Mistress Olympics Continued

Part 1 My Be Found Here:


Intro Note  From Author:

Hello everyone.  I want to thank Mistress Fiona’s anonymous caller for suggesting this interesting topic for a guest blog writing project.  Also, I must thank Mistress Fiona herself for her great inspiration for these stories and also that she not only accepts these guest blog entries, but also suggests and encourages them.  Of course, I also must thank Mistress Fiona for passing on this interesting idea that her anonymous caller had suggested.  Once I had heard the idea of a ‘Mistress Olympics’ concept, it got my thinking about the many different directions that the story could go and the numerous possible themes that such an adventure could follow.

The story below is dedicated to Mistress Fiona and her creative inspiration, and also to the anonymous caller who made the suggestion.  I do hope that what I have written and the direction that I have chosen to take this idea meets with the approval of the caller.  All of you Mistresses, other callers, general fans, and any other readers, please enjoy the story.

As a final comment, let me add that anyone who wishes to carry the story forward for other ‘Mistress Olympics’ events, whether that story stars Mistress Fiona or any of the other fantastic LDW Mistresses, please feel free to do so, and have fun with the concept.  Everyone, Enjoy!



Mistress Olympics Blog Entry – Part 2

My name is Brad.  I have been a submissive and boy toy pet to Mistress Fiona for nearly six months now.  Wow, how the months have just flown by, in her wonderful care.  I have a high powered day job in investing, and I deal with many different people in my daily work.  One of my workers and I discussed our girlfriends last year, and somehow the topic of the conversation turned much more personal.  In the end, we both told the other that we were submissive and that we had Domme women as our girlfriends and Mistresses.  Even though we shared that we each other, we didn’t inform anyone else.  As time went on, we hung out for lunch occasionally and discussed things about our Mistress girlfriends and other topics of interest.

One day my coworker told me about a very interesting competition that would be taking place in just a few months time, a ‘Mistress Olympics’ event with awards and prize money for each event.  I read the flyer that he showed me.  Immediately, I wanted to tell my Mistress Fiona all about this event.  Also, I wanted to convince her that she should join up.  Some part of me briefly contemplated the idea of entering Mistress Fiona into the competition without her prior consent, but I quickly convinced myself that would be a very bad idea.  I instinctively knew that my Mistress would most certainly be quite upset with me for doing something like that without her prior approval and consent.

I made a copy of the flyer and I brought it home with me.  One of first duties after work is that I fix my Mistress Fiona her dinner and serve her.  Once dinner is done, my Mistress relaxes with wine and television while I clean up.  After my Mistresses’ dinner is cleaned up, I am allowed to heat up my own dinner.  Later that evening, after I had finished my dinner and everything was cleaned to Mistress Fiona’s specifications, I knew that I could approach her with my suggestion.  Politely and quietly, I waited by the recreation room door while my Mistress was watching her favorite television shows.  I wouldn’t dare do or say anything before I heard her acknowledgement of me.

“Yes, my pet,” Mistress Fiona asked me, as she turned my direction and her smoldering blue eyes looked me up and down.

Very politely, I replied, “I’m sorry to disturb my Mistress, but I heard about something at work that I thought you would find interesting, Mistress Fiona.”

“Tell me,” my Mistress then said, as she looked at me with a curious expression on her pretty face.

I carefully handed the photocopied flyer for the Mistress Olympics to Mistress Fiona.

After she did so, I mentioned that I would like to discuss something that I had heard at work.  She allowed me to do so and I told Mistress Fiona all about the ‘Mistress Olympics’ that I had heard about from my co-worker.

The idea of the Olympics did intrigue my Mistress a lot and she asked for the flyer.  I handed it over to Mistress Fiona, and she read it over.  She informed me that she would think about it and that I should finish my evening duties.  I understood that to mean that the conversation was done and my Mistress wished to return to her television shows.

As she ate her breakfast, which I had prepared, in the morning, Mistress Fiona said, “I slept on that little flyer idea of yours, about the ‘Mistress Olympics’ and I think it looks like fun.  You, of course, will be my partner for the cock stroking contest.”

“Yes, Mistress.  Thank you, Mistress,” I said with a huge smile on my face.  “Would you like me to take care of the entry paperwork for you?”

Mistress Fiona answered, “You may start the paperwork, but you will not submit anything until I have read it over and signed off.”

“Of course, Mistress,” I replied softly, but I beamed happily.

That evening after dinner Mistress Fiona read over the application paperwork.  “Good job,” she purred as she signed her name and then gave me back the paperwork to send in the application.


Time ticked by and it was over three weeks later that Mistress Fiona received a later back from the local ‘Olympics’ entry review committee, and her application had been accepted.

After my Mistress had been accepted to the Olympics competition, she told me, “We both need to train up to be ready for the Mistress competition.”  Mistress Fiona added, “The rules state that I will be stroking my opposing Mistress’ slave boy, and she will be stroking you off, my pet.”  On went my Mistress as she said, “The slave boy toy who can last the longest under the opposing Mistress’ erotic touch wins that round of competition for his Mistress.”

The following morning, Mistress Fiona told me, “I am going to bring a different girlfriend home every night for the next several weeks.  You will be blindfolded and you will stand at attention with your hands tied behind your back, just like you will be for the competition.  My girlfriend will then stroke you off until you cum, and I will time you to test how long you last under these different female touches.”

The end of Part 1.


Mistress Olympics Blog Entry – Part 2

Hello again everyone.  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.

With that said, please enjoy the second part to the ‘Mistress Olympics’ storyline.



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 and that 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 place, so 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.

To be continued….



Thank you JJ Darling for another wonderfully rollicking installment!