April 1987

It had become a bit of a Saturday ritual. I’d cycle over to Matthew’s house mid-morning, and we’d spend the day doing boy stuff together. We were both into sport and keeping fit, so we’d maybe go for a three-mile run, do some fitness training in the garden, then watch TV or goof around in his room in the afternoon.

Matthew’s mum and dad were very pretty laid back. They usually went shopping after lunch, and Louise, Matthew’s hot younger sister, was mostly out with her latest boyfriend, which meant we often had the house to ourselves. I say house, but the four of them lived together in a cosy little cottage on the edge of the village. Occasionally, I’d stay over for the night, and we’d spend the evening in his downstairs bedroom talking about girls and jacking off.

Speaking of which, at seventeen, Louise was two years younger than us, and had recently started her A-levels. I’d had a crush on her since forever, but she barely tolerated my presence. She was tall – as tall as me – and somewhat haughty. I thought she was fabulous, and that the sun shone out of her backside, whereas she tended to look at me like I was a piece of snot on the end of her finger. I spent a lot of time wanking over her.

This particular Saturday, Matthew’s parents were away for the day, visiting friends. Louise was, of course, with her latest Romeo, so we had the run of the house for the whole day.

Final exams were coming up, so after our run, we spent the rest of the morning doing homework and revision. After a couple of hours, however, we were both getting bored and fed up with it all. We needed a distraction.

Now, of course, Matthew knew I had a crush on his sister. And he loved to tease me about it! Giving an exasperated sigh, and slamming his book down, Matthew looked up at me with a calculated look in his eye.

‘Would you like to see my sister’s room?’

Startled out of my reverie, I wondered if he’d been reading my thoughts. I’d been fantasizing about Louise, and my cock was hard in my pants. Feeling guilty, I didn’t want to sound too enthusiastic. On the other hand, the thought of entering her room made my heart flutter.

‘Yeah, why not,’ I responded with a poor attempt at nonchalance.

Unlike Matthew, Louise slept in one of the two upstairs rooms. Matthew led me up and opened the door. Surprisingly, Louise had a fairly spacious room for such a small cottage. It was quite a bit larger than Matthew’s, and had that classic teenage girl feel to it, despite the oak beams and wonky floors. Pop groups were tacked to the walls – mostly Wham by the looks of it, and she had an old pine desk with school work scattered across it. She even had a queen-size bed, which instantly gave me an image of her lying on it with one of her boyfriend’s doing I’m not quite sure what! An old pine dressing table and wardrobe completed the picture.

It was quite messy. There were several sets of footwear next to a wicker laundry basket with the lid half off, and various items of clothing were strewn around the room. It felt very intimate, and as I stood there in the doorway, I felt as if we were invading Louise’s privacy. But at the same time, I couldn’t help feeling excited, especially as I looked at her discarded clothes. I recognised jeans, and at least two blouses either on the floor or over the back of her desk chair. I found myself wondering what was inside the laundry basket.

Matthew could see where I was looking.

‘Why don’t you have a look? See what’s inside?’ he suggested. He looked amused, watching me staring around her room in fascination.

Moving the lid to one side, and peering into Louise’s laundry basket, the first things I saw were several pairs of white socks, and two pairs of cotton panties; one pair was peach, and the other was pale mauve. I felt my face heating up, and I hesitated, wanting desperately to touch these forbidden items, but knowing that if I did, I would be stepping over a huge line.

Like Matthew, I was still wearing my running kit from our earlier exercise. I could feel my cock rapidly growing in my shorts, and I reached down and ran my fingers subconsciously over the outline of my engorged member as I continued looking at the enticing objects in the basket below me.

I couldn’t help myself. Taking a deep breath, I leant down, picked up the peach panties, and lifted them out of the basket. I glanced at Matthew, who was watching me intently. He could see what I wanted to do.

‘Go on then – you’re dying to, aren’t you…?’

‘She’d kill me!’

‘Yes, probably,’ he laughed. ‘But she won’t know, will she?’

Nervously, I raised the panties to my face. I hesitated for a brief moment, and then pushed my nose into the material, inhaling slowly. They had a musky, heady scent, and I felt my excitement grow with the thought of where they had been – how they had been in contact with her warm and most intimate and private parts at the top of her long legs.

Thinking of those parts, I folded the material so I could see the gusset more clearly. Here the material was crusty and stained; once more I put the material to my face and breathed in, absorbing new tart and tangy aromas along with the previous muskiness, all of which were sending my senses into overdrive. I tentatively put out my tongue and licked the material.

Matthew watched me with a huge grin on his face.

‘Perv,’ he said.

‘It was your idea!’

‘I didn’t tell you to sniff and lick my sister’s knickers…’

I felt myself go even redder, but didn’t put the panties down. I was too captivated.

‘You know she’s fucking Brad at the moment?’

‘Is she? No, I didn’t know. He’s supposed to be hung like a horse.’

‘Yeah – you’ve no idea what might be in those! Essence of Brad, perhaps?’

The thought seemed to amuse him. But I still held onto the panties, thinking about Brad fucking Louise, and her putting her panties back on afterwards. I held the gusset tight over my nose and mouth and closed my eyes.

‘Why don’t you put them on?’

I felt my cock twitch again at his words. God, what a thought! Wearing this most intimate of garments, that had been right next to her pussy…

I looked at Matthew, who was smiling at me. I wondered if this was why he’d suggested coming in here in the first place; when we’d been messing around in his room one night, I’d foolishly admitted that I found the idea of dressing in girl’s clothes a turn on.

‘Don’t be silly…’

‘Go on – I bet you’d love to! I could take some pictures.’

‘Don’t you dare!’

We continued looking at each other silently for a few more moments. Then, slowly, I took off my shorts and pants, conscious of my stiff cock, and of Matthew watching me. Taking Louise’s panties, I slid my legs through the holes and pulled them up. My first thought was how they felt so different – lighter and skimpier than my own pants. And there was nowhere for my cock to go. The thin material wouldn’t support the weight of my engorged tool, so it flopped out the top, looking foolish.

I felt very naughty, standing there in Louise’s underwear. But at the same time, I was incredibly aroused. The thought that the material now clinging to my bottom and cock had, until fairly recently, also been nestling against Louise’s wonderful ass and pussy. I thought that if I touched myself, I might cum on the spot.

I realised that I wanted more.

Looking in the laundry basket again, I spied a lacy white bra. I picked it out and looked at it, thinking of Louise’s firm tits in them. The label said 36B.

‘Here, let me help you with that!’

Matthew walked over and took it from me. I took off my T-shirt, and he held the bra out for me to put my arms through, and then, stepping behind me, he hooked it up.

‘There! Now you’re starting to look like a proper girl!’

I blushed again, enjoying the unusual sensation of the bra over my shoulders and round my chest. I looked down at the lacy material, wishing I had my own small tits to fill the cups. All of a sudden, the idea of being a girl was utterly compelling. How lucky they were, to wear such items!

‘We’ll have to see if we can find you a whole outfit,’ Matthew said with a serious smile. I wondered what he was thinking, watching his best mate wearing his sister’s bra and knickers.

Yet, the thought of wearing a whole set of Louise’s clothes had my heart hammering. I could feel myself shaking. I’d never been so excited in my entire life.

‘Smile!’ I looked up in time to see Matthew clicking a camera.

‘Now I’ve got the evidence!’ he said with satisfaction.

‘Hey!’ Ashamed and mortified, I reached for the camera. He held it out of my reach.

‘Uh uh,’ he said, ‘and anyway, they’ll just be for us to look at – so we can wank over them together!’

Somewhat mollified, I went to see what else was in the laundry basket. I lifted the pale mauve pair of panties out and, already addicted, put them to my nose. The aroma was stronger in this pair – more recent perhaps? They were more stained than the pair I was wearing. I pushed the whole gusset into my mouth and sucked. I moaned at the acrid, tangy flavour, wondering if there were elements of Brad in here too. I didn’t know why the thought excited me so much – only that it did!

Matthew had been looking in the wardrobe. He pulled out a light grey pleated skirt and a black and gold tie.

‘Hey, look what I found! Louise’s school uniform! Do you want to try in on? It’d probably fit, given your relative sizes. Her school blouse is probably in the basket.’

I rummaged, and found the white blouse. It was a bit crumpled, but smelt divine. A mixture of Louise’s own scent, and her deodorant. I put it on, and found it just about fitted. It helped that I had a very slim build, and weighed no more than 130 pounds soaking wet.

Looking at Matthew holding the skirt, I desperately wanted to put it on. Up until now, it had seemed like a bit of a game. But the skirt was something different. Putting that on would be making a statement – crossing another line. I felt like I would be saying, I want to be a girl – please treat me like one! Or maybe that was just my subconscious, playing tricks with me again?

I wasn’t sure why I was so keen to dress like a girl. Or why it made me feel so excited. I only knew that it felt really good, and that my insides seemed all topsy-turvy, making me feel things I’d never felt before.

Nor was I sure whether it was just because they were girl’s clothes, or if it was because they were Louise’s clothes. Or was it because it was a school uniform? There was something about that, too. Maybe it was a combination? I also didn’t know what this all meant, or where it was leading. Was I less of a man because I wanted to dress like this? Was I gay? I still fancied girls – I knew that because I had the hots for Louise, as well as having a girlfriend.

All these questions raged through me as I stood there, in Louise’s panties, bra and blouse. but I also felt bizarrely content. I decisively reached for the skirt and Matthew handed it to me. I stepped into it, pulled it up and did up the side zipper. It was snug, but fitted amazingly well.

‘There! Perfect!’ he said, admiringly.

I went back to the laundry basket and fished out a pair of knee-high white socks. I removed my own sports socks and put on the knee-highs. Then, finally I looked at the shoes by the basket. There were Louise’s black Mary Jane school shoes. Louise, it transpired, had big feet for a girl – size sevens. I was a seven and a half, so her shoes were a tight fit, but I got them on.

I stood up straight in front of Matthew and looked at him coyly. I felt incredibly girly, and also very sexy.

Matthew had his camera in his hands again.

‘Smile!’ he said.

I looked at him thoughtfully. I might as well embrace it, I thought, and posed, hand on hip, one toe pointed away. The camera clicked. I stood in several different slutty poses, pouting, whilst Matthew took a series of pictures.

Matthew put the camera down and walked up to me. He looked into my eyes, and then reached out and slipped his hand under the skirt and found my cock, bulging out of the panties.

‘How does it feel to wear my sister’s clothes?’

‘It feels good,’ I whispered, slightly disconcerted by his hand on me.

‘Dressed like this, you could be my girlfriend,’ murmured Matthew. Then he leaned forward and kissed me softly on the lips.

I was stunned. Matthew had never done anything like that before. Nor had I ever been kissed by a guy. It was totally different to being kissed by a girl. Well – maybe not that different. It felt unusual, and had a distinct taste, but at the same time it was sort of okay.

I couldn’t deny that part of me was excited at the thought of being Matthew’s girlfriend – though he already had one – a real one! I’d never fancied another guy – only ever girls. But when I’d stayed over, we had occasionally stroked each other’s cocks, and made each other cum. It had originally been Matthew’s idea and I hadn’t been very comfortable with it at first, but we’d done it more than a dozen times now, and it was actually quite nice when somebody else did it for you. I hadn’t thought either of us had read that much into it, though, but now I wasn’t so sure.

‘Would you like to be my girlfriend?’ Matthew continued, in that soft voice.

‘Um, you already have a girlfriend…’

‘Yes, I know, but Elizabeth’s not here, is she? And, frankly, you look damned hot dressed like that…’

‘Um – I don’t know. What – what would I have to do?’ I asked tentatively.

Taking my hand, Matthew pulled me closer to him. He kissed me again, this time using his tongue. I parted my lips and all of a sudden, we were mashing our mouths and tongues together. Then he put my hand onto the crotch of his shorts. I could feel the outline of his cock through the material. He was quite hard.

‘You would stroke my cock,’ he whispered as he looked into my eyes.

Responding, I found myself stroking him through the material. My breathing was elevated. I thought I was spiralling out of control.

Then I felt Matthew’s hands on top of my shoulders, pushing me down. Partly in a dream, I followed his lead and dropped to my knees, so that I was looking directly at the bulge in his shorts.

‘Then you would pull my shorts and pants down and play with it. I think you might want to put it in your mouth and suck it. I think you’d look really good in my sister’s school uniform, sucking my cock. Would you like that? After all, it’s what Elizabeth would be doing…’

His words sparked a memory. A memory of the one time I’d taken the initiative when we were masturbating together…

Once – just once, when I’d been on a sleepover with Matthew, we’d been lying side by side on the floor in his room, slowly wanking each other; I’d reached over and put my lips round his cock. To this day I don’t know what made me do it – I’d just done it because it seemed like something to do. It was quite dark in the room and there hadn’t been much reaction from him for about fifteen seconds. Then…

‘What are you doing?’ he’d asked, sounding puzzled.

‘Nothing!’ I’d replied, quickly removing my mouth, flushed with embarrassment.

Neither of us had ever referred to that moment, but I remembered it. I remembered it because I had found the sensation of having Matthew’s cock in my mouth incredibly erotic, and forbidden. I’d been fascinated by the velvety texture of his glans and for a moment had wondered what it would be like if he actually came in my mouth.

I’m guessing that Matthew also remembered that moment. His behaviour now certainly indicated it.

Wearing Louise’s school uniform, kneeling in front of Matthew like that, I very much wanted to know what it felt like to have his cock in my mouth again.

I looked up at Matthew.

‘I’d love to be your girlfriend,’ I whispered.

Matthew smiled down at me. ‘Excellent!’ he said, ‘then I think we need a new name for you. A girl's name. I can’t call you Jason, when you’re dressed like that. Any thoughts?’

I looked down. I knew what I wanted to be called. Had known it for a while. I looked up again, coyly.

‘Jessica,’ I whispered.

‘Jessica,’ he repeated. ‘All right, Jessica, how about you take my shorts down?’ he said with an assertive smile.

I took a deep breath. In for a penny… I thought to myself! I slipped my hands into the top of his shorts and tugged them down, collecting his undies on the way. I pulled them down far enough to free his thickening, uncut cock. It sprang out, and I gazed at it, unsure of myself. Matthew’s cock wasn’t as long as mine, but it was a lot thicker! I put a hand round the shaft and tentatively stroked him up and down. Matthew let out a soft, breathy moan of pleasure. Then I pulled his cock towards my mouth.

I kissed the tip, and then slipped my lips around the end, licking him as I did so. Like me, Matthew wasn’t circumcised, and I enjoyed sliding the foreskin up and down, sliding it over the bulbous, velvety tip, and back down again.

I heard the sound of another picture being taken with the camera.

‘You look good, Jessica,’ he breathed.

I looked up at him again. He raised an eyebrow at me. ‘Don’t stop!’

Slowly, I slid my mouth down on him. Matthew’s groan was louder this time. My mouth felt very full, and I was careful not to get my teeth near him.

I started to stroke and play with his balls with my other hand, and then began to bob up and down on him, getting more of his length into my mouth each time I went down. I was sliding my mouth down his shaft, towards his stomach, wanting to see if I could reach the base of his cock with my lips. I tried to imagine his girlfriend doing this for him, but couldn’t quite picture it. I wanted to do it better than she did!

Part of me was still a bit worried about him coming in my mouth, and part of me was excited at the thought of having Matthew spunking down my throat. My own girlfriend didn’t like me coming in her mouth at all. She said she didn’t like the taste, but I thought it was more the idea that put her off.

I’d never tasted my own cum, never mind someone else’s. Why did the thought of another guy spurting in my mouth make me so hard? I could feel myself on the verge, the edge of Louise’s cotton panties rubbing across my hard penis as I bobbed up and down on Matthew. I felt very naughty and wanton.

Matthew didn’t keep me waiting in suspense for much longer.

‘Oh yes, I’m cumming! I’m cumming! I’m going to cum in your mouth! Swallow it all, Jessica!’ he said, as he started to shoot his load. I tried to keep my lips round his thick rod, wanting to fulfil my role as his ‘girlfriend’ properly. All of a sudden, I desperately wanted his spunk in my mouth! It felt very exciting being his girlfriend, and doing what she was expected to do. I thought I could imagine what being a girl was really like, kneeling in front of Matthew with his cock in my mouth, being used by him.

At the same time as Matthew came, I reached under Louise’s skirt to stroke myself. I pulled the cotton material over the tip of my cock, and with two quick strokes I came hard, soaking the thin cotton instantly with my cum, saturating it and feeling it spill out onto her skirt and onto the bedroom carpet.

I could taste Matthew’s spunk now – I’d swallowed most of it, but the salty, viscous liquid was coating the inside of my mouth. It felt very slutty, having spunk in my mouth – the baby-making sperm of another guy. But It wasn’t at all unpleasant – in fact I realised I was enjoying the thought of what I’d just done. I would have smiled if my mouth wasn’t still full of cock.

Matthew was stroking the back of my head, as he started to shrink between my lips.

‘You’re a very naughty girl, Jessica - look what a mess you’ve made! You should be spanked for being so naughty!’

I looked up at him.

'You're probably right, Matthew - if that's what you'd do to your girlfriend...'

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