Julia is the youngest senior executive in her company’s history. She is in her early 20s, is stunningly gorgeous, a perfect brunette with 34c breasts and an ass you could bounce a quarter off of. Her husband, Milton, works for the same company in an executive role as well on his wife’s team. Both excel in their jobs and live an upper-class life.

Office Cuckold Stories: Married Senior Executive Wants to Fuck the Janitor

Milton’s buddy, Joseph, has coasted from job to job over the last few years, mostly general labor. One day, Joseph tells Milton that he was just fired, and to make matters worse, he is also facing eviction from the bachelor apartment he lives in. A sympathetic Milton insists Joseph stay with him and Julia for a little while. Joseph didn’t need to be asked twice. However, being the alpha male that Joseph is, he convinces Milton to do all the packing and moving on his behalf. Joseph didn’t even need to give Milton a reason, as Milton simply asked for the keys to the bachelor pad. It’s evident that Milton is always a little too eager to please the alpha male.

Julia isn’t thrilled with Joseph staying over, as they are polar opposites – she likes things clean and tidy, while Joseph is a slob, with unkempt facial hair and a bit of a growing gut. In comparison, Milton is metrosexual, relying on product to keep his hair groomed and skin toned. Milton is overly concerned with personal hygiene and style, unlike Joseph, who spends minimal time in front of a mirror.

Julia takes notice of the stark contrasts between her husband and his friend every day. At first, she detested Joseph’s habits and fashion sense, but the more she observed Joseph, the wetter she seemed to get. Julia had never met anyone so ghetto before, which makes sense considering she came from a rich family in the suburbs. The habits Joseph had, like leaving his dirty dishes out on the coffee table, or not lifting the toilet seat up when pissing, were not unusual for him. Julia would have normally been offended by Joseph’s disgusting habits, but instead became infatuated with Joseph. She thought about her husband’s slob of a friend during work and sometimes even in bed. It got to the point where she was masturbating in bed thinking about that beast having his way with her while Milton was asleep.

Julia starts going to bed early every night, knowing Milton will be up late watching TV. Every time she inserts that lifelike rubber dildo inside of her, it goes in a little further, and she exhales Joseph’s name repeatedly while pleasuring herself. She begins sneaking Joseph’s dirty laundry into bed with her, sniffing his sweaty t-shirts, mostly when she’s on the verge of cumming. She can’t take it anymore- she needs Josephs’ big cock. She knows everything will change if she became an unfaithful wife, but she’s so obsessed with her husband’s stocky friend that she easily convinces herself it would be worth it.

Joseph knows she watches him. He has caught her staring at him time and again, but he’s used to getting attention from women. Still, the fact that she was doing so told him she wasn’t getting the fucking she deserved. Milton was a good guy, but as far as Joseph was concerned, Julia way out of his league. She needed to be with a real man like him.
Joseph also notices that her eyes land mostly on his crotch when she’s not looking at his face. She loves staring at his bulge while licking her top lip and biting her bottom one. He is going to fuck her, but he wants to play with her a little bit. He wants the faithful housewife to come to him.

By week’s end, Milton suggests to Julia that it might be time for Joseph to leave as he has gotten too comfortable in their home. However, Julia insists that he stay. She offers to get Joseph a job in her company so that he can contribute to the household’s expenses. Now all three of them will be working for the same company, in addition to living under the same roof. Joseph is now the newest janitor in the company, a job that pays well, comes with benefits, and has fairly short hours.

Julia intentionally overworks Milton so she can spend more time Joseph. When Milton comes home, he sometimes catches Joseph and Julia in various places together: swimming in the pool, eating in the kitchen, and even cuddling up on the couch. Milton is appreciative that his friend is kind enough to keep his wife company while he’s working so hard.

Unemployed Friend Fucked My Wife in My Swimming Pool
For more pics in this series see “Cherry Pop“.

Workplace Cuckold Stories: Your Buddy Fucked Your Wife at Work

Rumors circulate at work that the boss is sleeping with the janitor, a rumor Milton never even considers might be his wife and his buddy. One day, Milton sees Joseph in Julia’s office through a window. He sits in her office chair with his head cocked back and his hands behind his head. He assumed his friend was waiting for the boss to arrive, but strangely Julia was nowhere to be found.

Milton jokes to Julia that he thinks Joseph might have night terrors, as sometimes he is awoken by Joseph moaning and even screaming profanities for several seconds behind closed doors. Julia insists he’s fine and that he should ignore any noise coming from Joseph’s room in the future. Milton realizes that Julia never heard those noises since she was never in bed when they happened.

After a major screw up at work, Julia fires Milton, as someone had to be the scapegoat, and Milton, being the company guy that he is, agrees to take all the blame. If he hadn’t, the outcome would have likely resulted in other staff losing their jobs, so Milton’s decision was considered noble. However, Milton used his time off to loaf around the house for the next week rather than find new employment. Milton turns into the slob of the house: leaving dirty dishes around, eating chips in front of the TV in the middle of the day, and even drinking all night. Meanwhile, Joseph becomes a superstar at work, the most popular guy in the company. All the guys love the janitor, and all the girls want to fuck him. The office gossip is that Julia is getting Joseph’s big cock every night behind her cuckold husband’s back.

Julia, sick of her husband’s laziness, tells Milton that he can come back to work if he starts from the ground up. She tells him about a head janitorial role, which Milton assumes is going to be his, and is shocked to learn that Joseph would be promoted to that position. Taking his place would be none other than Milton. Yes, Joseph would be Milton’s boss at work. It was quite the step down – weeks ago he was a top executive, and now he was going to be bossed around scrubbing toilets. Still, Milton takes the job because he knows his wife is right. Like a man, Milton shakes Joseph’s hand and congratulates his friend on his promotion. Joseph tells Milton that he should start referring to him as ‘sir’ now that he’s the boss. Julia orgasms without touching herself seeing the status quo changing in front of her, and cums again when Joseph gives her a wink and a smile.

Tenant Cuckold Stories: Your New Boss Took Your Girl, Your Job and Your House

A few minutes later, Milton is finally included in their private conversation taking place in front of him.

“We’re gonna need you to move your shit outta the master bedroom,” Joseph tells Milton. This catches Milton off guard.

“You gotta earn the right to live like a king,” Joseph continues. “Do you really want your girl to share a bed with some bum?” Milton was thinking of the irony of being asked that by Joseph. He looked over at Julia, who didn’t speak, but her facial expression told him she as in complete agreement with Joseph. This was something they clearly discussed together. Milton instinctively suggests that he can sleep on the couch for a while if Julia is feeling uncomfortable around him, but Joseph corrects him.

“Nah, bro,” Joseph says. “We’re gonna put you down in the basement. You’ll be right under the master bedroom.”

Milton didn’t challenge the arrangement and began moving his stuff out of the master bedroom, which was humbling. Afterward, he spent the day cleaning up the basement and making it his new living quarters. After finishing, he is met in the stairway by Joseph, who looks around and nods his head in approval, making Milton feel a sense of relief.

“Good job, buddy!” Joseph tells Milton with a thumbs-up. “Now go up to my room and move my shit into the master bedroom.” Joseph claps his hands twice to make Milton scurry. Milton pauses to tell Joseph that Julia won’t want to move out of the master bedroom.

“She ain’t moving,” Joseph assured Milton, slapping his cheeks a few times. “Why should I be all alone in that big room, eh? Besides, she deserves to be in bed with a real man, know what I mean?”

This sentence rocked Milton. Mike was going to be sleeping in the master bedroom with Julia?! Sure, they had chemistry and would often fall asleep together cuddled up on the couch, but she was his wife, he was supposed to share the bed with her. Joseph smirked watching Milton nod his head in approval without questioning his instruction, as usual. Joseph stood back and smiled to himself at how easily he became the man of the house.