How had I been volunteered?

Hi my name is Joseph Smith but friends call me Joe. I am twenty four years old, live on my own and at the moment haven't got a girlfriend. To be honest I am Mr Average. I do an average admin job in a College and have been there since I left education at eighteen. My height is 5'8" and although I don't watch what I eat, I am pretty slim as I do quite a bit of exercise but nothing remarkable, just average.

One summer two weeks before the finish of the academic year a few of us were having a chat in the canteen during a break. We had all seen the local paper about a animal charity in the town running out of funds and potentially having to close. We all came up with ways of raising funds and eventually got down to someone doing something very silly for sponsorship. How the decision had been made that it would be me doing the silly thing, I had no idea.

The girls were having a quiet laugh about something and I made the mistake of asking them to share it. Sharon spoke about no point in a gunge tank or anything like that, it had to be a bit outrageous and daring. I suddenly was thinking, what are they going to suggest, get me swimming with sharks or worse??? Sharon went on, "Well Joe, you are a bit of a blokey bloke. You know, drink beer, belch, scratch your bum, etc.!". "Oh thanks, is this a character assassination or an idea to raise money for the animal charity?"

Sharon blushed as did the two other girls and none of them wanted to say what the suggestion was. It was my mate Stuart that finally got them to tell us. Sharon spoke up "Three weeks from now all the students will be gone and it will just be skeleton staff here for the summer right! Well what if you came to work dressed as a lady as a dare!" The lads and especially Stuart burst out laughing and the girls joined in. I was dumbstruck!

Before I had a chance to reply, one of the guys had opened up his laptop and was getting a sponsorship form together. I had not said a single word and all the others had made the decision that it was a brilliant idea.

Just then the principal walked past to get his mid morning coffee. Stuart quickly asked him if it was ok and filled him in. We soon saw a big smile on the principals face and he laughed out loud. That was it, decision made.

Over the two weeks staff from all the various departments asked me what I was going to wear and I was getting updates on how much sponsorship had been raised. At the end of the first week it had already passed £1,000. By the end of the second week the final figure raised was just over £2,500. The principal and my boss added their all in by saying that they would double it. So £5,000 was raised for the animal charity. I couldn't back out now....could I???

Over the two weeks I had time to prepare, I had done research, bought a few bits on Amazon and visited a few charity shops for clothes. So Sharon thought I was a "blokey bloke" did she!!!! My mind was set to blow them away and not just look like a chap in a cheap dress. The weekend before the fateful day I had a strict diary of tasks to do. That Saturday had me visiting a beauty salon. They helped show me makeup and how to apply it. My eyebrows got a good plucking, they made holes in my ears for proper earrings and fitted a couple of simple studs. I then had a waxing that was torture I would never want anyone to ever suffer. I was then passed onto another lady who put a cream on my face which stopped hair growth for a few weeks and removed anything there at the moment. After that was nail time and I soon sported crazy red nails on hands and feet. The final thing was for a spray tan. Now I was expecting to at least have my underpants on for this, but the lady was pretty insistent that I be naked and she seemed to take an age over it with help from two other ladies. Not sure if that's normal but once everything was done and I was "dry", I got dressed and headed home wearing a pair of gloves.

Saturday evening rather than do my usual of going to the pub, I spent it relaxing with a pizza delivery and a few beers and left the other tasks to Sunday. I should have got all the purchases out of their packaging way before Sunday, but you live and learn. Leaving it until Sunday evening, firstly I checked the underwear from Amazon. A nice white bra and matching knickers. From a charity shop a good pair of black court shoes with a small heel. From another charity shop a bob wig that just needed a good brush out and a few snips for stray hairs. I had a very small football for skill practice and the wig sat on it perfectly. The jewellery from another shop was a pair of dangly pearl earrings and a matching necklace and they checked out fine. A white blouse I had got from a clothes shop fitted fine and was great after an iron. Finally I got to the grey skirt suit I had found in a charity shop. The jacket fitted perfectly as it had in the shop and wasn't too long, only just covering the waistband level. I was nervous about the skirt as I had bottled it in the shop and not tried it on. I had checked the size of the waistband was right for me, so I was happy to buy it. But when I put it on, I was in for a bit of a shock. It was far shorter than I had imagined and it had a slit at the front, to one side. As I looked in the mirror at the skirt for the first time, it was a good six inches above my knees. It wasn't indecent, just quite a bit shorter than I had expected. After carefully pressing the jacket and skirt and hanging them up ready for the morning, I relaxed and watched some sport on TV. That night setting my alarm really early, very early for me anyway.

In the morning I had my usual breakfast and orange juice and then set about getting ready. In the shower I used the stuff the beauty salon had suggested and afterwards my skin looked particularly soft and had an aroma of flowers. It took me an age to get some of the makeup right and at a point it looked ok, so I thought quit while your ahead. The only way of hiding my dick bulge was forcing it between my legs and lifting the knickers up a bit higher and that seemed to work. Actually getting dressed only took minutes although the bra was a pain to put on. Fitting it with the chicken fillets purchased from Amazon, I suddenly had a reasonable breast area.

Once everything was on, I then took my first proper look in the mirror. I could tell it was me from the eyes, but I was dumbstruck. The rest looked nothing like me and when I put on the ladies glasses, found in another charity shop with the same lens magnification as my own glasses, I was someone new and definitely female.

The skirt was really way too short in reality but I had to just go with the flow and it was after all just one day and a lot of money for the charity. I put all my usual stuff in a black patent shoulder handbag. I covered myself in the perfume suggested to me. To stop me having second thoughts, I just went for it and headed to my car outside. For those that normally just slouch into the drivers seat, in a short skirt and heeled shoes, that wasn't an option. It became a sort of ballet, keeping my legs together and swinging in.

The journey was uneventful but pulling into the half empty carpark at the College, I started to get seriously nervous. My mind was doing overtime as I sat there for ages. I was suddenly shocked to see Stuart pull up next to my car and get out. That seemed to break the ice as he insisted on seeing the finished article and I had to get out and show him.

With many "Fuck me!" and "Bloody hell!", he just couldn't take his eyes off me. Sharon and her friend pulled up next and we soon had quite a gathering chatting away in the carpark. Sharon jokingly suggested I was here for an interview, I looked so smart. Just before 08:30, we headed into the building. Where ever I went people were gobsmacked. From reception to canteen, they all wanted a look and were impressed. It must have been 09:30 by the time I finally got to my desk to do actual work.

The morning was pretty boring, apart from learning new skills pertaining to short tight skirts. Reaching down to the bottom filing shelf was the most difficult I found, but it was ok. The Principal and my boss visited our department and were seriously impressed by the way I looked. They didn't care about my work, they just wanted to show me to everyone including the governors who were there for a meeting.

After lunch my heart sank a little when I was asked to go to reception. Not knowing what was there, I pensively went down the corridor dreading what was waiting. Entering reception, the Principal introduced me to a lady reporter from the local paper and the lovely lady that ran the animal charity. She was over the moon about the money and couldn't thank us enough. I thought to myself 'Hang on a second, "thank us", its me dressed up in the damned outfit and no one else!'

After a few photos and some questions from the reporter she asked me a question that knocked me for six. She had a copy of the sponsorship form and it stated I would be dressed lady like ALL WEEK! "What was I going to wear tomorrow?" I looked round and there in the corner Stuart and Sharon were laughing as quietly as they could and doing high fives. I shut my eyes and contemplated saying "Sorry I cannot do it all week." Thinking through though, I had done it one day, four more to go and the five grand was a god send to the charity. The reporter did suggest I looked a bit too convincing, but a photo of me after a cross country run half covered in mud was ideal for the article of a before and after.

Me being centre of attention soon came to an end when my boss said I needed to go to the bank with some cheques. I am sure he did it on purpose, but he was keeping a very straight face. So I found myself having to clamber into the passenger seat of a minibus. These short skirts really are a pain. Stuart was to drive me into town as he had a special licence to drive the bus and was laughing all the way. I wanted to punch him, but I probably would have done the same thing to him, if I had thought of it.

In town there are two carparks, a little one near the bank and another the other end of the high street. So you can guess the little one was full. Rather than drop me off at the bank, Stuart just drove straight to the other carpark and made me walk. He said he had a couple of things to do and those shops were near that carpark. After calling him "A complete Bastard!" I set off on the hike along the high street, him still laughing. I was waiting for someone to call me out for being a bloke, but no one did. I even got smiles from a few men wanting to catch my eye. This was weird stuff.

After depositing the cheques at the bank, I thought about visiting a few shops for more clothes for the rest of the week. I wanted Stuart to have to wait ages and serve him right. I must have been gone an hour and when I returned and he looked angry. When he realised what I had done carrying the evidence back with me, he was laughing again at my predicament. He was laughing even more when I realised how much this was all costing me.

Back at the college, I deposited the bags in the back of my car and returned to work. We had a meeting of the whole department and I found my name card had been changed from Joe to Jo. At my desk was a new ID badge with my new photo on and the name Jo Smith. Even my damned Email address had been altered to Jo@xxxx.

The day finally came to an end and I headed home with lots of staff laughing and saying "See you tomorrow Jo!"

That night once out of all the clothes I thought about relieving myself of the days stresses, but didn't feel in the mood. I knew something was wrong as I am always in the mood. I sorted out all the purchases and hung them up or ironed them ready. It was quite a collection. My wardrobe needed extra room so I pulled out a few of my "man clothes" and folded them carefully into my big case and put the case away. As I hadn't the time to try anything on in the shops, I had just bought them and kept the receipt for if they didn't fit. The plan was I was going to play a bit of roulette. I now had an outfit for each day and I wrote down on four bits of paper what they were and put them in a bowl. In the morning I would randomly pick an outfit and only then find out if it fitted.

The next morning came and it was a lovely warm sunny day. Before anything I picked a piece of paper and it said "White Stuff dress". The White Stuff dress was a grey tunic summer dress with purple, white and pink flowers on it.

Once ready for getting dressed and makeup a bit better than the previous day, I got the dress out. It had a side zip and a tie at the back. I hung it up while I put on the fresh underwear of pink bra and knickers. With chicken fillets in place I tried the dress on. For the life of me it was a contortion act to get it on without ruining the makeup. Once on as I zipped it up, the dress went from a slouchy mess to a perfectly tight fitting dress. Looking in the mirror I rolled my eyes as it was as short if not shorter than the skirt yesterday. It did show my legs off well though. I hadn't noticed the previous day how good they looked, all shapely and tanned, well fake tanned.

With new earrings and necklace I now went for the shoes I had found in a charity shop. It was a pair of strappy sandals from Dune. The heels were a bit higher than yesterdays shoes, but I had found yesterdays shoes pretty comfortable, so went for it. To finish off the outfit I had a short cardigan.

When I went outside I was thankful for the cardigan. Yes it was sunny but there was a cold breeze and my legs instantly goose bumped. For the first time I felt a breeze go up and around my knickers. With lace knickers, they didn't protect my intimate areas from the breeze. It felt quite strange feeling the breeze on my bum cheeks.

Although the dress was short, it did make life easier when getting in and out of the car. My only worry was showing the bright pink knickers if the hem of the dress was caught in the breeze. Overall I was far more relaxed heading into work and once parked didn't think twice about getting out and going to my office.

Again I was greeted by many positive comments. As I chatted to a lady from another department in the corridor, I suddenly had my bum smacked. Stuart had quietly walked up behind me, lifted the hem of the dress and swung into action. I was in shock as he said "Good morning sweet cheeks! That's a nice short dress!" Before I reacted, he was gone. I said goodbye to the lady I was talking to and headed to my desk.

I was to find out that the dress was really quite short. As I sat at my desk, I found the dress didn't fully cover my bottom and legs, so the course material of the seat felt rough against my skin.

That lunchtime I found myself with my friends out in the grounds of the college sitting eating sandwiches. They all marvelled at my second outfit. Stuart and Sharon were shocked at how well it fitted me and how I looked. I felt this was a victory having been classed as a blokey bloke only a couple of weeks before.

After work, I went for a walk at the local park and enjoyed the peace and quiet. The sun was still pretty warm, but that chilly breeze was still there. A couple of times I had to quickly react to the hem of the dress flipping up. I left the park, I felt, with my dignity intact.

At home I again didn't fancy a session of relieving myself. My brain had loads of sexual ideas to wank to, but it just didn't feel right. So it was another quiet night.

Wednesday I had picked "Monsoon Summer Skirt" from the bowl. The skirt I found was still short but thankfully a little longer than the previous day. I was thinking I must have a warped sense of skirt and dress lengths. The skirt was a flared cotton summer skirt from Monsoon. It had big blue flowers on a white back ground. Today I had chosen white bra and knickers again. This was a good move as the top I had was a white chiffon material. I had one hell of a fight with the top getting it on. It buttoned down the back and in the shop I thought it was an interesting idea, so got it. I quickly realised men are not as flexible as women. It was incredibly difficult getting the damn top on and buttoned.

When ready to go I had a look in the mirror and this time I was shocked at how easy it was to see my white bra under the chiffon material. Plus the way the top was semi tight around my bust, added to the view. I wasn't going to back out now though and I headed off to work. Walking to the car it became patently clear it was more than a breeze. The light cotton skirt was doing everything but stay covering my white knickers. I had to forcibly hold the hem down until I was in the car.

My Wednesday at work was pretty uneventful. At lunchtime I had a little internal cheer to myself as I was half way through the ordeal and it wasn't going that badly.

In the afternoon I needed to visit the farm which was a good mile walk across the College grounds. The wind was still being annoying and on more than one occasion the skirt flew up above my waist. Once the farm visit was complete, I had the walk back to contend with. "How can women cope with this?" I was thinking to myself.

At the end of the day I needed to go to the supermarket and do my weekly shop. It was a very strange feeling. Apart from the goose bumps on my legs and arms when going through the chilled section, when I got home I noticed what I had bought was different. I didn't have any chocolate or beer. Instead there was grapes, strawberries and wine. No sausage rolls or burgers, but more salad and veg. I actually was subconsciously watching what I ate so I wouldn't put weight on.

It was another sparse night as far as wanking goes. Again it just didn't feel right and my mind strayed to other things.

Thursday arrived and the piece of paper said "Pink". So today I was to wear a surprise find in a charity shop. It was a Laura Ashley flared knee length silk skirt. It was pink with black and white flowers on it. What had made it special was that I had found the matching top as well that was in a plain pink.

With the wind having dropped, I was completely at ease out walking and the skirt had a lovely way of swaying. I couldn't believe what I was thinking. I was actually feeling positive as the silk of the clothes felt wonderful on my skin and made me feel special. As a man, this was just really strange and novel to feel this way.

The working day went with a blur, it just seemed as if everything was perfect. After work I went for another walk in the park and the whole experience was so uplifting.

Once home though, I was concerned that I still didn't want to have a wank. In my normal bloke mode, I was a wank every night kind of guy, but here I was on my fifth night without any relief and it felt normal. That night I knew what I would be wearing on my last day. It had been purchased as a bit of a self dare and seriously, could I get away with it?

On the Friday morning when ready to dress, I picked up the final piece of paper and it said "Oh, you tart!" From the wardrobe came out a River Island black bodycon mini dress. I already had black bra and knickers on and the dress fitted all the way from top to bottom, well literally just past my bottom really. To go with it, I had purchased a pair of high heeled black patent stiletto shoes. With everything on, my legs looked as if they went on for ever. The hem of the dress was only a couple of inches below where the knickers ended.

Again, rather than have second thoughts, I grabbed my stuff and shot out of the flat and headed to the car. Today though I found how difficult high heels were. One and two inch heels I could easily cope with, but these were four inch heels and I teetered around like a fool. Walking to the car and looking ladylike was not an option, but I refused to head back and get more sensible footwear.