My second full length book (34,000 words) published

Karen's submissive adventure book 2, is now published (July 31st)

Monday, August 29, 2016

Chatting with Karen - online submissive (MD / FS, masturbation)

This is a real online chat  with a friend, Karen, who helped inspire the "Karen's Submissive Adventure" story.

That 24,000 word novel is available here:  

This chat gives you an idea of how I get story ideas from my submissive friends. 
Spanking Jack


Chapter 1: The journey begins

Karen sat at her computer and waited for her online Dom to sign into Yahoo chat.

As she sat there she thought about how this started. She read a story of his on Literotica and emailed him to say how much she liked it.

She hoped he would just write more of the Submissive Mistress story. Instead he contacted her and asked her lots of questions. She replied to everything he wrote, even sending him dozens of nude photos of herself. 

Instead of writing more of the one story he wrote up her story, her fantasy. He wrote down the things she told him, things she hadn't told anyone else. He made her fantasy come to life as characters on her computer screen. Little did she know how much more would come from that first email.


Waiting at her computer nude, as required be her Dom, she had her sex toys within reach. She was already wet, very wet, and her clit begged to be touched.

She knew she wouldn't get to cum today, it was too soon, but she hoped she might be able to convince him to let her cum before Friday. It was Wednesday so it would only be two days early and she had been good since her last orgasm a week ago. Still she didn't really expect to cum this afternoon.

She squirmed in her office chair, squeezing her thighs together to try to get some pressure on her clit. Finally he signed in.

Aug 21st, 2008

John Dough: Hello Karen, did you like chapter 3?

KarenCum: Yes very much

KarenCum: have your written part 4

KarenCum: I was hoping to read your story and get myself off

KarenCum: I was determined not to get myself worked up today, but well things did not go as planed.

John Dough: You like getting yourself off

KarenCum: I dont know, you make me so horny now

John Dough: Are you ready to cum for me, like you did the other day...

KarenCum: Not sure, my clit is so swollen. Cumming should help with the arousal, but we will have to see on the swelling.

KarenCum: im not close right now, but well a bit worked up.

John Dough: You know how I like you when we chat...

KarenCum: lol, how is that.

John Dough: I know you're not close yet, but I'm fairly sure I can get you there before 4:20

KarenCum: i was thinking more like 3:15

KarenCum: and im not sure I will come that fast

John Dough: I like you totally naked my dear, you know that

KarenCum: yes, and I am naked as you want

KarenCum: i was hoping to read the story.

John Dough: I can give you the story details here in our chat

KarenCum: really?

KarenCum: but last time we did that, it changed a bit before you wrote it.

John Dough: Yes it did. The wording is not the exact wording of the story, just what I plan on doing in the chat

KarenCum: ok

John Dough: I was starting when you signed in and we started chatting, so it won't be verbatim, but it will be the same general action

John Dough: and now we have less time, and time is not on our side today

John Dough: I start that chapter with you naked in the mini-van, Jenny has just left

John Dough: I'd remind you what happened in the story, but you've re-read it a few times today, you might know it better than me.

KarenCum: ok

KarenCum: lol

John Dough: So, you're naked, and very horny

KarenCum: normally I would rub my thights together, but it kinda hurst to do that right now.

KarenCum: yes

John Dough: She had you on the edge, you thought you were going to get to cum, but she left you there, hanging.

John Dough: She told you to go home and if Tim asked for sex to just blow him, (much like last night it seems)

John Dough: So you get dressed in the van, now I'll add a bit of detail about how your clit feels from her spanking you

KarenCum: yes it seams i cought up to that in reality, shaved already, and did that last night.

John Dough: Now you don't have your bra or panties and have to drive home in just your shorts and top.

John Dough: Right, you have to shave for her, and you know you'll be horny from that. I suspect you were horny when you shaved the other night?

KarenCum: im sure I would have a hard time with the shorts as they would rub my sore clit.

John Dough: Yes they would, but that would be part of your punishment

KarenCum: yes verry horny

John Dough: You would think back on all that she did to you, how horny you were in the van, how she teased you

John Dough: How she got you to admit things that you didn't think you would

John Dough: It would make you even more horny than before

KarenCum: exactly

KarenCum: im sure htat is acurate.

John Dough: You would be tempted to rub your clit but you know you're already going to have to suck off three men or something to make up for the 3 orgasms you had before

John Dough: You know that you can't hide anything from Jenny, when she gets you aroused like this, you admit everything you've done.

KarenCum: im sure I would rub it some, and tell myself it might help, and not let myself cum.

John Dough: Right, and we might bring in how you pinch it to stop from cumming

KarenCum: ok

John Dough: You end up doing it so much that your clit ends up very large, very red, very sensitive

John Dough: You get home, you've soaked your shorts through again

John Dough: You're embarrassed that your cunt is so needy, that your so soaking wet

KarenCum: yes

John Dough: You can't believe how your needy cunt has gotten you into this position

KarenCum: I cant understand why im flowing so much, or why thinking about what she has done, and will do has me so worked up.

John Dough: You can't believe that your going to go back to her for more.

John Dough: You'll drive past the security guy in the car, he'll notice that you don't seem to be wearing a bra

John Dough: your big breasts will be bouncing around as you drive past him and he'll see you big nipples too

KarenCum: im not sure that would be obvious would depend on the top.

John Dough: You'll see his eye open wide and it will embarrass you

KarenCum: ok

John Dough: In the story my dear it will be obvious.

John Dough: Are you rubbing your needy cunt right now my dear?

John Dough: Are you picturing all this?

KarenCum: and I will be thinking about, and wondering how she will find the men she intends to make me suck.

KarenCum: yes

John Dough: yes what slut?

KarenCum: yes i am rubbing myself

John Dough: What are you rubbing slut?

KarenCum: my cunt sir, i am rubbing my needy cunt

John Dough: That's better slut.

John Dough: So, you remember back to when you were both in the van

John Dough: You'll wonder about that, who will she find, how will she find them. Will they be attractive or ugly?

John Dough: You'll wonder

KarenCum: and it will scare me that the thought of having to suck off men other than Tim, and swallow their cum is makeing me even hotter.

John Dough: Your needy cunt will pulse with each beat of your heart

KarenCum: wondering how I will feel having thier cum in my mouth.

John Dough: You'll wonder what it will taste like, you don't know but you suspect she will make you swallow and laugh as you do.

KarenCum: sucking thier cocks, and how it will feel knowing Jenny is thier watching, making me do it.

John Dough: Right, she'll make sure you're naked as you suck them off, you know that.

John Dough: Your body will be on display for her, for the men, it will be humiliating to be forced to do that but the thought will excite you

KarenCum: yes

John Dough: You also know Jenny will notice how big your clit is as you suck them off

KarenCum: knowing she will tease me, and show them how im begging to cum.

John Dough: She'll comment on your big pussy lips

John Dough: Right, she'll literally have you on your knees, naked, begging to cum

John Dough: She'll get you to promise to suck the men off so you can cum.

John Dough: Then when you suck them off, she won't let you, she'll make you beg some more.

KarenCum: she will tell me if i do everything she tells me she might let me cum.

John Dough: Right, it's always "might let you cum" it's never "Will let you cum"

John Dough: She do it, just hoping that you get to cum.

KarenCum: yes

John Dough: She'll let you rub your nasty, needy cunt while you suck the men off

John Dough: She will want to watch you, keep you on the edge

John Dough: She might reach down and pinch your clit when she thinks your close

KarenCum: yes I imagine her behind me and pushing my head telling me to take all of them.

John Dough: Yes, and she'll call you names, like pussy licker and cum slut

John Dough: She'll tease you about your big cunt lips and your big, red, swollen clit

KarenCum: yes she will tell me she see how may cunt is so needy, and how she loves watching me hump the air.

John Dough: good, good, yes and the men will laugh as well

John Dough: I hope you are getting close to cumming my dear, your time is running short

KarenCum: yes

John Dough: Is your cunt nice and wet, your clit, throbbing and ready to cum?

John Dough: You can picture yourself on your knees, sucking the men off

KarenCum: she will tell them its a good thing im sucking them as I look so streached the probibly would not enjoy it anyway.

John Dough: she's forcing your head up and down on their long hard cocks

John Dough: Right, right, she will say she has a nice tight pussy but yours is big and stretched

KarenCum: she is trying to make me cry

John Dough: She'll laugh and taunt you about your cock hungry cunt

KarenCum: yes

John Dough: She wants to see you cry as you suck their cocks

KarenCum: she will tell me she wants to streach it so much Tim will not want it anymore.

John Dough: She might tell you if you get them off quickly you can have one minute to cum

John Dough: Ah, yes, very mean like that

John Dough: She'll want the biggest cock or dildo she can find for you needy cunt

John Dough: She will watch you lick and suck and swallow their cocks and cum and then say, "No, not good enough." and laugh as you beg to cum

KarenCum: yes

John Dough: She'll let you touch your clit but not let you cum

John Dough: she'll have the men shoot some of their cum on your face

John Dough: and then have you lay down on your back, spread your legs and pull on your cunt lips

John Dough: she'll let you try to cum

John Dough: watch you as you finger you cunt, eager, desperate to cum

John Dough: but you'll run out of time, you won't get off

John Dough: she'll slap your hand away and not let you cum

KarenCum: I imagine her making me lick her like this while she pulls me open and blows on me, and plays with my clit but wont let me cum.

KarenCum: not nesasarly now but at some point.

KarenCum: yes she has to hold my hands to keep me from getting myself off.

John Dough: that could be another scene

John Dough: She might even have handcuffs or something so you can't touch your pussy

KarenCum: she likes how I put three fingers from each hand in as she was pulling on my clit..

John Dough: ah, so you can get three fingers from each into your cunt, she will want to see that for sure

John Dough: she will probably pull on your cunt lips too, now that you are shaved

KarenCum: yes have to reach from under legs, and cang go deep but can do that.

John Dough: she will want to see that, she will laugh when you do it - tell you that your cunt is stretched wide open if you can do that

John Dough: but she will get you to show off for her

KarenCum: yes

KarenCum: she will take pictures of me doing it.

John Dough: that's good - yes, she will want pictures and more evidence against you

KarenCum: I need go sir, but im so close

John Dough: do it then slut, cum for me while you picture Jenny taunting you as you suck each man off

John Dough: picture yourself on your knees, naked, horny, on the edge,

John Dough: eager to cum, she's laughing, holding your head on their cocks

John Dough: she tells you if you're good and if you suck them all off you might get to cum

John Dough: you're eager, you do it, you're so horny you do it

KarenCum: her taking pictures of their cocks in my mouth.

John Dough: you suck each cock one by one

John Dough: your hand on their cock, your wedding ring clearly visible

John Dough: visible, so clear, so horny

John Dough: you have no choice, you have to submit to her so you can cum

John Dough: she's holding your head on their cocks

John Dough: you can feel their cocks pulse in your mouth

John Dough: you can feel the cum spurting

John Dough: she's taking pictures

John Dough: she's going to have you do more and more kinky things

John Dough: you won't be able to stop

John Dough: she's going to have you over a barrel

John Dough: you'll suck each one off, they will wipe their slippery cum covered cocks on your lips and face as she takes pictures

John Dough: you'll have an orgasm even though she didn't allow it or want you to have it

John Dough: cum for me Karen

John Dough: Cum while Jenny takes pictures of your mouth stuff full of cock

John Dough: your face dripping with cum

John Dough: are you there?

John Dough: Did you cum?

------ Chat ended --- KarenCum has signed out

Karen moaned and bit her lip as she fingered her wet sloppy cunt. Just as she got close she heard a noise. The school bus pulled to a stop in front of her house. Her son and daughter would be at the door in an instant. 

She panicked and grabbed her clothes, turned off the PC and rushed to the bathroom to cum.

She locked the door, got on her knees as if sucking some strangers cock, took the big 8" red dildo and sucked on it. Fingering her cunt and rubbing her clit she imagined herself kneeling naked and sucking cock after cock. She pictured her tormentor / Mistress taking pictures with her camera phone as she licked and sucked each cock.

She pictured the men pushing her head down on their cocks as Jenny laughed and called her a cum sucking slut. That image pushed her over the edge. She came in a flash, a powerful orgasm wracked her body.

She rolled her clit and shuddered as wave after wave crashed over her. She set the dildo down and licked her fingers clean of her cum. The mental imagine burned into her mind. 

She stood up on shaky legs and looked at herself in the mirror. Her face was flush from her orgasm and her clit was as big as a marble, red and swollen. She could picture everything in the story and it made her want more. She didn't know how far she would go with this but she loved it.


End of Chapter 1

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