Pain. Or Pleasure?
As I was regaining my wits after the bukkake where I served Sir’s five Black friends, I realized that neither Sir nor Lt. had taken part. Still on my knees, I scanned through the naked legs of my assaulters and found them both relaxing on the couch, casually stroking their hard cocks. I wasn’t sure what to make of that, but there was no doubt they weren’t intending on sitting out the entire evening.
Like clockwork, Sir rose from the couch, walked over to the circle of panting men still surrounding me and pulled me to my feet. “Let’s get you cleaned up before the night starts”, he said. WTF, the night hasn’t even started?
Sir walked me to the bathroom and sponged off only some of the cum from my face and torso telling me, “I want you to smell like dried cum like the pig you are.” Could the humiliation be more complete, I thought to myself. I’m sure they’d find a way.
“Let’s go” he said as he marched me back to the suite where the other men and Lt. seemed to be waiting for us. “Lt.?” Sir called, as he walked in, indicating he needed Lt.’s expertise for the next step.
Without hesitation, Lt. attached my cuffed right wrist to one of the ropes hanging from the ceiling and walked around and repeated that with my left. He pulled each snugly, but not too tight (yet.) After that, he secured each ankle and pulled them equally snug, making sure my ankles were spread as wide as possible. Then he meticulously circled me, tightening each wrist, ankle, wrist, ankle, making sure the tension was consistent across my body, until my arms and legs were pulled into a rigid “X”. I was bound exactly like I was last night in bed, but this was more intimidating because my balls and cock were exposed and vulnerable, and there was a roomful of still horny men waiting to use me.
I waited, bound and helpless, aroused beyond words. I saw myself on the screen and gasped at the eroticism I was projecting. Skin taut and covered with sweat, stretched muscles bulging, slow, sensuous writhing, and my cock now purple and engorged with blood. Just the sight of me nearly made me cum.
I then looked around the room at each of my assaulters. Glistening with sweat themselves, fully erect even though they had cum just minutes ago, slowly stroking themselves, staring at me with unbridled lust in their eyes. I wanted nothing more than for any one of them, better yet all of them, to surround me, paw me, press their hard cocks into me, and stroke my cock until I came. Just feet away from all that skin, sweat, muscle, and erect cock, yet not being able to reach out and touch any of it was pure torture.
Taking charge, Sir walked up to me, stood directly in front of me and grasped each side of my torso at my ribcage. It didn’t hurt, but the message was clear. He had full control over me.
Stepping even closer, he wrapped his arms around me and grasped my back, and then my glutes with both hands, then again harder. There was little pain; frankly if felt like a loving way to establish our mutual roles. He was in charge, I will submit.
He then grabbed my throbbing cock, and while squeezing it painfully hard, stared into my eyes without saying a word. Although he said nothing, his message was clear to the room, and me: I own you. He then put one hand on each side of my head and pulled our faces as close together as possible and stage-whispered for everyone to hear:
“What is your role, tonight?”
“To give you pleasure sir”
“Me and who else?”
“All of you, Sir.”
“Yes Thomas, your role is to give us pleasure. Your pain is our pleasure. You will experience pain, and the more pain you experience, the more pleasure you provide us. They are equal. We expect nothing less from you. Are you ready?
“Yes sir.”
I had officially submitted to the Stockholm Syndrome. All I wanted was his approval, and strangely, his love. His two words, “Good boy”, felt like the most meaningful words of my 40+ year life.
I sighed in relief, but knew we were only getting started, so I wasn’t surprised when Sir walked over to a table and picked up a flogger. I hadn’t seen it before, but now it was all I could see.
He held it in the air in front of my face, taunting me with it, then gently caressing my torso with it. First my back, then my chest, and then my obscenely erect cock. It felt so soothing and comforting, it was like he was tormenting me with what was to come.
Remembering that everything that happened these two days was being video taped, my eyes returned to the video screen. Unknown to me, there was more than one camera operating. The screen was split into three images, one a long shot of my writhing body, another a shot of Sir gently caressing me with the leather flogger, and the third a closeup of my face, showcasing my anticipation and….fear.
Like the expert he was, his strokes started so gently I didn’t fully realize it was happening. He was remarkably graceful knowing exactly how, where, and how hard to strike me, and I luxuriated in the feeling. Then he slowly picked up force and velocity, intoxicating me with the aroma and feel of the leather tails that caressed me. He continued to accelerate both intensity and speed, but took me along with him. The harder the whipping, the longer he waited for the next one, leaving me begging for the next. Each stroke was so erotic I pleaded for more. And before I knew it, he was fully flogging me and the sensation had evolved into pain. But not like any pain I’d previously encountered….it was pain I welcomed, even got off on. If you don’t believe, me, you should’ve seen my cock. Not only was it harder and thicker I'd ever experienced, the tip was dripping precum. I only know this because I glanced at the video screen and it now included a close up of my rigid, angry cock.
His beating took an even more erotic turn when he slowed down the pace, stood behind me, and flogged up between my legs so the leather tails surrounded and embraced my cock and balls. OMFG. The first time he did it my head almost exploded, and every time after took me to a state of euphoric helplessness. It makes zero sense, but the eroticism of having your extraordinarily vulnerable cock and balls being lovingly tortured by a leather flogged is indescribable.
He walked back behind me and decided it was show time. Each strike on my back was now harder than the one before, creating an X-pattern of welts across my back. Every flog was 50% erotic/50% painful. There’s no other way to describe it. Just when he reached the point where the pain exceeded the pleasure, he stopped.
In the most loving way possible, he gently rubbed my back up and down, first with his palm and then with his fingertips. Pressing them into my spine, I almost wept with the feeling and instinctively, pushed my ass out hoping he’d slide his hand down there. He didn’t disappoint, as his fingertips erotically slid into my ass crack where he pressed into me expressing ownership. I couldn’t help myself and dropped all my weight and hung from my shoulders, accepting his affection and care. I didn’t know what was yet to come, but so far, I’d died and gone to sub heaven.
My heart was pounding and what he did next startled me even more. Standing again in front of me, he took a dramatic step back from me and assessed my body, up and down, and, without warning slapped my engorged cock with his open hand, once from the left, once from the right, and most painfully, from above. Each time a let out a muffled scream, as much from the shock as from the discomfort.
Then he stepped back up closer to me, grabbed my head by the ears again and came in for a kiss. I instinctively opened my mouth to accept it, but before he kissed me, he spit into my open mouth, and then followed with an aggressive, passionate, tongue-filled kiss.
He pulled away, turned his back, and picked up a riding crop and handed it to Raymond, who was now standing by his side.
“He’s all yours”, Sir said to Raymond.
Now it was Raymond’s turn. He was nude now as well, wearing only his leather cap, leather boots and armband around his left bicep, and his massively hard 10”cock. But he picked up a different instrument of torture….a riding crop.
He placed the riding crop right under my balls, as if he was using it to hold them in place. The coolness of the crop actually felt good there. Then he started tapping it slowly from below. At first it was tolerable, but my balls are so incredibly sensitive it quickly became painful as he increased his force and speed. This would be the first of many times that night I’d remember Sir’s words: “Your pain is our pleasure”. As I grimaced from the increasing discomfort, I made a point of observing the closeup of my face on the video. My agony was giving them their money’s worth. Now all of Raymond’s friends, along with Sir and Lt., were in a semi-circle around me grotesquely enjoying my torture. They were stroking themselves and each other getting off on what was happening to my balls. When it was becoming intolerable, he slowed down the pace so I was given more time between each strike to prepare for the next.
“Spread those legs, boy”, Raymond ordered. I actually had little control as the ropes had my legs pulled as far apart as possible, but it seemed to be part of the show.
“Whack” he administered, the hardest so far, that sent chills up my body.
He slowly walked around my back and, without warning, another “whack” to my balls, this one from behind even harder than before.
I began to wonder how much more I could endure. My balls had never been abused in this way, but the state of my cock—erect and rigid—was telling me I loved it. Now back in front of me, Raymond administered the hardest “whack” yet, finally forcing me to surrender, “Mercy, Sir…” I wept. Looking into the eyes of the circle of men who were getting off on my pain, and then Sir himself, I didn’t want to disappoint him or them. But I had reached my limit…at least for now.
Thankfully Raymond moved away from my balls and now targeted my torso and back with small, stinging hits. It felt strangely good to feel the sting of the crop on my main body and not on my balls. I was proud of my muscled torso and this gave me the opportunity to show how much I could take. Now, in a completely weird head space, I begged him…“More sir. Please sir, punish me.” Damn, if that didn’t get him revved up. He took me at my word, took aim at my ass and quickly ordered me to “Push it out”. Now I was near heaven. I was quickly learning my limits, and my ass had a high tolerance for pain. “Please sir, I want more”, I pleaded.
“Oh, don’t worry, boy. You’re going to get plenty more”.
Raymond paused and walked toward the table; I thought this chapter of the evening was over. As usual, I was wrong. Raymond picked up a flogger whose tails appeared heavier and longer, and likely more stinging than the one Sir had used. He teased me a little by stroking my torso and cock with the flogger like Sir had but I could tell this round would be more intense.
To begin, he stood in front of me and flogged down over my shoulders, going back and forth, each strike more forceful than the last. He then walked to my side and, at first softly, and then more vigorously whipped my ass to the point where I could feel the burn on my cheeks.
Now directly behind me, again starting slowly, he whipped my back in the same X pattern Sir had, allowing more time between each lash to allow my back to absorb the previous blow, adding to the drama. It worked.
My shoulders, ass, and especially my back were on fire. On the last few strokes of each, I cried out in pain, which I could tell was exactly what my audience wanted from me.
And once again, although my skin said I was in pain, my cock told a very different story. If possible, it was getting even harder.
Next he moved to the back of my legs. Soft at first, and then with power. Then, from the front, my thighs, each time getting closer and closer to my cock and balls. I didn’t know what I’d do if he flogged my cock and balls with the intensity of what I’d already endured. I feared I’d faint from the pain.
After one last scorching thrashing of my thighs, he slowed down and started to work on my cock. Remember, my cock is crazy thick and reaches to the sky when erect, so he had a plenty big target. He went back and forth, hitting it with the flogger from the left and then from the right, and occasionally from above. And like before, each time was slightly harder than the one before. Before long I cried with every strike.
Raymond’s brothers were getting off on this as much as I was. Their bodies were now covered in sweat and they were stroking themselves as they watched, and, although I was in pain, I couldn’t escape what Sir had told me earlier: “Your pain is our pleasure”. If that were true, and it appeared to be, they were in fucking heaven.
Raymond appeared to be taking a break, or possibly even concluding this chapter, I couldn’t tell. Having a moment to take a breath without fearing a beating, I slumped so that the rope completely supported my weight from the ceiling and looked at the screen on the wall. There I was, bound and hanging with lash marks covering my body, sweating from head to toe.
Two things ran through my mind simultaneously. First, I was horrified at my appearance. My battered body would take days, if not weeks to heal. More importantly though was that I wore those wounds like a badge of honor. The pain I felt was a physical manifestation of what I had endured for Master, and how much I had enjoyed the beatings myself. I came here to see how much I could endure and whether, like in my fantasies, I’d get off on the pain. The night wasn’t over, but I was getting my answers. But overriding everything remained my inescapable desire to cum.
As I hung there, Sir and Lt. encircled me and released me from my bondage. Without thinking, I dropped into Sir’s arms and quietly broke into tears as much from gratitude as pain. I was careful not to openly sob, but I was overwhelmed. Overwhelmed with lust. Overwhelmed with pain. Overwhelmed with pride that I’d survived. And overwhelmed with the excruciating need to cum.
“Please Sir”, I begged with my voice cracking. “Please…..” I was begging him to let me cum, but didn’t have the courage to say the word. But he knew.
“Soon, Thomas”, he answered. “Soon. Now on to the sling…”
