Lessons Ch. 01

Chris Young was not having a good day. It was Friday a week past his 18^th birthday, and he was home alone for the evening. He couldn't get a date to save his life, mostly because he was too scared to ask, but his friends were out tonight. He sat on the couch playing video games, angry and bored.

The front door opened with a slam, he looked over to find his older sister Amanda home from college. "Hey Chris! Thought I'd come home for the weekend. What are you doing home, shouldn't you be out with some hottie?"

"Yeah, right. You know me, Amanda. I'm home, as usual."

"I still have to get you a birthday present. Maybe I should get you a girl!"

"The way things are going I can't even buy one. It is what it is, Amanda." His body language emphasizing his discouragement.

She stopped and took a look at him, then shook her head. "Chris, you just need to put yourself out there. Go to a party, something. It's not like you're a hideous beast or anything. You're actually a nice guy, some girl probably already likes you."

"Riiiight. I wish I could be like you, but, honestly, I just can't. You know me. I shut down in social situations, I just can't do it."

"Well, lucky for you I'm home to keep you company tonight. Pick a flick, I'll make some popcorn for us!" as she attempted to brighten his mood.

This was a reversion back to earlier years at home when they would do this at least once a week. He'd help with her homework and she'd try to get him to go out. He had much more success than she did.

The weekend went by quickly. When she left, she whispered to him "I know what to get you for your birthday now. I'm late, but it'll be the best present ever, I promise!" He just shook his head as she got in her car and left to go back to college.

Two weeks later, his parents went out of town for a 'weekend getaway', as Mom had put it. He'd overheard his Dad call it a 'weekend fuckfest'. At least one guy in the house got laid, he thought. His friends were all out again as he settled in front of the TV.

He heard the door open quietly, then a pair of hands covered his eyes. "Guess who?"

"Satan?" He knew it was Amanda.

"Uh-uh."

"Santa Claus?"

"Close enough. How ya doing, Chris?"

"Ok."

"Chris, this is Theresa, but call her Terri or she'll hurt you. I gotta make a quick run to the store, I'll be back in a bit." There was a blonde standing beside her with a big smile on her face.

"Sure."

He looked over at Terri. Tall enough, blonde, nice looking. He already couldn't speak.

"Hey Chris, whatcha watchin'?"

"Nothing." He couldn't think of anything else to say.

"Chris?"

"Yeah."

"Are you gay?"

"WHAT?" He said in shock.

"Are you gay? I mean, it's ok if you are. If you're not, that's good too."

"I'm not gay."

"Good. Chris, Amanda said you have a problem talking to girls. Do you?"

"Kinda."

"I figured. Look, maybe I can help. I'm experienced with this sort of thing."

"You can't talk to girls?" He responded with a bit of sarcasm.

She giggled. "Oh, I can. Chris, your sister says you're a nice guy. She says you never date, she says you need some help. Here I am, Chris."

"What do you mean?"

"Well, Happy Birthday Chris! I'm the present. The girls I hang with have a nickname for me. They call me..." she changed her voice to a bad Ahhhnold impersonation, "The Devirginator!"

"Huh?"

"Look, let me be blunt. We all have our kinks. I happen to like teaching inexperienced men the art of sex. You just need some confidence, some education, and you'll be fine with the ladies. I promise. This won't hurt. I'm going to enjoy it just as much as you, but you have to relax some. Please."

"What about Amanda?" He asked, worried Amanda might interrupt whatever Terri was planning.

"She's not coming back until I text her," she assured him.

He turned and stared at her, his mouth open but no words coming out. She stood facing him, then climbed onto the couch with her legs spread over his as she sat on his lap. She took his chin and lifted it up.

"Chris, do you find me attractive? Do you like blondes? You have to talk sometime."

"Redheads are my favorite." He croaked.

She giggled. "Like your sister? We all have kinks, Chris."

"No! I mean, she's pretty, but, just no!"

"Got you to talk, at least. Now, I agree your sister is hot. But I have a cute face, decent boobs, and I've been told my ass is amazing. Is it amazing, Chris?"

"S-sure."

"How do you know, Chris? Feel it. Grab it. Squeeze it. Then answer me."

His hands shook as he reached up and slid them over her denim-clad butt. "I-it's great."

"You didn't squeeze it. You don't know. What about my boobs? Are they big enough?"

She took her t-shirt off in a quick move. She had a white lace bra on, holding in her 34 B's. She reached back and took his hand, squeezing her butt with it, then sliding it around to her breast.

"What do you think, Chris?"

"Th-they're nice."

"Nice? Just nice?"

"I've got nothing to compare them to." he said defensively.

"Ok, but if a girl asks you if you like any part of her, you need to be far more effusive in your praise. We're just as insecure as you are, some even more. When I ask if you like the way my tits feel, you need to tell me just how amazing and fantastic they are, how no one's could ever be better, how much you want to touch them forever. We'll know you're lying, but it's part of the mating game. Now, try again. Do you like my tits?"

"They're amazing, the best I've ever touched! I love them!" He responded sounding like an automaton.

"Better. A little less robotic would help, but much better. Now take loose my bra." She remarked undeterred.

He reached both hands behind her and managed to get it loose after much fumbling. She reached around and reattached it. "Try again. We're doing this until you can do it in your sleep."

He undid it seven more times, each time it was getting easier and he was getting faster. The last time, she rolled her shoulders forward. "This gesture means she wants you to slide it off her."

His shaking hands reached up, took the straps, slowly sliding them down her arms one at a time. She sat in facing him with her chest bare, her 34 B's sticking out with dark pink hard nipples.

"Now say something, Chris. Use my name. Tell me how much you like them."

"Terri, they're beautiful. I want to touch them, but I don't want to ruin this perfect moment."

"Very good! Now put your mouth on them, lick them, suck them, use your hands. I need you to make me believe what you just said."

He leaned forward and just barely licked a nipple, then groaned and put as much of her breast as he could fit in his mouth. His hands ran up her sides, one taking the breast he wasn't sucking, and squeezed, pulling instinctively on her nipple. Terri groaned and pulled his head into her.

"I just knew you'd be good at this. I love this, Chris."

He pulled his head from her breast and looked her in the eyes. "Thank you."

He returned to her chest, going to the other breast this time and giving it the same treatment. She rocked back on forth on his groin, then pulled his head from her and looked at him.

"I-is that all you down there? Really? I'm going to find out soon anyway, don't answer. I think I'm really gonna like today, Chris."

"I don't really know what you mean. I promise you won't enjoy today more than me though." It had finally sunk in for Chris what was going to happen.

She let him play with her breasts for a few more minutes, then pulled him off again. "This is fun, but there's so much more fun to be had. I'm going to stand up, but I'm not rejecting you. Pretend this is the back seat of a car, Chris."

He nodded as she stood, her chest wet, and then sat next to him. "Ok, Chris, now if a woman does this, she's gonna want to see it. The least you'll get is a handjob, the best is everything. One thing. If she says no, she means no. Stop. Now and forever. OK?"

"If she says no, she means it." He confirmed.

"Right. Now, here we go."

She slid her hand over the bulge in his pants and began to pull on the zipper. Once it was down, she put her hand in the hole and began to explore. Her eyes got big and she looked up at him.

"You've been keeping this from all the girls? Jesus, Chris, this thing... I gotta see this!"

She unbuttoned his jeans and slid them down as he lifted his butt up to allow them to come down. His boxers were tented, she grabbed the waistband pulled it down to his knees, then looked him in the eyes.

"Chris, I don't know how to say this. I don't want you to get a big head, or think you're weird, but that's the fattest dick I've ever seen. I've seen longer, but you got some girth, boy! You're built like a soda can! Maybe your future is porn!"

She reached out and stroked it, sliding her small hand up and down smearing the precum from the tip down its length.

"P-please stop. I'm gonna, well, y'know!"

"Cum. You're gonna cum. I want you to. You'll think clearer and last longer once you do. Cum on my tits, Chris!"

That was all it took. A woman's hand and some dirty talk and he began to spew like a fountain. He shot seven shots, the first going up to her chin. She milked him until he stopped and he was trying to get her to let go.

She licked her hand. "Not bad. I recommend some pineapple juice, it makes it taste better, but not bad. You were kinda backed up, I think. Don't worry, you'll do this at least three more times today."

"That was just amazing."

"I'm sure it was. The first time someone else does it for you it's sooooo much better." She took his t-shirt off and wiped herself off, then sat beside him.

"OK, now, if I make you cum in the back seat, you have to do me too. Any idea where to begin?" she quizzed.

He shook his head side-to-side.

"I didn't think so. First, back to kissing. We like that. Keep feeling my tits, then slide a hand down to my pants. I'll direct from there once you're on the right path."

He was nervous again, but once he started kissing her again he felt like he knew what he was doing. He squeezed then sucked on her tits for a bit then ran his hand slowly down her belly then between her legs as she spread them. He rubbed up and down and she moaned a little.

"Not bad, but if she doesn't spread her legs you don't force it. Again, no means no. If she doesn't spread her legs, you don't go. Lucky for you, I did. Now, unsnap the top of my pants, then slowly unzip them."

He did as instructed, having some problems with the snap at first. The zipper came down easily.

"I know you thought it was awkward, but honestly it's pretty hard to take someone else's clothes off. You did good. Now, slide your hand in over my panties. Just do exactly what you were doing before. Oh, yeah just like that!"

He was eager to touch his first pussy and started being a little bit more assertive. Her hips arched up as he rubbed her. She moaned as he kissed her, then grabbed his hand.

"Slow down a little. We need to be revved up slowly. Guys are zero-to-sixty in two seconds, but girls need more time. Rub slow, see if her panties get damp. Mine are, I'm sure you feel it."

He nodded yes.

"Good. Now take your hand out and smell your fingers."

He did as she said, and the smell was intoxicating for him.

"Chris, that smell is an aroused woman. Learn this smell, remember this smell. Now put your hand back in, rub just a little faster and harder. When you feel comfortable, pull my pants down."

Again, he did as she said. She could have told him to rob a bank and he would have at this point. He began rubbing the wet spot and found it got wetter quickly. She began to arch her hips toward him as he tried to get her shorts down. She helped, and suddenly they were off. She was wearing white bikini underwear with lots of lace. He started to rub her again over her panties and she moaned in his ear, "Inside the panties!"

He slid a shaky hand down inside, touching a girl for the first time. She arched her back, kissed him, and said, "Put a finger inside!"

It was almost a religious experience for him. He slid his finger around until he found the entrance and pushed forward. His middle finger rubbed against a nub at the top of her slit and she quivered.

"You OK?"

"Better than OK, Chris. That's my clit. It's a magic thing, it makes us cum. Put your middle finger in me, use your thumb to gently rub on that bump." He did as he was told, and she began to shudder before she fell back into the couch. He stopped, thinking he'd done something wrong.

She was breathing hard for a moment, then grabbed his face and kissed him. "Good job, Chris. You made me cum with your fingers. That was pretty good, I know some much more experienced guys that couldn't achieve that."

While she knew she was an easy cum, she wanted to build his confidence. He began to smile.

"OK, next lesson. I'm gonna do something for you first, then it's your turn." She crawled onto the floor and between his legs. "You're lucky, Chris. Some girls don't like doing this, but me? I love it. It's a power trip for me."

He watched as she grabbed his dick and kissed it lightly, then opened her mouth wide sliding her tongue over the crown. She only managed about half, but her fist was working the other half. She gave him a messy wet blowjob, because she knew lubrication was key and that most guys liked it "dirty". She gagged herself intentionally a few times, then pulled off with a "pop!" and looked up at him.

"Grab my hair, move my head how you like. I like it rougher than some, you can fuck my face. If a girl objects, just stop. No biggie unless you keep trying to force something."

He put his hand on the back of her head and began to direct. He pushed her farther down and she gagged, then pulled her off as drool connected her mouth with his dick. She smiled at him and he pushed her again, his hips moving without his conscious thought. He didn't last much longer, as he tried to push her off, she shook her head 'no'. He began to cum down her throat and in her mouth. She coughed a little and the last spurt just went all over him. She swallowed and began to lick him clean, not stopping until he was hard again.

"Again, not bad. Some girls hate to gag, so you'll have to be more gentle. Some girls will spit it out or not let you cum in their mouth. Some want it on their face or tits. Again, their choice. I like it. Now, if you expect a girl to do this, you have to learn to reciprocate. You ready?"

He nodded yes. She could have asked him for anything at that point. She got up on the couch and laid back. "First a little education." She reached down and spread herself out. Using her fingers, she pointed out things as she talked. "These are the outer lips. Some are bigger, some smaller. Generally, they get fatter when a woman is excited. These are the inner lips. Some hang out, some don't, but never, ever, ever let a woman hear you call them 'meat curtains'. This up here is my clit. You've felt it, this is what it looks like. Right now it's sticking out, like a baby hard-on. Normally it's inside the hood. Now, start by licking outside, then put your tongue inside. Lick between the inner and outer lips, then start trying to see how far your tongue will go inside. Use your fingers too, move them in-and-out and around, rub the clit a little. Do what comes naturally. When you stick your finger in upside down, try to find a rough patch with your fingertip. That's the g-spot, use your finger to rub it."

He nodded and bent down between her thighs. He hesitantly took a first lick, then decided the taste wasn't bad and began to lick with more fervor. He licked for a bit then put his finger in, swirling it around and taking it out.

"Fuck me with your finger, Chris. Use two," she moaned.

He began with just one finger, then put two in as he licked, moving them in and out. He flicked her clit with his tongue then using his fingers found the rough patch she'd mentioned. He flicked her clit and rubbed the patch and was rewarded with her bucking into his face and clenching his head with her thighs, cumming like a freight train. When she let go, he moved back, grinning.

"Chris, that was pretty good. For a first time, it was excellent. I'm gonna say you've watched a lot of porn, but you did learn something. Now, one more thing. We need to go to your bedroom first, then we're gonna fuck. Imma teach you every position I can think of. I like you, Chris, and that helps." She took his hand and they stood. "Lead the way!"

He took her to his room and she sat on the bed. "First things first. This part is great, but it can have consequences too. Babies. So make sure both of you are protected for that first. If you don't know for sure, use your own protection. Use a rubber, especially if you don't know her. You're going to break that rule today, because I'm safe and clean. I get tested. I've been on the pill for years. Understand?"

"I get it. I don't want to be a dad yet. I trust Amanda, so by extension you."

"Just to be clear, you shouldn't normally. Just this once." With that, she laid back on the bed. "Now Chris, come over here so I can show you how this works."

He got on the bed with her. "First we're gonna do the traditional missionary position. It's easy and fun. Just crawl up here between my legs, I'll show you the rest." He crawled up between her spread legs and she pulled him down for a kiss. "Kissing is always good. Kiss her, touch her, stroke her. Find what she likes and keep doing it. Now for the best part!"

He looked down, his cock was almost touching her. She reached down and took him in her hand, pulling him forward until she had him at her entrance. "Push Chris. Become a man."

He pushed, feeling something he couldn't even begin to describe. The velvety smoothness, the tightness, the wetness, it all came together for a sensation he couldn't explain. Once he was all the way in, Terri smiled at him.

"You did it. You're not a virgin anymore. Now, for the future, you always need to go slow. You're big, and we ladies gotta get used to it. I've been waiting for this all afternoon, Chris. Start moving in and out, you know the drill. Let's get you some experience!"

He began to move, awkwardly at first. He developed a rhythm and she began to fuck back at him. It made everything even better for him. He remembered what she said and began to stroke her, squeezing her breasts, pulling her nipples, kissing her where he could reach. All to quickly for him, however, it was over. He thrust hard one time and everything was too much for him. He came, spewing his third load into her. She felt him cum, causing her to have a small orgasm as well.

He held still until he was done, then she pushed him out and off of her. He was panting with exertion and excitement. She was smiling at him, watching his eyes. "So, Chris, definitely not gay!"

"Definitely not!"

"I'm going to give you a minute, then we're gonna do something else, another way if you will. I'm going to suck you hard first. I'll give you a sec, I know you're kinda overwhelmed right now."

She was right. He was overwhelmed, excited, insane, a blend of emotions he had to process before he could start again. Once he had his breath back, he leaned over and kissed Terri, surprising her.

"What was that for?"

"Just a thank you."

"Hey, I'm enjoying this too! I wouldn't do this if I didn't. Before we go any further, one more thing. I don't love you, and you don't love me. This is just sex. It's fun, but it isn't love. Do you understand?"

"Actually, yes. I mean, I'd love to do this with you again. I can't love you, I don't even know you really."

"Good. Some guys confuse this for love, then I have to be mean to make them go away. Maybe we will do this again, maybe not. We'll see. But it seems your head is screwed on straight, so how do you feel about me on top?"