Regrets (or A Very Long Weekend) (M/M)

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Chapter 1: Arrival

I arrive at the airport and meet you at the bag claim. I’m in the white tennis uniform that we pre-agreed on, with only a hoodie over the shirt to hide that I’m fully kitted out for sports. I hand you my duffel bag and keep my backpack on. We walk awhile to your car, going to the far back of the parking garage where I see your car alone in a dimly lit corner. You have me walk around to the passenger door as you put my duffel bag into the trunk. You have me remove my backpack and hoodie and also place those in the trunk. You check my pockets, easy to do since I’m just wearing tennis shorts, to be sure I don’t have my phone, keys, or anything else.

Then you have me get into the car, where I see the tools to be used on the ride to your place. First, you lock leg irons around my ankles, which are already locked to something under the seat to limit my leg movements. Then you put on my seat belt and cuff my hands behind me, smashing my arms against the seat back. You pull the seatbelt out and then let it retract locked, keeping my body pushed against the seat with my restrained hands behind me. A short length of chain then goes around my neck and is locked in, then tied off to the headrest so I can’t even lean forward the little amount the seat belt allows.

Now secured, you go around and get in the car and start to drive. You ask me to verify what we both know is in the printed contract in my backpack. That we’ll get to your place and do my first challenge to determine how things go until morning. I’m yours for a full 48 hours, so you have all evening, overnight, the full next day, a second overnight, and part of the last day. It’ll be a long time if I find myself in uncomfortable positions the whole time. I’ll have four challenges during the time, and each one determines what happens until the next one…or in the case of the 3rd challenge, how I spend the rest of the trip.

In addition to that, the document spells out limits that we’ve agreed on, a couple pre-agreed positions aside from the pre-determined challenges, and the position I’ll be placed in should I fail a challenge or otherwise earn punishment from misbehaving. Once I sign it and agree at your place, I’m locked in for the duration…especially since the document gives you permission to physically force me back into restraint should I resist. Besides, you’ll keep enough restraints on me even when moving me around that I won’t have much of a chance to fight back.

We get to your place and you leave me in the car while you take my things inside. Then you come back for me. I’m already starting to shiver without the car’s heater running since I’m just wearing shorts and a jersey for warmth. You undo the seat belt, then unlock the chains from the car seat, and finally unchain my legs & neck. You stand me up and walk me inside, staying close behind me to keep any neighbors from seeing my cuffed arms.

I don’t see my bags in your living room, but I do see that you’ve pulled the contract from my backpack and laid it out on the kitchen counter. You offer me a pen and tell me that now is my last chance to back out. I can refuse to sign and you’ll let me use my phone to book a hotel room near the airport to stay in until my flight home. I came all this way, and wasn’t about to back out now, even knowing that I’d be your captive until my flight home. I grab the pen you offered and awkwardly sign with cuffed arms. You point to a door and say that’s the bathroom I’ll be using if you decide to give me any bathroom breaks…and that I should use it now before we get started.

I go in and do my business, then spend some time to wash up after the flight. I do notice a douche ball you left out and think it best to make use of it, so I clean out as well.

I come out five or so minutes later and see that you’ve set up my first challenge, as well as some of the other key components of my captivity. There’s a sturdy wooden chair in the middle of the living room. Above it, attached to the 18 foot ceiling is a sturdy eyebolt with a cable hanging from it. The cable ends in a loop with a padlock locked to it, and goes up through the eyebolt and down to a winch bolted to a large board that you’ve put about 250 lbs of weight plates on. On opposite walls, just at floor-level, are another pair of eyebolts bolted in. Those will come into play later…but for now the chair is of concern.

[60Cancer]

A nice little session.

[slider40337]

Chapter 2: First Challenge & First Night

You sit me in the chair and pull my cuffed arms over the back. You then chain my legs with the leg irons, running the chain between the chair legs so my legs are spread on either side of the chair with my ankles pulled underneath. Then you buckle a ballgag on me super tight, then cover it up with 10 duct tape wraps fully around my head. I look down and watch as you tie the handcuffs’ keys to my tennis shorts waist string using many tight and complicated knots. Once you finish, you also put tape over my eyes to blind me. I hear you twist an egg timer, and you tell me I have 15 minutes so I’d best get started.

I get to work and try to work my body around so my hands can get to the string. It takes a painful stretch, but I’m able to manage it eventually. I start working on the knots, having to take breaks sitting normally in the chair due to the stress of it. Just as I feel that I’m on the last knot or two, the timer dings.

Wordlessly, you unzip the fly of my shorts and pull out my hard dick. You put lube on a hand and start stroking. The stroking feels amazing, but I know that I lose the challenge if I cum. I keep working the knots, noticing that you just adjust your position and keep jacking as I twist my body. The keys come loose and I put a finger through the keychain so I don’t drop the keys onto the floor out of reach.

I’m getting closer and closer to cumming as I keep trying key after key in the locks. Just as I feel that telltale feeling of being about to shoot, the key turns in a cuff and I get an arm free. I reach forward to stop you from making me cum, and you laugh and let me finish freeing myself so I can chain myself up for the night.

Once I finish getting free, you cuff my hands back behind me and take away the keys, then let me blindly find my way to the bathroom for a break. You order me not to close the door, and to clean out again. Once I finish, you chain my legs together and lock that chain to my cuffs for a light hogtie as you watch some TV for the evening. Eventually you let me out of that and tell me to chain myself for the night as we discussed. You lead me to a spot and reach my hands up so I can feel the hanging cable from the ceiling, which is just above my head currently and has an open padlock on it.

You hand me the handcuffs, keys, and a couple lengths of rope. I take off the tennis jersey and my athletic socks, leaving me only in the shorts as agreed. Then I sit down and proceed to use the rope to tie my ankles and knees together. I put the handcuffs and key in my shorts pocket and stand back up. Then I put on the cuffs, double lock them with the key, and then slip the key into the rear pocket of my shorts (which I then zip closed after). I reach up and find the open padlock on the cable and use it to padlock my cuffs to the cable.

I then hear you click the winch, slowly raising my arms up high until I’m standing fully straight with my arms above my head, slightly onto my toes to relieve tension on my hands.

A few moments later, as agreed, you unzip my shorts and start slowly jerking me. Since there’s no time limit for this edging, I can only do my best to hold out and keep from cumming. You seem to be determined after my success earlier, so you eventually go fast and hard. I can’t do anything about it as I eventually moan into the gag as I shoot my seven-day load all over the floor.

I sag with defeat against the cuffs holding my arms up. After cumming, I really want out, but I know that our agreement doesn’t give me a way to have you let me go. You untie my ankles, as agreed for the consequence of cumming, and retie my legs spread so wide it hurts a little from the stretch. I’m totally helpless as you unbutton my shorts and pull them down. I feel the pressure from behind, but can’t do anything about it as you force in a large plug. You tie a short rope around my waist, thread both ends through my crotch, and tie them tight to the waist rope. The tight rope harness will make sure I can’t have any chance of pushing out the plug. I also feel you tie paracord to my balls, then pull up my shorts. I know you’ve left the ends of the paracord hanging out the legs of my shorts and, once again as pre-agreed, you tie a weight to each paracord end.

The ball weights just add to the torment of being strung up with spread legs and a big plug in me. I recall the contract I signed saying “here overnight, no way out or safeword to release me early” and wonder what trouble I’ve gotten myself into as my gagged begging goes unheard as you walk away to go to bed.

[dwild]

Super hot, looking forward to more ...

[tickletied84]

Excellent - loving the mix of knowing what will happen, and then experience of actually having it happen to him.

A lucky/unlucky way to spend the night!

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The night seems to last forever. The handcuffs are biting into my wrists and the only way to relieve that is to force myself onto the tips of my toes. Sometimes I find myself trying to push out the plug, but the crotch harness ensures it’s going nowhere. I quickly learn not to struggle too much, as it makes the ball weights swing. I eventually fall into a pattern of holding myself on my toes as long as I can, then enduring the pull on my arms as my legs rest. I just focus on the pattern of alternating between legs aching and wrists screaming.

Suddenly, I notice the click of the winch and feel my feet fully hit the floor. I moan with relief as I’m able to stop and am looking forward to even the short bathroom breaks we agreed on. I’d had to pee for awhile but was managing—barely—to hold it. I feel you unzip my shorts and pull my dick out. “Go,” you say.

I don’t even wait to guess what you mean. I relax and let my urine flow. From the sound, you’re holding up a pitcher or bucket or some such. The relief is tempered by the realization that I’m not getting even a short break. Once I finish, I feel myself cleaned up with a wet cloth before you zip my shorts back up. You cut the tape over my gag and painfully rip it off, then unbuckle the ballgag. “No words, or I winch you up for the next 24 hours,” you say as you remove the gag.

You shove a straw in my mouth which I eagerly drink from. The cool water is amazing after my rough night. Then I’m fed a meal bar and given more water before the gag is once more buckled on tight and covered with wraps of tape.

Now securely gagged and still blinded, I feel you uncuff my arms. I go to rub my sore wrists but you grab my arms and put them through a shirt: the soccer uniform I’d brought. You get the shirt on me before cuffing my arms behind me. To secure me in place, you loop a chain around my neck and lock it to the hanging cable. Then you free my legs and remove the tennis shorts. You put on the shorts that match my soccer jersey, followed by the socks and cleats. As a last touch, you tuck my jersey into my shirt.

Having been changed, I’m ready for my next challenge. You shackle my legs together and undo the neck chain. You get me onto the floor and padlock my handcuffs to my leg shackles for a hogtie. Then you roll me onto my side and tie the keys to my cuffs to the waist string inside of my shorts. You roll me back onto my stomach and complete the final bit of this restrain: padlocking both my handcuffs’ chains and leg shackles’ chain to the hanging cable. You winch it up, pulling high enough that my knees are totally unable to reach the floor and my shoulders are also pulled up off the floor. “Thirty minutes,” you way, as I hear the twisting and subsequent ticking of the egg timer.

My first move is to try to lift my waist straight up, but that swiftly fails as that maneuver makes me fully hang (due to my shoulders and knees being pulled up off the floor) and I don’t have the muscle to pull up while hanging. I then grin behind my gag as I reveal the trick I hadn’t told you about. I turn my body over so I’m leaning my weight on the cuffs and slowly exhale. I squeeze by butt between my cuffed wrists and it doesn’t take long before I push my body through and find my hands cuffed in front of me instead of behind. It takes only a few seconds to get the key and unlock one of the cuffs. You quickly grab my hand and take the key away. I grunt in protest, but you just speak calmly. “I’d call that cheating, but it’s not fair to force you to lose after already succeeding. You win this one, but you stay like this until your next challenge.”

You roll me back over and cuff my free hand back into the cuffs. To be sure I can’t get my cuffs in front again, you lock the short chain around my neck again, and then run another chain from that to my cuffs and secure it with padlocks. There’s no real pulling on my neck normally, but I can’t get my arms low enough to bring my hands in front anymore. I squirm and moan into the gag at the evil semi-suspended hogtie, but I know that I have no way to make you let me out so all I can do is deal with it and wait a few hours until my next challenge.