🌴 Tropical Permission 📖 Chapter Four: The First Time

Her husband asked about her past. She told him how it felt to be used—and loved it all over again.

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The villa was dim and quiet, but for the distant hush of the ocean. The balcony doors were cracked open to let the night air in. The curtains stirred slightly in the breeze. Diane stood at the foot of the bed in a camisole and nothing else, her bare legs catching the last of the moonlight spilling in through the windows.

James lay against the pillows, shirtless, the sheet rucked low on his hips. His chest still warm and flush from the day’s sun. His arm was behind his head, his other hand resting just above his waistband. He looked relaxed—but anticipatory. His eyes tracked her as she moved toward the bed, curiosity sharp behind them.

She crawled up beside him, then swung one leg over and straddled his thighs. His breath caught.

“So,” he said, quiet and expectant. “You gonna tell me?”

She nodded, leaning down to kiss his collarbone. “Yeah,” she said. “I’ll tell you.”

Her hand slipped beneath the sheet. He was already half-hard. She touched him lightly, teasing, and began to speak.

⸻

It was right after college. I was living in D.C., broke, in this awful garden apartment that smelled like mildew no matter how many candles I lit. I’d just started seeing this guy—Colin—who worked in the same office building as me. He worked for some human rights NGO. Kind of a grungy hippy, but he was cute. Cocky in a way that I didn’t totally buy but still found charming.

He had a place off U Street even smaller than mine. Twin bed pushed against one wall, a nightstand made out of cinder blocks and a piece of wood, records stacked on the floor because he didn’t own shelves. He had this terrible neon sign above the window. “Good Vibes Only.”

James let out a soft, skeptical groan.

I know. I should’ve left right then. He had a lava lamp, too! Whatever. I was young. And he was cute.

So one Friday after work we were hanging out at his place. Just the two of us. We’d been drinking gin and tonics all night and got a little sloppy, and...you know.

Anyway, we were just hanging out in his bed - I think maybe I’d put one of t-shirts on but that’s all either of us were wearing - and his roommate Nate home early from his bartending job at some fancy hotel by the White House.

I guess he went in that night and he wasn’t on the schedule. And he was sure the manager was screwing him. Whatever. He just barged into the bedroom, sat down on the end of the bed, and started complaining about what had just happened, all the tips he was going to lose on a Friday night, how his manager was a prick, how he’s definitely sleeping with the new hostess. He went off.

At some point he stopped to take a breath and it dawned on him: his roommate is shirtless, in bed with the girl he’s been seeing, her clothes are on the floor, there’s a condom wrapper on the nightstand, etcetera.

He turned bright red and began apologizing profusely. I leaned up in bed and reached out to touch his shoulder. I genuinely felt bad for the guy, for the work stuff and especially the embarrassment. He started to get up and I lightly pressed him back down onto the bed.

“Nate, relax,” I told him, still with my hand on his shoulder. “That all sounds like a nightmare. Hang out with us for a little bit. I swear we don’t mind.” I offered him one of the G&Ts we were drinking.

He accepted and I got out of bed to make it for him. So now he knew I wasn’t wearing any pants, but I was in Colin’s shirt - and Colin was a pretty tall guy, maybe six-three - so he couldn’t see anything. But there was a little coffee table in the bedroom that we were using as our makeshift bar, and I made sure to bend over while I mixed in his drink, directly in Nate’s line of vision, so he could see I wasn’t wearing any panties either.

She was rubbing James through his boxer briefs now, which he was visibly, rigidly straining against.

I handed him the drink and he said thanks and I got back in bed with Colin. I swear I hadn’t planned anything, but Colin looked at me mischievously when I was curled back next to him. Then I kissed him. He responded in kind like he really meant it. The next thing I knew we had kicked the sheets off and I had relieved myself of Colin’s t-shirt.

Nate was still sitting at the edge of the bed, nursing his drink. He didn’t say anything but he was watching us intently. Colin had started sucking one of my breasts while he worked his fingers between my thighs.

She kissed James again, this time lower, dragging her lips over his chest as her hand slid along the waistband of his shorts.

“I think it’s time for these to come off.”

He let out a quiet groan in agreement and slid his thumbs down his hips, helping the process along. She slipped them off his feet, tossing them to the foot of the bed. Diane had never seen him so hard. She put her hand at the base of his shift and it twitched and started to leak. Slowly, she wrapped her hand around him fully and started stroking slowly.

I could feel Nate’s eyes on us and it was really turning me on. He was keeping this intense eye contact with me while Colin kept his focus on my body. He was rubbing himself over the top of his black work slacks while he watched.

“Why don’t you get more comfortable,” I suggested and then I gently pushed Colin onto his back and took him in my mouth while Nate quickly started to undress.

She tightened her grip on James and he moaned loudly. There was a steady dribble that had run onto Diane’s fingers. She licked it off from her knuckle to his tip.

Nate had taken off all his clothes and I looked up at him while Colin was still in my mouth. Colin was cute, but Nate was...*hot*. I told you, Colin was tall, Nate was at least an inch taller. Probably six-four or six-five. And he had an incredible body, clearly a gym rat, firm and sculpted. Oh and he had a ton of tattoos - a full sleeve on one arm, some sort of tribal symbol on one of his pecs, just all over his body.

”Did he have a big dick?” James asked between groans in a throaty whisper.

Yeah, I kind of buried the lede. Right away I noticed he was huge. Definitely the biggest I’d ever seen to that point. Maybe ever. And it didn’t take long before I found out it got bigger.

Suddenly, James grabbed Diane’s hand, startling her. He held her wrist.

“Is everything okay?” She was worried she’d touched a nerve. James had never been insecure about his size. He had absolutely no reason to be.

“Just...slow down a little bit.” And he loosened his grip on her wrist, let his hand fall back to his side.*

Nate had moved over to my side of the bed, still watching us, touching himself now. I told Colin to stay where he was and I got out of bed and pressed my naked body against his roommate. He cupped hand under my ass and the other on the back of my head as he put his lips on mine, worked his tongue into my mouth. I reached down and grabbed him, feeling how big it was in my small hand. Felt it grow with my touch. I used my hand to guide him to the bed, pushing him down on the mattress next to Colin. Then I crawled onto the bed in between them and took as much of Nate in my mouth as I could, gagging as he quickly hits the back of my throat, repositioning myself so I could take more of him.

Colin watched eagerly. I reached to take him in my hand but he gently batted me away. “Keep sucking,” he instructed.

Now, if Colin had said something like that to me when it was just the two of us fooling around, I don’t think I would have taken it well. But in that moment, it was maybe the hottest thing anyone had ever said to me.

When I was in my twenties I mostly thought of sucking dick as a detour to the main event at best, a chore at worst. But that night, on my knees in that tiny bed, I was voracious. And Nate was so big, I had to really work at it: spitting and drooling all over him, repositioning myself to try and get more and more of him down my throat, using both of my comparatively tiny hands to pull on his slick, rigid shaft, using my tongue and my palms to tease his swollen head.

She paused and stopped telling the story, deciding to show James instead. She took him into her mouth and all the way down her throat in one fluid motion, almost to the base, gagging slightly, then pushing herself further down, choking herself on him until she couldn’t take it, before coming up gagging and drooling.

James’ whole body shuddered and he grunted something unintelligible. Diane used her index finger to wipe some spit from her chin, keeping her focus on James as she did.

“Shall I continue?”

“Yes, please.”*

I was so lost in Nate that I didn’t even notice that Colin had gotten off the bed and moved behind me. Then I felt his hands grip and spread apart my thighs, then my ass cheeks. He buried his face into me. I let out a muffled moan with my face buried in Nate’s lap. Colin made me come like this, mouth full, struggling, breathing through my nose. I’d never climaxed with a guy in my mouth before, and it kind of took me by surprise.

Nate pulled me up and kissed me. I remember my mouth being so wet with saliva, it was just running down my chin, onto my breasts, all over the bed. Nate lapped it off my chin between kisses, grabbing and groping at my tits as he did. Colin was rubbing his hands all over my ass and my thighs, continuing to tease my inner thighs with his lips.

What’s that idiotic terms that guys use? Spank bank? Well, I just remember in that moment - right after I came the first time, but before they were inside me - thinking to myself ‘don’t forget what this feels like.’ And I haven’t. I felt like a goddess. Exalted. I felt like I was being claimed from both sides but that I was claiming them too. Like their desire for me was a superpower I had absolute control over.

James was hanging on every word. She could feel his reactions to each turn of her story as she gripped him, each new detail causing him to twitch and pulse.

“Does that sound silly?” She asked.

“Not at all,” he answered without hesitation. “In fact, I was just thinking to myself, ‘Jesus, my wife is a secret sex goddess.’”

That answer pleased Diane greatly and she showed her appreciation by swallowing him whole.

Alright, it gets a little blurry from here on out, but I’ll do my best.

I’m kissing Nate and he whispers in my ear, “I want to fuck you.” It was the first thing he’d said since we all started fooling around. My response was something like, “what are you waiting for?” I told you, I was feeling like a goddess!

The boys did a little musical chairs while I waited in bed on my hands and knees. Colin took Nate’s spot on the mattress, and it occurred to me that I had all but forgotten poor Colin while I was so focused on tending to Nate’s... significant... needs. So while Nate got himself situated with a condom, I used my lips and my tongue to show Colin he wasn’t being neglected.

Then I could feel Nate’s weight at the end of the mattress. His strong hands gripping my ass. His fingers sliding between my lips, dipping inside me. I was literally dripping with anticipation.

Finally I could feel his head start to push against my lips, then between them, and then inside of me. He knew what he was doing, was fully aware of the relationship between his size and my tightness. He started thrusting slowly, gently almost. I didn’t realize he wasn’t even halfway inside me. That he was just working it in. Opening me up for the full length of him.

When he did slide all the way inside me, it literally took my breath away. When it happened I reflexively tightened my grip around Colin so hard I was worried I’d hurt him. Nate stayed there for a second without moving, letting me get used to this new feeling of fullness. I melted into it, melted into him, melted into Colin. The sensation of being so thoroughly filled up by both of them was exhilarating. Again, I just lost myself. This simultaneous feeling that I was being taken and used, but also that I was the one doing the taking. I was in control.

It really gets fuzzy from there. I was overwhelmed by this beautiful, dark wilderness. Four hands, two mouths, two dicks. They took turns inside me. They moved me into different positions, my knees, my back, my stomach, my side. I couldn’t stop coming. They wouldn’t let me.

James’s eyes were fixed on her, wide and dark. She couldn’t believe how hard he was now, thick and pulsing in her hand.

She could tell he was right on the edge. And that she was in total control of his pleasure.

He swore under his breath.

She pulled back slightly, stroking him with one hand, rubbing his rising chest with the other and continued.

It felt like the three of us were locked together for an eternity. I didn’t want it to stop, but I wanted their come. Desperately. I was on my back, Nate had just made me come again in missionary, and Colin was laying at my side, watching and stroking himself. I put one hand on the back of Nate’s head, the other on Colin’s sweaty thigh.

I looked at Nate as he thrust into me and said, “do you want to come all over me now?” Immediately, he pulled out and started ripping the condom off. I turned to Colin and he understood the question was also for him, and positioned himself over me. Nate came around my other side and sprayed all over my face and chest within seconds. Colin bent down and kissed my dripping mouth and then shot his load all over my chest.

There was no cleanup plan, no towel in reach. I started laughing, dripping. Nate ran to get a T-shirt for me. He tossed it to Colin who wiped me off delicately. We were all soaked in sweat. I can’t imagine what it smelled like in there.

⸻

She took him into her mouth again, deeper this time. Her tongue moved in slow, firm circles as she sucked, working him steadily. He groaned, fingers tightening in the sheet. His hips began to rise toward her, helpless.

She pulled off with a pop.

“Want to know what I was thinking during dinner?”

He nodded, eyes wild.

“I was remembering what it felt like to be completely used up. Ruined. And how powerful that made me feel.”

That did it.

James grunted, hips bucking, as he came hard into her hand. She stroked him through it, slow and steady, until he collapsed back into the pillows, chest heaving.

She crawled up beside him, pressed a kiss to his temple, and curled into the crook of his arm.

For a while, neither of them spoke. The breeze shifted the curtains again. Somewhere outside, a gecko chirped.

Then James exhaled and said, “Jesus, Di.”

She smiled into his chest.

After a beat, he added, “Tell me about the second one. Sometime.”

She kissed his chest. “You’ll get the whole story.”

Outside, the sea went on and on.

⸻

Want more? Read Chapter Five here.