole. I gasped as she entered me with her finger, slipping it all the way up to her knuckle. I began to squirm and wriggle on her lap as she continued to twist her finger in and out, opening me up for what was to come.
"Now then Samantha," She said, her finger still inside me.
"I think I'm going to have to be a bit more firm with you from now on, you're obviously enjoying your spankings far too much," She reached down and picked up the item on the floor.
"You need to learn some humility, when we get home there are going to be some changes." I suddenly felt her fingers widening my hole as she inserted something into it, I moaned softly as she began to slowly push it in further and further.
"Kirsty's going to be spending alternate weekends with her father when we get back, which means that every other weekend you'll be with me." She continued. I parted my legs as wide as I could and arched my back as the devise was slowly inserted up inside me inch by inch.
"I can see I'm going to have to think of another way to exert my authority over you." She said, as she pushed it in as far as it would go.
It certainly felt strange, I'd never had anything pushed up inside me before, and it made me feel a lot more exposed and vulnerable, a lot more dominated and almost abused. But it did have the desired effect. The servant/master relationship had been re-affirmed, here I was lying across Miss Granger's lap, totally naked, about to be spanked, and with a sex aid pushed up inside my bottom for all to see. The spanking that followed was particularly hard, the stinging slaps must have been heard for miles, by the end of it I was quite sweaty and exhausted, having been writhing around on her lap and kicking out in pain. Miss Granger kept me on her lap for quite a while afterwards, gently stroking my reddened cheeks and telling me I was a good girl and that she would look after me. After she had removed the devise from my bottom, she smoothed in some more cream around my hole, occasionally slipping her finger into me, giving me a tingle of excitement, before sitting me up on her lap for a cuddle and to wipe away my tears.
It was a shame to be home after such a wonderful week away. I slipped back into the usual routine of life, (although looking back on it now it was a very unusual routine. I don't think many people can say that they spent their late teens dressed as a girl). But little did I know that my weekly routine was about to change again.
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