Mistress Olympics Blog Entry – Part 5

 Last Installment (pt. 4 & links to the first 3 preceding posts)  is found: Here

Mistress Olympics Blog Entry – Part 5

Once again, I want to sincerely thank everyone who posted feedback and comments about the fourth and prior parts of this story. I am beyond thrilled that so many of the LDW Mistresses, callers, and other readers have enjoyed the storyline up to this point.

Everyone please enjoy this next part of the ‘Mistress Olympics’ story, presented now, courtesy of Mistress Fiona and her blog. It is my hope that all of you greatly enjoy this part and all future parts of this story.

As is always the case, I am always interested in any thoughts or suggestions for any future parts of the Mistress Olympics. If there is some event or activity that you would love to see, please leave it here as a suggestion on the blog or notify Mistress Fiona. She and I talk and e-mail on a very regular basis. While I can’t guarantee that I will be able to use every idea submitted, I do give you all my word that I will do my best to incorporate as many of the suggestions sent to me that I possibly could in some way.


This is Brad writing to you once again. When she entered the Mistress Olympics competition, my Mistress was informed that tonight would be the last night for my preparation and training for the cock stroking competition. This morning, after my Mistress finished eating her breakfast and I was cleaning up the kitchen before I left for work, Mistress Fiona told me about tonight being my final night of training. She told me that after training this evening, and for the next three days and nights, the Mistress Olympics rules required that I stay locked in my cock cage until the official start of the event. This way, Mistress Fiona explained, all the slave boys had last shot their last load of cum at the same time and have remained locked in their cages for the same amount of time. That way the field of slave boys would be as even as possible when the competition started, at least in terms of build-up of cum.

Once again, Mistress Fiona told me that she had dinner plans with one of her Mistress girlfriends. This time, though, the pair of lovely ladies would not be joined by one of the other Mistresses bull lovers, as had happened on the two previous dinner meetings. Instead, the other Mistress was bringing one of her slave boys along, and he and I would have our dinner here at the house, while the two gorgeous Mistresses enjoyed a fancy dinner out together.

Mistress Fiona hovered and waited by the front door for me to get home. I immediately knew that my Mistress was displeased because I was late, and the moment I returned home after my work day she pounced. Even though I tried to explain to her about a late afternoon meeting called by my boss, she lit into me for being home late on such an important evening. I knew that there was no way for me to win the argument, so I simply lowered my head and then said softly, “Yes, Mistress. Sorry, Mistress Fiona.”

Not long later, the doorbell rang. I scurried away from Mistress Fiona, and I answered the door. As I opened the door, I saw a gorgeous, but slightly older and more mature woman. Mistress Fiona stepped up behind me and called out, “Hi there, girlfriend!” to the other woman.

“Pet,” she said to me, “this is my dear friend, Mistress Delia.”

“Hello, Mistress,” I said respectfully, as I bowed to the older, gorgeous woman in the door way.

“This is my pet, Brad,” Mistress Fiona said to her girlfriend.

Mistress Delia smiled at me and then said, “A pleasure, Brad.”

“And who is this?” Mistress Fiona asked curiously, as she noted the submissive male who stood behind and to the side of Mistress Delia.

With a soft smile, Mistress Delia answered, “Ah, yes. This is Tim, Timmy, as I call him. He is here to help out for tonight’s training.”

“Hello, Timmy,” Mistress Fiona purred at the man with his head bowed.

“Hi, Timmy,” I added quickly, as my Mistress nodded in my direction.

“Nice to meet you, Brad,” Tim replied.

Mistress Fiona spoke up, “Mistress Delia and I have some shopping to go do before our dinner reservation.”

“Brad, Timmy, you will have your dinner here and be ready for Mistress Fiona and I when we return from our dinner plans. Am I understood?” Mistress Delia asked

Timmy answered fast, “Yes, Mistress. Of course.”

“Yes, Mistress,” Brad added.

Mistress Fiona went on, “Brad, you will make dinner for yourself and Timmy. I will call as usual about twenty minutes before our arrival back here.”

“Yes, Mistress Fiona,” the submissive Brad responded.

“Bye, pets,” Mistress Delia purred, as she waited at the doorway for Mistress Fiona. A few moments later, Mistress Fiona walked up to her friend and then waved as she said, “See you soon, pets.” A moment later, the two lovely Mistresses were gone.

A short time later, Timmy joined me in the kitchen and we made and ate our dinner there. After we finished our food, we cleaned up after our meal and put everything away where it should be kept. Once the kitchen was once again immaculately clean, as Mistress Fiona always expects it to be, Timmy and I went to the small living room area where I was allowed to spend my down time. I had a smallish television there and we watched a couple shows while I waited for Mistress Fiona’s call or message that she and Mistress Delia had finished their dinner and were on the way back to the house.

Unfortunately for both Timmy and myself, we were both caught up in our television shows and neither of us noticed the text message or phone call on my cell phone from Mistress Fiona. We both realized, when we heard the unmistakable sound of the click of the front door lock, and then the door open. The soft clicks of my Mistresses high heels were unmistakable on the hardwood floor as she walked across the room. I then heard Mistress Fiona as she said, “Brad had better have a damn good reason that he didn’t answer my text message or phone call earlier.”

I quickly scrambled over to the doorway. With my head down, I mumbled, “Sorry, Mistress. We …..”

“I don’t want to hear excuses,” Mistress Fiona told me in her soft but commanding voice that told me that I was going to be in trouble later. “Get upstairs and get ready for your training tonight.”

I groveled, “Yes, Mistress. I’m on my way, Mistress.”

“Sorry, Mistress,” Timmy said softly to Mistress Delia, a moment later.

Timmy and I quickly went up the stairs and went to Mistress Fiona’s office on the second floor, while the pair of lovely Mistresses talked and giggled with each other in the large family room.

Nervously, Tim and I got prepared in the office. We both quickly undressed, with the cages still securely attached to our less than adequate cocks. Silently, we stood there in the dimly lit room, our hands held behind our backs, and our heads lowered submissively. It was probably my nervousness, but it felt like the pair of lovely Mistresses kept Timmy and I waiting a lot longer than normal. As much as I thought it in my head, I wouldn’t dare question my Mistress Fiona, about the time. I had already gotten in trouble for too much television time and consequently not being prepared when my Mistress arrived home. If I then questioned Mistress Fiona on her timing, I would certainly get into even more severe trouble, and I was not going to walk into a mistake like that willingly.

Finally, Mistress Fiona and her good friend Mistress Delia made their way up the stairs. The clicks of two pairs of high heels on the hardwood steps got louder and louder with each second and each step that passed, until the door opened and the pair of lovely Mistresses walked into Mistress Fiona’s private office area.

Mistress Fiona paced the room for a short time, while Mistress Delia took a seat in the comfortable padded leather chair. Then, my Mistress Fiona spoke, “Brad, my little pet. Since this is your last training session, I thought that a training session as close to the real competition as possible would be best.”

After a short pause, Mistress Fiona took the seat in the comfortable padded chair, while Mistress Delia stood. Mistress Delia then explained, “Therefore, rather than bringing one of my bull lovers over to help with the training, I instead brought one of my subbie pets, which is how the Mistress Olympics cock stroking contest will run, subbie against subbie, both being stroked by the opposing Mistresses.”

Once again, my Mistress Fiona spoke up as she told me, “I’m sorry to tell you this Brad, my pet…. But, you are at a clear disadvantage in this contest. You see, my dear friend, Mistress Delia had just told me that Timmy here had just cum this morning, while you haven’t cum since your last training night, two nights ago.”

Mistress Fiona purred into my ear softly as she told me, “I hope you are UP for the challenge, my sweet subbie.”

“Yes, Mistress. I’ll do my best,” was all I could manage to reply to my Mistress Fiona.

Neither of the lovely Mistresses said anything more after that. Silently, the two gorgeous Dommes handed each other the keys to their subbie’s cock cage. Mistress Fiona walked over to Timmy and she used the key provided by Mistress Delia, and she unlocked his cock cage. Mistress Delia did the same with my cock cage, as she used the key that Mistress Fiona had given to her. A few moments later, both Mistresses had the cocks released from confinement and they were ready to begin.

Mistress Fiona readied her timer, and she called out, “3… 2…. 1…. Begin!”

At the announcement to start, both Mistress Fiona and Mistress Delia grabbed the cock before them and they began to stroke. Faster and faster they both stroked.

Mistress Delia stroked harder and faster as she whispered into my ear to “Let it go. Cum for me.”

A short distance away, Mistress Fiona had whispered into Timmy’s ear a very similar order, which I could only partially hear.

I fought against it as Mistress Delia worked on my less than adequate prick. I thought about anything except pleasure and cum, as she continued her erotic assault on my dick.

Mistress Fiona called over to me, as she worked on Timmy’s cock, as she told me, “You hold back, Brad, my pet. I know you can do it. Don’t you dare cum!”

Hold back, I did. I focused my thoughts on work, puppies, anything except the sensual pleasure that coursed through my body.

Meanwhile, a short distance over, Mistress Delia called out to Timmy, “Timmy, you better hold that cum back. I just let you shoot for me this morning. Don’t you dare shoot again! You can hold it. Hold that load of cum back.”

Both gorgeous Mistresses kept up their erotic touches as they each stroked, rubbed and massaged the pet boy’s inadequately long but hard cock. Mistress Delia worked her magic on my prick, while I struggled my best to follow Mistress Fiona’s orders and I thought about anything except her erotic touch. Similarly, Timmy seemed to struggle to keep himself composed as my Mistress Fiona worked on his small dick. I could see it in Timmy’s eyes that he was losing it, that even though Mistress Delia had made him cum earlier on this same day. Mistress Fiona’s touches were obviously having the desired effect and he was about to cum.

As Timmy struggled, it just increased my resolve and I held back, even as Mistress Delia worked even harder to make me cum first. I could see Mistress Fiona’s big bright smile as she stroked Timmy harder and faster, and finally, he let out a loud gasp, as he shot his big wad of cum all over my Mistress Fiona’s perfectly manicured fingers.

Even though Mistress Delia still kept up her erotic attack on my useless prick, I still held back my load of cum, and didn’t waver. Mistress Fiona stepped over and she purred into my ear, “You may cum, my pet.” At my Mistresses’ command to cum, I did cum and shot a nice wad of jizz all over Mistress Delia’s fingers and hand, as I panted and sighed after I blew that load of cum that I had built up.

Mistress Delia got up and she walked over a few steps to her pet, Timmy. She put her hand and fingers in front of his mouth and hold him, “You lost, pet. Clean me up.” Obediently, Timmy did as he was ordered and he licked Mistress Delia’s fingers and palm clean of every drop of cum on them. “Go clean Mistress Fiona’s hand too,” Mistress Delia ordered. Timmy did as ordered and he scurried over to Mistress Fiona and he took her hand and fingers and cleaned up her stroking hand as well.

“Your pet did very well, girlfriend,” Mistress Delia said warmly as she gave my Mistress Fiona a hug and a quick kiss on her cheek.   The more mature Mistress turned to her pet Timmy and told him, “It’s time we said our goodbyes and went back home.”

Timmy bowed and said, “Yes, Mistress.” He turned to me and shook my hand as he said, “Congratulations, Brad. I think your training is about done and you are ready for competition. Good luck.” Timmy then turned to Mistress Fiona and bowed as he said, “Thank you for having us over to help with the training Mistress.”

“You’re welcome. Good night, pet,” Mistress Fiona said with a smile to Timmy. As she turned to Mistress Delia, Mistress Fiona smiled again and said, “Good night, girlfriend and thanks for the training help.”

Finally, it was my turn and I said, “Thank you, Mistress Delia. And thank you, Timmy. I appreciate both of your help getting ready for the Olympics.”

At that, Mistress Delia and her pet, Timmy got ready to leave. I saw them down to the front door and I let them out. I closed and locked the door behind them, and then I returned to Mistress Fiona’s office.

Once I returned upstairs to Mistress Fiona’s private office, I quietly went inside and closed and locked the door, as my Mistress desired. I saw that Mistress Fiona was in her comfortable padded leather chair, relaxing. I stood before her, with my hands held behind my back and my head lowered.

“I am ready for my punishment,” I said softly with my eyes still lowered.

Mistress Fiona picked up my head with her delicate finger and looked into my eyes. She told me, “This was your last training night, pet, and you did very well against Mistress Delia’s pet. I am very proud of you for that.”

“Thank you, Mistress,” I said proudly.

My Mistress then went on, “Therefore, I think I will give you a reprieve, and you will not be punished tonight.”

“Again, Thank you, Mistress,” I said happily. “But, Mistress, I messed up earlier about my television time and being ready for you and your arrival. That was wrong, and I deserve to be punished for that inconsiderate behavior.”

Mistress Fiona smiled. “Thank you for your honesty, pet,” she purred at me. “Very well, I agree that you do deserve to be punished for your lack of obedience being ready for my arrival, and you do deserve to be punished for that.”

“Yes, Mistress,” I answered softly. “As you wish, Mistress.”

Mistress Fiona opened one of the drawers to her desk. She pulled out two large objects and she showed them to me. One was a large paddle and the other was a strap-on dick. My Mistress told me, “Since you did so well on today’s training, I will give you the option of picking your preferred device.” She paused and then said, “Think wisely and choose a device carefully.”

“Mistress, I pick the paddle,” I told Mistress Fiona. I knew that the paddle would be painful on my butt, not nearly as bad as being fucked in the ass by the very large and thick strap-on.

Mistress Fiona smiled as she picked up the paddle….

A moment later, she put the device away in the drawer. She picked up the strap-on cock and then walked out of the room. “Oh… Pet…. Now, don’t look so sad. I never said that I would USE the device you picked on you, just that you would be picking out the device,” Mistress Fiona explained. “What I didn’t state so clearly was that I would use the OTHER device from the one you picked. Had you wanted me to use the paddle on you, you should have picked the strap-on.”

“I understand, Mistress,” I gulped nervously. I had wanted Mistress Fiona to use the paddle, not the strap-on, and therefore I walked right into the dilemma myself.

Nervously, I waited in silence as Mistress Fiona walked to the bathroom. Her steps echoed loudly off the hardwood floors with each high heeled click. Even though it was just a few minutes of time, it felt like an eternity as I waited, and I knew what would happen upon my Mistress’ return. The office door creaked open again and Mistress Fiona stepped back in with a huge smile on her pretty face. She still had on her tall black stiletto high heels along with a white tank top and black booty shorts. Over the booty shorts, she had the strap-on harness fixed in place with the extra thick and long dildo standing out proudly in front of her feminine form.

“Squat down and suck my cock,” my Mistress ordered.

I did as I was commanded and I dropped down into a squatting position in front of the desk. Mistress Fiona stepped over and I took her strap-on into my mouth. I licked and sucked on the long, thick dildo and got it wet with my tongue and lips.

My Mistress told me, “That’s right. Get it wet. Do a good job. It’s going in your ass as wet as you make it.”

That implied thread made me work even hard to get the dildo completely lubricated. Greedily and hungrily, I licked and licked on the dildo, as I got every bit of it wet.

After several more minutes of my licks and sucks on her huge cock, Mistress Fiona told me, “Stop. Now turn around and bend over the desk.”

Without having to be told what was about to happen, I knew what my Mistress had in store for me. Slowly and nervously, I did as I was told.

“Faster,” Mistress Fiona commanded as she didn’t like the speed that I moved.

I gulped, “Sorry Mistress. I’m going faster.”

I did as I was told, and I sped up and moved into position. My ass faced Mistress Fiona, while I bent over her heavy oak desk.

Mistress Fiona grabbed my hips and she maneuvered that large dildo right to my ass hole. “Get ready,” my Mistress told me.

A moment later, Mistress Fiona pushed the intrusive length of dildo into my ass. I gasped and groaned as the cock forcible pushed its way deep into my ass, inch by inch. After my Mistress had pushed the object as far into my butt as it would go, she backed it up almost the whole way out, but she left the head of the dildo inside my ass. Then she pushed it back inside my butt, this time faster and in a more fluid, single thrust motion. I groaned even louder this time as I shifted around and tried to make it more comfortable for my ass to accommodate the intrusive object.

Mistress Fiona backed the dildo all the way out of my ass. She squirted some sex lubricant on the shaft and she had me spread it around on the cock. Then, a moment later, she inserted the artificial dick back inside me. This time, my Mistress wasn’t at all slow or gentle in her first motions, but she grabbed my hips and she forced and thrust her shaft deep inside me. Quickly, Mistress Fiona found her rhythm and soon, she pumped that cock in and out of my ass hole with a fast and furious sexual pace. Again, I moaned as I gripped the massive oak desk for extra support.

It didn’t take too many more thrusts into my ass by Mistress Fiona’s huge dildo before I squirted my cum all over myself and the hardwood floor. The ass fucking by my Mistress had made me shoot a huge load, much more cum than my usual tiny drip. This was an actual puddle of cum under my dick.

Mistress Fiona smiled and told me, “There you are, pet. Now, you got to cum too.”

“Thank you, Mistress,” was all I could say in response. My Mistress knew that this wasn’t really how I would have prepared to cum, but I knew that this would be the best that my Mistress would give me, so I knew to be glad for what I could get, and not expect more.

My, even tiny while erect, dick shrunk back even smaller than normal, after I had cum. My tiny member made me even more embarrassed as it wilted away. Mistress Fiona, her hard strap-on dildo still in place between her long legs, went over to her desk and she grabbed my cock cage. She picked up the device and she took her time as she reattached all the components and then closed the cage up to lock my dick away. She turned the key and the lock clicked in place and I knew that meant that my cock would then be locked up until the start of the Mistress Olympics Cock Stroking contest began.

With my cock locked up, Mistress Fiona then told me, “Now, clean up that cum you dripped on the floor, before it messes up my hardwood floor.”

“Yes, Mistress,” I said softly as I got up to the bathroom.

Mistress Fiona snapped, “Stop! I didn’t tell you to get anything to clean. Your tongue, pet!”

I blushed I returned to my Mistress’ desk and then dropped to my knees. I used my tongue and lapped up all the drops of cum from the hardwood floor. Back and forth I went as I licked up all the sticky, milky baby batter from the floor. Mistress Fiona watched and made sure that I swallowed every drop before I bent back down and licked up more of salty semen. After several long minutes, my Mistress was happy with my cleaning job, and only then she allowed me to go to the kitchen and get some hardwood floor cleaner to return the floors to their previously pristine condition.

Once I had completed the floor cleaning, then Mistress Fiona told me, “One last thing to clean, pet. My cock needs to be cleaned!”

“Yes, Mistress,” I replied. “Of course, Mistress Fiona.”

Mistress Fiona didn’t have to verbally tell me how she wanted me to clean the strap-on cock. She made her intentions very clear as she pushed down on my shoulders to make me squat down and then she thrust the dildo forward toward my mouth.

She wanted me to clean the dildo ass-to-mouth. Even though I was hesitant at first, I did as I was ordered and I took the dildo into my mouth and completely cleaned it up. Back and forth I went with my tongue and lips as I washed off every inch of the massive shaft and cock head.

“It doesn’t look very clean yet,” Mistress Fiona scolded.

“Sorry, Mistress,” I panted as I continued to work on cleaning the huge dildo.

On I went as I licked and sucked the artificial dick clean. Mistress Fiona thrust the device further into my mouth to make clean faster and more vigorously. I cleaned and cleaned until I licked off very bit of the phallic device.

“That looks better,” my Mistress said with a soft smile.

At that, Mistress Fiona sat down on her comfortable leather recliner chair and she removed the strap-on cock and put it away.

“You may relax for night now, pet,” Mistress Fiona told me. “I’m retiring to the master bedroom.”

“Good night, Mistress,” I responded. “See you in the morning.

The end of this part.

More to come…