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Girl's night out I hadn't seen Caryn, in months I was looking so forward to seeing her. I had fancied her for a long time and hadn't seen her since she had left to go to Italy. As she entered the arrivals hall, she ran straight for me and planted a kiss on my lips and screamed, "I missed you so much". I was so happy to see her; we talked virtually non-stop the whole journey back to her flat. I helped her carry her bags upstairs, and collapsed on her bed. Next thing I heard was she and her flat mates chatting, I went up and watched some TV while they nattered and shrieked at the stories that Caryn had got up to while she was away. Eventually Caryn and I went back into her room and we chatted while she unpacked. She sat down next to me as she sorted her underwear. I couldn't help myself any longer; I reached over her and started kissing her. I was shocked when she started to kiss back. Things got hot and heavy and eventually I was without my shirt and she was down to her bra and skirt. Eventually the bra went as well but she wouldn't let me into her skirt. I decided to stop, after all this was my best friend, whom I hadn't seen for ages. Suddenly her phone rang; she exclaimed that it was her parents calling to make sure that she was ok. I decided to run to the urgent toilet break, which I had been holding back for ages. I came back and she was still talking, I thought for a laugh I would start touching her inside leg to wind her up while she was talking to her mother. She pushed me back, into her pile of clothes. I grabbed one of her maroon bras and put it over my arms and started doing a lap dance in front of her. She was holding back her giggles, and she struggled to get her mom off the phone. Eventually she said goodbye and pushed me away saying jokingly. "You Bastard", while laughing. She said "you have it on wrong," and grabbed the bra clasp and fastened it behind my back. "Owe you got my skin," I said as I jumped on top of her. We kissed for a few more seconds when the bedroom door suddenly flew open followed by a shout "Ha caught you shagging". Suddenly her flat mates had appeared with a camera and a flash. Next thing I hear is giggling and laughing. I suddenly realised that I was still wearing Caryn's maroon bra. Caryn started laughing as well, as though she enjoyed my humiliation. I ran out the room and pulled the bra off. I was going to leave when I thought that I had better get the photo back. There is no telling what Caryn's flat mates would do with it. I went back and saw them all giggling on the bed. Sarah, Caryn's flat mate, said "ah darling where's your pretty bra gone?" "Very funny" I replied," What did you do with the camera?" "I have it here but there is no memory chip in it. You will have to some things for us to get it back." Sarah said with a huge grin on her face. "Like what?" I asked hesitantly. "Oh, I have a few ideas" Sarah sneered. Chapter 2 A new girl in the flat "We need some stuff from the shops here's the list go get it" Sarah said. As I left I heard a girly giggle coming from the TV room. I bought the groceries and went back to the flat, only to find the place quiet. I left all the stuff on the kitchen table and went into Caryn's room. Caryn was there and had now finished unpacking. "Have you got the photo?" I asked her. "Why not its only fun" "This could ruin me" "Nonsense" A knock came on the door, and Sarah screamed from outside the door" Anyone in their underwear?" Tina and Sarah walked in. They were both pretty girls in short black skirts and tight t-shirts of varying colours. Sarah said "we want you do something for us" "What?" First of all "Put these back on she said as she handed me a bag sealed shut. Inside was the maroon bra and matching maroon panties. "You must be joking!" I said. Sarah said "oh and you better remove that body hair, I have left a spare Gillette razor in the bathroom". I looked as Caryn who giggled along with Tina. "Go on" said Tina "its just a bit of fun. "Do you promise to give me the photo back afterwards?" I asked "Of course" Sarah said. I went into the bathroom and ran the shower and removed ever inch of hair from my legs, chest and underarms. It stung like crazy. Caryn had told me to put some moisturizer on it to stop the stinging. I gently massaged it into my body and eventually the stinging subsided. I looked in the bad and pulled out the lacy pair of knickers. I would have loved to give them as presents but the thought of me wearing them made my stomach ache. I pulled the maroon panties up my smooth legs. The material felt wonderful against my skin. I pulled the bra over my shoulders but I couldn't do the clasp at the back, so I left it and pulled on a white gown to go outside. Caryn was waiting for me at the door and asked to see. I told her that I couldn't do my bra clasp. She responded by pulling my gown off and reaching behind my back and fastening the clasp. I was now stuck in the middle of the flat in girl's sexy underwear. Just then Sarah and Tina walked out of their rooms and saw me. "You look really cute," said Sarah. Tina said, "Yes you look just like a model in Maxim magazine in fact here is the mag you left here last year". Sure enough on the front cover was a model wearing exactly what I was wearing. "You're right but I think that she is wearing make up though." Sarah interrupted "all in good time". "No way" I said. Sarah replied, "Ok, well if you want me to call and invite the neighbours over". I lamented and said, "I'll do what you want." Sarah led me into her room and sat me down in front of the mirror. I felt my panties begin to bulge as Sarah bent down to pick something off the floor. I grabbed for a towel and put it round my waist to cover up. "Oh shame, are you really cold, don't worry here's a top you can borrow, and a nice short black skirt that you can wear. If your legs are cold you can have a pair of tights, if you want" Sarah said through a grin. "No I am fine I will just wear the towel" "Oh no you wont" she said as she held the skirt out to me. I grabbed for the skirt and gently slipped it up my legs and pulled up the zip on the rear. I pulled on the red Morgan top but the sleeves only went up to the ends of my elbows. "It doesn't fit, I won't be able to wear it," I said trying to get out of wearing this overtly feminine top. "Yes it does. That's the style, the top is quite tight so you can see you bra straps sticking out. Let me look at you. Wow what a difference that makes; now you dress like one of the girls! I think we should show the other girls what you are wearing." I meekly stepped outside; Tina caught a glimpse of me and laughed hysterically. "You look really pretty," she said out loud. I snuck back into the room my face really red from embarrassment "Come and sit down so I can make you up," Sarah said motioning to her mirror. I gingerly sat down, feeling very exposed in my skirt. "This will equalise your skin tone" Sarah said as she began to apply some cream to my face. I was feeling very uncomfortable, as the panties were really tight forcing me to move to get comfortable. "Cross your legs it'll be good practice". Sarah said harshly "For what?" "Close you eyes" so I can apply your eye shadow" Sarah said impatiently, "But its daytime none of you are wearing any makeup." I said trying to get out of being made up. She replied that girls always wear at least a bit of makeup She said that if I didn't want to wear a lot she would put on more subtle makeup that would probably make me look more like a real girl. As I closed my eyes I felt a light brush move over my eyelids. "Open your eyes" she sneered. I opened my eyes only to see Sarah's body covering the mirror. She was moving a mascara brush close to my eyes making me flinch. "Don't move." I kept still whilst she wet my eyelashes. Eventually she pulled out a pink lipstick and quickly applied it to my lips. My lips felt all moist as I rubbed them together. She gave me a tissue so I could blot my lipstick. "I should be a make up artist," she said as she stepped away from the mirror, to display an effeminate looking girl, who looked vaguely familiar. "Come on Stand up, let's go and show the other girls what a pretty girl you make". Sarah said. I stood up and was about to walk into the next room when Sarah told me to put some shoes on; before I left. She had opened her cupboard to reveal shoes made up of multitude of colours with leather straps in gold, pink and black. I picked out a pair of nice unisex white trainers. "No you don't" said Sarah, "nothing without a heel. Here take these sandals." She gave me a pair of black, high-heeled sandals with diamond straps. 'Aren't these a bit fancy?" I asked, grasping the trainers. "Ok try on these plain ones," she said passing me a pair of plain black strappy high heels. I sat down on the bed and slid one of the shoes on to my foot and did up the strap. Just as I was doing the same for the second shoe, Caryn walked in to the room. She didn't really look at me but just walked to the bathroom and asked if I was in the bathroom. I couldn't believe it she thought I was Sarah. It suddenly dawned on her when she saw Sarah emerge from the bathroom. She spun round to look at me in disbelief. 'Come on Sarah, enough of this game. This is too much; you said we would only make him wear underwear. I never would have expected to see James in a skirt and make up doing up the strap on his high heels' "Its only fun" said Sarah, "and aren't you impressed with the result?" "Well he does look quite sweet in the Morgan top!" Caryn said with a giggle. "James come and sit in my room." Chapter 3 The New Girlfriend I stood up shakily on my heels and followed Caryn into her room and sat down on her bed. She told me that I could take off my heels if I wanted. I looked around for my male clothes, but couldn't find them anywhere. I undid my sandals and stepped out of them. I was still quite cold so I asked if I could borrow some tracksuit trousers. Caryn searched through her cupboards and pulled out a pair of trousers, which looked way too short. "None of my trousers are going to fit you except, for these skirts and these cropped trousers which are really elastic "I wouldn't turn down the chance to get back into trousers," I said as I grabbed the trousers. I slipped on the cropped trousers and zipped up the zipper on the side. I sat down on the bed and asked if I could change out of top as my bra was really constricting. 'Now you know how I feel, its not easy wearing a bra and walking around in heels all night" said Caryn. I slipped off my top and threw it on the floor, leaving my maroon bra exposed. I could see this was turning her on and next thing you know we are kissing again more passionately than before. After a few minutes of kissing we were both lying on Caryn's bed. Both of us were in our panties and bras and Caryn was looking really hot. She was wearing a matching set of blue lacy knickers and bra. We kissed for ages until there was a sudden knock at the door. I quickly threw on a bathrobe when Tina came in and exclaimed, "Oh wow! This is the second time I caught you in your sexy underwear James, you must really like wearing them" "Come into my room with Caryn so we can have some fun" said Tina. I looked at Caryn who was getting dressed already. I pulled my trousers on and began to walk out. "Put on a top you can't walk around showing your bra off". Tina said I picked up my red top when Tina threw me a white strappy vest. "Put this on to show off your bra if that's what you want. It will make you look girlier" I didn't even bother to argue, as I pulled on the vest. I felt really exposed, my shoulders and back were showing except for the thin straps that covered hardly anything. "Fix up your lipstick James". She said handing me a tube of raunchy lipstick. I carefully applied the lipstick making my lips a metallic pink. I picked up my heels and was about to walk into Tina's room when she turned around and shouted, "Put on your heels, I want you to get used to wearing them." "Come on" I said. "Just do it". She hissed as I began to slide them on. As I crossed the passage into Tina's room, Sarah was walking through and exclaimed nice outfit James or should I now call you Gemma!" "No James will be fine" I replied indignantly. "Whatever you say Gem! By the way walk on the balls of your feet when you wear heels it'll be easier" I walked shakily into Tina's. It helped to walk on the ball of my feet however it also, made me swing my hips when I walked. I got into Tina's room and slumped down on chair. "Come on Caryn lets teach James to sit properly for the next time he is wearing a skirt." Tina laughed. "I am not going to wear a skirt again," I said, making my stand. "Well now you definitely are going to!" says Tina " and if you don't watch what you say you'll wear one tonight when we go out." Just then Sarah walked in with her camera and snapped a picture and ran out. I tried to run after her but tripped up in my heels. I sat on the floor and started shouting at Caryn. "How can you let them do this to me?" I said almost in tears. She could see that I was upset and said "don't worry it'll be over by the time we go out tonight" Tina said, "that's right but we can play now. Anyway back to the subject of you not wearing a skirt. Caryn go and pick James out a nice pretty skirt. Caryn stood up and opened Tina's cupboard. She searched through the cupboard while I waited. I could see a ton of feminine looking dresses and skirts that I had no intention of wearing. I was horrified when she pulled out a bright pink skirt. "If you are going to wear a skirt you might as well have as much fun as possible" she said as she threw me the skirt. I took off my heels and pulled off the cropped trousers exposing my panties. I pulled the skirt up my legs and fastened the zip on the rear. "Here is a belt you can wear with it" Tina said as she handed .me a thin chain that looked more like a necklace than a belt. "Its latest fashion" says Caryn. "I have got one as well" "That's really reassuring" I responded angrily. Tina asked Caryn what shoes I should wear with the outfit. "Lets giver him something sexy, like those sexy pink sandals with the white straps!" Caryn said, who was obviously beginning to enjoy my humiliation immensely. "You mean the ones I wore last night? Here they are" said Tina as she pulled out a pair of pastel pink high heels with straps dangling everywhere. "Don't worry I will help you put them on, they are easy once you get used to it." Tina said helpfully. "But I don't want to get used to it!" I said. " Tina ignored me and was already setting the shoes down next to my feet "Come-on James stop whining you are starting to sound like a girl!" she giggled. I slipped on one of the shoes and Tina tied the straps around my ankle. I did the other foot: It was really complicated, you had to wind the strap around one ankle and the other strap went round the same ankle and then fastened to the other strap. It felt quite tight and uncomfortable. Caryn said "You should probably wear some tights with those shoes do you want me to get you some?" "No I am fine," I said "We are only going to give you some tights if you ask" Caryn said, trying to be helpful. "Fine with me, is it ok if I don't want to wear this outfit?" I said but was ignored as they talked together. I could overhear Tina say that I would be begging for some after I walk in those shoes for a while. She could hardly manage to wear the shoes without them. "Ok James lets stand up and se what you look like" Tina said gleefully. I stood up uneasily on my heels; the skirt came down to just above my knee and was quite tight. The pink heels seemed to be bit higher than the other ones so when I walked I had no choice but to walk on the balls of my feet. The skirt also helped to feminise my walk. "Wow James you are a real stunner. Come and sit next to us so we can teach you how to sit like a lady" Tina said. Both Caryn and Tina showed me the various mannerisms and how to move and sit. 'Cross your legs like us" said Caryn, trying to be helpful as she crossed her legs and placed her hands in her lap. "This is the way you must always sit" Tina said " and just think if you would have cooperated before, you could have done this in your cropped trousers and not in a pink skirt" 'Yes I am sorry about that" I said sincerely as I did my best impersonation of them including holding my hands in my lap Very good you even had the mannerisms down to pot; anyone would think you have been doing it your whole life" said Tina happily. "Oh that reminds me," said Tina as she looked at my hands, "we have to do your nails. You can't wear shoes like that without painted toenails". Caryn had always been partial to her nail varnishes; she probably had one of the largest collections of any of the girls I knew. Caryn walked back into the room and sat down next to me. She pulled out a metallic purple nail polish. "This will match your underwear" Tina said with a laugh. She gave me the bottle and after I had done a terrible job of applying nail polish to my one toe she said, "I'll do it or we will be here all night". When she had finished I looked down at my legs, and realised that they could have been my ex girlfriend's with painted toes pink strappy heels and pink skirt. "Enough I said no more" I said as I stormed out as quickly as I could. I realised that I didn't have any male clothes and if I went out, it would be in a skirt. Tina came into the passage and said "oh if you are going out maybe we should finish doing your hair and nails so no one will recognise you. Although they will probably recognise you when they see the clip of you putting on your lipstick in Caryn's room dresses like a girl, she said holding up a small digicam. "I think you had better go and finish getting changed." Said Caryn. I couldn't believe it, from being on my side, Caryn appeared to be siding with the girls. She whispered in my ear "sorry but I am not going to side with you against them they will never speak to me. Come on I'll finish doing your nails," she said with a smile. "I'll make it worthwhile later." I went into Caryn's room and she opened a box full of false nails in the same colour as my toenails. "I did these while you were painting your toenails." She said, helpfully. She could see that I was visibly upset. "Don't get upset you'll smudge your make up and it'll give Sarah another excuse to make you up again," She said sympathetically. It was nice to know that I had at least one person looking after me. Eventually when Caryn had finished sticking on the nails, I looked down Caryn held out her hands, which were done in a similar style nail polish to mine, and she said, "You're lucky you have girls hands". It was true now that I had the long nails, our hands looked similar. "Very nice" said Tina and Sarah. "Give him that blond wig and that necklace and bracelet that are on you desk" I looked at the jewellery and realised that I had given it to Caryn as a going away present when she had left. The necklace and bracelet were very thin except for the Tiffany heart on the necklace. Sarah exclaimed, "I think we have finished" Stand up and look in the mirror. Staring back wasn't a boy and three girls, but four gorgeous girls. My eyes were confused for a second, as the sight was so unexpected and I didn't know which of the girls I was. Chapter 4 Shopping Trip "Ok James, we are going to run out to the shops and guess who's coming." "No way" I said, "I am not going out" "Ok you have a choice; you can otherwise stay here with me while my friend Kerry comes over" threatened Sarah. She is much more of a gossip than us and she would tell like there is no tomorrow, your choice." "Ok I'll go"! I said, but I can't go like this I am way too dressed up" thinking that I could try and get an outfit more unisex. "You're right" Sarah said, I breathed a sigh of relief at the thought that I would be back in trousers soon. "Come with me into my room and I will help you to pick out an outfit. Your makeup is also running a bit, I will help you touch it up so you will look pretty again." Said Sarah "How are the shoes still comfortable?" "Actually it hurts each time I walk, the straps are really tight and rub each time I walk, I can practically feel the blisters coming." I was so close to giving in and asking for a pair of tights when the suddenly the doorbell rang and Caryn got up to open the door. My heart dropped as Kerry, Sarah's friend for ages, walked in and took one look at me and said "Hi I'm Kerry" I was shocked for two reasons, firstly that she hadn't recognised me and secondly because she was wearing virtually the identical outfit to me except for different colour tops. "I'm Gemma," I said in a false girly voice causing Sarah to smile. I went and sat down on the chair and did my best to appear as effeminate as possible sitting with my legs crossed and my hands in my lap as I had been shown. My shoes were really uncomfortable it had hurt every time I walked in them and my feet were burning. I wasn't sure how long I could wear them for. I was horrified when Kerri sat down next to me and started chatting to Sarah. Kerry said to us "I hope I am not interrupting anything" "No actually we were just getting ready to go to the shops. Gemma just wanted to get changed before we left," said Tina with a grin. Kerry replied, "You don't have a lot of time the shops close in about 15 minutes and it's a good 10 minutes walk. Its quite cold outside, put on a pair of tights so you aren't cold and a coat and lets go" "Oh wait, Gemma, didn't bring any tights with her" said Sarah with a grin. "That's ok, I am sure that if you ask Tina nicely she can lend you some. You look about the same size" All the girls looked at me in glee. Just as I saw Sarah about to start talking I said, "Can I borrow a pair of tights, Tina?" I was quivering inside. "Sure come with me, I need to touch up my makeup anyway" I walked with Tina into her room. She threw a pair of skin coloured tights at me and said, "Put these on" I looked at them and exclaimed, "These won't fit me " "Its ok, they stretch, these ones will give you amazing legs," said Tina. She showed me how to put on my tights and as I was doing up my shoes she said "Hurry up GEMMA, I need to fix up your makeup" "My name is James" I replied angrily. "Ok JAMES", Tina Said "Do you want to tell everyone inside what your name is or shall I?" I ignored her question and carried on fastening the straps on my heels. "Ok then fix your tights, Gemma so that I can touch up your makeup" I rolled my hands up my tights to straighten them out and sat down in front of the mirror in front of the feminine figure, which was gradually becoming the familiar site I recognised as me. I crossed my legs like I had been taught and adjusted my vest and bra straps, which had slipped, down my shoulder. I felt a pair of soft manicured hands grasp my bare, exposed, shoulders "Very good, you should always look neat and tidy. Because we are running late I am only going to put some eyeliner and mascara on you so at least your eyes will look convincingly feminine. Close your eyes, now you may feel a weird sensation on your eyelids. She was right; I felt a wet sensation on my eyelids as she applied the eyeliner. I opened my eyes and couldn't believe the difference. My eyes looked the same yet they appeared to be wider and prettier. "The liner emphasises the line of your pretty eyes," she said. Just as I was getting ready to flinch for the mascara, she placed the mascara tube into my hand and said "go on try it out yourself, its easy, just don't poke yourself in the eye" I followed her directions and gently teased up my eyelashes, until they were beautifully curled. I touched the mascara brush along the bottom eyelashes to further define them. Once I had finished, I couldn't believe the difference that it made. My eyes were deep set with long curling eyelashes and you could still make out wisps of the colour left over from when Sarah put eye shadow on my eyes. The effect was really breathtaking. "Come on lets go," said Tina as she stood by the door. I took one more look in the mirror, my make up looked great except most of my lipstick had faded. I decided not to risk being caught so, after making sure Tina wasn't in the room, I grabbed the tube of pink Lipstick that I had used before and applied it to my lips. As I walked out, most of the girls were already out of the flat. Tina was standing there with a black cardigan ready for me to go out. I pulled it on and tied the string fastening it closed. "Oooh nice touch with the lipstick, the colour really suits you," she said. I said thanks as I walked past her. My heels clicked along the pavement as I walked. The other girls were only about 100metres; a quick jog when you are in trainers but in heels it seems a much greater distance. The heels force you to take smaller steps so the only way to go faster is to make more steps, which makes a hell of a clicking noise. Eventually the girls stopped to wait for us to catch up. When we met up with them, Kerry said, "We could hear you coming so we decided to wait" Caryn whispered in my ear " You had better start acting and walking like we showed, I think Kerry realises that something is different about you" I immediately slowed down and concentrated on walking as daintily as possible while swinging my arms like the other girls were doing. Eventually when we got to the store I excused myself to go and buy some cigarettes. I suddenly realised that I had no money, so I asked if I could borrow some from Caryn. "I thought you would never ask", she said as she rustled through her bag. She produced a soft leather purse and gave it to me. "The contents of your wallet are in this purse. You should probably get a bag to carry it in after all you don't have any pockets. Come on I'll pick you out a nice bag that you can use." 5 minutes later I was paying for my new soft leather handbag. The girl at the cash register didn't notice anything; in fact she said she had the same one, which she used to wear when she went out at night. Eventually we all met up at the store entrance. Sarah and Tina were carrying large bags, Caryn had a few smaller bags and Kerry was carrying a box filled with wine bottles. "It would be nice to have a bloke to carry some of this stuff for us" said Kerry. The girls all started giggling, not to be left out I let out a few girlish giggles, which surprised Caryn. Eventually we arrived back at the apartment; I slumped down on the couch while the girls unpacked their stuff in their rooms. 'James won't you help me unpack the bottles?" "Sure" I said only to bite my lip when I turned around and realised that Kerri had called me James! I thought she didn't know Chapter 5 Learning how "James, you look really sweet, honey however you have to master the art of running in heels. When you run you look like a man in a dress. You have to be more feminine if you want to look like a girl" Kerry said with a chuckle. "I don't want to be a girl," I said angrily. I stormed into Sarah's room and started looking for a pair of trousers I tore off the cardigan, vest and bra and ripped the tights and skirt off in disgust. I pulled on a pair of jeans and a normalish t-shirt and began to walk out. I grabbed a pair of socks and some trainers and just as I was walking out Tina and Sarah said, "don't forget your makeup and your nails" Sure enough I still looked like a girl and I was horrified that my shirt had a pink heart in the middle of it. I ran into the bathroom and threw water all over, my face, which only succeeded in smudging my make up. My nails also wouldn't come off. I shouted for Caryn who came in and told me to calm down. She took some pads out of a bowl and poured a liquid over them and started rubbing my eyes gently. Eventually most of the make up was gone, however there were still a few remnants on my familiar face. The one problem was that the fake nails wouldn't come off. Caryn said "sorry I must have used too much glue, you will probably have to wear gloves for a day or two" Just then we heard a knock on the bathroom door. We then heard Tina's voice call us to the lounge for a meeting. I walked into the lounge and sat down. Sarah looked at me and said "why are you still here, we are going decide who to show the pictures of you to. All because you didn't keep your part of the deal" "Ok, let's set out the terms I said, trying to be conciliatory. "You will have all the photos back tomorrow morning" "What do I have to do?" I asked hesitantly, "You have to come out with us tonight as one of the girls. You do everything that we do or say" "What choice do I have?" "None really", said Kerry, "but don't worry, I am going to pick you out a sexy outfit so you will look great tonight." Tina came up behind me and started rubbing my shoulders and said "Just think how much fun you will have, you'll be dressed just like the rest of us girls, you will look great, your face will be beautifully made up; you'll be wearing a slinky, sexy dress, with your shoulders and long legs exposed for the world to see. Matched up with a the right pair of high heels, you will look dynamite" "Ok, but you promise to give me the photos back" 'We have to start preparing, do you know how to dance?" asked Kerry. I nodded. She carried on "We are going to have to show you how to dance in heels like we do." I suddenly realised that this would be more challenging than I thought. Tina, who used to teach dancing, said, "First of all I want you to go and pick out something to wear while we are practising today, go and get changed, then I will come and help you with your makeup" "Why do I have to wear make up?" I asked. "For the rest of today you will be treated and are expected to act like a girl. If you start being all macho then you will just have be a girl tomorrow again. If that happens I have a drawer full of lingerie waiting for you." I was shocked into silence. Caryn had sensed that I was getting myself into trouble and decided to intervene. She stood up, took my hand and led me into Sarah's room. "Why don't you choose your underwear," Caryn said motioning to the drawer." I said that because you are going to a club with us you should practice in something a girl would wear to a club." she said as she opened up Sarah's underwear draw. I was visibly upset, but I asked her to make sure that they didn't take things too far. She said that I was stuck in this situation, but I should make the best of it, she would do her best to help me but only if I was putting in maximum effort. I agreed and walked over to the cupboard and began to look through Sarah's draw. I finally picked out a matching set of black lacy knickers and a black lacy bra. Caryn told me to put them on. I pulled off my other clothes leaving just my knickers on. Caryn turned around so I could change into the black knickers. I pulled on the bra making sure that I did the clasp first. Once I had pulled the last strap over my shoulder, a weird sensation came over me I started to feel really sexy and feminine. I thought that if I was going to be a girl for the rest of the night I might as well do it as well as I could and from tomorrow everything would be back to normal. I said, "Ready!" as I did a showgirl like posing. Caryn said" Wow James you look really sexy! I had an outfit picked out from my cupboard for you but its too small" she said as she put back a pastel blue outfit. "I have looked through this cupboard and I can't decide what you should wear," said Caryn. I replied "Don't worry about that I will choose, just help me to do my makeup and I will get changed" I sat down at the mirror and started putting foundation on my face like Sarah had done. "That's it James you are being a really good sport, enjoy yourself" Once Caryn had showed me how to equalize my skin tone, using the foundation. I started to apply my eye shadow. I chose a dark blue colour and a silvery glitter colour. Caryn told me how to apply and blend the colours. I had to apply the eye shadow carefully, which isn't easy when you have long purple nails, so that it looked pretty. After I had finished I looked in the mirror and for a second my masculinity reasserted itself when I felt revulsion at what I was doing to myself. It was only when Caryn put her head next to mine that I looked at her beautifully made up eyes, smelt her feminine perfume and felt her soft silky clothes rub on my skin that I realised that I wanted to look and act like a girl tonight. Caryn sensed the revulsion that I was feeling tried to help me by complimenting me "You have really pretty eyes" as I picked up the purple eye shadow and added wisps of purple to the edge of my eye to match my nails. "That's a nice touch" she said, "You're a natural, I wouldn't have thought of that, come on lets do your eyeliner." Caryn carefully applied eyeliner to one of my eyes and let me do the other one. I did quite a good job, even adding an extra line to the edge of my eyes like Caryn and Sarah did to their eyes. She then took a brush dipped it into blush and dusted my cheeks just around my cheekbones. This gave me a healthy bit of colour around my cheeks, which had been removed by my foundation. Caryn started reaching for the mascara when I said, "Don't worry Caryn I can finish the rest of my make up, you go and watch some TV" Caryn was originally stunned but agreed and left the room. I couldn't believe what I had just done, I had asked a girl to leave so that I, a boy, could finish putting my make up. I picked up the mascara and gently applied it to both eyes. I then looked at several different coloured lipsticks, finally deciding on a pinky red colour, which I applied to my lips. I stood up and looked at the final finished product and thought "Wow, girl you are going to knock them dead" I stood up and walked over to the cupboard and opened it up. I looked at the various items of clothes and acknowledged that I could wear any of them I wanted. I had the choice of all Sarah's dresses and skirts and even her sexy lingerie to wear. I had the choice of her various colours of heels and high heel boots to try on and wear, as I wanted. I looked at several items of clothes and eventually chose a black skirt with a slit on the side to expose a bit more of my legs. I held it up to my waist and though that it would look quite sexy. I looked through Sarah's pile of tops of varying pastel colours and eventually I decided on a soft pink strappy top. Next it was time to decide what heels to wear. I looked through Sarah's various colours and decided on a black pair of wedge-toed shoes with a thin strap and really high heels. I thought if I practised walking and dancing in really high heels then it will be easier when I dance tonight. I remembered how uncomfortable it was wearing those heels earlier without tights, so I opened her underwear draw and picked out a pair of black opaque tights. I gently slipped the tights up my legs being careful that my long nails didn't ladder them. I was amazed at how long and sexy my legs looked in the black tights. I pulled on the skirt and adjusted the slit so that it exposed a bit of my right leg when I walked. The feeling of the soft skirt rubbing against my tights was erotic and only added to myself feeling sexy and feminine. I pulled on my pink top, making sure that I didn't smudge any of my make up. After which, I sat down and started putting on my heels when Caryn walks in, and stops stunned. 'You look incredible" she said, shocked. Just then she walked towards me. I noticed that she had on a virtually identical pair of heels in preparation. She bent down and held my other shoe out to my foot. My dark nylon clad foot slipped into the heels and as she did up the strap on my heels, her other hand gently rubbed up and down on my tights. The sensation was electric. When she had finished I stood up on my heels. We hugged and I gently started tickling her back with my long nails. This was obviously turning her on as she started rubbing her legs against mine. The feeling of her tights rubbing against mine was really sexy. She could sense that I was getting turned on so she put her lips to mine and started kissing. I could taste our lipstick intertwined, her lip- gloss tasted like bubble gum. I was enjoying the scent of her perfume when she suddenly pulled back and said "Hold on James I just want to add a final touch" She reached over and picked up her perfume and sprayed it onto my chest and onto my neck. "Now you're perfect she said. You are not wearing a single thing that a bloke would wear, I think we can start addressing you in feminine terms, with that she turned around opened the door and shouted to the other girls "She's ready!" I heard laughing in the background. I looked at myself in the mirror, every inch of me looked like a girl, even with shortish hair. I looked at my lipstick and noticed that it had been smudged again so I carefully reapplied it and said to Caryn to do the same. "Can I use your lipstick James," she said I picked it up and gave it to her. She walked out the door and as she shut the door she said "I want to surprise them with how much of a sexy girl you've become" I could hear what they were saying through the door. Kerry had the loudest voice and through the door I heard her say, "what is she wearing? Giggles ensued after which Caryn's voice popped up and explained" James is wearing roughly what I am wearing, the same high heels, the same colour top and skirt except James' skirt has a revealing slit down the side. Oh yes and he is wearing your black opaque tights. Suddenly the door swung open and I was faced with four girls. "Wow you DO look great," they all said in turn. Tina grabbed my hand and said "come on, girl lets go dance" I walked behind Tina into the TV room. As Sarah was enjoying humiliating me she obviously wanted to try and make me feel as uncomfortable as possible. She said, "Do you know what James, I just realised that everyone here is wearing a skirt, heels and tights. Just think if your friends saw you now. "They wouldn't recognise him with his make up on," said Kerry trying to be helpful. "Come on lets start" said Caryn as she switched on MTV. There was a girl band on, singing and dancing. Kerry pointed to them and said, "You now, have more in common with them, than with a boy band. You have worn the same clothes, worn makeup and soon you will be dancing like them. "He hasn't worn a dress yet," said Tina. "No not YET but soon." said Sarah. "James will look really sexy in a slinky cocktail dress" I could do nothing but blush, which was thankfully hidden by my makeup. After a few hours of dancing and drinking, I was dancing just like the other girls; I was walking and dancing femininely in heels and a skirt as though I had been doing it for years. In fact, my actions were so effeminate that I thought that by tomorrow I would have problems adjusting to normal life again. 'Come on its time to get ready" said Tina. Chapter 6 Getting ready to go out "I am going to run back to my flat so that I can get ready, see you later!" said Kerry as she walked to the door. Caryn said, "I will shower first," said Tina "help James remove his makeup" "Its okay I can do it myself," I said as I walked to Caryn's room. I sat down at her mirror and gently removed my makeup. When I had finished, Caryn walked in, dressed only in a towel and exclaimed "There's the James that I recognise, without any girly makeup" I stood up, she came up to me and rubbed herself up against me. I was getting really hot just thinking what was under her towel. She whispered, "Unfortunately, the tights, heels and skirt don't do wonders for your masculinity, maybe later when you are back to normal, we can play. I don 't like the idea of the guy I am kissing wearing more girl's clothes than I am. For tonight, you are more of a girlfriend than anything else." I was furious but I didn't say anything I adjusted the hem of my skirt, which had moved up due to my "excitement" and walked out. Sarah was just walking out of the bathroom, with a pink towel wrapped around her body. "Come on dear hurry up, come into my room when you've finished in the bathroom." Caryn was the only girl in the house who didn't get upset when I spoke in my normal voice. I said, "ok" in my girl voice, which I was getting used to using when I wasn't around Caryn. I quickly went into the bathroom had a shower, wrapped one of the pink towels around my body like I had seen the other girls do. I walked out and into Sarah's room. She was sitting there in sexy black underwear, on her bed talking on the telephone. When she saw me walk in she motioned to her cupboard. I walked over and picked out similar underwear to Sarah's, except I think mine was lacier! I pulled on the panties under my towel and put on the bra. I dropped the towel and turned to face Sarah. She gave me the thumbs up. I went over to her cupboard and started looking through it for a nice dress to wear. Eventually I picked out a slinky black dress with a crossover back. Just then Sarah put the phone down and came up next to me and looked at the dress, I had chosen. "You have great taste," she said as she started looking for her outfit. I picked out a pair of skin coloured tights and pulled them on after which I slipped on my dress. The dress felt wonderful against my skin as I pulled the straps over my shoulder. I turned around to face her and Sarah exclaims, "wow that look great! What do you think of my outfit?" She had also chosen a black dress but hers was strapless. "It looks really pretty," I said. She slipped on her dress and I helped her with her zip. I started to look through her cupboard for a pair of heels. Sarah stopped me and said "don't worry, when we went shopping I bought us all a pair of gold high heels so we will all have the same high heels when we go out. Here you are James your first pair of high heels!" I tried to act as girlishly excited as possible as I took the box removed the pair inside and tried on the shoes. I looked over to see Sarah fastening the straps on her heels. I thought that from her perspective I would look identical to her. I stood up and looked at them in the mirror. I tipped onto my toes to see how comfortable they were and the were surprisingly comfortable. I think from walking on higher heels, it made these heels seem like they were as comfortable as trainers are, even though the heels were definitely high. "Come sit at the mirror and we can do our makeup together," said Sarah as we both sat down next to each other. We had quite a laugh trying on various looks eventually I chose a light blue eye shadow with a tinge of pink glittery eye shadow to blend in. Sarah pulled out a case from her shopping bag and inside was a pair of false eyelashes with a line of white glittering gems along the base. Sarah applied hers to her eyes and then I applied another set to my eyes. I applied some eyeliner to the edge of my eyes and began to apply mascara. I looked into the mirror and saw Sarah teasing up her long eyelashes as I was doing myself. Once I had finished I looked at the final result and couldn't believe my eyes. If my eyes were looking feminine before, they were now looking super feminine with the long eyelashes and the white gems sparkling along with the glitter. Sarah handed me a bottle of gold glitter stick, which I applied to the edges of my eyes and to my chest. I finished up by clipping on a black thin chocker and a thin bracelet to my right arm. Sarah and I stood up and posed next to each other by the mirror. We were looking great. Sarah looked me up and down and said to me "Just think this morning you had no idea you would be dressed up the same as us going clubbing!" "I had no idea I said as I put some perfume onto my neck. I packed a small bottle of perfume and some cosmetics, as well as my purse into my bag and put it over my shoulder and walked out of Sarah's room. I walked into the Lounge where another shock awaited me. Caryn was sitting there with a drink on the Couch with Kerry and two of her friends who I hadn't seen before. Kerry was wearing a short red skirt and gold heels like mine. In fact everyone was wearing the identical heels. Caryn was wearing a tight leather strapless top and a short black skirt. Kerry saw me and exclaimed "Gemma there you are, let me introduce you to Sally and Dinah. I looked at the girls and said "hi". I commented at how pretty everyone looked. Dinah returned the compliment. I poured myself a vodka and orange and sat cross- legged on one of the stools at the kitchen table. The girls chatted and I played along as the shy girl type. The good news was that no one worked out that I wasn't Gemma. Eventually Tina and Sarah walked in. Sarah said, "The cabs are here. Tina, Caryn and I will go pickup Rachel and we will meet you in the queue." I had a horrified look on my face but since everyone was walking out, I just followed behind. I took a soft furry coat from the cupboard, which I put on and tied, closed. The Coat went down to just above the hem of my skirt so all you could see were my long legs and gold heels sticking out. All of us walked down the cabs waiting outside. We got a few looks from passers by, as a large group of girls would. I was concentrating on walking as femininely as possible. We all clicked across the road in our heels, and I got into the back of the cab, I made sure to smooth my skirt so that it didn't get creased as I sat in the cab. Kerry was sitting next to me and started to hold my hand as we talked. I was looking at my legs while we were sitting in the back seat. All three of us in the back seat had short skirts on, so it was easy to compare legs. All our legs were smooth and shined as the light reflected off our tights. My legs were the longest however Kerry's friend had really stunning legs. Her short gold dress added to her sexiness. As she moved around I could see her heels glinting in the light. We joked and giggled the whole way there. Chapter 7 The Club We arrived at the club at about 10.30pm, so there was already quite a big queue. As we were walking down the length of the queue, I heard various insulting phrases such as hello gorgeous. About halfway down the line I feel a tug on my arm I turn around to see a bloke in a leather jacket. "What's your name?" he said. "This is my friend Gemma" Kelly answered for me "Can we push in front of you in the line?" "Anything you want," he said as he grabs my hand and pulls me next to his body. He was just putting his hands around my hips when I pushed him away. He smiled and said, "Ok too quickly". I ignored him. I stood in front of him and started to talk to Kerry's friends complementing them on their dresses. They complemented me on my make up and my dress. Eventually a taxi pulled up and out popped the rest of the girls. They all looked amazing. Eventually Rachel got out of the car and I realised that I had seen her chatting to my sister a few weeks ago. I thought that that would be the end, I was so nervous that I started talking to the bloke who had let us into the queue. I knew that I was convincing when it came to talking and acting like a girl, so I didn't worry. Eventually we got to the front of the queue. Caryn and I held hands as we walked past the bouncer. He took a long look at me and smiled. I just grinned back and walked into the club. We all sat down at a table, and continued drinking, for a while. A group of blokes came and sat down near the girls on the other side of the table. Caryn and I started chatting and laughing, I didn't even notice when she put her hand on my leg. She put her mouth next to my ear and whispered do you want to go to the toilet with me. We stood up and excused ourselves. We walked hand in hand to the bathroom. I walked into the ladies toilet, it was really full there was a queue for the toilet stalls and there were a whole bunch of girls talking and fixing their makeup. Caryn pushed her way into one of the stalls while I touched up my make up. I felt a tap on my shoulder I turned around and recognised the girl immediately. It was my friend's old girlfriend, Rebecca. I thought it was you James, I saw you push into the line earlier. You were chatting to my friend Jason," she said, " What are you doing dressed up like that?" "Its a long story" I said." Maybe we could chat later and I'll tell you the abridged story"' "Good idea, she said " I would love to hear the story of how you ended up in a dress, heels and makeup. By the way could I borrow your lipstick, James?" I gave her the lipstick and watched as she applied it to her lips. Just then Caryn emerged and came and stood next to me. "Have you found a friend Gemma?" "This is my friend's ex girlfriend." "Was it you who made James dress like a girl tonight?" "No darling he is a girl tonight" she said" and please call her by her proper name Gemma" "Ok Gemma," said Rebecca with a giggle" Did you take a fancy to my friend Jason earlier" "I had to talk to him he let us into the queue." "Whatever you say," said Rebecca. I grabbed Caryn and walked into one of the cubicles. She was obviously hot at the thought of me be being picked up by a guy. She pushed me against the wall of cubicle started kissing me. She hitched up my skirt as I put my legs around her. We kissed and played for ages. Eventually Caryn stopped and looked at me almost in disgust. I was on the floor of the cubicle with my legs spread apart and my skirt hitched above my waist. My lipstick was smudged all over my face. She said "fix yourself up you slapper you look like a mess." I was shocked. I stood up fixed up my dress and went into the bathroom where I redid some of my makeup. I considered what had just happened and realised that Caryn was feeling revulsion after she had been kissing a girl. She now saw me more as a girlfriend than as her best friend and looking in thee mirror I could understand why. I walked outside and back to the dance floor. As I was making my way through the crowd, I felt a hand on my back. I spun around to see Jason. He offered to buy me a drink and in order to delay going back to the table to confront Caryn I stayed and chatted and drank with Jason. He chose a metropolitan for me and ordered himself some vodka. We chatted for ages, occasionally he would touch my arm and sometimes my hand until eventually he hand was touching my hips. His head had gradually moved closer to mine, almost as though he was going to kiss me. I pulled back and took his hand off my hip. He grasped my hand gently and led me to the dance floor. He held me as we danced to slow music. Eventually he moved his head closer to mine again. This time I felt really girly and thought to myself, what's wrong with a kiss? We kissed for what must have been ages, eventually he led me back to the table and sat down and pulled me onto his lap. I could feel him bulging through my dress. As the night went on we kissed and danced more until he said that he was ready to leave. I kissed him goodbye and went back to the table. The girls were all sitting there, and started talking when I arrived back. "At least one of us could be bothered to try and pull" Sarah laughed. We all got up and started dancing. I danced next to Kerri who was holding my hand while we swayed in time with each other. We had a ton of blokes around us. One of them approached Kerri and said, "Fancy a snog?" "I don't think my girlfriend would like it very much", she said holding my hand. "Well if you are lesbians then kiss her" I don't know whether it was the alcohol but we were also kissing soon rubbing our hands over each other. He jokingly asked if he could join in. Kerri grabbed him by the hand and we all went into the corner of the club. He held us both in his arms as he kissed Kerri and touched my bottom at the same time. I gently started kissing his neck as I moved my purple nails along his chest. I gradually moved my hands down until they were on top of his trousers. He was really hot and was bulging badly. He whispered into my ears. "Put your hands inside gorgeous" Caught up in the moment, I unzipped his trousers and put my hand inside and started rubbing on the outside of his boxers. He was really enjoying himself. I eventually stopped. He whispered in my ear " You are amazing" He was now almost ignoring Kerry. He eventually stood up, grabbed me around the waist and took me and sat down on the couch in the corner. He sat next to me and we started kissing passionately. I put one of legs over his leg so that my legs were intertwined with his. He put one hand on my legs and started gently stroking them. The feeling of his hands rubbing up my tights sent a chill down my spine. He gently worked his hands up until he had his hands in my skirt and on my panties. When he finally touched me, I froze at the thought that I had been caught, but instead he smiled and carried on kissing me more passionately than before. I was waiting for him to give me a wonderful complement about my body when he pulled back and whispered in my ear "You had better give great head girl otherwise everyone in the club is going to know what a freak you are" I opened my eyes in surprise and jerked back in surprise. I looked around and realised that kissing the bloke at the next table was my sister's friend, Rachel. I freaked out. I felt him pull my head down to his groin. I had no choice, I opening out his zipper and took him into my mouth and gave him a blowjob. Just as I was finishing, I felt a tap on my shoulder. It was the bouncer, he was really angry "We don't approve of that sort of thing in this club" I was so shocked I stood up and ran back to Caryn. I was nearly in tears. I said to Caryn that I had to leave. "Why?" she said. "Because I was caught giving head to bloke" She smirked and stood up and said "ok I'll leave, but I was right about you being a slut" She got up said goodbye to the other girls, left the club and got into a cab with me, Chapter 8 Going home As we drove back she tried to cheer me up. When she could see I was feeling a bit better, she said to me "so how was it?" "I hated it", "I said because he blackmailed me into doing it" I could see the pity in her eyes, just then she got down onto her knees she hitched up my dress, pulled down my tights and starting giving me head. I was in ecstasy as I looked down. I realised that a short while ago that was me doing the same thing. The thought of that set me off and I came harder then I ever did before. We arrived at home and walked back to the flat hand in hand. As I got back I immediately got changed I found my old clothes in Caryn's bedside drawer. I took off the entire make up and walked out with the cameras and film. I never saw the girls again except recently when I saw Sarah who winked at me as she walked past me at a shopping mall. I am not sure if I want to see them again.