Finding Rachel

It had been four days since I'd tried on her panties, and the first three days she asked me to put them on as soon as she got home, then pulled them to the side and climbed on top of me. Last night, I had been wearing stockings and panties when she came home. She attacked me, fucking me with a wild abandon I'd never seen before, kissing me hard and smearing her lipstick on my face.

Afterwards, I'd cleaned up, still in the lingerie, cock tucked back inside, bulging obscenely. But what caught my eye was the lipstick. My lips were redder than ever, and my image in the mirror looked decidedly feminine. I'd spent the whole day thinking about it. Did Claire want to see more like that? Did I? A part of me certainly did. A part around six inches long. Over lunch, I worked up the will, and went to her make-up drawer. I pulled out the first lipstick I could find, pursed my lips, and immediately made a mess. I tried to clean it with a tissue, and eventually mostly succeeded. The image in the mirror was unrecognisable. Even this small change looked so feminine I could hardly see myself as a man. I was rock hard. I burned with shame. Was this for Claire? Or for me?

I wiped the lipstick off and went back to work.

An hour later, I was in front of the mirror again, and an hour after that. I came back again, this time in lingerie. Just to see the effect it would have on Claire, and not for any other reason. The whole effect was astonishing. My panties couldn't contain my cock, which felt like it had grown another inch. The deep red of the lipstick was captivating, and the woman in the mirror was so hot.

As the key entered the lock on our front door, time crawled to a halt.

A blur, and a hope of escape dashed. 'Why are you wearing my lipstick?'

Oh fuck.

I was trembling. I'd gone too far. 'I wanted to be sexy for you'.

'Oh baby, you're already sexy for me. You don't have to put on any make-up. Unless you want to'.

'Okay'.

'Do you?'

'Do I?'

'Do you want to wear make-up?'

'For you?'

'For you'.

'It... just feels so sexy wearing those things. The make-up makes it even more'.

Claire nodded, and I had the feeling she was about to turn and leave. She surprised me, as she always did.

'Well then you need to do a better job of it. Sit', she commanded. I sat.

'We have so much to do here, but first, I'm going to show you what you can look like'.

She picked up a brush, and another brush, and some tubes, and a million other items. Her hands blurred over my face, brushing, dusting, drawing, until an eternity later when she gestured to the mirror.

I was blown away.

The woman staring back at me was radiant. Her hair was short but still feminine, her eyes seemed huge, her skin glowed, her lips shone.

'Careful Narcissus. Don't fall in love with your own reflection'. I closed my mouth. 'But', said Claire, 'you really do look good. Do you feel good?' I nodded. 'Why don't you try it with your lingerie. I'll be waiting right here, on the bed. You come join me when you're ready'.

I walked away in a haze, quickly changing into stockings and panties. By the time I came back to the room, Claire was naked on the bed, phone at the ready, snapping pictures of me.

'Hey!' I shouted.

'No way I'm forgetting this. I'm going to be cumming to this for years'. Her words made me blush, and as I approached the bed, she spread her legs. 'Don't worry', she reassured me. 'The make-up is waterproof'.

'Well I wouldn't want to ruin all your hard work', I said with a wink, crawling from the foot of the bed to my prize. I reached her tongue-first, eagerly lapping at her dripping slit. She was as wet as she had ever been, and my mouth had to work hard to keep up. Even with minimal attention to her clit, she still clamped down hard on my head, writhing in ecstasy in only a few minutes. She pulled me up, impatient, and kissed me deeply. She turned her phone to me and swiped through the most recent pictures. A beautiful woman going down on her, ass in the air, long lashes on display as her eyes stayed closed, focused on the pleasure she could give. 'This is the hottest thing, ever, ever, ever', Claire said. 'Please, fuck me hard'.

I came in about three seconds, images of myself eating her out in my head. Claire could barely hide her disappointment, so I sank back to my knees, and ate her cummy pussy until I was hard again. Thankfully, it didn't take long, and I mounted her again. 'Do you like eating your cum out of me?' she asked.

I shrugged, trying to be casual. The flavour was fine. The act was so naughty that it gave me a thrill. 'Mostly, I just like going down on you'.

'Well', she continued, 'you can do it whenever you want. Or maybe even whenever I want'.

Her words made me throb within her as I thrust hard.

'Do you like that?' she asked. 'Do you like me telling you to eat your cum out of my well-fucked pussy? Do you like dressing up, and putting on make-up, and sucking it out of me? You're so fucking dirty, it's so fuck- ah, fuck, yes'.

She tailed off, her tongue invading my mouth as she clamped down on my cock, quickly bringing me to orgasm for the second time. I slowed, barely thrusting within her, as the aftershocks tapered off within her. We both lay back on the bed, and I saw her reach down to her slit. Her hand came back dripping with a mix of our cum. She licked it, and then offered it to me. I couldn't resist, closing my mouth around her fingers, sucking them clean. Her eyes sparkled. 'Good girl'. My cock twitched.

Later, we had a very frank conversation.

'Do you want to be a girl, Alan?'

'I don't know. I know that you like me dressing up. And it feels somehow wrong and right at the same time'.

'Do you just want to dress up?'

'What else is there?'

'Do you want to be with a man?'

I was taken aback. I thought of kissing a man. Thought of his face on mine. It didn't appeal to me at all. 'I don't... think so? I can't imagine myself kissing a guy'.

'Would you suck a cock though?' I was flabbergasted. I hadn't even considered it. The thought of a smooth, hard dick in my mouth was surely unpleasant, right? If I didn't want to kiss a man, why would I suck a cock? And why was my own so hard? 'I think your blush is a "yes". Good to know'

'I didn't say that!'

'What about getting fucked? Would you like a nice big cock inside you?'

'Claire, I don't know what I want. I think... I want to try being a bit girly for you. Is that okay?'

'Have you thought about this for long?'

'Just since you made me shave. I think it opened up the idea in my mind'.

'And probably you watch too much porn'.

'Ha ha, very funny'.

'Well I mean, you see a bunch of hot dicks being sucked and now you aren't saying no to sucking one or fucking one, don't you think that might have something to do with it?'

'I don't know. I don't know!'

'It's fine though. If you wanted to kiss a bunch of men, I might be worried you'd leave me for something you wanted more. But if you just want to experiment, you're probably not going to run off with a man any time soon'.

'I don't want anyone but you'.

'And maybe a dick or two?' I flushed with embarrassment. 'You can be girly for me. We'll see what else happens. I won't force you into anything'. She reached out to take my hand. 'If you're ever uncomfortable, just tell me. We'll stop everything. But if you don't tell me, I'm going to try to find out what you really want. I think we can have a lot of fun'. I smiled.

'Thank you Claire. I do love you'.

'I love you too. Now let's eat. Someone made me work up an appetite'.

* * * * *

Claire began a campaign dedicated to broadening my horizons. I tried to live up to anything she asked for.

The next day, she sent me a set of make-up tutorials. I threw myself into them, and within a few days I was producing passable results. Even with a poor job, I was astounded at how feminine I could look. I worked to make it better. The nights following, Claire came home, gave me a few more pointers, and pulled my face to her dripping snatch. She was clearly enjoying it. On Friday, I greeted her at the door in garter belt, panties, stockings, and the best make-up I could manage. She fell to her knees and sucked me off, drawing the cum from me in a heartbeat. She swallowed hard, and dragged me to the bedroom. We fucked for hours, Claire alternating her head from tossed back in pleasure to staring at my smooth, feminine appearance.

On Saturday, I woke up alone. Claire left a note in the kitchen, letting me know she needed to do some shopping. I shrugged, made coffee, and relaxed. A short time later, I got a text.

Coming home. Be ready.

Ready for what? I replied.

Be READY.

I ran to the bedroom. Twenty minutes later, I was on the couch, dressed in my lingerie, and my face was well made up. I had thrown on a t-shirt, too, because lounging around in underwear turned out to be cold. I didn't know how models did it.

Claire came into the room, beaming at the sight of me, laden with bags and bags of shopping in a wild array of colours, shapes, and sizes.

'You know we have bills?'

'Hush you. I do this all for you'.

'Oh I'm sure, there's no pleasure in this for you at all'.

'Not even a little'. Her grin could have swallowed me whole. 'I bought a few things for you. I am going to lay them out on the bed, and I would like you to use any of the ones you feel comfortable with'.

I gulped, and nodded.

Claire bustled away, and a moment later, I heard her calling me. There, on the bed, lay a point of no return.

A short black skirt.

A loose white blouse.

A heavily padded bra.

A dark wig, with hair medium length.

A pair of black high heels.

I was ready for all of it.

I picked up the bra first, and Claire sat at the head of the bed, watching me. Distracted by the items on the bed, I hadn't noticed she'd slipped into a thin silk robe. She parted it as I put the bra on, revealing herself as I did. I clasped it behind me, and looked back to Claire, who was already two fingers deep in herself. I pulled on the skirt, zipping it up, covering my stocking tops. I pulled the blouse over my shoulders, buttoning it. I put on the wig, tilting it this way and that until it felt natural. Finally, I stepped into the heels, and almost fell over. I took a step, hesitant. Then another. I stood, hand on one hip, and became aware of a buzzing.

Claire lay on her back, head propped up to watch me, slamming a vibrator in and out of herself, biting her hand to keep from crying out.

'Like what you see?' I asked with a toss of my hair. I expected a laugh, but instead she gave me a long drawn-out moan of pleasure. I looked in the full-length mirror and almost moaned myself. The woman staring back was incredible. Slim, but with curves where they should be. A beautiful, feminine face, with a hint of a pout. Long legs shaped perfectly by the shiny black heels.

She grew a bulge in the skirt.

I looked back to Claire, who was clearly lost deep in the throes of an orgasm. I tottered over to stand beside her. 'You like?' She nodded, half-dazed. I watched the vibrator slide in and out of her, and was hypnotized. She looked so full. I leaned in to kiss her, and she came again.

'This is too hot, fuck, I can't stand it', she gasped out.

'Do you want me to take it off?'

'Yes! No! I- aaaah'

She finally finished cumming a few minutes later. I leaned in for a more tender kiss. She reached out to cup my face, and slid her hand down, brushing my neck, squeezing my "breasts", before settling on the firm lump in my skirt. Her hand dipped to caress my leg, then traced up over my stocking tops to find my cock bursting from my panties. She grabbed it firmly, and stroked me hard.

'You're such a bad girl'. Hearing her call me a girl did strange things to me. Mostly, it made my cock surge in her hand. 'Dressing up like this, are you trying to seduce me? I'm a married woman. But you're so hot. Maybe my husband doesn't need to know. What's your name?'

I answered without thinking. 'Rachel'.

'Oh how cute'. I flushed red. I hadn't thought of a name before, and I was sure Claire knew that. But this one fit. 'Do you like me rubbing you Rachel?' I nodded. 'Are you going to be a good girl and cum for me?' I nodded again, panting. Claire wriggled out of the bed, and in a second my skirt was flipped up and her mouth replaced her hand. I couldn't hold off, releasing my load in her mouth, draining everything I had into her. She paused for a moment, then reached up to kiss me, pulling my mouth to hers, and pushing my cum back into my mouth. It was unspeakably erotic, the hot wetness drenching both of us, our tongues flailing wildly. She broke the kiss, and we both swallowed whatever portion was left. I leaned back in for another kiss, and we tumbled into the bed together.

Soon I was hard again, and Claire straddled me, sinking hard onto my cock. I thrust back at her, but after a few minutes, she jumped up, lifted my knees to my chest, and sat back down. She took me back inside her, but the angle was so unique it felt like nothing else. She ground her hips on me, and it was as if our roles had fully reversed, and she was the one with the cock fucking me. Her stamina somehow lasted long enough for us both to cum again, totally ruining my nice new skirt.

'That was amazing. I'll need to wash this'.

'Not right now. I bought you three of them'.

'What!? What if I didn't like them?'

'I know you by now, Rachel. Now you have enough to wear whenever you want'.

I kissed her tenderly. 'Thank you'. We basked in the warm feelings for a time. 'Seeing you with the vibrator was incredibly sexy, by the way. Is that new?'

'Mmm, yes, it is. There are a couple of other things too but I'm saving them for later. Tomorrow maybe. For now, let's have a nap'.

I couldn't have agreed more.

* * * * *

With most of our sexual energy burnt off, the rest of the day was normal. We ate, watched a film, drank, and, mostly, were a normal husband and wife. But I kept the heels on, for practice, until we collapsed into bed. Sunday morning was more of the same, until midday, when Claire could contain herself no longer.

'Can I show you what else I got you!' This was not a question. She ran to grab the rest of the bags, then ran to drag me to the bedroom. She pulled garment after garment out, arrayed on the bed, and begged me to try them all on. The first was a pair of hot-pants and thin tube top. I tried them on, quickly, and saw Claire pout.

'What's wrong?' I asked.

'Put on a show!' She commanded, peevishly.

I turned, and pulled the hot-pants down slowly. I looked over my shoulder to see a broad grin plastered across Claire's face, and the vibrator whirring to life in her hand.

The next item was a longer very light skirt, floral pattern, with a sleeveless white shirt. I pulled it on and had never felt more like a woman. Squishing sounds from the bed let me know Claire was enjoying it too.

The last was a simple blue sundress, cinched at the waist, and falling over my hips. I pulled it on over my head, and crawled up the bed. The vibrator sped up. I kissed my way up her legs, face just beside her sopping wet slit and its silicone visitor. I tilted my head to look at Claire, mouth agape, approaching her first orgasm. I batted my lashes, and put my tongue on her clit. She exploded, ramming the vibrator inside her and mashing my face down with her other hand. She tried to stroke the the vibrator out and back in, but succeeded only in pushing the cock-like tip into my mouth.

I licked it.

Then I sucked.

Claire was watching me, so I pulled off. 'You taste good'.

Claire pulled me in for a searing kiss, hiking my skirts to my waist, reaching for my cock, aiming it at her now-empty slit. I sank straight to the hilt, thrusting slowly. Claire moaned into my mouth, and pushed me back up. She brought the vibrator, now still, to the narrow space between our mouths. 'Do it again?' she asked.

I looked into her eyes as I licked the soft flesh-coloured tip. She shuddered beneath me. I sucked on it, and felt her clamp down on me. I pushed it further into my mouth, and her eyes lit up. 'Suck that cock, Rachel', she said, 'take it deep'.

She definitely felt me throb within her, and she ground her hips against me. I didn't move, focusing instead on the thick fake cock in my mouth. It was wider than I expected, filling me completely. I continued to slowly suck and started to thrust back at Claire, driving deep within her. She was transfixed, watching me, watching my jaw moved as my tongue worked, copying all the moves I know Claire liked to use on me. 'Do you like that big dick Rachel?' she asked.

'Mmm'.

'Does it taste good?'

'Mmmmm'

'Are you going to let it cum in your mouth?'

The image sent me over the edge. I shot a huge load into Claire, even considering how drained we were, and felt her cum around me. I knew it was as much from watching me cum at the thought of sucking cock as it was my hardness inside her.

I rolled off her, my dick still half-hard. We sat quietly for a moment, but Claire could only hold back so long.

'Would you do it for real?'

'I don't know'.

'But wasn't this hot?'

'Yes but it was just your taste on it'.

'Real cock tastes better you know'.

'Are you trying to convince me? What happened to only doing what I'm comfortable with?'

'If you say no, I'll stop. But you haven't said no'.

'Well, this is me saying... maybe'.

'God you are amazing'. Claire rolled on top of me, kissing me fiercely, until I pointed out that any more action would cause my cock to drop off. She was clearly still eager, so I told her to lay back and used the vibrator on her. The sight of it was incredible. I hadn't seen her getting fucked from this angle before, and the erection it gave me was painfully hard. After she came, and came again, she finally relaxed.

We had a light evening meal, and then lay on the couch, eventually dragging ourselves back to bed, thoroughly fucked out.

But Claire's mind couldn't stop.

* * * * *

The next night, she stood as soon as we had eaten. 'Let's go for a walk. Get dressed'.

'Sure'. I stood, and reached for the t-shirt I had discarded earlier.

'Rachel, let's go for a walk'.

I froze. Claire bit her lip. Our street was well lit, though the sun was down, and I was well known. I couldn't do that. Could I?

I thought back to my image in the mirror. The stranger I saw there, who looked more like my sister or cousin than me. I slowly nodded.

I pulled on my stockings, skirt, heels and blouse. I touched up my make-up, which I'd applied for practice that morning. My bra was already on; Claire had insisted on it when she came home, so she could feel me up. Nothing more was needed, as it was a warm night. Claire took my arm in hers, partly for moral support, partly physical; I still wasn't an expert in heels.

We clacked out of the driveway. 'How far do you want to go?' I asked.

'Until we get tired. It's a nice night. Let's enjoy it'.

'Claire! What if someone recognises me?'

'They won't. I barely can. We'll just pass you off as your cousin, visiting while you're away for work. Simple'.

'They'll recognise my voice'.

'Rachel, you just have a slightly husky voice for a woman. Even as Alan you're in-between. The only way they'll spot you is if you worry. Oh hello Marie!'

I felt woozy as our elderly neighbour came to say hello.

'Hi Claire, who's this?'

'This is Rachel, Alan's cousin. She's staying with us for a few days. Say hello Rachel, be polite!'

'Hi, nice to meet you'. My voice sounded higher pitched in my ears, whether from a desire to hide or pure fear I couldn't tell.

'Ooh she's very pretty. Lucky she's his cousin, or you'd have something to worry about'.