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Chapter 42
by
Uno1Dos2Tres3
Check in with Mandy?
Yes
______________________
MANDY
______________________
I couldn't believe my luck. My own room. I wouldn't have to go anywhere after it was all over. I could shower in my shower right away, get dressed in my pajamas (or not), and relax in the bed I would fall asleep in until my husband came back from... well, fucking one of the other beautiful women at the table. Or me, I suppose. There was a one-in-five chance he'd draw his own card as well. Why am I doing math right now?
"Alright, ladies," Mia said, looking around the table. "Let's head out."
The men watched in silence as the women stood up and walked out of the restaurant to the open pool area. We were all about to go our separate ways when Mia piped up.
"So," she said, stopping us all in our tracks. "Is there anything we should know about your men. Anything that gets them going?"
Everyone looked around the circle at each other, a hint of trepidation on their faces.
"Oh, come on, we need to help us girls out!" Mia said. "OK, I'll start. Glenn likes it if you stick a little finger in the booty."
She held up her pinky for emphasis. "Just the tip. Don't go too far. And definitely no thumbs."
The girls laughed, cutting through some of the tension.
"Scott is really good at oral," I offered. "Like, really, really good."
Eyebrows raised around the circle as the girls seemingly imagined my husband burying his face between their legs.
"Robert loves his abs and pecs," Ariel chimed in. "He's really proud of them. I rub them during foreplay and it drives him wild."
"Good to know!" Mia said with joy. "Now we are getting it, girls! OK, Madeline, what about Eric."
"Hmmm..." Madeline thought for a moment then said, "He loves a good, sloppy blowjob. Really go at it, cup his balls, he'll melt in your hands... and your mouth."
Everyone turned to Dora.
"Manny loves foreplay," she said. "He might take a while to get to where you ultimately want him to go but, trust me, be patient. It will all be worth it."
"I can second that," I said.
"OK, then," Mia said. "Let's get to it!"
Luckily our room was just a few steps away. I stopped at the door, watching the women disperse up the stairs and down the exterior walkways to the rooms they had selected. Madeline strolled up next to me. She must have drawn Dora's room.
"Have fun," she said. She disappeared into the room before I could reply. I pressed my card key to the lock and pushed the door open, exhaling forcefully as I stepped inside.
Drawing my own room didn't only come with the perk of not having to go anywhere once we were done. Home field advantage here meant that I had all my clothes here, including the extensive lingerie sets I had brought to show off for Scott, most of which, I hadn't even gotten around to wearing yet. I sorted through the various bras and thongs and teddies and bodysuits before settling on a green, lacy, silk teddy with a matching thong. The top was a bit snug, which I liked because it held my breasts together without having to wear a bra.
It also meant I had all my tools and amenities. I took full advantage, brushing and flossing my teeth, using my straightener to do my hair all fancy, and dabbing on just a bit of makeup. A million thoughts ran through my mind as I dolled myself up. Part of me was expecting to wake up from a dream. I still could barely believe this was happening. Everything had moved so fast the last few days. I went from being shy about taking off my top, to floozying around the nude beach, to fucking in front of strangers, to swinging with those same strangers, and now the tables had turned to where everyone else seemed to be unsure of themselves about something I felt very comfortable doing.
Was I really that comfortable, though?
I had just picked up my eyeliner when I heard the door open. I froze, listening intently for any signs of who it might be.
"I'll be right out!" I shouted from the other side of the bathroom door. "Make yourself comfortable." I brushed on a bit of the eyeliner then looked at myself in the mirror.
Hell yea
Then I took a deep breath and opened the bathroom door.
It was Glenn.
I know Scott and I referred to Glenn as an "older" guy, and in relation to most of the rest of the group we had at the table, he was. But 42 was far from old, and he was far from old looking. He stood tall, a few inches over 6 feet at least, at the foot of the bed, a bottle of water in his hand. His shaggy brown hair poked out from underneath his bucket hat. His blue button-down shirt hung perfect on his slender shoulders, hiding that nice, trim surfer's body I had watched from the beach. A bit of chest hair escaped through the top button of his shirt.
"Wow," he said, his eyes scanning me up and down as I posed in the doorway.
"I had a bit of an advantage," I confessed. "This is my room."
"Well, good on you," Glenn replied. "I can't say I'm complaining. Though I feel a bit underdressed."
"You could always slip into something more comfortable," I suggested.
"I'm not sure I have anything to slip into." I honestly couldn't tell if Glenn was going along with my suggestive flirting or if he really was answering the questions genuinely. Maybe he's just a really good actor.
"Well instead of slipping into something, maybe you should... slip out of what you're wearing?" I think he got the hint.
"That sounds like a good plan," Glenn agreed. He kicked off his flip flops.
"Here. Let me help you." I walked over to him and grabbed the top of his shirt, working open the buttons. I watched his slender, toned frame come into view as I continued downward, popping open each button until his shirt was resting open. A light dusting of hair covered his pecs and continued down past his belly button. I slid my hands up and down his chest and stomach. He was all lean muscle, not quite as defined as Robert, but he seemed to take good care of himself. I slid the shirt down his arms, letting it fall to the floor. He took off his hat and tossed it onto the dresser.
"Not bad for an old guy, huh?" Glenn said.
"You're not old," I said. "And no. Not bad at all. Far from it, in fact. You know you're quite the surfer out there. I've watched you a few times throughout the week."
"Thanks. I've been surfing since I was a little kid. The swell here could be better but a day on the board with a bad swell is better than any day off the board."
"Maybe you could teach me how to surf?" I asked, though I wasn't entirely serious.
"How much time do you have?"
"Tomorrow's our last day."
"I don't think you want to spend it falling off a surf board," Glenn said. "You're probably looking to relax a bit."
"Well, maybe I'll just come float out there with you on a paddle board or something."
"That would be nice," Glenn said with a smile.
"So, you look better but I feel like you could probably be a bit more comfortable. Let's try this."
I untied his shorts and slid them down to his ankles, leaving him in just a pair of black boxer briefs. I could see the outline of a very promising cock hanging down one of the legs of his underwear. I rested my hands on his shoulders and looked deep into his eyes.
""I'm going to be honest," he said. "I don't know how to do this. Are we just supposed to start kissing? Do we even kiss?"
"Would you like to kiss me?"
"Well, uh, yea."
"Then you can kiss me." Glenn hesitated. "Why don't we lay down in bed," I suggested. Glenn liked that idea and the two of us slid under the covers into bed.
"We can go at your own pace," I told him. "We can do whatever you want. Well... mostly whatever you want."
"Is there anything that's off limits?" Glenn asked.
"****," I answered much quicker than I would have thought. It's not like I thought about being choked during sex all the time, it just popped right into my head when he asked the question.
"Yea, I'm not going to do that to you," Glenn laughed.
"I don't like things in my... rear end."
"Noted," Glenn said, though I quickly remembered what Mia had said about Glenn. No thumbs!
"That's pretty much it," I said. "Oh, no smacking. Maybe light but definitely nothing rough."
"I'm starting to wonder what you think of me," Glenn joked.
"No! It's not like that," I insisted. "You asked so I answered."
"I know, I know. I'm only joking. Trying to ease the tension a bit."
"Are you feeling tension?" I asked.
"Honestly, yea. A bit," Glenn admitted. "I mean, you're beautiful. Look at you. You're gorgeous." I couldn't help but blush.
"Thank you," I said. "You don't have to say that."
"It's true. I wouldn't be surprised if every guy was hoping they'd get you."
"Were you?"
"Sure."
"Really?" I asked. "All those sexy, hot girls and you wanted me?"
"Yea," Glenn insisted. "Believe me, I wouldn't have been mad if I drew Madeline or Ariel or Dora. I wouldn't even have been mad if I drew Mia. Part of me wonders if I'd actually be relieved. I could make love to her until the sun comes up. I know because we have. But there's something about you that's different. Something that... glows."
I felt my face growing redder. "Are you sure it's not just because of my boobs?" I asked, somewhat sarcastically.
"That... might have something to do with," Glenn said with a grin. "But certainly not all of it. Mia's got great boobs. _Great _boobs. But, like I said, there's something different about you. The way you were so shy about just taking off your top was adorable and that adorableness never seemed to go away even after we found out you guys were, well, swingers, even after I'm lying next to you while you're all done up looking sexy ready to..."
His voice trailed off. He seemed unsure how to describe our current situation.
"Ready to... what?" I asked, slyly. Glenn continued to search for the right words.
"Ready to..."
"This?" I finally said, cutting him off by kissing him. The kiss was light and gentle. Inviting.
"Well, yes," he finally said. I smiled. He leaned forward, pressing our lips back together. He was a good kisser. Strong but not overly aggressive. Full of passion but tender. His hands slid across my upper body, teasing his fingertips across my shoulders, my collarbone, the top of my chest. They became more aggressive, gripping and groping as they found my breasts then continued down to my hips, finally landing on my ass. His hand slipped up underneath my nightie, gripping the bare flesh of my buttocks.
I suddenly realized how idle my own hands had been. Gently, I caressed his hairy chest, down to his abs, so nice and toned to the touch. He took my gesture as a sign to move forward, rolling over and propping himself on an elbow as he hovered over me. His other hand found my breasts again, squeezing them through the silk before snaking its way under the fabric, touching my skin directly.
"Oh," I gasped as he found my nipple, rolling it between his thumb and forefinger. He broke our kiss and descended down my body, planting his lips down my neck, over my collarbone, to my chest. His mouth found my other nipple through the thin silk and I gasped again, this time much louder as he suckled gently. He was taking it slow. Too slow. Not in a bad way, just in a way that left me wanting more. And more is exactly what I wanted.
I rolled him over so he was on his back grabbed his briefs and pulled them down to his knees. His cock sprang out, snapping from the elastic waistband, bobbing aggressively like a metronome until it settled, pointing straight to the sky. It was nice. Maybe a bit smaller than Scott's, but there was little doubt that Glenn knew how to use it.
I settled between his legs then leaned forward, crushing my breasts to his pelvis, trapping his cock between the squishy pillows of my cleavage. Slowly I slid forward, dragging my tits along his shaft, then backward until my nipples grazed his groin.
"Oh, Jesus, Mandy," Glenn groaned. "That is so fucking sexy." Forward and back, forward and back I slid, feeling his erection pulse between my breasts, harder and stiffer with each pass.
"Do you want to cum on my tits," I asked in the most seductive voice I could muster.
"Oh, fuck yea," he groaned in response. "But not yet."
He took my by the shoulders, guiding me back up his body until our lips met once again. I instinctively straddled his waist, settling down onto his lap. His hard cock was pinned beneath me, his shaft pressing into my pussy through my thong.
"Oh, yea," I moaned as I began to grind back and forth over his pole. Glenn's hands gripped my ass, pulling my cheeks apart as I dry-humped him. His hips began to move beneath me, pushing up against me as we moved together.
"Oh, that feels so good," I groaned. "Are you ready?"
Glenn smiled. "I'm ready."
I lifted my hips, reaching back to pull my thong to the side. Glenn took his cock in his hand and guided it to my opening. I lowered myself down onto him, groaning as he filled me up.
"Oh, Glenn," I gasped, my voice trembling with pleasure. I slipped the straps of my nightie over my shoulders, the think silk fabric slumped down my chest, stopping at my hardened nipples for a moment before falling completely to my lap.
"Jesus," Glenn groaned as my breasts filled his vision. I grabbed his hands and placed them on my chest. Mia's breasts were quite large. And round. And impressively perky. But there was no question Glenn was overcome with lust and desire as he groped and massaged my tits like a teenager feeling his very first pairs. Maybe he was looking forward to blowing his load all over them.
"Fuck," Glenn groaned as I slid my hips forward then back. I began riding him, slowly at first, pulling myself forward until just the tip remained inside me before thrusting backward, impaling myself to the hilt. My clit ground into his pelvis. His fingers found my nipples.
"Oh God!" I moaned. I slumped forward, my hands planted on his chest, my tits swaying into his face as I began bouncing on hips lap. "Oh, yea!"
Glenn craned his neck forward, sucking one of my puffy, pink nipples into his mouth. I cried out in pleasure as my arms went limp. I collapsed forward, smothering him with my tits, nearly pulling myself completely off of him.
Glenn never missed a beat. He used his legs as leverage and twerked his hips to get the right angle, driving up into me from below.
"Oh, God, Glenn," I moaned. "I'm gonna cum. Oh, Glenn, I'm gonna cum!"
"Mmmmph," Glenn moaned into my chest. His tongue attacked every part of my expansive cleavage. His hands clenched my ass, slamming me down to meet his upward thrusts.
"I'm cumming! Glenn! Oh, I'm Cumming!" My body writhed in pleasure as my orgasm surged through me. I could have laid there for the next 45 minutes, letting Glenn pound away until 12:59 before letting him scamper out the door to the bar, but I wanted to see what other positions he was capable of.
"My God, that felt incredible," I said as I finally came down from my orgasmic high. "I could let you do that all night."
"I wouldn't mind that," Glenn replied. He gave my ass a squeeze for emphasis.
"No," I said. "I want to see what other tricks you have up your sleeve." Glenn's eyebrows raised and a smirk spread across his handsome lips.
"OK then." He rolled us over with ease so that he was on top of me without even dislodging himself from my depths. He sat up, pulling my legs up with him until they were resting on his shoulders. My ass was lifted off the bed, angled up at him as he hovered over me.
"Oh," I yelped as he drove himself into me. Deep. His pace was slow but steady. Each thrust came after a brief pause, allowing me to anticipate the impact as he buried himself deep inside me.
"Oh, wow," I moaned. His hands gripped my ankles, pulling my legs even wider apart. I'd never had my legs stretched this far. It was a bit uncomfortable but that was easily ignored as I enjoyed the feeling of him piercing me at such an angle.
God, he was sexy
With each forward thrust, his abs would clench. His pecs would bounce. The hair on his chest glistened with a light sheen of sweat. And his cock... well, it just kept finding its way deeper and deeper into my depths with each thrust. Once again, I found myself deciding between letting him do that to me for the rest of the night or seeing if he had anything else in his bag of tricks.
I went with the latter. Glenn happily obliged. He rolled me over onto my stomach and grabbed my hips, pulling me back into him doggy-style. I was a bit disappointed for a brief second until he grabbed my leg and extended it outward, once again stretching me at my groin. I was balancing on my hands and left knee as my right was extended, held up by his strong forearms and shoulders.
"Oh, yea," I moaned as he started thrusting again, slow and deep. I could feel every inch on him drag through me.
"You like that?"
"Oh, yea," was all I could think to respond again as I luxuriated in the slow sensual movements, the exhilaration of combining sex with the thrill of balance. I felt like I was his surfboard and he was riding me like the curling, crashing waves.
God, that sounded corny
I didn't care. I wanted to test him. To see just how creative he could get. And how much I could handle before one of us collapsed.
We did it in three more positions, each one more adventurous than the next - both physically and sexually. It was more a yoga session than sex. OK, maybe not more, or even as much, but it was certainly much more physically demanding than any sexual experience I'd had. And a much different pace. Instead of pumping into me, building a pace where both of us were lost in the frantic friction our private parts were making, Glenn took everything slow. Deep, elongated thrusts penetrated me from various angles. His cock brushed and bumped parts of my vagina I hadn't ever felt stimulated, at least not in that way. It was all fun and new, but it got to a point where I wanted more.
What do you have up your sleeve?
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Open Marriage - Cancún
A heated vacation
Scott and Mandy take their trip
Updated on May 30, 2026
by Uno1Dos2Tres3
Created on Dec 19, 2025
by Uno1Dos2Tres3
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