Cumming Twice in Uniform and Boots

“Report in your military uniform and boots.” That was my reply to him when he wrote to me requesting me to dominate him and a chance to try on the CB3000 cock cage and butt plugs.

His place was located at a heritage-looking building in the quiet part of the city. I arrived at his house when the noon sun was shinning furiously at one o’clock in the afternoon.

He was in his military no. 4 uniform, complete with boots and a pair of non-requested sunglasses when he opened the door. Nervousness was in the air when I entered the room. Today was considered his first real BDSM experience.

His previous encounters were restricted to the wearing of uniforms and mutual jerking off – a personal insult to me when he mentioned that he had tried BDSM before. To me, BDSM is not just about having a fetish for certain clothing, but a mind-fuck, a pushing of limits and temporarily moment of living in a world we so longing for.

He was told to remove his sunglasses. I questioned him on this additional eye gear which I did not requested for and forced him to put on his blindfold otherwise I would be turning my back to go.

After he complied, I laid him on the bed and tied his hands above the head and covered them with a pillow. I proceeded to fondle his toned body as a warm-up activity before undoing his buttons one by one. Once his chest was reveal, his nipples were given a royal treating of pinching, biting, squeezing, licking and fondling by the master.

I went down under to unbutton his military pants and was greeted by his monstrous seven-and-half inch dick. It wasn’t the length that made it amazing, but the fact that he was Chinese and he was a petite man, hence in proportion his cock looks wonderfully big and hard.

The first toy I tried was my vibrator on his gigantic penis. I applied some lotion on his cock head and rubbed against his manhood causing him to moan. When the vibrator was turned on, there was no turning back.

The vibration simulated his cock head and soon he was oozing precum and moaning in ecstasy. I took this opportunity to attach nipple clamps onto him. But the clover clamps were too painful for him to endure and I had to remove them.

I lubed up his ass and pushed the small size butt plug up his butt hole sending him to for euphoria. The small size one was replaced by the medium size butt plug and he seemed to be enjoying the experience even more.

Seizing the chance, I rolled a condom over my erected penis, lubed up my dick and positioned myself to penetrate his hole.

I took aim, ready myself and pushed my cock up his ass hole. It was very tight or loose, the feeling with just right. I had great fun fucking his man hole and using it for my pleasure and he was enjoying the sensation of being tied up in uniform and getting himself fucked.

He requested to wear the CB3000 cock cage as he had never tried it before. I had to pull out from him to attach the chastity device onto him. It was difficult trying to squeeze his enormous dick in. I gave him time to cool down and ordered him to go for a cold shower but he was too horny and his erected cock refused to back down.

After half an hour of trying, I have no choice but to allow him to cum, in order to attach the CB3000 onto his penis. Loving to abuse his ass, I took the large size butt plug and forced it up his hole while I jerked off his rod.

It didn’t take long for him to shot his first load, cumming all over his 6-pec abs.

He rested for a while as we cleaned up the mess and attached the chastity cage over his semi-hard dick. It was a really tricky situation as he was still very horny and got erected very easily. I had to be quick to attach the cage to the base to firmly secured his growing member within the device.

Once locked in, his dick was pushing hard against the cage pleading to be erected as I played with his nipples.

I lifted his legs up in the air and forced my hardon a second time into his warm ass. I started slow and then faster and faster humping his man hole while he was moaning for mercy.

It came to a point that became to painful for him as he had cummed earlier and the sensation of fucking had turned from pleasure to pure pain and torture. I had no choice but to stop my enjoyment of his ass and to pull out.

I removed my dick from his perky butt and the cock cage from his dick. The relieved member immediately sprung into a fully-grown seven-and-half inch meat rod. I poured lotion over his rock hard cock to mercilessly tease his endowment.

He begged for the large anal plug to be pushed up his ass and I happily obligated to his request. Cum-controlling took another 30 minutes, forcing him to moan non-voluntarily, before I finally allow the grace for him to cum.

The first load was messy and this second orgasm was massive. His ejection shot all over his torso, chest and onto his bed.

The School Boy’s Torment

It was a difficult choice for me to make – choosing between getting him to report in his army officer uniform or his crisp white set of school uniform.

Finally I decided that he should put on old junior college (JC) uniform and report to my place for detention and punishment.

He arrived punctually at my place five minutes before 10 a.m. for his torture session. Earlier on, in our message exchanges, he had mentioned that his dick head was extra sensitive, torturing it will send straight to hell in heaven.

Bingo, how I love boys who obediently announced their weak spot to me for torture.

It was going to be my favorite kink – cum control, and the goal was to break his previous record of an hour-long of dick teasing with ejection. He was instructed to withhold from jerking off since Thursday.

On Tuesday morning, he arrived in his Bermuda shorts and officer cadet trainee’s white polo shirt. He told me that he had to drop off his younger brother to school and hence was unable to change into his old school uniform before meeting me. It wasn’t the reply I was hoping to hear from him and I made a mental note to torture him later for this.

I instructed him to change in one of the bedrooms and to wear the tighter pair of swim trunks underneath his white attire. Once he was dressed up, I secured the leather restraints around his wrists, placed the blindfold covering his eyes, and led him into my room for his torture.

He was made to sit on the torture chair while I secure his hands behind the back of it. Button by button, his shirt was opened slowly revealing his nipples. I gave his tits some teasing and it was so not sensitive to touch.

I made my way down to his groin and found that his dick was already semi-hard. A light rub against it and blood gushed in to fully erect his manhood. He let out a soft moan in anticipation.

For the warm-up, I fondled his cock for 15 minutes before stripping off his white pants. By this time, his rock-hard dick was showing a contour inside his swimming trunks. Feeling inspired by Japanese porn, I squeezed lube onto his swimwear and began massaging his dick head.

He was fighting back the torture and bit on his lips as I took joy in fondling his frenulum and glans.  This went on for another 30 minutes and he was given the choice between continuing the play with his swim trunks or for me to remove them.

He chose the latter and within seconds his trunks were lying on the floor and my hands were busy once again working on his penis. I adjusted his hand position to lock them behind his neck before slapping a generous helping of body lotion on his dick head for torturing.

He moaned as I continued my work on his sensitive body parts. I also found out that light fondling of his right inner thigh would give him an euphoria.

I released him from the restraints and motioned for him to grab the side of the chair as I carried on the third round of cock head teasing. But now, most of the pleasure had turned into prolong torture.

He endured an hour of cock torture without ejection and was given a two-minute break.

Onward to next phrase, he was made to stand and lean against the wall with his hand behind the back – a vulnerable position which I could continue torturing his dick for my enjoyment.

I came to stand behind him and adjust his hands over the head such that his arms were wrapping around my head while I took a handful of lotion to work on his manhood.

Every motion I made on his dick became a torture. There were moments which he could not stand still, with knees bent in reaction to my actions on his cock. His moaning had also become more intensified.

I released my grin around his chest with a sinister plan – I sat on the chair facing the boy and positioned his hands to grab on to the back of the chair. His legs were made to spread wider. I helped myself to more body lotion and comfortably jerking off his dick while he was in a compromise position. 

The fact that his hands were not chained or tied adds to his humiliation and torture. When the suffering was too much for him, he would attempt to lean back but I would beckon him forward making it look as if he was willingly accepting the torment. This was perhaps the more intense part of the session.

Finally, I allowed him a chance to lie on the bed – not for resting, but to carry on the last segment of agony. I cuffed his hands above his head and placed a towel underneath his smooth ass. After which, I slapped lube onto my palm to tease his cock head. Using my other hand, I unwrapped the butt plug from my gear bag, wetted it with KY gel and positioned it at the entrance of his butt hole.

It was his first time having a plug inserted into his ass. I leaned on the side of caution not to inflict only just pain to him. Using my right hand to finger him while my left hand continued to cum control him, the boy was moaning louder when my finger went into his butt hole. Soon, I replaced my finger with the small size anal butt and it slipped comfortably in. I was surprised that his ass was not tight at all. I made a mental note to insert a bigger plug for the next training session.

I proceed to tie up his legs to prepare for the finale. I edged him with faster strokes and gave him even shorter breaks between the sets. Using both hands I rubbed against his dick pretend that I was trying to start a campfire, in this instant it was to ignite his mini fireworks.

I remembered he moaned and begged me twice, “Let me go! Let me go!” he cried. And groaned, “I’m cumming!” I paused for a two-minute cooling off period and proceeded with my campfire trick.

There was no word of warning when he cummed. Like a volcano, his white lava oozed out from the top of his dick onto my palms.

I slapped his stomach in objection of his poor communication. He protested and exclaimed,  “I told you just now that I was cumming!” Another mental note – this boy definitely deserved a second detention torment.