Mistress Olympics Pt. 2


Mistress Olympics Pt. 2

Continued from Pt. 1

Intro Note From Author:

Hello again everyone. please enjoy the second part of the Mistress Olympics Pt. 2 storyline.V  I want to thank Mistress Fiona for posting the story on her blog, and for the wonderful creative inspiration that she provides.  I also want to thank everyone who commented or in any way responded to the blog entry, your thoughts are very much appreciated.  Finally, I thank everyone who took the time to read the story, whether you commented or not, it’s great to know that the story is being and enjoyed by the Mistresses, callers, and readers out there in the LDW community.  -JJ

It was the first night that Mistress Fiona had said the she would bring a girlfriend home with her to stroke me off.  My Mistress had told me that she and her friend already had dinner plans. I didn’t need to ready dinner, as I normally did for her.  After work, I cleaned up the house and then I prepared my dinner.  Once I finished my meal, I cleaned the area and put everything away in its plac., The kitchen and dining area was once again spotless.  I returned to my room and waited.

Approximately fifteen minutes later, Mistress Fiona text messaged me and informed me that she would arrive soon with her friend.  I stripped as I was told, and I put on my blindfold.  Quietly, I stood in front of the comfortable sofa in my Mistresses’ office, where I was told to wait.  My far less than adequate prick twitched in the cock cage, as I thought about my Mistress and how her friend’s touch would feel.

I heard some soft giggles and two feminine voices immediately after I heard the front door open and close.  One of the voices I immediately recognized as Mistress Fiona’s sweet sound.  The other voice I only recognized from phone calls, but I had never seen the other woman’s face.  High-heeled steps softly echoed against the hardwood floor, and the two voices became louder as the women walked closer and closer to Mistress Fiona’s office.

The door creaked softly as it opened and the two gorgeous women entered.  “Hello Brad, my pet,” Mistress Fiona purred in her soft and feminine, but still commanding, voice.

“Good evening, Mistress,” I replied.

Mistress Fiona took her usual seat in the comfortably padded leather chair.  She leaned back and then said, “Pet, this is my friend Holly.  Holly is going to unlock your cock cage and then she is going to stroke you off, while I time you, to see how long you can hold out under her touch before you cum.”

“Yes, Mistress,” I answered nervously, unsure about how long I could last.

First, I heard the soft click of the lock as Holly unlocked the padlock which held the cock cage securely in place.  Next, my Mistress’ friend removed the clear plastic cage and released my limp cock from its confinement.  The next thing that I felt was that Holly took my hands in her own, and she brought my hands up to softly squeeze and caress her ripe and firm medium cup sized breasts.  Holly’s soft breath blew sexily into my right ear as she teased me.  Her soft feminine hands moved away from my hands, leaving my hands in place to continue to fondle her perky boobs.  Miss Holly then reached down and began to massage my cock and balls with her expert fingers.  One hand rubbed and played with the balls, while the other hand stroked and worked my cock.

Holly purred at me in her soft feminine voice into one ear, “Cum for me, baby.  Do it!  Shoot that load.  I know how bad you want to.  Give me that cum!”

While in the other ear, I heard Mistress Fiona as she told me, “Hold back.  Don’t you dare cum!  You only cum when I tell you!”

As much as I tried and I wanted to make Mistress Fiona proud of me, Holly’s erotic touches and her soft voice as she cooed softly at me were just too much.  I didn’t even last for five minutes before I blew my load all over Holly’s hand.

“Stop!” my Mistress called out.  “Four minutes and forty two seconds.”

“I’m going to go clean up,” Holly said, the disappointment obvious in her tone and words.

Mistress Fiona took off my blindfold and looked at me.  She just looked me and sighed, “Four minutes and forty two seconds.  You are going to get us both laughed out of the ‘Mistress Olympics’ competition if you can’t do a LOT better than that.”

“I’m sorry, Mistress,” was all that I could manage to say, even though I knew it wasn’t nearly enough.

My Mistress’s friend Holly took her leave at this point.  After I had shown her out and locked up the doors once again, Mistress Fiona called me back to her office.  Even though it was already late by the time Miss Holly had departed, Mistress Fiona spent the next nearly three hours in edging and ‘tease and denial’ bliss.  Expertly, Mistress Fiona squeezed and massaged my dick until I panted and my prick jumped in excitement that it was ready to explode.  A wicked grin on her beautiful face, my Mistress then squeezed the head of my penis hard, and she gave me a horrible case of blue balls as all of that cum that was ready to shoot suddenly had nowhere to go.

She gave me a short respite before we continued the ‘tease and denial’ and edging game.  Once again, my Mistress showed off her expertise at pleasing a man.  Mistress Fiona stroked my not so big, though erect and hard, dick and she gently massaged by aching balls.  Her supple and delicate fingers worked their magic on my shaft and soon I was ready to blow my load again.  I sighed and panted for release, as I begged Mistress Fiona to let me cum.  My aching blue balls needed to be relieved and to blow my wad of cum was the only thing that would really help me.  Mistress Fiona knew exactly what I needed for my sore balls, but just as before, she stopped the flow of my baby batter from my dick and ruined my orgasm.  I groaned loudly as the ache welled up inside me for a second time.

“Maybe this will be a good lesson for you to learn not to disappoint Your Mistress so badly,” Mistress Fiona said in her sugary sweet, but venomous, silky soft voice.

My Mistress spent the next two hours as we this same rollercoaster up and down.  She repeatedly built me up just so very close to that orgasm that I have dying to have and relieve my balls, only to snatch it away from me just at that very last moment when I think I am finally going to get my release.  On and on we went.

Finally, as the evening grew to an end, Mistress Fiona said, “Enough of this, pet.  It’s time to let you have your reward for the rest of the night.”

“Yes, Mistress,” I said with a smile.  I just knew that she meant that she was going to finally stroke me off and give some relief to my sore, achy balls.  I didn’t dare say it though, because I knew that would be the end of any chance to cum, if I said it.

Mistress Fiona then said, “That’s right, pet.  I am going to let you back into your cock cage, so you can spend the whole night just like you are.  Maybe tomorrow when I bring my next girlfriend over, you will have learned, and you will do a better job holding back MY cum.”

I was crushed at those words.  I had wanted to cum so badly, but I also knew that Mistress Fiona had every right to leave me caged up all night with no release.  I had disappointed her, and I had disappointed myself with my performance.  This had, after all, been my idea to suggest to join the ‘Mistress Olympics’ and I couldn’t do this badly for my Mistress.


The next morning I fixed Mistress Fiona her breakfast as I always did, before I quickly ate my food, cleaned up and then departed for work.  Mistress Fiona took her time to finish up her meal and it nearly made me late to catch my usual train into work.  I made it on time, but only just barely.

After work this evening played out similar to the previous night.  I ate my dinner alone in the house, while Mistress Fiona and her friend went out to dinner together.  Once again, my Mistress messaged me when dinner was done and she and her friend started toward the house.  That was my cue to go to the office and get undressed and blindfolded.

I waited in the office for what seemed like a painfully long time.  Finally, I heard the front door open and I heard the feminine voices and giggles, as my Mistress and her friend walked closer.  The clicks of the high heels on the hard wood floor was unmistakable, as Mistress Fiona and her friend walked and talked their way up the stairs and down the hallways.  I heard the door creak open as my Mistress opened the door to her office and stepped in.  I heard the steps as Mistress Fiona and her friend stepped into the room and settled into position.

“Brad, my pet, this is my dear friend, Mistress Eva,” my Mistress said softly.

“Good evening, my Mistress,” I said respectfully.  Then I turned to where I thought Mistress Eva stood and added, “A pleasure to meet you, Mistress Eva.”

“And a pleasure to meet you, too,” the new Mistress replied.

With my blindfold in place, I couldn’t see Mistress Eva.  I had no idea what she looked like.  Later, I would learn and see that she was a beautiful raven haired woman, well-endowed in the bust department, and all perched on a leggy, wiry shape, similar to my Mistress Fiona is some respects, but completely different in others.

Neither Mistress said anything.  The room was quiet for a while, then I heard the soft click as one of the Mistresses unlocked my cock cage lock.  I felt the comparatively cool room air hit my prick as the cock cage was slid off.

My balls and cock were still sore and achy from all night with that blue balls treatment.  A few moments later, I felt an amazing soft feminine touch on my cock.  I knew Mistress Fiona’s light amazing touch very well. I didn’t have to be able to see or hear to tell that this was a different woman’s erotic touch.  I knew that it had to be Mistress Eva as she used her feminine wiles on my body.  Her fingers and palm worked all around my cock and balls as she built up my impending pleasure.

In my right ear, Mistress Eva whispered to me, “Come for me baby.  You know you want to explode.  Let it go.  Shoot that load for me.”

“Don’t you DARE cum, Brad,” Mistress Fiona whispered softly into the other ear.  “You hold it back.  Think of anything but your dick.  DO NOT CUM!  You hold it, pet.  Hold it.”

The whispers went back and forth as I got the conflicting signals from the left and right ears.  Mistress Eva’s touch felt so wonderful, and her soft silky voice, she made me want to cum so badly.  But, at the same time, I knew that Mistress Fiona would be horribly disappointed, and I would be in such trouble if I didn’t make a better showing this time.

In the end, the conflicted signals that I heard allowed me to hold off and hold back my cum long enough that I gathered my thoughts and held back my impending orgasm.  All the while, Mistress Eva continued to pump and massage my dick.  I felt her full round and ripe breasts against my face, as she fed me a nipple to excite and arouse me in a different way.

Finally, even with Mistress Fiona’s prodding, Mistress Eva’s touches just went too far.  I let out a loud groan and grunt before I let go and shot that gooey stream all over her hand.  Not too happy that I made a mess all over her new manicure, Mistress Eva gave me her fingers and palm and made her lick the cum off her digits, one by one, until I had completely cleaned up her hand..

Mistress Fiona took off my blindfold, and I saw the big smile on her face, and I finally saw Mistress Eva for the first time.

“Good job, my pet,” Mistress Fiona said softly and warmly.  “You lasted just under 30 minutes that time, before you had to cum.  A much better performance.  You held out for twenty eight minutes and thirty three seconds to be exact.”

Mistress Eva smiled and said, “That was good, pet.  And I really pulled out the stops to make you cum.  You showed some great restraint.”

I blushed and smiled, “Thank you both, Mistresses.  But, I know that I still have a lot more work before I’m ready for the Olympics competition.”

“Yes, we do have more work, but this was much better,” Mistress Fiona added.


Hope you enjoyed Mistress Olympics Pt. 2



To be continued….



Thank you JJ Darling for another wonderfully rollicking installment!

Thank you so much

XOXOXO, Enchantrix Fiona