The Emergence of Sarah Ch. 01

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Getting ready for a night that will change his/her life.
2k words
4.52
30.6k
13

Part 1 of the 2 part series

Updated 09/22/2022
Created 08/31/2012
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This is the first in a series. Although there is no sex in this chapter it sets the scene for what is to come.

Finally I must say a big thank you must go to g1dnshwrgr1 for editing assistance with this story.

Please feel free to leave any comments etc.

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I knew the routine inside out, but I was more nervous tonight than I could ever remember being before.

My parents had left 30 minutes earlier to go visit my Aunt for the weekend and my sister was abroad for a friend's wedding and was due back for another 4 days; which meant for the duration of the weekend, I had the house to myself.

I had only recently turned 18 and this was the first time I was left home alone overnight. I had been planning this weekend for a while, but it still didn't stop the nervous excitement I felt. Rather than the few short hours I grasped when I could, tonight I could be Sarah without the risk of family coming home unexpectedly.

The idea of the weekend had been my jacking-off fantasy ever since my parents announced they were going to visit my Aunt. At first they wanted me to go with them, but I knew my sister would also be away and it would give me the perfect opportunity to have some serious Sarah time. Ever since I started to cross-dress, it was an opportunity I had dreamt of and I wasn't about to pass it up for the sake of visiting my Aunty. Hence I convinced my parents my time would be better spent if I stayed at home and spent the weekend studying. To be honest, I can't believe how easily they accepted that idea, especially when all I could think of was the amount of fun I was planning.

I had read plenty of stories online about cross-dressers being home alone and knew I should give myself a bit of time before I started getting ready just in case my parents made an unexpected return for something they had forgotten. So here I was, 30 minutes after they left, eating a light meal as I figured the time it would take to eat and wash up would be more than ample.

After washing up, I jumped into the shower with a packet of disposable razors. I bought them on the pretence that I was sprouting facial hair and wanted to shave, in reality, the only things I needed to shave were my legs and my genitals as I didn't seem to be the hairy type. I quickly lathered up my legs and got down to the act of shaving. At first it wasn't too difficult but I have to admit I found my knees and ankles tricky to do and ended with a small cut on my ankle.

Ever since I found my Dad's porn magazine, I had always wanted a small landing strip above my boy clitty, but as my pubic hair was soft and downy, it seemed easier just to remove the whole lot. I finished with my armpits just in case and after what must have been a solid hour I stepped out of the shower with the only visible hair on my body being my hair and eyebrows.

I quickly dried myself and rubbed some of my sister's moisturiser in over my freshly-shaved areas. Wrapping myself in my sister's white towelling robe, I headed off to her bedroom as I let the moisturiser absorb into my skin. My sister is a makeup junkie - she had everything you could ever need in all possible colours. Although she had taken quite a lot with her there was still large amount for me to play with. I had previously spent hours watching YouTube videos and practising how to apply makeup, but until now had never combined it with my dressing. My first port of call was her nail varnish.

Even though I knew my toes would not been seen, I have been dying to paint them, and like many cross-dressers the first colour I wanted was what I called "Slut Red". I began to paint my toenails with the brightest shade of red I could find while I waited for the moisturiser to dry. Thirty minutes later, both my nails and my legs were completely dry. Even though it probably wasn't the best job in the world, the sight of my painted nails started to make me go hard. If it wasn't for wanting to see this through to the end I would have jacked-off right there, however, I knew there was a bigger goal ahead.

I returned my sister's robe to the bathroom and headed for my Mother's room and her lingerie drawer. Ever since I can remember, I would sneak into my Mother's room when I had an opportunity and look through her lingerie. I was always drawn to her silk and satin underwear. I loved the feel and the touch of it against my skin. In the past, I would try on her underwear and would jack-off looking at myself in the mirror, but today jacking off would have to wait. I quickly selected the items I wanted and was relieved they were still there. After all, she might have taken them with her, but I guess stopping at my Aunt's was no reason to take sexy underwear.

I lay the items out before me. I am slightly taller than my Mother but in other respects, we are similar in size. Well that's one of the advantages of having no car and having to cycle everywhere. The items I selected were all black and were a combination of satin and lace. The bra was a full cup and made of satin. I slid the straps over my shoulders and fastened it. Next came a satin and lace basque. This was perhaps my favourite item of underwear my Mother has. It has satin panels front and back with lace connecting them on the sides, and four suspenders dangling from the bottom. I slid it over my head and down over my bra, fastening it at the back. Next, I put on the stockings, black and sheer. I slowly rolled each stocking up my leg. I had worn stockings before but I wasn't prepared for the sensation of them sliding up my legs. My clitty went hard instantly.

Once my stockings were fastened, I immediately picked up the panties; black satin with lace edging. I always loved how these satin panties felt covering the cheeks of my ass. As I stepped into them and slid them into place, the caress of the material against my skin immediately made me produce some pre-cum. Usually this would be a sign to start jacking-off, and then remove the panties but tonight not only did I want to prolong the experience, I also wasn't worried about staining them. As hard as my clitty was, I couldn't yet tuck it away so I decided to go and apply my makeup and headed back to my sister's room.

I knew the look I wanted to achieve with my makeup and after watching hours of YouTube and the practice I put in, I felt confident I could get the look I wanted. I started first with a little foundation and a little powder to make sure my skin looked flawless. I then set about highlighting my cheek bones and adding a little blush, just for the right effect. Next came some eye liner and then with a bit of shadow I started to create the smokey eye look I wanted. It took a couple of attempts but finally I was happy with what I saw.

Being very careful I added some mascara to my lashes to give the illusion of length, although I have been told my lashes are already quite long for a boy. Then it was on to my lips. As I had gone for a smokey eye look, I knew I would have been better off with a more natural lip colour, but I couldn't resist a voluptuous red colour my sister had and began to apply using a brush. It felt like a painstaking lot of hours, but at last my makeup was finally done. I don't think I would have won any awards but I didn't think it looked too bad.

Given the amount of concentration it took to put on my makeup it had the desired effect on my boy clitty and it was now soft enough to tuck between my legs to give me a more feminine appearance. Once done, I headed across to my sister's wardrobe to grab my dress for tonight.

My sister loved clothes and she had plenty of them. Every time she got paid at her weekend job, she seemed to come home with a new item or outfit. Her tastes ranged depending on what she was doing and her mood and she could go from slutty one minute to angelic and demure the next. She had slimmed down in the last year and most of her new stuff didn't fit me, God knows I had tried most of it, but she still had quite a few items from when she was slightly larger - much to my relief.

As far as I know my sister had only ever worn the dress once, but I had worn it a few times and each time it ended with me jacking-off looking at my image in the mirror. I just knew this was the dress for me. It was archetypal little black dress. It finished just above my knee and had long sleeves. It was a ruched black and just wearing it made me feel as sexy as hell. I carefully slid it down over my head being careful not to smear my makeup and move it into place. Boy, did I feel sexy.

I quickly checked my makeup and then headed back to my Mother's room to select some shoes. Although my sister had a better selection, she actually had bigger feet than me, (UK size 7 against my size 6) and although Mother's feet were slightly smaller again (size 5) I had found with a taller heel, I could fit into them without any problem - especially when my feet were in stockings. Besides, Mother had the perfect pair to match my dress - a pair of black suede platform court shoes, with a 5-inch heel. They had a piece of gold at the top of the heel just to give them an understated but glam look. They were by far my favourite shoes of my Mother's, and I would wear them at every opportunity.

Sliding them on to my stocking-clad feet always gave me a thrill and today was no different. My boy clitty twitched in my panties. Next came the jewellery. As I wanted to keep it simple, I selected just a gold chain and a pair gold bangles for my right arm.

The wig was the finishing touch.. My sister has a number of wigs, which she has bought for fancy dress and other parties. Most are outrageous like her giant blonde afro wig or her long-haired rainbow one; however, my fave is her long, red wig which she got to dress as Jessica Rabbit for last Halloween. I gave it a quick brush before fixing it into place and then brushing again. All done I couldn't wait to look at myself in the mirror.

What I saw looking back at me was no longer the shy, slim, gawky teenage boy, but a redheaded vixen! Sexy and alluring, the type of girl I would be too afraid to speak to in real life. I know I'm biased but I looked hot and my boy clitty was getting hard just seeing my reflection. I was so tempted to get it out and start jacking off there and then but I wanted this experience to continue and besides tonight, I, no Sarah, was going to go out.

To be continued...

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AnonymousAnonymousover 11 years ago
GETTING TURNED ON

When I got to the end of the first part of your story I was disappointed that there wasn't more. My "clitty" was getting really hard in my panties and I had to cross my pantyhose legs to keep from cumming. P L E A S E write the next part so I can feel better, OK?????

Molly

sally_spandexcdsally_spandexcdover 11 years ago
Had to read this one again

2nd time was better than the first and so I had to fav it so I will be sure not to miss part 2...if any sluts want to ,,,send a note

cdmichelle61cdmichelle61over 11 years ago
Excellent

Can't wait to read the next chapter!

sally_spandexcdsally_spandexcdover 11 years ago
HOT TO TROT SARAH

So sexy and such a great start to what I know will be a CD's fantasy cum true,,,Hurry with the next part as I cant wait to hear how Sarah handles herself in public for the first time and just what she wants from this

amylin456amylin456over 11 years ago

wonderful start- great details - and I can tell.. can't wait for the next part !!!

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