A Stupid Bet (MM)

Siren-BookStrand, Inc.

Heat Rating: Sextreme
Word Count: 32,588
4 Ratings (4.8)

[Siren Classic ManLove: Alternative Contemporary Romance, MM, HEA]

Dexter Houghton should know better, but he's bored. Jared Master, his best friend, bets him he can't make anyone fall in love with him in ten dates or less, and Stephen Howard, his other best friend, also goads him into it. He's wealthy, successful, and good-looking, and he knows he has an amazing body. Everybody wants him. It's an easy win for him, but falling in love with Isaac Robbins is unexpected.

Isaac works many hours at the diner to earn enough to pay for rent, utilities, and the school fees for the classes at the community college. He has nothing going for him, not even physically. Hence, he's surprised and rather suspicious when a man like Dexter suddenly asks him out on a date. However, Dexter gets past all his defenses, and he falls in love with the older man. Then he discovers he's nothing more than a bet.

Will the discovery end their relationship for good?



A Stupid Bet (MM)
4 Ratings (4.8)

A Stupid Bet (MM)

Siren-BookStrand, Inc.

Heat Rating: Sextreme
Word Count: 32,588
4 Ratings (4.8)
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Cover Art by Harris Channing




Isaac was an anomaly in many aspects. Dexter enjoyed cuddling with Isaac. He loved kissing the top of Isaac’s head or running his fingers through the younger man’s hair as he hugged his date tightly in his arms. He didn’t want to let go of Isaac. It was almost painful to be separated from Isaac even. Unfortunately, he had to do just that when they arrived outside Isaac’s apartment building. When Isaac alighted from the car, Dexter followed him. He accompanied Isaac all the way into the apartment building until they were standing next to the elevators.

“This is me,” Isaac muttered softly while gesturing at nothing in particular.

Dexter looked around the hideous lobby of the building. The building was so dilapidated from the outside, and the inside was so much worse. “Is this building safe? What about the area around it? There’s no security here at all.”

Isaac chuckled. “The building is old, but it’s cheap, and my share of the apartment fits right into my budget.”


“Dexter,” Isaac interrupted while grinning at Dexter. “I’ll be fine. I’ve lived here for a couple of years now, and so far, it’s safe.”

Dexter wanted to argue further, but he refrained from doing so at the last second. “Okay, but you’ll me know if you need someplace else to stay, right? I have several penthouses all over the city. In fact, I own houses and penthouses all over the nation and around the world. Just say the word, and we can go on a trip somewhere. Any place you want. I promise.”

Isaac snorted. “You’re moving too fast, Dex. Our second date isn’t over yet, and you’re already thinking too far ahead into the future.”

Dexter’s cheeks grew warm almost immediately from the embarrassment that washed over him. “Sorry.”

Isaac shook his head. “Don’t apologize. You really are a good man. Certainly a lot better than the first impression I have of you.”

Dexter felt even worse now because he couldn’t forget about the reality that Isaac started out as nothing more than a bet. A tiny part of him yearned to confess to his mistake, but he was also terrified of losing Isaac for good. He didn’t expect to like Isaac for real, but he did, and he was determined to be with Isaac for as long as possible. Preferably for the rest of their lives together. That thought astounded him. He had never imagined he would ever find somebody he wanted to settle down with, but now he had Isaac, and the younger man was quickly seeping into every bit of his being. He pondered if he should come clean, but in the end, he kept his mouth shut and simply smiled at Isaac. His parents would be over the moon, though. They had been urging him on and off to settle down as quickly as possible. If he someday managed to get Isaac to agree to spend the rest of their lives together, his parents’ wish was about to be granted.

“Thank you.”

After that, there was a brief moment of silence between the two of them. Isaac seemed to look everywhere, except in Dexter’s direction. Dexter desperately yearned to kiss Isaac. This felt like the right time for it, but he had no idea why he hesitated or why he was so nervous about it. It wasn’t as if he was a virgin. He had kissed and done a whole lot more with plenty of men and women in the past. Kissing Isaac should be a piece of cake. However, he was astonished to discover he was actually trembling a little as he reached for Isaac’s cheeks with his hands.


“May I kiss you?” Dexter blurted out.

His heart felt as if it was going to burst out through his chest at any second now as he waited for Isaac to respond to his request. Then he heaved out a huge sigh of relief when Isaac nodded gently at him. He stepped in closer to Isaac and slowly bent his head down before capturing the younger man’s lips with his own. He was delighted to find out he wasn’t the only one who was anxious about their first kiss together. He could feel Isaac’s whole body quivering slightly. He tightened his embrace and deepened their kiss.

He was then taken aback when Isaac turned out to be a, for lack of a better word, lousy kisser. Isaac desired him as much as he craved for the younger man. He could feel the evidence of Isaac’s arousal throbbing over and over again against his own hard cock even through the layers of their pants. Isaac was also kissing him like a frantic and frenzied sex-starved man who hadn’t gotten laid in years. However, Isaac didn’t seem to know what to do with his tongue. Isaac also had too much spit in his mouth. It was messy, and Dexter knew he had to take charge, so he did just that. Mere seconds later, he almost lost control of all his senses when Isaac groaned loudly against him. He was dying to tear their clothes off their bodies and fuck Isaac right there in the lobby of the apartment building, but he didn’t want their first time together to occur right then and there. It took everything in him to pull away from Isaac.

“More,” Isaac pleaded. “Please.”

Dexter obliged. He couldn’t deny Isaac’s request.




Dexter gaped a little as he openly took in the delectable sight of a naked Isaac once again. His cock, which had deflated slightly, hardened again within seconds. He gulped as he reached for the bottle of lubricant once again to slick his dick up before putting some of the sticky liquid over Isaac’s hole. He also pushed his fingers into it for several seconds to loosen it up again. Then he braced himself with his left elbow as he hovered slightly above Isaac and held on to his cock. He placed the tip of his dick right against the rim of Isaac’s hole before he pushed it in slowly. Unfortunately, Isaac’s hole was too tight.

“Baby, you need to relax.”

“Shut up,” Isaac retorted. “I’m scared. Your cock is huge.”

“It’s not. There are plenty of larger dicks out there.”

“It’s big enough. I can already imagine how painful it will be to have that being shoved into my ass.”

Dexter chuckled. “Then don’t think about it.”

Isaac snorted. “Easier said than done. You’re not the one who’s about to have a ten-inch dick being crammed into your ass.”

Dexter refrained from rolling his eyes. “My dick is barely eight inches.”

Isaac scoffed at Dexter. “It looks more like ten inches to me. Besides, just ’cause it’s two inches smaller than my rough estimation, it doesn’t mean it won’t be painful when it goes up my ass.”

Dexter huffed at Isaac as he continued to try to thrust his dick into his lover’s ass. “Babe, focus. I can’t fuck you if my dick can’t even get inside your ass.”

Isaac snickered, but he stopped talking after that. The silly banter between the two of them must have been helpful somehow because Isaac was more relaxed now, and Dexter was able to pop the head of his cock into his lover’s ass a few seconds later. He hissed as the pleasurable feeling threatened to overwhelm all of his senses. Isaac’s ass squeezed and massaged his pulsing cock over and over again. He felt bad for Isaac, though. His lover must be in pain because Isaac was literally gripping onto his biceps with the tips of his fingernails and digging into them really hard. Isaac gritted his teeth and tried to push Dexter away.

“Dex, it…it stings. It burns. Take it out.”

Dexter leaned down and kissed Isaac’s face from the forehead, the tip of the nose, cheeks, and all the way down to the younger man’s lips. “Baby, it will go away soon enough. You just have to calm down. Breathe deeply.”

“No. I can’t. Dex, it hurts.”

Isaac was sweating profusely. So was Dexter, for that matter. He leaned forward and kissed Isaac on the lips once again. This time, he slipped his tongue into Isaac’s mouth as he licked at his lover’s tongue. He deepened the kiss while caressing Isaac’s body everywhere he was able to reach with his hands. After a brief moment, Isaac stopped trying to get away from him. In fact, Isaac was actively clenching his ass all over Dexter’s cock. Dexter took that as a signal for him to proceed. He slid his cock inward inch after inch. He rumbled deep in his throat when his cock was completely buried inside Isaac’s ass. He broke away from the kiss and wiped the sweat away from Isaac’s forehead and eyes.

“You got it. I’m all the way in you, babe.”

Isaac panted and chuckled at the same time. “Fucking…fucking finally. I thought your dick would never end.”

Dexter snorted. “I’m sorry to disappoint you, but I don’t have that much dick for you.”

Isaac rolled his eyes. “You have plenty. Trust me.”

Dexter chuckled as he slowly thrust in and out of Isaac’s ass. He did his best to remain patient, but he almost wept in relief when Isaac pleaded with him to move faster and harder. He obliged immediately. He wished he could fuck Isaac for hours, but he had been holding himself back for a while now. Moreover, he had been yearning to make love to Isaac for so many days now. All of those pushed him over the edge a lot quicker than he wanted to. He could feel his balls tightening.

“Baby, I’m going to come.”

Isaac reached for his cock and stroked it at a rapid pace. “I’m close, too. Fill me up, stud.”

“Almost there, baby.”

Isaac huffed and puffed much louder now as he raised his head off the bed and leaned in closer to Dexter’s left ear. “Fuck me, stud. Yours is the first cock inside my ass, and you’re fucking me raw. No condom. Come on, stud. Fill me up with your cum.”

The filthy words that came out of Isaac’s mouth left a lot to be desired. It didn’t even sound that sexy. However, the reminder that Dexter was the one who copped Isaac’s virginity was more than enough for him to lose the last shred of his self-control. He gasped for a second or two before he reached his orgasm. He pumped out load after load of his cum into Isaac’s ass as the incredible climax overwhelmed all of his senses.

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