Rehearsing for a Proper Marriage

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Bridesmaids and Groomsmen help us prepare for our marriage.
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After a long and virtuous engagement, our Wedding Day is nearly here. It's been a long day of dreading the rehearsal, especially the Rehearsal Dinner. Lots of pressure to be on our best behavior, especially in front of all our extended family. And friends of each of us. They're all quite different. It's been something of a nightmare for us, leading up to this point. I mean, my family is extremely straight-laced. Jen's, not so much uptight about sex as they are about career success... to a fault. Anything that impedes a quick ascent to the top, to the corner office, so to speak, is expendable and should be excised, no matter your sentimental attachments.

So her family has been chomping at the bit to get on with things, a short engagement, a small wedding so as to save our money for more practical things that will advance our careers, like a lake house when we can afford it, and hosting parties -- you know, where you have to pay a featured celebrity to come and act like your former high school boyfriend or girlfriend, right? So today's extravagant wedding was exactly opposite of what her parents wanted to spend (waste) their money on. But Jen always manages to get her way, and her parents have no one to blame but themselves for raising her to do so. So they caved, and they spent, spent, and spent some more.

Even paying for our honeymoon trip to an obscure island retreat.

The long overnight flight would pretty much ensure one thing: There would be no Wedding Night fucking. And after the long engagement (to satisfy my parents), our Wedding Night would be a rocky -- ie, hard as a rock -- disappointment. Especially for me. But Jen promised it would all be worth it. That's what she says about everything. Delayed gratification is the key to success, she says. Just as her parents taught her to say. It kept her virginity (and mine), didn't it? And considering she was the hottest cheerleader and class valedictorian, I would have to agree. She knows how to get things accomplished, even sacrificing desire as necessary -- her desires or mine.

So I can imagine flying through the night, only able to hold hands on her father's corporate plane -- it's too small and intimate, with too many of his staff waiting on us hand and foot. We would kiss... if we had a chance. Attendants would undoubtedly keep coming at just the very wrong times. And for sure, I will have to minimize those intimate moments, as my encased penis will be continuing to drive me crazy, til we arrive and my bride can do the honors, so to speak.

Yes, encased.

The very night I had proposed to Jen, her parents -- especially her mom -- had prepared her well. When I (thought I) surprised her with a small box containing an efficiently small diamond engagement ring, Jen surprised me right back, producing a git-wrapped box with an efficiently-small plastic device from her purse. It had to go both ways, she said. If I was to expect her to say 'yes' to my proposal, then I also would have to say 'yes' to her proposal. It was "for our own good". Remember, delayed gratification is the key to success. So what else could I do?

And we were officially then engaged.

She immediately called her mom. "We're engaged. He said 'yes'!". And her mom couldn't have been happier. Her dad? Well, maybe notsomuch, but glad to see his daughter and wife happy, even excited. Jen told me later that it sparked a reenactment that night, of their own engagement-proposal many many years ago.

And so the engagement had begun for us. Jen's girlfriends were all abuzz about it too. They had previously given me the cold-shoulder anytime they were (had to be) around me. They kind of even treated me like dirt, like I was household staff, just like Jen's parents' home staff. They knew better, but I think they were always telling Jen she could do better. Thankfully she didn't listen to them (or her mom, for that matter). And now it was apparent to me that Jen told them about the 2-way proposal that I had said yes to. How embarrassing. But at least they knew I was that head-over-heels in love with Jen, and committed to our virginal relationship.

On the other hand, I tried desperately to keep my guy buddies away from her friends, for fear they would hear of my penis-predicament. I had for many months let on like I was secretly banging Jen, despite her cool temperament when they were around her. I made like I was forceful with her and she was embarrassed not to be able to control me in bed. And that's why I always tried to let her have her way any other time -- at least that was my narrative to them. They all thought I was the ideal boyfriend. The stud behind the scene, but ladies-man in public. That storyline worked well for me, unless her friends ever intersected with my buddies and spilled the beans. I couldn't let that happen. So you can imagine the pressure at our Rehearsal Dinner, when the groomsmen spent the evening with us... and importantly, with all the bridesmaids. Dang.

Thankfully my parents were the evening's host, and my talkative mom pretty much carried the evening with funny little stories from my childhood. The evening had come to a close and everyone was leaving... when her Maiden-of-Honor pulled my Best Man aside over in the corner. I could see her hand him a small box, and I didn't like the looks of it. Especially when he laughed out loud and readily accepted it.

"Sure, I'll do the honors", he said loudly enough to ensure I heard him. And everyone went back to talking and saying their goodbyes with hugs and well-wishes all around. Even Jen begged off early: "We have a big day ahead of us, Harold. So I need to go home and get some last minute prep done, and get to sleep. You boys have some things to do too, apparently. So we'll let you get on with it. Goodnight, dear little Harold, my sweetie.". And left with a peck on my cheek. Her Maiden-of-Honor also gave me a peck on the cheek, and left with a wink.

And there I was. With only my Best Man, who was beaming like a cat that had swallowed a canary.

"Ok, what? What did she say to you? And what's in the box, Fuckhead? I know you two are up to something. Spill it."

"Harold, oh Harold. My longtime buddy. Mr. Stud, you led us to believe. How the tables have turned now, as your little secret has leaked just a bit. But as your longtime buddy, you can count on me to keep it just between the four of us. I only ask that you don't give me any problem tonight. Or for that matter, you will of course need to treat me quite well for the foreseeable future. Right, buddy? Can you do that? It's a small price to pay for my loyalty, wouldn't you say?"

Dang.

"Of course. Please just keep this as a matter between close friends. I'll make it worth your while. Just keep it under wraps, ok?"

"Oh indeed, I'll keep it under wraps ok! In fact, that's the whole point of this little present from the Maiden-of-Honor: Keeping IT under wraps, so to speak. So Harold, you say you'll not give me a problem tonight, and that you will always make it worth my while not to share your little secret, so we're going to see about that. Come on, let's go out to my truck. You wouldn't want to do this here, would you?"

He tapped the box, lifted me a bit by the arm and hustled me through the revolving door and pointed me toward his truck. You're in luck, Harold. I had to park way out in the lot. If you're lucky, buddy, no one will see this.". And laughed. And gave me a shove toward the back lot, albeit well-lit with those tall parking lot lights. (...not to mention, nowadays way too many of them have cameras embedded in the lights.)

Arriving at his truck, he personally ushered me in, almost like I was his date for the evening. It was embarrassing.

"Get in. And scoot over, nice and close to me. We're best buds, right? And we have some friendly business to attend to, my little buddy. Now would you like to chance it here... or up on Make-out Point in the dark?"

"Oh c'mon, what is the big deal? Out with it, you fuckhead."

"Uh, I'd be a bit more cautious, calling me the fuckhead, Harold. Or you just might find your head doing some fucking tonight. Got it?"

"Ok sorry. Let's get this whatever over with. And I sure don't want to be seen here in the lights. So sure, up on the bluff in the dark if we must. But I'm not doing any head-fucking on you tonight. Don't even think about it. I'm not queer, and you know it."

"Oh do I? Until tonight, I apparently thought a lot of things that weren't entirely true. Didn't I, Harold?" And he gunned it, peeling out of the lot to be sure everyone saw us together."

When we arrived up on the point, he turned on the overhead light, and told me to show him my little secret. I complied. He laughed. And started unbuckling his belt, and unzipped. Oh no! And pulled it out for me to see. His purpose was all too clear.

"So whaddaya say, Harold? Am I your Best Man or what?"

"Ok, ok. You're bigger than me, and yours is free -- mine is not. Is that what you wanted to hear from me. Ok, I said it. Now can we go?"

He laughed again. "Oh no, no, no, Buddy. We're not done at all. If I'm going to be your Best Man, then we have a long night ahead for you to prove it. You can start by handling it a bit and getting me hard. And if you do a good job -- you know, like a Best Man should -- then I might just unlock your encased penis. I have Jen's key right here. Whaddaya say to that, Harold? A little you-scratch-my-back and I'll scratch yours. Do we have a deal?"

It is unavoidable at this point. I took hold of his cock, and massaged it enough to get harder than it was already. Shit. I can't believe I'm here doing this, jacking off my buddy on Make-Out Point in the dark... with our cab-light on, even. What perverts might be watching us even right now?

"Ok, but only a handjob. I'm not gay. And neither are you. Let's not start down that path on my wedding eve. This is wrong on so many counts. So humiliate me if you must, but just please get your rocks off as quickly as you can and let's get out of here. You don't even have to unlock me. Ok? Hurry. Please." And I jacked faster.

He began laughing even harder, and said:

"Ok stop, Harold. I was just punking you, man. It was just a joke by the Maiden-of-Honor. I don't even think Jen knew what she was up to. So get your eyeballs back in your head, and keep your hands to yourself, Ass-hole. But I'm honored to know you would... maybe even will someday... jack me off." And continued laughing his head off.

Aw shit! You bastard. I jerked my hand back quickly and wiped it off on the truck seat, and scooted way over to the window. Dang. I went to zip up again, but he stopped me.

"Wait Harold. We're not done with the business at hand. Just the punking part. The reality is, I do have Jen's key. And I have been commissioned to unlock you. Ok? So keep it out here; in fact, scoot back over here and lift up and arch your back a bit so I can get it off you."

I reluctantly complied, glad to finally be free.

He massaged me once I was loose, a bit too much for my own comfort, but I figured he was just still fucking with me a bit. Still, it didn't keep me from hardening. Dang.

"Nice, Harold! Real nice. Further proof that you really would have finished me off -- probably even hoping I would get you off too, huh little buddy?" And again, laughing at my predicament.

"Hell no. You know that a guy's dick is sensitive to any handling. So shut up and let's go."

"No, not just yet Harold. Removing your little temporary plastic guardian is just half the deal."

And with that, he produced the small box that the Maiden-of-Honor gave him.

"Here's your new marital friend and companion now. This time, steel, and just in time for your appointment at the altar. A present from your new Mother-in-Law."

"No fucking way!"

"Yes fucking way, Buddy. Turn your head and say hi to the camera. That's right. Your Maiden-of-Honor has done the honors for your wedding album, Harold. Well, unless you comply, that is. So let's get this one on you, and we can keep this our little secret. We won't even have to tell Jen about your, how shall I say, desires for another man?"

I let him lock it on me. Silent. Speechless. Anything I would say at this point would only get me in deeper. So he locked the steel cage on my dick. The night before I'm to be married. Sigh.

"There, Buddy-Boy. You're good to go, for a lifetime of marital bliss. Able to fuck anytime... that Jen approves of. Ha ha. And now for MY reward for carrying this all out according to the plan. Your Maiden-of-Honor has promised me some pussy tomorrow after the wedding if I'd play along. And she even told me how turned on and jealous she has been throughout your encased engagement. And she wants to role-play with me, pretending she's Jen and I'm you, Harold, reliving the past year leading up to the Wedding Night fuck! So help me out, Buddy. She said I need to be wearing your little plastic cage during tomorrow's ceremony. It'll make her so hot as she stands there knowing what we will be role-playing tomorrow night! The only difference between you and me is, I'm no fool -- I'll be holding onto my own key. You won't. So help me get it on. C'mon, before I get hard just thinking about it."

It wasn't easy. His balls were bigger, harder to get through the base-ring. And helping him stuff his slightly hardened penis into my-sized cage was no small undertaking.

"Hey I want to see! Lemme see. Lemme see!" The Maiden-of-Honor was banging on his window. He rolled it down to show it off to her. She leaned in and kissed him hard as she fondled the cage. So turned on!!! I had always wished Jen could have been so passionate about that cage. But now her bff was fully fucking my Best Man's mouth with her tongue as she got off on the pretend control that the little cage symbolized. She toyed with the lock, threatening to close it."

"You know you'll be forever mine", she pretended.

He played along, not at all worried that she might close it, since he had the key safely tucked in his jeans watch-pocket.

"Oh no! Please don't snap that lock shut!" he pretended, carrying on the scene for my benefit, knowing I have been locked, without orgasm or even a proper erection for nearly a year. "Oh please, Miss. I'll do anything you want. Just don't do that, I beg you." He was fucking with my head still.

"Ok, big boy. Today's your lucky day -- I won't snap it shut... BUT HAROLD WILL!"

It was only fair, after what he had done to me. So I played along, snapping it shut just as hard as I could, hoping it would jam there.

Holding out her hand, she said, "Ok, hand over Harold's new key, and yours too, big boy. You need a keyholder too. Remember, you bad little boy. I saw you BOTH out here in the dark, playing with each other's ding-dongs. I even have it on video. Without sound, it pretty well looks like both of you were enjoying a boy-on-boy relationship, doesn't it? And don't think I won't show the preacher tomorrow, if I see either of you misbehaving or playing with your cages during the ceremony tomorrow. Now let's have 'em. Both keys. It's the Maiden-of-Honor's duty to be the official keyholder during the ceremony."

Wow. His key too! I couldn't help but see the ironic turn of events here. He looked like a whipped puppy as he reached into his pocket and reluctantly turned over both keys as directed.

And with that, she laughed at us sitting there together in his truck, stunned... and scurried back into the darkness of the night... to get ready for the TWO weddings soon to take place.

***

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3 Comments
AnonymousAnonymousalmost 2 years ago

Great twist. Will you continue this story?

AnonymousAnonymousalmost 2 years ago

I really hate these stories. Trying to make a guy sound like he's straight, but goes along. No straight guy would marry a slut, who would lock him up and no straight guy would go near his best man's dick. If the subject in the story was anywhere close to being a normal young heterosexual male, he would have told his girlfriend to fuck off when she produced her little box. The story doesn't work.

AnonymousAnonymousalmost 2 years ago

great going so far, definitely need one or the more chapters. how stupit could his best man to not see what was coming..

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