u/altb3

Submitted for image 10

I pressed the send button on an email and leaned back in the booth. “With that our time working together is over.”

“Cheers! It’s been a fun couple of months, Sarah.” Glenn smiled as he lifted his glass.

“Yeah I’ll miss this, it’s been fun. Well, as fun as work can be.” I lifted my drink to meet his.

Glenn was handsome. Older than me, but fit and with a solid build. For the last two months I had been working at his company as a temporary consultant. Tonight we weren’t colleagues anymore, just two attractive people having drinks.

While I worked for him there had been some long looks, a couple of suggestive jokes and one time I playfully kissed him on the cheek to say goodbye. I noticed he how red his face got afterwards. Nothing unprofessional had happened but I found myself wishing something might between us, and I’d begun to fantasize about him the last couple of weeks.

We’d decided to celebrate at a bar not too far away from the office. I was kind of thinking that drinks might loosen him up a little. Every time things had gotten a little flirty at work, he quickly clammed up. Maybe he didn’t approve of office romances, or maybe it was the age difference; whatever it was I intended to find out tonight.

“So no wife or girlfriend, aren’t you a little lonely sometimes.” The Jack and Coke in my hand might be making me a bit more forward.

“Ummm… yeah I guess, but I’ve never been a relationship guy.” He shifted in his seat a bit.

“Too busy hooking up with all the hotties then?” I leaned forward a bit and made sure my cleavage was as exaggerated as possible.

“No not exactly, it’s a bit more complicated than that.” Glenn polished off the remainder of his scotch. His eyes lingered on me for an extra second, he was trying very hard not to look at my tits.

“Well you’re certainly good looking enough to be with someone, and I know you like girls, I’ve seen you looking at me.” I held up a hand to stop his protests. “You were always professional and I never felt uncomfortable, but I know you think I’m attractive.”

“You’re very pretty. I’m just looking for a specific type of relationship, it’s nothing personal.” A subtle reddish hue had spread to his cheeks, I was pretty sure it wasn’t just the alcohol.

“What about casual hookups or a friend’s with benefits type thing, is that what you’re looking for?” I flashed a hungry smile at him, this was no time for subtly.

“Why? You offering?” He laughed nervously, I think he was trying to play it off as a joke.

At this point i decided that we’re going to fuck tonight, he just doesn’t know it yet. I looked around to make sure the coast is clear and summoned my crazy college girl days. I lifted my top and flash him my tits, making sure to pinch the pierced nipple. “Would you really pass this up?” I tease him.

His eyes go wide, and I know he liked what he saw. This time I polished off the last of my beverage and waved my hand to signal a waitress we want two more.

Waiting for our drinks, we make a bit more casual conversation, I’m not good at waiting but I managed. Once the server leaves, I dive back in. “So tell me what you are looking for, I’m open minded.”

Glenn let out a long sigh. “I don’t do girlfriends or hookups, what I’m looking for is a Domme.” Glenn can’t even make eye contact as he tells me this, just starring at his feet, like there’s something interesting down there.

To say there was a long silence would be an understatement. I took a pull of my new drink before letting out a long laugh.

“See, I knew this was a bad idea.” Glenn buried his head in his hands.

“No, no I’m not laughing at you, it’s just a surprise. That’s all. So you want someone to, like, tie you up and spank you?” I’ll admit I was surprised at how much I was turned on by the idea.

That’s pretty tame actually, but yeah I want someone who’s going to take charge and make me their submissive.”

I tried to reset myself, I was shocked but I knew I needed to take this seriously. It ment something to him. “So have you ever had someone do that for you before, or is this a new thing?”

“Yeah, I had someone, but it’s complicated.” He sipped his drink looking a bit defeated.

“Did you guys brake up? Is that even a thing that happens in that kind of relationship?”

“She married my brother.”

“Wait WHAT?!?” We had been talking in more hushed voices, but obviously I couldn’t hold back after that bombshell. “So she married your brother and now she won’t do it anymore? That sucks, I’m sorry.”

“No, she’ll still do it.”

I just barely caught myself before I yelling again. “She’ll still do it! Your brother’s ok with that!” I managed in a harsh whisper.

“He doesn’t know. He never did. I didn’t even know they were dating. She just showed up to a family get together on his arm, engaged. They got married a few months later.”

The last five minutes of conversation had revealed more about Glenn than everything I’d found out while we worked together. I didn’t remember finishing my drink, but I found it was empty. I took a very deep breath and tried to push past the incredible series of revelations.

“So, do you think she got with your brother just to mess with you?”

“I honestly don’t know. Probably. Listen, Sarah, can we just forget all this go our separate ways?”

“So wait you never told your brother that his now wife has been your sexually dominant girlfriend?”

“Girlfriend isn’t the right word, and what am I supposed to tell him? That the woman he knows as Amy, I know as Mistress Sadie. Or that she used to peg me with a 12 inch strap-on and made me swallow my own load. There’s no real way to start that conversation.”

“She really made you…wait 12 inches? Really?” I thought I was done being surprised. Wrong. He simply held up his hands to indicate length and girth. “Damn where’d she get something that big?”

“There’s plenty of places, I got this on online. I still have it back home in my dungeon.”

I couldn’t believe I was getting turned on by all of this, but I very much was. “So you have a sex dungeon? With a bunch of naughty toys and stuff?”

“Well yeah you can’t do that shit in your kitchen, anyone serious about being that kinky needs a room dedicated to depravity.” He was very matter of fact about it all.

“Take me there, I wanna see it!”

Glenn waved his hand at me. “Sarah, look it’s nice to get some of this off my chest, but I don’t think you’re really ready for that yet.”

“So you doubt me then? You don’t think I can be a domme?” I tried be as serious as I could be under the circumstances.

“Well usually we wouldn’t work together first, that might be weird. And I mean, you’re cute but you just don’t seem like someone who’d be a natural dominant.”

“What because I’m not some goth girl covered in leather, latex and tattoos I can’t boss you around?”

He chuckled at me. “Yeah kind of, plus there’s your voice. It’s light and sweet, the one time I heard you yell at someone, you sounded like an anime character.”

It was true, I don’t have an overly commanding voice, but I was in now. Now backing down. I summoned my most intimidating presence.

“Take your dick out.”

He looked like a deer in headlights “What here, now?”

“I showed you my tits, only fair. Plus I just realized I shouldn’t go through all this trouble without seeing if it’s worth it. You might have a pathetic little cock.”

“Listen I don’t think this is a good ide-“

I cut him off “Shut up and do it pussy.”

Glenn looked around nervously and stared to undue his pants. I could not believe he was really doing it. He reached in and took out a very nice member. Now it was only a little engorged, still mostly soft, but even so I could see he was going to have a well above average dick when hard.

If I was really going to be his new Mistress Sadie, I couldn’t acknowledge how fucking hot all this was. “That’s it? That’s what all this has been about, trying to get that little guy off?”

I kicked off a shoe and placed my bare foot between his legs. I began to rub him ever so gently. I spare a second to look around, I like this bar and don’t want to get kicked out. Fortunately, we’re alone in a corner booth and no one seems to be paying us any attention.

“So Mistress Sadie, was that supposed to be short for sadistic?” I’m hold eye contact and acting like this the most normal conversation in the world.

“I asked her that once.” He swallowed hard.

“And?”

“She kicked me in the balls so hard I almost passed out.”

“I guess that’s your answer then. Did you like the pain?” I don’t give him time to respond. I slam my heal into his crotch and smile.

Glenn does everything he can not to cry out in pain, it might be a quiet night but screaming about his balls would draw unwanted attention. He doubles over with his mouth silently hanging open. “Fuck.” He manages in a horse voice.

I giggle at him. “So are you gonna take me to your sex dungeon now, or do I have to keep correcting you.”

He takes a few moments to recover, and finally after a deep breath starts to put him self away. He had grown in size quite a bit, so he struggled a little tucking everything back in. I sat and enjoyed the show biting my lower lip. Eventually he won the struggle with his pants and looked at me with what seemed like hunger in his eyes.

“I’ll get us a car.” He says sheepishly.

The ride back to his place is quiet. I could have tried to embarrass him in front of our driver, but decided that a silent, almost awkward, ride would build more tension. I made Glenn hold every door and continued to silently follow him until we entered his house.

“Take me to your sex room, perv.” I was enjoying giving commands to the man who was basically my boss until a few hours ago.

“Right this way Sarah.” He holds out a hand to indicate I should follow.

Right there I knew I was going to need a new name. Sarah, or even Mistress Sarah, wasn’t going to cut it. I mentally workshopped names as we walked to his dungeon. As I stepped into the room a wide smile spreads across my face.

The room itself is fairly stark. A single bed with a handful of pillows sat in the middle. The main event was the nearest wall. Mounted like trophies are cornucopia of sex toys, whips and restraints.

I walk towards the wall and let my hand run over several of the more interesting options. Holding a special place in the center of everything is the aforementioned strap on and it’s 12” dick, waiting.

My hand wrapped around a stiff leather whip with a small pad a the end. “Oh, I like this one! It’s the thing they use in horse racing right?”

“Yeah, it’s called a riding crop.” He replied.

I spin around to face him with a raised eyebrow. “Why do you still have clothes on?” I point the crop at him menacingly.

“I didn’t know I was-“

“Rule one: you’re no longer allowed clothes in this room. I doesn’t matter if I’m here or not, you wear even one stitch in here and I’ll punish you with this.” I swing the crop in the air in front of me.

I’m still a little surprised how quickly he obeys me. He’s a strong man, almost twenty years older than me, and yet here he is doing whatever I tell him. In a matter of seconds he’s fully nude hands behind his back.

I circled him, the tip of the crop dragged against his flesh as I do. “Good boy. Very good!” I bring the whip up to his nipple and give him a good flick. Glenn stifled a groan as my smile grew wider. “So your old mistress abandoned you, when’s the last time you were with someone.”

“I haven’t cum in 108 days Mistress.”

I’m stunned my the number, but an evening full of crazy shit has the inoculated me from the surprise of it all. “You haven’t jerked off since she left?”

“I’m not allowed.”

“Good, I like that. Well keep that, it can be Rule Two: Only I can make you cum.” I smack his other nipple. “And it’s Mistress Ani. That’s what you’ll call me, understood?”

“Yes Mistress Ani.” He obediently replied.

“108 days? I’m can’t believe you didn’t pop when my foot touched you at the bar.”

“I almost did Mistress, I’m sorry.”

“Well, let’s clear your pipes.” I removed everything but my panties and enjoy his eyes on me. I can see him getting harder, swelling at my nudity. “Oh and you’re going to buy me a nice table for this room. Something to put my clothes on, I’m not happy I’ve got to keep them on the floor while we do this.”

“Yes Mistress Ani. Please forgive me!”

I grab a bottle of lube from a pedestal on the wall and coat my hands. I rub them together and take my time, watching as his eyes beg for me to start. He continues to grow. I kneel beside him, but still deny touching the throbbing cock in front of me. Instead I run my hand along his ass, finding his crease and bury my hand deeply between his cheeks.

For a moment it looks like his hands move slightly, reaching for his dick. “Keep your hands behind your back, or I’ll punish you.”

“Yes Mistress, sorry. It just been so long, it hurts.”

I continue rubbing his ass, fingers slowly zeroing in on his opening. Teasing his hole, as we both know that I’m going to use that strap-on before the night is done. With my other hand I slowly wrap my fingers around his swollen balls. “Is this where it hurts?” I tug on them slightly.

I can tell he’s trying to hold back, but a low grunt escaped him. My hand slowly slides up from his sack, a firm grip traveling from shaft to tip. I use my thumb to massage the underside of his dick. He’s leaking already, and I stroke back down the length of him.

My other hand probes his hole, two fingers easily slide in and I love the sounds Glenn is trying not to make. I’ve never fingered a man before, but I know the basics, find his prostate and attack. He rocks onto his toes and I know I’ve found what I’m looking for. I focus on his ass, introducing more fingers. If he can take 12” he can take more than a couple fingers. I want to work him more, but he’s dripping so much I don’t think he can last much longer.

I decided that it’s time. I take his shaft with both hands and work him hard. Only a few seconds of pumping and I feel pleasurable pulsing turn into a hard forceful straining. My left hand continues stroking as I use my right to catch as much of him as I can.

“Nnnnaagghhhhh, fuck!” Glenn groaned as he unloads into my hand. His cock keeps pumping as 100 days of build up drains form him. My cupped hand fills with his milky white cream.

“You know all the best anime characters have finishing moves.” I stand and look Glenn in the eyes. I raise my voice to inmate the characters I’ve heard. “Do you wanna see my full power?”

“Yes Mistress, please.”

I pull my filled hand back, and smiled. “CUMMMMY SLAPPPP!”

I could feel a warm wet mist tickle my face as his cum sprays everywhere. Glenn dropped to a knee, and when he looked up at me a wet red handprint covers his left cheek. I couldn’t help but laugh. I had done this to him, and he had needed me to do it.

“All those toys are clean and ready to use, yes?” I asked, back to using my normal speaking voice.

“Yes Mistress Ani, I thoroughly clean and sanitized everything after use. I also change the sheets and scrub the entire room.”

“Good, that can be the Third Rule: You’re responsible for all the cleaning. Now, help me with the strap on then. We’re gonna fuck some more cum out of you.” I removed my panties and step into the rigging, letting Glen secure all the adjustments until everything feels tight. “Is your phone in your pants?”

“The right pocket, yes Mistress.”

“Good, unlock it for me and get on the bed face down.”

He hands me his phone and climbs onto the bed like I commanded. My hands are full of cum and lube. It makes navigating the menu tricky, but I open his camera and climb on top of him. I make sure the large dildo covers his entire crack, and snap a picture.

The click draws Glenn’s attention. “What are you doing my Mistress?”

“Claiming my property. Your old mistress, her number’s in here?”

“Yes, under Sadie.”

I type out a message:

He’s no longer yours. A NEWER, YOUNGER, Mistress now owns this submissive pet. Do not contact, failure to comply will have severe repercussions!

I attached the photo, and for the second time that night hit send on a life changing message.

Looking at the sheer size of the toy against his ass, I still have doubts it’ll fit. I apply a good helping of lube and work my new dick between his cheeks. He slowly opens for me, and I press down into his waiting hole.

“You ready to be my slut.” I taunt.

“Yes Mistress Ani, I’m yours.”

I rock my hips forward and I can’t believe my eyes. His ass parts and accepts the thick dildo. I pushed in half way, and felt only a little resistance. I pull out and then back in, this time I go all the way in. The last two inches are a tight fit, and I hear him start to groan. I lean forward and use both hands to push in his back, my legs pin his down. Now I can really work him hard.

I surprised how good it feels. Fucking him is fun, but there’s also a nice friction against my pussy as I hump him. The harder and faster I go, the better it feels. I lose myself for a moment, it’s no longer about punishing him, but pleasing me. I only notice his loud moans because my arms and hips begin to tire.

“Get on your side slut.” I’m not ready to stop, but I needed a new position. We roll to together and Glenn lifts his leg, opening his ass wide. From this angle I can reach between his legs and stroke him. I feel the pulses in my hand, but I’m not sure what’s more cum and what’s just me slamming my big dick deep inside him. I don’t care.

My body is tired and covered in sweat, it’s time to get mine. “Eat your Mistress’s pussy, she wants to cum.” Glenn slides off my dick, there’s a wet popping noise as does. When he gets up I can see just how much creamy goo is pooled on the sheets. “How many times did you cum? I got a lot of milk out of you didn’t I.”

“I’m not sure, I lost count. My Mistress was very generous. Everything aches.”

“Good. I want you to think of me tomorrow, as your ass throbs sitting in your office.”

Glenn is quite gentle as he obediently undoes all the straps, releasing my slick opening. I thought some of my wetness must be the lube, that worked its way under the strap on, but no it was all me. I couldn’t recall ever being so open and ready.

I grab Glenn by his hair and push him between my legs. His face stubble rubs on my outer lips and sends a tingle up my spine. His tongue is eager as it slides into my folds. The skill of his mouth is very impressive, he’s clearly been taught well. He works in deep as his upper lip sucks on my stiff clit. For a moment he tries to lift his head and come up for air. I don’t let him.

Pulling him hard into me I yell. “You can breathe after I cum.” My hips use what strength I have left to flex in his face. A warm feeling begins to radiate from deep within me, eventually building to an explosion that radiates throughout the rest of my body. I let go of Glenn and collapse back. The pleasure hits me in waves and I soak up every moment.

I lay there for a minute as slowly the ecstasy fades, turning into a satisfying relaxation. Once I have finally caught my breath I prop myself up and see the state of the room. A large pool of cum on the bed next to me, lube everywhere and my thighs are so shiny and slick I can see Glenn’s reflection in them.

“Go got me a wet washcloth to clean up a little.” I tell my new submissive. As he gets up to walk out of the room I stifle a giggle when I can see his ass hasn’t recovered yet, it gapes open when he leans over.

He returns a moment later, and as he’s about to hand me a towel his phone chimes. I look at it and belly laugh at the message. “Your old ex is the jealous type huh?” I flip the phone to show him the text.

HE’S MY PROPERTY! HE DOESN’T GET TO DECIDE WHO HIS MASTER IS! I’ll PUNISH BOTH OF YOU FOR THIS!

“We should have her and your brother over for dinner. It’ll be fun don’t you think.” Glenn’s face turns ashen. I type the invitation.