Country Club Fun
written by:
cptn_average

Country clubs are places that most people tend to avoid; most likely because of the stereotype that only rich stuck-up snobs belong to those places and those people definitely can't have any fun. That's what I thought too, until I met Mrs. Anderson. I had been a caddy at one of the local country clubs for several years and have had both very good and very bad rounds. Seeing that I was 18, it was the beginning of my last summer as a caddy when I first crossed paths with Mrs. Anderson. She was in her mid-forties, took very good care of her body and knew it by what she wore. Nothing too slutty, but enough in the right places to give almost any man an instant hard-on.

The first time I caddied for her was a fluke, she was playing with her husband, we spent most of the round talking amiably about little things. Normally you don't pick you who caddie for, and rarely will they request you. As the summer wore on, I began to caddie for Mrs. Anderson more and more frequently; almost to the point I suspected she started requesting me. I wasn't complaining at all, the more time we spent together the friendlier our behavior became laughing and joking, especially when we weren't too close to other members. Not that we flirted, but we still had a clear member/caddie distinction between us. Then there were the other jealous caddies that desperately wanted to caddie for her and never quite seemed to achieve it.

Mrs. Anderson and I spent most of the summer as boss and employee until one particular morning she hit a particularly bad drive in the opposite direction of her husband. It didn't hurt playing from a different tee gave the hole a vastly different look. He offered the cart to her, telling me to take a break and ride along with her to get her ball for the next shot. Once we were by ourselves, she placed her hand high enough on my leg where she could nudge my balls if she chose to. Instead all she did was ask if I liked it would like more, which I quickly said I did. By the time we got to her ball, I had a raging erection that my towel was hiding, but once I got out of the cart she saw and thankfully only laughed and smiled that she still has that effect on men. Her second shot got us back by her husband, which ended it for that hole. Which thankfully gave me time to control my cock. Unfortunately we didn't have another incident that round. However, I had some very vivid dreams with Mrs. Anderson and what I'd do to her naked body.

It took a week before I was able to caddie for her again, and from the first tee my mind was going crazy wondering if or what she might do this time. Well, it only took her until the second hole when she got another opportunity to have some fun with me. She bent down to dig in her bag, not finding what she wanted, stood back up with her ass facing me her hand raised her skirt just enough for me to catch a glimpse of her panties. Once again I had the difficult task of keeping my erection under control. All Mrs. Anderson did was turn around and flash me a quick smile.

Later that round she flashed me again, although this time I got a much better view. As was custom, the members take a quick break at the turn before finishing the round. All the ladies went to the restroom and of course Mrs. Anderson came out first. For a few minutes it was just the two of us, her sitting on a bench and me sitting on the ground off to the side of the tee box. She called my name and I dutifully turned to look, just in time to see her legs spread wide open and a bare, clean-shaven pussy peeking back at me. It takes a moment for the picture to register, but when it does I feel myself turning red and looking away. Again, all she gives me is a coy smile and the question of if I like what I see and want more. Again, I was speechless, but nodded yes and luckily regained my wits as everyone else started to find their way back to the hole. When suddenly Mrs. Anderson says she has to go again before she tees off and runs off and back before looking at me again. Which made me think she regretted the whole thing, however, that next hole she leaned close whispering how wet she is thinking about what she'd do with my cock.

The rest of the round passed normally; as did most of the rounds the rest of the year, but those weren't too many as it was late August and the rounds got fewer and fewer. I was beginning to think nothing would happen and it would end up being a case of flirting gone cold. Then things had the glimmer of turning around when the restaurant manager asked if I would want to switch inside and bus tables. Now that is normally something reserved for the younger guys, I thought of it as another chance to run into Mrs. Anderson. Besides, all the parties were coming up and the tips were split evenly among waitresses and bus boys so there was good money to be had.

It took a few shifts bussing tables before the inevitable happened and she discovered I had moved inside for the time being. Just the sight of her made my cock stir, thinking back to her flashing that gorgeous body of hers. That night she played a big role in my fantasies.

As usual I was working the late shift on a Saturday night when Mrs. Anderson approach me with the dining room manager. At first I thought I was busted and was going to be tossed out on my ass. Instead I was informed that I should follow Mrs. Anderson up to the women's locker-room and help her take something out to her car. Following her up the stairs, I got a wink and a smile once we were well out of the way of anyone seeing us. Once in the locker-room, she quickly pulled me off to the side so we were hidden from any doors and would have enough warning if someone should walk in on us. Dropping to her knees in front of me, while freeing my cock as fast as she can Mrs. Anderson half-growls, "God, I've been waiting all summer to see what that tastes like."

All I can do is steady myself because there is no way to stop her and not give us away. Not only that, stopping her was the furthest thing from my mind. Seeing her head bob up and down my shaft and fingering herself with a free hand pretty much chased all thoughts from my head. Quickly she shifted to running her tongue the length of the shaft, stopping at the base to pop my boys in her mouth and at the tip to swirl her tongue around the head. With one look at me and mouthing the words 'cum for me' I leaned my head back and shot my wad deep into her throat. Like the experienced pro she is, Mrs. Anderson never skipped a beat nor let a drop of cum escape her mouth. After milking me dry, she came up for a kiss and I could taste myself on her lips.

A short moment later we heard the door open to the lockerroom as another member entered and went to get something out of her locker. Luckily we were hidden enough and done with the fun part of helping her out that Mrs. Anderson and I were able to arrange ourselves to look normal enough that the lady walked passed us, gave a quick 'hi' and glance, and kept walking. Not wanting to mess anything up, I got the package from Mrs. Anderson's locker and followed her to the car.

Once out to her car, and the package safely stowed, Mrs. Anderson pressed her hand against my cock after a quick look around, and told me she had waited and dreamt about that all summer and it lived up to the dreams. Now it was my time to bury my face in her, and then the grand finale of being fucked by me. All I could do was smile and agree with each proposition. I had seen her well-groomed pussy once or twice before from a distance and had many dreams of seeing it up close and tasting her sweet juices, that it took all my strength to not take her right then and there. I could tell she was just as close to letting me take her too. Except we both had a flash of where we were and decided we couldn't take the risk. Instead we agreed on the following Saturday morning because I had the morning shift and her husband always went to the gym then.

Settling that, we walked into the dining room and went our separate ways as though nothing had happened. Unfortunately I didn't have a watch on me so I had no clue that so much time had passed. What seemed like five minutes was really closer to thirty. I got a stern look from my boss, but I only apologized saying I didn't think it took that long and I'll get cracking on my tasks for the night. Luckily they weren't busy and she bought the story. I got to work and tried as hard as I could to get the pictures out of my head. I had to wait until I was home to dream about her lips on my cock and then some. It helped that I didn't see Mrs. Anderson again that night. I couldn't get out of work fast enough that night, but when I did, I had some of the best dreams I've ever had.

The next week dragged as I couldn't wait until Saturday morning. However, it was getting to be the middle of the week and hadn't seen Mrs. Anderson Since the previous Saturday and all we decided on was the day and a general time. Well, when I went to work on Thursday, there was an envelope taped to my locker. Opening it up I saw it was a note from Mrs. Anderson telling me where she wanted to meet me. Looking around to make sure I was alone, I skimmed the letter and found out she would drive their black Durango SUV and park it in a department store parking lot nearby early on Saturday. All I had to do was show up and let my tongue and fingers do the rest. The only thing she asked is that I put the enclosed blank business card in her golf locker and she would see it tomorrow afternoon. The rest of the night was great, simply because my mind was definitely elsewhere. I was able to put the card in her locker. My hand was shaking as I placed inside and closed the door.

I know that Friday happened, but don't remember it, I just know it came between the note and the day I could eat Mrs. Anderson's pussy. I got up extra early on Saturday to make sure I got to the parking lot so I could take my time pleasuring her. As I pulled in and drove to the appointed spot, I saw her SUV off to the side and her sitting in the driver's seat. Parking next to her, I started to get in her car, but she had already gotten out and started to lead me to the side door. Where she could lay back and spread out so neither one was cramped for space or sticking out of the car.

She was wearing a loose fitting sweatshirt and sweatpants. Once Mrs. Anderson was comfortably settled in, I slowly removed her pants to expose a neatly trimmed and already glistening pussy. I leaned in giving her a deep, passionate kiss, before lowering myself to her honey pot. Teasingly I kissed all around it making ever smaller circles before planting one on her clit and another over her hole. Then I started to gently run my tongue the length of her slit, barely touching her soft skin. Mrs. Anderson started moaning at my touch. I grabbed one tit with my hand and started to massage it when she removed the top revealing her bare breasts. My hand again settled on a breast, kneading the nipple with my fingers.

By now I was lapping up her juices with full strokes and flicking my tongue across her clit. Sometimes I would suck in her clit and flick it or run my teeth across it, much to her delight. With my other hand, I inserted it in her pussy and started fucking her with it. Now she was grinding her hips into my face, trying to get the best angle for herself.

Wanting to see how far she would go as excited as she was, I started to randomly slap her breasts and nipples switching between each one. Not hard, but enough to get her to jump each time. However, her moaning and bucking increased as I worked her over.

The next move I made could've ruined everything. Yet, I took the chance because when I moved my finger to the bottom of her slit, near her asshole, she didn't back away, but almost moved closer as if she wanted that. Watching her face intently, her eyes were closed and a blissful facade covered her face, I pulled my finger from her pussy and started to run it the length of her crack, and each time I moved over her asshole I pushed a little harder. I kept up working with my tongue the whole time.

Instead of backing away, she pushed down on my finger, impaling herself on it. She even went so far as to get out the phrases, "God, just push it in already." and "I'll take over these."

I did push my finger all the way into her ass, pausing a few beats to let her body adjust to it before fucking her with it. She grabbed her tits with both hands, allowing me to fuck her pussy with it while working her own tits over.

After several minutes in this position her legs started to squeeze around my head as they began to spasm from wave after wave of Mrs. Anderson's pent up orgasms are released. Her body convulses as she grinds into me even harder. Who knows how many there were, but after a seeming eternity her body finally calmed down enough and all I could do is sit back and gaze upon the glow of a sexy older woman who just had too many orgasms to count.

After sitting there for a few minutes, she put on her clothes before someone came along and saw us in this position. I'm not quite sure how we escaped notice, but glad for that fact.

I broke the silence be saying how incredibly sexy and erotic that was to watch her buck and moan like that; and that too lived up to my dreams and more. She told me how it's been years since her husband had gone down on her and she forgot how wonderful it was and how she couldn't wait until I could enter her for real.

Looking at the clock, I had more than enough time to wash my face and hands, clean myself up and get to work on time. I wonder how I made it through that day at work without getting slapped, fired, or showing off a huge erections; because my thoughts were always about fucking Mrs. Anderson, and if I happened to be looking at a beautiful woman, she would either join or replace Mrs. Anderson in a fuckfest.

I didn't see Mrs. Anderson for a few days after that, so again I started to fear we had gone too far and wouldn't get a chance to fuck her for real. The first time we did cross paths, however, she shot me a sly smile and wink win nobody was looking and that settled me down while almost giving me a hard-on at the same time. For almost two weeks that is all it was; a glance here and smile there, which was driving me crazy. Finally, I got the note I had been waiting for, shoved inside my locker.

On the Saturday two weeks from now, there was going to be an event for the women members taking place in the afternoon and going into late evening. At 7 PM, as it is winding down, I am to meet her on the fifth tee which happens to be the furthest from the clubhouse. Again I was to drop the card back in her locker if I was going take the next step. With my heart pounding in my chest, I looked at the posted schedule and saw that I worked until 6 that day, which would be perfect. Later that shift I was sent to bring some things down from the women's locker room giving me the perfect chance to let Mrs. Anderson know I was ready for the next step. Which on some levels I was, but on others, I still wasn't quite sure what I was getting into.

The weeks passed by at a slow pace, but finally the appointed day had arrived. I made sure to have loose fitting clothes to wear for the rendezvous with Mrs. Anderson. That was probably the hardest day I have worked in my life. All I could think about was fucking her, but the last thing I could do was let myself get an erection or stare at her. Thankfully, she didn't arrive until about 2 PM, so I had some time to work without her being around. But the skirt and blouse she wore hid enough for the members, but fitted her enough to turn any and all heads.

The only thing I stared at was my watch, which didn't help at all, but it was better than staring at her. My mind kept running various positions and scenarios, but I didn't want to have any preconceived expectations about actually fucking her, regardless of how mind-blowing the past encounters have been. That is not to say we didn't glance at each other because we did.

Once it was time for my shift to end, I practically ran to my locker, changed clothes, and tossed my work clothes in my car while I waited. Since it was starting to get dark and cooling off, most of the members had gone inside so it was going to be a lot easier to get to where I needed to be. About 6:45 I started to pick my way towards the fifth tee, being careful not to be seen by anyone. I could only hope that Mrs. Anderson was on her way to the spot as well.

As I closed in on the tee, it was getting dark and harder to see, but I could still make out a pile of clothes right in the middle of the men's tee. With a huge smile on my face and rock hard dick leading the way I snuck up to the women's tee, where I could see Mrs. Anderson's back and it looked like she had started without me. As I came up to her, her legs were spread wide and one hand was playing with a breast while the other was buried in her pussy.

Quietly I stripped naked behind her, there was definitely no going back now. Leaning in, I whispered that I would take over for her as I grabbed the other tit and started playing with it. She simply smiles and responds that I can gladly take over and she thought I'd never get here so she had to start without me.

I quickly moved in front of her and dove into her sopping wet pussy. As aroused as she was, I didn't waste any time being gently and warming her up. I still had to tease her though, planting kisses around her pussy, and using my tongue to 'draw' the letters of the alphabet on her pussy. Her hands kept moving from my head to her breasts while moans kept escaping her lips. I decided to have more fun with her and start randomly moving my hands between squeezing her ass and slapping her breasts and nipples. This drove her even more crazy.

Eventually she couldn't take it and pushed me down on the ground, telling me she wanted to suck my cock. I told her as long as I could keep eating her out. This brought an almost quizzical look from her, but after positioning Mrs. Anderson on her side, I got into position and we both went to work. I had to focus on her or else cum within minutes if not seconds from her blowjob. She starts bobbing up and down on my cock, frantically trying to make me cum. Then she grabs my balls with her hands before sucking them into her mouth and jacking me off with her hands.

At the same time, I was focusing on her clit while stuffing her pussy with two fingers. Suddenly her legs clamp down on my head as she grinds her pussy into me and her body starts shaking from the first of many orgasms I hope to give her. After several orgasms and lots of moaning and groaning from both of us, Mrs. Anderson breaks free and after a deep kiss and a thank-you, she makes a request of her own. Her husband was never into experimenting, and neither was she until now, and she recently started looking at porn and one thing that got her real turned on was seeing pictures of women being fucked from behind. With that, she walks me over to the fourth green which happens to be elevated in the back and gets on her hands and knees.

I obligingly take my place behind her and enter her. Never having fucked a woman her age, I wasn't sure what to expect, but what I received was a tight fitting and extremely wet pussy. There was nothing left to do but grab her hips and start thrusting. She was bucking wildly and as hard as she could forcing my cock deep inside. I would alternate playing with her pussy and tits. She would join in and also play with herself.

By now I'm surprised that nobody has come to see what is going on because no matter how hard we try and be quiet both of us keep letting out various sounds and noises. Letting Mrs. Anderson take over pleasuring herself, I focus on her lovely ass. First I begin by light taps on each cheek to gauge her response. Which can be summed up by her emphatic squeal of delight and comments like "spank me harder" and "save fucking my ass for next time." Of course hearing those phrases, I couldn't help but oblige and began to spank her several more times as hard as I dare being out in the open.

Yet I could feel if it went on any longer, we were sure to be discovered, so I grabbed her hips and reached for her asshole with my thumb and started massaging it and running my thumb up and down her crack. After a few minutes of pumping I could feel her legs start to quiver and entire body shake as more orgasms rocked her gorgeous body. A request to "Please cum in me, I can't wait anymore" pushed me over the ledge and my body shook as I thrust deep and hard into Mrs. Anderson to release my seed.

Once drained, my limp cock slipped out of her pussy as I rolled off her, thinking we should get cleaned up and go before we're found out, but not before Mrs. Anderson leans over to clean my cock off while trying to scoop any cum leaking out of her pussy with her hand and cleaning that off as well. All I could say was how mind-blowing that was and how I'd love to do that again. She simply smiled and told me I could fuck her pussy anytime, any place, and any position that I wanted. Regaining our sense we scrambled to get dressed and leave our separate ways. I managed to get back to my car without anyone stopping me, I could only hope she also got out untouched.

It took me a long time that night to fall asleep, with the adrenaline of fucking a sexy older lady out in public coursing through me. Luckily I had a few days off before I had to work again, and I wasn't sure how it would go; if anyone saw or heard us. The shift came and went with no mention of it by anyone, not even through the rumor mill that someone heard something like the sound of people fucking on the course last Saturday night. I had to wait another day to see Mrs. Anderson and her reaction to me spoke volumes; she acted the same way as before we fucked and right then and there I knew I'd be able to get another piece of that ass. As I was getting ready to leave for the night, I opened up my locker and another envelope fell out. The instructions were for me to open when I got home, and this was a present for me. I waited as long as I could to open the envelope, in the car and a few miles away from the club, and out came the panties Mrs. Anderson wore last Saturday night.

After that Saturday night at the country club, Mrs. Anderson and I hooked up on a somewhat regular basis when our schedules allowed it. That was some of the most exciting and mind-blowing sex I've ever had.