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 4

Fiction Sex Story: Chapter 4 - 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  

We kept the conversation light and got our shopping in at the Publiks and we drove across the street to the Wynn-Dixie to get the weekend specials. She let me go my own way as she had certain things she wanted. When we met up she had a bottle of champagne and a blue paper wrapped seafood purchase.

“What are you planning on celebrating?” I said with a chuckle, “Your new car when you get it?”

Suddenly she seemed to turn sullen and quiet and moved close to me like she was going to tell me a secret or something and said, “I was hoping you didn’t have any plans tonight and would come over for a Champagne and shrimp dinner.”

She didn’t look directly at me and avoided steady eye contact in a fit of nervousness or embarrassment.

I immediately got the connotation that another intimate night was at hand and stupidly said, “You don’t have to do anything because I helped you out today.”

Her face turned red and she walked to a close by cooler and dropped the blue package and champagne bottle into it and stormed out of the store.

I was dumbfounded, not knowing what I said to make her do this. I took my hand basket with just 5 items in it, added her two and went to the express check-out and went out to the car where she was standing.

Before I could ask her what happened she turned an lit into me.

“If you think I’m the kind of WHORE that gets men to do things for her for a fuck and blowjob you are sadly mistaken. That dinner and evening I asked you to was well planned long before my car died and you helped me out. I’m an independent woman who doesn’t need your help and isn’t about to trade her body for it. Give me my bags from the trunk and I’ll call a cab to get me home.”

“Emmy, I meant nothing of the sort in my remark to you. I know that isn’t you and if you think for a minute I don’t respect you, and that I don’t hold our special moments together as times I cherish, you are wrong. I just wanted you to know that you didn’t need to do anything to “pay back” my kindness. I love making you happy, seeing you smile. I never thought you were offering yourself as a payback. I love you too much to ever hurt you.”

“What do you mean, you love me?” She spat back.

“Emmy, I hold you in high esteem in my heart of hearts, you are truly a special woman and friend. You say I brag about my friends with benefits, you are NOT one of those women. I don’t love you in a relationship sort of way, but you’re so special to me. I would never hurt you.”

“OK, then I’m sorry I misunderstood your meaning.” She said cutely, “Let me go in and get my things I left.”

I handed her the bag with her two items that I picked out of the case and paid for.

“You didn’t have to do that.” She said reaching for her purse, “Let me pay you.”

“You don’t need to, it’s my cost of hurting your feelings.” I insisted.

“I won’t have it” she said as she pushed 2 twenties in my shirt pocket.

The ride home was smooth until we came upon a traffic jam of sorts, a modular home piece was being backed onto a lot and traffic was held shut for a few minutes. We said nothing as we watched when she blurted out, “Could you? Could you love me in a relationship sort of way? Am I the type of woman who could tie a man down?” She asked.

“So, you don’t mean me specifically, do I think any man could fall in love with you? I’m sure one could. You’re special in so many ways.”

“Thank you.” She said softly. “Aaaaaaaa . . . . . Are you going to come over for that champagne and shrimp dinner?”

I looked to her and she winked in a devilish grin, and then put her tongue out just slightly, licking just the edge of her upper lip.

“I’ll come.” I said and she shyly said, looking away, “You sure will.”

Once home I wondered if she had become enamored with me and wanted me for “her man”. I hadn’t really been anyone’s “boyfriend” for a long time. There were girls, or women if you prefer, that I stayed with exclusively for weeks or months at a time, but love was never mentioned in a permanent sort of way. We were convenient to each other, had great sex, were great companions, but when any thought of permanence came up, our incompatibility flaws glared. Plus, I wondered about my wandering eyes, I loved women, I liked the chase, but I also liked being chased and women 10 to 30 years younger than me found me attractive and sexy, and it isn’t like I did things to enhance myself. I was always confident, and was always told I had bedroom eyes. There were few women that I “wanted” that I didn’t get. When I didn’t, there was no pouting, no going to extremes to get my way, there were always too many others to choose from.

I put groceries away and folded clothes and worked about my home until I sat in my recliner and fell asleep for what I thought was a nod, and ended up being a couple hours and then was only awakened by the flatbed delivering a loaner and picking up Emmy’s car. Even on the back of a flatbed car carrier, her Cimarron was a stunning car, over 30 years old and looking fresh from the showroom. It struck me that she took as good care of herself as she did the car.

At 6 o’clock I dialed her number to ask, “What time do you want me?”

There was a long pause and she said in a low voice, “All the time.”

“Excuse me, I didn’t hear you.” I said although I did, clearly, but she repeated “Any time.”

I showered quickly and dressed in Florida clothes, a nice Tee and light shorts, commando underneath, and went over and knocked. She came out quickly and let me in and showed me to a little alcove built in the side of the unit, big enough for a high cafe table and two bar chairs.

“I got cold Land Shark Beer, or I can make you a mixed drink, soda, anything. I’m drinking the Land Shark.”

“So, I’ll have that too.” I said as she came from the kitchen with a bucket of beers and a bowl of chips with a light dip insert.

We chatted about her car and a couple things about our golf games as we nibbled the chips. Her outfit was one piece and made for cool comfort as well as accenting her tight body as I kept looking her over, being excited about unwrapping that package.

“Let me speak for a couple minutes, I have a few things to say, points to make, and things to get out in the open. Let me finish before you comment, OK?” She said nervously.

I sat back and took a long hit on my beer and nodded to her, “Please.”

“I hardly know where to start, but here goes. Before I met Robert I was just the kind of girl you always seek out and I put myself in the position TO BE sought out, . . . . for a good time. I slept with a lot of guys, some regularly, others once or twice for a good time. I liked sex, enjoyed being pursued, enjoyed the teasing, and it was all to be popular, and have a good time. My girlfriends used to kid, it was all about the O . . . getting off, . . . . feeling free, . . . . . feeling powerful as a woman who had something men wanted. I never thought of myself as a whore or slut, until I met Robert. He was so special. Before I invited you here, he was the last man I had any kind of sex with. After sex episodes with him I didn’t feel the need to look for my underwear and get a ride home, or ask him to lock the door as he left. He was the one and I knew it. I’ve cried all night in his arms realizing what a slut I was before him. I regretted every time I slept with someone for the sake of the O . . . getting off, . . . . feeling free, . . . . . feeling powerful as a woman who had something men wanted. He comforted me and I realized he was different. We fell in love in a few hours. We were married in about 3 months. That first night with you I channeled Robert in my stupor, and I WAS in a stupor. I thought he was here, I even called you his name. I had a terrific nightmare some weeks after that and recalled some of the hot nights we had, and we had lots of them. I wanted to be taken like he took me, treated like he treated me, like I had you do that second night. Being your whore that night was about the best I ever had, and you were so tender, like Robert was, AND you stayed with me, tended to me and were like Robert. You treated me like you loved me, and I KNOW you don’t treat your so called “friends with benefits” like that. You roll off and leave them. I KNOW I’m special to you, and maybe that’s just because of our friendship. But, I’ve come to think it’s something else, and I think you suspect it too.”

She looked at me as if trying to make me say something I felt was obvious, but I wasn’t quite sure what to say.

“Is your silence trying to tell me I’ve got it all wrong? You don’t feel for me any different than any of your sex partners?” She asked like she was about to cry.

“No, Emmy, don’t think that for a second. You are so special, such a friend, and such a tender and complete lover. You’ve willingly offered me all of you and I’ve accepted and looked forward to the next time. That anticipation is because of my feelings for you, I’m sure.”

“Jake, your next time is here, today, but you need to know something. I no longer think of Robert when I dream of sex or when I pleasure myself, and that’s become pretty often. My thoughts are of you. I’m not saying I’m falling in love with you, but I think it could happen, if I let it. Seeing you parade women to your home, or seeing you come home at all hours of the night tells me to keep my distance. If I give you my heart, that can’t be. When I’m ready to do that, I’ll tell you, and I think you feel the same way about me. I see the caution in your actions, but because we’ve compartmentalized the friend Emmy, and then the sex Emmy, it’s been easy for you to ignore. So, I’ve spoken my peace, brought things out into the open for you. I know I’ve been a mystery to you, I hope this solves a bit of it.”

I sat back and finished my beer as she stood saying, “I’ll bring out the first course, those huge shrimps and the bubbly that goes with them.”

She cleared the cafe table and returned with a lovely silver plate with 10 of the biggest shrimps I’ve ever seen, and champagne under her arm. She handed me the bottle and the towel over her arm and turned to the window ledge for 2 wine flutes she had waiting. I popped the cork and poured and we each drank a toast and dug into the shrimp. As we took each our fifth and last prawn I asked, “That was a marvelous and filling treat. What’s the second course?”

“YOU are mine, and I hope I’m yours.” She said as she stood and came to me as I swiveled towards her.

She kissed me hard on the lips and our tongues met and played for a moment before she stepped back and knelt in front of me. She ran her hands up the sides of my legs and under my little shorts. They glided up and over the tops of my thighs to my cock. One of her hands came out and went through the leg hole to cup my balls.

“I dream of sucking this, running my mouth over the velvet head, feeling it surge in my mouth, for me, because of me. Then putting each of those balls in my mouth, knowing that the juice in your little sack is going up and out and into my tummy. So nice to suck, lick, and kiss all of you down here because you have it so neat. Do you trim it, or do you have one of your girlfriends do it for you?”

“Depends” I said as moved her hands out and to the waistband to pull them off as I lifted a bit. She put a hand under my balls and let them rest on the edge of the seat while she smiled at my junk before her.

“I would shave and keep this cleaned up for my own pleasure, . . how often? Every 10 days?” She asked as I nervously nodded, my erection standing up, turgid and waiting.

“Knowing I could give you a shave and big blowjob every 10 days would make me happy, if you were mine alone, but that’s a thought for later.” She said before her mouth went over me and sucked back up to the tip.

Her eyes went wide and looked up to me as she unzipped her outfit all the way, right to her belly button. She bent forward a bit and began a no hands mouth fucking. Her mouth was magic as both of her hands parted the top of her outfit to let her tits show before they went under my balls to lightly run them through her fingers. As she had done before, in a couple minutes she had me ready to spout. Once she knew it was cumming she knelt up straighter and moved her hands to the top of my thighs and she was going straight up and down on me and then I groaned and wailed as I shot for her and she ate it all hungrily and continued sucking every drop before she felt my over sensitive discomfort. She backed off me and smiled, licking her lips.

“That was awesome for me, and I believe I judge it was for you.” She said kneeling back on her legs and taking her arms from her outfit, her perfect breasts coming out and her hands shooting to pinch the nipples, causing her to sigh and roll her eyes.

“Will you bring me to my bed and eat me, fuck me, and then spank your bad girl?”

She said as she began to stand.

I went to my feet and picked her up in my arms causing her to whoop as she put her arms around my neck and kiss me as we walked.

“Why would I spank you? You’re not a bad girl.” I said playfully.

“I have a little toy in my asshole.” She admitted with a pouty lip.

“How can I eat your cute little asshole if there is a toy in there? You ARE a bad girl.” I said as she shrieked with glee as I set her down.

I pulled her clothes the rest of the way down and off and knelt on the floor, pulling her down to get her pussy to my mouth I ate her with the same fervor she did me and once her orgasms started I had to hold her down as she lifted her torso from the bed trying to get more in my mouth. It was then I became aware of the anal toy. I stopped eating her and tipped her up to see the little knob sticking out. I took it in my teeth and pulled. It was 3 beads, then one large bulb and then 3 little beads. She gulped when the fat bead came out and growled when it all came from her. Her little hole was dilated and I stuck my tongue to it causing her to clench and lose her breath for a second.

I played that little hole with my tongue and the small end of her little toy. She got to a point where she couldn’t handle the tickle and rush anymore and pulled away from me, laying back on the bed, spread eagle.

“Fuck me till I can’t breathe, then let me flip over. Spank my ass red and fuck my ass again, you made me crazy before.” She asked in an ordering tone, but I was happy to accommodate her.

While riding hard on top of her she took her hands away from pinching and holding her nipples to grab my arms at the bicep and pull me close.

“Jake, I love you and your big delicious cock, why can’t you save it all for me?” She said meeting me eye to eye.

“I thought we weren’t that way.” I whispered back.

“I dare you to deny you love me in some way beyond friends.” She said her eyebrows set low, showing me, she really meant it.

I smiled to her and braced my feet and rammed her hard for 15 or more strokes causing her to cry out in orgasm before I pulled out and flipped over and filled her pussy. Before I forcefully pounded her a few more times I rained down 5 hard slaps on each side of her incredible ass. She hissed and strained her head up as my hand set her ass on fire and I stayed pressed hard to the hilt in her as she whispered “yes, yes, yes,” to the burn of her behind. When I pulled out from her and she put her head down and shoulders flat to the bed. She knew I was about to violate in her little hole.

Our last time she took me and pushed back to take it all in one stroke, that clears all the entry pain at once. Her challenge that I couldn’t “deny you love me in some way beyond friends” was going to cost her, and only because she was right.

I wiggled the head of my cock at the little hole she already lubed for her toy. It didn’t open up and she began to reach back, but I slapped her hand away. I placed the head right back on her wrinkle and pushed down with my thumb, just behind the plum of my tip. It broke the surface and went in to her with a howl as she tried to push back, but I let it pop out again. I repeated the process and she stayed still this time and I slowly began to push up into her as she grunted and hissed at my rude insertion.

Before I started fucking her butthole I wanted to make some points clear.

“Do I love you?, of course I feel a deep affection, love, for you.”

(Pause to let the words sink in)

“Do you think I treat the rest of my fucks like this, with patience and passion? No way, just like you called it before, I fuck them and go home or send them home.”

(Pause to let the words sink in)

“Don’t think you sought me out and roped me in, I LET you worm your way into me.”

(Pause to let the words sink in)

“Don’t think you’re so fucking irresistible either, you were such a cunt when I first got here I would have moved if I could have worked it out. I had enough of your horseshit, name calling and insults early on, and fact is, you wanted me then and couldn’t admit it to yourself. Don’t think I’m going to put up with any of that shit if we decide to become exclusive. If you think your 3 holes alone are going to keep me, remember, all women have those holes, there has to be something else, like mutual respect and trust for each other, patience and affection. Sex binds all the other things together, none of them can hold a relationship together by itself.”

(Pause to let the words sink in)

“If we are on the same page with all of that, I’m willing to give this all a go, or should I stop right here and we just go on as we have, without the sex?”

I could tell she was crying what I hoped were happy tears, and I wasn’t sure if it was because she was going to have to tell me she couldn’t continue with me, fully trust me, or if she was just relieved her loneliness was over.

She cleared her throat and whispered through her tears. “Please fuck my ass, make love to my ass and shoot your stuff up into me, and stay tonight. I’ll work at everything to have you for mine.”

Resolutely I railed her ass while she cried and came, loving being my dirty girl. After I shot in her I repeated as I did before, I held her until cramps began to bother her, then picked her up and carried her to the bathroom, then cuddled and fell asleep with her until morning, but not pre-dawn so I could get out unseen, we slept until 9 o’clock.

I had heard her get up once in the night and the one time I got up to pee she rolled to me when I came back to the bed, she placed an arm over me. It all felt very affectionate, and really quite different for me.

When I woke I saw the clock in the hallway read 9 and I just laid there with my eyes open, gathering thoughts.

After a few minutes she said, “you’re thinking, . . . . . .any regrets?”

“Just hurting you, hearing you cry.”

“You didn’t “hurt” me. Good Lord it was so intense, and they were tears of joy.”

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