A Randy Retirement Pt. 05: Halley Ch. 03

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 involved in sex are 18+ years of age and fictional. All stories can stand alone, but reading the series gives added insights and descriptions as it unfolds.

Synopsis: Teen blonde leaves her graduation party to visit her step-uncle and experiences first anal.

June, 2016 - River House

Locally, the first Saturday of June is traditionally high-school graduation day and Halley's had arrived. The eighteen-year-old had invited her step-uncle by marriage, Randy, to the ceremony, but he had declined.

Being a retired teacher, he had texted her, "Halley, I've been to over 30 in my life and it's hot as hell, I don't need to go to another and sweat amongst all those people. I'll see you at the party Saturday evening."

They had developed a special fucking relationship over the past two months (see previous stories), he became her carnal mentor, and despite her inexperience, Halley was blossoming into a sensual creature as she learned to play with his ten-inch cock.

He arrived at her home just prior to the 5:00 p.m. invitation and parked down the street from the modest brick home. Attached to its side was a two-car garage that held tables and chairs and had upward of 30 people milling about: aunts and uncles and cousins and parents and step-parents and grandparents; an overabundance of kinfolk, by blood and by marriage.

Halley was mingling amongst the guests as Randy sat in a corner near one of the open garage doors. He had brought with him a card and a box and placed them on the table as he sat and took her in. She was dressed in a knee-length black dress that was low-cut and had spaghetti straps. She wore a gray cotton bra whose straps showed on her lightly tanned shoulders and Bohemian leaf fringed feathered earrings in turquoise.

Her sister Gabbie stopped by and asked him if he wanted anything to drink and he asked for a water. He watched her walk away. Other than the blonde hair they were nothing alike, but Randy could see that Gabbie too would be a good-looking woman as she aged. It was then that Halley arrived at his side.

"Congratulations," he told her as he stood to give her a hug, noticing the thin nose ring in her left nostril, but hiding his irritation, "how does it feel to be a high school graduate?"

"Great," she mocked enthusiasm and re-hugged him, whispering in his ear, "Get me out of here, these people are driving me nuts."

Randy chuckled, "Now, now. We must serve our penance for all those graduation presents. Speaking of which, we need to go somewhere private so I can give you yours," and he nodded to the box and envelope on the table.

Gabbie brought his water and Halley held her reply as he thanked her sister for the bottle. Once she had walked away, Halley whispered, "Follow me," and she started off toward the house.

Once inside they went through the kitchen and he asked her as he followed, "Are you sure we'll be alone?"

"Yeah, they're all outside gossiping about each other. It'll be ten minutes before they miss me." She opened the door to her room and motioned him in, shutting it behind them and then she turned and rushed into his arms.

Randy kissed her briefly and then handed her the envelope. She opened it to at least a dozen hundred-dollar bills, and he told her, "No one is to know you got that much money from me. There's a twenty in there for public consumption, but the hundreds are your secret emergency stash for college, kapisch?"

"Kapisch," she replied, her head still tilted down at the bills in her hands, until she looked up and grinned, "What's in the box?"

"Are you wearing underwear?" he asked.

Halley pulled up her dress to reveal a small Lycra thong in turquoise over her bare pussy. Randy opened the box and brought out a pink item that had a bulb about the size of a golf ball and a long thin tail that was about five inches in length.

Halley looked at it as he held it up by its tail, "What is it?"

"It's a Lush remote-controlled vibrator. Open your mouth," and as she still held her dress up, she obliged and wet it with her saliva. When she had it fully wet, Randy pulled her thong aside and inserted the bulb into her pussy with two fingers and slid it up until only two inches of the tail were visible as she rose on her toes and sighed. "That should be enough of the antenna left outside," and he reset her thong.

"Antenna?" she questioned warily.

"There you go, all ready," he ignored her question and brought out his phone, smiling deviously at her. "I have the app for it on my phone, I'll show you how to download it later, but I can control it's vibrations from 40 feet away," and he gave her a short taste of its feel and she whooped and dropped her dress to look at and to feel her abdomen through the fabric.

"You're evil," she smiled as her head upturned to look at him.

"Yeah, yeah, we established that last time, although I believe you called me mean then. Now out you go to commune with your guests and let me play with you without you letting on. Good luck," and he motioned her out the door.

Other than during the short speeches to acknowledge Halley's achievement, he tormented her over the next ninety minutes, discretely working the controls on his phone in the various modes and cycles of the vibrator. He never let her get all the way there, although she did dance on the edge when he put the earthquake mode on high while she was talking with one of her grandmothers.

Eventually she made her way back to him, her thick puffy nipples evident through two layers of fabric and sat next to him. "You ass," she hissed quietly as she sat beside him.

"What, you don't like your present?" he asked in mock seriousness and increased the vibrations.

Halley put her elbows on the table and held her head in her hands, "I love it," she barely managed to say.

"Unlock your phone and give it to me," he demanded as he dialed down the vibrations, and she did so.

As he made sure she had her Wi-Fi hotspot on and downloaded the app to her phone he told her, "Don't take it out when I leave. There you go, now you can control it if you want to after today," and he passed her phone to her.

"You put that on my real phone?" she asked.

"Yep, don't get caught," and he smiled at her as she shook her head.

"In all seriousness, congratulations Halley. I'm proud of you and all you've come to be. Just remember, the best is yet to come," and he rose, kissed her on the forehead and departed, saying his goodbyes to his hosts on the way out.

Before driving away, he sent Halley a brief text on her other phone, the burner he had supplied for their clandestine communications.

"If you want to cum to my house tonight #PunctuationMatters"

*

Randy continued to play with the Lush on his phone after he left; all the way home and after he got inside. Almost an hour later the security system alerted him to someone coming down his driveway and he checked the cameras to see Halley's yellow car speeding down the pavement. He opened the front door and waited for her as she hurried up the steps and put hands on hips.

Blonde hair the color of wheat straw with long legs, she was a tall vision of beauty with a nice ass and tits that came in at a B-cup. He drank her in as she approached.

"You almost made me wreck," she said with a tremble in her voice.

"How'd you get away?" he queried her.

"I couldn't read it until the party was winding up and I made an excuse to go to the bathroom. That burner is small, but it's still not easy to hide. I told them I was going to a friend's party and not to look for me until after midnight," and she then took his hand and led him straight upstairs to the playroom by way of the main stairs and through the library.

Before they got there, he detoured her to the familiar guest bedroom and once inside, turned her to face him as he held both of her hands in his. "There are some things I need to say," he started. "It's your body and you can do anything with it that you want. I only control it when you give me control. But I must express my opinion and wishes this once," and he pushed her against the wall and placed his right hand around her throat, but did not squeeze it, and with the left he pulled up the hem of her dress. He found that she had removed her thong as he removed the vibrator and dropped it to the floor and replaced it with two fingers in her snatch and his thumb on her clit.

"You can do anything you want when you're with me, explore whatever you want sexually, I will never judge you and no one other than us will ever know. Do you understand this?"

Halley nodded, not quite sure what was happening, but not afraid either. Actually, she was getting wetter.

Randy continued, "But, no tats. And take the damned ring outta your nose. No facial piercings other than your ears. I may pierce you myself someday, but that would be your nipples or your clit," and he felt her get wetter.

"Why no tats or facial piercings?" she whispered.

"Because to me, they are a distraction, they take the attention away from you and puts it on them. It's all anyone focuses on, trying to read it or figure out what the hell it is. I don't know, it's just a pet peeve I guess, and seeing your nose ring today set me off."

Randy kissed and released her and then removed her dress and let it fall to the floor beside the vibrator and saw that Halley's juices were leaking down her leg. He wiped his hand on her thigh and brought his damp fingers to her face, "Miss me?'

"Little bit," she teased by holding up her thumb and forefinger, a half inch between them.

He began to unbutton his shirt and she stooped to remove his pants, both in a frantic hurry as the temperature was rising in them both. When she helped him step out of his pants, her face was greeted with a semi-erect cock which she immediately took into her mouth. She stroked him and sucked him and used her tongue to tease him and Randy thought of how far she had come in the last few months and smiled.

When she was satisfied that he was ready she rose to face him, their foreheads and noses touching as her right hand still embraced his dick with the same pressure that he had earlier held her throat.

"I want my real graduation present," she told him, and she squeezed him tighter.

He moved his hands to hers and entwined his fingers in each and then backed to the bed, leading her along with him. When they got there, he fell backwards and pulled her on top of him with his feet still on the floor and told her, "time for you to learn how to control the action."

She freed her hands from his and placed them both on his chest as she bent down to kiss him deeply and rubbed her ass crack on the rigidness of his now upright dick. When she could wait no longer, she rose on her knees and moved her right hand to his cock to insert him into her, sighing as she did so.

"Oh, how I've missed you," she purred down to him.

"Un-huh, you missed my dick," he replied in sarcasm.

Placing her right hand back on his chest, Halley started to rock until she had half of his ten inches inside her and grinned deliciously, "Well, yes, this is true," and then pressed down to engulf the rest of his hardness and sighed loudly, "Ohh yes, I've missed you both."

He let her set her own place, resisting the temptation to pound her from below, and watched as her face contorted in different ways with each stroke she made. She settled into a rhythm of slow and sensuous strokes that brought her body up and down the full length of him and built her orgasm in the same slow and sensuous way.

Halley became increasingly lost in the feeling of fullness inside her. Over the past month she had longed for him in a way that her fingers or the dildo he had given her just did not satisfy and she relished each movement of his wide cockhead and long shaft inside her now. The twitch that befell her pussy each time her hips seated on his pelvis was a feeling that was some sort of elixir to her sexual soul and she knew was becoming addictive, but she did not care. It was amazing.

She tried with some difficulty to sit up straighter and change the angle of his entry and he reached for her hands and clasped them in his own and let her use them as braces as she moved from her knees to her feet and squatted on his cock. She opened her eyes in wonder as it allowed his dick deeper inside.

His cockhead was now striking her cervix with each downstroke and she felt the discomfort at first, but the reaction of her body sexually was multiplied, and she started to move faster, rotating and twisting her hips with each stroke.

Randy turned his head to the right to watch her work on his cock in the mirror that hung above the headboard. He was holding her hands out to her sides and her ass was tamping down upon his cock with a steadily increasing force that revealed her growing need and caused her dangling earrings to swing wildly.

When she came, she gripped his hands tightly and momentarily stopped with his cock buried inside to its full length and after a few seconds slowly started to ride him again in full strokes as she continued to cum silently.

Randy folded her arms behind her and sat up, releasing her hands to caress her buttocks, and encouraging her to grind on his fully buried cock as she left her freed hands at her back. The friction on her clit brought her immediately to another orgasm as she placed her forehead against his and panted.

He did not wait for her to recover, instead placing her arms around his neck and hooking under her knees with each arm while cupping her ass cheeks. He stood with his dick still buried inside her and began to use his arms to pound her pussy, the sound of the 'slap, slap' of their bodies mixed with her vocal exhortations to him filling the room.

This time when she came, she spasmed, her long legs locked tightly around his lower back and pinning his arms to his sides. Her own arms pulled him tightly into her chest and she softly bit his shoulder.

Randy wondered if she had squirted as he felt her juices on his legs as her pussy twitched on his cock.

With her grip on his body limiting his ability to hold her up, he let them fall backwards to the bed and then sideways as he pulled out.

Reaching to rub between her legs, he found her pussy lips were palpitating as if he was still fucking her and slowly rubbed them to stillness.

Halley repositioned her body to lie lengthwise on the bed and Randy followed suit, so that her head lie on his chest and he could rub her back with his right arm. He had a pang of regret about how forcefully he had expressed himself earlier and revisited the subject.

"Do you understand what I was saying about the tats and piercings?"

She began tracing her finger on his chest, something that she had done before, and her reply came as she watched her finger move,

"Yes, that they distract from natural beauty and that you don't like them but that in the end, it's still my choice."

"Absolutely, correct. I knew you were a smart girl."

"Ha, not too smart. I lost my virginity to someone who didn't know what they were doing," and she continued to trace.

Randy let that set for a moment and tried to figure out what she was writing, but couldn't. He then ventured into what had been on his mind for this day for weeks, "But you're still a virgin in one sense."

Halley's face turned to him, puzzlement in her eyes until Randy stretched his right arm and placed his forefinger on her asshole. "I told you that the next time I was taking your ass," and her eyes widened as they found understanding.

Randy started stroking her asshole with a light circular motion; Halley looking at him with her mouth open and wonder in her eyes.

Eventually she voiced what was foremost in her mind, "Will it fit?"

Randy sat up and exited the bed, reaching out a hand to aid her to her feet as he told her, "Your asshole will expand quite a bit. You just have to take it slowly and let it adjust on its own."

What he did not tell her was that he wasn't sure he could hold off on pounding her once his cockhead got inside. He had wanted to do this since the first time he fucked her doggie and watched her asshole tempting him months ago.

He had her remove the earrings and then led her to the adjacent bathroom and got in with her as she turned the water on.

"Make sure it's luke-warm, we don't want it too hot or too cold," he told her as he stood behind her.

He reached for a bottle of lube on the shelf at the other end of the over-sized stall and used the front of her body to block the water as her squirted a palm full and proceeded to slicken her asshole and she flinched when he inserted first one and then two fingers.

"Hand me the nozzle," he told her, and she reached to take it from its holder as if it might bite. Randy spread the excess lube that remained on his palm liberally over the black rubber. "Ok, reach back and take it by the bottom and then bend your knees and put it in," and she uttered a guttural groan as she did so.

"Good girl, now I'm going to turn the water on slowly. Just hold it in place and clench your butt cheeks tight to hold it in until you feel your bowels start to distend. Then unclench, but still hold it inside, got it?" and Halley acknowledged that she did.

Randy turned the nozzle on the shower head slowly and watched Halley fidget as the water began to fill her. When she could take no more, he had her hold on for ten more seconds and then told her she could let go and the brownish water cascaded from her ass and swirled down the drain. It was all liquid.

"When was the last time you had a bowel movement?" he asked.

"Uh, I went right before I left the house," she told him as she turned her head to her shoulder.

"Do it again," and he moved to her side and caressed her cheek and kissed her as she clinched her ass again on the black rubber. He held the kiss deeply as she began to squirm and then he rubbed her growing abdomen until she began to moan into his mouth.

He briefly broke from her mouth, "Let it go," and resumed kissing her as she again allowed the water, just slightly tan this time, to flow down her long legs.

Again, he broke the kiss and reached to take the nozzle from her hand and removed it from her ass. He used the jet of water from it to wash down the back of her legs and her feet until all the discolored water was gone. Randy then stepped up close to her just off her right flank and told her to put her hands on the tile and bend over for one more time. Halley drew in a deep breath and followed his direction and he worked the nozzle back into her, the water helping to open her asshole and allow entry. This time when he told her she could let it out, it ran all but clear.

He turned off the water to the nozzle and the shower resumed its flow. They soaped and washed each other's bodies and he asked her how it was.

"It was," and she halted, trying to find the right word, finally she settled on, "different."

"Oh baby," he hugged her soapy body with his, "you ain't seen different yet."

As they dried off, he had her put her hair in a ponytail with a thick rubber band and then, sans towels, they headed back to the guest room and as they left the bathroom, he picked up a full bottle of lube and a cock ring.