My wedding dress story
by Lauran
Don’t ask me how it came up at the beginning, I was round at Mark’s house and we had had enough of his new game and were just sitting about chatting. We touched on our lack of love interest, how possibly girls weren’t keen on gamers, what game we should get next. Usual seventeen-year-old stuff, well we thought so. Mark came out with the statement that his ideal woman would be someone like me, except she would obviously be female and not a weedy lad, someone who would play x box and chat, like we did. I thanked him for what I think was a compliment and tried to change the subject, though he was my best friend and got on really well I was not sure I saw him as my ideal partner.
It was at the end of college on Friday that Samantha caught us on our way home, gave us an invite to her party then ran off with her boyfriend. We read it, looked at each other and just said no. It would be couples and trying to pretend they were grown up, and for Mark and myself a gooseberry situation. Anyway Mark’s mum found the invitation and I happened to walk in on the conversation, Mrs Jones thought Mark should go, he had not been to a party in ages, and sitting playing games with me was no way to spend a Saturday evening, besides it was fancy dress which would make it more fun. Mark was not keen and suggested we had no costume or money to hire one, then I saw her face light up, she spotted her wedding photo and told Mark he could borrow his fathers wedding suit, a proper morning suit with hat and tails, the lot. Mark was not keen and pointed out I still had no outfit and dressing up as a groom would look odd, what did she have in mind for me, the wedding dress. Her answer took the wind out of our sails, she said why not, I am about the size she was twenty years ago, and we would make a good pair. I chipped in suggesting my mother might not be too enthused about her boy running around in a dress, and after a moments thought she rang her and asked her to come round, which is only three doors away, so was there in no time. I was trying to play it cool, I did not want to let on that I had enjoyed a few evenings alone in her bedroom imagining myself in her clothes, and the idea of wearing a wedding dress was secretly quite appealing. Anyway my mother and Mrs Jones quickly covered the discussion so far, and as I brought up the fact that my mother would hardly like to see her son parading around in a wedding dress, she just asked why not? I was a little stuck for words, coming out with things like, it’s not right, men are men, men wear trousers. They both shot me down, told me not to be sexist, that men wear trousers and so do women, women wear dresses so why should men not wear them also. I gave in as I was clearly losing the argument, but inside was having mixed feelings about how this adventure would work out.
Our mothers left us to discuss our fates, Mark only had one comment, that he would get his ‘wish’ I would be his girlfriend, how could I forget his statement a few days before, and told him I expected him to be a perfect gentleman. It was not late when I left with my mother and a dress bag that I assumed correctly contained the wedding dress. Mum was trying to get me talking about how I wanted to play the part, did I want to be a drag queen type, a clown style or a proper looking woman, when I asked which she thought would be best, she was in favour of a straight forward woman look, because Mark would be a normal looking groom so I might as well compliment his approach.
Mother started on me the next morning, it was Saturday and she was not that busy so it would be a good time to get the outfit sorted, I had hoped to do this all privately but mum had other ideas, I was in my briefs letting her put the dress over my head soon after breakfast, and she was making notes, I needed a chest, the hem dragged on the floor could it be turned up? My arms looked quite hairy, that needed sorting, and my hair was a scruffy mess that needed attention. Many other items were mentioned but not noted and I was feeling this might not be as much fun as I first thought. Over a coffee Mrs Jones arrived and discussed how things were going, Mark had had a fitting also and was apparently a spit of his father back then, he needed a haircut and a good shower and that seemed to be it for him. I overheard the topic of the hem come up, and Mrs Jones asked how short was I, only a couple of inches my mother informed her, they did not want the hassle of alterations and decided if I wore heels it would fall right. Then they talked about hairstyles and make up, then how to get them organised. I was starting to feel left out of it but waited for Mark’s mother to leave.
I asked mum if all the things discussed were essential, she was sure they were, so I asked if walking in heels was difficult as I hear women complain about them, not sure what the answer would be, she might even encourage me to try them, and she did, I tried not to look too pleased at the prospect of wearing heels but I possibly did not do very well at lying as she went to her wardrobe and found some sandals that could be adjusted around the ankles and told me to give them a try. She said they were only a low one and I agreed I had seen higher, but that did not help me as I staggered about hoping to find my balance, which prompted her to say that I did need practise because the dress would need me to wear at least a three inch heel. This was not going to be easy she reminded me as she told I should wear the sandals around the house for the rest of the day, and that seeing as I have never worn a skirt, let alone a full length dress it might be good to get some practise in there also. Anything else I thought, when she came out with ‘If we are going for authentic, maybe we should get your ears pierced?’
I asked if I had any say in the matter, to which she replied, not really, if I was going to be ready in a fortnight I would need to start getting ready now. Saturday went fine, when I was in the house I wore the sandals but changed when I went to Mark’s, who was quite downbeat about the affair, his mum wanted him to loose a few inches from his waist and get a proper haircut, like men should have with ears and collar showing, I told him some of what my mother had in store for me but assured him it was fine and in fact could be something of a challenge, for which I got an odd look of him.
Sunday morning and mother had been through her old clothes and found an old maxi skirt from her college days telling me I should try it so I can get accustomed to the feel and length of a long skirt. I agreed hopefully not to quickly and as I had lots of homework to catch up on spent the day in the sandals and skirt, and came to no harm.
That is except for early afternoon when I changed into my jeans and trainers and went with her to the shops, I came back with two sore ears and ring sleepers fitted in my lobes.
Monday I had a few at college ask about the ears, most saying how cool they looked which made me feel better, but it was when I got home my good mood wore off, a note from mum saying ‘Get changed then make a start on tea, don’t forget to use an apron’ I could only find her apron but wore it to keep the peace when she got home. Then I had another shock, she was late because she had been shopping at a discount shop and had me so I had some heels of my own, a plain court shoe with a towering, at least I thought so, three inch heel, to get used to the height she assured me. They were a tight fit which stops them slipping off, and I was to wear them whenever I was in the house instead of the sandals.
Tuesday I went round to Mark’s for a rest in the evening, he loved the earrings.
Wednesday, Mark came round unexpected, I was in the long skirt and high heels, he said nothing but I would catch him taking sideways looks at me, and I told him not to tease as I would get my own back later if he did.
Thursday, mum is making plans for the weekend, I am not sure of them all but I shall be busy it seems if all the calls she has been making are anything to go by. Got the skirt and heels of to a fine art I think.
Friday, mum wants me to get into an authentic girl mood and had got me a nightie, to prepare me for Saturday she adds. What will happen on Saturday I ask, nothing I won’t enjoy she reassures me. I put on the nightie before going to bed and showed her how it looks, I get a kiss, that has not happened for years, maybe she likes this as well.
Saturday, in the morning she gives me a make up lesson, first showing me how it is done, then cleaning it off and guiding me while I try to repeat what she had created. This feels a bit weird as I am in the nightie with her silk wrap tied around me. Once she was happy I had mastered the basics she tells me it is time to get everything sorted with the dress, a pair of control pants to keep everything controlled at the hips, a bra stuffed with tights to give me a big enough chest she hopes, then the slip, then the dress. To my embarrassment Mrs Jones is invited round for advice, the bra needs to be bigger, and my waist thinner to get the dress fitting right. Fifteen minutes later Mark’s mum is back with a corset and one of her bras, twenty minutes later I am putting my arms through the sleeves again and letting them button up the rear closure. I am uncomfortable but told it fits perfectly. Stepping into my shoes Mrs Jones asks if I would mind trying four inch heels so the hem is just that little bit higher, my mother says it wont be a problem, I just let out a girlie squeak and they have a fit of giggles, and hug me.
After Mrs Jones has gone and the dress hung up, mum tells me I should keep the corset and bra on so I can get used to them, and gives me one of her knitted tops to wear along with the long skirt which now sits more on my hips and therefore lower down, this causes me to be extra careful not to stand on the hem as I walk, I had already got used to lifting the hem when I walked upstairs, but this was needing a different gait to keep it out of the way, I was developing a very affected female walk by mid afternoon. Though I was not told to keep the make up on, I made no move to clean it off which prompted mum to suggest we try something extra on Sunday, when I asked what she clammed up.
I did not go round to Mark’s, so he came round to ours and got to be the first person to see a fairly complete female version of me, he said I looked hot, and asked if the tits were real, I told him to grow up and turn the X box on.
Sunday. Woke with nightie wrapped around my legs, which was very nice. Over breakfast, still in the nightie, mum tells me to have a practise with my make up and to wet my hair. Then while I am brushing cosmetics onto my face she is brushing and combing, then using her tongs on my hair, by the time we are done I look completely different, especially now my face is framed by my neat hair style, but all the while she was talking about how it would look best the next weekend. Instead of the long skirt she gives me a pair of cream silk cargo trousers and a green vest top, saying I could do with a change.
The afternoon is spent studying and trying to tell myself I will get used to the corset and bra. Then as I am expecting mum to tell me tea is ready she comes in with a jacket and a shoulder bag, ‘Right time you had a go at being outside, and being seen. Here put this on we are going to pizza hut.’ I would have objected if I could get a word in as she explained how I needed to be comfortable out while looking female, and learn some of what I need to know about female behaviour.
The next shock was the Mrs Jones and Mark were at the pizza hut already, Mark looking more nervous than me. Our mothers got on well chatting about this and that, but mostly about us, the comment to cause the most reaction from us was that seeing as we were bride and groom next weekend, at least we should be boy and girlfriend at least once beforehand, they had even got us to sit side by side on a small bench seat. Mrs Jones was full of praise for how mum had transformed me, and that the party would be great. Then to cap it all, mum invites Mrs Jones to go with her, and leaves Mark with their car to run me home.
This was getting a bit to much, a bit too fast I thought, our mums were setting us up like a blind date other than we were best friends. We drove to our house, I invited Mark in for coffee, and as we relaxed he comes out with ‘you don’t realise how good you are do you. No one took a second glance at you. You are prettier than most of girls in our year. You are great at this you know’ all I could do was blush and drink my coke.
When mum got home she made Mrs Jones a vodka and tonic, and then asked how we had been and did we want anything, I asked what was she offering as we had already had a coke, to which she said what did I fancy, a drink like Emma (Mrs Jones to me), I said I would try one and Mark had a lager because that was what he felt a man would drink. The next set up was that I ended up getting Mark a fresh lager only to find my seat taken and the only free one was next to Mark. Emma and mum then started teasing Mark that he has a pretty girl next him and why has he not put his arm around me, they hoped he would be more affectionate to his bride in a weeks time. The lagers and vodka relaxed us and after much teasing I cuddled up with his arm over my shoulder. Last blushing episode came as they got up to leave, as we said our good byes and Mrs Jones put her coat on, she nudged her son and told him he should say thank you for a lovely evening, I imagined what was coming, he said the words and his mother reminded him I was his girlfriend for the evening and had he never said good night to a girl before? He gave me a peck on the cheek, that was not good enough, and was asked if he needed showing what was expected, so he kissed me on the lips, which got an approval, ‘Now we are just going out to the car while you two practise properly, and we shall be checking’ they both grinned as they left us.
‘So are we going to do this and keep them happy?’
‘If you are ok with it’
Then I leaned forward and kissed him properly, hand round his neck so he couldn’t escape and moved my lips in an appropriate manner. Mother came back after a few minutes, ‘There is no stopping you’ we separated and both said ‘what’ together ‘it was your idea in the first place’
Anyway after they had gone I sat with mum cleaning my face and getting into my nightclothes discussing the evening. She had had a great time, she admitted some of it at our expense, but I was a great girl and that I would be terrific in the wedding dress.
Monday, it was back to earth and college, and a hangover, three vodkas when you are not used to them is hard and Mark was the same, added to which neither of us knew how to react after our good byes from the night before, something had changed in the friendship and we could not explain it to each other or ourselves.
The evening saw me in heels and skirt preparing tea once again, when mum came in with a shopping bag, ‘For you’ I opened it to find a pair of what I guessed to be four inch white stiletto sandals, ‘For the wedding’ I let out a exasperated mother, but she assured me I should get them on and get used to them as quickly as possible.
Tuesday, I was going to put on the long skirt when mum asks if I would like to try some other styles, ‘like what’ I asked and from nowhere she produces a mini skirt and tells me to be careful not show the world my assets. It was just a short straight denim skirt, but it did ride up at times making for a different sort or care needed too the long skirt, but after a few mishaps I pretty much had it under control, but there was a question about where it came from, mum would never have bought this for herself, at least I had never seen her wear it, had she got it specially for me?
Wednesday, I have only one session in the morning so get to spend most of the day free. I got home for lunch and found mum’s note alongside a couple of round soft jelly like balls. ‘Try these in your bra, see how they look and feel. Mum.’ I played with the latex blobs for a bit, and then went to do as she asked. The initial feeling was cold and damp, but that passed and I was left with two tits bouncing around on my chest in a most unfamiliar way. Now as I was undressed and in the bra I felt I might as well carry on and went into my mother’s room and had a look through her wardrobe thinking that she would not mind now. It was a warm day and choose a lemon cotton dress that had its waist just below the bra line and felt light and cool as is wafted around my body, then with my make up applied and heels on I settled down to some studying.
I was deep in reading when the bell rang at the door, I hesitated about answering and sneaked a look through the curtain, a delivery van with a package, so I steeled my courage and went to answer, he looked at me smiled and asked me to sign for the package, then left, and I had been frightened he would say something, but it was as if he did not care, maybe he sees people like me everyday I thought.
‘Getting into this?’ was a surprise question as mum walked in behind me later in the day.
‘Just practicing’ I replied
Then she came over and gave me a kiss, ‘It is nice to see you like this, you are more relaxed and easier to get on with than usual’ then she dropped the stunner ‘And you don’t need to hide the fact you are looking through my clothes now, do you?’
I went bright red, she knew about my nosying times, what an embarrassment.
We chatted over our meal about how I felt, then later in the evening took me out to a pub she felt we would not be recognised in, but it had to be while I was still in the dress, so I got used to being outside she insisted. But not before I had depilated my arms and legs because a woman in a dress does not have hairy skin. It was worth it just for the closer feel of fabrics next to my skin. Wonderful.
But that was not the end to the days surprises, the package contained a thing she called a gaff, designed to keep my male parts looking female and flat down below, I asked why and she pointed out how I had a little bump at times and if I were to get excited it would become a big give away bump.
Thursday, I have several preparations to do, moisturise with a tanning lotion, file me nails neat, let mum ‘tidy’ my eye brows, try on the gaff.
Friday, Mark noticed the eyebrows, we had not really had a gaming session in ages and he invited me round that evening, adding that he would like me to go in a skirt so he can get used to me before Saturdays big moment.
I went round wearing the denim mini, white heels, fitted blouse, make up and a smile. I was greeted with a wow you look the part, we chatted about what I had done to myself for this effect then went onto the X box.
Mrs Jones came home a while later and just stood looking at me ‘Oh my god, look at you now, Mark this is now way to entertain a girl’ he defended himself saying it was agreed before and his girl would like gaming anyway. No excuse she said with a certain authoritarian tone, asked me to help make the tea, and told us we should go for a walk with the dog after.
We did as we were told and took the dog out and I discovered that 4” heels are not the best shoes for walking on soft ground in, besides needing to clean the shoes, my ankles were killing me, what was even better this was a local walk and though we walked past people and a couple said hello to Mark, no one seemed to know who I was.
When we got back my mother was at Mark’s drinking wine and setting out a timetable for our Saturday. They would get us to the party for seven so worked back going through everything we would need to get done before then. From their good mood we could tell they were enjoying themselves.
Saturday. I wore the silk cargo pants, which now felt delicious on my bare skin, I wore the lower courts and mum said she had a treat for me once I was ready. That treat was to take me shopping first for the groceries then onto a department store where she lead me to the lingerie section informing me a bride will always have a special set of undies for her big day. I walked out with matching white satin bra and pants along with two pairs of white stockings, the corset she was confident had tabs to hold them.
We had lunch out then headed home.
I had my last moisturising session and liked how my white skin had got a healthier colour, and then mum started on the beauty treatments. First she washed my hair, but as she was running some liquid through my hair she spoke as if to herself ‘Maybe we should have discussed this, but it will look good, I know it will’ it seemed as though hair washing had become far more complicated than I ever thought possible. In the end I asked what had she doing. She had given my hair a good wash, next she bleached some streaks into it, finishing of with a setting lotion so it holds its style better when we finish. When I asked if it was necessary she just said yes. Soon I had my curled streaked hair arranged on my head and looking nothing like it used to. Next she took my hands and first glued long nails to my fingers, then painted them a pink colour followed by doing the same to my toes, after three coats she was satisfied they looked good. Now I was to get into my new underwear and discovered the limitations of long nails, but mum helped me when she saw me struggling, it was as the second stocking was easing its way up my leg I thought ‘How odd for a son to be so comfortable with his mum while letting her fasten the tabs to his stocking tops’ that all done I was handed me the silk wrap and told it was time to eat. She was asking me how I felt again and I was trying to be honest telling her how nice the clothes felt, the feeling of being pretty and attractive, and the attention I was getting, also the bonding between us that had happened in the last week or more. She confirmed that she had enjoyed this time together, liked the challenge, and enjoyed my new personality as I became more relaxed and feminine. We hugged and thanked each other for the special time it turned into.
But we had to finish me off, first make up, mum did it this time so it was perfect, then it was into the dress, as she fastened up the endless tiny buttons that ran from my neck to the small of my back I realised I would never get it off alone. I stepped into my heels and fluffed the skirt out feeling quite special as I stood there thinking how great brides must feel on their real wedding day when they look and feel this good. Mum had some finishing touches, a fine gold necklace, her gold watch on one wrist a gold bracelet on the other, then with care she hung a gold chandelier from each ear and finally took off her engagement ring and slid it onto my third finger. I was declared ready when she had dabbed scent on me and it was off to wait for my groom to call.
Mark turned up with his mother, he had had an equally image altering day, gone the scruffy lad, in walked a smart man, neat hair, close shaved, and looking immaculate in the morning suit. Mrs Jones was looking rather dew eyed especially after she saw me, mum had warned me that seeing the both of us dressed might bring back happy memories for her and I was not to worry, she was going to spend the night with her and make sure she was alright. I got a fantastic hug off her and told I was beautiful and fit for her boy. Mark by contrast looked a little awkward and shy, maybe the clothes maybe the situation. As a last touch Mrs Jones pinned a carnation to Mark’s lapel, presented me with a posy of pink roses and out of her bag brought out the veil. I was told to sit for a minute while they fitted it with the combs to my hair; it was down to my arse at the back but to my shoulders at the front. Mrs Jones then said ‘Nearly complete. Mark’ he stepped forward looking more sheepish, took my left hand and pushed a gold band up to the diamond ring.
It was my mum who spoke, ‘I now pronounce you man and wife, you may kiss the bride.’
‘Mum!’ was all I could manage, but Mark had been primed for this little scene as he leaned forward lifted the gauze before my face and gently kissed my lips. For some reason I said thank you and kissed him back as he pulled away.
‘Sweet’ my mum commented and then took photos of us, even a family shot with the mums on it. Then it was a short walk to the car and off to Samantha’s house and the party. The car was a challenge; mum had to help me in with my dress, and make sure I did not sit on the veil, Mark had it easier and took of his top hat and tails for an easy ride.
Mark was still nervous and let me know he was not sure how this costume would go down, Samantha knew what we were doing but he still wondered what the rest of our circle of friends would make of a wedding couple, especially one like us. I told him to relax and put a girlie hand on his knee, if anyone was going to get into bother it would be me as I had got rather to convincing and I was not sure how many knew besides Samantha.
We arrived at Samantha’s rather large house and let Mark help me from the car, arranging the dress then lifting the hem to keep it of the pavement as I walked to the door. We were greeted by a rather lovely Tudor couple who on closer inspection was Samantha and her boyfriend, ‘Mark how lovely to see you’ he got an air kiss ‘and your bride’ she came to kiss me then repeated Mrs Jones words ‘Oh my god, Jens it is you, brilliant, don’t tell anyone lets see who works it out’ she pulled the veil over my head and kissed me, her boyfriend knowing the truth was a little less affectionate in his greeting but smiled all the same.
I linked my arm into Mark’s ‘Come on hubby, time we mingled and got a drink’. The night was far more fun than either of us expected, neither of us were great party people preferring our games up until then, but Mark got chatting easily with some of the other lads there, while I was picked up by the girls who at first did not know me, but one by one recognised me, mainly from my voice it seemed and then it was the oh my god scene all over again. Samantha had us play silly parlour games, and I drank more than I should, Mark as the driver had his limit and stopped, what a thoughtful partner I have I told him and gave him a quick kiss, to which he said ‘Not here’ my reply being ‘Where then?’ as I slipped my arm into his elbow playing the girlfriend part for all it’s worth. ‘Just not where everyone can see, all right’ he said in a strong whisper. ‘So later then, when we alone and you can have your wicked way with me?’ he was blushing, ‘That’s not what I mean, just not here, I am getting enough comments about you being the best looking girl here and are we a real couple, that sort of thing, so don’t reinforce the misconceptions will you’ I had one last teasing comment ‘What misconceptions, darling’ leant over and kissed his lips. He went so red it was unbelievable and I made a quick retreat to the food table.
As I said the party was much better than I expected, laughing and joking with both sexes, but it was later that as couples paired off for their private intimacies that we were left with the singles who were trying to chat up some one who did not want to be seen with the others, which left us rather at a loss, so we called it a night thanked our host and made our way back home.
Mark revealed a text from his mother, telling us that my mum was spending the night at Mark’s so we would not need to worry about disturbing them when we got home late, and that Mark should sleep at my house.
It was on the table that we recognised a set up, a bottle of champagne and a wedding card addressed to us, Mr Mark and Ms Jenny Jones that is, with a message saying ‘Lovebirds. Enjoy your wedding night. Xxxx’ I was reading as Mark poured the bubbly into two flutes, ‘Well Mrs Jenny Jones, how does that sound to you’
‘Funny, I can’t believe how much ours mums are playing along with this.’ As we sat together on the sofa drinking our champagne I explained some of what I had told my mother about feeling comfortable in skirts, then it was Mark’s turn for a confession, some time ago he had admitted to his mother that his lack of girlfriends was down to him being gay, he was not sure he meant it, but it did stop her suggesting he find a nice girl. And now this scene of me cuddled up, head on his shoulder with his protective arm around me, at some time we realised we had been set up to see if Mark was gay and how I would deal with dressing for real not just poking around in a wardrobe.
‘Well they got you right didn’t they, just look at you, the most beautiful girl there tonight, and if you get the voice no one would have known, I bet you’
I got up so I could refill our glasses, and as I crouched before him asked ‘And what of you, do you fancy boys or girls?’
Reaching out he caught my hand and pulled me onto his lap, ‘I fancy something else I have now discovered, and I fancy boys who look like girls’
‘So can I kiss you now without being told off?’
He did not give a verbal answer, rather he pulled my face towards his and gave me a proper kiss that left me in no doubt he fancied me. What a shame we were so self conscious at the party, we could have danced and kissed and done so much more at the party if only we had had the nerve too.
I have never had a boyfriend before and Mark has not had a proper girlfriend before so we enjoying the new sensations of intimacy, then as the wine disappeared I suggested I should take the dress off and go to bed, making it clear I needed his help with the buttons. At the top of the stairs my door was shut, but mothers open and my nightie draped on the bed, I was not sure that a mother should be leading a son into these situations but giddy from the bubbles I led Mark into the room and asked him to undress me. It was as I hung the dress up the Mark whistled, he had a full view of my satin undies and stockings, ‘Still gorgeous’ he declared,
‘Glad you like it Mr Jones’ as I started to unfasten his shirt.
‘And the nightie?’ he asked
‘Mine’
‘You are taking this serious’
‘Mother suggested it’
‘I like your mother’
I put a finger under his chin and gave a mock pout, ‘I thought you liked me?’ then as his trousers fell and his erection sprang free, ‘You do like me I see’
He blushed as we rolled onto the bed and continued our intimate learning. His erection kept on touching me and at times he would press it against me, until I was so high I borrowed under the covers and kissed it, nervously at first to get a feel and a taste, but then more confidently until I had the whole tip in my mouth and sliding my lips up and down its length. There were a few short thrusts and a moan just before I got a mouthful of semen and I knew that was him done. After licking it clean I tucked it back inside the boxers and returned to the pillow, ‘I think you enjoyed that’
‘I love you’ was all he managed, he was drained. However I still needed to clean my face and finish undressing before slipping into my nightie then slipping between the sheets next to my lover.
Sunday. The day after, I woke to sound of mum downstairs. I found her drinking a coffee reading the paper, ‘Good night I take it’
‘Definitely different, thanks for everything, still not sure why though’
‘I take it Mark knows about the nightie then’
‘Yes thank you, did you really mean for all that to happen?’
As I sat down with my coffee she looked at me, ‘You might never do this again, I wanted to give you as much of the female experience as possible, and sleeping with a man is one of them’
‘How long have you been planning this?’ I asked
‘Me only since the idea was suggested, Emma I think was looking for an opportunity for months now. Anyway, I think my questions about your cross dressing have been answered in that I have a pretty son sat in a lovely nightie opposite me, what of Mark, is he gay do you think?’
‘I don’t know if he fancies me as Jens, but as Jenny we had some new experiences together’
Mark came down in my towelling robe he found behind the bathroom door, and looking rather subdued when he saw mum, ‘Morning Mark, good night?’
‘Yes thanks Mrs Christen’
‘There is a bag of clothes Emma sent round for you to go home in, help yourself to coffee and toast’
Mark made a quick exit, changing and leaving, I tried to kiss him but it was only a quick one and he was gone.
‘He will need time to sort his head out’ mum comforted ‘it is not everyday you wake up to find your best friend in a nightie after wearing what you did yesterday. You ok sweetheart?’
‘Fine’
‘Well that was your end of year party really wasn’t it, so what do you fancy doing today, you could go and play on Mark’s X box or we could go shopping and get you some new clothes, that nightie for one needs a wash every now and then, and though I like the idea of you thinking my clothes are good, I think we ought to get you some of your own if this is going to continue. What is it to be?’
I went over and hugged her ‘You are the best I cried into her shoulder, I would love to go shopping, but it is no longer for a party so what if someone questions me, what do I say?’
‘Just tell them the truth, that you are a trans sexual and your true nature is female’
I mean who would have predicted my mother knew I was playing with her clothes, that she would encourage me to walk about the house in heels and a skirt, that she would take me out dressed as a girl and buy me alcohol, that she would set me up with my best friend so that we end up in bed together, finishing off the adventure with my first sexual encounter.
The summer holiday was alot different to what I had expected it to be. First of all the end of term party had been something of a revelation, I mean who would have predicted my mother knew I was playing with her clothes, that she would encourage me to walk about the house in heels and a skirt, that she would take me out dressed as a girl and buy me alcohol, that she would set me up with my best friend so that we end up in bed together, finishing off the adventure with my first sexual encounter. Though I was doubtful about my mother's motives at first, about my own feelings and about Mark's reaction, I have to say what my mother has encouraged me to do has opened up new doors and I am loving every one of them.
I had set up a summer job before term ended so spent alot of time selling ice creams from a kiosk in a local park, but when I was not selling i was home trying out new feminine touches to my appearance. No one had made much of my ear peircings, some friends who saw me after the party told me the streaks were unusual but looked good in an off the wall way, but what I wanted was for my hair to grow a bit longer and get a really nice cut, but I dare not say that to friends who think I am only into games. The summer did allow me go out with my mother on occasion as Jenny, when she would buy me clothes and make up further encouraging me to be her girl, which could be unnerving at times, other times were really good as we grew closer and better able to talk. Mark was still the gaming friend he had always been, but something had changed in the relationship. There was a day mid week when we were both at home and having bored of our game sat back drinking a lager each in the sunshine. Mark was working up to asking something, and ended up blurting out that he wanted to take Jenny out. I was not ready for such a direct request, but once I had made sure he was genuine I offered to go and change, he should call round in a while.
I was always half ready to dress as I was clear skined and hair well groomed, so i only needed to apply make up, change my clothes and style my hair to be pretty much reasonable. I choose the denim mini and a loose silk top which exposed the bra straps. Mark came round and let me know he approved by giving me a kiss. Not sure what to do next I let him take the lead, soon we were cuddling on the settee like a proper couple, but before my mother came home i made sure my face was repaired and the preparations for tea were well underway. When she came home and found me dressed and Mark watching the tv, she invited him to stay and invited his mother round as well.
Mrs Jones was a little off gaurd when she saw me dressed, but recovered quickly to give me a greeting hug and kiss then let me get on with the meal. Our mothers just chatted as though it was normal to have a son dressed as a daughter making their meal for them. In the end I served the meal before sitting down to join them, rather like my mother would have done in the past. We all drank too much wine and I relaxed enough to let Mark kiss me when he left. I knew my mother would see but the expected questions never came, just a compliment on how good I was looking.
Mark and I once tried kissing when I was not in full Jenny mode, we were alone and sat next to each other when we moved to get up and lost balance so we were on top of each other, I went to kiss Mark but he pulled away as soon as I touched. I apologised and said it was spur of the moment thing, then he tried to explain how he finds girls and not boys attractive, and how he has not really come to understand why Jenny is attractive, even though he knows I am a boy. I confessed to being confused as well, that I like being Jenny and to have Mark treat me as a girl and react to me as he does is a mystery, but a very nice mystery.
And so our eight week holiday slipped by, a lot of work and money saved, but also a growing wardrobe and the odd liaison with Mark, mostly at home on the settee, but a couple of times out in the big wide world when we thought no one would catch us.
The return to college caused my life to change, weekdays were spent studying as it was going to be a hard last year, then working either Saturday or Sunday at the park, which only left one day free which was spent doing a variety of things like college activities, going out with mother or just being busy doing nothing, well everyone needs a rest sometime. Then when I was off, Mark was often working or having to catch up on the studies, so Jenny did not get out much at this time, I could sleep in female sleepwear but getting myself fully dressed was too much effort just to sit around at home for a couple of hours while I studied. I was persuaded once by mother to join her on a shopping trip as Jenny followed by an evening with Mark going to the pictures and having a pizza after, clearly we had our girl/boy friend moments but nothing too heavy. At the end of the evening Mark asked if I would be Jenny for him at least once a week because he enjoyed my company in a differnet way to when I was Jens which was still happening at college and at home when we found time to play our games. It did not take much persuasion for me to agree to being Jenny at least one evening at the weekend, this decision was followed by a poster going up at college the following day advertising a halowen dance.
Mark did comment on it and picked up a flyer, but I was more cautious we had done it once and had fun but what were the chances of doing it again and not attracting cruel comments. I told him to forget it. That was until about a week later, it takes that time for Mark to put his clothes in the wash, his mother to find the flyer, and for my mother to receive the flyer from Emma, finally catching me and asking if I was thinking of going and what was I going to dress up as. I tried very hard to explain how I thought it was not a good idea to do a fancy dress with Mark again knowing both she and Mark would want me to go as a female partner to Mark's male. In the end I was beaten into submission when later that day Mark came round to play a game and his mum came round for a gossip with my mum. It did not take long for the subject to come up and even though it was me who would be doing the main dressing up it was decided that on a democratic vote ot 3 to 1 I lost, they had even discussed the outfits and Addams family had won. It did not need great intellegence to know that Mark would get to be Gomez while I would be Morticia. My mum had not really seen any of the films and everyone else had been younger when it was last out but Mark had a CD and nipped home to get it so we could all sat down that evening to watch what we would be imitating. The story clearly was not what we were watching and as the characters appeared we, well more they, spoke of what we might be able to achieve. Mark fancied a velvet smoking jacket look, while Morticia always seemed to be in long, tight black dresses that gave her great trouble moving around. I dreaded to think how this would turn out, but I knew I was getting steam rollered into it so might as well go with it and enjoy what I can.
Within days mum was round to the costume shop and had booked a dress she knew would be ideal, and with a week before the dance she was making plans on my behalf, black stiletoes, dark burgundy nail polish and lipstick she had wanted black but I wanted some colour and not just the blushing of my cheeks, I had black underwear so thought that would be it. On the Friday she came home with the dress and asked me to try it on, it was close fitting but stretched enough to allow movement, but the bit mum liked was the way the skirt flared out below the knees, the way my knees were kept together causing we to swivel as I walked made the hem spin out and exagerate the swivelling that my hips and knees were doing, added to that the heels affected my walk, I was just going to mince everywhere. The sleeves were another thing as well, huge frilly cuffs which started at the elbow and finished below my fingers. This costume was going to take some getting used too.
The hours at the park were getting less as the evenings got darker so I was home early which pleased mum, she had been shopping for bits she said. I recognised the false nails but there were others I was not familiar with but did not have time to look at carefully before mum suggested she helps me get ready, with a hair session first. While she washed, conditioned and rinsed my hair I did the nails when not leaning over the shower, then as she styled my hair I painted them. sometimes I am thick and dont see things coming, this was one of those times, I got up to go and dress when I caught sight of myself in a mirror, my hair was jet black. Mum must have noticed my shock and reassured me it was not a permanent colour and will wash out after a few goes. In my underwear she then applies my face, quite pale skin, burgundy lips and dark eyes with the added extra of false eye lashes making the eye look even bigger. Followed by black stockings and the dress which between us we manage to wriggle me into with her pulling the zipper up, securing me into my most limiting outfit ever. She had even got me a black cape to keep me warm, then with a squirt of perfume I was ready. It was about this time I noticed that mum was wearing a rather nice new fashionable dress that I had not seen before, I complimented her on it and asked if she was going somewhere special, just out with Emma and some friends she replied, that will be nice I told her, she then felt the need to justify her getting dolled up and going out which she had not really done since dad died. Seeing me wearing nice clothes and enjoying myself being pretty had encouraged her to do the same, and the invite they had to go out that evening seemed ideal, ending with if we I can go out looking great and have some fun why can't she, why not indeed, was the ony response I could think of.
Mark had borrowed his mother's car and parked close to the door, but it was seeing him in the velvet jacket, black trousers, white shirt, red cummerbund and slicked back hair that got my attention, that and the Gomez style greeting of arm for me to link and formal greetings, once in the car he let out a whistle 'Did not like to say in front of your mum, but you are hot tonight' I squeezed his thigh and told him he was pretty hot himself.
We parked and the first person we saw was Samantha who let out a delighted squeal and came over to hug me, she and her new boyfriend were vampires, only she had the long black spike heel boots, tight black top and a riding crop which said something different, Paul just looked compliant as he wore an ill fitting black suit and fangs, I later discussed with Mark his chances of being long term and we agreed he stood no chance unless he liked the riding crop and doing as he is told. I walked in with Samantha linking arms like girlfriends and giggling as we tottered in on our heels. That was a great start to a fun evening, lots of people did not recognise us, even Mark's costume changed his appearance enough so that only close friends made him out, a few like Samantha knew me and for some reason none of them spread it about that I was really Jens, but spent the evening calling me Morticia or Jenny, so when I was with Mark I could use him as support and link his arm as I minced along by his side, when alone he was even brave enough to show some of the affection we had kept to our private times, gradually getting used to each other and the other party goers so that we even had a few dances, though I had to make them slow ones. But the close contact was not missed by Samantha and Clare who were treating me more like a girl than I was used too.
Though the dance had opened us up to new experiences of being a couple in public and for me being Jenny in a more convincing role, it was later on that our relationship moved on. I invited Mark in when we got home asking him that I would need help getting out of the dress. Once again my mother had set us up, a note to Mr and Ms Jones-Addams, Hope you had a good night, stopping at Emma's, see you in the morning. It was leaning against a bottle of vodka mix. So we opened the bottle and settled back for a drink and nice cuddle. Things moved along very nicely, mum was round at her friends again so we had the house to ourselves, and with a note similiar to the wedding dress night I knew she had set this up. After a good session on the settee I mentioned that I would need help unzipping the dress, so picked up my glass and the bottle and minced upstairs followed by an eager Mark. If boys are ever considered to be on heat like dogs, then that night I must have been, he was keen and obvious what he was hoping for. Again my mother had left her door open with a nightie draped across her double bed, he undid the fastener and helped me to wriggle out of my second skin, then we undressed Mark and fell into bed for more passionate cuddling. I was about to blow him off again when he tells me he wants to give this time not just recieve, puzzled I ask what he means, now it was his turn to look puzzled, he had seen a tube of KY jelly on the bedside and guessed I had put it there, not me must be my mother setting us up some more, so I asked what he had in mind, and soon we had worked out the basics of how Mark could make love to me and I feel him inside me making me feel the way I looked, feminine. He erupted inside me, then sadly he shrank away leaving me wanting to feel him inside me still. I knew then I would be wanting his attentions again and soon. But not that night, neither of us knew how a man can get erect again, so we cuddled until sleep took us.
The morning found me looking a mess, as well as the pillow, I had not cleaned up so make up was everywhere, it took a while to get clean and presentable, but when I finally made it to the kitchen found Mum and Mark eating toast and chatting about the evening. Mark left after breakfast and a good kiss form me to say thank you. Then it was just me and mum, I thanked her for the card and drink, and the use of her bed, fine she said just wanting to open up new experiences for me, which made me think of the KY jelly, so I thanked her for leaving it out. This rather caught her out, the jelly was for her she had not meant to leave it out, now it was my turn to be embarrassed as she rightly guessed what we had used it for and asked how it was, maybe I was feeling a closeness but whatever the reason I told her how nice it had felt, and she hugged me telling me how lucky I am to enjoy such things, then I told her I was getting really confused over my identity and did not know if I was a boy or a girl, she just told me to be myself.
Then it was time for her confession, the night out she had had with Emma was more than just the two of them, it was actually four of them, Jack and Sean being the other two, and yes they had had an enjoyable evening, it was the first time she had been out on a 'date' since dad had gone so it was never going to be much, I was fine with that as long as I did not have to call her man 'dad' and he was good for her then I would be fine with it. Then came the bigger confession, the topic of where we, Mark and I, were the night before came up, they said a fancy dress dance as Morticia and Gomez, and somehow they assumed I was a daughter and not Jens dressed up as Morticia. She reassured me that if she saw them again she would correct them but it had been fun letting them think I was a daughter.
The Sunday was going to be a quiet day, but as I was still glued to my breasts and nails I dressed in my mini kilt and pink angora top before settling down to do some course work. Just before lunch mum came in and told me she was going out with Emma, and she was looking good again so it was not just for a gossipping chat. This was followed by Mark texting asking if I would like to go round to his. As soon as mum and Emma were gone, I was round at Mark's and kissing for all I was worth, I had the jelly in my bag and had already squeezed some inside my hole in anticipation. It took us no time at all to be on a bed with my knickers down and my legs up with Mark filling me, this time I was sober and tighter, but Mark lasted better but still came without me, though he did touch what I guessed to be a g spot several times and wished I could have done more to get him to stay in there till I enjoyed these new sensations.
The second event in what I expected to be a quiet day was to find myself meeting Jack and Sean, I was watching tv with Mark after our sex adventure when I had a text off mum asking me to be scarse or be Jenny. I was already Jenny so stuck around to see what was happening. The four of them came back mid afternoon having spent their lunch in a pub, seemingly mother had not managed to tell the truth, and I could see why, both men were good looking and seemed to be good fun, Jack being well over six foot and toned why would she risk losing him when they were just being friends by admiting to a lie. I immediately realised that if I was to ever meet these men again it have to be as Jenny, mum was not going to spoil her fun by admiting the lie, it also meant she could ask me to dress, and it also meant I had another little excuse to make myself pretty.
Later at home I questioned whether she had explained to Jack that her daughter was really a son, with a hug she asked if I was sure about that. Going on to tell me how she liked Jenny, Mark clearly liked having Jenny around, and now Jack and Sean would be expecting see Jenny if they meet me again. My life as Jens was being restricted but also encouraged by those close to me, and deep inside I could not find the fight to say no, I knew that I was enjoying the whole experience far to much to stop it right then.
Life was getting very interesting, I had a boyfriend, a supportive mother and a desire to be a girl, but a caution about giving up my birth gender.
Life through the rest of the year was pretty much one of, Jens for college, Jenny for most of the other times. After our heart to heart after the halloween dance mum offered to treat me to a hairstyling that would allow me to switch easily between genders, so when I came home I would only need to change and add light make up to feel right. They also took away the black and dyed my hair a more natural light brown.
Christmas came and I got lots of Jenny gifts off all those who knew. We had a big dinner with Jack and Sean turning up to make it a busy day. Of course I had a lovely new dress for the day, dark red stiff cotton with new red spike sandals off mum, 3" chain ear rings off Emma and a set of silk underwear off Mark, which he gave me in private to save my blushes.
I had grown more confident about my presentation as Jenny so for new year I went with Mark into town to join in the celebrations as a girl. My eighteenth birthday came next, I could drink legally but my ID card proving my age was not very flattering even though I tried to let my hair look girly, it was still going to be hard not to be questioned over who it was on the card when I was Jenny. Mum got over this by using the ID maker at work and generating a new one identical to the student card except in the gender it was female and in the photo it was a fully made up Jenny.
Mark was still keen on our dates and as my job disappeared in the winter, he was able to persuade me to go out more often if he was paying, this was not a problem as mum had virtually got me to be Jenny every weekend since the turn of the year. As easter came we both put our heads down to get our best grades, Mark suggesting as a reward when we were finished we go away for a weekend, our mother's on hearing this suggested a nice city break and they would pay for it. Exams over and summer jobs not started we had our cases loaded into Mrs Jones' car and we were off on our first holiday without parents, but the fuss my mother made about what I packed made me think she was taking too much interest. It was summer so she had me use tanning creams on my body, then sent me for a trip to the hairdresser for a trim, then she had me do the long nails and fix my chest, which only left the packing. Long ago I had learnt how to hide my male member with glue and tape, so now I could wear pretty knickers of any design, but she had thongs in mind for my time away, she also fastened me into a new corset she had treated me too, then I was allowed to choose my clothes as long as she approved. You would have thought Mark was picking for me and not my own mother. Once packed and dressed in nothing but skimpy, light or revealing outfits, I was allowed to go. Then when we arrived in York at the hotel and unpacked I found a fresh tube of lubricant and a pack of tampax, she really was setting me up for a weekend of passion, but I was not going to object, it had been weeks since the last opportunity to have my hole filled.
Mark took his chances and asked if I wanted help changing before we went to look for somewhere to eat, when he found that I was only in a corset and thong under my cotton wrap over dress, he took it to mean I was randy, soon he had me over the side of the bed while he pushed into me till he could last no longer and came in a heaving rush. While he recovered I dressed in my christmas dress, smart but short enough to please him was the idea, and it worked. We had a nice pasta meal and a walk around a few bars, before heading back for round two. Only this time he was not fully recovered and I was relaxed more, so as he touched my excitable spots I became more keen to get him to push against those spots, eventually I had my first orgasm, I had masturbated as a boy but this was totally different and far more satisfying, then Mark came. He asked what had happened to me. I told what had happened is what I want to happen every time, I might allow him a quick shag but what I wanted was a long slow fuck that made me come. And bless him he said he would try.
We had Saturday sight seeing, followed by a evening of trying to satisfy me but failing. Then on the Sunday more sight seeing followed by a new approach, while getting ready to go out for a meal I knelt in front of him and sucked him off, my reasoning being, I liked having him totally at my whim, I liked the taste and lastly it would slow him down later. It worked so well I came well before him and was able to enjoy relaxing as he pumped away at my arse. I had never had sex as a boy but I doubted it could be better than this. I was filled with cum and happiness, what a post exam experience.
We arrived home on the Monday afternoon and had time to recover from the drive before our mother's got home and wanted to know how our break had been. We ate together and chatted about our weekends, Sean and Jack had been around but we were not brave enough to ask if they had stopped for the nights as we were not there to hinder any night time activities. It was when Mark and Emma left that my mother came out with it. 'You have lost your virginity properly now, haven't you' I was at a lose at to what I should say, mother's I thought kept off such topics, but I blushed 'thought so, you seem more confident with your touching and your smile tells me something special happened, I made up the rest........am I right' I hugged her and told her I was in love, that Mark was so kind and considerate I could think of no one else I would want to be with. She hugged me back and told she was pleased for me. Next she asked if I had thought what I was going to do next, get a job, go to uni, do some job training. I had not really thought that far ahead and just wanted a break from studying.
Until the results came out I picked up my old job selling at the kiosk, so I was back to being Jens a lot of the time, except my hair was now a swept back bob that had a feminine feel to it, and did not go unnoticed as a camp look. The results came, Mark got great results and was accepted onto the course he wanted, for me it was not so easy, my results were poor, maybe all the gender confusion had taken its toll on my studies, whatever, I could not do the course I wanted or anything like it at any of the unis I preferred so I had to consider getting a proper job.
It was on a Sunday afternoon, I had been at home since I finished work on the Saturday, had got dressed for a night out with Mark and was now flicking through the local newspapers and college brochures in what might be called Jenny's morning look, tits still in place, nightie and silk wrap. I was admiring my pink nails which I had now grown a bit so they had a nice oval shape but were not too long, when mum comes in and asks if I have found anything I will apply for, I point out a few trainee jobs, but then mum picked up a college leaflet, I had not done it deliberately but it was just on top so mum thought it significant. The course was for a one year hair and beauty foundation training, with options to take the training further in future years. Mum seized on it saying it would be a great asset, Jens as a boy would be able to do the course and see it from a different perspective, male hair dressers are always the best she convinced me, and as a secondary result my time as Jenny would improve with a greater knowledge. I promised to enquire on the Monday. When they said they had places and no objections to a male being on the course, I was unexpectedly pleased that I had a way forward that could leave me with many options and oppurtunities, though I would be expected to participate fully in all aspects of the course, there was nothing that should prevent me from completing and passing the course work and final exam. I also rang some of the trainee jobs but I was either to well qualified with my A levels or not qualified enough having not got a degree. What clinched my decision was that mum offered to pay for the course fees and give me an allowance if I failed to pick up a part time job, she just explained how much Mark was going to cost Emma and if I had gone to uni she would have had to find that money from somewhere or see me go into debt. All I had to do was sign up and wait to see what my classmates and tutors would make of me.
Two weeks later I found out, I was the only boy among twenty one teenage girls, all who had made a special effort to get themselves dolled up for the first day, seemingly competing to show how much make up they could use. Myself I had chosen to wear smart jeans a nice Jens jumper which made me feel rather drab, but I was a boy in this situation and not Jenny so I settled for my boy look. The first week was finding our feet, where places are, what topics we need to study, who our fellow students are, which was interesting as I got different reactions from the girls, some saw me as an intruder others an interesting novelty. The comment that stuck me most was a tutor who explained how, when we were doing practical sessions we would be taking it in turns to be the model, because we need to know how it feels to have all the treatments done to ourselves so we can explain better to customers what is happening, and rather pointedly I was told I was to take my turn regardless of the treatment being practised. Unknown to both her and myself this instruction was to have profound effect on my life, let me explain.
Three weeks later we had been doing lots of listening to tutors doing the theory of the course, then we began to use the equipment that the college had for training, our first practical was washing and conditioning hair, we had done the theory of why and how this worked and is good for hair, now we were told to pair off and wash each others hair. I paired with Kim and washed hers, then she washed mine, followed with blow drying each others as we clearly would not want to be leaving with wet hair. Kim had long wavy hair that had got more curl from the wash, so I just dried it with a volumizer to give it body. Next she dried mine which was at the time a sort of bob cut that stopped short of my shoulders, as Jens I would sweep the fringe hair over the top without a parting, but Kim dried it with a parting so the fringe came across my face leading it into the bob which now curled under. Some of the other girls had restyled their partners hair, but I was the most self conscious of those who had been restyled. It was when the tutor congratulated me on taking a full and active part in the session, I said I had every intention of learning as much as possible, good she replied I might remind you of what you just said later in the course if you refuse to participate. Kim then chipped in with her own comment that she would make sure I did not miss out on anything, and when I looked at ther she had a very cheeky smile on her face. I just said thanks with what I hoped was a wry grin on my face.
Mum was a little surprised to see the restyled hair when I got home but told me it looked nice, I told her it should as it was how I wore it as Jenny and the cut had been designed to be that way really. What she meant was it looked nice without me being Jenny and just being me.
My next practical of note was a manicure, the girls had all been told to come in with their nails clean, I just made sure all traces of my weekend activities were removed so as not to arouse suspicion. Again with Kim who had become a good friend by this time, removed cuticles, filed, polished and buffed each others nails, Kim had brought her own polish in but I used the clear offered. Kim did comment on how I kept my nails longer than her brothers did, I said I did not like them short and stubby, it stopped me chewing them. As we chatted future practicals came up and the one where we put acrylic nails onto each other made for interesting conversation, she had long nails and hoped not to have them put on her fingers as real long nails look better than acrylics, but I had short enough nails for the nails to make a dramtic effect. I tried to explain how it might look odd a boy having long nails, but my eagerness to learn statement was returned to me and I knew that with Kim as my partner I would not get away with the excuse of being a boy, besides I was sure one tutor in particular saw me as a challenge and did not want a boy on the course and used practicals to try and drive me off the course, I also felt a couple of the girls wanted me to fail and leave, it felt a bit like sex descrimination reversed.
As the year progessed, we worked through massaging hands and feet with oils and moisturisers, waxing which we only did on arms and I knew when it was coming so did not depilated for a month before so I had something like a boys arms to show. When I said I liked the feel of smooth arms I got some odd looks from a few girls, but stated that I might just keep them clear as they felt so nice, to which Kim asked if she could do my legs, Sally then offered to do my bikini line, I told them I would think about it and if I decided I needed help they would be the first to know. What they did not know was that my pubic hair was already trimmed back to take my thong, and there was no way they were going to wax me up there.
Towards christmas I noticed an advert for a Saturday girl at a salon, and feeling brave went in and asked if a Saturday boy would do, I told them about the course I was studying, and was told to start that weekend. This would be great experience and much needed cash so I was pleased with myself, as a bonus the manager was a man which made me feel a little more confident about being there. He was not quite the stereotype gay hairdresser but not far off, his hair was long and luxurious, and his clothes had a feminine look about them. I was only sweeping up, making drinks for customers and at times washing hair, nothing hard but it was a job. Over the weeks I got to like Ray and the other two stylists, they behaved like three girls not two girls and a man, so it was no surprise that with all my exposure to the girl students as well, I too became one of the girls at the salon imitating Ray, touching customers in a gentle feminine way, chatting about nothing, letting my vioce sing a little, and make gestures with my hands that when I caught myself recognised Ray in them. Besides which Ray was the first real gay man I had meet properly, I found this out on my very first day at work, as we were closing up a man came in, very muscular, tanned and in tight fitting clothes to show off his physique. I very nearly said we were closing when Ray came past me and greeted the man with a proper kiss. I was really shocked at this up front display, the other two stylists, Sara and Kate just laughed at me when they saw my reaction, which made me blush, and wish a hole would open up below me. How embarrassing. Needless to say I was not so shocked next time, and as my demeanour became more feminine at work Sara jokingly asked if Ray could set me up with a date, when I said I did not need a date they asked if I already had one, I said yes, then as a joke I think they asked 'Is he nice?' I stumbled over my answer and stammered, which got a clap of Sara, and of Kate 'Excellent, another fairy like you Ray' I was getting truly embarrassed and upset at being teased like this, so it stopped and Sara gave me hug and told me they meant nothing by it, I had a long way to go before I was anything like Ray and some of his friends.
Christmas was a special time, no college, just dressing down for work but I could keep myself feminine if I wanted, I bought myself a pair of tight hipster jeans and a long sleeve T shirt similiar to what Ray wore, and felt at home wearing them to work. Of course Mark being home for more than just a weekend meant we had some catching up to do, he was enjoying his course, making new friends and getting into the student way of life, I told him about my life, the course and the job and the incidents that happened and laughed at the times I was nearly found out, but most of all I loved being with him, having sex again and being able to be his girlfriend was just so special.
The next term brought new challenges to my identity. We had a series of lessons on hair colouring, at the end we all knew we would be doing something to our partners and had to discuss with them what they would like doing, Kim said she would like to try an all over auburn colour, I was still unsure after my black hair experience, but I had the salon girls I could ask for advice from as well and they all felt I should try highlights. And so mid February Kim got a auburn head of hair one day, followed by me leaving the next with silver and gold highlights, the tutor was around to avert any disasters so it came out fine, and I unexpectedly liked it more than I thought I would, the texture of my hair seeming to have more life, so I promised Kim I would be more adventurous next time we have a chioce in a practical session.
For practice we were encouraged to use the college facilties outside lesson time, so myself and Kim plus a few others would spend Wednesday afternoon when we had no classes pampering each other. This usually meant manicures, pedicures, massages and hair styling. The girls would also make each other up, I did not join in with that but did Kim's make up on several occasions. The main benefit for me was the manicure, my nails became elegant but not long which was nice, and my hair was treated to several different styles though a bob cut is rather limiting compared to what I could do to Kim with her shoulder length locks.
I also started to wear more feminine tops to college, mostly the long sleeve T shirt style that fitted rather better than a boys would, plus my large shoulder bag I used to carry college work in, not to mention my more effeminate gait and gestures, I hardly could not believe it when Angie pointed out how gay I was behaving, and when I said sorry, they said what for I was just being me and I looked lovely the way I was. I gave her an air kiss and a hug, thanking her for being so nice. But it did rather let me lower my Jenny/Jens divisions. I nearly always wore hipster jeans and tops I had bought from the women's rail in stores, plus I stopped hiding my hairless arms, and started wearing nail gloss all the time. I was just feeling more myself like that rather than trying to be a college boy and dress scruffy.
Towards Easter we had classes on make up and fashion, I knew practicals would follow and worked out how to aviod being totally dressed up by Kim. After the holiday it came about and I managed to do Kim's make up but created a new challenge of what make up would work for a boy or man, we had plenty of fun experimenting with subtle shades until we had a barely noticed make up which just made my face look better with clear eyes and soft lips, no strong colours just shades. We thought it worked well and we got good marks but you could tell one of the tutors felt Kim should given me the full works.
Next we had to dress our partner differently to their usual style. Kim nearly always wore a mini or long top and footless tights, So I scoured the charity shops with her and found a pair of long black silk culots, and a big flouncy paisley top. For me, we found a short lemon kaftan top and white linen trousers. At the end of the week we had a fashion show where we all went out changed and came back to show the class our new look. Kim got a eight for hers, I got a seven, not bad we thought as we had not been able to fully accesorize the outfits. Some of the others felt the same and a new show was scheduled for the next week. We had the morning to fully prepare our partner, I gave Kim a big hair do, with eye shades picking out the paisley colours, lilac nails and lips also from the paisley, then stood her on a pair of light purple shoes she owned. She got a ten this time because she was stunning and so different to her norm. I was given a bob full of body and a fringe sweeping across one eye, which covered some of the make up she had used giving me darker eyes, paler skin and creamy lips, my nails had a slight pink tint but nothing noticable, and I wore some plain sandals on my feet. I got a nine, based on the use of different styles and that I did look good, but it was not that far removed from what I might be expected to wear. 'Make up and a girls hair style?' I questioned, and nearly to a girl they all said yes if I turned up with make up and styled hair it would not be a surprise, the lemon top was no real break with what they felt I wore already, just a slightly more camp top than usual.
When we had all been judged and marked, some did much better than Kim and myself had done, while others had not faired so well, the three tutors made general comments about what had been seen followed by a challenge that was going to affect me. It was Patricia, the tutor I felt had it in for me, who came up with a suggestion 'You have all done very well and we are all impressed with your work, but we notice that given the oppurtunity of having Jens in the group no one suggested possibly the biggest change of look' I had a good idea what was coming 'I was thinking someone might have dressed their partner as the opposite sex. So what we would like you to do is split the group in two and one from each group is restyled as a man or woman.' the pairs were all separated and we looked at each other no one volunteering in either group to be restyled, the girls were all girlie and having that stripped away would be more than they could take on board, for myself I worried I might give away my secret. With no progress Patricia intervened 'As no one is volunteering I would like to suggest Jens and Kim are the models. This will give us the chance to see how the genders are similiar or different, and the different challenges involved.' I looked at Kim she looked in shock, I was just feeling very nervous and worried how to handle the situation. 'The look we hope to see is nothing outrageous, something quite mainstream and positively cross gender' Kim was going to object when she continued 'And for Kim who I think will have the biggest challenge I will offer to take her for a full spa day to compensate for the shock she is now feeling' there was a wow from some of the other girls and Kim's smile crept back onto her face.
This decision brought about animation to the groups, most of the talking was done by the other ten girls in our respective groups, they were all trying to put forward their ideas. By the end of the session we were told to come back after the weekend and each person should have their ideas on paper and then try to put the best of them together. My more immediate problem was how would I deal with the after effects, how would my mum take it, probably well, my friends outside the course and work on the day after might be hard depending on what they actually did to me. I was right my mum had no problem with the thought of me being girl at college. The surprise was work, I mentioned what had been happening at college as I often did, they knew about my lemon top and linen trousers actually suggesting I come into work in them, and I was wearing them that day. So now I was telling them about the project to dress me as a girl, all three thought I would make a good girl if done well, and when I asked what I should do if they do something rather permanent and hard to cover up, like what they asked, I expected my hair to be coloured and restyled in some way, I also knew they would want to extend my nails. All three agreed that if I had long nails they would not be removed easily or if I had a style that would need another cut to return me to a boy look, then the only solution was for me to come into work as a girl. Then the stunning final statement from Kate 'We rather expected you to become more girlie already if truth be told, just enjoy the experience and we shall look forward meeting a new girl next week possibly' So that was it, no get out from anywhere it seemed, I could even go to work as a girl.
By the time Monday came around both Kim and me were very nervous as to what our teams would have come up with. Kim would not allow them to cut her hair, but they could shorten her nails. For me I could not think of anything I strongly rejected, my only request was that at the end I did not look like a freak, just a girl. There were a lot of ideas and it was decided to do two styles, one a student look, the other smart going out in the evening look. There was a college wardrobe that the drama courses used, plus the ever affordable charity shops to rummage through, and for me the offer of my teams own wardrobes. By Wednesday we had the styles sorted, college would be footless tights, short pea green pinafore (Siobhian's), 3" wedge sandals, tons of bangles and chunky bead necklace, Leah was in charge of make up, Suzy of hair and Emma had the nails to do. For the evening a red bias cut, one shoulder/diagonal hem dress was supplied by Suzy, red platforms, a white wrap, fine gold jewelery, a red clutch bag. Geri was to do my face, Sam would finish the nails and Alice would restyle my hair. I promised to be hair free and pick up my own underwear, I hoped I gave the impression I would need to buy some and not just look in my drawer for something suitable.
Come the Friday morning I was almost ready to accept whatever happened, but nervous about how it might affect me afterwards, I still had to go to work and finish the course, how would I do these if they did something extreme. I spent the morning with my college team. They told me to sit back and just let them do all the work. As I expected the nail trolley was wheeled over and Emma proceeded to fix full length acrylics painting them a pale green colour. Suzy gelled my hair and with small bows created and mass of tiny pony tails all over my crown. Leah then gave me a plain make up with no bright colours just a daytime style. Finally I was dressed. They loved my lace knickers, and had found some bra inserts to fit in my matching bra. I was finished and along with Kim who looked like a weedy lad in jeans, trainers and a sweat top, her hair hidden in a baseball cap, they had darkened her face to look less pretty, and cleaned her shorter nails of colour. We entered the main classroom to applause, Kim blushed I tried to look unsteady on the heels, no point in being to obvious. Then the tutors and class marked and commented on our appearance.
For Kim the next event was a shock, being lunchtime every one went to the cafe, she felt her credibility would be ruined if anyone saw her, especially her boyfriend. I tried to look nervous but told her I would do it if she did, and getting changed back just for a buttie and coffee, then having to change again would make things more long winded. We walked out of the building surrounded by our classmates, rather like we usually did any other lunch time. When it was noticed how easily I was walking, I replied that I did not know what all the fuss about heels was they were not that hard to walk in.
After a quick lunch my second team had me back in the training rooms. Alice did the full works on my hair, shampoo, conditioner, colour, then a cut. She would not let me see what she had done. Like wise Geri did my face, Leah had plucked a few eye brow hairs out in the morning, Geri now pulled more out, I did object but was told no girl had bushy brows. The only thing I could see was the red polish Sam was applying to my toe and finger nails. Then it was time to dress, I had brought red underwear, but they told me to only use the knickers, then they sprung a corset on me, I had to be strapless and this would give me a waist as well. They seemed to enjoy pulling the laces as tight as possible but I did finish up with a great figure, then it was on with the dress, short gold neck chain, gold bracelet and watch, long dangling gold chains hung from my ears. I was then allowed to see the mirror. I shall start with what they had done to my hair, my bob had gone, well nearly, at the front I still had the length and a fringe which parted in the centre, but the back had been trimmed right up the nape of my neck the longer outer layer of hair being nearly level with the top of my ears at the back coming forward in a diagonal line to the long hair infront of my ears, The short exposed hair was a darker colour than the lighter top and sides. That was not the end though, my eyebrows now had the tadpole shape the girls all seemed to like, below which my eyes had a smoky look, there was foundation and blusher but it was the full red lips I now had, something they had painted on them before applying the red gloss had made them tingle and now I could see the results. Plumped up kissing lips.
All happy besides me I was lead of the meet my partner Kim, she was in a smart suit, shirt and tie with a tribly hiding her hair now, the jacket gave her the look of broad shoulders without looking like an american footballer, she looked quite good for a girl. We made our entrance linking arms as if I were the girlfriend, again applause and excellent marks for everyone and great comments. It was now late afternoon and the tutors suggested that rather than waste the effort we have a class night out, all the other girls would go home and change meeting up about seven at a pizza hut. Kim was not keen but her girlfriends persauded her to have some fun and she could go home with one of them if she did not want her family to see her. Which left me dressed up to the nines and only a bus ticket to get home with. Patricia who seemed to have enjoyed the days activities offered me a lift home. I was relucant, but what else would I do for three hours dressed like this.
Mum was home when I walked through the door, 'oh my look at you' she squealed, she had known about the project but was not ready for the results, 'those girls have done wonders with you, they are so talented............. And you are going out tonight as well....... brilliant' She stopped making tea and called Mark's mum who was round like shot, took pictures on her phone and sent them to Mark, which resulted in me getting a text 'Gorgeous, wish I was there, remember you are my girl' I sent back 'always,love you'
The evening was good fun, some girls were not eighteen so could not drink, but still came to the bars with us, all dressed up and with no boyfriends except Kim we were like honey to any man who fancied his chances, some got a terrible time as over twenty excited girls would tease them or try and pair them off with me, I obligingly played along and Kissed a few before telling them I was really a boy, which got varied responses from 'I don't believe you' to angry homophobes calling me a pervert and the girls unladylike names.
It was back to earth with a bump when I got home, it was not late and mum was still up and clearly wanted to have a chat. She was pleased to see me looking so good but wanted to give me support as I worked through what I was going to do in the morning. I would have to go to the salon and we did not have the time or equipment to do anything then that might alter my appearance. I felt that wearing my jeans or white trousers and a t shirt, like I normally wore would be fine, mum was keen to point out everything about me looked female so why not embrace it, be brave and go to work as a girl. I still felt it was too much for me and the salon to handle in one hit, I would wear trousers and a top. In the morning mum got up to check me out before I left, she was clearly dissappionted I was not taking this oppurtunity to be Jenny, but I was not prepared to be so reckless.
In my white trousers, flat shoes, purple slash neck top a base ball cap and no make up besides the coloured nails and waterproof mascara that I did not work to hard at removing that was about me, oh and the darker lips that was a reminder not to use staining lipsticks in future. Other things like neat eye brows and still swollen lips I could do nothing about either, but I felt as though I was not to different to the Jens they saw a week ago. I arrived on time as always and started with my duties. Before all three staff had turned up, but before any customers, I had been hugged and congratulated on my look, mum had sent them pictures of me from the night before and now they wanted to know why I had come to work looking like I did. Being professionals it took no time at all once they had got me in a chair to give my hair a quick blow dry, and to whizz some light make up over my face, mum turned up with a bra and fillers, as well as some jewelry. They now were calling me Jenny and I had no excuse to stop them, besides they seemd to be enjoying the fun of transforming me. Work turned out to be fun as well, I tried very hard to be girlie with most customers not realising the change, some regulars twigged that Jenny was Jens but whoever was serving them at the time would explain how I was on a course and having to look like a woman as part of that course, which made them ask more detailed questions, which made any time I spent with them interesting to say the least.
Towards the end of the day Ray invited me to join him that evening, he was going into town after work for a 'nothing planned just see who I bump into night' I asked if I could go home and change, he said only if it was to put on my dress, I blushed and said I would think about it, the women then told me they fancied coming as well so I was steamrollered into going. As the last customer left at gone six we had some cleaning still to do, but Sara pulled me to one side and told me to use her make up bag and brighten my colours, what could I do but play along and do my face for night time, then finding her scent, tested it, like it, and used it. Going back to help with the final chores. I told mum what I was doing and when I was overheard on the phone Kate told me to invite her along, which she heard and said she should come along later, and did I want her to fetch me anything to change into, I said no but just knew she would bring me some extra female items of attire.
By seven thirty we were all in a bar eating salads and drinking wine. Mum had brought along some heels and a dress if I wanted to get changed I was persuaded into the shoes, but the dress would be too much hassle to change into given the state of many toilets in the bars. The first thing they all said was how well I walked in the heels, then over the evening I could not stop mum telling them about the parties I had been to with Mark as his female partner, they all thought it sounded a hoot and loved the idea of me in a wedding dress. They had also worked out that I was possibly getting more feminine in behavior and looks, and that it would be quite possible for me to go full time if the situation arose. They already knew I had a boyfriend, now they knew who it actually was. Ray now loved the idea of taking us to gay bars where I would easily be accepted without question. I was with my mother and not completely sure how she would take this development, nor how Mark might feel about being in a gay bar. We parted later on with everyone, but not me, being keen on me turning up to work in a weeks time wearing a skirt, I could only say maybe but knew the pressure mum would put on me would be constant.
My next problem was how should I turn up to college on the Monday, we only had two weeks left but I felt I should maintain my place as Jens, I rang Kim and asked for help on the Sunday, she told me to play along with the tutors and turn up in my college girl outfit, I pleaded with her to at least trim my hair and remove the nails, but she was busy with her boyfriend and told me to be the person the whole group knew I really wanted to be, I asked what she meant, she bluntly told me everyone in the class had expected me to come out ever since I first walked into the introduction classes, now I was speechless but struggled out a 'you are joking' she told me she was not and she had to go.
Monday I dressed in the pinafore and leggings, I did a muted face, filled my wrists with bangles, gelled my hair to give it volume, then slid my feet into the wedges. Getting to college was not too hard besides the nerves that were playing in my stomach. For the first time in ages I felt very self conscious thinking everyone was staring at me, but I had my worst moment as I went into the study room and faced my class, there was a squeal and several jumped up to greet me, Kim turned to a couple sat by her 'Told you Jens is one of us really'. No one called me wierd, maybe they had got used to me over the year, maybe they did not care, whatever it only took minutes for the novelty to wear off and our usual conversations to return. When Patricia entered the room she scanned us to see who was there, she then came over and quietly said 'Glad the true you has come to class at last' then to everyone 'Right girls revision ahead of exams at the end of the week, any one want to suggest a topic?' And that was it I was one of the girls and it was not a problem.
I had gone a year not being that open about being a cross dresser and then everything happens at once. I had had a week of going to college as Jenny. Mark had come back mid week as he finished for the summer, and loved the fact that I was a girl fulltime, taking me out every evening that week, we even had a night when we decided we should stop hiding from our old friends and went to our local pub to see who was about, Mark got a warm welcome from one of the guys there who he had been a good friend through school, I did not fare so well, no one at first recognised me, then when they did I got a hostile reaction from one who I did not really know, and I was ignored by most of them which made me think they were talking about me. A couple did chat and ask how I was and what I was doing. Cherri who had been at the parties and was not phased by meeting Jenny again, reflecting what others had said then it seemed ineveitable that I would do this after seeing me at the haloween dance especially where I allowed myself to be less restrianed. I left the pub not keen on repeating the experience but Cherri did exchange numbers and told me we should meet up some time and maybe include some of the other girls like Samantha, I said that would be nice.
The weekend was a big turning point though, mum and Emma decided that it would be nice to have a meal with Jack and Sean, they had been around all year, I had not gone out of my way to dress for them and would hide in my room if I was not Jenny, to keep the peace with mum more than anything else. Jack had stopped overnight on occasions I was away with Mark and sometimes when I got home from work mum would look less than smart, more just a got up look, so I guessed something other than chatting was going on, if you know what I mean. Well that Saturday we all ate together, Emma cooked the main course, mum and I cooked the pudding and provided the wine. It was going very well, I was wearing the red dress I had now been given to keep and had enjoyed more compliments on my new look. As we finished our puddings and I served coffee mum tensed up and went quiet, I think only I noticed at first but Emma looked at her as well. I have something to tell you, she finally said, everyone looked at her, I have been lying to you, she looked at Sean and Jack, I think I have to tell you the truth now, I should have done this ages ago but did not want to change things, she had everyones attention wondering what announcement she was about to make, 'Jack, Sean, this is going to be hard to understand but Jenny is my son.' There was a silence, Jack started laughing, I started blushing bright red, Emma was doing a good shocked look, she clearly knew this truth but the situation was a surprise. Sean was looking around, 'you aren't joking are you' he said calmly, 'I never guessed you, are a great trannie Jenny.' I could stand it no longer and ran to my bedroom, I heard Emma tell Mark to go after me. As he hugged me in my bedroom we could hear the mothers talking to their boyfriends, Jack was clearly not happy with the truth and could be heard raising his vioce, then shortly after the front was closed and Mark went to see if the coast was clear. Mum was crying in a chair, as Emma and me tried to comfort her Mark made another coffee and tidied up the table. Jack had said some cruel comments, Sean to be fair had tried to calm things down but Jack was not happy with the fact that he was going out with a liar, a woman who encourages her boy to be a girl, a boy who had managed to fool him for a year into thinking he was girl or that Mark was somehow gay. Whatever mum was hurt, she said she had to do it sometime and had run it through her mind and after my good outcomes at college and work somehow expected everyone to be OK with the idea of me being a girl, clearly she got that wrong. Emma tried to say he will call her when he cools down but she did not convince anyone.
The positive outcome from this busy two weeks of revelations was that I had nowhere to go that I needed to be Jens, if I choose my friends carefully I could be Jenny fulltime, not just at college and at work. Then as if to seal my fate the following week Ray called me to ask if I would work full time at the salon as an apprentice, he then put on a condition, that I present as Jenny while at work, my fate was sealed when I said yes and turned up to sign the forms wearing a skirt and heels, at least with these three there was no chance of a negative reaction, it was a good place to start my career from for sure.
The end