Chat Me Up

(Disclaimer: THIS DIALOGUE IS NOT TAKEN FROM AN ACTUAL ONLINE CHAT.)

Chat category: Adult
Room: Role-playing

Private Chat window:
wellhung69: Young lady! Yes, you. Come to my office.
wellhung69: You have detention!
slipperywhenwet: At three, right?
wellhung69: Right! Do not be late.
slipperywhenwet: What happens if I'm late?
wellhung69: Come late and find out.
slipperywhenwet: Okay, it's 3:15 and I show up in your office.
slipperywhenwet: Books in hand, a shy look in my eyes...
slipperywhenwet: I'm sorry Mr. Wellhung. I meant to do my homework. I didn’t mean to skip class.
wellhung69: First you don't do your homework...
wellhung69: now you are late for detention!
slipperywhenwet: I'm sorry sir.
wellhung69: Do you know what the punishment is?
slipperywhenwet: No...
wellhung69: You’ve been too bad for simple detention.
wellhung69: Go close and lock my door. You need special attention.
slipperywhenwet: Okay. Whatever you say.
slipperywhenwet: Now what?
wellhung69: Come over here. (I pat my lap)
slipperywhenwet: You want me to sit in your lap?
wellhung69: No, I want you to bend over my knees.
slipperywhenwet: Okay, if I have to…but my skirt is so short...
slipperywhenwet: my panties might show.
wellhung69: I don't care.
wellhung69: Get over here now young lady!
slipperywhenwet: Okay, sorry.
wellhung69: Now bend over. Just like that.
wellhung69: Your skirt is short.
wellhung69: I rip off your panties…
wellhung69: …showing your cute lil ass.
slipperywhenwet: My white panties rip off easily...
wellhung69: I give each cheek a nice lil slap.
slipperywhenwet: I look back at you. Fear and apprehension in my eyes.
wellhung69: Good.
wellhung69: How does that feel?
slipperywhenwet: I deserve it. I've been bad.
wellhung69: I give you another smack, but this one is harder.
slipperywhenwet: *whimper* Ouch, it stings.
wellhung69: …and another. Harder this time.
slipperywhenwet: No, no more. Please. I’m sorry.
slipperywhenwet: I’ve been bad...
wellhung69: Well what are you going to do to make it right?
wellhung69: This is not over, young lady!
slipperywhenwet: Uh, I don’t know if this will help, but can I unbutton your pants?
wellhung69: Okay. Let’s see if you can do it.
slipperywhenwet: I unbutton your fly and pull out your hard cock.
wellhung69: You better be good or you’ll get more punishment.
slipperywhenwet: I get down on my knees in front of you and pull you into my wet, warm, soft mouth.
wellhung69: That’s nice.
slipperywhenwet: Will this make up for it?
slipperywhenwet: Or do I get more spankings?
wellhung69: You must do better than that to get out of this one.
slipperywhenwet: What if I put your cock so deeply into my mouth that I was able to lick your balls while my lips pressed against the base of your penis.
wellhung69: Try it and we will see.
slipperywhenwet: If I rub my tongue up and down, under your cock...
slipperywhenwet: suck on your head...
slipperywhenwet: …make you moan.
slipperywhenwet: I'll try my best.
wellhung69: You better.
slipperywhenwet: Let me take off my top.
wellhung69: Let me see your perky lil tits.
slipperywhenwet: I unbutton my blouse. My bra unsnaps in the font exposing my hard, dark nipples…
slipperywhenwet: …soft, ivory skin.
wellhung69: Ah, that’s real nice.
slipperywhenwet: will you touch them?
slipperywhenwet: Is it wrong for me to show them to you? Will you punish me for showing them to you?
Wellhung69: Yes. Of course I will punish you. I am the principal after all!
Wellhung69: I will punish you good!
slipperywhenwet: *wait* There's a knock at the door.
slipperywhenwet: Should I see who it is?
wellhung69: No, you should play with your nipples.
slipperywhenwet: Should we just ignore the door?
wellhung69: Are you expecting someone?
slipperywhenwet: I will do as you say, but I think you should get the door.
slipperywhenwet: I'm busy playing with my nipples...
wellhung69: Okay. Go get behind my desk. I hope you remembered to lock the door!
slipperywhenwet: Okay.
Wellhung69: I go answer the door
slipperywhenwet: Who's there?
wellhung69: It's your friend.
Wellhung69: Can I help you? Oh, you’re here for detention too?
slipperywhenwet: Really? Did she get in trouble too? Was she smoking behind the gym again?
Wellhung69: Yes. She got caught again.
Wellhung69: I smack her ass and make her join you.
Wellhung69: Do you think she deserves the same punishment as you?
slipperywhenwet: Yes.
Wellhung69: Come on out from behind the desk then.
Wellhung69: What should we do to her?
slipperywhenwet: Can I take off her panties?
wellhung69: go ahead
wellhung69: rip them
slipperywhenwet: okay.
wellhung69: now I think u should spank her
wellhung69: hard
wellhung69: this could get u out of trouble
slipperywhenwet: okay. I'll do anything.
slipperywhenwet: Her ass is nice to spank. My hand tingles with the smacks. Can I spank her again?
slipperywhenwet: Will you spank me as I spank her?
wellhung69: do it
wellhung69: bend over then
slipperywhenwet: Okay.
wellhung69: I give u a nice rap on the behind
slipperywhenwet: Can I put my fingers in her?
wellhung69: no not yet
slipperywhenwet: She seems wet though.
wellhung69: spank her again
slipperywhenwet: Okay.
wellhung69: How wet is she?
slipperywhenwet: I can feel it when I spank her...of course, my hand isn't entirely on her cheek.
wellhung69: ok, a little at a time
wellhung69: I get on my knees
slipperywhenwet: okay, just a little.
wellhung69: and spread your cheeks
slipperywhenwet: yah...?
slipperywhenwet: okay...
slipperywhenwet: am I wet too?
wellhung69: I start licking your pussy as you finger her
slipperywhenwet: nice...this is good punishment.
wellhung69: You're really wet!
wellhung69: You’re naughty getting all wet like this. You'll need more punishment tomorrow after school, young lady. You may need to spend your afternoons in the principal's office for the rest of the school year!
slipperywhenwet: I know. Your tongue feels great against my clit.
slipperywhenwet: I know, I’m a bad girl.
wellhung69: I flick my tongue real fast...
wellhung69: ...then slower. You moan.
slipperywhenwet: aaaah.
slipperywhenwet: I finger our friend, putting my thumb in her and playing with her clit with my fingers.
slipperywhenwet: I stop, though, to tear her shirt off and let her tits free.
wellhung69: How does she like that?
slipperywhenwet: she's moaning.
wellhung69: I say muffled
slipperywhenwet: she likes it.
wellhung69: Play with her tits.
slipperywhenwet: so I spank her for liking it too much.
wellhung69: I stick my tongue deep in you.
slipperywhenwet: she has nice tits. Round, firm and soft.
slipperywhenwet: hard nipples.
slipperywhenwet: I pinch them
wellhung69: You better do something.
slipperywhenwet: aah. I like your tongue in me.
slipperywhenwet: What should I do?
wellhung69: I lick all around u
wellhung69: DEEP!
wellhung69: Suck on your clit...
wellhung69: I stop...
slipperywhenwet: I spread my legs further apart.
slipperywhenwet: Don't stop. Please
wellhung69: Hey, I’m supposed to be punishing you! This is your punishment!
slipperywhenwet: Oh, I'm bad.
slipperywhenwet: Our friend needs to pay for her schoolyard crimes too.
wellhung69: Get her over here!
slipperywhenwet: I force her to get on her knees in front of you.
slipperywhenwet: I tell her to put your head in her mouth.
wellhung69: Now pay!
wellhung69: Oh yeah...
slipperywhenwet: It's too big for her, though, and she can't take it all in her mouth. I push her head down
slipperywhenwet: She gags, but knows she deserves the punishment.
wellhung69: Slippery, get over here now.
slipperywhenwet: Okay, sir.
wellhung69: Put your pussy in my face.
wellhung69: Put your lips to my lips!
slipperywhenwet: Okay, sir. My shaved pussy is glistening with wet...
slipperywhenwet: ready to be licked.
slipperywhenwet: and probed.
wellhung69: I lick it
wellhung69: a little...
slipperywhenwet: My clit is hot to the touch!
wellhung69: Then I lick a little more...
slipperywhenwet: Our friend sucks your cock...hard.
slipperywhenwet: I turn around to watch her as you eat me.
wellhung69: I want YOU to cum all over my face.
wellhung69: I suck your clit hard. I run my teeth gently and nibble on you.
slipperywhenwet: oh, I must do everything you say.
wellhung69: nibble a little
wellhung69: turn her around now
slipperywhenwet: Okay.
wellhung69: Help her stick her tight little pussy on my dick.
wellhung69: I want her to ride it hard.
slipperywhenwet: I hold it up as she sits down on your cock.
wellhung69: I go back to your dripping pussy.
slipperywhenwet: I play with her nipples as she bounces around on your cock.
wellhung69: I'm sucking in all your juices.
slipperywhenwet: Bite my clit harder!
wellhung69: I bite very hard.
slipperywhenwet: Stick your thumb up my ass...and make me cum!
wellhung69: u like that
wellhung69: I like u deep
wellhung69: lube my thumb
slipperywhenwet: She's bouncing up and down on your cock like a pogo stick. Her tits are flying...I hold them in my hand and bend forward to suck on her nipples.
wellhung69: stick it deep in your pretty little asshole
wellhung69: time for u to cum
slipperywhenwet: please? I promise I won't be bad again...just fuck me hard from behind.
wellhung69: get off
slipperywhenwet: Let me suck on her clit as you fuck me...
wellhung69: lean over the desk
slipperywhenwet: Okay.
slipperywhenwet: However you want me.
wellhung69: get her up there
slipperywhenwet: Okay...as you say, sir.
wellhung69: u better eat her good
slipperywhenwet: I will...cum dripping down my chin.
wellhung69: I rub my cock all over your ass
slipperywhenwet: Oh, it's so hard and wet from her pussy.
wellhung69: Gettin' juices all over it
slipperywhenwet: dripping them all over me...
wellhung69: I enter deep into your pussy.
wellhung69: start pumping u
slipperywhenwet: my pussy is throbbing, waiting
wellhung69: slow at first
slipperywhenwet: I arch with your thrusts...
wellhung69: then building speed
slipperywhenwet: moaning, muffled by the wet pussy in my face.
wellhung69: u feel me deep in u
slipperywhenwet: Grab my hips tight.
wellhung69: I smack your ass.
slipperywhenwet: And penetrate me DEEP.
wellhung69: fuck u deep
slipperywhenwet: Spank me, fuck me...hard.
wellhung69: and fast
slipperywhenwet: AAAAh, my pussy is so wet!
wellhung69: I stop w/ my cock deep in u
slipperywhenwet: Don't stop!
wellhung69: rub it all around
wellhung69: inside u
slipperywhenwet: AAh, I whimper and moan...
wellhung69: start pumpin again
wellhung69: pump very hard
wellhung69: and fast
wellhung69: spanking u very hard
wellhung69: is she cumin yet?
slipperywhenwet: Yah, do me like that...reach up and pinch our friend's nipples...her head is thrown back with the ecstasy of getting her pussy licked.
slipperywhenwet: She is about to cum.
wellhung69: I continue fucking you hard…as you scream for mercy.
slipperywhenwet: I’m going to cum too!!!
wellhung69: I reach up and pinch our friends nipples hard
wellhung69: and fuck u deep
slipperywhenwet: She cums all over my face...her muscles contracting violently with pleasure.
wellhung69: time for punishment
slipperywhenwet: Punish me.
wellhung69: I pull out and go in your ass. Tight.
wellhung69: start fuckin your cute lil ass
slipperywhenwet: I lift my hips for you.
wellhung69: my balls bangin against your pussy
wellhung69: I fuck your ass hard
slipperywhenwet: I get on my knees so our friend can slide under and lick my pussy while you fuck my tight ass.
wellhung69: u ready to cum?
slipperywhenwet: She toys with your balls as they smack against her chin.
wellhung69: I fuck u even harder
slipperywhenwet: My pussy is dripping wet.
wellhung69: get ready time to cum in both of our mouths
slipperywhenwet: I need to touch myself...
wellhung69: r u ready?
slipperywhenwet: Hold on...I must cum…
wellhung69: u haven't yet?
wellhung69: ok…I’ll wait…
wellhung69: u better be doing a good job
wellhung69: think of my big hard cock in u
slipperywhenwet: AAAAAAAAAAhhhhhhhhh, woah.
slipperywhenwet: I did. It worked.
slipperywhenwet: Have you cum already?
wellhung69: of course
slipperywhenwet: Oh, okay.
wellhung69: r u ok?
slipperywhenwet: TOTALLY. More than okay!
slipperywhenwet: U?
wellhung69: great
wellhung69: whats your name?
slipperywhenwet: Jan.
slipperywhenwet: You?
wellhung69: Marty.
slipperywhenwet: Are you really in the military? That’s what it says on your profile.
wellhung69: yea for right now
slipperywhenwet: Army, huh?
wellhung69: yea
wellhung69: where r u?
slipperywhenwet: I’m in Seattle.
wellhung69: oh that’s too bad…we’re too far away.
wellhung69: may I ask what u look like?
slipperywhenwet: Thanks for talking dirty with me. Uh, sure...I'm tall, muscular, short hair (straight, dark), dark eyes...
wellhung69: very nice
wellhung69: I love tall women
wellhung69: so u wanna do this again sometime?
slipperywhenwet: Well, you seem pretty open with the whole role playing thing...I like that.
wellhung69: how do u mean
slipperywhenwet: I mean you're open minded with the role playing.
slipperywhenwet: Some people aren't very open minded about exploring new things sexually...even on chat where everything is imagination.
wellhung69: I know
wellhung69: I like a bunch of different things
wellhung69: what else u like?
slipperywhenwet: I like boats, I like hiking…general outdoors kinda stuff.
slipperywhenwet: What do you do in the Army?
wellhung69: I work in the missile area
slipperywhenwet: That seems risky, no?
wellhung69: yea a little
wellhung69: I like to take risks
slipperywhenwet: Risky is good.
slipperywhenwet: Are you really 20?
wellhung69: yea
wellhung69: is that bad?
slipperywhenwet: I'm 37
slipperywhenwet: is *that* bad?
wellhung69: of course not
wellhung69: I love older women
wellhung69: what other scenarios do u like for role playing?
wellhung69: u r not that much older though
slipperywhenwet: I like forced sex, I like group sex, I like toys, I like police-type scenes...
wellhung69: thanx for the tips
slipperywhenwet: No worries.
wellhung69: we'll have to try some different things later then
wellhung69: when u goin to be free again?
slipperywhenwet: Hey sexy...it's 3:36am here...I'm going to head off to bed. I'm online about this time any evening. Bye…and thanks for the spanks.
wellhung69: Oh, ok. See ya.

by Sly Ivy