I never knew what fun there could be if only I tried a new style.
Well how to start? A bit of background, my name is Dan and I live with Marcus and not that we shout about it but we are more than good friends who share a house, we do have separate rooms but at times enjoy the comfort and affection of sleeping in the same bed. Marcus is a big bloke, he used to play rugby but was never one of the huge ones just a well built bloke who could run and handle the ball. Me I keep fit running and riding a bike, meaning I like to stay thin and carry as little weight as possible.
Well things changed between us when Marcus came home from work, he hardly ever makes comment about what he calls a boring accounts office because nothing ever happens, well something happened this day, the top management wanted to have a theme party and everyone was being pressured to bring their plus one. I said no problem I would go, he thanked me but recounted a story of bloke who came out of the closet to the office and eventually left because of the low level homophobia, nothing that could be taken to a tribunal but enough that he felt uncomfortable especially from a small number of staff members. So the answer was no, I would not be going with him. On the plus side to this party was that everyone had been given a decade to choose their style from and Marcus had picked 1950s out of the hat. We both loved rock and roll, Marcus even had a teddy boy suit, drainpipe trousers, long jacket and shoelace tie, going out to jive events more to watch than take part, two blokes dancing could cause a bit of a stir whereas two women went unnoticed. So unfair we would mutter and console ourselves with another coke.
A few days later I asked Marcus how his plans to get out of the dance were going, he was not to happy about how things were going, a woman who was doing a lot of the planning was asking questions about if he had got a plus one yet and one of the homophobic managers was trying to get him to admit that he was gay and would be fetching a bloke. I was a supportive as possible but he was not that positive telling me a broken leg might just be his only option with a hospital bed being his out.
That Saturday I arrived at my sisters after discussing the problem with her earlier in the week, I was unsure this was a good idea but felt it was the only thing I could do to help. With quite a few nerves and a lot of trepidation I knocked on the door.
‘Come in Daniele, how nice to see you.’ My sister gave me big hug as we kissed cheeks.
‘Please let’s just see how this works and will I make it.’
Soon I was in the shower washing my body hair down the plug hole before washing my hair with some very feminine smelling shampoo and conditioner. In a pink towel dressing gown I was seated in front of her vanity and told to look the opposite way, mirror behind me. She coated my face with her cosmetics before she took the towel turban off my hair and got to work with her hair drier and then heated tongues. I was allowed to see myself once my head was done and I was amazed at the pencil straight hair style she had got out of my shaggy locks, but on top of that my face had big eyes and very inviting lips if you like women looking pouty, and all thanks to makeup. While I was taking in the image I was seeing, she was sorting out my clothes. We are similar sizes and so I was soon wearing her scarlet bra and panties, zipping up a sheer red blouse before pulling a pair of her tight jeans on, thinking a skirt might be too much for me to handle on a first dressing, last dressing experience for this time she showed me how to buckle up the low heeled sandals to my feet.
I was taken to see what I thought of the redressed me in a long mirror.
‘Just wow, that is amazing, we look like sisters, Daniele and Christine.’
‘Well Daniele, if I say it myself, I did a good job. Now you have to decide can you walk out that door?’
‘Oh er, do you think I look that good?’
‘I think you look like a girly girl, what matters is do you? If you do then get yourself home and surprise Marcus.’
It took a while before I had talked myself into driving home.
I was home before Marcus came in from his day in town shopping. I was busy cooking when he came in.
‘Hi Dan, I’m home……………….oh sorry Christine I was expecting Dan to be home.’
I tried to make my voice softer and higher ‘He is home, just making your tea.’
There was a pause in which I did not dare turn round I wanted to see how long it took for him to work it out ‘Dan, what have you done?’
‘Come up with a solution to your plus one problem, say hello to Daniele.’ Making an exaggerated curtsey in front of him.
To be fair this was quite a bit for him to take in as he had no idea what was coming. ‘Did you buy anything nice darling.’ Hanging onto the darling to make it hopefully sound sexy. ‘Well sit down and I shall put the food out for us, do you want a glass of wine?’
As we ate I was very aware of him watching me carefully as I hammed up the feminine gestures. I explained how I thought I could pass as his girlfriend. How Christine had done the transformation. How it felt to be wearing unfamiliar clothing. How I felt about being seen as a girl. I told him I was fine with everything and actually liked the new sensations, and I was already his girl in all but name and dress, he smiled at this but it was true I liked doing the house stuff, cooking and cleaning were my domain and we knew it. At about eight he had been quiet for a while and looked at me with a serious face. ‘So let’s test this new look. Not been in the flying swan for quite while, white wine and soda for you no beer for my girl.’ He smiled and that was it I slipped on a denim jacket and picked up a shoulder bag Christine had given me to put my keys and money in.
We got back home a few hours later, a few drinks and plenty of close encounters with customers who took no notice of me as Marcus’ new friend. Marcus even commented how nice it was to be able to hold hands without fearing someone staring at him like happens when holding another man’s hand. In bed later I asked if he thought it was a good enough idea to work. I loved it when he nibbled my ear and whispered ‘yes’.
This was the start of a hard training period for me. Christine taught me how to do makeup and lent me a few outfits she did not wear anymore. The following weekend I wore my first skirt, a plain grey cotton A line. Christine made me up well before I had to make my own way home once more and be taken out by Marcus once more. Soon I was coming home and to start with walking about the house in my new heels which increased in height until I bought a pair of truly high heels thankfully with a platform sole under the ball of my foot so the 5” was really far less. I also started to look forward to getting home and changing into a skirt and tights, which soon turned into full make up and styling my hair if I had the time. Off course my weekends became purely Daniele time. Besides enjoying learning and experiencing a feminine style and life, it allowed me and Marcus to be affectionate outdoors, our reserved attitude towards one another broke down as I was slipping easily into the role of his girlfriend. Being able to hold hands, kiss and cuddle in public meant that when we got home single beds was not an option and after an early tenting in a skirt disaster, I took to using surgical tape to hold any future embarrassing erections in check meaning that I was always going to be the bottom if I was Daniele which seemed appropriate really and even more in keeping once I started wearing satin nighties to bed. At first to help me feel more feminine but later to help in the arousal of our love making.
In the few short weeks between Marcus being so despondent about this party he has changed completely to someone actually looking forward to it, he had got his teddy boy stuff out and after cleaning it found the trousers were now too tight, the jacket was fine and with a pair of black trousers and black shirt he looked quite good. But we both knew that a suit did not change much over the decades whereas women’s style was more defining, we needed to find a proper 1950 disc skirt. We looked online but once I was confident to go to shops in a skirt we went looking for the real thing and not just pictures.
Fancy dress shops had some half decent dresses but when we came across a vintage dress shop down a side street. We found ourselves looking along the rails while explaining what we were after to a more than helpful proprietor, soon I was being ushered into a changing area, this was not the plan, we were only looking. A glance over my shoulder towards Marcus hopefully saying ‘Help!’ did not help as this woman smelt a sale. She almost helped me undress as I tried to keep my back to her, I could not believe this over helpful attitude was normal, no one had ever come into a changing room when I was trying on gent’s things, maybe this is what women do in smaller shops. Whatever, I was working hard to not let her see my slight bump in the panties and socks for boobs. She had three dresses for me to try on. The first pink with bows on it was just too fancy and thankfully tight though she said a corset would sort that out. Second was a blue satin dress that felt fantastic to touch and was a possible, Marcus nodded approval when I was ushered out to show him. Last was a yellow one, net skirts, a bit more frilly and satin type underskirts, my favourite and when I showed Marcus he agreed, but being a man (I teased him about that later) felt obliged to pay. The woman found me a small clutch bag and some sling backs in a matching yellow. We thought we were sorted but as we paid she pushed a pair of seamed stockings into our bag, telling us they would finish the outfit off. I said a little too loudly that I did not have a suspender belt which she heard and told me that I should always treat myself to new underwear when getting a special outfit, I nearly blushed to my bones. But even more devastating were her last words.
‘You are so convincing I would never have guessed if you had not made so much fuss about keeping your back to me, you must really love being a girl and your man is just great, you will make a great couple on the dance floor. One thing though, there is a shop which you might have heard of, Bois and Gurls, go and get yourself some life like bra fillers.’
I did not know whether to be insulted, praised, embarrassed or encouraged.
Marcus was rather enjoying shopping with me and the thought of going into lingerie shops for the first time meant his curiosity would have me in something suitable for the dance. He teased me with black and red saying they were dead sexy and white was for virgins only, that was said with a wink, thankfully I found a set in lemon and we could leave for home. But not before Marcus followed through on the woman’s other suggestion of going to Bois and Gurls and fixed me up with a very realistic feeling pair of tits and a bag of lozenges that when sucked are supposed to raise the pitch of my voice. I sucked one on the way home and was soon speaking in what sounded to me like a squeaky voice making Marcus laugh and for me to giggle in a peculiar way which made us laugh even more.
With just a week to go I spent all my free time improving some aspect of my feminine appearance, makeup, posture, deportment, hair styling, even just being a girl about Marcus, who responded by coming home one evening and telling me he is going to treat me to a salon appointment so I can get my hair and nails done for the big event.
My sister, Christine, was never too far from developments and would come round to see how I was getting on, making constructive comments when needed, though suggesting I go all submissive now I was a sissy girlfriend did not go down well. I still saw my relationship with Marcus as the same even if in bed he was always screwing me.
The salon was a big step. I dressed as feminine as possible in a blouse and short denim skirt with my hair up in a pony tail. After a little chat about what sort of do we were going to she persuaded me to let her trim my hair, give it a colour to deepen the richness of my hair and fix it up ready for the evening. She wanted to extend my nails but I turned that down in favour of just having a manicure and polish, just how could I get long nails off for Monday but pink polish should come off with remover.
Christine was at our house when I got home and loved the sight of me walking in the door wearing a short skirt and high heels, with my hair up and nails flashing the pink. She hugged me, I asked was I being sensible, she told me I looked fantastic and would be a fool not to go through with it. And when she helped me into the dress told me I definitely had to go. She was good enough to drive us to the hotel where the dance was, giving us a lovely hug as we parted. It was now just Marcus and his ‘girlfriend’ hoping not to get found out.
We had a great time dancing, some of the others had good outfits but I reckoned ours was best even if Marcus did not really look like a teddy boy. I drank champagne most of the time and got rather giggly which only made me worse as the lozenge had its effect on my voice. I am sure no one noticed that I was really a man as plenty of people came to me and made comments like ‘We had Marcus down as gay, he never talks about a girlfriend’ ‘He’s a dark horse, where has he been hiding you?’ I tried to be ambiguous in my answers but my best reply was ‘He is man enough for me.’ In reply to someone who suggested Marcus was a bit camp.
It was late when we got home but my boyfriend wanted to impress on me that he was man enough as he insisted on making me scream as he pumped his semen into my hole. Sunday was such an anticlimax, by Monday I would have to strip away all this lovely femininity and go back to being a regular Dan again. After using the cleansers and removers I was looking more male but my hair now had a fringe which was a big change and I was sure would not go unnoticed. But it was as we talked in the evening and I expressed how much I had enjoyed playing the part and would be happy to be his girlfriend for the next party, Marcus smiled at me and asked me why wait that long, we could go out the next weekend with another couple from his work who liked rock and roll and fancied learning how to jive. I thanked him with a big kiss, it was then he added that he would not mind if I retained something of my feminine clothing fulltime. I was thinking of wearing panties all the time but with his consent I virtually threw out my briefs on the spot. I made love to him again in one of my lovely satin nighties grateful that I could pick the best bits of both genders, I would not miss makeup and heels everyday but I did enjoy dressing up and feeling the luxury of female fabrics was great.
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