DATE NIGHT
Glen looked down at his phone sitting on the bar. It was likely the thousandth time he had done so in the last three hours. But still, there was nothing, not a single message, no update, nothing. The knot in the pit of his stomach seemed to twist and grow tighter as every minute passed.
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The only distraction was from the bartender asking if he would like another drink. But even that hadn’t happened in the last hour as he had been sitting on the previous whisky he had ordered, the ice long melted.
Glen’s mind was awash with the vision he had witnessed earlier in the evening how his wife of only a few years had readily accepted the drink from the tall, handsome stranger. Or the way she had flirted with him, laughing at everything he said, or the way she placed her hand on his arm as she did so.
But when the stranger had placed his hand on Monique’s bare thigh just below the hem of her skirt, the very skirt Glen had selected, knowing it was too short and extremely slutty looking. Completely tore Glen’s insides apart, especially since the stranger's hand was now less than a few inches away from the black lace thong Monique was wearing.
He knew tonight would be painful, but he had no idea why seeing Monique flirting and being touched still caused him so much angst and agony. On the one hand, Glen was full of jealousy, and on the other, his cock was painfully hard. He had been adjusting his raging hard cock in his jeans ever since the stranger had first leaned in and whispered something in Monique’s ear that had made her audibly gasp and then playfully slap his thigh, her hand never leaving it.
Glen had been sitting close enough to watch their interaction but not close enough to hear their conversation. Why did seeing his wife openly flirting with another man in a busy bar both turn him on and destroy him at the same time? Was it the humiliation of watching his wife being turned on by another man, or was it the thought that someone they knew finding out his wife was a whore, and he was a cuck?
Glen’s thoughts drifted back to how it had all started—to the night he found out he was never going to be enough for Monique sexually. They had just finished making love. It was date night, and Monique had suggested some role-play. They were sprawled out on their bed, the covers thrown back. Glen's body is covered in sweat, his chest rising and falling in rhythm with his racing pulse and heavy breathing.
“That was incredible; how was it for you, baby? Did I fulfill your dirty little fantasy of being taken by your college professor?”
“It was lovely, honey. I mean, you were amazing, and I love how you really got into your role. But just so you know, my college professor was a lot rougher than that with me, and his cock was much bigger,” she said, getting up from the bed to head to the bathroom.
Glen laughed, “Yeah, in your fantasy, right?”
Monique stopped in the doorway. Turning her head, she looked at Glen and said, No honey, not in my fantasy. My college professor had the most incredible cock I’ve ever had. His cock stretched my tight young pussy so good, and he really knew how to throw me around on the bed,” smiling at the fond memories of her college days.
“Shit, thinking about it not just on his bed but on his desk up against the basin in the faculty lounge, damn, the man could fuck,” Monique said before disappearing into the bathroom.
Glen lay there completely stunned and shocked by Monique's statement. He jumped off the bed and raced toward the bathroom. Reaching the bathroom, catching Monique wiping her pussy of cum and pee after peeing.
“What do you mean? I don’t understand. I thought we were role-playing. Did you really fuck your professor? Wait, were you thinking about him while I was making love to you?”
“Glen, relax! It was a long time ago, and yes, I fucked my professor. It’s no big deal. I wasn’t a virgin when we met, you know.”
“It is a big deal, honey! How old were you? Shit, how old was he? Oh my God, I have so many questions.”
“Not now, Glen; I’m not answering any more questions tonight. I’m tired. We’ll talk about it in the morning if it bothers you that much. But you never asked about my past, so I assumed you were one of those guys who isn’t threatened by previous sexual experiences.”
“Fuck Monique, I think fucking your college professor is on an I needed to know basis. Don’t you?”
“Oh, for crying out loud, Honey, did I ask you how many women you fucked before we met? No, I didn't! Do you know why I didn’t? Because I don’t care. We both have a past, so let’s leave it there. Now come to bed,” she said, patting the bed beside her.
“Fine, I guess. Can you at least tell me one more thing before we go to sleep?”
“Sure, shoot, what do you want to know?”
“You said his cock was much bigger. Like, how much bigger was he bigger than me?
“Do you want the truth, or do you want me to save your feelings?”
“Oh well, fuck I think you just answered it, didn’t you. But go on, tell me. I want to know now.”
“Ok, he was big, so fucking big I think I measured it once, and he was like nine and a half inches. But it wasn’t just the length. He was thick, like so fucking thick; I thought the first time he fucked me that he was going to split me open. And trust me, I was no virgin. I had fuck oodles of frat boys by the time I hooked up with Professor Dryer. Even after a year of fucking that magnificent cock I still couldn’t walk normal in the morning. And the orgasms fuck he used to make me squirt everywhere, every time.”
Looking over at Glen after reminiscing about how good her ex-lover was. Monique noticed two things. The absolute look of shock on his face and the fact his cock was completely erect again and that was a first for Glen so soon after having just fucked.
Glen remembered the conversation like it was yesterday; how could he not? It was the day he had found out his wife of less than a year had been a total slut at college and a size queen. Over the next couple of years, Glen learned that his beautiful bride, whom he loved more than anything, had fucked her way through college. She loved to pleasure older men, old enough to be her father and loved having her pussy stretched to its limits by the biggest cocks he could find her.
And Glen discovered that he loved every single sordid story, every tiny detail of every fuck fest Monique had shared with him. Glen was hooked on his wife’s hot past, and upon hearing he had never made Monique orgasm and never would, he evolved into the permanently caged, pussy free cuckold he is today. He understood his tiny five-inch cock would never truly satisfy Monique’s sexual needs. That was a task he now left to better equiped alpha males.
This brought them to this point: Friday night date night, but instead of it being Glen fucking his wife Monique on date night now, they drove to a nearby city where Glen watched from the sidelines as Monique weaved her sexual spell on random strangers at the hotel lobby bar frequented by traveling businessmen.
They always rented a room upstairs where Monique could quench her thirst for fresh cock, using the excuse she was there on business and she had an early flight in the morning so they wouldn’t be tempted to stay. And after every time another man had the pleasure of fucking his beautiful wife, Glen had the pleasure of cleaning her up with his mouth.
The chime from his phone snapped Glen from his deep, fond memories. He looked down at the screen. It was a photo of Monique, her legs spread wide, her cunt lips swollen, puffy and red. With a river of thick creamy cum running from between her now gaping pussy down to her arsehole and onto the sheets below.
The message accompanying the photo simply read, “he’s done; he fucked me so good, baby, his cock was perfect, but he made a big mess. Now be a good little cuck, and get up here and clean me up.”
Glen swallowed the remaining watery contents of his glass and sprung from his seat. Racing to the elevator, the door opened as he got there the stranger stepped out. He had the same shit-eating grin Glen had seen so many times before. It was that I just fucked some suckers slut wife grin.
As the doors closed behind him, his phone chimed again. Looking down, he saw a photo of Monique on her hands and knees, getting railed by the stranger. His thick veiny cock was coated in Monique’s creamy pussy juices. The bed sheets soaked in her squirt. Glen knew immediately that the stranger had done his job quenching Monique’s carnal desire for the orgasm his pathetic little cock could never give her.
This time, though, it was the message that sent a shiver down Glen's spine, “We are going to start making some changes to date night; I think it’s time you learn to suck cock so you clean us both up. Dan had an amazing cock and was a great fuck. I wanted him to stay and fuck me all night. So It’s either you learn to get over your angst of watching me fuck, or we start renting another room for you, but you don’t get to do clean-ups anymore. Your choice, cuck.”
Glen's cock was instantly hard.
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