Andy to Amy

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A young man's first venture into crossdressing.
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"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 kids 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."

"Four."

"Two."

"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 family 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 kids 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?"

"No!"

"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."

"OK."

"Promise?"

"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."

"OK."

"Promise?"

"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, utterly clueless about sex and standing stark naked in my 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 everything...no 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.

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