Masturbation is something that we usually learn by ourselves. Nobody will dare tell you where to touch this and that, and how to touch it—unless you’re talking to a horny stranger online. No, the internet won’t give you the most crude experience of erotic self-stimulation like how young people did it in the ‘50s, but you’ll learn quite a few important things chatting with someone like Jack (more below).
Teen Masturbation 101
We often hear experts say that masturbation is completely normal and, when done regularly, can produce positive effects on your overall health and well-being. Although you’re not supposed to make your regular morning sessions of self-play the main topic of discussion at brunch with your friends, we generally accept this notion as true.
But what if you’re young and clueless and haven’t done it yet? You only have two lessons to learn:
1. Know where your clit is.
2. Let your fingers do the job.
Annie Learns How To Play with Herself
Today’s Chat Erotica session features Annie, a curious, innocent teen who’s eager to ask all sorts of questions and learn how to talk sexy. And when she stumbles upon Jack, a horny, married guy who’s more than willing to teach her the basics of teen masturbation, she discovers what it feels like to play with herself for the first time.
Watch below.
Part 1
Part 2
Part 3
Part 4
Part 5
Part 6
Part 7
Prefer reading the actual chat? Here you go.
Here’s the transcript for the video above:
Jack: Hey sweetheart.
Annie: Hey.
Jack: Like older guys?
Annie: Sure i guess.
Jack: How old are you, baby?
Annie: I mean I’m old enuf to be here. I’m still in school tho.
Jack: Cool.
Jack: What are you into?
Annie: I’m still kind of figuring out actually, that’s why i’m here i guess. How bout u?
Jack: I’m open to most things. Chat, rp
Annie: Oh ok. So ure married?
Jack: Yeah.
Annie: Does she know u come here?
Jack: No.
Annie: So what kind of stuff do u like to do here?
Jack: Often role play, or maybe just chat.
Annie: What do u chat about?
Jack: I don’t wanna sound too pervy, but things that turn us on, things I’d like to do with you, etc.
Annie: Oh no that’s cool, i mean it’s sex chat, right?
Jack: Haha, yeah.
Annie: So what turns u on?
Jack: Cute (legal) teens…
Annie: That’s natural enuf.
Annie: Is ur wife cool with that? I mean she should be.
Jack: I don’t think she would be!
Jack: Probably be jealous!
Annie: Why not? Isn’t that just natural tho? And like fantasy and stuff?
Jack: I guess kinda, yeah.
Annie: Well, isn’t being attracted to younger girls natural? I guess if i was married i don’t think i would try to fight that.
Jack: Mmmmm you sound like you’d be a hot wife!
Annie: Lol idk.
Annie: I don’t even know what i’m doing yet.
Jack: What would you like to chat about?
Annie: Learn how to talk sexy and stuff.
Jack: You like when guys, older guys, check you out?
Annie: Yeah it’s kind of cool. Makes me feel cute.
Jack: Trying to look at you without being too obvious.
Annie: Totally. It’s fun.
Annie: There’s this one dad i know who’s always trying to look when he thinks i’m not looking.
Jack: Mmmmmmm.
Jack: I’d totally be that guy!
Annie: Um yeah i guess. My leg are skinny.
Jack: Skinny legs can be hot.
Jack: He’s probably thought about you while he touches himself…..
Annie: No!
Jack: Oh he def has.
Annie: That would be a lot.
Jack: What would?
Annie: Thinking about me and doing that.
Jack: You know guys are almost all kinda pervy?!
Annie: Haha yeah i’ve heard that.
Jack: You’re hot and young, he checks you out…..
Jack: He definitely jerks thinking about you…..
Annie: Omg idk. Not sure he’d think of me that way.
Jack: Trust me. If he checks you out, he does.
Annie: I’m friends with his daughter.
Jack: He probably likes that….
Annie: Do all guys do that?
Jack: I don’t know about all…..
Jack: But most do.
Annie: What about ones who aren’t supposed to?
Jack: Haha…. especially them.
Jack: May I ask a question?
Annie: Yeah.
Jack: How far have you gone?
Annie: I haven’t really. I kissed a guy.
Annie: He wanted to do more but i was scared.
Jack: Awwwww baby.
Jack: You’re sweet.
Jack: Did you wanna do more?
Annie: Yeah maybe.
Annie: I just don’t know what to do.
Jack: Just do what comes naturally.
Jack: Kissing…… touching.
Jack: The right guy will build up slowly.
Annie: Kissing was fun.
Jack: You’re making me remember when I was your age.
Annie: Is that bad lol.
Jack: Not at all.
Jack: Was hot building up to it. Kissing then cuddling…
Annie: Were u nervous?
Jack: I was, to start with, yeah.
Jack: My gf would lay half on me, kinda straddling my hip.
Jack: As she got turned on, she would grind against my hip.
Annie: That sounds cool.
Jack: It was hot.
Jack: I would hold her ass at first, helping her rub against me.
Annie: Did she just know what to do?
Jack: Kinda. I don’t think she planned it, just knew that it would feel good.
Annie: Hopefully that would be how it goes.
Jack: And we did it a few times.
Annie: Did what a few times?
Jack: Kissing and grinding.
Jack: Then touching.
Jack: Then we would kiss each other’s bodies…..
Jack: Until she sucked my cock….
Annie: Oh wow lol.
Jack: I’d love to build up like that with you…..
Jack: But I’d teach you if you seemed unsure.
Annie: I wish u could.
Jack: I’d be gentle with you….
Annie: I want to learn how to make a guy cum.
Jack: Mmmmmmm.
Annie: Can i ask u something?
Jack: Sure.
Annie: R u supposed to squeeze it or just move ur hand?
Annie: And doesn’t it hurt when u move it up and down?
Jack: Squeeze and move.
Jack: It’s doesn’t hurt.
Annie: Doesn’t it like rub ur skin all rashy?
Jack: Not too tight, but if you gripped too tight, I’d just tell you….
Jack: Not really, but some people use lube.
Jack: Or, and this is gonna sound pervy, spit.
Annie: Oh ok! Thanks! Lol.
Annie: I’m sorry this is so lame.
Jack: To be honest, you’re cute.
Jack: Very sexy.
Jack: And thinking about you is a turn on.
Annie: Really? Thanks.
Annie: I wish it was okay for u to just show me how it happens.
Jack: Mmmmmmm.
Jack: What would you want me to show you?
Annie: How to touch it.
Annie: What to do.
Jack: I’d get really hard doing that.
Annie: Idk i’m afraid u wouldn’t.
Jack: Pretty young teen learning to touch my cock…..
Jack: I’d be rock hard baby.
Annie: I wish i could touch it.
Jack: Me too.
Jack: Does it turn you on?
Annie: Idk i guess. Like i said, i’m still kind of figuring stuff out.
Jack: Maybe you’d be turned on when you felt how turned on you made me.
Annie: But i would definitely touch u.
Annie: I mean it feels nice to talk about it and i feel warm.
Jack: Mmmmmmmmm.
Jack: I’d love to be touching you right now.
Annie: And it’s kind of funny to breathe.
Annie: I would let u.
Jack: Big hands caressing you.
Jack: Brushing between your legs gently.
Annie: That would def be new.
Jack: Taking it slowly to see how you react.
Annie: Would u teach me how to make it cum?
Jack: Mmmmmmm fuck.
Jack: I’d love to!
Jack: That would make me feel good.
Jack: I’d get really hard.
Annie: How would u want me to do it?
Jack: Maybe with your hand at first…..
Jack: Then when you felt happy and confident, with your mouth, if you wanted.
Annie: Guys like it when they cum in a girl’s mouth, huh?
Jack: Very much!
Annie: R u hard right now?
Jack: Very.
Annie: I like that.
Annie: Can u make it happen?
Jack: Can I make my cock cum?
Jack: Oh yeah.
Annie: I’d like it if u would.
Jack: I’d have to warn you if I was there, I cum hard…..
Annie: What does that mean?
Jack: Means it squirts hard….. kinda messy….
Annie: That’s ok. I wouldn’t mind.
Annie: I want u to make it squirt.
Jack: That made me throb!
Annie: I wish i could see it cum out.
Annie: Wish u could teach me everything.
Jack: Fuck.
Jack: So hard for you right now.
Jack: Mmmmmm.
Annie: That makes me feel good.
Jack: You could touch yourself when you’re ready too.
Annie: Never done that before tbh.
Jack: Just do what feels natural.
Jack: Or I could show you how to touch yourself.
Jack: What to do….. where to touch.
Annie: Yeah i’d want u to just show me.
Jack: I’d take your hand in mine, and rub your pussy.
Jack: Pressing your fingers against yourself.
Jack: Guiding you
Annie: I want to just do it for u. I don’t know how to do it to me.
Jack: You know where your clit is?
Annie: No
Jack: Aww baby
Jack: Slide your hand down your tummy, until you reach the top of your pussy……
Annie: Idk what to do it’s not like anybody teaches u
Jack: Your clit is the sensitive part at the top of your pussy….. it swells a little when you get turned on
Annie: The top u mean like the outside?
Jack: Yeah, not inside.
Jack: I’d lick my finger. Then rub over it gently.
Annie: U mean like the skin that’s around the outside?
Jack: Gently caressing round and over it in little circles.
Jack: Yeah, but just at the top
Jack: I want you to touch yourself for me.
Annie: R u sure?
Jack: Very sure.
Jack: Rub your fingers gently just above where you pee.
Annie: Oh ok u mean the nob thing there? That’s it?
Jack: That’s it baby.
Annie: Ok.
Jack: That’s your clit, it should feel good to rub it gently.
Annie: It does, but it feels weird.
Jack: That’s ok baby.
Annie: It makes my legs tingly.
Jack: Maybe slide your fingers down over your pussy for a second, and see if you’re wet.
Jack: If you are, rub it over your clit.
Annie: Kind of sticky?
Jack: Rub the stickiness over your clit for me.
Annie: It feels weird i’m kind of scared.
Jack: Don’t be scared babygirl.
Jack: It’s just supposed to feel good.
Annie: It makes me feel heavy, is that bad?
Annie: My chest feels heavy.
Jack: No, sweetheart.
Jack: Keep touching for me.
Jack: Do you wanna know something naughty?
Annie: Doing it.
Jack: If I was with you, I’d rub my cock there……
Annie: That made me feel heavier.
Jack: Yes sweetheart…..
Annie: Feels good but weird.
Annie: Heavy.
Jack: Mmmmmmmm.
Annie: I’m all sticky.
Jack: Sticky is good baby.
Jack: What are you thinking about baby?
Annie: It’s bad.
Jack: Shhh it’s ok.
Annie: Embarrassed.
Jack: Don’t be!
Jack: It’s ok to get horny.
Annie: My friend’s dad. Omg that’s the first time anyone said that to me.
Jack: You can get horny baby
Jack: Maybe he’d touch you like I would
Jack: Rubbing your clit……
Annie: I can’t stop doing it
Jack: Good girl
Annie: It feels so good
Annie: R u doing it to u?
Jack: Oh I am.
Jack: Annie baby, you’re making me very, very hard.
Annie: Why does this feel soooo good
Jack: It’s supposed to feel good baby.
Jack: I’m really hard for you Annie.
Annie: Jack it’s hard to stop.
Jack: Don’t stop baby.
Annie: My chest feels funny.
Jack: Mmmmmm keep rubbing Annie.
Jack: Rub that sticky pussy for me.
Annie: Wait i think i have to pee it feels weird.
Jack: That’s good.
Jack: That means you’re close to cumming baby.
Annie: I’m scared what’s going on.
Jack: Shhhhhh Annie.
Jack: Keep touching.
Annie: I’m scared.
Annie: I can’t stop.
Jack: You’re just touching yourself.
Annie: Oh gosh.
Jack: It’s natural baby.
Annie: So good.
Jack: Thats what I’d be doing to you Annie.
Annie: I’m all wet.
Jack: That means you like it.
Annie: I’m a slut oh no
Jack: You’re completely normal.
Jack: Not a slut.
Annie: Wait i feel weird.
Annie: Waittt
Jack: Keep rubbing.
Annie: Somethin
Jack: Press against your clit.
Jack: Not too much.
Jack: Don’t you dare stop.
Annie: I shou;d it somethin
Jack: Rub for me Annie.
Annie: Ohon
Annie: Wi
Jack: Rub that teenage pussy babygirl.
Jack: You’re gonna cum.
Annie: Oh no.
Annie: I think i did.
Jack: Mmmmmmmmmmmmm.
Annie: I thought i was gonna pee and then it’s like i sneezed.
Jack: Did that feel good sweetheart?
Annie: Oh no oh noooo yes it felt too good.
Jack: I love that.
Annie: But it’s bad.
Annie: Oh no it’s bad.
Jack: It’s normal baby.
Jack: All your friends do it.
Jack: Trust me!
Disclaimer: All names, characters, businesses, places, and events are fictional unless otherwise specified.
