Fucking That Guy You Hate Pt 01

I want to share one of the stories that makes me squirm every time I think about it. My worry is that it'll come off pedestrian in writing but put yourself in my shoes and think about how intense the humiliation was in these moments.

Ash and I were in a full-fledged cuckolding lifestyle at this point where I was in chastity 24/7 unless she wanted me to have a release. Those were happening between 45 to 100 days apart. We were in such a good rhythm and although we didn't have a bull at the time, we were having plenty of fun.

One thing I'd fantasized about quite a bit over the years was Ash fucking a complete asshole that we couldn't stand. Just the thought of some arrogant prick fucking her and knowing he'd "bested" me turned me on so much. Ash was on board but we didn't have anyone we really hated... made it a bit difficult to hate fuck.

One day, Ash was at the office and a guy from a different department, sales, came into her office. They'd only seen each other in passing so she didn't really know him. He'd joined a couple of months ago from another large company.

His name is Andre. He's a black man, about 6' tall, and really good looking. He knew it, too.

He introduced himself to my wife and said he was needing some data about some land plots. I'll spare you the work park of this.

"We could grab some lunch and I tell you what the client is really looking for," he said.

Ash smiled, "Well, I am a married woman, so I'm not sure that'd be appropriate."

"We could keep it as appropriate as you want it," he said putting his hands up nonchalantly.

She blushed and told him she would get the data for him.

He stood up to leave and said, "Send me a message if you need anything or change your mind."

When she told me about this at home all I could think was, "What an asshole. Didn't even care you're married." Then I realized I was straining a bit.

"Yeah," Ash said, "You know how brokers are. They think they're the shit."

We'd made a rule when we started this lifestyle that we'd never fuck with coworkers. Just not worth it. Neither one of us said anything beyond that about it.

She messaged him the next day and included the site data, he replied it looked great, they moved on.

Two days later Ash was in the breakroom getting her lunch together when he popped up close to her and leaned forward. He said, "Damn, still married." She laughed it off and they talked for a minute. She said he always had that cocky "big dick energy" that made her want to take him down a few pegs.

I told her it was hot listening to how he hit on her like that.

Ash kept doing whatever she was doing and said, "I know you've been busting in your pants hearing about it." She smiled.

Time went on and every now and then there'd be a story about Andre being forward with her.

One time she told him, "You know I could go to HR and get you fired for what you say to me?"

"Yep. Sure could. If you didn't like it," he said, trailing off.

Ash said she just smiled at him and said, "You're such a dick."

"That is one of my best attributes," Andre said as he walked away.

About 7-8 months after they met, he left the company for one of their competitors. If you know this world its not super unusual. Ash liked his LinkedIn post about his move and wished him well.

"I'll miss the flirting, I'm not gonna lie," she told me after telling me about him leaving.

"You know, he's not a coworker anymore..." I said, suggestively.

"I'm well aware," she said while laughing.

"Do you want to fuck him? If you don't then let's just drop it."

She shifted her head while smiling, "The guy is an arrogant asshole, which I know excited you, but he's just a lot."

Ashley walked her fingers up my chest, "On the other hand... a girl starts to wonder."

I felt my dick shift in the cage.

"If he can even halfway back up that attitude he'll he an amazing fuck."

"I'm sure he'd back it up," I said while trying not to drool over the thought of her getting impaled by a huge cock while he laughed about me.

"Why don't you send him a message on LinkedIn and see what he says? I have a feeling he'll make this easy for you.

We talked about it for a while but she finally did decide to shoot him a message.

"Innocent enough, wishing him well, right?"

She opened her phone and sent him a message telling him he'd be missed and she wished him well.

It was about 5 minutes before he sent back, "Thanks, Ashley! I'll definitely miss our break room run-ins.

I can't check for that ring from over here either. Haha."

Ash responded, "Haha. The ring isn't going anywhere. Pesky little thing."

"It is pesky. It has blocked a lot of fun."

I could see her getting turned on as she typed.

"Well, if you ever want to stay in touch here's my number."

He hearted it and then text her almost immediately.

"Hey, it's Andre. If nothing else we can be pen pals."

She sent an, "Lol."

"So, how is your husband? He better be a badass to be married to you."

She replied that I'm awesome and that I do "whatever it takes" to make her happy.

"Whatever it takes, huh?"

"Yep."

He didn't say anything back.

The next day I could tell she was disappointed that he didn't say anything back.

"Text him again," I said.

"That's desperate as fuck," she replied.

"Who cares? Your goal is to fuck him, not date him."

She looked like she was weighing her options then shot him a text.

"If you want to get together for lunch and discuss those site locations sometime, I'm down."

She showed me what she'd written.

"Well there goes any ambiguity," we both laughed.

This dude was quick at the reply, "The ring fall off already??"

"Nope, its steady. I don't think it'll burst into flames if we have lunch."

"Yeah, totally... let's have "lunch," he shot back.

She told him I was busy helping my family and she was free in just an hour or two.

They picked a casual spot where they could get a midday drink or two.

When she stopped texting him I asked her if she wanted me to to down on her. That was usually a strong yes.

"Yes, but I don't want to cum."

We went to the bedroom and I got on the floor next to the bed while she sat on the edge and put her feet on my shoulders. She was incredibly wet. I realized them how much she'd been wanting this for ages.

I got her going and she grabbed my head to hold me so she could cum but I pulled back so she edged and it drove her crazy. Whenever we do this I have zero sympathy with how infrequently I cum at all.

"I hate you," she said as she laughed.

"Hey, you told me to edge you."

We got her up and she started looking at what to wear. We only had about 45 minutes until she was supposed to be there.

She picked out a tannish dress that showed serious cleavage and hugged her body until right below her ass.

I had picked out some of the sexiest panties she had and handed them to her and she paused.

"Panties?" she looked in the mirror, "It feels silly and honestly disrespectful to wear panties for a guy this alpha."

She tossed them back to me. She then had me shave her pussy fresh. It was perfect. I gave it a kiss before I got her down off the counter.

We drove to the restaurant to meet him. Of course I wasn't going to go in or anything but I'd wait in the car.

As we drove I asked her if she especially excited since she hadn't been with a black guy in a while.

"Not really," she played it off as she perfected herself in the mirror. "I've been with black guys before. I don't care what color the meat is as long as it gets me full."

I couldn't help but chuckle.

"What a life we lead." I said.

She put her hand on mine and she laughed.

When we got to the restaurant I dropped her off at the front like an uber. He was already there and I watched as she went inside.

I backed into a spot nearby and just waited. I had brought some snacks and I started eating them.

I saw my wife calling me and I answered but heard no answer on the other end. She'd done this once before when she eas meeting other guys to fuck with me. She'd call me on speaker then turn down the volume the whole way so I could hear their conversation.

It sounded like two old lovers talking. They knew what they were there to do.

"You look so damn hot," Andre said.

"Thanks," she said, "My husband loves this dress."

"I bet he does. Is that why you wore it? You're a cruel bitch huh?"

They laughed.

"This is going to be the longest lunch ever," she said.

"How about an appetizer?" he said back quickly.

I heard them looking for the waitress and he finally said, "Hey, we'll be right back, ok?" She said fine.

I heard rustling as they got up and I saw them walking quickly out of the restaurant in front of me. They walked to a black Audi suv parked right in front of me.

Ash knew I was right there and pulled her dress up over her ass showing me the whole damn thing as she got in the backseat.

I heard a lot of noises and could tell they were making out. The car was moving every so slightly and I desperately tried to see more than I knew I ever would be able to from there.

I heard the belt, heard the zipper, and then a "Oh my god your dick is perfect..." I heard her say. More noises I assumed were the beginnings of a blowjob. "I can't fit this whole thing in my mouth," she laughed.

"You can fit your husband's whole dick in hour mouth?" he said, making it clear I was inferior, "no wonder you're back here sucking mine."

I heard just noises for a bit then her moaning. I had to guess he was fingering her. I had pulled my cage out from my sweatpants and was moving it slightly as I strained. That's about all the pleasure I can get in there.

"Have you ever fucked a married woman?" she said.

"Plenty," he said smugly. "That I know of. I'm sure plenty were that didn't tell me."

He continued, "There's something about a black cock that makes a married woman go crazy." He laughed a little.

"I always say I don't care what color it is... but fuck your so hot," she said. She kept sucking.

"Good girl," he said as I heard the slurping. "Why don't we just go back to my place?"

"Fuck yes," she said.

I heard them moving then saw the car doors open and he got in the front seat holding his pants with one hand. She looked over to me as she was getting in the front passengers seat and smiled while giving me the finger.

She got in and I heard the phone rustle before she hung up on me.

I went home with a smirk on my face and straining against my cage.

After around 20 minutes I got a text from my wife.

"Call me. Ask what I'm doing."

I was excited as I called her.

"Hello?" she said.

"Hey babe, what are you up to?"

"I'm just over at Danielle's house hanging out."

"Ah nice," I said, "Tell her I said hey."

"Will do," she said.

I think she was blowing him at the same time and he was getting a kick out of it.

"I was thinking about making you dinner tonight. Filets and sweet potatoes?"

"Ugh you're so sweet! I don't deserve you."

I told her I loved her and then we hung up. I was so turned on. She was so creative.

I knew Andre was probably about to fuck her brains out after hearing my voice. I'm sure she did that to rile him up.

About an hour later I got a video and my wife was barely recognizable with her long brown hair matted against her forehead and the sweat on her face smearing her mascara. She was a complete and total mess.

As I hit play I saw it was a selfie video and she had her head and shoulders down on the bed with her ass in the air. Andre was pounding her. They were both naked and he was slapping her ass as he pounded her hard.

"You're taking a video?" he asked

"I want to watch this later," she said, "what would you say to my husband if you could right now?"

"I wouldn't say anything to that bitch... except 'she's mine now.'"

He pounded her and she was loving every second of it. The camera lowered into her face more and she stared into it before the video ended.

"Holy. Shit." I said out loud. We'd done a lot of hot things over the years but this was immediately one of my favorites.

She had to take an uber back home. She said even that made her feel hot. Like she was used and then sent out.

She walked in and the first thing she said was, "That uber driver knew exactly what I'd been doing."

I laughed with her for a second.

Ash walked into our bedroom and collapsed on our bed. She was on her back and she pulled up her dress and didn't even have to say anything.

As I was licking her sore pussy she moaned slowly and quietly.

"Baby," she said, "I know I said I'd been with black guys before... but that guy? That guy is a black man."

I stopped long enough to say, "I'm glad you enjoyed it. It sounded hot."

"That was the best sex I've ever had," she looked down at me, "it won't be the last time."

She handed me her phone with a text from him open, "I'll try and be discreet if you want that to be a regular thing. You're a good fuck."

I got mad he only called her "good" and she said he probably did that because he wanted to take most of the credit for how good it was.

"Him not knowing you know is hot but if you want some serious humiliation he is the one," she said, exhausted. "He talked so much shit about you."

It was a super hot idea, having a bull of sorts who was that arrogant. Its something we hadn't had to this point.

"That was the best sex I've had since Jason... maybe ever. He was the biggest I've had."

I kept licking.

"I want you to see it and what it does to me..."