I continue the tale of how I got involved in the amazing sexual exploits of Lupe, my uncle’s second wife when I stayed at their guesthouse on the Pacific coast of Colombia.
I had travelled to Colombia on my first paid photography assignment after graduating from university. I was staying in a small remote town, as my uncle had moved there from the UK many years ago, and had bought a guesthouse.
My Uncle Gerry was almost sixty, and I was stunned on arrival at the guesthouse to meet his wife Lupe, who was in her mid-thirties. She was gorgeous, with an incredible busty, curvy figure. For a young twenty-three-year-old guy like myself, I considered her the best MILF I had ever seen.
On my first full day there, I caught Lupe having sex with one of the other guests. She had certainly been enjoying herself and had also worked out that I had been spying on her. Lupe later explained that my uncle’s financial situation was dire and that she had made a financial agreement with the only two other guests. Lupe would sleep with them twice a week for an increase in the rent.
Lupe had then asked if I wanted to make a similar arrangement with her, which I absolutely did. Of course, these arrangements had to be kept secret from my uncle. Since then, I had already enjoyed sex with Lupe on numerous occasions.
But then I had spied on one of the guests with a different woman, Lupe’s friend Izzy. It later became clear that Izzy also ran a guesthouse on the other side of town, and that once-a-month Lupe and Izzy swapped over, and ‘serviced’ each other’s guests.
Izzy, a gorgeous blonde Latina busty MILF, had visited me in my room on a couple of occasions to service me since. I had even spied on Izzy and Lupe as they together had entertained six young men at the same time during an epic gangbang session.
Just recently I had been in bed with Lupe, and she had told me about numerous sexual adventures she had participated in when she was younger. Not to be outdone by her friend, the next time I was with Izzy, she had also begun to tell me about the naughty escapades from her youth.
Izzy had been telling me all about when she worked as a ‘guest liaison officer’ at a high-end resort on the coast near Cartagena. The resort had access to book a luxury yacht for the day, for guests to go island hopping. Izzy had manipulated a group of older men to pay for the inaugural trip, as she had promised to come along and ‘serve all their needs’…
Izzy led Mike down the steps, down the short corridor, and into the master cabin. It was nicely furnished, with a huge queen-sized bed, and an ensuite bathroom with a shower.
“Well, Mike, why don’t you strip off for me, put your clothes on the chair over there,” Izzy told him, kissing him again, “Then I’ll strip off for you.”
“That won’t take long,” Mike joked. Izzy was wearing tiny red bikini panties, high heels, and nothing else.
Izzy giggled, as Mike did as he was told, and began undressing. Izzy raised the vent in the ceiling above the bed, so it would let in fresh air from the sun deck above. She then closed and locked the cabin door, ensuring their privacy.
Izzy put some music on. Mike sat naked on the side of the bed and was soon experiencing a wonderful topless lap dance from Izzy. She ground her ass into his lap, feeling his cock getting harder and harder by the second. Mike’s hands ran across her body, from her tits to her ass and back again.
“Are you really gonna fuck all those other guys?” Mike asked, still grinning, as he desperately tried to undo the side ties on Izzy’s bikini bottoms.
“Absolutely,” Izzy giggled. “But you’re first Mike. You had to be my first. I just love fucking a married man.”
They both laughed. Mike finally untied Izzy’s bikini bottoms and removed them. Izzy took her bikini panties from Mike and threw them to land on his pile of clothes folded over the chair.
“There, you can take them as a souvenir,” Izzy purred, turning to kiss Mike. “Just don’t show them to your wife.”
Izzy chuckled, as she ground her ass back against Mike’s now fully erect and rampant cock.
“You know, Stanley is married too,” Mike told her, smiling, his hands back on her tits again.
“Yes, he told me,” Izzy grinned.
“And Gilberto,” Mike continued. “Not sure about Herc though.”
“Well, I’ll be sure to find out later,” Izzy told him, giggling.
Izzy then spun around in Mike’s lap, to sit astride and face him. Mike buried his face in Izzy’s tits, as she began to jerk his cock. After a few minutes of enjoying Mike nibbling and sucking on her nipples, Izzy dropped down onto her knees on the floor, spreading his thighs.
Izzy grinned up at him as she took his cock in her mouth, licking the head and shaft, before slowly sucking him. It wasn’t long before she was taking Mike’s cock to the hilt, as she massaged his balls with her fingertips.
“Oh fuck, yeah,” Mike moaned.
Izzy slobbered, spat, and slurped as she sucked, giving Mike her very best sloppy blowjob performance, only occasionally coming up for air. Mike was loving it, and Izzy was enjoying herself too, playing with her clit as she blew him.
“Does your wife suck your dick?” Izzy grinned up at Mike.
“Yeah, occasionally. But not like this,” Mike replied, smiling back.
“Has she got big tits?” Izzy asked, licking and kissing his balls.
“No,” Mike replied, his hands moving down to grope Izzy’s boobs. “I don’t think any man could resist such a gorgeous girl with tits like yours.”
“Good answer,” Izzy giggled as she got up from her kneeling position. “Mike, why don’t you sit back on the bed for me?”
Mike nodded, shuffling back until he lay on the bed with his head propped up by three thick pillows, pressed against a comfortable-looking padded headboard. Izzy clambered onto the bed and sat astride Mike facing him. Izzy reached toward a clear bowl on a cabinet at the side of the bed, that she had earlier filled with a very large number of condoms.
“Planning on getting through all those today?” Mike joked.
Izzy giggled, tearing the wrapper off one with her teeth. She took Mike’s throbbing member in her hand, looking at it lovingly. She then leaned forward to look closer into his eyes.
“Can you keep a secret?” Izzy whispered as Mike nodded. “I mean, from the other guys?”
“Sure,” he replied.
“Good boy,” Izzy said, giggling, placing the unwrapped condom behind Mike’s ear.
Izzy reached back to take Mike’s bare, rock-hard cock in hand, and guide him into her waiting pussy. Izzy was so wet she easily slid down his shaft. Then putting both her hands on his chest, she began to ride his dick. They both had huge smiles on their faces as they looked into each other’s eyes.
Izzy rode Mike’s cock slowly at first, enjoying the sensation. Mike was loving it too, watching this gorgeous young busty blonde, wearing nothing but her stripper heels, slowly slide up and down his dick. He ran his hands from her hips up to her breasts and back over and over again.
Soon Izzy began panting and whimpering, and she started bouncing up and down on Mike’s cock with more speed and urgency. Mike gripped Izzy’s waist, encouraging her, as he stared at her huge bouncing tits.
“Oh shit, yeah, I haven’t had any cock in months,” Izzy confessed. “Oh Mike, I’m gonna get so much lovely cock today.”
Mike laughed, nodding.
Izzy was getting very excited, moaning louder, as the thrill of knowing that her plan had come to fruition took hold.
“Oh fuck, yes!” Izzy cried, “Yes, yes, yes Mike! Oh, fuck!”
Now Izzy began riding Mike’s cock in high gear, her bouncing tits a blur in front of Mike’s face. Izzy was close now and was determinedly headed for her destination: Planet Orgasm. Izzy moaned and whimpered even louder, as Mike thrust up into her as she rode his dick for all she was worth.
“Oh fuckkkk!” Izzy finally cried out very loudly indeed, as she enjoyed what she hoped was the first of many, many orgasms she would be experiencing today.
Izzy collapsed onto Mike, kissing him. Mike took Izzy by the waist and rolled her over onto her back. He then immediately got on top and pushed his rampant cock into her sopping wet pussy.
“Oh yeah, fuck me, Mike,” Izzy whimpered, “Fuck me.”
Mike began happily pounding away at Izzy’s pussy. He spread her legs wider, forcing his cock in right up to the hilt. Izzy grinned up at him, reaching back to squeeze his pumping buttocks.
“Oh fuck, Mike. I love fucking an older married man,” Izzy panted, smiling.
Mike moaned from his efforts. Izzy sensed he might not last too much longer. It wasn’t surprising, with Izzy’s legs spread as wide as possible for him, her tits bouncing on her chest in time to his thrusting, as she whimpered and moaned.
“What’s your wife’s name?” Izzy asked, grinning.
“Ada,” Mike moaned as he grabbed at her right tit.
“Well, next time you fuck your beloved Ada, you can think about me, can’t you?” Izzy teased. “All about this moment and what fun we had.”
Izzy giggled as Mike groaned louder. As he wasn’t wearing a condom, Izzy thought it best she offered him another place for him to spill his seed, and she better do it soon.
“Do you want to come all over my tits, Mike?” Izzy asked.
“Fuck, yeah,” Mike moaned.
“You look like a man who desperately needs to come over a nice big pair of boobs,” Izzy giggled.
Mike pulled out of Izzy’s pussy and shuffled forward to kneel astride her chest. Izzy pushed her tits together, as Mike pushed his aching cock in between them. They were still slightly slippery from the baby oil all the guys had rubbed into them earlier up on deck. Mike easily slid back and forth between Izzy’s huge tits.
Izzy smiled up at Mike, encouraging him as he fucked her amazing, young, firm, glistening, bouncing tits. His cock was almost a blur enveloped in her cleavage, as he furiously pumped away. The engorged head of Mike’s cock appeared at the top of her cleavage and then disappeared back inside again, over and over.
“Oh, that’s it, Mike, fuck my tit pussy,” Izzy whimpered, her hands clamped on the side of her boobs, looking down at his cock pumping in between.
Finally, it was all too much for Mike, and with a last long groan, he erupted, blasting spurt after spurt of white-hot spunk, splashing it across Izzy’s chin and neck. Izzy giggled as he did so, watching the last few drops dribble out between her breasts.
Mike collapsed back on the bed, a huge smile on his face.
“Oh, Izzy, thank you,” Mike sighed, “You’re such a lovely, lovely girl.”
“Oh, bless you, Mike,” Izzy grinned, getting up from the bed. “That’s very sweet of you to say.”
She stood and started to move toward the ensuite bathroom.
“Plus, you’ve got the best tits and ass I’ve ever seen,” Mike chuckled.
Izzy burst into laughter at that one, as she finally removed her high-heeled shoes.
“Well, that’s very sweet of you to say too,” Izzy giggled. “And I very much enjoyed your lovely big hard cock, Mike. Your lovely wife Ada is a very lucky lady.”
Izzy told me Mike’s dick was of average size but wanted to make him feel extra special by telling him he had a big cock. Certainly, it wasn’t a lie that she had enjoyed his cock very much.
Izzy cleaned herself up in the bathroom, wiping away Mike’s jizz from her chin, neck, and chest. She then took a shower, before quickly drying herself off.
She then appeared back in the cabin, a small white towel wrapped around herself, just about covering her bust and bottom. Mike sat up on the bed.
“Are you ready for round two, Mike?” Izzy grinned.
“Round two?” Mike asked, looking surprised. “Oh, I’m an old man, honey. I’m not sure if I could manage it. I’m afraid I might disappoint you.”
“Nonsense, you’re not old. And I’m sure you’ve got plenty of lead left in your pencil,” Izzy giggled. “I’m sure I’ll have you all big and hard again in no time.”
“Oh my god,” Mike said, grinning, laying back on the bed as Izzy removed the towel to reveal her naked body again.
Izzy then moved a large mirror on a stand in the corner of the cabin closer to the bed
“Besides we must have a round two. You didn’t get to fuck me doggy style in front of the mirror yet,” Izzy continued, as she clambered onto the bed. “But first Mike, I want to sit on your face.”
Izzy giggled as she pushed Mike back onto the pillows, and moved to sit astride his face. Mike gripped her hips and immediately began kissing and then lapping at her pussy. Izzy sighed with pleasure, grinning down at him.
Lupe had told me during her youth she had enjoyed immensely sitting on an older man’s face after fucking his brains out, and having him bring her to ‘oral satisfaction’. Apparently, Izzy was of the same mind as Lupe when she was younger.
Mike continued to expertly lap at Izzy’s clit and pussy with his tongue, and it wasn’t long before she was panting and whimpering again. Izzy looked back over her shoulder to see some small stirrings in Mike’s cock. She spun around, lowering herself into the classic sixty-nine position, taking his cock in her mouth, as Mike returned to pleasuring her.
After a few minutes of Izzy teasing his balls and shaft with her tongue, and Mike was back to full power again. Izzy was very wet indeed now, and excitedly moaning at all the attention from Mike’s tongue. Eventually, it all became too much for Izzy, and she had to remove Mike’s cock from her mouth as she screamed in pleasure.
“Yes, yes, yes, yes, yesss,” Izzy cried as she climaxed for the second time today.
Izzy turned around on the bed, kissing Mike, and wiping away her pussy juice from his mouth.
“Come on then big boy,” Izzy ordered, as she moved onto her hands and knees, facing the large mirror on the stand next to the bed.
Mike didn’t need to be asked twice and moved to kneel on the bed behind her. He then pushed his cock into her lovely, tight wet twat. Izzy moaned in pleasure as she felt him enter her.
Mike began pumping in and out of Izzy’s pussy, as he gripped her hips. He grinned, obviously enjoying the view in the mirror of Izzy’s huge tits dangling beneath her, swaying in time to his thrusts. Izzy stared at Mike’s reflection in the mirror, giving him lots of eye contact, smiling, and blowing him kisses as he fucked her.
Mike slapped Izzy’s stunning ass, enjoying the sensation just as much as she did. But after much thrusting from Mike, the view of Izzy’s ass slapping against him, and her bouncing swaying tits in the mirror became too much. He groaned loudly, and pulled his cock out, slapping it on Izzy’s ass cheeks.
Izzy turned her head over her shoulder to look back at Mike, sticking her tongue out in the vain hope he might be able to shoot his seed that far. A few more slaps of his cock on Izzy’s ass put him over the edge, and Mike climaxed again, shooting his jizz across her back, and over her ass. One spurt made it as far as Izzy’s shoulder, but he couldn’t quite make it to her open, waiting mouth and tongue.
Izzy giggled, as Mike collapsed back on the bed, now completely spent.
“Have I drained those balls now?” Izzy chuckled, kissing him.
Mike put his arms around Izzy, and they lay on the bed in a sticky embrace, quietly kissing for a few minutes.
Eventually, Izzy broke off their coupling, thinking she should probably clean up.
“Well Mike, I should shower, huh?” Izzy told him, getting up from the bed. “But you have my panties as your souvenir. And if you’re a very good boy, I let you take a photo of me naked, if you like. Just don’t show either of them to your wife.”
“Oh, yes, I’d love a photo,” Mike admitted. “I have my camera upstairs.”
“Ok naughty boy. But we’ll do it later. After I’ve fucked all your friends upstairs,” Izzy giggled and headed for the bathroom.
Izzy told me she wanted the guys to feel they had gotten their money’s worth. It was an extremely expensive trip they had paid for, and even though two-thirds of it had been paid for by Mike’s company, Mike had paid for the other third with his own money. Plus, Mike, Stanley, and Drew were presumably going to have to justify the cost of the day trip to their bosses when they returned home.
Izzy figured if the three Americans convinced the two Colombians upstairs to sign the sales deal, the cost of the day trip would have been worth it to the American company. It was now up to Izzy to make sure the Colombians, and everyone else, of course, had a great time.
Izzy wanted everyone to feel they’d had a great day. To Izzy, that meant she was planning on two rounds of sex for each guy. She figured she wanted each guy to leave that master cabin with a huge smile on his face, and feeling like a real stud. Two rounds of sex with an insatiable busty young blonde would surely do that.
She also wanted to leave them something to remember her by. That was why she had given Mike her bikini panties as a souvenir. She had other little sexy gifts planned for the other guys. It didn’t cost her much at all, but knowing they had a sexy little souvenir of their time with Izzy might mean all the world to some of these guys.
Izzy also knew guys loved a photo of a naked sexy lady, especially one they had gotten to fuck. But she was only going to offer this to the American guys. If they showed it to their friends, she was fine with it. But she didn’t want the Colombian guys, who presumably lived not far from here, owning one, and potentially showing it to someone she might know.
Izzy figured two rounds of sex with her, a souvenir, and a photo (at least for the American guys) would make them feel they had gotten their money’s worth from the day trip.
She didn’t want to see any slightly disappointed faces at the end of the day. Firstly, because she was a people pleaser, or perhaps more specifically a man-pleaser. Secondly, if the guys left thinking they had been ripped off or swindled in some way, they might complain to the resort manager, and it would all come out about what exactly Izzy had been up to. Izzy couldn’t afford for that to happen.
The last thing Izzy offered Mike was to share a shower. She called him in, and he happily let Izzy wash him all over before he massaged lots of soap suds into her breasts. She then dried herself off, and Mike too, before helping him dress.
Finally, she embraced him whilst she was still naked. They had a long hug with lots of kisses, as Mike got a final grope of her tits and ass.
Izzy then unlocked the cabin door, and let Mike exit along the short corridor toward the steps that led back up to the deck above. Izzy then closed the door behind him.
A moment later Izzy heard a big cheer from up the deck. Presumably, Mike had emerged, and the other guys were having a bit of fun at his expense. And Izzy suspected she knew exactly why.
Izzy had opened a vent fitted into the ceiling of the master cabin as soon as she and Mike had left the rest of the guys. Izzy had told Mike it was to let in some fresh air. That was true, but Izzy knew it also meant any sounds made in the master cabin were quite clearly audible in the covered lounge area up top. Izzy knew the guys would have tired of being out on the sundeck soon enough and would retire into the shaded lounge area.
It was all part of Izzy’s carefully calculated plan for the day. She knew the guys might get bored for an hour all by themselves, with no pretty girl’s face to see. No tits and ass to stare at.
But if now and again they heard that busty, pretty girl panting, whimpering, moaning, and crying out in pleasure as one of their colleagues fucked her, well that might entertain them enough until it was their turn.
Izzy smiled to herself at the thought of what all the guys were chatting about up on deck. She guessed they were quizzing Mike about all the dirty details of what had gone on. Izzy suspected Mike was just smiling and going along with all the jokes, but acting as the gentleman he was, and not giving out many details.
Izzy busied herself in the cabin. She changed the sheets on the bed and the pillow covers. She had brought replacements from the resort, as she figured no guy wanted to go to bed with spunk stains on the sheets from the previous guy.
Izzy then got dressed into her next outfit, one she had put in her bag of tricks she had stowed down here earlier, and then made her way out of the cabin, up the steps, and out onto the sun deck. She then slowly turned back toward the covered lounge area behind her, to cheers and clapping from the guys, and appreciative comments about her outfit.
Izzy wore black hold-up stockings, her stripper heels, tiny black panties, and a black bra with a see-through front so that her tits were still on display for all to see. Izzy could see the guys were sat all around the lounge area, with Mike in the corner looking rather sheepish, perhaps from all the jokes at his expense he had received a few minutes earlier. But he still looked up and smiled at Izzy.
“So, what’s been going on guys?” Izzy said with a knowing smile, acknowledging with one question that she had been away for a little while, but not what she had been up to.
The guys gave out more compliments on how she looked, as she moved behind the small counter in the lounge to serve up some more drinks. There was some general chit-chat, but nothing referencing the fact Izzy had just been fucking Mike for the last hour, and the guys had probably heard the whole thing.
“Well guys, did you do what I asked? Have you come up with a way to decide who I’ll be er... escorting downstairs?” Izzy put it politely, grinning.
Herc smiled and pulled out a pack of cards from his pocket. The guys had decided to play one round of poker, with the winner getting to bed Izzy next. They had it all worked out, with a box of matches they had found, which they shared out to use to bet with.
Izzy got them the two American guys, Drew and Stanley, and the two Colombian guys, Gilberto and Herc, sat around the countertop. The cards were dealt out and the game began. There were lots of jokes as the game continued, and from the comments, it was clear to Izzy that the guys had heard pretty much everything she had gotten up to with Mike earlier. It was also clear each guy was desperate to be the next to get to fuck Izzy, which she loved.
Mike pulled Izzy to one side as the game continued.
“Do you want me to go down and close the open vent in the cabin?” Mike whispered in Izzy’s ear. “I think they could hear everything, you know, before, with me and you.”
“Oh no, it’s fine,” Izzy whispered back. “It’s just a bit of fun.”
Izzy appreciated Mike was trying to be a gentleman, but Izzy liked the fact the other guys were going to hear her enjoying another good hard fucking.
I thought to myself that perhaps this was the beginning of Izzy becoming the exhibitionist she would eventually become, as I had now watched her fuck numerous other guys, which she clearly enjoyed.
Izzy quickly went around clearing up discarded plates of food and glasses from the bar out on the sundeck, and then here in the lounge. She brought out some fresh food and snacks and refilled everyone’s glasses. She wanted the guys happy and well-fed, as she would soon be disappearing again for the next hour or so.
The game continued until it came down to just Gilberto and Stanley. Stanley eventually turned over his cards, showing he had three of a kind. But Gilberto turned his over to reveal a straight flush, smiling at Stanley, and then Izzy.
“Oh never mind, Stan,” Izzy told him, giving him a quick kiss on the lips as a consolation prize, and allowing his hand to grope her ass for a moment.
Izzy then moved to the other side of the countertop, putting her arms around Gilberto, and kissing him on the lips too.
“Congratulations Gilberto,” Izzy grinned. “You’ve won… me.”
Everyone laughed, as Izzy helped Gilberto up from his seat.
“I love those stockings,” Gilberto said, sighing.
Another round of laughter from the other guys.
“Oh, thank you, sweetie,” Izzy told him. “I can keep them on for you if you like?”
Another round of laughter.
“Or I have a whole bunch of sexy costumes downstairs for you to choose from,” Izzy continued, then turning to the rest of the group and winking. “That goes for all of you guys too.”
Izzy then remembered she hadn’t offered to change into anything for Mike earlier. But she had been just too horny and desperate to fuck, so it had slipped her mind.
Izzy then left the deck with Gilberto, hand in hand, and helped him down the steps to the lower deck. He was an older gent, so seemed to need a little assistance.
Once in the master cabin, Izzy closed and locked the door again. She then put her arms around Gilberto and kissed him. Izzy told me they spoke with each other in Spanish, but she had to translate what they had said so I could understand. Gil soon returned her kiss, and they spent the next couple of minutes locked in an embrace, quietly snogging.
“You know Gilberto,” Izzy finally said. “Mike told me you’re married?”
“Yes, but please, call me Gil,” he replied.
“Well, Gil, I just want you to know, I love married men,” Izzy continued, kissing Gil again, “You know why? Cos married men are discreet. Are you discreet Gil?”
Izzy just wanted to ensure Gil wasn’t going to go blabbing to anyone about some local busty blonde strumpet who fucked five guys on a yacht.
“Of course, Isabel, don’t worry. I won’t tell a soul,” Gil promised. “Is it Isabel or Isabella?”
“Just call me Izzy,” she replied.
Her full name was Isabel, but she decided it was better the guys didn’t know too much of her personal information.
“So Gil, did you want me to change into another outfit?” Izzy asked, getting him to sit on the side of the bed in front of her, “Or do you just wanna watch me take this one off?”
“Oh yes, just take it off, please” Gil pleaded.
Izzy giggled and began slowly stripping for him. First, off came the bra, before pushing her boobs into Gil’s face. After allowing Gil to fondle and suck on her titties for a few minutes, Izzy turned, bent over, and removed her panties, revealing her stunning ass.
Izzy then backed that ass up, and into Gil’s lap, and began grinding away. Gil’s hands were all over Izzy’s ass and hips. Izzy leaned back to whisper in his ear.
“Can I make an educated guess about you Gil?” she asked.
“Of course,” Gil replied, his hands moving to grab her breasts.
“I think you’d quite like me to keep my stockings and high heels on when you fuck me,” Izzy continued. “Am I right?”
“Oh, yes, please,” Gil sighed.
“Is that what your wife does for you?” Izzy giggled.
“Oh no, sadly not. She’s very conservative, my wife,” Gil explained. “I suggested stockings once, many years ago, when we were young, but she refused.
“Oh, I’m sorry, darling,” Izzy whispered. “But don’t worry, I’m not conservative at all. And I won’t refuse you anything.”
They kissed again, as Gil continued to massage Izzy’s huge tits.
“Now, let’s get you out of those clothes,” Izzy said.
She stood up and helped Gil to remove all his clothes, placing them over the chair in the corner, just as Mike had done earlier. She then returned to a naked Gil and sat on the side of the bed. Izzy parted his thighs, got down on her knees between them, and then with a big smile on her face, took his now rock-hard cock in hand, and bent down to begin sucking him.
Izzy slobbered over and sucked on Gil’s cock and balls for the next five minutes, as he panted and moaned in pleasure. Gil admitted to Izzy he hadn’t had a blowjob for decades. Izzy thought that was rather amusing, and turned her on, knowing Gil probably hadn’t been blown since before she was born.
Then it was onto the bed, as Gil lay back, with a brief pause for Izzy to roll on a condom, before she sat astride him and rode his cock energetically. Gil enjoyed the sight of Izzy’s bouncing tits and the sound of her ass slapping against his upper thighs. Izzy loved looking down on Gil as she fucked him, his face in ecstasy. Gil’s hands endlessly caressed the top of her stockings.
Izzy whimpered and moaned, loving the feeling of this elderly gent’s cock inside her. It turned her on further knowing the boys up on the deck above could hear every sound she was making, and probably discussing amongst themselves as to exactly what Gil was doing to her right now to illicit such lovely noises. She felt very much the center of attention and was loving it. These guys might think today was all about them, but Izzy knew this was her day, and she was going to enjoy it to the fullest.
It wasn’t long before Izzy climaxed again, and she then immediately got on her hands and knees on the bed, in front of the mirror, just as she had done for Mike earlier. Soon Gil was pumping away at her from behind. Izzy knew Gil would enjoy the sight of her ass high in the air, with her stocking tops just below to give him an extra thrill.
Izzy’s tits swayed and jiggled in the mirror, as she bounced her ass back against a rampant Gil. He panted, moaned, and groaned until it was all too much, erupting inside this busty young blonde who must be more than forty years his junior. Gil collapsed back on the bed, trying to catch his breath. Izzy giggled as she cleaned him up, removing the spunk-filled condom.
Izzy sat beside Gil as they caressed and kissed each other. But soon Izzy decided she wanted another good tonguing from an older man, and so clambered across Gil, to lower herself onto his face. Gil began happily lapping away at Izzy’s pussy, licking and teasing her clit. It wasn’t long before she was again panting and whimpering in pleasure.
Eventually, Izzy creamed herself, crying out loud and long, as her eyes rolled up in ecstasy. Her young firm, stocking-encased, thighs tightened around the side of Gil’s face, which he seemed to enjoy.
Due to his age, Izzy felt Gil might need a bit more time before he would be able to get it up again, so she told him to turn over onto his front, and gave him an oil massage. Izzy oiled up her tits and slid them up and down Gil’s back, as she whispered all about what a dirty young girl she was.
Gil turned over, so Izzy could slide her oily, slippery tits all over his face, chest, and cock. That seemed to do the trick, and Gil was soon well on the way to being ready for round two.
“Do you want me to just blow you, honey?” Izzy purred, slapping Gil’s half-erect cock across her big firm breasts.
Gil nodded, sighing, as a huge grin spread across his face. Izzy figured a guy that hadn’t had a blowjob in decades could do with a really good one right about now. Izzy positioned herself on her knees, in between Gil’s spread thighs, and bent down to take him in her mouth.
It wasn’t long before Gil was fully erect, as Izzy’s lips and tongue slid up and down his shaft. Soon Gil took Izzy’s bobbing head in both hands, getting her to speed up her sucking and slobbering. Gil moaned and groaned as he got more and more excited.
Izzy came up for air for a moment.
“Fuck my mouth, darling,” she purred, looking up at Gil with a grin.
Gil held Izzy’s head still and began thrusting his cock up into her mouth. Saliva ran from Izzy’s bottom lip and dripped off her chin. Gil panted as he fucked Izzy’s mouth furiously. Izzy moaned too, encouraging him.
“Oh fuck, I’m gonna come,” Gil groaned.
Izzy pulled his thrusting cock from her mouth for a moment.
“Where you wanna come baby?” Izzy asked, jerking his aching cock, “Face? Mouth? Tits?”
“Face,” Gil moaned.
Izzy knew what Gil wanted, slapping his cock over her face as she furiously jerked his cock, opening her mouth wide and sticking out her tongue as far as she could. A moment later Gil was groaning loudly, as he pumped his seed all over Izzy’s face and tongue, and all over himself too.
Izzy giggled, Gil’s sperm dripping from her lips and chin.
“Oh, thank you, darling. That was lovely,” Gil panted.
Izzy leaned over, kissing Gil. Some of Gil’s spunk got smeared across his own face. But he didn’t seem to mind as they snogged for some time, both covered in Gil’s love juice.
Izzy then took Gil to the shower, finally removing her stockings and high heels. She cleaned herself up, and then Gil, before drying him off and assisting the older gent in dressing.
“I got a little souvenir for you,” Izzy said, giggling, stuffing her stockings into his jacket pocket. “Just don’t let your wife find them.”
They embraced one last time, Gil’s hands wandering from Izzy’s naked ass to her tits as they kissed.
“I really appreciate all your efforts, my dear. You have no idea how much,” Gil told her, smiling, as he bid her goodbye, leaving the bedroom, and back up onto the deck above.
There were more cheers to be heard from upstairs and Izzy busied herself getting ready for her next encounter. She imagined the guys upstairs had once again heard all the lovemaking noises coming through the vent in to master cabin’s ceiling, and were now ribbing Gil about it.
After changing the sheets on the bed again, Izzy made her way back up and out onto the deck. There were more cheers and comments, as the guys saw Izzy now wore a very skimpy, sexy nurse’s outfit. It consisted of tiny white panties, an extremely short, white mini-skirt with red trim, a tiny white bikini top with matching red trim and little first-aid crosses over the nipples, a little white nurses hat with red trim, and white high heels.
Once again, Izzy busied herself getting drinks for the guys, making sure they had fresh snacks and food available, and generally fussed over them. She also happily allowed any man who wanted to grope her boobs and bum or grab a quick kiss to do so, as she moved around the table.
Soon the cards were pulled out again, and Stanley, Drew, and Herc began playing poker to see who was going to get to fuck Izzy next. Stanley folded rather quickly and then Drew produced a winning hand against Herc to declare himself the winner.
Drew was then led by Izzy down the steps below deck, to loud cheers and whistles from the guys.
It was then very much a rinse-and-repeat scenario for Izzy, albeit another very enjoyable one. She undressed Drew, then stripped for him, gave him a lap dance in just her nurse’s hat and high heels, and then dropped to her knees to suck his cock. Later they moved to the bed, for Izzy to ride Drew’s cock all the way to another orgasm before Drew had her spin around to ride him reverse cowgirl, so he could stare at her magnificent bouncing ass.
Then he got Izzy on her back so he could pump away at that pussy, as her legs flailed around in the air. Soon, Drew began to groan heavily and blew his load deep inside her.
As Izzy cleaned themselves up, she could hear the jet skis now being used by some of the guys out on the water. Izzy was glad they were having some fun, although not as much as she and Drew were having right now.
Izzy then clambered back onto Drew, sitting on his face, and for the third time today began enjoying the thrill of a man lapping away at her pussy and clit. Drew was the youngest of the guys, and seemed a little inexperienced at going down on a woman. But after a few hints and pointers from Izzy, Drew soon got the hang of it, and fifteen minutes later she was in the throes of another wonderful climax and coming on his face.
Drew was then ready for action again, and took Izzy doggy style, before eventually pulling out to shoot his load all over her stunning ass. Once again Izzy showered with Drew, dressed him, and gave him her little white panties as his souvenir.
Just a few minutes after Drew left to go back up on deck, Izzy herself reappeared there. Again, there were lots of admiring comments about her outfit. Izzy wore thigh-high black leather boots, little black thong panties, and nothing else. Once again her tits and ass got felt up as she passed amongst the guys.
Soon the final poker game began between Herc and Stanley. Eventually, Herc was the winner and was led back below deck to the master cabin.
When Izzy undressed Herc, she found he had a rather large cock, quite thick, and around eight inches long. Once she had stripped off, it wasn’t long before the head of Herc’s cock was being rammed into Izzy’s mouth as he stood in front of her. Izzy was on her knees as he fucked her mouth with his large member. He tried to get her to deep-throat him, but Izzy explained at that time she was still rather young and inexperienced at such things, and so had to politely refuse.
Izzy then rode his big cock to another glorious orgasm, before Herc took her doggy style in front of the mirror, eventually pulling out to empty his balls all over her face. After a quick clean-up, Izzy sat on Herc’s face, and got all hot and bothered, until she saw Herc was also ready for action again. Izzy span around to suck his cock whilst he continued lapping at her pussy until she achieved yet another orgasm. After a few more minutes of sucking, Herc made a creamy mess in Izzy’s mouth.
Then a shower with Herc followed, before Izzy gave him her black thong panties as a souvenir, kissed him farewell, and cleaned herself and the room up before changing outfits once again.
Izzy soon appeared back up on deck in black high heels, black suspenders held up with a black suspender belt, and nothing else. Izzy had decided for her final journey upstairs, she would show off everything she had, a fact the guys were very appreciative of.
Izzy once again made her way around the guys, refilling their drinks and generally fussing over them. The guys knew the score now, and they all got in a good feel of her tits and ass. Izzy slowly moved from one to the other, generously giving each of them a few minutes of her time, so they could get one final kiss, a cuddle, and a nice long grope of her firm young body. Drew even managed to get a finger inside Izzy, rubbing her clit with his thumb, as she poured him another drink.
Eventually, she made her way to Stanley, and after a few minutes of having his face smooshed between her tits, she waved goodbye to the other guys and led him down to the master cabin below.
Whilst undressing, Stanley insisted Izzy keep her suspenders on, so as there was nothing to strip off, she immediately began with a lap dance, and then moved to her knees to give him a blowjob. Izzy enjoyed asking Stanley numerous questions about his wife whilst she blew him and he played with her tits.
Later Izzy bounced up and down on Stanley’s cock, as she enjoyed thinking all about the fact his wife had no idea what she was doing to her husband right now. These thoughts led to yet another orgasm, and then Stanley got on top and pounded her pussy until he popped his cork.
After another clean-up, Izzy sat on the face of her fifth man that day. To be honest, she was starting to tire a little. But once again the thought of Mrs. Stanley back in North America having no clue that her husband’s tongue was happily buried in between Izzy’s thighs really got her going, and it wasn’t long before Izzy was noisily climaxing all over Stanley’s face.
After a few minutes of Izzy’s expert cock sucking, Stanley was back to full power and took her from behind in front of the mirror. Izzy stared at her reflection in the mirror as Stanley pumped away behind her.
Izzy had enjoyed her day on the boat immensely and had made five older men very happy too. Izzy decided she had made exactly the right choice in targeting older married men to sell her day trips to. She imagined a whole bunch of young single guys on a day out like this would have been much more difficult for a lone girl to handle. She could have gotten herself into real trouble.
But older married men seemed to know how to behave in such a setting. They didn’t drink too much or get rowdy. They were some naughty comments of course, but nothing that got ugly. Younger men seemed to want to continually compete with each other, which caused ugly scenes sometimes, but older men were happy to relax and go with the flow.
Izzy could just imagine if she had proposed the poker game to decide who got to fuck her next with a group of younger men. She was certain there was a fair chance that guys would start arguing, perhaps even fighting, over her, especially when alcohol was involved.
No, Izzy was sure she had made the right decision in whom she had brought out on her inaugural ‘luxury yachting day trip with benefits’. She hoped it would be the first of many.
Stanley continued to bang away at Izzy until his groaning indicated he was close to coming. Izzy got down on her knees on the floor as Stanley stood in front of her, forcing his cock into her mouth and face-fucking her. Soon the inevitable occurred, and Stanley pulled out to blow his load all over Izzy’s face and tits.
Izzy told me she had taken quite a few facials that day but had lost count. But I had a good memory for such things, and by my maths, Izzy had taken three blasts of cum to the face, from three different men.
After showering with Stanley, and giving him her suspender belt as a souvenir, Izzy had a quick kiss and hug with him at the cabin door. She apologized that he had had to wait so long for his turn.
“I would have waited in line behind twenty men to have the chance to go to bed with you,” Stanley said, smiling.
“Ooh, I don’t think I could manage that many!” Izzy laughed.
Stanley tucked her suspender belt into his pocket, got in one last grope of Izzy’s tits and ass, and then made his way back up to the deck above.
Izzy changed the sheets on the bed back to the original ones the boat company had provided. She put on a dressing gown and made her way upstairs. After fussing over the guys for a few minutes, pouring drinks, and generally being a good host, Izzy told them it was sadly time to head back to shore. It was late afternoon now, and the captain would certainly want to get the yacht back before it got dark.
Izzy asked Gil and Herc if they wouldn’t mind raising the jet ski back onto the platform at the back of the ship. She briefly showed Herc the controls that raised or lowered the platform, and the two Colombians got to work. Izzy said she could use the other guys’ help with all her bed sheets and other stuff down in the cabin. Mike, Drew and Stanley duly followed her back down to the master cabin.
As soon as they were in the cabin, Izzy took off her robe, revealing her naked body underneath.
“Mike said he wanted to take a couple of photos?” Izzy said, smiling.
The guys stood with Izzy and had individual photos taken with her, some with their faces pushed between her tits. They also took a group photo using Mike’s camera’s timer function, as Izzy wanted a souvenir of the day too. Mike said he would send it to her later.
That concluded the fun part of the day trip. The guys went back up to the deck, and Izzy called the captain on the radio for him to return to the yacht. She got dressed, back into her jean shorts and black T-shirt, and joined the guys back on deck.
The captain and his deckhand returned, and they were soon on their way back to shore. Neither the captain nor the deckhand made any indication that they knew what had been going on onboard the yacht all day.
Back on shore, everybody said their polite farewells. The captain reversed the yacht back and headed back to the boatyard. The Americans trudged off to their rooms, and the Colombians took a taxi back to the city.
Izzy reckoned everyone had enjoyed themselves and felt they had gotten their money’s worth from the very expensive day trip. Izzy had had a blast and was also looking forward to receiving her commission from this trip, as it would be quite substantial.
The next day, Izzy swung by Mike’s room and chatted with him at the door. She asked what had happened with the sales deal he had been trying to convince the Colombians to agree to. Mike happily told her the day trip had swung it, and the Colombians had signed the contract this morning. Mike said his boss was going to be very happy with him, Stanley, and Drew for pulling it off.
“Of course, my boss will have no idea the part you played in it,” Mike said, laughing.
Izzy was happy it had all worked out. She liked Mike and knew he was heading back to America that evening. She decided to give him a final treat. She looked around to check no one was watching, and then with a big smile, pushed past Mike and closed the door behind her.
Soon Izzy was topless, and on her knees in front of Mike sucking his cock again. She liked the feeling of sending him back to his wife with his balls completely drained. Mike eventually blew his load into Izzy’s mouth, and she happily swallowed all the evidence that anything had occurred between the two of them, before kissing him goodbye and making a quick exit.
Izzy never saw Mike again, or any of the other guys from her inaugural luxury yachting day trip. But she obviously still had very fond memories of that day. Somewhere, Izzy told me, she still had the photo Mike had sent her of the four of them together. I told her she better hope her husband didn’t come across it someday.
Izzy told me from then on, whenever a group of older men checked in to the resort, she would immediately target them. She would upsell one of them on an upgraded room first, with of course the added benefit of a topless blowjob. But her main aim was to sell them on her luxury yachting day trips.
I asked Izzy how often this happened. She couldn’t be sure but guessed it probably happened about every four to six weeks or so.
Izzy said she always looked forward to these day trips. She had so much fun, away from any prying eyes or malicious gossip. Izzy felt it was a safe space, where she could do what she wanted, with no repercussions, or slurs on her good name. She could just act like a total slut for the day, which she loved to do, fucking and sucking, and generally making several men very happy indeed.
The groups of men who agreed to pay for the day trips were generally wealthy married businessmen, much like Mike had been. The groups’ sizes were usually at least three to five guys. Occasionally she had taken trips with two guys, or even just one. But that made it much more expensive for the individual, and so were less likely to agree to the large cost.
If the cost were split by three men or more, it became more affordable, even though it was still quite expensive. Of course, there were extremely wealthy men out there, and she had enjoyed a few trips with just one guy. As they had the whole day together, Izzy spoiled them with multiple sex sessions, and they always left happy but exhausted.
On other occasions, the groups were a little larger. Izzy had entertained groups of six and seven men. It meant she was a very busy girl all day.
On one occasion she had entertained a group of nine guys. On that trip, she had decided each guy was only getting to enjoy one bout, limited to forty minutes. Izzy stripped for them, blew them, fucked them just once, showered, and then went back upstairs to collect her next victim. It was a fun, but very exhausting, day, and Izzy decided not to take such a large group out for her yachting trips after that.
Izzy told me on one trip just two guys had agreed to pay for a day trip. Izzy planned on fucking one guy down in the master cabin, then the other, having some lunch, and then fucking them both once more in the afternoon, before heading back to shore. However, after lunch, it became apparent these two horny older gents had other plans.
Izzy soon found herself on the deck of the boat, completely naked, sucking off one of the guys, whilst the other fucked her from behind. Izzy loved getting spit-roasted for just the second time in her young life, but this time there was no one else around to possibly see and get her into trouble. Those two old fucks spit-roasted her all afternoon, later moving the action to the more comfortable cabin below. They continually switched around, between her mouth and her pussy, and Izzy loved every minute of it.
That was the beauty of the luxury yachting day trip. There was no one around to see what she was up to. She could do whatever she wanted. Izzy said there were so many wild stories she could tell from those yachting trips.
Izzy said she worked at the resort for almost three years. She said she continued to be careful whom she targeted for ‘special attention’. She told me she usually managed to get some older guy to upgrade his room once a week and managed to arrange a luxury yachting day trip with a group of guys every four to six weeks.
In three years, if Izzy blew a guy as a thank you for him upgrading his room on average once a week, that added up to almost a hundred and fifty guys. If you took a conservative average of four guys on each yachting day trip, on average every six weeks, and the fact she didn’t start her day trips for a few months after she began working at the resort, that added up to around eighty-five guys she had fucked out on that boat. She had certainly been a very busy young lady and had enjoyed it all immensely.
I asked Izzy why she eventually stopped working at the resort. That was where, once again, her story turned rather sad.
Izzy told me the captain that took the yacht out during her trips, with whom she had an arrangement for him to leave the yacht once they reached the island, got sick and decided to retire. The boat company provided a new captain, and Izzy managed to make a similar arrangement with him.
However, after a couple of trips, the new captain wanted a cut of Izzy’s commission, rather than just the hundred dollars they had agreed upon. Izzy didn’t want to cut him in on her commission but agreed to up his bribe to leave the yacht for the day to two hundred dollars.
But a couple of trips later, the captain wanted to change the deal once again. He told Izzy he knew exactly what she was doing with these men on the yacht whilst he was gone and wanted in on the fun. Izzy refused, telling him there was no way she would ever sleep with him. The captain said if she didn’t agree he would ‘sell her out’.
Izzy again refused his demands but wasn’t quite sure what his threat had meant exactly. In the following days and weeks, she found out. Izzy turned up to work at the resort one day and was immediately called into the manager’s office. One of the owners of the resort was also present at the meeting.
The manager had said it had just come to light exactly what had been going on during Izzy’s luxury yachting day trips, that her behavior was completely unacceptable, and she had brought the resort’s name into disrepute. The owner then fired her.
Izzy didn’t believe her manager’s explanation that all this had ‘just come to light’. She had suspected for a long time that the manager knew exactly what Izzy had been up to. But as it brought in a large amount of income to the resort, which the owners would be very happy about, he turned a blind eye. But now that official complaints had been submitted, the resort had to take action.
As if that wasn’t enough, a week later it got worse, much worse. Izzy had stayed in Cartagena, thinking perhaps she might get employment at a different resort. But then an article appeared in the local newspaper, telling all the scandalous details of Izzy’s luxury yachting day trips. Izzy was mortified. It was obvious the captain was the one who had sold her out to the resort management, but apparently, he had sold the story to the media also.
The next day there was a follow-up piece in the paper, with a photo of Izzy. Izzy recognized it as a photo of a picture that hung in the reception of the resort, so guests could see who was working on any particular day. Izzy assumed some journalist had gone to the resort to get a photo some time ago, as surely that picture was taken down when she was fired.
The following day a local cable television news channel picked up the story and ran a piece about it. Izzy realized this could turn into a witch-hunt, and she had to get out of town. If she didn’t, they were going to find her, and make her life hell. She packed up her things and headed straight to the airport, flew back to Cali, and had never been back to Cartagena since.
It was yet another sour note on which her amazing sexual adventures seemed to always end. First the strip club in Bogota, and now the resort in Cartagena. Once again Izzy felt ashamed, that people would look at her and gossip, judging her.
But in Cali, no one had heard of Cartagena’s local newspaper article, or the local television station report. But it had left a lasting mark on Izzy’s psyche. She never wanted to be caught out like that again and changed her behavior accordingly.
For the next few years, Izzy had a series of regular jobs, mostly office based. She had a few boyfriends, but certainly wasn’t the very busy young lady she had been previously.
One thing that she did have from her time in Cartagena was money. She had earned an enormous amount from her commissions there. Sadly, she was convinced to use her cash in a series of unwise investments and ended up losing most of it.
Years later, when she met her husband, she used what she had left of that money to buy the Casa Rosita guesthouse.
I could see now Izzy’s guesthouse, and more specifically her unique way of encouraging renters to stay here long term was a way for her to relive the wonderful, naughty, sexy adventures from her youth. Also, it was much more controlled here. She decided who stayed at her guesthouse, and to whom she would offer her ‘extra services’.
As long as her husband never found out about what she was up to with the guests when he was away at work, Izzy really had no one else who could threaten to expose her. She wasn’t technically doing anything illegal. It felt like Izzy had learned from when things had gone wrong for her in the past, and built this setup here at Casa Rosita guesthouse to avoid the same pitfalls.
“Honey, turn over for me,” Izzy instructed.
I did as I was told, to reveal a stonking hard-on.
“Oh, Mr. Jack did enjoy hearing about what a naughty girl I was, didn’t he?” Izzy giggled, taking my cock in her hand, “Let me suck that lovely big young cock of yours, darling. Then you can get on top and fuck me senseless. I really need a good, hard pounding.”
What an absolute delight this woman was…
TO BE CONTINUED.