I blushed and continued working. Then he yelled, “Playing hard to get, huh? I’m a nice guy—you’re beautiful and I’m nice. It’s the perfect match, don’t you think?”
“I don’t think you could handle me,” I called back, and his friends all laughed. They drove off, leaving me feeling flustered and glowing.
Another group of young men whistled at me before I went into the house for lunch. One of the men asked me to flash my tits—which I didn’t, of course, seeing as I had no tits to flash. But I did turn around and lift up my skirt, showing him my tush. That got a good rise out of him, and the group of young men left satisfied.
Jenna made me a sandwich for lunch. It was turkey, bacon, Havarti, lettuce, tomato, and ranch dressing on fresh whole wheat bread. She also gave me a mug of warm barley soup to go with the meal, and a glass of her homemade iced tea with the salted rim. It was delicious—one of the best lunches I’d ever eaten in my entire life. I had the biggest smile on my face until she said, “I know what you were doing in the bathroom yesterday. That was very naughty of you.”
I felt all of the colour drain from my face as I looked over at her slowly. She wasn’t kidding around—she really knew that I’d taken her dildo and fucked myself with it. “I hope you know that I have to punish you now—a young lady shouldn’t go through someone’s private things.”
“I—I’m sorry,” I said. My lips suddenly felt dry.
“Follow me upstairs so we can get this punishment over with, so we can put this whole thing behind us.” She started ascending the stairs. I was slow to follow, my heart still pounding ferociously. I was feeling a whole new level of humiliation—beyond what I thought possible. My friend’s mom knew that I’d stolen her dildo and stuck it up my ass. I had no idea how she knew, but I wasn’t surprised that she knew. Her house was so perfect and so meticulously organized—she probably saw that her little sex toy box was one inch out of place.
I followed her into her bedroom. She pulled that box out from behind the nightstand and then she pulled out a little purple egg-shaped device with a long wire sticking out of it. “Get up on the bed, on your hands and knees like a kitty cat,” she said.
I was too terrified to argue with her—too terrified to even plead for my life. So I climbed up on the bed. I got up onto all fours and then she walked around behind me. She flipped up my skirt and then she tugged down my panties. I looked back and saw her squirting lubricant on the egg device, and I knew where it was going. “I’m really sorry. I was just… I was just curious,” I said. “I cleaned everything—and I was only playing with it for five minutes—maybe less.”
“I still have to punish you. Now take a deep breath.” I felt her press the egg up to my butt. I took a deep breath. I was clenching, but I couldn’t unclench. She started by sticking her pointer finger into my asshole. She pushed it deep and then she pulled it out until the tip of her finger was teasing my rim—and then she pushed it in again. She was trying to get me to unclench. I closed my eyes and took a deep breath. I managed to unclench for a few seconds, which was apparently long enough for her to press the egg into my asshole.
I perked up and all of the muscles in my body became tense. The whole egg was in my ass. How was she going to get it out? I clenched and tried to push it out, but it wouldn’t budge. “Calm down,” she said. “It’s not going to hurt you. It’s a new toy I got a few weeks ago—I didn’t realize it was for boys when I got it, so I haven’t had any reason to use it until now. Now prepare yourself—the vibration is pretty intense.” She pressed a button on the end of her long wire, and then I felt the inside of my ass vibrating. I became tense again, clutching the bed sheets with both hands.
I squirmed but she held me in place. “It should only take a minute,” she said. “Just stay on your hands and knees. Warm me if it’s about to happen.” I didn’t know what she was talking about. But I could feel something happening: a warm euphoria growing between my legs. The vibrating felt good, and it was pressed right against my sweet spot. My legs trembled. Jenna gently rubbed my bare ass with her frequently moisturized mature hands. “Does it feel good?” she asked.
I nodded. “It feels good,” I said. I let a moan slip. I felt so humiliated, and that humiliation was only growing stronger with every passing minute that I was being harvested like a prized bull. Jenna gently reached between my legs and ran her gentle fingers up my shaft. It felt so damned good. I let out another long, loud moan. I looked over and saw myself in the reflection. I liked the way I looked—I looked especially cute with my dark red cheeks. “Oh God, it feels so good. I think it’s happening—something’s happening.” There was a hot sensation filling my cock. I felt like I had to pee, and I was worried I was about to pee all over Jenna’s bed. But instead, I started coming, and Jenna was ready for it.
She held out the palm of her hand and caught every blast. A small pool filled the palm of her hand after thirty seconds. Then she carefully brought the palm of her hand up to my face and said, “Now for your punishment. Swallow all of it,” she said.
My heart skipped a beat. I looked down at the little puddle—which was a surprisingly large amount of cum. I closed my eyes and took a deep breath. Then I leaned forward and sucked up the cum. It didn’t taste as bad as I was expecting—just warm and salty. That saltiness lingered in my mouth. I swallowed all of it in one big gulp. Then she gave me a nice pat on the ass. “That’s a good girl. A proper lady always swallows—remember that,” she said. And then she headed back downstairs to continue preparing for her big upcoming party, as if nothing had happened.
I reached around and tugged on that wire. I had to pull hard to get the egg out from my asshole. It was still vibrating as it hit the bed. And once again, I found myself feeling emptier than ever before.
CHAPTER IX
Day four went by shockingly fast. I did a bit of gardening, and then it was suddenly lunch. Then I did a bit of decorating, and it was suddenly time to go home. Jimmy came home and I waved at him as he went up towards his bedroom. He blushed and waved back, and then I found myself laughing—he really thought that I was a chick. He really had no idea who I was.
Day five went by too fast. I knew that I only had one day left before the party, and I knew that my time as a pretty girl was coming to an end. Soon it would be back to normal—going to school as myself: jeans, t-shirts, hoodies, and nothing more than that. There would be no more skirts, no more dresses, no more lacy panties, no more stockings, no more heels, no more bracelets, and no more chokers. There would only be one was to style my hair, and makeup would once again be off limits. So I tried to revel in the final couple days of my sissification.
I spent extra time in the morning doing my hair and makeup. And then I spent some extra time admiring myself in the mirror. And as the hours passed, I found myself feeling sad—knowing that I was one hour closer to being Ian—my regular old self. But I knew it was for the best. I knew I wasn’t supposed to be enjoying myself. It was supposed to be torture—I was there as punishment, after all.
I only had an hour left of my fifth day when there was a knock at the door. “He’s early,” Jenna said. “Do you mind answering that for me?” So I went to the door, though I didn’t know we were expecting any company. I didn’t look through the peephole before opening the door, seeing as I didn’t know too many of Jenna’s friends anyway. But I knew the man at the door.
It was Principal Andersen. My heart stopped as I looked into his eyes. “Hello there,” he said. But I didn’t respond. I was petrified. I didn’t know what to say or what to do. Was this the man Jenna was expecting?
“Principal Andersen! Come on in! Can I get you a tea or a coffee?”
“A tea would be great,” he said. He looked at me again before entering the house. I still hadn’t uttered a word. He left me standing in the doorway, confused and terrified.
“That’s Chelsea. She’s helping me prepare for the party this weekend,” Jenna said. Principal Andersen looked back at me again, and I became a p
etrified statue all over again.
“Shouldn’t she be in school? She looks awfully young to be a graduate.”
“She graduated last year, isn’t that right, Chelsea?” Jenna said. She winked at me. I managed to force a smile and a nod. But I still wasn’t able to speak.
Principal Andersen looked around the house. “Well it looks like the two of you have done a tremendous job so far. I can’t wait to see it finished.”
“I can’t wait for you to see it finished. So were you able to get the smoke machine?”
“It’s in the trunk. I’ll need a hand getting it into the house—it’s awfully heavy.”
“Thanks so much for bringing it,” Jenna said.
“It’s no worries. The thing’s been sitting in the gym storage for eight years. I almost couldn’t find it; it was lost under an inch of dust.”
“Well thanks for going through the trouble of dragging it all the way over here. Chelsea, why don’t you give Principal Andersen a hand with the smoke machine?”
I tried to say ‘okay’ but I was still at a complete loss for words. Principal Andersen walked by me, out towards his car. I was slow to follow. I looked back at Jenna who was motioning for me to go—so I went. Principal Andersen popped his trunk, revealing a large black box with thick tubes sticking out of it. “So just take an end. It’s heavy.” He looked up at me. “Did you graduate from Dover?” he asked.
“No. I, uh, went to a school in Surrey,” I said, lying.
“Oh. Which one?”
“Madison High,” I said. I didn’t know any schools in Surrey, so I just made one up. I watched as Principal Andersen’s brow lowered.
“I don’t know it,” he said.
“It’s a small school.”
He stared at me for another long moment, directly into my eyes. “You look so familiar,” he said. I looked away quickly.
“I get that a lot,” I said. I grabbed one end of the heavy fog machine—and it truly was heavy. I had to yank with all of my strength just to get it out from the trunk, and then it nearly fell on my toes. Thankfully Principal Andersen was able to get his arms around it before it toppled over. I grabbed my handle again, but not before noticing the tan line around his ring finger. He wasn’t wearing his ring—had he lost it? Or had he taken it off before showing up at Jenna’s house?
We hauled the heavy fog machine into the house. “Where should we put this?” Principal Andersen asked.
“Just in the back yard. You’ll see an extension cord running along the fence—just put it at the end of that cord.” I watched as Principal Andersen’s gaze quickly explored Jenna’s body. He had a crush on her. Of course he did—why else would he be doing her a favour? He didn’t do anyone any favours, ever. He was a selfish little man.
We hauled the fog machine out into the backyard. We put it down while we looked around for the extension cord. I spotted it running along the eastern fence. And it ran all the way down her entire property, which was over an acre. We had to pull the heavy thing down her winding stone path and across the little bridge that went over her little pond. I was worried the combined weight of Principal Andersen, the fog machine, and me would be enough to make the bridge collapse, but somehow it remained intact. We finally plopped it down in the back corner of the large lot.
Principal Andersen looked around as he caught his breath. “You guys really are doing a phenomenal job out here,” he said, admiring the little ghosts hanging from the branches.
“Jenna’s done most of the work,” I said.
“She’s really good at this kind of stuff, huh?” he said.
“Yeah,” I said. I looked around the yard at all of Jenna’s hard work, and then I looked back at Principal Andersen. I couldn’t help but notice he was staring down at my body, checking out my tush. He looked up quickly once my gaze was back on him, but not quickly enough. His cheeks turned a shade of pink. “You really do look familiar,” he said—and I didn’t believe him anymore. Now I was fairly sure that he was just making up an excuse to stare at me. He kept looking down at my body, as if my body would spark his memory.
Principal Andersen was a secret pervert. And out of nowhere, I had the urge to tease him. “You know you’ve got some white stuff on your pants,” I said. He looked down and saw the white stuff I was referring to—some residue from the fog machine. He reached down to wipe it off, but I beat him to it. “Let me get it,” I said. I started wiping his thighs, and I moved north with every wipe. He became tense as my fingers brushed over his crotch. I could feel his bulge. I brushed again. “This one is tougher to get out. It might need a really good rub,” I said. So I sunk down to my knees and I started rubbing his crotch, even though the white powdery residue was now gone. He didn’t protest. I stopped and looked up at him with big eyes. “What is that in your pocket? It’s so big. Is that your phone?” I said, wrapping my fingers around that bulge. I could feel it pulsing now.
He laughed nervously. “Are—Are you thinking what I’m thinking?” he said.
“That depends on what you’re thinking,” I said. I slyly slipped one of my bracelets off and I left it on the ground as I stood up. Then I looked down and said, “Oops, my bracelet fell off.” I turned away from him and then I bent over to pick up the bracelet, keeping my legs straight and showing off my whole tush. I took a few extra seconds than necessary to pick up the bracelet, which was just enough time for his hands to find my bare ass cheeks. He caressed them and then he squeezed.
“You’re so young and tight,” he said, his voice low and shaken.
“You really think so?” I said, remaining bent over. I was smirking, trying not to laugh. I wasn’t sure why I was getting such a kick out of teasing Principal Andersen—but I really was getting a kick out of it. I stood up straight. His hands remained on my ass for a moment before sliding up my sides. He cupped my breasts.
“And your breasts are so perky,” he said. He squeezed. I let my head rest back against his collarbone. I turned my head and looked into his eyes. I could feel his cock becoming erect against my tush.
“What is that against my bum? It’s so hard,” I said. “And it’s so big.”
“Give me your hand and I’ll show you,” he said. So I gave him my hand and it began to press it down the front of his pants. I could feel his soft pubic hair, and then I could feel his warm, hard cock. I wrapped my fingers around it.
“Is this your penis?” I said.
I could hear him smirking. “Do you like it?”
“I’ve never touched a penis before. Are they all this big?”
I felt his nose nestle into my hair and I felt his warm breath teasing my scalp. “No—this one’s special, baby. Just stroke it up and down—yeah, just like that. Oh, that feels good.” He was taking deep breaths.
“We should probably stop before Jenna finds us out here,” I said. I firmed my grip around his cock and I pumped harder and faster.
“I just need a minute—just one minute. Keep stroking. Fuck, that feels good,” he said, right into my ear.
“Like this?” I asked, directing my attention towards his tip. I could feel his throbbing getting more and more intense. His cock was as hard as a marble statue.
“Just like that. Don’t stop. Just give me thirty seconds. I’m already close, baby. You’re so good at that. Don’t stop.”
And he really was close—I could feel his cock beginning to bloat up. I could feel the wet tinge of his pre-cum oozing out from his tip. “A few more seconds,” he said through clenched teeth. And then I pulled my hand out from his pants.
“We should go inside and see Jenna. C’mon,” I said. I caught myself smirking—I couldn’t help it. I’d left him with the bluest balls possible. He was standing there groaning and squirming—probably wondering if he should just finish himself off or try to convince me to finish him off. I’m not sure if he stayed out in the yard and jerked off into Jenna’s bushes, but it was a minute before he came inside to say goodbye to Jenna. I tried not to laugh as he left.
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br /> CHAPTER X
On my second last day as Jenna’s sissy assistant, we spent most of our time in the kitchen, baking cookies and preparing food for the party. She had me do a final clean around the house, which didn’t take long because the house was already immaculate, as always. Jimmy was upstairs in his room. It was Saturday—the day before Halloween. Jimmy was spending the day painting a small squad of miniatures.
The outfit Jenna had set out for me was my favourite of the week: a whitish pink frilly dress, that almost looked like something a ballerina might wear. I wore the knee-high white stockings again, and a pair of black heels. Jenna taught me how to do my hair into a loose up-do. It was the first time that week that I’d really pulled the hair off of my face—and I was surprised to see that I was actually prettier when my whole face was visible instead of hidden behind long dark hair.
“So tomorrow,” I said, “am I coming in the morning and then leaving at the same time? Or do I have the day off tomorrow?” I said it as if I was hoping for the day off—but in reality, I was hoping I would get to spend one more day as a woman. I wasn’t ready for the fun to end. I wasn’t ready to go back to my normal life—I wanted to keep feeling sexy, just for a little bit longer.
“You can come over again tomorrow,” she said. My heart leapt up into my chest, but I did my best to pretend to be disappointed. “And then I want you to stay for the party. You can serve drinks and clean up, so that dishes don’t start piling up and getting in the way.” My heart suddenly sunk into my gut. I couldn’t stay for the party—all of my friends from school would be at the party. Tony would be there—my own parents would be there! I couldn’t let them see me as a girl.
“You mean as myself, right? Not as Chelsea…” I said.
“No—as Chelsea. I even have your costume picked out and everything.”
“But—But my parents will be here,” I said, my voice shaking.
GIRLIFIED: 15 BOOKS MEGA BUNDLE Page 39