And she laughed. “It’s fine, Ian. Really—it’s all good. The guys are going to get the siding all cleaned up and then I’m going to have you do a quick coat of paint. No worries at all.” I was relieved to hear she wanted me to paint her house—at least I could help make my wrongdoing a little bit better…
“What can I do now?” I asked.
She looked around the house. “Why don’t you help me carve some new jack-o-lanterns?” she said, looking over at her kitchen table. There were a dozen pumpkins waiting to be carved—a few to replace the ones Tony and I ruined, and then some more to spread out throughout her large property. So for the next three hours, we sat and carved pumpkins. It was actually kind of fun—she let me come up with my own designs, and then she showed me some techniques to carve more accurately. My jack-o-lanterns weren’t nearly as spectacular as hers. Every pumpkin she carved looked like he could have been in a magazine. She was a surprisingly great artist.
We brought the lot of jack-o-lanterns to her basement. She closed the blinds and then we tested them all with cheap tea candles. They looked great. “Wonderful. We’ll probably carve some more tomorrow to put in the back yard,” she said. And I found myself actually looking forward to returning to Jenna’s house for more party planning.
Maybe Jenna really did believe that I didn’t mean to egg her house, and maybe she didn’t have it in her to truly punish me. Maybe I was better off at her house than at my own house, where I couldn’t even leave my small jail cell of a bedroom.
“What’s next?” I asked.
“Are the workers gone yet?” She looked out the window. “No, they’re still there. Okay, then I’m going to have you pick eggshells out of the rose bushes. You’ll need gloves because the prickles can really hurt. Oh, but before you go out there, I want you to put something on for me. Follow me.” She started up the stairs, so I followed. It had been a long time since I’d been up those stairs—but I remembered that they led to the bedrooms. All four bedrooms were upstairs: Jimmy’s bedroom, Jenna’s bedroom, Jimmy’s older sister’s bedroom—what was her name again? Linda? And then there was the spare bedroom.
We went into Linda’s bedroom. The walls were painted lavender and the room was immaculate, just like every other room in the house. “Don’t worry,” Jenna said. “Linda is away at her first year of college.” I thought it was a strange thing to say to me—why would I care if Linda were away at college? Why would I be worried about anything?
Jenna started digging through Linda’s closet. “It’s in here somewhere…” she said. “Ah-ha!” She pulled a little white dress out from the closet. “I bought it for Linda’s prom last year, but she didn’t end up wearing it. See? The tag is still on it.”
She handed me the dress. My heart stuttered and skipped a beat. “What do you want me to do with this?” I asked as I stared down at the thing.
“Wear it. And it’s cold out, so you’ll probably want these, too,” she said, handing me a pair of thigh-high white stockings. “And then you’ll need this, and this…” She pulled out a bra and a pair of panties.
I stood frozen—even my heart was hesitant to continue beating. I finally was able to take a deep breath. “You want me to wear your daughter’s clothes?”
Jenna smiled. “Yes. And her makeup, and I’ve got a wig for you in the other room.”
“But why?” I asked. I could feel the colour draining from my face.
“Because it’s not much of a punishment if I just have you outside picking up eggshells, is it? I mean—I bet you’d rather be cleaning up my yard than at school, and I need to make it a punishment somehow. Now go ahead and get dressed.”
I felt sick. I was worried I was going to throw up on Linda’s bedroom floor, and then I would have to clean it up dressed like a French maid or something. I looked down at the dress again. “But people will see me—and they’ll recognize me. Everyone will make fun of me.”
“Well if you do a good enough job with your makeup, no one will recognize you. I’ll even help you out—today, anyway. But for the rest of the week you’ll probably be on your own. I’m only going to get busier and busier as the big party gets closer!” She started towards the door. “I just remembered that I made some pads for you—they fit perfectly in the bra. I’ll go grab them. Go ahead and get dressed!”
My legs trembled slightly. My head was light and spinning. Now I was sure I was going to throw up—I wanted to throw up. I even gagged slightly after she left the room, but no vomit followed.
CHAPTER IV
I felt stupid in the dress—and I felt even stupider in the panties. They were hardly wide enough to hold my cock and balls in place, and they were uncomfortably tight. Jenna kept insisting that I would get used to them, but I had a hard time believing that. Jenna had me stand in front of the mirror while she got the wig snug on my head. It looked okay, but I still felt ridiculous. At least with the wig I didn’t look terribly familiar.
We went into the bathroom to get my makeup done. She sat me down in a seat, which she pulled in from another room, and then she told me to pay close attention. “You’ll be doing this yourself tomorrow morning.”
“Do I really have to do this? Can’t you punish me in some other way?” I asked, my heart still aching.
“This is the best I could come up with. The punishment needs to be good—and clearly this is uncomfortably for you. Now we’re going to start with foundation.” She rubbed a flesh-coloured cream all over my face. And then she pulled out a tube of mascara. She kept reminding me to pay close attention. I did my best, but it was hard to focus on anything with my mind racing and dreading the moment I had to step outside in the disguise. “What about when Jimmy comes home? Is he going to see me like this?”
“He’s going to be out late tonight—he’s got chess club and then he’d got his karate class after that. But tomorrow he might see you—he doesn’t know you’re here helping me though, so maybe he won’t recognize you. It depends on how good of a job you do with your makeup.”
“But if he recognizes me, then the whole school will find out about this. Everyone will come to the house after school to see me like this. You’re going to ruin my whole reputation!” I said. I was already considering dropping to my knees and begging her to think of a different punishment. I would even accept a daily whipping if that’s what she wanted.
“Then you’d better pay close attention, so no one recognizes you,” she said. “Now where were we? Oh right, the eye shadow. I always do eye shadow before eyeliner—that way I don’t smear my eyeliner with my brushes. Now I want to do something dark—maybe with a hint of purple. What do you think?”
I was too nauseous to respond. Now, all of my willpower was set on not throwing up all over her pristine bathroom. I took a series of deep breaths and I watched as my face transformed. She tried to explain contouring to me, but my ears were ringing and I couldn’t hear more than five words in a row before zoning out completely. Though I did hear when she said, “This will probably make you the most unrecognizable.” So I tried to watch as she brushed dark shadows under my cheekbones and on the sides of my nose.
And when she was done, I really was unrecognizable. Though when I looked closely at the mirror, I could still recognize myself. So I just had to pray that no one would look too closely at me.
She went and found me a pair of sandals, which surprisingly fit. Jenna was extremely excited to discover that I was the same shoe size as her daughter. “That makes this all so much easier,” she said, and I wasn’t sure what she was talking about. “Now you can go out and pick up all those egg shells. The garbage bags are under the sink. Have fun!”
I got a garbage bag and then I found myself standing at her front door, looking out the small peephole, watching as cars drove by. A young woman was strolling past with a stroller, and about ten paces behind her was a man on his cellphone. Then I looked at the rose bushes—there were a dozen in total. It wasn’t going to be a quick job. People were going to see me out there.
I took a deep breath and stepped out. I tried not to make eye contact with any of the pedestrians or the workers up on the ladders. I went straight towards the first rose bush and I started picking up little bits of shell. A light breeze picked up the skirt of my dress. I dropped my garbage bag and reached down with both hands, stopping my dress from flying up like Marilyn Monroe standing on a subway grate. The dress was so light and dainty—why couldn’t she have given me a more conservative dress—something ankle length—something that would hide my bum from all of these strangers?
I looked up and saw that one of the workers was looking down at me. I didn’t look for long enough to decide if he was about to laugh at me or if he pitied me. I went back to picking up eggshell bits and I just assumed he was having a good laugh. When the next breeze came, I was ready for it. I threw one hand down between my legs—though my one hand wasn’t enough to stop my skirt from lifting in the back. I’m not sure how much of my bum became visible to the public in that moment—I could only hope it wasn’t the whole thing.
Getting the eggshells that were under the bushes was tricky. I had to get down on my hands and knees and I had to carefully crawl under each bush—and then I couldn’t make any sudden movements, or I would risk getting scratched by the sharp thorns.
Jenna came out and brought me a glass of iced tea. A perfect lemon circle sat on the meticulously salted rim. “It looks like you’re doing a good job, Chelsea,” she said. Apparently she’d decided that my name was Chelsea. Where she got the name from, I have no idea. It wasn’t the worse name—I didn’t mind the name Chelsea. In junior high school, there was a girl I liked named Chelsea—I wonder what happened to that girl…
I was bent down, underneath one of the bushes at the front of the lot, when a man whistled from across the street. I looked back and saw that he was looking at me—right at my ass. A breeze had flipped my skirt up onto my back, exposing my whole tush to anyone who wanted to see it. I looked away from the man quickly and I fixed my skirt. My heart was somewhere in the pit of my stomach. This really was torture. Everyone was mocking me—and I still had six more days to endure.
I went inside with my bag of eggshells. I’d accumulated a surprisingly large amount of the shell bits. Jenna was in the kitchen, getting dinner started. She looked over at me. “All done?” she asked.
“I think so,” I said.
“Tomorrow I’m going to make you talk like a girl too—so maybe tonight you can practise your voice. I’ll be having some friends over for tea. Some of them are mothers of kids at your school, so getting your voice down would probably be in your best interest.” I didn’t think that my stomach could sink any lower into my gut. “But for today, I think you’re done. You did a good job—I really appreciate all the help, Chelsea—I really do. It kills me to have to punish you like this, but I told your mom I would do it.” A smile crossed her face. “Oh—I think I have an idea of how I can make it up to you. Here—follow me. This way.”
She headed back up the stairs. This time she went into her bedroom. She told me to take a seat on the bed. I took a seat and found myself facing a full-length mirror. I stared at myself for a moment. I kind of did look like a chick. Seeing myself in that dress and wig made me wish I had broader shoulders and maybe some muscle on my arms. I never really realized until that moment that I was thin like a girl—I always knew that I was thin, but I always just thought that I was boy-thin… whatever that means.
“Flip up your skirt,” Jenna said. So I flipped up my skirt. Then she sunk down to her knees and reached towards my crotch. I became tense and frozen as she slipped her fingers under my panties and grabbed my cock. She pulled it out.
“What are you doing?” I asked sharply. I reached down to cover up but she wouldn’t let go. I didn’t want to jump back suddenly and injure my private bits.
“Consider it a thank you for the help today. Do me a favour—reach into the nightstand and grab the little purple bottle in there. Yep—that’s the one.” I handed her the bottle. She popped it open and then squirted a large glob of lubricant onto my cock. Then she started stroking. I was still tense and upright like a slab of wood. Was this really happening? Was Jimmy’s mom really giving me a handjob?
I looked down. The skin on her hand was loose and adorned with faint wrinkles that were moisturized twice daily. She had light sunspots on her hands and up her arms. And she held my cock with the perfect grip. She twisted slightly as she pulled up my cock, and then she pulled back slowly, making sure to pull my foreskin back completely. She had me rock hard in a matter of thirty seconds. “How does that feel?” she asked with a big smile.
I nodded my head, unable to think of any words. My lips were parted but I couldn’t close them. I wasn’t sure if I was breathing properly or not. Finally I was able to take a deep, sharp breath in. She squirted more lubricant onto my cock. Now her hand was making a squishing noise as it stroked the length of my rod.
“Just let me know when you’re going to come—okay, sweetie?” she said. That’s when I noticed she already had a wad of tissue paper in her other hand, ready to catch my load.
“I think I’m going to come soon,” I said. I could feel my face turning red. I wasn’t lasting long. I tried to clench to hold my orgasm back, worried she would think I was a premature ejaculator—which is exactly what I was. I bit down hard on my tongue, but nothing could hold that orgasm back. She was too good with her hands—she knew exactly where to rub and she knew just how much pressure to put in. She held the wad of tissues over the tip of my dick and then I erupted. Once I started coming, she started rubbing just my tip with just her thumb and pointer finger. She pulled upwards firmly, getting every last drop out of me, and then she discarded the tissues into the waist basket next to the bed. She grabbed another wad of tissues and used them to wipe the excess lubricant off of my cock.
“You can go home now, darling,” she said. “I’ll see you in the morning—bright and early. My friends will be here at eleven, so you should probably come around eight so we can get everything ready.”
She left me alone in that room with my cock still upright and throbbing. I looked forward at my own reflection, which now looked especially ridiculous: a dolled up young woman with a large throbbing erection. It wasn’t something I ever thought I would see in a mirror.
I stood up and quickly got undressed. The makeup wasn’t so easy to get off. I spent ten minutes in the bathroom scrubbing my face with face wash and hot water, and still there was a bit of mascara in my eyelashes.
As soon as I had my proper clothes back on, I got out of that house as soon as I could, making no eye contact with any of the workers on my way out. I couldn’t hear them snickering up on their ladders, but I knew it was happening. I didn’t bother looking back to confirm my suspicions.
CHAPTER V
Day two of my sissy punishment started out rough—before I even got out of bed I was feeling like crap. I’d only gotten maybe a single hour of sleep—I’d finally drifted off when the sun was coming up, and then my alarm went off. Maybe I didn’t even get twenty minutes—it felt like I’d gotten nothing. I had forty minutes before I needed to be at Jenna’s house but I wasn’t even sure I was going to be able to pull myself out of bed.
I started wondering what would happen if I bailed. My mother would probably ground me for the rest of the year, but I was wondering now if I would be better off grounded for the rest of the year, instead of getting dolled up and paraded around for the rest of the week. I still couldn’t believe Jenna came up with such a cruel punishment—she was such a nice lady, so where did she get such an extreme idea?
I finally peeled myself out from my bed around 7:30 AM. My parents had already left for work. I brushed my teeth and I rolled some deodorant onto my pits, and then I shuffled down to the kitchen to make myself some breakfast. But by the time I got a bowl and a box of cereal out, I realized I had to go—Jenna’s house was a fifteen minute bike ride away, and it was now 7:45. So I left the bowl on
the counter along with the box of cereal, and I took off. I arrived right on time, but I was hesitant to go into the house. I knew she was in there, waiting for me, with an outfit already picked up. I knew I had to do my own makeup, and then I was going to have to serve a group of women—the mothers of my friends at school. One little slip and my friends would surely find out and my reputation would surely be ruined. I hadn’t practiced my feminine voice at all like I was told to—my parents had been home all evening and I didn’t want them to hear me repeating lines with a girly voice. I didn’t want my parents to know that my old friend’s mother was dolling me up.
I walked up to the door slowly and then I checked my watch. I was late now, but I wasn’t too worried about it. Jenna didn’t seem like the type to crack down on small mistakes—not like Principal Andersen. But as I stood on that doorstep, I wished I was spending my week with Principal Andersen—he would have just made me do endless amounts of homework and studying. Homework and studying at least weren’t humiliating.
I didn’t ring the doorbell, but the door opened regardless. Jenna was standing in the doorway with a big housewife smile on her face. Her hair was done up into an immaculate up-do, her dress was freshly ironed and perfectly tailored, and her toes were newly painted and slipped into a pair of open-toed heels. “Ian! So nice of you to make it this morning,” she said, as if I’d been given the choice. “Come on in, come on in! You’ve got a lot to do this morning before our guests arrive. You need to get started right away. But first, you look hungry. Did you eat? I’ve made some fresh breakfast melts. They’re for our tea in a few hours, but I made a few extra. I had a feeling you would come hungry. Have one. They just came out of the oven.”
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