Punishment Dare - Day 3

Was up way too late last night, but was worth it. Put on my domme hat for a little while and had a very nice guided masturbation session with an online friend. He was nice enough to give me permission to write about it as long as he remained anonymous. He's not into denial unfortunately so I did have to let him cum at the end.

That's fine though I decided to tease the shit out of him before I did. I had him pinch his nipples and play with his balls for a couple of minutes before I touched his cock.before i even allowed him to move one had down to lightly run his fingers along his shaft for another couple of minutes. After he told me he was dripping lots of pre-cum, I had him switch to very lightly fingering his cockhead for a little while, all the while his other continued plying with his nipples. Once I had him nicely turned on I made him leave his cock for a little while and go back to pinching his nipples. We did that for a couple of minutes before I had him grab his dick with one hand and rub his lotion slicked palm across his dickhead. He completed his first edge within a couple of minutes. Let him co back to pinching his nipples for about a minute and then asked him to polishing his knob, I told him if he edged himself that way for 10 minutes he could have 5 minutes of actual stroking. After this his third edge he had about 3 minutes left. So I told him that he'd edged enough, if you had to edge again to cum, but take his hand away immediately. He lasted 1 minute before he stopped. Realistically I should have forced him to ruin, but I decided to be generous. I told him to finish the 2 minutes, if he had couldn't do so without edging he would have to ruin. I may have restarted the timer once or twice, in my defense he was typing so clearly not polishing. He did manage to finish his time without coming, so I had him rest for a minute and then let him have 5 minutes of firm stroking. It didn't last 5 minutes.

Fate it seemed determined to pay me back for my teasing ways because I ended up with CLIT PAINT X5 in my inbox this morning.

I started of doing the first 15 minutes using my labia spreader again to make sure the bristle could easily tickled my clit. By the time the I was done I was very wet, but no where near the edge. I'm pretty tired from staying up way to late the last couple of days, but I don't think that was it. The paint brushes bristles rub and lightly scratch my clit, the blush brush gently tickles it.

Once the first 15 minutes was up, I took a 30 second break and restarted the timer. I was pretty much in the same state when the next 15 minutes where up. I can honestly picture being tied up spread eagle, blindfolded and having a dom tease me this way for hours. Feeling constantly aroused, but never enough. 

I decided to go for broke. I grabbed a blindfold and set the timer for the remaining 45 minutes. I day dreamed about what it would by like tied up for hours being teased this way. When the timer went off, my pussy was sopping, but I hadn't come near the edge once.

Even though I should have called it a day at that point, I decided to at least get one task in. 

• 50 spanks to my clit with the wooden spoon
• 50 spanks to the pussy with my red paddle
• 20 minutes with ginger up my ass

The spankings were quite enjoyable on my sensitive little clit. It's been a long time since I indulged in figging though and I initially wasn't able to stand it. I had to try 3 separate times before I was finally able to go through with it. I did simmer down a little during the delay so I ended up having to finger the whole 15 minutes again. 

The thread was very active today so I didn't manage to make any headway. 

Punishments remaining before I can cum:

Orgasm Denial - Penalty Day 2

Penalty Day 2:

• Number of edges9
• 2 edges must be held for 90 seconds
• 2 Punishment sessions
• 200 hard spanks to each butt cheek with the brush of my choice. Punishment to be completed over my naked bottom. 
• Denial.

 My Pet ended up flipping tails (milking) on Sunday which he completed, but he forgot to report. He flipped heads on yesterday and gave his balls 5 spanks between each edge. Then he rolled an 11 (A full orgasm, that must include anal stimulation). Since he'd forgotten to report on Sunday, I told him that he had to redo his 20 minuted of milking before he was allowed to cum. Did I mention he hates milking? It makes him all leaking, but leaves him frustrated as hell. He did and then proceeded to cum intensely about 30  seconds after he was allowed to touch his cock. Well at least yesterday wasn't so bad. 

We've decided to continue with the dice game until I get back from my vacation next week. I haven't decided what well do yet, but I have a feeling there might be quite a bit of milking involved. 

For myself, I decided I didn't have a proper brush for my spankings so I went out and bought a nice wooden hair brush. I also figures out that I'd delivered my prevbious spanking wrong. I'd done a total of 125 spanks total, instead of 125 to each cheek. So first order of business was to deliver the missing 250 spanks from the previous night.

Once that was done. I edged with the Magic Wand. I tried to get closer to the edge when I held it for the 90 seconds and in fact reset the clock several times. Once I finally edged to to my satisfaction I delivered that nights first set of spanks 200 to each cheek. Ouch! I did my best to land as many as I could on my sit spot. My ass was red and smarting by the time I was done. 

After that I edged with the Magic wand again twice and then made sure to hold the second edge 90 seconds. Once that was done I delivered the second set of spanks to my already sore ass. After that it was off to the shower where I used the showerhead to complete my remaining 6 edges in record time.       

Orgasm Denial - Penalty Day 1

Penalty Day 1:

• Number of edges 6
• 2 edges must be held for 60 seconds
• 2 Punishment sessions
• 125 hard spanks to each butt cheek with the brush of my choice. Punishment to be completed over my wet naked bottom. 
• Denial.

I stayed up ridiculously late on Friday. As a result I was in bed most of the day on Friday. So, I decided that I would take Saturday off.

My Pet on the other hand had an active Friday night Saturday morning. He was behind 3 daily tasks and decided to do them all at once. First his coin flips, heads, heads and tails. For some reason he decided to do all 100 ball spanks at once. Once he was done his cock was dripping, but he'd gone completely soft. I did give him the opportunity to spread them out. Oh well, I'm guilty of that myself often enough. Once that was done he completed his prostate milking.  He still managed to edge from it though. Once he completed his milking he decided to edge another 10 times before going to bed. 

That left him with 20 edges to catch up  the next day, plus new edges for Saturday. As you can imagine once he'd completed those he was very horny. But he still hadn't completed his ruined orgasm from earlier in the week. For those who don't recall he'd rolled a 9 which is 50 spanks to his cockhead followed by a ruined orgasm. He completed the 50 spanks and then ruined his orgasm. Then there was a little confusion with the rolls because he delivered another 50 spanks to his cockhead post orgasm. He hated that. He hated it even more when I told him that wasn't required for a 9 roll. Poor thing. 

Sunday, I stayed in bed for quite a while, but did manage to complete my spankings and  my required edges. 16 days left. 

New Orgasm Denial Dare - Day 17 - Denial

Day 17:

•     May not wear panties (Optional)
•     Wear a butt plug for 6 hours (Optional)
•     Number of edges 4
•     2 edges must be held for 90 seconds
•     No Punishments
•     Denial
  

On Monday my denial pet, ended up flipping tails so he had to milk his prostate for 20 minutes. He ended up dripping precum all over the place. Apparently then his luck ran out because he rolled an 8  (Which means denial and an additional 10 edges) 

I didn't have any punishments Monday so I ended up using the magic wand to complete my punishments.

Wednesday's punishment schedule:
4 sessions were I spank my my wet pussy hard with my hand 125 times.

Penalty Days to date: 16 

New Orgasm Denial Dare - Day 16 - Denial

Day 16:

•     May not wear panties (Optional)
•     Wear a butt plug for 6 hours (Optional)
•     Number of edges 7
•     2 edges must be held for 30 seconds
•     3 sessions of 50 hard spanks on my wet bottom with a flogger.
•     Denial
  

My denial pet, ended up flipping heads. His balls were very sore when he was done. I rolled for him again. The lucky boy ended up getting a 6 (Which became a full orgasm after his 15th day of the dice game. And he thought he'd never get that far. Silly boy) 

Before bed, I spanked my ass 150 times with a heavy flogger again. Then I I edged in the shower. I tried to wear a butt plug to bed, but couldn't manage.

Tomorrow's punishment schedule:
3 sessions were 1 clothespin/clamp is attached to my clit and 2 on each pussy lip for 20 minutes.  

Penalty Days to date: 16 

Orgasm Denial Week 2 - Day 3 - Next Orgasm August 24th.

PM dares I pilling up. Starting to wonder if I'll be able to complete it one evening. One thing is certain, I'll have a very sore backside and clit. I didn't do very much yesterday, but edging has kept me busy. 

I also gave an online sub jerk-off instructions, along with anal and a spanking. He'd displeased me a few days ago and promised anything to get into my good graces. Poor thing wasn't expecting I was going to tell him he had to wait until tonight to cum. Frankly that's letting him off easy, but I didn't think he was capable of any prolonged denial. That lasted a well into the night. So much for catching up on sleep.

Orgasm Denial Week 2 - Day 1 - Next Orgasm August 24th.

OMG, taking a chance on my new pet was completely worth it. Very happy with him. Very happily teased and yesterday I edged myself reading his report of the first task I assigned him. Poor baby spanked his ass cherry red for me. As the second part of his task he's completing daily edging sessions for me and will be in denial for a few days.

I also got a new semi-permanent dare. I need to edge any time I go to the bathroom. If I'm somewhere where I can't edge like work, I have to edge twice when I get home. If I don't complete all my edges, they are carried over and I have to double them again. It's left me a horny mess. 

Also stayed up until 2:00 AM milking a male friend, which is probably why I've spent most of my Saturday in bed.

Orgasm Denial Week - Day 4 - Next Orgasm on August 17th.

So tired. Mostly played on Get Dare yesterday during the day. Sent a couple of dares, made a couple of new friends.Then yesterday, started playing with a sub I've been playing with for a while. He'd been in denial, with only two ruined orgasm to show for it for over three weeks. He teases himself in the shower for me everyday and for the last week he'd been edging every night before going to bed, adding incremental edges each night. To make things even worse he was instructed to spank his cockhead with a wooden spoon every after every edge. I made him understandably sore and sensitive. 

We started out the session with a regular spanking, followed by a ball spanking. After lot's of edging and spanks to his cockhead and his balls with a wooden spoon, he was finally allowed to cum. All and all we played until the wee hours of the morning. 

My dog was not understanding at all about this and insisted that I wake up this morning to take her out.   Despite the fatigue, I'm still extremely horny and managed to play with myself several times today. Starting to really look forward to Wednesday.

Orgasm Denial Week - Day 2 - Next Orgasm on August 17th.

Did some morning edging while getting ready for work in the shower. After finishing work I received the final draft of my next dare and I have to said I'm very excited to start. I was also asked to do two edges which I completed before bed.

Also played with 4 other online friends throughout the day. One doesn't like denial just teasing so I went easiest on him.After an hour of teasing he got to have a nice orgasm. And he'll be returning the favour at some point, minus the orgasm of course.

The second boy, got to ruin his orgasm.

The third as permission to cum, but only from anal stimulation. He's still working on that, along with nightly edges.

My last unfortunate playmate only got to edge while spanking his cock-head with a wooden spoon prior to each edge. He hasn't been allowed anything but 2 ruin orgasm in over 2 weeks.

Obviously all that playing has left me very horny.