The Bet Sequel

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The Bet Sequel Max Swan

  • Years after the original Bet that sees Sam turned into a cuckold, Helen again ensnares him into the more extreme lifestyle of sissy shemale. Includes a reworked version of the original story that sent SPH and cuckolding to the edge.
As Sammy Buford pulls into his daughter’s school parking lot, he cannot help feeling a pang of nervousness at the prospect of seeing his ex-wife Helen again. Even after five years of divorce, the thought of having to talk to the brown-haired beauty makes him sweat. However, they have two kids together though he doubts they’re his, Sam has never said anything about it. Sam loves Katie and Tim and is grateful to have them in his lonely life.

Of course, it didn’t help that his ex-wife Helen chose to live on the other side of town, a good hour’s drive these days, and was always coming up with excuses to deny him his visiting rights. Sam actually had to get court intervention to stop her from doing that, and this only added to the tension between them. Still, when in front of the kids they put a good face on it because their problems weren’t their children’s.

Helen always had a power over him, and ever since that fateful night he lost ‘the bet’ and Helen plunged them into a hot wife/cuckold relationship, Sam never realized just how weak he is. Because of losing the bet, Sam had to allow his wife to cuckold him to men with big cocks. To make matters worse, every time a new stud arrived, he had to measure them and compare it to his own small dick. Helen made him keep a diary of all the cock measurements and had a photo album with all those pictures of Sammy’s small dick beside some bull. The man even had to eat her creampies, fluff the bulls sometimes, and generally act like a brothel maid.

Sam divorced her when he decided he’d had enough of being her sissy cuckold husband. Helen didn’t seem to care though; she had plenty of men in her life. In fact, she helped Sam pack his things.

Her last words when he left that final time, “You can’t deny what you are, Sammy. Run from it if you want, but you’re only fooling yourself.”

Those words often made him wonder in the deep dark night when sleep was difficult, and his mind couldn’t stop obsessing over his problems. I’m not a cuckold or a sissy, Sam would tell himself repeatedly in those early hours. Helen’s wrong, she made me do those things. I didn’t enjoy it. She stole my manhood from me.

Helen’s successful sex life after their marriage just made Sam more acutely aware of his failures. For his attempts to get back into dating and having a proper relationship with a woman had come up extremely short. The poor man just couldn’t keep a woman; they always leave him because he’s so bad in bed. Even though Sam is relatively wealthy, he’s just so utterly hopeless at sex it drives even the most enthusiastic woman away.

Why is he so bad? For a start, his small dick is barely three and a half inches hard, and just an inch when soft. The man has chronic premature ejaculation (PE) and can’t last ten seconds once he penetrates a hot cunt (the reason he lost the bet in the first place). Even masturbation has become so bad Sam doesn’t orgasm anymore when he ejaculates. Sam has tried to make up for his shortcomings by eating pussy etc., yet it seems he can’t also do that right and any women brave enough to sleep with him eventually just gave up.

Still, he has his kids, and that gives him some joy.

*****

Sam enters the school hall to watch his daughters play and in the foyer spots Helen hanging off a much younger man.

The man has short red hair, and a goatee with a mustache is about six foot tall, slim build, and handsome in a rugged way with a square jaw and high forehead. He looks like Michael Fassbender, Sam thought, screwing his nose. Is she bringing her tinder dates to the kid’s school events these days?

What galls Sam the most is the way Helen is hanging onto this man, it reminds him of those dark years he served as her cuckold. Why doesn’t she just fuck him on the floor, the dirty slut, Sam thought. Sam glances at his watch, the show starts in twenty minutes, and he wonders how he can avoid having to talk to Helen and the man. Discretely staring at the redhead man, Sam knows already what it is about him that has his ex-wife so exuberant. The man is handsome in an everyday way, sure, but physically he appears kind of skinny or scrawny even.

Sam convinces himself he’s only checking the stranger out because his kids are involved.

Yet Sam can’t take his eyes of the redhead boyfriend of his ex-wife. Suddenly, the man excuses himself and walks toward Sam, and the jealous ex-husband finally sees the reason for Helen’s attraction. The Michael Fassbender look-alike has a massive bulge in the front of his jeans that extends considerably down the pant leg on the left. She always liked them big, the bigger, the better, Sam thought. Fucking hell, that’s a Marty-sized dick. Marty was a bull that often-fucked Helen when Sam was married to her, the man was eleven inches hard. The biggest cock Sam has seen. Sam can’t tear his eyes away from the bulge as Helen’s new boyfriend walks past heading for the toilets.

The Bet Sequel Max Swan

  • Years after the original Bet that sees Sam turned into a cuckold, Helen again ensnares him into the more extreme lifestyle of sissy shemale. Includes a reworked version of the original story that sent SPH and cuckolding to the edge.

The glum man glances at his ex-wife and realizes Helen had noticed him staring bug-eyed at the redhead’s bulge. She’s smiling in a way Sam recognizes all too well. Helen gives Sam a little nod and a wink.

Why did I do that? Why did I stare at his bulge, Sam wonders?

Sam turns away, deciding if he should just flee the scene. Yet he doesn’t want to upset his daughter, so instead, Sam goes into the theater and takes a seat deciding immediately he’ll avoid the couple for the remainder of the night. He can’t face Helen, and what if she tells her boyfriend? Sam’s stomach churns, and his hands shake, his eyes dart around wondering if people are watching him. He doesn’t lust for Helen anymore, he hates her too much for that, yet the image of that bulge is all he can think of.

What the fuck is wrong with me, Sam wonders? I’m not that man anymore. I’m not her cuckold. Omigod, Helen is gonna bust my balls over this, I just know it … fucking bitch.

*****

Eventually, the evening winds down and Sam says goodbye to his daughter and leaves without speaking to Helen.

In fact, Sam’s proud of himself he got through the night without having to speak to his ex-wife at all. The man gets into his car and drives away as fast as the speed limit allows. Yet, the thought of that bulge is still ticking through Sam’s tortured mind, so he turns on the radio to distract himself.

After driving for about ten minutes, Sam’s phone buzzes indicating an incoming text message. He glances at his phone to see who it is, and there’s Helen’s face smiling up at him. The phone uses pictures for caller ID.

“Ugh, what does that bitch want?” Sam groans. “Can’t she just leave me alone for once?”

He pulls off the road and stops to see read the text message. The text said: I saw you checking out Luke’s big cock. It looks tasty, doesn’t it? Did it make your itty-bitty clitty go hard?

“Luke, so that’s his name,” Sam said coldly. “Tasty? I don’t wanna taste Luke’s cock.”

Sam gasps trying to calm his nerves, and texts back: Leave me alone. I’m not your plaything anymore. Then throwing the phone down in disgust, Sam continues the drive home. Try as he may, Sam cannot stop wondering why Helen is playing this game with him again after all these years. It takes forty minutes to drive the rest of the way home to his house on the other side of town, and all the way Sam keeps repeating he won’t let Helen control his life again. Never, ever again, he thought.

*****

When home, Sam heads for the fridge and gets a can of beer, half of it drunk as soon as he pulls the tab off. The rest soon follows, so he gets out another beer. Then the shaky man heads to the bedroom thinking a shower might help him relax, and starts to undress. Sam’s phone buzzes.

“Oh, fuck, Helen again.”

Her text said: You’ll always be my cuck, no matter what lies you tell yourself.

Sam replies: Never. I’m free, and if you try anything, I’ll get a court order.

Helen texts: Do you want me to tell the kids about the real you? About the bet?

Sam texts: Please, don’t ruin the only good thing in my life.

Helen texts: I’m going to call in ten minutes, and you’d better answer.

“Fuck, this isn’t going to just go away…” Sam said to his reflection in the mirror across from him. “I was just trying to figure out why she hung over him like a two-dollar whore, that’s all. I didn’t want anything else.”

He sits on the bed and sips his beer, turning on the bedroom TV. The phone rings after a while making the man jump and grimace. With shaking hands, Sam touches the screen, and said, “Hey, Helen.”

“Hi, it’s a good thing you answered, Sammy,” Helen said smugly.

The Bet Sequel Max Swan

  • Years after the original Bet that sees Sam turned into a cuckold, Helen again ensnares him into the more extreme lifestyle of sissy shemale. Includes a reworked version of the original story that sent SPH and cuckolding to the edge.

“What do you want?” Her laughter coming through the phone turns Sam’s face red and makes his chest hurt. “Why are you laughing, bitch?”

“It’s simple; just listen to what I have to say.”

“I’m not gonna entertain your sordid humor, just leave me alone.”

“SHUT UP. You’ll listen or else…”

“OK, what…”

“I realized tonight I’ve missed you and the fun we used to have.”

“You mean the fun you used to have,” Sam said screwing up his nose. “I’m not your sissy fluffer anymore.”

“You lost the bet, remember,” Helen said coldly. “You could’ve asked to stop at any time, and I would have, but you never did. You know why?”

“Why?”

“Cos you loved every humiliating minute of it,” Helen said with triumph.

“It’s not true, I left you because of it, remember?”

Helen laughs. “You left because you’re a coward. You didn’t want to embrace the real you.”

“You don’t know me as well as you think you do,” Sam said unconvincingly.

“I ran into Jan a few weeks ago,” Helen said coldly. “You remember Jan, your last girlfriend?”

“Shut up…”

“Jan told me you were the most useless fuck she’s ever had. The woman said you couldn’t even eat pussy well. That’s why she dumped you; Jan couldn’t stand your tiny dicklette.”

Sam gasps. “She told you that?”

“You know how we ladies like to talk,” Helen said smugly. “I told Jan she had you all wrong. You’re not the type for a regular relationship; you need the woman to control you. To humiliate and belittle you, that’s what you like. That’s what makes your tiny clitty dick cum the hardest.”

“Stop it.”

“I never forced you to do anything. Oh, sure, I ordered you, but if you said no at any time, I would have stopped. I never told you to suck cocks, for example. But my sissy cuckold husband couldn’t wait to taste real man meat.”

“That’s not true…” Sam whines.

“You loved those big cocks just as much as me,” Helen said coldly. “That’s why you were staring at Luke’s cock tonight. Everyone saw it…”

“Saw what?” Sam asks shaking his head.

“Hell, Sammy, you were biting your bottom lip as you ogled that meat. I captured it on my phone too. You’re still a cockslut and cum dumpster.”

“I’m not a cockslut, you are,” Sam shouts, balling his fist.

“Oh, I know you sucked them for me, my sissy fluffer, swallowed many loads of fresh cum too. But you never went all the way, did you,” Helen said coldly. “You never let them take your sissy cunt.”

The Bet Sequel Max Swan

  • Years after the original Bet that sees Sam turned into a cuckold, Helen again ensnares him into the more extreme lifestyle of sissy shemale. Includes a reworked version of the original story that sent SPH and cuckolding to the edge.

“STOP,” Sam shouts.

“That’s gonna change, after seeing you mentally fuck Luke’s cock tonight it’s time I did something to help you,” Helen said.

“I don’t need your help.”

Helen laughs again. “Tomorrow night Luke and I are coming over to your place about seven, and you’ll be ready for us. We expect drinks and food, and something else…”

“What?”

“You’ll greet us at the door wearing pink panties, a pink bra, pink stockings, and women’s perfume. You’ll shave your body smooth, and don’t forget your little dicklette.”

“Where am I supposed to get all that?” Sam asks shaking already.

“I’m sure you still have it from before,” Helen said sarcastically. “A sissy doesn’t change his spots.”

“Helen, you can’t do this to me again…”

“Shut up. We’ll be there at seven pm, Sam. If you don’t answer the door, I’ll tell the kids all about the bet. I’ll show them our special photo album…” Helen said coldly.

“No, not that … Please…”

Sam feels his heart nearly explode in his chest. He thought the photo album no longer existed, Helen had promised him she burnt it after the divorce. The man’s beaten and knows it.

“Sam, DO IT.”

OK…” he said with a sigh.

“Good, see you tomorrow night,” Helen ends the call and is gone.

*****

This is an excerpt from the SPH/Cuckold story The Bet Sequel, buy the ebook or join our members area to read it.

 

 

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