My First Customer Ch. 02 Pt. 02

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My 2nd session takes a turn as I'm hung, bent, and violated.
3.5k words
4.72
21.2k
9

Part 3 of the 3 part series

Updated 06/08/2023
Created 02/24/2018
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Darkwatch
Darkwatch
281 Followers

The warm sun felt wonderful, caressing my skin as I was hanging in my daze. The gentle breeze cooling the sweat from my tortured skin. Mistress Wendy had left me hanging from a tall tree in her back yard after whipping my ass soundly, and I wasn't sure just how long I had been left outside. My hands were pinioned behind my back and tied off to the collar around my neck. My left leg was also tied, rope wrapped around my knee raising it high and pulled from my frame. I just knew that it was an amazing thing: the quieting of a hectic mind that keeps analyzing everything around you all the time, and just giving yourself a chance to simply feel and experience.

I was startled by a darkly seductive voice from behind me rousing me from my reverie, "You've done well to take your punishment and not give in to weakness, Danny. I love the red stripes I've added to that backside of yours. I think I've toyed with your body enough, it's time to shift to messing with your mind. Let's get you back inside because I really desire to hear your moans, they so excite me."

She went to my leg and unwound the rope holding my knee up and out, allowing me to finally put both feet on the ground. That in itself was a relief and I shook both my legs out to unknot the kinks in my muscles that had formed, contorted as I had been. She undid the rope from behind my back to my neck but leaving my hands secured. Coming to my front she sighed in discontent, "What's the matter with that dick of yours, Danny? It seems to have lost interest in our little session, are you trying to express some sort of displeasure in my treatment of you?"

I grunted "no" against my ball-gag and shook my head as she reached down with her gloved hand and took my balls firmly in her grip. "Come along now, I guess if you can't be led by your prick, I can still take you by the balls."

She pulled hard and led me back across Her yard, naked and helpless as my hands were still tied behind my back. As soon as I felt her fingers wrap themselves around my sack, my dick instantly responded, growing rock-hard, but She was having nothing to do with it as I was led mercilessly by my balls. Through the yard, across the patio, and into the cool dungeon I was dragged, my eyes blinking to readjust to the dark red interior. Mistress Wendy brought me to the far side of the room and released her iron grip on my balls and barked, "Sit, sub, on your ass. Right here!" She indicated with a tapped boot where I was to place myself.

As I lowered myself she smiled, "There is no playroom as well equipped as your mind. My little dungeon will have to do, so lay there and take what I have to give. Embrace every bite of pain, every humiliation. Your whimpers make me smile, but your begging feeds my Dark Goddess."

I had to wince as my sore backside rubbed against the floor. I was sure I was going to feel Her marks for a week at least. She went to the wall and returned with the spreader bar and kicked my legs out wide, fastening first one ankle cuff then the second forcing my legs into a wide split. Going behind me, I could feel her untie the wrist cuffs. Finally, I was able to release my hands from behind my back and it felt so good to get the blood back into my overworked shoulders. Prodding my chest with the toe of her booted foot Mistress commanded, "On your back, hands at your side, now."

I lowered myself to the cold floor again wincing from the pain of the welts that were already forming on my back. Mistress Wendy first turned my head and unbuckled my ball gag. It came out trailing a line of slobber against my chest and she put it to the side and next gathered up a length of green parachute cord. She went to my right wrist and fastening it to one cuff, ran it down my body, past the spreader bar to the wall by my feet where it looked like some eye-bolts were set. She ran it through two that were set in the wall a few feet apart then up to my other arm. Pulling tightly she tied it off effectively pulling my arms down and apart flat on the floor. After all the time I had spent hung from the tree, it actually felt good to be stretched in a completely different way.

"It's time to make use of my hook in the ceiling, Danny. I know you two got along fabulously last time you were here, so let's get you both reacquainted." She took a rope hanging down from the pulley and ran it to the spreader bar and clipped it off with a carabineer. Going back to the wall where the small winch was, she began to take up the slack to the pulley hanging from the ceiling. I noticed it was not directly above me, but further down in the center of the room above my head. Once the rope was taught, She began to use the ratcheting device with a loud, sinister "clack, clack, clack..."

Slowly raising my legs from the ground, I began to get a bit nervous once they were straight up in the air and my butt began to rise as well. With my hands tied off the wall, I was slowly being bent in half as my legs continued into the air and I was hoping she wasn't going to try to suspend me upside down. My fears were unjustified, as she stopped before I became totally lifted off the ground, but I was left with only my head and shoulder blades still on the floor, arms stretched downward and my legs and butt raised high, my midsection bent directly over my head.

She came over and stood between my raised and split legs. Putting both hands on my ass and leaning between my legs to leer at me she sniggered, "Oh Danny, another fine pickle I've put you in! From that vantage point, you'll have a good view of what I'm about to do to you next. I reread your list of hard limits and lo and behold you didn't put 'anal' on it. One thing you are going to learn about me today is that I have a bit of an anal fixation. Violating men makes my Dark Goddess smile. Have you ever had anyone fill your ass before Danny?"

"No Miss Wendy," I gulped

"Well, today is a day for firsts then, isn't it? I'll be a considerate Domme and start off slowly. You'll take what I give you, your body is mine, I can't wait to break you and hear you say "Thank You"."

She smacked my upturned ass and went off to her toy chest and came back with a small black dildo with a flared base and a bottle of lube. "Ready to lose that anal cherry of yours, Danny?" she queried with an evil smile playing across her lips. She turned over the bottle and I felt a trickle of cold fluid drip onto my exposed butt hole sending shivers through me. I admit I had been curious about this for a while, and even though I was scared, I was also excited to experience this for the first time. I felt her finger rub the lube across my asshole sending shivers throughout my body and making me wiggle in my bondage.

She took the little plug and put the head against my tight puckered hole and I could feel it part my flesh. Closing my eyes, I involuntarily squeezed my sphincter muscles, but she just slowly pushed it past the muscles and I could feel it invade my inner recesses. I was expecting pain but was happily surprised that none was coming, just a feeling of being exposed and penetrated.

"There, that wasn't so bad, now was it?" Miss Wendy said and I opened my eyes to see her grinning down on me.

"No, I didn't know it was all inside me," I replied.

"Don't worry, I'm just getting started," She laughed. "I plan to have thoroughly violated your ass and mind by the time I'm done."

She took hold of the dildo and then pulled it out of me, and I could feel the void is created as it exited. She didn't give me time to relax as she then pushed it back inside making me gasp. Out, then back in it went and it felt really weird, but also good in a very strange way. My brain was still foggy from the whipping I had received, and it finally dawned on me that Miss Wendy was now fucking my ass with her dildo!

"Oh Danny, it seems you like being fucked up the ass, don't you?"

"No Miss Wendy," I gasped

She pushed the dildo to the hilt until it popped in and then took her left hand to smack my ass hard, "You shouldn't tell lies like that in the position you're in, besides your cock gives you away." Her hand found its way around my left leg to grasp my now erect cock and I gasped as she took hold. I hadn't realized that I had gotten hard again, but she had me under her spell and my body was surely not my own.

"For that little bit of prevarication, I'm going to get a bigger dildo to fuck you with. You aren't ready to take a real one, yet... but you'll get there with my training."

I had no idea what she was meaning but was not about to ask. She left me upside down, staring at my throbbing dick with her dildo still forced into my asshole as she went and got another larger dildo. Coming back she smacked the long phallus shaped piece of rubber against my forehead. "Time to continue your training, Danny. You really won't sit down straight for a few days when I'm done with you today."

I felt the smaller dildo pulled from my hole, but then the new one press up against it. It didn't want to go at first, and she worked it around in circles getting lube all over it. I tried to shift position but was held bent over too well as she pressed hard and forced it past my sphincter muscles to suddenly invade my rectum. "Ow!" I yelled as I was taken by the sudden pressure deep inside me. "Oh my god, it hurts!"

All I got back was a chuckle, "So?" as she continued to lean into me pushing the dildo deeper into my body. Red flashes of light flashed across my vision as my anus struggled to expand to take Her dildo inside me. "Relax, just breathe in and out. You have no choice but to take it up your ass so you might as well enjoy it a little," instructed Miss Wendy from somewhere above me. I realized I was holding my breath and forced myself to release it and try to do as I was told and found that the pain was subsiding and being replaced by a feeling of immense fullness between my legs deep into my core.

Slowly, ever so slowly she filled my backside with her dildo until I thought I was going to be split in half. I had no idea what bigger ones she had, but I didn't want to find out as I would never have guessed I could take this one. Satisfied that I wasn't going to give in and use my safe-word, Miss Wendy began again slowly fuck my ass with her toy. Opening my eyes I saw her using both hands to inexorably use her dildo, sawing into my upturned ass and my engorged cock pointing straight downwards at me.

She obviously noticed it as well because once I was sufficiently enlarged, she just used her left hand to continue my ass-reaming and reached around me to grab my dick. I shuddered, "Fuck! Oh my god, that feels so good."

"Being fucked up the ass? I had to ream my main sub many times before he began to enjoy it, I guess you're a quick study?"

"No, not that," I gasped, "Your hand on my cock."

"Oh, does this feel good, Danny?" she mocked me as she used her fingertips to rub the sensitive spot under the tip.

"Oh please yes... oh shit, oh shit, that feels so good."

She stopped rubbing leaving me gasping. "No, don't stop, please."

"Why would I continue?" She asked. "This isn't about your pleasure, remember?"

"Miss Wendy, please."

Her hand returned to my dick sending shocks throughout my entire body. She continued to fuck my asshole, but again slowly stroked my cock and it felt so good I was quivering all over. I could feel myself start to climax, waves of pleasure emanating from my dick being rubbed by my Mistress. "Oh yes, that's it, I'm close," I groaned.

"Oh no you don't," She sternly said. Gripping my shaft tightly she redoubled her thrusts with the dildo dragging me back from the edge. "You are not allowed to cum in my dungeon without my approval, Danny. That was not in our arrangement. You must remember that male submission isn't about being used, submission is about being of use - to Me."

I couldn't take the edging and said in a guttural voice, "Please Miss Wendy, may I cum? I'll do anything. Please give me a release after all this."

"Hmm." She mused as she again ran her thumb along my shaft making me quiver as I began to rise again. "I suppose we could renegotiate our contract if you want. It'll cost you double my price for starters, plus you have to write down this experience so I can share it with my readers."

"Done, done," I hurriedly agreed.

"Okay, and it will also cost you in a more personal way too, stay right there."

She went away leaving the dildo protruding from my gaping asshole and me breathing hard as my cock was left wanting again. She went to her toy chest and returned with what looked like a ball-gag, but with a large ring instead of the ball. Bending down she ordered, "Open wide" and fitted the ring between my jaws, then buckled it tightly leaving me mouth agape and unable to do anything but grunt and groan as she stood up and forced the dildo back fully inside me splitting me wide open.

She reached around and began to stroke my prick which was now throbbing and making me senseless. I was just groaning and doing my best to feel the rise inside me as she was distracting me with the constant drilling of the dildo against my prostate. "You really want to cum, Danny? See where that dick of yours is pointing? Straight down at your face. If you really want to cum, you can, but you'll also get to feel what it's like to get a facial, and I'm going to do my best to aim it straight for your open mouth, won't that be delightful?"

With a hard smack on my ass, she continued, "This is reduction: You have been reduced from being a human to just an object. You have been reduced to a body, an ass and cock for our pleasure. You are a slave, an object, human stock. You own nothing. Not even your body. I decide how we use it, how I punish it and when, how and where I display it. Isn't that right?"

I could only thrash about, unable to even grunt a response.

Her masturbating my dick, as well as her thrusting the dildo was causing my excitement to climb. I could feel my orgasm that had been denied me for so long rise and was spellbound watching her rub my purple straining cock and seeing that she was right, it was aimed right for my face. "Grunt once if you want to cum, Danny."

I couldn't stop it and gave a loud grunt as I felt all my muscles clench up, and even more amazing was feeling my sphincter pulsate around the dildo which surprisingly only heightened the sensations. My Mistress firmly grabbed my dick, her thumb right below the head, "Ok, you may cum. Do it, cum now!"

I felt my climax arrive and my cock strain. Then I saw it, a stream of my white semen explode from my dick right at my face! Laughing, my Mistress adjusted her aim after the first spurt splashed against my forehead, and the second one jetting across my mouth getting a healthy gob past the ring-gag into my throat. Augh, it tasted salty and was hot and thick. Oh crap, another spurt and another followed as my body spasmed, writhing across her dungeon floor.

I couldn't control my muscles as my legs shook against the spreader bar over my head and I could still feel my anus pulsing around the dildo as my orgasm went on and on for what seemed like an eternity of release. While I was coming down, Miss Wendy continued to milk my sensitive cock and draining the last drops onto my face. Finally spent, all my muscles finally just went limp leaving my hanging there as I semi-consciously felt the dildo being pulled from my asshole. In a haze, I saw my Mistress set it aside and going to the winch slowly release it letting my legs relax and it was a relief as my body was straightened back out. I was sure my back was going to be sore tomorrow from being bent in half for so long.

Miss Wendy came over to me, bent over and after unclipping my feet, released my hands from the cuffs. She turned my head and unbuckled the ring-gag and began rubbing my wrists to get the blood flow back into them asking, "Now how was that, Danny? Was it worth the extra cost?" She chuckled, "As they say, was the juice worth the squeeze, pun intended?"

I cleared my throat and wiped off my face with a proffered towel. "Oh yes," I sighed, "I don't think I have ever cum so hard in my life."

"It looked, shall we say, 'explosive'. I bet you've also never been forced to taste your own cum before."

"No, that along with pretty much all of today was a first. You did an awesome job pushing my limits, I thank you."

She removed my collar and ruffled my hair. "You need anything? I don't want you to think I'm neglecting your aftercare."

"Just a drink of water perhaps."

She dropped off some of the tools of her trade on her workbench and got the requested glass of water. She seemed to glow as she returned and I received the proffered glass with a, "Thank you, Mistress."

With a rub of my shoulders, she reminded me, "Now don't forget. You owe me for letting you cum. That's not something I plan on making a habit of in the future. I expect you to fulfill your promise and write down your experiences here today and email it to me."

"Of course, Miss Wendy, thank you for being so kind."

"That's not a word usually associated with me, however, take your time getting ready and let yourself out when you're good to drive home. Feel free to contact me if you need another session," She said as she sauntered out of the dungeon and down the hallway. "I am able to release the tight rein you have on your mind, your self-control. Vanilla people don't realize a Domme can provide what you need, sometimes something you didn't even realize you needed." I relished being able to watch her ass sway as she left me on the floor pondering what she had just said.

I heard a door close and I lay prostrate across the floor for several minutes trying to do my best to regain my senses. I thought to myself, "Holy shit but that was intense. I'm not sure how badly I'm marked up, but she sure did a job on my back." I considered if my "itch" had been scratched, and if so was it gone for good?

I got up and went into the entryway with one last look at Her dungeon where I just had experienced one of the most intense, painful, satisfying, and weird afternoons of my life. I gingerly put on my clothes after returning the cuffs to the table. "Yup, it's a good thing I wore these boxers," I thought as it stung putting them over my cheeks. I added some more bills to her payment envelope and let myself out the door.

With a wistful sigh, I thought, "I have homework to do to write up this story when I get home. I wonder if my "itch" will return and bring me back again for Mistress Wendy to scratch?"

Darkwatch
Darkwatch
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DarkwatchDarkwatchalmost 2 years agoAuthor

thanks for the truly constructive input, Emirus

EmirusEmirusalmost 2 years ago

An enjoyable story particularly the first chapter. The first chapter got across her sadistic tendencies very well but I don’t think the second and third chapters were as effective in respect of his masochism.

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I thought the telling of the first chapter from her point of view and the second chapter from his worked well. Although the third chapter (this one, was good I think it would have been even better, and a really good finale, if it had been told from both his and her point of view.

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Some minor grammatical errors but rarely have I read a story, no matter how good, which don’t contain any.

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I think you would enjoy reading Cruel Mistress by Saffyre which is my favourite sadistic mistress/devoted masochist story.

AnonymousAnonymousabout 4 years ago
Intense and beautifully written.

Having read the three parts of 'My first customer' I can only say Wow what a excellent work of erotic writing. I especially liked the first part told from Mistress Wendy's point of view and then the next two sessions from the customer Danny's angle. Very well written, extremely sexy with a fantastic description of anal penetration with a sweet ending for Danny. Thank you Darkwatch, will be reading more of your writing and five stars yet again.

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