Cuckolded After Boss’s Son Moves In

Note: This story contains cuckold, humiliations, and cheating. All character are 18+ And is only intended for such and audience.

My Name is John and I'm married to an amazing woman named Hailey. She happens to be 34 to my 35. She also happens to be my second wife. I split from my first wife Jennifer amicably. Although Hailey never wanted any children, and shot me down every time I tried to bring the subject up, I had a daughter named Jessica from my first marriage.

We're both pretty much average people otherwise at 5'9, 150lbs, brown hair, with a bit of lean muscle. My wife is 5'6", 120lbs, 36C, 28, 34, and yes she's blonde. I would describe her as closer to thin than athletic.

I have a pretty boring job that consists of me working on financial documents and charts.

My boss's 19 year old son Jake needed a place to stay. Wanting to score points with my boss for an upcoming promotion, I let him stay at my place. We barely noticed him the first couple of days. But that completely changed when Saturday came around.

He would bring a new girl back every Weekend and they'd be quite vocal. My wife kept telling me to kick him out. I couldn't risk getting in trouble at work for it, and told her he'd only be here until the end of the month.

One day, she had enough of all the late night ruckus, so she went down there to tell him off. I was unsure about what to do, so I stayed in the room for a minute before going after her. When I approached the guest room I noticed she was just standing at the doorway with one hand over her mouth. As I got closer I closer to the door I could see why.

There was such a length going into and moving out of the girl on the bed. The couple were too busy to notice us, and we eventually left but still very much in shock.

The next day my wife firmly told me that Jake had to go. I agreed. But it was easier said than done. Jake must have left early. It looked like I'd have to talk to him after work.

I was busy typing away on my computer before my boss threw his hand on my shoulder and asked me how everything was going, including the living situation with Jake. Like most people I told him good things about his own son, before getting to the issue at hand. But before I could he cut me off and told me he had to go before giving me a raise.

Back home, I brought some champagne home to my wife. We got slightly drunk and made out for a while. Jake eventually came back to the house and noticed we were in a fit of giggles.

"If I didn't know any better, I'd say you two were celebrating something," he said.

"John got a raise!" Hailey exclaimed.

"No way!" Jake said mind if I join you two?" he asked before coming with another glass. Not wanting to be impolite, we didn't ask him to leave. We got drunker and drunker. Jake then suggested we play a game of Strip Poker.

"Don't think I don't know what you're doing, young man!" Hailey slurred trying to sound stern while holding back giggles.

I ended up losing my shirt and pants while Hailey lost her shoes and earing. I started to get tired.

"I think I'm calling it a night," I said.

"I'll meet you in the bedroom soon," Hailey said before she winked and blew me a kiss.

I passed out as soon as I hit the bed.

I groggily woke up to some moaning and realized that it was probably Jake and another girl. I had to go tell him to quiet down before the noise woke Hailey. That's when I realized she was no longer in bed. She either went to quiet the couple down, had to use the bathroom, or get a drink of water. Either way it was best I got to Jake's room as soon as possible.

As I made my way closer to the guest room, the groans and moans got louder and somewhat familiar. Had he brought the same girl over again?

As I peered into the room that's when I saw and remembered how long Jake's member was. The second thing I noticed was honey blonde hair, almost like Hailey's! Then I noticed the ring on the woman's hand as she placed it on his back. It was unmistakably , it was Hailey's ring! I've never heard Hailey being so loud or making the sounds she was making now even though I've heard all the other girls that were with Jake making those same sounds.

"Ohhh, yesshhh, maaah, mahhh, make me cum again!" she stuttered out before she started shaking and throwing her head back. That's when Jake's motions became more jerkish and less rhythmic. I knew what was coming. He then impaled himself inside. They both gasped for breaths as if they had just ran a marathon. What followed next was lip smacking kisses. As he became limp I saw the jizz pool out of her, down her crevices, and onto the bed.

I went to bed. I woke up temporarily forgetting everything that happened last night. I was hoping it was all a dream until I passed the guest room. That's when I heard her moans again. I told myself he was just giving her a message as I left for work. But as I was leaving I made eye contact with her through the partially open blinds as she was in doggy style. I had to drive around for a while before I could calm down enough to get to work.

When I came home, I told her that we had to talk.

"I know," she said, "And I'm sorry, John. I just had too much to drink and felt so alone with you at work so much."

We both cried for a bit and she apologized some more. She told me that I had to kick Jake out. I agreed.

But I couldn't immediately kick him out because I was already in trouble at work for arriving late.

Once I found Hailey's black lace panties with a small red bow at the front in Jake's room. I confronted her about this, but she mentioned how it must have fallen from the hamper as she was collecting laundry.

One day I came back early because I forgot some paperwork. That's when I started to hear moans coming from the guest room. The door was ajar and I peeked in. That's when I saw Hailey blowing Jake. We briefly made eye contact before I ran off. Drool was running down her mouth and her makeup was a mess.

After that moment, Hailey would sneak out and go to the guest room. The door was always ajar. And I regret to say I would go and watch sometimes. And a few times Hailey and I would make eye contact. I never knew if Jake knew. They'd always start by making out and groping, before she'd give him a blowjob, and then move into sex. He'd always finish by cumming inside her.

Hailey and I's sex life completely died. Eventually Hailey and Jake became less discreet around me. When they did it, they would do it during the day, and wouldn't keep quiet. Hailey said a lot of things to Jake as well as a lot of gibberish. One day, Jake walked up to Hailey and started making out with her right in front of me. He eventually bent her over and pounded her. Hailey even borrowed some of my money to buy Jake a new watch.

I told Hailey she had to be careful when Jessica came to visit from college. Hailey didn't, so her and Jessica got into an argument full of screams. I was too embarrassed to get involved.

I went to check up on Jessica later that night and heard an odd noise. When I peeked in I saw Jessica in just her pink panties struggling to take Jake's monster penis in her mouth. She would gag and salivate all over his penis. Her mascara ran down her face.

Not being able to take much more of this I turned around and too long after, I started to hear her moan in pleasure.

From that night on, I would hear grunts and groans either coming from my daughter or my wife. One night, I came back from work to see them both licking and kissing Jake's penis in my own room. Jake smiled at me when I made eye contact. He then said, "Ready for anal, girls?"

They both moaned, "Mhmm,"

Anal? Hailey would never let me do that, she was stubborn about it like the pregnancy issue. After years and years of begging. She would just reply that she didn't find that kind of thing interesting. And she finally snapped and told me to fuck off.

"Turn around so we can get started," he said.

Their smiles disappeared and their pupils dilated when they noticed me. Jessica placed one arm across her chest before looking at Hailey and then at Jake.

"Jake, I'm not sure about this with him here," said Hailey.

"We either do this now, or you can give this dick up forever" he said.

They both looked at each other before Jessica got behind Hailey, and started to kiss and lick Hailey's asshole. Hailey's chest started to heave and she groaned every now and again. Jessica started finger and lip smacking Hailey's ass. Hailey really started grounding her ass back in Jessica's face.

"I think she's ready, get under her," Jake said.

Jessica got under Hailey and the two started making out. Jessica alternated between kissing Hailey's neck and breast as well, I think she even nibbled, pulled, and sucked on them. With her hands she would either pinch or rub Hailey's tits or rub her pussy. And at some points Jessica would rub herself. Hailey let out a scream as Jake pushed his penis head into Hailey in one quick thrust. She grunted as he pushed halfway before pulling out.

"Baby, please take it easy and slow down," she strained through gritted teeth and heavy breathing.

"Look at your husband and tell him how much you love this and how he could never do this for you," he said.

He smacked Hailey's ass quite hard when she didn't say anything.

"Ugggh," she started blubbering and I could barely understand her. With a few tears and between grunts she said, "I never loved you. Keep anal fucking me Jake because I loved it! I never knew what love was until I met Jake, and I love only him!"

He really started to pound her with full strokes. Her grunts of pain turned into moans of pleasure. She started pushing into it and circling her hips when she was fully backed into him. I don't know how long this went on for.

"I'm cumming!" she yelled before starting to shake. Jake started to shake not too long after. Hailey slumped over.

"Get over here and clean me up," he said to Jessica as he finally pulled out of Hailey. Jessica went over and sucked him off enthusiastically, fully cleaning his glazed penis. "It's time," he said.

Jessica bent over and Hailey crawled under her and reciprocated Jessica 's actions as best as she could. Jessica grunted and groaned with pleasure. "Who's your daddy?" he asked as he smacked her left cheek.

"You, you're my daddy!" she yelped between the thrusts and reactionary grunts.

"Don't stop," he said. And she kept repeating it over and over again. She tried to look away from me a few times, but Jacked pulled her by the hair to look at me.

That was the last night that I ever saw them have sex. As a matter of fact, I got kicked out of my own room and had to use the guest room.

He would bring them both to the office both wearing skimpy outfits such as mid-drifts or low hanging tops with leather pants, yoga pants, short skirts, or figure hugging dresses. They would always wear fuck-me heels. And they would often make out in front of everyone. Behind closed doors they moaned and made other sounds that could be heard by the entire office. Not being able to take this public humiliation much longer, I quit my job.

Hailey and Jessica barely looked at me anymore. Jake told me I had to leave my own house because both Hailey and Jessica were pregnant and there was no more extra space.