My Best Friend Is a Domme

I didn't jerk off the night Patty and I last saw each other, like I had promised. We didn't see each other for a few days after that though, and I hadn't made any promises about those days. And since Patty really had my gears going, I jerked off a lot.

One day I even wore my chastity cage to work again. Not because I had too, but because I wanted too. It made me feel sexy. It wasn't the same though knowing I had the keys in my pocket, so I did it only for the one day.

Patty and I texted a few times. Just friendly messages, nothing kinky about it. I actually wasn't sure if our little games had been just a little sexy fun between friends or if they would continue in one way or another.

I had asked her on Wednesday if she wanted to come over, but she had replied that she was really busy at work that week, and wasn't sure when, so she said she'd let me know.

That Friday evening, around 9 o'clock, she texted: "Had a fight with Ben. Can I come over?"

"Of course," I replied right away.

I hoped she was okay. During the years that we'd known each other this had happened quite a few times. She had the habit of walking out the door after a fight and this had happened with most of her previous boyfriends, sometimes arriving at my place really angry or in tears. So this wasn't the first time she came over to my place after a fight, but it was the first time this happened since she was together with Ben.

Within a few minutes my doorbell rang. I jumped up and let her in.

She looked to be fine though. Maybe she sounded a bit annoyed, but there were no tears or screaming rants on what an asshole her boyfriend was, as I had witnessed often enough. She just walked in, hung up her thin coat and asked: "Do you have any wine? I really could use some."

"Are you okay?" I asked, a little concerned.

"Yeah, I'm fine," she sighed. She walked into the kitchen and opened the fridge, grabbing a bottle of her favorite wine. I usually had a bottle waiting for her.

I grabbed her a glass and opened the wine for her.

"Are you sure?" I asked.

"Yeah," she said. Her voice sounded fine. "I just needed to get out of there for a little while, since I was agitated and he pretty angry with me. I didn't want to make it worse, so I left."

I poured her a glass, grabbed a beer for myself and we went into the living room. I put on some relaxing ambient music and sat next to her, giving her some time to collect her thoughts.

"What happened?" I asked after a few minutes. "Want to talk about it?"

"It was my fault I suppose," she sighed. "I just got annoyed and may have been a little harsh." She paused for a minute, sipping her wine. "We were having sex. It started out fine, you know, kissing and feeling each other up. And then we started fucking and I was just getting into it and then he just came, in like no time. Again."

I looked at her, studying her face, gaging what she was feeling.

I sighed again. "I may have told him he was an egocentric asshole with a useless cock or something." She paused. "While he was still cumming, actually. He really didn't like that, so we had a fight."

I chuckled, imagining the scene, poor Ben cumming while she yelled at him that his cock was useless. My chuckle made her chuckle and then I knew she was actually fine and she had a clear understanding of her own behavior leading into a fight.

"Yeah, you probably should have waited until he was done cumming before scolding at him and degrading his penis." I said sarcastically, grinned at her.

"Yeah, of course," she said, rolling her eyes. "I may have been a little bit of a bitch. I felt bad right after, but didn't want to admit it, since at the time I really wanted him to feel that I need more from a guy than a 40 second fuck."

I just smiled at her for a while. I loved her, but she could be a bitch every now and then and luckily she knew that. She had little problems admitting it if she had been a bitch. The hard part for her was usually apologizing.

"Did you tell him you're sorry?" I asked carefully.

"No. And I know I should, but I really don't want to yet," she said. "That's why I left and came here. I need some time to let my feelings calm down and to get my head straight. And then I'll fix it, since he didn't really do anything wrong, I guess."

She looked at me like a guilt aware little puppy for a second.

"Except for cumming so soon," she added. "I hate it when he does that. I'm not putting up with that. I just can't do that."

I chuckled. "Honey, he's nineteen and his girlfriend is hot as fuck, what do you expect? He doesn't do it on purpose, he just can't help himself." I thought about adding: I would cum in a minute myself if I would fuck you, but quickly swallowed that sentence. "Give him some time, he'll get better in postponing his orgasms."

She shrugged. "I suppose," she said and briefly put her head on my shoulder. I kissed her hair.

"More please," she said, grinning, holding out her glass.

I took her glass and got up. "You know that's not lemonade, right?" I asked, hoping that she wouldn't keep drinking at that speed all night.

"I know, dad," she said, cynically empathizing the "dad."

"Give me your keys, that will make me feel better," she said before I left for the kitchen.

And that's when I realized I had forgotten to put my cage on.

"Erm, they would be useless, since I have forgotten to put my chastity cage on," I confessed.

She sighed. "Why is it that guys just don't listen when I say something?" she said, throwing her hands up, feigning despair.

I chuckled.

"Well then," she said, "go to the bedroom, strip, and put your cage on. You can get me my wine after you've given me the keys."

The lighthearted atmosphere made me agree easily, but still I felt a little embarrassed and vulnerable when I returned to the living room, wearing nothing but my chastity cage. I walked towards her while she stared at my naked body moving, feeling my cock swell a little in its cage, and handed her my keys.

"See, that's better," she said as she took the keys from me and threw them in her purse. "Now, more wine!"

I turned to walk to the kitchen and she slapped my ass, playfully, but pretty hard. I yelped and almost jumped in the air from the sting it gave. Patty just giggled.

While pouring her wine, I felt my butt cheek still sting. Nobody had ever slapped my ass before. I liked it.

When I returned, she had my laptop on her lap.

"What's the password for this thing?" she asked.

"It's face ID," I responded. She turned the laptop a little my way and I sat down next to her, leaned into her a little, feeling her body heat. It felt really weird to sit next to her naked, while she was fully dressed. It made me feel sexy and dirty at the same time. I held my face in front of the camera to unlock the screen.

"What are you going to do?" I asked her, curiously.

"Show me where you buy sex toys," she half asked, half ordered.

I named a website where I had ordered some things before and she entered the address.

I just sat next to her and watched the screen as she clicked through the pages. She went for dildo's first, scrolling through list of different sized and colored dildo's, before discovering the bdsm section.

She went through a couple of categories. Cuffs, collars, gags, ropes, chains, leg spreaders, hoods and arm binders scrolled by. Sometimes she looked at an item closer, just briefly. I watched, silently, wondering what she was thinking and which items she actually liked. She never gave a hint on what she liked though, she just silently consumed the information.

"Hey, no touching!" she said when I leaned a little closer and my naked shoulder touched her shirt, and she gave me a little push. "I'm not going to let a naked pervert shoulder hump me."

"Sorry," I said. I really felt like she put me back in place. Why does my cock always react when she does that, I thought.

"I don't even know what this is," she said.

"That's a ball crusher," I said, looking at the clear plastic device with holes and screws in it.

"Ouch," she said and continued looking around.

"And this?" she asked.

"Ball stretcher," I responded. "You can add weights to it."

"Interesting."

She looked around a little longer and then stated: "I don't even know what half of this is, let alone what to do with it or how to use it. How do you learn something like that?"

"Most of the little I know I learned by watching porn," I said.

"Where?" she asked, a bit hasty and business like.

I named a website I often used and of which I knew they had pretty good bdsm videos on it and while she typed in the address, I knew I was going to be caught out again with something I was embarrassed about. I swallowed but kept silent.

She scrolled through the list of videos on the opening page.

"These are all guys," she said.

My cock swelled again, this time really waking up and going erect instead of the smaller stirs I had felt until now, while I my heart skipped a beat. I felt really awkward when I stammered: "It's still on gay. You can put it on straight on the top." I pointed at the drop down control, but she didn't even go there.

"Conrad, have you been jerking off to gay porn the last few days?" she asked, like a mother asking a her son if he had been secretly smoking.

I cleared my throat. "Erm, I may have."

"No, don't evade the question by being vague. Did you jerk off to this?" She put on her stern face and looked me straight in the eyes, carefully watching if I was telling her the truth.

Why did I get so turned on when she does this?, I thought again.

"Yes, I have," I confessed to her, glancing down in shame.

"Do you get all turned on by guys?" she asked, half interested, half teasing me. "Does it get really hard if you watch this?" She looked down at my cage where my cock was visibly struggling against its bars. "Never mind, I can see the answer."

It felt really warm in here all of the sudden.

Patty clicked on a video and it started playing. It was a cute, young guy, sitting on all fours with a ball gag in his mouth, being fucked in his smooth ass by a fucking machine. His rock hard boner bounced up and down in rhythm with the machine, visibly dripping precum.

I felt busted. For some reason, I really hated Patty knew I watched stuff like this. I felt like any form of relationship between us would be destroyed forever and I actually feared she would see me as a perverted gay guy. I was okay with being bisexual, but knowing Patty previously having trouble understanding bisexual guys even existed, I feared she would forever see me as a being gay and she'd lose any interest in playing with me or even would never see me as a man again. My erection even started to go down in fear.

"When you watch this, would you like to be him or be with him?" she asked, studying my dumbfounded face, while I couldn't look away from the video.

"I don't know," I stammered.

"Conrad, just answer the question," she said. She sounded sweet. Like a girl talks to a gay guy who doesn't dare to come out, I thought. For a moment, I feared I might even cry.

"Both," I answered.

"You really are such a pervert," she said, closing the video and scrolling through the list of videos, selecting another one. This one was of a guy sucking a huge cock with his hands tied behind his back.

"And this one, would you like to suck a cock like that?" she asked.

I feared to answer her question, but she would get me to answer it truthfully anyway, so I said, dead honest: "Maybe, if I like the guy to whom it's attached."

Patty smiled briefly, studying the video. She shrugged: "It is a pretty nice cock." She watched the video for a second, smiling sheepishly. Was it the light or did I even see her blush a little.

She closed the laptop and put it away. She changed her position, as if she needed to compose herself for a second, and downed the rest of her wine.

"Do you like guys?" she asked me, her brown eyes on lie detector mode again.

Here it was, the moment Patty would conclude I was totally gay. The moment I would lose her forever.

"Sometimes, yes," I confessed.

She nodded. "And girls?"

"You know I like girls Patty," I said. "You know I lived with a girl and you even made me cum just by looking at you. In a way anyway." I really hoped she would take my attraction to girls, and to her specifically, seriously.

She stared at me for a few seconds, gaging me.

Then she smiled at me deviously.

"So, the truth comes out," she said quietly, grinning like she had an evil plan in mind. "And it just got crystal clear to me. I don't even know why I haven't realized it before, but now I do: you have been jerking off the last few days when I specifically said you weren't allowed to jerk off."

I was completely dumbstruck. I couldn't even think for a few seconds.

Wait, what?, I thought as a came to my senses. Here I was, all conflicted and scared of her opinion of me and about me losing her forever, and now she somehow started about me jerking off? And about not being allowed to jerk off? What was she even talking about? I didn't do anything that I wasn't allowed to. A thousand feelings and thoughts raced through me and I couldn't even think straight for a few seconds.

"Erm, yes, I did jerk off. But you only said: no jerking off tonight when you left last time."

"No, I didn't," she said. "I said: no jerking off. Period."

On top of all the other feelings, I felt a little bit annoyed now, like being accused of something I didn't do.

"No, you didn't," I stated.

"Yes, I did," she said, pretty sure of herself. "Why would I allow you to jerk off while the only pleasure I get from this whole ordeal is knowing that I control your cock?"

Now I seriously started doubting myself. I knew I had payed attention, I was sure she said 'tonight'. But what if I was mistaking? And all of the sudden I realized it didn't matter if I heard correctly or not. I wouldn't win this discussion. And I wasn't even sure if I wanted to win it.

"I'm not sure now," I said, shuffling my feet.

"Well, I am," she said. "And you just didn't listen. Or you didn't want to listen probably, since you seem so determined at playing with your thingy."

Now I felt ashamed, knowing I disappointed her. And knowing that she thought that I had a 'thingy'. I didn't know what to say.

"You know what," she said when she noticed I was dumbstruck again. "You go pour me another glass of wine and I'll go look through your toy drawers and think of a way to make you understand you are to listen more carefully when I say something, alright?"

It took another few seconds for me to realize I just got instructions, and I nodded when it sank in.

She got up and walked to the bedroom, leaving me alone for a second. I recomposed myself and grabbed her glass.

In the kitchen, I took a moment to get myself together. I tried to shrug off all the feelings about my bisexuality, about Patty maybe drawing conclusions that weren't true and about the discussion about what she actually said. I took a deep breath and told myself that it didn't really matter, it would all work out fine and that I'd better focus on what she had in mind next.

I became aware again of my nakedness. I looked down, at the little black cage hugging my cock and balls. I realized Patty was looking through my toys and that this smoking hot girl that I dearly loved was enjoying herself with me.

I returned to the living room and placed her glass right where she left it before sitting down on the couch again.

When she came back, she was holding my prostate vibrator and a bottle of lube.

Oh shit, I thought, she's not going to make me put that up my butt in front of her, right? But of course I knew what was coming and I swallowed nervously.

"Show me how this works," she said, smiling and stretching out the hand holding the vibrator.

"You'll need the remote," I said.

"It's got a remote?" she asked, pleasantly surprised.

"Yes," I said. I wanted to get up and get it, but suddenly realized I should probably ask for permission. "Should I get it?"

"Yes."

I got up and hurried to the bedroom to get it.

She seemed to be studying the vibrator when I returned to the living room.

"Here, I'll show you," I said, sitting down next to her again.

I briefly took the vibrator from her and held the button on the bottom for three seconds. "This is how you turn the power on," I said. Then I used to remote to let it vibrate.

Patty chuckled as the vibrator turned on and vibrated in her hands. I showed her the button on the remote and how to cycle through the different speeds and patterns. She seemed to like the vibrations because she smiled sheepishly for a second.

"And also, with this button you can inflate it," I said, pushing the button. The toy made a soft buzzing sound as the built in pump inflated the tip.

"Wow!" she exclaimed, watching the toy in her hand grow and grow with wide eyes. "That's so cool! How big can it get?"

"Pretty big," I assured her, showing how to deflate it again.

"That's amazing," she said. "Put it in!"

I knew she was going to say that. And still, part of me hoped she wouldn't. It would be really awkward for her watching me put that thing up my ass, I thought. But I knew that resistance would be futile and a part of me wanted her to watch me while I inserted it into my butt. The little part between my legs to be exact, since my cock seemed to love the idea.

"What, right here? While you watch me?"

"Yes, of course. I want to see how you put it in."

"May I get a towel first?" I asked her, having some experience with lube, but most of all desperately postponing the awkwardness of inserting it in my butt while she could see me.

"Sure. Hurry up."

I quickly got a towel from the bathroom, my cock growing in my cage in anticipation of what was to come.

When I got back, I needed a place to perform this procedure. Next to her on the couch would be too close, I decided. So I put the towel on the floor and sat on it.

"Are you sure you want to see this?" I asked her. I really had the feeling it would turn her off to see a guy put something up his butt.

"Yes. Stop procrastinating, Conrad. I know you want to."

"This is going to be awkward," I said, to both her and myself.

"I'm counting on it," she chuckled, taking a big gulp of her wine. That made my cock grow even more.

She leaned forward, watching me sit on my towel. "Now, do it," she ordered.

There was no way I was getting out of this, I realized. I sighed, took the bottle of lube and poured a big glob of it on top of the toy. With my hand I smeared it over its shaft, making sure it was covered completely. I took one last look at Patty, who watched me with twinkling eyes, her glass of wine in her hand.

I laid down on my back on my towel and pulled my knees to my chest, really glad I'd shaved my ass, exposing my asshole to my best friend. This felt really, really awkward for me. My cock seemed to love it though, since I felt it produce some precum already.

I lubed up my butthole with the lube still on my hand. Then I put the tip of the toy against it and pushed slowly. I felt it move in, stretching my butthole. I exhaled and tried to relax my ass as I moved the toy slowly in and out, getting ready to push the thickest part of it inside.

I pushed it in, slowly increasing the pressure, and once the thick part passed my sphincter, my ass seemed to suck in and swallow the rest of the toy in one go. The curved tip of the toy pressed against my prostate and the base of the toy pressing against my perineum, making my cock grow almost full size immediately. I heard myself sigh a soft moan.

I put my feet down, ready to sit up, just pausing a little to postpone feeling the embarrassment of looking Patty in the eye after what I just did.