This is a print version of story From Andy to Amy by justpeekinout from

From Andy to Amy

Story codes: CD TV mf voy mast nosex

If you are looking for serious one handed reading, then you are in the wrong place. I hpe you like this. It's the stopry of a young man's first venture into cross dressing. Any similarity to me is entirely coincidental!

Title: Andy to Amy

"Why are you staring at my knickers?"

I jerked upright. God, I really had been staring at her knickers - not the ones she was wearing, sadly, but a pair on the floor, presumably yesterday's pair. They were perfectly normal white knickers with little pink flowers on them and a tiny satin bow on the front - unremarkable in every way other than they were right there in front of me and, as she had noticed, I couldn't tear my eyes away from them.

'She' was Nikki and 'I' was, and still am, Andy. At least most of the time. Sometimes I am Amy, but we'll get to that. The day in question was an early summer morning and I was sitting on the floor at the end of her bed. She was sitting opposite me, and we were supposed to be studying for a biology test that we had coming up, but it seems my mind was wandering. I can't recall what the card game was, as it was an awfully long time ago but I do recall that I was 18 and Nikki was as well, and we were sort of girlfriend and boyfriend. I say 'sort of' because all we did was kiss occasionally and sometimes hold hands. This was the 1970s, after all! We were both very naive about sex, although we knew the mechanics from biology lessons at the school we both went to. In truth, we were each other's best friends and had been so since I had moved to the area with my parents when I was around 6. We had played doctor a few times when we were little, and she had more recently read some porno mags with me that I had found in a bag under a bush in the woods that we used to play when we were k**s and which we still liked to walk in, but that was as far as our sexual experimentation had ever got. We certainly never `did' anything or even talked about sex but then no-one else in this small rural corner of England was doing anything either.

Not that I was completely naive, you understand. I had discovered masturbation at an early age, and when I say 'discovered' I mean that someone had shown me, but that's a story for a different day! But once the path to ecstasy had been revealed to me I never looked back. I was playing with my cock absolutely every chance I got. On a quiet day, it was just once in the morning and once in the evening, but generally it was at least 3 or 4 times and often many more than that. I was, and in fact pretty much still am, an orgasm addict and just loved playing with myself. Anyway, back to the day in question.

I was busted! "I, err, look, erm, sorry. Didn't mean to," I mumbled.

In truth it was because they fascinated me. Not just her knickers, but all her clothes. I envied her - in fact I envied all girls. They had much nicer clothes to wear, much greater variety and everything was so much softer than the thicker, more robust and utilitarian clothes - including underwear - that I and the rest of the male half of the population had to make do with. It just wasn't fair!

"Well, don't, it's weird." she said, scooping up the crumpled cotton vision of perfection and throwing them on the desk chair across the room. "It's not like I go around staring at your underwear."

"You can if you want," I replied quickly. Now what on earth had possessed me to say something like that? I didn't want to show my pants to Nikki, and I am sure that she would have been grossed out by seeing them. They were just a pair of light blue briefs with red piping on them - not in the least attractive! Anyway, it would be embarrassing, and like any normal 18 year old boy back then my embarrassment threshold was set pretty low.

"OK." I hadn't expected that response!

"Don't be silly, I don't have any to show you. They're all at home!"

"Yes you do. You're wearing some." Yeah, that wasn't going to happen! I was wearing them so she would see me in my pants, and that had to be bad, right? I mean, seeing me in a pair of tight speedos which left nothing to the imagination whilst playing around her pool (I was SO jealous!) was one thing, but this was my underwear we were talking about! I couldn't let a girl see me in my underwear!

"No way," I replied, reddening.

"You have to now 'cause you said I could and I caught you looking at mine. Anyway I double dare you and no rebounds!" That was it. The double dare. The ultimate order. Some of the daft things I did over the years because I had been double dared...but that had been some time previously, and it had been years since the double dare card had been played.

How bad could it be, I wondered to myself. I just show her the waist band of my pants and it's all over and maybe she'll forget that she caught me staring at yesterday's knickers on the bedroom floor.

"OK," I said, and put my book down on the floor. I turned to one side, bringing my knee up so that I could stretch out my upper leg and felt for the waistband of my shorts. Slipping my hand under them, I found the elastic of the blue briefs that I was wearing and pulled the side of them up so that the material was clearly visible above my shorts. "There. See? Not very exciting!"

"no, you have to do it properly," she said. "You have to stand up and show me the whole of your pants and turn around so I can see them all."

What? Was she seriously suggesting that I should stand in front of her in my pants with my shorts down? "No way!" I replied.

"You have to because you saw all of my knickers so I get to see all of yours."

"Yeah but you weren't wearing them at the time!"

"Well, you should have thought of that before you started to stare at them. Anyway you have to because I double dared you and you have to do what I say until the dare is done and so you have to drop your shorts and stay that way for 5 minutes." There was no escaping her logic, or her interpretation of the rules of the double dare, but 5 minutes? Not exactly reasonable!

"One minute."



"Two and a half," she said as she picked her watch up from the desk.

"OK, two and a half, but you can't ever tell anyone about this, OK?"

"Deal. Now drop your shorts."

Grimly I stood up and prepared to take my punishment like the man I thought I was. My hands went to the button on the front of my shorts and I unsnapped it. Then I grasped the zip with my hand and pulled it down. I took a deep breath and then with a sudden motion I pushed my shorts down my thighs and let go. They fell to the ground. Instinctively my hands went to cover the f****y jewels.

"Take your hands away. The time doesn't start until you take your hands away." OK, now she was becoming unreasonable. Not only that, she was behaving weirdly in playing this double dare game that oly k**s usually played. But it was the only way to get the clock to start running, so I did as she asked, dropping my hands to my sides.

A pretty silly figure I must have looked. A skinny 18 year old standing in this girl's room in a t-shirt that was too short to cover anything, a pair of blue briefs which were about as sexy as a stick, and a pair of denim shorts sitting atop his otherwise bare feet.

"OK, now turn around," she ordered.

I turned about, having to kick the shorts loose as they threatened to tangle my feet, and faced the wall, allowing her a view of my cotton clad bum. To be honest I remember being relieved at this change of aspect; at least my bits were now facing the other way!

"All the way, silly," she ordered, and so I completed the turn, once again facing Nikki.

"Nice," she said, her eyes glued to my crotch as mine had been to her discarded knickers only a few minutes before.

"Huh," I snorted. "Hardly. Boy's clothes are never nice, and boys' pants are just dull. Girls' knickers are nicer."

"What makes you say that?"

"You get nicer material that's soft and light and we get big thick heavy cotton like this." Her eyes shifted back to her knickers, sitting on the chair where she had thrown them.

"Yeah, I see what you mean," she mused.

"And your other clothes too are nicer. All we get is trousers and stuff.

"You like dresses?" she asked.

"Yeah, they're pretty," I replied. Now I meant that they were pretty to look at, but that's not what she thought I meant. No -- honest I did!

"I think you would look good in a dress," she said. "You hair's quite long for a boy." Well, it was the 1970s!

"What?? No, that's not what I meant at all. I meant that girls look nice in them and can wear lots of different things, but boys are stuck with just the same few things and the material is not as soft."

Nikki picked up her knickers from the chair and rubbed the soft cotton of the rear panel between her fingers. I swallowed heavily as I watched, trying not to think of the fact that, the previous day, that same material had been covering her bum. Then, so suddenly that I could do nothing to avoid it, her hand darted out and she touched the thicker heavy cotton of my briefs at my hip. I felt her fingers open the leg hole a little as she compared the two garments.

"Yeah, you're right. It is much thicker. Why is that?" she asked.

"Dunno," I replied. Even if I had known I would have been unable to answer as my attention was now firmly focussed on my left hip where the backs of her first two fingers were brushing my skin as she concluded her comparison of the two garments. Unfortunately for me the unexpected stimulation of having someone touch me for the first time was having the entirely predictable effect and I could feel my cock, all six inches of it, begin to swell.

As any man will tell you, all young men go around with a perpetual hard on, or so it seems at the time. I used to get hard in class for no reason, hard when watching TV and I always got hard when I got on a bus. It must have been the vibrations. They will also tell you that there is absolutely nothing that you can do to persuade it to go away until it wants to. Well, nothing except masturbate of course, but that is hardly practical on a London bus and neither was it an option here. Given that I couldn't persuade the thing not to poke out, I took the only course left open to me and swiftly turned my back on Nikki causing her fingers to be pulled from by briefs which caused them to snap back against my leg. As I turned I looked down and sure enough the front of my briefs had started to tent as the little bugger woke up.

"What are you doing," asked Nikki.

"Nothing," I replied.

"It doesn't count if you are facing away. You have another one minute and thirty seconds before you can put your shorts back on so you have to turn around again."

"I can't," I replied.

"Why not?"

"I just can't, OK?"

"Sure you can, you are just being silly. You were doing really well too. Turn back and finish your penalty."

"No I can't," I said, my voice sounding a little desperate.

"God, Andy. You want to stand there all afternoon? I've seen it all now anyway so what's the sudden the... Oh." Her voice tailed away. "Is it your willy?"


"Do you have an – an erection? Is your willy hard?"

"Alright, if you must know, yes I do, OK? Can I put my shorts back on now please?" I begged.

"No. You owe me another one minute and thirty seconds and you have to go through with it." She could be really mean sometimes. "Turn back around."

"No, Nikki, I really can't `cause it's not funny."

"I wasn't laughing. Turn around. I want to see."

"Please don't make me," I begged again.

"Come on Andy. Turn. You have to `cause it's a double dare." The irrefutable proof of the double dare again!

"Oh all right then. But you're not to touch me again."



"I promise," she replied.

Slowly I turned back towards her, my hands once again in front of my crotch.

"Move your hands," she said, her voice quieter now. It was more of a request than an order, her voice rising at the end of the sentence. After a moment or two of hesitation I did as she asked.

As I write this I have an image in my mind of that bedroom and the two of us there as clear as if it had happened yesterday. I was standing next to the foot of her bed, facing her. She was sitting cross legged on the floor in a pink strappy top and matching shorts, holding yesterday's knickers in her hand. I was wearing a green and red hooped t-shirt which was a bit too small and which left a gap of flesh above my blue and red briefs. Apart from that I was naked. Of course Nikki had seen much more of me over the years when we had been swimming than she was seeing now, but there was something more naked about her seeing me in briefs rather than in speedos. The other difference was that the front of my briefs was poking out very obviously as a result of the erection that they were containing, an erection which felt as though it was made of solid steel.

Nikki just stared at it, absolutely transfixed.

"Oh my God," she whispered, her eyes riveted to the front of my briefs.

"Do you have to stare like that?" I demanded, although if the situation had been revered I'm damned sure I would have been staring too. I rolled my eyes to emphasise the inappropriateness of her staring and, as I did so, I felt her hand close around my package through my briefs. I folded over faster than a pen knife!

"You said you wouldn't touch!" I accused.

"I had my fingers crossed," she replied. Of course -- that invalidated all promises. How could I have missed that one! "I want to see."

"What?? No way. Look, I've done way too much to pay back for staring at your knickers so what say we let me put my shorts back on now, huh?"

"I want to see," she repeated. I could feel my cock now throbbing within the tight confines of the briefs and I was desperately horny. What I wanted more than anything was a bit of privacy so that I could have a wank, but that didn't look likely! I was so horny that exposing myself to my oldest and closest friend began to seem like a pretty appealing option. Clearly I had begun to think with my little head instead of my big one!

"What's in it for me?" I asked.

"How about I let you put some of my clothes on?"

Now that was not the answer that I expected. What I wanted was the good old `if you show me yours, I'll show you mine' or ‘well, I’ll suck it for you’ but clearly Nikki had another agenda. It says something about the state of my arousal that, rather than reject such a ludicrous situation out of hand, I began to think about it. Nikki and I were about the same size height wise – maybe I was a little taller – and other than her development in the chest department we were about the same build. So that meant that her clothes would fit me. My mouth was suddenly dry.

"OK," I croaked. "But just looking. No touching."



"I promise," she replied.

"Show me your hands and promise again."

She held her slim hands out. "I promise." Her fingers were uncrossed.

I licked my lips and swallowed. My hands went to the sides of my briefs as I considered whether or not this was really a good idea. All logic and reasoning failed me and I hooked my thumbs into the sides of my briefs and pushed them down. As the waist band went past my crotch my cock slapped up against my stomach. I pushed a little further and the briefs fell to the floor. I raised one foot to step out of them and they tossed them on top of my shorts with the other foot. Finally, and I have no idea why as it wasn't part of the deal, I pulled my t-shirt over my head and added it to the pile. So there I stood, standing in front of my kneeling best friend as naked as the day I was born and sporting an erection that felt as though it was going to burst.

Nikki looked up at me and smiled.

So there I was. Eighteen years old, a virgin and standing stark naked in my 11 year old neighbour/best friend's/girlfriend's bedroom sporting a rock hard stiffy while she knelt there in front of me with her eyes glued to it.

Now I know what you lot are expecting. You are assuming that I am about to say that Nikki immediately leapt forward and started to suck my dick and then we went at it all afternoon like a pair of crazed polecats, but you would be wrong and you have probably spent too much time reading stories on this site. Like I said, both of us were very naive at the time and I don't think that either one of us had ever heard of oral sex, much less given it. They didn’t cover that in O-Level biology back in 1974. In fact, I'm pretty convinced that had someone walked into the room at that moment and explained oral sex to us we would have been completely grossed out - I mean putting someone's dick in your mouth?? But that's where people pee from - gross! And as for licking a girl between the legs - ew! Periods and pee and way! Having said that, of course I was so horny that I thought I was going to explode and my cock was so hard it was painful. It was also starting to leak. But there were no blow jobs to be had. What happened was that she spoke. She said "Cool."

I said nothing. To be honest I couldn't think of a thing to say and all I wanted to do was play with my cock to get some relief from the overwhelming desire that I was feeling and to ease the throbbing of my cock and the feeling in my swollen balls. I guess I had some vague notion that Nikki might help or do something or even do it for me, but that wasn't going to happen!

"It's bigger than I remember," she said. I was at a bit of a loss until I twigged that she was talking about the playing doctor games and 'you show me yours' about a decade earlier!

"Err, yeah. I guess." Eloquent, wasn't I?

"Is it often hard like that," she asked?

"Yeah, sometimes."

"So what makes it hard?" she asked.

"Err, sometimes it just goes like that." Well, it was an explanation of a sort and she seemed satisfied.

"Where are your balls," she giggled at the 'naughty' word which she had presumably picked up in the girls' loos or something. My embarrassment increased as I pointed to my scrotum, dangling loose beneath my hard penis but hiding in a forest of coarse hair. "In there," I said.

"Oh, right." She knelt on the floor for what seemed like about 10 years, but was probably closer to about 20 or 30 seconds staring at my rock hard penis and hairy balls, inclining her head this way and that to get a better view. Finally she seemed satisfied.

She stood up and turned towards her wardrobe and opened its door. "OK. So let’s see what there is that is nice and soft so you can compare."

She ran her hand along the gorgeous row of flowing dresses and skirts, soft blouses and trousers that filled the wardrobe until she alighted on a red and white gingham print dress which was actually the summer school uniform for girls at our school, even the ones in the Sixth Form which was where we were. The boys had to wear the same uniform as they wore in the winter but the girls had a choice of either short sleeved blouses with the usual skirt, or of this delightful (or so I thought) light, flowing soft dress that came to just above the knee. We had to wear blazers, long sleeved shirts and ties al year. How was that fair? She pulled the dress and its hanger from the rail and turned towards me again. "I think we're about the same size so I guess that my stuff will fit you, won't it." It was a statement rather than a question. I eyed her up and down, and glanced down at my own naked body and was pretty sure that it would. With me a skinny 18 year old and she a girl who had filled out nicely we were actually almost exactly the same size.

"Try this," she said.

I swallowed. It was a strange moment - a dream about to come true. I could feel my heart thumping within my chest and my mouth had gone dry. As long as I could remember I had been fascinated with girls' clothes - with the way they felt, with the material that they were made of and with the softness and prettiness that they had. I had wanted so much to try them on and to experience the sensation of wearing such lovely creations for myself and now here I was with a real live girl offering to help me realise the dream of becoming part of those lovely soft clothes. And she was my best friend.

I reach out a trembling hand towards the dress, but Nikki stopped me.

"No," she said as she removed the dress from its hanger. "I'll do it. Raise your arms for me." I did as I was told, standing there with my arms raised above my head, which of course made my rock hard cock stick out even more from my hard flat stomach.

She bunched the dress a little from the bottom and then reached up and slipped it over my hands, feeding my hands through the arm holes. I felt the soft cotton slide down my arms and then was nearly overcome as my face was suddenly buried in the red and white gingham of the dress. I felt her hands brush my sides as she grasped the hem of the dress beneath my arms and gently pulled it down over my thin body. It fell into place, brushing softly at my chest, my stomach, my thighs and my hard penis.

The sensation was incredible. My body was screaming with the tactile stimulation of the soft, thin cotton touching every part of my body. She reached up and grasped me gently by the shoulders and started to turn me around. I was experiencing some form of sensory overload and offered no resistance to the pressure of her hands. As I faced away from her I felt her hands at the base of my spine and then both felt and heard the zip being pulled up. As the zip was pulled slowly upwards I felt the dress become a little tighter around me, adding to the intensity of the sensation.

"OK," she said. "You're done." I felt her hand on my arm just below the end of the short sleeve of the dress as she turned me around to face her again and I saw myself in the mirror on the inside of the wardrobe door. I was wearing a dress. It was me in the reflection and I was wearing a dress. I was absolutely mesmerised by the site. "Your hair won't do," I heard her say. Now you must remember that this was the 1970s. The era of the mullet and some of the dodgiest hairdos ever seen on men. Even worse than the ones that women had in the 1980s. Just think Kevin Keegan without the perm and you're not far from the truth, but it was what passed at that time for a boy's haircut and she was right, it didn't quite go with the rest of the look.

Nikki turned away again, leaving me staring at my reflection in the full length mirror. When she turned back she had in her hands an Alice band that matched the gingham print of the dress and a hairbrush. With a determined look on her face she set about arranging the mop of hair that sat atop my head, turning me this way and that as she sought to bring order to the chaos that was my head. Finally satisfied with her efforts, she pulled the hair back from my ears and fitted the Alice band, making sure that it was firmly in place behind my ears. She turned me back to the mirror, standing back to admire her handiwork, and once again I was mesmerised. Now, instead of seeing me there wearing a dress it felt as though I was now looking at myself as a girl. Not a boy in a dress but rather me as a girl. The boy seemed to have gone. Almost.

Nikki giggled. I looked at her and saw that her eyes were fixed on my lower abdomen. I followed her gaze and saw a gorgeous flat expanse of gingham print spoiled by a protrusion from my crotch. None of the dressing or hair arranging had done anything to decrease my arousal, and the shape of my rock hard erection was quite obvious, upsetting the line of the dress and, to be honest, the overall look. I was also leaking, and there was a hint of damp spot on the dress.

"Oh dear," she said. "That doesn't look quite right!" She had a point. "Can you make it stop or go away or something?"

I swallowed. ", not really. It like just comes and goes."

"Wow that must be pretty inconvenient!" We all know she was right, don't we guys?

"Isn't there anything you can do to make it go quicker?"

"Err, well, sometimes if you like stoke it and stuff you can make it go." Well, it was worth a chance and to be honest I would have sold my soul at that point for her to touch it just once.

"How do you mean?"

"Well, you know like they talk about masturbation in the biology books, yeah?"

"Yeah," she said, although I don't think she really understood at all.

"Well if you do that to it it goes away."

"Go on then," she said, still looking a the lump in my dress.

I swallowed again, my heart pretty much in my mouth. Slowly my fingers grasped the front of the dress somewhere around mid thigh. I started to gently lift the hem, savouring the sensation that dragging the edge of the soft material across my naked thighs brought. As I drew it higher I felt the hem rub against my tight hairless scrotum and then the base of my cock. Nikki's eyes were glued to the front of the dress. Finally I drew the dress along the length of my now madly pulsating and dripping cock, revealing it once again in all its glory. I turned back to the mirror and the image that I saw there was burned into my memory for all time. There was a girl with tidy hair and a lovely Alice band standing in a red gingham print dress but she has pulled the dress up to her waist and rather than reveal a pair of white knickers, she has revealed a six inch or so rock hard penis sticking out of a nest of brown wiry hair with a scrotum swinging beneath.

"You could do it if you want," I said. my voice wavering as I spoke. Well, if you don't ask...

"What? No way, I'm not touching that!" Oh well. I tried. "If you want to sort it out you can do it yourself!" There was an ironic element to her protestations. I mean, there I was stark naked under her dress with a raging hard on, but she couldn't bring herself to touch it!

I began to turn away, but again she stopped me. "No, don't turn around. I want to watch."

"OK," I said and slowly my right hand moved to my erection and took its familiar firm grip around the shaft, with my thumb on my foreskin. My left hand held the hem of the dress above my waist. I stared at the image in the mirror and a girl with a cock stared back at me. Slowly I began to work my hand in its well practiced strokes up and down my shaft, savouring the sensation that I could already feel rising from the base of my spine. Nikki's eyes were glued to my crotch, fascinated by what she was seeing, while mine stared at the same image in the mirror in front of me. I could tell that the crisis would not be long delayed. The girl in the mirror's hand worked slowly up and down the hot hard shaft and I could see her legs start to tense at the coming explosion of sensation. I gripped a little tighter and rubbed my foreskin against the sensitive ridge of the head of my penis. I felt my stomach and leg muscles tense and my head went back a little as the familiar wave of ecstasy rose higher and higher from my cock and from deep within my body until with grunt the feelings swept through me from top to bottom. I held my breath, my back arched and my hand tightened against my cock as my scrotum constricted. Throughout all of this I managed to keep my eyes open and glued to the girl in the mirror as her own orgasm swept over her and I watched as the hot cum shot from the end of her cock, splashing down onto the carpet.

"Wow. Did that hurt or something?" Nikki asked. Happily she didn’t seem too concerned about the splashes of cum on her carpet!

I said nothing for a moment a I recovered from the orgasm. "No," I finally managed. "It feels great! You should try it some time!" She gave a non-committal "hmm."

"Will it go soft now?" she asked.

"Yeah, in a minute it will," I replied, and as I watched the girl in the mirror I could see her erection begin to lose some of it firmness and begin to transcribe the arc back to its normal position and as I watched it I savoured the sensation of what had to have been one of the most intense orgasms I had ever experienced as the afterglow washed over me in ever decreasing waves. If only Nikki knew how good that felt!

As my cock gradually softened I let go of the hem of the dress and allowed the material to cover my nakedness whilst I watched my reflection in the mirror. After a few minutes my little cock had returned to its regular position, but there remained a lump in the front of the dress where it brushed up against the material even when soft. Not much of a lump, perhaps, but it was definitely visible and Nikki had noticed it too.

"It's still there," she said.

"Duh! of course it is!" I replied. What was she expecting?

"It's because you don't have any knickers on. If you did it would be kept down." She had a point. "Put some on."

Automatically I reached for my underwear, lying discarded on the floor to my side, but Nikki stopped me. "No," she said. "Use these."

She half turned and reached down to pick up - of all things - the very pair of knickers that had started all of this in the first place. A pair of white cotton knickers with pink flowers printed on them, and a pink satin bow at the front. I simply longed to touch them.

"But they're yours," I said. I was sharp that day!

"I know. Put them on," she said, holding them out for me to step into. I raised my right foot and stepped into the garment, putting my hand on her shoulder to steady myself. Then, after I had repeated the manoeuvre with my left foot, Nikki drew the diaphanous garment slowly up my claves and past my knees. She paused only briefly to change her grip as her hand disappeared under my dress and then I felt the soft fabric caress the cheeks of my buttocks and then cup my genitals. Had I not just masturbated, I would have been instantly hard. As Nikki snugged the garment home the back of her hand rubbed across my still sensitive penis making my jump a little. "Sorry," she said with a mischievous grin. "Accident!" Yeah. Right. "That seems to have done the trick."

I looked in the mirror and sure enough the out of place lump was now gone and all that was there was a perfectly flat fronted dress. The image was complete.

"You look great, Amy," she said.

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