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 5

Fiction Sex Story: Chapter 5 - 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  

“Now you!” I demanded.

“Me! What?”

“Something about you, a secret no one knows, and remember, . . I spilled, . . . . . it better be a good one.” I said pointing to her.

“You see me on the porch all the time, on my cart, on the golf course, right? Well, any other time I’m in this house, I’m always naked. The sweat pants and tee you see me in casually is always on that little table by the door and if I have to go out, to get the paper, knock on your door, check emails on the porch, I throw them on. I like being naked.” She admitted.

“You mean all those times you’ve came to my door, you’re commando underneath?”

She smiled and nodded.

“Geez, I thought for the longest time you were somewhat of a spinster, and now you’re about the hottest woman I’ve ever known.” I exclaimed.

“Oh sure, feed me more bullshit, I’ve already told you I loved you, you don’t need to put frosting on it.” She said waving her hand in self-deprecation.

I took her hand and pulled her to me getting face to face. “EMMY, you have proved to me that you are beautiful and stunning under those frumpy sweats and tees, have a loving heart and nature that could allure ANY man, and know how to make a man happy while making sure he knows how to make you happy. I can go out and find younger, beautiful women who desire me, for whatever reason, and have younger men jealous of whatever lure I have, but when they are through with me, or me them, there is little worth hanging around for. Even this conversation is beyond the scope of most of them.”

“If they’re so socially invalid in your eyes, why do you keep going back?” She said, obviously rankled by my constant skirt chasing.

“Wet mouths, tight pussys and the knowledge they wanted nothing more of me than a good fuck that left them satisfied. I always give as good as I get.” I admitted.

“See? THAT’S the Jake I despise. The user, . . but I see you were being used as well. You have to stop those ways, cool those urges, if we are going to give this our best.” She said expressing her doubts.

“I know, but being with you will make that easy to do as long as I don’t see that side of you that scorns me, constantly judges me.”

“That scorn was always just my jealousy of you, of the girls you saw. I’m naked inside this house and walk by a mirror and say to myself, “What does he see in them that he can’t see in me?”. I’m not the type to throw myself at someone. Even when I made my first sex play for you, it wasn’t that way. It was a cold offer, yes or no. I just had to make sure you saw me that way. I wanted you and you didn’t want me back, . . . which is OK, but I had to be sure you saw what I had, besides a golf partner.”

“I think I can be everything you want, but you have to trust me. Plus, you say I didn’t want you. The first day I saw you walking to the board meeting, I watched your ass intently, and when I saw your face and realized you weren’t the young girl I expected, I was put off, I admit, but a lot of that was because of the snide remarks you made, and you didn’t even know me.”

She giggled and flushed with embarrassment, confounding me a bit, causing her to say, “I need to make another admission to you.”

‘‘I was at a particular low when you moved in, and when I saw my new neighbor wasn’t going to be a single old man, or single old lady, or even worse, and old couple, I was intrigued, so intrigued that I sat on the arm of that chair, (pointing to a Queen Anne by the side window) and rubbed myself raw watching you move in and work around the house. It was the first time I felt sexual in a while and when I saw you bring that tramp home I was furious I didn’t approach you before that.”

“OK,OK, enough of this tale telling and admissions, how do we proceed from here.” I finally said. “Do I just go home and let life go on, or do we make an effort to grow together.”

“Will you go to the pool with me today?” She asked.

“You told me you NEVER go to the pool.”

“I will today, and be with you. Let everyone see you and I together, the cold witch and Studley McFuck-a-snake.”

“WHERE DID THAT NAME COME FROM?” I demanded.

“It’s what I call you when you’re whoring with trollops at your house. I’m sorry, but it seemed to fit, AND you should know, your reputation is not un-noticed here in the complex. Ladies at the last board meeting shared their stories they heard about you. “

“So, they already suspect that you and I have gotten together?”

“Not in so many words, they don’t think it’s possible, behind my back I’m known as Cold Witch, and Black Widow. I’m just your golf partner.” She said, disgustedly.

“So, going to the pool together . . . . .” I started to say.

“ . . puts me on the map as one of your trollops until they realize we might be an item.”

I took a few moments to think about it all and made a proposal to her.

“I’ll do it, IF you wear a bikini and show everyone what you’ve been hiding.”

She scowled and smiled, saying “I don’t own a bikini”.

“But, I do!” I said happily.

“I don’t want some other woman’s drawers you’ve washed the cum out of.”

“Sorry cold witch, I have new ones, at least 2 with tags still on them, I was a boy scout, always prepared.”

“Me? A bikini?” She protested.

“Yup, and I’ll dive in the water and come right up beside you and hug and kiss you on the lips. You’ll show off how awesome you look and show that you and I are together. “

“Just what am I proving?” She demanded.

“First off, that you aren’t the cold witch or the black widow, secondly, that I’m not just your golf partner, or what I overheard you say to someone, that I’m not like the brother you never had. Brothers don’t have sex with their sister. Thirdly, you can prove to me that you are serious about me and I’m not just a behind closed door lover.” I pointed out.

She exhaled in defeat and said, “Go get what you have and I’ll pick one.”

“Nope, you walk across the street with me and you can check them out. You want to be a couple, right? Be seen?”

“Oh, I suppose you’re right after all the times I made you keep distance so people wouldn’t talk. I let NO man anywhere near me for a year after Robert so everyone could see I loved him so. Sometimes I would get drunk alone and try to convince myself to tell the world he cheated on me and now I’m horny and want another. Only when you moved in did my juices start flowing again.”

She dressed quickly in her frumpy tee and sweats and we crossed the road holding hands as she smiled at me, her face red in embarrassment.

“Oh, for God’s sake, who’s going to see us? 4 people, tops, IF they’re in their windows.”

“Forgive me. I’ve been pretty private.” She said shyly.

“Don’t wonder why they call you the cold witch.” I said as we went up the 3 steps to my place.

She waited while I went to a closet to get the two bikini’s I kept for “guests” (actually picked out by Stacy) One was a soft, almost pastel, green and the other a bolder bright yellow with orange. Both were on store hangers with tags. When I brought them out, there stood Emmy, naked once again.

“Sorry, once I get inside, I like to take off my witch costume.” She said with a grin.

She looked at the two beach outfits and held up the green saying, “They’re both quite nice, but this is more subtle for now . . . . for my pool debut.”

“You’ve never been to the pool?” I wondered.

“Once with Robert the day after we moved in, our A/C was being worked on and it was ungodly hot, we took a break for a swim. I’ve come and read here in shorts and dangled my feet in, sometimes after book club.”

“You don’t look that void of sun exposure.” I said looking her over.

“My back bedroom has a skylight and unfettered eastern exposure from the big windows on the side. I can lie naked and read from 7 in the morning to early afternoon in the bright light. You’ve never seen that room, it’s the one you use for a workout room.”

“So, put it on and we’ll take the cart to the pool.”

“You don’t have a cover up, boy scout?”

“As a matter of fact, I do, but it’s not new . . . . and no I’ve never had to wash anything out of it. If you must know, Stacy left it here.”

In 5 minutes, we were headed to the pool in her cart. As we walked to the white gates I saw a few heads turn, but when we came in, found 2 chaise’s and set up, there was an old biddy buzz, for sure. Most of the women there were much older, except for a daughter or grand-daughter, and there were only a few older men. She took off her cover-up and I walked her to the steps down into the shallow end and once the water was to our waists we swam to the deep end. Emmy looked stunning. Her body was a wonder, but at 59, never having children, exercising and eating right, she could pass for much younger. She smiled at me and I moved to hug her and kiss her, a blatent PDA.

She let her hands move underwater to my junk for a loving squeeze and whispered. “I’m going to suck your dick good before you fuck my brains out later. Try hiding that hard-on now, let it make its debut here as well.”

She quickly swam away and was on a chaise while I struggled to hide the problem that had arisen. When I finally got to my chaise I looked to her and saw a different, more relaxed face. Her smile beamed and it seemed some lines in her face disappeared, especially across her forehead. Right away I thought to myself that maybe the security of a man she loved was what she always needed to feel complete, happy. Where I originally saw a dour and sour face that looked old, now I saw a beam in her smile, a glow to her face.

She leaned to me and asked, “If you didn’t know me and came to this pool, would you be interested in making my company, and how would you go about your seduction?”

“Well,” I answered, “once I saw your body, especially from behind I would add you to my memory of women I’d like to meet.”

“I’d come over and introduce myself as new to the park, or ask if you were new, depending. You know, shake your hand, find some way to touch you. Strike up a conversation and as soon as there was a lull, ask you to join me in the pool. I’d find another reason to touch you, offer my hand as you got up, and walk you to the pool, making small conversation Once we both got to where our genitals were wet, I would say something semi-sexual, because like it or not, when your hoo-hah gets wet with the pool water it gets your attention, a man is nearby and he’s made you think of sex in some way by his comment, plus you’re scantily dressed. As long as you’re open to meeting new men, enjoy their company, and have regular orgasms, I’m half way in your pants.”

“My, you’re pretty confident. How do you know a woman has regular orgasms?” She asked, as if doubting me.

“Before you were married, and since you became widowed, would you say YOU had regular orgasms, . . . masturbated?”

“I’ve already told you that, but I suppose with any woman it might be true. How often have you met women at pools where that worked?”

“Only a few, just one here, Stacy, but I have successfully used that tact other times. My looks don’t hurt either.” I said with a smirk.

“Now that we’ve proclaimed love to each other you can forget that little maneuver, or do you have others?” She said with a tentative smile.

“Don’t worry about me for a second. I would never deceive you, but other moves? Hmmmm, remember, I AM fucking you.” I told her with a wink.

“Don’t ever think that YOU seduced me” She said as she broke out a wide smile and leaned in to assure privacy. “You were about to turn and run until you knew I was going to give you a blowjob that night.”

“No man turns down a blowjob.” I assured her.

“Don’t think that I don’t know that, and once you had me I knew I had you in my web.”

“Believe it or not, I knew I was falling in love with you, but I didn’t see the sexual side of you, and that scared the hell out of me.” I admitted.

She smiled and her face brightened, I could see she was terrifically happy and she suddenly stood. I went to stand and she held her hand out for me to stay. She moved her chaise right next to mine, touching, and laid back down, rolling to my side to kiss me and then looked around at any faces who might be ogling us and showed them a satisfied grin. It looked like the first time in her 4 plus years at Wyndtree at Thousand Oaks she was totally happy.

Over the next 3 months Emmy and I lived at each other’s places in a state of total joy. We never argued, disagreed rarely, still spent our 2 days on the range, and two days golfing, one day at Thousand Oaks and the next at one of 3 other local courses. We took turns cooking for each other, each styling ourselves as gourmets in some ways. We did most everything together, but in doing so, I had alienated myself from my 3 friends that made up my weekly foursome. They were known as Jack, Arnie, and Shark. We always referred to each other by these names because of the bevy of women they, and I, saw, not wanting to get too personal. I always remained Jake, for some reason. After telling them I was busy, over and over again, they finally showed up at my door to convince me to rejoin them. They had a hard time filling my spot and rarely did courses fill in their “fourth” with anyone of my caliber and they were sick of dragging the fourth they were stuck with, they wanted to play with me. Emmy and I discussed it and she agreed to my joining them twice a week as I had before Emmy and I became a couple, on Saturdays and Sundays. She claimed she wanted her “me time” as well, and wanted to get more involved with club functions. Usually it was Saturday afternoon and a 19th hole stop, and then 9 holes on Sunday morning and joining them to watch baseball or football at the 19th or Snappers. While it was strictly male bonding, there were girls around, and some I used to date (fuck), but they were seeing some of the other 3 and all knew I wasn’t out on the prowl.

One particular Sunday there were 6 of us at a round table at Anclote Keys after our round. Besides me, it was Arnie, Jack, Shark, Stacy (that Stacy), who was with Shark, and Maria, who was trying to hook up with Jack. The Tee Party had become a popular place besides for after golf, it was also quite a good place to grab a quick bite, and meet girls.

We were laughing it up talking about our round, ball busting, waiting for our food, I think we all ordered wings. We had 2 beers each on the course, so Arnie and I were drinking soda as we had to drive. Since this was a new watering hole, the Police were keeping an eye on it and those leaving. There had been complaints from the locals. As we talked Stacy was hanging on Shark and I think trying to make me jealous. I knew where my bread was buttered and didn’t need Stacy in the least. When the waitress came with the food and moved around the table I was getting glimpses of the bar and at one point I swore I saw Emmy. I sluffed off the thought as she had no reason to come here and would have called if she needed me.

We ate and talked as the fellows and I charted out our Sunday morning 9. Everyone had something going on in the afternoon, so we made no plans for Snappers. As we talked I, once again, caught a glimpse of the bar and swore I saw Emmy. I excused myself using the bathroom as an excuse and circled around to the bar and sure enough, there was Emmy, sipping a coke and peering around a pole at our table.

“I snuck up behind her and whispered “Looking for someone?”

She startled and turned to see me and flushed red in embarrassment.

Now, I’m not one to fly off the handle much, but here I near blew a fuse.

“You profess your love to me and declare trust, and come out to sneak around and spy on me?”

“Please I can explain,” she started to say but I cut her off and said, “No, let’s go outside right now and settle this.” and took her by the arm to and out the door.

“Jake don’t be mad at me, I was sitting home thinking you were out and maybe you were tempted . . . . .”

“So that’s your version of trust!” I shouted. “Your coming out here to spy on me is about the same as cheating on ME! It’s a broken bond of trust. So, you’ve been watching, what have you seen?”

She started to cry and said “Nothing, just you and the guys bull shitting, eating and I see you just drank soda. But Stacy . . . .”

“Stacy is with Shark, and has been for a few weeks. She knows my situation. As a matter of fact, she’s tried to tease me a bit tonight, but I haven’t taken the bait.”

“I’m so sorry for being such a jerk, a bitch.” She said looking to hug me and have me forgive her. But this was not going to pass that easy.

“Go home, I’ll call you in the morning if I have time before I meet the guys for golf.” I told her as I walked away.

“I’ll wait for you at your place, I’ll make it up to you.” She called out.

I turned to her, “NO, you go to your house, not mine. I told you I would call you.”

I went back to The Tee Party and as I went in I heard her crying and looked to be sure she got into her car and left.

I was fuming when I went back in but put on a good front to finish my food and bid goodbye to everyone. I got home and poured myself a double of Jamesons and sat and stewed. I knew she was watching from her porch so I got up and drew the shades.

She knew enough to know that coming to my door to beg was the wrong tact to take and whether she got any sleep that night I don’t know, but Mr. Jameson settled me just fine after playing 18, going through the stress of her betrayal, and sitting back in my recliner. I woke up at 8 o’clock Monday, well rested, but in need of a shower that I took, even before I made coffee.

Once I dressed I decided I would go out for breakfast to just relax and let the day unfold before I confronted Emmy. I took just my keys, my license and a $50 bill when I left. I was wearing thin exercise pants and any kind of weight in them caused me to keep yanking them up, never having much of an ass to hold them up.

The Waffle House was my favorite morning stop and where I was headed. I noticed as I left that Emmys car was gone, but she usually did nail spa first thing every Monday. I settled into a booth and the waitress’s all knew my usual, 3 eggs over, scattered hash browns, no toast, but all of this on top of a waffle (which I rarely ate more than half of).

As I ate and drank my coffee (with 3 quick refills) I thought how to approach Emmy, sitting back and scanning the area outside the window looking for answers. As I watched traffic go by I saw a familiar car in the Office Max lot next door, it was Emmys custom painted, Florida Turquoise, Camaro. (Her replacement for the Cimarron)

I no more than thought she parked away from the Waffle House lot, knowing I would not stop if I saw it, when she swooped into my booth.

“Don’t make a scene Jake, can’t we talk?”

I was calm and surprised she was acting as if I had dumped her, and I clearly hadn’t, but her paranoia had gone to work on her.

“Let ME talk, Em.” I said taking her hand.

“We say, and agree that love is trust. You’re going to check on me last night was anything but trust. You don’t truly love me, you see me as some sort of security blanket. “

“I do, I truly love you more than I’ve ever loved any man, even Robert! He cheated on me and made me insecure because I knew I couldn’t trust him.”

“Emmy, think about what you just said, because last night, you may as well had gone home with another man, you cheated on me.” I told her.

“NO, NO, I would NEVER cheat on you. I know the pain!” She implored.

“Then you know how I feel.” I said as I looked at her face that no longer beamed with the young glow that I saw just a day ago. The worry line over her forehead was prominent once again.

She went to make a point and suddenly stopped, letting “Then you know how I feel” sink in.

“Oh, my God, I did betray you, your love and your trust.” She realized as tears began to form in her eyes.

She thought for a moment, “I had no reason to doubt you. I’m so sorry Jake. How do we get back to where we were, please tell me we can?”

“Of course, we can, the fact you came here to confront me proves we can, but you have to get over the trust issues. I am with you heart and soul until the time we both see it not working, we will know if there are problems. Trust your heart, trust me, I’m more than your security blanket, I love you.”

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