I wish I never walked in on Joseph after he came out of the shower that day. Because if I hadn’t, I never would have blabbed my big mouth to my wife, Gina, about what a big cock he had. She would never have taken an interest in him. And I never would have had a front row seat of her tiny lips tasting his giant cock.

Homeless Cuckold Stories: Unemployed Slacker Could Fuck My Wife If He Wanted To

I let Joseph stay with my wife and me, as we had a spare room, and he was down on his luck. Joseph and I met as fellow employees at a video store. I had a meek Jimmy Olsen-type build while he was big, beefy, and burly. He often joked how ridiculous it was for me to land a girl like my wife, with her Jessica Alba-looks. I never took that personally, because I knew he was right. She was way out of my league.

Flash forward to a few months after we both stopped working at the video store. I ran into Joseph working some shitty job. We talked about what he had been up to since we last saw one another. In comparison to him, I did rather well. He was broke and not living up to his potential, at least in my eyes. I looked at Joseph and saw an alpha male in hiding, someone who could take charge at work, live in a big house, and nail a girl like Gina. I was living the life Joseph should have been.

I convinced my wife to let Joseph stay with us until he got back on his feet. Gina was fine with it, even though there was no set date on when he would leave. Despite Joseph being a bit of a slob – I found myself cleaning up after him a lot – he and my wife became pretty tight. In fact, as each day passed, the more time the two of them spent together, almost always without me.

Gina talked about Joseph a lot when we were alone. She talked about things he did like he was some kind of celebrity. She also liked to describe Joseph in detail, saying things like “…when he lifted it with his big, strong hands…”, very descriptive.

The sex life between my wife and I wasn’t as strong as when we first met, and just before Joseph moved in, wasn’t even existent. We were affectionate towards each other, but I could tell I wasn’t doing anything to turn my wife on anymore. So, you can imagine my surprise when I would wake up in the middle of the night sometimes and listen to my wife touching herself under the covers, laying right beside me. I took it as a hint the third time I caught her rubbing her tight little pussy, but she pushed me away, told me I was being silly, and told me to go back to sleep.

My wife got Joseph a job at the bar she managed, where I also worked part-time when she needed me. Joseph started off as a busboy, like me, but ended up being elevated to a bartender. It felt weird taking orders from Joseph. For him, ordering me around seemed like second-nature. In fact, when he wasn’t telling me to do things at work, he was doing at home, telling me to fetch this or tidy up that. Joseph liked the lifestyle he had, and in a very short time, became the alpha male I knew he could be the day I asked him to move in with my wife and I. Normally, this wouldn’t have been an issue, but I took the exception to coming home and finding her cuddled up in Joseph’s arms watching TV, or having Joseph whisper things in her ear passing through one room to another. She didn’t flinch when I was that close to her, but when Joseph was, you couldn’t scrub the smile off her face. I chalked it up to her being immune to my touch after so many years together.

Joseph was bringing in wads of cash from bartending tips alone within weeks of working at Gina’s bar, more than enough to get his own place with. When I suggested to my wife that it was time for Joseph to take the money and get his own place, she seemed panicked that he would leave – she clearly liked having him around. I hadn’t predicted how close the two of them would get upon moving in with us.

I finished work early one day and decided to head to my wife’s bar, and my heart almost stopped when I saw Joseph sitting on my wife’s executive chair, in her office, with her on his lap. My wife’s face buried in Joseph’s neck. He had a smile on his face; his head was cocked back, and the bulge in his pants was evident from across the room. When I cleared my throat, both jumped at my presence – Gina leaped out of his lap, while Joseph got slowly rose, winked at me, patted my cheeks a few times and left the office. It was too awkward of a situation to bring up, so I didn’t, and Gina and I talked about everything besides the elephant in the room.

The day afterward, I opened Joseph’s bedroom door to discuss the possibility of him moving out and getting his own place. Not seeing him in the room, I heard the shower stop. I walked towards the bathroom in “his” room and found him walking out of the stand-up shower, dripping wet, naked. My eyes immediately went to his package: his balls were enormous, like a giant orange, completely shaved, and his tool was what I would call a “beer can thick”, at least 3 times the size of mine. I don’t know how long I was standing there gawking, but by the time I looked up at my house-guest, he was almost completely dry, his right eyebrow cocked at me. Joseph grew an ear to ear smile that turned to a smirk, shook his head in disbelief, told me to throw him the towel on the bed beside me, and leave. His demeanor suggested that he figured out something…

That night, Gina and I were having dinner while Joseph worked at the bar. She began telling me something that should have offended her, as it certainly shocked me – Joseph made a bet with about 7 of the regulars at the bar that he could have his big fat cock in her mouth by the end of the month. I didn’t know what to say. My fists were clenched, while my cock was hardening. I couldn’t get over how much of a non-issue this as to my wife. When I asked how she knew that, she told me overheard one of the busboys talking to another about the bet. Apparently, everyone bet against Joseph, since they all knew Gina was married to me and wasn’t some slut. Add to the fact that Joseph was recently almost homeless and jobless, no one thought she was in his league anyways. Joseph didn’t tell them how he would do it, only that it would take him less than a month to fuck my wifes mouth. My cock was ready to burst out of my pants when she told me Joseph apparently said this to everyone who bet against him:

“Once my dick is in her mouth, she’ll do whatever the fuck I tell her to”.

My Buddy Bet Me $100 He Could Fuck My Wife's Mouth
For more pics of Lilly Ford see “Team Skeet: Itsy Bitsy Hot Spot“.

“I Bet You $100 I Can Get My Dick in His Wife’s Mouth”

My day at work was very unproductive the next day, all I could think about was Joseph’s bet. The audacity of him – I let him stay with us when he was down on his luck, rent-free, and now he was going to take my girl from me?! Sure, boys will be boys, and that’s just how guys talked, and sure it was a rather expensive bet, but I knew he was basing it on my reaction to the size of his package. I realized that he knew I wouldn’t be staring if I had goods as big as his, if not bigger. He realized what I saw was foreign to him, and that he had something to offer my woman that I couldn’t.

My heart was racing, because while my wife looked like a knockout at under 30, and every single guy who saw her wanted her, she always had a thing for jocks, bullies, and tough guys…like Joseph. Joseph was built like a linebacker, stocky, husky, big football player hands…while I was built like Jimmy Olsen, only meeker.

I called my wife in a panic, asking her why she told me about Joseph’s bet. She told me that while she was highly offended at first and almost fired Joseph on the spot upon finding out, the thought turned her on like she had never been turned on before. Here she was, her perfect life, all men kissing her ass, and here comes this kid beneath her, my friend, no less, assuring everyone he’d have his way with her. She said she came home early that day, lay in Joseph’s bed, smelled his pillows, and fingered herself while sniffing his dirty laundry. I made another accident in my pants when she said that.

I decided to man up, confront Joseph about his inappropriate bet, and give him a piece of my mind. When I walked into the bar, Joseph sat on a bar stool, while my wife stood in front of him, between his open legs. Her arms were wrapped around his neck, and his hands caressing her ribs. She leaned in for a kiss, a soft peck, followed by a smile that was reciprocated. Another peck ensued, followed by an open mouth, passionate kiss…which everyone around them cheered for. My wife was whispering in his ear while he smiled and gave his boys the thumbs-up. The bet was almost about to be won, and it was only week-one!

I ran back to my car and my cell went off. It was my wife, calling to tell me she was going to the movies with Joseph and to not wait up for her. I asked her not to, that know where this was heading, but she just told me not to worry about things, that she “had it all figured out”.

That night, I walked in on them cuddled up on my couch. Their lips were touching as they talked, looking into each other’s eyes.

“You wanna see it, don’t you?”, he asked her, with a smirk.

The next few moments were a blur. My wife got down on her knees, with Joseph hovering above her. He put his big catcher’s glove-sized hands on her head, gripping her hair as she unbuckled his belt, unbuttoned his jeans, and slid down his pants. A sweaty aroma filled the air, and his fat hog hit her right in the face. She leaned in and took a whiff, moaned, and looked up at him, his dick laying on her lips.

“It’s fine, baby,” he said to her, smiling. “Give it a kiss, you know you want to.”

My wife didn’t even look at me, even though she knew I was only a few feet away, staring at them both in shock. I watched in slow motion as she opened her mouth and licked the head of his big dick, then around his shaft. She lapped, slowly, his big balls while clutching his hips. When I walked over to them intending to put a stop to this outrageousness, Joseph grabbed me by the throat, then pushed me down on the loveseat across from them.

“Stay out-of-the-way and shut the fuck up.” he commanded me, his eyebrow raised.

I looked at my wife, who was smiling at Joseph’s superiority over me. A quarter of of Joseph’s big dick suddenly disappeared into her mouth. She gagged, took out his meat, and moaned in ecstasy as Joseph began thrusting into her mouth, shoving a little more meat between her lips with each motion. My big cock roommate then snapped his fingers and commanded me to take her dress off.

“Your girl is a fast learner,” Joseph said to me while my wife worshiped his enormous cock. He was taking to me as if I was one of his buddies and she was just some random horny chick.

I got to my feet, but suddenly had an accident in my pants – I came, and Joseph saw it happen. He laughed uncontrollably, which caused my wife to look over. Much to my relief, my reaction to what she was doing to my buddy snapped her out of the hypnotic state Joseph’s big cock had put her in. She excused herself to the bathroom, while Joseph sat back down on my couch, his arms extended across it, his feet crossed, a smile on his face.

“You know about the bet?” he asked me.

“Yeah, Joseph, I know about the bet,” I responded, trying to pretend there wasn’t a wad in my pants.

“Then you know I just won $700”. he said.

“Please don’t tell them what just happened”, I begged him.

“I’ll tell you what, man,” he said. “I’m gonna tell them. I want the $700. But I’ll bet you the full $700 that when she comes back, she’ll get back to work on me.”

“No, she won’t.” I panicked. “She’ll apologize to me.”

Joseph just laughed.

“Joseph,” I asked him. “Please, please, please don’t tell anyone what just happened. Please don’t make her do anything more with you.”

“I’m not making her do anything, bro. And by the way, $700 is a lot of money to me.”

“I’ll give you $1000 to keep your mouth shut.” I flat-out told him. “I’ll write the check right now.”

Joseph thought about it for a second.

“$1500, and you obey me for the rest of the month. You clean for me, you cook for me, you drive me around, and you call me SIR when I summon you. That’s my price for not telling everyone your wife just licked my balls.”

I swallowed hard and shook his hand to accept his deal. Here was a guy who was down on his luck only a few weeks ago, unemployed, and practically homeless, and now he not only had he messed around with my girl, but had bullied me into obedience and servitude.

When my wife came back down, she was flabbergasted watching me on my knees removing Joseph’s shoes and socks. She smiled as Joseph put the bottom of his feet against my face and pushed me down to the floor, telling her she married a sissy cuckold.

My wife didn’t come to bed that night. I spent the rest of the night sleeping alone on the couch, while my wife rode my buddy’s big dick all night long in our marital bed.

When I woke up the next morning, my big cock roommate and my wife had already left for work. I didn’t call or text either of them, intending to talk to them both when I returned home later that day.

Then evening, when I got home and opened the front door, I could see the back of Joseph’s head cocked back while sitting down. The top of my wife’s head went up and down while she on all fours on the couch. With his right hand on the back of my wife’s head, his left hand was filming whatever they were doing with his phone.

I closed the door slowly, as neither one noticed my arrival. I sat down on the front steps of my house. I could hear Joseph moaning, shouting profanity, grunting, and a loud exhale…followed by cheers and laughter from them both.

I don’t know what Joseph’s intentions were with the video he had shot with his cell, but Joseph did, indeed, keep his word. Even though he fucked my wife, our arrangement was that he was not to tell anyone about it.