Three Cam Sessions

Lol

Mistress D, 9:25 AM

You need more lube It should never be hard to push in

9:25 AM

It's OK I'll put more lube just feels dry when it in deep

Ok back in on pspot

Mistress D, 9:32 AM

good keep going

9:34 AM

Starting to get a little hard from pressing in on p spot

Mistress D, 9:39 AM

I have a meeting put on a timer for two minutes and then take it out wait 1 minute then put it back in do this 5 times

9:40 AM

Yes miss

Thank you for guiding me

10:01 AM

I'm complete. I'll stand by. Working from home today?

12:30 PM

Removed.

Omg. Thank goodness.

Mistress D, 12:57 PM

Good boy

12:58 PM

Thank miss.

I hope you have fun this weekend. Do you have big plans?

1:51 PM

Mistress D, 6:54 PM

As for your punishment from Tuesday. No touching at all until next Tuesday 5/30. The only time you should be out of your underwear is off is when you shower. No rubbing No grinding nothing but to keep you stimulated I'm going to give you homework. I want you to write me a dirty story. I want you to pick a kinky thing you want to try and I want you to write your fantasy out by Tuesday it has to be at least 1000 words but it can be more. If/when you deliver your story to me I might let you touch yourself. I want your story idea by tonight. Do you understand boy?

What are you doing now slut?

10:47 PM

Sitting at my pc. Mr is back roaming around. Why how can I be of service?

She has a headache hope she might got to bed early! Lol.

Mistress D, 10:48 PM

hows your ass feeling?

10:49 PM

A bit tender it's more that it's uncomfortable when stuff is in it lol

My taint is a bit bruised from edge

Nothing I can't manage

Mistress D, 10:50 PM

So sensitive slut.

10:50 PM

I know... I had no idea.:)

Mistress D, 10:51 PM

go put your edge in I found a fun pattern I want you to try out

10:51 PM

Yes Miss. I might need to do a bit of prep? Do u have time?

Mistress D, 10:52 PM

Yes do it right and do it quickly

11:01 PM

In

Doing kegels is interesting with this in.

She laid down fyi.

Mistress D, 11:03 PM

Can you feel that?

11:03 PM

Yes miss

Mistress D, 11:04 PM

Good

How does it feel?

11:04 PM

Throbbing and vibey

On my p I'm trying to settle in on it.

Mistress D, 11:07 PM

Have you been learning you lesson on punishment?

11:08 PM

Yes Miss. UN authorized touching is a bad idea

Mistress D, 11:08 PM

Is that something you will do again?

11:09 PM

No Miss.

I hope not!

Mistress D, 11:09 PM

Good boy

Thank you

Mistress D, 11:10 PM

Hows your ass?

11:10 PM

lol

I'm trying to keep it on p

It's loud...but I have music on

Mistress D, 11:10 PM

Sit back a bit

11:11 PM

Oh shit

How did u know

Mistress D, 11:12 PM

Lol I know your body better then you slut. It's mine remember

11:12 PM

Yes miss

Do you do this with your other sub boys?

Like this?

Mistress D, 11:13 PM

Yes I do sometimes

Still vibrating?

11:16 PM

Yes miss

Right there

Mistress D, 11:16 PM

Oh?

11:16 PM

I'm on the spot.

Feel pressure in my head

Not hard yet

Or anything

Mistress D, 11:17 PM

Who said you were supposed to be getting herd? I'm just playing with what's mine

11:17 PM

Yes miss

Mistress D, 11:17 PM

tell me when it stops

11:18 PM

Yes miss

so this counts as playtime!

Mistress D, 11:19 PM

lol yes

Rock back and forth a little

11:23 PM

Yes miss.

Omg another 10 minute 1!

Mistress D, 11:27 PM

I have a 20 min one if you want to complain

11:27 PM

No miss!

Mistress D, 11:27 PM

Thats what I thought

11:34 PM

Omg..lolol

I nearly spilled my drink

Mistress D, 11:36 PM

You're welcome slut

11:36 PM

lol. You are trouble arent you.

Mistress D, 11:37 PM

We really need to fix these little comments

11:37 PM

Miss?

I thought we were playing!

Mistress D, 11:39 PM

I don't want you too comfortable

11:39 PM

Trust me I'm not

I have a plug up a very tender dry ass

Next Saturday:

Oh and Ty, for allowing me to share notes. I understand I'm not important to u or worthy Miss.

8:46 PM

Fuck my wife just asked if she could play with my cock...why now? It's like u 2 r in cahoots.

Mistress D, 8:46 PM

Let her

8:46 PM

I'm still on no orgasm right.

Mistress D, 8:46 PM

Yup

8:46 PM

No miss please.

Mistress D, 8:47 PM

If you cum you can't talk to me until Wednesday

But you cannot deny your wife

8:47 PM

Miss.

Noooooo

OMg. Shit.

Now I regret that extra cocktail.

Mistress D, 8:48 PM

Go enjoy your wife sub

8:48 PM

That's not funny. MISS.

Wish I could put camera on to show u what happens.

Mistress D, 8:49 PM

Dirty boy

30th Tuesday

Sounds like you had fun last night

1:00 PM

Lol. Sort of. I'm just glad I stopped or redirected her and explained I wanted to edge

Mistress D, 1:00 PM

Lol you should have cum it might be a while until you cum again (devil)

I sent you your new task in keep

1:01 PM

Miss. Really? How long is awhile?

Lol.

Don't you want to play with your bits

Mistress D, 1:02 PM

Playing with you doesn't mean you cumming

1:02 PM

I understand.

Mistress D, 1:02 PM

Especially this month I might make you wait until July lol

1:03 PM

LOL... wow.

Mistress D, 1:03 PM

You can do it can't you?

1:03 PM

im still reading. holy shit.

So 3 sets of strokes a day no orgasms five days in a row then I get 5 questions.

Mistress D, 1:07 PM

Yup easy right?

1:07 PM

at least we wont be using that gravity or edge or binding stuff. Should be ok I think. But your cock sure is sensitive.

I was really worried about having a session with you anyway.

Mistress D, 1:08 PM

Who said we wouldn't be using it?

1:08 PM

the instructions....

oh...boy

Mistress D, 1:08 PM

What were you worried about?

1:08 PM

cumming without permission

based on how I was touched last night.

this is the longest Ive eve gong without touching or coming in over a year

gone^ 7 days and last 1 was ruined

Mistress D, 1:09 PM

That's not even that long lol

What are you going to do when I make you wait a month?

1:10 PM

MISS

MISS

WHAT

Mistress D, 1:10 PM

what slut?

1:11 PM

I know you gave me those stories to get 'juices' flowing.. but a month.

no way I could do that.

how would i

Mistress D, 1:11 PM

If I tell you to you will. We'll build up to it

1:11 PM

but why torture me like that lol.

Mistress D, 1:11 PM

Because you like it

I'm starting a timer for 1 hour when it goes off I better have ten questions got it

1:34 PM

yes miss.

Mistress D, 1:35 PM

Starting now

1:44 PM

Will you answer the questions fully ;)

.. Or will I get your Miss 'I was bored' answers.

These strokes, I can do skin on skin yes!? hallelujah.

Mistress D, 1:45 PM

Lol Yes for now

And you get what you get lol

smartass

1:45 PM

OMG.. I knew it. You are sneaky Miss.

lol thank you.

Mistress D, 1:48 PM

I will answer as honest and fully as I feel comfortable if you stroke your cock well I will answer well deal

1:49 PM

Yes Miss. I suspect a trap!! But Im game for a challenge, maybe even 30days. Which sounds impossible, but what would you allowing me to come after that feel like? hmm.. would I even want to? so interesting. Thanks for the thought provoking way you manage me.

Mistress D, 1:51 PM

Wow I'm not trying to trap you, you just easily fuck up lol

1:51 PM

lol. aint that the truth

sent

Oops..... I just saw this bit.

"won't have time for you everyday but when I do I will use you how I please and those days will obviously be harder."....shoot.

Mistress D, 1:54 PM

Lol

You are always trying to be sneaky no two part questions lol

1:54 PM

...ok. sorry.

Mistress D, 2:05 PM

go ahead boy

Stroke that cock slowly for me

2:06 PM

But it was 20 fast?

Mistress D, 2:06 PM

So go slow because I said so

2:06 PM

Yes Miss. Starting

Done 20 slow miss

Mistress D, 2:08 PM

Now 20 fast

2:09 PM

oh. Yes miss

Done miss

Mistress D, 2:09 PM

Again

2:09 PM

Miss?

Done.miss

Mistress D, 2:09 PM

What boy?

Do 10 slow

I told you days with me were going to be harder lol

2:10 PM

Yes miss

Done miss

Mistress D, 2:11 PM

25 fast

2:12 PM

Done miss

Thank you miss

mistress D, 2:12 PM

Again

2:12 PM

Thank you do e

Mistress D, 2:13 PM

Again

2:13 PM

Going to have to pinch my thigh!

Done Miss

Mistress D, 2:13 PM

Pinch your thigh for what slut

2:14 PM

to make me not so hard

mistress D, 2:14 PM

lol your supposed to be hard boy

2:14 PM

Yes miss

Mistress D, 2:14 PM

do 30 fast

2:15 PM

Yes Miss thank you

Done

Mistress D, 2:15 PM

Again

2:16 PM

Done miss

Mistress D, 2:16 PM

Do 30 three more times

2:16 PM

Yes miss

Done

Thank you Miss may I be done now?

I like the 5 questions you chose!

Mistress D, 2:26 PM

do 20 more slow and then you can be done for now

2:27 PM

Thank you Miss.

Whoa got close at 18. Paused for a second

Done thank you miss

Mistress D, 2:29 PM

When you pause grab your balls instead

2:29 PM

Yes Miss.

Mistress D, 2:31 PM

I was going to let you ask me a question but I think you are tapped out lol Talk to you later slut

2:31 PM

oh miss please.

Let me.

Mistress D, 2:31 PM

lol I thought you were done?

2:32 PM

I'll play as long as you want me too and Mr is on the ph

Mistress D, 2:32 PM

If you can't stroke you can't aske questions

2:32 PM

I can stroke.

Mistress D, 2:32 PM

lol

2:33 PM

I just ordered the 1.5 inch wide doohickey thing.

Wider than gravity.

Just

Mistress D, 2:35 PM

lol good

2:35 PM

I think you are excited about it miss

Mistress D, 2:36 PM

Of course I love a well fucked sub

2:36 PM

:)

...!!!

Lol we'll have to do an anal month where you only explore your ass and really focus on the pleasure it brings and how your body likes it

2:47 PM

Yes Miss. I'd like to learn how from you.

I'm getting better relaxing into things and ignoring poop pee urges.

Mistress D, 2:47 PM

It's hard online but it can happen

2:48 PM

:(

I know you are young and I'm old but I'd let you drive I'd trust u.

Mistress D, 2:49 PM

good boy

2:49 PM

But this works

God that makes me horny.

Imaging be under your control in person

Silly I know but exciting

Did u like my story?

Mistress D, 2:50 PM

lol

It was okay a bit boring but fine for your first story

Wednesday 31st

hows my cock feel?

1:57 PM

Tingly. A little swollen and it knows the predicament it is in

Mistress D, 1:57 PM

Good

1:58 PM

I think I can make the 5 days, through sat nite. And even being successful, it still fails. As it won't have cum! U win either way miss.

I've had one or two moments of thrashing around in need as your cock develops a mind of its own.

But I'm not touching or rubbing unless told to

Tomorrow will be hard as I'm going to be alone from noon onwards thru Tuesday.

Mistress D, 2:03 PM

Oh really?(devil)

2:03 PM

You scare me! 😱

Mistress D, 2:03 PM

Good

2:04 PM

You must know how bad my entire groin is aching. Do t u miss.

Mistress D, 2:06 PM

I'm sure you can handle it slut

2:07 PM

Yes Miss. I'm starting actually enjoy the pain. The constant throb. I spent a lot time last nite researching estimm accessories cages and kinks.

**Friday nite 2nd

We pick up with Miss having me do extra strokes, as I close in on getting through the challenge.

Mistress D, 8:41 PM

Again [30 strokes]

8:41 PM

done

thank you miss

Mistress D, 8:42 PM

Againnnnnnnnnnn

8:42 PM

thank you miss

tip is tingling miss

Mistress D, 8:42 PM

Again slut

8:43 PM

close to spear miss

Mistress D, 8:44 PM

Again

8:44 PM

thank you miss

Mistress D, 8:45 PM

Again quickly

8:46 PM

done

Mistress D, 8:46 PM

Again

8:46 PM

done

Mistress D, 8:46 PM

Again

8:47 PM

done

Mistress D, 8:47 PM

Faster

8:47 PM

done

Mistress D, 8:48 PM

A

g

i

a

n

8:48 PM

thank you

done

Mistress D, 8:49 PM

Do more

I hope you know I saw that you went over by 5 stokes

8:49 PM

yes i forgot what time it was miss

Mistress D, 8:49 PM

hmmmmmm

Stroke 20 slow

8:51 PM

done miss

ive had an erection most of the day, having hard time stay ing hard now lol

but still super tender edgy

Mistress D, 8:51 PM

I don't care about your being hard slut

8:51 PM

Yes miss

Mistress D, 8:52 PM

Again slowly

8:52 PM

yes miss

done

Mistress D, 8:52 PM

Again

8:53 PM

how come i feel like i want to come but im not hard.

done

Mistress D, 8:54 PM

Because it's my cock

8:55 PM

yes miss it is and it is hurting for u

im going to use some lube now

Mistress D, 8:56 PM

Quickly you should have been using it from the beginning

8:56 PM

yes mam i got it here

Mistress D, 8:56 PM

Go 30 quickly

8:56 PM

done

Mistress D, 8:57 PM

Go

Again

8:57 PM

done

Mistress D, 8:59 PM

Again

Go

Go

Go

Go

9:00 PM

4 times?

lol

Mistress D, 9:00 PM

Go

9:00 PM

spear

close to spear

done

Mistress D, 9:02 PM

Slowly 25

9:02 PM

done

thank you miss

Mistress D, 9:03 PM

go again

9:03 PM

done

Mistress D, 9:04 PM

Go

9:05 PM

done

Mistress D, 9:06 PM

call me

9:06 PM

Yes Miss let me get blue tooth

Mistress D, 9:06 PM

Quickly slut

CAM SESION 3

1h 11m 47s

[This session is strictly stroke and stroke control. For an hour we go slow fast, do count downs again and I get to our pre orgasm safe word 'spear' many times. I even have a dry orgasm as a tiny bit of pre cum ejects and my body thrashes uncontrollably. Though I am happy, as I find a way to control my orgasms via laughter. As I mentioned earlier she puts on the sultry voice, as as it does not really come naturally to her, as she really does like to be in control and not seductive it is sexy if I let it be, but sometimes when she does it it just cracks me up. So laughing takes the cock tension away, and she ignores me and makes me work all the harder. There is a lot of banter backward and forward. I try distracting her, she challenges me, I once I get control let her know I got it and wont come and will not let her make me. It's a true war of wills. I want my questions I asked answered, she wants to break me. I love it.

Lost connection

Mistress D, 10:21 PM

Hold on

If you don't cum tonight by 12 my time I'll answer a question for you

10:22 PM

(laugh)

Mistress D, 10:23 PM

Stroke slow until I come back

10:23 PM

Yesmiss

Mistress D, 10:24 PM

Add extra lube

10:24 PM

Yes miss

Mistress D, 10:27 PM

Slower

10:28 PM

MISS Yes it's slow!

on ph for a second

Mistress D, 10:31 PM

ph?

10:32 PM

wife call

be off in a sec stroking 1 hand

Mistress D, 10:34 PM

oh you dirty boy

stroking for me

while talking to your wife

10:34 PM

yes miss:)

Mistress D, 10:34 PM

you like that don't you

being my slut in front of her

10:34 PM

yes mam

i like how you take control and own my cock miss

Its petty but yes makes me feel like she is missing out

Mistress D, 10:36 PM

bad boy

go faster

10:36 PM

yes miss

Mistress D, 10:36 PM

10

9

8

7

6

10:37 PM

oh shit.hard!

Mistress D, 10:37 PM

5

4

5

6

10:38 PM

omg

Mistress D, 10:38 PM

7

10:38 PM

no fair

Mistress D, 10:38 PM

8

9

10

11

12

13 or 11

10:39 PM

11 plz

Mistress D, 10:39 PM

1

3

12

11

11

11

10:40 PM

omg thank goodness she is gone

can i stop miss

Mistress D, 10:40 PM

no keep going

10

9

8

7

6

10:41 PM

plz dont make me come

Mistress D, 10:41 PM

5

4

3

2

10:41 PM

mis please

stop

Mistress D, 10:42 PM

telling me to stop?

call now

10:42 PM

mis please no.... no I dont know

yes

57m 21s

[Yes...another 57 minutes. Count downs. At one point I have to count to 80, stroking fast, she controls the cadence. Then takes over right at 70 and takes a full 5 minutes of me stroking to get to 80. I'm a raging bull, im sweating, but exhausted also. But I pass the midnight mark and we eventually get one question and reach the mark to just have one more day to survive to earn the rest of the questions. All this time she is building my stamina up in this game. But also denying me orgasms. It this part of transitioning from orgasm led play to service led play that I am working the hardest on. Instead of being needy, or resentful, look for pleasure in the denial pain, the satisfaction of holding coming for so long, in hearing her say 'good boy'. I am instantly getting aroused when I see skype 'Miss is typing' or especially when she says get NAKED. Gosh its so hot.].

So what happened Saturday? Nothing. Here is the hard part for me. It has to do with compartmentalizing. How do we effectively box out sections of our lives, that threaten to overwhelm us. I went a 100 times to message her. But she is not going to respond. She is busy. Even if she is not its been made clear my needs and timing are not hers, and in any case, why not make me wait. So I do my tasks, I go to bed early, I read, I'm super frustrated calling her out in my mind as I read my kindle. I turn out the light. 'bling' off goes skype, up comes my cock. Its then I realize I have got myself into a pavlovian response mode. I'm truly trapped.

I succeed at my 'game' She graciously answers questions I had asked. We text back and forth. She has no time this month [June] for me. So I have a new challenge. No touching. So now she will break me down mentally. This essay is part of it, as is researching kinks, and writing about them and finding stories on Literotica about those kinks. Oh...and while my wife is out of town I must wear her under wear. My wife is tiny., I'm 6'2' and 190LBs. this is really awkward. But my cock is hard as a rock again as I walk around the house, all her underwear is lacy, some with satin backs. The satin rides up my crack, the lace chaffs my cock. I'm squeezing my thighs together to rub on the lace. I need to pee, to cum, to have something shoved up my ass and told to rock on it. Instead I suffer for her.