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I was 16 years old.
I came home from school having just finished some exams.
Mother was waiting to for me to come home.
No smile upon her face this particular day – yet mom and I seemed to get on so well usually.
I have something to say to you – or rather something to ask you – why were two pairs of my lovely silk-nylon lace trimmed panties, one white satin floral pattern bra and a lovely full white soft satin slip in your wardrobe drawers young man or should I say young sissy-boy-girl. Well – I am waiting for your answer.
Red faced, I did not know where to hid my blushes.
I had been found out. I had been wearing her things for years. This time though I had kept items and not put them back in her drawers. How stupid of me.
Oh and by the way, you were seen wearing that bra by a neighbour, she told me yesterday she had seen a young girl at my bedroom window and wondered who she was as she looked remarkably like you with short hair too.
Ok mom, what can I say to make things better, I am sorry to have kept your slip, bra and panties.
Sorry just does not begin to make up for what you have been doing.
I knew someone had been in my drawers, always things not neat where I put them away, stockings out of packets I know I had not opened or worn as yet, slips not folded correctly, panties with some marks on them – yes miss – for if you wear these things you are not a proper he are you – marks that betrayed your enjoyment a little too much.
So what am I to do with you my dear?
What did you tell our neighbour mom?
Well she is coming round later to meet your cousin.
You told her it was a cousin of mine.
So who will she see and meet mom? Who have you got coming to play that role?
Nobody is coming round, you wore the bra, so she will be meeting you of course.
You have about an hour before she is due round here.
I have put out some things on your bed, you had better go get ready.
My face probably was crimson as I went upstairs to my room.
On my bed was the white satin floral bra, a garter belt, stockings panties – all matching satin – and looked new and unworn too. I shouted to mom – what else to go with these things. Nothing just make-up heels and brush your hair and style it girly. Ok yes you can borrow my white satin wrap. Hurry she’ll be here soon.
I had showered perfumed with talc in the bathroom cabinet and brushed my slightly longer now hair into something more like a girl style.
The matching bra and panty set with the sheer stockings and garter belt were soon on my slim boy frame. Some cute kitten heels were near mom’s bed with her wrap so on they both went. Some red lipstick and light blusher to my cheeks, eyebrows pencilled in and some mascara. I looked in the mirror and smiled.
Mom shouted upstairs, Samantha dear Mrs Jones is here to meet you.
I gulped. I had never thought of a girl’s name when dressing.
Coming mom I shouted back but trying to be girl-like with the tone.
My Mrs Jones did say.
A lot prettier close up and then from the street I must say.
There was me thinking it was Sam your son in that bra. Obviously I was mistaken. This young lady is far prettier than your Sam for sure. How long is she staying with you? I am sure my boys would enjoy taking her out partying and such.
Mom looked at me smiled and said. Oh she is here for a long time she will be studying at Sam’s school after the summer holidays. Sam is going to stay with her mom and it is a sort of family exchange. They study his subjects better and Samantha is keen to study here are you not dear. I blushed – what do you mean mom – I am your aunt dear you forget yourself. Mom is now looking after Sam but I am flattered you think of me as your mom so soon.
So Mrs Jones send the boys round anytime to meet her and see where they wish to take her. She is quite shy at first as you can see. Show her your sexy lingerie and figure dear girl. I stood and looked ‘mom’ in the eye concernedly. Go on don’t be shy we’re all ladies together, in fact Mrs Jones has the dress hop just round the corner and am sure would love you to work Saturdays for her wouldn’t you? Oh of course as she is so pretty and am sure all the young ladies will shop when they see her assisting and maybe modelling corsets, bras, slips and dresses for them to see how they look up close before trying for themselves.
The wrap dropped to the floor.
Mrs Jones walked round me, she patted my bottom and felt the garter straps and looked into my bra cups. Needs some more bust development I feel, how old 17 and not yet fully developed. We shall have to help her there. Here try these dear. She handed me some pink pills. They will work wonders. I sell them at the shop to all young girls who need help in the boob department. Hubby brings them back from overseas. Then she touched the front of my satin pants. It was a good job I tucked everything inside my body so nothing protruded and the satin panty-line was smooth and soft and welcoming. She fingered my boy pussy hole between my legs too through the satin pants. Tight there but with time it will open up am sure like the boobs we can develop there too.
Mom smiled – well son you said you wanted to be a girl. Looks like your wish will be coming true sooner than you thought. I always wanted you to be born as a girl too. We hugged. What did the future hold for me – we shall see soon. Tonight you will sleep in a baby-doll nightie and for every night from now on darling Samantha.
I slept well that night and yes my first night in a sweet pink frothy baby-doll nightie plus mom had put satin sheets on my bed. I was in heaven I felt just like a girl. Hot horny and sexy. My dreams were many and sexy. I was dating and being used as a girl by men of all shapes and sizes, my what a whore I was in those wet dreams.
Next morning mom said nothing over breakfast about what had happened the day before but as it was the weekend and she reminded me that I had promised to go to help out at Mrs Jones’s shop – “Shirley’s sexy slip shop” as she termed it now. I was soon to find out why later that morning. You had better go casual but smart Samantha, remember she is expecting a girl not a boy. Those loose jeans and a plain tee-shirt but don’t forget your bra panty garters stockings too and some flat heels, borrow those kitten heels you wore last evening when she came round. The shop is just round the corner so not many folk will see you walk there – it is Saturday and early yet – even your dad is still in bed – we would not want him to see his ‘son’ leaving as a – well – you know – hurry now.
I washed shaved what little hair I had on my face and body. Talc powdered onto me again and then I slipped into the items mom had told me to wear. Applied some lippy and eye shadow for daytime and slipped on the shoes. As I quietly crept back downstairs mom greeted me – here darling and gave me a small purse-bag – and sprayed some flowery scent on my wrists and neck before placing the small ampule into my new bag. Also she clipped two hoop earrings onto my ears and gave me a ring for each hand and a bracelet. We must look like a girl when we go out darling. I smiled and kissed her cheek. She smiled back. Enjoy your first day out as a girl Samantha, don’t do anything your mom would not do.
I walked out the front gate and started along the street to Mrs Jones’ shop. It was about half a mile to walk. The sun was shining and I was in my tee-shirt and jeans but conscious anyone could maybe see my satin bra cups and the traps too as I walked and of course my kitten heeled shoes clicking along the pavement. Could be heard too.
Then I saw him, one of my mates güvenilir bahis form school.
Had he seen me, would he come over and say something – but nothing happened but then I heard a wow sexy you look hot to me. I tried to ignore him. You look like a lad I know, sorry darling, not meaning to upset you but I was sort of thinking of him when I saw you but now I can see you are an attractive young lady. I smiled but still tried to keep walking. What’s your rush love? I tried to say as softly as possible – I have work, a new job, first day there today and can’t be late. Where is that – oh a dress shop up the road, bye. Let me walk you there he said. Ok. What could I do but accept his offer so as not to cause upset and get him riled some too.
I tried to walk quickly but felt his arm on mine holding me back, no rush darling the shop will still be there and am sure Mrs Jones will forgive you being late. You know the shop I quizzed how come? There is only one ladies shop this way silly and mom uses her shop often. If I may say so there are some sexy things at her shop and I hope you are ready for that and the ladies who shop there. I blush when I think of my own mom shopping there.
We reached the shop and I looked at the window display and knew what my mate meant. Looking down were mannequins dressed very scantily and very sexily in bras, panties, stockings and what dresses where showing were tight satin, leather or pvc.
Mrs Jones came to the door as if by magic – oh Samantha dear you’re early and who is this charming boy with you, hello dear, not sure you should be looking at my shop too deeply it may ruin your eyes dear, run along and go play football or such with your other school chums. I have to get this young lady ready for her day. Bye I said and off the lad went.
The shop was well lit and spacious with even more items stacked on rails and shelves. Mostly ladies wear and mostly sexy. I didn’t realise, I said. Of course not dear why would you, just having arrived here from out of town.
Mrs Jones – Elaine – was dressed in a sleeveless tight figure hugging and outlining satin dress in jet black with a white pussy bow blouse under. I noted a glimpse of seams stocking tops and 6inch pumps plus a white lace edged slip peeping from her dress hemline when she reached up to find some forms for me to fill out. Just merely name, address, next of kin sort of thing for our personnel records and if you are still a virgin, your measurements at bust waist hips and such. Intimate but needed for your uniform and other fittings dear. If you fit in we can make good use of a sweet sexy young lady in this emporium. We have a varied clientele from near and far and odd times you may find a gentleman or tow browsing needing help to find something for a special lady in their lives if you know what I mean dear. Why did she wink? Did she know the truth about me after all?
Here are the other girls juts arriving, of course they’ll all be new friends to and for you to get to know. Jenny, Sarah and Rose – Jenny is boss when I am not here and Sarah and Rose will show you your locker and uniform and where to make teas and coffees for us all during the day –as the new girl that will be your job – milk and no sugar for me and don’t you forget that young madam or else you’ll find some of these extra toys on display will meet your sweet pretty fanny ass dearie. I saw what she was talking about – on a wall were whips, chains, cuffs, gags, floggers, paddles, canes and such that only what I heard about were to be found in dungeon paly rooms and that was in a magazine of dad’s I found one day.
Jenny looked beautiful – make-up and hair and sweet smile, Sarah and Rose looked a year or two older than me in fact I recognised them form 6th form having left this last summer. I recalled they wore thigh high boots a few times and the head went ape about that, us boys – whoops – yes us boys – had enjoyed the show whilst it lasted. The two girls welcomed me with a hug and kiss and showed me where to change into a skimpy dress thigh length and showing stocking tops when I out it on, the girls helped zip me into the satin dress but both commented that my boobs needed feeding and giggled. They smiled and said worry not we get pills here to help. Here try a couple now before work, the two pills looked like the pink ones Elaine had mentioned to mom yesterday. I took two ad swallowed them down with a glass of water, at least I T thought it was water as the two girls gave it to me, tasted sweet to me but hey on with the day I thought. I felt slightly weird and my dress tightened on my chest – see they said the drink and the pills of extra strength are working on you already, two nice boobs on show now and my bra cups felt tight as did the dress, I looked down and saw cleavage at the neckline of the dress. I almost feinted. I looked lovely.
Elaine noticed when I went back into the shop as did Ms Jenny – well quite the young lady now are we not dear Samantha. They playfully patted my satin covered rump. Well girls time to open the shop. Sammy dear make the first drinks of the day and then you can learn the ropes– well maybe quite literally.
Having made the drinks I went back into the shop and noticed the first customers of the day browsing the rails including one or two gentlemen. They seemed to touch a lot of the silky satin items with their hands, pulling the items fully out and running fingers all over the soft satin. Very interesting I thought to myself. I would be doing just the same giggle. I looked at Elaine and Jenny, they both seemed busy with ladies and the other two girls were nowhere to be seen. I went over to one of the browsing men and asked if I could help him in anyway? He looked at me surprised. Oh just looking for my wife. Fancied something a little sexy as a gift to cheer her up and me too. Well that is soft satin and a very sexy little maid’s dress.
What size is she, oh about your size he said without thinking.
Could you show me how it looks by modelling it for me dear?
I tried to catch Elaine’s eye but she was still busy. Well, I suppose I could, but I am new here perhaps one of the other girls could help, but there is nobody else nearby is there dear. You’re right sir, ok, come with me. Then Elaine did look up and having heard the conversation winked and said – good girl – could be your first sale of the day – be good for him and you may get a tip too. What did she mean ‘be good for him’? We walked to the back of the shop where there was a room for trying on and parading in front of walls of mirrors, erotically decorated with satin wall d****s and pictures of various sexy ladies and well men too. On with the reason for us being there now, well dearie don’t keep me waiting, I am anxious to see what that sweet satin maid dress looks like on you. I went behind a curtain into a spacious cell, well there were chains on the wall and weird brick décor and well it looked prison like to me.
I took off my uniform dress and slipped into the maid’s dress I turned and he was facing me – lovely – let me feel it on you – next thing his hands were stroking my body through the skimpy dress. He tugged the elasticated neckline down to show more of my shoulders and my ‘new’ tits which to me seemed bigger than earlier. He stroked them hardening my new nipples. Yes lovely. Now here – he suddenly dropped his trousers and satin panties appeared bugling – on your knees dear and take this – his big cock emerged and he thrust it towards my face – I‘ll sort the fee with Elaine later – just massage my cock with your dress and mmm if you like canlı casino to you can suck me too. What the hell – next thing Elaine popped her head round the door – everything ok Bert?
Yes dear, your new girl looks lovely, oh Samantha dear just do what he says, I’ll settle up with you later and explain too.
My first cock experience and me on my knees. I just did what I’d seen in magazines and pictures. His cock responded to my fingers and then my mouth – I gagged at first because as I opened my mouth he thrust it right in – then slowly fucked my mouth. He did not take long before he said where would like you my deposit – again confused I just opened my mouth he withdrew and spurted his cream over my face and the dress got some drips too. I looked up – what about the dress – oh worry not – welcome to the shop – I am Elaine’s partner. I run the sexier seedier side of the business. You did well for a first if I was your first. Well yes sir but before you think – worry not we also know your little secret too – that is safe with us both and the other girls – we are one big family and special girls are like gold dust in our business – you will get special treatment – top dollar for sex work and more. This is just the beginning darling girl. Elaine returned – she know darling – and she knows we know about her too. What oh well done Samantha – welcome – your mom will be so pleased too – you see she and I are lesbian lovers and so she told me that she thought you may be a dresser and that maybe we could help you find your true self by having you work here.
I did not know what to say. I just smiled and handed the ruined maid’s dress to Elaine and asked what next for the new girl. He advised I could look around the rear of the shop and see what else there was that was available for sexy fun times including a small 10 seater cinema room where some men and ladies too from time to time liked to view porn and have sex. So off I went back in my simple full but short skirted satin uniform dress – bit like a cinema usher – as you found selling ice cream or such from her tray hung around her slim sexy neck and her long sexy legs tempted one and all to buy from her.
Imagine my surprise when opening the cinema room curtain to find a few people in there and obviously looking for or already having fun. Elaine and hubby and not warned me there could be or even would be people playing already. Unsure of what to do I closed the curtain and started to look around the outer room where ropes, cuffs, gags, whips and chains were displayed alongside spanking benches crosses and other pieces that seemed more suited to medieval torture chamber than this high street shop. I heard the sound of high heels on the stone flags which also seemed more akin to dungeon than shop. Turning again I saw a statuesque figure in thigh high laced up books, under bust corset showing magnificent breasts a collar and eye mask all in black, whip in hand and heading towards me.
A voice suddenly called in my direction. A new girl, how lovely, come here girl. Me I asked, yes you, kneel before your goddess. What, I am new yes, I am just looking around as Elaine told me to do. Well you have wandered into my domain young lady and must now submit to the whip and be chained up a while. Sorry but not sure Elaine would – quiet young lady, Mistress Elaine knows as she sent you here, she knew I would be here and also knows what dark pleasures I would enjoy with you as our latest recruit dear girl, so on your knees now. I hesitated. Submit girl – on your knees louder this time came the command and her face even with the eye mask showed this madam meant business with her whip raised high. I fell to my knees and looked up. Good girl. You learn quickly. You will do well. Kiss my whip sissy. I did so. Now kiss my boots from toe to thigh. I did so. Respect due. She was awesome in looks and stature. A goddess if ever I saw one – in truth she was my first. The whip cracked through the air. I stopped kissing the boots. Why have you stopped girl – carry on. I did so until I reached her open skirted thigh stocking tops, the jet black pvc skirt was open to the waist and formed a sheath around her thighs above the boot line. The smooth material shone in the lamp light of this dungeon setting.
Time for tea girl, go fetch me one and hurry, milk no sugar. On the way back to the kitchenette area I saw Elaine, looking for me I asked, no girl there should be a tall lady in black with maybe a whip who plays as a dungeon mistress. Yes I am fetching her some tea – you have met, good. You may serve tea for two back in the dungeon.
I made the tea, found a tray and delivered it to the dungeon. The two ladies were stood waiting for me – good girl – thank you – sit – I sat – they remained standing, talking and pointing to items in the room. They suddenly left the room and headed to the cinema returning with a guy on a leash. I stood up – they tied him to a cross. He was in pink satin panties, stockings and high heels but no make-up or wig. They put a ball gag in his mouth. Elaine stood watching Madam taking the sissy through his-her paces with whips, paddles and finally nipple clamps. The gag kept her subject silent but the body movements showed the pleasure and pain.
Elaine looked at – your first morning has shown you what we’re about dear girl. I do hope you are finding life here interesting and maybe rewarding too? I nodded yes but could not speak as I was so in awe of my new surroundings and all the hot horny sexy action going on and potentially going to happen with films, books, clothes and more. The dungeon room had me in its spell. I so wanted to try out the ropes, cuffs, gags and more but how to do so? That could wait for another day. I took the empty tea cups back to the kitchen area and washed them and stacked them for the next tea break.
Soon my first day was over I had met a few more customers sold a few items of sexy lingerie and felt at home. As the shop was closing at 6pm Elaine said the playrooms were hired out for evenings and the cinema too and if I ever wanted to earn a little extra I was welcome to sign up for being used in the late evenings – of course dear this would be after your normal shift here so think carefully – we are open 7 days a week until 2am so it could be a long day for you but also very rewarding. You see after 6pm your time is yours and your rate of pay you decide for what you’re offering I mean doing with the clientele. We shall discuss this in more details if you decide you like us and the shop. Talk it through with mom, she knows me and how we operate. Oh before you go, here take this with you – Elaine gave me a holdall – feels heavy I said – it has in it some clothing – call it uniform – various outfits – lingerie, blouses, skirts, dresses – you decide each shift what you want to wear. The shoes and heels you must get from stock and pay for them dear. Thank you and I gave her a hug and kiss and left for home. The walk back was in the twilight and a few guys were lingering by the shop and they whistled as I past – you on tonight darling they asked – stunned I walked on – hope to see you later gal you look hot. I was conscious my heels were high, my skirt for home maybe a little too short and were my stockings on show. I forgot that I had tried on so many items at work that I didn’t think to change back for home. The guy I’d seen earlier in the day was waiting near my house why how did he know what time I’d be back – Hiya he said as I got close – wow you look hot babe – where did you get those clothes – oh from work – my new job – sexy – I kaçak casino asked your mom if I could wait she said you’d be home by 7pm and here you are, well worth the wait. Fancy a drink later – well I am needing a freshen up and something to eat – no problem pick you up at 10 maybe grab last orders and I know a sexy club we could sneak into after closing too. Oh my god a date with a guy what was I doing when I said ok see you later.
So dear how did your first day go? Did Elaine think you would be an asset or not to her little enterprise – I have known her since moving here and she is so sexy don’t you think – I must confess she and I have quite a sexy time together darling – she can do things to me your father never would or could – things only another woman would know about – maybe one day darling you will too.
All went well mom, but why did you tell John what time I would be home? Well dear it is time as you are coming out as a girl to go on date, no time like the present dear. Go freshen up I’ll make some food for you. I have laid out a nice full skirted pink floral dress for you first date – matching pink satin lingerie and high gloss tan stockings and some cute sandal style pumps. Go and have a lovely relaxing bath and when you’re all pretty and sexy I am you’ll have a lovely time.
The bath did me good. Soaking in sweet foam and dreaming of my new life, what could be, what may be and what had already happened so fast to change my whole outlook and life was looking good. I lay there reflecting on how my life was changing so fast. I expected mom to blow her top once she found out about my wanting to dress and present as a female but no she was encouraging and supporting her new found daughter.
I reached for the new fluffy towel and dried off and looking in the mirror for the first time decided the refection was me as female. My thoughts were now turning to my date. My first date going out as a girl. I slipped into my new pink satin bra, panties and suspender belt and attached each nylon stockings to the clips and smoothed them down my long slim sexy hairless legs. The bath foam containing hair removing cream too, they had just melted off my body from neck to toes. The stockings felt sexy and were high gloss shine. Make – up time – mom what about my you know what I shouted down not thinking dad might be in and here, was not sure what mom may have said to him about their new found don-daughter. She came upstairs and looked at my satin panties. Put your wrap on and come and have some tea then we’ll sort that out after you have eaten.
Dad was at the table when I got down, he looked up and took two looks and smiled, see what you mean love, we now have a daughter wow she looks sexy, hands off dad before you think about it, any sex in this house she has will be with me showing her how a lady really likes to have sex so she’ll know good sexy lover when she finds him. You are just a horny wham bam man. So it seems dad was ok about me being a girl and no longer a boy.
After eating mom led me back upstairs to deal with my non-girl like problem.
I felt kind of strange as mom took hold of my girl-boy-clit as I now called it. Here let me milk you darling, you can drink it all down, good for your sissy complexion then we’ll put it safely away – what did she mean but before I could think anything further she had me rock hard aroused and pumping cum into a glass she had in her free hand. I gulped it sown like a whore and stood before her all limp and she tucked it between my legs and up an opening I had not realised was even there. She then applied some flesh tone pads and minute tape. There dear. The sex-cream you have drunk will also stop you needing to pee again until you are released. Magic isn’t it but wonderful for you I am sure. I felt good.
Make up was applied, soft tone foundation, eyeliner, eye shadow just enough to reflect my green eyes and lips shone as I applied hot pink lippy and rouged my cheeks, dab of powder and hair brushed out femme. Sandals, petticoat and dress. Wow, the image worked. A sweet sissy girl all pretty in her frocks and curls. The dress was prom style – pink floral and a soft satin sheen – knee length – quite demure and elegant for her first date.
I walked downstairs and mom handed me a furry pink short jacket, felt soft and warm too for the late summer’s evening being out. Both mom and dad approved of my final presentation look. Mom gave me a hug. Welcome to the family Sammy darling. There was a knock at the door, well are you going out or staying in young lady. I tottered to the door in my strappy sandals and greeted my date. John just looked and whistled, hey babe you look a million dollars, wait ‘til my mates see you. What do you mean I thought it was going to be just me and you for the evening? Well they’ll be in the pub babe for sure.
We walked to the pub round the corner and sure enough ten of my old school friends with their girlfriends were there. Oh hell, what a baptism. Would anyone recognise the true me beneath this femme me I wondered.
Hey gang this is Sammy, she’s our old mate Ken’s cousin. Staying whilst Ken is away at his aunts. A kind of sex-change not realising what he had said he laughed, you know Ken a boy,
Sammy being a girl and they’ve exchanged, oh forget let’s have a drink.
He took me to the bar and sat me on a high stool where my full skirted petticoat dress could swish around my long legs for all to enjoy the silky satin material shining in the lights as I moved and crossed and uncrossed my legs. I am sure a few guys deliberately touched it as they walked past to go to the toilets and there did seem a regular flow of them too back and forth, including several of our old school friends and their girls enjoyed touching the dress too. Well it was a lovely feminine dress for sure.
Samantha enjoyed their touching her and it also very much. It made her feel warm inside. Her nipples hardened in her sweet pink satin bra cups.
John was in heaven he had the hottest girl in the pub or so he thought and everyone was eyeing up his date too. He slipped his hand around my waist as he stood by my seat and caressed my body in satin and I was horny for sex. But John was a boy and I am a confused person at this moment in time, what do I want being femme – how far does a girl go on a first date?
John continued to enjoy our evening with a few beers and caressing my body through my sexy dress, feeling my tits as he thought and kissing me from time to time. He even got his tongue in my mouth but I wanted a man to fuck me. What was I thinking? My time at the shop and all I had seen had made me so hot sexy and horny. I put my hand on John’s thigh and slowly moved up to his own panty line and felt his bulge, yes he was hardening – now was that the beer or the other girls in the bar – several quite attractive sexy ones too – short skirts, high heels and their blouses bursting with lace-edged- satin bra cups and more – or was he attracted sexually to his date?
I was looking and learning as these various girls – some in girl only groups and others with dates – watching how they behaved. A few chaste kisses and yes a few hands wandering under the tables but this after all was just an everyday bar not a sex club.
What did I expect or want.
From the shop earlier I knew what guys wanted.
But I was still young and inexperienced learning about my own body and how it was now changing.
Even my mother’s attitude and dad’s to my dressing and presenting female.
Now on a date with a lad and wanting cock and how to get it.
I decided a trip to the toilets – I know mom said I would not need to pee but I needed to think.
As I left my seat at the bar – I told John I needed to powder my nose – as ladies say and do – I went into the corridor leading to the toilet area – I felt I was not alone………………..
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