Sam's Suffering

I was seated comfortably opposite him for our discussion. Sure, we chatted about a lot of our interests online, but now it was about to happen. It was real. We needed to be clear as this was no normal bondage hookup.

“Such a handsome boy.” he said.

“Thank you, Sir. I find you extremely sexy, too.”

Sir Tom is his name. Very funny. He’s Forty-five, super handsome with great salt and pepper hair. What really caught me off guard was his height, 6’4” to my 6’ 1”  and dressed in his full leathers looking like Tom of Finland. Leather shirt, leather tie, leather pants and tall riding boots. This guy committed to this, he spent serious money on this lifestyle, judging also from what pictures I had seen of his home dungeon.

“Now that you’re here, tell me again what you wish to experience tonight.” he bit his leather gloved thumb as he inquired.

“I wish to be tortured, Sir.”

“Define torture, Sam.”

I started shaking. Never had I expressed these hardcore desires verbally. Here goes nothing.

“I wish to be kept bound, preferably in leather restraints or rope, but Sir can restrain me however he likes. Being gagged is also very important to the experience for me. To feel powerless, like nothing I have to say matters, and to further increase my discomfort.”

“Good boy. You will look hot in a ball or bit gag. You will wear one the entire evening. What else, boy?”

Crazy. It was starting to feel easier to share. Liberating to discuss these taboo thoughts with someone who wants to make them real.

“ From there, I want to suffer. Stress positions, predicament bondage, whipping, caning, TT, CBT, e-stim.”

“Hah. Boy wants it all. Sure you can handle all this? It sounds hot as an idea, but very few people are the masochists they think they are with their cock in their hand.”

“To be frank, Sir, I can’t get the thought of this out of my head. Since I got my first hard-on, everything pointed me deeper in this direction. Every dirty thought. Every porn video that got me off. Every partner that didn’t quite satisfy. I’ve just turned thirty and I need to know.”

“I respect your confidence, Sam.”

“It will either be everything I’ve needed, or closure on something I didn’t enjoy but glad I did. Either way, I will make it through to the end, Sir.”

“I like you, Sam. I’m going to enjoy this one.”

That comment made me rock hard.

“Bringing you pleasure from my suffering is the hottest thing I can think of, Sir.”

“If I felt like it, would you let me fuck you, Sam?”

Creaking leather clung tight to his muscled chest as he relaxed his posture. Very masculine. I couldn’t take much more of  this anticipation.

“Sir has free reign to enjoy my body. Whether you want me in agony or ecstasy is your decision.”

He smiled crookedly at that response.

“Ten minutes til eight. Last chance to back out. You will remain in my dungeon from eight pm until eight am. You will not sleep, nor will I.  You will be bound and gagged the entire time other than when transferring you from one post to another. There is no safe word to get out. There is no stopping. Seeing as this is your first time only, I will grant you one mercy. You will have to figure out how to say it with the gag on to use it and all it will do is grant you thirty seconds to recover before returning to your suffering. It will not be given in any future sessions and it will not make me think less of you for using it. I respect you and thank you for trusting me with your body. Do you wish to continue, Slave Sam?”

“Yes, Sir.” It came so effortlessly. 

He came to me, took me by the arm and led me to his basement. My heart began to race. Not second thoughts, but I was now a little scared.

He flipped the switch to reveal his dungeon. Dimly lit. Moody. Hot. It was fully decked out with a St. Andrews Cross, Bondage Table, Suspension Station with leather restraints dangling down. I had no doubt that in a twelve hour session, I would spend hours suffering unique torments on each. 

On the wall, tons of toys and implements. Rope, shackles, ten types of gags, maybe twenty whips and paddles. My cock was leaking through my tight white pants, tucked neatly into my shirt.

He led me to the cross first, buckling my ankles into the restraints. Clothes still on. I was confused. Then came my wrists. 

Off he went to select some items from the wall to start. When he returned, he placed everything on a small table near me, keeping a fairly large red ball gag in hand, holding it up to me at eye level.

“Sam, every dom has their own system when it comes to play. Many like to collar their slaves. I use gags. This is your gag and your gag only. I have them color coded depending on how the boy likes to play. Black is for slave training, blue for FF players. Red is for guys that want a pain trip. You will wear many different gags depending on what I feel like, but this is your default. Understand?

“Yes si–”

He shoved it tightly in my mouth as I responded. I groaned as he buckled it tightly.

“Fucking hot, boy!” He licked my gag in my mouth as I groaned. “Red looks good on you, Sam. You are my first boy to wear this color, but don’t worry. I wore it when I was your age.”

Sir Tom ran his gloved hand over my pants, fondling my cock. Whispering in my ear. “Bet you’re wondering why you’re clothed.” Warm breath tickled my ear. This was pleasurable and I was caught off guard. The time hand not started and he was fucking with me. He continued, “Don’t worry, your flesh will see whips and clamps before long, but first, your body will hurt itself.”

He undid a strap holding my wrist restraint to the cross. My body fell from the cross and my knees buckled. I was nervous and fell to my knees.

“Ah. The slave’s body knows where I’m going with this.”

He began by locking my ankles to an anchor point directly below me. Next he took my right wrist and locked it against an anchor point on the floor behind me. He repeated on the other side. The result had me arching my back and my chest to the sky. My quads tried to compensate for the position, bringing them quickly towards exhaustion as well. I’m somewhat flexible but this sucked.

He came behind me, running his fingers through my hair. Medium-length, brown, and I was quite proud of it.  Sir ran his fingers down my chest and through to my belly, making note of every line, every muscle.

“Boy is fit under these clothes. It will be a delight to watch your muscles give out on you, Sam.” Sir spoke in my ear as he flicked my right nipple mercilessly.

I groaned harder into my gag. This was more than I could have dreamed of and it was just beginning. God help me.

With his free hand he traced my strained ab muscles, exploring my body, making certain not to support my body at all. His index finger explored down further, poking into  where my shirt was tucked into my pants, plucking at a few pubic hairs to force a whimper out of me. The remaining fingers rested on my belt, a wide, heavy brown leather with a black buckle. His fingers danced on the strap as he squeezed my nipple hard on the other hand. For the first time so far, I screamed into my gag.

“All for you, boy.”

He kissed my cheek and moved to my front. He grabbed my belt again and undid the buckle. I hardened and squealed. This was fucking hot and I couldn’t stand it. Sir Tom pulled the strap back  to release the prong from the hole. Biting his lip he grabbed my hips and pulled up. I instinctively compressed my waist as he pulled the strap tighter before fastening it back on. 

“Feels better this way.” He observed the line of my cock through my pants and slapped it. I moan.

He enjoyed it, licking my cock through my pants up to my belt and back down again. My shirt was drenched in sweat and my pants in his spit. He pulled out a pair of scissors, slicing off my shirt to expose my torso.

“Fuck, Sam. Such a hunky slave.” He returned to the wall and approached me with a crop, the business end of it resting on my sweaty abs. “Your body is a dream to torture.” He whacked me hard. I yelped. “If you’re enjoying this,” WHACK “half as much,” WHACK “as me,” WHACK “ then maybe I’ll keep you until Saturday 8pm instead of am.”

He pulled my gag out for an answer.

“I like you, Sam. It’s early, but you suffer beautifully. Would you like to extend? If not sure you can call mercy later to confirm.”

“I’ll think about it, Sir.” He shoved my ball gag back in and tortured my bare torso for another hour. My body ached, my skin stung, and I was considering the extension very seriously.