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Closing the Deal

Category: Anal Sex
02.11.2019
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I opened the door to the plush real estate office late on this gorgeous Autumn Saturday afternoon with a full-blown hard-on ready and willing to go.

No, it wasn’t that I was that excited about some pending coastal resort home purchase, not that there’s anything wrong with that. The object of my arousal on this particular visit was the anticipation of finding my real estate agent girlfriend, Mikki, waiting for me in an unoccupied office, with the idea that I would have her writhing on the conference room table within minutes, my cock buried deep inside of her.

Mikki and I had started a long-distance relationship several months back, when she was visiting her family in her native city of Philadelphia. We met at a barbecue of a mutual friends’ house, found we had a lot in common, including recent ugly divorces and a dormant sex life. Mikki had moved to Wilmington, North Carolina about a decade ago to become a partner in a family-owned real estate development business, hitting it big during the blooming market of the late 1990’s and earlier this millennium. She had parted ways with her philandering husband, who gradually became more interested in bedding his clients’ trophy wives.

I had hit the jackpot in more ways than one with Mikki. She was beautiful, buxom, slender, personable, rich, and exceedingly horny. She was also relatively sexually inexperienced, having confessed to me that her ex-husband was the only man with whom she had ever been intimate with before she and I met. She had married young, a marriage of convenience, arranged by wealthy Main Line old-money families and she was still a virgin on her wedding night. I was having great fun teaching her, and she was charmingly insatiable, quickly wanting to make up for lost decades of adventurous sexual escapades. We were making the flights from Philly to Wilmington almost every weekend now, and our sex was fresh, non-stop, and creative. That’s the wonderful thing about long-distance relationships, for those among us who embrace such a concept.

In fact, Mikki had only a few minor flaws that I could ascertain, since I always seemed to be looking for imperfections in the gem, no matter how strong the relationship or how incredible the sex. I guess it was a defense mechanism of my own, built up over the years to ward off deeper emotional investment. I always somehow found the gray cloud in the silver lining.

In Mikki’s case, the sexual imperfections were relatively minor, I suppose, not to pick nits. She wasn’t the most accomplished or enthusiastic of a cocksucker, though God knows I was willing to be her recipient. I’m selfless and altruistic that way. She also had never ventured into the world of anal sex, and was more than reluctant to explore, virtually shuddering and recoiling whenever I would delicately broach the subject.

Last, above all else, she was essentially addicted to her residential real estate profession. All of those years in a loveless, sexless marriage had forced Mikki to throw her passions elsewhere, and it was into her relentless pattern of ‘closing the deal’. More than one of our steamy fuck sessions had been interrupted by the incessant ringing of Mikki’s cell phone, never more than a reach way from her, no matter when or where we were, and she ALWAYS fucking answered it.

I was beginning to accept her lackluster oral talents and anal-phobia, as I called it, but I admit to being more than frustrated with this habit of hers of putting business before pleasure. On this trip to her firm’s office, however, this finally worked to my advantage.

My hard-on and me strode expectantly through the vestibule of her firm’s office. Mikki had volunteered several times in the past to stay in the office during the comparatively slow time of late Saturday afternoons under the auspices of graciously sending her fellow agents home early. This would leave her alone in the posh office, and we had gotten into the practice of greeting my arrivals with wild fucking on couches, conference tables, mahogany desks, Oriental rugs, and assorted other nooks and crannies. Let’s face it, there is something inherently forbidden and decadent about office sex, and I was fully expecting to find Mikki by herself in her usual professional attire, knowing that there would be nothing on beneath, and I planned this time to pin her against the wall next to the fireplace and the floor-to-ceiling plate-glass window.

As the door shut behind me (and my hard-on, yep, it was still there!), I stopped dead in my tracks as I heard a vaguely familiar though completely unexpected voice come from the other room. “John, is that you?”

My hard-on tip-toed from the room as I struggled to come to grips with the surprise verbal greeting. So much for pin-against-the-wall office sex today, I thought.

“Uh, yes, it is,” I stammered. “Um, is Mikki here?”

She appeared from around the corner, smiling, adorned in a lavender-pastel sundress, and I immediately recognized her as the receptionist, Cindy, who Mikki had introduced me to on my first visit to the office several months back. Cindy was very easy on the eyes herself, a petite, fit, tanned, platinum blonde in perhaps her mid-30’s with short, almost spiked hair and a mischievous twinkle in her bright blue eyes. I recalled that Mikki had told me that Cindy had just been recently divorced herself, and had inherited a luxurious house overlooking the Intra Coastal waterway with a view of the hotels of Wrightsville Beach in the distance. As was her nature, Mikki spoke dreamily of the inheritance, estimating the value of the asset at over two million dollars. Cindy would never have to work another day in her life, according to Mikki.

None of that resonated within my mind now, however, as I was taking mental inventory of this unexpected turn of events, while simultaneously trying not to gape at Cindy’s very visible nipples poking precariously through the sheer, almost transparent material of her sundress.

Cindy walked directly towards me and greeted me with a more than cordial hug, pressing those pert breasts into me more than was necessary. This resulted in my hard-on sprinting back into the room and leaping into my lap, lurching my hips involuntarily forward, trying to latch himself onto Cindy’s pelvis.

Cindy smiled wryly, undoubtedly taking notice of my hard-on’s less than subtle return, and released her hug and walked over to slip the latch on the entrance door to the locked position. “Come in, John, let’s get you comfortable. Mikki has a message for you that she wants you to hear.” I followed as Cindy led me by the hand to the back room, puzzled, but still not confused enough not to rivet my eyes on Cindy’s tight, wriggling buns dancing under the tight dress.

Cindy motioned to me to sit in the leather chair in front of her desk, and I watched as she unclasped another button on her dress, teasingly exposing just the hint of a matching lilac bra strap. She crossed her legs, the dress running up to mid-thigh, licked her lips, and grinned at me wickedly. Lustfully, I imagined. Or was I not imagining?

She leaned over, exposing her cleavage to me unabashedly, and hit the button on a desk-top voice mail speaker. I heard Mikki’s voice come through the speaker, though my eyes never left Cindy as she ran her fingers lightly over her long, sun-kissed neck.

“Hi, hun! I know it drives you crazy when I chase my deals, but I had to go up to New Bern to sign some papers at the last minute to close a deal. I’ll be back in about two hours. Or more, maybe. But, Cindy and I have had some very specific discussions about the tradition that you and I have started in our office, and she was feeling a bit left out. You see, it’s been awhile for her, and, well, she asked if she could substitute for me today until I get back. I told her I thought that you would be more than willing to fill her in. And, you see, I can learn something from this, too. Cindy will show you what we mean. See you in a few hours, baby, enjoy. I love you lots, babe.”

Mikki’s voice had barely ceased to echo in my ears when I saw Cindy reach into the desk drawer and pull out a hand-held camcorder. Cindy’s eyes glowed in amusement as my jaw gaped in astonishment.

“In the real estate business, John, we call this sharing the commission,” Cindy seductively purred, rising from her seat and easing towards me. “You see, it’s a symbiotic relationship.” My eyes bulged, my throat constricted, but most of all, my cock twitched as I grasped the reality and inevitability of this situation.

Cindy placed the camera on the desk and pointed it at me, then kneeled in front of me and with one hand began to unbuckled my belt, shifting my hips so that she could have unfettered access, while slowly unbuttoning each of the buttons on her dress, which fell to her navel.

“You see, Mikki wants to learn how to suck cock better, and I oh, so desperately need to suck a cock,” she said, releasing my manhood from beneath my pants. “Ooooo, commando, bad boy.” She slapped the head playfully, and then gripped the rock-hard shaft in her tiny hands. “Nice, Mikki didn’t lie, you are quite a well-endowed fellow.” She licked around my mushroom head as I placed my head back and closed my eyes, preparing to enjoy wherever this ride would lead, still not believing that Mikki had orchestrated such a wild fantasy for me. “And I am quite the cock-whore, John, as you and your girlfriend are about to find out.” With that, my entire seven inches disappeared into Cindy’s hot, wet throat, and she slurped and gobbled and spit on my long dick, like the cock-deprived slut that she was.

Cindy came up for air for just a second, leering at me, strands of drool and pre-cum dangling off of the corners of her pink lips, hanging down her chin.

“But the really big surprise, Johnnie boy, is that Mikki wants to see first-hand if she can really fit this big, fat cock of yours into her asshole, so I’m gonna prep you to show her how its done.” She stroked my shaft furiously with a vice-like grip of her one hand, while massaging that ultra-sensitive spot beneath my scrotum and above my anus with the other. “You won’t mind fucking my tight little asshole for your girlfriends’ viewing pleasure, will ya, darling?” Cindy teased in an exaggerated southern-belle drawl. “It’s all in the spirit of continuing education.”

At this point, I decided that if Mikki wanted a show, then she was going to get a show. With one hand, I picked up the camcorder and zoomed in for a close-up on Cindy’s expert deep-throating techniques, while with the other, I grabbed the back of her head forcefully and face-fucked her. hard. I spoke into the tiny microphone to Mikki, “This is how you suck cock, baby, not that lollipop-licking excuse you call a blowjob. This is a slut who loves her cock, who knows how to please her man.” Cindy gurgled her excitement, my words obviously serving the intended purpose to spur her on. “She’s getting my dick so fucking hard so I can fill her asshole, honey.”

I maneuvered Cindy’s head back and forth on my impossibly rigid member until I was at the pint of explosion, and then swiftly picked up Cindy’s lithe frame and carried her to the conference table, the one that I had fucked Mikki on countless times before. Cindy’s legs wrapped around my waist as i put the recorded won on the table top, spinning Cindy’s legs towards the lens and pushing her dress up to her belly button and violently ripped the purple thong covering Cindy’s dripping snatch and plunged deeply into her with one motion. She came instantly, her howls of ecstasy reverberating through the tiny room.

I continued my narrative for Mikki’s sake as I plunged mercilessly in and out of Cindy’s sopping cunt, her juices dripping down into her as crack and onto the table, forming a small puddle beneath her, as she splashed up and down on her own puddled cum. As I continued to fuck Cindy with all my strength, I pulled open the walls of her anal opening and turned her ass right into the eye of the camera lens.

“See that, baby? See that juice in her ass? That’s natural lube, honey, all natural, as wet as you always get when I’m fucking your own tight little cunt. Watch how easy I slide into her tight little ass, baby, just as I’m gonna do to you right after we watch this tape together.” I slid just the very tip of my throbbing cock into Cindy’s sphincter, still holding her legs open lewdly for the camera to capture the close-up anal assault of my cock entering her puckered hole.

Cindy growled in impromptu bliss, “Yeah, you fucker, fuck my ass with that big cock, give it to me, show your timid little girlfriend how to fuck a slut’s ass.”

The camera was all but forgotten for the next ten minutes as I relentlessly pounded Cindy’s tunnel, the sounds of hard, rough sex echoing into the speaker, and culminating in six, seven, eight loads of hot seed shooting deep into Cindy’s bowels, each one accompanied by a wailing shriek of orgasmic delight from Cindy.

I hopped off of Cindy while still keeping her legs spread high in the air and again grabbed the camera to capture the white, hot sticky flow of semen dripping from Cindy’s hole and onto her thighs and cunt, pooling on the tabletop in a odiferous nectar of our cum.

Before turning the camera to the off position, I leaned over to run my lips around Cindy’s still-pulsing crack, rimming her, and then kissing the lens of the camera, smearing it with cum. “That’s what awaits you, Mikki, dear. Thank you for sharing this deal with your friend here.”

Cindy lay panting on the table, her legs still spread wide, rubbing her fingers over her clit, her pink, swollen labia glistening in cum. She glanced at the clock on the wall.

“We still have forty-five minutes or so until Mikki gets back. Let’s wash up. Do you know we have a shower here?”

“And, I have a blowjob to finish. This one is just for you and me, John.”

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