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 3

Fiction Sex Story: Chapter 3 - 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  

I had cautioned her about drinking three splits, but she assured me that champagne was a favorite of hers and not a problem, and it wasn’t until the ride back to our homes she wavered. She stopped about half-way and claimed the fresh air had her a bit tipsy and would I mind finishing the drive. I hopped out and she scooted over and I drove us the rest of the way. At her place I told her to go ahead in, I would get her clubs for her, and I did, placing them in their familiar spot on her lanai (porch).

“Jakey, can you come in and sit with me for a couple minutes?” She called from inside.

I went in and she was in a recliner smiling at me.

We chatted for a few minutes until I was sure she wasn’t going to be sick or anything. I was watching her carefully, not wanting to leave her if she was to get up and fall, not really gauging how drunk she might be. The depth of conversation had become detailed enough to where I was sure she was not drunk and I was preparing to leave, steering the tone of my words.

Emmy began to get up, saying she had to use the bathroom.

“Are you OK?” I asked making sure she wasn’t going to be sick.

“Yes, I’m fine, champagne and I get along just perfectly. Wait till I come back if you want.” She assured me as I watched her walk down the hall, looking to be sure she was OK on her feet.

After a few minutes I began to get concerned and called out, “EMMY are you OK?”

I didn’t get an answer right away so I stood waiting to hear something and she called back, “Jake can you come here for a minute?”

I was afraid she had gotten sick or fallen so I went back to her bedroom, where the master bath was (like in my place), I stood outside the door, not being able to see in the bathroom door, on the same wall where I was standing.

“You can come in, (chuckling) . . . bet you never thought you’d be invited into my bedroom.” She said mysteriously, but I still thought she had gotten sick.

I cautiously stepped into the room so I could look into the bathroom to check on her, but she stepped out, . . . . naked.

“EMMY!!” I shouted but she remained calm and simply smiled and said “Not what you expected, huh? Not having kids and staying in shape keeps your body young.”

I started to retreat and she cried out, “PLEASE! As my friend, and we’ve become good friends, STAY, and at least listen to me.”

“Well, cover up then.” I asked averting my eyes.

“No, I want you to see me as a desirable woman who is capable of being one of your so-called friends with benefits. I don’t want a love attachment; my body just longs for the touch of a man. I thought those longings had stopped, but you’ve reawakened them. I see the little parade of bunnies at your place, even stood at the door once and heard the cries of love. Robert and I were at least as active as you, and after golfing a good round we would have champagne and go home and make love all night long. My first taste of that bubbly today lit my fire. I wasn’t tipsy when I asked you to drive the cart home, I needed a moment to touch myself, just a grab and squeeze as you got out and I scooted over, I was that bad.”

Truth was, she did look quite delicious. Her skin was smooth, there were no sags or wrinkles of age, even her breasts were round with just enough gravity to form perfect firm teardrops with bright nipples atop. When she did a pirouette, I saw the ass I had admired many times and realized that nothing was holding it up or together, no spanx, she truly had the tight butt of a twenty-five-year-old woman.

Emmy stepped towards me and truthfully, I couldn’t walk away. She put her arms around me and held me tightly resting her head on my shoulder and I felt her shiver and heard her sob as my arms went around her.

“Happy tears.” She whispered softly as her arms tightened around me and my hand slipped down to hold one of her supple cheeks.

I felt her pull her head back and I looked to her and she pasted her lips to mine and we kissed long and hard and then she stepped back pulling my crew shirt from my waist and pushed it up to get it over my head and before I could lower my arms her mouth went to one of my nipples and she suckled and moaned as if she needed to be nourished, fulfilled. She slid her tongue across my chest to my other nipple and continued her moans and sounds of wanting. Her hands dropped from my back and went to my belt. She pulled her head back and looked into my eyes as her fingers worked my belt.

She showed a little grin and in a low voice and very sexily she said, “You know what comes next and I want this, I love this. I want you to want me the same way. I can please you. I don’t want anything but a lover. No boyfriends, no husbands, no jealousy’s, just like the women I see you bring home now. Before I was married, I was one of those and I’m not ashamed to admit it. I knew then and now, how to have a good time with a man.”

As her words ended my belt was loosened and her hand worked the button and the fly, letting them drop to the floor. Her soft hand slid inside my boxer brief, around my hardening cock to cup my balls.

“You’re going to smell so good, taste so good before you’ve showered, like a real man tastes, like I always liked it.”

She went to her knees and pulled my undies down letting me pop up in front of her face. I saw the brightest smile I had ever seen from her as she looked at my cock intently and then took it in her hands, stroked it, rubbed it on her face, and then gently kissed the tip and brought her eyes to mine. She said nothing, just opened her mouth and closed over my cockhead. Her tongue went around me and she moved her mouth over half the shaft and then almost half the way out and then back in, 5 or 6 times. She took her mouth off me and smiled like before, and then repeated the whole thing.

“You taste delicious and I would love to excite you and have your juice in my mouth, but my pussy is literally dripping on the floor. Would you like to taste me, fuck me, and then fuck me some more?”

I lowered my hands and she took them and pulled herself up and I walked her back to her bed. When the backs of her thighs hit the edge of the bed she sat down and I went to my knees and put a hand under each of her knees, tipping her back with her smooth pussy right before me. It was as wet as she promised and I put my mouth and face into it to taste and excite her. I fancy myself as a great pussy eater, but she was delirious in mere seconds and flopping like a fish out of water until my hands went up and began to rub her stomach and play with her nipples. Her “flopping” stopped and she began to moan and breathe heavy and soon make grunts and breath catches when she would bear down and orgasm with muffled squeals. I knew she was cumming, I was getting copious amounts of discharge from her sopping pussy. Soon she was starting to rotate her hips as if to move me away. I pulled back, wiped my wet mouth across her thigh and stood enough to kneel on the bed, where I aimed and impaled her with my aching dick.

She was, without doubt, the tightest pussy I ever went into. Her eyes rolled to the back of her head and she pitched her head back so hard she lifted her neck and shoulders from the bed as she sighed loud and then made a long “ahhhh” as I began to fuck her. She was all moans, squeals, and grunts as I stroked into her. She was in her own world, she called me “Rob” at least twice, and when I spoke in a low voice saying “so tight”, she moaned “like my ass Rob?”. If any woman ever enjoyed her time under me more, I could not remember. Her appreciation of my screwing had me brewing already and I still wanted to flip her and doggie her, looking at that ass I had admired all those weeks.

I pulled from her and put a hand under her hip to encourage her to move, but she was still in orgasm, I guess. I tried again and finally asked, “Do you want to flip?”

She looked at me with glassy eyes and smiled as she rolled to her knees and put her ass prominently in the air and rested her head on her clasped hands. I moved to her and slipped back into her tight slot only to hear her moans, groans, and grunts again. At one point I heard her trying to say something among her cries of ecstasy and I finally deduced the words “bad” and “spank”. I took a chance and gave her a crack, not too hard, on the gorgeous ass I was holding on to.

She shrieked with delight and I gave her another one harder, and another before going to the other side and repeating, 3 fairly hard open hand spanks.

Her shoulders slumped down and I almost thought she might have passed out, but again we groaned out more words, ending with “Rob”. Her tight snatch and sexy performance had pushed me beyond the point of being able to thwart my orgasm. I knew it was close and wasn’t sure if I should go for it and fill her and blurted out, “I’m gonna shoot Emmy, where do . . . . .” before I could finish she laid out flat, and turned to get her mouth onto me. She was about 3 seconds late as I put my hand on myself to keep the friction and a long wet surge hit her below the chin and one surge of cum hit her under her nose, but she willingly opened her mouth and pumped her lips and tongue over me repeatedly, getting the rest of any I had and moaning and savoring it to her great delight.

I suspected that once she had a moment or two to swallow (no pun intended) everything that had transpired she would rage at me and toss me out, realizing all that had happened. We both collapsed on the bed, me falling straight on my face, and her to my side, her face about at my knees. We stayed this way and I figured once she stirred I would leave. The clock on her bed stand read 6:30. We finished golf around 3:30, had drinks and got back to our places around 4:30 or so. So, we had spent a couple hours, give or take, getting sexed up. I thought she might be falling asleep so I thought I might wait until she did and sneak out.

I rested and thought I caught myself nodding off so I looked up to check if she were sleeping and caught sight of the clock-radio on her bed stand, . . . 11:45!!

We had both snoozed over 5 hours. It was then that I realized what had woken me up, she was softly blowing air on my cock and kissing the tip. I startled at first until I got my bearings and realized what was happening.

“What’s the matter? Was I too much for you? Have you been afraid to find out what an experienced woman could do with an experienced man.” She whispered.

“No I just like the . . . . . innocence of a young girl’s face, I guess.”

“You don’t think any of those girls are innocent, do you? I haven’t had sex for 4 years, isn’t that pretty innocent? I’ve been one of the girls you chase before, chasing guys, chasing a good time. That was how I met Robert. My friend JoAnne and I would hit the links using the Mens tees and would let a men’s two-some catch up to us and we’d “four-up”, as she called it. If they didn’t seem the type, we’d let them play through, wait for another. We could match most men, we were good, and you know I’m good, and not just at golfing. Robert was the pro where I met him. He was special and made me feel special and I never thought I wanted another man. You made me want a man again, that spirit you have. I was envious of you, but never put myself out to be like you again, . . until I got to tasting that champagne today. That reminded me of the fun we had, what I needed to feel whole again. I’m not trying to corral you, I don’t need that. But you talk of your friends with benefits, I might just be one. We’re certainly friends, I just may not be the fresh-faced girl you find out there, but we did well tonight. You brought me to places I haven’t been in years. I know I called you by his name, and I’m sorry for that. When you slept with one man for 30 years several times a week you associate certain feelings. . uh . . you know what I mean.”

I nodded as a whirlwind of thoughts and feelings ran through my head. She was one sensual, incredible sex partner. I was contemplating all her words when she kissed my dick again. I startled at the kiss, breaking my reverie.

“Go and pee and bring this back to me. I have to take care of him before I send you home. Don’t worry about me, you’ve more than satisfied me, . . except I want one more taste.” She said in a bright voice that ended with a welcome smile.

“Have you been up?” I asked, she seemed so fresh.

“Just to pee and wash up a little. You were dead, I wore you out.” She giggled like a little girl.

I was still in a daze, I guess, I NEVER thought I could ever let her seduce me from the first time I thought she was flirting, and we had gotten to a point of friendship and I never saw her as a sex partner. I knew she was attractive, but older, AND devoted to the memory of her husband. I never pictured her as the type of good time girl I usually bed down. She tells me she was just what I look for now, a good time, no commitment, no strings, no second thoughts, a chance to let yourself go behind a closed door and not be judged.

I had to pee like crazy and was glad she gave me the chance. Once I stood up the urge came on me fast, I did have some of the effects of being over 55, but I had avoided any of those “dysfunction” problems men get as they age. I worked under the adage “use it or lose it”, and I damn sure used it.

When I came back to the bed she was patting the spot I lay before, on my side, where I fell away earlier. It put my business right before her face and upper torso. She smiled and reached out for me holding my cock in her hand.

“Good, you didn’t pee the steel out of it, did you? I guess that means I still got it. Guys like blowjobs, and I like giving them. They make me feel sexy, powerful. If I ever want you again, or you ever want me, this will be what we’ll remember to fuel the want.”

She opened her mouth and took me deep once or twice before moving her mouth over me taking 2 or 3 inches in and out with her eyes closed as her fingers held my balls. Her tongue was talented and it kept the pressure most girls use their first two fingers and thumb for. She was stroking it from inside her mouth as she sucked. She was a pro at this and what she said was apparent, she liked giving head.

I began to sigh and moan a bit as she began to get me fast. I reached to stroke her hair and touch her cheek and she opened her eyes to me with a smile of appreciation, I guess. Watching her was all I needed to get my end in motion. I felt my breath catch a couple times and involuntarily begin to move my hips to her mouth. Her eyes closed shut tightly and she hummed a sigh of anticipation as my cum oozed into her mouth. I felt like my second load in 6 hours or so was thick and copious, I know it didn’t shoot into her mouth, but the teasing and mouth stroking kept the good feelings going until I got a little numb, where I normally became over sensitive. As I began to soften she gave it up, licked her lips and swallowed, and kissed my thigh before rolling to her back.

“It was fun, we may have to do it again some time. Don’t let this affect our friend ship. You made a lonely woman very happy tonight, I hope you’re happy too. Be quiet going home so other neighbors don’t notice.” She said sitting up and puckering for a goodbye kiss.

I kissed her, got dressed as she stretched out on the bed and covered herself. I let myself out and walked quietly home to lay in bed and evaluate the last few hours. That didn’t last long, I was truly all fucked out.

Wednesday morning, I was up early, it was my laundry and shopping day and usually played nine holes at Anclote Keys, a newer course near Holiday. Their back nine was nearly finished with 10 starting across a canal, the bridge nearly done. Their nine proved challenging enough for a few guys I knew to play an afternoon away. It wasn’t well known enough yet to make getting in on short notice a problem. Their clubhouse and bar were getting to be a good spot for meeting up. But, all morning long as I puttered and did laundry before I hit the grocery store, I half-expected to see Emmy on my porch either embarrassed and apologetic, or mad as hell. I never saw her, I just noticed her golf cart gone, opting not to walk to her afternoon social meeting

Once we finished our nine and showered at Anclote Keys the four of us were having drinks at the bar checking out that days après golf scene when I got a tap on the shoulder. It was Marlene.

“I didn’t know you came here, this is my first time, I just heard about it.” She bubbled, clearly glad to see me.

We chatted for a few minutes and she was about to rejoin her girlfriends when she leaned in to me to say, “Why don’t you stop by later, I have nothing planned.”

I nodded and was happy I didn’t have to work at it that night. I certainly was not “in need” and was probably going right home otherwise. My friends and I shared drinks and happy hour foods until about 8:30 when Marlene caught my eye and she waved to me with a smile and a wink.

I gave it about 10 minutes and I bid adieu to my friends and agreed to meet for 18 holes at Eagle Crest on Sunday. When I got to Marlene’s she answered the door in just a tee shirt and a smile. She took me by the hand and we went to her sofa where we talked and began to flirt and neck. She ended up taking the upper hand, undressing me and then screwing me on the edge of the sofa and floor. It wasn’t even 11:00 when she was laying on me and whispered, “you don’t mind my throwing you out, do you? I’m flying out early to my Mom’s in Atlanta for a week.”

I didn’t mind at all, I hadn’t planned on spending the night, Thursday I usually hit the driving range with Emmy and then meet an old work buddy at a local watering hole that had buy one, get one fajita dinners and always drew a large crowd and a sometimes a chance to meet women. After a few nights of whoring around I was sure Thursday was to be a quiet night. What really began to eat at me, once again, was how Emmy and I would get on after our sexual episode. I truly didn’t want to fuck up our friendship and she had to know that the sex was all her idea.

If I used any good judgement and willpower with Emmy that night I would have just left her in her sexual lurch, horny and alone. She may have thanked me in the morning, OR she may have rebuked me in the morning for tossing her aside like she was used up or undesirable, OR blamed me for the whole thing. I did know that on Wednesdays it was normal for me not to see her at all, she also doing laundry and then attending “Book Club” in the clubhouse. It was one social thing she did in the park and amounted to a coffee and tea bull and gossip session after discussing that week’s book.

Thursday morning, I decided to continue as I had, as if nothing happened between us. I had contemplated calling her the morning after and scuttled the idea as sophomoric. I was up and around at 8 o’clock, as usual, got my paper and made coffee. I had the last half of Wednesdays bacon and egg sandwich to heat up and at 8:45 I was showered and stretching for the driving range. I looked out at 9 and saw Emmy had put her bag on the front step as normal, so I took my bag and walked over, placing both our bags on the back of the cart and she came out all smiles, as usual.

“Good morning Jake, you didn’t get in too late last night. I was just locking up and saw your car pull in. Did you play your 9 at that Anclote Keys again?” She asked.

“You should try it sometime.” I said nodding.

“When they have 18 open we’ll go instead of here. You know the paper said you can play 15 through 18 now. You have to start on 15 and then play 5 through 9.” She noted.

“Only if you have a cart, and they only have 15 to rent right now. They’ll have 20 more next week.” I updated her.

The rest of our ride was small talk and I waited for an uncomfortable moment to come up, but it never did. If anyone ever suspected that we had any sort of affair, they wouldn’t have gotten any evidence from our talk, actions, or demeanor. We hit our usual two buckets, her correcting my little flaws as she saw them, and then went down to the putting greens and played to a draw, each two putting each practice hole . . . again. We originally agreed to a dollar per stroke, but after 10 of these sessions, we were even.

When we got back she parked the cart and paused a moment where I thought we would talk about “IT”, but she simply said, “Be ready for rain tomorrow. I doubt we’ll really get it, but it’s in the forecast.”

I took her bag from the back of the cart, despite her objections, (“Please, I can get that!”) and set it inside her porch. She thanked me and smiled as I took my own bag off and went to my place.

I had barely gotten home and ready to shower when the phone rang and seeing it was Emmys number I answered. Knowing it was her, I simply said, “Yeeeessss?” and heard her nervously reply:

“Don’t think for a minute that I don’t remember us fucking the daylights out of each other, or that I regret a single second of anything we did. It will always be one of the most sexually gratifying nights of my life. It made me feel like life had begun again for me, even more so than the golfing or our friendship has. It may never happen again between us, but I want you to know how wonderful you made me feel. Please don’t make our affections public in any manner, it’s not that I’m ashamed of you or that you should be ashamed of me. It’s just the way I want it. Whether it happens again will be my decision and don’t think that’s unfair. I still love my Robert and you made me feel as close to him again as I could ever imagine. You are a real special friend and I think you get me, where many others here don’t. You’re a great guy Jake, don’t ever change and don’t let any woman ever hurt you.”

Before I could respond, she hung up.

It was not a declaration of love, (which I feared) it wasn’t a promise, it was a sincere thank you and assurance that there should be no worries or wonderment about where we were, who we were. I knew by the way she had called me his name that night, or at least cried out his name, that she was channeling him. I wondered if she recalled when I uttered she was “so tight” that she said, “like my ass, Rob?”. Those four words had served as a fantasy since I heard them. I would love to fuck that beautiful ass, and apparently, she was familiar with the act and I could not imagine any man who was familiar with her, married to her, not wanting to sample that inviting tight little hole between her sweet cheeks.

I decided to let it be and not pursue her words or try to figure anything else from her little declaration. I smiled the rest of the day. She acknowledged that I had rung her bell, but she also knew she had done the same for me. They were both important to her and that made her one notch above the other “friends with benefits” I was seeing. Sure, they all wanted to get my money shot, but they were all in it for their own satisfaction, first and foremost. I was happy Emmy was so cool about it, and it was probably the reason Robert was attracted to her in the first place, and he clearly knew what kind of girl she was. She stopped her loose ways once she met him and devoted her life to him, a lucky man indeed.

Not long after Emmys acknowledgement Stacy called me from the pool saying she was going home around 4 o’clock, if I wanted to stop by, and she would make me dinner. I was excited at first but after some flirty talk, I reconsidered.

“You know what Stacy, I just looked at my calendar and I have to be somewhere at 5:30.” (It really wasn’t a lie, they were drawing teams for a Texas Scramble at the park, but no one really knew me and I would be among the last picked anyway)

“Are you SURE?” She said, “I’ve been thinking about you all afternoon.” She teased.

“Stacy, you know I would be there if I could, we always have a good time, and I love everything you cook and serve up.”

“Well, it will be hot and juicy if you change your mind. Raincheck?”

“Without doubt.” I assured her.

Although I wasn’t with Emmy at that moment I felt obligated to sit and ponder the night we spent together, just as I knew she was doing at the moment. Although we shared no commitment to each other, I felt I owed her that, even though she would never be aware of it. It was a special moment between two friends, and one especially trying to mend a long-broken heart. I imagined her trying to explain to his memory of the joy she felt in the feeling of his spirit being close as she enjoyed what she missed most from him after all those 4 years. Maybe the reverie I felt from her phone call was corny and sappy, but I felt better respecting my friends’ thoughts and words.

Over the next few months I seemed to fall into a strict regimen of life that I had only dreamed of in my working days. It was golf four days a week, driving range twice, and one full day of working to keep my home clean and up to date with the menial tasks of life, laundry, grocery shopping, and fulfilling commitments to my home, my investment. I was seeing 5 different women on occasion, Sonya, who would call and drop by every couple of weeks, Stacy, who would always be available on her day off from her nursing job, or on a hot morning when she would visit the pool, Marlene, who despite denials that she was “that kind of a girl”, made booty calls usually after 10 and either stop over or invite me to her place, MaryJo, a waitress at Snappers (local bar) who flirted her way into my life. She too would call when she wanted me, and Penty, a foreign newswoman I met while she was covering a local tournament that featured a native of Mumbai (her home) who was somewhat of a National hero there. She was an insatiable hornball who could not seek out her pleasures freely in her home country. She had hooked on with local Florida TV after rumors of her “permissiveness with men” reached home and her network called her back, but she refused and since was becoming an American citizen. She said she feared jail and prosecution for liking sex. (I still hope she was exaggerating). She was the weekend sports anchor and did sports support stories. Anything to do with golf and she called me as “her expert” and we got the sheets sweaty a few of the times I helped her reports. (she was drop dead gorgeous, a beauty queen there)

Golfing, getting laid, living the good retired life, and I was one of the youngest, if not THE youngest at the over 55 community known as Wyndtree at Thousand Oaks, basically right on Thousand Oaks Golf Club, a course I had seen on TV many, many times. With little variance Emmy and I hit balls and putted on Monday and Thursday, shot 18 at Thousand Oaks Tuesday and Friday. I had golfing buddies who I usually met on Saturdays and Sundays at different local courses for 9, 18, or sometimes 27 holes if it weren’t too hot.

My regimen of life became almost set in stone for 9, maybe 10 months, and I was happy in middle January, just over a year since I moved in. Emmy and I had just finished our two buckets of balls, and putting the practice greens. She pulled her cart into her charging slot next to her porch and stepped out waiting for me to take her clubs and set them inside her porch, as always. She smiled and said, “Thank You Sir!”, as always. I usually said “My pleasure Ma’am” or “My honor Ms. M”, a name I called her if there were more than a few watching us tee off (some were shocked to see a woman on the men’s tees).

This day she paused as I turned to walk home with my clubs. She looked in my eyes and said, “I hope you don’t have a date or plans later, I plan to have a hot shower later and I would love the company. 8 o’clock sharp, the door will be open, lock it behind you.”

She slipped inside the porch door, I heard her click-lock it and went through the main front door, and heard her lock that, leaving me dumbfounded. Was I to assume this was the “re-match” she said would likely never happen? . . was this a test to see if I were interested? . . . what was this?

As I walked across the road home questioning her intentions 2 things were going on, I was repainting the picture of her well-preserved body, I was thickening in my pants remembering her sexual skills.

I knew her well enough to know that if I called and confronted her with any of these questions she would pull the invite from the table and never, ever ask me again. Since our first intimate encounter and the admissions she made in her odd “Don’t think for a minute that I don’t remember us fucking the daylights out of each other” phone admission she made without facing me, I had come to one theory or realization, once she was naked and alone with me it was as if she were in another dimension, one where the rest of the outside world or reality did not matter, as best as I could guess.

There was a rare threat of storm that evening and the wind had already started and before I could call either of my golf mates, I got a text from one who said the other had cancelled and maybe we should put off until a better day. So, I was free for the evening and even as much as my last intimate episode with Emmy left me questioning so many aspects of it, the sex was incredible.

I had dinner and wanted to nap but falling asleep was impossible with so much anticipation in my head. My stomach was doing flip-flops wondering what the “shower” might involve and if this might change our relationship. She had showed no signs of wanting to deepen our friendship or get involved. She was, in every sense, just one of my golf mates who did receive some extra consideration because she was a woman, i.e.: holding doors, ladies first, etc.

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