Maddy's Wedding and Honeymoon Ch. 03

Story Info
Maddy finds a rougher lover.
5.8k words
4.26
26.7k
29
6

Part 3 of the 4 part series

Updated 06/09/2023
Created 09/04/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Thadsgood
Thadsgood
646 Followers

{Cuckold story, no reason to continue if that bugs you, if it does and you still do...man there's something wrong with you}

***

We'd been in Miami only a couple days of our trip and Maddy had already fucked a 22 year old guy, Jimmy, and then followed it up by sucking him off again the next morning. That day Maddy was very tired from the night before so she pretty much went to bed early that night, leaving me still worked up from her previous exploits since we'd gotten married. It seemed like a long time ago but it hadn't even been a week since the wedding. I was already losing count of how many guys she'd done things with...3? 4? There was my cousin, a limo driver, Jimmy? Am I missing anyone? I probably am, it's all been such an incredible rush. I'm used to being cuckolded, or being a "stag" depending on your definitions. I've been used to her fucking around for quite a while now, but usually it happens over longer periods.

Even though she needed the rest, I was becoming hooked on her adventures, so any down time made me antsy for more, which I'm sure she'd use to her advantage later. While she slept I went down to get some coffee. I wondered if she'd be up soon to try and fulfill her "morning duties," that is, sucking someone off each morning so she can taste him and think about that throughout the day. Would it be Jimmy again? Or perhaps his roommate Brett, who she described as a younger, rounder Jonah Hill. The thought of a guy like that getting Maddy's mouth kept me sexually charged.

I stayed by the pool and watched as guys swam and walked around and I judged each and every one of them, as they all could possibly be dalliances for my wife. I found myself wondering what they were packing, as it's often hard to tell, most guys now wear swim shorts, not speedos, thankfully. I stood and looked out over the ocean. I spotted a familiar face, and even though repulsed, I seemed drawn to go over to him. It was Diego, that fat bastard with the gold chains and the huge ego.

I walked past him, he grunted a nod of recognition. I was torturing myself, like a moth flitting around a flame, so precariously close to being burned, but still drawn to it by nature. I stopped. I turned and said, "hey, remember that yellow bikini'd "chiquita" you were talking about the other day?"

His eyes opened wider. "Yeah? That hot bit of fluff? Hard to forget. What about her?"

"I saw her earlier in the lobby, she heads for the pool at the hotel first thing every morning," I lied.

"Clevelander, right?" He asked interestedly.

"Yep."

"Why are you telling me this?" He asked, somewhat suspiciously.

"I knew you were interested," I said truthfully.

"And you aren't, what are you, gay? You'd have to be not to want to hit that."

I smiled, "no, I'm not gay. I'd love to "hit that" as you say, but as you told me the other day, women like that aren't interested in guys like me."

"What guys, boring guys?" He asked, without realizing it was a jab at me.

I just laughed, "no, NICE guys. They want alphas. Me, I'm a, live and let live guy, not a taker."

He grinned, "too bad for you then, because guys like me LOVE to take that kind of shit."

"Which is why I'm telling you."

"How do you know she's "like that?" He asked. "I mean I only talked to her for a minute and it seems she's a bit wild, but how do you know, Mr. nice guy?"

"Well, I did notice the wedding ring," I said. "And, I heard her talking to a guy at the pool yesterday and she said her husband is back in michigan."

"So?"

"So, it just seemed strange then that two nights ago I saw her leave in a cab with a guy who couldn't have been more than in his early 20's and when I saw her the next morning, early, it looked like she had just gotten back."

"That's what I'm talking about," he smirked. "I knew she was the type."

"Are you going to go for it?" I asked.

"What are you, her agent?" He said suspiciously.

"No, I just thought, if I can't have her, at least maybe I can enjoy it somehow."

"Like a voyeur?" He asked.

"Kind of, yes."

"I ain't letting you watch, pervert," he grinned. "But, if I do anything and I see you again, I'll buy you a beer, or a wine, or a shirley temple, whatever it is that you drink, and tell you about it."

"Wine," I said. "Cool, good luck."

I walked away, still smarting from the obvious zingers, but smiling inside wondering if I'd done something good for Maddy and I. I didn't see her much of the day, except from afar, at the pool. We had an early dinner together but not much was said the entire meal until the end.

"Have any plans?" I inquired hopefully.

"Not really," she said, as if bored. "I got hit on all day, but, nothing stood out. They were almost all young, like Jimmy, and we did the Jimmy thing."

"What about Jimmy, then, are you done with him?"

"Yes, mostly I guess. He needs to be on hand though, in case I need the cock for my morning suck."

That she said it so matter of factly, that she was so blase about it tormented me.

"What about that morning thing, by the way. Did you...this morning?"

"No, sorry. I wanted to, but I got up late and really didn't want to repeat the Jimmy thing again, at least not right away. We have to amend the rule anyway, I'm not often even home until the wee hours of the morning. Let's say that if I didn't do anything else the night before THEN I have to suck some guy in the morning or at least early afternoon or at least try. But if I'm busy the night before then probably no."

"But you didn't do anything last night, shouldn't you be doing it today? No thought of Brett?" I wondered aloud.

She laughed, "No, you pervert. Not that I wouldn't, for us, it's just that if I went to their room, both would want something. Even though that might get you off, I really want something different, something new and exciting to get us BOTH off. But yes, I "owe" an extra blowjob, I'm sure I'll be able to "catch back up," before we're done."

I was disappointed but understood. "So nothing tonight either?"

"We can talk about it," she said. "I could hit the bar and pick someone up. Maybe you can give me some ideas about who you want me to target. Like, do you want me to try a black guy, a hispanic guy, an older guy? These are your fantasies too."

"Actually they are mostly my fantasies that you've done, what are some of yours?"

"You know mine, silly. They are pretty much the same as yours. You know I love dominant men, rough men, I love humiliation, just like you do. Most of the stuff lately has been for your humiliation, not that I'm complaining. But you know I love that stuff too."

"I know, I actually have something really challenging, dirty, right up your alley," I laughed.

"Oooh, I like the sound of that," she purred.

"I knew you would, even rape sounds good to you."

"Shhhh," she said excitedly, looking around. "Don't you bring that word up to me like this, in public, you know what that does to me."

"I know," I smiled. "That's why I often do."

"You know what I mean," she said. "I love the thought of it, being taken, the possible danger, some guy getting what he wants from me, for only his pleasure, while at the same time giving me MY pleasure. That, but without the actual risk of getting hurt or ending up dead."

"Right, we've talked about it, fantasized about it. I've loved the times we've play acted it out, where I was the "intruder."

"Yes, I loved it too, it always makes me hot, but it still lacks the element of "real" rape."

"I love your evil mind," I said proudly. "But for now, I had something sort of set up."

"What is it?"

I told her all about Diego, his boasting, his belly, his ego and then what I told him about her.

"Well, he sounds totally disgusting," she laughed. "Which I'm sure gets you off."

I nodded, sheepishly. I told her that I'd informed him about her daily morning "tan" sessions at the pool. "I have a feeling this guy is all about dominance and taking what he wants, from everything he's crudely said to me about you."

"Sounds like it, it's making me kind of wet just thinking about it. So yeah, tomorrow morning, I'll be at the pool, bright and early. I bought a new suit, it's mostly for tanning, it barely covers anything. I think I'll let him enjoy it, if he'll show up."

"I think he will, he really really seems to want to "hit that" as he keeps saying."

She smiled, "Oh, one thing for you to think about tonight is that I found a guy for the morning cock sucking tomorrow."

"Oh really? Who?"

"It's one of the bartenders."

"How do you know, did you already make plans?"

"Not exactly, but tonight I know he's working, he's tried to get me to meet him after work, but he doesn't get off until 4AM, bars go all hours here. But, tonight I think I'll lay the bait and see if he's interested."

"Do you think he'll be up for it?"

She grinned at the inference. "I'm sure he will be, I think he'd be up for it," she giggled.

She went back to the pool bar for the night and I didn't see her until she curled into bed with me after 1AM. Nothing happened, I know we were both getting antsy.

She awoke first the next day of the honeymoon. I acted like I was sleeping and watched her get dressed. She put on one of her sundresses that highlight her magnificent figure so well. It showed plenty of cleavage and I noticed she didn't put on panties. I also noticed she had on her favorite shade of lipstick which she refers to as her cocksucking color, a very sexy shade of red. I pretended to be sleeping as I saw her take a peep at me while she tried to sneak out the door without waking me. I was hard already. She was gone for an hour. She came back with two coffees. I noticed her lipstick was pretty much gone.

"Hi honey, good morning," she said huskily while giving me a big, sloppy kiss. There was no mistaking the aroma and the taste on her lips.

"I guess someone got lucky this morning," I said with a sigh.

"I was the lucky one," she chuckled. "His cock was soooo fucking nice."

"The waiter?"

"Yes, Fernando, and Fernando loves your wife's mouth, baby, he said so many times."

"I'll bet he does. So a hispanic guy?"

"Actually, he's black. Well, maybe mixed, but definitely black."

She knew that would perk me. "So you just sucked him off?"

She hit my arm, "Just? Just? Like that's nothing?"

"Not at all," I protested, "I meant..."

"I know what you meant, tiger, I'm just teasing you. He did finger me, I didn't wear panties, of course. I know he wants to fuck me, but I told him about my fantasy of sucking a different guy off every morning I'm here, and he was good with it, for now."

"But you'd like to fuck him?"

"God yes. But I know you had another plan first, there's always Fernando, Jimmy, or Brett to fall back on, if we must."

With that she got up and redressed, this time in her micro bikini. It was totally wicked, something you could only normally get away with wearing in the privacy of home, or some wild place such as we were in, South Beach. The bottoms were basically just strings over her hips, the two triangles were smaller than small, barely covering her pussy lips and in the back making it basically a thong. The top had the two triangles as well, again, the triangles so small it barely covered her aereolas. She adjusted herself and smiled at me wickedly before blowing me a kiss on her way out the door. " Enjoy yourself today baby, don't let me have all the fun."

She knew that this WAS my fun, though. I just sighed and reluctantly rose, no doubt to face another day of denial and torturous anticipation. It always was worth the payout, of course, but agonizing to be in the middle of it. Even though I longed to be back home where our depravity was somewhat contained, I still wanted this, all of it, whatever I could get of it.

I sat at the bar most of the afternoon, occasionally getting up and walking short distances on the beach, so as to not get too drunk. I thought about everything we'd done, all the way back to the first times I shared her. Well, more accurately, the first time SHE shared herself, even though it was with my blessing most of the things had been her ideas, built on our mutual fantasies. I thought of how she'd given me pretty much everything I fantasized about. She'd fucked Jeff, a coworker of mine because I had a fantasy about it. She sucked the nerdy older neighbor, just because it fit my particular fetish. She'd even gone along with fucking her brutal ex, just because it turned me on just to hear about the things he'd done to her in the past. Even though one could say, she was having all the fun, in truth, it was also MY fun, the things I enjoyed. I thought a lot about what turned her on and it kept coming back to the dominance, roughness thing. She'd always craved that. I also couldn't get the word rape out of my head. A plan started formulating. I was so engrossed in my own head that I realized I'd turned down a drink offer from a very pretty MILF type, probably in her forties, cleavage to spare. I knew Maddy would've loved me to "partake" in that. But, I was so in love with Maddy and so turned on by her exploits that I hadn't even considered it.

I finally got a text from Maddy. "Hey sexy, guess what? Some guy named Diego was all over me this morning. You are right, he is such a pompous ass, and crude as a sailor. Does that turn you on? Thinking that jerk might be pumping your wife later?"

"Oh god, Maddy," I responded.

"Well, I don't know what will happen, but he invited me to go on his boat this evening and watch the sunset."

"I don't think he's interested in the sunset," I said.

"Hee hee, no, I doubt it. And no doubt I'll be in no position to see it either *g*"

Man she knew how to play the game and twist the knife. "Are you going to be safe?"

"Yes. I told him that I told my "roommate" his name and his boat's name and where we were going and when I'd be back. Hee hee, get this, his boat's name is Alpha , fitting right?"

"When did you say you'd be back?"

"I said midnight, it's six now, we're having dinner at some really expensive place. I think he's trying to make me feel like I owe him something. Hee hee, if only he'd known he was going to get it anyway, even if we'd gone to McDonald's!"

"God Maddy, you are so sexy, be careful."

"I will, we won't be alone, he has some friends that are coming, I guess it's a big boat!"

Immediately thoughts of gang bangs entered my head.

"Are you sure that's safe?"

"It's another couple, I think maybe his brother, his brother's wife, and another guy, not sure really."

I felt a little better about that.

"I'll see you late, I'm sure it won't be midnight *blush*."

I slept in short, fevered stretches. I kept looking at the clock. 12, nothing, 1AM, nothing, 2AM, still no Maddy. Finally, she woke me up at about 3:30 and just crawled into bed with me. I could smell the sweat, the sea, and the sex. She just shushed me and curled up with me. "In the morning, baby, in the morning."

I woke early, around 7. I noticed a note on the nightstand. "Check your voicemail."

She knew I loved hearing her adventures in story form, she'd often done this via voicemail or email.

I checked my phone for the voicemail. It was from Maddy. I noticed it was timestamped at 1:30AM.

She said "hi baby! I'm still on the boat. I'm on deck, they are fast asleep, and Diego is snoring like a walrus, by the way, don't think I'm sleeping any here. I just thought I'd tell you everything while I can, and so I don't have to do it when I get back, because I know it'll be really late, and we'll both be tired. Well, at least *I'll* be tired, he wore me out. That's right baby, he fucked the shit out of your pretty wife. He may be arrogant, cocky as hell, but he sure can fuck."

My dick began to stir at the thought of that.

"We got to the boat, and it turns out he either was wrong, or just flat out lying to me because it was just him, the guy who I think might be his brother, and another guy, there were no women. I almost didn't get on. I started to text you but John, the third guy, told me he was a cop. He showed me his badge. He told me to call the station. I did, don't worry, it wasn't a scam, I didn't use the number he gave me, I googled it. Sure enough, he's a Miami Policeman. I made sure the receptionist knew my name and that I was getting on a boat. I gave them his and Diego's name."

I thought that was smart thinking on her part.

"Now I knew the night could go in any direction. I knew your fantasy was for me to let Diego have me, but I wasn't sure about a gang bang, or whether you even wanted that for me. I'm like more of the one on one action. Gang bangs aren't usually our style, right baby? The only time I'm into that is when there is one "making" me do it, directing things, then it becomes a different thing altogether. Diego saw my hesitation and pulled me aside and said, " don't worry, no one touches you here but me."

"I liked the way he said that, like he was in charge. You know how that gets me going? So we sailed out for a bit. It was beautiful babe, the setting sun was shining on the water in a rainbow of colors."

I couldn't think of anything but the thought of her alone on a boat with three strange men.

"He brought up some wine from below, it's a really nice yacht, baby. Anyway, we all sat around drinking and looking at the Miami lights from the sea. We were all feeling good and after the sun went down John and Jorge started playing drinking games. They tried to get me to play but I wasn't about to get too drunk out there. Diego just kept feeding them wine and they were laughing and getting drunker by the minute. Ooooh, just a minute honey, Diego is awake, call you right back."

Now obviously I didn't have to wait, I opened the 2nd voicemail.

"Sorry, where was I? God, for his age that man is insatiable. I just sucked him off. Five minutes later, bam, he's out like a light again. Anyway, we were all feeling good, John and Jorge were drunk, but a mellow, relaxed kind of drunk. They were quiet as Diego talked to me about himself, naturally, how he got his boat and all his money, etc. He had his arm around me and his one hand had been massaging my tit the whole time he talked. John and Jorge noticed, I could see their eyes on me filled with lust. I felt comfortable though, baby, I could see Diego was totally in charge of this whole deal. "

"So, I heard from a little birdie that you've already been naughty on your trip," Diego said smugly.

"Who told you that?" I asked, even though I knew it was you.

"A little birdie, or fairy, maybe," he laughed.

I know my baby isn't a fairy, don't worry, hon.

"I'm just having fun, a nice relaxing trip," I said to him.

"And married, too. You don't bother hiding the ring," he pointed out.

"No need to, I'm a big girl," I said.

He was ogling my tits when I said it. "Yes, big in all the right areas."

"Pig," I said, playfully hitting his arm.

"You love it, I know your type," he said knowingly.

Obviously he was right, I am exactly that type. I wondered what he'd do with that knowledge. His hand was now pulling my top down slowly, his fingers were casually, softly playing with the exposed part of my breast. It was making me tingle, especially knowing the other two were watching. He saw me looking at them.

"You don't even mind that they are watching, do you?"

He was challenging me. "We're not doing anything illegal, are we officer?" I joked to his friend John.

"Not from where I'm sitting. Everything seems to be on the up and up," he said with the double entendre. I noticed the two onlookers shift in their seats, no doubt trying to hide their growing erections.

Diego was watching me the whole time. "You like people watching, don't you, chickie?"

"Sometimes," I admitted, I'm sure the alcohol was helping loosen my lips.

Thadsgood
Thadsgood
646 Followers
12