Gimp Weeend

I climb in the back of his black suburban, the windows tinted so dark that it looks as though no one is in the car. I adjust in the heated leather seat, which feels nice. It's January in Chicago and this is a particularly harsh winter. The temp on the nearby bank sign reads -4 degrees outside.

"Good morning James, hope you slept well," he said as I close the door.

"Good morning, I slept okay, more nervous than not, but I'll adjust," I reply, avoiding eye contact.

"Okay, let's get moving then," an order to his driver. His apartment was about 40 minutes away, which meant plenty of time for small talk in the back of this very nice SUV, something I couldn't afford.

"Okay, James. Do you have what I asked you to bring?"

"Yes, I have it," as I fish the paper out of my pocket and hand it to him.

"Good, did you sign it yet," he asks?

"Yes, I have."

"Let's review verbally, and with my driver as a witness. I hope you understand, I always need to protect myself. Many boys have tried lawsuits and failed."

"I understand."

He begins reading the contract out loud and I am required to verbally agree to each one, or the driver will turn around and drop me off. I've already signed a NDA, so this never happened if it should come about.

"I, James Griffin, agree to submit as a leather gimp beginning the date of 12th of January at 8:00am through the 14th of January at 7:00pm and will agree to the following activities;

To be clothed in any outfits decided by the Master, including, but not limited to Leather, Rubber, Latex, and Lace.

To be locked in a metal chastity cage, provided by the Master, for the entire duration of service, and only the Master may unlock and remove the cage after locking it.

To be subjected to bondage, oral sex, anal sex, household chores, and serving in houseboy capacity as the Master requires.

Any anal penetration will be bare, as both parties have been recently tested and abstained from sex for a period of at least fourteen days prior to dates of service.

To service any and all guests that the Master has during the dates of service as the Master requires. Any identities of guests will be kept confidential by both the Master and the gimp. If anal penetration occurs from a guest, it will be done with LambSkyn condoms. The Master also agrees to be present for any and all service with guests to ensure safety of the gimp.

Any additional requirements during the dates of service must be discussed between the Master and the gimp, the gimp will be allowed to agree or refuse any additional services once the time of service begins, with no negative repercussions.

Signed below by gimp and the Master on this date, the 12th of January."

"Good boy, now you're my gimp as the clock just struck 8:00am, so strip gimp."

"What? Here? In the car? But what if someone sees me?"

Master reaches over, unbuckles my seat belt, grabs my hair, and pulls me over his lap so quickly, I didn't have time to react. He swats each ass cheek, hard, three times each, my groans of pain quite loud in the back of the moving car.

"Listen to me gimp, you do not disobey me. When I give you a command, you are strictly to obey. You may say, yes Master or thank you Master, but that is all. Now, get these fucking clothes off before I punish you further."

He sits me back up, my ass cheeks on fire, and I remove my shirt, handing it to him. I then slide my sweat pants and underwear off together, also handing them to him. He fishes my phone, wallet, and keys from the pockets.

"Socks and shoes gimp. Let's go."

I remove both my socks and sneakers, handing them to him, as I am now stark naked in the back of this SUV, thank goodness the heat is on.

He grabs the box that was sitting to his right that I hadn't noticed, throwing all my objects in it. He turns off my phone before tossing it in. He removes my driver's license from the wallet, handing it to his driver, then putting it in the box as well. He replaces the lid on the box, and holds in front of me, "look gimp."

He locks the box closed, with a timer lock on it. It reads just short of 59 hours on it.

"This box will not unlock until 6:55pm on Sunday, which means all of your belongings are now secure and you are truly MY gimp. Your driver's license will be held by my driver in the case of law enforcement, as well as the contract we both have signed."

"Yes Master," was all I responded with. The sting of my previous punishment kept me in line as I did not want to experience that again.

I was looking at Master as he was fidgeting in another leather bag, and he pulls out a pair of leather gloves, sliding them over each hand. He was a leather Master who enjoyed using leather gimps, as his profile read. When I messaged him I didn't know who he was, but we've gotten to this point, and I've fantasized about being a gimp for years, and now I get to do it.

I had been in between jobs, and while this wasn't a paid gig, it gave me something to do on this cold weekend in January.

I was watching Master intently, when he looked over, grabbed my hair again, "Why are you looking at me Gimp? Objects don't look at their Master, just the floor. You are only to be used for my pleasure, and have no reason to watch what I am doing."

I drop my gaze to the floor, "yes Master."

I hear some more rummaging, but do not dare to look in his direction, "Gimp, on your knees in the seat, facing the window, your hands on the door."

I immediately follow directions, and I feel his leather fingers pushing against my hole. The cold lube on his fingers makes it easier for his two fingers to push past the ring. I remember to try and push out, easing the pressure. It doesn't take long for me to relax the ring, and begin to enjoy the sensation of his fingers pushing against my prostate, and a stream of precum drips from my cock.

"Gimp likes his hole played with. Good. I'm going to be using this hole quite a bit this weekend. Now, I'm going to push the plug in, take a deep breath gimp."

I do so and he pushes a medium to large size plug inside me. Just as the largest part of the plug gets through, the pressure begins to settle as I get used to the size of it.

He grabs my hair, pulling me down to the floor in front of the seat, "you made a mess of my seat gimp, clean it up."

He pushes my head down to where the small pool of precum gathered, I stick my tongue and lap up the precum, tasting the wet leather. Once the seat is clean, Master grabs my hair and pulls me up to the seat.

"We may have to put you in a jockstrap gimp, you're making a mess in my car, and I do not want you ruining the upholstery. Here, put this on," as he hands me a leather jockstrap.

I slide the jockstrap up over my legs and it's just big enough to contain my erections, but also catching my precum as I've never been more turned on.

"Give me your hands gimp," he commands.

I turn slightly and present my hands, "make a fist," and he slides two leather mitts over my hands, rendering them useless as he locks both of them on with little gold locks. Both of the locks have been engraved with his initials, ensuring that I remember I belong to him this weekend.

He reaches into his bag one more time, pulling out something that I can't see because I'm intently staring at the floor. He puts the thick leather collar around my neck, and with the click of another gold lock, it's secure.

"Good gimp, now, sit back, and let me put your seat belt back on. We will be at my parking garage in ten minutes, I need to check some emails."

I lean back into the seat, he reaches over me, his cologne invading my nostrils, causing a drop of precum to escape into my pouch. The seatbelt clicks, and I'm secure in the seat. I leave my mitted hands on my thighs and continue watching the floor.

Ten minutes go by like a flash and we are pulling into an underground tunnel of a large building in Chicago.

"We have arrived Sir," his driver announces as he steps out of the vehicle.

The door next to me swings open and the driver reaches in and removes the seat belt, "get out gimp," Master commands.

I look around and see that there's no one else here, so I step out of the car, stumbling to the pavement as his driver steadies me. Master soon climbs out behind me and attaches a leash to my collar, pulling me behind him. I follow him, looking at the cars in the lot, hoping that his neighbors don't stumble out and see me.

He pulls the leash tighter and now I'm closer to him. As he changes positions behind me, his body against mine, his leather gloved hand wraps around my face, "these cars are all mine. This is my own private section of the garage, and the elevator is also privately mine. When we get in, you are to get on your knees while we ride up to the top floor. I own this building, so we have complete privacy."

"Yes Master, thank you Master."

The elevator doors open, and Master walks in, pulling my leash with him, and once I step into the doors, I drop to my knees, kneeling next to him.

"Okay gimp, you are to position yourself next to me, on your knees, with your mitts behind your back, head facing downwards. When I need you, I will call for you. Otherwise, gimps are there, but not heard. Do you understand?"

"Yes Master."

"Good gimp, and if you're lucky, you may be rewarded for your good service."

The elevator zooms up the floors, and very quickly the doors are opening again, Master steps out of the doors, pulling my leash with him. I have not been told to get up, so I'm guessing I crawl behind him.

I begin to crawl, my mitts making it a little easier, as I attempt to keep up with his long strides, and we reach his door which is then opened for him, and we pass through to his luxurious penthouse apartment.

He pulls my leash until I'm in the middle of the living room, between the large black leather sofas, "When I'm not using my gimp, you are to be right here. You will either be sitting on your feet, with your mitts behind you, or wherever I may lock them, or you will be on all fours, whichever I decide. Again, you are not to make any noise, I will call for you when I need you."

"Yes Master, thank you Master," I push out of my mouth.

"Good gimp, now, we need to get you into proper uniform, let's go into the closet."

I follow him as he pulls the leash, crawling on the nice lush carpet, making my knees hurt a lot less than wood floors would have.

"Get up on this ottoman gimp," he commands, and I climb up. It's just tall enough and large enough for me to be on all fours, my ass exposed and out.

"Damn gimp, that hole does look inviting, I think I may fuck my new toy now. Give it my first load, which is just the first of many loads. Deep breath gimp."

I do as he says, and he pulls the plug from my hole, which makes a suction noise as it lets it go. I hear him fidgeting with a belt and I feel his cock plunge inside my hole, all the way to the base.

"Oh fuck, damn," escapes from my mouth before I can stop it.

He grabs my hair, his 8 inches firmly inside me, "What did I say gimp? You are not to be heard unless I tell you to, now you'll be punished for your lack of control."

He pulls his cock from my hole, and I feel the sting of a leather belt hitting my ass.

He hits my ass five times, and stands in front of me. His leather glove grabbing my hair again, "what did we learn from that gimp?"

"Gimps are only to speak when commanded to Master. My sincerest apologies Master, thank you Master for reminding me how to behave Master."

"Good gimp," as he drops my hair, returning behind me.

He pushes his cock deep inside me again, without much warning, but the plug has loosened me up.

He begins his thrusting, holding my leash, pulling my collar back towards him, forcing my head up, and my ass down.

His moaning is increasingly fast, he doesn't talk much, but he's focused on one thing. His thrusting feels so good, filling me up with his thick cock, and I'm in heaven.

He pulls out from me, leaving me empty and wanting more, but I dare not speak for it. I do not like the punishment. He reaches under me, putting his leather gloved hand inside my pouch, "damn gimp, there's a bottle of lube in this jock. Perfect, now I'm going to breed my gimp."

"Thank you Master," is all I say before he thrusts deep inside me once more, his cock now buried once again inside me, but covered in my own precum.

"Fuck gimp, that feels so good, I'm going to cum," he says as he grabs my leash and his thrusts becoming long and deep, until I feel him push once more against me, pushing as far into my hole as he can get, grunting as he unloads his cum inside my hole.

He stands behind me, his dick still inside me, breathing heavily while I feel his cock twitching inside me.

He finally pulls from me, and pushes the plug back inside me, keeping me open, as I'm assuming it will be all weekend long.

He walks around me, standing in front of me, "clean my dick gimp, get those ass juices and cum off it."

I open my mouth and he pushes his cock forwards in my mouth, tasting the lube, precum, and his cum, sucking hard to get every drop off.

He seems satisfied as he pulls his cock from my mouth, then walks away from me for a moment. When he returns, he pushes a ball gag in my mouth, "get off your knees, and just put your stomach and chest against the ottoman,and your mitts and feet on the floor."

I do so, and the ottoman is the perfect height as he begins tying the mitts to each leg of the ottoman. Once the ropes are secure, he walks behind me and ties my ankles to the back legs. He swats my ass a bit, not hard, but enough to make a mild sting.

He walks in front of me, and holds a little black object in front of my face for me to see. "See here gimp, this is a remote, it controls the plug in your hole. I'm going to take a shower, and my driver here is going to make sure you don't get into trouble while I'm away. You don't need your sight for this."

He places a thick leather blindfold over my eyes, and now I'm left with very few of my senses.

I suddenly feel the sharp intense vibrations of the plug in my hole as it roars to life, and then begins to thrust inside me, pushing right against my prostate. I begin moaning into my gag, and Master slaps my ass again, "Good gimp, enjoy that, I'll be back in a bit."