Correspondence: 3:27am

Darren had found her in a chat room. Sky had gone in, curious but not even sure how interested, much less committed, she was. But suddenly, she and some named Darrren2145 were pinging back and forth in the midst of other people's conversations. Though she was a little shocked at the thought, they were actually hitting it off. Darren private messaged her and she excitedly accepted.

D: So you're new to this? I'd like to jump right in.

S: Right now?

D: Right now. Do you think you could give me the next hour or two?

S: Yes. I mean, I don't have anything else going on. I'm nervous but... okay.

D: Okay. Let's explore some limits shall we.

S: Gulp. A little afraid at the thought of that but alright.

D: Good. Shall we start with your tits?

S: Gulp. You don't waste any time do you. I am very nervous

D: As you should be. I want you to tie them up for me. Nice and tight.

S: Tie them?

D: You really have never done this before have you? That's okay. I'll walk you through it. Do you have rope or something like it?

S: Yes

D: Okay, good. Now I want you to lean over so your tits hang down. Now start at the base and begin wrapping the rope around. Let's get them just tight enough so they swell

S: Okay

D: Be thankful I'm not making you tie tighter

S: I am very thankful!

D: Do keep them tight enough though

S: Okay, I will try

D: You will not try. You will do exactly as I ask

S: You're so demanding!

D: Excuse me?

D: Stop. Wait a minute. Sit up and spread your legs open, as wide as you can. Tell me when you're ready

S: Ready

S: I just got them tied up as well

D: Smack yourself on your clit as hard as you can, then say "I was not respectful. I will always be respectful to my Master."

D: Do that 5 times

S: Won't that hurt? Am I being punished?

D: Yes...and yes.

S: Okay

S: Ouuuuuchhhhhhhhhh!

S: Okay, done

S: My bound tits are heaving and my mouth flew open with each strike

D: Do it twice more

S: Do I have to?

D: That's 3 times now...would you like to go for 4?

S: No.

D: Would you like one more?

S: No, I'm sorry, doing it now

S: Ouchhhh!

S: Done, I'm sorry

D: Much better. Now, back to those tits

S: Yes, they are starting to feel slightly chilly to the touch

D: Lets give those nipples a good squeeze and twist. Pretend it is me doing this. Do it just as I would. Get them hard for me.

S: Okay

S: They're hard now. Everything feels so much more sensitive when you have them tied up

D: Good

S: Gulp. Okay

D: Now, do you have lounge chair in your living room?

S: Yes

D: Good. I want you to mount one of the arms

S: Gulp. Okay

D: Put your weight on there. Press your clit against it

D: Hard.

S: Ooooooooh yes

S: That feels so good

D: Move slowly backwards and forwards

S: Ooh that feels great

D: Now I want you to pinch your nipples and squeeze your tits together

D: Try to make your nipples touch.

S: Yes

S: It hurts a little to pull them like that

D: Good.

D: Give them a little rub each time after you pull them.

S: Oh yes

D: Wet your fingers and gently rub them

S: Thank you

D: Imagine it's my tongue

S: Oohhh yes

S: I would give anything for that to be your tongue

D: Now put your hand between your legs. Slide a finger into your pussy. Ride it

S: Ohhhhhhh yessssssss

S: Thank you

D: Keep going. I want you to want to cum

S: I want to cum!!

D: Stop.

S: I stopped. My face is scrunched up with frustration but I've stopped

D: Do you have any clamps?

S: No

S: Wait... come to think of it, yes I think so actually. There's an old box from a bachelorette party in my closet. They gave out a lot of sex toys... I think there was something with a chain...

D: Good. Go look

S: I'm worried about what is about to happen... but okay

D: Worried is good.

S: Gulp

D: You swallow a lot. That's good as well

S: Okay I have the box, let me see

S: Yes. Gulp. I have them

D: Good. What color are your tits?

S: Slightly darker than normal

D: That's good.

S: For you maybe!

D: Excuse me?

D: Let's go ahead and punish you a little bit

S: Something tells me this is not going to be pleasant...

D: I'm telling you.

D: Now, sit down on your couch. Legs spread. Wide.

S: My eyes are cast down. I'm in position

D: And put a clamp on each pussy lip. Make sure they're tightened very tightly. And I mean tight.

S: Noooooooo!

S: Okay, yes I'll try

D: Yes what?

S: Yes... um, sir? master?

D: Better. Master will do

S: Yes master

D: Stop what you're doing.

D: Hit each tit. During this you will say, "Master has a capital M."

D: Do this 3 times each. As hard as you can.

S: What? Noooooo! Please?

D: That's 4 times

S: Yes Master

D: Better

S: Ouchhhhhhhhhhh ouch ouch ouch ouchhhhhhhhh

S: Done Master

S: My head was thrashing side to side as I spat out the words. It felt like my tits were about to explode

D: Good. Go get a tube of lipstick

S: Yes Master

D: And draw a big Capital M on each tit

S: My eyes are cast down. Yes Master

S: Done Master

D: Good

S: I will not be forgetting the capital again Master

D: I know. Now, back on the couch with your clamps

S: I still have to clamp my pussy lips after all that?

D: Yes.

S: Yes Master

S: Ouchhhhhhhhhhh

S: Pussy lips are clamped Master. You would love the sounds I'm making right now

D: Yes. I would. Now, pull on the clamps and stretch your lips while thinking of what your Master is going to do to you next

D: Count to 10 and let them go

S: You mean I have to pull on these? But they already hurt so bad

D: Count to 15

S: Nooooooooo! Yes Master. I'm groaning Master

S: Done Master

D: Good

D: Move the clamps to your nipples

S: My tits are so sensitive right now tied up Master. Please Master

D: And you may finger yourself slowly for awhile once they're on

S: Yes Master

S: On Master. I am in so much pain I am shaking. I have never felt anything like this Master

D: Finger yourself

S: Ohhh thank you Master

D: DO NOT CUM

S: No Master no cumming

D: Good

D: Does it feel nice

S: I can barely breathe

S: Am I pleasing you Master

D: Take your finger out. Spread yourself open and expose your clit

D: Yes, you are pleasing me greatly

S: Yes Master

D: Now give it a squeeze

S: A squeeze?

D: Yes. Pinch your clit. Hard.

S: This is going to hurt Master

D: Yes.

S: Ouchhhhhhhhhhh Ouch Ouch Ouch it hurts so much Master

D: Good girl. Now take the clamps off and put your finger back inside

S: My tits feel like they're about to explode Master

S: Thank you for removing those Master

D: What color are they?

S: Slightly darker than before Master

S: Thank you so much for taking the clamps off

D: You're welcome

D: Does it feel nice with your finger in your hole

S: Yes very much Master

D: Is it all nice and wet?

S: Dripping for you Master

D: Take your wet finger out and slide it into your ass.

S: My ass Master?

D: Yes. Move it in and out. Like it's me fucking you

S: Ouchhhhhhh

S: Okay, it's starting to feel good Master

D: Good.

S: I wish it was you inside me Master

D: Push it in further. As far as you can stand

S: Ooooohhhh yes Master

D: My cock would stretch your ass wide open

S: I would love that Master

D: Now rub your clit with your other hand until you feel like you're about to cum, then stop.

S: Yes Master

S: I'm already so close Master

S: Okay, I had to stop Master

S: I'm squirming everywhere

D: Good. Where are the clamps?

S: Gulp. Next to my leg Master

D: Put them back on your lips

S: Please Master

S: Yes Master

D: And one at a time twist them 90 degrees

S: I have to twist?

S: Yes Master

S: Ouchhhhhhhh! Done Master.

D: Was that bearable?

S: I'm afraid to say yes Master

S: Very painful but bearable Master

D: Now do it again in the other direction

S: Yes Master

S: Ouchhhhhhhh!!

S: Done Master

D: Good girl. You may finger yourself again

S: Oooohhhh thank you Master

S: Wait that jiggles the clamps Master

D: Yes. Yes it does

S: That was not very nice Master

D: Would you like to take the clamps off?

S: Yes Master please please

D: Then you may move them to your nipples.

D: And let's have you mount that chair arm again

S: Noooooooooo I'm groaning so much Master

S: Yes Master

D: You've been a good girl today. You may use the arm until you cum

S: Oooouuuuchhhhhhhhh my nipples

D: Grind against the chair. Grind fast on the arm

S: May I cum Master?

D: Not yet. Make those big tits sway and bounce

S: Yes Master

D: Slow down to avoid cumming

D: If you have to lift off the chair to stop then do it

S: Yes Master

S: I had to lift off Master but I did not cum

D: Good.

D: You may resume

S: My tits hurt so bad Master

S: May I cum Master

D: What color are they?

D: No, lift off the chair

S: The same shade still Master

D: Smack your clit 3 times. Hard.

S: Nooooo please noooo Master

S: Ouchhhhhhhhh!

S: Done Master

D: You may resume grinding on the arm chair

S: Thank you Master

S: May I cum now Master?

D: Have you been good today?

S: Yes Master

D: Do you think you pleased me?

S: I hope so Master. I want to please you Master

D: Pull your nipple clamps off and then you may cum

S: Pull?

D: Yes. Pull them off

S: But my tits hurt so much Master

D: It would please me

S: I am so scared Master

D: You may cum while you pull if you like

S: I want to please you but I'm so scared Master

D: Pull them off.

S: I'm shaking Master. Okay Master

D: If you delay and further I'll make you twist as you do it

S: Ahhhhhhhhhhhhhhhh Ouchhhhhhhhhhhhh Ohhhhhhhhhhhhhhhhh Ahhhhhhhhhhhhh

D: I take it they're off

S: Yes Master

S: I'm panting. I've never... That hurt so much. I'm a mess now. My mouth is still hanging open from my scream.

D: How do you feel?

S: Spacey Master. Spacey and sleepy

D: Good girl. You did great. Go to sleep now...