I walked over to Ground Central Coffee Company on Tuesday. I had agreed to meet Dan there at nine thirty, half an hour before meeting Anna and Mark, so I could update him on the situation and what we were walking into.
Dan was already sitting there with a coffee at a table for four when I arrived. He had ordered for me as well and put a lid on the cup to keep it warm.
I sat down across from him.
“You should sit next to me. It’s better for when they arrive,” he said.
“Smart.”
I moved across to his side and removed the lid from my coffee.
“I already put half-and-half in there. I brought four packets of sugar. I know you take three, but better to have too much than too little.”
“So, I guess I should tell you why you’re here?”
“Protection, Leah said?”
“Maybe? I don’t actually know what’s gonna happen here. But the TL;DR is that I sorta arranged and oversaw someone having sex with his fiancée. Very dirty, very disrespectful sex, specifically for her husband-to-be. And now he wants to meet.”
Dan stared at me.
“I think I might need the long version of that, because right now I’m worried he’s going to bring weapons and go all Death Wish on us.”
I gave Dan the long version, ending by showing him the Twitch chat I had with Mark.
“Okay, that sounds… less dangerous. I think he just wants the video you made.”
“But I don’t have it!”
“Then we tell him that.”
I sat back in my chair, and Dan put a hand on my shoulder.
“We’re in a busy public place. This is the right place. We need to resolve this thing with Mark. Letting it fester could go wrong in so many ways. You did the right thing.”
“Not sleeping with his fiancée is the right thing.”
“Okay. Right thing for everything after that part.”
At ten, I saw Anna walk in with a man who I assumed was Mark.
He was a little taller than her, lean, neatly dressed, with glasses and short brown hair. Not intimidating. If anything, he looked like the kind of guy who apologized when someone else bumped into him.
Anna walked half a step ahead of him and spotted me fast.
She turned to Mark, pointed, and whispered something in his ear. Our eyes met.
I did not see hatred. I saw hesitation.
Perhaps fear.
“I don’t think we are in danger,” Dan said to me.
“Oh, I don’t know about that.”
They both sat down across from us, Mark across from me and Anna across from Dan.
“Hello, Miriam,” Mark said.
I grimaced at someone using my full name.
“I go by Mia, but nice to meet you too, Mark. I’ve heard so much.” I looked over at Anna.
Mark touched Anna’s hand, then leaned over and whispered something in her ear. She nodded, got up, and walked toward the counter.
He wet his lips, clearly nervous about what came next. I folded my hands on the table and waited for him to talk.
“So, you’re most likely wondering why I asked to meet?”
“It has crossed my mind.”
“It all started when I found an empty Plan B package in the trash. It was after Anna came back from the wedding.”
I swallowed.
“We had a fight, but she eventually told me everything that happened. And… I was more interested than I was angry.”
Okay.
“The story has featured heavily in our intimate moments since then, and I’ve asked Anna if she would like a repeat. My biggest regret was not seeing it in person.”
I sat back in my chair.
“Why are you asking me? Anthony was the… main participant.”
Anna returned with two cups and set one down in front of Mark.
“The way we see it,” he said, looking over at Anna, “Anthony was more like a tool you used. You were the one in control.”
“Well, okay, but even if we took that at face value, I don’t have the… tools to do that to your fiancée.”
“We are open to you picking someone else, as long as they are healthy and willing to take orders from you.”
“It’s not like there is an app that lets me select for those features, Mark. You are asking for a very difficult thing.”
Dan leaned over and whispered in my ear.
“I can do it for you if you want.”
I gave him a look and whispered back.
“You sure you want to get involved in this?”
“It’s what I signed up for.”
I shrugged and looked back at Mark.
“So, what do you want?”
Mark looked over at Anna, who seemed more interested now that I hadn’t turned him down.
“I want to be there this time.”
He paused.
“I want to watch her choose someone else. I want to know she wants him, and that I’m not the person she’s focused on.”
He swallowed.
“And I don’t want to be in charge of it. I think that’s part of it.”
His eyes came back to me.
“What Anna told me about the wedding… you decided what happened. You told him what to do. You made her do things she wouldn’t normally do.”
Anna shifted beside him.
“I want that. I want you to decide how far it goes, and I want to have to sit there and watch it happen.”
I took a sip of my coffee again.
“I don’t just want to watch her have sex with someone else.”
He stopped for a second.
“I want to feel… unnecessary.”
That got my attention.
“Like she doesn’t need me there. Maybe like I shouldn’t even be there, except that I have to watch.”
“That is a very particular fantasy, Mark.”
“I know, but I decided I wanted to see if we could make it work. If there was a chance.”
“I have some requirements.”
“Anything,” Mark said very fast.
“I need a clean STD test from both of you. I don’t care if you’re just watching, Mark. Both of you.”
He nodded.
“You provide the location. We are not using my home for this.”
“Of course,” Mark said.
“If you want to film this, you provide the equipment for it.”
He nodded again.
“Lastly, I want you to film yourself acknowledging what we are doing and giving consent for it. I don’t want any problems coming out of this if you decide you don’t like what you see.”
“Of course. I can, no, I mean, we can sign a waiver or NDA if you like.”
I nodded, grabbed a napkin, and wrote down my phone number.
“Here’s my phone number. The next thing you do is send me pictures of clean STD tests. I don’t want to hear from you before that point. Got it?”
“Yes. We’ll get right on it.”
I got up from my seat.
“Okay, then I think our talk is done.”
I looked at Dan.
“Let’s go.”
When we got outside the coffee shop and away from Anna and Mark’s eyes, I let out a huge breath.
“Holy fuck, that was intense.”
“You handled yourself well, though. Put them right in their place.”
“You think so? Didn’t look like I was faking it? Because I was.”
“Nah. Looked real stoic. Leah would be impressed.”
“Well, let’s see how she reacts when I tell her about it.”
Dan and I went our separate ways. He needed to get back to work, and I had received the offer from the company I’d interviewed with and accepted the position. I needed to go to their office and sign the contract.
The pay was better than at my last job, but it was around twenty percent of what Leah made, so it didn’t really change much about our day-to-day life.
The office looked exactly like what I expected from a company that still called itself a startup despite clearly having enough money to stop pretending.
White walls. Glass meeting rooms. A huge open-plan work area with rows of desks and monitors, broken up by couches, plants, and little breakout spaces nobody was using.
There was a ping-pong table near the kitchen, two arcade machines against one wall, and a shelf full of board games that looked more decorative than practical.
Everything was clean, bright, and just casual enough to make you forget somebody had probably spent a lot of money designing it to look casual.
People were dressed in the usual office spectrum between jeans-and-hoodie and I have a client call in twenty minutes.
The HR lady guided me into one of the glass meeting rooms and presented me with several documents to sign. She walked me through the healthcare plan. It would kick in thirty days after I started, and the premium would be deducted from my paycheck. I was given a pamphlet with a nurse hotline I could call for guidance, along with a list of in-network hospitals and clinics.
My start date was set for November 16th.
A handshake later, and I was out the door.
Less than a week left of my hobo lifestyle, and I decided to use it efficiently by going home and playing video games.
Mossybyte was online when I started streaming.
“Do you ever sleep?”
Mossybyte: Just back from lecture. Just killing time.
I booted up Dispatch.
“So you still think Courtney is the right pick for Robert?”
Mossybyte: Look at her. She needs a Robert.
“Yeah, but maybe Robert needs someone like Blonde Blazer.”
Mossybyte: She is competent. She don’t need no man.
“I still think I want to go with Blonde Blazer.”
Mossybyte: There is an achievement if you get both. Maybe go for that?
“Sounds hard.”
Mossybyte: All the best things are.
“Don’t I know it.”
I had chicken katsu curry almost finished by the time Leah got home. The rice cooker had done its part, and the curry came from one of those Japanese roux boxes Leah kept in the pantry. I had fried the chicken myself, so it still counted as homemade.
“Good day?” I asked as Leah hugged me.
“Better than most. I’ve got a ton of VV work tonight, though. Sorry.”
“It’s fine. Still don’t want to hire anyone?”
“I feel like I need to hire a bizdev person to scout for me, but I don’t want some rando. I’d hire Rina, but it’s not a big enough job for her to leave LA for.”
“Rina not good at working remotely?”
“I need more assistant work, really. Booking flights, hotels, organizing food and transportation. Rina is good at organizing people, not things. If I get big enough, I’ll hire Rina to manage the assistant I hire.”
“Mm… I made us food.”
“I can smell that. Curry?”
“Katsu curry. From a box. But I used the rice cooker and fried the chicken.”
“So it’s homemade.”
About halfway through the meal, I brought up that I had met with Mark.
“I was waiting for you to bring that up.” Leah smiled.
“Did Dan already tell you?”
“He sent a text saying no one got hurt, and that you handled it well. I had texted him earlier to remind him about the meetup, so it was really more of a reply to me than a report about you.”
I told her the story of Mark and what he wanted. Leah listened, asking a question here and there, mostly for clarification.
When I was done, she nodded.
“Okay, so my wedding invite was not far off.”
“Shit… I did not ask about that.”
“I’m sure you’ll get a formal invitation if it’s still on the table.”
“So, what do I do now?”
“I guess Dan gets to fuck Anna?”
“We good with that happening?”
“Dan is. Are you okay with being there?”
“I think so?”
“You have shown signs of liking power play before. I know you like to think of yourself as my good little sub, but you also like it when you get a bit of power to play with.”
“I’m not sure I identify as a sub or dom yet.”
“Yeah. A good switch, I called you.”
“Mm… yeah, I remember that.”
“It just means you can slide pretty easily into either role during sex.”
“It makes me feel a bit… undefined? Like I don’t have a strong sexual identity?”
“I see it more as broad. I think you like playing in dominant positions, but you prefer being the sub. Or the bottom. And that fits me well. I lean much more toward the top than you do. It’s a good match.”
I smiled at that. I’d never really thought about whether Leah and I sexually fit together or not. We just did. But knowing Leah had thought about it, and found a good reason for why we fit, made me feel warm and fuzzy.
“Okay, but, like, what do I do?”
“I think you need to send Mark a kink sheet.”
“A what?”
“A sheet of things he likes, accepts, and redlines. And both he and Anna should fill it out.”
“What does that help?”
“It sets guidelines for what you can do in the session.”
I nodded.
“Okay, so kink list. Anything else I should get?”
“The NDA and contract idea sounds good. Let me write something up for you and have a lawyer look it over. Then you can have them sign it.”
“You’re gonna use real lawyers to write up a sex contract?”
“More like… a contract that says everyone knew what they were agreeing to. If they lie about their STD tests, they’re liable. If something happens afterward, we have a record of what everyone agreed to. Stuff to keep us safe.”
She chewed her curry.
“Maybe also something about pregnancy. If Anna gets pregnant, I want it documented that Mark intends to be the parent and Dan does not. Especially if Mark has a cuckold fantasy. An impregnation fantasy is not far away. It won’t override family law, but I want everyone’s intentions in writing before anything happens.”
“You think Mark is into that?”
“Mark wants his fiancée to have sex with Dan while he watches. We should not underestimate what this guy has thought about.”
“Good point. Anything else?”
“I feel like we should contact Lin and let her know this is happening.”
I drew in a breath.
“Lin was very clear that she wanted nothing to do with me. I wasn’t supposed to reach out. If she reaches out, that’s different. But she said she needed distance.”
“But don’t you think this is more of an emergency?”
“I don’t think she cares. The apathy she showed over what I did to Anna last time… I worry she wouldn’t care that we did this, and would be really mad that I contacted her about it.”
“You know her best. I’ll defer to your judgment.”
I wasn’t sure I did know best. But I remembered how we left things, and I really didn’t want to go through that again.
We finished our meal, and Leah and I retreated to the desks. It was weird how we had this huge apartment, but still spent so much of our time in this room. It was a huge room, make no mistake. But it was still only a small part of our place.
I booted up Twitch and saw Mossybyte was still active.
“You really need to get out. I can’t be your virtual girlfriend.”
Mossybyte: You wish.
“No plans for tonight?”
Mossybyte: Gonna head over to my FWB later.
“Oh, so you do have a life.”
Mossybyte: I wish it was a bit more, but I’ll take what I can get.
“I know that feeling. Maybe it will work itself out.”
Mossybyte: Maybe, I hope so.
“Can’t force things. If it’s meant to be, it’ll be. But enough of that. I found the guide so I can get both Blonde Blazer and Invisigal, so we’re gonna cheese this next game session.”
Mossybyte: That’s my girl. Not satisfied with just one.
I played until Mossybyte left at around nine. I said I’d wait for her to come back before continuing, then booted up True Colors.
Of all the Life is Strange spinoffs, prequels, sequels, and whatever else they were doing, True Colors was my favorite. Maybe it was how they fixed Steph. She had been a weirdly written character in Before the Storm, but here she felt more grown-up.
I was in chapter two when my phone made a sound.
No one was watching my stream, so I decided to pause and see what it was.
It was Mark, and my eyebrows went all the way up before I remembered that he was supposed to be texting me.
Mark: STD tests done. Should get the results tomorrow. Will send photo proof when we receive them.
Me: If you wouldn’t mind, could you also fill this in, and have Anna do one as well?
Me: Sent link
Mark: I’ll have them for you early tomorrow morning.
I nodded to myself, looked back at the screen, and saw my game paused with no one watching.
It was getting late, so I said to the empty stream,
“See you tomorrow, guys. Gonna head to bed.”
True to his word, Mark had delivered two PDF files with filled-out lists of wants and dislikes for both him and Anna.
I went through the sheets twice. There wasn’t much they were against. Some blood play, necrophilia, Nazi roleplay. All fair. Happy to oblige.
They had checked off all the normal stuff. Vaginal, oral, anal, kissing, rough sex, toys. Then there was the cuckold stuff, which I guess made sense. Watching, being ignored, not being allowed to touch, Anna praising Dan, Mark being ordered around. Fine. Weird, but fine.
Then I got to the bits that made me stop scrolling. Mark had checked yes to nipple clamps, face slapping, cock slapping, being made to kneel, and cleaning up afterward. Not just Anna. Dan too.
Chastity cages were also marked yes.
I had to Google that one.
“Okay. Not a first-date thing, if you ask me. I’ll put that down as a maybe.”
Sloppy seconds was yes as well, which at least made more sense. Almost wholesome compared to everything else he was into.
I forwarded the files to Leah, who gave me a thumbs-up and said she would include them in the contract.
I had a really weird feeling about all of this. A mix of excitement and fear. I knew I really wanted to do it, but I was also scared it was a horrible idea that would get away from me.
I decided to go shopping. I still had to figure out what to make for dinner, and while I could probably find something in the pantry, I needed to get out of the house.
I also wanted to go a bit further and shop at a normal grocery store. The Whole Foods a block away gave me political tensions every time I saw pickles for nine dollars a jar.
I ended up walking to Trader Joe’s on 59th Street. I always liked Trader Joe’s because it let me find weird stuff I never would have thought about otherwise.
I settled on ravioli, garlic bread, and one of those salad kits. I wanted salad, but I really hated using the salad spinner. The soaking. The cutting.
Then I found the tiny peanut butter cups. A treat for myself for making the long walk.
My phone pinged again. It was Mark, with a picture of both his and Anna’s test results.
Negative across the board.
Okay. I guess I was doing this.
Me: Good. When do you want to do it?
Mark: Does Friday work? We can do dinner and discuss the finer details.
Me: Let me check with Dan, but tentatively yes.
Mark: Looking forward to hearing your reply.
I scratched my forehead.
Fuck. This was really happening.
I made dinner and had it ready for when Leah came home. Dan had replied that he was free on Friday, and when we sat down to eat, I told her that everything had come through on Mark’s side.
“Sounds good,” Leah said. “You want to go shopping tomorrow for accessories?”
“Accessories?”
“You are going into this as a dominatrix. You’re not gonna show up in a hoodie, right?”
“You already know what I’m gonna wear, don’t you?”
She smiled at me.
“I might have ideas.”
“You making me into a production plan?”
“I like playing dress-up. Hell, I run a company for people who love playing dress-up. If I can’t dress up my girlfriend, is life even worth living?”
I rolled my eyes.
“It better be respectable. I’m not gonna be some latex dommy trope.”
“Okay, well, in that case I’ll have to redo my plan.”
I smiled at her, and she smiled at me.
The next day, Leah had taken a long lunch to go shopping with me, and we met outside Bloomingdale’s.
“This seems very plebeian for you, Leah. Don’t you have some secret luxury department store where you need a black Visa card just to get through the door?”
“Bloomingdale’s has everything we need. Well, okay, not everything. But the core parts.”
Bloomingdale’s was enormous. Floor after floor of clothes, shoes, cosmetics, furniture, and whatever else they had decided belonged in a department store. Leah took me up to the fourth floor, which appeared to be where clothes for serious women were located.
Leah quickly found the things she wanted for me. A black high-waisted pencil skirt that stopped just above the knees. A black bodysuit with a deep front opening and a closed neck. Knee-high black leather boots, and a structured black leather blazer fitted at the waist.
I took everything into the fitting room and came back out looking like someone people were supposed to listen to.
Leah gave me a long look.
“I think I’ve outdone myself. You should wear this on your first day at work.”
“Dress for the job you want?”
“I’d hire you.”
She looked at the time.
“Let’s hustle. We have a pickup close by, and the car will be here in thirty minutes for the final stop.”
We made our way to Sermoneta Gloves, just across from Bloomingdale’s.
The shop was smallish and focused mostly on gloves, with some hats and scarves as well. Leah headed toward the back desk, which I assumed was for special orders, and started talking to the woman behind the counter.
I followed her over and watched the woman disappear into the back for whatever Leah had ordered.
When she came back, she was carrying a long box. Inside were a pair of long black leather gloves.
Leah must have ordered them in advance.
“Black kid-leather opera gloves, silk-lined. Size seven,” the woman said.
I touched the leather. It was very smooth.
“Try them on,” Leah urged.
I took off my jacket and handed it to Leah, rolled up my sleeves, and pulled both gloves on.
They felt smooth and comfortable around my arms, and when I made a fist, the leather gave a faint creak.
“Very nice.”
The car arrived shortly after we left Sermoneta Gloves, and it was the same driver who had taken us out to the spa.
“Hey, it’s you again,” I said.
“Hello, Miss Williams.”
“I don’t think I ever caught your name?”
“Thomas, Miss Williams.”
He opened the door for me, and I stepped inside. This was one of their city cars. Smaller than the ones that had taken us to the spa, but still a huge car.
“Thomas, are you, like, assigned to me and Leah?”
“I am the preferred driver for TEG requests. I will usually be the one driving you if I am on shift, or if you book in advance.”
“In that case, you should call me Mia. You’re probably going to see a lot of me.”
“I’m not sure Miss Takahashi would approve of that.”
Leah suddenly started paying attention to my conversation with Thomas.
“What now?”
“Can you make Thomas call me Mia instead of Miss Williams?”
“Who is Thomas?”
“Ohh, bourgeoisie burn! Thomas is our driver. He handles most of the TEG driving requests.”
Thomas tried to suppress a laugh.
Leah looked up at him, and this time actually looked at him.
“Oh. You’re the same driver we had for our spa trip.”
“Indeed, Miss Takahashi. I handle most of the TEG driving.”
“In that case, Thomas, I think it’s fine if you call us by our first names.”
“I will do my best, Miss… Ahem… Leah.”
It was about a forty-minute drive to Purple Passion/DV8, and when I saw what the store sold, I genuinely wondered what we were picking up here.
“We need to pick up a few things. Should be quick,” Leah said.
“I’ll wait somewhere close by. Give me a text when you’re done and I’ll come back around,” Thomas replied.
Purple Passion was a sex shop of the highest quality. Rows of latex and leather outfits, vibrators and dildos, every possible tool for every possible scenario.
We were greeted by an older woman with purple hair.
“Hello there, I’m Lolita. Anything I can help with?”
“Looking for a leather riding crop, a collar with a chain, and a humbler.”
“Let me grab the crop, and I can show you our selection of the other two,” Lolita said.
“A humbler?” I asked Leah.
“It’s a restraint thing. It was listed in the green section for Mark.”
“I thought it meant, like… he wanted to be humbled.”
“Oh, this will most definitely make him humble.”
Lolita came back with the crop. It was black leather and looked pretty much like I expected a riding crop to look. Nothing particularly exciting.
I took it, and Lolita guided us over to the collars.
We picked something fairly simple, but with enough weight and width to look deliberate. This was mostly for show, after all, so it might as well show.
Then we reached the humblers.
I suddenly understood what the word meant.
They looked like black wooden bars with restraints attached, and there were little line drawings beside them showing how they were supposed to be worn.
Oh.
That looked uncomfortable.
Leah picked up one that also attached to his legs, forcing him into a kneeling position unless he wanted to make things considerably worse for himself.
“Okay, I think we got what we needed. Lolita, will you ring us up?”
Leah pulled out her phone and sent Thomas a text.
“You think Mark is into that?”
“He put it on the list, so I have to assume he is.”
Thomas drove Leah back to the TEG office in the Flatiron District before taking me home.
“You like being a driver, Thomas?”
“Pay is good. Much better than driving Uber or a taxi.”
“What about us? Like, me and Leah? Are we demanding customers? We made you show up early that time at the spa, I realized.”
“Nah. You usually book in advance, and you behave much better than a lot of the people the company drives for. The spa trip wasn’t an issue. Miss Takahashi…”
“Leah,” I interrupted.
“Sorry. Leah let the company know about the change the evening before, so I had plenty of notice.”
“You have other companies you’re the main driver for?”
“No. We have one primary account and three secondary ones. Then we can get assigned random trips if they’re short on drivers.”
“You still get paid if we don’t take any trips?”
“I have a guaranteed minimum every month, then overtime and weekend bonuses depending on the work. You shouldn’t worry about me, Mia. I’ve got it good.”
“So you make more if we take trips on weekends?”
“I like my weekends, though.”
“So don’t go on trips on weekends?”
“Don’t worry about my pay, Mia. That’s for my manager to handle, and for TEG to pay for. You and me, we’re not exchanging money.”
I leaned back in the seat.
Enough class warfare for today.
When I got home, I booted up Dispatch again.
Only a minute or so later, Mossybyte showed up in chat.
“Caught you at a bad time, Mossybyte?”
Mossybyte: I was studying.
“What’s your field of study, Mossybyte?”
Mossybyte: Music.
“What type of music do you like?”
Mossybyte: Soundtracks, video game and movie stuff mostly. Musicals. I like music that is for something.
“That’s why you like watching Twitch?”
Mossybyte: A bit. I like games a lot as well.
“You game much?”
Mossybyte: Used to, don’t really have the setup here.
“Lack of TV and a console in your student accommodations?”
Mossybyte: Got that straight. I hardly have space for my coffee machine, let alone a TV.
Mossybyte: BTW, who texted you last night? You looked shocked.
“Eeh, you weren’t there. How did you see that?”
Mossybyte: I looked at your VOD.
“Oh, right… those exist. Yeah, it was an old friend asking for help with something.”
Mossybyte: Looked like you got an impressive dick pic or something.
“Was just surprised to hear from them, is all.”
I went back to playing Dispatch and talking shit about how Malevola wasn’t a romance option.
I met Dan a block away from our dinner with Anna and Mark. I had a backpack with the contracts and the things we had bought, which I handed to Dan because it completely ruined the look.
I had my hair in a tight top bun, and Leah had helped me with dark eye shadow and lipstick. I looked sharp as hell.
The green backpack did not.
Dan was dressed more casually than me, but not badly. Shirt and jeans. Black shoes instead of sneakers. The backpack didn’t look weird on him.
We walked to Scarpetta, where we had agreed to meet Mark.
I spotted Anna and Mark at a table. Anna was wearing a dress that looked a lot like the red one I had worn at the wedding where we first met. Mark had on a nice shirt and vest combination. He looked professional.
We joined them at the table, and Dan complimented Anna on how she looked.
She smiled and thanked him.
I guess the play had already started.
I pulled a leather letter case from the bag and took out the contracts I wanted Mark and Anna to sign.
Mark took the contract and started reading, then looked back up at me.
“Proskauer?”
“Yeah?”
“As in Proskauer Rose?”
“I’m told they’re very good.”
“You had Proskauer write a contract for this?”
“I thought it was best to have someone more professional look it over.”
Mark stared at me for a second.
“Proskauer Rose has thousand-dollar-an-hour lawyers.”
I shrugged.
“Is that a problem?”
“No, it’s just… I’m a lawyer. I know Proskauer Rose.”
“Good. Then you know I’m not fooling around.”
“Clearly.”
He continued reading, nodding at certain parts.
Dan and Anna were flirting like no one was watching.
A waiter came over and asked if we were ready to order.
I went for the black tagliolini, and Dan chose the duck and foie gras ravioli.
Anna and Mark had apparently already ordered, but had asked them to wait until their guests arrived so everything could come out together.
A bottle of red was brought to the table, and Mark poured us all a glass.
“So what room are we using?” I asked, tasting the wine.
“I thought we could use our hotel room?”
“That works. You picked a safe word?”
“Yes. Green Apples.”
He signed and initialed the contract, then poked Anna so she could do the same.
“We also recorded the consent videos you asked for and sent them to the email address you gave us.”
The waiter came back with our food, and I made sure I spoke loudly enough for him to hear.
“Well, sounds like you’ve been a good boy and done everything right. Shame what’s gonna happen to you tonight, though.”
He blushed and looked down when I said it, and I smiled.
“You liked that?”
He nodded.
“Good. Eat your food. You’re gonna need your strength.”
We wrapped up dinner, and by this point Anna was playing footsie with Dan and feeding him dessert, very much into the role she had been assigned.
“Give me the keycard to the hotel room,” I told Mark.
“Why?”
I gave him a disapproving look.
“What did you say?”
“I’m sorry. Of course. Here.”
“Take Dan and Anna up to the room in five minutes.”
“Of course.”
I looked down at the card he had given me.
Penthouse Suite.
Very impressive, Mark.
I took the elevator up and noticed it required a keycard to reach the top floor.
I hoped Anna had a spare, or this was going to get awkward.
The suite was basically a small apartment. The bedroom alone was bigger than my old bedroom, with a king-sized bed and enough open floor around it to actually move. Through the hall was a separate living room with a couch and TV, a little kitchen area, and a table by the windows. There were two bathrooms because apparently one bathroom was for poor people.
I started setting things up. I placed the humbler and collar on the stool in front of the bed, dimmed the lights, grabbed a bottle of champagne from the minibar, and poured myself a glass.
Then I sat down on the couch in the living room with the riding crop across my lap.
Anna came stumbling into the room a few minutes later, hanging off Dan’s neck.
“Dan, you good at fucking?”
“I’ve been told I am,” Dan laughed.
“Good, because my fiancé is fucking horrible. Big dick, barely knows how to use it.”
“I’ll be sure to show him how to properly fuck.”
Anna smiled and looked back at Mark, who was following a few steps behind and hearing all of this.
“You gonna watch? Learn how to properly fuck a woman, Mark?”
“Anything for you, Anna.”
I stood up, holding my riding crop in one hand, and smacked it against my other palm.
“Dan, go have a drink. I need to prep these two.”
“Yes, Miss,” Dan replied.
I pointed the crop at Anna.
“Into the bedroom. Lose the dress.”
I pointed it at Mark.
“Follow her. Pants, underwear, and shirt off. Keep the T-shirt and socks.”
They both moved toward the bedroom. A moment later, Anna was naked and Mark was standing there in nothing but a T-shirt and socks.
It was not a dignified look.
He saw what I had laid out on the small stool in front of the bed and swallowed.
“Anna. Put the collar on your fiancé, take him over to the cuck chair, and attach the leash to it.”
Anna did as instructed. When she was done, I handed her the humbler.
“You know how this works?”
“No,” she said, in a much more sober voice than she had used with Dan.
“Your fiancé does. Let him explain how to put it on him.”
There was a quiet exchange between Mark and Anna. Anna sounded shocked once she understood what the humbler actually did, but she pushed through and clamped it into place across his balls, then secured the restraints around his legs.
“Go get Dan,” I told Anna.
I looked down at Mark. He was fully erect, and true to Anna’s word, he was not poorly endowed.
“I don’t want to see you come until this is all over. You got that?”
He nodded.
“If I see you come before it’s over, I will not take it lightly.”
He nodded more firmly.
I gave his dick a quick smack with the crop, making him yelp and start going soft.
“Next time, it’ll be much harder.”
Mark licked his lips and tried to adjust his position, but the humbler made the whole thing difficult. I saw it cross his face when he moved a little too far and caught a jolt of pain.
Anna came back in with Dan. She had put her shoes back on. Black heels, sharp, and nothing else.
She looked at Mark once. A flash of doubt crossed her face, then disappeared as she slipped back into the horny act.
“Anna, how good of a cocksucker are you?”
She looked confused for a second before Dan put a hand on her head and gave her a small push down onto her knees.
He unbuckled his pants and let them fall.
Anna started stroking him through his boxers, finding that horny smile again.
I put the crop under Mark’s chin.
“She deep-throat you, Mark? Ever let you face-fuck her?”
He shook his head.
“Says it’s too big. She can only handle the tip.”
I looked over at Dan. Anna had gotten his dick out and was stroking it, licking along the length.
“I dunno, Mark. Dan looks bigger than you.”
My riding crop lowered toward his dick. He was hard again, the head pressing against the hem of his T-shirt.
“I mean, you’re a decent size. But Dan is big.”
Anna tried taking more of Dan’s cock into her mouth, but she still wasn’t getting very far.
“Oh, I think you can do better than that, Anna.”
I walked over and looked her in the eye.
“Open up. Swallow when it goes in.”
Dan held her head and pushed again. I saw Anna try to swallow around him, and this time it worked. He slid deeper, and her eyes went wide.
“Good girl.”
Dan pulled back, and Anna gasped for air.
“Again.”
Dan made it all the way in again, his balls resting against Anna’s chin. He stayed there a little longer this time before pulling out. Anna gasped for air again.
I moved back to Mark and sat in the cuck chair beside where he was kneeling.
“It’s beautiful to watch, you know. When I first saw her suck a dick, she was using her hands like some teenager. I had to pull her hair and tell her that hands are for balls and ass.”
Mark grunted, and I saw that the wet spot on his shirt had grown considerably.
“I don’t want to see you blow your load just yet, Mark.”
I stood up and gave him a hard smack across the balls with my crop.
He let out a yelp that made Anna look over, but Dan put a hand on the back of her head and turned her attention back to him.
“Dan, put her on the bed. Ass toward Mark, and start fucking her.”
“Yes, Miss.”
He lifted Anna from the floor and moved her onto the bed.
“I want you to see how wet she is. How ready she is for Dan.”
Dan climbed onto the bed and positioned himself behind Anna before sliding in and starting to fuck her.
Anna started moaning immediately.
“Fuuuck, you’re so much bigger than Mark.”
Dan slapped her ass.
“Damn, your woman is freaky, Mark.”
“I’m not his woman anymore. I’ll do whatever you want,” Anna said to Dan, loud enough for Mark to hear.
“That’s a lot of things I might want,” Dan warned.
Anna let out a moan in reply.
I looked over at Mark. He was hard again, his dick twitching beneath the thin, wet fabric of his T-shirt.
“You’re hard again? I don’t know what to do with you. How about this? If you come, I’ll move you to the living room and you won’t get to watch anymore. That threat enough?”
He gave me a look of fear. I had clearly touched a nerve.
I crouched down and grabbed the head of his dick with my gloved hand.
“Or maybe I should make you come right now? Just to get you out of my sight?”
He bit his lip and took a deep breath.
“I won’t come. I swear.”
I smiled at him.
“Good boy.”
I looked over at Anna. She sounded like she was having her first orgasm of the night, gripping the sheets and groaning more consistently now.
My eyes went back to Mark.
“You hear that, Mark? That’s the sound she makes when she does not fake it. I suspect you’ve never really heard that before.”
He looked down at the floor, clearly trying to concentrate.
“You ever had anal with your wife-to-be, Mark?”
“No. She says it’s disgusting. Doesn’t even like me touching her asshole.”
I laughed.
“She didn’t even let you try? She told me she’d tried it with several people before giving up. Guess you just weren’t one of the lucky ones.”
Dan was giving Anna a breather after her orgasm, but he was still hard.
“Any requests, Miss?”
“Turn her around to face Mark. Lube her up and show him what she looks like getting fucked in the ass.”
“As you wish.”
Dan shifted Anna around until she was facing Mark and me.
“You ready for this?”
She nodded.
“You really never let Mark even try your ass?” I asked.
“He never made me feel like he deserved to. Such a loser in bed.”
I nodded as if the reasoning made perfect sense.
Anna groaned and closed her eyes as Dan started working lubed fingers into her.
She grabbed the bedsheets with both hands.
“No, no, no, Anna. I thought you knew this.”
She looked confused.
“Ass up. Face down. Spread your cheeks.”
She bit her lip, reached back, and spread herself open for Dan.
I gave her a pat on the head.
“Good girl. Now make sure you describe how it feels to Mark. Tell him all about the things he’ll never have.”
She looked up at Mark, and I followed her eyes.
Mark was biting his lip and leaning forward, clearly trying to use the discomfort to keep himself from coming. He was really putting in the effort to keep his promise.
I heard Anna gasp when Dan pushed into her.
“Tell Mark how it feels, Anna.”
She kept her face down for a second, breathing hard while Dan slowly worked the head in.
Then she looked up at him.
“It hurts. He’s thick. So thick.”
Dan pushed another inch. Her knuckles went white against the sheets.
“Keep going,” I said.
“I feel so stretched. Feels like he’s forcing the air out of me. I can feel every vein.”
Mark made a low sound. His cock jumped beneath the wet T-shirt.
“Eyes on her,” I told him. “Don’t look away.”
Dan sank deeper. Anna’s voice cracked.
“He’s all the way in. Fuck. I feel so full. Fuller than I ever felt with you.”
I walked around behind Dan and watched him start moving. Slow at first. Careful. Then longer strokes once Anna relaxed.
“How is Mark in bed, Anna?”
Her answer came out broken between thrusts.
“You were always careful. Like I was a doll you were afraid you’d break. He just takes it. Like my ass belongs to him.”
Mark’s breathing had gone ragged. The wet patch across his shirt had spread even farther.
I crouched beside him again and took his chin in my gloved hand, making him keep his eyes on the bed.
“You’re never getting that,” I said quietly. “She’ll always know what it feels like when someone who actually knows how to use a cock decides to claim her ass. Maybe she can describe it to you while you jerk off?”
He nodded against my fingers.
Dan picked up speed. The wet slap of skin filled the room. Anna’s moans had turned higher, more continuous.
“You liking that, Anna?”
“God, yes.”
I walked back over to them and reached between her legs, rubbing her clit with my gloved hand.
She let out a deep moan, and I kept a steady rhythm that matched Dan.
“Thank you, Mia,” she whispered.
“This is what I wanted. Thank you.”
I felt unnerved by the break in kayfabe, but I didn’t stop rubbing her, and Anna soon broke into another orgasm.
Dan kept pounding through it, and by the end he couldn’t hold out anymore either.
Anna’s orgasm faded while Dan was still pulsing inside her.
I looked over at Mark. He was breathing heavily. I lifted his shirt and found him still hard.
“Good boy, Mark.”
I started stroking his dick with the tip of my shoe, and he came almost instantly.
I stopped immediately and pushed his dick upward so the cum hit his face instead of me. He kept pulsing for another four or five spurts before finally stopping.
“You followed the rules, Mark, so your reward is to go clean up your fiancée.”
I went behind him, unlocked the humbler, and unclipped the leash from the chair. He slowly crawled over to Anna and started kissing her.
Dan came over to me while I was wiping cum off my shoes.
“Good job,” I said.
“Nothing to it. Happy to help.”
We both looked over at Anna and Mark. She was mounting his face so he could clean Dan’s cum out of her ass.
“You go take a shower. You’re sweaty as hell, and I don’t want you ruining your shirt.”
“Mm. Smart.”
Dan walked into the bathroom, and I sat down in the chair to watch Mark eat Anna’s ass.
After a few minutes, Anna sat up on the bed and gave me a smile.
“That was fun. I’m glad you did it.”
I gave her a bored look.
“Go join Dan in the shower. I want to talk to your fiancé.”
She looked over at Mark. He nodded, and she walked into the bathroom.
“Was this acceptable?” I asked him.
“More than I ever could have hoped for.”
“I’m glad. Our business is concluded, then?”
“Can we do this again?”
I gave him a questioning look.
“I thought this was a one-time thing you wanted to try.”
“Maybe a few more times?” he suggested.
I heard Anna moan from inside the bathroom, and we both looked over.
“Let’s discuss it later. Send Dan out to me when he’s done with Anna.”
I went out into the living room and poured myself another glass of champagne while Mark remained in the bedroom.
About an hour later, Dan came out fully dressed and smiling.
“Took you long enough.”
“It’s hard to come a second time that soon.”
“Never takes you that long with me.”
“Well, being sexy helps.”
“You flirt.”
I gave him a weak punch in the arm.
“Need a ride home?”
“That would be nice.”
I opened the car company app Leah had installed on my phone and saw that Thomas could pick us up in fifteen minutes.
“Mark wants to do this again.”
“Not surprised.”
“You knew this was gonna happen?”
“He looked very ‘happy’ during the session. He just had the best sex he’s ever had in his life, and you think he’s gonna go, ‘Yeah, that was nice. Now back to missionary every Thursday’?”
“Oh. I didn’t think about it that way.”
“Yeah.”
“Is that bad?”
“Nah, but we’re not anywhere close to done.”
We stepped into the elevator, and I started regretting saying yes to all of this.