Amateur Photographer Ch. 07

A quiet night at home, a few beers, feet up in front of the ball game on TV. The perfect midweek evening. The game was just starting when the phone rang. Damn.

It was Kate.

"Hi David, what are up to? Hope I haven't interrupted one of your photoshoots."

"Nah, just relaxing here alone in front of the TV."

"Can I come over?"

"Um, yeah OK," I said.

"Alright, see you in twenty," she said, and then hung up. I had been looking forward to the game, but it didn't go close to beating an evening with Kate working on my cock. I felt my loins stirring already in anticipation. And she's coming here – kind of like a home delivery service, I chuckled to myself.

Before long she was at the door. She greeted me with a lovely open-mouth kiss before coming inside.

"Drink, Kate?"

"Yeah. Glass of white if you've got."

She was wearing that same little black dress she'd worn when we met at the bar. Very fetching. She was a stunning looking woman, so fair in her features; there just something quite indescribable about her. She also had with her a big paper carry bag.

"What's in the bag?" I said as I handed her the glass of wine.

"I've bought something for you," she grinned. How sweet, I thought; she's come over here to suck my cock, and she's bought me a present, too.

"What is it?" I said, settling down in the sofa alongside her, admiring her shapely legs and black pumps. "What have you got me?"

"This," she said as she reached into the bag and pulled something out. It was black; it was an item of clothing.

It was a dress.

"I got you this," she said, standing up to show it off, draping the short black dress across her body by way of modeling it. "I thought you would look hot in this."

The memory of the dildo sucking saga came flooding back. Jesus, she wants me to wear a dress! I was about to speak, but I didn't actually know what to say. I was dumbfounded. She wants to dress me up like a woman?

She could see the look of alarm on my face.

"Look," she said, "before you lose your cool..."

"You want me to wear this?" I almost shouted.

"Yes. I want you to dress as a woman while you suck my strap on."

No. I'm not doing it. I can't believe that you're asking..."

"Look," she cut me off, "I know you think it's a bit weird, but I'd really love you to do this for me. It's just a fantasy of mine. David, it's only you and I here, no one else would ever know, and it's only a piece of clothing. What do you say?"

"Kate, in a word, no. The other night at your place, that was one thing, but this? This is just too far for me. Way too far."

We sat there in awkward silence for about half a minute.

"OK, she said. "How about we make a deal? If you do this for me, in return I'll let you take pictures of me sucking your cock. How does that sound?"

I had to admit it sounded good. Very good.

"With my memory card?" I said, remembering that she'd insisted on using her own card for the raunchy shots when we first did the photoshoot.

"Of course. And I'll make it look hot. You can cum all over my face and take pictures of it," she purred, her hand now stroking my cock. "Wouldn't you like that?"

Her fingers continued to work on my now hardening shaft. Yes, I thought, as my mind conjured a mental image of the shots she hadn't let me keep the last time, oh yes, I would like that.

"OK."

"Great!" she almost squealed in delight. "OK, now take your clothes off and let's slip you into your new dress! Come on, let's go into your bedroom – we'll need a mirror!"

I stripped down to my underwear and showed her the way. She unzipped the dress and pulled it over my head.

"Arms up," she said, as she slid the dress over my body. It fitted well enough, bit tight around the waist, but OK. Then she reached into the bag, pulling out a pair of black pumps.

"You want me to wear heels as well?" I said.

"Of course," she said. "I want you to look as nice as possible."

Resigned to the situation, I sat on the bed and fed my feet into the delicate female footwear. They fitted perfectly.

"How did you know my size?" I asked.

"When you came over the other night, I checked your shoe size while you were 'recovering'. Looks like I got it just about right. Looks like I guessed the dress size too. I took a bit of a punt on that, but it seems to fit just about right. Actually, that was quite funny, buying the dress. I knew roughly what size you would be, but the problem was going to be the shoulder width, because guys have got much broader shoulders. I was trying to gauge the size by trying dresses on myself, trying sizes that were really loose on me around the top, and the pesky shop assistant kept trying to give me smaller ones that fitted me better. In the end it became so frustrating that I actually came clean and told her what it was for – for a man. You should have seen the look on her face! I told her it was a fantasy of mine to have my man dress up like a woman, and that's what the dress was for. And you know what? By the look on her face, I don't think she was disgusted by the idea. Quite the contrary, in fact."

As if that wasn't humiliating enough, it seemed she had some other items still in the bag. She pulled out a wig!

"So I'm expected to wear that as well?" I said.

"Yes. I want you to look like a woman, not some drag queen. It's lucky that you've got quite slight features for a man, and you're not at all hairy. I mean, don't get me wrong, you're very sexy as a man, but I think you're going to look hot as a woman too."

Now she was rummaging though the bag for more things. Clearly this whole deal, bizarre as it was, excited her tremendously.

The wig was auburn in color, shoulder length, with a slight curl at the ends. Not unlike her own hairstyle. I slipped it over my head. I looked and felt ridiculous.

"OK, two more items and then we're done," she said. In her hand she was brandishing a black bra and pair of fake breast cups, made of some kind of rubbery plastic. She came around behind me and unzipped the dress, so that it fell down over my shoulders and arms. She slid the bra around my chest and fastened the back, and then inserted the fake boobs. She held my boobs in both hands jiggling them around to settle them inside the bra, squealing 'nice tits!" as she fondled them. Then she zipped me up. Under the dress I was conscious of the bra and how unusual it felt; the thin straps over my shoulders, the elastic of the strap against the skin of my back.

"For the final touch," she said, "lipstick!"

I was beyond the point of arguing now. What does it matter if she wants me to wear lipstick – she's already got me in a dress and heels, a bra and fake tits. She came in close, studying my face intently as she started applying the lipstick. I pouted my lips to make it easier for her.

"All done!" she cried, grabbing my hand and hauling me over to the mirror. I almost stumbled, unaccustomed to wearing high-heeled shoes.

She stood beside me, hands around my shoulders as we looked at the image in the mirror of me as a woman.

"Oh wow, you look so sexy!" she said. "I can't believe it!"

Nor could I. I almost couldn't recognize myself. The dress was mid thigh length, and framed between the hem of the dress and my pumps, somehow my legs didn't look masculine at all. It didn't look like me. Kate was right, I am quite slightly built for a man, but I never would have expected I could so easily be transformed into a woman! Well, it wasn't something I had ever even contemplated before. Clearly my torso didn't show the shapely curves of a woman, but there were my tits, sticking out proudly, and remarkably firm. And they were bigger than Kate's. The dress was cut high at the top, so there was no 'cleavage', but in all respect my tits looked very real under the dress. Even the wig seemed to work; it was obvious a high-quality job, and it sat over my short-cropped hair just right. It was remarkable, bizarre; I looked like a woman!

"Mmmm," she cooed, "I think you would turn heads – male heads – walking down the street like this. You look like an attractive young woman. The only thing that gives you away is this," she said, her hand finding its way to my crotch: "Mmm, your cock appears to have become hard and it's showing through the dress. David, that's not very ladylike!"

Then she got up and scurried from the bedroom, yelling back to me: "Wait there!"

I sat there, turning red in the face. It was true, I had to face the fact: this bizarre little dress up game had given me a hard on. I was wearing a little black dress and heels, fake tits and wig, and underneath my cock was hard. I couldn't deny it, this was exciting me in a weird, kinky kind of way. I felt ashamed. She must think I'm gay! And that thought, the shame I felt, only heightened my arousal as I felt a rush of blood surge into my member and more precum leak out of the tip.

"OK," I heard her say from the living room, "you can come out now."

I stood up and walked into the living room. It was hard to walk in the heels, but I didn't stumble. My heels made a click clack sound on the polished wood flooring in the hallway. Kate was standing in the middle of the living room as I entered the room. She was scrutinizing me. She had shed her clothes, and was wearing nothing but the big transparent cock strapped to her waist. She came over to me, her cock sticking out in front of her, as if leading the way. She came up and embraced me, kissing me hard on the lips, grinding her cock into my abdomen, grabbing my ass and squeezing it tightly with her fingers. I kissed her back. She knew how to kiss.

She stepped back. She looked me up and down, rubbing her hand over my dress, around my ass, feeling me up. Then she reached up and grabbed my tits through my dress, squeezing them.

"Mmmmm," she purred, looking me in the eye. She was panting heavily; her chest was heaving. Her eyes had that glazed, lustful look. Clearly, she was wetting herself under that strap on. "Nice tits," she said.

"Now," she then ordered, "down on your knees. Suck my cock, girl!"

I obeyed. I slid to my knees and took her cock in my hands. She thrust her pelvis forward slightly so that the tip of her cock brushed against my lips. I knew what to do. I opened my mouth and let it slide inside.

"Mmmm," she purred, "good."

I began to suck gently on the head, swirling my tongue around it and gently bobbing up and down on the top of the shaft, only taking an inch or so of it inside my mouth. I looked down my body. The fake tits under my dress were occasionally grazing against her legs as I worked up and down on her cock. When my head bobbed down the hair on my wig would get in the way, so that I sometimes had to brush it aside.

"Harder, suck it harder, bitch!" she cried.

I sucked her harder. It didn't feel so unfamiliar this time. On the contrary, the memory of the first time was vivid in my mind. The tapered tip, the veins, the soft extremity but hard core of the shaft – maybe good wasn't how it felt, but it did somehow feel natural. Well, I thought to myself, this actually is a casting of a real cock, so in essence it's a natural thing. But natural for me to be sucking it? Natural for me to be wearing a dress, impersonating a slut – impersonating Kate? – and sucking a dildo?

I didn't have time to mull over these disturbing contradictions when I felt her cock jam against the back of my throat as she thrust it hard into my mouth. I almost gagged, but she pulled back a bit just in time.

"Girl, you need to learn how to deep throat your man," she said.

Part of me wanted to stop this right now. It was humiliating beyond belief, and that part of me was still wondering how in the hell I had got myself into such an unbelievably embarrassing situation. Then I thought about the photos I would take with my cum splattered across her pretty face. That would be my reward for this ordeal. But then another part of me wanted to please her. She wants me to suck her cock, wants me to deep throat her. I wanted to giver her pleasure. I had gone this far; there was nothing to gain by backing out now. I wanted to take her all the way, as far as she wanted to take this. I opened my mouth wide and plunged my mouth down over her cock as hard and as far as I could manage. But it was still only half way inside my mouth.

"Oh," she squealed, "now you're getting it, slut. Now, just hold it there, just so. Relax your mouth, get used to the feeling of it. Good, that's it. Oh, you look so hot with a big cock in your mouth! Such a little slut!" she hissed as she began to rock back and forth, gently pushing more of her cock into my mouth.

"Does it feel good?" she asked. "Hmm?"

I nodded.

"Good. Ohh, I knew you'd get to like this. Oh David, I wish my cock was real! God, you don't know how great it feels to have a man cum in your mouth! To feel through your tongue his cock pumping out the cum, ooh, the power of it; it's such a turn on! Ooohh, yes, you don't know what you're missing!"

As she spoke I found myself becoming more in sync with the rhythm of her hips as she gently fucked my face. She was right; I could take more of it in that I thought, much more. I felt almost pleased with myself as I watch the cock disappear into my mouth, taking all bar the last inch or so. God, I was almost deep throating her!

She was writhing above me now, pinching her nipples as she watched me take her cock in deep. She thrust it in a little harder, pulling it almost all the way out, as I watched in fascination the sexy sway of her hips and the way the cock slid in and out of my mouth so deeply and so easily.

"God, if I were a man I'd cum all over you pretty face!" she whimpered. "You'd like that, wouldn't you? Hmm? Oooohhhh, Goood!"

She was cumming. She was cumming hard. While one hand pinched her nipple, the other went for the back of my head as she went over edge, her legs and hips shaking so violently I could feel the tremors of excitement through her cock. She screamed as her orgasm took flight, her whole body shaking until finally I felt her muscles relax and she released my head, though she kept her cock firmly in my mouth. She just stood there, a gentle cooing noise escaping her lips until she finally regained a semblance of consciousness. She pulled her cock from my mouth and helped me to my feet. She embraced me in a tender kiss. I could feel my own hard cock rubbing against hers. She could feel it too.

"Mmm, two hard cocks!" she giggled as she wiggled her hips against mine. I smiled. She looked into my eyes. She was beaming, radiant. She kissed me again.

"Oh David, thank you! That was... that was unbelievable!"

I stood there with her, still in her embrace, for some seconds until I finally responded: "Well, yes it was pretty unbelievable!"

We both laughed.

But my cock was hard and I was in need of relief. Now it was her turn.

"Kate," I said. "I think you now need a big cock in your mouth."

"OK," she said. "You seemed to like it, so I suppose I should give it a try. Get your camera."

I dashed off and grabbed my video recorder. That would be better for this, I thought – I didn't think I'd be capable of holding the digital still enough while I was cumming.

"You better slip out of that dress," she said as I returned to the room. She stood up and unzipped me, and I let the dress fall to the floor. I reached around to undo my bra, but she stopped me.

"No, leave it on. The wig, too. You look kinda horny like that."

I didn't mind. I sat myself down on the sofa. She came over to me. She was still wearing the strap on. She kneeled down in front of me and took my cock in her hand. She looked into the camera that I was balancing on my shoulder.

"I see you're using a video camera to film me," she said.

"Yeah, you're about to star in my own private porno film."

"Do you think I'd make a good porn star?" she said, addressing the camera, as she began to swirl her tongue around the head of my cock.

"Oh yes, with your talents for sucking cock, you'd make a fine porno star."

"Oh yeah, well I can do other things besides suck cock," she said as her tongue slid down the length of shaft, down to my balls. She sucked them both into her mouth before letting her tongue slide down further, till it touched the top of my asshole.

"Would you like me to show you some of my other talents?"

Go ahead," I said.

She was looking straight at the camera as her tongue slid around the rim of my ass. Then she began to gently lap at my ass, licking my asshole up and down. Ooohh, that felt so good. This had only happened once before in my life, but I had been too disturbed by the idea of a chick licking my ass to really get off on it. This time was different. Ooohh, I was loving it. She began to lick me harder, and I felt her tongue almost invading my hole. Ooohh...

"Of course," she said, "it's better like this." She began to probe my ass with her finger. "Spread your legs wider for me," she said, and I did. I felt her finger break though the pressure of my muscles and slide inside my ass. And once inside, she seemed to have no problem pushing it further in. Again, it felt fantastic! She began to develop a gentle rhythm, sliding her finger in and out as her gaze alternated between looking at her fingers working on my ass and the camera. I felt myself relax under her attention. I realized I was moaning.

"Ever had this done to you before?" she asked.

"Yeah," I grunted, "but not as good."

"Good to hear. What about this?" she said as she shuffled back, so that now her cock was pointing towards my ass. She pushed it forward so that the tip was now pushing against my opening. I was a bit alarmed at this, but I was so turned on!

"Never had a big cock inside you? Ooh, look at that," she said, pointing to the fake cock that was exploring the rim of my ass. "God, I'd only need to give it little shove. Oohh, David, don't you think that would make a good photo? Look at you, sitting there in your bra and pretty blonde hair, legs spread wide and a big cock probing your cute little hole – looks to me as though you're asking for it."

I watched her as she gave a little push and the head of her cock began to push into my asshole. Oooh, it felt good; so wrong, so degrading, but so good! But this was too far for me. I gently pushed her away.

"Well," I said, trying to remain as calm as possible, "maybe looks that way, but that wasn't part of the deal."

"Guess you're right there," she said. "Pity. But a deal is a deal."

With that she returned to my cock. She looked up at me as her mouth slid over the shaft. She kept looking at me, looking at the camera, as she took me all the way in. God, just like that! She was deep throating me straight off – how does she do it?

She clamped down on my cock and sucked hard. God, how good did that feel? Well, it felt good, but then she simply shifted up a gear, pulling her mouth off me and then plunging straight back down, not even pausing as she built up speed and momentum – up and down, all the way, up and down, sucking hard on the upstroke. Ooohhhh...

God, already I was gong to cum. There was no way around it – it was impossible to last more than a minute with this chick sucking your cock.

"Oh Kate, I grunted, "I'm going to cum, I'm going to... arrgghh!"

She knew, and she pulled my cock out of her mouth just in time to catch the first blast across her lips. As I grunted and wailed, she squealed in delight as I sprayed my seed all over her face, across her nose, her chin, in her mouth, in her hair. Trying to keep the camera still stunted the experience a little, but even after I had dumped my load all over her, there she was looking into the camera, licking her cum-covered lips, licking up the cum that was on her chin and taking it into her mouth. God, I was totally spent, but the image of her doing that was almost enough to get me instantly hard again. She had certainly kept up her part of the bargain.