“It’s going to be dark and foggy—I doubt they’ll recognize you,” she said casually as she pulled a tray of fresh cookies out from the oven.
“But what if they do? What if someone recognizes me? Then I’m doomed! Please—I’ll serve drinks and do whatever for your party, but don’t make me dress up like a girl.”
“Sorry, Chelsea, but your punishment isn’t over yet. I promised your mom that I wouldn’t make it easy on you. Now do me a favour and move these cookies onto a clean plate.” She placed the cookie tray down on the counter. They smelled amazing and I’d been looking forward to eating them since Jenna started making the cookie dough—but I suddenly had no appetite.
The rest of that day dragged by slowly. I looked through Jenna’s medicine cabinet for something to quell my nausea, but I couldn’t find anything. I was no longer looking forward to being sexy for another day—now that was the very last thing I wanted. I didn’t want to wear whatever costume Jenna had picked out for me. I didn’t want to parade myself around in front of all of my classmates and friends and family members. Even if my parents didn’t recognize me in whatever costume Jenna stuck me in, they would still wonder where I was—and they would know that I was at that party, where I was living out the last of my punishment.
“You can go home for today now,” Jenna said. “I’ll see you here around ten tomorrow morning—that should be lots of time to get everything ready.”
So I got changed and I went home with a stomach full of dread. I looked briefly on Facebook and saw that most of my friends were planning on swinging by Jenna’s house before heading out to more rowdy house parties. I tried messaging Tony, “Why even go to the party at Jimmy’s house? Why not just go straight to a better party. Jimmy’s house is going to be lame probably anyway.” But Tony seemed to disagree. “There will be tons of free booze there—and I kind of want to see what she’s done with the yard this year.” I didn’t try to talk him out of it anymore, worried that I would end up looking suspicious.
I suffered through another sleepless night—only half nodding off once the sun was already up. It was Halloween—a day most young people should be excited for, but excitement wasn’t one of the emotions I was feeling. I got up slowly. My mom was making breakfast, but I passed. I had no appetite. “I’m supposed to be at Jenna’s house in half an hour,” I said.
“Can I drive you? It’s nippy out this morning,” my mom said.
“No—I’ll just ride my bike over,” I said.
“Okay. We’ll see you at the party then?” she asked.
“I doubt it,” I said. “I’ll probably be in the kitchen washing dishes all night.”
“Well then we’ll stop by the kitchen to say hello,” she said.
“I can’t promise I’ll be there. I might even be out running errands—picking up ice, that kind of thing.”
“I’m sure we’ll see you at some point. What’s wrong with you? It’s Halloween—why are you acting so mopey?”
I left without answering. I was on track to be early for the morning, but I was going to need all the time I could get if I was going to make myself truly unrecognizable. I left my bike against the side of Jenna’s house and then I went straight to her door and rang the doorbell. And then, as I waited for Jenna to let me in, I started wondering what costume she had picked out for me. I was hoping it would be something relatively conservative—maybe I could be dressed like a mummy—or anything with a mask. But another part of me hoped that it would be something sexy—though I knew sexy was the last thing I really wanted.
The door opened and I took a step forward, ready to let myself in. And then I looked up and saw Jimmy standing in the doorway. I’d forgotten that it was Sunday and Jimmy had no school. My heart swirled down into my gut. “Can I help you?” he asked.
My lips parted but no words came out. I tried clearing my throat, but that didn’t help either. How could I get passed Jimmy?
CHAPTER XI
I spat out the first words that eventually came to my mind. “I just came to pick something up for my mom—something your mom borrowed a few weeks ago.”
Jimmy stared at me. I could see that he was holding his hands away from his body, as there was wet paint on his fingers. “I’ll go get her then,” he said. He certainly wasn’t excited to see me—I was part of the reason he didn’t have any friends. After I stopped hanging out with him, my other friends stopped hanging out with him too. I was the one who deemed his model-painting hobby as lame and stupid. And he had to put up with years of ridicule because of me.
I felt strangely bad about it—Jimmy wasn’t a bad guy. He’d never done anything mean to anybody, but we still all made fun of him for so many years, and he hadn’t picked up any new friends since. He probably didn’t want new friends. He probably didn’t want to go through the same thing again: having his only friends turn on him because they didn’t think his hobbies were cool enough.
Jimmy didn’t come back to the door with his mother. Instead, he went straight back to his bedroom. Jenna let me into the house. She led me up to Linda’s bedroom where my costume was waiting for me.
It was a black witch costume, and it was designed to be sexy. The top was small, like a bikini top. And to cover my tush was a black skirt, which didn’t do a ton to keep me covered. I had to shave again before getting into the skimpy little outfit. Jenna went to the basement and found a pair of thigh-high black leather boots, which went great with the costume. And then she dug around in her lingerie drawer and found me a pair of fishnet sleeves, which extended from my shoulders to my elbows.
I felt the same way that I felt on my first day as a girl in Jenna’s house: exposed and vulnerable. I kept tugging down the skirt as if was riding up and showing off my whole tush—though I don’t think it was. Every time I looked in the mirror, it was positioned perfectly under the edge of my butt cheeks.
I spent most of that day in the bathroom doing my makeup. I spent close to an hour on each eye, making sure every little detail was perfect. I went thick with the eyeliner and heavy with the eye shadow. I found a black lipstick that complimented the costume, and made me look even more unrecognizable. When I finally went downstairs to see Jenna, it was only a couple of hours before the start of the party.
She was folding laundry. She’d cleaned all of the bed sheets in the house as well as the curtains and all of the clothes in her closet—just so her closet would smell fresh… as if anyone was going to be looking in her closet (or even her bedroom, for that matter). She asked me to go and put the sheets on the beds, so I started going room to room like a hotel maid. When I was done, I still had a set of sheets. “Are these spares?” I asked.
“No, those are Jimmy’s sheets. I did his bed, too,” she said. A cool shiver crept down my spine. I made my way slowly to Jimmy’s bedroom. He was inside—I could hear him humming as he painted his miniatures. I took a deep breath and then I knocked quietly. “I—uh—have some sheets to put on your bed,” I said.
“Come in,” he said back.
So I let myself in. He was sitting at his desk with his back to me—which was a relief. “I’ll be quick,” I said. I hurried over to his bed and I started getting it dressed. I looked up and saw his back. His attention was still on his miniatures. And then as I looked back towards the bed, I noticed the mirror on the wall, and then I saw that he was looking at me through it. He looked away quickly, his face turning red. I pretended not to notice and I continued making up his bed.
The silence in the room was awkward. I looked up quickly again, and I caught him looking my way again. He looked away shyly. Was he checking me out, or was he trying to figure out who I was? “So, um, what are you painting?” I asked.
“Warhammer models,” he said with a quiet voice.
“What’s that?”
“It’s for a game. You get these plastic models and you have to build them and paint them.”
“That sounds cool,” I said.
He shrugged.
“Can I see t
hem?” I asked. I walked over to his desk. He hesitated, but then he ended up handing me one without looking at me. It was surprisingly impressive. The detail was intricate. He’d managed to shade the little model’s armour. He’d even managed to get little pupils in the model’s eyes. His skill had improved dramatically since we used to play with the models together. “That’s amazing,” I said.
He reached out, motioning for me to give the model back. So I handed it to him.
“That really is impressive,” I said.
“Thanks,” he said softly, without looking back at me. His cheeks were still red.
“So do you have a girlfriend?” I asked. He didn’t look back, but his face got redder.
“No,” he said.
“Why not? You’re a handsome guy. And you’re very talented.”
“Girls don’t really like me,” he said. “I’m not really popular.” Somehow I felt guilty, as if I was responsible for his social anxiety—and maybe I was. Maybe my ditching him all those years ago had left him socially traumatized.
“I’m sure that’s not true,” I said. “You seem like a really nice guy.”
He just shrugged his shoulders.
“I should be getting back to your mom—the party is going to start soon. What are you dressing up as?” I asked as I moved towards his bedroom door.
“I’m just going to stay up here,” he said.
“You should come down—even just for one drink,” I said.
“I’d rather not. Thanks though.”
So I left the room feeling nervous and guilty. Now I really wasn’t looking forward to this party.
CHAPTER XII
The first few party guests were strangers to me. One of them was a single father who kept inadvertently looking at my ass, but I didn’t mind. I took it more as a compliment than anything. Ten minutes later an older couple showed up. The husband kept looking at my ass, and it wasn’t long before he got a sharp elbow from his wife.
Then some of my friends’ parents started showing up, and my heart started pounding. I kept the brim of my witch’s hat low, in an attempt to cover my face—but I could only keep it so low while I was walking around with a tray of drinks.
It was an hour into the party when my classmates started showing up. Danny, the guy who sat directly next to me during math, looked right into my eyes as I opened the door for him. He stared for a moment too long, and I found myself looking away quickly, hoping he wasn’t recognizing me. “Are you Jimmy’s sister? I didn’t know Jimmy had such a babe of a sister,” he said, smirking confidently, despite his face full of pimples. I found myself smirking—he didn’t recognize me, and he thought that I was a babe.
I got a few curious looks throughout the night, and a few guys came up to tell me that I looked familiar. My heart stuttered every time, but no one ever caught on—especially once all of the guests had a few drinks in them.
There must have been three hundred people at that party—maybe more. It was impossible to keep count, as people were showing up faster than I could count them. Some of the costumes were great—and some were less than impressive. Danny’s mom showed up dressed like a nurse—even though she worked as a nurse. Philip came dressed as a soccer player, even though he was on the school soccer team.
Tony’s disguise was a real relief. He came as Clark Kent, wearing his dad’s glasses, which had a strong prescription. I overheard him complaining that he couldn’t see very well—which was obviously for the best.
As conversations became louder, Jenna turned up the music, and then conversations had to come louder to compensate. Soon enough, the party could be heard from blocks away. People were having a blast. Jenna’s snacks were a hit, and everyone spent at least a few minutes gawking at the intricate decorations.
Jenna came up to me around 10:00 PM and said, “You’re doing a great job. Everything is going so perfectly!”
“Thanks,” I said. And I was having a blast. I loved strutting through the room and turning heads. I’d never felt so confident in my whole life. I was sure that no one recognized me. Even my own parents had no idea who I was as they took drinks off of my tray. Though it was a relief when they went home early for the night, and it was a relief when my classmates took off for rowdier parties.
But even without my classmates, the party was still going strong. Jenna came up to me and told me I could take a break. She had a few other friends show up to help pass around drinks. “You can probably even take off for the night. I guess your punishment is done,” she said.
I felt a wave of relief, and then I felt a wave of disappointment. Once I took off that sexy witch costume, that would be the end of my feminized days. I would never get to truly feel sexy again. I wouldn’t ever get to admire myself in the mirror, or spend hours perfecting my makeup. I wouldn’t get to feel my perfectly smooth legs after a few days, and I wouldn’t get to feel the fresh air all the way up to my tush when I was out in public.
“Thanks,” I said. I didn’t want to look disappointed, so I forced a smile. I couldn’t let her know that I’d actually enjoyed my punishment.
I went inside where the party was mostly desolate. I had a drink—my first of the night. And then I found myself in the living room, in front of the big fancy wall mirror. I took off my hat and placed it down on the table. I fixed my hair and felt a sadness filling up in my chest. It was the last time I would see myself looking so pretty, so I wanted to take it all in. I wanted to enjoy the moment—I didn’t want to feel sadness, but I couldn’t help it.
I made my way upstairs slowly. As I walked up to Linda’s bedroom where my male clothes were stashed, I noticed the light glowing under Jimmy’s door. I hesitated a moment and then I walked over to Jimmy’s room. I knocked gently and waited. “Who’s there?” he called out.
“It’s me,” I said. “Chelsea.”
There was another silence. “Come in,” he said. So I let myself in. He was on his bed, reading one of his miniature books. He looked over the book at me and then he looked back down at his book quickly. “What’s up?” he asked.
“I just wanted to come say hi before I took off. You really should have come down to the party. It was a lot of fun.”
“I didn’t really want to see anybody,” he said.
“Well you should have come to see me.” I hopped up on his bed and took a seat next to him. Our shoulders were touching. His face quickly became a shade of red, and I wondered if he’d ever been that close to a woman before. “You really shouldn’t be shy,” I said. “You seem like a really nice guy—and you’re really good at painting your Warhammer guys.”
“Thanks,” he said, his voice cracking slightly.
“And you’re cute,” I said, smiling.
He looked at me slowly. His cheeks couldn’t have been redder. “Thanks,” he said. I leaned over and gave him a kiss on the lips. He remained frozen and he didn’t kiss back. Even after I leaned back, he continued to remain still, his gaze fixed on nothing in particular.
“W—Why did you do that?” he asked.
I shrugged my shoulders. I wasn’t even sure why I’d done it. I thought I’d done it out of guilt—as a way to repay him for hurting him all those years ago. But as I stared into his eyes, I realized that there was more than that. So I kissed him again. This time he kissed back. His lips were soft and he was a gentle kisser.
I rolled on top of him and we continued to kiss. He was slow to wrap his hands around me. He had gentle hands. They moved slowly up and down my back. I felt him becoming tense. I opened my eyes and leaned my head back. He was staring at me with a frightened look. “What’s wrong?” I asked.
“Why do you like me?” he asked.
“I don’t know. You seem sweet,” I said.
“It’s just… Girls don’t really like me.”
“I’m willing to bet that’s not true, Jimmy.”
“How do you know my name?”
My heart skipped a beat. “Your mom told me,” I said.
“Oh,” he sai
d. There was an awkward silence, which I ended by leaning in again for another kiss. He accepted the kiss, and he even let me stick my tongue into his mouth. His hands continued to caress my sides, carefully exploring my body. They wrapped around me slowly and he slipped his fingers onto my ass. I could feel his heart beginning to surge, pounding against my chest as I laid on top of him.
“Are you a virgin?” I asked.
His face became that shade of red again, but he didn’t answer—he didn’t have to. So I sunk down and I began to undo his belt. He was nervous: tense and breathing heavily. I knew he would relax soon.
I reached into his pants and then I fished out his cock. And then I saw it and I became the frozen one. His cock was huge: almost nine inches long, and it was still mostly flaccid. I lifted it up—it was heavy, too. And it was starting to pulse. I was not expecting such an impressive member to be hiding in those pants. “Is everything okay?” he asked.
I nodded my head slowly. “Yeah—you’re just… you’re really big,” I said. I wasn’t sure whether or not I’d blinked.
“Is that okay?” he asked.
“It’s okay,” I said. “It’s more than okay.” There was something so mesmerizing about his massive cock. I just wanted to touch it—I wanted to stroke it and suck it. I wanted to see it hard and I wanted to feel it inside of me. I wanted to watch cum explode out from his bulbous tip. I wanted to fuck him. But first, I had to get him hard, so I started massaging his length. I leaned my head in and I sucked his tip while I worked his shaft. I could feel him getting harder. I could hear him breathing heavily. He was enjoying it, which had me feeling strangely satisfied.
Once he was hard, I couldn’t even believe his cock was real. It was so big—at least twelve inches long, and curved slightly to one side. It was heavy, like another leg. I couldn’t even begin to fit the whole thing in my mouth, so I just sucked what I could while pumping with both of my hands. “That feels good,” he said.
“Good,” I said. “I don’t know how you can be shy with a cock like this.”
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