A Randy Retirement Pt. 12: Merry

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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: Former student, now in real estate, lured to play.

April, 2017 — River house

Her first name was Merry. Her mother had a strange sense of humor because her middle name was Christmas. She had been born on Christmas Day and the mother had insisted until the father had relented. She was a former student of Randy’s who had gotten a business degree in college and then gone into real estate. They had run into each other on a Saturday night at some community function in town that Randy had been invited to, the directors hoping to get their hands on some of his money.

She was mid-twenties and petite, about 5’3″ and 110 pounds. Decent body, but not overly smoking, with a 32B-24-32 figure. But she did have a certain allure as her father had been full-blooded Cherokee and she had inherited his skin tone, facial features, and hair which gave her a sultry look.

Randy wanted to see her naked and wiggling on his cock, but knew he had to play this very carefully. There was no flirting in their pleasant conversation and the aura he felt around her was one of innocence and a hint of repression.

In her job, Merry was a go-getter and inquired if Randy might want to put his house on the market. He didn’t, but there was no reason to let her know that. Instead, he asked if she might want to come out and assess it for him so that he could have some idea of what she thought she could sell it for. They set up an appointment for the Friday following and Randy hugged her briefly and loosely before departing with his wallet still intact.

The next week she had gathered as much information about his property as the public records would allow and realized that this could be the sale that would make her reputation in the local real estate market. Merry was excited and ready as the appointed day approached.

For his part, Randy had spent the week contemplating how to play her visit in such a way as to manipulate her into allowing him to fuck her. She had been prim and proper in most all his observations of her in high school, but there were those rare occasions where he had seen a little wildness that would rear it’s suppressed self. He suspected that, despite her innocence, she had a faint awareness of some of the self-indulgent aspects of life, and sex. Finally, on Thursday morning as he walked along the riverbank, he settled on how he would steer the meeting and reminded himself that it was no loss if it failed.


As the clock ticked toward the appointment, Randy took a Viagra and kept watch on the security monitor in the kitchen cabinet. When he saw Merry’s car come down the drive he started the video recording system in the house and went to wait in the foyer.

She had showed up at the exact appointed time in a black sundress with small lavender and white flowers connected by green vines printed on it and a pair of sensible flats. He noted that she wore gold, hand-beaten, leaf-shaped earrings that dangled and a large gold watch as he let her inside.

She carried a black leather folder with brass at the corners and thanked him profusely for allowing her to do this as she opened it, Cartier pen in hand, and asked about the septic and water systems while they stood in the foyer; Merry with her mind on making money and Randy with his mind on making her cum.

Her ass was petite like the rest of her, but he was reminded upon closer inspection when she turned her back to him and made notes of the entrance to his home that it had that certain peach shape to it. Her long brown hair was chestnut colored, parted on the left with a swoop of bangs pulled over to her right ear and clipped there. She had a second metal clip holding back the long hair above her left ear.

Merry’s breasts were not pronounced, but looked firm as they sat high on her chest with a cleavage that was slightly visible; almost as if she had taped them, like the beauty pageant contestants sometimes did.

He took her first to the right and showed her his office space, asking if she would like something to drink. She requested water and he took two bottles from the mini-frig and continued to the Master bath done in Italian marble. Merry scribbled furiously in her notepad as she gushed about the workmanship and the view bursa eskort from the elevated tub. The tub was obviously built for two, as was the shower with its dual heads on opposite ends. If she noticed the anal enema attachment in the shower, she did not acknowledge it as she wrote.

He let her inside the huge walk-in closet and washer-dryer area and stood by the door as she made notes and gave more compliments, asking the occasional question. He had to give her credit for her verbal stroking skills and wondered about her other stroking skills.

Continuing, they walked through the Master bedroom with the atrium of smoked glass and again she scribbled and gushed, inquiring if he intended to sell it furnished or not. He thought for a moment, considered a blatant sexual reference, but decided against it and told her he would sell it furnished if that was what the buyer wanted.

On they went, to the sunken living room with the large windows and the open plan kitchen, breakfast nook and dining room. Merry was doing more writing and gushing in each area, asking more questions and noting the answers each time.

He took her through the breezeway to the pavilion and she stopped to ask about the pool and hot tub before following him to the octagon shaped party area with its own windowed view of the river. “Do you entertain many guests?” she questioned as she made notes on the grill and stove.

Randy reflected, “The visits I get from guests are usually one on one affairs, so no,” and she turned and gave him a wary smile. She did not allow whether she approved or not to show through and Randy was more convinced than ever that she was a master at repression.

He backtracked her to the foyer and they ascended the angled stairway, turning to the right and the media room. It was at this point that his phone dinged with a text and he checked to see it was Halley (previous stories).

He turned the lights on so that the reddish-brown toned woman could inspect the room and excused himself back to the catwalk outside to read Halley’s text.

‘what’s up. just wanted to say happy anniversary and ask for a date in august. unfortunately i won’t get back until then, save the date!!!!’

Randy tapped out a reply, ‘That’s unfortunate, but I understand. Happy Anniversary! Love you and miss you dearly,’ and he added a heart emoji.

A moment later she responded, ‘i know, me2. what are you up to?’

Randy smirked and decided to be honest, ‘Showing the house to a real estate lady,” and followed with the big eye-ed emoji.

Halley replied instantly, ‘WHAT!!! you’d better not be selling MY HOUSE!!!’

More honesty came in his next reply, ‘Oh, I’m not, I’m just setting her up to fuck her,” and he followed that with a wink emoji.

Halley replied with the laughing out loud faces, several of them, and then texted, ‘well, have fun and hit it hard, but don’t have too much fun. save some for me!’ and added a beating heart.

He sent her a kiss and pocketed the cell before walking back to the entrance of the media room. Merry was at the far end and headed back his way up the cantilevered floor.

“You have all this room and you never entertain guests?”

He mugged his face as she approached and told her, “Nope. I had this room built for me to watch football in. I had to do something with the space and this seemed like a good idea. I had visions of having large groups here for movies and big ball games, but it’s never worked out.” He paused purposefully before continuing, allowing her to stop beside him, “Only one-on-one encounters in here so far.” He winked at her and she shook her head and laughed nervously as he led her back out and across the catwalk, pointing out the view of the first-floor areas below them.

He showed her the library and mentioned that he would be taking his books if it sold and continued to the two guest rooms, allowing her to enter and ask questions as he stood at the doorways of each, arms folded across his chest.

When she exited, he went ahead toward the spiral staircase and elevator and pointed to the guest bathroom on the right. She scribbled a note about the elevator before turning to enter the bath. Randy again stood at the doorway and watched as she inspected the room, waiting and watching.

“This is a very well-equipped bath,” she was saying as the opened the door to the over-sized shower, “I love how you,” and she paused when she saw the anal enema attachment hanging there next to the doorway before finishing the sentence slowly, “have laid things out.”

The first crack in her self-assuredness appeared as she pointed and slowly turned her head toward him, her mouth forming a small ‘o’ in wonder. “Is that?”

Randy finished the thought for her, “An attachment for cleaning out someone’s asshole? Yes, it is. I’m impressed that you recognize it. You missed the one in the Master bath,” and Merry slowly closed the shower door. She coughed and Randy watched as she struggled to regain her composure while she exited the bathroom.

He smiled at her as she bursa otele gelen escort checked her writing pad, stalling for time, and then looked at him, “There is no storage area in the space above the garage?”

‘Bingo!’ he thought to himself.

Unfolding his arms, he headed to the seemingly blank wall with the small seam in the middle, “There’s a space, but it’s not for storage,” and he reached for the small box that was out of sight on the right and flipped the switch.

The doors whooshed open and her eyes widened.

Merry entered as Randy followed and stopped beside her. He remained silent as the same small ‘o’ formed on her mouth again and her grip on the pen, pad and water bottle loosened. He reached and took them from her hands before they could tumble to the floor and Merry slowly moved further into the room and took in the various bondage devices.

She started on the left and began a slow circle, silently touching each device as she went. Randy placed her items on the computer table and then traversed the right side of the room. He met her at the entrance of the small room with the twin-sized brass-railed bed after she had touched the cold of the stainless-steel autopsy table with the leather cuffs at each corner.

She stopped before him and lifted her head, finding words difficult to form, “You use this,” and she searched for the word, “stuff?”

“Well, not alone, but yes, I use this stuff,” and he placed his hands on her hips and waited for her reaction.

Merry reacted by placing her hands on his biceps but did not resist him as she continued to look around the room, finally settling her eyes back upon him.

“You really aren’t interested in selling the house, are you?” she asked him.


“You schemed this all out just to get me here, in this room, at this moment.”


“And exactly what did you think was gonna happen?”

“I think you’re gonna let me make you have the best orgasm of your life,” and Randy lowered his hands to her ass, palming it firmly.

Again, she did not resist.

“I,” she started and then paused for a prolonged moment.

“It’s a one-time shot Merry. Either you take it or let it pass. Kinda like a comet that comes by once in a lifetime, if you miss seeing it, then you’ll never experience it.”

She opened her mouth, but no words came, and he gave her time to decide as her eyes bored a hole in his sternum for almost a minute before she spoke.

“I can’t,” and again she paused. After several seconds she began to pull away and he did not resist. “I’m,” and she trailed off again as she broke the embrace and started for the door.

She had only gotten ten feet away when she heard a noise but did not stop until Randy called her name.

“Merry,” and she paused and then turned. He had dropped his pants and his 10-inch cock was standing at attention and she immediately froze. The small ‘o’ returned to her mouth and when he bounced on the balls of his feet and his long, thick cock waved at her she put her hands to her cheeks in disbelief.

“That would have never fit in me,” she whispered as he came to her.

“Would have?” he asked as he came toward her, and she removed her hands from her face. For a moment he thought she would grab his dick but Merry just stood there staring down at it from two feet away. Finally, he told her, “Why don’t you just reach down and touch it. Just to make sure it’s real before you leave?”

Merry glanced back to him briefly and then licked her lips as she tentatively reached down with the fingertips of her right hand and gently touched the crown of his two-inch thick cock. It was hard and stiff, and she began to marvel at it as she wrapped the palm of her hand around the shaft just below the head.

It was then that Randy told her, “Don’t let go,” as he reached out with both hands and tweaked her nipples through the fabric of her sundress, making her gasp as she again looked into his eyes. Both nipples were hard enough to cut glass and it was the first concrete sign he’d had that she was more than just flabbergasted. “How wet are your panties Merry?” he asked.

Suddenly she was aware of the dampness between her thighs and she squirmed as he held onto the nubs of breasts, each the size of a small marble. She did not resist as he pulled her to him by her nipples and kissed her on the lips. She opened her mouth and began to give him her tongue and when she did, he again moved his hands to her ass and began to bunch the sundress up to her hips.

Merry still had her hand firmly around his dick as he broke off the kiss and told her, “You’re gonna have to let go for a sec so I can take off your dress.” She did, but not before bending at the waist to kiss his cock lightly on the head and Randy smiled.

He turned and began to herd her back toward the smaller room with the bed as he removed her dress and bra while she removed her earrings and watch. When they arrived at the room, he stood her in front of the bed and, from behind, removed nilüfer escort her shoes and panties, placing all her belongings in the corner. He noticed that she had trimmed her pubic hair into a tight triangle of stubble.

Putting his tongue in her right ear, he began to finger her wet slit, Merry responded by subconsciously widening her feet to give him greater access. She purred and nuzzled his face with hers as she palmed her breasts with her hands. When her breathing changed, he stopped playing with her pussy and turned her to face him.

“Clasp your hands behind your back and no matter what I do, leave them there,” he told her in a stern voice and she hesitated but then complied.

Randy reached for the clips, releasing her straight brown hair and then held the clips in front of her face. Merry stared at the metal jaws as he opened and closed them before her. Without warning he attached each of them to one of her nipples and she rose on her toes and hissed, but did not unclasp her hands.

He sat her down on the bed and then rolled her onto her back with her ass hanging off the edge. Her hands were still clasped and now underneath her as he pushed back her legs and stooped to lap at her pussy. She had a toned and muscular body that gave off a medium brown glow owing to her Native American heritage, but at the moment her was eyeing the deep pink of her slit.

Pausing from his ministrations, Randy announced “You taste like Sprite,” to which she did not respond. He reburied his tongue in her snatch and watched the rise and fall of her diaphragm as her breathing quickened. Her belly button was of the split type and looked like a lowercase ‘i’ without the dot and it rippled with her breathing.

Without stopping his eating, he reached under the bed and brought out four leather bondage cuffs and tossed them on the bed. Between licks of her pussy, he told her to put them on and watched her struggle to do so while he focused on her clit.

When she had her limbs encased in the cuffs, he stopped eating her and used double ended clips to secure wrist to ankle and pushed apart her thighs, inserted a finger and found her G-spot as he bent to suck on her emerging clit. Like her nipples, it was the size of a small marble and already stiff.

Merry began to arch her back and force herself toward his finger and mouth. She murmured in a little voice that matched her petite body. When he got her so worked up that she lifted her ass entirely off the bed he stopped and she looked up at him. He smiled at the beginnings of the wildness that showed in her eyes.

Pulling her off the bed to the floor, her wrists now behind her and still connected to her ankles, she looked up at him with expectation. His dick at attention and in her face, he told her, “Your turn now,” and she viewed the wide head with a look of trepidation.

Surprising him, her mouth was wide enough to accommodate his cock, but she gagged immediately with less than half of it in her mouth. Randy felt the fit and knew it was too tight to push the issue and let her work on the amount of his cock that she could handle.

And handle it she did, bobbing her head eagerly on his shaft and using her tongue on the crown of his cock. Drool escaped and coated her chest and abdomen as she continued.

He let her work on him for a good ten minutes before he bent and pulled her head off his dick by her long chestnut brown hair and asked her, “What do you want Merry?”

“I want you to do me,” came the reply.

Unclipping her bonds, he stood her up and brought her to the main playroom where he affixed her ankle cuffs wide to the floor and brought her wrists together and clipped them high to a bar so that her body was taut and had a slight lean forward to it.

He walked to her front and released the clips on her nipples and her eyes shot wide as she looked down at them while the blood rushed back and then alternately to him with her lips pursed. Randy took her chin and kissed her savagely, sucking her tongue into his mouth and not letting go for several seconds as she began to moan.

He drew his head back and looked into her still wild eyes as he held her by the chin. Her hair askew and her lips still pursed as if she were about to spit. He pronounced, “You’re going to enjoy this.”

Behind her now, he teased his cock between her spread legs and the top of his shaft became coated in her juices. He used a hand to spread the natural lubricant on himself and then placed a hand around and on her stomach and took his cock in the other and began to probe her pussy with it.

When he entered her, she squealed and tried to close her legs, but he pressed more of his meat into her and she shouted, “You’re gonna split me open!”

Randy paused, flexed his cock, and asked, “Do you want me to stop?”

Merry cried out in a lustful tone, “No!”

He took it easy on her, using only half his cock and slowly fucking her. Merry’s body was tense and she strained her arms as her shoulders bunched in a slow motion that one could take as torment. As she became even wetter the juices of her pussy allowed him to stretch her further and he managed to get eight of his ten inches inside. She was crying out in a mix of agony and ecstasy as he fucked her for several minutes and then removed his cock from her and came back around to the front.

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