This story could be under "teen" or "forced" or maybe any number of places.
Our dad worked for the government and we hardly saw him more than a few days a month so when I was 13 he separated from my mom. As time went by mom had to work more and more and then she started drinking but we didn't know about that untill years later. All we knew was that we were mostly on our own and she mostly came home and went to bed very late. My little sister, Jan started cooking when she was young so she almost always did the cooking, and she was very good at it.
One day when I was about fifteen or so I was going through some things that my guidance councelor gave me to take home. I had layed it out on the coffee table to concider the carreer path I wanted to take. I had narrowed it down to business management or accounting. Jan, who had just turned 13 was sitting in the easy chair with her leg hanging over the arm. She was bored with the TV so was just killing time talking to be before dinner. "Don't be an accountant. That's boring."
"Maybe it's boring but someone has to do the jobs that are boring, even dirty and smelly. Someone had to clean the pig sty or no one can eat bacon. Besides, just because you think it is boring doesn't mean I won't like it."
"I couldn't do it. But I'm not good at math either." she said.
"What do you want to do then?"I asked. And that is how it all began.
"I don't know. I don't want to be a firefighter or astonaught or policeman. Maybe women can do those things but I don't like those things that women had to struggle to be able to do. I want a more traditional job for women."
"Like what? Like a school teacher? Or a housewife?", I proded.
"Maybe, those are good choices." Jan said thoughtfully.
"But a housewife isn't a carreer." I said.
"No, but I don't just want a carreer. I want to make my life what I want it to be. Something I can be proud of. Something to leave a legacy. I want to do something that is timeless. Something that women have done for centuries from the times of old. What have women been doing since old times? What do you think is the oldest . . . um, profession?"
"The oldest profession? Prostitution." Evidently she had not heard the saying before. She was just searching for words and that's just how it came out.
"Yeah, I could do that." She said. But I just laughed at her. Up til then I just thought of her as the scrawney kid I lived with who cooked my dinner. Sex and my sister were so diverged in my mind that her having sex seemed rediculous to me. "What's so funny about that?"
"You have to be sexy if you want to sell your body for sex." I explained. But she was annoyed by my finding humor in it. If not for that she might have dropped it and we might have never remembered this conversation. But now she had something to prove.
"I can be sexy." She insisted. "I can be sexier than hell."
"Wanna bet?" I said trying to call her bluff but she wasn't bluffing. I bet her fifty dollars that she couldn't be sexy. I thought it was a moot point because I had the fifty dollars and she didn't. She had to go to mother whenever she wanted some cash but I did kept busy in the summer doing odd jobs in the neighborhood, mowing lawns and stuff so I had money. Jan just wouldn't let it go; she even raised her side of the bet to a hundred dollars because she would have to pay on time. Mom would want an explaination if she asked for $50 all at once but she could give me pieces of it at a time without raising suspition.
The next question we had was who would be the judge of if she was or was not sexy. I insisted that I had to be the judge because I was the only one besides her that was even there and only a guy could truely judge if a girl is sexy. She said that it wasn't fair because I was biased against her. Finally she made me strip down to my shorts. If I was lying when I said she wasn't sexy she could tell by the bulge in my pants. That was the gage then. If she could give me a hard on she got fifty dollars. If not, she would have to work it off for the next year. I thought I had it made.
"No good," she said, "You have to take those off too. I need to be able to see it to tell. Your boxers are too consealing." I protested but since she was likely to be shedding her clothes too it seemed only fair. Chances are, I figured, she would chicken out like a shy school girl. I dropped my boxers and stood in the middle of the living room buck naked with my limp worm druping low and swinging with my nut sack. "You have to watch now; you can't look away." she said still setting terms determined to win her fifty dollars but mostly to make me eat my words after laughing at her. For her right now it wasn't about a bet or money; it was about me telling her that she couldn't do it.
"I won't look away." I promised. I was convinced that this would be an easy bet. She put on some slow jazz music from the college radio station in town and started to sway this way and that like a sensual seductress. I wasn't very impressed at first but then I began to see Jan in a new light. I noticed things about her that I never had before. When did she fill out like that? She never had hips before. I guess she just covered them up with baggy clothing. As she stripped down to her bra and panties I reallised I might be in trouble. She was sexy! My little sister - Who knew! My only hope now was to bluff my way out but as she danced away and unfastened her bra I could feel the blood surging into my dick. Her tender little mounds cried out to be fondled. Her nipples to be nibbled. I wanted to look away but now I couldn't - and not because I'd promised not to. I started to lust after her. By the time she stepped out of her panties I my Johnson was pointing right at her as if to identify the winner. She stayes in character, still in seduction mode spinning her panties around on her pointer finger walking crosslegged towards me with her eyes staring into mine saying, "I want you." When she got close to me she hung her panties on my protruding member as if to make her claim of victory.
There we stood naked together in the livingroom with her underwear suspended from my pole. We were both speachless now. We had never done anything like this before so we didn't know what to do at this point. I knew she had won the bet, that much was obvious, but I wanted to weazle out of paying her. On top of that I didn't want her to leave or get dressed. I just wanted to look at my hot sister with her clothes off. "Okay, its one thing to get a guy all hot and excited," I began looking for any excuse to keep her there, "but now what do you do? Bet you wouldn't know what to do with a penis now. After you did your little dance."
"Wanna bet?" she said falling for the trap. I bet her double or nothing she couldn't get me off. I had jacked off before but had never had a girl friend - not that I couln't have had one if I'd wanted one; I was a popular guy. But the girls at school were so high maintenance I stayed away from them. Of course for me it wasn't that I didn't believe her now. It was that I did believe her and wanted her to prove it on me. The hundred dollars seemed worth it to me as payment for services. She knelt down in front of me and started to devour my cock. She licked and sucked and squeezed her with her hand jacking me off and bobbing her head taking me deep into her throat and pressing her nose to my pubes. Her hands and mouth played with my balls untill they drew up tight ready to release my hot juice. I didn't warn her but held her head against me as I injected her mouth full in many gushing pulses. She just sucked me off swallowing it all down as if she'd done it a thousand times before.
much more to cum