In Need of Direction

Finishing university with a first in maths, I, Matthew Scott, was ready to set the world on fire. I found though, the jobs market was not what I expected. A twenty two year old man, all I could find was work in a local coffee shop. The money was just enough to keep me afloat. This was all to change when a special customer came in.

On a boring Wednesday, when nothing exciting ever happens, in walked the tall slender outline of a lady I instantly recognised. It was my school maths teacher Mrs Williams. As she came to the counter to order her drink, she instantly recognised me. Mrs Williams had been a great teacher to me. In fact all the boys paid attention in her class as she was a very attractive lady in her 40s, slim, long blond hair, just over six feet tall and she always wore killer heels making her taller than most. At twenty Two, I was just five foot eight and slightly under average sized. As I was blond, I had very little facial hair and knew it would be impossible to grow a beard, that was the latest fashion trend. Instead, I grew my straight blond hair a little longer, well maybe a little too long, but it was my rebellion to the lack of a beard.

I quickly organised a break to chat with Mrs Williams and we sat and chatted about stuff. Her husband had made it big and she had retired from teaching. Mrs Williams was over the moon at me getting a first in maths, but was concerned where it had got me. As we chatted and drank, Mrs Williams had a brain wave. Her daughter was twenty four and had finally decided she wanted to go to university. Trouble was she had failed her A Level Maths three times and desperately needed it to get to the university she wanted. Maybe I could do some private tuition. I was well up for that and we soon had arranged everything.

Two days later I was walking up a long drive to an impressively large house. As I neared the front door, it swung open to reveal Mrs Williams standing there with a smile on her face. She gave me a whistle-stop tour of the house and organised a tea for me in the kitchen. The kitchen was bigger than my entire flat. Mrs Williams then walked me to the library where her daughter was waiting. As we entered, I recognised the daughter instantly from school and my heart sank. It was super bitch Debbie. Her and her two friends Donna and Diane were the nightmare of all at the school. How on earth could she possibly be Mrs Williams daughter. Debbie was nearly as tall as her mother but thicker set with broader shoulders and nowhere near as attractive. I guessed she looked like her father.

As we sat to chat, Debbie was different. I mean completely different, all polite, friendly and quite charming. Even finding me a coaster for my cup of tea.

Mrs Williams left us alone to go through what was needed and we soon had the text books open. I first needed to assess how far off she was and at the end of that first two hour session, I realised Debbie was a long way behind. Before leaving, I had a quiet chat with Mrs Williams about the task in hand, but she was confident of my skill in helping her daughter.

A week later I was back at the house for the two hour session. As I entered, Mrs Williams said she had some chores to do in town and Debbie was in the Library ready.

Soon Debbie and I were back at the studying and many notes were being written in the hope they would be remembered or help as aid memoires in revising. Our study was interrupted though by the door bell. Debbie leapt up and I soon heard two voices I remembered from school. It was Donna and Diane. So the three super bitches were together and a feeling of deep foreboding came over me.

After a few minutes I went to find where Debbie was as she hadn't returned to the studying. All three were in the kitchen. It looked like Donna and Diane were helping themselves to some red wine and maybe Debbie was trying to stop them and failing.

Very quickly they got louder and louder, and that's when I made the mistake of stepping in. Donna chose that moment to chuck a glass of red wine over me. Donna and Diane were laughing like drains. Debbie though looked mortified. As she looked for tea towels to clear up the mess, Diane then poured a bottle of wine down the front of my trousers. I was now covered from head to foot in red wine.

As laughter continued in the kitchen, Debbie directed me carefully upstairs to the guest bedroom. She suggested I have a shower and while my clothes were washed, she would find me a dressing gown.

Once in the guest shower I heard Debbie say she had taken my clothes to wash and had left me something to wear. She then said about coming down to the kitchen once finished.

After the shower I noticed there were only hand towels in the bathroom, so dried myself as best I could. Opening the door to the bedroom carefully to make sure nobody was there, I then walked in to find a dressing gown on the bare bed. Oh my god, I thought to myself. It was a short pink satin gown . I frantically looked around the room and there was nothing. All drawers and wardrobes were empty. The bed was bare of sheets. There was nothing for it but to wear the dressing gown.

Putting the dressing gown on was a very strange experience. It fitted perfectly but was quite short, ending half way between my knees and bum. I tied it as best I could and then left the bedroom.

As I descended the stairs, Donna was at the bottom filming me on her mobile phone. This was going to be a terrible, terrible day in my life. Would it ever be the same again. As I entered the kitchen the laughter was at fever pitch and Donna was still filming every moment.

Things soon got worse when Diane showed me my clothes, well the remnants of them as they had been cut into tiny pieces. Only Debbie showed any remorse and suggested she find me some clothes to wear as it had been Donna and Diane's idea to destroy mine. At that the two girls chinked glasses in a form of celebration.

Either I go home in the pink satin dressing gown or I agree to Debbie's suggestion of other clothes. There wasn't much of a choice so Debbie took me upstairs to find something.

Debbie went through a thought process and spoke out loud. No her fathers clothes wouldn't fit as he is seven foot and a big guy. Mums clothes wouldn't fit as she is far slimmer than me and much taller. Debbie's own current clothes wouldn't fit me as she was much taller and far more broad.

She then came up with an idea. Some of her old clothes from when she was 18 and 19 may fit me, but that's when she dressed a bit more girlie. Much of the designer stuff had already gone to charity, but there were still a couple of bags full in her room. So Debbie directed me back to the guest bedroom and then headed off to get the bags.

On entering, she handed me a pair of under pants to wear. As she didn't want to embarrass me, she had found a simple pair of black knickers in a silky and stretch fabric. Dejectedly I slipped them up my legs and they stretched perfectly over my body.

I looked in horror as Debbie pulled out the items from the first bag. It was all skirts, dresses and fancy tops. The sort of thing a very girlie girl would wear. As Debbie pulled out the last item from the first bag, it looked denim and I hoped it was a pair of jeans, but it was another skirt.

The second bag was equally torturous as every item seemed to be more girlie, pink and lacy, than the last. Debbie commented, this was much of her party wear. In both bags there wasn't a single pair of jeans or trousers, or even a check shirt. Nothing remotely masculine was in sight.

We surveyed what was on the bed and after a quick discussion we agreed there was nothing for it, but to find whatever would fit. It was the most embarrassing half an hour as dress after dress fitted perfectly. Well everything fitted perfectly in reality.

After further discussions, we decided it would be best to avoid a dress. Instead we chose a shocking pink chiffon blouse and a denim skirt. Although the skirt wasn't a mini skirt, it was well above the knee. To finish, a pair of black ballet pumps fitted my feet.

I looked in the mirror and was shocked with what I saw. Before me was a nineteen year old young lady. Not a hint of facial hair and none on the arms or legs for that matter.

After a bit of help from Debbie, I got the confidence up to leave the room and head down the stairs. At the bottom, yet again was Donna with her phone filming everything. When both Donna and Diane had a proper look they were amazed.

Debbie looked at the clock and realised her mum would be home shortly, so she grabbed my arm and dragged me to the library and do a bit more study.

Five minutes passed and we heard the front door open. Mrs Williams was greeted by Donna and Diane in the kitchen. After a little chat she came into the library and Debbie took my hand, in what I thought was to support me.

Mrs Williams looked at me in disbelief. She said Matthew a couple of times and then took a closer look. Debbie said there had been an accident in the kitchen and my clothes had been ruined. I was about to speak up but Debbie took my little finger and twisted it in such away as to make pain shoot up my arm. Mrs Williams then said the transformation was amazing and asked me if I was ok dressed like this. Debbie hurt my finger again making me say yes, I was fine. Debbie then went on to suggest my new name be Maisy.

Mrs Williams called in the two other girls and the three of them marvelled at how I looked. Right there, Mrs Williams said this called for a Pizza and soon we were being shoed out the front door to her large 4x4.

As soon as we were outside, I felt the breeze between my legs and the skirt moving in the wind. Debbie took shotgun in the front. Donna and Diane had the next two seats and I was made to get into the third row at the back. With the short skirt it was difficult to get there with any dignity, but I only heard a couple of sniggers from Donna and Diane.

What was I doing, in the back of a 4x4 dressed as a young lady and heading to a Pizza restaurant. I had no choice but to front it out.

As we ate our food, Debbie told her mum, she preferred I was dressed this way and it would help her studying far more. I caught a little smile on Mrs Williams face, but she was very open to accept Maisy and if she paid me £5 more an hour, would I dress this way for the lessons?

I couldn't refuse. Not because of the extra money but Debbie had my little finger again and made it hurt.

After the Pizza Restaurant, Mrs Williams dropped off Donna and Diane at their homes. We three then headed back to the big house. The rest of the evening Mrs Williams spent selecting outfits and placing them in a case for me to take home. Once the case was almost full, she squealed at seeing a particular dress. It was a coral coloured short stretchy skater dress with no sleeves. Mrs Williams spoke of remembering Debbie wearing this dress and it felt not that long ago. As she folded it into the case, she demanded I wear that next week.

Finally packing a few pairs of the ballet pumps and a bag of I didn't know what, Mrs Williams finally zipped up the case and it was time to give me a lift home.

The combination of Mrs Williams being very excited and the threat of pain from Debbie, Donna and Diane, I said nothing in the car on the way home. Luckily it was late and none of my neighbours spotted me cart the case up the stairs, while dressed as a lady.

As I only had a few items of mens clothing, there was plenty of space in the wardrobe for the many dresses, tops, blouses and skirts. Soon it was all packed away, apart from the bag Mrs Williams had put in. Opening the bag, I found a whole rainbow of coloured knickers and a few bras. I cleared some drawer space and put them all away. I didn't worry as I wouldn't have to think about it for six more days.

That night, my mind was all over the place and I have to admit, I had the greatest session on my cock. I must have cum three times and still my cock was ready for more, but I needed my sleep ready for the coffee shop in the morning.

Next morning, I did my usual shower and breakfast, but as I went to get dressed, I opened the drawer and before me were the blues, greens, yellows, pinks and reds of knickers. I had a thought, no one would notice under my uniform. So I picked out a pink and lace pair and when I slipped them on, they felt amazing. Once I was fully dressed, I had an inner smile thinking what was beneath my trousers.

That day at work flew by with a smile on my face. Customers and colleagues noticed and liked the new me.

I almost skipped or ran home and soon my cock was hard into action. Not sure how many times I came that evening, but I didn't bother with food. The next day was the same apart from me choosing a great pink striped pair and I actually ate something in the evening. Day after day disappeared in a strange glow.

The day of the next lesson arrived and I took great care in washing, especially my hair. As I was ready, the coral skater dress almost lit up the room, but first I needed to choose my underwear. A rather brief pair of white knickers with lace panels took my fancy. My cock instantly wanted to perk up, so before it got too hard, I pushed it back between my legs as I slipped up the knickers. I then looked at the bras and a nice white one seemed to match the knickers. After a hell of a fight, I managed to get it on and although it didn't do much for my chest, it strangely felt right. Pulling the stretchy dress over my head, it was only once it was in place that I realised just how damn short it was. Adjusting it this way and that made no difference. It only covered my bum with a couple of inches to spare.

Thinking no more of it I put on a pair of pumps and found my secret weapon. During the week I had purchased a big pair of sunglasses. Slipping them on, I looked in the mirror and now I definitely didn't look like me dressed up. Now confident my neighbours wouldn't recognise me, I waited until the hallway had been quiet for some time, then nipped out of my flat and without a second thought headed for the main road towards town.

As I walked, my feeling of nervousness quickly went and my confidence grew. The hem of the dress swayed as I walked, but it felt so right. I took my time as I walked around town. Funnily I even plucked up the courage to go into Newlook and a couple of other ladies clothes shops. A whole new world had been opened to me.

Once it was time, I headed off for Mrs Williams house and she greeted me at the door as usual. This time though she had a wonderful smile on her face. On greeting she said she wasn't sure if I would come in the dress and I replied, I didn't want to let her down.

Debbie was in the library waiting for me and we cracked on with the maths. Even Debbie treated me differently and was far more gentle almost like a sister.

Once the two hours were us, Mrs Williams said she had a surprise for me and within a few minutes we were in the car and heading to town. I just went with the flow, enjoying every moment in a sort of daze. My mind only came round when we entered a beauty salon. Staff soon busied themselves around the three of us and after a couple of hours I now had wonderful red finger and toe nails. The colour matched my lipstick and other makeup accents. What puzzled me was my gut felt most giddy when they pierced my ears and fitted stud earrings. When all was done and paid for we were off to the posh restaurant in town for a wonderful meal.

That night my cock exploded on multiple occasions. It was only in the morning when I got up ready to go to the coffee shop that my stomach dropped. The previous night I had taken the makeup off as guided, so that was fine, but what would I do with the red nail varnish and the earrings?

I tried different ways of getting rid of the varnish, but without success and I had to leave or I would be late for work. Putting my brave face on I headed into work with red nail varnish, trying to think of excuses.

On arrival, almost instantly the manager noticed and called me into her office. We chatted for a few minutes. None of the excuses I had thought of would have worked, so I just said I had worn it the previous day. The manager smiled and said she was a friend of Mrs Williams and knew all about me. Without me even having to think about it, she went on to say that company policy was very pro-LGBT. So she could adjust my record and she actually said she would dearly like to see me the next day properly dressed up! She reminded me of the rule of black skirt or trousers and a white top.

The next morning came around sooooo fast and after showering I selected a black short skater skirt and a white semi sheer chiffon blouse with my white bra slightly on show.

I haven't looked back from these events and now live extatically happy as a young lady and just awaiting the transition surgery that Mrs Williams has kindly offered to pay for.