I stopped suddenly and looked at her with a dark glare. “I’m never doing this again. You’re lucky you’re even getting me this one time. If you think you can just blackmail me over and over and over, you’re mistaken.”
She grinned. “So what are you going to do to stop me?”
And she made a good point: what was I going to do to stop her? If she asked me to do it again, I would probably do it, as long as she kept threatening to tell everyone in the school. How could I ever break free from her stranglehold?
Suddenly, she started laughing. “Look—I told you I wouldn’t tell anyone if you do this one shoot, and I meant it. But I think you’re going to like my pictures so much that you’ll be begging me to shoot you again after this. And when that happens, you’ll be on the hook for your own makeup. That’s all I’m saying. Now let’s get this show on the road.”
Quinn got me undressed, down to my boxers. Then she sat me down and started putting makeup on my face. My eyes were closed for the most part, but she talked me through everything she was doing, as if she was hoping that I was taking notes. But I was just trying to count down the seconds until this whole embarrassing ordeal was over and done with. I asked the same question a few times: “Are you sure I’m not looking recognizable?”
“As long as you don’t leave any mascara on your face this time,” she replied with a laugh. She got the job done much quicker than I did the night before. It only took her twenty-five minutes, versus my three-hour attempt. And her makeup job was much cleaner. It helped that she had years of practise on her own face.
I leaned in close to the mirror to admire some of her finer techniques. I really liked the way the orange eye shadow blended into my face around my eyes, and I loved the way the eyeliner blended into the orange eye shadow, giving me a sexy smoky look.
“Are you going to stare at yourself all day or are we going to shoot? Go get that wig that you wore for your other shoot.”
I found the wig, right where I left it. I got it snug on my head and I rustled up the hairs to make it look a bit more natural. Then, while Quinn was off setting up lights in one of the mansion’s many bedrooms, I stared at myself in the mirror. I couldn’t get over how girly I looked. It was an eerie sight, and I wondered: could all men look like this with a bit of makeup and a wig? Or was I some sort of special case?
I didn’t necessarily mind the fact that I looked like a girl, but I did mind the fact that I kind of liked it—especially after watching all of my classmates ogling my pictures, as if I was a famous super model. And then when my instructor compared me to a young Kate Moss—that was a powerful moment. When I was a boy, no one ever compared me to a young anybody. But to be compared to one of the most famous models of all time… Surely that meant something. Surely that wasn’t something any guy could do with a wig and a bit of makeup.
“Are you coming or what?” Quinn called out.
It took me a minute to find her. She’d set up in one of the guest bedrooms. She had the sheers closed and just a couple of flashes set up—she didn’t need anymore than that because the room got so much natural light. She already had her camera around her neck, ready to shoot. “I’m thinking we’ll start by the window,” she said. “Maybe we’ll start in a sitting pose.”
“I don’t think this is a great idea,” I said, standing still in the doorway.
“What? Why not?”
“I don’t really want my picture in a magazine—not like this. I mean—what if my family members see the pictures?”
“Darling—you let the instructor show your pictures to the entire class, and now you’re worried about a magazine you’ve probably never even heard of? Why don’t you just admit that you like the attention and get in front of my camera so we can shoot?”
I bit down on my tongue. That was the problem: I did sort of like the attention. I liked all the compliments—I wasn’t used to getting so many compliments. In fact, I wasn’t used to getting any compliments, except the ones I got from my grandmother whenever I fixed her Internet connection.
“Just sit down already so we can get the show on the road. I still have to edit these pictures, you know,” she said.
So I sat down where she wanted me to sit and then I posed the way she wanted me to pose. “You need to relax,” she said. “You look so tense and awkward. I can’t use any of these shots.”
I closed my eyes and I tried to breathe. I didn’t want the photos to be bad—that was the last thing that I wanted. It would have been a terribly waste of my ego to put on that little outfit and all that makeup, just to look like an idiot. If I was going to get dolled up like a lunatic, then I might as well look good doing it.
“Just think about how hot you are,” Quinn said, taking me off-guard. I looked at her curiously for a moment. She was looking at me with a grin. Behind her was a mirror. And she was kind of right: I was hot. My long legs looked sexy and smooth, and my eyes were particularly stunning. I looked into the lens and then she snapped a photo. “Perfect!” she said, even though I hadn’t done anything other than look into the lens.
“What do you mean?” I asked.
She turned her screen towards me so I could see her shot—and she was right: the photo was perfect. My expression was classic: sexy and confident and happy without smiling. It was the perfect model look, the same look I had in my pool photos.
Quinn snapped a few more shots. I remembered my time in front of the camera from the night before, changing my pose every time I heard a few shutter snaps. So I did the same thing now in front of her camera. After a few minutes, she didn’t even need to direct me. The poses were coming naturally, and I felt good. I was in my element.
“You really are a natural,” she said. “And believe me, because I’ve shot over a hundred models before.” I had to strain to keep the smile away.
We were on the bed now. She was standing above me, shooting down. I found myself biting my bottom lip, feeling overwhelmingly sexy. I rubbed my hands gently and slowly up and down my body. She was snapping photos quickly now, as if she didn’t want to miss a single moment. “These are all so great.”
Next I was on my knees on that bed, and Quinn was on her knees next to the bed, getting some low angle shots as I ran my fingers through my hair. I still had that lingering embarrassment in the back of my head, but the strange sense of confidence in my bones was much more powerful. I flipped up my hair and then I cupped my breasts.
“That’s it, baby! Work it!” Quinn said. She turned her camera on its side to get some portrait shots.
Quinn switched her lenses quickly—faster than I’d ever seen a photographer switch lenses. It was as if she really didn’t want to miss a single second of my posing, even though she was getting many, many shots.
We found ourselves in the hallway. She had me walking up and down, one foot in front of the other as if I was on a catwalk. Then, we were back in Jenny’s bedroom, picking out a new outfit. We shot for hours, going from room to room, using all of Quinn’s lenses, and trying on many different outfits. Quinn’s face was bright and glowing. We eventually stopped when she maxed out her second SD card. “I could grab another one from Jenny’s gear room,” I said.
Quinn looked down at her camera. “I’ve got thirty-five hundred shots here,” she said. “That’s probably enough.”
And a part of me was disappointed. We were having so much fun. I’d never felt more confident in my entire life—and now it was over. But that was probably for the best. I probably shouldn’t have been enjoying my time as a sissy so much.
Quinn spent the next ten minutes flicking through her pictures on her camera, admiring her favourites—and there were many favourites. “I really owe you,” she said.
“Just don’t tell anyone about this,” I said.
“No—like, I really owe you. These are the best pictures I’ve ever taken.” She looked up at me with those glowing eyes. “Can I repay you?”
I shrugged my shoulders. “I guess, if you really want to.”
> And I thought that she was talking about money. I figured she was going to give me fifty bucks for my time. I wasn’t expecting what she really had in store for me.
She walked up to me and sunk down to her knees. She lifted up my skirt and slipped herself underneath. Then, I felt my panties shimmying down. “W—What are you doing?” I asked suddenly.
“Repaying you,” she said. And then I felt the warm wetness of her mouth enveloping my cock. She was sucking me off. I became tense. I reached out suddenly for something to hold onto. I found an antique side table and held on tight.
“Q—Quinn—I don’t think this is a good idea. I mean—you really don’t have to do this.”
She suddenly slipped her head out from under my skirt. She had my cock firmly in her grasp. “You don’t like it?” she asked.
“No—I like it. It feels really good. It’s just. I mean—look at me. I’m all dressed up. Don’t you want me to change first?”
She smiled. “Use a girl voice. Tell me how much you like it in a girl voice.”
“What?”
“Just do it,” she said.
So I cleared my throat and gave a ‘girl voice’ a try. I don’t think I sounded too bad. Her grin grew even bigger and her eyes glowed even brighter. “Keep talking,” she said. “Keep telling me how much you love it when I suck your sissy cock—and keep using that voice.”
“I fucking love the way you suck my cock,” I said.
“Call it your sissy cock,” she said.
“I fucking love it when you suck my sissy cock.”
“That’s better.” She got my cock deep in her throat—so deep that she gagged. Drool ran out of her mouth, dribbling down her cheeks and dripping on the floor. But she wouldn’t spit out my cock. She loved sucking it.
I was hard—as hard as I’d ever been, maybe even harder. She had a few fingers slipped under my ball sack and she was massaging gently. It felt good—too good. I was starting to worry that I would come in her mouth in a matter of seconds. I didn’t want her to think that I was a premature ejaculator—especially while I was all dolled up. The last thing I wanted was for the school to find out that I not only got dolled up for my photo-shoot, but that I also got off very easily while dressed up.
She suddenly spat my cock out and took a deep breath. She sprung to her feet quickly and said, “Come to the bedroom with me.”
“But we’re in a bedroom,” I said.
“Jenny’s bedroom.” She dashed off and I followed awkwardly, with my erection bouncing around under my skirt. When I finally caught up to her in Jenny’s room, she was rifling through dresser drawers.
“What are you looking for?” I asked.
She suddenly pulled a long dildo out from a bottom drawer. “Voila!” she exclaimed, holding it high. “Now get on the bed—on your stomach.”
“You want me to—to do what?” I said. My legs were trembling. But once again, I could see myself in the mirror, and I was completely captivated by how good I looked. I stared at myself for a moment while she repeated herself. My reflection was strangely mesmerizing, and almost hypnotising. I walked over to the bed and I crawled up, on my hands and knees. Quinn crawled up behind me and pushed me down, so that I was flat on my stomach. “What are you doing?” I asked, even though I already knew exactly what she was doing.
She didn’t reply, unless you count the little giggle that slipped out from her lips. I heard her spit. I looked back and saw her glob of saliva slowly running down the tip of the dildo. She brought it down, out of my line of sight, and pressed it between my butt cheeks. I felt the wetness of her spit against my tight hole. She started rubbing.
“I thought you wanted to thank me, not punish me,” I said.
“You will like it,” she said with that grin now in her voice.
She started to push. I closed my eyes and clenched. I took a sharp breath of air in through my nose. “Oh my God, you’re so tight,” she said, as if she was in shock.
“It’s not going to fit,” I told her. But apparently I was wrong. As soon as I said it, the dildo penetrated my asshole. It sunk in deep and I let out a sharp gasp. She paused for a moment, holding that dildo in so that I wouldn’t push it out.
“Just relax,” she said, putting one hand gently on my lower back. I remained clenched and tense. It wasn’t until I started running out of air that I finally took a deep breath. Then, I felt my muscles relax and I felt that dildo sliding in deeper. I had to focus hard to make my body remain relaxed. There was no pain, like I was expecting. It just felt… strange, like something was filling up my insides. I could feel every inch of it, squirming through me, pushing up towards my sternum. I opened my eyes and looked over at the mirror. I was shocked to see that Quinn almost had the whole dildo inside of me.
“That’s a good girl,” she said. Now she was pumping it up and down. I could feel its ribbed texture sliding against my anal walls. It still felt strange and unnatural—but there was still no pain. “We should get a towel under you, in case you come.”
“In case I come?” I said. I couldn’t believe it was a possibility. But Quinn went ahead and grabbed a tower and shoved it under me anyway. Then she continued to pump. After a few penetrations, I could feel that warm tingling: that pleasant euphoria. Maybe I could see why some guys liked taking it in the ass. Maybe there was something to it.
That euphoria started to become stronger. That tingling became more intense—and bigger; I could feel it up in my stomach and down in my legs. I squirmed slightly, trying to fight it back so that I wouldn’t do anything embarrassing, like moaning or screaming out in pleasure. But my attempts to hold the pleasure back only made that pleasure stronger. I ended up moaning.
“She likes it,” Quinn said with a big happy smile. She was pumping faster, making sure to get that whole dildo inside of my body.
“I like it,” I said. Though I don’t know why I said it. She was pumping fast now, using both hands for extra leverage. It felt like she was an Albertan oilrig, trying to find oil: in and out, in and out, in and out. My eyes started to roll into the back of my head. Now I was squirming constantly and I couldn’t stop. The moaning was constant too. “Oh God!” I kept saying, over and over.
I bit down hard on my tongue in a final attempt to push the ecstasy back. But it wasn’t enough. I trembled all over, and then I felt a warm, wet discharge between my legs. I reached down to see what was happening, and I stuck my fingers right into a growing puddle of sticky cum. “Shit,” I groaned, pulling my fingers out to look at my mess. Maybe the towel was a good idea.
Quinn pulled the dildo out from my ass, leaving me feeling empty. She looked at it with wide eyes. “I got this whole thing inside of you!” she said, as if it was some kind of record. I felt my cheeks turning red, but in a weird way, I was kind of impressed with myself—and maybe even a little bit proud.
Quinn helped me clean everything up, and then she brought me back to her apartment, which wasn’t too far away. We looked through the photos together. I asked her to send me the photos—then I was excited when I saw that she had gotten a copy of my pool photos from our instructor. I asked her to send those too. She looked at me with wide eyes when I told her that I deleted them. “How could you delete them? They’re literally perfect!”
Though once I got home, I wasn’t sure what I was supposed to do with all the photos. Maybe they were better left deleted. Maybe I didn’t need to remember the last two days of utter humiliation.
CHAPTER VIII
I got the best mark in the class for my swimming pool shots: a perfect A+. And I was excited about that for a week, and then I got a call from the school administrator. The school wanted to meet with me in private.
My first thought was: they realized it was me in the photos, and that would somehow disqualify me and leave me with an F when my A+ once was. The whole point of the assignment was to work with models, and I hadn’t worked with one, unless you count Tae—but they didn’t know about Tae, and it was probably best that they
didn’t know about Tae.
I made my way over to the school. On my way, I had a more optimistic thought go through my mind: maybe they loved my pictures so much, they wanted to feature them on their website. Maybe they were going to ask if they could use my shots for their marketing. Hell—maybe they were even going to pay me. But why would they bring me in to chat about that? I’m pretty sure I signed a form when I signed up for the school that said they could use any shots I took while I was enrolled without having to ask for permission. But maybe they were just going to be courteous?
I arrived at the office and I was told to wait in the lobby. I took a seat and admired the photos on the wall—all taken by students from previous classes. Some of them were pretty good. There was one particular photo of a model that stuck out to me. She was striking an interesting pose, with her elbows against her sides and her hands in the air. It was a cute shot—and I found myself storing it away in my memory so that I could do a similar pose for my next shoot.
What next shoot? Why was I thinking about doing another shoot as a model? There would be no more modelling—no more getting dolled up. That was all behind me.
“Frankie—they’re ready to see you now,” the secretary said. So I stood up and walked over to the department head’s office. A chill crept down my spine.
Three department heads were sitting in the office, all on one side of a long boardroom table. They told me to sit down, so I sat. “What’s this all about?” I asked.
“We need to talk about your grade, Frankie,” said the lone man of the three. The two women shook their heads in agreement.
“What about it?”
“You’re failing,” he said.
“What? How is that possible? I just got an A+ on the most recent assignment. I can’t be failing.”
He pulled out a folder and held it close to his face. He had old eyes and his vision was poor, even with the spectacles on his face. “You’ve missed forty classes, and you have sixteen lates on your record.”
“Forty?” I said. “I haven’t missed that many.”
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