Ruined Orgasm or Continuously Milked Pt. 05

Ruined Orgasm or Continuously Milked - I couldn't tell. (FEMDOM m/f) - part 4

The timer seemed to fly by, like it was counting 2 seconds for every 1 as before I knew it, I heard through my ear buds the following message.

"15 minutes is over, I certainly hope you remember the rules and how you have to 'pay' for your pauses. In case you do not, here's a refresher"

And with that, a smack on my ball sack that almost made me pass out, I know I may have yelled louder than ever. Now with laughing, I heard.

"Oh my Toy, really? That was just a reminder, I now get 1 full minute, to be paid for me allowing you to have a timeout, of course, the payment method we agreed to earlier is that I would get to punish you during that minute. So, without further "ado", let's get to it"

I am not really sure what got into my Mistress for this evening, but this was becoming one of the best nights, or weekends, or weeks, or months, hell, I'm not even sure what day it was, but let's just say, "time of my life". The voice, the mood, the laughing, the enjoyment, made it all worth it for me, I loved to see my Mistress like this, fully enjoying her abilities and capabilities, and bringing out the true Mistress, that she can be.

While these thoughts flooded my mind, I felt my dick being pulled to an incredible angle and, what I can only assume was the dick pump, being used again. But, as if that was not enough, the ass fucking now stopped, and what I am guessing was the inflatable dildo now reinserted into my ass, being pumped. In addition to all of this, my Mistress got the idea apparently to not only perform these tasks on me, but then to commentate, like a seasoned TV announcer doing the super bowl.

"Toy, timer is now at 50 seconds, your, sorry, MY DICK, is in a penis pump and set to full intensity, while also set at a 90 degree angle behind you. Don't worry, I am watching to make sure there is no damage done to OUR DICK. What helps the angle is that, your balls are also still tied up, and with every"

All of a sudden, and without warning, there was a WHACK on my balls, with an increased tug, that I certainly was not expecting.

"10 seconds, you will receive a smack on your balls with my small flogger, along with another tug to the ceiling for your ball sack. If you cum, well, let's just hope that does not happen"

Again, WHACK

"without permission. 35 seconds left, and let me tell you how "

WHACK, and tug

"purple your balls are getting. I can't really make out your dick color, but it is quite large. I am not sure you can tell, but you have had multiple applications of numbing cream applied to your dick. On your "

WHACK

"balls, not so much, as we went for the ICY hot idea there. I am not sure it's doing that much, since the intensity is probably being covered up by the other sensations"

WHACK, oh my God, I was so close to coming, at least I think I was, because while she was right about my dick being numb, the smacking on my balls was bringing me to the point where I may not be able to even yell for yellow. I mean, what would the punishment be like for my rest period after this next timeout? Not sure I wanted to find out, WHACK, again.

"nicely done Toy, that's my minute of payment for your timeout request. Now, give me a few minutes to remember where we were before you asked for this timeout, and let's get back to it, okay?"

I was pretty sure, she really wasn't looking for an agreement from me, but for whatever reason, I emphatically nodded like she was waiting for my approval. I imagined my Mistress laughing, assuming she even saw my head move.

Without delay, my ass was repositioned for the fucking 'dick', the pump was removed from my dick, and surprisingly the restraints from my dick and ball ties were loosened. I really believe that for the first time that night, my balls and dick were without a harness of any kind, but I could not be totally sure, as my dick was really only feeling 'pressure' sensations, the numbing cream definitely was doing it's job. I guess though, since she released my members, my ass was in for a bit harsher treatment, as I soon found out on my next announcement.

"Toy, one of the main reasons I could not stop from chuckling when you called for your last timeout, was that, in a matter of just seconds, I was about to release your dick and balls and just concentrate on watching your ass be pounded, as you like to either watch mine or do mine. So, I commend you on your honesty and not cuming without permission, but I have to say, that was unfortunately a "pause" that you did not need to use. You now have 3 pauses remaining, I would strongly recommend you keep a few because remember, this is only day 1."

Again with the chuckle, and at the same time, my ass was fucked.

"Toy, one more thing, I am not sure how long I will be fucking your ass, because it is incredibly hot for some reason watching this take place. So, because of that, I believe I will have a drink, watch, rub my pussy a bit, enjoy the sight and sound, and just take it all in. Please 'try' to enjoy."

Time seemed to pause, sort of like those Matrix movies, I could see and hear things happening, but I could not really seem to move myself. The ass pounding that I was taking, was honestly not hurting that much, as my Mistress made sure to use the right sized dick, I guess, but it also wasn't really doing that much for me. Every once in a while, it did hit the 'right spot' I guess, and the weirdest part about all of this is, I was having these logical thoughts in my head, while being fucked in my virgin ass.

Without warning, the ass fucking stopped, apruptly.

"Toy, I had to stop the entertainment, as I was about to cum, again, and did not want to ruin my last orgasm of the night on an empty show."

Empty show, I thought, wow, what in the hell is she planning still?

"So, with that said, I am going to remove all of your restraints, I will roll you over on your back, and I am going to sit on your dick. You do NOT move, if you move, you will be severely punished, and when I say severely, I mean it."

With that, I felt the ass torture being removed, and my restraints around my wrists and ankles being removed. My Mistress grabbed my cock, hard, and forced it so that I would have to roll over on my back, she then, retied my hands above my head, my feet down to the floor or board, and immediately sat on my dick and began to bounce on it as never before. I am not sure if there was lube involved or just her juices, but it was effortlessly moving in and out. Of course, I could not really feel much, again, just the pressure and the understanding that it was inside of 'something'. There was no real feeling coming from my dick, nothing that could help me cum, other than my mind at this point in time. Over my ear buds, the music stopped.

"Toy, I have added a dick sleeve to your dick, so not only are you numbed up, but you also have what is basically a dildo ON TOP of your dick."

She said with panting breath.

"I am going to literally fuck myself to sleep. When I orgasm, I will get off of your dick, and if I can compose myself enough, I will unlock you. If you cum, you will lose a pause, if you do not, you will gain a pause. When I am done, you will know it. I would like you to get up, and begin to make us some refreshments and some snack foods. Please put on your leather skirt before heading downstairs, and you may have all you want to drink. I would recommend some water, at least a bottle, before you indulge in liquor, but it is your choice. It is now 11pm, on Day 1."

Those are the last words I heard from my Mistress until I returned from the kitchen with some cheese and crackers, some wine, and grapes, along with some freshly cut mango's.

End of Part 5