Keith wanting to share me with another man was never something I expected. He’d never even brought it up — until we went away to the Caribbean for two weeks to escape the frigid Chicago winter.

During our first night out on the island, the waiter brought us delicious tropical drinks and appetizers, while we waited for our main meal. I was already excited to be on vacation, but when Keith casually stroked my arm, he created tingling sensations within me that made me shiver.

The evening was warm and breezy, and the sun was just beginning to set.

“You think he’s handsome?” Keith suddenly asked.

“What? Who?” I replied.

Keith was looking very relaxed in the purplish light of dusk. The first few buttons of his white shirt were opened, and I saw his skin was already sun-kissed from being outside that afternoon.

“The waiter, silly,” he said to me.

“Oh, him? Yeah, I guess?” My response sounded like a question because I was slightly confused and wondering where his comments were leading.

But our waiter was indeed a very handsome man. Tall and lanky, but with lean muscles and a bright smile. His dark hair was tousled by the sea breeze. His all black outfit seemed to highlight his slender, rock-star physique. Back when I was a single girl, I’d have been drooling over him without any prompting.

Keith tangled his fingers through mine and said, “I thought since we’re on vacation we might spice things up.”

I’d initially assumed he was angling for sex on the balcony or maybe getting busy on a deserted spot of beach. I was more than a little surprised when he said, “I thought maybe you’d like to try some hot new men.”

My mouth popped open, and I stared at him. But I realized he wasn’t joking, and my pussy became instantly wet as my heart thrummed with unexpected excitement.

“Are you really serious?”

“I am. Very serious,” he said as his eyes reflected his fiery passion.

As I took a healthy sip of wine, my eyes fell on our handsome waiter again, and I said, “So, him.”

“Him, or whoever else you prefer.”

“Wait, you’d said ‘men.’ As in plural. More than one?”

Keith shrugged and smiled, his playful expression was one I hadn’t seen in ages.

“If you want more than one adventure. No pressure. But I’d be OK with it, if you are.”

The waiter was swiftly coming our way. My heart pounded even faster, and my panties were thoroughly drenched. He served our entrées, and after he walked off, I turned back to my husband to ask, “Well, who’s talking to him? Me or you?”

His hand slid up my thigh beneath the table, and he gave my leg a squeeze.

I was going to fuck him so hard when we got back to the hotel room.

“I’ll do it. Leave it all to me,” said Keith, who did indeed leave our table to chat with the lanky server before whisking me up to our room.

Kneeling on the bed, I sucked Keith’s dick like my life depended on it. I was so turned on by the idea of him watching me with another man that I felt like I was going to come before he even touched me.

I brought my husband so close to climaxing, he practically growled. Keith pulled back from me, and then positioned me on all fours. My hands clutched the bedsheets as he hiked up my skirt and yanked down my panties. I wriggled and shifted, helping him pull my undies all the way off. Then he grabbed my hips and thrust into me eagerly.

We fucked like animals, quick and dirty. He reached around, bringing his fingers to my clit and strumming me to a fierce orgasm. I climaxed seconds before he came inside me.

As we relaxed together, Keith said, “So I talked to Ken. Ken the waiter. And we have a date with him tomorrow in the late afternoon. Before his shift starts.”

“I can’t wait.”

Keith’s fingers slipped inside my cunt as he said, “Me either.” Then he worked me to another orgasm with fingers that knew my pussy almost as well as my own.

The following day came quickly. Ken seemed bigger than in the restaurant. Even when I was standing, I had to look up at him to meet his gaze, and that sent a thrill through me.

The waiter said hello and gave me a kiss, sparking a sensation that shot straight to my pussy. Knowing Keith was sitting nearby in the upholstered, high-back chair — and intently watching us — made it all the better for me.

Ken pulled me hard against him and slid his hand beneath my skirt as he whispered, “Is this OK?” But he didn’t wait for my answer and pushed his hand into my panties.

Yes, yes, yes. I nodded crazily as his fingers grazed my crotch.

Ken tugged down the front of my top and latched onto my nipple with his warm, wet mouth. As he drew on that nub, he also slipped a finger inside my pussy. My body sagged against his, overwhelmed by the feel of him penetrating me and the sensation of him suckling my tender tit.

Ken pushed a second finger inside me. He curled his digits within me, nudging his fingertips against my wet walls as he moved his lips to my other nipple. He was hunched over me like a hungry lion protecting its prize.

Keith grunted from the corner. It was a husky sound of approval that sent butterflies fluttering in my stomach.

I stood on tiptoe, arching my back and pressing my body closer to Ken’s. His fingers flexed and thrust. I gave in to the pleasure he triggered, coming easily.

When Ken withdrew his fingers, they were wet with my juices. He pushed them into my mouth, and I sucked on them.

Keith uttered an animalistic sound that made the hair on the back of my neck stand on end.

“I think you really need to fuck her,” my husband said.

Ken didn’t need to be told twice. He hooked his arms around my waist and lifted me up. He deposited me horizontally on the hotel bed and stripped me, taking his time to run his fingers over my nude body.

Then, he stripped himself, keeping his eyes locked on me. I glanced at Keith, who was sitting there with a raging hard-on in his shorts. He had an odd look on his face. Expectation? Desire? Excitement? Or maybe all of them at once.

Ken spread my legs and dropped down to give my pussy a few hearty licks. He dragged his tongue along my clit and lavished my folds with oral attention. After a few more maddening swipes of his tongue across my clitoris, he pushed his body between my thighs and dragged the head of his cock across my slit. My body bucked involuntarily at the sensation of his hard-on traversing my sensitive clit.

“Fuck me,” I begged. I tilted my head back and looked at my husband, upside down. Keith’s expression was intense, and I wanted to fuck him just as badly as I did this stranger.

But Ken stopped my train of thought by plunging his big, hard dick into my pussy. I gasped, my cunt quivering around him. My insides were practically singing at the blissful intrusion.

I gripped his lean hips and moved against him with every thrust, so our bodies collided in the best possible way. His cock hit all my sweet spots, and when I glanced toward my husband, I saw him leisurely jerking off. I knew the combination of Ken’s cock and Keith’s excitement would send me over the edge.

I squeezed my pussy muscles around Ken’s cock and slammed up to meet him. He grunted and sighed loudly.

“That pussy of yours,” Ken said. “Too good. I don’t think I’ll last much longer.”

“Me either,” I confessed, giving him one final squeeze with my internal muscles as he drove into me fiercely.

I came, crying out at a startlingly loud volume. Ken, set off by own orgasm, flooded me with his come. His warm load filled me, dribbled out of me and coated my upper thighs.

I laid there catching my breath as Ken put his clothes back on as quickly has he had removed them. Once he’d dressed, my husband — still sporting a woody — led our guest to the door and showed him out.

Keith returned to me wearing nothing but a happy smile.

“You were a hit. He’s already asking if he can see us again.”

I eyed my husband’s erection and said, “You enjoyed watching that.”

“Yeah, I did.” Keith pushed my thighs apart, so he could see my messy pussy — flushed, plump and leaking jizz. “Let me show you how much.”

He pinned my arms above my head and slid his cock into my cunt with ease. As we lay belly to belly and face to face, he started to move his hips.

My clit was so tender. Every thrust of his pelvis sent a zing of pleasure through me.

“Oh!” I exclaimed as my pleasure built. “Oh, fuck.”

He latched his mouth onto my throat, drew on it and marked me as his own as he fucked me faster and harder. I wrapped my legs around his waist and moved with him. When he came, I came, too, feeling the hot rush of his cream inside me and his warm breath on my shoulder.

He looked down at me, panting and flushed with pleasure.

“I have someone else in mind for you,” he said.

My interest was piqued, but I wasn’t allowed to know who he’d chosen until we went to dinner the next night.

I wore a short green dress with strappy sandals and my hair in a high ponytail. It was probably snowing back home, but it was balmy and nice where we were.

We sat at a table outside, and I couldn’t help but look around as I tried to spot the next person my husband wanted me to fuck.

“He’s not here,” Keith said, guessing what I was doing.

“Damn!” I laughed. “Well, where is he, and how did you meet him?”

“At the hotel. He runs the joint.”

I gaped at him in shock before asking, “The manager?”

He nodded.

I remembered him well. Said manager was six foot six easily. The day we first met him, he was wearing a well-tailored light summer suit, and he filled it out very nicely. He had dark yet luminous skin, an adorable smile and intense brown eyes.

“He has an ass to die for,” I blurted out.

Then we both laughed.

“When?”

At first, Keith looked like he wasn’t going to answer me. But then he said, “We’ll have a light dinner, a drink or two, and then go back to our room. He’ll be waiting there for us.”

“How will he get in?” I asked, but instantly realized the obvious answer.

“He is the manager,” Keith explained needlessly. “He’ll get in.” Then he leaned forward and whispered in my ear, “Into the room, and then into my wife.”

I could barely contain myself through our dinner.

As we walked back to our digs, my whole body was buzzing with excitement. I wanted it all over again: a stranger inside me and my husband keeping watch.

We walked into the room, which was filled with lit candles, and I gasped at the stunning sight.

“I can do that. I’m the manager,” a deep voice said.

He was sitting in the chair in the corner. He rose when we entered, and I marveled again at how tall he was.

“Curtis,” Keith said jovially, shaking his hand.

Curtis nodded and asked my husband, “Are you sure about this?”

“Very,” Keith said. “You’ve met my lovely wife.”

Curtis kissed my hand gently, and I couldn’t help myself, I giggled.

“I look forward to getting to know you much better,” he said, and I sighed in response. “May I?” he asked.

I nodded, and with that, he whisked my dress up over my head.

Keith took a seat and deliberately faded into the background.

Curtis peeled down the cups of my bra. His thumbs stroked my nipples until they stood up in hard little peaks. Then he bent to suckle one. The sensation of him drawing on my tit went right to my cunt, and I let out a lusty sigh. He moved on to the other nipple, and I shivered. My aching pussy was unbearably wet.

He whipped off my bra and panties, leaving me naked.

“Touch her,” Keith whispered from the dim corner. “I bet she’s absolutely soaked.”

And I was. I got even wetter when Curtis spread me out on the bed, parted my legs and went to work licking my pussy. He lapped at me softly and with a rhythm that wiped my mind. It wasn’t hard. I was already half gone with horniness.

Curtis lapped at me heartily, and I pushed on the back of his head with my hand. I shoved my pussy hard against his busy mouth. My orgasm hit so swiftly, it stole my breath. I tried to move back, so I could encourage him to get on top of me. But he grabbed my hips, hauled me back and challenged, “Who said I was done with you yet?”

Upon hearing his words, I nearly came again.

Curtis’s mouth went back to work, delivering whisper-light licks along my folds. His tongue nudged my clit, then two broad fingers slid deep inside me. He finger-fucked me, and I bucked my hips, eagerly taking every stroke.

“Oh, fuck. Yes, right there,” I gasped.

Curtis stayed on target, moving his fingers in and out swiftly and sucking my clit eagerly.

I heard Keith groan, and I came once more, my juices flowing from my pussy and coating Curtis’s fingers.

My handsome lover stood and stripped off his clothes, while keeping his intense gaze focused on me. He’d worn a casual polo and shorts since he was off duty that evening. But when his shorts and briefs came down, I saw his hard cock was ready to get to work and please me.

I took hold of his shaft, stroking him eagerly. There was no hiding how much I wanted him.

Curtis urged me back gently and pressed his erection against my pussy. My body parted for him and took him in, my muscles milking his thick cock. He thrust deep, and when I relaxed fully and freely accepted him, he increased his pace.

He settled most of his weight against me and licked my earlobe, then he gave me a nip. That sharp bite of pain blazed through my center. My pussy clenched around his girth, and he made a satisfied sound.

“You want it harder?”

“Yes,” I gasped.

He pulled free of me and then flipped me onto my belly. He was a strong man, so rolling me took little effort. At his urging, I got on my hands and knees as his hands skated over my hips. Every touch was pure pleasure and made me crave him plunging back inside me.

On the bed on my hands and knees, I could see my husband watching us.

This time his hands were on his lap, but he wasn’t touching his cock. However, his face spoke volumes, and I knew his dick had to be achingly hard.

Curtis got behind me, his hands squeezing my hips as his dick slid along my slit teasingly. And then finally, blissfully, he plunged into my wet recesses and started to fuck me. He filled me to the brim with cock, jamming into me so fast and hard he rocked me forward.

I saw a flash of excitement in Keith’s eyes, and that excitement amped up my own.

Curtis looped his arm beneath my belly, holding me tight as he rode me hard. Every thrust pushed me forward, while every withdrawal pulled me back. I shut my eyes, feeling the intense pleasure of his thick shaft driving in and out of my tight pussy. I squeezed myself around his dick, and he moaned.

At the very same time, Keith exhaled loud and slow. That was the sound of my husband trying to keep his control. I knew it well.

Curtis slid his hand down, cupped my mound, found my clit with his finger and stroked it. He used simple, even strokes, up and then back. It was as if he was painting my flesh with pleasure.

I moaned and found my rhythm, pushing back to take every inch of his thrusting cock.

“That’s it,” he said. “Come all over my dick.”

I pushed my hand beneath my body, moving him out of the way and taking control of my satisfaction. I stroked my clitoris, dragging my fingertip over that swollen knot of flesh and drawing whirls on my tender skin. I was so close to climaxing.

Keith approached us and placed his palm on the hand I had braced on the bed. I was trembling, trying to balance myself and keep stroking my pussy at the same time.

“Come for him, baby,” he said, leaning close to my face.

The sound of his voice made my nipples grow hard, and my skin rippled with excitement.

Curtis slapped his hand against my ass, the impact making a loud crack. I cried out loud, and he repeated the act, spanking my ass firmly. I moaned as the intense sting faded into a warm, syrupy pleasure. My pussy flexed around his shaft as Keith continued watching us intently.

I pushed back to take Curtis’s cock as another blow landed, then another, and every burst of pain made my pleasure more intense. I gave my clit a smack, paused, and then went back to stroking myself. I soon came, falling forward against the bed. My orgasm was sudden and intense, and it stole my breath.

Curtis pumped into me a few more times, and then I felt his sudden withdrawal, followed by the warm rain of his come splashing on my ass cheeks.

Keith’s face wore a look more intense than any I’d ever before seen.

Shortly afterward, Keith sent Curtis happily on his way, and then I was on my back, with my legs spread and my husband nestled between my thighs.

Keith fucked me furiously, his body trembling over mine. I was really worked up from my encounter with Curtis, so it didn’t take much to push me toward another release. I came, my pussy milking him. In response, he went taut and emptied into me with a gruff cry.

“Did you enjoy your adventure?” he asked. “Will you remember our time here?”

I snuggled closer to him, thinking our trip had featured the most memorable sex I’d ever had as I said, “I believe we’ve made more than enough memories to keep us warm through our cold Chicago winter. Very, very warm.”