I hadn’t even taken three steps into Jenna’s house and there was a plate of fresh breakfast melt’s being thrust towards me: ham, egg, and melted cheddar inside of a steaming English muffin. I ate one, and then I ate a second one. And then I looked up and there was a plate of warm cookies being held out in front of me. “They’re peanut butter. You aren’t allergic, are you?” So I ate a few peanut butter cookies, and then I was stuffed.
Jenna showed me up to Linda’s bedroom. She had it all set up for me: the dresser was covered in makeup supplies, there was an outfit laid out on the bed and a pair of heels on the floor below it. The wig was on a mannequin head, and it looked like it had been brushed, and possibly styled as well. “Go ahead and get started. I’m going to be very busy in the kitchen, so you’re on your own. I hope you were paying close attention yesterday.” She left me alone with the whole ensemble.
So I did my best to imitate what she’d done the day before. I got into the little white and red striped dress she had laid out for me, and then I slipped out from my boxers and I pulled the fresh pair of panties up my legs. I got into my wig and then I looked in the mirror while trying to remember which step came next. I looked down at the dresser, at all of the different makeup options. Was it he concealer that she started with? The powder? No—it was the foundation. I grabbed the foundation and I started rubbing it all over my face. The cucumber-esque scent of the foundation made me remember the day before with more clarity. Jenna had done my eyes next, so that’s where I went. I grabbed the mascara and gently rolled it onto my eyelashes. I could already see the transformation happening in the mirror.
I didn’t do the best job—not nearly as perfect as what she’d done on me the day before—but I was satisfied with how I looked. I was especially satisfied with how unrecognizable I was. I started repeating a few lines over and over, trying to get used to a feminine voice. I had no idea how I sounded. I didn’t even have my phone to record myself, so I was stuck trusting my own ears. While I was repeating lines over and over, I looked down and noticed the hair on my legs. It had to go—if the visiting mothers were going to think I was a real woman, then I was going to need smooth legs.
So I found myself in Jenna’s upstairs bathroom. I found a razor in the medicine cabinet, and I found some shaving cream in the vanity drawer. I ran the tub and hiked up my dress and then, after taking a deep breath, I shaved away my hair. I was October and the weather was getting colder. By the time it was warm again, my hair would be grown back—so I wasn’t too worried.
Jenna knocked on the bathroom door. “Are you almost done? I need some help setting up. My friends are going to be here soon.” I wasn’t wearing my watch, so I had to ask for the time. “It’s 10:30,” she said. My heart skipped a beat. 10:30!? I’d been getting ready for over two hours?
“I—I’ll be right out,” I said. My legs were suddenly trembling. I’m not sure how I managed to stay up in my little heels. Her friends were going to be showing up in just thirty minutes. The fact that I would be facing my friends’ mothers suddenly seemed very real—and very terrifying. I took a series of deep breaths, but somehow that only made me feel sicker. I looked in the mirror. At least I actually looked like a girl… Though I wasn’t sure that was any consolation…
CHAPTER VI
Jenna had managed to turn the kitchen into an immaculate space in those two hours that I was upstairs getting dolled up. Her entire kitchen island, which was at least twelve feet long, was covered in plates of snacks: breakfast foods, desserts, cured meats, cheeses, and baked goods. She had a jug of homemade iced tea cooling in the fridge, and there were candles burning throughout the room.
Jenna looked up at me as I stepped towards the kitchen. Her face lit up with a big smile. “You look lovely,” she said.
Once again, the dress felt incredibly short. I wasn’t convinced my ass wasn’t hanging out. I wasn’t used to my legs being so exposed. Even when I wore shorts, they extended down to my knees. I wasn’t sure if my thighs had ever seen sunlight—but they were seeing sunlight now, through Jenna’s large picture windows. I tried tugging down the skirt of my little dress so it would cover more, but I almost ended up pulling the dress off of my body. I had to be careful—the little outfit was only being held up by two dainty straps on my shoulders. If the dress came off, then everyone would see my padded bra, my cock bulge, and my boyish body.
“Why don’t you salt the rims of the glasses? You’ll have to set up a salting station—the decorative salt is in that cupboard there and the little bowls are in that cupboard there.” I could feel my curled hair bouncing with each step that I took. It was a strangely satisfying feeling, though I wasn’t sure why. Even the pads in my bra bounced slightly, as if they were real tits. I’m not sure what Jenna used to make the pads, but they even felt sort of real to squeeze, as if there was a latex or silicone inside of them… Knowing Jenna, I’m sure she used something expensive and authentic.
I was still getting used to the heels. I wobbled slightly as I reached up for the decorative salt, and then I wobbled slightly again as I bent over to grab a small bowl to pour the salt into, so I could rim the glasses. I was walking back to my little open station on the counter when I noticed Jenna was staring at me. “You need to work on that, dear,” she said.
“Work on what?” I asked.
“Your walk. You look so—I hope you don’t mind my saying this—brutish. A woman should look elegant when she walks. Try stepping one foot in front of the other—like this. See? Keep your back straight and lead yourself with your hips. Good, just like that!” I felt silly, as if I was pretending to be a model on a catwalk, but I welcomed the advice. I didn’t want to give any of the visiting ladies any excuse to think that I was actually a man under that dress and that wig and that makeup.
There was a knock at the door. A cool shock ran up my spine and I became tense. I turned slowly to the door and could see the up-do of the first guest through the small crescent window at the top of the door. “There’s our first guest. Why don’t you answer it, Chelsea?” Jenna said.
My stomach turned and my legs were suddenly trembling—almost buckling at the knees. I held onto the edge of the counter. I couldn’t let anyone see me like this—I would never be able to forget the humiliation. As I stood there terrified, I couldn’t even think of anything more humiliating. It would have been less humiliating to answer the door completely naked, jerking myself off with some questionable porn playing in the background. Pretending to be a lady was a whole new low that I couldn’t even begin to wrap my head around.
“Well? Don’t leave her waiting out there. A good host takes no longer than fifteen seconds to answer the door,” Jenna said.
I found myself walking towards the door, but I’m not sure where I managed to find the confidence. I reached my arm out and grabbed the door handle. I was still stiff as I pulled the door open, and I’m sure my face was pale. I opened my mouth to speak, but no words came out. I was staring at a woman I knew: Tony’s mother.
She was staring at me with a big smile. “Hello,” she said. “Is Jenna home?”
I opened my mouth wider to reply, but I was too terrified to speak. I still hadn’t tried my voice out on anyone—not even Jenna. I could feel my jaw trembling. I must have looked so foolish standing there, looking like one of the possessed humans from Invasion of the Body Snatchers. “She—She’s inside,” I finally managed to say. My eyes were dry—I’m pretty sure I hadn’t blinked since opening the door. “C—Come on in,” I said. I stepped aside.
Tony’s mom looked at me strangely, still with that smile on her face, and then she walked into the house. “Thank you,” she said. But she still hadn’t figured out who I was—I knew that for sure. If she had recognized me, she would have surely reacted, right? I was fairly sure that my identity was still safe.
As Tony’s mother entered the home, another car pulled up on the street. I recognized the woman who emerged from the vehicle: it was the mother of another friend of mine. And t
he next mother to show up was also the mother of a friend. I was starting to worry my own mother was going to show up for the tea party.
I greeted everyone at the door. I had to fight myself to stare into their eyes. I was terrified they would see into my eyes and recognize me, but I was more terrified that I would shyly look away and immediately look suspicious.
CHAPTER VII
The ladies were over for three hours total. I served appies through the room while everyone mingled, and then I cleaned dishes as guests finished with them. Throughout the first hour, I probably yanked down on my skirt one hundred times, trying to make sure my ass wasn’t out for all the party guests to see. And then I started getting used to the little outfit. By the third hour, I wasn’t pulling down on my skirt at all. In fact, I would find myself stopping whenever I passed a mirror, just to check myself out. I looked good. And my reflection served as a nice reminder that I wasn’t recognizable—I could relax knowing that no one would recognize me as long as I didn’t have a wardrobe malfunction or a voice slip.
When the ladies left, I started the long process of cleaning up. I must have washed two hundred dishes. And then I swept the floors, and then I mopped. I had the house all to myself, as Jenna was out back, hanging decorations for her upcoming Halloween party.
I ended up finishing the cleaning process sooner than expected. The house was shining as if Jenna had cleaned it herself. So I slipped into the backyard to ask what I could do next. I was shocked by how much the yard had transformed in just a matter of a few hours. There were little ghosts hanging from every branch, jack-o-lanterns along the fence and along the many paths through the large yard, and she’d even managed to set up a speaker system, which would play Halloween classics like Thriller and Monster Mash during the party.
“It looks great out here,” I said. And then I realized I was still using my girly voice, even though all the tea party guests had already left. But maybe it was for the best—maybe I was better off getting used to the feminine voice, in case Jenna threw any more parties with all of my friends’ moms.
“Thanks, sweetie,” Jenna said. “How’s it going inside?”
“I think I’m all done,” I said.
“That’s great. You’ve still got a couple hours before I can send you home. Why don’t you go and tidy up the upstairs bedrooms?”
She continued to set up the exterior, and I went up to the bedrooms to get them nice and clean. They were already clean—I couldn’t even find any dust, but I figured I would give them a safety vacuum and a mopping, just for the sake of something to do more than anything.
I got down on my hands and knees to get into the corners of her wainscoting. I was getting around her bed when I noticed a small box hidden behind her nightstand. I slipped it out and then I looked around before opening it. Inside was a number of small sex toys, and one not-so-small sex toy. I lifted it out. It was a flesh-coloured dildo with a suction-cup base. It was slightly floppy and surprisingly heavy. I wondered if Jenna fucked her pussy with it—of course she did; why else would she own it?
I looked into her closet mirror and saw myself holding the large dildo. I looked shockingly sexy with the thing in my hand, as if I was on the poster of some kinky porno. I lowered the dildo to my crotch and I rubbed it between my legs, pretending to be promiscuous. But the sight was surprisingly erotic. I ended up getting hard watching myself. And that’s when I got the idea to slip into the bathroom with the toy and the little purple bottle of lubricant, which I knew was in the nightstand drawer.
My heart was pounding as I wet the suction-cup base so I could stick it to her bathroom’s tile floor. I looked down at the cock, which was standing straight up, wobbling slightly. I wondered if I could actually do it—if I could insert it into my asshole.
I’d never fucked myself in the asshole before, and I’d never even wondered if I would be able to do it—or even if I wanted to do it. But seeing myself in that skimpy little dress, I found myself with a head full of thoughts that didn’t seem to belong to me. I was feeling risky and kinky and strangely horny. I slipped my panties down to my feet and then I stepped out of them. I lowered myself down, squatting over the dildo, and my heart started pounding even more. I poured some lubricant on the toy. Now my heart was out of control. I was starting to worry I was going to have heart failure right there, and my body would be found in a dress next to a suction-cup dildo. Thankfully I didn’t have a heart attack as I lowered myself down further.
I felt the tip of the dildo press against my tight anus. It felt big and dull—too big to fit into my ass, surely. But I still wanted to try—though I still had no idea why I wanted to try. I hated myself for being in that bathroom, squatting over that thick fake cock. I hated myself for agreeing to dress up like a little slut. I was quickly running out of reasons to like myself.
I took a deep breath and I let gravity bring my body down lower. I thought the dildo would just bend under my weight and that would be that—but it ended up penetrating me, and it quickly sunk deep with some help from all of the lubricant I coated it with. I nearly screamed. It didn’t hurt but it sure felt strange—like my body was suddenly full—like someone’s entire arm had penetrated my butthole.
I covered my mouth and I forced myself to sink lower, just to see how much of the artificial cock I could take. I sunk lower and lower, doing my best to control my breathing every inch of the way. And then suddenly my butt cheeks were pressed against the heated tile floor. I had the whole giant dildo pressed up my ass. I wasn’t sure if I was supposed to be disappointed with myself or impressed.
But it still didn’t feel good—it just felt like my ass was suddenly occupied with a very large object. I wasn’t sure why gays loved taking it in the butt so much, but I was still willing to give it a shot. So I started to bounce up and down slowly, feeling the false veins rubbing against my anal walls. It felt weird, but I kept going. I was enjoying it—not because it felt good, but because I looked so sexy. I couldn’t keep my eyes off of the mirror in front of me: my own beautiful reflection staring back at me while she pumped her ass with a long suctioned dildo. I reached up and grabbed my tit so that I could watch her grab her tit. Fuck, she was hot—I was hot. I really made a sexy woman.
I bounced faster, pressing my bum against that warm tile floor harder. I started moaning slightly and then I covered my lips again. My legs were trebling. I couldn’t believe that I was doing it in high-heels. “Fuck, that feels good,” I heard myself mumble in my girly voice. I was starting to like my girly voice—it was sexy. It was fun being sexy. It was satisfying knowing that I looked so good.
I started moaning louder, so I pressed my palm against my lips harder. It was starting to feel good inside of my ass—really good. My legs were shaking now. I had to plant a hand down on the floor to keep myself from falling over. I looked down and saw a puddle forming on the ground, just in front of the dildo. It was a white puddle and the thick fluid was pouring out from my flaccid cock: I was coming. I couldn’t believe what I was seeing—I hadn’t even touched myself, and there I was, unloading all over the bathroom floor. And my God, did it ever feel good.
There was a knock at the door. “Chelsea, are you in there?” Jenna’s voice said.
I froze. My cock was still drooling cum. “Uh, yeah—I’m in here. Just using the potty,” I said.
“I just wanted to let you know that you’re done for the day—you can go home now!”
“O—Okay. I’ll start getting changed then.” I stood up, slipping the cock out from my ass. Suddenly I felt emptier than ever before. I quickly cleaned up my cum puddle using a wad of tissues, which I flushed down the toilet, and then I stepped out from the bathroom, to retrieve my clothes from Linda’s bedroom. And as I stepped out, I found myself face to face with Jimmy, who had just come home from school.
“Hi,” he said, looking into my eyes. His gaze slowly drifted down my dress, to my legs, to my feet, and then back up again. He looked back into my eyes and his cheeks turned a shade
of red. I was waiting for him to point at me and scream, ‘Ian! Why are you dressed like a girl in my house?!’ But instead he said, “Who are you?”
There was a lump in my throat the size of my fist. I tried to swallow it, but it wouldn’t go down. So I forced myself to speak through it. “I’m Chelsea. I’m helping your mom with her party coming up.”
Jimmy nodded slowly. “How do you know my mom? Do you go to my school?”
I shook my head. “I, uh, know your mom from the Internet. We met on the Internet. She was looking for, uh, someone to plan interior designs with.” I knew I sounded ridiculous. I knew I sounded like a complete knob—but I couldn’t think of anything else. I was sure he was about to recognize me at any moment. He was looking right into my eyes, and my eyes were still my eyes. I wasn’t wearing coloured contacts and I hadn’t modified the shape of my eyelids. But still, he seemed oblivious.
“Well you look familiar. Maybe I’ve seen you around the house before, I guess,” he said, and then he continued on towards his bedroom. And it wasn’t until the door closed behind him that I realized I was holding the suction-cup dildo behind my back. Thank God he didn’t see it…
CHAPTER VIII
My third day at Jenna’s house wasn’t so bad. She only had one guest pop over, and it was a woman I’d never seen before in my life. They had tea together while I pruned the rose bushes out front. I was actually a big fan of my outfit for the day: a green plaid skirt and a black blouse. Jenna let me help myself to her costume jewellery, so I grabbed a few faux-gold bracelets and a cute black choker, which helped to hide the slight bulge of my Adam’s apple.
I got a few catcalls from people on the street. A car drove by and honked at me, and a young man leaned out the back window and yelled, “Hey beautiful! Want to grab a drink with me sometime?”
GIRLIFIED: 15 BOOKS MEGA BUNDLE Page 38
