Three Cam Sessions

First some context. I reengaged with my Domme after being cast out into the wilderness for being a frustrating and annoying sub frenzied noob. I have spent the last few months since then working on learning about being a better sub. Subjecting my self to IRL experiences and experimenting with all the kinks I can reach out to safely. A few weeks ago, lets call her Miss D re emerged with a like on a post I made here. Nothing I had sent to her previously had received a response. She had cut all ties, deleted are shared folders and ghosted me.

But I took a chance and pinged her 1 more time on Skype. We reconnect, have a nice chat. Played for a little bit. One of the things I think is key right behind good communication is being honest. I can lie and say I didn't touch, didn't come, did do the task or w.e. but if I do I cheat myself. Now it may have been foolish and it's a key reason why the following sessions go the way the do, but I did touch myself however briefly when tasked not to. In our very 1st week... Yikes, talk about panic. Suffice to say Miss came down on me like a tonne of bricks. I spent a week doing difficult tasks, and much to Miss's satisfaction behaved.

This led to Sunday afternoon...

Session #1

During this time we discussed when we could meet online, which if my behaviour was ok would be Tuesday. This Sunday afternoon, we get together after discussing via shared files with images what tools and toys I currently have as we get reacquainted with each other. Chat picks up on anal stretching instruction and reminders for me. Note I am to address 'Mistress D' for want of a real name as Miss, as I have not earned the right to be much more than a cumslut to her at this time.

Sunday

5/21 5:03 PM

ME: ok. Lubing/stretching is running finger around rim, then 1 finger then 2 inserted

Mistress D, 5:03 PM

Thats right

5:04 PM

The white toy is not super big FYI. it fits pretty easy well it did anyway

Mistress D, 5:04 PM

That's not the one I'm worried about and not matter the size you prep. I know your a horny slut but you still need to take care of your body

5:05 PM

yes miss. you aren't going to make me do the gravity [Gravity is a Lovesense thrusting dildo we bought but have not used yet at this point] without are you?

Miss, please.

Mistress D, 5:06 PM

Did you even read what I just said?

5:07 PM

lol... yes. ok. Sorry. I was focussing on "thats not the one"

Mistress D, 5:09 PM

let me know about Tuesday but Monday and Wednesday are busy days for me so you'll be getting instructions

5:10 PM

yes Miss. I will definitely be in a hotel Tues from 8 or 9 pm onwards. I got some b.s. awards thing to attend which if I am seeing u I will cut out early.

Mistress D, 5:11 PM

Lol no stay the whole time either way

5:12 PM

I dont want to be too hammered lol...its gunna be a party

Mistress D, 5:12 PM

Then you need to control your drinking huh?

5:12 PM

netowrking b.s. bunch of losers. yes miss

5:13 PM

Yes Miss.

you are making my dick throb already

I would you..know...hate to appear...oh... impatient. But when do we start today? :)

Mistress D, 5:17 PM

Hmmmmmm

5:18 PM

such a tease.

Mistress D, 5:18 PM

Oh really? lets test out the tens shall we? [ I have a TENS unit I use for healing my elbow...and yeah it feels awesome on my cock too]

5:19 PM

oh boy.

how would you like me to arrange that?

Let me go get shorts on

Mistress D, 5:20 PM

lol take a breath

5:21 PM

yes miss, of course.

doah

Im going to make a cocktail while you devise my evenings torture.

Mistress D, 5:33 PM

Shorts no underwear. Place one pad on your taint and another under your penis at the base. I want it on the lowest setting but don't turn it on until I say

5:33 PM

now?

Mistress D, 5:33 PM

Yes now

5:34 PM

I just got a boner. yes miss. I need to set this up so its innocuous. give me a minute.

[Family is roaming around our small place outside, we are building a home and living on site, so a high risk gig....silly of me really. But I need my Domme]

Mistress D, 5:34 PM

quickly slut

Mistress D, 5:40 PM

Good turn your camera on

You don't have to talk I just want to watch you so I know you are behaving. [We one way skype, she can see me, I can only hear her. I have never seen Miss.]

When you see this time, its the duration of a 1 way video call.

32m 2s

Mistress D, 5:50 PM

where's your edge? Is it near by go get it. Pants off when you come back

[In this section I am speaking and she is typing to me, as I have a Bluetooth headset on. This is the most risky I have been, family members are outside doing 'stuff' Im taking a nap, and using the TENS to massage my elbow injury.]

No its just as a vibrator today [ tells me to place on my balls]

balls

[Miss proceeds to have me stroke by cock, and hold the vibrator at the tip, for periods of time, with long breaks. Building me up to a frenzy by slowly reducing the break times. She is now on voice, and watching me via skype. She hears me regulating my breathing, and sees me flexing to keep control of my orgasm. However Mistress D is on a mission. This evening she wants me to come, and ruin the orgasm for me. She has me squeezing my cock, pressing the Edge 2 against my balls and tip and glans repeatedly. Im deep purple and throbbing after being unallowed to touch for the past few days.]

Mistress D, 5:57 PM

Put everything up by one [tens unit]

Take it off

pause just sit with your hands at your side

32m 2s

[finally I explode, she laughs her sexy chuckle and admires the huge load of cum I deposit, even as I come she instructs me so she can see everything, she is a true voyeur of my shame, my orgasm and my suffering.]

Mistress D, 6:53 PM

You instructions have been given in keep if you have any questions I will be back in 2 hours

7:03 PM

Thank you Miss. I will read again after dinner. But I think I have it. Got it now. Delete rest of message.

7:17 PM

That was an amazing orgasm by the way. I hope you noticed I did not try to stroke further Miss as I knew that would make you mad!

Mistress D, 10:56 PM

Savor that feeling slut you won't be feeling it again for a while. Be good this week and Do Not FUCK UP!

10:57 PM

Yes Miss

5/22

On Monday per my instructions and punishment that is continuing from a prior infraction, linked up with my as she calls it 'naughty boy' orgasm on Sunday I have new tasks to perform for the week. I must wear my tightest underwear and stroke through it at different times of day, morning, noon and pre bed. As build up to Tuesday where I will be in 'sessions' with her again via skype. Monday and Friday my job is to sit for 1.5 hrs with the Edge in and available for her to connect. Wednesday and Thursday I am to execute the stroking via underwear as many times as possible during the day.

11AM

ME: im in Edge 2 inserted in rectum. ready. on a call. She randomly appears 20 minutes later with no warning turning the vibration on

12:04 PM

OMG. I HAVE not had something in my ass this long for a long time. Probably great that we are doing this today. Whoa...u minx Miss my wife is 10 feet away

That was making my head feel very full.

I finally relaxed down on it, can feel every damn thing.

Mistress D, 12:22 PM

Good boy

12:23 PM

May I please remove it now. It went in 10.45...please Miss.

I want to come some bad. How is that even possible after y.day

I'm so hard

Mistress D, 12:25 PM

5 more minutes then you can remove it

12:25 PM

Yes Miss. It's right on the p spot.

Mistress D, 12:25 PM

Thats where it should always be slut

12:26 PM

Lol. I'm still learning

Plus older guys get enlarged prostates... but tmi.

Ohhhhh

Mistress D, 12:27 PM

oh what slut?

12:27 PM

Intense

Miss

Mistress D, 12:27 PM

What?

12:28 PM

Intense sensations.

Miss please.... it's 12.30

Ahhh. Darn it

Mistress D, 12:31 PM

What was that?

12:31 PM

Please stop.

Lol.

Mistress D, 12:31 PM

You can take it out now slut

12:32 PM

Thank you Miss.

Mistress D, 12:32 PM

I forgot how much fun that toy is lol

Go clean up and be a good sub;)

12:33 PM

[Here I send her a snap of my engorged cock]

Look what u did too your cock miss!

That edge slides out unless I sit on it. Dunno why.

Also fyi. Saw a tiny drop of precum on my jocks.

4:20 PM

That toy is fun! See aren't you glad you were bored. Imagine if the gravity is the same???!!! Eek.

9:01 PM

Finished punishment #1. Waiting to shower and do #2.= #2P. Popped a note. [ I send her updates in Keep that we share. She tasks me there and this avoid long email chains, etc and I can add images as requested without spamming skype.

9:07 PM

I'm going to jump into shower and do 2nd round for u now.

9:31 PM

#2 complete. Going to bed shortly. Mrs asked why I had a hard on just now and asked if I needed servicing...I said no I punished myself enough this weekend!

May need to get your approval to let her touch me at some point ate this week Miss. I'm sorry for the inconvenience.

Tuesday 1:22AM

Mistress D:

As for the Mrs. If and only if she initiates it can you let her touch you. And you better thank me in your head the whole time

TUESDAY

CAM Session # 2

I'm prepping. Lost a little of my voice, function was loud. I'll message when I'm on my knees waiting for you.

Couldn't handle the losers any longer.

9:34 PM

I'm prepped Miss. Nervous but ready when you decide my punishment should continue.

Mistress D, 9:44 PM

Put your edge in

9:44 PM

miss

Yes

In with underwear on

On bed

Ugh got to connect

Got rope and gravity near by too miss.

Mistress D, 9:52 PM

Call me

36s

2h 33m 54s

15m 6s

This session is long. After a while she has me bind my C&B and rub my cock with the rope on. After not touching my cock for the last few days unless through underwear it all feels very raw. Im super aroused.

After the Edge we experiment with the Gravity which has a thrusting device. We start with me attempting to enter it in my ass while it is suction cupped to the floor. There is a mirror next to me and near the bed. I'm on my knees with the camera angled to attempt to allow Miss to see everything. It's a hug shock to feel 5 inches go in me, and that width. It's the widest thing that has ever gone in me. It presses very hard against some 'wall' deep inside me. Then she starts the thrusting. With some practice it works but the motor struggles if not perfectly straight and aligned.

We attach it to the mirror. I'm on my knees in the most degrading position I've ever felt. She takes control of the unit and beginning thrusting, slow at first with a high vibration setting. By cock doesn't know what to do. It goes hard and soft, as the discomfort despite lube is intense. She starts 'double thrusts' or double pumps, its intense. I am to be thanking her constantly but I cannot concentrate, I start tell her to fuck me, that Im a cum slut and a ass whore and I want her to fuck me harder. Finally I request a break, using a safe word.

We transition to the bed. With my camera on the night stand, she instructs me to get my knees up around my ears and insert and hold the toy in. She starts thrust again, im getting aroused.

After 30 more minutes We begin edging me. This exercise is one where Miss takes me up to the edge and I call out when I'm close with a key word. She then takes me just past that. Tonight we spend a lot of time going for soft to hard and back. For nearly an hour. Fast and slow counts, she is in my ear [earbud] commanding, counting, controlling. Her voice turns me on. Sometimes she drops from the harshness to a sexier tone. But she does it almost comically, its makes my cock throb but at the same time I can laugh and it helps me not come. We do count downs from 20 to 1, from ten to 1 always stopping at 2, then going back up, always while I am jacking fast. I beg for orgasm and get denied again and again. The veins on my cock a bulging, the entire shaft is a deep, angry purple. No red, not just purple, but a deeper more primal color. The color of lust. For the first time I begin to wonder what it would be like to fuck the Miss. Then STOP. Shit.

I collapse. Sweating exhausted. My cock dies.

I tell her I don't think I can get hard again. I should of shut up. She takes that as a challenge. We go again. In a purring sexy voice she asks if 'I want to make her cock come for her' I beg yes. She starts at 20. Im to stroke slow. I prop to attention, around 10 we go faster, the numbers come fast and slow go up and down. I'm lost. Stroking, looking in the mirror at my frantic face, listening to her its too much. We get down to 2 three times. On the third time I hear her breath in to say one, and its perfect timing, I can come right now. She says stop. But its too late. I explode, I pull down hard, holding the base. She instructs through my thrashing, hands off, hands off. You fucked it up. Stupid slut. You have no control.

I lay there panting, covered in come, in sweat and lube. I'm in trouble I can tell, I get the self control lecture and how I really missed out of a fun reward. So mean, she beats me down hard. I was almost there Miss I beg for mercy. Then we settle down and she chats to me a little more, and I beg to try again. She says no 'I ruined it all'. She is now bored. This theme is so awesome with her. I think she secretly takes delight in being mean to losers like me who have no sex life, who want a Domme and maybe even need a domme. Her mean streak aint spiteful, just exacting and terrifying. I love it. She must be some sort of psychologist or studied human behaviour or perhaps I'm just a fucking vanilla easy to read simpleton. In fact she called me a simply boy once lol.

Thursday

Mistress D:

You need to practice with that gravity so you ass gets used to it

3:14 PM

yes miss.

Not sure how when Mrs is in in town..

its 'loud'.

Mistress D, 3:15 PM

Legs up in the air was my favorite

3:15 PM

oh really!

Mistress D, 3:15 PM

You looked like at true slut

3:15 PM

I wonder if I can re position camera next time when Im sitting or doggie style?

lol

Yes Miss.

I was going to ask what u liked..

Mistress D, 3:16 PM

You can practice without turning it on

3:16 PM

true, yes i can.

eek. that thing is big.

Mistress D, 3:16 PM

lube it up baby

3:17 PM

I will! I need to buy more!

May I try practicing for you Friday morning when she leaves at 8am?

what should I do.

im alone all day friday until 5pm

I think

Mistress D, 3:18 PM

I'll think about it

3:18 PM

yes mam.

What else made Miss happy or maybe even wet?

Mistress D, 3:20 PM

Mind your business slut lol

3:20 PM

:(

Mistress D, 3:21 PM

You don't get to ask questions when you can't even control your whore cock

3:21 PM

one second off Miss...:(

ill do better next time

Mistress D, 3:24 PM

Those are just words I want actions

3:24 PM

Yes Miss.

I have been doing my punishments for unallowed touching thru my underwear diligently.

despite how sore I am. I am trying to show by those deeds I can do as u say

Mistress D, 3:27 PM

sore? how sore?

3:27 PM

tender from stroking. 2 hours of touching then the punishments.

you worked me hard.

its been a long time since I have had motivation to play even 10% that long.

you made me hard, then soft so many times I lost count. now Im sitting here, throbbing wanting to get hard, but afraid to!!! Lol.

Mistress D, 3:30 PM

Good. I want you to play at least 3 more times today got it

3:30 PM

Miss!!!

please.

THREE

Mistress D, 3:30 PM

please what slut?

3:30 PM

yes mam.

Mistress D, 3:31 PM

No say it slut. please what boy

3:31 PM

Please have a little mercy Miss.

Mistress D, 3:31 PM

no its a punishment 3 won't kill you

3:31 PM

lol

Mistress D, 3:32 PM

tomorrow you won't even touch it

3:32 PM

if I die Miss.. :)

Mistress D, 3:32 PM

you'll die full of cum

3:32 PM

Thank you Miss. No touching Friday.

I'll keep my hands to myself, and your cock safe.

I am full too. my balls a really full for some reason, despite my ruined orgasm.

it is hard to pee, im partially hard nearly all the time

its a reminder of my ownership by you Miss.

Mistress D, 3:34 PM

you kiss ass so much lol

better than whining yes?

Mistress D, 3:35 PM

both are annoying lol

Prep your ass first thing tomorrow

3:35 PM

yes Miss.

Mistress D, 3:38 PM

yes

Yes miss

Did you have instructions for me for in the morning Miss? I should I just wait to hear from you? Today/Nite I will do 3x more punishments.

I dare not say anything else as I dont want to annoy you :)

Mistress D, 3:46 PM

I was just joking little slut just worry about today for now

3:47 PM

:)

. phew.

Am I dismissed miss? I was going to go and try and do 1 of the 3 I owe you now.

Mistress D, 3:52 PM

dismissed lol yes you may go

3:52 PM

Thank You Miss. I really enjoyed our time together Tuesday nite. Thanks.

4:00 PM

Done.

4:45 PM

2nd of 3 done.

Mistress D, 4:49 PM

Do the last one before bed

4:49 PM

Yes Miss.

Torture Queen

Mistress D, 4:50 PM

Name calling gets you nowhere do another right now

4:50 PM

OMG.

Yes mam

It was a compliment...

Mrs is making noises about playing with my dick or perhaps even sex tonight....yikes.

Your dick^

Mistress D, 4:53 PM

Let her

And you better make her feel good too

4:54 PM

Yes Miss I will if I get the chance. Am I allowed to cum?

Mistress D, 4:55 PM

No

4:55 PM

Miss please how? Do I manage that? Omg.

Mistress D, 4:56 PM

Figure it out slut. If you didn't mess up Tuesday I would have let you cum but you don't deserve it

4:56 PM

If u could see how hard I am right now damn it. Lol

Yes miss

Mistress D, 4:57 PM

Take a picture and show me

[I send her a shot ]

5:12 PM

Good point. Yes Miss. It's getting very hard to not cum.

Or making me need to cum. How's that.

Mistress D, 5:15 PM

Do another then thats it until bedtime got it slut

5:16 PM

Yes Miss. Thank you.

I'll let you know if anything happens with Mrs? And then I will be propped and ready by 0900 my time central.

5:49 PM

10:43 PM

sigh....just got home.

Your penis is safe for the night. 'I have 20 minutes left on my show I'm watching..then Im going to sleep, I got to leave early in the morning'

No wonder I love tease and denial. I fucking live it.

12:05 AM

3rd done g.n.

FRIDAY

Mistress D, 7:26 AM

When you are alone I want you to use your edge to stretch your ass. Don't turn it on just lube it up and pound your ass. I want slow strokes that touch your prostate every time. And turn it on so I can control it if I want. If/ when you think you are going to cum pull it out and beg me to et you put it back in only when I reply can you continue.

8:00 AM

yes Miss. About 1/2 an hour got to cleanse etc and finish hitching this trailer.

when you say 'pound'... stroking. OR like pushing hard?

Mistress D, 8:14 AM

Both

8:16 AM

yes miss. Going to do prep now

8:50 AM

Think I. Ready. Lubing the edge

8:56 AM

Slowly stoking super tight

Hmm back to bathroom for a minute

Back

9:10 AM

Stopping for minute

Leaving it in

Stroking shallow

In deep short moves

Rocking with my hand against p spot get most stimulus it seems fyi

Stopping inserted again.

Mistress D, 9:18 AM

keep going

9:18 AM

Yes miss

So tight

May plz stop for a minute

Mistress D, 9:23 AM

Yes

What's wrong?

9:24 AM

Thank you Miss

Tight tender