Cuckold Dilemma Ch. 04

"I love Florence."

"Me too Jess. It's like we've finally found our perfect place in this life."

After my evening of entertaining Jeremy, changes in our lives happened quickly. We packed up our home, arranged flights to Italy and bid a tearful farewell to family and friends.

Jeremy and I selected a lovely apartment while I sucked his cock and he flicked through images of our shortlist on my husband's iPad. They sat beside each other on our sofa, comparing prices, while my head skillfully bobbed up and down. When I emptied his balls, then looked up and swallowed, gazing affectionately into his eyes, my husband's boss would have bought me the Sistine Chapel.

The owner of the apartment, Blue Lily, sent his agents on the day we took over and signed for an exquisite inventory of antique furniture. Ours was a stunning second-floor, three-bedroom, spacious apartment in a historical Florentine building, six hundred metres from 'Piazza del Duomo'.

I felt at home, strolling through our new apartment while ushering the agent through the front door. I was relaxed and could see my husband was too.

In the centre of an intricate gold and silver compass design inlaid to a light mahogany, highly polished parquet floor, Simon took me in his powerful arms. He swept a few strands of the long hair obscuring his my face, then kissed me.

"We did this together, Jess."

"This apartment is well worth a mouthful of your boss's salty cum, babe, but you did the hard work for years."

"Speaking of that evening, I enjoyed sharing his cum with you and kinda hoped for more soon."

I pecked him on the lips, disengaging our tryst because my panties had moistened beyond their ability to cope and the bulge in his pants had provoked me.

"I'll decide when, husband, but your request is duly noted. For now, how about you fuck me over the balcony while I look down on the crowds passing by?"

Our first weekend was delicious. We dined at local restaurants, drank wine to excess and made love more than we had in months. I was stress and care free and knew it was a perfect time to entertain a bull for both our enjoyment.

We felt the itch for me to have a stranger's cock inside my pussy and I knew Simon would enjoy a creampie clean-up and his reclaiming sex ritual as we settled into our new life. Each time I stepped out on my marriage vows, it twanged a taboo string deep inside both of us for different but complimentary reasons.

For me, the feeling of being desired by other men was intoxicating and lifted my self-esteem. Simon revelled joyously in his humiliation and my domination of him in controlling our sexual journey.

"I love competing with bulls to have you, Jess."

Jeremy had a bigger cock than Simon and I'd enjoyed it, perhaps a little too much. Thankfully, I didn't like the man much, so it hadn't affected me and I hoped that would hold true every time I fucked a bigger cock.

"They've all had smaller cocks than you so far, except Jeremy. What happens if I tackle another one who's bigger?"

"I'll have to compete with him, it's as simple as that and I relish the challenge. I love the feeling that I have to work harder to have you and remain your first choice."

"You'll always be my first and only love, Simon. That will never be in doubt, or we'll stop cuckolding immediately."

"I'll be working hard at the new office this week, so it would be good if we dined out in the evenings to spend quality time together."

Our belongings arrived on the Monday morning and the men who unpacked them seemed ready to fuck me at the slightest encouragement. They didn't appeal because I wanted to be seduced, demanding an element of sophisticated behaviour from my bulls. A few sweaty guys, however good looking, fucking me in between removal jobs wasn't happening.

In between moving furniture around, I strolled along the piazza to our new favourite Cicchetti cafe, where I ordered two of my favourite small plates and a carafe of Barolo red wine. I considered my life choices while swirling wine in the oversized glass, admiring its dark, almost taboo redness that brightened in the sun where the alluring liquor ran thinnest.

Simon and I are bringing our deepest desires into the light.

A man peering at me from outside a rope boundary of the cafe caught my attention.

"Is that Jess Miller?"

"My god, Professor Simms. Fancy seeing you here."

I stood up and hugged my old history professor. I say old, but he was only ten years my senior and had been the star, and my crush at University.

"May I?"

"Of course, I'd be upset if you didn't join me."

Another glass hit the table almost as his backside slid into the chair opposite me and he helped himself to my carafe.

"It's Roger, by the way. All that stuffy professor shit is in my rearview mirror."

"You've left the University?"

"Two years ago next month. I'm advising the Florence city museum curator on literature that belonged to the Medici family. It's far more fascinating and I get to live here, at least for now."

We caught up for nearly two hours, devouring five small plates and three carafes. When it was time for me to meet Simon, I excused myself, exchanging cell numbers, leaving my professor languishing alone.

When I entered our apartment, I reached beneath my skirt and peeled off a very damp pair of knickers, presenting them proudly to my husband, who was resting on our balcony.

"I can smell you but nobody else. May I?"

"Of course, that's why I stripped them off, so that you could eat them."

I made two espressos and joined Simon at the small table on our spacious balcony. While he enjoyed my underwear, I regaled him about my lunchtime liaison and how that made my pussy ooze its approval into the gusset of his new toy.

"Have you considered inviting him here?"

"I did, but I feel we should discuss and agree when selecting my bulls. They should work hard to have me, as should you."

"I love the chase and that definitely works for me."

My phone buzzed, and I scanned the message, showing my husband once I knew it was Roger.

It was great to see you today, Jess. I'm sorry to bother you so soon after lunch, but could we meet up again, please?

I stared at my husband, who chuckled.

"That's great timing, and it seems to me he's champing at the bit to slide his cock inside you. Do you want to fuck him?"

"Yes, would you mind?"

"Not at all. What role will I play?"

"You'll have to wait and see, husband."

I reverted to my phone, sliding my fingers across its glass keypad to return Roger's message.

What did you have in mind, Roger?

I thought perhaps another drink or maybe dinner.

Do you mean as a professor/former student catchup like today?

I was hoping for more, to be honest.

Honesty is best. Could you be more specific?

A casual encounter, some fun, maybe?

Are you asking to fuck me?

Yes.

You aren't being forthright about it.

There was a pause in the flow of our messages and I considered perhaps I'd pushed him too far. If he wanted me, he'd damn well better ask.

May I fuck you, Jess, please?

I'm married. Not sure I mentioned that.

Ah, Sorry, forgive me for asking then.

Are you giving up so easily?

Sorry Jess. I don't understand. Are you pulling my leg?

Not at all. I assumed you were serious when you asked to fuck me, so I'm being honest.

But if you're married, won't that be a tad unfair to your husband?

Why don't you come over and ask him.

Simon laughed loudly, watching over my shoulder, having slid across the few inches separating us on our brown calf leather sofa. He wrapped his arms around me, planting kisses on my neck while I exploded in a raging storm of happy hormones. My pussy lips engorged while my face flushed in absolute arousal.

"How do you feel, Jess?"

"Like my favourite crush Professor is going to fuck me this evening."

"I can't wait either."

"Lick my pussy honey, I'm flustered and could do with settling down before he arrives."

Simon was kneeling in front of me in the blink of an eye, pushing my legs high and wide while I shuffled my pussy to the edge of the sofa.

"I can see the effect he's had on you. Your pussy lips are as puffy and creamy as an eclair."

"Just hurry and lick it, babe, because I'll need to shower and change afterwards. Can you cook dinner for us as well, please?"

"Of course, right after I enjoy my starter."

He kissed and licked his way up my thighs while I kneaded excess sexual tension out through my breasts, squeezing hard with both palms, moaning loudly.

I needed to be fucked but couldn't allow my husband access to my pussy with his enormous cock because I enjoy being tight and clean for my bulls while remaining dirty and wet for Simon.

He'd become much more accomplished in cunnilingus since our foray into cuckolding. Simon sucked air through the corners of his mouth with my swollen labia inside, passing a tickling vibration across the slick surface of my sensitive tissue. I moaned like a whore, which was good practice for later when I'd undoubtedly feel, and maybe even be one.

My phone buzzed, and I swept blindly around the sofa with flailing arms for it, half dazed by an approaching orgasm.

"It's Roger. Keep licking my pussy darling while I deal with him."

Simon didn't stop and his tongue had reached my spangled sphincter, so I knew that would occupy him greatly. He loved licking the ridges around my anus before dipping his tongue inside my back passage. He told me that it satisfied his deep desire to be humiliated, feeling more worthy of me after cleaning my anus properly.

Sorry, slight issue, I have people staying with me. It might be better another day, but I don't want you to think I'm not keen.

Ah, okay. If you have guests, then we can hook up another time.

Its Professor's Kendrick and Samuels. I'm providing them accommodation for a free holiday, sorry.

"Oh, fuck!"

"What's up?"

"He's got two more of my old Professors staying with him. What the fuck shall I do?"

"It's up to you, wife."

My heart raced because my first instinct was to arrange a gangbang but I wouldn't and couldn't... could I? Simon licked my pussy with enormous intensity, sucking hard on my clitoris, flicking the juicy hidden pearl with the tip of his tongue.

"Fucking hell, Simon, you're trying to get me to invite all of them."

"Mmmm."

"What the fuck do you mean, mmmm? Now's not the time to mess about. What shall I do?"

He stopped and looked up at me lovingly with my pussy cream slathered on his lips and chin.

"It's your choice, babe."

"But I want your opinion, Simon."

"You should fuck them."

"All three?"

"Definitely, and me too afterwards, if that's acceptable."

I pulled my husbands head back into my crotch, where he continued his excellent work sucking and licking my clitoris. Billions of synapsis exploded in my head like a New Year's firework display, forming the image of three cocks from my college tutors, reaming me.

My vision went hazy while I tapped my cell phone screen scribing a message with fluttering waves of bliss rising from my pussy and womb.

If everyone is well behaved, why not bring them?

To hang out?

To fuck me.

I put the phone down, resolved to answer no more questions and let him decide. If they came by, fine, but either way I was cumming just thinking about my professors gang banging me while my husband attended to dinner.

Simon swallowed my squirting pee and hormone mixture with an eagerness that only a cuckold husband could manage, knowing three bulls were coming to do a lot of cumming inside his wife.

I showered quickly, wore a knee-length cocktail dress with white French Kicker set and suspenders holding sheer tights to around mid thigh.

"They haven't got a prayer once they see you."

"That's the general idea."

"How old are these guys?"

"Early forties."

Simon ground salt and pepper onto filet steak strips preparing our dinner, watching me pace to the balcony, peer over, then walk back to him. He was serving tagliatelle in a blue cheese sauce with pan fried steak draped atop the sumptuous tower. I love his cooking, but right now, I was desperate for another mans cock inside me, preferably three of them.

I wanted to be fucked before dinner, then again afterwards, feeding my husband a dessert privately later on.

When my swains arrived, I could tell Roger hadn't shared my offer with his friends because they were too relaxed. He was sheepish when shaking Simon's hand while the others got stuck right in, helping my husband in the kitchen with glasses, bottles and a corkscrew, telling tales on college days.

Watching Sean Kendrick screw a curly silver steel shaft into the cork of a bottle of Barolo ensured my husband wouldn't want for soiled knickers for a few days. Roger drew me to one side, whispering nervously.

"I've said nothing to the others because I wasn't sure if you meant it. I'm really confused, Jess."

"I can understand why. Simon and I are liberated, he's my cuckold husband and we're both happy."

"Oh."

"Come on Roger, don't tell me you're a prude?"

"Not at all, I just didn't expect my favourite student ever to ask me to fuck her in front of her husband."

"I didn't ask you to fuck me. It was the other way around."

"Yes, sorry, but you take my point, surely?"

"My husband may not be there."

"Oh, why not?"

"I decide what's best for Simon and our marriage, and I'm currently on the fence."

I drew Roger onto the balcony, where a light breeze snuck under the hem of my dress, refreshing my pussy. The city was dark and its lights gave our piazza a sultry and comforting feeling that relaxed my soul. A light chatter from the many street cafes below drifted up as Italians at play added to my arousal.

Roger stared at me with a desperate hunger I have rarely seen in any man.

"The trouble is, having to teach you girls at that age is fucking torture. Although you're legal, it's absolutely forbidden for the teaching staff to go anywhere near, and I really fucking struggled with you."

"I had a few afternoon rub sessions looking at your photos too, professor."

"Will you please call me Roger?"

"After you fill my womb with your professorial seed? Yes."

"How are we going to tell the others about you wanting a... err, a-."

"A gangbang?"

"Yes."

"I thought you might fuck me out here on the balcony. If they don't see us and figure it out, then I'll just ask them directly if they want to take turns inside my pussy."

"O-out here?"

"Right here, yes. Simon has already fucked me out here, so I'm sure nobody below will notice and if they do, they won't care. This is Italy, after all."

I sat on the wall ledge where iron railings were sunk into the concrete. There was a two-foot width of fuck platform to accommodate my ass, and a sheer drop below if the railings gave way. There was easily enough space for Roger to rail me.

I spread my legs wide open, displaying what he could enjoy. He pressed my knees together, slid his palms gently down my silken thighs, then expertly peeled my knickers over tight suspender straps.

"Hang those on the door handle and my husband will collect them later."

"He must be an incredible man."

"Wait till you try his blue cheese pasta."

I pulled Roger's belt buckle loose, unzipped his fly and was relieved by his average sized, beautiful cock. Since my discussion with Simon about cock size, I feared the day when a bull entered our lives with more length and girth than him.

I licked Rogers glistening glans, cleaning the delicious, slimy treat the slit on the end of his cock had oozed for me on the way over. His salty, musky hit of hormonal delight on my taste buds sent my body on a journey towards its orgasm and I felt a stream of gratifying shame dribble down my thighs.

"I need to fuck you now, please, Jess."

"Do you have an itch that needs scratching, Professor?"

"Yes, desperately."

My legs were raised before he knelt, and I felt his cock nuzzle between my soaking labia. I turned my head, looked down and watched dozens of people pass underneath while my old history Professor buried his solid erection deep inside me.

I gasped, pressed my forehead onto Roger's and wrapped both arms around his neck. I planted soft kisses on his face, licking, then sucking a line to his earlobe while he sobbed with pleasure and from the release of pent up sexual tension.

"Did you need my pussy badly, Professor?"

"You don't know how good it feels for me to be inside you, Jess."

"Your cock feels wonderful."

With his cock balls deep inside me, my lips brushed lightly against his, electrifying mine before my tongue probed deep inside the mouth I'd yearned to kiss while still a maiden.

We French kissed deeply, and I delighted in his desperate need for me, amplified when he sunk his fingers between my ass cheeks, prising them apart until my puckered sphincter scraped tantalisingly against rough concrete.

He rocked back and forth on his kneecaps, fucking me gently with a perfectly sized cock. Roger glanced down at my pussy with his cock embedded inside it in awe as if he couldn't believe the gift I'd granted.

I recalled masturbating over surreptitiously obtained photographs and looked into his eyes enjoying the absolute explosive desire he felt for me while fucking my pussy with all the force he could muster. On every stroke he went balls deep inside me and I felt his pubic hair scratch my alabaster smooth, freshly shaven mons delightfully.

I rested my chin on Roger's shoulder and saw my husband through the living room net curtains. He watched intently, beaming proudly at me while entertaining our guests at the exquisite blue enamel Corneu cooker we both loved.

To be fucked by a fabulous man who desperately wanted me while another looks on while cooking our dinner, is a great feeling. I looked skywards to a starry night, thanking the universe for sending Simon and Roger into my life.

My orgasm began as a whisper of blood rushing into my reproductive system, beckoned by oxytocin to encourage an insemination that couldn't happen tonight. I felt the warmth of a coming eruption as my thoughts drifted to sandy beaches at sunset and the loving embrace of my husband on a Sunday morning.

My forehead repeatedly knocked gently off Roger's shoulder as I whimpered to the timing of his cock reaming my cunt while he pulled me hard onto him.

When I felt his surging orgasm, I kissed Roger deeply, edging my cunt further onto his cock while he increased the intensity of his pumping. He gripped both of my ass cheeks, pulling my cunt closer, reaming its tight hole but not quite bottoming out as Simon could and would later.

"I-I-Im-"

I pressed a finger to his lips to quieten him.

"I know, Professor. Please empty your load inside and fill my pussy before Simon serves our dinner."

Roger was balls deep when he exploded inside me, and rope after rope of his cum splattered the walls of my pussy, flooding into my womb. He seemed incapable of controlling his body, because my dirty talk was too much for a professor who'd wanked his way through my study years at his University.

My fluttering orgasm struck in crashing waves, quickly sweeping through me like a tropical ocean storm that subsided slowly.

I felt sated but glad there was plenty more cock available between now and a restful sleep later. I smiled encouragingly while Roger squirted his seed inside me, lifted when he jerked and twitched violently until all his prostate and balls were exhausted.

He stood up, and I noticed bloody grazes on both of his knees. I smoothed my dress down, picked up my knickers and walked past him back into the apartment while he fixed his clothes and straightened his hair.

"Simon will get you some cream and plasters for that if you ask him."