My boss, so strict and demanding at work, used my mouth for his pleasure. All the sensations go through my head, anguish, fear, and embarrassment but also pleasure.
My boss then takes my face in his hands and kisses me. My breath must smell of cum and all the cocks I’ve been forced to suck. He doesn’t seem to mind that.
In my ear the voice of Master Paul speaks to me again. You spent your first night as a prisoner. You were great and the Masters had a lot of fun with you. You will be freed from the Pillory and I will take off the collar and the hood. Your first task will be to rectify your outfit and make it as less wrinkled as possible. We will have a drink at the bar so that you find all your means.
Once released, I pull up my pants, adjust my tie and close my jacket. Master Paul supports me and we go to the bar. He sits me down on a stool. My head is spinning a bit. The other prisoners are also released. Master Paul asks me to sign a document in which I agree not to reveal to anyone what happened tonight. I agree and sign it.
It is 4 AM when we are again in Master Paul’s car. On the road back home he tells me that we can now be just George and Paul again.
How did you enjoy this night he asks me? I tell him that there were times that were difficult but that in general I enjoyed it. But I tell him that seeing our boss in this place makes me uncomfortable. Paul tells me that his involvement in society is no accident. He has known the boss for a long time thanks to this private club. As he had just been free from the army, the boss offered to come and work for him with the main task of seducing me and confirming his feeling that I was a lover of gentlemen in a suit and tie but above all of bondage . The news leaves me with a weird impression in my head, I don’t know how to take the news.
We arrive at my house and Paul parks on the side and stops the engine. He kisses me for a long moment. I’m going to get out of the car and Paul holds me back by the arm. Do you want us to spend the next night together he asks me? If you want I let you pick up the rest of the night and see you in the late afternoon?
With pleasure Paul I answer him.
Perfect, check your emails, I’ll send you my instructions. I get out of the car and Paul drives off.
A quick shower and I fall to sleep.
When I wake up I check my emails and only pay attention to Paul’s.
It is written that I must take with me two suits, tie and whatever it takes to be a gentleman. I also have to take a toiletry bag. I’m expected at 5 p.m. I have to go to Paul’s house in a suit and tie, of course.
So that doesn’t give me a lot of time. Shower, shave and get dressed. I chose a light brown suit, a blue silk print tie, and brown shoes. I choose two other different outfit. It’s time to go if I want to be on time at Paul’s. It is 4:55 pm and I am in front of the door with my luggage. Paul opens the door and greets me with a big smile. Always perfectly dressed in an elegant suit, he kisses me with passion.
I’m so glad you accepted my invitation. He takes me to a guest room, make yourself comfortable and use the wardrobe for your clothes. See you in thirty minutes. I open the wardrobe and find that there is a tuxedo and leather outfit already hanging. I join Paul. He gets straight to the point. You are mine until tomorrow morning. Tonight I have a guest coming for dinner and you will be our butler. I know you’ve never done this but I’m counting on you to be on top of it, you’ll be punished for any mistakes you make while on duty. A chef will be arriving for the meal in a few moments you will help him set the table and prepare for the evening. My guest arrives at 7:00 p.m. so at 6:00 p.m. you will change and use the tuxedo you must have seen.
At 6 p.m. as agreed, I dress in the tuxedo. The tuxedo is perfectly my size and looking at me in the mirror I feel precum in my pants.
At 7 p.m. someone knock at the door and Paul orders me to go and open it. I go to the door, open and it’s my Boss again in front of me. Good evening Georges he said to me.
The evening goes by quickly and I try to do my job to the best I can.
Coffee is served and Paul tells me: you have 15 minutes to change and introduce yourself to us in suit and tie. When you are ready you will come back to us and put yourself at attention. I walk quickly to the bedroom and put on a black suit, black shirt, black tie, and black shoes. I look at myself in the mirror and I am hard again. I come back to the living room and stand at attention in front of my Boss and Paul. While I’m away the table is filled with different kinds of shackles, , blindfolds and gags. I am impressed and my cock tightens more in my pants. Paul in his dominant voice said, Master Georges is at your disposal, tied him as you please.
My boss first chooses a shoulder to wrist restraint and places it on top of my suit. He closes it tight and I already know this position is going to be painful. He then puts on a spandex hood on my head that leaves only my mouth open. I am taken by the tie and taken to what I guess is Master Paul’s dungeon. I am placed in the center of the room and order to kneel down.
Directly a cock is introduced into my mouth, Make me come, says Master Paul. I start to suck this cock and apply myself to satisfying my Master. My boss is now behind me and he opens my shirt and takes care of my tits. Caresses, twists, everything goes. In my pants I feel the pre cum on my penis. It is obvious that Master Paul wants to make the pleasure last and he is holding back as long as possible. He finally explodes and I greedily swallow his hot cum. When he is satisfied he withdraws and directly the cock of my boss takes the place. Master Paul is now behind me and continues to work on my tits, he goes down with one hand and opens my pants, brings out my cock, which is hard as a rock. My boss comes in my mouth, and I swallow again.
I am put to my feet and someone takes the restrain off my arms and neck and also the hood. Undress yourself completely prisoner said to me Master Paul. I find myself naked in front of two elegant men in suits and ties and I find that very humiliating.
A heavy duty collar is placed around my neck and my head is now immobilized, then comes a steel hook in my ass. A rope is stretched between the collar and the hook. At this moment enter the chef in the dungeon he is dressed in leather from head to toe. Low rise jean, dress patrol boot, uniform leather shirt, officer belt, Sam Brown, a biker cap and CHP motorcycle gloves. From his belt hangs a baton. There is also a pair of handcuffs.
I see in the mirrors the image of my two Masters in suits and ties, this athlete in leather and me naked in the middle. The chef places leather restrains with rings on my wrists and ankles. My two Masters take me by the arm and lead me to The St Andrews cross that I know. They tie me up with my back towards them. Master Paul tells me: you made mistakes during the service and you are going to be punished. It will be in various ways.. You will have to count every stroke you received out loud and thank the giver each time.
In the mirror I see the chef heading towards the prop wall. He chooses a simple whip and a riding crop. My whole body is shaking and trying not to panic. I didn’t had any impact play before. The chef begins his work with the whip. My back is hit and I’m counting every of it. I say as loud as I can Chef Thank you Chef. And it goes on until 20. Then my butt gets 20 strokes with the crop. At the end my back and my ass are on fire but I had pleasure. Master Paul comes up to me and kisses me. He gently massages my back and the pain subsides.
My boss removes the steel hook, and the heavy duty collar. Then he unties me from the cross and takes off the leather bracelets. He tells me you have 15 minutes to go to the bedroom and put on the leather outfit that is in the closet. I comply and quickly goes back to my Masters in the dungeon dressed in leather from head to toe. I stand at attention in front of the 3 men. The chef puts the leather restrain back on my wrists and ankles. I fear another passage on the cross but it is towards the table that they direct me. They make me lie on my stomach and tie my wrists and ankles. I am immobilized. They place plugs in my ears, a scream hood on my head and mittens on my wrists. I hear Master Paul’s voice in my ears. You are ready for the rest of the night. I’ll meet you tomorrow morning. And then the silence., I sweat, I lose track of time, cramps keep me company but to my surprise I have a hard on. The smell of leather, which I hadn’t really noticed, pleases me more and more. Impossible to sleep in this position despite how tired I am.
After I do not know how long Master Paul enters the dungeon. He takes off the scream hood and I can see us in the mirrors. He’s also in leather with a tight-fitting chaps and his chest is bare with just an English Top Harness. I realize this is the first time I have seen my Master’s chest. He drops my leather pants he stands behind me and begins to fuck me. He takes his time and goes deeper and deeper in me. I am hard. Master Paul comes, he remains in me and begins to masturbate me, and it is my turn to come.
We stay a while without moving to take advantage of the situation. Master Paul withdraws and frees me from my bonds. He hugs me and kisses me.
Paul leads me to the bathroom so that I can take a shower. Before leaving Paul tells me that he is not going to put me in chastity this week, but that I have to place it every night. He gives me an appointment next Friday if I wish.
Yes I want it, Master I answer him.
To be continued …