Fictional story.How I started and first sexual enc How do I start this. Perhaps from almost the start. Back in late 60’s and early 70’s it was fashionable for guys to grow their hair longer than the conventional short back and sides of the previous generation. I had grown mine till was resting on my jacket collar and over my ears. My parents didn’t like and we’re forever telling me to get my hair cut, I looked like a girl. One afternoon I decided to prove them wrong. I was home alone so I went to find a dress or skirt and blouse to try on and see if I did look like a girl. My Aunt, Uncle and cousin were staying a few weeks while their roof was being repaired from storm damage. My Aunt was approximately the same height as me although a little more plump but she still did have curves in the right places. I went to the spare room which they were using. Hung in the wardrobe was a flowery summer dress. I quickly took out and almost ran to my room. Breathing heavily with fear and excitement I undressed till I was only wearing my y-fronts. I took the dress and slipped over my head, I’d seen my mum put a dress on like that. That’s when I noticed a zip running up the side. I took the dress off and unzipped it then put it back on again. I reached to my side and zipped myself in. Standing in front of my wardrobe mirror, I looked at my reflection. Oh my days, my parents were almost right, I needed to add something to get the correct shape. I needed boobs as the top was most definitely flat. What was most confusing was my cock was growing in my underpants. For some inexplicable reason I did a twirl and the skirt flared out exposing more of my legs. I thought how was I going to grow boobs. Then it struck me if I borrowed a bra I could pad it out with my rolled up socks. Unzipping and taking the dress off I put my jeans back on and went I turn to the bedrooms of the three females currently staying at our house. Mum’s first, I found a black bra over the back of a chair. Slipping my arms in the straps I tried to hook it behind my back. No luck with that and the bra was to tight anyway as my mother had very small boobs. I replaced the bra where I found it. I did notice there were some tan stockings over the chair as well. Next try was my Aunt. Again no good to big and cumbersome it came down almost to my waist. This was my first encounter of a long line bra. Finally my cousins room there on the stool was what I now know was a zip fronted basque. I wrapped it round my naked chest and zipped it up. It was a near perfect fit, I adjusted the straps slightly but otherwise great. I must get the size off the label I thought. Back to my room, I opened my drawer and took two pairs of socks. I rolled in a ball and pushed them into the cups, the dress went back on and what a difference that made. Now I did look very feminine with my long hair and wearing a dress. Something inside made me do another twirl in front of my mirror. This time the added shaping and the long straps hanging from the corset thing brushing against my thighs caused an explosion inside me resulting in an ejaculation in my pants. I collapsed on my bed breathing hard feeling my cum seep into my pants. Feeling now full of guilt at my reaction and to wearing the borrowed clothes. I quickly took the girlie clothes and my very sticky pants. I put a clean pair of pants on and my jeans back on. I looked at the labels in the dress and corset and made a mental note of the sizes. I thought it a coincidence that both dress and corset fitted but had different sizes. I was later to discover that feminine clothes have different labels. Dressing again was something I wanted to repeat with perhaps a few more feminine items of clothing. Next it was to replace the borrowed clothes were I had found them. I returned the dress and hung it back in the wardrobe, when I put the corset back I noticed a pair of matching knickers on the chair. I picked them up and they felt so silky, I held them to my face and smelt my cousins aroma on them. Fantastic. I looked at the label, hmmm same size as my Aunts dress, I put them back and put the corset back. So my cousin was a 36c and 14 knickers my Aunt was a 14 dress. So everything was back in place, I’d not been caught, all was right with the world. Or so I thought. A couple of days later I was home with just my Aunt, she sat beside me on our sofa. “Now then young man have you got something to tell me?” “What? Um no nothing, why what should I be telling you?” I blurted out a reply. “It’s just that I noticed some stains that look remarkably like semen on my summer dress and Kirsty said the straps on her basque had been altered”. I didn’t know what to say I just mumbled incoherently. “It’s ok don’t be embarrassed, I quite like the idea of you wearing my dress and I can sort Kirsty, I just wish you had taken a bit more care about where you left your cum stains”. “I’m so sorry, I don’t know what came over me. I just got carried away with all the moans about the length of my hair, I thought I would see if I did look like a girl”. “I know what came over my dress”. She said with a giggle. “Your parents will be back soon so it’s our secret, next time we are alone together I want to see you dressed, and don’t worry about underwear I’ll sort it for you and make sure you don’t leave any tell tale stains”. “Thank you”. I said feeling very relieved. “Enough said for now, let’s watch TV as if nothing has happened”. She finished, then stood up went to an armchair and sat down. From my position I could see up her skirt to her knickers and stocking tops, she was teasing me and she knew it. When my parents came home she adjusted her skirt to make herself respectable. It was about a week later that I was at home with only my Aunt, about 3/4 of an hour after everyone had left. My Aunt came to my room she had some carrier bags with her which put on my bed. “Undress down to your briefs and then join me in the bathroom” she instructed. I quickly took off my clothes leaving my briefs on and entered the bathroom room. “Now stand on the towel”. She said. She put a shower cap on my head tucking my hair in. Next she put on some blue latex gloves, then she picked up a can of aerosol and aimed it at me. She covered my chest, arms and legs. Then she told me to turn round and she sprayed my back under my arms and backs of my legs. “Stay where you are, touch nothing and I will be back in a few minutes”. She said, me covered from neck to feet in a white foam that was getting warm. She came back about 10 mins later although it seemed like hours. She had kitchen paper and what resembled a car ice sc****r only slightly smaller. She started on my back scr****g and wiping the sc****r on the kitchen paper. Then she moved to my legs, arms under my arms and finally my chest. “Now take off your briefs and shower yourself throughly”. She told me. I did as I was told and as I was showering I noticed most of my body hair had gone. And what was left was rapidly falling off and washing down the plug hole. “We must remember to remove the hair from the plug hole in case it blocks it”. She said. When I had finished showering I got out and started to rub myself dry. “STOP”. She ordered. “Pat yourself dry don’t rub”. When I had dried myself she took out another bottle and then she smoothed it all over me where she had sprayed the foam. She smoothed it in to my skin which as she caressed me caused me to erect in front of her. “Mmmm something is enjoying the attention”. She said glancing down at my hardening cock. “We might need to deal with that”. She added, as she took a gentle grasp of me and stroked me up and down making even harder and gasp as the emotions flooded into my cock. In hardly any time at all I gasped. “I’m cumming”. Aunt grabbed some toilet paper and my semen pumped into it as she held it in front of me. She gently wiped me clean squeezing gently to extract every last drop. Then flushed it away. She wrapped a towel round me and said. “Back to your bedroom, young lady”. She instructed. What young lady I thought. “That’s what I am going to refer to you as when we are alone”. She said as if she had read my thoughts. When we arrived in my bedroom there were several items of female clothes including underwear. The first thing she did was to remove the towel and she picked up a pink underwired lacy bra, she held it out for me to slip my arms in, then standing behind me she clipped it together, next she picked up a matching suspender belt and wrapped it around me again fastening it behind me. She told me to sit on the bed while she opened a pack of very sheer stockings, she gathered each of them in turn and rolled them up my legs to my thighs. She told me to stand and she finished each stocking by attaching them to the suspender belt, adjusted the tension. The feeling of the nylon on my now hair free legs was just incredible. She held out a pair of pink lacy panties that matched both bra and suspender belt, she tucked me in so in my reflection I had a smooth front with no obvious bulge. She took two balloons that were filled with some sort of gel and put them into the bra cups, adjusting the bra straps to give them support. Next she took the dress I had borrowed from her wardrobe and slipping it over my head and getting it to hang properly, then she zipped it up. “Just a few more minutes”. She said. Picking up a small bag she sat me on the bed and applied a minimum amount of make up topped with some bright lipstick, then brushed my hair into a more feminine style. She stepped back to admire her work. “Hmmm what’s missing, I know. Wait right there”. Aunt instructed. She left and was back in moments, she had a flared net waist petticoat in her hands. “Lift your dress, and step into this”. She said, holding out the petticoat. I bundled the dress up and stepped into the petticoat, she drew it up my legs running the backs of her hands against my nylon clad legs the naked flesh as she passed my stocking tops. I shuddered at her touch. “Control yourself”. She said, “or you will make a mess in your panties”. Having set the petticoat in position she then arranged the dress over. I looked in my wardrobe mirror to see the finished look. WOW, I looked like a 50’s girl my hair curled not too much make up a shapely chest, a full flared dress, sheer stockings. The only thing missing was shoes. “What size shoes do you wear”? Aunt asked. “Seven, sometimes seven and a half”. I replied. “Let me check to see if your mum’s or Kirsty’s” she said and left. When she returned she had a pair of black shiny heels. “I found these at the back of your mum and dad’s wardrobe, it does look like they have been worn outside much and they are an eight”. She said with a sly grin. I did not pick up on what she had said. She just put them on the floor and told me to step into them. “Now walk around and take small steps and not put your heel down first as that could break the heel off”. She said. She cleared the bags off my bed and sat down, hoisting her skirt hem to just show the lace of her stocking tops. I tried walking very nervously almost twisting my ankle once. Suddenly I lost my balance completely and fell forward onto her, knocking her on her back across my bed. I started to apologise. “Just shut up and kiss me”. She said. I did and before long her hand was under my petticoat and releasing my hardening cock from its lacy prison. We continued kissing as she aroused me even more. I managed to find my way under her skirt to her stocking tops and found her suspender clips, as I ventured further she parted her legs to allow me access to her pleasure palace. As I got further up her inner thighs I found her pussy warm and very moist. She was not wearing panties. I teased her pussy with my fingers, making her moan as I was also moaning as she stroked me. She stopped kissing me and instructed me to get my head between her legs and give her pussy a good licking. “I’ll tell you what to do while you pleasure me”. She said. Waisting no time I quickly knelt on the floor and lifting her skirt above her waist I bent forward between her legs and started licking. She reached down and opened her pussy with two fingers, out popped her clitoris like a tiny penis. I licked, lapped and tongued her pussy probing as far as my tongue would reach. She writhed beneath me until she suddenly collapsed on to my bed, almost flooding my mouth with her sweet juices. She was laying on her back, panting hard her legs still spread wide. Her juices were still dribbling out of her pussy, so I quickly licked them up causing her to shudder again. “Oh don’t stop, I’m cumming again”. She gasped. I licked, lapped and probed again until she once again orgasmed. “That’s a first for me”. She gasped while trying to catch her breath. “Me too”. I replied “What the first time you have made a woman cum twice”? She asked. “No, the first time I have ever licked a woman”. I answered. “You’re joking, because if you’re not you are a natural, you knew exactly how to get me off”. “Thank you”. I replied “No, THANK YOU, now I think it is your turn to have some pleasure”. She said. As she stood up she told me to lay back on the bed. I did and she knelt on the floor she lifted my skirt and petticoat up and smoothed it onto my chest. Then she reached towards me and eased my panties down and off. “Now you know why it’s best to wear panties over your suspenders, it’s easier to remove them without undoing your stockings”. She said. Her next action was to ease my cock from between my legs and as she did it sprang forward directly towards her waiting mouth. She quickly engulfed my cock and started to bobbing up and down. “Please don’t cum to quickly I really want us both to enjoy this”. She murmured. Her mouth having my cock in it made it difficult for her to talk. “Why don’t we lay head to tail on my bed then we can pleasure each other”? I said. She stood up and unzipped her skirt, then told me to stand where she unzipped and removed my dress and slipped the petticoat off. Then she unbuttoned her blouse I saw her black corset that stopped just under her proud firm breasts with very prominent erect nipples. We lay head to toe on the bed on our sides, she quickly took my cock back in her mouth and I moved her leg to once again gain access to her pussy. Once again my tongue was licking, lapping and probing her pussy. I parted her pussy lips to get to her clitoris again. As soon as my tongue touched her clitoris one of her legs came over my head and onto my back, trapping my head firmly between her legs. I continued my licking of her pussy as she was sucking and bobbing up and down my cock. Slowly she clamped her legs together as she had another orgasm. I felt myself tense and I knew soon I would be also pumping my second load of the day, this time into her mouth. I lapped up her juices as fast as I could. The familiar sensation started in me as my cream started to pulse from my balls up through my cock into my Aunts mouth. I could hear her mumbling as her mouth filled, she was not letting any spill out. Her tongue teased all my cream out. Then quickly she released my head and turned round on my bed. She leant in and kissed me passing my cream to me and tasting her own juices. When we had finished our love making we lay together caressing, kissing and talking. “We must do this again” she said. “Yes please”. I replied. “Now we better get you undressed from your lingerie and dressed in your boring male clothes”. She helped me undress and I dressed back in my usual jeans and t-shirt. “Have you a suitcase that you can store these clothes”? She asked. Don’t worry it’s only till our repairs are finished, then I’ll take them to our house and you can visit and we can have lots more fun. Next time I want your cock in my pussy”. She continued. “Yes I have a case, but isn’t it taboo to have sex with a relative”? I said. “Normally yes, however your mother is my hubby’s sister, so you and I are not blood relations”. “Then it’s ok for us to continue our fun”? I asked “Of course although we had better keep it our secret, and I think I know another fairly well hidden secret. I need to investigate a bit more first”. She said. So that’s how I started cross dressing and my first sexual experience with a slightly older woman. My Aunt and I still meet for fun even now. I am due to spend a week with her while my Uncle is away on a works training event.