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 

Submissive Bottom & Bound Jock

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Smooth, Muscular Sub

I'm not normally a fan of legs, but last night's session hit the spot. He is a mid-30s guy with smooth, hairless legs and sexy, muscular thighs. Nowadays, I start to workout more and I have a new found appreciation for guys who invest time and energy in body building.   

It was a session which we had planned for a long time. We spoke about it before my USA trip to San Francisco. He is a newbie, curious about the world of BDSM. I was hoping to be the first guy to introduce him to kink. But he had already scheduled to meet another dom and I had to be away. But he promised not cum for 7 days before we meet as a treat for me.

Yesterday was another stressful day at work. I was worried that I might not be able to complete my work before meeting him. During lunch, he texted to say that his regular fuck buddy had messaged him, asking for a quickie. Knowing he was extremely horny, I was expecting him to sneak out for the escapade. But he was quick to say that he had rejected the request and saved his load for me to milk him instead.

As I initially told him I might be late, he decided to head for a workout first. He said pumping iron would make him more horny, so I was looking forward to fondle his hard muscles and a good time squeezing his chest and pecs. Luckily, I managed to finish work on time and have time to head to my gym for a quick workout before meeting him. 

My taxi drove into along the street and picked him up after his gym session. He wore a button up shirt as instructed. On the way back, we chatted on casual stuff, while my eyes were staring at his muscles and thinking of ways to induce pleasure till it tortured.

After our shower,  I led him into the bedroom. He was blindfolded with his arms stretched above his head bound by the door straps. Slowly, I undid the buttons on his short sleeves shirt. I unbuttoned the top 3 buttons and teased him by grabbing his big, smooth chest and fondling his nipples. I enjoyed caressing his fit body, grabbing his butt and feeling his crotch.  

I peeled open his shirt to lick his nipples which caused him to moan softly. His semi-hard cock immediately turned rock hard. I unbuckled his jeans and allowed them to drop down at his knees. I continued to toy with his sensitive nipples before stripping his jeans away.

Turning him to face the door, I removed his shirt and secured his hands to the door straps once again. I grabbed his hair and pulled back his head leaving his exposed nipples in a vulnerable situation. My hands reached for his pink nipples to tease him and grabbed his hard chest and abs.

My right hand invaded his white undies and I reached lower to finger him. I pulled back the elastic band and let it smack against his lower back. His briefs were pulled down slowly exposing his bubble butt and I knelt down to rim his ass. When his ass was properly worked on, I took the Aneros and gently probed it into his hole while playing with his nipples to relax him.

I turned him back to face me so I could have easier access to suck his nipples. By now his precum was already leaking. I scooped it with my finger and fed him with his own juice then licked his cock head.

Using the ropes I had, I did a shibari bondage on him. Once completely, I removed the blindfold and showed him in front of a mirror while fondling his smooth body. I pulled out his cock from his undies and stroked it gently. 

I guided him towards the bed and got him to lie on his bed in spread eagle position while I bound his hands to the side of the bed. Pouring some silicone lube onto my left palm, I began to edge him slowly. Once he got on the edge, I would slow down and stroked his hard cock gently. 

Several times he was so close to cumming. I would form an O with my fingers and made him thrust against my hand. My free hand went on to molest his smooth thighs and big, hairless chest. It was an intense session as he almost shot his load several times but was held back by me.

Finally, he couldn't hold back anymore and cum without permission. I stopped edging to give him a ruined orgasm and watched his non-stop massive outflow of his cum juice which had been stored for 7 days. When he thought it was over, I grabbed his hardon and began to milk his cock for another load again. He struggled as his dick had gotten more sensitive and his balls were almost dry. I managed to squeeze out the remaining load before he had a dry orgasm.  

I kissed him as a reward for being a good boy. He was untied. We embraced and rest until we both had recovered before heading to the shower to clean up. 

Horny, Naughty Officer (Part 1)

It had been a nasty week for me, stress from work coupled with negative comments about me spouting online. In need of a relief, I texted him and asked if he would be free to meet.

Me: What are you doing tonight?

Him: Nothing much.

Me: Do you want to meet later?

Him: Hehee.. What are we meeting for?

Me: Something naughty I suppose.

He drove over around 7 pm and fetched me from my office to my place where I packed up my gears. I took the chance to pack two different full face hood into my bag as well as a CB6000 cock cage which he always wanted to try. After packing, I changed into a set of singlet and shorts without underwear, tooked my stuff together with a set of my army uniform to meet him downstairs.

Throughout the journey, I was caressing his crotch while he attempted to stroke my thighs whenever we stopped at a red light. He had not come since Monday, after his return from a trip overseas. His balls felt full and heavy as I squeezed them gently.

We reached our destination which is a secluded office toilet, and both changed into our pixelated uniform. I took my time to change while staring at him stripped off his t-shirt to reveal his lean abs. I told him to keep his red lycra underwear on as it felt more sexy on him. We embraced each other after we were done.

I buried my nose into his neck. He smelled fantastic, a mixture of cologne and his manly scent. My hands moved along his back, feeling the smoothness of his lean body. He was an officer during National Service and we had been discussing this uniform session for a long time.

Taking out the two hoods from my bag, I gave him a choice between the synthetic leather hood or the spandex one which he had tried before. As a lover of full face hood, he naturally chose the black synthetic leather one this time. 

Once he was hooded, I pinned him against the wall and slowly unbuttoned the shirt of his uniform. I proceeded to suck on one of his nipples while I pinched on the other. His hands reached for my shirt and began undressing me and playing with my nipples too. 

Pulling his hands away from my nipples, I tied them behind his back while I knelt down to undo his flyer. By now his crotch was already wet. His precum stains were obvious. I buried my face into his bulge and rubbed my nose against his shaft while I nibbled on the base of his shaft and played with his low-hanging balls. 

After half an hour of playing with his crotch and nipples with a vibrator, I untied him and pulled down his red lycra briefs. There was a web formed by his precum and his cock continued to leak strings of Cowper's fluid.

I helped him to remove the hood and replaced it with the spandex hood, which was more breathable. I ordered him to suck my cock. He hesitated for a moment but carried on with my instruction to lick and suck my dick. After he had finished sucking, I placed a ball gag over his mouth since I won't be needing his oral service anymore.

Grabbing his dick I squeezed it hard until it began to soften. I fixed the ring part of the CB6000 around the base of his shaft and continued pinching on his hardon until it was deflated. With his cock semi-erected, I forced it into the cock cage and locked it. 

Once I made sure there was no way he could escape from the cock cage, I released his wrists from bondage and guided him to feel the plastic case enveloping his semi-hard cock. I took his other hands and made him feel my hardon, giving him a mindfuck and a mental agony of not being able to jerk off.  

I went back to my bag and took out the pair of nipple clamps and attached them to his nipples. I watched him moaned in pleasure and torture as I turned on the vibrator to work on his nipples till they became sore. 

His cock struggled to get hard but the plastic casing restricted it. I tugged on his nipples and slowly pulled it off his chest causing him to groan. Grabbing this opportunity, I licked on his sore nipples while he wriggled in helplessness. 

Releasing him from the wrist cuffs, I guided his hands to pinch my nipples while I jerked off my cock. He began pinching harder which made me stroked myself faster and eventually I managed to shoot a huge load onto his abs. 

He was feeling extremely horny for having not relief himself for 5 days and my constant teasing over the past 90 minutes made him even more sexually aroused. I released him from the cock cage to edge him but he was begging to be allowed to cum. 

Feeling tired from my orgasm earlier, I removed the wrist cuffs and gave him 30 seconds to ejaculate otherwise I would cage up his cock for the weekend. As I counted down he stroked himself faster while my fingers pinched his nipples. 

Before I could finished counting, he shot a massive load forming puddle of semen on the floor. And he continued to stroke himself until he drained the final drops of juice from his balls. 

It was 10pm when we finished the session. We washed up and headed to a nearby eatery for some refreshment. 

Over dinner, I told him about the negative comments about me on Twitter over the past days. As my Twitter follower, he told me not to be bother by the gossips as those people who know me in real life knows what kind of person I am. 

To me, I feel that many times people confused my online personality with who I'm really now.  And I wonder if those people who sprout negativity about me had really done their reference check or do they just listen to haters such as my ex-boyfriend. And there has to be a reason why I broke off with my ex-boyfriend, right? 

The internet is a free world but it doesn't mean we should not be responsible for what we say. I'm ready to move on and I hope that my haters will eventually find peace within themselves.