I got up carefully and tiptoed over to my computer. I clicked on the notification bell and saw that I only had a single notification, from my aunt. She liked a photo I’d posted a week before. There was nothing from my friends, as if they hadn’t been watching the TV when my picture came on. But surely they had been—and it wasn’t just on the TV. I went over to our town’s official Twitter page and saw my picture there. It had been liked dozens of times. And it was already finding its way onto news pages—being shared by towns that were one hundred and fifty miles away.
I looked into my mirror and saw that my face was bone white, and starting to turn green. I really was going to be sick. I really was going to throw up. Why weren’t my friends reaching out to me? Why weren’t they posting on my social media pages? Were they saving their humiliation for my face, so they could watch my reaction when they started rolling on the floor with laughter?
Finally, my phone buzzed. I rushed over to it and lifted it up with my trembling hands. It was a number that wasn’t saved to my phone. “Congratulations,” the message read.
“Who is this?” I asked quickly.
“It’s Jenna,” read the next message. “I hope you don’t mind that I submitted you.” She ended her message with a little blushing faced emoji.
“I do mind. Are you insane? You think this is funny? Call the contest and tell them to take my picture down.”
“They’re expecting you to make an appearance tomorrow,” she said, as if she didn’t hear me or my frustration. “I’d be happy to help doll you up to get ready.”
“I’m not doing it. This is insanity. Are you crazy? I’m seriously asking.”
“If you do it, I’ll suck your dick until you come.”
I opened my mouth to continue shouting at her, but I was suddenly at a loss for words. A warm tingle crawled down my back and then I found myself with an awkward smirk on my face.
“Your place or mine?” she asked.
“I want you to give me your address, but not because I want to go through with this. I just want to talk to you face to face, so I can try to understand what the hell is going on in your head. That picture could ruin my career—do you understand that? I’ll be the laughing stock of this town, and it will probably haunt me for the rest of my life.”
“382 Willow Street. I’ll see you there in the morning—let’s say at seven. Bye, Todd! See you tomorrow!” And then she hung up the phone. My head was spinning. I couldn’t believe what was happening—and I couldn’t believe that the girl I thought was the love of my life was actually a complete lunatic.
CHAPTER IV
I went to her house on Willow Street, with her dress and her pair of panties, but not because I had any plans of getting dolled up. I just wanted to return her things and then dig into her. I wanted to make sure she understood how crazy she was, and how horrible she was, and I wanted to see her face once that reality sunk in.
Though as I sat on the bus with her dress and panties in a white plastic bag, I started to consider the other option: going through with the nonsense and getting that blowjob. I could try to convince my friends that I was just doing it as a joke. I could even reveal myself on live local television, and then the town would be laughing with me instead of laughing at me. Maybe they would even think that I was just trying to make some sort of social criticism—as long as they didn’t think that I was some cross-dressing weirdo.
Jenna’s house was nice: three stories, recently updated, professionally landscaped front lawn, big windows, and so on. I approached the large red door slowly, still unsure of what my plan was. Maybe she would give up the blowjob right away, and then I could chicken out as soon as I came. Sure, she would probably be mad, but that was her own problem—and she couldn’t possibly be as mad as I currently was at her.
A cool breeze tickled the back of my sweaty neck as I reached for the doorbell. My mind was suddenly blank. I couldn’t remember why I was standing there, why I didn’t just chew her out over the phone. If she wanted her dress back, she could have come to my house to get it.
I didn’t have to ring the bell. Before I could press it, the door opened and there stood Jenna, leaning against the doorframe with a big smile on her face. “Ready to have some fun?” she said. And I immediately remembered why I was obsessed with her for so many years. She was beautiful—even in her pyjamas, without makeup. I loved the way that she smiled—it was a mousy kind of smile. And I loved the way her messy hair cascaded down her shoulders.
I had to clear my throat before I could speak. My heart was pounding all of a sudden. “I’m not getting dressed up for you. I just came to, uh, tell you that I think, uh…” I couldn’t remember my lines, which I’d gone through over and over on the bus ride over. My mind was suddenly blank, which shouldn’t have surprised me. It was going blank a lot over the past twenty-four hours.
“You just came to tell me what? That you don’t want me to suck the cum out of your big cock?” Her grin grew a little bit bigger, and my mind went a little bit blanker.
And then I decided to go off of my mental script. “Why are you doing this to me?” I asked. “Do you get a kick out of this or something?”
“The Miss Beautiful winners are always so ho-hum. I thought it was time for a real cutie to take the first prize. So I made it happen.”
“I don’t understand. What do you mean, you made it happen? Did you cheat somehow? Do you know someone on the pageant committee?”
She let one of her trademark cute giggles slip, and my heart melted a little bit in my chest. “I don’t know anyone on the committee. I just knew that you would win. How could you not win with a beautiful face like that?”
And now I felt my face turning red. Was she mocking me, or was she serious? It was impossible to tell with that grin on her face. I would have guessed mocking had it not been for the fact that none of my friends had reached out to me. My Facebook page was still desolate, as if no one could tell that I was the girl in that winning photograph. And I had to admit, I did look surprisingly convincing in that picture. It helped that I had a short and relatively scrawny figure.
“Look,” I said. “I just want to give you your dress back. That’s all I came for.”
“Just come inside for a few minutes. You’ll love the outfit I have picked out for you.” She reached out and grabbed my wrist, and there was something about the warmth of her fingers that made my body freeze. My heart shot up into my throat. I could suddenly smell that amazing perfume she wore, and I could feel the warmth radiating off of her beautiful body. I was suddenly reminded of every single heart-pounding moment over the past eight years: every time I passed her in the hallways at school, every time she looked at me with her adorable smile, every time I caught a glimpse of her panties under her gym shorts…
“I’ll come in for a minute, but I’m not going on TV,” I said.
The main floor of her house was one large, impressive open space. The ceilings must have been twenty feet high, being held up by thick marble pillars. It could have been the lobby of a very expensive hotel. “What do your parents do for a living?” I asked.
“I don’t know—boring stuff in other countries,” she said. “They’re both in Sweden now for some conference. So make yourself comfortable.” She grabbed a remote off of a side table and then she pressed a button. A fire erupted in the large fireplace in the middle of the room. “It sure is cold out, don’t you think?” She meandered through the amazing space towards the large kitchen area, where she already had her changing station set up. The kitchen island was covered in dresses, and each barstool had a different pair of heels on it. And next to the sink was a mound of hair, which I thought was a severed head for a split second before I realized it was a wig on a foam head. “I say we start with your makeup,” she said.
“I told you that I’m not doing this,” I said.
“Then why are you here?”
“Because,” I started, but I couldn’t figure out an answer. Why was I there? Why wasn’t I just
turning around and leaving? “Maybe I should just go.” But I couldn’t bring myself to turn around. I couldn’t just turn down a blowjob so easily.
She smiled. Then she tossed a pair of white panties at me. “The white won’t show through your dress,” she said. “Strip down and put them on.”
And then I took a deep breath and I bit down on my tongue. “I thought you said you were going to suck my cock,” I said.
She nodded her head with big glowing eyes. “I will—as soon as you’re all dolled up.”
I stood still for a moment, not fully trusting her. She couldn’t be trusted—I knew that much for sure. She’d already screwed me over once. “If you take out your phone and snap a picture, I’m done with this,” I said. “And I mean it.”
So I took the panties over to the bathroom on the far end of the large room and then I went inside to get undressed. I realized how silly it was to seek privacy while I got into the panties. It’s not like the panties did anything to cover me up. They were so tight that they became translucent when stretched over my cock, so Jenna could see everything regardless.
She took one look at me and then sent me back into the bathroom to shave. “I want you to be hairless. And run some moisturizer on your skin, so that you don’t get razor burn. We want smooth, perfect legs under your little skirt.” I was halfway through shaving my second leg when I started to think that maybe I was the crazy one. She wasn’t forcing me to do any of this—I was doing it all voluntarily, all because I wanted her to suck my cock. Surely that level of desperation made me crazier than her fulfilling some silly little fetish.
I came out and she did a full inspection, walking around me and running her fingertips up and down my smooth legs. “You did good,” she said. She ran her fingers all the way up to my panties, and then she slipped a finger under the lacy undergarment to feel my ball sack. I perked up and let a gasp slip through my lips. “You even shaved your lady bits. Good job,” she said. I didn’t like that she called my ball sack ‘lady bits’, but I kept my mouth shut. I was a little bit closer to having the cum sucked out from my cock. I still didn’t have to go through with any live television appearances or any party circuits.
We spent the next hour and a half perfecting my makeup. She did all the work, but she made me watch. “You’ll be doing this yourself for the rest of the week,” she kept saying. And I paid attention to appease her, even though I had no intentions of doing my makeup again, unless she sweetened her end of the bargain with some pussy or maybe even anal.
She went a lot dark with my makeup: darker eye shadow, thicker eyeliner, more mascara. She brushed on plenty of blush and then she spent a good thirty minutes working on contouring. I lost count of how many times she said, “Quit moving or I’ll screw up and we’ll have to restart.” I only had a tiny makeup mirror to watch in, but I still did my best, strangely hypnotized by how effortlessly the whole process was for her. And it was actually really interesting to watch my face change so drastically after the application of each little product.
“Ta-da,” she said, stepping away as soon as she was finished the final few details. I picked up that mirror and looked at my face from multiple angles. I looked good and I looked convincing—but most importantly, I looked unrecognizable. I smiled and watched as my eyes sparkled, but that moment of elation was short lived as reality crept into my gut. I didn’t want to look like a convincing woman, and I especially didn’t want to look like a pretty girl. I was a man, and men should look like men. Men should be rugged and tough and they shouldn’t even be able to fit into pairs of panties or dresses or little heels.
But everything fit me perfectly. The dress she had picked out for me was red and short and it looked incredibly tiny as Jenna held it up, but it looked perfectly fine on my body. It even made my hips appear wider and my waist appear smaller. She passed me two pads from one of her bras, which fit perfectly in the dress’ chest, giving me a little bit of a bust. “You’ve got small tits, but they’re super cute,” she said with a lip-biting smile.
And in case I wasn’t already unrecognizable enough, she got that long brunette wig onto my head, and suddenly I was a completely different person. It’s amazing how a hairstyle can completely transform a face.
“You’re all done,” she said. And it took a minute for me to remember what that meant: I earned my blowjob. My heart skipped and stuttered and I stood up straight.
“I guess it’s not your turn to put up your end of the bargain,” I said, smiling awkwardly. My cock was already pulsing in my panties.
“Not if that’s the voice you’re going to use. If you sound like that on live television, then you’re screwed. And I have to admit, it’s not very sexy.”
My cheeks turned red as the thought of going on television crossed my mind. But I shook the thought away. I didn’t actually plan on going on TV. As soon as my load was in Jenna’s mouth, that dress was coming off and that wig was hitting the floor. I was just there for the blowjob, and nothing else.
So I cleared my throat and in my best female voice I said, “Is this better?”
She smiled. “Better, but not perfect. Keep talking. Don’t stop until I tell you to.”
“What should I talk about?” I asked, still using that voice, trying to make small adjustments based on her facial reactions.
“Just talk,” she said.
So I just talked. I started by talking about my college classes, and then I started talking about my college professors, and then Jenna sunk down to her knees and slipped her head underneath the skirt of my dress. I took a deep breath in and perked up as I felt her fingers gently toying with my panties. I felt a plume of her warm breath tickling the bare skin of my recently shaved cock and balls. And I kept talking, rambling on and on in my female voice. My mind started to go blank and I paused for a moment. “Keep talking,” she said, pausing until I resumed. So I quickly tried to think of something to say—I ended up telling her the plots of my favourite horror movies.
She gently slipped my cock through her lips and started to suck. Warm pulses of euphoria surged through my body. I reached my hands down and grabbed her head. I pulled it in tight, pushing my cock down the back of her throat. Impressively, she didn’t gag. She just kept sucking. She even let a little giggle slip.
I was still rambling on, now talking about her. “You’re hair is so soft and your face is so beautiful. I really love the way that you smell. I’ve had the biggest crush on you for almost ten years—since I first saw you, basically.” I wasn’t even in control of what I was saying. It was like my mouth was falling down an endless flight of stairs and there was no one there to stop it.
She looked up at me with warm glowing eyes. I paused. “Go on,” she said, before sinking back under my skirt to continue licking my throbbing erection. It felt so good, so that’s what I said. “You’re so good at that. Oh my God, it feels so fucking good. I love the way you eat me out. I love the way you suck my big, hard pussy. You’re going to make me come, you filthy slut. Oh God, you’re going to make me come.” I was still using my female voice, but I was hardly having to think about it. It was starting to feel more and more natural, with every word that slipped out from my lips.
I heard her moan, and that’s when I noticed that she had a hand underneath her skirt, pressed firmly between her thighs. Her body shuddered and then I heard a subtle splashing noise. She was squirting onto the marble floor.
And now I could feel my orgasm approaching—how could I not come after watching that? I grabbed her head firmly with both hands and I started to thrust, using her head like a glorified sex toy. Drool was running down her cheeks and dripping off of her chin. “You’re so fucking beautiful,” I said. And she smiled with my big cock in her mouth.
Instead of coming in her mouth, I pulled her head back by her hair and I came all over her face. Maybe it was a little bit of revenge, or maybe it was just a spur of the moment decision with no thought process behind it whatsoever. She flinched and shut her eyes, but she wasn�
��t able to look away as I held her head in place by her hair. I made a real mess of her makeup, and I even landed a blast in her left eye.
And once I was finished, a guilt filled my stomach. She stood up slowly, wiping the cum from her face. “You asshole,” she said.
“I’m so sorry,” I said, still with that female voice.
“It’s fine,” she said with a sigh. “But now I have to redo my makeup. It took me an hour to do this, you know.”
“I said I’m sorry.”
She shook her head and went off to the bathroom to wash her face, leaving me with a powerful guilt swirling in my gut. And now I felt guilty about my original plan. I couldn’t just take off my outfit and my wig and leave. I couldn’t just make her think that I only came to come all over her face.
I looked in the mirror. I looked convincing and more importantly, I looked unrecognizable. Maybe I could go through with this live appearance. Maybe I could just get it over with and then feel less guilty about this whole thing.
So I kept practising my voice. I walked around Jenna’s kitchen in a pair of tall heels while repeating random sentences that had nothing to do with anything. If I was going to do this, then I had to pull it off. I couldn’t let anyone realize they were seeing a man on their TV screens, because it wouldn’t long before they realized they were seeing me once they realized they were seeing a man.
CHAPTER VI
Jenna went with me to the TV station, which wasn’t too far from her house. Before we walked into the building she smacked me on the ass and said, “I hope you’re not planning on doing anything stupid.”
I looked at her and saw that there was legitimate concern on her face. And I realized that I was the one in control now. I could easily go in front of the camera and reveal my true self, pretend the whole thing was a joke, and ruin the fun for Jenna. Or I could tell the whole town that Jenna set me up, and that she was trying to blackmail me and bribe me with sex—though that would probably be just as embarrassing for me as it would be for her. Jenna probably didn’t want the world knowing that she could only get off with boys in dresses and makeup. But I didn’t want the world knowing that I was so desperate for a blowjob that I was getting dolled up and going on live television.
Big Hard Girls Page 27