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Author's infos Gender: Male Age: 19 Location: N/A |
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| Introduction: A slender male decides to win $200 for dressing as a girl for a day. | ||
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"Dude, I'm telling you, if you grow a beard, no one will mistake you for a girl. It's that long ass hair." John Said. "Yeah, but I don't want a beard." I told him. My hair is almost to the middle of my back, it's black and straight. Apparently I look like a flat chested girl, because everyone calls me a lady. And, not to tease, people who don't know me just make a mistake. "Alright Seth, but seriously... All you have to do is put on a padded bra and a dress and you're a chick." John said laughing. "Fuck you, man. Even if I dress like a girl, I'm more of a man than you are." I said hitting his chest with the back side of my hand and laughing. "What the fuck ever, bro." We were both laughing. "I bet you 50 bucks that if your skinny ass threw on your girls dress and walked the street, nobody would suspect a thing! I dare you to, haha!" "50 bucks, huh?" I said thinking it over. "Make it a hundred and I'll fuckin do it." I said, knowing he wouldn't put up a hundred. "Alright." He said, and I stopped laughing. "Do it, and I'll pay you a hundred bucks. But, you gotta wear it for an entire day." John said. "Man, an entire day?" I said kinda bummed. "Hey..." Tyler jumped in. "If you wear it for an entire day, I'll throw in an extra hundred." He said waving it in front of my face. I couldn't turn down $200 just to wear a stupid dress. No one would know it was me. I am a very good impression artist and voice actor, that's actually what I do for a living. I could make myself sound like a girl, easily. "Fine." I said blankly, snatching the hundred from Tyler. "I'll do it, just so you fags shut up, everyone will know I'm a guy." "Okay, but we also have to see you do it." John said, handing me his hundred in 20's. "No problem." I said. "But you can't tell anybody else about this shit." "We won't, don't worry." Tyler said starting to laugh. The next day, at 6am before my girlfriend went to work, I told her about the bet. "I need to borrow one of your dresser for it, if that's alright." I said questioningly. "That's fine, but only a dress?" She asked. "You're gonna be one ugly ass girl, and everyone will know it's you in a dress." Gabby said laughing quietly. "What the hell else am I supposed to do?" I said to her sort of giggling. "I don't know..." Gabby started. "Put on a bra and stuff it, and wear my panties so it keeps all your junk from swinging and showing out the bottom." "Well, I was thinking of using a long dress, and my shit doesn't swing that low." I told her. "I only have above-the-knee high sun dresses unpacked, the rest are in boxes in the basement." She explained. "Just do what I tell you, it'll be fine. And, we'll dye your hair a light brown, we can dye it back later." "Dye my hair?" I asked skeptically. "Do you want people to recognize you?" She teased. "Because I promise, they will if you have that hair." "Fine." I gave in. I guess Gabby was right. She dyed my hair a light brow color and then curled it. "I look like a girly headed fuck, already. Do I need a dress?" I said, and she started laughing. After my hair was done, Gabby painted me with makeup. I even thought I looked like a chick. I would probably fuck me. Then, she put a bra on me, and stuffed it with a fake breast implant she had for testing. She said they were 38B. When this was over, she gave me a light red dress, almost pink, and white panties to match the bra. I put on the panties, and my dick was pressed up against me. Gabby said I had a nice ass to be a girl, and it fit perfectly inside her panties. I slipped the dress over my head, and it was tight around my fake boobs, and stomach. Around my waist, it got loose, and it hung around 4 inches above my knees. This dress was really short. It had no sleeves. I was a skinny guy, almost hairless, and pretty tanned. My ass, back, chest, and thighs were baby smooth. "You have to wax your legs and arms, and shave your face completely." Gabby told me. And so I did. It hurt like a mother fucker, but at least I didn't have too much hair. "Okay, here." She said, handing me a pair of flat, black shoes. "This is so you don't have to walk in heels." She said smiling. "But now you're ready to go, and you're a pretty hot girl. I doubt John and Tyler will know it's you. And, it's anti-smear makeup, but don't cry or anything because the mascara will run." Gabby told me, but I never cry anyways. Me and Gabby switched cars, since my friends have never seen hers. I went over to johns at around 3:20pm. I pulled up into John's driveway, and they were sitting on the porch. He gave Tyler a: "who the hell is that?" look, and then I stepped out of the car. "Yeah, can I help you?" John called out. I disguised my voice and said "Mmhmm, I'm looking for um..." I paused and look at my hand, as if something were written their "Johnny Samuels?" I said in a questioned form. "Yeah, just John.." John said. "Who are you?" I undisguised my voice now. "What up bud?" I said smiling. "Holy shit... Seth?!" He exclaimed. Tyler was dying on the right side of him. I was laughing my ass off walking over to him. "Dude!" Tyler screamed. "You are fucking hot!" He was still cracking up so hard, I could barely understand him. "Yeah." I said laughing. "I just wanted a dress, and Gabby did this shit." "Jesus Christ, I can't even tell it's you." John said laughing. "Yeah, just needed you to see." I told them. "I'm gonna go to the mall to see if anyone I know is there." When I got to the mall, I didn't see anyone I recognized. I walked over to the cushioned bench they have along the wall and sat in the corner. I pulled my phone out of one of the small pockets this dress had, and started to text John. Some guy walked up and sat next to me. "Hey." He said. I looked up and realized it was some guy from my english class in college. I didn't know him at all, so I wasn't going to risk letting him know it was me. "How are you, girl?" He asked, putting his right hand on my right shoulder. "Fine." I said in my disguised voice, smiling. The guy's name was Andrew, he had short, dark brown hair, and bright blue eyes. "You looked kinda lonely, so I wanted to know if you'd like to come hang out with us." Andrew said softly, and looked over at two more of his friends at the table. I knew the girl, Becca, but I didn't recognize the other guy. Andrew slid his hand to the middle of my upper back. "Sure." I said, still smiling, and he stood up. "Cool... Let's go." Andrew said, helping me up off the bench. I took his hand to be nice, even though it was a little weird. "You have soft hands." He said smiling. Andrew's voice was so nice and gentle. "Thank you." I said back to him, still exchanging smiles. "I was going to text my friend to meet me here, but now I guess it's fine." I said when we got in earshot of the table. "Yeah, just chill with us, it'll be fun." Becca directed t'wards me. "I'm Becca." "I'm Sami." I said to her. "I'm Andrew, by the way." Andrew told me, while we both sat at the table. "And that's Tim." "Hi." He said holding one hand up to wave, and smiling. "Hey." I said smiling back. They were both pretty broad, a lot bigger than me. Andrew was more muscular than Tim, and had to be 6'5 tall. I was only 5'8. Tim has shiny black hair that reached over his ears, and was wearing all black, except for his neon green shoes. Andrew had on a red shirt, with blue jeans. Becca had long blonde, straight hair that reached her lower back. It really stood out from her dark red shirt. She had on a lacey white skirt, and knee high red and white striped socks. I saw her light brown eyes almost immediately, because blondes don't normally have that. We all talked and had a nice time at the mall. I forgot I was even being a girl, I was just having a fun time. We were there for almost 4 hours. I got there around 4pm and it was 8:47pm. It was pretty dark out, and the mall was closing at 9. Becca went home 5 minutes ago, and now we were leaving. We exited in the back side of the mall, since it was closer. We had to walk In between the mall and another shop sharing the same parking lot. It was a long walk, and no one else was back there. Andrew wrapped his arm around my waist and kissed me on the side of my neck. I pushed him away gently. "Stop it." I said. But I was unknowingly smiling because I forgot I was a "girl." He stepped t'wards me again, and pushed me with his shoulder. I stumbled to the side a couple steps, but I was laughing kind of quietly. He wrapped his arm around my waist again and pushed me up against the brick wall. I was short and scrawny compared to him, but that's why I made a convincing girl. I put my hands on his chest and tried to push him off, but I couldn't get any leverage. He pressed his lips against mine, and forced his tongue inside my mouth. It rubbed against my tongue, and the roof of my mouth. My entire body was against the wall, so I couldn't pull away. Andrew lifted me, and my knees ended up around his waist. I felt his hard cock through his jeans. I put my forearms on his shoulders and tried to pull my mouth off of his. I finally managed to get his mouth off mine. "Ah.." I sighed. "Get off!" And Tim turned around. He saw me pressed against the wall. "Hey you two. Hold on for like five minutes and get a room." He called down to us. "Stop!" I shouted, but Andrew and Tim didn't seem to care. "Tim, get outta here." Andrew said loudly. "Oh, alright buddy." He replied laughing. "Make sure she doesn't get away." And then he walked away. Andrew tried to kiss me again, but I dodged my head to the side. "Don't kiss me." I said. But, he did it anyways. Then he started massaging my fake breast, and I pulled his hand away. "Stop touching me." I demanded. But, Andrew continued. He reached down and pulled the panties off a little ways, only enough to expose my cock tip and asshole. Andrew lifted my legs and my ankles were just over his shoulders, and the stayed there. My hole was wet with sweat. He pulled me down and his cock slid right into my asshole on the first try. I screamed loudly in pain and tightened my grasp on his forearms. Andrew started bucking his hips back and forth, and bouncing me up and down on his cock. He put me down, but still had a hold on me. He turned me and pushed my chest and face against the wall. Andrew unhooked his belt with one hand, and tied my hands together, in front of me. He lifted my dress over my ass. Then, I heard footsteps. They were really close. And I saw Tim coming back. I felt a thick warm thing prod my asshole. It was Andrew's cock. Andrew grabbed me on both sides of my waist. He forced his cock into me, deep. I took it all into my depths. It didn't stop where it hurt to go into. Andrew ass fucked me until my eyes started watering. He pulled out and dropped me to my hands and knees. Now Tim was in front of me. "Help." I pleaded. "I'll help, don't worry." But I was worried anyways. "I'll help you be a little slut." He said unbuttoning his pants and getting on his knees. Tim tried to grab my head, but I jerked it to the side. Then, he yanked me back into position by my hair. I held my mouth shut tight, but Tim slapped me really hard and made me open my mouth. Right when I did, he shove his cock in my mouth. I was going to bite him, but he fucked my face, going clear down my throat and back out repeatedly. His balls were slapping me in the chin. It was hard to breathe for a while, but then I got a pattern. Drool was running down my chin, and I felt strings of it waving back and forth from the two thrusting in me. Tim was going fast, my mouth was wide open and my tongue was hanging out. Andrew was plowing my ass so hard that it echoed when he hit me. It started to feel good getting my asshole pounded so nicely after about 10 minutes. And I didn't mind getting my throat stretched either. A few minutes passed the 10 minute mark and both of them pressed into me and didn't come back out. I felt Tim shooting loads down my throat and into my stomach. Andrew left a big pool of his babies inside my asshole. Tim slid out before he was done, leaving a line of jizz trailing from inside my throat, along my tongue to the tip, underneath my tongue, over my teeth, and hanging in long strands off my lips and chin. A huge sticky goop of my slobber, along with smaller lines, and long strands of cum were hanging from my face. Tim lifted the huge goop and rubbed it all over my face, first my forehead. My mouth was still hanging open with a cum trail to my throat on it. Andrew yanked out a couple seconds later. My asshole wouldn't close. Streams of semen were pouring from my gaped hole. I felt cum slipping down my throat still, and some jizz dripping deeper into my hole. I closed my mouth and swallowed. Then I smiled at Tim when he smiled at me. "Thanks." I said. "That was amazing." Sitting up on only my knees and holding out my hands to Andrew: "Could you take this off now?" So he took the belt off from around my wrists. I stood up, still about 7 inches shorter than Tim, 9 shorter than Andrew. Tim rubbed some more of my goopy drool on my face, and some lines of his cum. I still had a ton of strings of drool and jizz hanging off my chin. I smiled at him again. Then I looked at Andrew. "Thanks for the deposit in my ass." "Any time." I yanked my panties back over my ass as the two walked away. "By the way." Tim turned around. "You were one of the best I've ever had." And then they walked out of sight. |
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