Who Wants To Be A Millionaire?
by Emily Ross

 

So you want to know how all this started? I was sixteen, I guess. Still in High School. I'd been friends with Pete McBay and Tony Cabrini since we were in eighth grade. We were what people call inseparable.

We weren't exactly the most popular guys in school. We were all what you might loosely term nerds. Pete was a photography nerd. He never left home without one of his cameras. He took picture after picture of nothing at all and dreamed of being a highly paid fashion photographer. His nickname was Pap, short for paparazzi.

Tony was your typical computer nerd, spending thousands of hours in front of a screen. His nickname was RedEye because he got red eyes from spending so long staring at his laptop. I bet he was born knowing all about web-sites and stuff.

He only had a second hand machine but he had upgraded it and added new hardware. He'd only spent around three hundred dollars on it but it was better than any computer I'd ever seen. He dreamed of being a highly-paid computer whiz-kid, working for Bill Gates.

Me? My name's Kevin Mitchell. I was the most timid, unselfconfident kid in the school. I could never stand up to anyone and always gave in. I was painfully shy and to hide it all I became a comic nerd. I devoured them. Hundreds. Thousands.

Most kids have grown out of comics by the time they're eleven or twelve. Not me. Did you know you can even go to college and take a degree in comics? That's what I planned to do before starting my own comic and making millions.

Making millions? The three of us often talked about how we'd make our first million. Who'd be a millionaire first? We never doubted that we would.

I don't know why we thought we'd be successful. None of us was an alpha student and none of us what you'd call God's gift to women. RedEye was somewhat skinny, Pap too was a weed and me, I was just small. None of us had ever had a girlfriend. No wonder we were nerds, staying in and messing around with our hobbies.

By now, I'd started drawing my own comic stories and sending them to the publishers hoping they'd be published. They never were.

One day after school we were at RedEye's house chatting away about becoming millionaires when RedEye said quietly, "My sister's had an idea about how to make millions."

Did I tell you that RedEye had a twin sister called Gina? She was in our class too and was the best looking girl in the school. Every guy fancied her. Every girl envied her good looks. It's hard to believe that an under-developed, plain guy like RedEye could have a gorgeous sister like Gina, let alone a twin sister. But sometimes nature works like that.

We all fancied Gina but she was way out of our league. I remember one evening Pap and I were round at RedEye's house while Gina was getting ready to go out with her boyfriend. The three of us; RedEye, Pap and I were in the den talking when Gina popped in to say goodbye.

There was a powerful smell of expensive French perfume. She looked absolutely stunning; her hair was breathtaking and her make-up out of this world. She wore a royal blue dress that hugged every curve of her gorgeous body, sweeping over her hips, ending halfway down her thighs and revealing her fantastic legs. She wore impossibly high heeled sandals that made her look even more glamorous and mature. She was sixteen going on twenty five. I seem to remember her boyfriend arriving in a Jaguar or some other expensive European car.

"So what's Gina's idea?" I asked.

"Well," said RedEye taking a deep breath, "we set up an Internet site. With Pap's photography skills and my computer skills, it will be very professional. We charge people a subscription to look at photos."

"Photos?" I asked.

"Yes photos of models," said Pap, who was obviously in on the idea.

"You mean Gina?" I asked. She was pretty enough to be a model.

"No, that's where you come in," said Pap.

"Me? Why would anyone pay good money to see a photograph of me?" I asked naively. I had a thought. "There has to be a catch. It's not pornographic is it? I won't have to take my clothes off, will I?"

"No, Kevin," said Pap. "There will be no nudity. You will wear clothes all the time. But there is a small catch. The clothes you will be wearing will be girls' clothes."

"Girls' clothes?" I echoed.

"Yes, Kev," said RedEye. "Gina says that there are many Internet sites that charge punters to see pictures of t-girls - boys dressed as pretty girls. Nobody will recognize you, honest. If we charge, say twenty five dollars, we can undercut their prices. Our overheads are very low. If we get forty subscribers that's a thousand dollars. If we get forty thousand subscribers, that's one million dollars. There are billions of people using the Internet. We've only got to get a small percentage of them to subscribe and we've made our first million."

I was speechless.

"Look," said Pap, "I don't expect you to make up your mind right now, but perhaps you can think about it and we'll discuss it later."

RedEye changed the subject and was chatting to Pap about school but I was miles away, thinking about the idea. The good point was the money. As much as a million bucks? The bad point was that I'd have to wear girls' clothes. My family was not well off. I came to the conclusion that the money would be useful when I went to college. I thought that I might as well try it once. Who knows what I'd look like or whether the website would be a success but if I didn't agree, we'd never find out. Like I said, I always gave in.

So later that evening I told Pap and RedEye that I'd do it. Just once to see if it was a success. RedEye said that his parents would be away the following Friday evening. He would try and persuade Gina to stay in and help get me ready. We arranged to meet at seven on Friday for the photographic session.

-

With only a towel wrapped around me, I walked from the bathroom to Gina's bedroom, where she began my transformation into a t-girl model. She removed my towel and gave me some lacy pink panties to wear. I put them on and was surprised how nice they felt against my skin. I was feeling a little aroused. Was it Gina? Or was it the panties? I hoped it didn't show.

Gina didn't seem to notice as she stretched a white bra around my body and did it up. A few Kleenex stuffed in the cups gave it a bit of shape. Then she passed what she called a waist-nipper around my body. She did it up. It was tight and a little uncomfortable. Then she pulled a lacy white petticoat over my head and smoothed it over my body. I loved the feeling of her hands stroking my body through the petticoat.

I was grateful that the petticoat, which came a third of the way down my thighs, was loose enough to hide any embarrassing bulges in my downstairs region. However I now had the difficulty of threading a pair of nude pantyhose up my newly shaven legs.

Next came the dress. When I say the dress, I mean the dress. The royal blue one Gina had worn on that night out. Made from an amazing material which was both stretchy and shiny, anyone would have looked great in that dress. It was tight over my new body-shape, flaring out below the waist and ending two or three inches below the hem of my petticoat.

Now Gina started on my face and nails. She told me that she had been working weekends at a local hairdresser and she used what she had learned to good purpose. First she put a long, blonde wig on me. Then she brushed it while blowing hot air from the hairdryer at me. Next she did my face with foundation, eye-shadow, eye-liner, blusher and lipstick. I wanted to look at myself in the mirror but Gina insisted she did my hands first, gluing on false nails and painting them deep crimson.

A year before I'd been hanging out down the mall with RedEye when he'd suggested we had our ears pierced. I agreed but when we got to the store I was surprised when he had both ears done. So I had to have both mine pierced too. Now I was glad as Gina fitted a big hoop in both my ears.

A few more items of cheap jewelry and I stepped into a pair of shoes that Gina gave me; exactly the same color as the dress, they had the thinnest and highest heels imaginable. They pinched but they looked fantastic.

Gina let me look at myself in the mirror. Was that really me? I looked nearly as good as Gina had on that night out. The stretchy royal blue dress hugged my curves just as it had Gina's. My legs looked just as good as hers had done.

I was nervous but amazingly I felt good. I went right up to the mirror. My hair, long blonde wavy trusses, looked fine. It had taken ages for Gina to get that natural look. My make-up was first-rate; Gina had done a wonderful job. The gold of the thin necklace glistened. Oh yes, I looked good. I looked bloody good.

Gina checked carefully that I had no runs in my hose. "Are you ready, honey?" she asked.

I looked at Gina. She smiled at me. "What should we call you?" she asked me.

"I like the name Natasha," I said smiling back.

"Good luck, Natasha," she said and kissed me on the cheek – bliss.

I smiled again. She could see I was nervous. My two best friends were going to see me in a mini-dress and full make-up. "Don't worry," she said, "you'll be fine. You look absolutely stunning. You look like a million dollars.

"Let's hope we make a million dollars," I whispered.

"Good luck," she said again.

"Thanks." I took a deep breath and hobbled in my high heels down the stairs towards the den and my debut as a photographic model. My heart was pounding and my palms clammy.

As I entered the room, I was aware of RedEye and Pap sitting on my left. RedEye was typing into his laptop. Pap was fiddling with his camera. Sheets were draped against the far wall and bright spotlights pointed at them like in a real photographic studio.

A wolf-whistle hit the air and I think it was Pap who muttered, "Fucking hell," and then there was silence as if a stun gun had stopped them from communicating. Two pairs of disbelieving eyes looked at me as I sashayed to the centre of the room. I heard the door close behind me and knew that Gina had come into the room.

"You like?" I whispered.

"Are you gorgeous or what? Are you fucking gorgeous or what?" mouthed RedEye.

"I see you've met Natasha," said Gina. "Tasha, say hello to Peter and Tony."

I mouthed a "Hi" to them both and did a twizzle so they could see me from all angles.

"You know something," said RedEye. "We are going to make a fucking million. Just you wait…"

"Are we going to get some great shots of you tonight, Tasha," said Pap, who seemed just about to have recovered the ability to speak. He stood up and motioned me to stand at the far end of the room under the spotlights. "Now relax, look at the camera and smile." There was a click and a flash and Pap was preparing the next shot. "Relax and smile."

It wasn't easy. I was wearing a short dress, a too tight waist-nipper and uncomfortable shoes. Click. "That's good. Hold your head up a bit more." Click. "Can you lift your chin a little more?" Click. "Now put your right elbow back and push your chest out more. Yes, that's it." Click. "Smile. Think of that million we're going to make." Click. "Yes, better. Hold it." Click. Click.

"Now hitch your dress up a bit." Without thinking I complied with the instructions. Click. "Yes, that's good. Your legs look great. Can't you hitch it up a little higher?"

"My petticoat will show, Pap," I said worried.

"Don't be silly, Tasha," said Pap, "your petticoat's been showing in the last six pictures. That's what the punters love to see, a bit of lace. Can you show us a bit more?"

There wasn't much of the dress left to hitch up but I tried. "Smile. Relax." How could I relax when I was dressed as a girl, my waist pinching and my underwear was showing?

Click. "Right, just a few more. Hitch that dress up more, honey. Yes you can do it." I gave the dress a final hitch. I was holding the hem next to my butt. I was sure that my panties would be showing as well as the petticoat. "That's great, Tasha, what lovely pink panties. Smile." Click. Click. Click. Click. Click.

The camera clicked and clicked. The memory card was full. 128 Megabytes of pictures had been shot in the last five minutes.

"OK, Tasha, we'll stop there."

"I'll have those photos uploaded onto the web in ten minutes," said RedEye as Pap handed him the camera's memory card.

"That quickly?" asked Gina.

"Sure," said her brother. "I've bought the domain name tgirlzz.com and registered with all the big search engines. All I need is the pictures. Tomorrow I'll set up the secure area and we're start selling subscriptions. I've set up an account for the credit card payments. Some of the shots will be free but most of them will be some subscription only shots. You only can see them if you pay us twenty five bucks. We'll be millionaires. Now let's look at the pics."

RedEye clicked the mouse and one of the photos appeared on the screen. Pap, Gina and I craned our necks to see it. It actually was very good. It looked professional and I looked beautiful. Except my panties were showing. Then we saw another. And another. Every one of them had my panties showing.

"You're not going to put those pictures of me with my panties showing on the web so that anybody can see?" I asked RedEye.

"Of course. How else will we persuade people to part with twenty five bucks? Anyway you look great and nobody will know it's you. We'll need to take some more photos tomorrow though."

"More?" I asked. "But I only said I'd do one session."

"Natasha, honey," said RedEye, talking to me as if I really was some troublesome girl, "we'll need more photos if we are to make a million. Lots more photos. We can take them all tomorrow. You're not telling me, that when you on the verge of a fortune and you look so fucking drop-dead gorgeous, that you're backing out now?"

"Oh, Natasha," said Gina, "you mustn't back out now."

"All right," I said giving in too easily, "I'll do another session tomorrow, but that's it. OK?" Like I said, I always gave in.

"OK. Now do you want to go and change into something more comfortable?" Gina suggested.

I nodded and followed her back up to her bedroom leaving my friends to choose which pictures they wanted to display, crop them and resize them before uploading them.

"Well done," said Gina kissing me again, this time on the lips. I swooned. There were some good things about dressing as a girl! "That wasn't too bad, was it?" Gina asked me.

"Too bad? Don't you think it's humiliating dressing as a girl in front of your mates with all your frilly underwear showing, knowing that tonight those photos exhibiting my panties will be on the Internet for everyone to see. Still as RedEye had said nobody would recognize me in a million years and a million bucks is a million bucks." I kicked off the stilettos and pulled off the blue dress.

"You looked like you were enjoying it," Gina said. "Posing and smiling for the camera."

"I suppose in a way I did. The clothes feel really nice and I actually got a buzz from being dressed as a pretty girl."

"A very pretty girl. You'll have guys chasing after you. Wait till you get your first date, Natasha," Gina laughed.

"Gina, I have no intention of going on what you call a date. Anyway, you know that tomorrow will be the last you see of Natasha."

"That's a shame. You've really enjoyed it and you make such a nice girl."

"I suppose I'll take that as a compliment, Gina. Now how do I get these false nails off?" I asked.

"Oh, Natasha," said Gina. "They take ages to get on and off. As you've got another session tomorrow morning, I think you should keep them on."

I tried to butt in. I had to go home that night. I couldn't go home with long, bright red nails. Nevertheless Gina continued, "I think you should stay dressed as Natasha until tomorrow. The more practice you can get, the better model you will be."

"Until tomorrow? I can't go home like this," I said stating the obvious. "My mom and dad will throw a fit. Particularly if they find out pictures of my panties are plastered all over the Internet."

"You don't need to go home," she continued. "My parents are away all weekend. You can stay here. I'll lend you some more comfortable clothes."

I wanted to argue.

"It would be a really good idea to stay as Natasha tonight as there will be lots more outfits to model tomorrow. Pap will be taking dozens of pictures."

What had I let myself in for? Hours in front of the lens in skimpy clothes and painful shoes with my girly underwear on display, not daring to touch my face for fear or ruining my hair or my make-up, I guessed.

"Phone your mom and say you're at a sleepover. You can sleep in mom and dad's bed or you can sleep in that bed if you like."

She pointed at a second bed in her room. I could sleep in Gina's room? I could see her undressed? Did I need a second invitation? Like I said, I always gave in. I took off the petticoat and put on the clothes that Gina had got out for me; a pink top, a denim skirt (a few inches above the knees - no chance of my panties being on show) and shoes with a small heel and phoned my mom with my cell phone.

"You are pretty," said Gina when I put the phone away. She stroked my hair. When I say my hair, I mean the wig of course. "Let's see how the boys are getting on."

We went back downstairs.

"I've uploaded the pictures," RedEye said. He didn't seem surprised to see that I was still en femme. "Pap's been out and got some pizza. Are you hungry, girls?"

'Girls?' I thought.

"Not too much for Natasha," said Gina. "She's daren't put on weight."

I smiled. I didn't feel hungry anyway what with the nervous tension of the evening and the tightness of the waist-nipper. RedEye complimented me on my new outfit and we went into the kitchen and ate the pizza. I had only a tiny slice while RedEye and Pap ate nearly all of it between them.

RedEye showed us the web-site on his laptop and I must say it looked very professional. I tried to blank out the idea that the 'girl' in the pictures was actually me. "We've had over a thousand hits already," boasted Pap. "We'll be millionaires by Christmas."

After we'd cleared away Pap said he had to go home. He'd need to buy some extra memory cards and he'd be back around ten in the morning. Gina said that I would be ready for the next modeling session at ten sharp. The two siblings spent the evening chatting and dreaming of what they'd spend the money on. We agreed that we'd divide the money four ways. Gina should get a quarter of the income – after all it had been her idea and they were her clothes. It was good fun to be in Gina's company. She was gorgeous even if she was out of my range. I completely forgot that I was wearing a skirt after a while.

Around eleven thirty we went up to bed. Gina stripped naked in front of me with no embarrassment at all. She had a gorgeous body and I thought she enjoyed flaunting it. She put on a baby-doll nightie and gave me a similar one to wear. Off came the wig and she helped me remove my make-up.

She climbed into her bed and I was just about to get into mine when she said, "Natasha, that spare bed is hard and lumpy. I don't suppose you want to get into my bed with me, do you?"

Does an elephant have a trunk? I happily climbed into her bed and we cuddled exploring each other's bodies a little. "Won't your boyfriend mind you going to bed with another boy?" I asked her innocently as she stroked my back.

"Another boy?" she replied. "Natasha, you ain't a boy, you're a girl."

OK so the clothes, wig and make-up were gone, but I was wearing red false nails and a baby-doll nightie. Maybe she was right. Pretty soon, cramped in the small bed, we were both fast asleep.

I woke up and vaguely remembered where I was. Gina was already up and had left a note beside he bed saying, 'Natasha. I've put some clothes out for you on your bed.' I looked at the clock. It said 8.15.

I got out of bed, showered and dressed myself in the clothes; a padded bra, panties, jeans, T-shirt and strappy shoes with a two inch heel. I put on the wig and not bothering with make-up, went downstairs to the kitchen. Gina was there, looking immaculate in a silk robe over her baby-doll nightie, not a hair out of place. She was drinking freshly squeezed orange juice.

"Hi, Tasha," she said standing up and kissing me on the lips. I hadn't been dreaming then. "You look magnificent. Want some OJ?"

I nodded and Gina poured me a glass. "Oh, Tasha, are you going to like the outfits you'll be wearing for today's photo shoot? When you've finished your juice I'll do your face and hair ready for when Pap comes. I sipped the juice slowly, in no hurry for the completion of my next feminization.

"Hey, come and look at this," said Gina when I'd finished. "Look at all the clothes I've got out for you." We went into the den where every chair was covered in clothes. Gina was positively gushing as she described each outfit. "This is the dress I wore to the prom last year. I went with Brett Holden. Do you know him?"

I shook my head.

"The bastard was two timing me with some slut from the other side of town. I soon finished with him but the dress is gorgeous, isn't it?"

She was right. It was striking and I half looked forward to wearing it. As it was calf length, I didn't think I'd have the problems with exposing my underwear that I'd had the previous evening. Oh, I was so naïve.

"This is the cheerleader uniform I wore last year. Don't you just adore it? Brett was the star running back for the school football team and I swore he played better when I was wearing this uniform. You'll love wearing it." I noticed how short it was and knew it would be difficult to stay decent in it.

"Isn't this dress pretty? It's a little girl party dress. I used to have one of these when I was eight. I loved going to birthday parties in it. Can you imagine blowing out the candles on your cake wearing this dress?" I didn't have to imagine it. I knew I'd be doing it later.

"This is a French maid's outfit," she said, pointing out a black dress with a white lace trim. "It has an apron, a cap and black fishnets to go with it." That's a bit weird I thought. Why would Gina have a French maid's uniform? Yes I was naïve.

"This is an English schoolgirl's uniform," Gina went on. She picked up a black pleated skirt and showed it to me along with a blouse and a striped tie. "You'll look great in this with your hair tied in bunches." She smiled at me, almost as if she was jealous.

Only when I saw the school uniform did I realize that these weren't just Gina's clothes. They'd been bought or hired especially for me to wear.

I didn't know whether to be appalled or excited by the clothes I would be wearing. Next came a small, black, leather jacket with a matching leather mini-skirt. In fact micro would have been a better word for the skirt. It looked sexy and fun.

-

Pap turned up at five to ten. RedEye was already in the den working on his laptop when Gina and I went in. I was already dressed up in Gina's prom dress, which amazingly fitted me like a glove. Gina had spent nearly an hour on my make-up and hair and I must say I looked good, possibly even better than the night before. I wobbled in on shoes that had a spike heel that must have been at least five inches high.

"Hi, Tasha," said RedEye hardly looking up from his computer.

"Hi, RedEye."

"Guess what. We've already had forty seven people subscribe to our site and another two hundred and fifty six have emailed me expressing an interest."

"Wow," I said trying to do a mental calculation of forty seven times twenty five dollars.

"That's over a thousand dollars," said Gina.

Little did I know that that this would barely cover the cost of registering the site, the hire of the clothes and the purchase of the memory cards. Still two hundred and fifty six times twenty five would be six thousand four hundred dollars. My cut from that would be one thousand six hundred dollars. Not bad for a night's work, even if my panties were showing.

"Why are there so many outfits here for me to wear?" I asked naively.

"Well," said RedEye, "if you want to keep getting subscribers, you have to keep adding more to the site. Each month we'll add a new collection of shots. We've got six outfits here - the prom dress, the cheerleader uniform, the little girl's party dress, the French maid's outfit, the school uniform and the leather mini. That'll cover the first six months. We should get them done this morning. Then this afternoon we'll do the next six months."

"What will that be?" I asked wondering what other outfits might have been ordered for me.

"You'll have to wait and see."

There followed a hectic three hours of photography and changing clothes. My face hurt at the end from all the smiling. Every time I changed outfits Gina had to check my make-up and redo my hair. No wonder it took so long. And yes, with every outfit I had to hitch up the hem so that most of my thighs were visible, then hitch it up a bit more until my panties were fully in the view of the lens.

Yes, I even had to hitch up the little girl's party dress. In white knee high socks, black shoes that Redeye called Mary Janes, the cornflower blue dress and a white pinafore, I looked about eight year old. But Pap still told me to hitch up the dress to show the lacy white panties I had put on especially.

I didn't need to hitch up the cheerleader's skirt. It was so short that the hem was forever flipping up and revealing my panties. Pap made me hold a pom-pom in each hand and wave my arms above my head. Well, of course, this made the whole outfit rise up. Next he made me jump in the air. As I came down the skirt flipped up and the flash went off. Again and again and again.

By the end of the morning I'd got used to my panties being on display and no longer found it degrading for my friends to see my underwear. By now I had my first experience of garters and stockings – fishnets for the maid and black sheer stockings for the last two outfits. So I had to make sure that as the camera flashed my garter straps were visible.

Whoever invented garters? Uncomfortable and impractical, we sat in the kitchen eating lunch - this time RedEye got the pizza – with me worried that my garters were showing, forever tugging at the hem of the leather mini-skirt.

"OK, so what are we doing this afternoon?" I asked.

"Well," said RedEye, "Things are going very well. We now have eighty three subscribers and we've got enough material for the first six months and very good it is too. I've uploaded the pictures of the blue party dress. They are this month's specials. Next month I'll upload the French maid shots. But now the punters will want something more. We need another girl."

I felt relieved. This meant I wouldn't have to mould my face into a permanent sickly smile all afternoon. "So you won't need me then," I announced. Maybe I could change back into being Kevin and go home early.

"No," explained Pap, "by another girl RedEye meant an additional girl; you and another girl - two t-girls."

"Another girl?" I asked. "Who?" I wondered who else my friends had persuaded to be photographed in a dress.

"That's where I come in," said RedEye.

"You?"

"Yeah. Since Gina made such a good job of prettying you up, RedEye and I decided on setting her a harder challenge," said Pap.

"Are you ready, brother?" asked Gina. "Or should I say, sister?"

Gina and RedEye stood up and left the room. Pap told me to put the school uniform back on again. Forty minutes later Gina came back. "OK," she said, "let me introduce my twin sister, Antonia."

RedEye came into the room, wearing a similar school uniform to mine; black pleated mini-skirt, white blouse and striped tie. He too wore black stockings, garters and high heels. His face was lightly made-up and he wore a shoulder length brunette wig tied in two bunches and held in place with red ribbons.

He looked feminine and quite pretty – but not nearly as pretty as me!

Pap told us where to stand and then started taking the photos. He made us hold hands and then put our arms around each other's shoulders. Then he made us both hitch up our little skirts and show our panties. Finally he made us kiss each other on the lips and hold it while he took a dozen more snaps.

I should have hated kissing another boy on the lips, particularly my old friend RedEye or should I say Antonia. But somehow it just felt natural. Weird or what?

Next Pap made Antonia and me change into something called a basque. I'd never even heard the word before but now I had taken off the school uniform and the garter belt and was hooking the basque around my body. I hooked the straps to my stockings and Gina gave me a pair of matching panties.

Antonia was identically dressed and his sister was checking his make-up and hair. Then she did mine and I stepped back into my heels. "What dress do we wear with this?" I asked innocently.

"You don't wear a dress," said Pap, "I want to take a photo of the basque."

"But if take the photos of us like this, the bulges at the front of our panties will show," I pleaded. God, I was naïve.

Pap and Gina smiled. "That's the idea, Tasha honey," said Pap.

Pap snapped and snapped. Again he got us to hold hands and then to kiss while he took the pics.

This continued all afternoon. Antonia and I were French maids, prom queens, little girls and finally fairies for the camera. Finally we were done about six. I could go back to being Kevin at last and go home.

RedEye, still in a fairy costume, was sorting out the images on his laptop. Pap was putting away some of the equipment.

Gina turned to me and said, "Natasha honey, I've got one last favor to ask of you."

"Go on," I said.

"Well, Tony, Pap and I would really like to take some more snaps of you tomorrow."

"Some more? Hasn't Pap got enough? He's taken sufficient for the next twelve months."

"No, Tasha, you don't understand. Tony wants to extend the site to include another subscription area with better quality pictures and a higher subscription; maybe a hundred dollars."

"And who would be in those pictures?"

"Why you, of course."

"With Antonia?"

"Oh no. You're so much prettier than her."

"And you want me to…"

"Stay here again tonight, Tasha – in my bed again. Then tomorrow morning take the final round of pictures."

"These pictures. They won't be smutty?"

"Tasha, how can you suggest such a thing? All these pictures are artistic. In fact I can promise that your panties won't show in any of them."

God, I was naïve. Lured by the thought of an evening and a night with Gina, I accepted. Like I said, I always gave in. I phoned my mum and told her I'd be home the following afternoon. She didn't seem to mind. But then she didn't know that I was dressed as a fairy.

-

Dinner that night was – you've guessed it, pizza. Pap had phoned a restaurant and had it delivered. I'd changed into something more casual – a pink T-shirt, blue mini-skirt, nude pantyhose and three-inch heels. Well I was getting used to them.

When Pap called us to say that the food had arrived I was surprised to see that RedEye was still dressed as Antonia. He had changed into a mauve cardigan and a knee length, black and white plaid skirt over black hose and sensible black shoes. He wore subtle make-up and the same brunette wig. He looked much better as Antonia than as the computer nerd RedEye. I suppose they'd say the same about me.

Antonia (RedEye) told us that we now had one hundred and three subscribers and over seven hundred people had emailed for details. After dinner Pap said he had to go home, RedEye (Antonia) said that he had upload a lot of images and do a lot more work on the site. That left Gina and me – alone. There were a lot of advantages to this website idea.

One hundred and three times twenty five? That's over two and a half grand. Split four ways that's over six hundred I calculated. Gina and I cleared away the dinner and then she went to he fridge and took out a bottle of vodka and a large bottle of Coke. She poured two glasses each; half vodka, half Coke.

"Are you trying to a get a girl drunk?" I joked as she proposed a toast to the new website. "May we be millionaires by Christmas."

"Cheers." We both gulped the drinks. With her social lifestyle Gina may have been used to alcohol. I wasn't. That vodka was one of many firsts that night. We sat in the den. Every time I emptied my glass, Gina filled it up. I wasn't counting.

"What shall we do this evening?" Gina asked. "Shall we go out? To a club?"

I couldn't go out dressed as Natasha. I could feel I was a little the worse for drink already. "Can't we just stay in and get to know each other a little better?"

"Get to know each other?" Gina laughed. "We've been in the same class at school for years!" She came and sat next to me on the settee. "But, Natasha, I don't mind getting to know you better." She put her beautiful hand on my knee and started to move it up my thigh. She was looking into my eyes and rolling her tongue around her lips as if to say, "I want to fuck you. Bad." I was in deep, way too deep.

She put her hand under the hem of my skirt and continued its movement until she was feeling my cock through the thin material of my hose and my panties. I was rock hard and as her hand touched my cock for the first time she whispered, "Oh, Natasha, you are so sexy."

We fell into a French kiss and I reciprocated, feeling her legs and up her skirt. Technically this was not a first. It was my second ever French kiss. My first had been that afternoon. Dressed as French maids, Pap had instructed Antonia and me to kiss like this while he videoed it for the website. "The punters will love it," he said.

But it was the first time I'd ever French kissed a real girl. This was all new to me but I didn't have to think what to do. The kiss was beautiful and erotic; the excitement only increased by the fact that we were in the den and my friend Redeye might come in any minute and find me, dressed in a skirt, about to fuck his sister.

"Come on, let's go upstairs," whispered Gina. As quietly as we could in our heels we went to Gina's bedroom. We kicked off our shoes, peeled off each other's pantyhose and panties and climbed on to the bed. Gina found a condom in a drawer of the bedside table and put it on me. The wait only intensified the excitement.

It was over in minutes, possibly only seconds. We were breathless. I was in love. No matter how many times and how often I have sex, that first time with Gina will always be the best.

We lay there for some time, getting our breath back and cuddling. I could feel a reawakening in my balls and I was wondering if I could manage it again. I looked at Gina. She was magnificent and I'd fucked her.

"Honey," I said to her. "What about your boyfriend? What if he finds out?"

"Don't you worry your pretty little head," she replied. "I dumped him last week."

"And do you really like me?"

"Do I really like you, Natasha or do I really like you, Kevin?"

"Whatever."

"Well even you must admit that Kevin is a bit of a nerd. On the other hand Natasha is sophisticated, pretty and sexy. Very sexy." She smiled at me. "I wouldn't be seen dead with Kevin on my arm but Natasha is something different…"

"Do you mean that you'll go out with Natasha but not with Kevin?"

"More or less."

"And if I want to be your boyfriend, I'll have to dress as a girl?"

"Yes. You do like it, don't you? You loved trying on all those clothes earlier. You should have seen the look on your face when you put on that prom dress, turning round in the front of the mirror and admiring yourself. You've got to admit it, Kevin, you like being Natasha."

I said nothing.

"And when you tried on that party dress, with the knee high socks and the Mary Janes and I tied your hair in plaits, you loved it."

I still stayed silent.

"Even this evening, you didn't have to wear such a short mini-skirt or such high heels. You didn't have to wear a skirt at all; you could have worn my jeans."

"OK, Gina, I admit it. I was apprehensive at first, but yes I have enjoyed dressing as a girl. It's not a crime. I loved wearing that blue mini-skirt and high heels this evening and the way you couldn't keep your eyes off my legs." Gina smiled. "I'd love to go out with you, Gina, and if I have to wear a bra, panties, hose, jewelry, a dress, stilettos, make-up and a wig to make you my girlfriend, you know that I will. But how practical is it? What would my parents say? Or yours? I can hardly change into a dress at home without anyone knowing."

"Don't be silly," Gina replied. "I just mean that whenever you come here, you can slip into something of mine like that skirt you're wearing. You don't know how sexy you look dressed as Natasha."

She suddenly started to French kiss me again. I was getting aroused again. Would I be able to do it twice in one evening?

"OK," I said when the kiss ended. "I'm willing to try it, if you are." I always gave in.

"Good girl," Gina said.

It was obvious that she didn't want me as her boyfriend but as her girlfriend. Maybe I was just a stop gap, a fill-in while she found some other rich guy with a Jaguar. Still there's something about beggars and choosers.

"I'm thirsty," said Gina. "Let's go down to the kitchen and fix ourselves a drink."

"Sure."

I picked up my panties from the floor and put them on. Then I slid my pantyhose up my legs. I loved the feeling of the nylon against my skin. Did you notice how I said my panties and my pantyhose? Imagine. A teenage boy with his own panties and pantyhose.

I stepped into the heels and did up the ankle strap. I was quickly getting used to them. I smoothed down my skirt and checked myself in Gina's mirror. My hair was a complete mess and my lipstick all smudged. Other than that my make-up was remarkably OK.

"Leave the make-up but brush your hair," said Gina as she stepped into her shoes. I realized that her panties and pantyhose were still lying on the floor. I hoped this was a sign that there was a lot of fun ahead.

Gina's didn't bother to do her make-up either. Mind you, the only person she might see was her brother. I tottered after Gina, following her down the stairs and into the kitchen. RedEye was in there, sitting at the kitchen table typing into his laptop. Amazingly he was still wearing girls' clothes. Over four hours after the photographic session had finished, he was still wearing a skirt.

In fact, I realized he was wearing a different skirt than before. I remembered that earlier he'd worn a mauve cardigan a knee length, black and white plaid skirt, black hose and sensible black shoes. Now he wore a very short white mini-skirt (it had to be short – it was shorter than mine), a pale pink blouse through which I could see the outline of a black bra, nude pantyhose and skyscraper heels (higher than mine). It even looked like he'd redone his make-up.

"Hi, Antonia," said his sister as if it was the most natural thing in the world. "How are we getting on?"

"Hi. A hundred and twenty one subscriptions, so far. There's over three thousand bucks in the account. And that's only started. Wait till tomorrow. With the second subscription site, we'll be made of money!"

Gina poured three glasses of Coke. We drank it slowly, chatting about the day, RedEye's predictions of how much money we'd make (millions of course) and what tidying up we'd have to do before Mr and Mrs Cabrini got home.

Eventually Gina and I headed back upstairs to bed. When we were safely in the safety of Gina's room, both dressed in our baby-doll nighties, I asked Gina, "Does RedEye normally wear girls' clothes around the house?"

"Oh sure," Gina replied casually. "He's done it for years. I offer him all my old clothes before I throw them away. You might just remember me wearing that white mini-skirt a couple of years ago. It's too short for me now but Antonia doesn't seem to mind. That pink blouse was mine too, but it's so last year…"

I nodded as if I was aware of teenage fashions. So RedEye was a transvestite, eh? That explained the double ear piercing. Mind you, what about me? I was wearing a wig, make-up, a pink T-shirt, a mini-skirt, nude pantyhose and three-inch heels.

"It was dad that got my brother started when he was about twelve or thirteen. Well, you must admit he's a skinny, awkward, unattractive geek of a boy, but put him in a dress and he's quite pretty. Not as pretty as you, though, honey." She stopped and smiled. "So he dresses quite a lot of the time when he's at home. I'm surprised he hasn't told you. Dad's a tranny too, by the way, so I don't think there'll be any problem in you wearing skirts when you come round here."

Well I suppose that was good news. It would certainly make it easier for Natasha to have a relationship with Gina. We undressed, cleaned up our faces and went to bed, making love again first and sleeping very soundly.

The following morning after breakfast, Gina told me I'd be wearing the royal blue dress that I'd worn first on the Friday. "But I've already had lots of photos taken in that dress, why do you want some more?"

"You'll see," she replied enigmatically. She told me that I'd be wearing white stockings and a white garter belt. I was worried about stockings with that short dress but I was thankful this was the last session of the photography.

At ten minutes to ten I went into the den, appreciating the luxuriant feel of the material of the dress, conscious of the tug of the garters as I walked. My hair was as good as ever and my make-up expertly done again by Gina. I was wearing the highest heels imaginable.

Pap was fiddling with his camera on the tripod, getting everything just right.

RedEye was sitting on the floor, laptop on his knees doing more work on the website. It didn't surprise me that he was still dressed as Antonia. He wore another outfit that I hadn't seen before; a sexy mid-thigh length denim mini-dress, a cream cardigan, two inch heels, pantyhose and red lacy panties.

How do I know about the panties? Well he was sitting on the floor with his knees raised and the mid-thigh length dress had got hitched up a bit and … well you've guessed it. He may have been dressing as a girl for some time but he hadn't learned everything about being a girl.

Or maybe he had. Maybe he was deliberately showing his panties…

"One hundred and forty nine subscriptions," RedEye announced. Things were going well, he told us. We were well on our way to our first million and with the second site going live later, we'd have even more money rolling in.

"Ready, Natasha?" asked Pap.

"Yes," I nodded. One last round of fixed smiles for the camera.

"OK, take your panties off," he said.

"You what?" I asked.

"Take your panties off," repeated Pap calmly.

I couldn't believe what I was hearing.

"Didn't Gina tell you?" asked Pap, shifting the blame on to someone else. "This morning we'll be doing some up-skirt, no-panties shots for the second website. They're going to love these pictures."

"You mean you want to take pictures of my cock."

Suddenly the other three were silent.

"You want me to take my panties off and hitch up my dress so that you can take pictures of my cock? No wonder Gina promised me that my panties wouldn't be showing. I won't be wearing any fucking panties. You told me I wouldn't have to take my clothes off, Pap!"

"Calm down, Natasha," Pap begged. "You won't have to take your clothes off. You'll still have the dress on."

"Oh yes, hitched up around my waist," I replied. "You said there wouldn't be anything smutty, Gina. What can be smuttier than a girl hitching up her fucking dress and showing her cock?"

"Natasha honey," Gina implored. "These pictures won't be smutty. They're art."

"Art? Art?" I questioned. "They're not art, they're porn. You said there would be nothing pornographic, Pap!"

"Look, Natasha," said RedEye quietly. "There's a big market out there for this sort of stuff. All we're doing is giving subscribers what they want. You wouldn't want to act as some sort of censor denying people the right to see what they want to see."

"RedEye. Antonia, rather, I've put on girls' clothes, I've put on make-up, I've had photos taken with my panties showing, I've even kissed another boy but if you want photos of someone's cock, it'll have to be your cock."

"But, Tasha," pleaded Pap, "You much prettier than Antonia. We need these pictures to make a million."

I wasn't giving in any more. "Well you should have told me what you wanted before we started. I don't care if we make a million any more. You've humiliated me. I'm going to get changed and go home. As Kevin." As I said this I minced out of the room in my girliest walk and slammed the door as I left.

"I told you she wouldn't like it," I could here Gina say as I stormed up the stairs. 'She?'

It was right what I'd said. I no longer cared about the money. I wasn't even sure if I wanted to go out with Gina. I wondered if her friendship was just an act to get me to do what they all wanted. I took off the wig, the stilettos, the dress, the garter belt, the make-up. Where were my boy things? And how do I get these bloody nails off? Fuck. Fuck, fuck, fuck.

I went crawling back downstairs. In my bra and panties I went back to the den. Of all the humiliating things I'd done that weekend this was the most humiliating. "Gina honey," I said, "Where are my clothes? And please can you help me get these fucking nails off?"

I could feel the tears running down my face. I realized that I'd made a bad job of removing my mascara when a tear dropped off my chin and made a big gray blob on the front of my bra.

"Sure, honey," said Gina getting up. "Come with me."

She led me back upstairs. I was still in tears and she started crying too. She sat next to me on the bed, put her arm round my shoulders and consoled me. "I'm sorry, Tasha. It was my idea to do the stupid website in the first place. Pap suggested the 'no panties' shoot. Apparently he's seen them with real girls. I told him you wouldn't like it. But he told me that was where the money is."

She was stroking my back, then she stroked my stomach and then she stroked my legs. I could feel a boner coming on and within a few seconds my cock was sticking right out of my panties.

"It's a shame though, honey," Gina went on. "You've got a gorgeous cock and it would look really good in those photos. They only want ten or twelve. It won't take two minutes. Look, I promise that if you let them take ten photos, I'll find your boy clothes, help you get those nails off and then I'll go over to your house with you and you can show your first girlfriend off to your parents. Wouldn't they like it when they find out that their nerd of a son has a good-looking girlfriend?"

"Two minutes, eh? Only ten shots?"

"That's what they said."

I could feel myself wavering. I liked the idea of Gina coming round to my house to meet my parents. It made our relationship more established. And the extra money from the second website would be useful. I gave in. Again.

But I was going to do it on my terms.

Three quarters of an hour later. I was ready. I was wearing the dress again, the cling wrap tight, short, stretchy, shiny, sexy dress. I was wearing the skyscraper heels again, I was wearing the garter belt and stockings again. My make-up was once again immaculate, the blonde wig looked stunning and just to see myself in the mirror turned me on.

Even if I never met Gina again, even if I never had another photo taken of me, I knew this would not be my last time in girls' clothes. I started to walk slowly downstairs. I could feel the sway of the dress, the pull of the garters and the restriction of the bra. And under the dress I could feel that I was not wearing any panties but I had the biggest, hardest erection ever.

I walked into the den proudly, assertively, confidently, almost arrogantly, head held up high as if to say disdainfully, 'Look at me. I'm beautiful. I'm not doing this because you want me to, you motherfuckers, I'm doing it because I want to, because I'm good.' I strutted up and down the room once wiggling my ass provocatively as I walked as if to say, 'Look at me, I'm a beautiful, feminine girl.' Two pairs of eyes followed me. They knew I was beautiful but now I was more beautiful than ever. And then, when both Pap and RedEye were looking at me open mouthed, I lifted the hem of my dress.

Pap gasped when he saw my cock. "Wow!" Drool seemed to slide out of RedEye's mouth. Awe, envy, surprise, astonishment, wonder, respect, admiration, fear. I saw it all in their eyes. I was in control. I was in charge. They would do what I said. No longer would anybody push me around.

"Fuck you, aren't you ready yet?" I said in a mock Southern drawl. Pap hurriedly stood up and got behind the camera. He told me where to stand. "No, I'll stand where I want to stand," I said. I hitched up the dress again. Click. I smiled more. Click. Click. I turned slightly. Click. Click. Click.

I sat on the floor. Click. Click. Click. I sat on a chair. Click. Click. Click. Was that twelve? Who cares? I'm enjoying this. They're in my power. I wanted more. Pap took more. Up my dress, down my cleavage. Cock shots, ass shots, tit shots. With Antonia, without Antonia. I called the shots. I told Antonia to take off her pantyhose and red lacy panties. I kissed Antonia. I cuddled Antonia. I hitched up her dress and she hitched up mine. Twenty, thirty, forty, fifty, a hundred. Who knows? I didn't care. I was in charge.

-

It was over. I was Kevin again. I was in my jeans, T-shirt and sneakers. The false nails had come off, but not very easily. It was time to go home with Gina. She had changed too. She was wearing a white mini-skirt. I was sure it was the one Antonia had worn yesterday. The one Gina had said was too short but I didn't say anything.

Gina had packed a plastic carrier bag for me. In it she'd put a bra, a pair of panties, a pair of pantyhose, the wig, the pink T-shirt, the blue mini-skirt and the three-inch heels I'd worn the evening before.

"I guess you might like these," she said as she handed it to me.

I thanked her and said goodbye to Pap and RedEye. Pap was still playing with his camera. RedEye was still working on his laptop, still dressed in the mid-thigh length denim mini-dress, the cream cardigan, the pantyhose and the two inch heels. I guess that underneath he was wearing the red lacy panties too. I felt strangely envious of him in his dress, me in my boring boy clothes.

"A hundred and sixty subscriptions," he called as Gina and I left. We walked the ten minute walk back to my house. My parents seemed pleased to see me after a weekend away. My dad seemed particularly pleased to see Gina. His tongue was practically hanging out when he first saw her, in her cute mini-skirt.

Of course, it couldn't last. She was way out of my league. A few weeks later she found a guy with a smart car and more money than sense. We never made a million. We got nearly two hundred subscribers. Still my share was over a thousand dollars.

Four good things did come out of that weekend.

Firstly I suddenly became confident and assertive. Friends remarked about the change. I guess I found something I was good at. So it was dressing as a girl, but it gave me confidence for other things too. And I'd learned to say no.

Secondly I discovered an interest in wearing girls' clothes. I found out that it's fun to get all dolled up and put on a sexy dress. I grew my hair long and started going round to RedEye's house. He would dress as Antonia and I would dress as Natasha. After a few months we were brave enough to go out dressed. We even got Pap into dresses a few times and he looked quite cute.

Thirdly I lost interest in those stupid comics. I think my parents were surprised when I told them I wanted to go to college and study fashion, but they had to think it was better than spending three years studying Spiderman and Superman! I'm in the final year of my course now and I hope to get a job with a fashion designer.

Fourthly I've made some money. Not the proceeds from the website you'll understand. That was hardly enough to keep me in dresses and cosmetics for a year. No, Gina showed some of Pap's photos to a guy she knew from a photographic agency. He passed them on to someone from another agency that specializes in girls like Natasha. They phoned me and asked if I would go on their books.

Of course I agreed. Now every month or so, I get a call from the agency. I take a day off college and head for the studio. I get prettied up and they take a few snaps. You may have seen them in magazines. I get well paid; more than enough to pay my way through college and satisfy my enormous appetite for clothes!

And that's how all this started.

 

 

 

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© 2002 by Emily Ross. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.