Disclaimer: The original characters and plot of this story are the property of the author. No infringement of pre-existing copyright is intended. This story is copyright (c) 2014 Deborah Karen. All rights reserved.

I had been dressing as a girl for something like a year by now. Not just for ‘work’ as I had euphemistically described the various females I had become at the behest of my employer, left to my own devices I had come to enjoy it for purely selfish reasons also.

I had become quite practiced at creating the illusion of femininity in the previous twelve months that I even felt a little resentment if the identity of the girl I had been asked to assume failed to provide me with what I considered to be enough of a challenge. After my first somewhat freelanced attempt, where I had disguised myself as the hotshot female lawyer whose company we were up against in court, my employer had utilised my unique talents when a new angle was sought in their quest for knowledge of what the other side was up to.

The reputational risk to my employer was such that I hadn’t been asked to do anything as ambitious as my first impersonation. There was still the possibility of having to pass myself off as an actual female, rather than a girl of my own creation. Sometimes I wouldn’t have been able to gather the information I needed unless I was moving freely in the world of a real woman.

These schemes inevitably took longer. Identifying a suitable ‘mark’, who I could bear enough of a resemblance to wasn’t always easy and definitely time consuming. There had been a couple of times when my employer had asked me to disguise myself as a particular girl and my own surveillance had soon made the impossibility of such a request obvious. I wasn’t tall for a guy and since taking own my little extracurricular job I had begun to watch my weight very carefully. I was confident that I could pull off playing a woman who was either slightly shorter or a bit taller; what were heels invented for after all? By now I had assembled a large collection of foundation wear and padding that allowed me by turn to be either androgynous and sporty or curvy and full chested. The same applied to hair. If I was impersonating someone I would source a wig that looked passably similar to their own hair. I had purchased a number of other wigs in various colours, lengths and styles that would cover most bases.

As my confidence that I could pass as female increased, along with the enjoyment I felt of dressing like one, each challenge my employer set left my wanting to push the boundaries further. Recently I had played much younger than my own age, dressing as a pupil at an all girls school in west London. As always, researching the ‘part’ was crucial. In this case finding the online store that supplied the school’s uniforms and appropriate accessories for a teenage girl. I wore a long, straight wig in a mousy shade, non-prescription glasses and made myself up with some strategically placed pimples. At least dressing as a schoolgirl didn’t cost me much; I could buy most things in Primark. Obviously the uniform itself wasn’t cheap, but I was always reimbursed (in cash) to give my employer plausible deniability.

I suppose i’m mentioning the schoolie get up as that was what I was wearing when Gary asked me if I would do him a favour. Gary was one of the clerks with my employer. That was supposed to be my job too remember, although it seemed that these days I was spending more time pretending to be a girl than learning the intricacies of being a chambers clerk. Gary was as much a protege of Tommy the senior clerk as I was but I was pretty certain we were taking a different approach about what we were learning.

Anyway I was sat on the bus making my way back to Hammersmith station when Gary texted me. I had been observing the mother of one of the pupils at the school who was in the middle of a protracted divorce case with the father, my employers client. The suggestion was that the mother might be in receipt of some serious financial aid from the new man in her life and the client was eager for proof to try and reduce his settlement. Enter me, disguised as a sixth former at the daughters school to see if I could overhear anything the daughter said at the school gates. As I didn’t want to attract any attention from boys on the way back I stuck religiously to regulation navy knee length socks if I didn’t wear the alternative of 100 denier opaque tights with my flat ballet pumps.

I fished my iPhone out of my schoolbag cum handbag that I was using. There were a few texts and emails and I wasn’t initially surprised to see a text from Gary; he occasionally sent something through if he was the senior clerk on duty. This was a bit of an odd message though:

“Can we meet? (not at work)” I thought for a minute, wondering what he wanted, but like most things these days I found that curiosity got the better of me.

“OK.. where?” I replied. A minute or two later an alert told me I had another text.

“Starbucks on the Strand, Fleet St end” I texted that I would probably be about an hour. I knew I wouldn’t have time to change and wondered how Gary would feel about sitting down with an apparent ‘schoolie’ in a busy coffee shop. Gary was about 10-15 years older than me, but probably not so old that people would look at us and think I was his daughter. On well, people would just have to think I was his niece!

By the time I got to the Strand Gary was already waiting for me. He did a bit of a double take when I sat down, which I was secretly pleased about. I loved to ‘pass’ and reveled in being able to walk down the street without anyone thinking I wasn’t really female.

“Hiya Uncle Gary!” I grinned at him as he looked discomforted.

“Leave it out Ia… um…”

“Amelia” I whispered quickly. Of course Gary wasn’t likely to know the name I had adopted for my schoolgirl disguise.

“Right.. Amelia.. um..”

“What was it you wanted to see me about?” I leant forward and spoke quietly. I doubted if the tourists at the next table could hear us. I wasn’t even sure if they spoke English.

“It’s not about work” said Gary. I had figured that much out already with our meeting place.

“So..?”

“Look, I don’t know if you heard about me and Karen..” Gary’s voice trailed off. I had heard he had split up with his wife of course. Tommy had mentioned it; said it was a subject to steer clear of. Another bloke involved apparently.

“No” I replied “I mean.. not really”

“Gone off with some bloke she works with” Gary said miserably. I looked at him. I mean I could kinda see why, Gary wasn’t exactly a looker. That said, he seemed an OK guy to me, fairly typical of your east London, Essex type guys. The sort of guy that I had imagined I might have been. Once upon a time.

Gary had taken out his mobile and was showing me pictures of his wife. Just as Gary fitted neatly into the stereotypical east London geezer, Karen was looked like a typical east London girl; dyed hair, ostentatious jewellery and fake tan.

“She looks nice” I tried to be helpful.

“She’s a bitch!.. but I love her.. I guess I still do anyway”

“Where do I fit into this exactly?”

“Look I don’t think she’s just gonna come back cos I want her to… and truth is I want to teach her a lesson at the same time”

“How exactly?” I still wasn’t sure what all of this meant to me. Did Gary think I could give him a ‘woman’s’ perspective? Maybe he thought I could pass on some tips for what girls liked in the romance department.

Gary looked me in the eye and began telling me his plan. It seemed that Gary had got with Karen a few years after leaving school, but not before his childhood sweetheart had emigrated to Australia. Although Karen had never met this other girl, Donna, she had always been jealous that she hadn’t been Gary’s ‘first’. Gary was sure that if Karen thought Donna was back on the scene for some reason then she would come running.

“So what I was wondering was.. could you be her? Be Donna for me” asked Gary. I looked at him. Part of me didn’t like the idea at all. I was imagining how this one could blow up in both of our faces. But there was that other part of me that was feeling the adrenalin surge at the prospect of impersonating another girl. I still wasn’t sure how it would work though.

“I can put it about that she’s heard about me and Karen splitting up and that she’s coming back from Aus for a holiday to see me” said Gary.

“What about her friends? Her Family? Won’t they suss something straightaway?”

“Nah.. she hasn’t been back in 15 years.. doubt if too many would recognise her that easily now. As for her family, they moved down to Margate soon after she left.. only child see?”

“Do you even know what she looks like?”

“For all Karen knows she’s married with loads of kids and has put on 10 stone! Important thing is that she remembers her then. She always used to say that I wished Donna had stayed and that I was still with her”

“How will I know what to look like then?” I asked.

“When me and Karen got married Donna was over seeing her mum and dad. I was never gonna invite her to the wedding but she saw me when I was on me Stag. Of course, I was pretty pissed and I didn’t notice Karen come into the pub, but she saw me alright! One of me mates managed to grab me and it was all we could do to stop Karen going on off on me.. or her for that matter. That’s the last time Karen will have seen Donna and that was across a pub. Just base it on that”

“Are you still pissed?” I wondered out loud. “This was when? what 10 years ago? You’re asking me to pull off a convincing impersonation of a woman you last saw in a pub when you had drunk 10 pints.. D’you even remember what colour hair she had?”

“Look, I know it sounds weird, but I have been planning this for weeks now.. I looked her up on Facebook.. she is married now.. has been twice in fact.. so i’m pretty certain no one else could track her down to check out the story” Gary showed me his mobile again and I looked at a picture of a woman, I guess in her thirties, with shoulder length hair and a warm smile.

“There’s plenty of photos I can send you.. She hasn’t changed that much to my eyes, but all you really need to do to convince Karen you’re her will be having the same colour hair I reckon” I knew it wasn’t that easy but Gary had it seemed planned things out fully. He would get me to set up a Facebook account in Donna’s maiden name and he thought some strategically placed status updates would get Karen’s attention. Would that be enough though?

“Well.. I was thinking if you and me went out”

“Like a date?” I asked

“Um.. yeh.. I s’pose so..”

“Would that make Karen jealous?” I had visions of her scratching my eyes out in the ladies.

“Yeh.. reckon that would work”

“Ok.. so what’s in this for me?”

“You’d be doing me a big favour”

“I’m not sure that’s a good enough reason, now you have told me about your psycho ex wife”

“£500 for the Facebook page and some photo’s… another £500 for two dates.. I reckon that should do it”

“OK” I said. I could always do with another thousand quid.

As soon as I got in I stripped off the school uniform and changed into something more comfortable and unisex. I needed to get a look together that would be a combination of ‘girl next door’ and yet sexy and attractive at the same time. As well as looking through the photos Gary had sent me I looked for inspiration from pictures of the 30 something girls that Sky Sports seemed to have on some kind of conveyor belt as presenters.

The ‘uniform’ for this type of girl seemed to be hair below shoulder length with figure hugging dresses and heels and an off duty look of tight jeans and boots. I already had some of these items in my wardrobe but I decided to add a few items to supplement this just in case. I had a good search online, trying to find some similar clothes to the ones Donna was wearing in the pictures and after a few hours had assembled a capsule wardrobe on the bed and awaiting delivery from online stores like ASOS and Very.

I thought I had a wig that would work; brunette that came just past my shoulders and the same length other than some choppy bangs. I could part it just off the middle or at the side with pins and I reckoned it look close enough to Donna’s style. As it was still quite early I decided I would do a bit of a ‘dress rehearsal. I ran a hot shower and carefully shaved my legs and underarms. I stayed pretty much hair free these days as I never knew when work would require my female disguise talents or if the mood would just take me to dress up as a girl for a while.

My make up skills were long since honed to a level that I thought would put many real girls to shame. I had become an expert at using various brushes, highlighters and shadow to make my face look slimmer or my cheeks more rosy. Donna was definitely in the rosy cheeked category with a wide mouth and full lips. I popped in some coloured contacts to give me the same hazel eye colour and glued on some natural looking false eyelashes to add length to my own. Warm toned makeup and a nude lipstick and gloss completed my make over and I stood to one side of the mirror brushing out my wig ready to do the big reveal.

I still felt a little rush whenever I revealed myself as a girl in the mirror and tonight was no different. Even though I was still in unisex mode from the neck down with a bare flat chest and tracksuit bottoms my face and hair had been transformed to that of a woman. I posed and pouted for a few minutes in front of the mirror and wondered if I looked old enough to pass as mid-thirties. I figured that wasn’t important for now and instead began to reshape my male body as a curvy female. As I said before I had amassed quite a collection that could give me an hourglass figure and everything approaching that. Donna had some curves so I began by stepping into a tight fitting set of control knickers that covered from just below my chest to my legs. They sucked in my waist into a more feminine size a look that was enhanced by silicone padding built in to the back and sides to give the illusion of a round bum and wider hips. I took a bra made from the same kind of seam free material and wriggled into the straps. I could fasten my bras pretty easily nowadays; I had had lots of practice. The bra was a D cup and I shivered as I popped in appropriately sized silicone breast forms into the cups. I carefully applied make up in a circular pattern above the line of the bra knowing this would give the appearance of real boobs.

I didn’t want to bother with any fake tan tonight so contented myself with a pair of nude sheer tights that gave my legs a nice sun kissed sheen. I put on a black shirt dress, careful to leave a few buttons undone at the neck to show off my bust. Finally I stepped into a pair of black suede shoes with a blocky 3” heel. I added simple silver jewellery and a few spritzes of perfume and returned to the mirror. With my ‘new’ curves I felt that I had made a passable impression of Donna. I retrieved my Blackberry and posed for a few ‘selfies’, some full length to show off my curves and others just face and shoulders.

Building my ‘Donna’ Facebook page was easy enough. I culled a few photos from Flickr that people had taken in Melbourne and added a few of my selfies. Copying photos of other peoples nights out gave the impression of pictures Donna might have taken, particularly when I captioned them with things like ‘my girlz’. Careful use of the privacy settings showed just enough to give the impression that the fake Donna existed while in reality it was a few hours work to construct the illusion.

I decided to give Gary a little taste and sent him a friend request from ‘Donna Brooks’. A few minutes passed and my mobile rang; it was Gary.

“So what d’you think?” I asked him.

“Bloody hell Ian.. I just dunno how you do it.. I mean.. that is you? Isn’t it?”

“Of course it’s not me” I teased “It’s Donna remember?”

Gary gave a wry laugh “Yeh, ‘course.. Donna”

“Do you think you’re ready to date me then?” I wasn’t overjoyed at the prospect of Gary taking me on a ‘date’. It wasn’t that long ago that I wouldn’t have imagined I would ever fancy a guy full stop, but a lot of water had gone under the bridge since then. In the right mood, I loved the attention and I got a kick from the reaction like the one Gary had just given my photos. It was a bit more enjoyable knowing that Gary knew the score. He was having to deal with the fact that he was looking at photos of a girl who was actually a guy and despite that he still fancied him/her. It was a lot less enjoyable flirting with a guy and always having the fear in the back of your mind that someone might ‘make’ me.

Gary explained that Karen had arranged a double date with one of her friends who was married to a mate of his. He’d heard through this guy that they were going to racing at Sandown Park. He thought it would be good if we could be there too and he planned to book a table in the restaurant.

“That should put ‘er off her food” he laughed. I said I had better get a hat. Women still wore hats to the races didn’t they?

The next week flew by as I rushed around trying to do my day job while refining my Donna Brooks impersonation. I had studied her ‘look’ as much as possible and with the help of a couple of different brunette wigs could fix my ‘hair’ in a few different styles including an up do. Most of the time I was sticking with the long bangs, but occasionally I would use a slide and part my hair to one side like Donna wore it sometimes.

I had been adding more to the Facebook page and I knew from Gary that his ex was beginning to get suspicious about some of his status updates about spending time with an old friend. I had kept in touch with him during the week as I wanted to make sure that I chose the right outfit for Sandown. Gary reassured me that I wasn’t likely to get one of my heels caught in the turf at the race course, although I should bring a coat as we would spend some time outside while the racing was on.

I eventually decided on an outfit. I was going to wear one of the new dresses I had brought after seeing Kirsty Gallacher wearing it on Sky Sports News. Although the dress wasn’t at all low cut it was made from quite a stretchy material that would show off my apparent curvy figure and D cup boobs. The dress had a large floral print all over and finished just above the knee. I teamed it with semi opaque tights and a pair of black suede shoe boots. Simple costume jewellery, a fake Cartier watch and dark red nail polish finished my look. To keep me warm I had a long wool mix coat in a shade of red that practically matched the flower print on my dress.

The morning of the races I spent plenty of time getting ready. A long soak in the bath, softening my skin with body lotion afterwards. I was, of course, completely smooth and I shaved twice before applying my make up. I used a medical cosmetic foundation that would give me the appearance of a light tan while keeping any beard shadow in check for at least 12 hours. I applied my make up with my laptop switched on to Donna’s photos to one side so I could get all of the little details right. I had noticed she had a little mole on her chin, more of a beauty spot really, so this was added with a dark pencil. I fixed my hair with a slide that was almost a perfect imitation of one she used.

I always packed a handbag when dressing as a woman and tried to fill it with the sort of items that would give the impression that I was in fact that person, not a guy impersonating a girl. Obviously I couldn’t get a set of Australian bank and credit cards, but a few of my own international branded cards fronting my own UK ones in a typically female overflowing purse looked quite convincing alongside cash in Aus $ and £. Make up, tissues, hand cream, even a couple of tampons created the set of believably female contents that would stand a cursory glance by another girl if we were touching up our makeup together in the ladies.

Gary had agreed to pick me up and I was pleased that he was keeping up his part of the bargain by arriving on time. When I was dressed as a woman and someone rang my intercom at the flat I always tried to answer in a voice that sounded neither to male or female. If someone was dropping something off to me I didn’t need a double take when I answered the door and they were expecting a young guy or today at least, a woman in her 30’s. I answered the intercom; it was Gary and when I asked what he wanted to do, he said he would come up. I suppose he wanted to check me out. He had only seen photos so far and very rarely saw me on the job as a girl.

I opened the door in such a way that none of my neighbours could see and so Gary wouldn’t get the whole effect until he was inside my flat. I let him in and then closed the door before turning to face him.

“How do I look?” I had changed to my girl voice now. I had even tried putting on a bit of an Aussie accent.

“Wow!.. you look amazing” I loved a compliment and I even now I blushed a little even though I knew I looked knock out.

“Will this do?” I asked, striking a bit of a pose.

“Yeh, totally.. you look really good”

I offered Gary a drink, even though he was driving he looked a bit nervous and I figured it might steady his nerves a bit. Guys always went a bit like this if they knew I was a boy, but we were heading out with me as the girl. I asked Gary if there was anything he was worried about.

“Nah.. everythings cool.. honest.. it’s just.. well y’know”

“It’s because i’m a guy right?” My own voice now, not heartbroken, just familiar with the scenario being played out here. Gary looked a bit sheepish.

“Try and remember why you’re doing this” I continued “You’re trying to make Karen jealous.. so she will come back to you. I’m just helping you to do that. I’m helping you by being Donna for you” I began softening my voice back to a girls as I spoke. Gary looked at me, swallowed hard.

“It’s not just that Ian” he said “I mean, you look so good.. I.. I.. I’ve always fancied her y’know.. Donna.. and now here she is.. here you are.. It’s a lot to take in”

“Do you fancy me?” I asked. I took a step towards him. Slowly. Looking him in the eye and then down so he would follow my gaze. Looking at the big D cup boobs, feminine curves, slim legs elongated by high heels. I was close enough now that he could clearly smell my perfume. I gently stroked his hand and said.

“Gary.. it’s me.. Donna.. i’m here right now.. for you..” I was close to him now, almost touching. I reached down with my other hand and held his lightly. I was a couple of inches shorter in heels that were almost 3” high. I looked up at him and smiled encouragingly.

“This” I glanced down again “is all for you. Haven’t you wondered? What it would feel like to kiss me again?” I looked him in the eye.

And then Gary’s lips were on mine. Forcefully. It was always like a weight had been lifted when guys that ‘knew’ kissed me for the first time and Gary was no different. He didn’t hold me, just squeezed my hands gently at my sides. I opened my mouth and allowed him to tongue me, making pleasurable little girly sounds as he explored me. Finally, I pushed him gently away but still held his hands.

“Was that OK?” we laughed a bit as we both said the same thing at the same time. I was about to answer when Gary threw out another question.

“What did you do that for?”

“I think you’ll find it was you that kissed me” I answered

“You know what I mean”

“Oh.. ‘that’... That was just to get you in the right frame of mind”

“What d’you mean?”

“The plan.. your plan let’s remember… is to use me, cunningly disguised as your childhood sweetheart, to make your ex wife come running back to your arms correct?” Gary nodded. “For that to work Karen has to believe i’m Donna. I know I can convince someone that i’m who I am pretending to be, but really i’m in the periphary. As soon as Karen clocks you with me, shes not going to be looking at me. She’s going to be looking at you. Why? because you have already done a job on putting it out there that Donnas back and I will look enough like the girl Karen remembers for her to accept that i’m her. What she’s gonna be looking to see is how you are around her. Are you at all physical with her? Are you guiding her to her chair in the restaurant? Do you put your arm around her? Do you kiss her? Do you only have eyes for her? If you’re going around looking uncomfortable because you don’t want anyone to suss you’re out with a guy in a dress you’re not going to get the reaction you want from Karen. I needed to see that you see me as female.. as Donna.. that you can fancy me” Gary looked at me and nodded slowly.

“You’re right y’know.. I hadn’t thought this through”

“So.. d’you know what you need to do about it?” Gary took my hands again and pulled me into him. He grinned a bit sheepishly at me.

“Don’t s’pose another kiss is out of the question?”

I smiled and let him hold me, closing me eyes and opening my mouth slightly to feel the press of his lips on mine and then his tongue again. Even through my tight fitting body shaper I could feel him stiffening. I gently put my hand on his hardening cock through his trousers. I rubbed the tip with my finger.

“I’m so pleased I came back for this” I said, Donna again. Gary kissed me a little harder, got a bit stiffer and I knew what I needed to do.

I stepped away from Gary again, still smiling up at him as this time I deftly undid first his belt and then his trousers. His hard cock seemed to spring from his pants and I immediately wrapped my hand around the shaft.

“Ooh.. you’re so hard” I giggled “D’you want me to kiss it?” Gary looked as if he had won the lottery, nodding his head, practically unable to speak now.

Careful to stop my dress riding up too much I bent my knees and crouched in front of his now glistening cock. I rubbed a finger up and down and looked up at him with a smile. I gently kissed the tip and then placed further kisses along the length, pausing only to lick his balls. Gary was moaning with pleasure, but he gasped when I opened my mouth and took his length in.

I began sucking gently, one hand on his hip to steady myself in my heels as I made love to Gary’s cock. I knew most married guys very seldom got a blow job at home so ever the ‘actress’ I made sure my performance was worthy of the West End. I started tickling Gary’s balls and when I thought he was almost there I gave one last gentle suck before pulling away with a little kiss on his pre-cummed tip.

I stood up carefully, knees together, as if I had stooped down to pick up a pencil rather than suck a mans cock. Gary looked like the wind had been taken out of his sails a bit.

“What happened?.. Why did you stop?”

“Always leave them wanting more darling.. always leave them wanting more”