HillBilly Cuckold: Back to Orlando Part 2

I know this has been a while. I wrote this out long ago, and decided to now finish...hopefully.

Where were we. My wife had just fucked around with her older ‘boyfriend’ and sugar-daddy Jarrod. We’re back in Orlando for a two week vacation at our time-share resort.
The reality was though, we weren’t REALLY there for Jarrod. He was just in the right place at the right time. We were there for her other Florida lover…that young bald tattooed punk kid (not really…he was twenty two but I’ll say kid compared to me).

She didn’t want to do “two boyfriends” in one trip. We use that term since its better than ‘suitor’ or ‘lover’ or ‘bull’. That shits kind of dumb to us. This was supposed to be the ‘punk kid’s’ birthday present….my wife.
If you forget, the punk was a guy who shaves his head, sort of really skinny but fit, about my height and has tattoos on his legs and arms. I think I used the term hillbilly or redneck in the other update, but its just a typical Florida guy. We found out in the year since we last visited that the dude was YOUNG. I mean Hillary met him on his twenty-first birthday.

I recall that day well. It was the afternoon, Hillary was in that black floral romper with her wedge heels. It was the year prior almost to the week. Bill was still with us but largely oblivious to the world around him. We were at The Hole in the Wall in the back alley behind Raglans pub at Disney Springs.
Note: This is our watering hole. Hillary loves the Bailey’s Shake with a shot of either rum or vodka. It’s a mix of Ice Cream, Coffee Liqueur and Bailey’s…duh. She’ll drink three in the sun and be wrecked. So if you’re in Disney Springs between September and December before sunset, stop by the back alley bar “Hole in the Wall” between Raglans and Cookes of Dublin. And if you see a loud, confident round assed pretty young girl with big tits in a sexy floral black romper/sundress and wedge heels who looks like she’ll ride you silly….buy her a drink and she just might.

There were two rednecks ogling my wife at the bar. ***** off their asses. My wife was seated away from them and acting like she didn’t notice. When Bill got up to piss, she turned to them, crossed her legs in that romper towards them and gave them a good shot of her legs and cleavage. And despite being Bill’s ‘girlfriend’ she was checking the bald guy out. Looking at him up from her phone. A lot.

He knew it too. I’d learn over a year of Hillary talking to him via Facebook that the day he saw her, he saw the most beautiful girl he’d ever seen. He told Hillary he could tell her friends (aka me and Bill) were losers. The thing was, he must have missed PDA between Bill and Hillary. I am pretty sure Bill had an arm LOCKED around her.
If you’re wondering why my hometown former high-school associates and these people DO NOT know I’m married to Hillary (and this redneck does not, but Jarrod does), it’s because I don’t have social media. At all. She does. Not me.

Hillary and this redneck (just a Florida resident…sorry) have continuous conversations about that first meeting. Just like Jarrod, Bill, the ‘hot teacher’ and well…ME, we all have that first time we met my wife story.

In looking at the conversations, which Hillary likes to show me, she admitted to ‘eye-fucking the shit’ out of him that first meeting at Raglans in 2019. He isn’t her type, since he’s rather skinny, but she does like tattoos. Plus he is young, which she doesn’t like.
It was the Punk who told his buddy they needed to go back to Raglans for the next few days, because he was certain that the ‘smokeshow’ would show up again. Sure enough, Hillary, me and Bill went back the next day (I think) around lunch after a park. That’s when she was in her biker shorts and the crop top gray shirt she ties on hot days. When she walked in the young Punk held the gate and they stared at each other. This, I saw up close, even if Bill didn’t. Hillary smiled and whipped her hair back like a school girl on a crush.

And the day after Bill left Orlando in 2019, and Hill and I stayed, I remember Hillary being OBSESSED with going back to Raglans around the same time we saw those ***** guys the previous times. I think we went to Universal the night after Bill left, and she sucked Jarrod’s cock. The next night we went BACK to Raglans, less than forty eight hours after seeing the rednecks.

Hillary put on the SAME romper she wore that first meeting. She did her hair and makeup and seemed on a mission. I told her they probably wouldn’t be there, but my wife insisted on going back, certain that young punk would come back.

“Did you see the way he looked at me,” she told me getting ready. “He wants to fuck me so bad it hurts. I bet he’s been KILLING his dick at night thinking of me.” She said he looked at her like he was starving and she was a piece of steak. “I bet that kid didn’t even fuck that fatty, because,” Hillary pointed to her body in the romper. “After seeing me WHY would he want to.”

You know what? She was one hundred percent correct. First, she knew he was young (again 21). That punk told Hillary that he became obsessed with going back there. He even said he didn’t fuck the fatty, and just got a blowjob imaging my wife between his legs. He was so confident he’d bang my wife, he kept telling his friends he was going to fuck ‘the hot girl in the dress’ on his birthday. Yes, we were there in 2019 when he TURNED 21. How he got into the bar before that is anyone’s guess.

We went to Raglans (in 2019) the day AFTER his birthday. I recall my wife sitting at the end of that small four seat bar, and she made me sit to her left, where there wasn’t really space. An open seat was next to her as she sat on the corner of the bar. The bar cut right to the wall after my wife and I sat on the side perpendicular to my wife. She kept looking at the alley area. She seemed SO nervous, and I guess a cuckoldress has her own weird gut feelings. Hillary was already ***** too. So when we saw those ***** young punks, I don’t think I’d ever seen her so nervous.
Sure as shit, the guy sat RIGHT next to my wife. He admitted to seeing her in the dress and getting a boner and his hopes right the fuck up. She’d done that for him, and he knew it. Before even talking she turned her body language all the way to him, legs crossed towards him, bobbing heels, stolen glances and her entire body turned to him. Her knees pretty close to his.

And he looked at my wife’s ice cream drink. “What’s that?” he asked. And if you're taking notes on scoring with my wife, this is what you do.

“It’s a Bailey’s Shake,” my wife added. “Wanna try?” She asked him and held out the drink with her straw towards him. He didn’t waste a minute sucking on the straw my wife used, which was subtly intimacy between strangers.

“That’s good,” he said and ordered one. “And one more for her,” he added (again….smooth). His buddy insulted him, but my wife defended her new friend. She introduced me, and he introduced his buddy, but neither of us really talked. Hillary and the young Punk began to chat, the usual “where you from” and “What do you do” and so on and so forth. He began taking my wife’s round of drinks. She can only drink so much ice-cream shit. So she did White Claws and tequila shots with him.
I remember getting phased out of the conversation with my wife, and so did his buddy. His fatter buddy was staring at my wife’s thighs and legs in the romper, and so was I. Beta males relegated to gawking while the alpha courted the female. And court they did. My wife laughed at the stupidest jokes. She has this way of morphing into whatever a guy wants; for Jarrod a conniving side-girlfriend, for Bill a confident cuckoldress, for the teacher a seductive student, and for this guy…a ditz.

The guy mentioned something about Ripley’s museum being around here and cheap, weird and fun. “Oh my god I’ve heard of that,” my wife said sipping a drink. “But like, where is it? Like I don’t know this area.” The amount of ‘likes’ was not um…like my wife.

There were sports on and they chatted about Orlando Magic games and my wife remarked, “Oh my god, I don’t know ANYTHING about sports.” Which is weird, because she does. I was kind of getting turned on by this new unique metamorphosis into a ditzy girl.

I have to admit, the ***** fool was smooth (take notes from this guy if you find yourself at Raglan’s and you think you’re talking to my wife), he touched her necklace getting close asking about it, and put his arm on her chair, getting closer. They began whispering and my wife was laughing. Suddenly, he asked her something and waited. She nodded and then he leaned in and kissed her lips. Nothing intense but quick and full. It was highly erotic for me. They continued close talking and he slipped another kiss which she allowed, more tongue.

The drinks flowed. I went piss and came back and my wife and the young punk were sucking face. Raglan’s is NOT that place. We were all pretty banged up at that point. We kind of did a crawl down Disney Springs towards the UBER area. Our new friend was intimately close with my wife now.

And yes, as I said I was sort of the butt of the jokes. How I’d been SUPER friendzoned by this smoking hot girl. We went back to our suite at the resort, all four of us. Hillary was helping them diss me now. She said she wasn’t sure ‘when I’d been laid last” and sometimes she throws me a bone by leaving used panties out.

We all smoked a joint on the deck with the mesh windows to keep the bugs out. Hillary sat in the young punks lap. They kissed and smoked, and Hillary showed the punk Bill’s ‘kissing shotgun’ move. She got up to use the bathroom (I think) and then he got up and followed.

I remember his friend stopping me with his hand when I stood up and shaking his head. “Wait for it!” The fatter punk told me.
Sure as shit, a few minutes later I heard my wife start moaning “OH FUCK! OH MY FUCKING GOD! OH FUCK!” Over and over as the bed creaked loudly.

In that bedroom he pretty much threw my wife on the bed and moved the romper bottoms covering her pussy to the side and slid his cock in. She said he’s HUGE. She was cumming quick and he had the stamina to stop after she came a few times. She then bent over for him, romper still on and he moved the cape piece to the side and fucked her from behind. She was shouting “OH FUCK!” The entire time. She ended up on top next. Finally he had her down, with those wedge heels up by her head, romper STILL on.

She said it felt like they fucked for hours, but it was like ten to fifteen minutes. She came a BUNCH of times and they finished together and kissed. She said she thinks she made noises like a pig when he plunged his whole cock up in her to cum.

I just remember the sounds and then that look on her face when she came out. She had on jeans at that point. She looked….well fucked. That glow, tossed hair and a dazed smile, almost hanging on the young punk. He left after a big kiss.

By the way, he made the claim he was born at 1145PM on his birthday, so he TECHNICALLY banged my wife on his birthday. Within that 24 hour span.

And they had sex a few times that trip.
Now it was 2020 and the world was different. We weren’t sure if going to the parks was something we really wanted to do. But we started at Disney Springs that first night. Why, because it was that young punks birthday. Now, he hadn’t seen my wife in a year. But she promised him pussy on his birthday, and she promised that romper.

So after Jarrod’s ‘attack’ Hillary did her hair (lighter this year than last years dark hair) and makeup, heavy eyebrows, red lips, looking wonderful. She’d fucked Jarrod earlier that day, but the young punk didn’t need to know that. She put on the romper and her wedge heels completing the same look from the year before. Her ‘Diva’ look. Her confidence was evident from the start, and we got ***** at the hotel bar near our suite (not the pool area) and then took a cab to Disney Springs. Hillary and I did another bar crawl, and notice that Florida really didn’t care about COVID. Sorry…it was like the Wild West down there.

She was building confidence drinking in all the looks from men, walking in those heels with her head high.

And if you’re wondering, YES, her ass hurt like hell. But we got wasted. As per usual.

We made our way to Raglans expecting like other places no stools at the bar. Except when we got there, the stools were sort of at the bar, sort of not, kind of like a table AGAINST the bar almost. It was weird. We sat at a table. When I sat next to my wife at the corner, she laughed. “FUCK NO!” She pointed across from her where two seats were. “Hon,” she looked at me. “If you get laid on this trip…consider yourself lucky.” Her stance that I wasn’t getting laid was new. I thought I was having a lot of sex. I liked the teasing though.

She had that same eagerness as she watched the alley checking her phone. I swear, when my wife saw the young punk and two of his friends she got up and sprinted out the little walkway/gate and hugged him. Then, she kissed him, and they were off to the races with the ‘ice broken’ so to speak. And oh man, did they kiss. Long, tongue filled, head moving kissing, with the dude’s hands on her back and then to her firm ass. They must have kissed for several minutes at least. Even his buddies, the fat one from the previous time and a new short guy who had the same vibe as Hillary’s young punk. He came over and sat with her. She handed him his gift bag. Inside was whiskey, a trucker hat ome cigars, and some suggestive lingerie with a bottle of whipped cream. Alcoholic whipped cream.

When the confused young dude asked. “What’s the whipped cream for?”

My wife laughed, as even I was confused. She laughed and said “Your birthday pie!”I was confused. I hadn’t even seen her buys these gifts, other than about $300 worth of cigars (my money) at the Disney cigar place. She held the metal bottle up and shrugged at a bunch of confused guys. “I put this on my shit and you put it on yours.” She could still sense the confusion. My wife, ever the brazen and open sexual woman grabbed the young studs dick. “I’m gonna put this on your dick and suck your cock.” She said and then pointed between her legs. “You’re gonna eat it out of my pussy.”

This made the gang of young punks laugh and cat call. The punk laughed “Told you guys she’s amazing.” He then looked at her, and I was shocked when my wife spoke at the same time. “Bailey’s shake?” They both said and they then laughed.

“FUCK YEAH…let’s go.” My wife said and the two walked over to the standing portion of the bar. You could hang out there and people didn’t bother you. I watched her and him get one of those shakes and two shots. Hillary began asking him questons as if they were old friends. They had been talking via social media for a year I guess. “Are you still dating what’s her name?” She was referring to the girl we saw them with last time. Sort of a meth-head version of Hillary herself, but much much fatter. When the guy nodded, Hillary sighed. “You got to get a better girlfriend.” She shook her head.

The young punk insisted Hillary move down and date him.

My wife shot the idea down. “I don’t have a reason to move down hon.” She then reached for his crotch. “It sucks having a guy with such a nice cock, but he lives too far away.” She kissed him. “I hate being single.” This along with the kissing was intoxicating to me. She openly pronounced that down here, she wasn’t married, wasn’t dating and was just a hot girl looking to get fucked.

It was rather awkward getting to know the two dudes. They asked how I knew her, and I had the canned and planned response. She was a friend I met through another friend, and she dated one of my other friends. We tried talking sports, but these young punks didn’t want to talk with me, maybe sensing I was WAY older. They let me in on the idea that none of their friends believed Hillary existed and only saw pictures. But now, here she was in all her sexpot glory in that same romper.

I heard her remark that she ‘wore it for him so he’d remember her’. As if he’d forget. The two stayed on their own for two rounds and two shots. Then they came back, my wife wrecked and he was *****. They bought another round of shots (he did…again…smooth) and paid their tab. Hillary was introduced to the others FINALLY. But suddenly, the others took off. It was just me, my wife and the punk. I ordered a flight of the beers they had and ordered the punk one. But it was as if my wife and he waited for me to get my drinks.

“I think we’re gonna take off,” my wife said standing up.

The guy paid for my tab, which was nice. The pair then left me. I got my sixty dollar tab paid, and he got my wife.

I got a text moments later. “Sorry hon,” my wife wrote. “It’s his birthday…let the kid enjoy some sex.”

That was it for me. Hillary insisted I relax and have beers at the place where the sun goes down. Then I should go back to resort and hit up those bars. She allowed me to come back at midnight, and I’d have her used yoga pants waiting to smell in the guest bathroom. No tub, but a shower only. Bad jerk off spots, those standing showers.

What you all want to hear is about my wife, I know. She told me. Here it goes.

Her and her young lover went to the sports bar in Disney Springs near the UBER pick up area. They got another drink, another shot and waited for an Uber.

They got back to our room, and the young punk showed some strength when he out my wife up against the wall. He was telling her he loved that outfit, the flowing romper She told him, “I wore it because I know you like to fuck me in it,” she said as they kissed. And that is what the punk did. He put her up against the wall, moved the romper’s crotch area and her wet panties aside and fucked her against the wall. Her legs wrapped around him and she was cumming in a minute. She was apologizing for cumming so much all over his dick as she always does. Apologizing for her pussy sucking on his dick and getting it wet. And my wife is a gusher and a squirter. Her shit was on that floor when I got back. But that was later.

After sex against the wall, he bent her over and fucked her over the loveseat in the living room. She said she was cumming all over the rug and screaming “You’re cock is so big.” Exactly what a young stud wants to hear fucking an older lady.

They made their way to the bed, and he had her legs up by her head, still in the romper.
Here is where fantasies in our head meet reality. Hillary had already cum a few times. This punk wasn’t cumming. They had been fucking over ten minutes with no breaks. So my wife was getting annoyed. She is adamant that you can’t keep poking your shit in her shit for that long. It will start to get raw, especially a big cock like this dudes.

She managed to get him to break, have a smoke and get naked and get the tub ready. My wife, ready to stop sex (remember she’d already been fucked by Jarrod) got on her hands and knees, put on her black glasses and put his dick between her huge tits. She fucked his cock with her tits using her own pussy juice as lubricant staring up at him the whole time. She sucked his tip, and I know that her tit-job/BJ combo will get any man cumming. And it worked like a charm. The guy got a pretty good twenty-second birthday present as he came all over my wife’s tits and her face.

Normally, my wife wants to have a few drinks and relax after sex. Which she had a LOT that day. Her ass hurt, her pussy hurt, her fucking feet hurt. This young punk wanted to go BACK out drinking. So she told him to meet his friends. They could ‘hook-up’ later. She had plans. Which she did not.

She took an hour to herself and then texted me to come back. I was at the bar by the pool. By myself. I went back and Hillary bitched and moaned. “That dude is TOO horny even for me,” she added and shower me her phone. He was texting about “more fun”. His cock was too big, she said, her ass hurt like hell, her pussy was raw. She was done. She said my dick was more fun than his. He kind of just ‘shoves’ it in you, she told me. No rhyme or reason.

Poor young stud fucked my wife TOO much.
We sat in the tub and watched TV.

That was day fucking one.