Last Friday Night, Master-Sir had me order some sandwiches and snacks from our friend’s pub. Something we haven’t done for a long while. As I called and talked to the wife, I had realized a major error on my part. I nor Master-Sir had really checked in on our friends in a long time. beyond visiting their family-owned business, we haven’t talked with any of them at all.
For newbies here, there is a local pub/restaurant here that is family-owned. The husband or His top employee would always deliver the pizza or whatever we ordered for the parties and I would give him a blow job as well as a cash tip. That eventually led to having His eldest son to being our almost exclusive delivery man.
The son is a nice kid. But like me, has some weight issues and so growing up, He has had some serious self-confidence issues. Not only would I suck His cock when he delivered, but other times, we would sit and just talk about life, sharing the trials and tribulations of growing up being overweight. I would offer my tips, from a female perspective, on gaining your self-confidence (especially when dealing with women), self-encouragement, and ideas that could help Him try to be the bigger man..
This year, with him nearing graduation and moving on to college, they started him on a split class schedule. Meaning most school days he spends part of the time doing His high school senior class stuff, then spends the last part of the day doing College prep work.
He was going to go to the university here for a major in business management. Then He changed that to a two-year degree when He and His advisor realized that growing up in the family business, He was probably going to be smarter than some of his teachers. And some of the classes for the four-year degree would not be of any benefit to Him.
Family Business
The parents are a wonderful couple we have become really good friends with. I mean ‘really’ good friends. Happily married since their college days. But when the wife discovered my submission, our relationship changed. She had a secret fantasy for a long time ot be a slave toher husband. Then she met a real slave and fantasy got real again.
In talking with her, I learned that she feared it was not possible this late in life and with a family?? Then you add the business into it, she cried a few days over that. However, I like to report that after a lot of talking and analyzing their world, we found a way for them to explore their hidden fantasy.
The husband has confided in my Owner several times, telling Him that this new relationship has probably saved the business and has made their marriage a lot stronger. In their new dynamic, He is The Boss and she is the loving, obedient wife. And together, they have been able to survive this COVID mess and still keep the business and their marriage.
So I guess I do need to keep talking more with them and even write more about them now that the old blog is gone!
For an update.
She knew from the beginning that I was giving her husband blowjobs as part of the tip. No problems because they have tried to be swingers, but it didn’t work out. So an occasional blowjob from a fluffy old lady? Go for it, sweetheart! Blowjob for an eighteen-year-old son? She tried to play the dumb mother and never asked about it. But she knew. She was able to let it go, just let Him enjoy the life experience..
In talking to her, I knew she had issues with it, but she also saw how her son started to change after each delivery to our house. She told me He always needed help with getting His self-confidence up with women. For whatever reason she noticed the positive change in Him once He started to deliver pizzas to our place! It works.
My Young Friend Has a Request
For this order, the wife said the son will deliver and she also asked if my Master could help Him with a little school/classroom project He had? Master-Sir agreed. So it was arranged that we would be His last delivery for the night. So no need to hurry after making the delivery. As she put it, “Keep Him as long as you need to get His project done”.
He needed to ask someone in business, just not the family business, some questions about real-world marketing and something about management. I had to smile. My Owner loves to talk shop like that and this just made Him very happy to be asked!
So just before the food arrived, Master-sir called me into His office. On a shelf, off to the side was a small plate and a glass from yesterday,. I should have caught that yesterday when I cleaned or tried to clean. When He pointed it out to me, I knew I was in trouble. Master-Sir from the first night i met Him, He and His friends warned me that He is really anal about His home always being clean and everything in its proper place. The house needs to be clean and organized the night before so we wake up to a new day and move forward. Last night I failed.
I apologized and said that would accept my punishment ( I always do) just as I heard the doorbell ring. ( I was saved!) I smiled knowing I was safe for now!
The eldest son and the one who now almost runs the entire restaurant himself most nights – was at the door. For various reasons, I named Him my “young Friend” I gave Him His first blowjob as an adult when he turned 18 (minus one or two years)and He has enjoyed learning sex from me ever since. Yes, I am very proud of that fact and like to mention it whenever I can!
I also smile thinking if only His lady friends really knew where He was learning it all from!!
Normally He delivers when we have friends over, so I take the food to the kitchen, then take Him to another room and suck His cock or let Him fuck me if He desires. Usually its a blowjob, then He leaves. This was different. I led Him into the dining room as I put the sandwiches in the kitchen.
There were three sandwiches and snacks, so I figured he must have brought one for Himself since they were going to talk. I brought the food and the drinks out as Master-Sir joined Him at the table. Having never joined us for a meal before, he was a little unsure how this worked as I sat on the floor between them. Master-Sir sensed His uneasiness and showed Him how to feed me from His plate. Doing this, I saw his already hard cock jump a little more in his shorts.
Again, He normally gets His blowjob right after the delivery. This time, Master-Sir was hungry, so we ate first, then He will get His tip, then they will talk. I was shocked, Master-Sir was hungry enough that he forgot, or I thought He forgot, that I needed to be punished.
Five minutes after they started to eat, they were talking when Master-Sir remembered my punishment. He smiled, then looked at me then to my young friend. Master-Sir offered to show Him how to properly punish a slave, or maybe a wayward future wife? He smiled at my Owner and agreed to the plan. I peered over to my Young Friend and saw that His cock gave another little rise in His shorts.
The rest of the meal was kind of a blur to me. I was trying to think about how this would go. My punishment, being naked and tied to a post. His watching and maybe even doing it. Shock Him? Disgust Him? Enjoy the show? How would he handle it? After eating, as I cleaned up, they went to the garage so Master-Sir could step Him thru the event. Show Him the post as well as the punishment tools.
when I walked in and knelt on the floor beside the post, i was uneasy, nervous, shaking a little at not knowing what was to happen. As they talked. Master Sir told Him that normally when the slave is punished, there is no sex afterward. it is punishment, not pleasure. So it’s up to Him, does He want the tip from the slave now or afterward? Do you want to use the slave now or after He punishes me?
He decided afterward. Master-Sir smiled as I was told to assume my position on the post. As Master-Sir strapped my hands in place above my head on the post, then had me step away from it so that my Ass was sticking out more. He was talking to my Young friend. Telling Him how, why, and what works best for the best effect, the most lasting pain.
He had some questions about punishment, sex, and such. He admitted to watching some BDSM movies online and actually liked watching the floggings. He just never knew if He could do it. I reminded him that I have plenty of ass to hit so no worry about doing damage!
The Moment
Master-Sir ignored any questions as to why I was being punished, just that I violated a very easy and very important rule. and no matter what, the slave needs to be punished.
Finally, they were ready. Master-Sir stood in front of me, holding the wooden paddle. This one is heavy and thick, it does not bend. it is used ONLY for punishment. As He held it for me to see it, He asked me why I needed to be punished? In aloud voice for both to hear, I explained why I was being punished. “I failed my owner. I am being punished for not keeping the house cleaned as I was trained.”
By this time, I already had tears in my eyes and i was apologizing for failing Him. He stepped behind me and had my young friend stand next to Him. They both were touching my ass as he told Him how to hit the ass and where to stand. How to wait for “the slave to respond as she was trained” meaning I will count the blows and apologize for failing my Owner.
Master-Sir laughed a little when He explained I was crying before the first swat and yet i had wetness down the inside of my leg.
I hear Him hand the paddle over to my young friend who commented on its weight and thickness. “Trust me, it hurts her worse than it hurts you!” Master-Sir told Him.
I could see Master-Sir from the corner of my eye, He was standing to my side and was watching as the virgin paddler lost His punishment cherry! Let me say that He had a mean swing that landed as it was meant to land in the center of my ass. making me jump a little more than usual. I counted “one” then apologized for failing my owner. I waited for the next. If this was “one” and he had 19 more, knowing His abilities, I knew each one was going to be that hard or worse. i was trying to prepare for the worst!
Master-Sir told Him to keep it up, don’t wait too long between swings and to make sure the slave does as she is supposed to (count out loud and apologize). if not, we start back at one!
At fifteen, I asked for a pause, not calling yellow, just a moment to get my breath and my balance. As I feared, He was still going strong! He resumed. Twenty was a tough one and I lost my balance on that one. I wanted to kneel but knew I needed to wait. I thanked Him and He even wiped the tears away.. I saw that He was smiling.
Seeing his cock was just about to rip out of His shorts, I smiled between the tears and asked if he plans to fuck me now? Telling Him that it will hurt for me but I was told men like to feel the heat on my ass after a beating? He looked at my owner in question. My Owner told Him i was right. Fucking a well beat ass is one that causes her pain but the pleasures for Him would be so worth the pain. He smiled “Really?”. Master-Sir smiled at the question, then excused Himself from the room. Reminding my young friend to not forget to unhook me and make sure that I clean everything up afterward.
I was having difficulty standing with my legs wobbling and my ass was still on fire. But to know He was wanting to fuck me like that! i made the effort to stay in place!! He unhooked me to get me into a better position. Doggie Style. Yes!
It was so worth the effort as I watched Him strip out of his clothes and to see that young, hard cock standing taller than i had ever seen it before. His smile was as huge as He went behind me and lined Himself up.
Feeling that cock at the edge of my wet pussy was heaven. I was wanting to feel that inside me no matter the pain. As it slipped in, I moaned. That feeling was short-lived as He pushed Himself into me full weight. Felling His cock inside me was heaven, but feeling the weight of Him and His pelvis hitting my sore, red ass, sent me into the orbit of pain. I know I screamed at the feeling.
I’m so glad His head was behind me because I know i screamed loud each time he pushed Himself into me and his body met my burning ass. When I did scream, I felt His cock inside me twitch a little more. “Thank You, Sir” was all I said. Well, that and a loud “OUCH” As I felt him pull almost out and push back in all the way and with His full weight.
I screamed each time followed frequently by a “Thank You Sir”. Until I felt the pulse and the last shove before He unloaded His cum inside my sloppy and wet pussy.
As he held himself inside me and the burning pain increased, I felt Him unlock the cuffs as we pulled apart and rolled on the floor. His cock was still standing tall and covered in our juices. My mouth watered as I saw my treat. Swallowing his cock as He tried to finger my pussy. Feeling my ass he told me it was cooling down.
Feeling Him in me, tasting the juices. I licked what I could before thanking Him for the punishment as well as the reward. That huge smile on His face told me everything i needed to know. When he stopped smiling, He told me “That Was Amazing”. The beating, the warm ass, and the fucking afterward were all a new high for Him.
He asked what it as like for me. I was honest in saying that He was better then i was expecting and that the fuck afterward was awesome. Knowing it was not supposed to be, I was being punished. But once in a while, you need to change things around for the benefit of the Master (Him). The pain was also very pleasurable because it made His cock so much harder. so I enjoyed the benefit from the pain.
Returning to the house, He and my Owner sat in the office for another two hours talking business. i sat on the floor near my Owner and leaned on His leg often. Not saying anything. Getting them refreshments whenever they needed them. Finally, before leaving, my Young friend needed one more treat. He wanted his usual blowjob.
I was happy to be used one more time for His pleasures. His cock wasn’t as hard as it was last time (smiles) but it was still a wonderful thing to put in my mouth and suck on! He came fast and tasted wonderful.
After He left and I finished my evening chores, my Owner even fucked me in my pussy before we curled up in each others arms and fell asleep!
I was a happy, well-punished and loved slave.