Silvery Hair and Golden Ops

Here's the original title that wouldn't fit: "Silvery Hair and Golden Opportunities."

Sometimes, the weirdest stuff just happens. That's life; I understand. Unfortunately for me, it tends to hit me more oftentimes than not, as bad luck; a deer running out in front of my car and DXing the front end, or getting my phone run over by a delivery truck. Just stupid shit like that. I have never found a lonely female hitchhiker looking for a ride in the middle of the desert, except the one time I did, my dad was with me, and it was in town. WTF?! Could someone please tell me why my luck is so bad?! Especially when it comes to women?

So the other day, I got a call from my best friend and bro, Trevor, asking for some help with his aunt, who was holed up in a nursing home or something.

"Hey Man!" he addressed me via my cell phone. "My Aunt Glenda needs her meds picked up and I'm out of town. I know you live about twenty miles away, but would you please pick her meds up and take them to her? I promise, I'll comp you, and pick up the cost at the shooting range next time."

"Yeah, it's okay," I grumbled, "but you owe me, Bro."

I dropped by the pharmacy and paid for Glenda's meds. It wasn't too terribly expensive I suppose, but it drained most of my available cash, and I was a little annoyed about the situation. I was still feeling annoyed when I went to the Shady Oaks Retirement Community to drop them off.

I parked my car and entered the facility. To my surprise, it looked nothing like what I had expected. It had an almost spa-like air to it. This was certainly no nursing home! There was a faux waterfall to my left, with tinkling waters and LED lighting, and a giant flat screen TV to my right that was obviously tuned to HGTV.

"May I help you?" a young female voice called out.

I turned to my right and focused my attention on a rather gorgeous twenty-something babe with naturally light red hair, alluring doe eyes, nice hooters and nodded in reply.

"Um, yeah... I'm looking for Glenda Carroll." I replied, my annoyance fading quickly at the sight of her.

"Are you a friend or family member?" the doe-eyed goddess inquired.

"Umm, neither and both I guess." I managed to reply. "I have her meds. Her nephew is a friend of mine, and he asked me to pick her stuff up and drop it off. I didn't know it would be this difficult though."

"I see." Miss Doe Eyes noted. "May I see your prescriptions, please, and do you have some identification?"

"Umm, yeah." I said, faltering as I stared at her. "Here you go."

I offered the prescriptions for Trevor's Aunt Glenda, as well as my driver's license, and the doe-eyed goddess nodded approvingly.

"She's in Room 114, Mr. Dawson. I'll let her know you are on the way."

"Thank you." I responded politely. "You are so sweet. I'm Jack. What is your name?"

"Kayleigh," she replied, "but my friends call me Leigh."

Before I could respond, she added:

"But my closest friends call me Kay."

I smiled as flirtatiously as I could.

"I'll be back soon, Kay."

She smiled and pursed her lips.

"Don't be too sure about that." she replied. "You're a good looking dude. If you can make it back here without losing your load, I'll be very surprised."

I was of course, at a loss for words. I had no idea what the drop-dead gorgeous, doe-eyed redhead named Kay meant, but I was determined to find out! I found Aunt Glenda's room and knocked on the door.

"Hi there!" she greeted me enthusiastically, in a pleasant Southern drawl. "You must be Trevor's friend. Please, come in."

I nodded in response.

"Yes." I replied, as I stepped inside. "I have your meds."

"Oh, I need those, Sonny Boy." she replied. "It keeps my old heart going, and the Grim Reaper off my ass for the others!"

I smiled at her remark, and took the time to actually look at her. She could have been anywhere from her mid sixties to mid seventies, but she was still really pretty. Unlike most women used to do, she had not had her hair whacked off, and it was her natural silver color that hung halfway down her back that really caught my attention. It had an almost bluish hue to it, that no dye could ever hope to duplicate.

I don't know why, but gray hair is really hot on a woman. Years ago, they would just get their hair cut off, which was a huge turn-off. Then, they started keeping their long locks, but dyeing it with Winter Wheat blonde, which gives that silvery-blonde color that is so overdone now. Even women in their twenties are using it now, and it just doesn't look right. To my surprise, Glenda was naturally gray, and she looked really hot. I handed her the package of medications and did my best to make conversation with her.

"If Trevor had told me how attractive you are, I'd have come here a lot sooner." I said, trying my best to be flirtatious.

Glenda eyed me suspiciously.

"And why is that?" she inquired. "Do you have an Oedipus Complex or something?"

"No," I replied, "but you're really pretty. Were you a model when you were younger? You have great features, and your gray hair is pretty hip right now. You'd shoot well."

"How would you know?" she asked.

"I'm a photographer." I explained. "I typically shoot nudes, but there are magazines looking for models of your age range too."

"Nude, or regular?" she inquired. "You're confusing me."

"Well, I meant standard photo shoots, but there is a growing market for nude models in their sixties, seventies and even eighties now." I said.

"Would you like to shoot me nude?" Glenda inquired. "What would it pay?"

I certainly wasn't expecting this when Trevor called me, but I was beginning to like the direction in which it was heading.

"It depends. A day shoot on location would pay more, but if you want a quickie in your room, I'd give you fifty dollars." I offered, feeling a tingle in my loins, and the beginning of an erection that soon followed.

Somehow, the thought of seeing this old broad without her clothes on was turning me on, and I was actually wanting to see her strip nude and show it all off in front of me. Glenda extended her arm with an outstretched palm and wiggled her fingers.

"Deal!" she said enthusiastically. "Put it here!"

"I spent more than that on your meds." I responded. "Wanna use this against that?"

Glenda thought for a few seconds and nodded.

"Sure, Sonny Boy." she replied. "I'm game if you are. Like seeing that old pussy, do you?"

"I have an appreciation for older women, if that's what you mean." I replied, trying my best to sound professional.

"If I get turned on by all of this, I might let you fuck me." Glenda suggested. "What do you think about that, Sonny Boy?"

"I think you still owe me fifteen dollars, and it would square everything up." I countered. "And my name is Jack; not Sonny Boy, thank you very much."

I was beginning to see how the old gal operated, and I was getting a feel for what was inside of her head. I was also getting a feel for the raging hard-on I had as well. I wanted to see her nude, and I wanted to fuck her very badly on top of it. I was beginning to understand what Kay meant earlier.

"Okay, Jack." she said brightly. "Photograph this old girl in the buff, and then do me doggy-style in front of the mirror. I want to watch you fucking me from behind. Don't forget to squeeze my tits either. I want to see that too."

"Very well then." I agreed. "Let me go and get my camera out of the car. I'll be right back, Glenda."

"I'll be waiting," she replied, "but hurry up! I want to get out of these clothes and model for you!"

"I'll be back in two shakes of a lamb's tail!" I promised, exiting the room and heading back toward the lobby.

"That was quick!" Kay called out. "She scare you off?"

I stopped and smiled at her.

"No, I'm a photographer, and we agreed to comp what I spent on her meds for a photo shoot." I explained.

"Oh really?" Kay responded, quite intrigued at the odd business deal. "You like photographing women nude?"

"I love my job!" I quipped.

"I see." she said carefully. "Stop by and see me before you leave. I might be interested in modeling for you."

I nodded, and retrieved my digital SLR from the car, along with a GoPro and tripod, to film our sexual encounter as well. I knocked on the door, and she immediately flung it open.

"Took you long enough!" she said in a huff. "I'm starting to get really horny, Jack. Let's get this show on the road!"

"Okay then." I agreed. "Let's start with you undressing. Take it off slowly, so I can get you in various poses, okay?"

Glenda nodded, and began removing her clothes. It took several minutes, but finally, she was completely undressed and fully nude. I was amazed at her tits. At her age, I would have expected them to be totally deflated and withered up, Don't get me wrong; that really turns me on, but these tits belonged on a thirty year old woman. They were probably three and a half inches in diameter, and at least eight inches long, but they were as firm as giant Russet potatoes of the same dimension. The only thing that gave her age away, was the fact that her areolae had lost their pigmentation. Other than that, I would have expected to see them on a chest one third of her age.

"Glenda, your tits are gorgeous." I breathed in awe. "So are you."

"Why thank you, Jack." she replied with a huge smile on her pretty face. "That really means a lot to me. What now?"

I instructed her to pose in various positions, all the while getting more and more turned on by all of this. In addition to her amazing tits, her pubic hair was trimmed into a silvery triangle that was absolutely enthralling to stare at. I shot close to 150 frames, before I was satisfied. I then mounted the GoPro on the tripod, facing the mirror from an angle, and had her climb onto the bed and pose on all fours. Once I had her centered in the frame, I turned the camera on and moved on to stage two.

I ditched my clothes in less than ten seconds, and mounted her from behind; sliding my cock into her surprisingly wet cunt. Not only was it wet, it was still rather tight as well. I couldn't believe how good it felt, to fuck her in genuine earnest, as she begged for more.

"Fuck me, Jack!" she demanded. "Fuck me harder! Squeeze my titties!"

I reached under her chest and managed to find them hanging far lower than I had anticipated. I squeezed them vigorously, as I continued pounding her seasoned cunt.

"Fuck, that feels good!" she bellowed. "Shit, Boy; I'm gonna cum! Make this old grandma cum, Jackie!"

I could feel her vaginal muscles clamping down around my cock, as she howled in pure orgasmic pleasure. I had no idea that women her age were still able to experience sex the same way as younger folks, but she was schooling me on that!

She shuddered violently as she climaxed; grunting and panting as her cunt continued its vice-like grip on my cock. I was no longer fucking her, but rather her cunt was jerking me off as I moved back and forth! It felt so good, that I couldn't control myself any longer. I squeezed her gorgeous tits again, and sighed blissfully, as I shot off inside of her geriatric cunt.

"Oh my god, I felt that squirt inside of me!" Glenda shrieked. "It was so warm. I felt it hit the back of my uterus! Holy shit, that was a magnum load!"

I fondled her boobs for a few more moments, as my penis softened up and finally slipped out of her aged and silvery cunt. I rested on my knees for a few moments, trying to catch my breath, and then finally managed to speak.

"Any time you want that again, you let me know!" I panted. "Jesus Glenda, I'd love to be your boyfriend."

She turned to face me with a serious look on her face.

"Don't you ever lie to me!" she demanded. "Don't say things unless you mean them."

"I'm not." I said, shaking my head. "I'd love to take you to dinner and the movies. Go for walks in the park. I don't care how old you are, as long as you don't care how young I am."

"If you really mean that," she said softly, "I'd like that too. I like sex, Jack, but I can't do it every day. As young as I look and feel, I still have limitations. I'd like very much to be your girlfriend, but there are also a lot of ladies in here who could use some extra cash too. Maybe you could do photo shoots with them as well. I wouldn't mind, just as long as I knew your heart truly lay with me."

I was stunned, and at a loss for words at her reaction to all of this, but I was certainly up for it if she was! At thirty eight years old, this could be a veritable sexual gold mine for me! All of these women in their golden years, with their silvery hair, was the literal pussy mother lode. Make that the pussy grandmother lode! Hell, it could even be the great-grandmother lode!

"Let's do lunch." I suggested. "When was the last time you went out on the town?"

"Several years," she admitted, "but I've had no reason to leave. Unlike most of the gals in here, I checked myself in by choice. When my husband Fred passed, I just lost all inclination to do anything. I guess that's why I'm kind of bitter. The thing is though, I chose this. Most of the other residents here, were dumped in here by their families. Some people have never had a single visitor. They've been abandoned. I feel so badly for them."

I felt a pang of pity for those people who by no fault of their own, found themselves all alone. It wasn't just the women either. As I would learn over the coming weeks and months, there were many lonely men in Shady Oaks as well. I was determined to help all of them find a path to happiness, but it would take time. As it would soon turn out, time was on my side, and would allow me to turn what was once a sad and lonely place, into a place of friendships and joy.

"Why don't you put a nice sundress on?" I suggested. "It's a nice day out, and I think you'd look cute. We can get some lunch and go to the park if you'd like."

Glenda brightened at my suggestion and nodded.

"Okay Jack!" she agreed excitedly. "Oh, I can't wait for that nosy Clara to see us! She'll be gossiping all over the facility!"

Ten minutes later, Glenda and I left her room arm in arm. Sure enough, as luck would have it, we ran into said "nosy Clara."

"Well hello, Miss Glenda." she said in a very patronizing tone. "How are we doing today?"

"I don't know how you are Clara," Glenda replied, "but I am just fine, thank you for asking."

"Are you feeling okay?" Clara inquired. "I see your grandson is holding you up by the arm. Are you feeling faint, Dear?"

"I'm not her grandson." I responded, with a one-sided smile tugging at the corner of my mouth. "I'm her date. And the last thing she's feeling is faint, I can assure you of that! We're on our way out to have some lunch at a delightful and rather expensive little French restaurant I know of, and then a matinee at the Bijou afterwards."

"What a hussy!" Clara sniffed indignantly. "Paying a hot cowboy escort to take you out on a date. Why, I never!"

"I'm sure you haven't, Clara," I agreed, "but she didn't pay me to take her out. I asked her, and I'm not just her lunch date, either. I'm her new boyfriend, so why don't you flap your yappy clap trap around these hallowed halls about that?"

Clara stared at us dumbfounded; unable to speak or move, so I escorted my trophy GILF of a girlfriend around her annoying ass, and proceeded down the hall toward the lobby.

"Hey Kay!" I called out, as we passed the front desk. "We'll be a while, so if you aren't here when we get back, don't worry. I'll be here quite a bit from here on out. I'll hook up with you later on though, okay?"

"Sure thing!" she called back. "I told you, didn't I?"

"You did." I agreed, as I looped back around and stopped at the desk.

I retrieved a business card from my wallet, and handed it to her.

"I'd love to get a text from you." I said with a smile. "I'm sure I could get you a lot of side work if you're up for it."

"I'll think about it." she replied, as she took the card and glanced at it. "I'll just let you wonder for a while."

"Toodles." I said in parting.

I escorted Glenda to my car and opened the door for her. She smiled and sat down.

"It's been a long time since a gentleman opened the door for me." she said sentimentally. "Thank you, Jack."

"Who says chivalry is dead?" I responded with a smile of my own.

"So where are we going?" Glenda inquired. "I know you're not taking me to an expensive French restaurant for lunch."

"I wish I could." I replied. "That was for Clara's benefit, but how about the hoagie shop?"

"I haven't had a good hoagie in ten years!" she exclaimed. "I'd love that Jack. However... and pay attention; I do want to take you to a nice restaurant for dinner very soon. Would that be okay?"

I looked at her blankly for a moment.

"Sure, I guess." I managed to reply. "That would be nice. Thank you very much."

"I gave up my car when I moved into Shady Oaks, so you'll have to drive," she continued, "but if you treat me well, I'll be your sugar mama. You had no idea who I was, when you offered to be my boyfriend and take me out. That means a lot to me, Jack."

"I don't understand." I said in a confused voice. "You're hot, and I really want to spend my free time with you."

Glenda smiled.

"Other than Trevor, no one in my family has bothered to visit me, except when they want money." she explained. "Trevor's a good kid, but other than bringing my medicine and dropping by every now and then, he's pretty scarce too."

"I still don't understand." I said in a perplexed tone. "I have no idea who you are, other than being Trevor's very hot aunt."

"My last name isn't familiar to you?" she inquired.

"Other than it being the same as that guy that built the amusement park outside of town, no." I admitted. "I'm sorry, Glenda."

"Do you remember his name?" she asked.

"Yeah, Fred Carroll." I replied.

"What did I tell you my husband's name was?" she inquired.

"Fred." I answered.

Suddenly, two plus two equaled four. I pulled to the side of the road and stopped the car, looking at her in utter amazement.

"Your Mrs. Fred Carroll?" I asked incredulously. "What the hell are you doing in Shady Oaks? You could be living over in Cypress Heights!"

"They're all a bunch of egotistical assholes." she explained. "Not my type. Fred and I both came from humble beginnings, just like you. He went to law school and did well for himself, eventually becoming a judge. He did some work for Herbie Hunt back in the Seventies, and put everything he had into silver, after Herbie told him what was going to happen. He managed to cash out a little before it hit the high, and took all of his earnings and built Adventure Land without any investors."

"How much did he invest, if you don't mind my asking?" I ventured cautiously.

"About a million dollars." she replied. "He bought all he could at around five dollars an ounce and turned it at thirty five."

"That's like what, two hundred thousand ounces?!" I almost shouted. "And he turned it loose for thirty five an ounce? That's like... hell I have no idea."

"Seven million." she replied coolly. "He put it all into that park, Jack. No outside investors. No one else owns any shares in that company except me. After lunch, why don't we go there instead of a movie? I'd love to show you around."

I was of course, at a loss for words.

"Sure!" I managed to blurt out. "Sounds great."

"Good!" she said with a smile.

After a few seconds, she followed up.

"Uh... Jack?"

"Yes?"

"We're still on the side of the road, Honey. We might get there a little quicker, if you get back into a driving lane and actually get the car moving again."