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My Second Tryst with Kelly Ch. 01

By: docmagnus



6 Months later

It had been 6 months since my first meeting with Kelly. That had gone remarkably well. She had been a willing, docile slave that night, and I had used her fully. I had exhibited no regard for her feelings, and only concerned myself with using her selfishly for my pleasure. I was glad I had. My instructions for her, to be implemented after that first meeting were to write up a detailed, honest account of our activities, and to post it on Literotica. She had it up about a week later.

Reading her account had been fascinating. She was reflecting on sexual activities that she'd never participated in, but had long fantasized about for the most part. Here Kelly was, in her late thirties, and she'd never been dominated before. She'd never been bound, gagged, whipped, or slapped. She'd never had a man make her come with a vibrator. She'd never been butt-fucked, and she'd certainly never been pissed on. 

According to her account, she had enjoyed herself immensely, and had been so turned on since our first encounter that she had been masturbating every chance she got. She wasn't necessarily sold on every activity (namely the golden shower), but she understood that to submit to me meant submitting to everything.

I was traveling through her territory again, so we made plans for another rendezvous, and met in the lobby of the same hotel we'd used the first time. When I walked into the lobby, Kelly was already there. She wordlessly rose out of her chair and joined me at the elevator.

She was dressed as instructed. She wore a black blouse, short black skirt, thigh-length black nylons, and shiny black heels. Her dark hair had grown out a little since I'd seen her last. It was straight, and trimmed into a bob, resembling Crepax' Valentina. I liked it, and assumed it was for my benefit.

We were alone in the elevator. I took her collar out of my bag and handed it to her. She put it on, and was still fastening it as we walked out into the hall. I leashed up the collar outside the hotel room door, opened the door, and led her in to the center of the room. 

We stopped there. I put my bag down, and instructed her to do the same. I took a ball-gag out of my bag. I grabbed her by the hair, bent her down, and gagged her. I pulled her back up by her hair.

"Put your arms behind your head." She did so.

I walked around behind her, bent down to retrieve a vibrator from my bag, and stood back up. I reached up into her skirt, and pulled her panties down to her knees. Then I reached around her chest with my left hand, to grip her right shoulder. After that, I put the vibrator in my right hand up against the crack in her ass. She instinctively moved her legs apart, straining against the constraints of her underpants. 

I crammed the vibrator down under her until it was wedged between her legs. It was a tight fit, due to the limited mobility imposed by the panties around her knees. It was time for the fun part. I turned it on.

It took a minute or two for Kelly to warm up, since we were starting from scratch. But slowly, I started to see results. She closed her eyes, and started moaning a little. Her cunt gradually moistened. Since she was wearing heels, I made sure to keep a good grip on her.

Kelly was moaning loudly after almost ten minutes, and seemed to be right on the brink of coming. I turned the vibrator off, and pulled it out. I could tell that she was surprised. I removed her gag.

"Get down on your hands and knees."

Kelly did as she was told.

"I read that you've had a lot of practice with masturbation lately."

Kelly nodded her head up and down furiously. I think she was breathing too hard to talk.

"Demonstrate for me. Bring yourself off, now."

Kelly reached between her legs and started fingering herself. There she was, almost fully dressed, on her knees with her face on the floor, since she couldn't use both hands anymore. Her right hand was between her legs, and her ass was up in the air. She started fingering herself, and came almost instantly. It was loud and intense.

I told her to stop before she could bring herself off again. I grabbed her hair, and ordered her back on her feet with her hands behind her head. She stood up, balancing uneasily on her heels. I put the vibrator back between her legs, and got her close to coming again. I stopped once again when she was on the verge, and ordered her back down to the floor to finish herself off. We repeated this cycle about four or five times. Her last orgasm on the floor was staggering. After she was through, I let her lie on the floor while I undressed.

Once I was nude, I took a blind-fold and a pair of handcuffs out of my bag. I bent down behind Kelly, and blindfolded her. Then I moved her hands behind her back, and cuffed them together. I shifted her off her knees, and onto her side.

I lied down next to her, with my cock level to her mouth. I took her 

ball-gag off, grabbed her by the hair, and pushed the tip of my cock up to her mouth. She started licking tentatively. I pushed the head into her mouth and held it there while her tongue worked it inside. Then I started slowly working my cock in and out of her mouth. I went slowly, and pulled it in and out irregularly, sometimes running the side of my shaft through her lips. I was having fun using her, and wasn't ready to just face-fuck her yet.

I took my cock out of her mouth, got up, and lay down behind her. I placed my cock between her ass cheeks, and massaged it. Then I slid it between her legs, and massaged it there as well. When I was done coating my cock with her cunt and ass, I went back to her mouth and shoved my cock back in. Now I started to get more forceful. It was an incredible turn-on to hold my slave by the hair and face-fuck her bound, gagged, and blindfolded, with her skirt pushed up and her panties around her knees.

I was getting close to coming, but pulled out. I swung her onto her stomach, and pulled her up by the waist so that's she was on her knees, with her face on the floor. I spanked her, and she let a yelp of surprise. I spanked her a few more times, then picked up my belt. I grabbed her hair, and whipped her 5 times. 

I put a condom on, and squatted behind Kelly. I placed my cock against the lips of her cunt, and slowly pushed it in. I grabbed her hip with one hand, and her cuffs with the other, and started fucking her slowly at first. We were both pretty warmed up by now. It didn't take long before our fucking had become faster, and I felt close to coming. I had to concentrate in order not to come too quickly. As I was fucking Kelly, I it occurred to me that this was the first time I had ever penetrated her vaginally. I had fucked her orally and anally last time, but just hadn't gotten around to good old traditional intercourse.

Reflecting back on our first session didn't help me much in holding back. I figured the hell with it, and rammed her with everything I had. Kelly had another orgasm, loudly, shouting, "Fuck, fuck, fuck." I stopped fucking, and held her hair and her hip tight as I came forcefully. 

After I was through, we slumped down onto our sides. We lay on the carpet for a few minutes while I got my breath back. My cock was still inside her. I reached around, and played with her breast until I felt like getting up. When I did, I pulled out, threw the condom in the trash, and kneeled in front of Kelly. I helped her up to her knees, and removed her blindfold.

"Clean me off, slave."

I held my cock up to Kelly's mouth. She took it in and licked it dry. When she was done, I uncuffed her.

"Excellent. I'm hungry. Let's get some dinner, and then I will use you some more. But first, I need to piss."

Kelly, rubbing her wrists, tensed up when I mentioned the word piss. She had probably counted on having a little time to relax. But the deal was that if I mentioned a need to urinate, she was obligated to offer herself for a golden shower. I crossed my arms and stared hard at her. It took her a few moments before she finally spoke.

"May...may I offer myself for you to urinate on like the worthless slave that I am?"

"Yes", I said, "you may. Assume the position in the shower."

Kelly looked dejected. She stood up and stripped off all of her clothes. I sat down in a chair and watched as I drank a glass of water. I looked through a magazine as she walked into the bathroom.

When I was ready, I entered to find Kelly kneeling in the shower with her hands over her head. I closed my eyes and tried to concentrate. My urine trickled out slowly at first. Even though I'd pissed on her before, it still wasn't that easy to urinate on an attractive woman. I had to really fight the urge to get turned on. But I persevered, and I emptied myself on her. Her chest and shoulders were now covered in piss. When I was done, I held my cock up to her mouth, and she cleaned it.

"Stand up and turn around", I ordered. She did.

"Put your hands against the wall and spread your legs."

I reached to the sink, where I'd put a few items. I spread some anal lube on my fingers, and turned back to Kelly. I spread one of her butt cheeks, and inserted the tip of my index finger into her asshole.

"Uhhhh..." Kelly yelped a little in surprise. She probably hadn't counted on a butt fucking yet either.

I eased my finger in and out until she was relaxed enough to take the whole thing. I eased in a second finger, and then a third when she was opened up enough. I grabbed her by the hair with my other hand.

"Did you clean yourself this time?"

"Yes, master. I had an enema earlier today."

I withdrew my fingers. I picked up a butt-plug on the sink, lubed it and inserted it into her ass. She was loosened up, so it didn't take long to work it all the way in.

"Assume the position. Don't turn around." Kelly got down on her knees, and put her hands behind her head. I felt a little more in my bladder, and figured I may as well empty it completely before getting dressed. I pissed on her, watching the urine flow down her back through the crack of her ass.

"Whose submissive bitch are you to piss on?" I asked.

"I am your submissive bitch to piss on, master "she answered.

"Good. I'm going down to the restaurant for some dinner", I said. "Clean up, and meet me there in 20 minutes."

My Second Tryst with Kelly Ch. 02



After using and humiliating Kelly in our hotel room, I had instructed her to wash up after being on the receiving end of a golden shower. She was then to meet me downstairs in the restaurant in 20 minutes.

Kelly sat down across from me in my booth 22 minutes later. She still had her collar on.

I checked my watch. "You're two minutes late."

"I thought I would be on ti..."

"You will be punished for tardiness. Is the butt-plug still in?"

"Yes master."

"Good."

After a light dinner, we got back to our hotel room. I ushered Kelly in. She walked to the center of the room, stripped down to her black heels and nylons, and assumed her position (on her knees, with her hands behind her head). I lay down on the bed.

"I'm going to close my eyes for about 10 minutes. Lay beside me." 

She crawled up next to me, and I fell asleep for about 10-20 minutes. When I woke up, she was asleep too. My arm was around her shoulder. I reached down behind her, and gently pushed on her butt plug. I continued as she woke up. Then I grabbed her hair and started kissing her. I started off tenderly, and ended by sticking my tongue as far down her throat as I could get it.

"Undo my pants and suck me off, slut."

Kelly sat up, loosened my belt, and unbuttoned my pants. She bent over, took my cock out, and started sucking it. I put my arms behind my head and closed my eyes. It felt good, so I let her go for a while. 

"That's enough for now, slave. It's time for your punishment. Assume your position on the floor."

"Yes master."

Kelly got down on the floor and re-assumed her position. I cuffed her hands behind her, gagged her, and put the blindfold back over her eyes. Then I stood in front of her, grabbed her by the hair with my left hand, and slapped her.

"Don't ever be tardy again."

I slapped her some more, each time a little harder than the last. When I was done, I removed her gag. A few tears trickled down through the blindfold.

"Apologize."

"I am sorry master. I apologize for my tardiness. I will never be late again. Thank you for punishing me like the worthless piece of submissive ass that I am."

I kneeled down to her level, and switched hands for gripping her hair. I put my hand up by her face.

"Good. One more to make sure you don't forget."

I slapped her once more, this time on the other side of her face, and she yelped in pain. I got up, and walked around her again. I was taking a moment to give her a little breathing space, and to appreciate what I had in front of me. Here was a desirable, submissive woman who was mine for the taking.

I put a pillow in front of Kelly. I then re-gagged her, gripped her by the back of the neck, and guided her down until she was face-down on the pillow, with her butt still up in the air. Then I took out my newest toy. It was a spreader bar. I'd been dying to try it ever since it arrived.

I spread Kelly's ankles out as far as they would go. I put her left ankle through the cuff and tightened it. When I tightened the cuff around her right ankle, Kelly tensed up considerably. She probably didn't realize what was happening until then.

I sat down for a minute to watch her, and to give her a minute to try and get used to her position. After she had seemed to settle a little, I got up. 

I took out my laptop, and pulled up a BDSM video I had downloaded. I put the laptop in front of Kelly's face and hit play.

The video was of a woman, bent over a table, getting whipped by a man in a mask while two other women held her down. She wore a pair of heels and a collar. The woman screamed loudly the entire time, begged her abuser for mercy, and offered increasingly ambitious sexual favors to stop the whipping. No one else said a thing.

As it played, I fondled Kelly. I started by playing with her cunt, and let my hands roam over her body. I played with her breasts, squeezed her butt cheeks, ran my fingers up and down the crack of her ass, and all over her body. I shoved my fingers as far up her cunt as they could go, undid her gag, had her lick them clean, and re-strapped the gag. I pulled out her butt-plug, re-lubed it, and shoved it back in as far as I could. 

Kelly was getting mighty warmed up, but I wasn't doing anything enough for her to come. She was really starting to sweat, though. I stopped the video, and sat there for a minute watching her. 

Ankles spread apart and cuffed to a spreader bar. Ass up in the air with a butt-plug inside. Hands cuffed behind her back. Facedown on a pillow on the floor blindfolded and ball-gagged. She continued to twitch and sweat. Her cunt dripped onto the carpet. 

I paused the video, and removed her blindfold. After waiting a few seconds for her eyes to adjust to the light, I hit play on the video. I let Kelly watch it for about two minutes. As she watched, I uncuffed her hands from behind her, and pulled them down below her. I then re-cuffed them to the spreader bar.

After I was finished, I paused the video, and put her blindfold back on. I sat back for a few minutes, certain that the images were now burned into her mind.

Now that her hands were out of the way, I could get to work. I picked up my belt, and whipped it across her ass once. She let out a loud scream, even through the ball-gag. I pressed play on the video, and commenced whipping her.

She yelped as I whipped her, but it was nothing like her first scream. Her yelps of pain were muffled by the ball-gag, only occasionally rising in volume. I whipped her exactly 25 times, hard. Kelly tensed her body and strained at her bonds as I whipped her. Her yelps mixed in with the screams and cries from the video. 

At 25, I stopped, paused the video again, and sat back in my chair for a minute. She was covered in sweat now, and still twitching.

I undid her cuffs to the spreader bar, removed her blind-fold and ball-gag, and commanded her to rise up to her position. She rose unsteadily to rest on her knees, and put her hands back behind her head. I stood in front of her. I was certainly ready to fuck her, but I wanted to clean off the sweat first. I also wanted to see just how far I could take her.

"I need to take a piss, slave," I said.

I'm sure Kelly couldn't believe my words. After all that whipping, I wasn't going to fuck her, but instead I was going to piss on her again? An extremely anxious look washed across her face, as I'm sure she was considering her options.

"May I...may I offer myself as a worthless submissive bitch to be pissed on, Master?"

"Yes, assume your position in the shower".

As Kelly got up, I lay down on the bed and closed my eyes. I had to concentrate for a bit to try and shrink this hard-on.

Kelly was in her position in the shower when I came in. I gave her another golden shower. I actually did have to go a bit, so it was probably a good thing I'd decided to urinate on her again. It would be easier to concentrate on fucking afterwards with an empty bladder.

After I'd finished pissing all over her, I held my cock in front of her face. She cleaned it. It felt good, so I grabbed her hair and used her mouth, running the tip in and out, and maneuvering her tongue around the shaft, balls and scrotom.

"That's enough," I said, as I pulled back.

"Stand up and turn around".

I pointed for her to lean against the wall and spread her legs. I took her butt-plug out and dropped it. Then I spent a few minutes fingering her in the ass. She groaned a few times as I did this.

"Do you have anything you wish to say to me?" I asked, as I fingered her.

"Yes Master. Thank you for pissing on me like the submissive little fuck-toy that I am."

"Good. Anything else?"

"Your fingers feel really good right now. Are you going to fuck me?"

"Where?"

"In my ass."

"Is that what you want? An anal fucking?"

"Yes Master, I want an anal fucking. Please...please take me in the ass."

I said nothing as I finger-fucked her.

"Please bend me over, and shove your cock up my ass, and butt-fuck me hard. Please master."

"Are you asking because that's what you want, or because that's what you think I want?"

"Both."

"You like taking it up the ass?"

"Yes Master."

"The last time we got together was your first but-fucking, wasn't it?"

"Yes Master."

"You didn't know you liked it yet, did you?"

"No master."

"Did the idea turn you on?"

"A little, but it also scared me. The idea of being made to submit turned me on."

"How do you feel now that you've had your first ass-fucking?"

"Turned on. I...liked being forced to take your cock anally like a slave. I think about it whenever I play with myself."

"Have you told your husband that you like it up the ass?"

"No Master."

"Why not?"

"I...I don't think I could be dominated by him. It just wouldn't feel right. We've been married too long and...I don't think I could look him in the eye if he knew how much I like being humiliated. Taking a cock up the ass is a submissive act for me."

I removed my fingers, and held them up by her face.

"I would like to see you lick these clean, but I draw the line at ass-to-mouth. For the time being at least."

My fingers were so close that she could definitely smell them.

"However, I reserve the right to change my mind. Is that clear?"

"Yes Master. I will lick them if so ordered."

I lowered my hand.

"Clean yourself up so that you may be of further use to me. You have ten minutes. When you come in, there will be something on the bed for you to put on. Do so."

When Kelly came in I was lying on the bed. There was a pair of thigh-length rubber boots next to me. She picked them up, looked them over and put them on. It took a little effort. They were tight. I'd had to guess at her size, and had done fairly well, but I think thigh-length rubber boots would be a little hard to slip into no matter what the size. 

After she'd squeezed into them, I had her stand with her hands behind her as I inspected her. She looked stunning in her boots and collar. I ran my fingers over her body, and squeezed and fondled here and there. I almost wanted to whip her with my belt again, but it was time to fuck her.

I ball-gagged her and pointed to the spreader bar. She got down on her knees, and put her hands underneath her. I cuffed her wrists and ankles to the bar.

I put a condom on, squatted behind her, and shoved my cock slowly up her cunt. She moaned with pleasure. After a few slow thrusts, I pulled out, and lubed it up. With her ass up in the air, it was a little tough to get the angle right for anal penetration. I had to pretty much stand over her. She was pretty loose from having a butt-plug in all night. I stopped after the tip was in, and then slowly shoved the whole thing in. Kelly's whole body stiffened. Man, it felt great. I hadn't penetrated a woman anally in 6 months, and was really missing it. 

I started to fuck her slowly, and built up speed very gradually. I didn't want to come too soon, and I easily could have if I didn't pay attention. She was really moaning about halfway through the fuck-fest, so I reached down and fingered her clit. It didn't take long for her to come. It was a long, loud orgasm. She was screaming through her gag as she pulled at her cuffs. During her third orgasm, I felt my own coming on. I fucked her as hard and fast as I could, and shoved it in deep as I came. Easily the best orgasm I'd had in 6 months. I kept my cock buried as I came, and then gently thrust it in and out while I was still sensitive. Kelly was still moaning from cumming.

I finally exited her ass and took off the condom. I removed Kelly's gag and shoved my cock into her mouth.

"Clean it."

She licked it obediently.

"Thank me."

"Oh god! Thank you Master! Thank you for fucking my ass so hard! I really needed that. I haven't come like that since the last time you butt-fucked me. Thank you, sir."

After uncuffing her, we relaxed for a while together on the bed. After about 45 minutes she spoke without permission.

"Master, I have to get going soon. "

"I did not give you permission to speak."

"I know, but I have to be home soon."

"Get on your knees. I am going to punish you, and use you one more time."

"Yes master."

Once she was on her knees, I grabbed her roughly by the hair and slapped her a few times for punishment. Then I treated myself to a nice, long, indulgent blowjob.

As Kelly dressed afterwards, I gave her a sealed envelope with this letter inside:

Slave,

If you are reading this note, then you have once again pleased me. We will resume this tryst once more in the future if you so desire. However, know that the next time we get together, I shall test your limits further. You will be farther out of your comfort zone that you ever have been. There will be activities involved that you may not be initially comfortable with, nor even enjoy. But they shall be required. You will have one opportunity for refusal, and only one. 

As per my last instructions, you are required to write up an account for tonight's session and post it on Literotica, following the same rules as before. I shall be looking for it.

Sincerely,

Your Master