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The Bet

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The Bet by SlvtreKlgmn (SlvtreKlgmn@aol.com)I was just the dorky neighbor. Next door to me lived my parents longtime friends and their daughter Charity whom I’ve known since I was four or five. She is tall, about five foot nine, long black hair, olive complexion, Kate Moss figure, always smiling. Of course I’d had a hard-on for her since before I could remember, but as I said, I was the dorky neighbor she sometimes said ‘hi’ to in school. But sometimes I would muster the courage to wander over there and hang out with her while she watched TV and recently, get ready for dates and such. I never went out on Fridays, so I would watch, then when she left with a dismissing flick of hair and a cold ‘bye’, I would run back home and into my bathroom to pleasure myself. This was about six years ago when I was fifteen. I guess it was pure luck. The once in a lifetime kind. Win the lottery kind. Saturday night I was bored, TV sucked, I peeked out our den window and saw the downstairs light on in Charitys house. I checked the time 9:00 pm. What’s she still doing in? I wondered. I snuck out the back door and peeked in the window. Charity was sitting in a bean bag watching her TV, wearing a t-shirt and sweat pants. Not too sexy, she must be staying in. I tapped on the window and she peeked up, recognizing me. Without expression she got up and unlocked the window and I hopped through and down into the room. “Whats up?” she said, plopping down again. “Nothing,” I replied, meek as a mouse. Just then the toilet flushed in her private bathroom connected to her bedroom. I suddenly felt a jump in my chest, she wasn’t alone. The door opened and Krissy, one of her school friends came out, and then jumped when she saw me. “You scared the shit out of me! What’re you doing here?” she said, sternly. “He lives next door,” Charity said, blandly. I looked at my feet, then back at Krissy as she sat down on another bean bag. She had long curly brown hair with blonde highlights. Athletic body, about 5 foot 5, big tits. I looked around the room and noticed a Smirnoffs bottle of vodka on Charitys desk and a bottle of Sunny Delight next to it. Both Charity and Krissy had plastic cups nearby them, Krissy took a drink from hers and screwed up her face. “Goddam, you made these fuckers strong, man,” she said. “Yep, hey Reggie, you want a screwdriver?” Charity asked me without looking. “No thanks,” I said quietly. I’ve never been much of a drinker, much less at fifteen. This went on a while, I sat down quietly in the corner, listening to their conversations get more and more slurred and muddled by their consumption. Time went on and they flipped through TV channels finally settleing on MTV where Loveline had just begun, the show was brand new then, Dr. Drew still had all his hair. The room got quiet as they took a call. The girl on the phone asked for advice. Her boyfriend said that if she really loved him she would swallow his semen when she gave him fellatio, she wanted to know what to do about this, she didn’t find it disgusting, she just didn’t think that was true. “That’s fuckin’ gross,” Charity mumbled, took a drink. “It can’t be that bad,” Krissy said back, watching intently. “Yeah, right. You’d puke your guts out,” Charity said back, chuckling. “No I wouldn’t, bitch.” Charity perked up at the insult, got a serious look on her face. “Fuck you, I’d bet you a hundred fuckin’ dollars you would,” she said, nearly angry. “You ain’t got a hundred dollars anyway, and fuck you back,” Krissy challenged. I sat with my legs crossed, aroused by the subject matter. “I worked three overtime days last week, I got it, I’ll fuckin’ bet you right now,” Charity said. “Serious as a heart-attack.” Not wanting to lose face, Krissy looked nervous. “Yeah, well, where you gonna get it anyway? It ain’t exactly at the supermarket.” Charity looked stumped, nearly defeated at the realization. Then I did it. I coughed. Both girls quickly turned thier head to me, they’d completely forgotten. Charity turned to Krissys horrified face, Charity started laughing hysterically. Charity rolled over and stood up, looking at me. “So will you do it?” She asked. “I don’t know...” I started, I was scared shitless. “Please! It’d be so fuckin’ cool! Pleeeeese,” she begged. I thought like mad, “how?” I finally said. “I got a bathroom right there,” she looked around her room and fetched something off her dresser. “Here, this is perfect!” and she handed me a shot glass. “Put it in there.” She stood beaming, nearly giddy. I looked at Krissy, she had her hands in front of her, rubbing them together, nervous as hell. “C’mon, go!” Charity said, excitedly. I moved to the bathroom, shaking slightly, probably white as a sheet. Once in I tried to lock the door, but their wasn’t one. I lowered my pants and sat down on the cold lid of the toilet. My penis had shrunk into my body like a turtle, I tugged on it a few times, but it wasn’t cooperating, I tried rubbing it on my leg and it grew a little, but not much. It went on like this for about twenty minutes when Charity finally knocked on the door. “What’s up in there? Almost done?” I was petrified, I’d been tugging on a semi for twenty minutes now and I wasn’t even close, the longer it took the worse the anxiety got and the worse the pressure. “I don’t think I can do this,” I whispered at the door. “Why not? Whats the problem?” She said back, louder than I would have wanted. “I, I...don’t know,” was all I could say. I heard an exasperated sigh from her, followed by silence. “Fine,” I heard her say. I thought I was off the hook. Then I heard the doorknob turn. I tried to jump up and hold it shut, but I wasn’t fast enough and Charity was in the room a second later. She looked down at me sitting on the toilet lid with my pants around my ankles and my limp penis laying on my balls. I saw her smile slightly at the sight, then took on a tone like an industrial problem solver. “So, like, what do you need here?” She said. I was stumped, “I don’t know, I was just...too much pressure, you know?” “Do you need any help?” “Like what?” I asked genuinely. “Ummm,” she looked around the room, I noticed that the door was still standing wide open. “Here,” she said. “hold out your hand.” I did, and she deposited a modicum of vaseline in my palm. She stood back analyzing. “Well, go ahead,” she said. I put my hand on my penis and began pumping, it started to grow slightly, until I had a full erection. “Do you want me to leave you alone?” She asked. “No, stay here,” I said. “You want any help?” she asked. “Sure,” I said, not knowing what. She got down on her knees and reached out and scratched my balls slightly with her fingernails. “Does that help?” she asked. It did. “Are you almost there?” she asked. I knodded feverously. She got the shot glass and held it, “let me know when.” A second later I was ready, “okay,” I said and she grabbed my penis from my hand and aimed it into the glass where I emptied my ejaculate, nearly filling it. I opened my eyes to see Krissy with her eyes glued to the sight of Charity milking my penis like a cows udder, and the shot glass full of sperm. Charity let go and stood up, “okay, moment of truth!” I got up, pulled up my jeans and walked out. A hundred dollar bill was sitting on the dresser, Charity walked over, set the glass on the bill and stood back. Krissy looked at it, then retrieved her cup full of screwdriver. “No way! No chaser, that’s cheating! You have to go a full minute with nothing but cum on your tongue!” Krissy muttered something like fucking bitch under her breath. Then she picked up the glass, held it, then slammed it. She screwed up her face, choked down a swallow and stood, breathing, hand on the dresser. Then she gagged once, twice. Then nothing. She did it. Charity was astounded, she clapped and said, “whoo-hoo.” Until Krissy picked up the $100 dollar bill and stuffed it in her pocket. “Fuck, well, there went a hundred bucks,” she said. She went and sat down, looking depressed. I looked at Krissy, she looked at me. “Wanna win it back? Krissy said to Charity. I arched my brows. “Can you do it again?” Krissy asked. “What are you talking about?” Charity said. “I’ll let you win it back, all you gotta do is match me, one for one.” Charity looked at me, horrified, then thinking. “He can’t do it again, he barely could do it once,” Charity said. Krissy looked at me, I was feeling much calmer after the previous ‘extraction’. “Well?” Krissy asked. I thought a moment, “okay, but I’m not going to be just some goddamn cow in a barn for you guys, I get something too or it’s no deal,” I couldn’t believe I was saying this. “What?” they asked in unison. “You both have to get naked while I’m doing it,” I said, nervously, my voice wavering. They looked at each other, then away at the walls. “Okay,” Krissy said first, then finally, reluctantly, Charity. “Alright...” Instead of the bathroom I walked over to the bean bag and sat down, I crossed my hands on my chest and acted like I was impatiently waiting. The girls started peeling clothes off. Charity’s tits were smaller than Krissys but she had nice B’s anyway. Krissy had big old C’s no doubt. They both stopped at their panties. “All the way,” I said. They both flustered, “well you too,” Charity said. I got up and pulled my jeans over my semi-and-growing-fast boner. The girls dropped their panties, taking care of my semi-erect state and gave me a painful erection. Krissy had just a tuft of pubic hair over her pussy lips and a fat clit that I could see clearly sticking out. Charity had a thicker bush that was only trimmed around her bikini line so it wouldn’t stick out of her panties. “Get going,” Krissy said. Charity brought me the tube of Vaseline and I went to work. The girls just stood in front of me, watching. I looked over their bodies as I worked my erection. I felt I was gettin close and signaled to Krissy to get the glass. Finally I let go and said, “here it comes!” Krissy grabbed my cock and aimed it into the glass but nothing happened. It was some plotting on my part, I admit. “You have to tug on it,” I said. Krissy started stroking my cock like mad, and I felt myself go over the edge. “Here it comes!” I said and started gushing. I filled the shot glass this time. Krissy let go and stood up, handing the glass to Charity. “Now it’s your t--” Krissy started to say, but was cut off by Charity throwing the shot back and swallowing instantly. She didn’t even flinch. “Shit,” was all Krissy could say. Charity smiled devilishly. We all looked at ourselves. I still had my pants around my ankles. My penis holding a steady flight pattern from the two visions in front of me. Charity naked, holding a shot glass a hundred dollar bill and Krissy also completely nude, looking defeated. “I should have kept my mouth shut,” Krissy said. Charity took one look at my still hard dick and said, “tell you what, I’ll give you the chance to win it back.” “Another shot?” Krissy said. “Nope.” “Then what?” Charity smiled a moment and then said, “Get on your knees and suck it out naturally.” Well, I won’t lie to you and say that it was easy, each of the girls were not without talent, as was I. For you see, for my fifth go, I won that hundred myself.

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