Billys Introduction to a Sex filled Weekend
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Chapter 1: Billy Meets the New Sitter
"Billy, could you come down here please."
Billy put down the comic book he had been pretending to read. He bounded down the stairs with a grin on his face. Meeting a new sitter was like getting a birthday present. It didn't matter whether it was wrapped in fancy, shiny paper, or cut up grocery bags; he was sure he would like what was inside. His mom had told him that this one was seventeen, and had lots of babysitting experience. Well, he smiled to himself, she may have experience, but I'll bet she's never sat with somebody like me.
When he reached the bottom of the stairs, he took a moment to settle himself before turning the corner into the living room. He wanted to act every bit the disinterested, surly teenager that a thirteen-year-old was supposed to be. He sauntered into the room, trying not to openly stare at the cute young girl standing next to his mother.
His mom smiled and did the introductions. "Billy, this is Michelle. She's going to be staying with you tomorrow night. Michelle, this is my young William."
Billy cringed. It always drove him crazy when his mom called him that. He was perfectly happy being Billy, even though that did sound a little childish. It was still better than 'young William'.
"Hi, Billy," the girl stuck out her hand in greeting.
"Hey." Billy gave her hand a tight squeeze, determined to show her how strong he was.
"Your mom was telling me that you like comics." She squeezed back. Michelle was no weak, girly-girl. She seemed to have a lot of self-confidence. He liked that.
"Yeah, I guess," He muttered in reply.
"That's cool. I do to. Maybe you can show me your collection tomorrow night."
"Sure, whatever." Billy was still trying to act uninterested and even a little shy, but was finding it a challenge to not stare at her. She looked a little like Hillary Duff, if Hillary Duff wore glasses, and had braces and brown hair. OK, maybe he just wished she looked like Hillary Duff. But still, she was kind of cute. Not much tit, he observed, but her tight jeans nicely emphasized her trim legs and nice ass. She looked kind of athletic, which could explain the confident hand-shake. Yeah, he was definitely looking forward to spending an evening with this sweetie. If he didn't make a quick exit now, he might start drooling. "See you tomorrow," Billy mumbled as he headed back up the stairs.
After he left, Billy's mom told Michelle, "He thinks he's a little too old for a babysitter, of course. But he's never spent a night alone, and I still like for someone to be here with him. My company insists on having these sales meetings every month, and they are always in Atlanta, which means I have to leave him alone one night a month."
"Oh, so he's used to having a sit... someone stay with him?"
"Yes, my schedule has been like this for a couple of years now. I know this won't be the kind of babysitting you're used to, but..."
"No problem, Mrs. DuBois," Michelle said. "Yeah, usually the kids I sit for are like five or six, so this is a little different. But I'll try to treat him like a young man, and not a little kid."
"I'm sure he'll appreciate that," Marge grinned. "He gets home from school about four o'clock. Can you be here by six?"
"Sure, I'll come straight from softball practice. Don't worry, Mrs. DuBois, it'll be fine. We'll have fun."
"I'm sure you will, dear," Marge replied.
The next day Billy did his homework as soon as he got home from school. He wanted to have as much time to spend with Michelle as possible. The last two times Mom had gone out of town, it had been Mrs. VanLandingham who stayed with him. She wasn't bad, but having a nice, perky high school girl was definitely better than a middle-aged housewife.
Mom had left him a casserole to fix for dinner, and at 5:30 he stuck it in the oven. He wanted everything to be ready when Michelle arrived. That would help convince her that she wasn't stuck with some snotty-nosed kid this time. He was beginning to worry a little when she didn't show up by six-fifteen, but a few moments later he heard her car pull into the driveway. "Sorry, Billy," she said as she burst in the door. "Practice ran late."
"That's OK," Billy smiled at her. "Supper's ready, but it looks like you might want to get cleaned up first."
There had been a lot of rain last night, and Michelle had the mud on her to prove it. "For sure," she said, grabbing her bag. "Where's the shower?"
Billy showed her the guest bathroom, and gave her a fresh towel. "I'll keep supper warm for you, OK?"
'Thanks, Billy. Sounds like you have everything under control. I'll be out as soon as I can."
When Michelle emerged from the shower, she looked even better than she had yesterday. She wore a tight, red tank top, and a pair of white cutoff shorts that just barely covered her cute tush. Her legs had the deep, glowing tan of someone who spent a lot of time outside. Her shorts were so white they almost glowed, and the contrast between the light cotton and her dark legs seemed to draw his eyes to the line where her thighs disappeared up into her shorts. She hadn't bothered to put her hair back in a ponytail yet, and her pug-nosed face was almost hidden by her still-damp, shoulder length locks. Billy looked at her in amazement. Last night he had considered her to be fairly attractive, but now he could she that she was downright sexy.
"Where are your glasses?" he asked, groping for something to say that wouldn't make him seem like a goofy kid.
"Oh, I only wear those when I'm driving. Hey, supper smells good. Let's eat!"
Billy had fixed a salad to go along with the chicken casserole, and had everything sitting on the breakfast bar. For a few minutes they sat next to each other, quietly enjoying the meal. Neither of them spoke until their plates were empty. When Michelle finally came up for air she complimented him. "That was really good, Billy. Do you cook a lot?"
Billy blushed slightly at the compliment. "Well, I try to help my mom as much as I can."
"Is it just you and your mom?"
"Yeah, my dad took off when I was about three years old. He told my mom he just didn't want to be a father anymore. Funny thing is, he remarried a few years later, and then his new wife had triplets. I guess that's some kind of poetic justice, right?"
"Umm, I suppose. So, no brothers or sisters either?"
She seemed kind of nosey, but Billy was used to that. Most sitters asked a lot of questions. "Nope, it's just mom and me."
"Well, this is a very nice house for the two of you."
"Yeah," Billy laughed. "My mom says the only two good things she got out of her marriage were me and this house."
After they finished eating, Michelle helped him clean up. As they worked around each other in the kitchen, Billy kept stealing glances at her tight little body. Yeah, he had to admit, she was a lot better than the slightly overweight Mrs.VanLandingham. Thanks, Mom, he smiled to himself.
When everything was cleaned up they moved into the living room. "Do you have any homework?" Michelle asked.
"Did it already."
"Geez, you really do have your act together. I almost feel bad about taking your mom's money for sitting... uh, staying with you. So, what do you like to do in the evening when you don't have homework?"
"Oh, watch a little TV, or read."
"Well, you go ahead and do whatever you want, but I've got some homework to do, OK?"
"Sure. I'll go watch TV in my room and leave you alone."
"Nah, that's OK. You can stay here, the TV won't bother me. I've got pretty good concentration." Michelle patted the sofa next to her, and Billy sat down and grabbed the remote.
He pretended to be interested in a 'Buffy' rerun, but his eyes kept wandering in the direction of the sexy young lady sitting next to him. He was surprised when he saw the title of the book she was reading, 'Studies in Human Sexuality'. "That's a schoolbook?" he asked.
Michelle smiled at him. "Not exactly. It's some extra reading that my psych teacher recommended."
"Your teacher has you reading a sex book?"
"It's cool. She knows I want to be a sex therapist after college, so she thought I would find it interesting."
"A sex therapist? What's that?"
"Well, it's a special kind of psychologist that helps people with sex problems."
"What kind of sex problems?"
"Umm, that's probably not something I should be talking about with you. You're a little young, and I'm not sure your mom would approve."
"Do your parents know what you want to be?"
"Sure. In fact, that's what my dad is. He's always said he wished there were more female therapists, so I decided to become one."
"So, you already know a lot about sex, I suppose."
Michelle spun around to face him. She put her feet on the cushion between them, wrapping her arms around her knees to hold them up close to her chest. That gave Billy a good view of her legs, and even a hint of ass cheek poking out of her shorts. If Michelle realized how much of a leg show she was giving the young boy, she didn't show it. She seemed unaware of how hard he was struggling to look her in the eye and not stare openly at her tight, tanned thighs.
"I guess I do, but don't get the wrong idea. I take sex very seriously, but I guess you'd say I have a lot more book learning than practical experience."
"Does that mean you're a virgin?"
She glowered at him. "I should slap you for asking that. It's none of your business, young man. But, I am trying to be more comfortable talking about sex, and not avoiding difficult questions, so I guess I should give you an answer. Am I virgin? It's complicated. Technically I'm not, but I've never had intercourse either."
"Huh? How can that be?"
"I told you it was complicated. I lost my hymen when I was horseback riding a couple of years ago. I thought I was dying, there was so much blood, but our doctor said it wasn't anything to worry about, and that accidental defloration occurs more often than people realize."
"But you've never let a guy..."
"Right. Like I said, I've never had intercourse."
"Do your have any boyfriends?"
"Sure, I've had a few. I'm going out with a guy named Kenny now. He's really cute."
"Doesn't he want to have sex with you? I mean, you are really pretty, and I would think..."
"Of course. Guys are always trying to get girls to have sex with them. That's normal. But I've been able to keep Kenny and my other boyfriends happy with some of the other things that girls can do for guys instead of intercourse."
"Other things? Like what?"
"OK, that's definitely not something I should be talking about with you. Sorry, Billy but that's one question I won't answer." Michelle turned back around to face the TV, and Billy knew that it was time to back off.
They watched a stupid situation comedy, then Michelle went back to reading her book. Billy grabbed the new 'X-Men' comic that was lying on the end table next to him. He pretended to be interested in the latest Marvel creation that was draped in his lap, but his thoughts were really all about the very interesting young lady sitting next to him, with her nose buried in a book full of what he assumed were sex stories. She hadn't said anything since refusing to answer his last question, and Billy didn't think it would do any good to show too much curiosity now. It was time to try a different approach.
"It's getting late, so I'm gonna turn in." Billy said, stretching his arms over his head. "Are you going to sleep in my mom's room tonight?"
"Nah, I think I'll just sack out here on the sofa, "Michelle said.
"No prob. Hey, look, if I said anything to offend you, I'm sorry. It's just that... well, you aren't like most girls. I usually get really nervous when I try to talk to them, but with you I feel comfortable, even talking about sex and stuff like that. In fact, I think I've already decided to add you to my club."
"Your club?"
"Yeah, I've had a lot of babysitters in the last couple of years, and I keep a list of the one's I really like. I call it Billy's Club. That way if my mom ever asks me who I would like to have stay with me, I just pick one from my club."
"Well, I guess being in your club is a compliment, right? Don't worry about me being upset by anything you asked me. You're just being naturally curious. Besides, I probably shouldn't have been reading this book in front of you. And," she glanced down at herself, "it might have been a good idea for me to wear more clothes around a mature young man like yourself. After all, I wouldn't want you to get the wrong idea about me."
Oh, that's OK. Billy thought, you could have wrapped yourself in a towel after your shower and I wouldn't have minded. Damn, there was going to be a hot teenager who wanted to spend the rest of her life talking to people about their sex lives sleeping in his house tonight. It was almost too much for his thirteen-year-old brain to handle.
Chapter Two: Billy Learns a Thing or TwoHe went upstairs and got ready for bed. After he showered and brushed his teeth, he settled into his big, comfortable bed. He pulled the covers up to his chin, but he wasn't ready to go to sleep. "Michelle," he hollered, hoping she would hear him in the living room.
"What?"
"Could you come up here for a minute?"
A moment later she stuck her head into his room. "If you are expecting me to tuck you in, or read you a bedtime story, you're out of luck," she said.
'Nah, nothing like that. I just have a... a problem I was hoping I could talk to you about."
Michelle came into the room, and sat on the foot of his bed. She looked concerned. "What is it? Is something wrong?"
"Yeah, you might say that," he said, almost whispering. His head hung low, avoiding eye contact. "My life is all screwed up."
"What do you mean?"
She was back in that knees-against-chest position, and Billy was finding it exceedingly difficult not to stare at the way the tight material of her shorts outlined her pussy. Be cool, he thought. Don't get out of character. "Well, this is kind of embarrassing..."
Michelle reached out and touched his arm. "Aw, don't worry Billy. This is just between the two of us. So, why is your life any more screwed up than any other thirteen-year-old?"
"Don't make fun of me, OK? This is hard enough already. Just let me ask this before I chicken out. Like I told you, I've grown up without a father, or older brothers. And my mom, well, she just panics every time I mention anything to do with sex. So... God this is hard to say... I just don't know much about sex, not nearly as much as other guys do. I mean, I hear my friends talking about things they have done with girls, or would like to do, and I don't know what they are talking about most of the time. I don't even understand some of the jokes they tell. Michelle, you're an expert. Can you teach me a little about sex? I want to fit in more and not be such a loser." He looked up at her, with what he hoped where his most convincing puppy-dog eyes.
"Gee, Billy, I don't know if I should be talking to you about sex. I mean, you're a nice kid and all that, but you are kind of young."
"If you aren't comfortable talking to me about sex, how will you feel in a few years when you are talking to adults about the same things?" Nice one, Bill, he congratulated himself.
Michelle let that sink in. "OK, good point. I'll give it a try, but I'm going to stop whenever I get uncomfortable. Darn, I don't even know where to start. I assume you've got the whole birds-and-bees thing down."
"Oh yeah," Billy grinned. "I know where babies come from. I'm just not sure how to get to that point."
"Hmmm, I can't cover everything in one evening, so where would you like to start?"
"How about kissing? I don't know much about that."
"Come on, Billy," Michelle smiled. "Everybody knows how to kiss. It's natural."
"Oh, I've kissed my mom, and my Aunt Susan. But I don't think that's the same as kissing a girl, is it?"
"You're right, it's not." Michelle thought for a moment, trying to come up with an easy way of explaining something that seemed so obvious to the unsophisticated young boy seeking her help. "Hmmm... OK, let's put it this way. There are several different types of kisses. We'll call kissing your mom and your aunt a 'relative kiss'. That's either a peck on the cheek, or, if they insist on mouth-to-mouth, with lips tightly closed. Right?"
"Yeah, that's what it is. Not much fun."
"Yeah, well I don't think that's supposed to be fun, it's just a way of greeting someone that you like, or at least are related to. I guess guys don't go in for that as much as girls do. OK, the next stage we'll call the 'first date' kiss."
"Huh?"
"You know, after you've had a nice evening with a new girlfriend, and it's time to say goodnight, you might want to try an exploratory kiss."
"Exploratory?"
"Yeah, just a quick smooch, without being too aggressive. It's like you're asking if she enjoyed the date and if she would like to go out with you again, without actually saying anything."
Billy looked puzzled. "Just how would I do that?"
"Well, first you start talking very quietly, so your date has to get close to hear what you are saying. Then you slowly bring your face close to hers, pucker up, and go in for lip contact. If she turns her head so you land on her cheek, it's not necessarily a put-down. It might just mean that she likes you, but she just isn't ready for more intimate contact yet. Don't let that bother you. Of course, if she pushes you away completely, you've got a pretty good idea what that means, right?"
"Yeah, strike out. That's probably what'll happen to me. But I'm still not sure exactly how to do it. Could you... would you... maybe... show me."
"You want to kiss me?"
"Please?" He tried the puppy dog look again. He hoped he didn't look too much like a spoiled six-year-old.
"Well, I shouldn't... but... I guess it won't hurt anything to give you a little lesson. Just don't tell you mom, all right?"
"Of course not!"
"OK," she sighed. "Now, sit up... lean toward me... good... pretend we are talking about the movie was we just saw... yada, yada... that's it... pucker up... lean a little closer..."
Billy planted his lips on Michelle's mouth for a brief second. "Like that?" he asked.
Michelle sat back. "That wasn't too bad, for a first time. A little softer would be better. You're not trying to show me how strong you are, but how gentle you can be. But your touch will improve with more experience."
"Thanks. It was easier than I thought it would be. You're a good teacher. So, what would I do after the second date?"
"Hey, not so fast. I just got you through the first date, now you want to go steady? Or are you just trying to trick me into giving you another kiss?"
"Come on, Michelle, please. I don't know if I'll ever have a chance to learn from anyone as kind and understanding as you are, and I want to take advantage of it. I really want to know how to do things right, and not look like an idiot, if I ever do get up enough courage to actually ask a girl out."
Michelle hesitated. She knew better, but something about teaching someone as innocent and naïve as Billy intrigued her. It was almost like she was doing a good deed. "Well, OK. I guess since I've started, I could take it one step further. Now, the next step is the 'romantic' kiss."
"Yeah, like in the movies. I have no idea how to do that. Why does everyone always close their eyes? And how do you keep from bumping noses?"
"So many questions! Geez, you've gotta stop thinking too much and just let it happen. People close their eyes when they kiss because it's weird to stare at somebody when your face is only a couple of inches away from theirs; you'd kind of go all cross-eyed or something. And don't worry about the nose thing. All it takes is a little turn to the side and it's no problem. Even if you bump noses, it's not a big deal. It happens to everybody. It can kind of break the tension. You just giggle about it, then try again."
"So, could you show me... ?"
"I still think you are conning me," Michelle said skeptically. "But, OK, I guess one more little kiss won't hurt. Now, sometimes it's the girl who initiates the kiss, so we'll try that. Close your eyes."
Billy pursed his lips and waited. Michelle leaned forward, but stopped before making lip contact. "You really shouldn't pucker up so much. You look like a duck," Michelle giggled at him. "Just relax."
Billy took a deep breath and tried to relax, and 'just let it happen'. He felt Michelle's face very close to his. She draped one arm over his shoulder and lightly pressed her hand against his neck. Her warm lips gently caressed his and this time they were slightly open. He opened his to match, and felt the tip of her tongue tickling his lips. He tried to return the gesture, but stopped when the tip of his tongue rubbed against her braces.
He was about to try putting his tongue further into her mouth, she pulled away and said, "OK, that wasn't bad. Either you're a quick learner or you have had more experience than you're letting on."
"No, really, that was my first real 'romantic' kiss. And it was wonderful. Thank you."
"You're welcome. But I think that's enough sex education for one night. You need to get to sleep. Sorry, I sounded like a baby sitter then, didn't I."
"That's OK." Billy smiled at her. "Uh, Michelle, can I ask you one more question? No demonstrations this time. There's something else that's been bothering me for a long time, and you're the first person I've met that I trust enough to ask. I know you'll give a straight answer, without making fun of me."
Michelle was still battling with her conscience, keenly aware that she was stepping way over the line of propriety. But she was still intrigued by his lack of social skills. Part of her felt that Billy knew more than he was letting on, but she also felt that it was possible that he had led such a sheltered life that there were significant holes in his knowledge. In a way she felt sorry for him. "OK, one more. What is it?"
"It's really embarrassing to talk about."
"Well, maybe we should wait until some other time, when we know each other better." Michelle started toward the door.
"No, wait. I'll try. OK, here goes. What's jacking off? I hear guys talking about it, but I'm not sure what it means."
"You really have grown up in a cave," Michelle sighed. "I thought all boys your age knew about that."
"I know. See what I mean, it's embarrassing to not know, but there's no way I can ask any of my friends. And my mom..."
"OK, I get it. 'Jacking off' is just another term for masturbation. You know what that is, right?"
"Uh, yeah. That's touching your own private parts."
"That's right. You masturbate, don't you?"
"Uh, not really. Mom tells me I should only touch myself when I'm going to the bathroom. But sometimes I wake up in the middle of the night, and my thing..."
"Use the right word, Billy. It's called your penis, not your thing."
"OK, whatever. My... penis... is all hard and swollen... and when it's like that it feels really good when I rub it against my sheet or underwear. Sometimes I wonder what it would feel like to touch it with my hand. That's masturbation, right? Darn, I'm so embarrassed talking about this. Please don't tell anyone."
"Aw, Billy, don't worry about that. Part of being a therapist is keeping patient information confidential." Besides, Michelle thought, nobody would believe that she had met a thirteen-year-old boy who didn't masturbate.
"Look, I don't mean to go against what you mother has told you, but from everything I've studied, I can say that masturbation is perfectly natural for a young boy, or girl. It's part of learning about your body. But if your mother says no, then I guess you have to listen to her."
"But you don't agree with her. Maybe mother doesn't always know right, is that what you're trying to say?"
Michelle didn't say anything, realizing that she had gone much further with this discussion that she had meant to. But Billy wasn't ready to drop the subject. "Umm, supposing I wanted to try it anyway. I mean, you said it was normal, right? So if I wanted to... masturbate, how would I do it?"
Michelle had reached her limit. "No way, Jose, I'm not doing anything like that. I'm not one of those babysitters that plays with little boy's peckers."
"Hey, I'm not a little boy! Oh, don't worry, I was just kidding anyway. I wouldn't want you to see my thi... my penis, anyway. It'd be too embarrassing. I'm... not normal."
Michelle knew it was way past the time for her to go back downstairs, but Billy's last comment had rekindled her curiosity. "What do you mean, not normal?"
"Well, I'm not like other guys, down there I mean. I don't even take a shower after P.E. class, because I don't want anyone to see me. I've seen them naked, and I know I'm, well... different."
Michelle sat down on the bed again. Billy's sad tale was touching her compassionate side again. She remembered when she was younger being embarrassed about letting other girls see her naked, because of her small boobs. Of course, that was before she found that a lot of guys like smaller breasts. "Billy, everybody is different. Heck, my breasts aren't as big as most girls, but they are what they are, and that's it. Actually, I kind of like my little bitty titties. They're good for sports. Some of my teammates have such big bags on their chest that it hurts just to watch them trying to run around the bases."
"Little bitty titties," Billy giggled. 'That's funny."
"Yeah, see, that's what I'm talking about. Keep a sense of humor, and just deal with what life throws at you. Don't get hung up on trying to compare yourself to everybody else. You are you, and you should learn to accept yourself as you are, and not worry about being like everybody else. Besides, you might be making more out of this than you should be. Maybe you're not as abnormal as you think you are. After all, who is to say what 'normal' really is? Size really doesn't matter that much anyway. The way you make love, with caring and compassion, is a lot more important than a couple of inches here or there."
"OK, but I still feel... unusual. Look, would you do something for me. It's really kind of a weird thing to ask, but maybe it'll help me get over my lack of confidence."
"What now?"
"Would you take a look at my penis, and tell me if it looks OK to you?"
"You want me to look at your coc... penis? I don't think so."
"Please, Michelle. Just take a peek and let me know what you think."
"Well," Michelle said, donning her therapist tone of voice again, "just a quick peek, kind of like a doctor examining you. Just a visual inspection, with no touching"
"Of course. By the way, just exactly how much experience with penises do you have? How many have you actually seen?"
"Just three, and one of those probably shouldn't count."
"Why?"
"It was my older brother, and it was an accident. I went into his room to ask him a question, and he was jack... masturbating. I only got a quick peek. But I've seen pictures in some of the books in my dad's library, and I've seen lots of statistics on penal size."
"OK, I guess you know what you are doing. But you have to promise not to laugh."
"Billy, I take this kind of thing very seriously. Let's keep this on a doctor, patient level."
"OK, doctor. But now I have another problem."
"What?
"Talking to you about this has got me... excited. I'm afraid it's kind of... swollen."
Michelle smiled at him. "Hey, I've seen erections before. And besides, that's how I should judge your size anyway. You want it to be as big as it can be when I see it, right?"
"I guess. Heck, I don't know. OK here goes." Billy quickly threw his blankets off and pushed his pajama pants and underwear down to his knees.
"Oh My God!" Michelle exclaimed.
"It's that bad?" Billy moaned.
"Billy, when you said you were different, I thought you meant you were smaller than the other guys. But this... geez... that's not a boy's cock, and it's not a man's cock... damn, that's more like a horse cock."
"You've seen those too?"
"My uncle has a farm. Damn, just how big is that thing?"
"I don't know, I've never measured it."
"Hmmm, does your mom have a tape measure?"
"You really want to measure it? But won't that mean you'll have to like... touch it?"
"Sure! Of course, it would be like a research project. I won't be touching you in a sexual way or anything like that."
"OK, if you think it's all right. There's a sewing machine in the room across the hall, and I think Mom keeps a tape measure in the box next to it."
Michelle jumped up and ran out of the room. "Where? Oh, I see it."
She was back in a matter of seconds, her face glowing like a kid on Christmas morning. "You know, if I am going to get an accurate measurement, we need to make sure that you are fully erect."
Oceana
- 12.07.2021
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