OCS Cadet Cumming 9 Times

My last blog post reminded me of this session that happened some time ago. 

Yes, I wasn't telling a tall tale when I wrote the title of this blog post. This was probably one of the most intense and tiring, yet fun and satisfying sessions I ever had. I have never known anyone who can cum so many times but this boy is really awesome.

When he contacted me, he was already super horny as he had not cummed for 5 days. He kept texting me to ask if I could meet him early as he really needed to relieve his blue balls. But as I was busy with work, he had to be patient and wait for me to edge and milk him. 

After several failed attempts at scheduling a session, we finally managed to meet up that Saturday afternoon. It was more than a week since he released his load. Being young, naturally his ranging hormones were causing him a lot of agony. 

The big day came and I booked a hotel room specially for our session. Being unfamiliar with the area, he went to the wrong hotel and was late. Though it was his first bondage session, I told him that I have a pet peeve on lateness, and I won't go easy on him as he had to be punished for making me wait for more than half an hour.

When he arrived, I was surprised to find out that he was fairly tall, only slightly shorter than me. He's easy on the eyes and has broad shoulder and a nice big chest. A pair of black frame glasses sat above his nose, giving him a geeky look.

I told him to remove his berm shorts. To my surprise, he was wearing a pair of grey tights that wrapped tightly around his muscular thighs. The tights hugged his bubble butt firmly and I couldn't resist the urge to squeeze and slap his ass.

He was ordered to change into his Officer Cadet School (OCS) red singlet and red shorts. I was enjoying myself by simply standing there watching the young meat changed as per instructed.

Once he was in the sexy red OCS attire, I pinned him against the wall and bound his hands together behind his back. His cock was super excited and was standing at full attention. I grabbed his hard rod and squeezed it, attempting to soften it so I could trapped his 6-inch boner in the CB6000 cock cage.

The boy likes bondage and it was hard to control his excitement. I put a neoprene hood over his head and sealed him into darkness. Once he was in the sub zone, it became evidently harder to squeeze his dick into the cock cage. I tried several times before giving up.

That's when I decided that if I couldn't deny him of an orgasm via chastity, I would make him feel worse by milking multiple ruined orgasms from him.

I had him lie spread eagle on bed while I tied his hands to the side and his legs to the bottom of the bed frame. Lubing up my finger, I slowly massaged my way into his hole. His ass was tight but I took my time to gently loosen him up. Once he was ready, I probed his hole with an Aneros. The moment the prostate massager went in, his cock was throbbing non-stop.

Then the edging started. I would jerk off his cock and gave it a few light slaps on his cock and balls to prevent him from cumming prematurely. After several times, he was moaning uncontrollably. I knew he would erupt soon and I managed to stop in time to watch his cum juice flowed from the tip of his cock onto his lower abdomen.

His cock remained rock hard and it was a sign that the little fellow was craving for more. After 30 seconds of rest, I continued on the routine of edging follow by light CBT until I was able to milk another 2 ruined orgasms from him. 

Total count now: 3 ruined orgasms

I felt that it was too easy for him to cum so I took a shoe string and tied it around his cock and balls. His dick looked very beautiful with the veins popping out. I removed the Aneros and replaced it with the small size anal beads. Again, I applied lube on the ass toy and slowly poked it into his tight ass.

I went on to edge him. This time the strokes were more rapid and he was grabbing onto the pillow as I attempted to milk another load from him. Soon, his body was jerking and it was a sign that he was close to climax. I pulled away my hands and heard him groan as another load of ruined orgasm was forced out from him.

"When the last time you cum before meeting me?" I questioned him. "More than a week," he murmured. "How many times shall I milk you today?" I asked, and he replied, "7, Sir." "Then I will milk you 10 times today!" "Yes Sir," he said.

I released the cuffs that had held him securely bound to the bed and guided him to stand facing the wall. Taking the coil of rope on the dressing table, I wrapped it around him in a simple Shibari style around his torso. I made effort to ensure that the rope work was tight to arouse him but not too tight to cut off his blood circulation. His cock was semi-hard and leaking precum. I licked his nipples through his red singlet, forming two wet patches on his chest.

His cock was throbbing non-stop, he was simply too excited from being rope bound. I gave his manhood a few light slaps and it jumped. He seemed to have a very sensitive boner. I stood behind him and sniffed his neck while grabbing onto his chest. I guided his hands downwards and let him fondled my hardon as I proceeded to edge him again. 

This time, I managed to find out the most sensitive spot on his cock. He struggled really hard, I had to hold on to the Shibari to prevent him from breaking free. I carried polishing his dick in a circular motion with silicone lube until he cummed again. 

Total count now: 5 ruined orgasms 

I guided him to sit close to the side of the bed and began slow teasing his cock in a circular motion again. His body kept jerking as I continue to edge him. I couldn't believe that his dick was still rock hard after 5 ruined orgasms. 

I went on to finger him, and realised that the anal beads had come out while he was struggling during the 5th ruined orgasm milking. 

The 6th ruined orgasm happened when he was seated facing me. He was on the edge and he cummed as I was fingering his hole. 

I continued to play with him by rubbing our hard cocks together. He struggled a lot and almost cum, all the while moaning and begging that he's going to cum. 

The horny boy was lost in his own sub space and was moaning so loadly forgetting that we were at a hotel. When asked how many time he had cum, he replied, "Five." But in reality, it was six. 

I was playing with his left nipple as I watched his 7th cum load dripping slowly onto the carpet. The housekeeping staff would have a hard time cleaning up the room tomorrow. 

I checked if he required a break for water but he replied No. When I asked if he wanted to cum some more, he eagerly said Yes. And his semi hard cock immediately turned fully hard again. 

Standing behind him, I proceed to edge him again. Changing position to stand facing each other, I grabbed his cock and rubbed it between my legs and alternate with rubbing our dicks together. 

The 8th ruined orgasm came while I was fingering his hole and I managed to force out a drop of juice from him. 

Finally, after more than 3 hours of non-stop edging, dickhead polishing and ass play, I was getting tired. I ended the session by jerking off his hard cock and milked a full orgasm from him. I kept stroking his dick until he was struggling with the post-orgasm torment. 

Grand total count: 8 ruined orgasm + 1 full orgasm