Date: Fri, 22 Jan 2010 16:16:46 +0000 From: deborah marshall Subject: Debbie When I was twelve, I started wering my sisters clothes. A year later my best friend Peter found out and from then on I was his friend Jon at school and his girlfriend Debbie when we could be alone. This is what happened, although I think I am remembering it through rose-tinted spectacles. Feedback welcome: Deborah.marshall@hotmail.co.uk I've told the story elsewhere of how I started cross dressing and eventually became my best friend's girl friend. Whenever we were alone, I would raid either his sisters or mothers laundry basket, then we would spend hours lieing on his bed, snogging or with me giving him blow jobs. However, after nearly five months, we still hadn't had sex and peter was starting to ask me about it every time we were together. It wasn't as if I didn't want to. In recent weeks, Peter had started fingering me during our marathon snogging sessions and I really enjoyed it. Peter knew I enjoyed it and it was usually only a matter of minutes after we started kissing before his hand would be up the back of my skirt and he would be fingering me deeply. It didn't take much of this to have the front of my knickers soaking wet. I don't know why I was hesitating. I suppose that even at the age of thirteen, I understood that losing your virginity was a big deal and that I wanted it to be special. The day it happened started like any other day. It was the Sunday after Xmas; I was in bed, thinking about having my second wank of the day. Downstairs I heard the phone ring and a few seconds later, my mum shouted up the stairs, "Jon, Peters on the phone." I hurriedly jumped out of bed and put my dressing gown on to hide the hard on I'd been toying with. "Hi," I said, picking the phone up. "Come round as soon as you can Debbie, I've got a surprise for you," said Peter. The fact that he'd called me Debbie meant two things. Firstly that he was home alone and secondly he wanted to fool around with his girlfriend. I was more than happy to go along, squirting into my knickers while Peter kissed and fingered me was a million times better than a solitary wank. "I'll just have a shower, see you in half an hour," I replied and hung up. Telling my mum I was going round to Peter's, I went upstairs to shower. Before becoming Debbie, I always had a shower, with a difference. I would use my mum's separate shampoo and conditioner, rather than the medicated stuff I usually used. Also, I had some Impulse shower gel and deodorant that I'd bought before Xmas, hoping the woman in the shop thought was a present for my mum or sister. After finishing my shower and drying myself, I went back to my room and got dressed. I had a pair of my sister's knickers I'd stolen out of the washing months ago. They were pink, with lace around the legs and with a little pink bow at the front. I put them on, feeling that amazing feeling as I pulled them up. I then put on a pair of my sisters socks; they were white, with pink toes and a pink band at the top. Sadly, the rest of my clothing had to be my boring boys Clothes, but I knew that underneath, I was ready to become Debbie in a matter of seconds. The walk to Peter's house was as exciting as ever. There was something about the fact that I was wearing knickers that made me feel different, I felt like a girl, even though I was dressed like a boy. Occasionally, I would catch the scent of my deodorant, a very feminine smell and this would excite me further. I didn't bump into anyone this day, once I'd met a girl from my class at school and I swear she looked at me funnily, maybe she smelt my deodorant or maybe it was the fact that I told her how nice her dress looked. I arrived at Peter's house breathless with excitement. We had a rule that I would only ever wear clothes out of the washing baskets, so I never knew what I would be wearing. I could wear both his mum's and his sister's clothes, it wouldn't be school uniform, not at Xmas, but I hope for one of my favourite dresses or maybe a skirt and top. Peter opened the door with a huge grin on his face. Quickly going past him, I asked, "So, what's my surprise?" "Wait and see," he replied and started climbing the stairs. I followed him upstairs to his parents' bedroom. On the threshold, he turned to me and said "close your eyes." "Do I have to?" I asked. "Yes, otherwise it will spoil your surprise." I closed my eyes and let him lead me into the bedroom and to the foot of the bed. "Don't open your eyes yet," he said. "Mum and Dad went on a Xmas night out last night, it was very posh. You can open your eyes now." I opened my eyes and stared in amazement at what was LAID out on the bed in front of me. The first things I noticed were the knickers, bra and suspender belt, along with a pair of very fancy stockings. Next I took in the sexy black dress I'd wanted to wear for months and the shoes with the high heels and the ankle straps I'd worn two or three times. Peter and I didn't usually kiss until I was fully dressed as Debbie, but I was so excited, that I threw my arms around his neck and kissed him deeply. The reason I was so excited, other than the fact I'd wanted to wear this dress for months, was the stockings. Because I only ever wore stuff from the washing basket, I'd worn tights dozens of times, his mum and sister both wore them all the time, but I'd never worn stockings. Breaking off the kiss, Peter said, "I'll leave you to get dressed." Once Peter had left the room, I kicked off my trainers and got undressed as quickly as I could. Then I took a closer look at my trophies. The underwear was a set I'd admired in his mums underwear draw before, black, very lacy, with a bright red bow decorating the front of the bra and thong and red lace trim on the suspender belt. Picking up the thong, I saw that the gusset was very dirty; Peter's mum and dad had obviously had some fun after the party. Next I looked at the stockings; they must have been new, because I'd never seen them before. They were black, with a wide lace top, decorated with red lace like the underwear, they felt amazing. Both were slightly stained on one side and I couldn't work out why. Then I realised that this must be the insides and Peter's mum's juices must have run into them. I confirmed this by smelling them, there was also a faint smell of come on them to, very interesting I thought. Although I'd worn a bra dozens and dozens of times by now, I still couldn't fasten one behind my back. So, I put the bra around me, fastened it at the front and then pulled it so it was the right way round and put my arms through the straps. Although wearing knickers feels amazing, they are still just a female version of something I wear all the time. Wearing a bra is different; it's a completely new sensation the feeling of being restrained around the chest and over each shoulder. We'd tried a number of ways to simulate breasts over the past few months, but after a balloon burst during a particularly heavy petting session, I'd settled on stuffing my bra cups with rolled up socks and tights. Peter's mum was a DD cup, so it took quite a lot of socks and tights to get the shape I wanted. Once I had that heavy feeling in my bra and that amazing shape I could spend all day looking at in the mirror, I turned to the rest of my outfit. I was briefly unsure as to what to put on next, the thong or the suspender belt. Then I realised that it must be the suspender belt, otherwise women wouldn't be able to pull their knickers down to go to the toilet without taking their stockings off. Like the bra, I fastened the suspender belt at the front and pulled it around the right way. It felt amazing around my waist, with the straps hanging down over my hips. Quickly picking up one of the stockings, I worked out from the stains which leg it was and sat on the edge of the bed. Putting my hand in the stocking to the toes, I then put it onto my foot and rolled it up my leg. It felt as good as it always did, the feel of nylon encasing my bare legs. The stocking didn't come up my leg as far as I thought it would. However, I managed, after a few tries, to fasten the front clip, it was far more awkward than I expected. I then stood up and reaching around behind me, took hold of the second clip. There seemed to be a big gap between the end of the strap where it went over my bum and the top of the stockings. Eventually I managed to get the two to meet and was able to fasten the clip. Then I felt for the first time that incredible feeling of tension between the belt around my waist and the stocking on my leg. The second stocking went on much more easily and I went over to admire myself in the mirror. I looked amazing, the stockings seemed to make my legs look longer and I was entranced by the slight bulge of flesh over the tops. I was already incredibly turned on, but seeing me in a suspender belt and stockings for the first time made my little cock even harder and I thought I might come right then. All I wanted to do now was get the rest of my clothes on as soon as possible. Going back over to the bed, I picked up the thong and stepped into it. Like most girls, I don't find thongs very comfortable, but I love how my bum looks in one. I was really turned on by now and wanted to be kissed, so I quickly pulled the dress over my head and zipped it up. It came to mid-way between the tops of my stockings and my knees. Peter's mum was taller than me, so she must have had to be careful not to flash her stocking tops. Sitting on the edge of the bed, I slipped my feet into the shoes and fastened the ankle straps. Then I sat for a moment, admiring my legs in the black stockings, crossing and then re-crossing them, watching my dress ride up. Peter would be getting impatient by now; I was feeling pretty keen to see him myself. So, I moved to the dressing table, sat down and put on some lipstick and sprayed some perfume on my neck and wrists. Then I crossed the room to admire myself in the full-length mirror again. God, I looked amazing, I looked like a girl. Even my hair looked right; I'd given it a quick brush after putting on my lipstick. My legs looked longer in the stockings and the heels made them look really shapely. The dress was tight fitting to the waist and then flares over my hips and looked amazing, even my bust looked real. It was then, looking at this sexy young girl in the mirror that was me, that I decided today would be the day. "Are you ready?" Peter shouted from outside the bedroom door. "Come and get me," I replied. The Dorr burst open and Peter practically ran into the room. Ten he stopped, dead, as I turned towards him. "Wow," he said, "You look amazing." He was right, I did look amazing. Neither of us spoke for several minutes, because within two seconds, I was in Peter's arms and we were kissing passionately and not long after that, peter's hands were under my dress and he was feeling my bum. After what seemed like hours, I broke off the kiss and leant back slightly, so I could look into Peter's eyes. This had the effect of increasing the feeling of his erection pressing into my stomach. "Peter?" I asked. "Yes?" "I want you to do it to me." The grin that spread across his face made him look like the Cheshire cat. "I'll help you get undressed," I said, and knelt before him. Reaching up, I unbuttoned his jeans and pulled them down along with his underpants. He stepped out of them and I leant forward and took his cock in my mouth, giving it a good suck before sliding my head forward until it was all in my mouth. Peter groaned and put his hand on the back of my head. Pulling back I asked, "Or I can carry on doing this if you want?" Then I kissed the tip and licked the precome with my tongue. I'd gotten a taste for come after four months of giving Peter six or seven blowjobs a week. "No," he said, taking a step back. "I want to do it." "So do I," I replied and climbed on the bed. I lay on my back, my legs slightly apart, and my arms at my side. "Aren't you going to get on your hands and knees?" he asked. We are going to kiss for a bit longer," I replied. He climbed onto the bed and lay on top of me. I put my arms around him and we kissed. "I can't believe I'm really going to fuck you," said Peter. "You are," I replied. "Get the stuff." The stuff was the lubricant that his mother kept in the bottom draw of her bedside cabinet. Whilst Peter was getting it, I rolled over and knelt up, bum in the air, leaning on my forearms. Neither of us had much idea of what we were doing, but this seemed the correct position from what we had learnt in the playground. Peter climb back onto the bed behind me and pulled my dress up. "Aren't you going to take your knickers off?" "No," I replied. "Just pull them to one side." Peter did so and I felt the cool gel as he squeezed it onto my bum hole. "Are you sure?" he asked. "Yes, I want you to fuck me." I felt Peter shuffle forward and he put one hand on my hip. I could feel his cock touching my bum hole; my own cock was straining the front of my thong. Then, Peter thrust the whole of his five inch cock into me. The pain was terrible, I screamed and shot forwards, bursting into tears. "What's wrong?" Peter asked, surprise in his voice. "It hurt." I rolled onto my back and covered my eyes with my hands and began crying properly. Peter lay down beside me and took me in his arms and kissed me softly. "I'm sorry Debbie, I didn't mean to hurt you," he said. I began crying even harder. "What's wrong?" he asked. "Is it still hurting?" I lowered my hands and sniffed in a most un-lady like way. "No," I said. "I'm disappointed, I really wanted to, but it hurt so much." "Don't worry, we can try another day," said Peter. "You don't mind?" I asked. "Of course not," he said. Then he kissed me, long and hard, his tongue probing my mouth. After about five minutes of passionate kissing, I had stopped crying and had started to feel much better. Better than better, I was turned on again and I could feel Peter's erection pressing into my tummy. After another five minutes, Peter's hand was up my dress, stroking my thighs. I rolled onto my back and spread my legs. After stroking the insides of my thighs, his hand moved to the front of my knickers and he caressed me through them. I was very turned on by this point and I was panting gently. Then I felt his hand move lower and felt my knickers being pulled to one side and Peter's finger touching my bum hole. I tensed, but he didn't put it in me. "Relax, we've done this before and you enjoy it." I was still lubricated, so when he slid his index finger all the way into me, it didn't hurt at all. Peter began kissing me as he fingered me slowly, his tongue moving in and out of my mouth at the same time as his finger moved in and out of my bum hole. After a few minutes of this, I was panting even more quickly and he had added a second finger. "Let's try again, if you promise to go slowly and stop if I ask," I said. "Are you sure?" he asked. "I don't want to be a virgin anymore," I said. Peter withdrew his fingers from me and I rolled over and got into position as he moved behind me. This time, he put his cock against my bum hole and left it there for at least a minute, then he pushed forward, ever so slowly an gently, until just the tip was inside me. I'd tensed when I felt him entering me, but all the fingering must have loosened me up, because other than a split-second moment of pain, it was far easier than the first time. "Are you OK?" he asked. "Yes, try a bit more." Peter entered me a bit further. It was a very strange feeling, almost like having a pooh. It didn't hurt; it didn't feel particularly nice either. \However, the thought that I was actually being fucked, that I had Peter's cock in my bum, was very exciting. After a few seconds, I slowly pushed my bum backwards, until Peter's cock was all the way inside me. "How does it feel?" he asked. "Amazing." I knew that was what he wanted to hear. As I moved forward until he was almost all the way out of me and then pushed back, I started thinking that it might actually be amazing after all. Peter's hands moved to my waist and he started thrusting in and out of me, slowly at first. Soon however his thrust got faster and he started breathing heavily. My head was spinning. Here I was, wearing stockings, being fucked doggy style by my boyfriend. Before long, Peter's thrust became almost frantic and I realised he was going to come. With a loud scream of pleasure, he pulled me back onto him and thrust forward as deep as he could and came, over and over again into me. I was sure I could feel his come as it spurted into me. We must have stayed like that for several minutes, him holding my hips tight, pulling me onto his cock that was all the way inside me. Eventually, Peter groaned and pulled out of me. I turned to face him and we just looked at each other for what seemed like ages. Then he leaned forward and kissed me gently on the lips. "Thank you Debbie," he said. I burst into tears. "Why are you crying?" he asked. "Did it hurt?" "I'm crying because I'm happy, it was amazing." We lay down and I cuddled into Peter's arms and we relaxed. After a while, we started kissing again and not long after that, we were both turned on again. We were teenage boys after all. "Can we do it again?" I asked. Peter's smile was the only response I needed. I rolled onto my back and pulled Peter onto me. I wanted to do it face to face this time, but it was awkward, my own cock seemed to get in the way. Then I remembered a position I'd seen in my parent's copy of The Joy of sex. I got Peter to kneel between my legs, and then I put my ankles on his shoulders and lifted my bum off the bed. He soon got the hang of things and he quickly pulled my knickers over and entered me, this time it was even easier than the first time. Soon he was thrusting in and out of me, his hands on my thighs and it felt amazing. Then he moved his right hand to the front of my knickers and began playing with me. This, combined with the feeling of him in my bum was too much for me and I began moaning loudly. Within a minute I had the most powerful orgasm I'd ever had in my life and completely soaked the front of my knickers. After regaining our breath whilst kissing and cuddling, we managed a third time that day. This time I was standing up against Peter's bedroom door.