Reengaging with Courtney Pt. 01

When the oldest son married Courtney we were surprised, and though we tried to be the best parents and in-laws, we had doubts this relationship would last long. Courtney was a very sweet and pretty young lady, and while she wasn't the brightest bulb she wasn't stupid either. Standing about five foot six, she had natural blonde hair and bright blue eyes, a great ass to compliment her nice figure with full 34C boobs. She was the very definition of a looker.

But she also had a reputation, with one rumor being she and some friends had posted nude under-age pictures of themselves on the net, which were quickly taken down. In short, both boys and men liked her, and wanted to be with her. And I'll be honest, I was definitely attracted to her, imagining all sorts of things we might do together if ever alone. In fact, once when they came to visit she complained of a toothache and went to lie down in the guest bedroom while our son and his mother went shopping at the local mall. I stayed home since shopping just isn't my thing, and more than one thought crossed my mind about going into her room and 'checking on her.'

Of course I didn't, but my mind went through a series of sexual adventures we could have together. That evening I banged my wife harder than I'd done in months, with her expressing concerns the kids would hear us. I told her they were probably going at it as well. That is, if Courtney's tooth condition had improved.

I'll give her credit, Courtney stayed in the marriage longer than I thought she would at the time. But looking back, maybe she was prepared to leave earlier and was just looking for another, or better, place to land. Couldn't blame her, it's a little crazy out there if you're a young, pretty divorcee. Thankfully there were no kids.

When we could get him alone, we'd ask the son, "Why her?"

"God, she's so pretty," he'd tell us, "I never thought someone so beautiful would want to be with me."

And therein lay the problem. He had low self esteem, and in order to make himself feel better he latched on to one of the prettiest girls around, and then he'd constantly put her down. And in front of others, how embarrassing for her. We would warn him, that's not how you treat someone you love, and you'll find yourself alone at some point, wondering what happened. And eventually it did. And while we love our son, we really couldn't blame her for finally leaving.

Fast forward several years and the son remarried and has a family. And while his behavior improved with wife number two, they still had their moments and I will say she gave as good as she got. Good for her. My wife had passed away a couple of years after he remarried and they gave us grandkids, and I used my now-expanded family as my support group. Truth is, we probably used each other for support, which is a good thing and brought us all closer.

The rumor was Courtney had also remarried and had a family of her own. This was born out when I went to watch the grandkids play soccer and saw her watching her own child on an adjacent field. I casually made my way in her direction while pretending to watch the game, and after a few minutes of standing within a few feet of her when I glanced in her direction, our eyes met, and she smiled.

In faux surprise mode I asked, "Courtney?" Then reached my hand out to shake hers.

"Hey!," she enthusiastically replied in her unmistakable manner, lightly taking my hand in hers and gently pulling me towards her and into a firm hug.

"It's so good to see you," she continued as I felt her firm breast press into my lower ribcage. "It's been so long, how've you been?"

"Oh, too busy half the time, bored to death the other half. Guess that's the life of an old retired guy," I said.

"You're not THAT old" she quickly replied. And with a smile continued, "Besides, you never looked your age. And certainly not like a lot of men with dad bellies."

"Well, thank you. But you're the one who's kept their looks, still as beautiful as ever. You'll have to let me in on your secret one day."

"Perhaps, one day," Courtney replied playfully. "Seriously though, thank you for the kind thought. Who knew being a mother was such hard work?"

"So which child is yours?" I asked as I turned towards the field.

"Number five, that's Gabriel. He's not the best player on the team, but he sure likes playing. Which is good, keeps him out of any mischief. How about you, I suppose you have some grandkids out here?"

"The other field," I replied turning and pointing to Field #2. "Which I should be getting back to, by the way. But it was great seeing you Courtney, you look very happy," as I reached up and gently touched her shoulder.

She quickly moved to embrace me, which was a bit of shock, albeit a pleasant one. With our cheeks touching and lips close to my ear she said, "Don't be a stranger, I'm out here every weekend."

As we started to part she lightly kissed my cheek, causing a pleasant thrill. I probably had a bit of a shocked look on my face as we stared at each other for a moment, while she displayed a bright smile.

"Take care Courtney," I said as I began to step away and turned towards the other field.

"See ya!" she quickly replied in her typically happy tone.

'Wow,' I thought to myself, I certainly wasn't expecting that when I went up to say hi. But then, I thought, that's just Courtney's effervescent nature I suppose. At least, that's what I recall from the short time she was part of the family. That, and her good looks were what made her so popular with others, she just had a way of disarming a person and making them as happy as she was.

It wasn't long before the horny old man inside started to imagine her happy mannerisms were a flirtatious invitation to see her shapely body in all its glory. Her 34C breast in one hand, nipple hardening under my manipulating thumb, while my fingers caressed the damp natural blonde-covered folds between her shapely thighs. In my mind, I could practically smell her sex.

The sudden loud cheers over my shoulder brought me back to reality, and I turned back to where her son was playing to see his team had just scored a goal. I then looked in Courtney's direction where I saw her clapping along with the other parents. Suddenly, she turned her head in my direction where her eyes once again met mine, and she flashed me one of her signature bright smiles. I smiled back. She then took her right hand and ran it through her hair, and then shook her flowing gold mane. That had to be one of the sexiest things I've ever seen at a soccer match, as she smiled again, then turned back towards her son's team and continued clapping.

She was definitely flirting with me, I instantly thought. Or teasing me. Probably both. I just laughed and continued over to our field. Later that evening I turned in early, but couldn't sleep because of the thoughts of Courtney playing in my head. So, taking matters into my own hand, I jerked off to images of her laying back and running her hands though her hair as I ate her pussy. Then the bright, wide smile on her face as I lay above her as we fucked. I fell asleep with a large load of cum pooling on my belly and around my cock.

Several weeks passed and the dirty thoughts of Courtney became less frequent. Then, out of the blue I recieved a text mid-morning on a Tuesday. "If you're in town around 12:30 tomorrow I'll be at Kathy's having lunch. C"

Kathy's was a sandwich shop in town, and I really didn't have any plans that day, but wasn't sure who was texting me.

"Sounds nice, but who is this?" I replied to the number I didn't recognize.

"Courtney," came the digital reply.

"Oh hi. Pleasant surprise," I responded.

After a few minutes she replied, "And so...see you there?"

'What the hell,' I thought, I didn't have any other plans that day. "Yep. See you at Kathy's, 12:30. Looking forward to it."

I arrived a few minutes early and chose a corner booth. Several minutes later I saw Courtney come in, looking around the room. I stood and waved, then saw her signature smile as she recognized me and came over. As I smiled and said hi, she leaned in and lightly brushed her lips across my cheek before saying hi and taking her seat.

"Thanks for coming for lunch," she said. "I've been running errands all morning and needed a break and some good company."

"My pleasure, I'm glad you contacted me. It's a nice surprise, but I'd have thought you'd want to spend time with one or more of your friends," I replied.

"We're friends, right?" she quickly replied.

"Well, sort of, I suppose," I said, a little confused. "Obviously we're acquaintances," I stumbled with my thoughts, "We were certainly family at one time. I mean, I've always thought highly of you..."

The waitress came over, thankfully putting an end to my stammering.

"That's sweet, thank you," Courtney said while leaning closer once the waitress had taken our orders. "I've always liked you. You were always kind to me, and I appreciated that. Still do."

"Well, it was easy because you were always a very pleasant person, and deserved better treatment than you received. Sorry, didn't mean to open old wounds," I replied.

"No worries, that's all in the past," she quickly said, with a smile. "Besides, I'm more interested in what the future holds."

"And what's that, if you care to guess?"

"To be the best mother I can be, while still enjoying a modicom of fun. And I'll be honest with you, if I can use your shoulder for a minute. I also try to be the best wife I can be, but it's hard when the other party doesn't cooperate. Sorry, didn't mean to lay that on you."

"No, that's fine," I said as I reached across the table and gently took her small hand in mine. "Not that I need to know your personal business, but I'll listen to what's on your mind and try to give you the best advice I can. Not that you have to take it, of course."

"You see, that's what I find so great about you. Your kindness," Courtney spoke as she preceded to squeeze my hand with hers, causing me to smile broadly back at her.

She then continued, "This may make you a little uncomfortable, and I apologize for that. Its just... well, I have a high sex drive and my husband has a problem, how should I put it, um, keeping up with me."

I was somewhat shocked at Courtney's openness about the subject matter, but the more I thought about it the more I realized she was always an open person, and never hesitated to speak her mind.

After a few moments looking in each other's eyes, I replied, "Nothing unusual about that, really. You're in the prime of your life and your body has needs. Completely understandable, although a smart man would do his best to keep his mate satisfied. Both really need to make time for each other, away from all the other distractions, and that takes work."

At this point Courtney leans in so far that her breasts are now laying on the tabletop, with the table's edge beginning to pull her shirt down exposing more of her tanned orbs. The top of her full white cups are clearly visible, and I swear I can see the outline of her areola. I quickly look up towards her smiling face as she begins to speak in a softer tone.

"I know, right? I've tried everything I can think of or read, spent a small fortune on lingerie and other aids, but am constantly left wanting."

"I'm so sorry," I reply genuinely.

"Can you help me? Will you help me?"

"Excuse me. I'm sorry, what?"

"Will YOU help me?" She asked again. "Will you help me feel fulfilled? Sexually."

I lean back in my chair, but she tightened her grip on my hand and wouldn't let go as I looked at her in shock.

"Wow, having a difficult time imagining anyone of my generation getting asked that question," I say, dumbfounded. After a minute I leaned back towards the table, "What? How?"

"I'd always heard mature men know how to please a woman. I want to see if that's true. Look, I'm not some slut who sleeps around, but I've been thinking about this for a while. It all came together in my head when we spoke at the soccer game."

"What about your husband?"

"We'll still be together, have sex, and all the other things a married couple do. I just need more than he can give me at this point, and besides, you're safe."

"Safe?"

"You don't fuck around. Pardon me, sleep around. And it's not like we're moving in together. It's just for our own sexual pleasure."

"Seems you've given this some thought, How would this work exactly? Find a hotel room?"

"No, nothing that sleazy sounding. I inherited my grandma's house. I go there from time to time during the day to go through stuff, clean it up, try to keep it presentable. We can meet there for a few hours. It's semi-isolated, no one would bother us."

"So, we fuck in granny's bed?"

"No, silly. She always kept a room for me there. Has my things. Childhood toys, curtains, quilts, pillows. All the things you'd find in a teenage girl's room."

"I'm still blown away by..."

"I hope so."

"...the thought of... Funny. At, at, why me? I know, you said I was safe..."

"That, and you're a good looking guy. You've been places, seen things. I know you'd satisfy me both mentally and physically. And if we find out that's not the case, well no harm. We both had some fun. So what do you say, deal?"

I looked at Courtney for the longest time, all kind of thoughts running through my mind. Why not? She's certainly hot, young, and actually sucking and fucking her would be any man's fantasy. And I could have the real thing instead of jerking off to her image

"Okay...," I started before she jumped up from her seat to reach over and hug me, knocking the plates around the table in the process, before sitting back down.

"So, that might be all the excitement I can handle today, walk you to your car?"

"I'll walk you," she replied.

She gave me one last hug before I sat in my car, and motioned for me to roll down the window.

"Yes?" I asked just before she stuck her head inside and her mouth literally attacked mine. It was one of the sweetest, wettest and most sensual kisses I'd ever experienced, and was out of breath when she pulled away.

"Thank you," she said with a sparkle in her eyes. "I'm really looking forward to this, and will text you the address later for Friday. Assuming you're available then."

"I don't know what could possibly keep me away," I replied.

Later that afternoon I was laying back and replaying the day's earlier events in my mind. I realized we never really got into her specific needs, and had only spoken in generalities. It wasn't a question of what women want, what did SHE want? So I decided to text her.

Me: Hey.

C: Cold feet already?

Me: Absolutely not! (ha ha) Just curious what to expect? What are you looking for/to do?

C: (smile) Not the best time to discuss, will talk when together next. It'll be fun, promise. Sweet dreams, C.

So much for that, I sighed. But as the imaginative possibilities ran through my mind I noticed myself getting hard. One last good jerkoff session couldn't hurt before she and I get together at the end of the week as she suggested. Stroking myself to images of her ass, and the tanned, soft and full-looking breasts had me approaching orgasmic bliss in no time. Remembering that sweet goodbye kiss, coupled with these images had me shooting a prolific load into the air, landing on both my belly and thigh before rolling over to sleep on now-cumsoaked sheets.

Friday morning I awoke after a very restful sleep. Checking my phone I saw Courtney had sent a text well after midnight.

C: This morning (Fri) @ 10 am work for you? Either way, I'll be at "granny's" (lol) Here's the address -

Me: See you there

Turning up a long, winding driveway off the main road I came upon a fairly secluded single family rancher surrounded by tall pines. Courtney's car was parked next to the house, and just as I'd taken a few steps from the car I saw her come out and walk briskly towards me, covering the twenty or so yards fairly quickly, dressed in a blue t-shirt and white shorts. I had to steady myself from falling backwards when she jumped up, and threw her arms around my neck while wrapping her legs around my waist.

After a deeply shared passionate kiss, she said, "I'm so thrilled you're here. Thank you so much."

"Normally I say something along the lines of 'it's my pleasure,' but that's not why we're here is it?" I replied.

"Our shared pleasure," she quickly responded. "But more to the point, take me inside. Just fucking take me!" she said excitedly as she kissed me once again.

Who was I to argue, so I carried her inside the house, the kitchen actually, closed the door behind us and turned and pressed her back against it. Her legs squeezed tighter around my waist, ensuring she was going nowhere, as her hands pulled my head tightly against her face, our tongues desperately fencing against each other's.

With my hands at her sides, I worked her shirt up to her chin, broke our kiss long enough to pull it over her head and tossed it back over my shoulder, resumed kissing while mauling her firm 34's through her bra. The heat from her guttural moan fed into my mouth as, instead of reaching behind and unfastening her bra, I pulled the straps off her shoulders and moved the cups down from her warm orbs. Fondling, squeezing and pulling on each I swear she tried to say the word 'yes' while still lip locked.

Wanting to keep the action moving, I turned away from the door and back towards the center of the kitchen. Spotting the granite covered center island, I sat her down, pushed her legs from around me, and started removing her shorts. As she lifted her ass from the countertop a white thong appeared, and I marveled at the contrast of the material against her tanned skin. Taking her left breast in my mouth, I slowly slipped the thong from her ass crack and down her legs while working her nipple with my tongue.

Except for a tiny arrow-like closely-cropped blonde patch above her slit, Courtney was clean shaven. I could smell her sex, filling my nostrils with her intoxicatingly sweet fragrance, and I just had to taste her. I spread her legs wide, past my shoulders, and leaned down to kiss her stomach as she removed the bra anf reclined onto her elbows. Her taut muscles fluttered as I slowly moved down to her dewy pink prize, and I looked up into her eyes in time to see her head fall back as my tongue delved across her soft lips.

"Ahhhh, fuckkk," I heard her moan. "God yes, taste me. Oh, yesssss, fuck yes, yes yes. Lick my pussy, just like that. Oh fuck yes! Feels so good, so fucking good. Oh, oh! God, yes. Mmmm."

It felt like I was holding onto her thighs for dear life, she was squirming so. But it was a pleasurable battle to kiss, lick and suck on her lips and clit, while delving into her sweet channel. Every once in a while I'd extend a little lower and rim her, causing her to squeal in pleasure. After what seemed like hours, but in a very good way, her bucking against my face and tongue let me know she was getting close, so I used my fingers to slide around her ass and pussy lips as I gave her clit the attention it needed. With her moans becoming louder I introduced first one, then a second finger into her lubricious canal, eliciting a string of pleasurable moans and grunts.

"Uh, fuck yes, just like that. Gonna cum you sweet pussy eater. Fuck yes, fuck fuck fuck. Cumming. GOD! FUCK! Gonna cum, gonna cum, oh fuck yes," she practically screamed as her quivering thighs clamped against my ears, squeezing my head as her hands pressed my face hard against her flowing pussy.

After a series of hard but quick spasms, she went limp, legs hanging over one edge of the long countertop, her head over the other. I kissed and nibbled against the soft flesh of her inner thighs as I watched her magnificent chest rise and fall for a few moments. Slowly, she sat up on her elbows once again, face and upper chest flush, her bright blue eyes glassy and a pleasured smile on her face.