A Randy Retirement Pt. 24: Cindy

Intro: The exploits of a man whose given name fit him perfectly, Randy, and he certainly was that. He was a high-school history teacher and coach until he hit the lottery and retired early at 52. While he was not averse to returning flirtatious quips from the girls in his classes, he did avoid giving in to the urge, telling the more enticing of them to, "come see me after you graduate." Some did, but these stories deal with his life after hitting it big and building two houses; one along a river bluff 45 miles inland from the Atlantic Ocean and another on a secluded portion of the Northern Outer Banks, both equipped with playrooms. And he still had over a hundred million to spare. All characters are 18+ years of age. All stories can stand alone, but reading the series gives added insights and descriptions as it unfolds.

Synopsis: One night stand with the Wedding Director

June, 2018 -- Hotel in Charlotte

Halley had called, which was a rarity as she and Randy did most of their communication by text and that had been slim to none lately.

The setup had been that she would instigate all contact, as he never knew who she was around, but still, he had not attempted to contact her either.

Still, she apologized for her sparse interaction and explained that she carried an exceptionally heavy schedule and was not going to be able to visit him until probably December.

"I had the max load last spring and am doing it again for both summer sessions and this coming fall. I more I can take, the faster I can get finished and the less money it will cost me. And don't start with offering me money." she had expounded.

"I wasn't," he replied without emotion.

Randy was not happy, but played it off and did not let on. Guilt would not do either of them any good. She told him she was going to try to make a quick trip in August, but wasn't certain she could swing it and apologized again. She finished up by trying to reassure him that she wanted to see him, but that she needed to get past this summer session and the fall semester and then things would free up.

Randy clicked off the phone and wondered immediately why it bothered him so much. It was not like he did not expect her to grow distant from him. He had just been preparing to head out to a wedding of a former student in Charlotte when she had called and he brooded over the situation the entire drive.

He briefly wondered if she had met someone, but Randy dismissed that out of hand. If she had met someone, Halley would have told him so. Randy believed they had an honest, open relationship. Still, the thought lingered in the back of his mind as the miles clicked by, his brooding worsening as he searched for a possible answer for why Halley's absence bothered him.

The afternoon rush hour in Charlotte traffic did not help his mood as he made his way to the fancy, upscale hotel downtown on the first Friday of June. Thankfully the check-in was all on the hotel app on his phone, quick and painless; it even had a digital key.

He pulled out his suit from the garment bag and hung it in the bedroom closet, checking for wrinkles but finding none. It was a suite, a nice one, and he wandered into the sitting room and pulled back the curtains. The home stadium of the Charlotte NFL team was so close he could almost reach out and touch it. Beyond it, the traffic on I-277 was crawling along and he grumbled to himself that he was thankful to be out of it.

The wedding was for a former student and player who was marrying a girl from one of the richest families in the state. It was to be a big affair, so despite his loathing of wedding hassles, he had made the trip anyway.

Around six he went down to the hotel restaurant and had dinner, but there were no unattached females in attendance that were of interest to him, and he spent the night alone, channel surfing aimlessly. Halley floated around his mind until he suddenly began to think of Ellie and their last few rendezvous. They had been very satisfying and a wry smile passed across his face. But eventually his mind found its way back to Halley and stayed there until he finally drifted off to a fitful sleep well past midnight.

*

The next afternoon he put on the charcoal gray, pinstriped suit and made his way down to the wedding forty-five minutes early of the 2 p.m. start time.

Everything was in the hotel; the ceremony in a large conference room that would hold upwards of 500 and the reception in an even larger banquet room just down the hall. Judging by the assembled mass, Randy thought they might need a bigger room.

When he walked in, he saw a woman he knew while he waited to be seated. She had her back to him, but he knew it was Cindy immediately. There was a sheaf of papers in her hand, and she was directing the wedding.

Randy's mind focused on the particulars: mid-forties, Amerasian by way of Vietnam but had been born in the US, black hair cut in a bob, black eyes that would mesmerize you, and 34Ds that were obviously bolt-ons because she was flat-chested when she was his student as a senior all those years ago at the first high school where he had taught and coached.

Cindy apparently did not know he was going to be in attendance because she froze momentarily upon seeing him, but recovered quickly. Randy thought he saw a brief flicker of something pass over her eyes when she saw him, but he put it off to his imagination or wishful thinking. He became certain it was his imagination when she did not acknowledge him at all as he passed by her on the way to his seat, even though he had looked at her and nodded.

He asked to be seated near the back. This was a favorite ploy of his and he would do it simply so he could watch the people. However, the enormity of the affair limited his enjoyment. The front of the room where the bride and groom would take their vows was so far away, he briefly thought he should have brought binoculars. His mind turned back to Cindy.

They had never hooked up. In the madhouse of her post-graduation ceremony, he had congratulated her, and she had told him as they hugged, "I'm legal now, almost nineteen and no longer a student. I'm coming to see you this summer," but she never showed. It had never come up in the few times they'd seen each other afterward; before Randy had moved away.

His mind turned back to people watching and trying to pick out those he could remember, while trying to decipher how much they had changed in appearance.

Weddings were a target rich environment, albeit a risky one. One had to discern attachments and he knew that in these situations the truth was sometimes scarce. He had a brief thought that he should have planned ahead, just in case, but he had brought only a travel bag without any toys, just an ever present bottle of lube. His hand came up to feel the knot of his tie as he wondered about using it if the situation arose.

Turning to the wedding program in his other hand, he studied the listing of the wedding party, searching for familiar names, but other than the groom, finding none. Randy was beginning to feel out of place. On the back of the program was a thank you to those that were in attendance for sharing the 'special day' and several acknowledgements. The one for Cindy mentioned her business, which apparently was for wedding planning and services. Randy pulled out his phone and checked the business online, finding that it was very high-end. He was impressed with what she had apparently built for herself.

Not long after, the wedding processional commenced. Randy was seated toward the outside of his row and, if he turned his head slightly, he could she Cindy standing at the back giving directions to the wedding party.

He noticed that she occasionally stole a very brief glance his way during the formalities, but she still did not acknowledge him. During the 'I do' part of the wedding his mind latched onto the idea that, 'She's high society now, prim and proper. I guess that she has to be in order to fit in with her clients. The upper crust of the Queen City's society ... can't be seen with the out-of-town riff-raff,' and he settled in on the couple that was far away, but front and center. He pushed Cindy out of his mind as well.

When the ceremony concluded, Randy made his way to the reception; placing a sealed envelope marked 'For the Honeymoon' on the table set up for gifts. He never knew what to give as a gift and usually settled on money. A thousand dollars could come in handy.

He mingled and greeted a few others that he knew from his first school and took the time to catch up. This slowed him from making his way to the hors d'oeuvre line, but he eventually did and loaded up a plate. He grabbed a plastic cup of red punch and then found a small circular table along the wall.

He sat in one of the two chairs and passed the time with his food while the couple and their wedding party took pictures in the other room. It had been over forty-five minutes since he had finished eating and he probably would have already left if not for former students from twenty-plus years ago stopping by to visit.

Finally, the bridal party arrived to cheers and applause and Randy noticed that Cindy brought up the rear. She searched the crowd as she mingled, accepting congratulations and salutations. Suddenly the thought occurred that she was looking for him, but he just sat there and let her work for it, if indeed his thought were correct.

Finally, she saw him. She stopped to get two glasses of wine and came over.

"No plus one?" she asked as she stood before him.

Randy rose and hugged her while replying, "Nope, just me. Did you bring me wine?"

She sat in the extra chair, "Yes, or I'll drink both if you don't want any. How have you been?" Her dark eyes sparkled, and he was drawn in, just like he had been all those years ago. They talked while drinking the wine, interrupted only by the toasts.

He asked her about her business and Cindy related how she had come to own the bridal shop and that she did between 35 and 40 weddings a year. It was a full-service business. She could provide the location, music, singers, catering, invitations, reception; all for a price and only the upper class could afford it. Randy commented on how that must be exhilarating, and Cindy agreed.

"Oh, it is, but it's tedious at times too. Nothing is too good or too expensive for their babies and as a result, I get in the homes of the city's royalty and I like it, plus I make a better than good living. But I'm telling you, some of these people are certifiable," and they both laughed. "Don't go telling anyone I said that now."

Randy traced an imaginary cross over his chest as a promise, and they laughed again.

The emcee announced that the newly married couple would be having their first dance and they both stood to watch. Over the music she told him that she did not direct many weddings anymore, she had employees to do that, but she did this one gratis because it was a former classmate.

"You paid for all this?" and he gestured at the room.

"Oh, hell no, I mean the actual directing of the service was gratis. All this," and she gestured to the room in the same manner he had, "cost about $75,000."

"Shit," he whistled.

"Yeah, exactly, but it pays my bills."

In the middle of the dance, and still over the music, he asked her, "Are you married?"

"Divorced."

"I'm sorry," he offered.

"No, you're not," she laughed, still watching the newlyweds dancing.

"No, I'm not," Randy replied, laughing as well. "915."

"That your room number?" she inquired, still looking at the dancing couple.

"It is."

"The nine-hundreds are the suites."

"They are."

"The expensive ones," she probed, stretching to continue to look out on the dance floor.

"Yep."

Cindy's eyes flitted around, taking in the large banquet room and noting where certain individuals were located. "Give me fifteen minutes to say my good-byes here and I'll meet you up there."

"Are you gonna stand me up again?"

Cindy turned to him for the first time since the dance had begun, "Oh no, not this time."

Randy simply nodded and left. As he rode the elevator up, he thought of her sitting there at his table just now. She was beautiful. She was wearing a pearl-colored, strap-less dress that came to mid-calf and showed off her figure. A very large pearl necklace and dangling pearl earrings completed her ensemble. His cock had begun to twitch from desire. When he got to his room, he didn't even turn on the lights, removing his jacket and tie as he went to the bathroom and his bag, taking a blue pill. He was going to make sure this one lasted a while if she showed. If she didn't, he was going to have a long night.

Walking to the open curtains of the sitting room, he stood there looking out at the lights of south Charlotte as he sipped from the bottle of water, the anticipation building as time ticked by, until there was an insistent knock at his door.

He checked the peep hole and relished the look of her for just a moment before opening it to a storm.

"Hello..." he started, but never finished.

Cindy was neither prim nor proper; instead, she attacked him passionately with her mouth without a word of greeting, a bottle of champaign in her hand. They made their way into the sitting room, and she relented long enough to put the bottle and her clutch purse down and then resumed, backing him to the loveseat that sat beside the large window. The only light in the room came from the open bedroom doors where he had left the light on in the bath and the dim glow from the window.

Adjusting her short hair, she told him, "I'm sorry. You got me kind of worked up."

"No need to apologize, I rather enjoyed it," he sniffed.

"I've had to be so damned straight-laced for so long," and she paused, "as soon as I saw you and noticed that you were alone, I thought to myself, I said 'Self, here is your chance to let it all go and have a good time and nobody has to know.' So, I decided to act on impulse."

"I like impulse Cindy."

She responded by reaching for his crotch

His dick is already hard from the tête-à-tête downstairs and the way she had entered the room; the pill he took was just now beginning to really work its magic.

She looked at him, eyes wide and mouth agape as her hand found its target. She was in cock shock and couldn't speak for several seconds, leaving her hand on his dick the entire time while Randy just stared at her. Finally, she looked up at his face, "If I had known this, I would have done something about it years ago."

"No time like the present," he told her, and she moved in to kiss him again, unbuttoning his shirt as she did so.

They stood and undressed; Randy whistled in surprise when he saw that she was as bare as the day she was born.

"You like?" she asked, looking down as her hands framed her pussy.

"I love."

"I was tired of messing with it and had it permanently removed," and she looked up grinning at him.

Her nipples were dark brown and distended; they looked like little buttes, an inch in diameter and extending almost two from her dark aureoles. The thought occurred to Randy that if he did it hard enough, he could suck them right off her breast. He reached out with both hands, Cindy's eyes following them, but not resisting. Tweaking them gently, he found that they were firm and solid.

Placing her hands flat on his chest, she sat him down on the loveseat again and grasped the base of his dick with one hand, the other on the seat as they faced each other. Her head was less than six inches from his and they both held still for a moment, the fire beginning to rage inside.

"You held out on us girls," her head bent down to wet the crown of his cock before she continued, "Back then when we were seniors and all of legal age, we all talked amongst ourselves about fucking you, but we were all scared we'd get in trouble because we were still students." She dipped her head again on his cock and took in the first few exploratory inches, drooling on it extensively. When her head rose slightly, she kept it pointed down at his cock, strings of saliva maintaining the connection between her mouth with his dick. Her eyes had teared up and the enormity of what she had chosen to do was affecting her speech.

"When you danced with us at the prom, we all got wet panties," she croaked and went almost all the way down on his cock for just a moment, came off again and cleared her throat. She brought her offhand up to wipe her eyes and mouth. "If any one of us had fucked you and shared the news of this," and she squeezed his cock as she put her other hand back on the loveseat.

Randy was rock hard, and his cock gave very little in her hand. She ticked her head at an angle at the implication. "Damn you're hard. I tell you, if we had known about this cock, we all would have fucked you," and she took all of it into her mouth and deep throated him for just a moment, slightly gagging. Then she did it again. All the way down and immediately, all the way back up; spending no more than a second at any one place along his shaft.

"Not until you were all legal," Randy added as the head of short, black hair bobbled in his lap.

"Gluck ... gluck ... gluck," filled the room as Cindy positioned herself on the loveseat for a better angle. She was dressed only in her pearls. Occasionally she would come up for air, never letting go of his dick, and he would marvel at her beauty. She was an enthusiastic cocksucker, and he did not interfere with her eagerness at first. In time he would be ready to participate.

She continued to suck his dick, not able to hold herself on him for longer than the one second, but she made up for it with the attention she gave to the full length of his cock, her head and shoulders moving in unison as her spit coated both hand and face.

Finally, Randy decided to get involved. He grasped the thick hair at the top of her head when she came up for breath the next time and watched as she tapped the center of her lips with his dick. She had what resembled a goatee, made of saliva, which coated her mouth and chin, and she blew bubbles as she kissed his cockhead.

"Oh, you sweet little cock tease, get on your back," he told her, and she giggled before licking his cock a final time and situating herself. Randy twisted her body so that her ass hung off the edge of the loveseat.

On his knees, he bent to reciprocate, burying his tongue in her pussy at first, but then working his way to her clitoris. It was where he did his best work. He reached up with his hands and pinched her nipples at the precise moment he first sucked hard on her clit, bringing a shriek of joy as her body tensed for a moment. Cindy raised her hands to clasp the back of the furniture and held on tight, her head between her elbows as she watched Randy delve into her nether region.

Her abs were not flat, but they did not show the flab of age yet either and he watched her abdomen undulate as he alternated between sucking and lightly biting her emerging sweet spot.

He brought his hands down and began to insert fingers into her, spending an inordinate amount of time prepping Cindy. When his hands told him she was well lubricated with her natural secretions, he stood and reached down for her hands, pulling her upright.

He drew her toward the large window and positioned her as he wanted; arms extended, palms flat on the glass and legs spread. Without prompting, she arched her back, forming a shelf with her ass that he could put a TV tray on and not spill anything.

Cindy knew what was about to happen and was hesitant about the window, "What if someone sees us?

It was then that Randy wordlessly put his cock in her pussy, driving it home and pushing her up on her toes as he held her hips.

"Ahhh, fuck it," she gasped. "Ohhh shit, you're cock's big. Arrgghhhh!" and her head dropped down as she looked at her pelvis rocking forward with each powerful thrust of his dick; moaning and groaning as Randy began to slowly plow into her. He increased his stroke in increments until he was power fucking her, her body yearning for release.