Cucked in Key West Ch. 01

"So you're not going to believe what my boss just told me, "I said as she picked up the phone.

"Your boss Will? What's up?" I could hear road noise, she was probably out driving uber in her little red Honda.

"So he just stopped by my desk out of the blue and said he was tired of working from the office when nobody else was coming in, so he'd decided to work remotely for a while... From Key West."

"Yeah, he does put a lot of hours in," She said. "It'd do him some good to get out and have some f--."

"That's not the crazy part..." I cut in. "He said he wanted me to come along so I could help handle calls for him and he wouldn't have to be on the phone the whole trip."

"Yeah, so what'd you say?" She was driving and sounded a little distracted.

"So at first I said I couldn't go because your parents were coming into town."

"Oh right..." she said. "But they aren't gonna to be here for three weeks."

"Yeah, that's the thing--he isn't going for a week, he's going for a month."

"Oh shit, I'll be pissed if you leave me for another shitty Minneapolis April while you're partying in the tropics with Will," she laughed.

"Of course, so when I told William I couldn't go because I had plans with you, he said that he expected you would come too--he has a spare room in some villa his family owns."

"Hold on--I'm pulling over," she said, and I heard her blinker come on and some bumping sounds as she pulled off the road into some parking lot. "So you're telling me that your boss Will is taking a vacation to a fancy beach house... And he wants to take his secretary and his secretary's wife? That doesn't make any sense."

"That's just it, He's not going on vacation, he's just going to work remotely, and I think he wants somebody there local to cover for him so he can go out and enjoy himself without it being obvious he's screwing off. I'll be handling his emails and screening his calls".

"Oh hell yeah! When do we go?" she half shrieked into the phone. I could picture her pretty green eyes wide with excitement.

"He said we'd fly out this Saturday, and to let him know today so he could buy our tickets."

"Okay I'll tell my job I won't be in." I heard her tapping on her phone. "Fuck you Uber, I'll be back in a Month!" she shouted. "And Done... Hell yes, this is the most exciting thing ever, I can't believe it. She was talking fast now. "Oh thank god I've been hitting the treadmill all winter, fuck you snow, fuck you winter, fuck you Minnesota--oh shit I better hit the tanning bed an extra time this week--and I need a bathing suit! I'm heading to the Mall right now.

--

"So what do you think?" she asked. I was off work, back at our Apartment and she was showing off the stuff she'd got at the mall. She had on an emerald green bikini that matched her eyes, and complimented her long blond hair. It lovingly cupped only the most private part of her breasts, showing off her fair skin, which had just a hint of pink from her tanning session. It clung tightly over her crotch, was connected by thin straps around her waist, to a thin ribbon of fabric in the back that was barely more than a G-string, showing her perfect ass.

I felt my breath quicken, and my dick twitched and grew pressing against the tight khaki pants I'd worn to the office. "You look so fucking hot." I said and I stepped across our little kitchen and slid one hand down the curve of her back to her nearly bare ass, and the other traced the soft skin of her flat stomach up to her breasts, her nipples hardened visibly from my touch.

She stood stalk still, puffed out her chest, and raised her chin while I fondled her. "I had a blast getting sloshed on Jaeger with Will at the Christmas party last year. He's going to be fun to hang out with. It's so badass, that you're working with a bigshot who can take us to something like this."

I slid one finger between the thin green suit and the cleft of her supple ass. "So what do badass men with sweet jobs get from their wives when they take them to the Caribbean?" I gently slipped one finger between her smooth ass cheeks.

"You know the rules," she said with a little sly smirk. "I just got off my period yesterday, you'll have to wait."

--

"The rules". I thought to myself later that night. I was naked between her legs in bed, my face wet from licking her to orgasm. My own cock throbbed erect and ignored.

It had started a couple years ago when we were still newlyweds. she had noticed that she hadn't gotten pregnant although we fucked regularly without protection. We wanted a family, so she'd gone in to the doctor, and when he said everything about her tight little pussy was absolutely perfect she made an appointment for me. The doctor had said my sperm counts were off-the-charts low, and even a bunch of follow up visits they couldn't say why, "some kind of an autoimmune issue" they said.

The rules came about after her friend, not a doctor, told her that it was known that cumming too much wasted sperm. She had decided to put some restrictions on when I was allowed to get-off. At first it started as a joke which was flexibly enforced, but she soon realized how frustrated and aroused I got by having her control that part of my life, the rules stuck... The rules were that I wasn't allowed to masturbate to finish, or even allowed to cum at all without her permission... And she only gave her permission during the time of the month when she was most fertile, and sometimes not every day of it.

But our physical relationship wasn't all bad... She recovered from her pleasures, and came up on her haunches, her chest still flushed pink, and directed me down onto my back. She looked down at me sternly with her bright green eyes "Tell me when." she commanded. She got on her knees, leaned down mouth-open to take my raging cock. My dick was tipped with precum as she opened her soft lips and slipped them over the head of my cock. She ducked her head down easily taking me all in her mouth with her lips at my base.

For only a minute she sucked and bobbed, I moaned, and felt pressure growing quickly "I'm close!" I shouted, and she opened her mouth and sat up watching me, her face serious, her large breasts perky and tight. "Good boy," she said in her sultry voice while I groaned and struggled to avoid peaking. "This is a reward and I'm going to do it twice more, but if you mess this up you'll get nothing until well after we get to Florida."

She let me recover for a while. When I was calm she continued, darted her mouth down again she took my swollen tip and swirled it with her tongue. The second time took maybe thirty seconds, but the feeling was incredible, but as I started to cry out, she sensed it was time and rose up again beside me with one hand on my thigh and the other on my chest. She waited...

I watched her plump sexy lips move "Once more, and then it's bed-time."

She took me again, deep. Her mouth was so warm and so caring. The last time was even much shorter, but when my legs started shaking she didn't stop, instead I had to push her lightly away. I knew the consequences if I came, and I didn't want to go back in the cage again.

It wasn't just my dislike for the male chastity cage she'd bought for me... I wanted a baby too, and although I didn't think orgasm denial was a realistic path towards that, I wanted her to know I was serious about it, and that I was doing whatever I could to help make it happen.

For a moment a string of spit strung from her lips to my still throbbing cock as she sat up and rolled away across the bed, my eyes following her taught and slightly sunburnt ass. "Put your underwear on and get some sleep," she said. "You've got to work tomorrow." I groaned and stood reluctantly up to comply.

We had an unconventional sex life, I thought, I was an office drone, with a kinky side, and she was a firecracker beauty who knew how to sniff me out and find out what I liked, even if I wouldn't admit it. We were young and broke, and living in Minnesota, but at least our sex life was fun.

--

Aria and I were holding hands waiting for my boss William at the busy baggage check at the Minneapolis Airport. The week had flown by with me working, and her packing, working-out, and tanning... Her Uber driving was "on-hold until after the trip".

"The line is pretty long and our flight is in an hour, do you think we should try to check-in without him?" I asked.

"Will!" she shouted in delight, spotting him approach through the crowd, and she left her roller-bag to run up and throw her arms around his chest with a hug. William was in his mid-thirties, a few years older than us, but he was tall and athletic with broad shoulders, blond hair, and piercing blue eyes. He was wearing a sharp grey suit with a blue tie, with a grey linen facemask. He had a strong English-South-African accent, which seemed to make him popular with the women at the office. It wasn't like I was a short guy, but She looked so small next to him, I thought. He put one arm around her, and they held for what seemed a moment too long to me, was that jealousy or am I feeling flattered? I felt something flutter in my stomach seeing them together.

He released her laughing "Aria, I haven't seen you since the Christmas party! Where has David been keeping you?"

"I know!" she quipped "That was such a blast, although the next morning I was so sick I haven't touched Jägermeister since that day".

"I'm surprised that bartender didn't cut us off," he said smiling, "or that I didn't get another letter from HR about having too much fun." He stepped up to me still grinning "David! You ready to do some work in paradise?" he said taking my hand in a firm grip.

"Of course," I said nodding enthusiastically. "I've got my laptop charged and the swim-suit ready."

"Good man" he said in his South African drawl. You've earned it, coming into the office every-day to help me when everybody else was hiding out on Zoom... Flight is soon, let's get checked in. Follow me". He had a large sleek roller bag in his right hand, and he took Arias purple polka-dotted roller in his right and walked. Skipping the long line, he strode with long-strides to the front down the empty walkway for first-class as Aria and I followed behind as quickly as we could.

He handed a rumpled passport to the young girl at the bag check. "William Allen" the young clerk said flipping open his passport "Lot of stickers in here, you've certainly been around. Bags to Key West Florida?" He nodded. "Headed on vacation? You don't really look like you're from the south?" she asked him with a flirty smile.

"Yes I'm from the South..." he said flashing her a grin "The deep south of Cape Town South Africa" she giggled and batted her lashes at him.

Yeah, he was popular with women.

The girl took our bags and gave us each a boarding pass, and a half hour later we were past security to the gate, just as they called for boarding first class. "Oh shoot," William said, "I waited a little too long to think of this idea, by the time I did there was only two seats left in first-class. I decided to give one to the pretty lady. Sorry David, you're stuck in Coach this time, but it'll be first-class for us all on the trip home."

"I'm flying first class!?" Aria asked, her pretty green eyes wide. "I've never been in first class before, this is going to be great! Those tickets are so expensive though".

"Don't worry," he laughed, "the company is paying for everything! The way David has been keeping me on-task, our department's revenue is going up faster than god" he leaned over and ruffled my brown hair. "After what we did last quarter, I could probably expense my a private jet without a question. Now come-on girl."

My wife gave me an excited mousy smile and turned to follow him in the first-class boarding line. I watched her ass as she walked away with her hands at her waist, but then for a flash of a second she twitched her thin wrist, and her short red skirt flipped up, and I was shocked to notice she wasn't wearing panties. God she was hot.

Twenty minutes later I finally boarded the plane. William and Aria were sitting together in plush seats at the front talking like old friends, she was turned towards him laughing, with one hand on his knee. He had a glass of bourbon, and she was holding a long-stemmed glass of champaign, with an already empty glass on the tray beside her. They looked good together, I caught myself thinking with a strange twinge in my core. She saw me as I shuffled through the aisle towards the back and mouthed "Sorry baby." and reached across William's lap to slap my ass as I passed, he laughed, then they went back to talking.

Aria was a gregarious drunk, and she knew all my secrets. I was pretty sure she was going to say something embarrassing, but I hoped she didn't get drunk enough to mention certain things I had talked to her about.

I had shared my fantasy of seeing her with another man, and every now and then she reminded of it, usually about five seconds before fucking me to a screaming orgasm. As I set down in the narrow coach seat by the aisle, I thought back on that those conversations, and pictured her following William to the plane in her short-skirt and seeing her hand on his leg. After a moment someone came to sit on the inside seat and as I stood to let them move in and realized that I had to hide an erection that was pressing noticeably out from my soft travel pants. I performed a pirouette of movement to avoid brushing anyone with my erection in the tight confines of the cabin and finally sat back down. Get it together David, I though, this is a work trip, not a swingers party. Then I tried to focus on picking out something to watch on TV.

--

A few hours later we disembarked in Key West. William and Aria were waiting arm in arm like old school buddies when I trudged off the plane. She was drunk and chatty, but not blasted, so I thought I had lucked out. I took Aria's other arm and we walked together to baggage claim like it was a yellow brick road. Quick stop at the car rental where William picked up a bright blue Escalade, "David can you drive, I've had a touch too much single malt." He said and handed me the keys. I loaded the bags in the back, as he helped Aria up the backseat, his hand on her lower back to steady her. Then he playfully pushed out and her tiny form bounced across to the far seat laughing, and he climbed in beside her.

Yeah he was definitely flirting with her. For some reason though I didn't want to intrude between them. I pretended like I didn't notice anything unusual. William gave me the address to our house, and the two of them chatted and laughed about how different it was growing up in Cape Town compared to Minneapolis.

It was only a few minutes before we reached the place, I stopped the Escalade outside a big wrought iron gate, and William jumped out and grabbed a fob that opened it from a lock-box, and then hopped back into the back seat. The path lead down a short but narrow winding path lined with palm trees and tall hedges that suddenly opened up to a circle drive that ended at a two-story bungalow with blue siding and white trim surrounded by palms and hedges.

Aria's face was pressed to the glass like a child who'd seen Santa Clause as I pulled the car up. "Oh my god that's so cute!" she said.

"Come on, I'll give you the tour. I'll grab Aria's bag," William said. He helped my wife down from the tall SUV, and we set off to explore with her at his side excited, and me following a few paces behind. He lead us up the stairs and unlocked the front door. "This property has been in my family since before Hemmingway moved to the Island in thirty-one" he said as he unlocked the door and ushered us inside.

"You own this place?" Aria asked.

"Well, it belongs equally to me and my dad's brother, my Uncle Calvin. My grandmother told me that she was socially friendly with Earnest's wife Pauline when she summered here, but she always found the writer himself to be a bit of a boar." William gave Aria a conspiratorial wink and lead us on. She turned to me, her eyes bulging with excitement, she was a big Hemmingway fan, we followed William inside.

"My father had the whole place rebuilt after a fire in ninety-two," William said with his South African inflection "But they kept the basic floorplan..." The downstairs he explained was mostly storage and a parking garage and laundry due to potential flooding, the upstairs all floored with bright blue and white geometric tile covered with Persian rug. Inside the front door there was hallway and beyond I glimpsed a luxurious looking living room. Our bedroom was just inside the door, directly across from his own, "This is your room," he said to me. Aria and I stepped inside. It was a small bedroom mostly occupied by a king-sized bed with a few paintings on the wall, a little door to a toilet room. The most notable feature was a tiled lined walk-in shower that was behind clear glass panel at the side of the room. Damn, I thought with a trace of arousal, she'd be able to keep an eye on me in the shower to make sure I was following the rules. I had no idea then how things would soon play out.

"Well, I'll let you get settled in here. And then I'll give you the rest of the tour, and we'll go down to the beach." Then he shut the door leaving us alone for the first time.

I took Arias hands in my own "This place is off the hook" I said enthusiastically.

"I know, this is nuts. Like no fucking joke, Earnest Hemmingway might have been here. You got a secretary job through a temp agency, and two years later we're on vacation in the tropics." She said squeezing my hands so tight her nails were digging into my skin.

"So how was the flight?" I asked.

"Shit, sorry you were in coach, he, I mean the flight was delightful." She said, suddenly looking a little nervous.

"So..." I said fake casual. "What did you two talk about?"

Her voice dropped to an urgent whisper "Shit, they kept bringing me champagne, and he was telling me all about himself. And then... I told him a little about us." She said as if in a confession booth.

"What did you say?" I said, trying to keep my voice even.

"Not that much..." She paused "really, except I did say that we were having trouble conceiving... And that the trouble was on your end."

"Shit Aria," I hissed, "He's VP of a major company, and my boss, he doesn't need to hear about our problems. What else did you tell him?"

"Well I didn't tell him everything." She whispered eyeing me reproachfully, her full cleavage huffed above her green dress. "I sure as hell didn't tell him about your dirty fantasies of seeing me with another man."

My breath caught in my throat and my dick twitched unexpectedly.

"But he did say..." She whispered and drew me closer; I could smell her flowery perfume and I hung on her words scared as to what she would say. "He did say that he would be happy to help you."

"How would he help me--I've been to the best urologists and--"

"That's not what he meant." She whispered. "David, he was really respectful, but he offered make me pregnant on this trip... And that you and I would keep the baby for ourselves, to start our family."

I sucked in a breath and held it, my mind was racing. This couldn't be happening. I turned my back to her, as if to think but really to hide my unintended excitement at the thought of William having sex with my wife.

"You can try to hide from me, but I'm not buying it." She whispered harshly. "Turn around... Now."

I reluctantly turned back to face her. The thin, soft sweatpants I wore gave away my dirty little secret... I was fully erect.