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Jim’s Eleven (and a half)

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Sitting across from him in the executive boardroom, it was easy to see why Jim was so popular with the office females: in his late twenties: handsome, charming, and intelligent. Despite his currency as an eminently dateable up-and-comer within the company, he had wisely avoided the romantic and/or sexual advances of his office colleagues. Yet this only served to pique even greater interest and make him all the more desirable. Was he already seeing someone? Was he gay? He had every woman in the firm between twenty and fifty eating out of his hand, but had only dated one of them once ‘ a gorgeous young blond in the legal department. And despite my reticence to kiss and tell, rumours persisted in the women’s washroom that Jim was seriously ‘packing’; something we women all agreed was simply too good to be true, given his looks, personality, and the amount of sex appeal he had to spare.

As a senior manager and a married woman in my late thirties with two children, I tried my best to avoid personal gossip. Still, I succumbed to the odd naughty daydream myself, especially during tedious meetings in the boardroom when he was present. Relatively speaking, I had been happily married for almost ten years, but even relatively happily married women can think naughty thoughts, yes? With his prominent jawline, stylishly cut locks, blue bedroom eyes, and sensual lips, Jim was a yummy visual diversion for horny women.

I suppose it’s fair to say that I had my own office admirers. As with Jim, I think I’m considered quite attractive by many; with straight, shoulder-length hair, green eyes, and pillowy lips. I’ve also worked very hard at maintaining my figure. Consequently I’m still a slim and trim 5 ‘ 3’. Still, girlfriends often tease me that a view of me from behind, however fetching and pleasantly curvy, does not prepare one for the view in profile. Measuring 42-26-37, with a size 32DDD bra, my bustline is, shall we say, formidable. As a self-conscious teen, I was incredibly sensitive about the size of my breasts (I was already a DD-cup in grade eight!), and despite the occasional back pain, I have come to accept being so conspicuously top heavy for all its plusses and minuses. And despite their size and weight, I am fortunate that they still retain much of their gravity-defying firmness.

As much as any woman who wears a 32DDD bra can, I do my best to dress in such a way that I don’t emphasize my boobs at work. That particular day I was wearing a nicely tailored pin-stripe skirt suit with a buttoned blouse, silk stockings, and black heels. Still, when you’re slim-waisted AND busty, there’s only so much you can do without succumbing to frumpiness.

I was in the middle of a yummy ‘Jim daydream’ — stealing the occasional glance his way (was I imagining things or was he doing the same thing to me in return’), when my ears perked up at the mention of my name. The CEO was selecting two company reps to fly down to the Carribean for a three-day trade show. My name came up first, followed by Jim’s. We smiled at each other and were briefed on what we had to do. Jim was to accompany me as my assistant.

Although a fairly standard itinerary, it was a little out of the ordinary that as senior a manager as myself would be going, but the CEO explained that the work was minimal and that a few days in such a lovely spot, with some free time, would make up for the fact that I hadn’t had time to book any holidays in the last six months. With his tongue firmly planted in his cheek, he told me to look at it as a ‘working holiday’, which drew laughs from the others in attendance.

‘Heavy on the work; light on the holiday’, quipped one of the executives.

Either way, the fact that Jim and I would be staying in neighbouring hotel rooms in a tropical resort was sure to make the rumour mill. We were scheduled to catch a flight out the next morning. I packed light that night; adding my bikini at the last minute just in case I had time to sunbathe by the pool. I kissed my husband goodbye and took a taxi to the airport. Jim, always so slim and fetching in his ubiquitous well-tailored suit, looked just as good semi-casual. The flight was long but uneventful and we were glad to be shown to our rooms at the resort hotel, arriving by shuttle from the airport.

The hotel and surrounding area of white sandy beaches and palm trees were stunning. The air smelled of tropical flowers, and the weather was beautiful: sunny skies; fresh, warm air.

The first day was quite hectic, and Jim and I never really had a chance to catch our breath until late in the evening. I confess it was enjoyable having such a handsome younger man at my beck and call; willing and eager to follow my every command. Power has its privileges and I took the liberty of checking out his sexy, tight ass at every opportunity.

We finished for the day at around nine in the evening and I told Jim I’d treat him to drinks in the lounge after we’d had a chance to shower and change.

As we never saw each other away from the office, rip her up porno I suppose it was just as unusual for Jim to see me in more casual attire as it was for me to see him dressed that way. I slipped into a form-fitting, somewhat low-cut summery dress and open-toed heels; my lacy underwire, push-up bra generated a significant amount of cleavage. And despite his best efforts to be discreet about it, I noticed that my cleavage and short hem line did not go unnoticed by Jim. We sat down at a private little table in the stylish, dimly lounge together.

In retrospect, I suppose that given we were spending so much concentrated time together, having drinks probably wasn’t the best idea. By my third girly martini, Jim’s drop dead looks and flirty wit and charm were having their effect on me. At one point, the hem of my dress had almost hiked up to where most of my thighs and even the delta of my lacy panties were showing. Jim, being a smart boy, teased me about it ‘ thereby affording him ample time to check me out ‘ rather than pretending not to notice. As the evening wore on, I found myself leaning closer and closer to him; enjoying the scent of his cologne and the sparkle of his eyes. Eventually, as the alcohol lessened our collective inhibitions, we even began to touch each other in subtle ways. Others in the lounge could have been forgiven for assuming we were lovers ‘ his hand touched my knee; my hand lightly brushed aside the hair of his bangs; hands placed quickly and gently on forearms. I knew it was inappropriate, but the atmosphere of romance and the thrill and the excitement of the flirtation carried me away.

‘I bet you’re quite good in bed,’ I said teasingly at one point.

‘Christine!’ Jim exclaimed with his voice lowered; blushing and looking adorably taken aback.

‘Rumour has it that Sarah from marketing could barely walk after a night of love making with you’ I continued with a wink and a twinkle in my eye. ‘Or was that just because you’re like this” I added, bookending my hands widely apart to imply a large penis.

‘Time to put you to bed, you naughty woman,’ countered Jim.

‘Oh?’ Are you going to undress me and tuck me in” I asked with a cheeky grin.

My panties were already soaked by that time, but Jim’s response made my tummy jump.

‘If you weren’t a married woman, you’d be in MY bed tonight,’ he said, grinning.

On the way to the elevator to go back to our rooms for the night, I could tell that my areolas ‘ bubble gum pink and saucer size ‘ were puffy and swollen inside my bra; my breasts undulating heavily as I sashayed across the hotel lobby.

Inside the elevator, my four martinis got the better of me at last. I pressed Jim up against the inside of the elevator and pressed my pillowy lips against his. Our kiss was soft and long and wet. I parted his lips with my tongue and we tasted each other as I made several breathy sighs. Suddenly, as if seized by a light of instant sobriety, I stepped back and bit my lower lip.

‘I’m sorry, I shouldn’t have done that,’ I blurted guiltily.

‘It’s okay,’ whispered Jim. ‘It will be our little secret. No harm done.’

We stepped off the elevator and said our goodnights quickly. I felt Jim’s eyes upon me as I fumbled with my keys and hurriedly closed the door behind me. I collapsed in the luxury of my king-size, soft-sheeted bed and fell asleep with the taste of his kisses still on my lips.

The next morning, room service delivered a bouquet of beautiful tropical flowers, compliments of Jim. I smiled as I read his note thanking me for drinks the night before. Then it hit ‘ I’d kissed and pawed him the night before like some sex-starved high school girl! What had I been thinking! Unfairly to Jim, I spent the rest of the morning being rather distant and demanding. I sensed he understood why, and he did his best to give me my space as we worked frantically to meet that day’s deadlines. By early afternoon, we were done for the day, leaving us a rare chance to get outside the resort conference centre and enjoy the sun. To make amends for punishing him for what was clearly MY indiscretion, I suggested we change into our swimsuits and walk along the beach. Jim seemed as pleased that my icy wall had melted as by the idea of a little well-deserved R & R.

Back in my suite, I packed a basket provided by the hotel with a towel, suntan lotion, some chilled chardonnay, and two wine glasses. I decided that I would have one glass, two at the most, to help me relax and unwind — no more booze-induced lust, I resolved.

I slipped into my favourite swimsuit ‘ a rather brief aqua-coloured, tie-sided bikini that I found in my size. Finding bikinis that allow for mixing and matching tops and bottom in different sizes ‘ a must for busty women who are otherwise fairly petite — can be difficult. This one was sexy and pretty and gave my boobs plenty of support, albeit with serious cleavage. I added a matching mini wrap and a too-tight t-shirt that was snug rus porno against my flat tummy and emphasized the size of my breasts.

I stepped out the ocean-view side entrance to my suite and made my way down the stairs. The gentle, warm ocean breeze was delicious, and the sun felt fabulous on my skin. Jim waved to me from the entrance to the long strip of white sandy beach and I ambled over to him. He was wearing a tight white singlet that emphasized his broad shoulders and tan, and a men’s sarong around his waist. I could only assume he was wearing a Speedo-type swimsuit underneath ‘ a thought that made my imagination run wild. Speedos aren’t for every man, but Jim was not every man ‘ the thought of seeing that sexy ass of his in a tight swimsuit gave me pause.

Chatting amicably as we walked, our feet pressing into the warm, white sand, we finally came to a spot that suited us and set down our towels. I caught Jim eyeing my body on more than one occasion, and perhaps he caught me doing likewise; scoping his Playgirl-worthy frame now and then as we walked together in the sun. If only the women from the office could see me now (oh, for a digital camera)!

I set out my things and poured us both a glass of wine before peeling off my t-shirt and undoing my wrap. Despite the night before, it still felt awkward being in a bikini around a colleague from work. I sat down on my towel and sipped my wine as Jim peeled off his singlet t-shirt. His chest, back, and shoulders were smooth and sculpted. I think I knew right then and there that the heat between us wasn’t likely to dissipate that afternoon. When he then stripped off his sarong, I felt my face go flush ‘ all he had on underneath was a tiny white men’s bikini, with about a half an inch of material at the sides. When my eye caught sight of the front of his swimsuit, though, I thought I might faint: the stretchy front pouch looked heavily weighted down and stuffed to the bursting point!

So the rumours were true, I thought — Jim was all too obviously a VERY ‘big’ boy. While I’d never had the experience of hooking ‘a big one’ myself, I have secretly always found them an incredible visual turn on. The eternal debate about size notwithstanding, I’d heard or read women’s’ stories on the subject: the initial discomfort, often followed by delicious feelings of being stretched and filled and all the attendant orgasms. My husband, bless his heart, is modestly endowed at best, and although I had no complaints vis-…-vis our sex life, it would be disingenuous of me not to admit to being intensely curious about the experience of bedding a big boy. Still, fantasies are fantasies ‘ would it hurt? Would the orgasms be more intense? Would it FIT?”

‘Oh my god, you look hot in that suit,’ I gushed. ‘It’s a good thing the front panel of my bikini bottoms are lined!’

Jim grinned and looked at me quizzically.

‘Um, because I’m getting wet just looking at you, silly!’ I laughed.

Jim had just settled onto his towel and taken a sip of his wine, when I noticed something rather strange. Looking around at the sparsely populated beach, I noticed that everyone ‘ though they were all off in the distance ‘ were nude! No sooner had I made the realization when a man who appeared to be in his late forties approached us. Like everyone else, he wasn’t wearing a swimsuit, and his sizeable organ slapped against his thigh as he made his way to us, smiling congenially.

‘Hi there,’ he said. ‘I’m not sure if you’re aware, but this is a strictly nude beach. You’re welcome to stay but you’d be required to remove your swimsuits if your do.’ He explained that the clothing optional and clothed portions of the beach were farther down, closer to the resort. With that explained, he headed back to his spot towards the water’s edge.

Jim and I grinned at each other red-faced. We chatted about it for a few moments; agreeing that packing up and moving on would be a nuisance. My heart was pounding in my chest as I summoned up some courage.

‘I’ll do it if you will,’ I offered.

‘Really” he replied with a sheepish grin.

‘Oh come on, sweetie!’ I beamed. ‘As if you don’t know I’m dying to see how big that thing is!’

With my hands trembling slightly, I reached back and fumbled with the clasp of my bikini top. My DDD-cup breasts, with their large pink nipples, sprang free, coming to rest heavily atop my rib cage. Next, I slipped my thumbs into the waistband of my bottoms, angled my hips, and slipped them off; exposing my neatly-trimmed pussy to the sun and my young assistant. In an effort to overcome my embarrassment, I got up and did a cute little dance in celebration of parading around in my baby suit.

‘So? What do you think?’ I asked; my hands on my hips.

Jim took a good, long look at my naked body.

‘You have SUCH a sexy body,’ he answered. That said, he stood and stripped off his own tiny restraint. What he uncovered made me gasp audibly and cover my gaping mouth with a smallish hand. Doubtless, sert porno he had grown accustomed to women’s reactions when they first laid eyes on the size of his penis, and mine was no exception.

“Oh my GOD!!!” I blurted out.

Jim’s flaccid penis hung down a good eight inches, with a large vein running along the length of it and; so thick that it obscured the sac suspended behind it. It slapped heavily against his thigh and dangled between his legs like some boneless forearm. I couldn’t stop staring at it.

“I’ve never seen one that big before!” I said, my voice rising like some school girl’s.

Jim grinned and sat back down on his towel; his fleshy, baby elephant’s trunk of a penis curving downward between his thighs and onto his towel.

I sat next to him, my large breasts swaying to and fro with every move, and, placing my hand on his thigh, gawked at his endowment.

‘I have to know ‘ how did Sarah HANDLE all of that!’ I asked. Again, Jim blushed.

‘With great difficulty,’ he answered quietly. ‘It was a really tight fit.’

‘Sweetie, EVERY woman is going to find YOU a ‘really tight fit’!!!’ I added.

I teasingly looked down at the size of my delicate little cleft, then back at his super-sized organ.

‘Woah!’ I sighed. ‘You really do take a girl’s breath away, don’t you’!’!’

We spent the next while covering ourselves in suntan lotion and basking in the sun. From behind his dark sunglasses, Jim watched as I squirted lotion on my breasts; working it in with my hand. Noticing that he hadn’t attended to his biggest asset, I playfully squirted lotion along the immense length of it.

‘We don’t want it to get sunburned,’ I giggled. ‘May I?’ I asked, motioning between his legs.

Jim obliged by parting his thighs a touch. ‘By all means,’ he grinned.

I tentatively reached down and placed my hand on his soft manhood; trying to close my fingers around it and succeeding only partially. I gasped once again as I slowly began to gently apply the lotion to his incredibly weighty shaft.

‘God, it’s so beautiful,’ I purred.

‘So are you,’ he countered.

I turned over and asked him to make sure my bum didn’t go without as well. He eagerly massaged lotion into the flesh of my curvy behind with his large, strong hands; a soft breeze cooled the wetness between my legs. In the end, the sun, the heat, the wine, the mutual nudity, and the size of Jim’s weapon all conspired to unhinge me like some wave of aphrodisia. Eventually, I was so filled with lust that I felt positively dizzy. Finally, I leaned over, and nibbling on his neck, whispered into his ear:

‘Let’s go back to my room. I want you to show me how tight a fit you are ”

He smiled a cocky smile and placed a hand on my inner thigh.

‘I thought you’d never ask.’

With barely a word spoken between us, we hurriedly put our swimsuits back on, packed our things, and headed back to the hotel. Desperate to get back and make love, we walked at a brisk pace. I put my arm in his and looked up into his beautiful blue eyes. Unable to resist, I groped his lycra-covered ass as we quickly made our way.

Once inside my room and the door locked, I approached him, placed my hand beneath his strong chin, and kissed him deeply, passionately.

His hands wandered — sliding over my hips and ass, feeling their smoothness — as our tongues met. I instructed Jim to sit on the edge of my luxuriously-appointed, king-size bed. He slipped off his t-shirt and his bikini swimsuit, leaving his sarong wrapped around his waist. Then, as if ‘unveiling’ himself to me, he untied it and drew it across his groin. What I saw next made me genuinely nervous. Jim was now fully aroused and much larger still. I drew my hand to my chest in utter disbelief.

‘Holy fuck ‘ how big ARE you?!?!?!’ I stammered.

‘Eleven and a half inches long; seven and half inches around,’ he answered matter-of-factly, perhaps wondering if I might throw in the towel at that point; something I WAS contemplating at that particular moment. He wasn’t just huge; he was SCARY huge.

‘Come over here and kiss it,’ he said.

I knelt down between his legs, no doubt with a tentative expression on my face. He took my hand and guided it to the huge, now rigid stalk that lay prone on the bed between his parted legs.

In countless boardroom sexual fantasies, I had imagined making love to Jim and taking him in my mouth. Now, in the flesh, I wasn’t sure that I could even manage to get my lips over the enormous head.

I gave it a gentle squeeze; just enough to cause a drop of clear pre-cum to ooze from the tip.

“I can’t, Jim,” I said, with a tremor of fear in my voice. “It’s too big.”

“Yes you can, Christine,” he answered. “Just relax and take it slow. Just try. I promise I won’t cause you to gag on it”

I pushed my lips against the large head, pursing my lips and sucking the droplet of pre-cum from the tip. In my daydreams, I had dreamed of tasting him. I gripped it with both hands. For several minutes I was content to just lick the length of his shaft; lifting his sac to lick the ridge of skin right behind it and between his legs. After several minutes, I still hadn’t tried to take him in my mouth.

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