Tiffany did this TV caption and I extended the story
This a picture of going to the leaver ball at the beginning of last month. That was after the last exams and was a significant day in my life for many reasons. Let me tell you a little about myself and how I came to look so pretty.
My name is Pete and live a few doors away from Kimberly or Kim for short. Our mum’s got on well so we would walk with one or the other to school as juniors, then at secondary we just carried on the tradition. We also played together as our mum’s shared the child care until we were old enough to play on our own and we just carried on being friends and played together into our teenage years. It did help that Kim was a tomboy and would play football with the boys, liked riding a bike and going swimming. Even into the sixth year we stayed friends, more just chilling out than running around doing sports.
There was an irony to Kim, she was this tomboy in jeans tee shirt and short hair, her mum was a mobile stylist who always looked ready for going out, never a hair out of place and make up perfect. There were a few times I walked in on the mother daughter argument ‘why do you want to look like a boy when you are so pretty?’ I was usually dragged out of the house by an angry friend who was just rebelling against her mum. Easy to see now.
Anyway enough background. The leavers ball, and me and Kim were sort of going as a pair, not a couple you realise, we never did anything like that. I was at home having my breakfast watching the TV, the mothers were in the kitchen having a coffee, I was summoned into their presence and went to find out what was so important.
‘Pete do you think Kim is going to wear a dress or even loose the jeans for the ball?’
‘Doubt it.’ I answered.
‘But she is so pretty, would you rather her look like a girl?’
‘This is Kim you are talking about, she is pretty but I can’t think how you would ever get her in a dress.’
‘Well Pete we have had this idea that might just shame her into letting Jill have a pretty daughter for one day at least.’
‘Yes if we made you into a pretty woman and showed Kim that you can look good and it is not a problem for you then she might see there is no harm in looking her best.’
A pause while this sank in ‘let me get this right, I let you turn me into a girl, let Kim see me not making a big deal out of it, and hopefully she will see it is ok and wear a dress to the dance.’
‘That’s about it.’ Agreed the mum’s.
‘Just one problem, I might not look that good, oh and a second I might not want to do it.’
Jill answered the first ‘You have a nice face with good bone definition and a slim figure, not forgetting that lovely mop of hair on your head.’
Mum answered the second ‘And you are intrigued to know what you would look like, you have asked too many questions and taken too much interest in women’s style for me to be wrong.’ I stood in front of them and blushed at mum’s very true answer ‘Jill I think we have our answer, Pete will do it.’ They exchanged smiles ‘Now remember you have to make Kim think this is no big deal, anyone can do it attitude.’
‘Ok, but the dance is this evening.’
‘Don’t worry, I bought Kim a dress and you should know I have everything needed to style a woman.’
What followed was a most remarkable day, ok I was interested in the whole woman thing about how make up changed the way a face looked, how a dress style looked better on one person than another, but to experience it is a whole different thing.
While mum took me upstairs for a shower and to denude my body of hair, Jill went home and returned with everything she would need. I spent an age sat on a kitchen chair being pampered. My head was massaged with several products and rinsed even more times by Jill, mum applied soothing creams to my skin which also added some tan to my pale limbs. Mum did have to go out shopping when she realised I had a different size feet to everyone else leaving Jill to make up my face and do my nails. I don't know what I was thinking at the time but never thought beyond the moment really as Jill thinned my eyebrows, she offered supportive words like ‘not that many just enough to create the effect.’ And when she did my nails adding a good 50% to their length reassured me with ‘lots of customers have them just for a special occasion, worth it just for the whole look though.’
When mum came back I knew Jill had done quite a transformation even though there was no mirror for me to see, I could see in her face and in her comments that everything was going to plan, I was looking pretty, which for an eighteen year old lad was not the most overwhelming endorsement of my masculinity.
Sorry back to the story. I was sat in the kitchen drinking tea in a cream silk kimono dressing gown, my hair up in curlers under a cap connected to a drier, my face was covered in non male cosmetics, my nails were longer and sporting a pale pink gloss finish which matched my toes. Mum poured herself a cup and opened the shoe box she had returned with, I did not need say a word my face told them I was shocked, she had bought skyscraper heels for me, her reassuring words ‘you are young and fit, these will be no problem to stand in, we only want you to look the part not walk into town in them.’ They both laughed as my face relaxed.
It was not long till lunch but Jill wanted to get a few more things done. She felt my hair was right for styling and removed the curlers and set about it with a scissors, hand blow drier, brush and spray until she was happy with the result. I was less than happy with the amount of hair on the floor but I had agreed and it was a bit late to start saying I wanted out. I have to say my whole head felt very different as I ate my salad sandwich, the skin was slightly greasy, my lips tasted of lipstick like they should and my hair felt so stiff it might break, but the longer nails were the weirdest thing to get used to, they got in the way so often that the mums commented about how easy boys had it.
After lunch I was given some underwear to get into, the bra was awkward but fastening at the front then spinning it round worked but with no straps I was not too sure where it should sit. The satin knickers were a delight though making my organ which I felt made me male, reacted to this feminine luxury. I had been able to change in private but was embarrassed when I stood in front of my mum with in underwear with a semi on. She just ignored my condition and asked me to try the dress on. I stepped into it and pulled it up before she pulled the side zip up. It was tight on me or fits well as Jill put it.
‘Fill out the top and squash that thing down there, men are so obvious aren’t they Fay.’ Said Jill.
‘I have some control pants upstairs.’ Mum said as she left for her room, a supplementary question from the bedroom ‘stockings or tights?’
Jill’s reply ‘I think he would like stockings.’
Minutes later mum appears with two stockings over her arm and more underwear. ‘Out of the dress dear and let’s see if we can improve your figure.’
The pants did indeed squash my dick inside me, so much that when I felt the erotic sensations of a fine stocking caressing my leg as I rolled it up, the erection had nowhere to go. Back in the dress and socks pushed into the bra to fill it out I thought I was nearly done. But no, shoes to contend with as I wobbled about the room holding onto the furniture until I got the hang of standing on my toes.
‘He is looking fantastic Jill, you really can work miracles, let me go and find some jewellery to finish him off, or should I say her off’ she left the room giggling at her joke.
I soon had a chunky charm bracelet round one wrist and a watch on the other, the last shock was ‘Jill can you do his ears I don’t have any clip-ons and these long ones would look great with that hair.’
‘Oh easy enough dear, come here Peta.’
I thought who is pet-a, then it dawned on me, gave them an enquiring look hopefully saying ‘is this really necessary.’
‘Just finish you off perfectly.’ And after a couple of painful stabs in my ears I was adorned with ear rings that tickled my neck.
‘Right now then love remember what we said this morning, act as though this is not a big deal, if you can do it Kim can do it as well sort of thing.’
‘Ok you just go and make yourself comfortable in the living room while we wait for Kim to turn up.’
I went with a little more grace than I had when I first put the heels on and settled myself into a chair with a magazine I had picked up. I had always puzzled why women sit on the edge of seats with legs tucked under, well I found out the heels rather make your feet sit back into the chair and a tight dress is rather restricting, I actually found sitting on the edge more practical. I was also finding out how nice the fabrics were on my skin, the dress was a satin sort of material which was cool and soft, the stockings were just silky on my legs, the satin knickers were a delight, even the ear rings on my neck, the flicked back hair, the charm bracelet, the taste of lipstick all made me feel very different and wonder what Kim had against such nice things, ok the long nails, bodyform pants, throbbing earlobes and uncomfortable shoes were on the down side but surely just for a special occasion Kim could give it a go and see that she would look fantastic.
I had stopped my musings and opened the magazine, oh heck, one of Jill’s beauty journals, and that just had to be the time Kim walked in.
‘Oh my god Pete what have they done to you?’ she shrieked as she saw me.
‘Kind of wanted you to see if I can look pretty then you could as well. I mean I look kind of pretty like this, just imagine how good you would look.’
‘But you are sitting all prim and proper reading a glamour mag, you not only are made up like a girl you are behaving like one. I can’t believe you let them talk you into this.’ Then turning her attention from me she went to the kitchen ‘Mum you don’t get it do you, I am not like you, I don’t want to be a model, I don't want to attract some stud male, I just want to be me, and as for doing that to Pete, well words fail me.’
Her mum was first to respond ‘I just wanted you to see how pretty I could make someone, and then you could go to this dance looking fabulous, and you have to agree I am good at making people pretty.’
‘But why Pete, I know you can do things with your stuff, just why pick on Pete.’
It was my mum who had a word now, ‘He agreed to it.’
‘Pete, tell me you didn’t.’
‘I did.’ I hung my head and fiddled with the bracelet as I mumbled the answer, as I felt every ounce of self esteem drain out of me.
‘I always knew you were a bit gullible but this is beyond that, how naïve can you be to let them talk you into it.’
I tried to defend myself ‘Have you ever tried any of these clothes, they feel great and your mum’s head massage is lovely.’
She was staring straight at me ‘you will be telling me next you like dressing up like this and like walking in those heels. Tell you what get up and walk over there for me.’
Kim is a fearsome person when fired up so I walked over to our mothers. I did quite well hands out a little just for balance.
‘Bloody hell, you can even walk in those fuck me shoes.’
‘Kim enough of the language and Pete did this to show you it is no big deal to look pretty.’ Jill put her arm round my shoulder ‘and we have not done anything he objected to or forced him into, it really is not such a big deal is it Pete?’
‘Well I suppose not.’
Kim just glared at me ‘I thought you were my friend, you understood me, well if this is no big deal then you might as well have my ticket, I am not going.’
‘But we were going together.’
‘God you think I want to go after seeing you dressed like this, how my mother thinks I should look, no thank you. But if it is no big deal and you do have a spare ticket now, let me call someone.’
I just stared at her while her mum asked who she was calling.
‘Oh hi Sam.’ ‘Yes Kim here, just called to ask if you were going to this dance.’ ‘No I’m not, and wondered if you wanted a ticket.’ ‘Well yes I know you are gay and that was why you were not going’ ‘Yes but Sam listen to this, if you could take a girl who is really a boy.’ ‘Yes a long story but my mum has dressed up this friend for the dance and he has no one to go with.’ ‘No I am not winding you up, come and meet him/her yourself.’ ‘Yes you know where I live, well a couple of doors up.’ ‘Yes Pete’s house.’
I was trying to not get upset as the day was turning into quite an emotional one, but managed a ‘Kim what the hell have you done, Sam he is gay.’
‘Perfect hey, a nice big gay bloke with a sissy boyfriend partner who no one will guess is really a boy.’
‘Mum help me here.’
‘Not sure you need any help, besides perhaps where your tears are making the makeup run. Kim is right you never complained once, you do look very at ease in the dress and heels, I think you should at least give it a try. I mean how many girls have you been out with.’
I started to think of names to make it sound more than zero, but Kim shot in with ‘I will tell you none, I reckon he is as gay as me, just not admitted it yet.’
I was just about to defend myself and I could see mum looking at me with questions building when the door bell rang. Kim went to answer it.
‘Sam come in, you know my mum and Pete’s mum.’
‘Hi’ he smiled at them.
‘And this Sam is your date, pretty isn’t she?’
‘Sorry Sam this is not what it looks like.’
‘Yes it is’ cut in Kim ‘we have one gay lad without a date, and here we have one undecided sissy lad all dressed up as if he is looking for a date. Simple.’
Sam asked the next question ‘But why?’
‘They thought if I saw Pete looking pretty I would want to look ridiculous as well.’
Kim’s mum stepped in at that and ordered her out of the house, ‘Sorry Sam to have let her drag you into this.’
‘Not a problem Mrs Smith, just glad to have seen Pete looking this good, I would not have believed it unless I saw it.’
‘We called her Peta.’ My mum put in.
‘Well, Peta, you agreed to all this?’ I nodded ‘And you look great, does it feel ok.’ Another nod ‘And it is no big deal looking like this?’
I started to say ‘Well actually’
But mum talked over me ‘Peta it would be a shame to waste all this effort on making you look so good, and Sam here is wanting a date, so why not go.’
‘What! You look the part, no one will recognise you and if they do tell them you are Pete’s cousin or something, but go and experience something totally different, be Sam’s girlfriend, see the world from behind a new set of eyelashes as it were.’
‘Tell you what, me and Jill will make ourselves scarce and leave you two to chat.’
As soon as they had gone I apologised again, and he told me I looked great again. I made us a coffee each and answered his questions about what they had done to me and more cunningly, how I felt. As our coffees emptied I could sense myself being stared at and I was looking at my fingernails in my lap.
‘You are quite cute you know. I reckon we could have some fun tonight. Everyone thinks I am gay so turning up with a good looking girl will be great, and I reckon deep down you would like to stay in that dress and see what it is like to be seen as a girl.’
‘Sam I am not sure about any of this.’
‘Ok well I am sure you can do this, get Mrs Smith to do a few repairs and I shall be back at seven in a suit to escort my partner/boyfriend/girlfriend to the dance.’
He got up came past me and gently kissed my cheek, it felt like he had electrocuted me I got such a buzz from it.
Five minutes later mum is back ‘Well?’
‘I am going.’
‘Not quite the result we were expecting but an interesting one all the same. Now slip out of the dress and into the dressing gown we don't want in spoilt. Jill will do you make up again and I shall go and find a hand bag and wrap for you.’
Sam turned up and mum rang for a taxi. Besides the memories in my head Sam took a few pictures as well as the professional ones. The picture above is on the balcony above the dance floor at the venue. Quite a good shot really of the architecture, and of me.
Well that was the first day and I had quite a good time, a few shots before the dance and I was relaxed enough to enjoy myself.
But that was not the end of it. I woke up the next morning feeling rough, a shower, some food helped a little but seeing long pink nails at the ends of my fingers and a rather feminine hairstyle even without the styling, framing my still pierced ears and narrow eyebrows I did wonder what life would hold for me as Pete. I was discussing with mum what I could do when the answer came from a text message.
‘Peta. Mum wants to meet you. Taking us out to dinner. Posh ’
Mum’s solution was simple at least for the short term, don't change anything be Peta for another day. She lent me a grey casual dress and showed me how to do make up and style my hair. I found her attitude towards me quite different, single mum and son is clearly not like mum and daughter.
Sam picked me up with his parents and took me out to a smart restaurant where I was on my best behaviour. His mum was nice if a little protective, his dad was charming but did not wear the trousers, she did.
At the end of the evening Sam’s mum looked me straight in the eye ‘Peta you are a perfectly charming girl and from what Sam tells me completely suitable for his erm preferences. Now like Sam I guess you have not found yourself a summer job, so I am going to offer you one as office junior at our warehousing business.’ I was about to say but I am not a girl when I was cut off, she was only pausing for breath ‘The job is only open to Peta, I am not asking Peter if you were thinking that. I also will understand if you need to get yourself some new clothes for such a job as the dress you have on would be inappropriate.’
‘Well er thank you Mrs Turner, I don't have job and I am not sure how much you know about me.’
‘Enough to know you made quite an impression on my son.’
Sam’s hand was on my thigh and squeezing. Flustered I stalled ‘I really should make sure with my mum before saying yes.’
‘I understand it is a big step for you to take.’
By the time I got home I felt I had been stitched up, our mum’s much have spoken by phone at some time because mum had a few extra bits of information, like the hourly rate and a clothing allowance was included. She told me I would never get such an opportunity, I asked if wearing heels and a skirt was such a great opportunity, but she countered with the point that I would be on good pay and Sam was nice boyfriend material.
Well as you can guess I took the job, filing, answering the phone, making the coffee, but also a crash course in how the female behaves and the effort taken to look pretty all the time.
By the time the results came out I had worn jeans only twice and had not dared go out as Pete for fear of being teased for the feminine alterations that had been made to my appearance. And after I got my results there was little point in hiding my female persona, I got terrible grades, no courses I wanted would take me, but Mrs Turner offered me a permanent position in the office. Mum said it would be foolish to turn down any job with my results and what with there being so many under 25s out of work. I checked with Mrs Turner that the job was for a female junior. ‘Yes Peta, now I am guessing you want to get off early and get ready, I hear Sam is going out to celebrate his results.’
And so instead of being a student at some university in baggy clothes I am Mrs Turner’s assistant and dressed like this.
Not quite the future I was expecting when I was sitting english, french and art exams only a few months ago. But one that is proving very agreeable with my mum, Mrs Turner and rather surprisingly, Sam my very nice boyfriend.
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