Reuniting With Regan

It had been over twenty-five years since I had last seen her.

Somehow, even at alumni reunions or homecoming outings, our paths had never crossed.

She was my college crush during my freshman and sophomore years at the University of Maryland, before I really knew what I was doing from a sexually active standpoint, that is. Sure, I had fucked my share of coeds (well, OK, three), but it was more from dumb luck and circumstance than it was from skill or cunning. And, the classically beautiful Regan Carter Fleming had always eluded my grasp, though she had always been my number one target, such was her timeless beauty and graceful demeanor.

Regan was as regal as her aristocratic name implied. She grew up on the outskirts of the Beltway, the only daughter of a powerful Washington lobbyist and his former runway-model wife, whose stunning looks Regan had inherited, and every slug on Fraternity Row and half of the Sorority girls wanted to get in Regan's tighty-whiteys. She was essentially unattainable though, due to a variety of facts, rumors, innuendos, and half-truth urban legends.

She was shy (which she was); she was stuck-up (perhaps a little); she was a lesbian (that was the hot one, WAS she?); she was a virgin (probably so); she had a boyfriend (girlfriend?) back home.

That last one was the oddest one, she lived less than ten miles from College Park. Though, back in those days, that was the easy, convenient excuse used by any boy towards any girl who refused to share her charms with the male population. As in, "I coulda fucked her, man, but she told me she has a boyfriend at home." A loser's lament, told by one who had a busy post-date self-flagellation session with Mr. Willie Blue Balls.

I, too, was on the short end of the stick when it came to taking my own throws with Regan. I had convinced her to go to a few frat parties with me, and even a trip to Atlantic City for a social function with my frat buddies (yep, an abject disaster), but the best I could show for it was a cold-fish perfunctory goodnight kiss after three dates. It was time to move on, I reckoned, but that didn't mean I ever stopped fantasizing about her.

That's why I was literally shocked dead in my tracks when, out of absolutely nowhere, over two-and-a-half decades later, I saw the e-mail inviting me to join her social network on one of the career web sites. Her photo was on her profile, too, and if possible, she looked even better than she had in the early 80's. She looked like a modern-day Jacqueline Kennedy Onassis, jet black raven hair and immaculately attired, her firm, petite body still remarkably intact. I tripped on my tongue reaching for the keyboard to reply.

Several e-mails and then phone calls over the next few weeks followed, where we learned that we were both happily divorced (she had changed her name back to Fleming after the rather contentious divorce) and now once-again single. I was invited by Regan to a dinner 'meeting', as she termed it, careful not to call it a 'date', near her home in Bethany Beach, Delaware. As I drove down Route 13 from my own home outside of Philly, her words resonated in my mind..."I have a spare bedroom, so plan on staying the night, I insist."

As a perfect gentleman should, of course I gladly accepted her insistence. Except I was hoping that she was thinking like me. If the night went swimmingly, no spare bedroom would need to be occupied.

I glided up the driveway of a beautiful beachfront house on the south side of the small coastal town, almost on the border of Fenwick Island, just north of the Maryland state line, and immediately saw Regan's compact frame as she huddled in the doorway, her arms crossed over her chest to keep her warm. As I approached her, admiring her still-silky hair blowing over her still-gorgeous face in the chilly winter air, her dark eyes sparkled. My dick hardened immeasurably. "How about that GOOD good-night kiss you've been waiting for?" she asked coyly.

We hugged as she moved her mouth towards mine. "I'm much better at this now, I've had twenty-five years to practice," she murmured, no longer shy. We locked in a kiss well worth waiting a generation for.

The soft, slow, gentle, increasingly passionate kiss in the doorway told me instantly that the chances of this being a one-bedroom, cohabitation evening were enhancing by the minute. An Atlantic Coast Bed and Breakfast, if you will.

Regan was elegantly beautiful as always, time had indeed been a friend to her. She wore the quintessential little black dress with a strand of obviously very expensive pearls draped around the flawless skin of her neck and throat.

We made small talk on her couch for a bit, sharing a wonderful glass of Washington State merlot, our conversation serving as extended foreplay. We soon headed down Coastal Highway to a cozy little Italian restaurant in Ocean City, Maryland, Regan allowing me have the pleasure of driving her late-model teal blue Jaguar while I ogled her slender legs in the passenger seat, squirming while trying to disguise my ever-present hard-on, which was behaving in a less-than-obsequious manner.

Dinner lasted perhaps two hours, as we tried to cram nearly thirty years of catching up in a short window of time. We covered careers, families, hobbies, travel destinations, but consciously avoided the true climactic intent, though the sexual tension was escalating with each passing subject as we gazed deeper into each other's eyes. The restaurant was nearly deserted now, the locals having scurried back to their warm bungalows on this frigid off-season winter's night.

Curiosity got the best of me as we sipped our second bottle of wine, and I finally popped the question. No, no, not THAT question.

"So, Regan, why? Why after all this time did you reach out to me?"

Her dark eyes lowered for a split second, so I hurried to reassure her. "Not that I'm not thrilled, by the way, I'm delighted to see you again, you were always the prettiest coed at UM, and still could win contests on campus, even today, I'm sure of it." She blushed deeply, and my mind flashed back to the vision of the shy girl of long ago as she rebuffed my advances for more than a good-night kiss at her dorm room door.

Regan sighed, took another deep gulp of the delicious wine, and cupped her chin into her downturned palms. "Ok, here goes. I turn fifty next month, and I'd been taking inventory of some things I hadn't done yet." She giggled at herself, listening to her own story. "Sort of a middle-aged bucket list, if you will."

I was quiet as a church mouse as she continued. "I was painfully shy when I met you, and yes, still a virgin. In fact, I invented an imaginary boyfriend at home for the first two years I was at school just so I wouldn't somehow blow my cover to my sorority sisters that I still hadn't had sex." She paused, her eyes scanning the distance now for some long-forgotten memory. "In fact, truth was, I was scared to death at the thought of having sex, it intimated me, though of course, I was extremely curious. All of the sisters in my sorority would talk about nothing else but sex, so I made like I was getting my share at home with my make-believe boyfriend, to whom I was true-blue."

She laughed again at her charade. "That part was true, anyway, I sure wasn't cheating on a boyfriend that didn't exist."

I had to literally catch myself from leaning over the table to kiss her, and then lift her onto it and make wild love to her right there and then. Nothing is sexier than sexual self-revelation. She continued.

"Anyway, one night at the end of my junior year, it was just after finals and we were getting ready to go home for the summer. Well, about twelve of us sat in a big circle at an impromptu slumber party of sorts and started telling stories about the men we had dated. The subject got a little more detailed as we drank more beer, of course, and it soon became a game of 'Who was the best lover you ever had' and 'Who was the most well-endowed' Silly, but fun, except I was petrified."

My own cock twitched wildly in my trousers and threatened to raise the table now in a personal levitation trick, imagining being a fly on the wall for that private group conversation between horny sorority sisters.

Regan took another sip of the wine, this time letting her pink tongue linger on the rim of the glass. "I knew you had slept with Krissy Byrnes and Patty Murphy, even before you and I had dated. Hey, it's a small campus, only thirty thousand or so undergrads, and girls talk." She smirked at her own joke. It seemed to suddenly be getting warmer in the small restaurant, even though the logs in the fireplace were dimming.

"So I wasn't really surprised when both mentioned your name. The words they used were, and I may be paraphrasing now, 'huge', 'all night long', and 'I've never cum like that before or since'. It made quite an impression on me, but I was starting to panic because my turn was coming up. What would I say? I didn't even know what an orgasm felt like at that point." Pre-cum leaked from my dick now, forming in a small pool within my boxers.

Regan's own face was flushed now, and her eyes bore into mine. We were the only two patrons left in the restaurant, but might as well have been the only two people on the planet. She went on.

"Fortunately for me, Phoebe Wilson was sitting just to my left."

My face betrayed my seeming stoicism. Phoebe Wilson was a cheerleader and gymnast who had, shall we conservatively say, a rather healthy carnal appetite.

Phoebe knew more positions than a political candidate during election week, even at that tender age, and had probably been through the Terrapin football team's backfield more times than an opposing pass-rusher. I had the pleasure of, um, 'dating' Phoebe for about two months during winter-term semester junior year, and in that brief time, had learned far more in her bedroom than in any classroom.

"I didn't even know you had been with Phoebe, but, of course, it was difficult to keep track of her inventory." Regan's button nose wrinkled in a grimace. Was it disgust or envy? "But her words saved me, they broke up the room in a series of squeals, and a pillow fight broke out afterwards, so that I didn't have to say anything. All I did was say, 'Hey, I can't top that', and I was off the hook."

Regan stopped her story right there, waiting for me to respond. Of course, I took her bait, hook, line, and sinker. Regan smirked at me, essentially daring me to bite. So I did. I had to, right?

"Um, eh, just, uh, what did she say, Regan?"

Regan flicked the raven hair off of her forehead and her smoky eyes blazed into mine.

"Phoebe Wilson, class slut, said, and I quote, 'Jack Charles is the best fuck on campus. I would pay to have that big, beautiful dick on my nightstand every night'. If you must know."

We sat there, letting the words hang in the air for perhaps thirty seconds. Or an eternity, whichever came first. Regan broke the ice, reaching over to take my hand. "So, you see, Jack, as I approach my fifties, I'm no longer shy, no longer a virgin, no longer intimidated, but most certainly very curious. It's been since the early eighties, I know, but some things don't change." She paused, caressing my palm with her impeccably manicured fingertips. "Do they?"

Phoebe Wilson's fantasy nightstand toy danced wildly beneath the cover of the table top. Regan rose, smoothing her dress down over her exposed thighs as she did so. "I'm going to the ladies' room to freshen up. Would you mind pulling the car around?"

I knew I should have just let well enough alone and been the obedient valet, but keeping my mouth shut has never been one of my strong points, I admit. "So, will we be needing that spare bedroom tonight, Regan?" I asked innocently, trying to be coyly cute.

She glared at me, seemingly not enjoying my charm and wit. "Probably so," she snapped, a flash of anger in her dark eyes. My ego and dick wilted as one in an instant. My big mouth had struck again.

She looked down at me, her tiny frame seemingly dwarfing me now, peering at me as would a scolding teacher to a petulant pupil in a tiny school desk. I cowered in my seat, figuring I had just screwed up everything. And then....Regan said.....

"Because I plan on fucking you in every room of my house before you leave."

Her heels clicked on the wooden floor as she sauntered determinedly to the restroom. I watched her pert little ass sway under the form-fitting dress. Some things may not have changed, but Regan certainly had. I LIKED this Regan, I liked her a lot.

I motioned to the splendid maitre'd, who knew enough to leave us alone for the last hour. "Check, please, Mario. Molto rapidamente, per favore."

He was the recipient of a very big tip. Regan would be shortly.

We somehow managed to keep our hands off of the other on the drive home, which only fueled the sexual anticipation. I wasn't going to make the mistake of opening up my mouth again, and Regan had said all that she needed to say, so we drove in silence as snow flurries started to drift from the sky over the Atlantic Ocean.

I maneuvered her Jag around my own Jeep Cherokee in the driveway and parked it gingerly in the garage. In beach front houses such as this one, the design of the house is usually up on stilts, with the garage being ground-level, as was the case in Regan's abode.

She took my hand, still silent, as she led me up the flight of stairs to the main floor, allowing me an unfettered 'updress' view of her perfect legs for the first time, enough so that I could now verify that she was wearing a garter belt that was attached to the lacy, silk ebony stockings. She walked to the stool in front of the grand piano and sat down on it, crossing her slender legs. Her nipples pointed like teeny missiles through the sheer material of her dress. It was cold, yes, but not THAT cold.

Even though I had noticed the piano while we were enjoying our pre-dinner wine on the couch, until just now I had forgotten that Regan was a sensational piano player. Even back in college she had performed solo classical concerts on campus, but I sure as hell wasn't going to make any 'pianist' comments. She spoke for the first time since she had departed for the ladies' room in the restaurant. She always was a woman of few words, a rare trait in any woman. I decided not to verbalize that thought, either.

Pointing to the embers dying behind the screen of the fireplace, she said softly, "Would you stoke the fire, Jack, please?"

I clumsily pushed the logs around the grates with the bronze toolset rods, trying to feign that I knew that I was doing, and more so, trying not to fall into the inferno as I squatted over it awkwardly. (Hey, YOU try to stoke a fire with a raging hard-on.)

When I turned, the fire successfully raging once again, Regan had risen and without a word, she seductively peeled the straps of her dress from her shoulders, and while still staring right at me, first into my eyes and then down to my bulging crotch, she slowly lowered the zipper on the hip, and shimmied out of the dress with a wiggle.

She stood before me in a sheer black bra, her dark-chocolate nipples poking through the lace, begging release, the stockings and garter ensemble snugly hugging her hips and thighs, a nearly transparent pair of black triangular thong panties pulled up into her slit, and the tasteful stilettos, now looking infinitely more alluring on her tapered ankles.

She was magnificent, her body could have easily shamed that of most coeds. She turned around, providing me a birds-eye view of her firm, pert buttocks, with the string of the thong tucked into her ass, serving as a fulcrum between two exquisitely rounded globes, and reached back to unsnap the hook on her bra, letting it, too, fall to the floor, landing directly on top of her dress. Her bare, shapely back curved downward, and I admired the dimple shape of her backbone just above her tight ass cheeks.

She turned once more, facing me now, her hands clasped over her breasts at first, and then dropped then to her hips, letting me admire the breasts that I had longed to see for well over half of my lifetime. I wondered for just a split second if I was the only UM alum to have seen them, but I'm not sure I wanted to know that answer. My mind works in funny ways sometimes when a beautiful, nearly naked woman is standing in front of me, go figure.

Her tits were small but perfectly proportioned to her frame, and the dark, erect nipples rose with each undulation of her chest as her breathing accelerated. Her tummy was flat, like a washboard, her hips thin, and a small tuft of finely-trimmed dark pubic hair formed an upside down 'V' right over her mound, serving as a directional welcome mat for the inevitable pleasures to come. Her sweet scent of sex wafted through the air, mixing with the swelling fire's aroma, and it was clearly apparent that her protruding labia lips were already puffy and swollen with arousal.

"You're more beautiful than I could have ever imagined, Regan." She smiled broadly at this statement, but again, I couldn't leave well enough alone. "And, believe me, I've masturbated hundreds of times envisioning you exactly like this."

She laughed out loud at my transformation from romantic gentleman to frat boy slug, but strangely enough, her countenance darkened in a lustful expression. My inadvertent confession seemed to further excite her. This truly was a different Regan. Her hand slid down to her crotch and she began to rub her slit which was still covered, barely, by the nearly-not-there thong. I rubbed my own dick in reciprocation. It seemed to be a race as to which would burst first, my cock or her nipples.

Her quiet voice lowered two octaves, huskily inquiring, "When you masturbate about me, tell me.....where on my body do you fantasize shooting your cum?" Her hand snuck under the top of her panty-line, and she pulled the thin lace to one side, exposing herself to me as she inserted a small finger into her glistening slit, patiently awaiting my reply while preparing herself.

I told her honestly, succinctly, taking another slight risk. "Your face, Regan. I imagine shooting my cream on your beautiful face. Always. Then watching you lick me clean."

She closed her eyes and ran a finger of her other hand over her pebble-like nipple, letting her head lean back in imagination. "Mmmmm, sounds wickedly tasty. I've never had a man cum on my face."

"You should add it to your bucket list then." I replied quickly. "Maybe you'll get lucky. 'Tis the season."

She giggled again, bringing me back in time to when I lived to make her laugh, even once. And now, she stood before me, a mature, classy, beautiful woman wanting to fuck me in every room of her house. Dreams come true. Thank you, Santa.

She walked back over to the piano bench and began to play, turning her back to me as I watched her the small crack of her ass part through the thong string as she sat. She began to play a soft, haunting melody that I didn't recognize, her ten fingers making love to the keys, her ten fingers like a mouth on the ivory.

I stood for a moment, not knowing exactly what to do, as she began to hum along with the tune, and she turned her head just a bit, almost whispering over her shoulder to me, not missing a note. "Take your cock out, Jack. Let's feel Phoebe Wilson's nightstand fantasy toy. Rub it on my back while I play. I want to feel your skin against my own."

This was definitely a new one. I wondered silently if Diana Krall or Norah Jones practiced this way as I stripped, but hey, I was just part of the road crew here, what the fuck did I know?

I walked behind Regan and lifted my cock head and gently placed it onto the curve of her spine, just below her shoulder blade, and she purred like a kitten, leaning back into me. She changed the song as I lightly rubbed her shoulders. I recognized this one, it was 'Music of The Night' from Phantom of the Opera, a favorite of mine.