I first got acquainted with him through an overseas master who was visiting Singapore. Unfortunately, the previous 2 doms + 1 sub session had to stop abruptly as we were late for the hotel check out. Since then, he had been busy traveling due to his work, and it was only recently that he could confirm his schedule to meet up.
He had to change the timing for an emergency meeting at work to accommodate our session. It was sure nice to see him in his executive shirt and slacks, in striking contrast with the casual polo tee and blue bermuda shorts he wore previously on that weekend. Our previous discussion centered on a scene involving helplessness and cum control:
Me: Let's role play a scene where you're kidnapped and tortured for cum control. I'll do my best to edge you and tease your cock and nipples, but you cannot beg to cum. If you beg to cum, then I'll milk you dry at least twice.
Him: Fuck. I've never had an experience like this before. Don't think I meet any doms who can milk me dry or give me a ruined orgasm yet. Fuck! I'm hard just thinking of it. I can feel the difference when you tease me, versus when the other guy touches me. My legs goes weak when you play with my nipples and cockhead. You really know which buttons to press.
Me: Yes, I'll play and torture your nipples, and make you moan like a slut with a rock hard cock. I'm going to stroke your dick and give it some CBT. Only when I'm satisfied, then you are allowed to cum!
The benefit of meeting a familiar face was that we could jump straight into play and waste no time on ice-breaking. I offered him a glass of water, but he didn't want to drink, so I led him directly to my bedroom.
Once behind the close door, I positioned him against the wall, placed a blindfold over his eyes, and locked his hands together behind his back with a pair of wrist cuffs. I started by rubbing his nipples through his shirt, causing him to moan softly. Then I reached down to grab his crotch. I was surprised that his cock was already rock hard. He hadn't cum for two days so he must be very horny.
He reminded him of the game we were going to play. It's called "Are You Man Enough?" For the next 90 minutes, I would be playing with his nipples, teasing him, making him moan and giving him a hardon. I would stroke his cock gently and some light CBT on him.
In order to pass the test, he has to prove that he is a real man by controling himself, and not cum until permission is given. At the same time, he has to moan like a slut to score points. Only when both criterias are fulfilled then he may be allowed to cum at the end of the session.
I began by chaining his feet together, and continued caressing his chest and nipples. He kept a coin in his left breast pocket and I was unable to stimulate his left nipple. After removing the coin, I told him I would punish him later for attempting to hide his nipple.
After stroking his hardon several times, I undid his pants to reveal his grey 2(x)ist boxer-briefs. His rock-hard cock was peeking out from the elastic band of his underwear. I noticed drops of precum leaking from his dick. I gave his balls a light slap and that made him jump.
I released his hands that were locked behind his back and removed his light blue executive shirt. He was repositioned onto the door frame in just his underwear and his arms in a crucifix position. A collar was added to his neck. I marked his bare chest with the words "Slut Boy" as a symbol of my ownership over him. After teasing his nipples constantly, by now, there was a visible spot of precum stain on the right corner of his boxer-briefs.
Using a cane, I gave him some light beating as a punishment for forgetting to remove the coin and causing me difficulty in playing with his nipple earlier. He moaned as I alternated the sensation between pleasure and pain - caressing his body sensually with my gym gloves and switching to light caning on his torso. He whimpered like a child in pain when I beat his upper body.
"Now you know why I offer you some water before we start?" I said. "Because you will be moaning and groaning throughout this training!" I continued. He nodded to acknowledge.
His limits were no kissing, no oral and no anal. But that doesn't stop me from stimulating his perineum (the area between his scrotum and anus) by placing a vibrating ball between his thighs. He wriggled and moaned too much, so I took the cane and disciplined him. I released the grip from his wrists and ordered him to play with his own nipples. Using the vibrator wand, I continued to tease him, sending waves of vibration to stimulate his cock, causing him to leak more precum.
My phone rang. It was a message from my helper boy. He had arrived and would be helping me to torture this gym-fit slut boy. I told him to hold the vibrating ball between his legs while I went out of the room to bring the other boy in.
The other boy helped me to secure slut boy's hands to a pole. We placed the sound muffle over his ears so he would not be able to listen to our conversation. I handed the vibrator wand to the helper boy and instructed him how to use it to tease slut boy. I slid on the scrub gloves and began caressing the fit slut boy's torso. He worked out regularly and his arms and thighs are really big and firm. We continued to play with his nipples, making sure he was leaking precum constantly.
We brought slut boy to my bed and had him bound up in the spread eagle position. We shared his torso and each of us took one side of his body to play with. We each took one of his nipples to tease and suck, ensuring that he was moaning non-stop.
With the toiletries I took from the hotel where I met slut boy, I poured a generous serving of body lotion onto my palms and edged him continuously for 20 minutes. Throughout the cum control, my helper boy was playing with the slut boy's nipples. Looking at my clock, I knew I was running out of time as slut boy had to return back to his office for meeting. I removed the ear muffle and told him that he had exactly 10 seconds to cum.
Me: Do you want to cum, boy?
Him: Yes, Sir..
Me: Okay, I'll give you 10 seconds to count. Are you ready?
Him: Sir.. Yes.. Sir..
I began to speed up as I countdown from 10. He was breathing heavily and struggling with all his strength. But he wasn't able to cum when I had counted to 0. Seeing how horny he was, I decided to give him one more chance.
Me: Okay, one more time. If you don't cum before I count to 1, you won't get to cum. 10.. 9.. 8.. 7.. 6..
Before I could count to 5, he was spraying his cum juice all over my hands, my bed, his chest and lower torso. It was a grand fireworks to end the training for this slut boy.