Let me relay a story about the craziest shit that happened to me a week ago. My name is Jamie. I'm twenty-two and a plumber just out of my traineeship. My boss Warren is a good guy and a real close buddy of my dad. My parents have been friends with Warren and his smoking hot forty two-year-old wife Shirley for many years.
I have had the pleasure of seeing Shirley first-hand in a bikini many times around their pool growing up, and she was always a go to for masturbation material when I was a teen. She was the woman that got me hooked on woman's underwear. Ok, that sounds weird. I should say my obsession with her soiled panties. I regularly masturbated into her panties fresh out of the laundry hamper when I was at their house as a teen.
Anyway, a week ago, I was returning from a quick job, changing out some taps in a restaurant, when my phone rang. It was Warren.
"Jamie, where are you at on that job this morning? You should be done by now."
"Yeah, boss, I am. I'm just on my way back to the workshop now, be there in about twenty minutes," I replied.
"Ok great. Listen, could you swing by my house, please It looks like I left the keys for the excavator on the kitchen bench. I need you to grab them. It's on your way," Warren said.
"Sure thing, boss. Will Shirley be home to let me in?"
"Oh shit, no, she will be at the gym. There is a spare key under the third pot from the left-hand side of the back door. Let yourself in. But don't forget to lock back up and put the key back when you leave."
"Rogie will do," I said, heading to Warren's house.
I pulled the pickup into the drive, headed straight to the side gate, and walked around the back of the house. Sure enough, there was a spare key under the pot plant, so I opened the back door and let myself in. The keys were right where Warren said they would be, but the noises coming from the master bedroom told me Shirley wasn't.
Now I know I should have just grabbed the keys and left. But my teen memories of Shirley in those skimpy bikinis got the better of me. If she was lying naked on the bed pleasuring herself with a dildo or something similar, I needed to see it for myself.
I tiptoed up the hall towards the bedroom but froze in my tracks when I heard a man's voice.
"That's it, my little married slut, suck my cock like the fucking cum whore you are. Deeper bitch take all my cock down that throat," I heard the guy say. The next sounds coming from the room were of Shirley gagging on cock.
I slid up to the door and peeked around the door frame. Shirley was lying back on the bed. Her head was hanging over the edge. A heavily tattooed white guy was face fucking her. I could see his obviously large cock bulge in Shirley's throat each time he thrust back into her. He had his head back and eyes closed as he pushed and pulled Shirley's head onto his cock.
Shirley's face was a mess as she took the thick cock balls deep. But it was those glorious tits that captivated me. As a teen, I had lost so many loads of cum imagining how they looked, and now here they were in all their splendid glory, only meters away from me.
I pulled out my phone switched the camera to video mode, and started recording the action for jerking material later. Just as I thought the guy was about to cum. So he pulled his impressive cock from Shirley's throat.
"Get on your knees bitch. I want to taste that pretty cunt and arse before I stretch both those slutty holes out," he growled at Shirley.
Shirley rolled over onto her stomach. Then she turned her head to face him before reaching back and spreading her arse cheeks open, presenting her lover with the most perfect shaved cunt I had ever seen. God, it looked so good and suddenly, a pang of jealousy coarse through me. I wished it was me about to push my face in her incredibly beautiful smooth, and very wet cunt.
I watched, mesmerized, as he pushed his tongue deep into her spread puckered pink butt hole. Shirley's head dropped, and she let out a long purr as the sheer pleasure of having her arse eaten took over her every thought.
Shirley's lover clearly knew what he was doing as Shirley's body shook and trembled as his tongue slid from her arsehole up through her dripping cunt lips. I was so close I could see perfectly how juicy her cunt was becoming with each stroke of his tongue. My cock was now painfully hard, but I reframed from taking it out and jerking off.
Satisfied, Shirley's cunt was moist enough to take his big cock. Her lover stood up and pressed the bulbous head against her dripping wet cunt lips and pushed forward. In a single thrust; he was deep inside her. Shirley screamed out in erotic delight as the mystery man's cock touched places Warren's cock never had.
I watched and filmed. My cock was so hard I thought it would burst through my work pants. Lover boy wasn't holding back and was soon pounding the absolute fuck out of Shirley's married cunt. And she was pushing her hips back at every thrust to meet his. Then things got a little crazy as the mystery man started to slap Shirley's arse cheeks really hard. He also started calling her filthy names.
"You love my big cock don't you, you filthy married whore, but I'm not the only one fucking this married cunt either. Cum whores like you normally have a few bulls lined up to fuck them," he hissed at her as he slapped her arse and pulled her head back by her long blonde hair.
"Oh, yes, I love your big cock. I love how you use my married cunt as your personal cum dump. I do have other lovers, but none of them fuck me like you can with that big cock. Fuck me, baby. Fuck me till I can't walk properly, then fill my married cunt with your superior cum," Shirley screamed back at him.
Holy fuck, Shirley really is a complete slut, I thought.
As much as I wanted to stay and watch, I had already been there too long, and Warren would wonder where I was, so with my ten minutes of hardcore video in hand, I slipped back down the passage and out the back door before putting the key back under the pot plant.
All I could think of was Shirley begging to be fucked and abused on the drive back to the workshop. I couldn't get the image out of my head. She was always so demure. Maybe it was the big cock that bought out the beast in her. Then all the other questions came.
"Did Warren know his wife was cheating? Were they secret swingers? Shit, did my parents know? Mom and Shirley were best friends. Wait, is my mom a secret slut as well? What the fuck," I said out loud. The whole thing was starting to fuck with my head.
"Jesus, Jamie, did you drive to China on the way back? You've been gone nearly 40 minutes since I called you," Warren said as I pulled the pickup alongside the workshop.
"Sorry, Warren, I swung by McDonald's to grab a coffee on the way and the drive-through was busy," I said, lying.
"Yeah, so where's my fucking coffee then?"
"Shit. Sorry Warren, I didn't even think about getting you one."
"Yeah, that would be right. Maybe I will not think about paying you this week," Warren said, sort of pissed I hadn't got him a coffee. He would have been more pissed if he knew what I was really doing, though.
A few hours later, we had finished on the building site, and we packed up the truck. I thought I would quiz Warren on his marriage and maybe drop in a hint or see if he and Shirley were swingers.
"Hey Warren, so how long has Shirley been hitting the gym?" I asked.
"Don't ask me. It's her new thing. The bloody gym, three times a week, I guess. It's been a couple of months now."
"I hope you don't mind me saying, but I never thought Shirley needed to go to the gym. She's in pretty good shape for her age."
"Steady on with the age thing, there, pal. She's only a couple of years younger than me," Warren laughed.
"Yeah, sorry old man," I said, laughing
"Warren, can I ask you a personal question?" I said as we climbed in the truck.
"Shoot, Jamie. I think I have known you long enough to answer pretty much anything you might ask."
"Ok, have you and Shirley ever been involved in swingers or shit like that?" I said, just throwing it out there.
Warren's head snapped around and looked at me with a what the fuck look on his face.
"Swingers, where the fuck did that come from? You want to have a crack at my wife or something?" He said, looking at me weirdly.
"No! Nothing like that. It's just me and my girlfriend Caroline were asked if we were interested in trying it out by our friends the other day, and I was just wondering if you knew anything about it that's all," I said.
"Wow, oK, I thought you were getting at something else for a minute there. No, we aren't swingers. The thought of someone else fucking my Shirley sends a shiver down my spine. I don't understand why anyone would want to become a cuckold willingly," Warren said, clearly having no idea that's exactly what he was and, by Shirley's own admission, by a few different men.
I sat thinking about it on the ride back to the workshop, and I started to feel sorry for Warren. He had no idea Shirley was a complete slut for stray cock. I was torn between keeping the video I had taken or deleting it and just forgetting the whole thing.
That night, I was at home with my parents having dinner, and I kept looking at mom and wondering if she knew what Shirley was doing. They were best friends, and there was no way mom wouldn't know about it. And was she doing the same thing to dad?
Later that night, I was in my room, having just finished talking to Caroline on the phone. I opened the video of Shirley and started watching it. No sooner had it started, and my cock was rock hard. I grabbed hold of my dick and began jerking off while watching it.
It only took a couple of minutes, and My cock exploded, shooting wad after wad of cum across my stomach and hand.
Fuck! I want to fuck my boss's wife more than I have wanted anything. I thought.
The rest of the week went by relatively quick, and every night I watched the video and jerked off. But it was that thing Warren had said about becoming a Cuckold that stuck with me the most. I Googled it and found multiple porn sites and stories dedicated to the subject. And the more I read, the more I began to see the obsession of watching your partner being fucked by another man. And not just any man. I understood he had to be superior to me in every way, but for me, the key factor was his cock had to be much larger than my own.
Caroline, my girlfriend, was at college a hundred miles away, so I had to drive up to see her. This meant I only got to see her on weekends. So during the week, I was reduced to jerking myself off, and the more I watched the video of Shirley being fucked so brutally and relentlessly by the mystery guy, the more I started to wonder if Caroline was being fucked during the week by someone else. The idea kind of got me all hot, and I found myself wishing I was fucking Shirley right alongside Caroline while her cunt was being destroyed by Shirley's mystery man.
The weekend came, and I drove up to see Caroline. And as normal, when I got there late on Friday night, we got straight into bed and started fooling around. When out of nowhere, she asked me if I had a fantasy I wanted to fulfil. The question was very random, so I wondered if it was actually Caroline who wanted to try something and asked me to see what I would say.
"That's a little random; honey, are you sure you aren't asking me because you have something you really want to try and are afraid to ask?" I said, pushing a couple of my fingers into her very wet hairless pussy.
"Oh fuck, Jamie, that feels soooo good, baby. And yes, there is something I would like to try, but only if you are ok with it," she said.
"Oh yeah, and what is it you want to try baby? Do you want another dick? Would you like to be spit-roasted on two big cocks? Would you like to be fucked hard by a stranger," I said out of nowhere, thinking that's what I would like to see after watching Shirley get fucked so hard and seeing her reaction.
"What? No. Where did that even come from?" Caroline said, sitting up and staring at me like I was an alien or something.
"I don't know. I thought that was every woman's fantasy. Isn't it?" I said, suddenly backpedalling on my response.
"Well, it's not mine... Wait, is that something you would even be interested in doing? Are you saying that's your fantasy? You want to see me being fucked by someone else while I suck your cock or something?" She said, looking at me with a perplexed look on her face.
"No, definitely not. Well, I don't know. I thought that's what it would be, that's all. It's something I'm open to if you would like to try it," I said, unsure if I had said too much.
"Well, ok, I find the whole thing weird that you would want me to fuck someone else, or you were even thinking of me fucking someone else. But I'm guessing that's a conversation we will have to have now you have bought it up. But that wasn't what I was thinking. I thought I would like to try it out with another woman," Caroline said, cuddling back up to me.
Instantly I got an image of Caroline pressing her face into Shirley's cunt and arse and licking her out while I fucked her from behind and then swapping over and fucking Shirley while she munched down on Caroline's pretty young pussy. My thoughts quickly jumped and stumbled. Suddenly I could clearly imagine Mr mystery man fucking the life out of Caroline with his huge cock while Shirley rode my cock, and we both watched as Caroline was used as a cum dump just like Shirley had been.
"Jamie, Jamie, where did you just go? You were off in another world. Are you ok?" Caroline said while shaking me.
"Oh, sorry, babe, I just got an image in my head of you, and another woman and my imagination went into overdrive."
"Oh really, do you like the idea of seeing me with another woman? I thought you might. Who did you picture me with? Was it Samantha? You already know she is a total slut, and you think she is really hot," Caroline said as she grabbed my hard cock and started sliding her hand up and down.
I thought for a minute and decided, instead of telling Caroline who I was picturing her with. I would just show her instead. I grabbed my phone from next to the bed and opened it up to the video I had taken of Shirley.