Cuckold Dilemma Ch. 03

"I'd like to switch things up, Simon."

"What do you mean, Jess?"

"I want to discuss our terms on my being a hotwife."

"Fuck, yeah."

After a few successful trysts, my husband and I got into the swing of things. I let him watch frequently but, having purchased a hotel do-not-disturb door swing hanger, there were times I forced or kept him out using that signage.

Simon loved the shameful walk upstairs only to be condemned to an evening of tension if I left the swing hanger on the outside handle of the door to our marital bedroom. On occasions when I allowed him into our bedroom for cleanup duty, he was grateful.

I caged Simon for a few days before any cuckold date, sometimes left him locked up while I played with my swain, then released him, usually the next morning, to fuck me all day.

"Caging works well for me, Jess. I feel more attentive and powerfully motivated to reclaim and satisfy you."

"It's good for me, too. All my dates so far had smaller cocks than yours. It's great to be fucked repeatedly by an enthusiastic stranger, then have my pussy stretched by you."

"What do you mean by switching things up?"

"I want to fuck your boss."

"Jeremy?"

"Yep."

"Why?"

"I think the humiliation will do you good and a promotion wouldn't do us any harm."

"Umm Jess, that sounds really taboo and already has me horny."

"Dinner, Saturday night. You'll cook while I seduce, then fuck Jeremy."

Simon's boss snapped up my dinner invitation in a heartbeat. He'd slid in behind me at the buffet table during their last office party, pushing his steel cock package in between my ass cheeks.

I rebuffed him with a wiggle of my butt and a sideways shuffle, smiling at Jeremy to avoid harming my husband's career.

Simon went shopping, bought steaks for two accompanied by an excellent wine choice. After he cooked and served us, my husband went to the spare room, with cock locked, awaiting the sign on our bedroom door, or not.

"Isn't Simon joining us?"

"No, Jeremy."

"I'm confused."

"Why?"

"This feels like a romantic dinner, which is odd considering your husband just disappeared upstairs."

I lifted my oversized goblet of red wine, smiled seductively, and sipped the almost black merlot swilling around inside.

"Do you think I'm cheap, Jeremy?"

"No, no.. wh-why would you think that."

"The last office party?"

"Oh."

"Yep."

"I'm sorry about that."

"You may not have to be."

He leaned closer, my flirting had piqued his interest. The horny Chief Executive of US Operations for the worlds biggest aerospace company wanted to fuck me.

"What do you mean?"

"We could help each other, Jeremy."

"You mean a collaboration?"

"We each get what we want?"

"What do you want from me?"

"Italy."

He settled back in the dining chair, deep in thought, processing his options while smiling in the most lascivious manner. Jeremy swirled his wine thoughtfully.

"Ah. I see. You want the Italy CEO position for Simon?"

"He says you can make it happen with a single email."

"Yes, that's true. The job might be his, anyway. Your husband is the best candidate."

"Have you decided who it will be?"

"No."

"Then consider this evening my persuasion."

"What are you offering me, Jess? You know I have the hots for you. It's unlikely I could refuse."

"Could I get away with a kiss?"

"Do you think that's a fair trade for the dream of living in Florence?"

"No."

I lifted my legs onto the dining table, hitching my dress high. I pulled my ass cheeks onto the slick mahogany, slid towards him, resting my pussy where his plate had sat moments earlier. When I leaned back on my forearms and elbows, spread my knees wide as if serving my cunt for dessert, Jeremy licked his lips.

His eyes almost popped out as if on stalks and a delightful smile flickered across his otherwise poker face expression when he saw I hadn't worn knickers.

"I had Simon shave this pussy, especially for you a few hours ago. There is absolutely no hint of stubble anywhere. It'll be like licking silk if you are thus inclined."

"You're a beautiful woman, Jess, and yes, I love the flavour of a well groomed, excited pussy."

"You can do anything you like to this pussy and everything it's attached to for the next ten hours. I'll even throw in a breakfast cooked by Simon."

"Oh, wow."

"I'll need you to send that email before any plowing of this furrow begins."

"I need more, Jess."

I drew my knees together, accentuating what Jeremy might lose if he wasn't careful with his negotiation strategy.

"Counter my offer then, Jeremy."

"I'll take your offer tonight. You can witness the email confirming the Job is Simon's before I fuck you. On your arrival in Florence, I want the first weekend with you. Just the two of us, from midday Friday until 9am Monday."

We eyeballed each other for minutes, while taking an occasional sip of wine. I noticed the surface of his Merlot ripple against the side of the glass when his hands trembled with excitement from the thrill of the chase.

All the power in the room was mine, but only because I could suppress my emotions, or at least not reveal them. I opened my legs wide again, signalling the resumption of our negotiations.

"I think you should sample the prize before we strike an accord and you send that email."

He eyed my pussy like a leopard slinking towards its meaty target. I encouraged his head in between my legs by raking his hair, then pulling it.

"If you enjoy the free sample I'm providing, we'll close this deal."

Jeremy licked me savagely, vacuuming the excess cream gathered in the folds of my freshly shaven pussy. I felt a desperate urgency to his licking and sucking and knew our negotiations had turned in my favour.

"Slide a finger inside my pussy and feel how tight it is."

He did, and his eyes told me I'd won Italy. By this time next month, my husband and I would enjoy one of the greatest cities in the world.

He sucked my clitoris, flicking the sensitive bean as if polishing a knot in a beautiful piece of wood. I bucked gently as my orgasm began, realising in that moment the danger he'd created for me and our deal.

Jeremy looked up at me with pussy slime dribbling from his bottom lip, down his chin, and onto the table below.

"I want a week in Florence with you."

"Hmm. I wanted to wait until you had some fun, Jeremy, then close our deal fair and square, but now you're cheating."

"What do you say, Jess?"

I left myself exposed, pushed forwards until my pussy lips grazed his chin, making sure my aroma slammed into Jeremy's psyche.

"This is my last offer, Jeremy. You'll get tonight, and your weekend, but my husband will receive one hundred percent of his bonus plan next week."

"Nobody gets one hundred percent, Jess."

"He deserves it."

"Yes, but nobody gets it. The maximum awarded is fifty percent or the shareholders go nuts."

"Alas, our deal is off then."

I lifted my legs, as if to move away, but Jeremy pinned them down to the table, panicking.

"Are you worth the extra seventy grand, Jess?"

"You're refusing to release my pussy. What do you think?"

He grimaced, shook his head vigorously and submitted.

"Oh fuck, yes, yes, okay. You're worth it."

"Good boy. Now finish licking my hole and we can open Simon's laptop for you to send that email."

"We have an accord, Jess."

He descended back amid my labia, but I hitched my ass high, arching my back so he could access my anus.

"You can clean that puckered hole since you tried to cheat me."

His tongue darted to collect the juices that pooled around my anal whorl. Jeremy licked enthusiastically, holding both cheeks in his palms, prising them wide open. I felt his thumbs splay my anus, and then a warm lapping of my rectum ensued when his tongue delved deep inside.

I lowered my butt so that Jeremy could focus on my pussy. He licked expertly, if a little desperately, while sliding a finger where his tongue cleaned moments earlier.

I shuddered, thrashing my arms across the table when my orgasm rose monumentally. The Uffizi gallery, Ponte Vecchio and Garden of Statues, flashed before my eyes, collaged with images of Simon and I enjoying lunch before a stroll through a delightful piazza or in between visiting boutique shops nearby.

"Oh Jeremy, that feels wonderful."

He cleaned my copious flow, swallowing greedily until the last flutter of delight shuddered from me and my soul rested back to earth.

Jeremy helped me down from the table and I unruffled my dress, nodding to a laptop on the kitchen breakfast table.

I carried our glasses to him while Simon's boss typed frantically. He turned the laptop towards me and I checked the email, nodding my acceptance. When he hit send, we waited for a minute and Jeremy showed me the read receipt.

"Just in case you didn't believe me, Jess."

"I have CCTV recordings of this room to make sure our deal sticks, Jeremy. Imagine what the shareholders would think of that."

His look of astonishment was replaced by anger in the blink of an eye.

"You bitch. Are you renegotiating?"

"Don't be silly, I'm rather looking forward to you fucking me now. I'll have the use of your company credit card when we enjoy our sordid weekend together in Florence."

"Oh, that's okay then."

"If you behave, I might make it a regular thing when you visit to inspect my husband's work."

"That may require bi-annual visits."

"We'll see Jeremy, now get upstairs and fuck me."

When we got onto the landing, I handed my lover a hotel do-not-disturb sign.

"You decide Simon's fate this evening, Jeremy. This sign goes on the outside or inside door handle."

I took my time undressing, presenting a show to delight Jeremy while he stripped in thirty seconds and lay on the bed with a monstrous cock pointing to the ceiling.

"That's bigger than Simon's cock."

"I've never had a woman tell me it wasn't the biggest she'd had."

"Seems I'm a lucky executive's wife tonight."

I crawled up my marital bed like a lioness, stopping once to look back at the door, pleased there was no sign on its inside handle.

"I'll have that lovely cock now, please, Jeremy. All night!"

"All nine inches?"

"Everything! I've been a good girl lately."

He held my hands while I squatted above his blue veiny monster. I have powerful muscles and especially the quadriceps holding me an inch above his swollen glans. When I lowered slightly, it was to rub his cock inside my pussy entrance to help it impale me down to his pubic bone.

I rocked gently on his glans, letting the top inch fuck me for a few strokes, before rubbing its shaft through the wet furrow between my labia. My slick juices transferred onto his dry, solid flesh.

I heard the squelching of two well lubricated pussy lips sucking on a fat glans.

When I took his cock inside my pussy, it felt much fatter than Jeremy's. When I reached half mast, I gasped because my soft tunnel walls clenched tightly on Jeremy's solid cock repeatedly.

My pussy stretched inside like at no other time I'd been fucked, and it blew my mind.

My head bowed to an overwhelming explosion of hormones surging through me, smashing every taboo, sacred vow and restraint that bound my marriage. I shook my head but couldn't clear my senses as I slid inexorably down Jeremy's amazingly fat, long cock.

I'll need this again.

"Do you like my cock, Jess?"

"Mmm, hmm."

I nodded, almost obediently. His cock was embedded inside me all the way down to his pubic bush, which bristled delightfully off my shaven mons. I smiled, bit my lip in subjugation and he knew he'd bested me.

When Jeremy flipped me over, his cock remained balls deep inside and my internal organs shifted slightly to accommodate its girth and length. He placed both palms on my bed, one on either side of my neck, pulling tight into the shoulder.

"You don't want me to move?"

"I'll never take advantage of you needing my cock again, Jess. I won't disrupt your marriage, so we'll do everything by your rules."

"Thank you, Jeremy. Good boy. Please fuck me now and make it loud enough for Simon to hear."

"That's in your swimming lane, Jess."

He retrieved his cock slowly, much to the regret of the pussy he was fucking. I kissed him deeply, breaking a rule, but it felt right because we were more like fuck buddies than a simple cuckold date.

We're business partners.

His lips sizzled against mine. My tongue jolted when it tasted the forbidden fruit outside marriage, breaking the hotwife rules Simon and I agreed.

When Jeremy thrust inside me, I held my lover tight, wrapping both legs around his waist, burying my face into his neck. With my body pinned, his stroke play was excellent and Jeremy fucked me, slowly at first, then harder and faster when my cunt widened, gleefully greeting its massive visitor.

He fucked me so hard we slid up the bed while he pummelled my ass deep into the mattress. I saw desire and delight in his eyes without feelings or love and felt pleased because I love my husband, but I now love Jeremy's cock almost as much.

My synapsis exploded, clouding my judgement as every taboo I'd chained down escaped, running amok inside my mind.

"Argh! Argh! Fucking Hell. Oh, my. Oh f-f-fuck."

"I think Simon will have heard that."

"Oh fuck, I hope so. Simon! I'm being fucked into oblivion."

A muffled shout vibrated through the wall, but I couldn't discern what my husband said such was the excellence of Jeremy's cock and his slut wife fucking technique.

I stared into his eyes, wiped the sweat from his brow while my lover reamed me at full pelt, ramming my pussy, which was properly stretched for the task.

"I'll ask him in the morning."

"May I cum inside you, Jess?"

"Definitely."

I clung to Jeremy riding his cock to orgasm ridge where he perched me until I felt a twitch, then a final bottoming out of his glans against my cervix. His hot seed flooded inside me like an ocean, flicking the switch to my climax as I shuddered, exploded, then lit up like a firework.

His cream mixed with mine, squeezing through the tight seal between his cock and my cunt. My ass cheeks felt soaked when Jeremy reached down, kissing me while in the throes of an immense orgasm.

It felt as though we were lovers, and that I was doing this more for myself than for my marriage or Simon's career. I tried to focus on Florence while Jeremy's cock jerked uncontrollably inside me, spilling the last remnants of his cum, filling my womb.

We kissed again, and again, and I felt terrified I'd broken a vow that could never be remade.

When Jeremy rolled off me, I felt overjoyed, satisfied, but slutty. He spooned into me as if we were married and I relaxed in his arms.

"That was the best fuck of my life, Jess."

"Jess."

"Jess, are you okay?"

"Yes, Jeremy. It was the best fuck of my life, too."