As a college sophomore at 19 years old, sex is always on my mind. I've been in a couple of relationships but have never really been satisfied, sexually that is.  You see I don't really know how to find what I want.  Sure I can get off online, but real life scared me as much as it excited me. Let me get to it, I want it rough, like really rough.  According to my BDSM test, I’m 100% masochist.  And I know it.  I can't get enough of watching the guys online doing all types of CBT. Nothing makes me harder.  I've got some toys I can use on myself, but I dream of someone tying me down and pushing my pain threshold to my limits and beyond. I don't need a "daddy" or want to role play as a pup; I'm just looking to have someone really show me their sadistic side.

That brings me to today, where I'm about to go to my first real live encounter with a guy into BDSM. I finally manned up and made a recon profile, describing what I was looking for and making sure I put my limits in there.  I also made sure it said I had no real life experience and needed someone who knew what to do with a newbie.

I saw his profile about a week ago.  He lived about 20 minutes away from me and his profile really jumped out at me.  There were pictures of men, men he has played with, in various states of bondage, specifically predicament bondage, which really got me hard. His profile said he loved tying guys up and torturing them to their pain threshold and beyond. He was fine with guys new to BDSM as well as experienced players. As I read through the list of his toys and what he likes to do, I found myself harder than I've ever been.  Before I gave in and grabbed my cock, I sent him a quick and anxious message while I was still extremely horny and wouldn't talk myself out of contacting.  He must have been online, because a few minutes later he responded saying that he liked my profile and wanted to play with me.  All horny, I messaged him back that I was in.

Over the next few days, we emailed back and forth to discuss limits, details of what to expect, and safety. He insisted I tell a friend where I was going for safety reasons, which I did.  I told him I had played by myself with CBT, self-bondage, chastity, and Clothespins and really got off on it.  He asked me to not cum until our play date, which meant 5 days of no Cumming.  I stayed true to the task, locking on my cb600 rip off from China.  It was the longest I had been without orgasm since I started jerking off.

So now I am on my way to meeting him at his house.  I'm nervous and want to chicken out but promised myself and him that I wouldn't do that.  I'm still wearing the cb6000, my balls are desperately full, and my cock is painfully pressing up against its cage.  I know we discussed what to expect and safe words but this is all new.  I'm sweating already.  I check myself out in the mirror before I go in.  I look good other than the sheen of sweat across my brow. My blue eyes are electric with nervous energy.  I've worn tight jeans and a comfortable shirt that hangs slightly over my relatively small frame.  It's now or never.

I arrive at his door, still thinking about bailing when I make the final push and ring the doorbell. He answers pretty quickly and invites me in.  He is about 6' tall with dark hair and dark eyes. He is wearing a tee shirt and jeans that cover his little belly.  He's not the hottest guy in the world but he is attractive.  He invites me to his living room and we sit down on opposite couches.  I'm beginning to wonder if this is a big mistake.  He recognizes my nervousness and attempts to calm me with some small talk.  After about 10 minutes, he asks if I'm ready and I say yes.  We review the safe words, one to slow things down and one to stop. He asks if he can photograph and video, promising never to show my face. I say yes but only for personal use, not for putting on his profile.  After I sip some water, I can tell he is ready for business as the look in his eyes changed dramatically. 

He asks me to take my shirt off and place it in a bin in the corner of the room. He then tells me to place my shoes, keys and wallet in the bin and leave my pants on.  He asks me for the key to my chastity device which I give him and then pulls out handcuffs from his pocket.  He grabs my right arm and cuffs it to my left hand behind my back. So behind me, he starts rubbing my right nipple between his fingertips, using his nails every so often to dig in. It hurts and sends a message immediately to my dick which is now straining again in the cage.  He teases my left nipple as well and really gets me going. Out of nowhere he pulls out nipple clamps and applies them to each nipple, biting as they dig in.  I let out a soft moan and I see him grin.  He plays with the chain of the clamps pulling them and letting them drop.  I start to pull away and he pulls the chain towards him and grabs my crotch with his other hand.

"Where are you going? We're just getting started"

He leaves me there for a minute and returns with a collar and leg cuffs. I've never really gotten into the slave or prisoner stuff online but seeing him put the leg cuffs on me and hearing the slow ratcheting of the cuffs got me extra hard.  He applied a lead to my collar and slowly led me to a door his kitchen which leads to his basement. I took a glance around the room and was mesmerized. He had equipment for bondage, a cross, a sling and a million torture devices, ropes, and whips hanging from the walls. Seeing it all had me a bit dizzy and scared and I felt my cock softening. What have I done?

He leads me to the cross and turned me around to face him. The nipple clamps were still biting and he gave them a quick tug.  He attached the lead to my collar to a hook in the ceiling and grabbed a set of leather restraints.  He applied them to my wrists and took the handcuffs off. He attached each cuff to the arms of the cross and looked into my eyes.  His face was flushed and his brown eyes smoldered.  My cock awoke again in its cage as he grabbed my bulge through the jeans.   "Well let's see what we have here.”  He undid my jeans and pulled them to the floor.  He then yanked down the sports underwear I was wearing, revealing my cock cage and my balls begging for release.  He grabbed my balls and gave them a big squeeze.  I yelped out more in shock than overwhelming pain and he simply smirked at me.  "Oh we are going to have some fun tonight!"

He undid the leg cuffs and pulled off my jeans and underwear.  Leather Leg cuffs were quickly applied and I found myself spread eagle against the cross. He grabbed a box full of Clothespins and returned to me. "We'll start slowly and work up to some real torture, ok?" I nodded and he began to place the clothespins.  He started in each armpit, at my navel, and went to my balls.  He had at least 8 across my nuts like a fan.  The pain shot through me and my cock danced in the cage.  I've played with Clothespins before but this was hotter.  Yes it hurt, but knowing it would be worse when he took them off had my dick leaking precum already.

He unlocked my cage and pulled it off, making sure he smacked the Clothespins on my balls as he was done.  The pain was immense and my cock shot out.  My 6 inches was as hard as it gets as he dangled more Clothespins in front of my eyes.  He tweaked the nipple clamps which reminded me how sore they already were.  He took off the clamps and started twisting each nipple.  I screamed in pain was yanking on my restraints which were secured quite well. My cock defied me and continued to drool.

He quickly grabbed my cock and played with the precum. "Well someone is enjoying this" he quipped.  I simply replied, "Yes sir." He let go of my cock and then whacked it bare hand across the top.  The impact stung but also made the Clothespins on my balls vibrate.  I danced in pain.

He then started with Clothespins along the bottom of my shaft all the way up to the head. I've had Clothespins on my cock before, but this was a lot.  My breathing quickened and I shook a bit on the cross.

He began flicking the clothespins all over my body.  I continued to shudder, which of course caused the clothespins along my balls and cock to shake and cause even more pain.  I could see myself in the mirror across the room, tied spread eagle with the clamps all over me.  My cock continued to drool as I slowed my breathing down and adjusted to all of this.  He gently caressed my cheek. “That’s it.  Breathe into it.” 

The gentleness of his voice slowed me down and I started to drift further into my body.  He gently whispered, “Ready for more?” I didn’t know what more meant but I shook my head in the affirmative.  “Say ‘hurt me’” . 

“Hurt me.”

“Very good.  Here we go.”  He put a blindfold on me and I quivered as the room went dark.  He slapped the top of my shaft which caused the clothespins to all vibrate together.  He jerked my cock a few times and then slapped my cock again, this time harder.  I leaned forward as much as I could to protect my cock, but the restraints held me helpless.  He continued like that for a few minutes, gentle jerking and then a powerful slap. 

“Ready for even more?” 

I didn’t know that I was but I shook my head again.

“You know what to say.”

“Hurt me more please.”

“As you wish.”  I heard more clothespins being played with.  As it dug into the head of my cock I let out a growl of pain.  Only once had I put a peg on my cockhead.  It was excruciating and I took it off immediately.  Now, here I was trapped, and he had it on my cockhead.  He played with the clothespins on my balls and shaft, which momentarily distracted me from the overwhelming pain at the tip of my cock.  Out of nowhere another peg bit into my cockhead. I was spinning in pain.  He continued across the head of my cock and I lost count of how many he put on.  I was writhing in torment.  He flicked all the clothespins across my cock and balls and on my body.  He shook my cock and the clothespins on my cock head danced around, causing immense pain.  I thought about the safe word but knew I could handle this, as least for a few more moments.

The blindfold was suddenly off and he held my head face down, staring at my cock.  It was hard as a rock, with precum oozing freely from the 5 days stored load in my balls.  He held my head downward with one hand, while twisting my cock and balls to show me the work he had done.  The head of my cock looked like a sunflower, with clothespins circling the rim.  He let go of me and grabbed a riding crop and began “playing” with the clothespins with his crop.  Just when I didn’t think I could take anymore he stopped and gently caressed my cheek.  “Good boy. You ready for these to come off?”

“Yes sir”.

He started at my armpits, pulling the clothespins off slowly and then twisting and rubbing the area as I twisted.  He went to my navel and then to my balls, tormenting the area slowly as he removed each peg.  The pain shot through me.  I was sweating, and hornier than I have ever been.  He removed the clothespins from the shaft of my cock, whipping the now exposed area with the riding crop as he removed them.  I really wanted to shoot my load but knew to hold on. 

He left ring of clothespins on my cockhead and said “maybe we should just leave these here.  You seem to be enjoying them.”

“No sir, please, take them off.”

“Oh really? Well I’ll give you a choice.  Leave them on ten more minutes or I’ll take them off now.   If you wait ten minutes, I’ll take them off like I took the others off.  Slowly then a little torment.  If you want them off now, I’ll use this,” he held out a flogger “on your cock and balls for the next 5 minutes to get them off your cock.  Your choice.”

Now I had a problem.  I don’t know if I could make it another ten minutes and yet I was terrified of the flogger taking them off my cock.  I could only imagine how much that was going to hurt.  I have seen guys getting flogged on the cocks and balls online and it always looked hot but never with clothespins on the cockhead.  Ultimately, my curiosity won and I said I would take the flogger. 

The first hit of the flogger got one peg off my head and it stung.  It wasn’t as bad as I thought it would be but still the pain was intense.  The next shot came underhand and directly hit my balls, which sent pain shooting through my stomach.  He came back hard on the top of my cock which sent a few more clothespins into the air and set my cock on fire.  He didn’t slow down this time and continued to whack my cock relentlessly.  All the clothespins were off but he didn’t stop the flogging.  He would alternate between overhand and underhand shots, getting my cock, the cockhead, and my balls.  It became hard to breathe as I yanked and twisted to try and get away from the blows.  Maybe I should have waited the ten minutes with the clothespins on. 

After what seemed like an eternity he stopped the flogging and again gently caressed my cheek and whispered, “Good boy, keep breathing.  Good job.  You took it like a man.  Good job.” 

He grabbed my cock and balls with his free hand and yanked upward on them.  He held my head down to look at them and said “this is what your cock wanted, isn’t it?”

“Yes sir”.

I was still hard as hell and couldn’t believe I just went through that.

“I’m going to give you a break to stretch your arms and relax before we start again.  One rule, no touching your cock and balls.  Understood?”

“Yes Sir”.

“Good Boy”.  He left and came back with a circular metal object that he put on my scrotum above my balls.  After he attached it and let it go I knew it was a weight as the pressure built up on my nuts.  It wasn’t a big weight, maybe one pound, but I knew it was there.  He then grabbed a leather sheath which he showed me was lined with little pin pricks and wrapped it around my cock, securing it at the base.  “Just because we take a break doesn’t mean your cock and balls can get comfortable.”

“Yes sir.”  The little pin pricks caused a weird sensation on my cock, not quite pain but certainly not comfortable.  He placed the nipple clamps back on and then released my legs and hands from the cross.  He handed me a bottle of water and asked if I needed to use the restroom.  He said he was going to set up the next part of the session and I was to wait here for him.  He reminded me not to touch myself.  I told him I wouldn’t. 

“I don’t think you will but just in case.”  He brought me to the wall straight ahead that had some mirrors on it and some hooks in between the mirrors.  He handcuffed me behind my back and attached the nipple clamps to a hook on the wall.  He then attached a length of chain to the ball weight and secured that to the wall as well.  He grabbed a head harness and secured it to my head, complete with a pecker gag.  The blindfold wasn’t attached so I could see myself in the mirror.  Just looking at myself in the mirror had me hot and horny.  What a night so far.

He left me for a little while.  It became difficult to remain the position I was in but every time I moved or adjusted myself the chains to my balls and nipples would pull sending me into more pain.  My cock started to softened, which was not a good thing as the pin prick lining started to scratch it my cock as it moved inside the sheath.  I began to realize that this wasn’t just him setting up whatever was next but also part of the torment.  As I dwelled on it my cock started to harden again, which again caused pain as the pin pricks did their job.  The mind fuck started to set in.

After about 15 minutes, he returned and asked how I was doing.  I mumbled through the gag that I was ok.  He chuckled at that.  He came up behand me and twisted my nipples and slapped my balls.  “OK? Just ok? Looks like you are loving this.” 

He unclamped my nipples and proceeded to continue their torture.  They were red and angry with me.  He unhooked my balls from the wall and led me by my balls to the next room.  Leading me my balls got me hornier as the pin pricks dug into my swelling cock.  I stood in the center of the room where a bar was hanging from the ceiling, connected by pulleys that lead to the ground between my feet.  He removed the ball weight and the cock sheath and I breathed a sigh of relief.  He smacked my balls and said “don’t be so relieved.  You may beg for the weight and pin pricks after this.” 

He removed the handcuffs and secured the leather restraints to the bar sitting in front of me.  He told me to hold the bar with my hands although it didn’t matter since my cuffs were attached to the bar.  He went back to my balls, securing them with a leather strap.  He then grabbed the rope between my legs, which was attached to the pulleys and to my hands, and pulled it.  My hands went into the air so that they were perpendicular to my body.  He ran the rope through the leather strap attached to my balls and continued to pull on it.  He told me to bend my knees slightly which relieved some of the pressure on my balls.  He tied the rope off by my balls and left me in this position, with my knees slightly bent and my balls attached to a rope connected to the floor, then the ceiling, and then to the bar my arms were holding out.  He grabbed another metal bar and attached one end to my collar and the other end to the bar connected to my hands so that I couldn’t pull my arms back in toward my body. 

He grabbed a length of what looked like heavy chain and attached it to the bar connected to my arms.  The additional weight made me have to work to keep my arms up, as the slight downward movement yanked on my balls.  He slowly added weights to the chain, and now I was really struggling.  My arms burned as I tried to keep the bar up.  I would rest my arms a little and then my balls were yanked downward by the additional weight.  I groaned into the pecker gag and tried to stand straighter to relieve the pressure on my knees.  Again my balls got yanked.  I looked down to again see my traitorous cock at full mast, leaking away as it apparently enjoyed this predicament.  He said he would be back in a little while and left me in the room.  The mind fuck just went up a notch. 

As time when on and my arms started failing me the pressure on my nuts became intense.  I started to panic a bit and began to groan loudly in the gag.  I continued to fight with the predicament and just kept yanking on my balls.  Sweat poured off my body.  Right when I thought I couldn’t take it anymore he reappeared. 

“Don’t worry; I was watching you writhe in pain.” As he pointed to a camera I hadn’t noticed before.  “So you want out?”  I nodded yes and looked pleadingly into his eyes. 

“Well, you know how this goes.  I can take you out now, and there will be a punishment.   Or you can go 2 more minutes with another 5 pounds of weight added to the chain.  Your choice. Be careful what you wish for.”

I thought my arms would fall off if he added any more weight.  I was fearful as he didn’t say what the punishment would be this time around.  The flogger was brutal on my cockhead with the clothespins but I handled it.  I could take the pain of that so I figured I can take another punishment.  If he added any more weight to the bar either my arms or my balls would rip off.   I mumbled “punishment” through the gag.  He just smirked.

He unhooked the weight from the bar and released my hands and my balls and removed the head harness.  “Remember no touching, or you’ll wish you never did.”  My cock had gone soft as he allowed me to stretch my worn out body.  I resisted the urge to grab my cock and shoot a huge load.  I was exhausted but hornier than ever.  For my first real life experience, this was incredible.  I didn’t think I could handle all this. 

He gave me more water and again asked if I needed the rest room.  I needed to pee I told him.  He led me to a rest room.  Before entering, he cuffed my hands behind my back and reminded me no touching.  He followed me into the bathroom where he told me to sit on the toilet.  I complied as he pushed my cock into the bowl.  “Go ahead”.  I became a bit pee shy and asked if he could turn around.  He responded by twisting my nipples.  He did turn around and eventually I began to pee.  I told him I was done and he shook my cock in the bowl to make sure there was no leakage.

I stood up and he grabbed me by the balls and led me back into the room we were in.   We stopped again in the center of the room and he connected my collar to a chain hanging from the ceiling.  He went and grabbed the ball weight he had previously, although it looked a little different this time.  It had two long screws angling downward from the weight.  He proceeded to attach it and I immediately noticed it was heavier than the weight he used previously.  He then pulled a metal bar from his pocket and secured it to the two screws hanging from the weight.  As it got tighter, my balls were now being weighted down and crushed by the bar.  I began to grimace in pain as my cock woke back up.  “I see you like this.  A few more turns then to make it less enjoyable for you.”  As promised, the bar got tighter and tighter around my nuts and sent pain up into my abdomen.  My cock was back at full erection again.  As a punishment goes, I think I can handle this more than the weights.  I breathed a sigh of relief.

He unhooked me from the ceiling and brought be back to the waiting area by the mirrors.  Again, he attached nipple clamps to the hook and attached my crushed and weighted balls to the hook in the wall.  He came back with a few items.

“And now for your punishment.”  Wait, the ball crusher wasn’t the punishment?  I became extremely nervous for what was next.  He put a gag in my mouth and secured it tightly around my head.  He showed me a countdown timer set at five minutes.  He reached up and showed me a handful of clothespins.

“Oh Fuck.” I mumbled through the gag.

“I told you to be careful what you wish for.  You wanted punishment.  I expect you to make it.  No safe word unless you absolutely need it.”  He began placing them across my cockhead like before.  They dug in and I knew I was in trouble. 

He started the timer in front of my eyes and left it there.  I stared into the mirror, looking at my cock and balls wondering how I was going to survive ten minutes.  I started struggling after only a minute and pulled back too hard and the nipple clamp on my right nipple disconnected.  He immediately returned and reset the clamp in the other direction on both nipples, increasing the pain tenfold.  “Naughty boys get punished” he said as he reset the clock from 4 minutes up to 6.  “Fuck” I screamed into the gag.  My balls were throbbing, my cockhead on fire and my nipples screaming.  How am I going to make it 10 minutes like this?  I felt my erection starting to subside and the pain became worse.  I knew I had to stay on the edge to make it through this without my safe word.  I gently pulled my balls to make the chain to the wall more taught and that sent a jolt of pain into my abdomen.  I closed my eyes and connected to the pain and tried to stay hard.  It seemed to be working.  I opened my eyes again and saw the clock was at 3 minutes.  Ok, almost halfway, I can do this.

At the 2 minute mark, he returned and placed more clothespins down my cock to the scrotum that was exposed above the ball weights.  He added clothespins to my ears as well.  I’m really starting to doubt I can do much more.  My limit is fast approaching.  He then smacks my ass with some kind of paddle.  Corporal never really interested me before but seeing him the mirror whacking at my bare ass increased the scene.  Every time he hit my, the shockwave went through my body, yanked at my balls and made the clothespins jumble around, shooting pain through my whole body.  My hands, still behind my back, try to block the blows involuntarily.  He grabbed my arms with his free hand and kept up his punishment.

The timer hits zero and he stops with the paddle.  He removes the clothespins and starts smacking my cockhead with the paddle. I jump and scream into the gag as the nipple clamps rip off.  He leaves me be for a couple of moments while I regain my composure.  He removes the gag.

“Ok, time for a break.  A real break this time.  You have taken a lot of punishment so far, especially for your first time.  I’m going to keep you restrained, to make sure you don’t go for cock and balls, but we will do some stretching first and then go relax for a little while. While we stretch, I will keep sheath on your cock so you know not to grab it, as the pin pricks will dig in. “

“Ok thank you sir.”  He puts the spike sheath on my cock and leaves the ball weight and crusher attached.  We take ten minutes to stretch as he said, and I give my body a rest.  My cock softens, pulling on the pin pricks, but I focus on stretching, drinking water and relaxing.  Once I’m done, the leather wrist and ankle restraints are removed and replaced with the metal leg cuffs and hand cuffs behind my back. He removes the cock sheath and ball weight / crusher and leads me to a couch in the corner.

“You’re doing very well.  I usually don’t push that hard with a newbie but you clearly can take it and want it.”

“thank you sir.  I admit that it has been pushing my limits all day but I didn’t want to use the safe word.  That last punishment was really hard.”

“Yes it was.  I thought you may not handle it but you really did fine.  Drink some more water.  You’ve been sweating and straining a lot and need to keep up hydration. “He held up a bottle of water with a straw and I gulped it down.  I was thirstier than I thought.

“We’ve now been playing for almost two hours and I don’t think I can push you much harder today.  So I will give you a choice.  We can do one last scene, where I push you to cum.  I will tell you it will hurt, as much if not more than what you have already experienced.  But it will be a little quicker to orgasm as I know you have been through so much already.  Or, if you want to really push, we can do a smaller scene with less physicality, no cumming, and you spend the night and we resume tomorrow with two or three more tough scenes.  I see you cock is interested in more, but really think it through.  Spending the night won’t be easy, as I won’t just let you sleep in a bed and give into the temptation of touching your cock.  There will definitely be chastity involved and maybe a few other things.  So, don’t just listen to your throbbing cock.  Think about what you want.  This is only your first play session and you will have many more.  So wrapping up tonight is no problem.”

It was a lot to think about.  I felt spent, that is for sure, but I also wanted more.  My cock was throbbing and begging for release.  As horny as I felt, cumming now would be great.  I looked around the playroom and saw so many other things I wanted to try.  I had nothing to do tomorrow, so I could conceivably stay the night. 

“I think I’ll spend the night and go for more.”  I didn’t believe the words coming out of my mouth.  But my cock saw all the other toys and torture devices and wanted to play.

“Ok, we will do one more scene tonight and get you set up for the night. Be sure, as once we start, I will not let you change your mind.  Tomorrow will bring much more torture than today, as you will be a newbie anymore.” He winked at me. “The rules of the safe words will change and your cock and balls will be abused.   You will still be able to use your safe words, but they will bring momentary release and a punishment.  And you saw what punishment is like today.  Once we start tomorrow you can expect heavy bondage to keep you very still while I torture you. We will change positions but you will be bound the entire time, much like today.” My cock started drooling again as he described tomorrow’s activities.  He grabbed my cock and pulled off some pre-cum with his finger and fed it to me.  “How come I talk about torturing you and your cock gets harder?  I wonder.” He smiled at me.  “so now, are you sure?”

As he continued to feed me my pre-cum, I could no longer think straight. I agreed to spend the night.