Will You Still Please Me, When I'm Fifty Five - Cover

Will You Still Please Me, When I'm Fifty Five

Copyright© 2018 by Pettybox

Chapter 2

Fiction Sex Story: Chapter 2 - A youthful man of 55 retires to a 55 and over community where he doesn't expect to find the sort of "bed fellows" he's accustomed too, but the price is right. But not to worry, he has the looks and the lines to go out of the community and keep his quarry about half his age. Inquiring eyes of a neighbor keep a watch on him and she has a hook the younger girls don't have, Golf. She just has to show him that she has the goods too.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   Consensual   Sports   Spanking   Anal Sex   Masturbation   Oral Sex   Safe Sex  

An hour later with clubs loaded she drove her cart through the roads of our little golf community to a driving range where you need only show your residency card for access. Inside she showed me to the tee boxes where we wheeled our clubs and then she showed me inside again where there were rows of buckets with balls. She took two buckets and said, “Let’s go!”.

I quickly said “Let me get those,” to which she said, “get your own, these are mine!”

We were going to do some serious swinging.

You had to set your own tees, they didn’t have ball loaders, which I like, it sets a more normal pace. We each hit around 5 or 6 balls before I stopped and watched her hit a couple. She had perfect form and drove the ball hard, straight, and far each time. If the distance markers were correct, she was 200 to 250 yards on each drive. To say the least, I was impressed. I drove consistently in the 200-225 range, it was the best part of my game. Not only was she 3 or so years older than me, she weighed 60 to 70 pounds less than me, yet she used her form and concentration to get the maximum on each drive.

“You have excellent form, you should give lessons.” I commented.

“I know, and I used to, back home. I still hit 4 buckets a week. I like the discipline and concentration of each drive. I don’t like to use a 2 or 4 wood, but with a 3 and a 5 I only lose 15 to 20 yards each club going down. With a decent lie, I can use a 2 iron and get as much as a 2 wood on a fairway, but I’m not as controlled. We can move down to the turf tees with our second buckets.” She said as she pointed down the line where a few others were experimenting with fairway woods and perfecting irons.

Her overall confidence with a club in her hand was so obvious, I wondered why she hadn’t turned pro when she was younger. As if reading my mind, she turned and leaned on her club and said “I could have turned pro, but that was always Roberts dream. We chased that until his back problems cropped up. If I had tried we wouldn’t have spent much time together, and he was always too immersed in his job to stay full time golfer.” She said as she teed another ball.

“That stress is what killed him. He carried it even after he retired. He spent an hour on the phone the morning he died talking to his oil cronies. He couldn’t let go.” She said as she lined up her drive and then, whoosh, she was through the ball and watched it soar, long and straight.

She looked at the arc of the shot and then back at me, “That was why I wasn’t with him that first day, I was pissed off he wouldn’t hang up the phone. I took my clubs from the cart and told him to go out alone. I didn’t want to be there in the heat of the mid-day. Down here in summer, you want to be done by noon. Now, let me watch you hit a few.”

Where I thought I might give her a few tips, I knew she could school me and relished her critiquing me. I hit 2 powerful shots, each 200 yards plus, but both with right pulling curls on the end.

“You’ll lose that tail if you keep your head in longer. Tee it with the ball ID up and try to imagine it there after you go through. You don’t need to follow the ball until you finish that swing. Head down, see the number and imagine it still there after the ball leaves. Resist the urge to watch it leave, head down through the ball, you won’t pull it, that’s where you keep getting that curl in the ending trajectory.” She said with authority like a teacher.

I looked up at her and teed my next ball and did as she said. I lost some distance on my first swing, just being more methodical, but I was arrow straight. Quickly I teed up again and tried it with my normal swing and I got straight and distance.

“You HAVE to concentrate on every swing, put everything else out of your mind, it’s you and the ball.” She reinforced to me.

When I looked up at her suddenly I saw her as a sexual being. She was 20 or more years older than any woman I had been with in the last 5 or 10 years, but suddenly she seemed sexy. I don’t know what turned that switch with me, but . . . . . when she turned to tee up a ball for herself I watched that pert ass of hers all through the swing and when she looked back to get my reaction, I know she saw me ogle her ass. Now it wasn’t like I wanted her or put her on my list of possible desirable conquests, she just went from being the older woman who lived across the way from me, to an attractive woman whose confidence in herself and skills made her seem special. I was happy she showed me that side of her.

She smiled and noted the fact I had watched her ass in the athletic stretch shorts she wore. She had a light windbreaker that came down over half of her derriere, but it had shifted up as she prepared to swing. I could see she enjoyed the fact I had ogled her. We finished our first bucket of balls from the tee boxes before she showed me the turf tees for irons practice.

“Don’t forget to take into your swing and result that these artificial turf lies won’t divot and can forgive getting too far behind the ball. You’ll feel the impact on those and discount in your head the result.” She schooled me as she laid out scenarios for our shots.

“Picture the red striped marker about 150 yards out as the green, anything in front as a trap.” She said as she used a 6 iron and nearly hit the marker, I used a 4 and got the distance, but way off the mark, some 15 yards right.

“Don’t let your ego tell you which club to use. A 6 would normally get me 125 yards but if my lie is like this and I stay on the ball and pick it clean, 150 is probable. With you and that 4 you should have been 20 yards past the marker. On any iron, figure lift and backspin. You want the ball to land close to target and stick, never play roll no matter how hard or soft the lie or your target is. I’m a little long for a woman, twenty years ago I could strike with most any man.” She said proudly and confidently.

She gave me tips all through our second bucket, and not like a know-it-all, but in a helpful tone where she saw flaws. I thought I could shave 5 or 6 strokes off my game, she made me feel so sure of myself.

We wheeled our clubs back to her cart and we drove to the path that led to the 1st tees. She looked down to the left and playfully said “There’s no one on the practice greens, let’s give them a run. We’ll putt through all 9, a dollar a stroke, OK?”

I could see she was competitive and she wanted to beat me, but we tied at 16 strokes each for the 9 little flags. We headed back up the hill and her cart didn’t cooperate with the weight of both of us and the clubs. I hopped out and jogged to the top as she easily followed and picked me up near the driving range. She stayed quiet on the way back and pulled into her little parking slot beside her unit.

“Thank you for making me feel alive again. You made me think a lot last night, mostly about wasting my life away, AND thinking how Robert would have kicked my ass for giving up, not playing and just doing nothing. You know I spent almost all of the time since his death stewing, like I was wishing revenge on someone or something that ruined my happiness. You have become a slap in the face for me. I see the life you lead, drawing as much pleasure as you can, and I remember my own life when I was the same way, before I met Robert. I was footloose and fancy free, just like you.”

“Oh? Is that what I am? So far you scolded me on two occasions for cavorting with prostitutes and whores.” I told her to remind her of her judgements of me.

She blushed deeply still sitting in the cart facing me as her face dropped a little like she was about to step off a plateau not knowing how far the drop.

“Before I met Robert, I would have been one of your conquests. I knew a lot of men, had a lot of fun, got high on life, booze, pot, and sex. He made a new woman of me while providing me with all those joys and love too, . . oh, and golf too. I was always addicted to golf. I started when I was 9 and have never stopped.”

“You told me you haven’t played since the day he died.” I challenged.

“No, I haven’t, but I’ve never stopped brushing up my skills.” She said letting out a long sigh.

“Come out with me, tomorrow. We can play here, if that would be too emotional, we can go elsewhere.”

“A golf date?” She asked.

“No, no date, just 2 friends, . . . neighbors, getting out together.”

“Hmmmm, that would be spitting in fates face. If I feel more alive now, maybe that would free me more. Let’s play here!” She said smiling before she slapped my leg and got out of the cart.

I alit as well and took her clubs to her porch where she just had to wheel them in, right beside Roberts clubs were, presumably since the day he died.

She thanked me for everything, including moving her clubs, and stood at her doorway, “Arrange a tee time and come over, I’ll be ready.” She said as she glanced to the 2 sets of clubs inside the porch.

“I have a half of closet full of his things, those clubs can go in there as well, until I get rid of everything. I’m going to try and start my life again.” She said emphatically and waved goodbye.

As I walked to my door I fully expected her to wake up the next day with a different view of all of this, and maybe not quite go to the extremes she was talking. It had been almost 4 years of grieving, feeling sorry for herself, wallowing in hate of something she would never have control of, . . . fate . . . and the cold hard fact that we are all mortal.

I arranged for a 9 o’clock tee time and at 8:30 I gathered my things and brought my bag out and wheeled across the way where I had seen her up and, on her computer, earlier.

True to her word, Roberts clubs were not next to hers on the porch and when she opened the door to push her clubs out I was taken by her presentation. She wore a clingy tight top, actually a one piece that snapped at the crotch (as I remembered unsnapping a few of those in après’ 19th hole situations.) and a short skirt. She wore a sports bra underneath that seemed to hide larger breasts than I had imagined, and the clingy material showed an incredibly flat and supple belly. She wore a pink visor that read Augusta 2001 and a Masters logo.

“Well, aren’t you the cover of Golf magazine?” I cracked.

“Is this all still stylish on the links? I wanted to look nice and be comfortable.”

“For sure, women’s golf outfits are pretty much the same over the years, although many just go out in shorts and polos.” I said looking her over.

“Are you saying I overdid it? I haven’t worn this in 3 or 4 years, the last amateur tournament I played in.”

“Emmy, you look fine, any woman would kill to put on something for the first time in that long and still have it fit.” I assured her.

We loaded clubs and I got in the cart and we started down the drive to the course entrance. She was quiet for a few minutes and then started talking, not looking at me, her eyes fixed straight ahead.

“Robert and I never had any kids, not that we didn’t try, but nothing ever happened. He was tested, and he had low counts and we were told it would happen eventually, but it never did. When I went through “the change” just before we came down here we finally faced facts. I never wanted any medical options to get pregnant and frankly, I liked how my body looked versus all my friends with children. You wouldn’t have admired my bottom if I had any children.”

“Any man would admire you if you dress in a way to show it off, without getting obvious. You are just a pretty woman.” I assured her.

“A woman pretty, . . for her age.” She said softly.

“Emmy, we all have a few wrinkles, age lines and signs of maturity, it’s to be expected. I’ve tried to avoid all that, but I can’t and I do my best to stay in shape, eat right, exercise, . . . . you know the drill.”

“That’s because you chase all those young girls around, ones with a Father complex, or who want an experienced man. Mature men can seduce younger women, women my age don’t attract young men, and if we did it would just be for sex, not a relationship.” She said as we got in the queue of carts lining for the starter to get registered.

“Are you looking for a relationship?”

“God no. I was a lot like you when I was younger, on the prowl, enjoying myself and Robert just swept me off my feet. I kept telling myself that the shine would wear off, but he was the one. After investing 31 years with one man, the one I expected to grow old with, POOF, he was gone. I haven’t looked at another man since, not interested.” She said, and I could tell a little disgust in her voice and demeanor,

“Emmy, you didn’t dress like that to NOT be noticed. You’re going to be ogled all day by lots of men.”

“Am I THAT over the top?” She said suddenly looking at me like I told her that her pants were down.

“No, not at all, you just have the goods and not displaying them overtly at all.” I assured her.

“Oh yeah,” She said sarcastically, “I have the goods. You’re a few years younger than me and wouldn’t think of even talking to me if we weren’t neighbors. You like women half your age to make you feel like you haven’t lost a step.”

“Emmy, I date women half my age because when I go into a bar, to a golf club, anywhere where I might meet someone, all those women in “my age bracket” are home, married, tending their families. Any more mature, or older women that are out like that have make-up spackled on, lipstick applied with a trowel and hair they put on a stand overnight.”

“You’ve never fallen in love? Never met the right one?” She asked as the line moved slowly.

“Oh, there were a few I felt special about, but after living together for a bit we grew tired of each other and split.” I admitted.

“You realize you can’t have sex EVERY night and after a while the urge isn’t as often. The old adage about putting a bean in a jar every time you have sex the first year, and then taking one out every time after the first year will leave you with a lot of beans is true.”

“Oh,?” You tried that?” I cracked.

“Well, we did it with quarters, and we proved it wrong, our jar was empty before our 4th anniversary, but all my girlfriends said it was true. Remember, we never had kids, kept all our energy.” She said with a little smile, perhaps recalling happy moments.

“What do your girlfriends say now, when they see you all fit and trim, ready to start again.” I asked assuming she had reached some sort of epiphany.

She laughed out loud, “Ready to start WHAT? And what girl friends? When your husband dies, your friends treat you like YOU died, they stay away in droves, plus I never made any real friends here, I suppose because they were married and saw me as a threat, like a black widow. In 4 years you are the closest I’ve had to a friend and you’ve only been here a few weeks. What does that tell you? I see people at owner meetings and they talk and act friendly, but besides a wave when they walk or drive by, no one stops.”

I was having a hard time understanding all of her words. Why wasn’t she an “in demand” commodity? Surely, I wasn’t the ONLY single man in the community, or did she just keep to herself that much. As I mulled my thoughts we got to the pre-starter who assured we had reserved a spot, and undoubtedly was going to ask us to join a foursome. As that question was being asked (joining with another couple) she tensed and put her hand to the top of the steering wheel to grip it with white knuckles, nervous to encounter others, when I saw the big diamond and wedding rings on her finger. Aha, that might shoo some men away. Then suddenly my name was called and the starter sent someone to ask us, “There are two 6’s that want to get off, if you go as a two-some now they won’t hold anyone up and you will leave their way clear. You’re up!”

We both hurried to the boxes stretching quickly as we had to hurry. I told her to go first pointing to the ladies’ tee, and she smiled at me. “I haven’t played a round of golf in near 4 years, but I’ll be damned if I have to give you an inch, I’ll play the men’s tees.”

“Emmy, we aren’t competing.”

“No, but I think I’m at least as good as you, so why don’t we just play the same course? Tell you what, loser has to walk up the hill if the cart can’t take the load.”

“You’re on, but it’s not much of a bet, I would never let you walk up.”

“Why?” She snapped, “Because I’m old?”

“No, because you’re a woman, and I’m a gentleman.”

As she stretched and went to the tee box I couldn’t help but think she was trying to feel me out and flirt with me, me thinking her loneliness had gotten the best of her. The thought of a 50+ woman undressing before me frightened me, no matter how good she looked in her outfit. Now I knew I was being both petty and shallow as hell, but young supple female bodies excited me, and drooping wrinkled ones did not. Yes, she was attractive, but I only knew the clothed version and I hoped to keep it that way.

Her tee shot drew a few hand claps among those watching and waiting, it was probably 175-200 yards straight and true. Suddenly I felt pressure to be at least as good as she. As I strode up to tee my ball she said, “Now, remember all the little things we worked on yesterday.”

I nodded and thought of how proud and happy she was to impart some wisdom on me, and I did not want to disappoint her.

While my shot was at least as long as hers, it wasn’t as straight, it didn’t hook, but the clubface must have turned a bit and I was a good 30 yards to the left of her ball taking my view of the green away. We rode off the tee both happy we had good shots for the group watching she commented as she drove, “Now without all those spectators you won’t have to flirt with me, your masculinity is intact.”

I smiled without looking to her, but inside my head my conscience shouted, “ME? Flirt with YOU? It’s all you’ve done since we left your house.”

After four holes, we were both 3 over and both quite happy with our long and short games. She kept me focused on every shot and showed me that concentration was a huge part of a successful round. As we went to the 5th tee we saw a foursome on the opposite adjoining 13th tee, it was Karl, his wife Lara, her sister Sonya and a 4th, a heavier man. While they waited to tee off and Emmy prepared her shot, I nodded to Sonya and she smiled back, so I stepped to her to say hello.

“Trying to stay in your own age bracket?” She wise cracked.

“No, my next-door neighbor, she has a cart.” I said nodding to it.

“Well, I have a car today, I won’t need a ride. Maybe I could stop by later and show it to you.” She said overtly winking to me.

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