Making Him Cum Twice

I have waited for three weeks before we are both free to meet. He is a dragon boat rower with defined chest, pecs and arms. He is not the super muscular type, but more towards lean and muscular.

He was given the command to hold his cum for four days and that was the start of his training. He agonized over unable to jerk off as it was the first time he was told to hold his cum. By Day Three, he was asking if I could lock up his cock with my CB300 in case he lost his determination. Unfortunately (or fortunately as the story unfolded), we were both too busy to meet. It was such a pleasure to know that my sub was mental wrestling with his horny self for me.

He came to my place on Saturday morning in his red dragon boat singlet, short black running shorts and no underwear underneath. Perhaps it was due to the fact that we had exchanged messages on Whatsapp frequently, we were able to connect immediately. After a quick washed up, I led this boy into my room.

As soon as the door was closed and locked, I pinned him to the wall, fondling his nipples while checking on his pubic package. His cock was rock hard and it did not seemed like a small willie and this had me excited.

This was actually his first time being bounded and cum controlled by a Master. He told me that he had previously been in a BDSM session before but was made to do a strip tease, have his package inspected and fingered by the Master.

“Why are you hard?” I asked. And continued, “I did not give you permission to get hard, did I? For trying to disobey me you will be punished later. You will learn that your body and your dick belongs to me, understand?”

I grabbed my chair and told him to sit down while I proceeded to tie up his wrists and ankles to the sides and legs of the chair. Boy was wearing a loosely fitted singlet and that made the nipple play session easier.

We started with a 30-min session of nipple play without me touch his dick. As he had not cum for four days, his cock was constantly hard. I discovered that his right nipple was extremely sensitive and whatever I played with it he would moan loudly. I told him that the nipple play was just the appetizer of the session. I didn’t want to touch his dick because it’s his punishment for getting hard in the beginning without my permission.

I picked up my blindfold and ball gag and fixed them on him. By now his singlet and shorts had already been removed. I applied body lotion to his nipples, cock head and balls. The coldness from the air-conditioner had a cooling effect on the lotion. The moment the lotion touched his nipples he was moaning like hell.

I started with massaging his cock head. Boy was cut and his dick head was super sensitive. I began with a circular motion to his penis then slowly intensity and speed was added and soon I was edging my first timer. By the third edging motion, the boy was feeling out of control. When I finished my fourth edging motion, he was screaming that he could not control anymore. We were both helpless, as I watched him shot his load without me jerking his dick.

Of cos that was only the tip of the iceberg. Having not cum for four days, his cock continued to remain rock solid. I did some mental training with him, telling him to think about the boring things of work so that his dick would go soft. I attached the base of my CB3000 onto his balls. The boy was super horny and whenever his dick went hard, I would slap his thigh and told him to think about non-sexual things to cool his penis down. I managed to squeeze his semi-hard joystick into the cock cage and lock it before his horny thoughts made his dick pushed against the cock cage, sending a painful sensation to his dick.

I removed the blindfold to let him see the product of my creation. It was the first time he was caged and he was excited. His excitement also caused him to erect which made it actually impossible to do so as he was in chastity. I untied him and he was made to lie on the bed for our second round of training. I could tell that the boy was getting tired but his sexual energy was able to keep him going for another round.

He was tied spread-eagle on my bed. I began by fingering his tight hole. Boy told me that he had not been fucked since three years ago by his ex-boyfriend and getting fucked for him was painful. I took out my anal plug and applied a generous helping of lube. Once I figured out the point of entry, I began to push the butt plug slowly into his tight ass hole. I have to teach boy breathe control to relax his muscles so I can push the plug deeper.

But boy was a fast learner, soon, we were left with the final 3 cm of the plug. He took three deep breaths and when he was exhaling, I forced the remaining part of the plug in.

Our anal muscles contain a lot of nerves. The butt plug must have triggered a lot of his muscle nerves, cos the boy was moaning in ecstasy.

To add on to my pleasure, I used a vibrator to play on his nipples. Every time the vibrator touches his nipples, boy will be moaning non-stop. But boy struggled the most when I applied vibration onto his dick head and in between his muscular thighs.

After five rounds of edging, boy was already reaching beyond his limits. Since it’s our first session and he is a newbie to BDSM, I felt that he had performed so much better than some of the guys I had played me. I decided to play nice and allowed him to cum.

I applied a handful of body lotion onto his cock. The coolness of the lotion already sent his sensual nerves crazy. I began by doing a circular motion on his dick and the speed was increased and intensity was added.

Boy was moaning and begging me to let him cum while promising that he would do anything for Sir next time. He promised to be caged up prior to the next training and allowed photos to be taken. Hearing this really pleases Sir and I decided to reward him by jerking faster.

Boy shouted twice “I am cumming!” before shooting his massive load all over his body. Honestly I have never seemed so much cum before. His abs were all completed with his man juice and some even fell on my singlet, which I told him he will be punish next time for dirtying my attire.