tagTranssexuals & CrossdressersInstead of My Sister Ch. 03

Instead of My Sister Ch. 03


After taking my sister's place on her driving test almost another year passed before my next opportunity to take her place. A month before we had moved as a family to a new part of the country where Mum had found a good job although we had yet to make any friends. I was still doing a minimum wage job in a supermarket, whilst Jessica was away on a holiday in Spain, before she started a new secretarial job at a firm of solicitors next week.

I still dressed up when I could. I did think I'd have the chance to go out and about, but Mum and Jessica didn't want me to, in case someone saw me and thought I actually was Jessica. That was only a good thing when it suited them. For now my dressing-up was restricted to the odd evening staying in and keeping Mum company.

The phone message that changed everything came on Saturday morning, while we were both out. From the time on the answer-phone it had been made shortly before Jessica was due to fly back. The line was bad but the message was clear. Apparently Jessica had injured herself in an accident, not too badly, but badly enough not to fly home. She might be able to get a flight on Monday or Tuesday, but wouldn't be home to start work on Monday. As I listened my stomach began to tingle with butterflies of excitement as my mind raced ahead to the inevitable request. It came right at the end of the message.

"Can Peter cover for me until I get home?"

The message ended abruptly, with the sound of pips indicating that the caller had run out of credit. There was no doubt in my mind how my weekend and the start of next week were going to be spent! Mum's planning skills went into overdrive. After a frenzied hour of internet browsing, telephone directory thumbing and phone calls, she was on her way to a nearby super shopping mall, whilst I was on my way to the shower, armed with some hair removal cream and the instruction not to wash my hair.

I was out of the shower wondering what I should wear, when mum returned. She explained that she had made the arrangements for me to make the best imitation of Jessica ever. The rest of the day was all such a whirl, its hard for me to remember all the details in the right order!

First there were two items designed to enhance my appearance. One was something called a 'gaff', a cross between a g-string and a jock strap, which was to be worn under my knickers and designed to keep my cock tucked safely between my legs. The other item, or should that be items, were a pair of fabulous synthetic breasts, that Mum swiftly stuck on my chest using some adhesive. She assured me that the glue was strong enough for me to go bra-less and would last up to 48 hours and probably longer if I was careful. Soon I was experiencing the feeling of 'loading' them into my bra. They were fabulous! They moved as I breathed, bounced slightly as I walked and accurately weighted to match the real thing; they looked frighteningly real. They actually took quite a bit of getting used to, but added to the realism. I spent the rest of Saturday perfecting my walk, trying on the clothes I would wear to work. Mum had treated me to several new matching bra and panty sets, all in pretty pastel shades with a lacy trim. With the new false boobs I looked and felt so curvaceously feminine, although their weight meant it took me a while to get used to walking in high heels.

We spent Sunday quietly. There was no news from Jessica and our attempts to contact her at her hotel were foiled by our inability to speak Spanish. I spent the day at home, wondering about the next day. I was so nervous I could hardly sleep!

I woke well before my alarm went off. Mum was up too, watching my preparations carefully, making sure my hair and make-up were perfect. I was wearing a tailored white long-sleeved blouse and a skirt suit, with a fitted jacket and a short skirt. In truth I felt the skirt was a little too short, but it was what Jessica would wear so I had no choice. I carried a matching black handbag and wore a pair of shiny black high-heels. As I walked to the bus stop the heels clicked wondrously on the pavement and I felt so contented.

The first thing I noticed was the difference in people's reactions to me. Before I had been trying so hard not to be noticed and I had wanted to get the deception over as soon as possible. Now I had more confidence. It started with the bus driver. I recognized him as I had often caught his bus to work, as Peter. He never spoke or showed any interest as I paid him.

Today, I got a smile, a 'morning' and my hand squeezed as he handed me my change. I was also fairly sure that he had been staring at my breasts. Normally it was hard to find a seat as men often sprawled over both seats. Now, two of them sat up, clearing the space next to them. An older woman took advantage and nipped into the first seat. I took the second one, which meant sliding past the guy into the window seat. I know his hand brushed my bum as I did and I'm pretty certain it wasn't an accident. As the journey went on his hand somehow found itself resting against the side of my leg, just below where my skirt ended. I generously ignored these incidents; pondering for a moment to wonder what his reaction would be if he knew the truth, I turned my attention to the view out of the window, watching out for my stop.

I got off at my stop and walked along the high street to the solicitors' office. I paused to read the shiny brass plate by the door: 'Jenkins & Jenkins Solicitors'. I knew it was Mr. and Mrs. Jenkins, but that was all. I took a deep breath and tried the door. It was locked. I didn't want to be late on my first day, or on Jessica's first day to be precise, but I didn't know what to do. I saw a doorbell and rang it.

A tall elegant woman answered the door. "You must be Jessica, I'm Catherine Jenkins." She held out her hand, with beautifully manicured nails, and we shook hands. The touch of her hand made my tummy flutter delightfully; I realized that I quite fancied her! Once inside I was introduced to Mr. Jenkins ("Call me Michael, unless we're with a client"). He flashed me a brilliant white smile that did credit to his dentist. To my surprise my tummy gave another little flutter. Michael was much nicer that the horrible weasel-like driving instructor or the slimy test examiner; I realized that I quite fancied him too!!

The morning passed uneventfully, as I began with some filing, some note taking and a little typing. As I went to get a sandwich for lunch I began to think that this might end up being quite easy!

In the afternoon I took a letter into Mr. Jenkins for him to sign. I ended up standing next to his chair as we looked at the letter and, to my amazement he began stroking the back of my leg, right up my thigh to the hemline of my skirt! My tummy fluttered again; it felt so nice, I was actually sad when he stopped. As I sat at the reception desk I kept replaying the moment over and over in my head.

We closed to clients at 5pm. Michael called me into his office.

"Well Jessica, not to bad for a first day, but you were five minutes late back from lunch." He went on to explain that I was on a week's trial and poor punctuality might be held against me. "Unless, um, no" he muttered, "I couldn't really ask you to do that."

"What Mr. Jenkins? I really need this job. Tell me what I could do." My mind was racing with possibilities as I said this.

"When my Father founded the firm, he used to administer reasonable physical chastisement for small misdemeanors like being late. If you were to sign this form accepting reasonable physical chastisement then we could overlook the lateness and administer a small spanking as your punishment."

My mind whirled; a spanking from Michael!

I heard myself saying, "Well Mr. Jenkins, if it will help me keep my job, I'd be happy to sign the form."

In a flash, he'd printed out a form for me to sign, I'd signed it, without even reading it, he had called Mrs. Jenkins in from her office and I was bent over, with my forearms resting on the desk waiting for my punishment.

"On this occasion, as it is the first time, you may keep your skirt in place," he said and with that he spanked me! He administered five, firm slaps, one for each minute, his hand lingering just a fraction on my bum after each slap.

"Thank you Mr. Jenkins" I said as when he finished.

The next day I made sure I was not late. I didn't want the Jenkins' to think that I wanted to be spanked, even if, secretly, I did. I started the day off taking notes for a client meeting. The client was a bit of a tart in my opinion. All fur coat and no knickers as my Mum might have said. To be fair I don't know for certain that she owns a fur coat, but from the number of times she crossed and uncrossed her long, tanned legs plus the shortness of her dress, I do know she didn't wear any knickers. After she'd gone Mr. Jenkins asked me to return to his office to show him my notes.

Once again I found myself standing by his side, at his desk and once again he began to stroke my leg, further up this time, beyond my hemline!

"That bloody woman, she always leaves me all flustered, flashing everything like that!" he exclaimed as he stood up. "Blast!"

"What's the matter Michael?"

"She's given me a bloody erection and my next client is due any minute. I'll never be able to concentrate."

"Can I help at all?" I said in a small voice.

"Not unless you're offering me a quick blow job!"

Trembling with anticipation and amazed at my own sluttish behaviour, I knelt down in front of him. I looked up through my fringe and said softly "Anything to help, Mr. Jenkins."

With his help I freed his cock from the confines of his trousers and pants. I let out a startled gasp. His cock, fully erect, the tip glistening with pre-cum, was much bigger than the others. I lowered my head and began to lick his monster cock from tip to balls and back again, before I tried to take it into my mouth. Using my lips to grasp it firmly, I felt his foreskin slid back and his exposed tip brushing against the back of my throat. I made a conscious effort to relax and his thrusting pushed his cock deeper and deeper. Sucking hard and swallowing seemed to be having a good effect as he let out moans of pleasure.

I heard a voice in my ear. It was Catherine!

"If you could be quick, Jessica, I have a client due shortly and I need you. By the way, make sure you swallow it all, I don't want my husband's suit needing the cleaners."

I was completely flustered and, to add to my confusion, Michael chose that moment to release his cum, filling my mouth. With each squirt his cock twitched, making it hard for me to keep things under control, but I swallowed as fast as I could and just coped. I finished by licking his cock clean as he let out a satisfied sigh. He handed me a tissue to clean myself up and thanked me for my 'assistance' as he put it. I wiped my face and hurried into Catherine's office for her meeting, only a few moments late, but late enough for me to realize from the look on her face I could expect a spanking later.

Sure enough, on my return from lunch, Catherine called me into her office.

"You can guess why I've called you in here, I hope?"

"I was late for your meeting. I'm very sorry."

"I'm glad you have apologized, but it won't spare you a spanking. I'd like to do it now, if that's convenient as I other things to attend to at the end of the day." I nodded. "Over here then. I prefer to administer my spankings over the knee."

Obediently I found myself over her knees, high enough for my toes to barely touch the ground and for me to feel very vulnerable. Swiftly she spanked me, six slaps in all, much less gently than her husband, even though she did rub it gently for me saying "this is all for your own good. Incidentally, don't think this has anything to do with the blow-job you gave to my husband. You can do that whenever you want, personally I can't stand the taste."

I returned to my desk, with my bottom still stinging. I shifted uncomfortably in my seat, comparing the two spankings. Surprisingly Catherine's had hurt more and for longer. It had also been more humiliating, being over her knee like a naughty child.

The day ended with a call from Catherine. She was in the flat above the offices and needed my help at once. I hurried up the stairs. The sight that awaited me took my breath away. She had taken her dress off and was wearing just her beautiful coordinated lingerie- black bra, panties, stocking and suspenders. She looked totally stunning and my cock strained against the restricting gaffe. She explained her problem. She had just painted her nails and she badly needed a pee!

As if in a dream I followed her into the bathroom, slid her panties down and helped to her sit. Then I waited while she pee-d, blushing a very deep shade of red and finding my gaze drawn to her beautiful body. It sounded so loud and I was amazed by how unconcerned she was.

"Thanks Jess, you're a life saver" she said.

Then I had to wipe her dry! My hands shook noticeably as I gingerly wiped some folded toilet tissue over her pussy. Then I slid her panties back up again. I was so turned on, so embarrassed and so confused I nearly tripped as I left.

That evening there was another message on the phone from my sister saying that she still couldn't get a flight and could I keep going to work in her place? Needless to say I was delighted to oblige, although she gave no indication of when she'd be back.

Wednesday began quite uneventfully. Again I found men noticing me on the way to work, but this time I also noticed that women looked at me in a very different way to before; perhaps sizing up the competition! From being an anonymous guy to a girl worth a second look was quite a journey. At work I took notes, typed letters but nothing unusual happened.

Just before the end of the day Catherine invited me up to the flat.

"Yesterday I put you in an embarrassing position, sorry for that Jess, but I couldn't help noticing the way you were staring at me. Are you bi or just bi-curious?"

I decided to be honest, up to a point. "Curious, I guess. I've never been with a woman, but I do find you very attractive."

(It was sad, but true; I had sucked cock, twice, no three times now, and been taken up the bum by the driving test examiner, but I still had no experience with women.)

"Jessica, I think what's good enough for my husband is good enough for me. How would you like to lick my pussy?" She stepped out of her skirt, slid her panties off and posed for a moment. "Well?"

"I'd like that very much Catherine."

She took control and was very dominant. I laid on the bed and she knelt astride me, pinning me to the bed. She lowered her pussy onto my face and told me to lick. I licked. Smothered by her moist pussy, I licked and licked, running my tongue along her pussy lips again and again. All the time she was writhing about, grinding her crotch into my face. I probed with my tongue, sometimes pushing it deep inside her, which she seemed to like. I also probed a smaller hole and was rewarded with a metallic-tasting tiny squirt of liquid that I assumed was her pee. She like it best of all when she had pushed her clit right into my mouth and I could suck really hard on it, pulling it gently between my teeth, allowing me to give it a frenzied licking. She reached her climax, grinding into my face and squirting more pee into my mouth as she cried out "Yes! Yes! Yes!" She stayed there for a moment, before getting off.

"That was great, Jessie; but I really need a pee. I didn't leak any when I came, did I?"

"Um, well, yes, you did a bit." I blushed, adding, "but it was ok. I didn't mind."

"Really? That's delightfully kinky of you Jessie. I'd kiss you, but your face is covered with ... well you know what. You'd better wash your face before you go home."

I took her advice, also wiping my cock clean -- I had suffered some dribbling fluids of my own!

I wondered what Thursday would have in store. While I was typing some letters my mind wandered to the events of the previous days and I made some errors. Michael was not pleased and before I went to lunch he called me into his office.

"You're still making careless errors but for now I'm prepared to allow you to carry on. Assuming you'll accept the punishment of a spanking?" I nodded and he added "very well, raise your skirt up above your waist and assume the position across my knees."

My knees trembled as I hitched up my skirt up, walked self consciously across the office to where he was sitting on the sofa and I laid across his lap. He pressed his hand on my back, pinning me in place. I could feel his cock hardening as he pushed me down and I could feel it twitch with every slap, all twelve of them. These were much harder than the first time. I cried out in pain the first two times and was told that if I made any noise the slap didn't count. I bit my lip and felt tears welling up in my eyes. After the ninth slap, I saw a pair of black high heels standing in front of me, so I guessed Catherine was watching, which didn't make it any better. Now my humiliation had an audience, making things even worse.

After my ordeal was over I stood up, my bum cheeks stinging. I was certain that they were as red as my blushing face. I started to pull down my skirt.

"Stop!" Michael ordered. "I don't like tights. Get some proper underwear. Catherine will advise you. Come to work in tights tomorrow and it'll be your last day."

He strode out. Catherine put her arm round my shoulders and comforted me.

"Don't cry, Jessie, we'll go shopping after work, my treat. It'll be fine."

After work Catherine drove us to a shopping mall which stayed open late. There she made a bee-line for a lingerie store. I was very nervous but also excited. The thought of wearing such beautiful lingerie as Catherine thrilled me. The thought of trying it on in a shop terrified me. Luckily I knew my sizes so didn't need the measuring service the shop advertised.

Together we went round the shop, commenting on the different styles and materials.

"I think today we only need to buy one set. If you like it and more importantly, if Michael likes you in it, we can buy more later." She handed me some items. I looked at silky, white, lace-trimmed garments. They were so much flimsier and so much sexier than the plain cotton undies I was wearing. I waited while she paid, then she handed me the bag, explaining that she had a few more things to buy and that she'd see me tomorrow.

At home I told Mum what had happened, as I had done every day. On her prompting I tried on the new lingerie. It felt great, but whilst the bra had an uplifting effect, it didn't cover my false boobs as well as my old bra. However, Mum used some foundation make-up which disguised the joins quite well. The knickers were just sufficient to cover my gaff, which came as a relief.

I got up early the next day, to allow for the 'camouflage' job. The new lingerie certainly had an effect. With my boobs virtually thrust into the faces of passers-by, I attracted a lot of stares, admiring ones from men, and some from women that I couldn't be sure about. Some, especially from women who were with men I smile back at, were hostile; some seemed to be sympathetic, almost pitying me. The stockings also affected my walk although this was a more subtle effect. Being without my tights made me slightly less self confident so I took smaller strides and the suspenders seemed to tug at my legs, giving me quite a wiggle in my walk!

At work I was kept busy as usual, but things eased off in the afternoon. Michael called me into his office, when Catherine was already waiting. He launched into a speech.

"Right Jessica, time for your evaluation. Your work and punctuality have been acceptable; you've been willing to do that little bit extra, so to speak, to keep things running smoothly. There are just two more things. Firstly if you could just take off your blouse and skirt, we can inspect your underwear and see if you've made the requested changes."

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byMisslexia© 8 comments/ 102392 views/ 28 favorites

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