A GenX/GenZ Love Story: Part Two – Front Row Seat [cuckolding]

Madi was ready to fuck the second we got to our cabin. It took a lot of inner strength, but I denied her. She was pissed, but then I explained she should save it for Troy and keep her pussy clean and ready. She accepted calling me a “wonderful amazing pervert”, and admitted that she’d rather wait for her new stud.

But I did get a hot sloppy blow job. She thanked me for being the best boyfriend ever and taking such good care of her. She said she loved me and that I was amazing because I let her “be herself”. She said she’d do anything to turn me on and make me happy and she wanted to be my perfect little slut.

When I asked her about her shower with Troy, she squeezed my cock hard and stared me in the eye. She licked and kissed and slurped on my stiff little prick as she told me all about it.

“I wanted to fuck him so bad baby…we tried…I bent over for him…but he couldn’t get it in… I was so fucking wet for him but there was no time…and I didn’t want to make noise….but I still wanted to make him cum….he was so cute and so hard….oh god baby fuck it’s soooo big…so thick….he wasn’t lying…..he said when we have time and lube he’s going to make me squirt….I want to know what it feels like baby….fuck what does that even feel like…I want to cum on his big fucking cock….I bet he can make it happen…”, she went on and on as she attended to me.

I was close and she could tell. “He came so much…” she continued. “I tried to swallow it all but I couldn’t…he tasted so good…he grabbed me by the throat….and shot the rest all over my face…I begged him for it…I swallowed as much as I could…did you taste him when I kissed you…”

I erupted in her sweet little slut mouth as she throated my cock and swallowed every last drop with ease. The bar had already been raised. My dick and my loads were nothing for her to take in her throat already. “What’s going to happen when she actually fucks him?” I thought.

Not once before the time came did Madi show any signs of hesitation or cold feet. Maybe it’s the younger generation, but her attitude towards all of this seemed extraordinarily receptive. It’s like she was a natural born hotwife. Once she accepted that I was all in, she did nothing to hide her enthusiasm. She was ready to cuck the living shit out of me. All my ex-wife ever did with knowledge of my kink was call me “gross”, and then cheat on me anyway. God, what an asshole. Upgrades.

I watched as she bounced around the room to her music butt naked and drinking straight rum. She kept saying, “Oh my God I’m so excited this is fucking crazy” and “baby I love you so much thank you for everything you’re so amazing” and “I can’t wait to show you how well I’m going to fuck Troy” and “Are we seriously doing this” and “when you see his cock holy shit you’re going to die” and “I’m seriously just going to attack him the second he gets here.”

I basically just handed Madi a Victoria’s Secret credit card and told her to get whatever she wanted a few months ago so she had a whole suitcase full of lace and straps and satin. She let me choose her outfit.

“What do you think he’ll like?” She asked me excitedly.

I assured her if she was in sweatpants with no makeup on when he showed up he’d still be impressed.

The set I picked out was white, lacy and minimal. The bra only covered the bottom half of her perky little breasts, pushing them up and together. The matching panties were hardly panties at all – they were a crotchless thong that had a tiny pink bow right above the entrance to her soft smooth mound. I slid thigh-length white stocking up her smooth toned legs. She moaned softly as my fingers grazed her exposed pussy to feel how wet she was. The girl was dripping.

She’d been rubbing lotion all over her warm tanned body all evening and had put on just enough makeup to make her pink lips and green eyes pop. She smelled intoxicating, felt like the softest thing in the universe and looked like a goddess. She was totally ready to get properly fucked by a real alpha bull stud.

Madi had herself covered in a short length, satin leopard print robe and was pacing around like a cat in heat when we heard a soft knock on the door at exactly 9:30. I was sitting in the swiveling office chair with a tall glass of dark rum, and I poured one for our guest.

Madi ran to the door and flung it open. She was immediately all over Troy, sucking on his lips and tongue, unbuttoning his shirt and clawing at his chest before the door closed behind them. Getting right to it.

“Fuck, I’m so wet for you, get in here.” Madi moaned into Troy’s mouth between kisses.

She slipped off the robe, dropping it to the floor revealing herself to him, eliciting a very sincere, “god DAMN!”

Madi grabbed a couple of Troys’s big thick fingers and led him to the small loveseat, pushing him down onto it. She stood between his legs and he kissed her tummy softly, caressing and squeezing her perfect ass as she stroked his head.

Madi dropped to her knees, and Troy pulled his shirt off, leaning back comfortably.

As Madi kissed her way down his smooth rock hard abs, I rattled the ice in the drink I poured for our guest, and was noticed by him for the first time. Not that I blame him.

“Thanks bro…you’re the fuckin best.” Troy said cooly, sipping his rum as my girl unbuckled his belt and unbuttoned his jeans. “You stickin around for this?” He asked.

“Yeah, if you don’t mind. She’s all yours though.”I said, watching with anticipation as Madi gripped his jeans and boxers.

As she slowly pulled them down, the thick shaft of his cock was revealed. She kissed it inch by inch as it appeared. Every time I thought it was done there was more dick. She finally got past the head and the whole beast came springing out, semi-hard and pulsing, lurching upwards as it continued to grow from Madi’s attention.

Troy had an actual, prize winning, 9 inch long, beer bottle thick, 99th percentile rare dick. Thickest in the shaft, slight downward curve, and a very large smooth tapered head. I could see why they weren’t able to make it work on the shower. Paired with large egg sized balls hanging low in a neatly shaved scrotum, this man’s magnificent genitals had their own presence in the room. Built for breeding. I was humbled. Humbled and horny. Madi looked like she was in love.

Madi grunted with satisfaction as she wrapped one hand around his veiny shaft, fingertips far from touching, and lightly caressed his balls with the tips of her dainty fingernails with the other hand, placing wet kisses and drooling on his head.

I tried to do the dick-math and figured if you stuck two of my dicks side by side with one underneath them, it might almost be as big at Troy’s magnificent endowment and half as long. There would be no turning back for Madi after this.

“Holy shit.” I said under my breath, but it was apparently loud enough for them to hear me.

“I told you it was crazy big.” Madi said, before opening her mouth wide and taking in his large, dark, glistening head.

She wasted no time putting in work, slurping as much of his length into her mouth and throat as she could, holding it there and gagging before slowly backing off. She worked the saliva slicked shaft with both hands as she sucked on his enormous head.

“Don’t worry, bro. I’ll be gentle and get her back to you in one piece. She’s going to love it, you’ll see.” Troy said polishing off his drink and passing me the empty glass.

Madi chuckled mischievously with a mouth full of dick. Troy was rock hard an could see his pulses. His engorged oozing head popped out of her mouth. His cock bobbed up and down, the weight of it struggling against gravity. I could almost feel the heat from it.

Saliva and precum trailed from Troy’s cock to Madi’s lips and she said, “You don’t have to be gentle with me…maybe just at first.”

Troy stood up and Madi sat back on her feet. He towered over her and firmly pulled her by the back of her head into his enormous ball sack, draping his wet throbbing cock across her face. Madi closed her eyes and moaned intoxicatedly as she continued to worship her new lover, her tongue exploring his balls and taint while stroking his shaft.

After a bit of rubbing his dick all over Madi’s sweet little face while calling her his “pretty little white slut” and such, which she gleefully indulged while vigorously rubbing her clit, Troy declared, “I need to taste that pussy.”

Troy helped Madi to her feet before scooping her up in his arms. She squealed with delight and kicked her feet excitedly as they exchanged wet, tongue sucking kisses. She stroked his face tenderly as he slowly lay her down on the bed. His heavy dick slowly wagged back and forth, a pearl of precum slowly dripped onto the carpet below.

As he laid her down gently, Madi reached back and unhooked her bra. Troy was hovering over her, kissing her neck tenderly and running his big, dark hands all over her slender, creamy, writhing body with his beautiful dick resting on her flat tummy. She looked over at me in the chair and I saw how watery eyed, rosy cheeked and plump-lipped she already was. Her chest was flushed, and her pussy was visibly glistening – her delicate inner labia swollen and blossoming, were peeking out – I’d truly never seen her look more beautiful.

She flung the bra at me and giggled, “Are you enjoying this baby? Is this what you wanted to see?” she asked breathily.

I snapped out of my trance. “Yeah this exactly what I wanted to see.” I slammed two fingers of rum and poured another.

I’d just been watching silently with a rock hard erection straining in my shorts. I didn’t want to do anything but focus on burning this memory into my brain – not even touch myself. I didn’t know if I’d ever get a front row seat for something like this again.

Troy pull her to the end of the bed and got down on his knees between Madi’s legs. “Jesus Christ look at that tight little pink pussy SHIT!” He said as he finally got face in the holiest holy.

Troy asked me if I had any lube and I silently passed it to him. Madi grabbed her thighs and spread herself open for him. As he skillfully teased her clit with his tongue, he lubed up his thick fingers and slid one then a second into her tight slippery little hole.

Madi was going nuts, bucking, clawing at his head and moaning as he kept at it until she came. And she came hard – I thought she was going to give him a black eye with her pussy. When she stopped convulsing, Troy slid his fingers out of her body and I realized that those two fingers were longer and wider than my dick.

Madi writhed and ran her hands down her own body stopping to feel her own pussy – you could hear how wet she was.

“Oh fuck…Troy…I’m ready…I want you inside me…I’m ready…please baby…give it to me….”, Madi whimpered as she writhed, rubbing her clit.

Putting on a fuckin show, indeed. I’d never seen her this worked up, and I don’t think it was an act. And this was just the warm up.

Troy stood up between her legs and rested his wide slab of a dick on Madi’s stomach, covering her navel, and handed her the lube before placing her ankles up on his shoulders.

Now, when she use lube with me – it’s a little squirt on the head, rubs it around with two fingers and a thumb, good to go. I was again struck by the qualitative difference between me and Troy as she drizzled lube up and down his cock like she was putting mustard on a foot long hot dog, then stroked it with both full hands. Talk about being in another league.

As Madi got him all greased up and ready to go, Troy sensually rolled the silk stocking off of her legs, kissing her toned calves and pretty little toes as they were exposed. He kept the crotch less panties on.

I was watching all of this from the side of the bed. I felt like I was lucky enough to witness something beautiful, natural, and hot as fuck. As with with the whole process so far, I felt like I didn’t want to react too much to anything as to allow things to proceed organically. I really tried to not be intrusive on their moment. That being said, you bet your ass I stood up and got a good view for first insertion.

I was surprised Madi noticed me as I approached slowly. She gazed up at me lovingly.

“Oh my god, baby. This is fucking amazing, you’re so good to me. I’m actually going to fuck him…I love you so much.” She said emotionally.

“I love you too, baby.” I said as I moved strands of hair off of her sweet little face, kissing her tenderly.

I was looking into her eyes and her face suddenly changed. Troy had spread her thighs wide again and was rubbing his shaft up and down her audibly wet slit. Her focus returned to her new lover, as she started swiveling her hips in rhythm with his gliding strokes, rubbing her own body and pulling lightly on her nipples.

“You’re about to fall in love with this dick.” Troy said as he pulled back and spread her lips open with one hand.

He lined his turgid, throbbing, black home-wrecker right at the entrance of her sweet, achingly tight little hole. It looked like it would never fit but I knew it would. I held my breath.

Madi propped herself up on her elbows – I guess she wanted to watch too – she squirmed and made little whimpering noises as she stroked his stomach, tracing his definition with her fingernails.

Troy applied firm, controlled pressure until her delicate membranes stretched to accommodate his broad, thick head. Troy gave a push and with a pop he was inside her. Her thin pink tube sealed around his dark shaft right below the crown.

Madi gasped and cried out “aaaaaahhhh fuck!” – it sounded like she was in pain. I was almost worried until I remembered something she always said: “Ouch doesn’t mean stop.” As I recalled that, she reached down and spread her lips for him and stroking his shaft. It was obvious she was dying to have him inside her. Troy leaned down and they kissed, again sucking obscenely on each others tongues and lips as she grew accustomed to having him inside her.

Troy drizzled more lube directly onto their interlocked genitals, flexing his cock and pulsing his head inside Madi’s tight little seal. Madi moaned every time he did it.

Troy began gently circling her hot pink clit with his thumb patiently and slowly working himself in and out of her pussy, gradually getting deeper with every skilled stroke until he couldn’t go further without making her wince. A little more than halfway in, and deeper already than I’d ever been inside her, stretched beyond anatomical reason.

Troy reached down and stroked my sweet little angel’s pretty little blushing face and asked, “Is this good, baby? Right there?”

She responded by grabbing his hand, staring him dead in the eye, and sucking on his fingers. She was writhing and breathing sharply, her toes were wiggling, she rubbed her tummy over where he was buried inside her. Moaning, she pulled herself another inch down his length. She’s no stranger to working through a physical challenge.

Troy started fucking Madi faster, using the high-water mark her cream left on his dick to make sure he didn’t go too deep. She was stretched so tight around his girth it looked like he was going to pull her inside out.

She wasn’t yet taking all of him and Madi was already in another world. Mouth agape, eyes rolled back in her head, making barely inaudible squeaking noises, no longer holding herself open as her hands flailed useless at her sides.

My girl groaned low, deep and primal. She never made noises like that with me before. So this is what she sounds like when she’s REALLY enjoying herself. Troy was most certainly obliterating her g-spot. I can’t imagine what it was like for her, having that much pressure inside her body for the first time. She was getting even wetter by the sound of it and Troy was slowly pushing himself deeper.

They must have crossed a threshold together because with one easy push, he went well past the prior maximum depth and buried himself to the hilt – his short trimmed dark bush tickling her smooth now enflamed pink mound.

“Ooooooohhhhhh my gaaaaaaaawwwwwddd wow shit wow oh my GOD holy shit…” Madi moaned and cried, eyes wide in genuine shock as Troy slid into this new, previously unexplored depth. This was definitely a new physical sensation for her, and I could immediately tell it was one she was going to seek out for the rest of her life.

She later told me that when she first felt him slide in that deepest, virgin spot, it was a life changing moment. That she finally knew what her body could do sexually, and how truly amazing she could feel. That explains why the look on her face was of someone who just saw God, or someone that now understands why big dick is so in demand. Troy held himself there caressing her tense, glistening body, flexing his cock deep inside her womb, slowly moving an inch or so in and out.

“You loving it yet, baby girl?” He asked, bending down, kissing and sucking on her long slender neck.

“Yes I love it…god damn you and your big fucking dick….fuuuccck….I love it…fuck you Troy….I loooooove your big fucking dick….fuck me Troy fuck me baby…oh god fuck me..” she groaned as she writhed, impaled and powerless. Her chest now flushed crimson, nipples erect, legs in the air. With that admission, Troy began taking long, gliding

10 strokes. It took Troy 10 fucking strokes at full penetration to give Madi her first deep, explosive, squirting, vaginal orgasm. I knew she had it in her. I was actually proud of her.

“OHHHH FUUUUUUUCCCCCK!!!” Madi wailed as her abs tensed up, pussy visibly contracting, gushed for the first time in her life all over Troy’s cock.

Troy was smiling proudly holding himself deep inside her watching her recover, “Good girl…there you go….”

Madi looked over at me, barely able to focus and moaned, “Oh my god did you see that baby! Holy fucking god that was amaz…ing….oooh fuuuck….”

Troy had begun smoothly pistoning again, picking up his pace. She was quickly reduced to a limp, whimpering doll as he grabbed her firmly by the waist, stood up to his full height lifting her lower half off the bed, fucking with a steady rhythm. After a few minutes, Madi was back to her senses, broken in and bucking in time, fucking him back. It wasn’t long before she was soaking the bed below again. She went limp and fell back with her eyes closed, tears rolling down her rosy cheeks, gasping like she just ran a 5k.

Troy picked her up, not tenderly this time but like a toy, and spun her around, tossing her face down on the bed facing towards me. Madi stretched like a cat, reaching her pretty little French tips out towards me as she instinctively put her back into a deep arch, popping out her ass and getting positioned on her knees. What a fuckin pro. I reached out and held one of her hands. She squeezed me tight as she settled into position, giving Troy the most amazing view on Earth.

I stared into her big, green, watery eyes as Troy positioned himself behind her – strong thighs holding himself low behind his tiny mount. He added more lube to his cock. He stroked himself achingly hard and when he saw me watching him he slapped his cock, making it rigidly spring back and forth.

He again slid his thick shaft up and down Madi’s pulsing hot slit, taking a moment to rub and spank on her firm round ass. I lost her again as her eyes rolled back when Troy slid his full length into her in one smooth motion. She was paralyzed again, mouth open and holding her breath, with him deep inside her.

Troy leaned forward arching over her tiny frame, gently brushing the hair out of her face. “You’re gonna fuckin get it now.” He growled.

Soon he had Madi’s long golden lockes wrapped around his fist, and his huge dick firmly locked deep inside her, grinding hard. Her mouth was slightly open and she was moaning low and soft, slowly gyrating her hips. I could tell she was squeezing him. She looked drunk and he looked like she was pulling him into the phantom zone with her pussy. Watching Madi paired with someone on her level of physicality, endurance, and sexual potency was truly a sight to behold.

“Goddamn…goddaaaam….shit is so fuckin tight…fuck….” Troy growled as he flexed and pulled her head back by her hair, giving her ass a smack, and she obeyed, pushing herself back into his thrusts.

Soon he was slamming himself into her, grunting and cursing to himself, the sound of wetness and tight young bodies smacking together filling the room interrupted by Madi’s wild screams and deep moans of pleasure as she bucked back in a frenzy.

I thought about how she tries to ride me hard with long strokes and I always slip out and noted the look on her face: pure joy. This is what she’s needed. This is what she’s going to continue to need.

Troy was a pro, but Madi quickly had him close to cumming. He was breathing hard and hissing through his teeth, abs tightly constricted, heavy balls pulling up towards his body. He was slapping her ass leaving big red hand prints all over her and she was squealing with delight with every smack.

“Oh fuck….I’m gonna bust soon….gonna cum…shit so good…” Troy strained, trying to hold on as she fucked him back relentlessly. She was trying to make him cum.

“Don’t stop don’t stop I’m so close I’m gonna come again don’t stop don’t stop…” Madi was chanting.

“Where do you want it?” Troy asked, like a gentleman.

“Inside me….inside me…just don’t stop fucking me….fill me up….Troy baby do it…just do it…I need it I need to feel it…oh god please daddy give it to me…fill up my little white pussy daddy oh please…” Madi gasped and squealed.

Fucking, “Daddy”? That was new.

That was all the coaxing and permission Troy needed. He yanked Madi’s hair, pulling her back towards him, grabbing her by her slender throat, and pulled her backwards towards him, bringing her back to his chest. Madi dropped my hand and reached back behind her grabbing Troy by his head, securing herself as Troy wrapped his other muscular arm around her torso.

They were both groaning and wailing, mouths and tongues finding each other as Troy absolutely dominated her from behind. He was truly massive compared to her. From this new angle I could see him sliding in and out of her, her lower lips gripping firmly, his heavy balls swinging forward slapping her swollen clit as their juices dripped onto the already completely soaked sheets below.

Every muscle in both their sweat slicked, well defined bodies tensed up and Troy held his breath for a moment – then he roared and squeezed Madi tight making her gasp and squeak. I watched in awe as his balls contracted and thick shaft pulsed probably a dozen times. Madi appeared to react to each pulse, breathing sharply each time before going limp in Troy’s arms around pulse 8 or 9. She came hard and her pussy gushed again, this time as he filled her sweet little pussy up with his seed.

They both collapsed. Somewhere in there I came in my pants – probably when she begged him to cum inside her. I got them both a clean towel and a bottle of water, and a shot of rum.

I knew my girl, she wasn’t done yet. I got down on my knees and I held her pretty little face in my hands. “How you doin baby?” I asked, kissing her on the forehead.

Madi laughed and sighed, “oh fuck….I’m great…shit…I came so hard oh my god…..I didn’t think I could…so good oh my god….did…did you see that?!?” she burried her face into the bed embarrassed and screamed “oh my god I made such a mess….there’s so much cum…WHAT THE FUCK TROY!”

“I’m good too!” cried Troy triumphantly as he hopped up and chugged his bottle of water. His cock was still 80% hard and he was stroking himself gazing at Madi hungrily. “I told you I’d make you squirt.”

I chuckled. “I’m going to change my pants, and go out to the casino for a few hours. You guys keep at it as long as you want.”

“Really? You’re leaving now? Are you sure?” Madi asked breathlessly, looking pouty and confused.

“Yes, I’m sure. I want you to enjoy yourself – enjoy Troy, just you and him. You’ve only got him for so long. Trust me, I enjoy the thought of you fucking him all night. You might be more comfortable doing or saying some things with me not here, you know shit like that. Be nasty. Go wild. It’s part of this for me.” I explained.

At that, Madi wordlessly rolled over and crawled towards Troy, and began cleaning the cum and cream off his dick with her mouth. I could see that her tiny little pussy was a bright red, swollen, slightly gaping, dripping mess, and she was already rubbing it vigorously as she sucked and licked him clean. My angel was just getting started.

By the time I came out of the bathroom cleaned up and ready to fly solo on the ship all night, Troy was laid back on a pile of pillows with his arms behind his head and legs splayed out, watching intently as Madi, face down in the opposite direction, slid herself smoothly up and down the full length of his cock. Dick so big she could fuck it from the other side of the bed.

I kneeled down in front of her and kissed her deeply as she continued to methodically stroke Troy’s length with her pussy. She tasted like rum, sweat and dick. She just looked at me in a dick drunk haze and mustered a weak “love you” before Troy started thrusting up into her and I lost her again.

“I got this man.” Troy growled.

Madi’s completely soaked panties were now on the floor. I took them with me, leaving silently. I could hear their passionate noises far down the hall as I walked to the elevator. I’m sure the whole deck heard her.

I actually had a great time wandering the ship alone that night. I lost $400 at the casino. I had several women, two couples, and one man approach me flirtatiously. It was really validating.

I think had I come alone I’d have done alright for myself. Yet I was wholly satisfied knowing my perfect angel was getting her perfect tight little pussy wrecked by a young stud in the room I paid for. I guess it never occurred to me that it would have been “fair” for me to get laid too. I was content. I fell asleep after god knows how much tequila on the highest deck of the ship I could find with chairs, staring at the stars. It was strange – I was the most sexually satisfied I’d been possibly ever and I didn’t even get laid.

Source: reddit.com/r/eroticliterature/comments/t40ohx/a_genxgenz_love_story_part_two_front_row_seat