Amateur Photographer Ch 08

Kate had given me another mind shattering blowjob before the end of the night. She literally sucked the life out of me – first thing I knew it was next morning and she was gone, and I was still spread out on the sofa, naked. Except for my bra, fake tits and wig...

As I got dressed for work (hastily removing the lipstick), there hanging in the wardrobe next to my business suits was the black dress. Kate had obviously hung it up while I'd been asleep. And there at the bottom of the wardrobe lined up neatly were my gym shoes, hiking boots and black business shoes. And now a pair of black high heel pumps. Well, what could I say, she'd bought them for me, and I had worn them...

I didn't ponder too much over that night with Kate. Sure, it was weird, it was very weird, but it was also horny in a bizarre, degrading kind of way. It was strange, but her telling me about trying on dresses before she bought that one for me, and how she told the shop girl what it was for, it made me feel embarrassed and somehow humiliated, even though there was no way that girl or anyone else could know Kate was talking about me, but at the same time that kind of gave me a thrill. It was something that was sticking in my brain. Or was it that she had just said that she wanted to dress 'her man' up. 'Her man', meaning me. I had enjoyed hearing that, I had to admit. God, was I falling in love with her?

I watched the video I'd made of Kate sucking my cock. The vision was a bit shaky – I hadn't kept the camera very still at all – but it was all there. God, she looked so sexy! So slutty! Cum everywhere, all over her face, her hair. And the way she looked straight into the camera – straight into the viewer's eyes, the sticky white fluid dripping off her lower lip like honey... Watching her on the screen as she licked the cum from around her mouth. Man, this was as hot as any porno movie I'd ever seen.

I must have watched it a dozen times in a row, gently giving my engorged cock a rub as I enjoyed the show, not wanting to bring myself off so I could enjoy watching it over and over again... Later, I thought, I'd take some still images from the video and see how they would scrub up photoshopped.

But for now, I was feeling frustrated. In need. And Kate, the cock sucking queen on my little home-made porno film, was probably just a phone call away. I picked up the phone and dialed her number.

"Hi Kate."

"Hi David, what are you up to?"

"Well, I've just been sitting here watching the hottest porno film I've ever seen."

"Let me guess – you've been watching some little slut sucking someone's cock?"

"Yep. She's a hot little slut, too."

"Is she now."

"Yes, she is." Then there was a pause in the conversation.

"So, is that all?" she said. "You've rung just to tell me you've been watching 'TV'?"

"Well, um, no. Can I come over?"

"Sure. Why don't you bring your camera?"

"OK, sure."

"Have you eaten yet? I've got a roast in the oven – we could make it a dinner date."

"Yeah, that'd be nice."

"And David, will you dress up for me?"

"What do you mean?"

"You know what I mean."

"OK, I'll bring it with me."

"No. Why don't you get dressed there? I want you to get dressed before you leave your place. I want to open my front door and see my woman standing there looking all sexy for me."

The import of her words were clear in my mind; there was no misunderstanding it. I knew what she wanted. It caught me by surprise, and I desperately didn't want to do it. But I wanted to please her. But calling me 'my woman' – how fucked up is that? And yet at the same time, it was funny how her addressing me as 'my woman' gave me a warm feeling just as it had when she'd said 'my man'. She was still on the phone. I didn't know what to do.

"Well, what are you waiting for?" she said, filling the pause in the conversation. "The black dress and heels are in your wardrobe. The rest of your outfit is in the cupboard. Go and get dressed. I don't want to be kept waiting up for you all night."

And then she hung up.

I sat there, perplexed. I could, of course, call her bluff and simply refuse to do it. Refuse to go at all, even. Damn it, that's what I felt like doing. She would be pissed, I knew that for sure. The fact was, though, that I wanted her; I needed to feel those lips of hers on my cock. I could refuse to wear the dress and simply go in my normal gear, but to turn up not 'dressed', when she had so firmly requested it – because that was how it came across in the tone of her voice, like an order, a non-negotiable directive – I knew that she was just as likely to shut the door in my face. And that, in a paradoxical way, would be more humiliating than it was to actually dress up as a woman for her. But more humiliating than dressing like a woman and then leaving the house, and going out in public? This was something else again.

Yet bizarre as it was, it really wasn't a complicated scenario: if I wanted to see Kate tonight, then it would have to be with me wearing the dress. Simple as that. It didn't really matter what I thought of it; she held the aces and she was calling the shots here – it was me who wanted the blow job. I just had to decide whether or not I wanted it on her terms.

Go and get dressed, I said to myself.

I lifted the dress off the hanger. The garment seemed so small compared to my normal clothes. I stripped off my workday suit, and was about to pull the dress over my head when I realized I had forgotten about the rubber tits and bra. I got them out of the cupboard and slipped them on. I'd had plenty of experience with undoing bra straps before, but it's not so easy trying to put one on your own body, I was learning. Eventually I managed to fasten the clasp on the back, and then slip the silicone cones inside the cups. I jiggled them around with my hands until they settled into place. I pulled the dress over my head and zipped it up at the back. I slipped on my high heels and wig. She had left the lipstick sitting next to the wig. Better put some lipstick on, too.

I looked at my reflection in the mirror as I applied the lipstick. It was uncanny. Yes, I did look like a woman. Well, close up, you could see there was something wrong with the image; certain masculine elements that couldn't be concealed by a short black dress, wig and heels. But from a distance, even a fairly short distance, I could certainly pass for a woman, I felt. I pouted my lips as I applied the lipstick – again, not that easy to do with no prior experience. My first attempt left lipstick over my cheeks and made me look like a drag queen. Not very ladylike. But I soon got the hang of it, and I was quite proud of my efforts with the lipstick in the end.

I was tingling inside with trepidation at what I was about to do. This was the wildest thing I had ever done, and I was more than a little scared. What if someone saw me? I only had to make my way downstairs to the basement carpark, and from there it was only a short drive. What if someone I knew from one of the other apartments saw me? What if I got pulled over by the cops on the way? I could always just say that I'm going to a fancy dress party. I was worried. Yet also a little bit excited. My cock was half hard. This was a seriously kinky thing to be doing. This was not what regular guys did. This was not the sort of thing that I did. Yet the thing was, I liked the way I looked in a strange kind of way – I looked like a woman; not a stunner, but certainly convincing enough. Yes, if I held my nerve I could pull this off.

I stuffed a pair of jeans, shoes and a shirt into my sports bag for the return home. The bag would be handy, I figured, too, because I could use it to conceal my cock, which under my dress was getting harder by the minute...

I was ready. Well, I was also shaking with fear, so I took a swig of Scotch (straight from the bottle) and opened the front door. No one. Good. I grabbed my bag and made my way down the stairs. The click clack sound of my heels echoed loudly all the way down the staircase, no matter how daintily I tried to walk. I made it to my car without seeing a soul.

Kate's house was not far from mine, so having run the gamut of leaving the apartment dressed like this, I could now relax. I found driving in heels especially difficult – how do women do it? – but I soon got the hang of it. The drive was uneventful, except for one time waiting at a set of traffic lights. A beige Lumina pulled up alongside, and I noticed the guy, round about my age, behind the wheel cast a glance my way. It was classic male traffic light stuff; you're driving up alongside another car, you recognize it's a woman at the wheel from the hair style, and once you're alongside you casually take a look across at her to see whether or not she's a babe. The Lumina guy lucked out a bit this time, I chuckled to myself as the lights flashed green and I nailed the gas pedal.

Soon I was in Kate's driveway. I had made it, and I almost felt proud of myself. I stepped out of the car – again, no one saw me – and walked up to the front door and ringed the bell. The door opened.

"Oh my, what a hot looking girl!" Kate said excitedly, eyeing me up and down. "Come inside baby!" She was wearing a business suit. A man's business suit. Her hair was slicked down flat, tied at the back in a little pony tail. She was wearing flat-soled black shoes. Jesus, this was getting even more bizarre.

As she led me through the hallway I could feel her hand rubbing my ass. Inside the living room, I put my bag down. As I did, she grabbed me from behind. She held me close, her hands roaming around my body, one grasping for my crotch, the other over one of my tits.

"Mmmm, baby you're looking hot tonight!" she squealed as she massaged my breast and cock. "Mmmm, you feel good too!" I felt her thrust her crotch into my ass as she said the word 'feel'. Then she let me go and headed into the kitchen. I followed her, watching her as she tended to the roast and grabbed a bottle of wine out of the fridge. Her suit was loose fitting; you could barely make out the shape of her hips and tits. She had taken on the appearance of an effeminate looking young man.

"Drink?" she asked, eyeing me up and down, literally gawking at me as a man might a sexily dressed woman.

"Thanks," I said. "You're looking quite dressed up yourself there Kate."

"Oh, do you like it? I thought since you've gone to the trouble of making yourself look sexy, I should do the same."

It did occur to me that there was some seriously weird shit going on here. But at the same time it all somehow seemed to fit together, in a strange kind of way, in the context of the relationship - the ARRANGEMENT, actually, that Kate and I had struck – it seemed somehow a reasonable way for us to be behaving. It was the second time I'd dressed as a woman for her, and having made it here looking like this with no dramas or embarrassments, I felt reasonably comfortable with the situation, dressed as a woman, about to sit down to dinner with a woman dressed as a man.

She had neatly laid out the table with a couple of candles, the whole deal. She was a good cook, too.

'Compliments to the chef," I said as I ate heartily.

"Thank you David," she said.

The meal was quite fun, notwithstanding the context of our weirdo dress code. We chatted for a while, and it was in fact the first time we had ever conversed naturally about matters that weren't sexual. We talked about work. She told me about the pressures of her job, the staffing cutbacks they were suffering, and the disappointing academic performances of many of the students.

"This will be my seventh year there and honestly, David, they just seem to get dumber every year. Really, with some of the girls, you're probably doing them a favor – given their intellectual capabilities, modeling would probably be better suited to a lot of them. On that note, have you been taking any pictures lately?"

"No, but I've got one girl possibly coming next week. Jodi, that's her name."

"Let me think... There aren't many Jodis; I wonder if it might be Jodi Stevens? Philosophy student. Short, dark hair, cute but kind of homely looking?"

From the picture Jodi had emailed me, Kate's description fitted the bill.

"That'd be her."

"Hmm, I'm surprised that she'd be into something like that," said Kate. "Very shy, that one. Quiet as a church mouse in classes. Wouldn't have picked it. Still, appearances can be deceiving – I mean, look at us?" she shrugged, as if it were an everyday occurrence for me to be dressed as a woman and her as a man. "Who knows? Little Jodi might turn out to be a hot little firecracker once you get her out of those drab clothes she wears."

I was surprised that she should be talking like this; once I was a disgusting pervert, but now she almost seemed like an accomplice to my 'perversions'. She was talking as if she was a buddy of mine and we were chatting about hot chicks. Well, she was dressed as a man...

"I'm surprised you can be so flippant about your students, Kate, given how concerned you seemed to be for their welfare when you first came round to my place."

"Well, yes, I am concerned about them. I was concerned about them then and I still am now. But what they do in their private life is no concern of mine, and really, as sad as it is, a lot of them might well be getting training from you that's going to serve them better in life than anything I can offer them academically – although little Jodi, ironically she's one of the brighter ones. But don't forget, when I first met you it was a concern, a genuine one, that you might be out to exploit them – or worse – and that's the reason I first darkened your door. Luckily for you, you turned out not to be the pig of a man I'd been worried that you might be. Actually, you turned out to be anything but a pig of a man."

She paused and took another mouthful of food. She was still looking at me.

"God David, I have to say you look just so fucking sexy sitting there looking like that," she said.

"Thank you," I said, slicing off another piece of the rather excellent roast she'd cooked.

"You know, I'd fuck you if I was a man," she said. I could feel the sheer sexual energy, almost menacing, in her voice as she spoke. There was no doubt she meant it.

"Do you want to be a man?" I asked. It was the first time I'd questioned her directly about her peculiar fetish, and after I'd said it I hoped she hadn't taken it in a double meaning kind of way: that I might have meant wanting 'to be a man' as if it was an invitation to 'be a man' and fuck me, which it wasn't. She gave me an inquisitive glance.

"Do I want to fuck you?" she said. "Yes, I want to fuck you. I'd like to bend you over this table right now, lift up your dress and fuck you hard like a man fucks a woman. I would love to do that. But do I want to be a man? No. It's purely fantasy. Just because I like role playing like this doesn't mean I want to be a man."

She slid over a little closer. Close enough so that she could reach under my dress. Her hand found my cock.

"David, your cock is hard. Just because being dressed as a woman gives you a hard on, does that mean you want to be a woman? Of course it doesn't."

It was hard to argue with logic like that.

Soon we had finished our meal.

"Feel like a smoke?" she said, as she got up to clear the table.

"Cigarette?"

"No. I've got some good stuff."

I nodded. Actually, I hadn't been wasted in years. I worried that this might be a ploy to loosen me up so she could fuck me with her dildo, but to be honest I was just enjoying being with her. I loved how direct she was, how sharp her mind was, her intelligence – even if I also found it a bit intimidating. I wouldn't say she made me feel stupid, but with her aggressive demeanor it seemed as though I was always a step or two behind her thought processes, always trying to catch up. Well, the woman is a professor...

"We'll have to go outside," she said. "I don't smoke inside the house."

We went out onto the back patio. She did have a nice place; small courtyard, leafy, very elegantly landscaped. We still had our wine glasses as she came out with a small bag of weed; it almost felt like it was some kind of formal cocktail party, except for the fact I was dressed like a woman might dress for such an occasion.

She handed me one of the joints she'd rolled as she lit one herself.

"Don't worry, this stuff's not too strong," she said.

I took a few puffs as I leant on the patio railing, both of us gazing out into the night.

"Nice night, isn't it?" I said.

"Yeah."

It mightn't have been strong dope, but pretty soon I was feeling the effects. After all, it didn't need to be that strong for me – I hadn't smoked in years. I looked up into the stars as that familiar mellow feeling enveloped me. Kate had gone a bit quiet; I assumed it was having the same effect on her. Then I felt her arms come round my sides as she embraced me from behind. She began to kiss me gently on the back of my neck. It was almost romantic.

"God, you look hot like this, out in the moonlight," she breathed into my ear. She kept kissing me, one hand reaching up to squeeze my tits as I stretched forward, still leaning on the patio rail.

"David," she almost whispered. Under the effects of the dope, her voice had a beautiful tranquility to it. "Take off your panties."

I reached up under my dress and pulled my jocks down. I felt my cock spring free, nudging the hem of my dress forward as it did. I pulled them down and stepped out of them. Her hand found its way between my legs from behind me. She began to gently rub my cock, her finger straying down to gently cup my balls. I could feel my cock getting harder by the second.

Her fingers wandered back behind my balls, gently ticking the skin at the base of my scrotum. It felt so good – so sensitive against her delicate touch. Her fingers wandered further back, till they grazed against my asshole. Oohh, such a light touch, but almost like an unbearable tickle. Now she began to concentrate on my ass, running her finger around the rim, then up and down. All the while she was kissing my neck. I could feel her hot, panting breath on my neck. She grabbed my hips and pulled me back a bit, so that I was bent down further. Then I felt her finger push firmly against my opening. Then harder, harder still, until soon I felt the tip of her finger force its way inside. She held it just so, not going any further, as her lips ravaged my neck, her tongue licking my ear.

After a while I felt her push again, and her finger slid inside a little more. It hurt. More than a little. Again she just held it there, but not for long, as soon I felt her plunge it deep inside. Somehow I had relaxed enough to let her inside – now I could feel her finger all the way in, because her other fingers I could feel now playing lightly against my balls. Ever so gently she began to move her hand, establishing a gentle, slow rhythm with the finger in my ass as her other fingers tickled my balls. It felt incredible; like nothing I'd ever experienced. I felt violated, but the pain was subsiding, partly due to the fact that I was getting used to the feeling of her finger's invasion, and partly because of the attention she was paying to my balls. And partly due to the relaxing effects of the weed. Because if this felt weird or confronting, to be bent over a railing wearing a dress while a girl gently fucked my ass with her finger, well, it didn't seem any more weird than warped reality induced by the effects of the drug.

She began to slide her finger in and out; slowly, but forcefully – she really was fucking me with her finger now.

"Oh David, that feels good!" she purred. "Oooh, yeah, you like it too, don't you? Hmm?"