When my wife of 10 years left me after years of a bad sexless marriage back in 2918, she’d been fucking one of her co-workers for almost a year. The divorce was fine. We signed a prenup, are both professionals with separate accounts, never had kids. Sign here sign here see you in hell. We had grown to hate each other anyway. I let her keep the house and the dog. I kept my cat.
I found myself jerking off to the thought of her cheating on me for months after our split. The guy was literally superior to me physically in every way. When we had our big blow out after I discovered her infidelity she made sure to tell me he fucked her better than I ever did, made her cum when I couldn’t, and that she loved his “big fat dick”. She said a lot of shit like that.
I’m packing a very sub-standard issue 5 inches that fits inside a TP tube, and she knew I was sensitive about it. She was trying to hurt me, and it worked, but I’ll be damned if it didn’t make me hard. Like, harder than ever. I had a girlfriend cheat on me once in college and it was the same reaction. Instant intense unrelenting erection. I jerked off for years thinking about what I saw when I caught her riding my roommates huge dick one night. Guess I’ve been a cuck deep down for years. I used to fight it. I’m more than fine with it now.
After about 8 months of obsessing over my ex and steeping my brain in a lot of Cuckold porn, I decided I needed to get my shit together, get back out there, and get myself laid. I was 42 years old and hadn’t seen the inside of a gym in almost 10 years. I got a trainer, starved myself and got in the best shape of my life.
Dating in your 40s sucks. Or at least I suck at it. I didn’t know what I was doing and I turned my nose up to anyone my friends would try to set me up with. Obviously, Satan must have owed me a favor because within just a few months I found myself with an extremely intelligent, sweet, kind, absolutely stunning 22 year old college senior. Dreams do come true, my friends.
Madi was an angel. The short version is, she worked for me briefly but quit because she needed to focus on finishing her degree. She’s the one that made the first move. We fucked on our 3rd date and she all but moved in after about a month.
This amazing specimen was mostly Scandinavian by descent. PolylSci major, pre-law, volleyball player until she quit two semesters ago. 5’6”, maybe 115-120lbs (idk I’m bad with guessing weight and I never saw her step on a scale). Worked out every day and ate like a T-Rex. Big green eyes, pink pouty lips, bright perfect smile, and a cute little nose. She had long straight golden blonde hair that went halfway down her back, a smooth fit and slender body that looked like it was carved out of marble by an Italian master. Tiny waist with a big firm round peach of an ass – dear. god. that. ass. – no thigh gap on this daily runner. She had bouncy round B cups with tiny pink nipples that begged to be sucked. The icing on the cake was her petite, delicate, bright pink innie slit so small and tight it felt like a vice grip even on my humble dick. She could crack a walnut with that thing. I swear to god her pussy tasted like a strawberry Starburst. As for me: she says I look like Bruce Willis, 5th Element era. I wish.
A lot of people thought it was age/life stage inappropriate. There was a lot of “sugar daddy” and “succubus” and “he’s using her/she’s using him” thrown around. Her friends and sister liked me, and that mattered the most to her. We liked all the same stuff and shared new things, she laughed at all my stupid jokes. We had a blast. She loved that I was “experienced”. I never at any point expected it to turn into a relationship like this. After all, she graduated in a year and had every intention to move to L.A. for law school with her best friend soon thereafter. I felt like I was trying to ride lightning, and I was going to hold on as long as I could even if it killed me or slipped away.
Even though she enjoyed booze and weed like any rational high stress hard working human. Madi had always been a relatively “good girl” and had only slept with three guys before me. She didn’t have the most “sex-positive” upbringing, and was a bit of a late bloomer. She was always focused on studies and sports, and never had a “wild” phase in her earlier college days.
According to Madi, I was the best, most passionate lover she’d had and she loved fucking me. She was incredibly limber. There was nothing she wouldn’t try. I was the first guy to cream-pie her and she gave me her anal cherry. Anal isn’t her “thing” but she almost always lets me do as long as I don’t try too often. I consider that small dick privilege.
So I felt like King Stud pounding this tight little coed into the mattress all night every night better than anyone had before – tying her up, spanking her raw, cumming in her ass – No functionality issues on this Gen X daddy. I was exhausted at work every day, I was covered in scratches and hickies, and it was fucking worth it. I could smell her on me all day long and it kept me going. Best post-divorce scenario ever and I highly recommend it if you can pull it off.
Sexually, she was insatiable. I kept up for the most part, but I wan never able to get her off by fucking her no matter how long we went how much of a knot I tied her limber body into digging her out as deep as I could. only been able to fuck about half of the women I’ve been with to orgasm, and I’m sure some of them were faking it, but I desperately wanted to give Madi that deep vaginal O.
It bothered me, but she said she “just wasn’t able too” and none of her exes could make it happen either. She was apparently afraid of large dildos and vibrators even though I advocated it. I tried not to dwell on it, but I felt like all she’s done is fuck guys with lame dick so far and she didn’t know any better. The girl was seriously built for fucking, and she hadn’t yet discovered her full potential.
I never directly told her that I got off on the thought of sharing her with a sexually superior man. However, she picked up on my lack of jealousy and bisexual predilections immediately. She was comfortable telling me about guys she thought were hot and how she’d get hit on when I wasn’t around. It seemed to turn her on too, but she was always cautious about it. Not that I blame her, most guys are insecure about shit like that.
I paid for her haircuts, manis and pedis, and to keep her sweet little kitty waxed. She always stayed unbelievably smooth. Every day when I came home from work she’d be on my couch studying or playing video games, in nothing but one of my old band T-shirts. She was going through a lot of personal and sexual changes, and I was there to be open minded and supportive. I was completely wrapped around her pinky and would have done anything to make her happy.
That following winter I surprised Madi by taking her on her first cruise over her winter break. Adults only, unlimited booze package, party themed, suite near the top of the ship. We live in what’s referred to in America as a “flyover state”, so 6 days and 5 nights of beautiful weather with her drunk in a tiny bikini sounded like true paradise. We’d been together for almost a year at that point and I wanted to do something special for her.
There were a lot of people her age, which I expected. There were other 30 and 40 somethings there having a blast, but they appeared to be mostly married couples looking to spice things up. I got hit on a lot by that crowd, but that’s not what I was there for. A 42 year old that had to shave his head to hide the natural balding with grey in his stubble hanging out with a young bubbly semi-nude blonde did stand out a little bit – but we weren’t the only couple with our kind of age difference for sure.
Every guy was checking her out and most of them tried to talk to her on day ones I always let her handle herself, not wanting to be the hovering insecure boyfriend. That, and I loved to watch her flirt back on the rare occasion it happened. I knew I was taking my little nymph on a sex and booze cruise full of other college age people, after all. I knew exactly what I was doing. Madi was definitely hard to get next too but a joy to watch work when she was into it.
One guy was overtly and relentlessly interested in her, and she took a liking to him immediately. He was the archetype of “tall dark and handsome.” Madi actually pointed him out day one saying he looked a bit like Michael B. Jordan and I couldn’t argue with the assessment. I caught him noticing her too and watched them make eye contact and exchange flirty smiles from across the deck. I could practically see the sparks. He saw me, smiled and nodded his head approvingly at me. I nodded back and returned the smile.
We had sex most of day 2, emerging only for meals and a bit of lounging on the deck that night looking at the stars. At one point, Madi went to the pool bar a level below us get more margaritas. That evening Madi was wearing what she called a “dress” but was really just a long black Lycra tube that barely covered her tits and ass. No bra of course and a basically non existent black lacy thong. The most substantial thing on her body was the diamond pendant I bought her for her birthday. She smelled like cocoa butter and traces of the expensive French perfume I kept her stocked in. I watched from the level above as the same young hot black guy from before approached her while she was waiting for the drinks.
I couldn’t hear what was said, but it was obvious he was flirting with Madi. It was also obvious she was really into it. She was leaning on the bar sticking her tight round ass out and biting her lip, giggling and twirling a strand of golden hair around her finger as he eye fucked her and inched closer – but the drinks arrived soon and she spun off looking back at him over her shoulder. I was extremely turned on by the scene.
“Who’s your new friend?” I asked coyly.
Sipping her margarita, Madi said, “His name is Troy.” She paused to lick the salt off her sweet pouty lips, “he said I was the hottest girl on the boat and he was hoping to meet someone just like me. He asked if I wanted to make some content.”
“He’s right, you are.” I said putting my arm around her waist and pulling her close. “What did you have to say to that?”
She stared at the dark sea and brushed a strand of hair out of her face and said, “I said I was here with my boyfriend, and I don’t make content. He said he could work with all that. He was all, “It’s 9” and real thick, you’ll love it baby girl , I promise.” He was reeeeally drunk.”
I chuckled as I looked for the right words trying not to sound insecure and and also not turned on by what was going on – but Madi interjected with her own nervous laughter.
“Like does he think I’m going to hook up with him with you here? Come on bro.” she said sarcastically.
“With me here? Would you if I wasn’t here?” I asked, genuinely aroused and curious.
There was a brief pause before Madi slapped me playfully on the chest, kissed me and said, “You’re the only one I’m going to fuck on this boat.”
Not a “No”, I noted. I decided not to push the issue after that, but my wheels were spinning. Guess what I thought about while I fucked her all night? I assumed she was thinking the same thing because she was putting it down extra slutty and was soaking wet by the time I peeled her out of her dress.
It was around 3pm on day 3 and I left Madi poolside to run back to our room for a book and fetch her piña colada number 5. She was wearing microscopic white crochet bikini. You could clearly see her nipples and the bottoms were no better – they were so low rise they began at the very top of the curve of her pubic mound. She’d been basking in the sun letting me cover her in oil all afternoon, flashing me a nipple now and then and talking dirty.
I come back after maybe 20 minutes and there was Troy – shirtless, fit and muscular, broad shoulders, thick thighs, ridiculous abs, and a perfect smile – sitting in my chair making my sexy little pink and tanned angel giggle like a school girl.
Madi didn’t even notice I’d come back until I cleared my throat, and when she did she blushed and squirmed a little. On the other hand, my dude was as cool as the cucumber it looked like he had stuffed in his flattering shorts. He stood up to introduce himself to me and was definitely 4 or 5 inches taller than me to boot. The man was a 6’4” ebony Adonis.
“Hey, man, I’m Troy.” he said smiling warmly and extending his hand, which I took. He had really long, thick fingers.
“Yes, I know. Madi said you guys had a nice conversation the other night.” I said, hoping it came off as cool and not threatened. I think I came off a bit possessive.
“Yeah that’s why I came over here. I wanted to apologize for coming on to her all sloppy like that. I was drunk and she’s so fine, you know?” he said gesturing towards my girl. “She let me know upfront she was with you.”
I nodded in agreement. “Yeah I know, and I agree. I’ve got myself a dime here. She does get a lot of attention. I’m used to it. I am the one who brought her here after all.” I said and we both laughed.
I couldn’t tell who Madi was staring at behind her big sunglasses but she was watching the exchange intensely.
“So uummmm yeah, hopefully I’ll see you guys around.” Troy said casually waking away.
“Sure thing, man.” I said. “We’ve got a few days left, you should definitely get to know her better.”
Not subtle. It just came out of my mouth. I didn’t intend to go there, at least not so directly, but I’d also had 5 pina coladas.
“Oh yeah bro, for sure! Bye Madi, until next time, baby.” he said now cockily strutting away.
“Bye, Troy.” said Madi timidly. She watched him walk away as I sat down and handed her a drink.
She stared at me.
“What?” I asked flippantly, like I didn’t just invite the hottest guy on earth to hang out with her.
“Wow – you are full of surprises. You did not react like I thought you were going to when you found him talking to me.” she said sounding confused.
“What’s the harm? Guys are gonna want to get next to you, I can’t prevent that.” I said. “Besides, it seemed innocent enough.”
Madi cleared her throat and shifted in her lounge chair, “Yeaaaah….I wouldn’t say innocent. I told you what he said last night.”
“What do you mean?” I asked. “What exactly were you guys talking about? He already came on to you, and is basically a sex party cruise. I think a lot of people are here to fuck. How, exactly did the conversation go? What had you all giggly like that?”
Madi blushed and swallowed a big gulp of her drink. “He was very direct. Very direct. Really trying to sell himself, if you know what I mean. Said he could show me a clean STI test from right before the cruise started…and having fun is the only reason he came….and now that he’s found me he’s…ummm….holding out for me. Or so he says.”
“Wow, ok – that is direct. This dude sounds pretty dedicated to the idea of fucking you.”, I said, genuinely impressed with the confidence.
“He seemed sincere, I’ll give him that. He plays college basketball out East, I guess. He thinks he’s a big deal.” Madi said, also sounding impressed.
“I mean, I get it though. You are pretty special, baby. He didn’t seem very put off by my presence. That was interesting.” I noted.
Madi continued, “I told him you’d be right back and that he should go and he said…um…he said he didn’t mind you being around. That you could watch if you wanted….if you were into it.”
“So, he thought I’d be into it? That’s pretty wild stuff, what do you think of all that?” I asked as my heart pounded in my chest.
Jesus Christ I’d have paid good money to watch Madi fuck a hot hung black stud. Fuck yeah I was into it. Let’s fuckin do this.
Madi stammered, not answering the question, “He assumed since you were older than me and you seemed cool that we were…open like that…I guess that’s not that uncommon, right? He said he’d leave it up to me to talk to you about it if I was interested. That’s when you walked up.”
I could barely contain my boner. “Soooo is this you talking to me about it?” I asked in a cool tone, trying not to spook her.
I’d never seen her so nervous. This was definitely uncharted waters and more extreme than anything either of us had ever done, especially her, and I would have understood if it was too much.
She was immediately defensive. “What?!? No, no, I mean why would I….”
“Because he’s insanely hot with a big dick and we’ll never see him or any other other people on this boat ever again after this cruise? Why wouldn’t you want to? You can’t tell me if you were here alone or with your friends you wouldn’t go back to this guys cabin in a heartbeat. It’s cool baby. I’m cool. We’re cool.” I said sweetly, reaching over and holding her tiny little manicured hand. It was trembling.
“We’re ‘cool’?” she asked skepticaly. “As in…you’d really be ok with me having sex with that guy? Seriously? I mean…I just met him. I don’t even know him.” Her breathing was heavy and she was nervously chewing on her lower lip.
“Yes. Seriously. If you want to hang out with him or have him hang out with us, let’s do it. If you decide you want to…do more with him, I think you should go for it. I want you to have fun, explore, and enjoy yourself.” I said bluntly.
More stunned silence from Madi as she processed what I said.
I paused and swallowed the lump in my throat, “And if nobody minds me being there I’d really like to at least be able to watch at least some of it.”
“Wha…..ok but why would you want to share me like that? You’d really want to watch me…I only want to belong to you baby. I’m so satisfied with our sex life already, really.” Madi said, unnecessarily trying to reassure me.
It was painfully obvious she was very interested in Troy’s proposition and trying to not appear too excited while navigating my reactions.
“It’s just sex, Madison. Just think about it. You’re always wanting new experiences….so here’s your chance to have casual sex with a hot, built, well hung black guy. No strings. That’s gotta check a couple of boxes right? I’ll follow your lead, babydoll. It’s not cheating if I’m into it. I mean, a basketball player? You’ve got to be curious. Didn’t he say it was 9 inches? I mean goddam.” I said as she just stared at me slack-jawed.
“You’re into it aren’t you…ok….so you’re into it….I mean, fuck, he is really hot…..but that’s so big” Madi laughed, “Like, physically, where would I put it? I’d at least make him wear a condom…well maybe, I don’t know….fuck…What are you, like 7 inches – and you feel huge!”
I burst into laughter – she had to know I was small. God bless her. “Maybe in ‘girl inches’. I’m honestly not even 6”, on a good day, rounding up, bone pressed. And you’re amazingly elastic, I’m sure you could find somewhere to put all that.”
Madi, clearly overwhelmed, flushed and breathless kissed me and said, “I want you to fuck me, right now, let’s get out of here.”
She was especially insatiable when we went back to our cabin. Madi moaned and cried out in pleasure, writhing and arching perfect naked body as she vigorously rode me. Troy had obviously gotten to her because she was soaking wet. As she bounced furiously in reverse-cowgirl, my small cock kept slipping out and breaking her rhythm.
She was obviously sexually frustrated and trying to pull moves that would only work on someone bigger than me. I was thinking about how good she’d look riding Troy like that when she used her finishing move on me – plunging down hard and swiveled her hips around like a pro, squeezing her pussy like a vice, forcing me to quickly cum inside her. As I lay there, spent and passing out for a late afternoon nap, I heard Madi in the shower with her vibrator.
We ordered room service for dinner and went to bed relatively early that night since we’d been drinking all day. Tomorrow was the excursion to a resort that had a topless beach, so we needed to rest up. Had to have the strength to drink in the sun all day again, and I had a feeling it was going to be a big day.
—————————————————————————
As luck would have it, Troy was on our shuttle to the resort that next morning. He was with his group of friends but split off and headed straight to Madi as soon as he saw her. He sat down next to her with me on her other side. I could see his friends were looking at us and talking. Probably placing bets. Fuck if I cared behind my dark sunglasses and big stupid tourist hat.
“Hiii, Troy.” Madi giggled shyly. Too fucking cute.
I may have looked and felt a little rough from several days of drinking in the sun, but Madi was fresh as a daisy. She was wearing tight cutoff jean shorts that showed the bottom 40% of her ass, thong bikini bottoms peeking out the back, and a small white ruffly top that’s coverage started right above her nipples and ended at just the right spot to flash underboob if she raised her arms up at all. Her long, smooth, toned abdomen was on on full display. Her warm blonde hair was pulled up tight in a bun under a large sun hat. Her slender, delicate neck looked irresistibly kissable.
“Hey, guys – you look incredible, Madi, wow….so my friends want to go to the spa at the resort. Sounds boring to me, so I was wondering if you guys were doing anything better.” Troy said as he slowly looked my girlfriend up and down. Madi was squeezing my hand tight.
“I’ve got to get this one to the topless side of the beach. You should hang out with us.” I said, trying to sound casual.
Madi giggled again and squeezed my hand harder. “Yeah, Troy, you should come with us.” She was getting bolder, I loved it.
It took 20 or so min to get to the island and the motor was loud so there wasn’t much conversation. I produced a flask full of rum from our beach bag and we passed it back and forth. Madi’s body language was telling. She kept nervously squeezing my hand and crossing and uncrossing her legs.
I leaned in close so she could hear me over the boat engine and said, “Relax, baby. I meant what I said last night. Have fun and get to know Troy a little better today. I’m not going anywhere, don’t worry about me. When we get to the beach I just want to nurse my hangover and read. You guys have fun.”
I was committed to getting these two together. This felt like a once in a lifetime opportunity and I didn’t even question it. It just felt natural and so hot, and I wanted her to feel as much pleasure as she could. And the way they looked at eachother – did I have a choice?
It was a quick shuttle ride and a bit of walk from the dock to the beach. I carried our bag while Madi and Troy walked behind me talking about school and music and sports and whatever stupid shit 20 year olds talk about when they’re trying to fuck.
The second we passed the threshold of the topless area, off it went. She tossed her shirt behind her and shimmied out of her shorts, kicking them off carelessly. Other than a thin strip up her ass and a postage stamp sized piece of cloth over her pussy, she was totally nude and in all her bouncy round assed perky tittied glory. I picked up her clothes and discarded flip flops as I followed loyally. Troy looked dumbstruck.
As Madi skipped off to claim three beach chairs close to the bar, Troy says, “Damn bro, you really know what you got there, don’t you. You seem to take real good care of her.”
“I do my best, but sometime I think she could go for more than I can give – in some areas at least. She’s an extraordinary girl with a really high sex drive, and I’m just one man. If you know what I mean.” I said, trying to make my approval as clear as possible. “I think she deserves to be…fulfilled.”
Troy patted me on the back, “You can say that again. I’m happy to be of service my friend. She’s fuckin perfection. I’m gonna take real good care of her for you, don’t worry about that. I’ve done this – the couple thing – a few times. I was kinda looking for it. My friends thinks I’m a freak, but it’s always the best pussy, you know? You seem like you know what you’re doing, but she seems kinda nervous.”
“My pleasure,” I chuckled. “We’ve never done this before, but I’m pretty sure she likes you. Have at her, she and I have already discussed everything.”
As soon as I got to the chairs with the bag and Madi’s clothes to permanently claim the spot, she flitted off into the calm blue warm waters. This time it was Troy that followed her like a puppy as I settled in. It wasn’t as crowded as I thought it would be, but there was still a lot of skin.
Madi and Troy were splashing and flirting and joking around in the shallows. I wanted to go out and join them, but I felt like it would have been weird. They were the ones to “looked like” they belonged together. Not gonna lie, I was loving it. It wasn’t long before they were putting their hands on each other.
At one point they were out in deeper water, Troy lifted Madi up in the air with ease, picking her up with his massive hands around her waist. She squealed with delight, and as he slowly lowered back down he pulled her close. They were bare chest to bare chest. She ran her finger nails tenderly across his strong shoulders and arms and I thought she was going to kiss him when she pushed off suddenly and splashed him in the face laughing.
After about an hour of this agonizing semi-nude flirtation, they came back to where I was kicked back sipping a Mai Tai. Madi had her hair slicked back out of her face and was breathing heavily – her tight slippery body shining wet, nipples rock hard. I could see how Troy was feeling by the creeping bulge in his already tight shorts. Jesus Christ the guy really did have a massive dick. I couldn’t tell if I felt more like a chaperone or a porn director.
“I want to work on my tan and drink…so…I’m going to um….go use the shower and get the ocean off me before I put some lotion on.” Madi said, pointing over to the row of enclosed beach showers hidden in the trees.
“Yeah, me too.” said Troy, looking like he wanted to bend Madi over right there in front of everyone.
I looked back and forth between the two of them. I don’t know if I’d ever seen two people more ready to fuck. “Ok” I said casually, “I’ll get you guys some drinks.”
I watched as they walked to the showers. It was semi-secluded in a shady area thick with palm trees. As they approached them they got closer and closer to each other. They stopped in front of two open separate stalls – then the magic happened. Madi grabbed Troy by the hand and pulled him into a stall with her. He shut the door behind them.
I almost came in my cargo shorts. I could only see their feet and the water running off of them – but they were obviously making out. There wasn’t an inch of space between them. She lifted one pretty little foot up like a princess. Then both her feet disappeared. I’m assuming he picked her up and she had her legs wrapped around him. It would have been really easy for him to do that and I could just picture her climbing him like a tree.
I tried to watch the situation best I could while I ordered the drinks and made small talk with a smoking hot milf with big gorgeous heavy swinging breasts as her fat old husband took a nap. Wouldn’t have minded going in that direction but I already had enough going on.
Getting back to my chair, I see Madi’s feet back on the ground pointed in the opposite direction Was he behind her? Jesus, how far was she going to go? I was briefly concerned they were going to get us kicked out, but nobody was paying attention.
As I came back with three mai tais. I noticed they were still in the shower together – except this time it looked like Madi was sitting on the bench and Troy was directly in front of her. She was definitely sucking his dick. His muscular calves were flexing and I could tell he was fucking her pretty little face. Goddamn, that escalated quickly. She did love giving head any time any place. “That’s my girl.” I thought.
After a really inappropriately long time, Troy emerged first and trotted over to me. I handed him his drink. He sucked down half of it in one slug and flopped down onto a towel covered beach lounger. He looked very content.
“I think she likes you.” I commented dryly. I couldn’t help but stare at his perfect body as he stretched and flexed in the sun getting comfortable. I would have totally understood if she let him inside her already.
Troy laughed, “Yeah man, she likes me. She’s fucking incredible, bro. Incredible. She’ll be out in a minute. She’s cleaning herself off.”
I got a mental image of my soaking wet little angel worshiping Troy’s massive cock in that public shower until he emptied his huge balls all over her face and tits, cum overflowing out of her mouth. “You should definitely come up to our room tonight after dinner. We’ve got a full suite with big bed. Let’s say 9:30. I’ll make sure she’s ready for you.” I said.
That’s when Madi came prowling over. She bent down and kissed me deeply – it tasted musky and salty. She leaned in and whispered in my ear, “Oh my god baby, he’s so hot……I love you so much…we weren’t able to fuck but I really really want it tried but he’s so…”
I cut her off, “I’ve already invited him up to our cabin tonight. Maybe you can put on a show for me.” and passed her a drink.
There wasn’t a lot of conversation for the next few remaining hours as we all relaxed in the sun. Madi held my hand most of the time. Troy “helped” her put on sunscreen. When got back to the ferry to the ship, Madi and Troy had a tense stare at each other to say goodbye before he returned to his friends.
Source: reddit.com/r/eroticliterature/comments/t2qn4w/a_genxgenz_love_story_part_one_cuckold_on_a_cruise