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The Emergence of Sarah

By: Sarah795



‘I’m a crossdresser’. 

A short, simple statement of fact. So easy to type, not so easy to say. I lie here looking at her; watching, waiting. My heart pounds. What is she going to say? What is she going to do? She moves. Pulling away from me; throwing back the covers and scrambling out of bed. No words, no expression. Is this it? Have I just thrown away the past 25 years with those few words? My mind races; going back to before.

I haven’t always been like this. My interest in dressing is quite new. I guess it started when we both changed jobs. In my old job we had moved around a lot, but Elaine had always worked found work as a carer; looking after old or young. She was always happy helping people; it was one of the things I loved about her. For my part I was happy too. We were ‘the ideal couple’. Happily married, nice kids, nice home, etc. Elaine enjoyed her work but it always came after me and the kids and the house. Sure I helped out but the house was her domain and that suited us both.

But everything evolves. The kids grew up and moved away. My contract ended and we moved back to my home town, bought our own house, and started a new life, just the two of us. Elaine found a job as a carer straight away and I soon found a new job, but it meant working shifts. Still the money wasn’t bad, and Elaine arranged her calls to match my hours, so we still had time together. Then after a few months she fell ill. Nothing serious, but she had to stay off work until she had her operation. The hospital promised to call her in as soon as possible, but because it wasn’t serious she wasn’t a priority, and she would have to wait a little while. The days stretched into weeks; the weeks into months. And still no date for the op. 

At first it was ok. She caught up on her reading, and her stitching. She spent time gardening, and enjoyed doing little projects around the house. Gradually though she changed. She lost her sparkle, and started withdrawing. Then one day I had a brainwave. Caring wasn’t the only thing she was good at. She was multilingual. Why not a change of career? It had worked for me. Reluctantly she agreed, and we went to work. There was nothing in the local papers, or the job centre. Then we tried the net. The results were amazing, more jobs than we ever imagined. That night we wrote a CV and emailed it to a few. I came home next day to find her sitting on the couch, grinning like the cat that’s got the cream.

“Guess what!” she exclaimed before I had time to open my mouth. “I’ve got a phone interview tomorrow!” She bounced of the couch, and threw her arms around me.

“They need a translator, and they’re going to phone me and see how good I am!”

She was excited. The old Elaine was back. The rest of the evening passed in a whirl. She couldn’t sit still, couldn’t stop talking. She was bouncing around, full of nervous energy. In the end the only way to calm her down was to take her to bed and try to work some of it off. 

Next day I left for work at 5.30. When I came home at 2 she was on the phone. She was held her finger to her lips, obviously this was the interview. I made a brew and waited. Eventually she put the phone down and turned round, a big grin on her face. 

“I’ve got the job!” she squealed, “I start tomorrow”.

“What am I going to wear?” the smile disappeared, “I haven’t got any office clothes”.

“You’ve got your grey suit” I said, trying to be helpful.

“That’s ancient, I can’t wear that. I’m going to have to go shopping”.

Two minutes later she was gone, leaving me sitting and wondering what had just happened. She came back a couple of hours later, laden with shopping. There were suits, blouses, shoes, you name it. Best of all, there was new lingerie. All sorts of ‘frillies’, which I didn’t really understand but knew would look good on her. That evening I was treated to a display of lingerie, the likes of which is normally reserved for catalogue and magazine pages, and which had a wondrous effect on both of us. Still, it helped us to sleep well afterwards.

Next day she was up at the crack of dawn. The only drawback of the job was the distance, at least an hour away, and that on a good day. I came home at 2 to an empty house. I wandered about and tidied up a bit, trying to remember what was supposed to go where. She finally arrived home about 6.30, looking tired but happy. This soon became our daily routine, and we both settled into it quickly enough. Because she was away all day the housework started to suffer, so I decided to try it, it only seemed fair. After a few days I found it wasn’t that bad, and actually enjoyed some of it, although it never looked as good as when Elaine did it. Still at least it was tidy.

The best part was the laundry. Each day I would come home and take the clothes from the bedroom and sort them into piles for washing. I found that I enjoyed the feel of her lingerie in my hands. The feel of the lace and silk. Her scent on them, especially if she had been feeling horny the day before; even more so if she had left them on as we made love. Little did I realise that this was the start of a slippery slope.

I wasn’t long before I started using them if I played with myself. I would come home and pick up what she had worn the day before. As soon as my fingers brushed against them I would feel myself harden. A few seconds and I would be lying on the bed, jeans and boxers down, playing with the knickers or the stockings, stroking myself, my cock hard. I’d lie there feeling the silk and lace in my fingers, stroking my rigid cock, thinking of how she had looked as she undressed, wondering what she was wearing today. It never took long, a couple of minutes of stroking and I was ready, spurting cum all over my stomach, and then wiping it away with the knickers, feeling slightly guilty. I soon found it was even better if I wrapped the knickers round my cock, while I ran the stockings over my legs, remembering the feel of her stocking clad legs rubbing against me.

Then one day she came home looking excited but a little guilty.

“They want me to go to Prague” she said, excited. “They’re setting up a new office and want some of us to teach the new staff how to use the system”.

“Oh”, was all I managed.

“I’ll be gone for a week” she explained, “Monday to Friday, all expenses paid”.

“You don’t mind do you?” she added, looking guilty.

“Of course not” I replied.

Monday arrived and she was off to the airport first thing. I went off to work and came home as usual. Straight away I was upstairs, looking for the knickers she had worn over the weekend. I liked Mondays as there was a collection of knickers from the weekend waiting for me. My cock was rigid before I even found them. In no time at all I was on the bed stroking, with the thought that I had plenty of time, and no rush to wash them. I could use all 3 sets. I was laying there, my cock wrapped in pale blue silk, a black stocking rubbing my leg, when it suddenly hit me. I was alone; there was no rush, why not see what the stockings felt like from the inside. My heart started pounding, I couldn’t do this, it was wrong; but who would know? 

I lay there, my thoughts whirling like a dervish. Slowly, hesitantly I undressed. I looked down. The stockings were there, lying on the floor where I had dropped them. Hands shaking I reached for them. I had seen her do it so many times, it looked easy. I picked them up. Slowly I bunched one up, and slid my toes in. The feeling was electric; any doubts vanished. I slid the stocking up my leg, smoothing out the wrinkles, feeling the elastic grip my thigh. The second one quickly followed, and I lay back. I looked down, gazing at my legs in her stockings, feeling them clinging to me. I rubbed a hand over my leg and my cock jerked, god this felt so good. Quickly I grabbed the knickers ready to wrap them round my cock. And stopped. In a flash they were round my ankles and sliding up my legs. She was a little smaller than me, but they fitted. I adjusted the elastic round my hips, feeling the thong slide between my arse cheeks. By now my cock was rigid, twitching, constrained by the lace of her knickers. I reached down and rubbed it through the material. It was too much. I lay there feeling dazed, watching the spreading stain on the material.

I spent the rest of that day in a daze. The feeling of her knickers and stockings was heavenly, yet I felt guilty. I had taken of the knickers and thrown them in the wash. I wandered round for a while in the stockings, constantly smoothing them, enjoying them, and hitching them up every few minutes. After I while I went back to the bedroom and grabbed another pair of knickers. I was hard again. I slid into them, a black silk pair, with lacy trim. The suspender belt was next to them. I picked it up. Without thinking I put it on back to front, snapped the fastener closed and spun it round. I laughed. She didn’t realise what a good teacher she was. I grabbed one strap and tried to fasten it onto the stocking. I soon stopped laughing. This wasn’t so easy. Eventually after much tugging and pulling I managed to attach all 4 straps. I tried a few steps. The straps held the stockings perfectly. Feeling happy with myself I sprawled out on the bed. I ran my hands over my legs, feeling the straps rubbing my legs as I moved. I was in heaven. My hand grazed my cock, rubbed it. This time I didn’t cum. I lay there contented, gently stroking, enjoying the feeling. Gradually I stroked harder, faster, watching my cock grow, the head poking out of the waist band, and suddenly thought of her hand doing it. A few more strokes like that and I came. I lay back enjoying the afterglow.

The sound of the alarm jolted me awake. I came to feeling confused. It was dark, what time was it? Then I remembered. I put the light on, looked down and saw my legs sheathed in nylon, red marks where the suspender had dug in whilst I slept, and a sticky patch on my stomach. A sudden wave of guilt came over me. As quickly as I could I undressed and threw them in the wash basket, ashamed of myself. I took a shower and went to work.

It was a quiet day at work and my mind was working overtime. Why had I done it? It wasn’t normal, it wasn’t right. What if someone found out? But it had felt so good. I could still remember the feeling of the stockings, of the knickers. My cock started to swell. I pushed the thought away, but it continued to lurk at the back of my mind. My cock was agreeing with it. I couldn’t get comfortable, I couldn’t concentrate, and the boss was giving me funny looks.

“Are you ok?” he asked looking puzzled.

“Yes, just feel a bit tired” I lied, “I didn’t sleep too well last night, and I feel a bit rough. I’ll be ok”.

“Yeah, well it’s obvious you’re not with it, so sod off home and get some rest”

“I’ll be ok” I answered, “honest”.

“If you can’t concentrate somebody’s liable to get hurt” he growled, “I’m not asking you, I’m telling you, Fuck off home”.

There was no arguing with that, and he was right. If I wasn’t concentrating somebody was liable to get injured, and knowing my luck it would be me. I took it steady driving home, trying to concentrate, while the memory of the feelings kept trying to push themselves to the front of my brain. I got in and went and sat down. Then got up to make a brew. Then opened the fridge and closed it. I was going in circles. Trying to avoid what I knew was coming, and not really succeeding. Eventually I gave up trying, and headed upstairs.

I headed for the wash basket in the bathroom and stopped. I walked into the bedroom, reached for her lingerie drawer, and opened it. I stood there, mesmerised, spoilt for choice. What should I pick? Silk, satin, lace? And which colour? I closed my eyes and drew something out. Satin, I could tell by the feel. I opened my eyes. I was holding a pair of bright red knickers, a lace insert in the front. I was hard now, my hands trembling. I reached in and took out the matching suspender, and the bra. From the other side I picked a pair of stockings; tan, seamed. Quivering with anticipation I dressed. First the stockings, then the suspenders and the knickers. This time I got it right and put the knickers on over the top of the suspenders. Finally the bra. Although we’re both fairly slim, I am a little bigger in the chest, but I managed to fasten it. It was tight, but not uncomfortable. I stood there enjoying the feel of the material, any doubts finally chased away. I was hooked and I knew it; and I didn’t care.

I paced around the bedroom feeling intoxicated, light-headed. I could feel the stockings clinging to my legs, the suspender straps rubbing over my skin as I moved. My cock was hard inside its satin prison, and my nipples were hard inside my bra. Then I saw my reflection. I stood there looking at myself, shocked. I had somehow imagined that I looked good like this. How wrong I was. My legs looked too fat, I had no waist, and although I had a bigger chest, it didn’t fill out the bra like hers did. I stood up straighter, sucked in my stomach and tried to push out my chest a bit more. It helped but not a lot; but what the hell, it felt good. I went into the bathroom and took her silk robe off the back of the door, slid it on and tied it.

I spent the rest of the day like that. My mind was clear now; the whispering, nagging doubts were gone. It might not be normal, but it felt good, and more importantly I felt happy. I wandered around the house doing various chores, then sat and watched TV. I had calmed down a little but my cock was still reminding me that it was there. Every so often I would reach down and stroke myself, or run my hands over my bra and feel my nipples harden. I was on a high but it was more sensual than sexual. I was aroused but not to the point of needing to relieve myself. Finally I wandered off too bed, feeling slightly disappointed as I undressed. I slide the gown back on and lay in bed. I drifted off to sleep, gently stroking myself with the corner of the gown.

The next 2 days followed a similar pattern. I would return home from work and head straight for the bedroom. Once there I would spend ages going through the drawer, examining the various sets of lingerie, enjoying the feel of the material on my fingers, feasting my eyes on the colours, trying on different knickers. I also became more adventurous, trying basques and other exotic items. I loved the way these hugged my body, and how my cock could grow without being constrained by a waist band. I found myself lying on the bed stroking myself, imagining what it would be like to fuck Elaine whilst dressed. The thought of 2 pair of stocking clad legs rubbing together, or her hands stroking me through the knickers was a real turn on, and usually required a change of lingerie. I also took to wearing one of her nighties to sleep in, drifting of to sleep with the feel of satin on my body.

On Friday morning I awoke from another deep and restful sleep, feeling happy and at peace with the world. Then it hit me. She would be back from Prague later that day. This brought things up which I had been avoiding. How long could this carry on? How long until she suspected? I could carry on dressing for a couple of hours each day, but what if she came home unexpected? There was already a collection of lingerie which needed washing before she arrived. I decided that I would stop. After all, I would soon be able to see her dressed, and she looked a heck of a lot better than I did, and I would still get the feel, even though it would be from the other side. That day when I got home I resisted the urge, and set about preparing for her return. 

By the time I heard her pull up in the driveway, I had finished all the laundry, and everything was back in its rightful place. I had made a clean sweep of the house to make sure there was no evidence, and I had bought flowers and wine; mainly because I was looking forward to her return, but to be honest, partly out of guilt. I was out of the house like a shot. She was getting out of the car as I got there, looking hornier than ever. She was tall and slim, with the highlights in her red hair catching the sun. She had a tight sweater which clung to her figure, and a short skirt topping her gorgeously long legs. As she slid out of the car her skirt rode up, giving me a glimpse of stocking top, and more. I pulled her to me, kissing her, my hands running over her hips and down, tracing the suspender straps. She pressed herself against my rock hard cock, wiggling her hips. God I wanted her. I wanted to just push her against the car and slide right in.

“Hello” she said, a dirty gleam in her green eyes, “have you missed me?”

I didn’t bother answering, just pushed the car door closed, grabbed her hand, and half led, half dragged her into the house. I pushed her against the wall, and kicked the door shut. We were all over each other. I ran my hands up her back as my mouth explored her neck. She was wriggling against me, moaning, hands clawing at my shirt, pulling my head against her. I slid my hand round to the front and grabbed a breast, rubbing my thumb over it. I felt the nipple go even harder than it already was.

“Oh god” she moaned, shuddering, “oh god”.

“Missed me?” I asked, my voice struggling. I was still rolling her nipple, knowing it was hotwired to her pussy.

“You bastard”, she whispered, “you know I can’t resist that”

“You didn’t answer my question”, I replied, pausing in my nipple rubbing, and looking at her.

“You know I did” she groaned. “Now shut up and fuck me”.

Who was I to argue? I slid my hand down and under her skirt. My cock almost exploded as I touched the top of her stockings. Slowly I moved it up, over the inside of her thigh. Her legs parted slightly and I reached her pussy. I rubbed one finger along, tracing her thong as it slipped between her lips, feeling the heat and the wetness. By now she had my belt undone and was trying to undo my jeans with one hand. I pressed harder with my finger, rubbing and she gave up trying and hung onto my neck. She was close to coming, and so was I. I slipped my finger under the material, and into her, reaching for the G-spot. I found it and rubbed gently, the heel of my hand rubbing her clit. It worked, her arms tightened round my neck and her body went rigid as she came, moaning with pleasure. After what seemed like forever her body relaxed and she sagged back against the wall. 

“Welcome home” I murmured as I kissed her neck, “now, shall we go upstairs?”

We took the stairs 2 at a time, her trying to take off her sweater, me undoing my jeans. As soon as we were in I pushed her onto the bed, and shoved down my jeans and boxers. My cock was rigid, almost painful, the head swollen and purple.

“Turn over”, I ordered.

“Hmmm” she murmured, “do you want me on my knees?”

“God yes” I croaked.

She rolled over, and came up on her hands and knees. Her skirt rode up showing her stockings tops, and her thighs, her thong tight between her cheeks. I knelt behind her, slid her thong to one side, and slid my cock into her. God she felt good. Her pussy was hot and wet, and I slid in with ease. She moaned. I grabbed her hips, pulling her against me, and started fucking her. Sliding in and out, hard and fast. She was pushing back against me, one hand reaching back to fondle my balls. I could feel the thong rubbing against my cock, and her stockings rubbing against my legs. The effect was overwhelming. I came, gasping; one of the most intense orgasms I could remember, almost painful as the cum shot out. Feeling drained, we fell over onto our sides. Holding each other and whispering ‘I love you’, we drifted off into the afterglow.

We spent the weekend on a high; making love, talking, and enjoying the feeling of two people being in love. But in the deepest recess of my brain the thought was still there. What if she found out? What would she do? I pushed it away. I told myself I was being stupid, she wouldn’t find out. I tried to bury it completely, but every so often it would come back. I found ways to fight it. I left tidying the bedroom until just before she was due home. I asked her to do the laundry, claiming that it seemed fresher when she did it. I found ways to keep myself busy, but the memories wouldn’t go. 


The Emergence of Sarah Ch. 01



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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... 



The Emergence of Sarah Ch. 02



Sorry for the delay between chapters, small IT problem but hopefully solved now.

A massive thanks must go once again to g1dnshwrgr1 for her editorial help and story suggestions.

You don't have to read chapter 1 to follow the story, but it helps set the scene for this and other chapters coming.

Please feel free to comment and rate. 

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Autumn was approaching and the nights had a slight chill, so I grabbed my sister's short faux fur jacket and a black handbag. I quickly put in the lipstick and mascara I had used, as well as some money, my phone and my keys and headed for the front door. It was now or never.

I had fantasised about this moment for so long but now that it was here my heart was racing. As much as I wanted this moment, I could also taste the fear in my stomach. What if I'm recognised? What if I'm ridiculed or beaten? What if....

Just then the doorbell went. Shit! I mean shit. Who would be ringing my door at this time? It was after 9:30pm and we don't get people at our door at this time. I stood frozen to the spot. I was half tempted to open the door to see who it was but then I remembered how I was dressed. Shit!! The best I could come up with was to stay still and quiet and hope they would go away. The doorbell rang again, this time followed by a series of knocks on the door. I don't know what was louder the knocking at the door or the sound of my heart beating inside my chest. The doorbell rang again.

"They'll give up soon, they're bound to give up soon," I kept telling myself. Again there was a series of knocks at the door, but this time I thought I heard something else. Shit!!! That something else was the sound of a key in the lock. Now if I had been thinking I would have put the chain on the door to stop anyone from entering but thinking didn't enter my head, all that was there was panic.

Now I admit, part of the reason I wanted to go out tonight was to be seen, that was part of the thrill, but not here and not now. I thought I had planned for everything but I hadn't planned for this. What the fuck was I going to do? In the milliseconds it took for that door to open a thousand scenarios ran through my mind. What if it was my parents? What if it was my sister? How would I explain this to them? What the fuck would I do?

"Erm, Hi, is Steven here?" The voice wasn't that of my parents or my sister it was my neighbour Emma. Emma must have been in her mid to late twenties and she moved in next door after Mrs. Johnson died. I had once called her Mrs. Thomas just after she moved in but she insisted that I call her Emma, as being called Mrs. Thomas made her feel like an old spinster.

She was about five feet and five inches tall and must have been a size 10 at the most. She had short, straight brown hair done in the style of a bob and was what anyone would call the sexy side of cute.

"Is Steven here?" she repeated. I stood staring silently at her for what felt like an eternity but I realized I had to say something.

"Er, no. He had to pop out." I tried to say it in my best feminine voice, but I guess it wasn't good enough as she stared at me quizzically.

She stood staring at me, as if to try and comprehend what she was looking at. I could have been physically sick at that moment. I knew I was busted, but I had no idea what to do next.

"Do you know what time he'll be back?" she asked.

Her question took me aback. I might get away with it I thought. "Five minutes." I replied.

"Oh good, you don't mind if I wait then do you. I have a message for him."

Shit, why couldn't I have said something different or better? I had no idea how to get rid of her.

"Er, I could take a message for him if you like. It would save you having to wait." It was lame but it was all I could think of.

"No, it's okay. I'm happy to wait, besides I bet you'd like some company. I'm Emma by the way, Steven's neighbor. I live next door."

" Er, high I'm Sarah, Steven's erm....friend." My mind was racing. How was I going to get out of this. "Actually, I just remembered Steven told me to meet him at the entrance to the park." I stammered. "I'd better go or I'll be late."

"But I thought you said he would be back in five minutes." Emma asked quizzically.

"Erm, sorry I meant I was to meet him in five minutes." I stuttered back.

"Oh. Well I tell you what, just let me grab my coat from next door and I'll walk there with you. That way I can give him the message and plus it's not the sort of place a young, pretty girl like you should be heading to by herself. I'm really surprised Steven even suggested it."

Pretty? Did Emma just say I was pretty? Without even realizing I found myself agreeing to her offer.

"One minute and I'll be right back." She said disappearing out the door.

Shit!! What now? If I back out or disappear she'll know something is up. My only chance was to head down to the park with her and hope I could think of something on my way there.

"Right, you ready to go?" Emma's voice shook me from my thoughts.

"Yes, I'll just lock up and be right with you." I said closing the door behind me. Well at least I'm getting to go out tonight, even if it is not how I would want. As soon as I finished locking up, Emma linked my arm. "So how long have you known Steven?" She asked as we headed in the direction of the park.

"Oh, I guess off and on all my life." I replied. I couldn't quite believe this was happening but I knew I had to play along to get through this if I wasn't to be discovered. 

As we walked we chatted, mostly small talk but she asked me more questions about myself and Steven, which I made up as we went. We went to the same school and college, hung out with the same friends, etc. Basically, I was trying to keep it as plausible as possible. She even asked if I fancied him, but I said we were just friends. 

It wasn't all one-way traffic though as it was a good distance to the park I had a chance to find out more about her. Emma was 26 and had never been married but was engaged once. She used to work in advertising but gave it up after being bequeathed money by an aunt to try her hand at writing, hence she spent more time than I realized at home.

The further we went the more my confidence grew, so much so that by the time we reached the park gates I almost believed Steven was meeting me here. More than that, I also realized we were acting just like any two girls who were friends, or at least I thought so.

"It doesn't look like he's here yet?" Emma said as we got to the gates. "No" I replied. "He'd be late for his own funeral." Emma smiled at my lame attempt at a joke.

"Shall we have a seat?" Emma motioned to the park bench just inside the gates. "Sure." I said heading through the gates. Although the walk would have been a relatively no problem in trainers, I had never walked so far in heels before and both my feet and my calves were beginning to ache. I was glad for the opportunity to sit down. I still hadn't figured out how to get home without Emma finding out about me, but the night was going so well I just assumed something would work out. 

"Hi Emma, how are you?"

The voice startled me and it took me a moment to register where it had come from. I had been so engrossed in talking to Emma I hadn't noticed the figure moving towards us emerging from the park. He looked like he had been jogging, or at least he was dressed for it in T-shirt and tracksuit bottoms.

"Paul!!!" Emma exclaimed. "What brings you to these parts?" She asked getting up to give him a hug.

Fuck, I didn't think this night could get much worse. I felt a stone drop in the pit of my stomach. I might be able to fool Emma but I wasn't convinced I could pull it off in front of a guy. Especially one that could probably beat me to a pulp if he found out.

"I just moved into a flat on the other side of the park and thought I'd go for a run." Paul explained. "I didn't realize this was where the sexy girls hung out. It seems my moving may have more benefits than I realized."

"Hey you, stop being a perv." Emma responded with a jokey punch at Paul.

"Well, aren't you going to introduce me to your gorgeous friend?" Paul asked.

At first I wasn't sure who he was talking about and was just about to look around to see who he meant, when I realized he was talking about me.

"Sure, Paul this is Sarah. She's a friend of mine. Sarah this is Paul, he's also a friend but also a major perv."

"Hey, not as much as you." came Paul's reply. "Don't listen to her Sarah, I'm lovely really and only a perv in the bedroom." He smiled at me.

I wasn't sure but I thought Paul was flirting with me. Far from being nervous I was flattered and a bit excited. I've never been attractive to guys before but the way Paul spoke to me began to make me have my doubts. I mean I wonder what it would be like. He was a good looking guy, about 6ft 3 and quite muscular. You can tell he worked out. Any girl would be proud to be on his arm. Anyway what chance would I have with someone like Paul? He could have almost any girl we wanted and he certainly wouldn't want me if he knew what I have hidden in my knickers.

What the fuck am I thinking? I'm not gay. I shook myself out of my daydream.

"Well, as long as you are okay I'll catch you later. I'll give you a call tomorrow." Paul appeared to be saying his goodbyes. I had been so lost in my own thoughts that Emma and Paul had obviously continued their conversation.

"Sarah it has been lovely to meet you." He said bending to give me a quick kiss on the cheek.

"Erm, bye" was about all I could utter as Paul headed off on his run. I watched him disappear along the path with my heart was racing. He'd just kissed me. Okay it was only on the cheek but he still kissed me. Maybe he does like me, maybe...

"Penny for them?"

"What?" I replied

"Your thoughts? You were miles away."

"Oh, sorry. I er, I was just wondering where Steven had got to." I couldn't tell her what I was really thinking.

Emma laughed. "I bet. Cute isn't he?"

"Who? Steven?"

"Paul. I saw how you looked at him."

I started to blush. "Errr, no I wasn't I was just.....I was just wondering how long Steven would be."

"It's okay, all my girlfriends fancy him as well. Besides I think he quite likes you as well."

"REALLY!!! I mean I don't think so. Besides he's not my type." Well before tonight he wasn't my type but now I was beginning to have doubts what my type was.

"Yes, I've known Paul a long time and believe me he wouldn't have been so charming to you if he didn't fancy you. Besides he couldn't keep his eyes of you when he was talking to me. He kept checking you out."

I didn't know what to say in response. I was excited and I could feel my clitty getting hard in my panties. Paul was checking me out? Wow was all I could think.

"Well anyway I guess I'm going to have to go. Are you going to be alright by yourself?" Emma enquired.

"Erm, yes" I said shaking the fantasies of me and Paul out of my head. "I'll be fine. I'm sure Steven will be along in a minute."

This was it. This was my opportunity. All I had to do was wait long enough for Emma to go home then sneak home via the back way. She'll never know and if she ever asked I could always say I (Steven) turned up five minutes after she left. The sense of relief was almost palpable, so much so that I completely forgot about Paul. Well maybe not forgot about him but put him to the back of my mind until I got home.

"Okay, well it's been lovely to meet you, Sarah. Oh, and before I go, could you pass on this message to Steven. I almost forgot." Emma said as she stood to leave.

"Sure, what is it?"

She leant over as if to whisper in my ear.

"You're a very sexy girl Steven, but the next time you are going to get ready I would make sure you close the bedroom curtains." With that she kissed me on the side of my cheek and stood back.

She knew! In fact, she had known all along. I sat there stunned. It felt like my world was spinning. I could feel the blood rushing out of my face. I didn't know what to do or say.

"Are you okay? Steven, Sarah? Are you okay?"

I could hear what Emma was asking, but I didn't know how to respond. She reached forward and grabbed my hand.

"But, but...." was all I could stammer.

"Oh, honey. Don't worry. Your secret is perfectly safe with me."

"You didn't tell Paul did you?" The thought that someone else knew horrified me.

"No, I didn't tell Paul and I promise I won't tell anyone. You really do look very sexy as a girl. You could perhaps do with some help with your make-up, and a bit of practice with your voice but honestly, looking at you now, no one would know."

I could feel the tears well up as I began to tremble.

"Oh, sweetie. Don't get upset. It's honestly okay." She tried to calm me but I was awash with emotion. Seeing my distress Emma continued "Look, why don't you come back to my house and we can talk about it in private? I think someone could do with a drink."

Taking a hankie from her pocket she offered it to me. "Here, I think you might need this otherwise you're in danger of getting panda eyes."

"It's waterproof." I sobbed.

"What is?" she enquired.

"My mascara. It's waterproof." Try as I might I couldn't control my sobbing.

Emma chuckled. "Well that may be so, but no girl wants to be seen crying in public. Come on we'll head back to mind."

With Emma's assistance, we started back towards her house. I don't remember how long it took us to get there but before I knew it, we were inside her front door. I had calmed down a lot since we left the park but I still felt overly emotional.

"Right, red or white?" Emma asked taking my jacket.

"Red or white what?" I replied.

"Wine, sweetie. It's the best drink to have at a time like this."

"I don't know, I don't really drink." I explained.

"White it is then." said Emma heading off to the kitchen. "Make yourself comfortable in the lounge and I'll be through in a minute."

I headed into her lounge. It was tastefully decorated in neutral colours with two sofas on either side of a small coffee table. There was large modern gas fire on one wall and two paintings on the other. I sat down on the nearest sofa and instinctively kicked my heels off, tucking legs under me.

"Here you go. This will help." Emma said handing me a large glass of white wine as she entered the room. She sat down on the sofa opposite me.

"So, how long have you been dressing as Sarah?" she asked.

"Erm, look I'm sorry. I was practicing for the college play. It's a....it's an all-boy production of... er..of." I thought I would try and come up with an excuse, after all, I didn't want it to get out that I dressed like a sissy. "....of, er, An Inspector Calls!" I basically said the first play I could think of.

"Oh, I love that. Which role?" She replied.

"Erm" Shit! I couldn't think.

"Look Steven, SARAH. It's okay. I know quite a few guys who like to dress like you do. Actually compared to some you are quite conservative in your attire. Honestly, it is no problem and I promise I won't tell a soul. Your secret is safe with me."

It wasn't so much what she said but the way she said it, which was reassuring. Although reluctant I felt I could trust her, besides I didn't really have much choice.

"So do you want to tell me about it? About why you dress? You don't have to. I'm just curious." 

"Erm," I hesitated "I guess I don't really know to be honest. I have been fascinated with girls' clothes ever since I was little when my sister used to dress me up like one of her dolls." It felt easy to talk to Emma about it. Apart from a few other trannies I met online I had never really spoken to anyone about it and certainly not face to face. Emma seemed different and for some reason, I felt that I wanted to tell her.

"So what do you like to wear?"

"I guess whatever looks good in my Sister's wardrobe." I laughed.

"Well, I really like your style. If I hadn't seen you through the window I would never have known you were a guy." Emma replied.

"Yeah, about that. How exactly did you see me? I thought I had been ever so careful." I was more than just curious, I wanted to make sure I wouldn't get caught the next time.

"I think you forgot that from the bottom of my garden I can see into the back bedrooms. I was out doing a spot of weeding when I noticed someone move in the bedroom and because your Mum had said you would all be away this weekend, I thought it might have been burglars. So I thought I would try and get a better view to see if it was."

"You're lucky in some ways." She continued "because if you hadn't stood near the window when you were putting your bra on I would have been calling the police and you would have had to be a lot more at explaining yourself to them than you were to me."

"I guess that would have been more awkward," I giggled. I don't know whether it was the wine or the company or both, but I was feeling very comfortable sat here talking to Emma.

"Wait a minute! It must have been a good 45 minutes to an hour between me putting the bra on and you knocking on the door. How come you didn't knock any sooner?"

"Erm, well." It was Emma's turn to be embarrassed and start to stammer. "Okay, well once I realized it was you I thought I would leave you to your fun, but as I was cleaning up I became more curious as to what you would look like. As I said before I have a few friends who like to dress up and to be honest some look really good and some look really bad, but I thought you might make an attractive girl. I have to admit in the end curiosity got the better of me and I just had to find out."

"When your Mum phoned it just gave me the excuse I needed."

"My Mother phoned?"

"Yes. She just phoned to tell me that you were staying at home at the weekend and I wouldn't need to go in and water the plants and see to the curtains etc. It's why she gave me a key a week or so back." Emma explained.

"Well, that explains the key, but now you have seen me what do you think?" I was dying to find out. "Do I look as good as you thought I would?"

"Probably better, but if you don't mind me saying you could do with a little help with your make-up and something needs to be done with your bust. Wait here a minute," she said as she disappeared upstairs.

I was beginning to feel light-headed and I don't think I was taking it all in. Here I was dressed like a girl, sitting drinking wine with my cute next door neighbour. The night wasn't turning out as I had planned but I didn't know if it was better or worse than I had hoped. Better in that now I had someone to share my secret with but worse in that someone else knew and might tell others my secret. It would be fair to say my emotions were pretty mixed up, especially if you added Paul into the mix.

"Here try these." Emma had returned and was handing me what looked like a pair of chicken fillets. "They're breast enhancers, designed to make you look like you have a bigger cleavage. I use them all the time when I'm out clubbing, they make me look a full cup size bigger."

"Erm, I'm going to have to take of my dress to put them in." I said a little nervously. "Is there somewhere I can change?"

"Just do it here. I don't mind after all we are all girls together." Emma smiled.

I was nervous about the thought of it, but also felt a need to please Emma. I stood up to step out of my dress.

"I think it might be better to take it off over your head, here let me help you." Emma was quickly lifting the hem of my dress and before I knew it my arms were above my head and I could see nothing as she helped take it off me.

The action of taking the dress off resulted in my wig coming off as well.

"Here, pop these into your bra and I'll fix your wig into place." Emma took my wig and started to brush it out as I inserted the breast enhancers into my bra. I had seen these being used on YouTube videos and knew I had to pull my chest across to give the appearance of cleavage. It didn't take me long to get them into the right place.