Discovering Olivia Ch. 03

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Older man meets a younger woman and his world opens up.
8.4k words
4.42
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Part 3 of the 6 part series

Updated 02/20/2024
Created 10/21/2023
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MrHMiller
MrHMiller
27 Followers

Disclaimer: All characters in the story are not based on any real people and everyone in this story is 18 years or older.

As northern snowbirds began re-establishing residence, drawn by the warm temperatures of Florida, Olivia and I were planning a celebration of six months together. Our small town, slowly overrun by the winter carpetbaggers filled the restaurants and cafes pushing out locals, who for six month of the year, contend with the competition for seating. I shook off the physical and emotional hiccups that came with the influx this year because I felt better than ever before, thanks in large part to my relationship with Olivia. Not only had I lost twenty pounds, but her youthful energy was helping reduce the stress in my life. Best, I was convinced my newly-added supplement regime, the gym, combined with my increased sexual activity had enlarged my penis. My doctor was hardly convinced.

"Rob," he said through laughter, "you lost twenty pounds; you've re-discovering the penis that was hidden by layers of fat. Bigger penis? That's a good one! You crack me up, Rob." I gave serious consideration to finding a new doctor.

Saturday morning's sun shone brightly and the serene salt air filled my lungs on an early morning trip to the nude beach to work on my tan before I saw Liv. It didn't hurt the beach was already full of beautiful women to watch. Were women look better as I grew older, or was that my imagination? I wondered what they thought of me, laying spread eagle on my towel, cock and balls hanging out. Was I just another old creep to these scattered groups of nude, nubile woman? I was definitely not like the "Old Nomads", walking up and down on the surf's edge; long ponytail's of white hair, full mahogany tans, saggy ball sacks, and leering eyes. They sought out young women for conversation and if they were naive enough, the dudes would take further liberties, carefully executing "accidental" boob or ass groping. I didn't want anyone mistaking me for one of those beach dudes.

It was nearly one in the afternoon, so my anticipation and excitement grew as the appointed arrival of Olivia drew near. I'd planned a surprise for the next day; we would go to the spa together for treatments, a waxing then a trip to the erotic artist to model jewelry for her anniversary gift. That evening we'd have dinner at our favorite bistro. Olivia made me feel a different kind of happiness that had been missing from all other relationships.

I was delighted by her ability to be simultaneously sweet, raunchy, and sensuous. She was earnest when it came to our bedroom activities, so each time she shed her clothes I knew it was meant for me. A natural exhibitionist, Olivia delighted in flaunting herself combining costumes and kinky antics, like the time she dressed as a ballplayer from 'A League Of Our Own', imitating a cock with a small bat or when she donned a bee costume equipped with a penis head stinger, Olivia had me rolling in laughter.

The memory of our first meaningful kiss still lingered in my mind. She suggested we move to the couch to get more comfortable, our lips finding communion in a drawn out lingual explorations. My hands roamed her body, exploring each soft curves of her figure and coming to rest on her pert 28 year old boobs. Our mouths let each other in, tongues intertwined as I was taken by her wonderful scent. In that moment she felt perfect.

I pulled back briefly, "You taste so good," I told her. This was one of my tried and true methods, being specific on the reasons you appreciate a woman. It could be anything. One of my favorites is, "Your boobs are so beautiful and they make you so look feminine. Very few woman make me feel that way."

Olivia stepped through the doorway at 1:10 pm, finding me in the kitchen, amidst the tomato-ish aromas of lasagna sauce. I was naked other than a few Olivia recent obsessions; toys, a gold cock ring and a metal butt plug tucked between my cheeks were my only accents. Pecking me on the lips, she sauntered to the bedroom and returned with her own new auric adornment. Olivia was nude, except for the intricately designed gold chains connected with two delicate gold ropes running either side of her labia, three jewels hung gracefully against her clit, bobbing and bouncing whenever she moved. Rob couldn't help but envy the options woman had to accentuate their sexuality. There was Olivia, standing in my living room, showing off jewelry that highlighted her pussy and not even realizing my eyes could stop following her perfect tits. What did men have; cock rings, butt plugs and nipple clamps? Or maybe was it money.

"That is unquestionably the sexiest jewelry I've ever seen," Rob said admiringly.

"The artist is a genius." Though it seemed repetitious now, I still wanted to give Olivia one of the woman's creations; because after all, the real present was Olivia choosing and modeling the artwork, naked.

"Thanks, I think it really compliments me and perfectly draws attention to my labia." Olivia spoke as she turned and posed.

"I'm sure we'll find the right occasion to wear it," Rob replied. "It makes your pussy look even more perfect than it already is."

"hank you, Uncle. That's so sweet" she cooed. "You know how much I appreciate your admiration but I don't want people thinking I'm...slutty."

His voice grew stern,"you're still calling me Uncle," he pointed out.

"What should I call you: Pops, Grandpa, Geezer...the Senior Citizen," she responded laughing.

"Come on, you know it's a sensitive subject. Just call me Rob."

"Okay, I'm sorry. I understand," Olivia sighed reluctantly, her eyes avoiding Rob's looks. "I get why you feel this way but I was only joking," she added defensively.

"Liv, you've changed my life for the better, Liv," Rob smiled at his lover, the minor disagreement passing. "My health is great and I just feel...happy."

"Yes, honey," Olivia replied lovingly trying to make him feel better.

"But there's something else I want to discuss...I think we should consider an open relationship instead of exclusivity. It really matches who we are," Rob said raising a subject they had talked about previously but not come to agreement on.

Olivia hesitated for a moment, unsure if she was ready to be open or if it was just exciting in concept. "I agree that it fit us both but right now, it makes me happiest to make you happy," she said softly. Rob smiled tenderly at her but Olivia could sense something still bothered him and thought she knew the reason.

"The age difference," she said with an expression of concern? "You're afraid of losing me to someone who sweeps me off my feet and take me away, aren't you?"

Rob squeezed her hands as if to say yes, then replied. "It scares me more than anything else...you're so smart, pretty and are already accomplished. Any guy would be lucky to have you in their life. It's weird, this never bothered me before. Relationships were always take it or leave it before you."

"Listen," speaking tenderly, "I'm being very serious, now. You're not some old fart, Rob; you're my old fart. Don't forget that and don't let others define us. I love you and you love me. Age is not a part of it, however, it's always amusing when people see us together and think you're my Dad! Can you imagine how difficuly it is not to tell those people, 'yeah, he's a super cool Daddy and also a great fuck!' I barely manage to keep a straight face." He shook his head in admonishment at her attempted humor.

Olivia enjoyed teasing him but quickly softened her tone: "Honey, I love that you respect me and enjoy being with me. You have a wonderful sense of humor, a beautiful body, plus, you're adventurous! There aren't many guys who tick all those boxes."

Rob gazed at her, "I think its time we start working on a new adventure," he proposed.

Olivia asked, "You mean another Ellen or will it be something completely different?"

Rob looked at her. "A new adventure. We could do something different or yeah, a threesome would be good too. I don't think it matters much," then realized he didn't answer the question.

"I think, we have to be careful and talk more about a threesome, Rob. We were lucky the first time, I mean, you and I bear the greatest risk in a threesome. The other person can walk away and never see us again. Do we at least agree why we're doing this?"

"Olivia I've never had these kind of feelings for a partner... It's confusing. I feel like I want more than just a girlfriend and that has never been me," Rob honestly confessed.

"Oh, this sounds serious," she said concerned. "Tell me more."

"Well, I feel we'd both be happier with things open but at the same time I'm asking myself is that what we should be doing now. Also how come you never wanted to know about my past sexual experiences," seeming confused.

"Does it matter," she asked?

"I think it does. My whole life, I've convinced myself that sex was more important than any kind of commitment but my feelings towards you make me doubt that. So why do I have this conflict when involves you?"

"I don't know," she said.

"I want this relationship to be something special but in the future what if you want marriage and children and I just don't. You deserve to have both."

"You're making a lot of assumptions," she replied indignantly. "Not all women want the same things. I'm not interested in settling down or having kids right now. Sex is my priority while my body looks like this," she gestured to herself. "Who knows how I'll feel in five years, maybe I'll want that commitment? I'm willing to change my mind when the time comes. Today if you ask me what I want, the answer is yes, and...?"

Rob was confused. What does 'yes, and' mean?"

"Yes, and," she said.... Do you want to fuck? Yes, and....how many people this sex involve? Yes, and...do you like spankings? Yes, and...have you ever done double penetration? Yes, and... lots of things. Since I've met you, sex between us was always assumed. That's never happened to me before. On my own, I'm willing to take some chances, but when I'm with you, I love being promiscuous. Maybe its the exhilaration of a new love, so let's just enjoy this while we have it. So what, if you're older. It frees me from being an adult and I can be, a gorgeous, sex obsessed, chick, with no consequences. Why? 'Cause, Daddy will protect me. That's an amazing gift, Rob. You make me feel safe when what we could be involved in is risky. Under those conditions, I could actually commit. You allow me to indulging the free spirit inside me. What if I wanted to wear nothing but three inch heels, grind on a pole in front of huge cheering crowds and flashing my pussy. I could do it because you're there to look out for me."

"Well that an intriguing mental picture," Rob said!

"This is what I'm suggestion. Let's just enjoy thing the way they are. When we're faced with an actual need to settle down or commit, we'll talk about it then. Okay?"

"Sounds good," they cuddled on the couch before dinner and looked forward to celebrating their anniversary the next day.

On Tuesday, Olivia was working at the client's office when she met Samantha Rogers, a new hire. The client had finally got around to implementing some of Olivia's finance recommendations, including hiring more finance talent. Samantha, a woman in her forties with experience from several large accounting firms, quickly became friends with Olivia and over the next few weeks, she got up to speed and eased the accounting workload.

"Hey, want to grab lunch today?" Samantha asked poking her head into Olivia's office.

"Sure, what do you have in mind?"

"That salad place down the street."

"Sounds good." The two women ended up at the Sandwich and Salad Salon, each ordering salads, fresh baked French roll, and a drink.

"I love this place," Samantha commented while pouring dressing over her romaine. Olivia noticed a small pineapple tattoo on her right forearm.

"I've never noticed that before," Olivia said, gesturing towards the tattoo.

"Oh, that? It's nothing."

"No really, why do you have a small pineapple tattoo on your arm? Does it have a special meaning?" Olivia asked curiously.

"It's a bit unusual. I'm a little embarrassed to mention it."

"I like unusual things," Olivia reassured her. Samantha hesitated for a moment before speaking again.

"Olivia, I believe we're friends, right?"

"I'd like to think we are, Samantha." Samantha studied Olivia intently.

"Well then, if we're friends you simply must call me Sam. I only use Samantha in a professional setting. With my friends, I prefer Sam."

"Okay, Sam. You should call me Liv."

"Great, Liv. So if we're friends, can you promise that whatever I tell you remains between us?"

"Of course, I can do that."

"Sam leaned in, a sly grin on her face. "I have an intuition you're not an average run-of-the-mill kind of person," she said. "What do you say, am I right?"

Liv tilted her head, surprised by Sam's observation. "You could say that," she replied.

"Well then, in order for me to reveal the meaning behind my tattoo, I think it's only fair we share personal information with each other to build trust. Why don't you go first and then I'll tell you my story and the meaning of the pineapple? Sound fair?" Sam suggested with a smirk.

After analyzing Sam's face for any signs of deceit, Olivia nodded. "Sure, okay I'm game."

"Tell me about yourself, Liv," Sam prodded. "I can see you're a skilled CFO, but what's your personal life like? With your stunning looks and great figure, I'm sure there are plenty of guys vying for your attention."

Olivia chuckled. "Actually, I've been seeing one guy for about six months now. He's sweet, fit, and very attentive. We've a lot in common."

"Sounds serious," Sam commented.

Olivia shrugged nonchalantly. "Yes and no. Neither of us are interested in marriage, if that's what you mean by serious. Whatever I tell you stays between us, right?" she double-checked.

"Absolutely," Sam reassured her with a nod. "Mutual assured secrets."

A small smile tugged at the corners of Olivia's lips. "Well, my guy and I have dabbled in some...unconventional activities. It's been mostly just fantasizing so far, except for one time..."

"So you've actually done something out of the ordinary?" Sam asked with her interest heightened.

Olivia nodded sheepishly. "Yeah, we had a threesome with another woman. But it was just a one-time thing."

"How did it make you both feel afterwards?" Sam inquired.

"The whole experience was wild, and Rob and I couldn't keep our hands off each other for the next three weeks," Olivia shared.

"That sounds wonderful! What's Rob like?"

Olivia paused for a moment before answering. "As I said, he's very attentive, great in bed, and has never been married. He's a little older than me."

"Older?" Sam questioned.

"Yeah, he's 62 years old," Olivia confirmed.

"62," Sam choked on her seltzer in surprise.

"Don't let his age mislead you. He may be older, retired, but he's still super sexy and knows exactly how to turn me on," Olivia continued with a sly grin.

"I didn't see that coming," Sam chuckled.

"And get this, he hates when people joke about him being my Daddy. It's just too easy to tease him on this because, let's be real, he is my Daddy...in bed at least," Olivia joked again.

"Oh wow," Sam laughed along with her.

"But in all seriousness, we've talked about having an open relationship. We both feel like it fits our personalities better. And even though this was supposed to be temporary, I've decided to move here permanently to be with him."

"Well that's quite the confession. So what about you, Sam? Any juicy secrets you want me to know about?" Sam leaned in her chair after finishing her salad and took a sip of her seltzer as she thought about what Olivia had just told her.

"I'm just a simple girl from the Midwest, 43 years old and divorced. I met my ex-husband in college and although we got along great, our marriage was troubled. After 8 years, my husband came home one day and said he was unhappy. We tried talking and working on our marriage, even went to a marriage counselor. It helped for a while, it didn't last. The counselor eventually suggested we explore other partners, leading us down a swinging lifestyle for two years. Hence, this tattoo - an upside-down pineapple that signifies being in the swinging community. My husband fell in love with one of our sex partners and filed for divorce five years ago. It was for the best, you can't make someone happy if they're not interested. I've grieved and now I'm moving on. I've seen some wild sexual things during those two swinging years. So now that you've told me about your situation, I'm wishing I could find a guy interested in something similar with me. I'm not ready for another marriage but that doesn't mean I don't still want to have fun."

"I'm sorry, Sam."

"Thanks but don't worry about it."

Olivia smirked, "I don't know much about swinging, but with your looks, you should have no problem finding partners. You sure have a cute body."

Sam chuckled nervously. "Thanks, but I'm not exactly a beauty queen." Suddenly, Olivia's eyes lit up in realization. It not about looks, it was about confidence. Here was another woman who didn't see her true appeal.

"You're beautiful, Sam. So beautiful that even I would sleep with you."

"What?" Sam's eyes widened in shock and disbelief. "A hottie like you?"

"I mean it. You're gorgeous." Olivia leaned in closer. "I definitely could imagine having sex with you."

Sam stared at her for a moment, speechless. "Wow, Liv. That's really sweet of you but I've only been with other men when I swung. My husband only wanted to watch me with other guys, maybe it was punishment thing." She chuckled bitterly. "There was one time where my husband insisted I fit one guy's huge cock in my ass while another guy was inside my pussy. It was really intense and I cried afterward because I felt used but now I feel like it is a badge of honor."

"Wow, you did double penetration," Olivia asked amazed. "I've fantasized about that. What does it feel like?"

"Yeah, DP." Sam smiled fondly at the memory. "If you're into feeling filled up it definitely does the trick."

"Listen, Sam," Olivia said hesitantly, "this might sound crazy but...would you meet my boyfriend Rob and consider having a threesome?"

Sam couldn't believe what she was hearing. "Are you serious? You want us to all be together?"

Olivia nodded confidently. "Yes, that would be so exciting. Of course I'll have to discuss it with Rob too," she said. And just to be clear, I knew the woman we had the threesome with," Olivia explained. "It was supposed to boost her confidence and show her that she was very desirable. The whole time all I could think about was how much I love Rob for doing it."

"Aww, that's so sweet," her friend cooed.

"I promise, you won't just be a third wheel," Olivia assured her.

"Okay, maybe I'll come over and we can all talk about it and see how we all get along," her friend suggested. "We'll figure out what everyone is comfortable with."

That evening, Olivia and Rob discussed the possibility of a new threesome. Rob was excited Olivia took the initiative to plan something for them.

"We should serve nice appetizers with drinks," Olivia said. "I want to make a good impression on Sam."

"Maybe she knows people in Florida in the swinging community," Rob suggested.

The date was set for their friend Sam to visit and they eagerly awaited to see where this adventure would take them.

The doorbell rang a few days later and Rob eagerly answered it, greeting Samantha with a smile. "Hi, Samantha. It's great to finally meet you," he said as he welcomed her inside. He couldn't help but notice how attractive she looked.

"Call me Sam, Rob," she replied before giving him a small kiss on the lips. "Liv wasn't kidding when she said you were fit and athletic." Rob felt a rush of excitement from her kiss.

MrHMiller
MrHMiller
27 Followers