Ava

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Teaching him what he needs to know.
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tailtales
tailtales
191 Followers

Ava

Teaching him what he needs to know

I prefer to leave out the blow by blow details in my tales. If you want that type of story there are many on this site that will satisfy those needs.

Part 1

Friday night and we were cleaning the kitchen after dinner. "Can I fuck you?"

"What...No...Why would you ask me that?"

Sunday night and we were cleaning the kitchen after dinner. "Could I fuck you tonight?"

"Are you nuts? Stop asking me that."

Tuesday morning and heading out the door to school, "After school I'd like to fuck you."

"Damn it Charley. Stop asking me. We're not doing that."

Thursday evening while watching the news, "This is boring let's go and fuck."

"For the last time I'm not doing that with you. You're my brother it isn't right. So just stop asking. Forget it, understand?"

Saturday afternoon while cleaning the basement, "Please Ava, let me fuck you."

"OK...What is wrong with you? We can't do that. Do it with your girlfriend, for pity's sake." Long pause. "Wait a minute is that the problem? Fancy won't? You're horny and she's not willing. Why not just do what boys do when they need relief?"

"I think girls do that to. I can hear you sometimes...At night...When it's real still in the house."

"Enough. I'm not having sex with you. The subject is closed. Period...Understand?"

Part 2

Friday night a week later "Can I ask you something?"

"You're the smart one. I'm the pretty one. It'd be better to ask you of your professors."

"No, that's not a good idea. You'd be better at helping me with this."

I relented and said I would help if I could but he really should ask someone with more knowledge than me. Well it turns out I did have the information on the subject that my brother needed. You would think that being the same age and all we'd both have the same amount of experience in the subject. Not true it seems.

It appears that his girlfriend was suggesting that they take their romance to the next level and poor Charley was afraid that he might not be able to satisfy her. Questions and answers flowed for the next hour or so. Thankfully our parents were gone for the weekend. It seems Fancy had been taking his hand and placing it on a breast as they were kissing, over her clothes. Then she would put her hand on his crotch and squeeze him a little.

"So let me get this straight...You've never touched her bare boob? Is it possible that is all she wants? How about you slip your hand up under her shirt and just do it? Touch her there. You'll find it's kind of neat. "

The problem with the bra came up. I told him he could just push it up and out of the way or better yet reach around and unhook it. I tried to explain how it worked and finally went to my room and brought out one to show him. I pulled it tight and let him try. He fumbled around and after a little struggle managed to get it undone.

"Could I maybe see if I can do it for real?"

"What on me? I don't think so. That would be weird."

He begged, I agreed. This was so wrong. "No kissing, understand? Just hug me and reach around and get under my t-shirt and do it."

The operation was a success and the patient survived. Actually it felt kind of good, especially when his hand came around and touched my side boob a little. Afraid of where this was headed I called a halt and headed off to bed. Unable to sleep I ended up using my vibrator.

Part 3

It was a week later and I had to ask, "Well, how was it going with Fancy? Is she happy now? You're doing things with her boobs?"

"Well kind of, I did what you taught me and she seemed pleased. But then she tried to take her blouse off and I got nervous and told her I had an early class and we should probably call it a night. What was I going to do if she really did that? Showed her bare breasts? To be honest it scared me. I knew I would be expected to maybe kiss them or something."

I had a real problem. My brother was a hopeless case. How could he grow up with the internet and everything and not know what every other guy knew. "Oh crap. Here I'll let you do this one time. You're a complete moron ya know that right?"

I started to pull up my shirt. "No wait...You do it. Take my shirt off me. Good, now the bra. Reach around like I told you and do it. All right now pull it off and toss it out of the way. Not too hard was it? Now look at my tits for a moment, nothing special right? That brown circle is called areola and then the nipples of course. Just liked a man has except we've got a bit more body to ours. Most have bigger ones than mine but I like what I've got. I can go braless if I want. I'm a b size. Looking at Fancy I would guess she's a large c. They run all the way up to humongous, like gg even."

"I can't believe I'm doing this. Touch me. No, touch my tit stupid. Gently, ya like that. Kind of squeeze it, not too hard. It's not a melon. Ok...now kiss the nipple. Good...now give it a little suck. Umm...Perfect. Now the other one, you gotta pay equal attention to both of them. While kissing and sucking one hold and caress the other. Don't let it get lonely. Some girls like their nipples squeezed and pulled on. Not me, ya have to try it and see how she reacts. Try licking around the areola. I love it when it's done. Makes me feel all tingly and stuff. Ok...Enough...Stop now. You got it." Another night with the vibrator, this was getting serious.

Part 4

"Thank you Ava. I did everything you showed me. I thought Fancy was going to never let me stop last night. We're even going out again tonight. She said if I played my cards right she'd no something special for me. What do you think she means?"

"Well...I expect maybe she might return the favor. You said she's squeezed you pecker before. Over your pants, maybe she's going to do more?"

"Oh my god, ya think she might?"

"Ya...Maybe take out your penis and play with it a bit. You better shower really clean especially that part. It might be a good idea to jerk off before you go out. I had a friend that all I had to do was touch him and he'd start squirting all over the place. I gotta tell ya, not a lot of fun when he's done before ya even get started."

"I don't know if I'm ready for something like that. I think I better call her and tell her I'm sick or something. Maybe my grandma died?"

"Really, your grandma passed, for shame on you? You idiot, go shower and come back here. I'll show you what she might do to you."

I'm not sure who's the bigger idiot, me or doofus for what I'm going to do. Ten minutes later my brother was standing in my doorway. "Ok...I can't believe I'm going to do this. Take your clothes off, all of them, shirt, pants, undies, everything. No wait stop. Don't get undressed, downstairs on the couch. That way we can play it out like it might happen in the car"

I actually let my brother kiss me before he pulled my shirt off and kiss me again as he was undoing my bra. I was kind of proud of the way he treated my tits. I'm a good teacher I guess. I almost forgot why we were here on the couch. Our parents had left for a party and please don't let them come home early.

As Charley was involved with my upper body I started to undo his pants, without any success. "Listen up buddy, if a girl is messing around with your belt and stuff ya gotta cooperate. Lean back let her get at them. Yes...That's better. You can still do what you've been doing, just let her do her thing...Understand."

"Now...Help me here...Lift your ass up. So I can pull these down. Good now your undies. Ahhh yes, there you are. Nice. You are blessed. I think that might be the biggest one I've ever seen. It's so long and so firm and so nicely shaped. Yup, it's a keeper."

He opened his mouth and before he could ask, "No...You...Do...Not...Ask...That...Question...Never...Ever."

I wasn't about to tell him I had seen six of them up close and personal. And two more that I didn't see but had been in touch with. Actually I was sure it was the biggest I'd ever seen. To guess I'd think seven inches long but I thought kind of skinny.

"Now just relax and let me do this for a bit. Lean back, I'm going to touch you. Like this. Ok, how's that? Feel good? Better than when you do it maybe? Now a little faster, are you getting ready, warn me before it happens."             

He tried, "It's going to" and it did. All over, it was a gusher, his shirt, his thighs and then my hand when it slowed down to oozing out the last bit. "Well, I think you need another shower but you should be able to hold back tonight and not spoil Fancy's fun."

Part 5

Our classes didn't start till eleven the next day. Mom and dad had both left for work and it was just the two of us eating breakfast. I couldn't wait, "Well tell me. How did it go last night? Everything work out ok? Did Fancy treat you to something special?"

"It was wonderful. Thank you so much for what you did for me and you were right. I was able to hold back for a bit, not as long as when I do it myself. But I think Fancy was impressed. If you can believe this she actually tested it. She licked her fingers. I could hardly believe it. She actually tested my stuff."

"Good I'm glad everything worked out ok with you two. It should be clear sailing from now on."

"Well not all clear. She kind of indicated that she wanted more. As I was sucking on one breast and doing stuff to the other she kind of put my free hand on her leg. Real close to her place, ya know what I mean? So I rubbed her down there and I think maybe she had a good time. She moaned and then went real stiff. At first I was afraid but then she relaxed so then everything was good. We kissed a little more before taking her home. As I kissed her goodnight she told me that it was the best night ever and she could hardly wait until the next time. She said that what I did was so much better than the other way. Do you think she was hinting that she might masturbate? Do girls really do that? I can't picture you or her doing that to yourselves."

"Well we might, just like boys we get the urge sometimes and then we have to...Ya known."

"Sorry dumb question. I forgot, I remember hearing you some nights. Oh crap...Do you hear me?"

"Nope, I'm not hearing a sound from your room, nothing."

"That's good. Maybe I don't do it."

"Liar, everyone does. One night I think I heard mom and dad doing it. Together."

"Oh gross, really?"

"Ok, it's time to get to school. Keep up the good work. Fancy is a nice girl. I'm glad you're keeping her happy."

Part 6

A week later my brother asked if we might talk after dinner. "I kind of have a problem."

"You're one big problem wrapped up in a bunch of little problems. Talk to your buddies. I'm out of information; I've told you everything I know. Don't bug me. Go away."

"Don't be that way, I know you can help. It's Fancy; I think she's going to dump me if I don't do something real soon."

"Come on Charley, you're doing her boobs right and rubbing her down there. You said she had an orgasm, right? You been giving her more of them right? She gives them to you with her hands right? What more does she want? Oh...Ok...More stuff right? Not happy with the way it's going, you've been getting her bottoms off and giving her a personal touch right?"

"Do think I should? Really take her pants off and stuff. What if she doesn't want that? What if it pisses her off? What if I don't do it right? This is not good. How about if you call her? Ask her what she wants."

"Listen jerk face, first I'm not calling your girlfriend and asking about her sex life or lack of it. Any girl is only going to be satisfied just so long with you doing her with her clothes in the way. Man up for sake. Take charge for once. If she doesn't want her bare pussy out there she'll tell real quickly."

"Could you maybe?"

"Could I what...Oh no. I've gone as far as I'm going. We've gone too far as it is. Forget it...No."

Part 7

The next morning, "Please Ava, you gotta help me. What if I do it wrong, hurt her or something."

"You're a certified idiot. I've got an idiot for a brother. Please, someone tell me he got switched at birth and my mom brought home the wrong boy baby. I demand a DNA test."

"Come on, will you please help me. I'm in love and if Fancy dumps me it'll be your entire fault. Just a little help, please my darling sister, I'll owe you big time. I'll wash your clothes; make your bed, whatever you want."

"Will you let me watch you jerk off?"

"Really, you want to watch me do that to myself?"

"Yep, I want to see you strip off all your clothes and then stand there right in front of me and do it. Masturbate until you come. Squirt big time. Show me how you do it. Then if you do a good job I might let you see what the other part of me looks like and give you a few tips on the care and feeding of a girls lady parts."

When Charley turned and stormed off I figured I had finally brought an end to his asking me for help with his sex life.

Part 8

For the first time in my life I was wrong. That night as I was getting ready for bed there was a gentle knocking on my door. "Ava, it's me, can I come in?"

"Sure, come on in."

As the door closed I asked him, "Were you going to show me something? The thing I wanted this morning? Are you going to beat your meat and let me watch? Watch every stroke of your hand as it goes up and down the shaft of your hard boner?"

He was blushing so hard I was afraid he might pass out from heat stroke. All he could do was nod his head yes. "Great. Let me get comfy here on the bed. Then you come stand right here and do it." And he did. First I was surprised when he was naked. Except for his head he was hairless. I mean nothing, nada, just completely bald, even around his man stuff, not a hair. I asked and when he reminded me that he was on the school swim team and it was kind of a competition thing.

I swear it took him more than ten minutes before he climaxed. But I enjoyed every minute of it. It was wonderful to watch his expression and then his hand and then his expression some more, especially as he got closer and closer. I might ask for an encore, before I show him want he wants. Of course that would be cruel except I never said I'd show him anymore. I just said maybe. But I'm not that way.

"Ok my little uniformed buddy. Help me. Let me stand up and you can take off my top and then my bra." As he did I realized he was good at it and told him so. "Now warm me up Charley. Show my tits some love. Be good to them. They're your best friend right now. Make me happy. Get my juices flowing, so I can feel some excitement."

I think I should change my major in school. I would make a super teacher, or maybe a sex therapist. I'm going to have to think about it. I wonder what my advisor think. But he's a man. He'd just want me to demonstrate my skills. Dirty pig, I'm going to report him to the school board, how dare he want that? Oh wait, I guess I should wait until he crosses the line, shouldn't I?

Back to my brother, he's expecting something, a show and tell, of my lady parts. How in the hell did I ever get in this mess? I tried to put my pajama top on but he insisted that all of me should be bare. Why not, he's seen and touched and messed with my tits already so no big deal, let's let them out. I'll just be all naked for him if that'll make him happy.

So I did, my slacks and panties came off. Then I was on my bed naked and it seconds I could see the effect I was having. It started with just a slight swelling of his organ. When I spread my legs a little the swelling grew, swiftly, until I swear it was bigger than ever before. "Liking what you're seeing Charley?"

He only nodded his head yes. I don't believe in the hairless look that's so popular right now. I trim a little, don't like the real bushy look either. The truth being told at this point I was enjoying the effect I was having on my brother. It's good to know that you can have a positive effect on someone. Yes the effect was very apparent and I was enjoying myself. Kind of sad to say isn't it? Showing off to your brother?

So I held school on the parts that are normally hidden by panties. You know, the inner and outer lips, the birth channel, or as I put it the pecker tube and the most important part the clit and the hood that kept it safe and warm.

"Can I?"

"Sure why not. You've seen it all. Ya, go ahead touch me, what the hell, just pretend I'm a big doll that can be manipulated for your pleasure." When he did, "Damn it Charley. Get your finger wet. Slip it up inside first. That hurts. Ya have to remember, that stuff is tender. Fancy will kill you if you aren't gentle."

I guess I'm not a smart as I would like to think I am. I let him explore until I could feel that I was getting close and when I realized what was going to happen I called a stop to it all. He was only out of my room for a few minutes when I exploded and I didn't need my vibrator. From the hall a voice, "I heard that."

Part 9

"You're the best sister ever. I swear I'll never be mean to you again."

"Well thank you. That was nice of you to say that. I appreciate it."

"There's just one little thing."

"No. No more. We've completely crossed the line. Nope, if anyone ever found out, we'd be banished to hell or even worse. Don't even ask."

"But, can I at least tell you what happened last night? It really freaked me out."

"Go ahead, you can tell me but that's it. I'm not giving out any more advice. It's time you stand on your own."

"She licked me, me penis. Then she put it in her mouth. And then did stuff. It was so great, but then I did it right in her mouth. I couldn't help it. It just happened so quickly. I tried not to but I just did it."

"So my brother got his first blow job. Neat, did she swallow or spit it all out? Make you kiss her and share the bounty? I want details, come on share."

"I don't know. She did kiss me. I thought it was saliva but oh wow do you think it was me?"

"That'd be my guess. She is one brave chick. I love her. You've got a keeper for sure. Did you return the favor?"

"You mean did I? Oh crap, do you think I should have? I did use my fingers, like you showed me." For a minute he just sat there and I knew what was coming before he even opened his mouth. "Ava, would you, could you, kind a do one more thing. I promise just one more thing. Then I'll never ask for anything more, ever, I promise. Please."

"You want a lesson in eating pussy, right? How to do a girl with your mouth and with your tongue is that right?" For the strangest reason I wasn't against the idea. I had to admit to myself at least the idea was intriguing. What could be better? Getting a little free action? I was between boyfriends and was feeling the need, so why not?

"Ok, tonight mom and dad are going out to the theater. After they leave but there's one condition."

"Anything, whatever you want. I'll do whatever, I promise. I'll never ask for anything else. I'll wash your car. Whatever, just ask."

"Understand this, I'm not doing you. This is strictly a one way street. You keep your pants on and zipped."

"Absolutely, that never even crossed my mind."

I have to be the stupidest sister ever. I'm naked, on my bed telling my brother to spend some time because a girl likes to be warmed up slowly, let the tension and anticipate build first. "Ya shouldn't just dive between her legs. Work your way there. Hugging and kissing. Spend some time on her tits. Rub her legs, especially on the insides of her thighs. Before ya slip her panties off touch her there. If she lifts her buns up it's time to take them off. Be careful, don't tear them, she may want to put them back on."

Of course we had skipped all of the ground work. This wasn't a seduction. It was a lesson. So after reminding him about being gentle and where all the parts are I let him practice. Practice my ass. If I didn't know better I would have bet he had been there before. I was ready a whole lot sooner than I would have believed before. I expected to have to suffer through his fumbling around and needing to direct traffic.

tailtales
tailtales
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