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Love Older Ladies

Category: Mature
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I was smiling as I looked down at this beautiful thirty five year old creamy smooth ass. I was enjoying this nice tight pussy doggie style. Watching my cock going in and out of it was very exciting. This was my first older lady and it was great. Not bad for an eighteen year old guy. Besides Mrs. Black was one of the most beautiful ladies in our town.

I had been dating her daughter Sherry for about three weeks when Sherry had a party at her house. There were maybe ten couples all class mates at the party. The Black’s have a large home and the party was held in the basement play room. There was some heavy necking and my buddy Arty and his girlfriend Rose did get pretty wild in the laundry room. But other than that it was mostly harmless fun.

The next day I stopped by to see Sherry and only Mrs. Black was home. She invited me in and we started talking about the party. She had some how found out about Arty and Rose and she wanted to ask me about it. Before we got into that and it was only oral sex any way I thought I should set her mind at ease about how I felt about Sherry.

I said “Mrs. Black I want you to know that I would never do anything that would hurt Sherry in any way. I know a lot of kids our age are experimenting with sex but I would not do that because of my size. So many girls my age are virgins and I just don’t want to hurt anyone that has not already had sex.” I did not elaborate any further and I thought that was going to be the end of it. But what I did not know was that Mrs. Black had not had sex in many years. Not since her husband was lost at sea.

She got a funny look in her eye and insisted I explain my statement. So I told her that my size was much larger than most boys and many men as well. I told her my Dad had told me to be careful about whom I had sex with or I might hurt the girl. I again felt that was enough said but she again wanted to know more details. So I said “Mrs. Black since you are an older lady and a mother I guess it would be alright if I showed you what I am talking about. I mean you have seen a man’s penis before so looking at my penis would be no big deal.”

She got bug eyed and in a weird voice she said “Yes by all means show me what you are talking about.” I asked if Sherry was due back any time soon and she said “No she would not be back till late afternoon.” So I stood up and came around the table so she could see real good and opened my jeans.

Dropping them to my knees all I heard was a gasp and “Oh my God.” I had seen that look before and knew she was shocked by the sight of my cock. It hangs limply down for six inches and as soon as I saw her looking at it, it started to grow and grow till it stood attention in all its glory.

She was still making sounds but no words were coming from her mouth. I moved closer and said “You can touch it if you want.”

I did not have to ask her twice her hands flew up and took a choke hold on it with a good four inches still beyond her two hands grip. This had happened before and I knew what was going to happen next so I said “You can suck on the head if you want.”

She never looked up into my face but she took as much of it in her mouth as she could. She sucked and worked her mouth on my cock like a professional, but maybe she was. How do I know what she did before? I was getting very worked up and my balls were beginning to tighten up but I did not want to cum yet so I said “Would you like for me to put my cock in your pussy. Would you like it doggie style? I like it that way.”

Well one thing lead to another and before I knew it there I was watching my cock going in to her pussy doggie style. All she could say was “Oh, Oh my God and Oh God.” Then she screamed she was coming and when she did she fell forward her arms folding under her. She passed out. I followed her forward as I was not done yet. I did not care if she was passed out or not I was going to keep going till I cum.

She was half on her side with her right leg pulled up out of the way as I had my knees on either side of her left leg my cock was still deeply embedded in her pussy. I pulled back and saw that my cock was covered with a thick creamy foamy. As I looked at the stuff my eyes wandered to her pink little ass hole. I had never had my cock in an ass but I had heard it was a lot of fun to fuck a girl in the ass so I pulled free of her tight pussy. Took my cock in hand and pointed it at her ass hole. After applying some pressure the head slipped out of sight. It was very tight and I was worried about hurting her so I just went in a few inches. But it sure felt good. I was getting excited and was about to cum when she murmured sleepily “Oh God that feels so good; fuck me Quincy, put it all in.” So I pushed and before long I had all my cock up her sweet ass and that is where I dumped my load. She never fully woke up before I left.

A few days later I saw Mrs. Black at the Market where I work part time. She smiled at me and said “Quincy would you carry my bags out to the car for me.”

My boss nodded at me so I picked up her bags and headed out to her car. I sat the bags in the back seat and when I turned around she handed me a ten dollar bill and a note. She drove off without a word. The note read “Tonight at ten, my home, Sherry is a way. I need you. Please come.” I smiled and planed on being there at ten.

At ten to ten I stood and told my Dad I was going out. He did not have to ask why I was going out at this time of night. He said “Well be easy on her son and don’t get her pregnant. Use something or make her swallow it. No chance of a baby that way.” I know he really wanted to know who I was going to see but I was not about to tell and he was not going to ask.

The Black home is only a few blocks away but even at that it is like a whole new world up there on the hill. A much finer class of homes and the check books up here were much fatter than down across the tracks.

No one saw me approach the back door. I knocked and waited as I look through the glass. On the kitchen table sat a whiskey bottle and soda can. That alone told me she was drinking. She came into the kitchen wearing only a silky black robe with symbols and colorful flowers on it. I guess it was supposed to be Chinese or something.

The gown was not closed tight and I could see her long legs and a dark patch between her legs. As she opened the door she hugged the gown around her fine body. She opened the door; I stepped in and slipped an arm around her waist. She sucked in a deep breath as I covered her mouth with my own.

Her fingers found the light switch and all of a sudden the room went dark. I was all over her hands groping her firm smallish tits. I felt the nipples grow hard under my hands. I found the thick bush wet and ready for what ever was about to happen. Her fingers found my jeans zipper and worked their magic. My jeans lay there on the floor a second later. I did not wear any thing under my jeans. Her fingers curled around my cock. I said “Mrs. Black.”

But she cut me off as she told me to call her Eleanor. Then she said “No call me Ely. I would like that.”

I said “Ely baby lets go to the bedroom and see what we can get into too.”

She giggled as I tasted the booze on her lips. She had been drinking for a while before I arrived.

The whole house was dark but we made it to her bedroom and to the bed.

I fell on the bed and lay on my back. She was at my side but resting up on an elbow. The room was dark but there was enough light coming in from the security light to see she was looking at my cock. Her hand was sliding up and down my cock but not jerking the skin. She was just feeling it and measuring it.

She said “Quincy in all my life I never had anyone long enough to touch bottom in me but I think you can. My husband said I had a big cunt and that is why he always wanted to fuck me in the ass after Sherry was born. That is also the reason we never had any more children.” I had wondered why she took my cock up her ass so easily and now I knew.

She was still rubbing my cock and leaning down to take the head in her mouth when she said “Oh my” and fell across my lap Mrs. Black passed out again. This fucking lady had a problem and I was not sure I was the cure for her loneliness. Unsure what to do since my Dad told me once “Never fuck a drunk or one that passes out.” I got up and went out. I headed down town to the drug store for a cup of coffee and to see who was around.

In a booth sipping on a soda as a lady I had worked for last summer. It was the widow Mrs. Verling he husband Dr. Verling died two summers ago and she has been living in that big old house all by her self since. I helped her around the house and mowed her lawn two years ago. But back then I was not into fucking older ladies, but I sure as hell am now.

I stood looking at her in a whole different light than I had before. Mr. Verling is not yet sixty and in my eye she looked pretty darn good. Not too big, not really fat just nice and round. Plus she has a mouth with the prettiest lips they are shaped for kissing or sucking cock I was not sure which. But hopefully I could find out.

She looked up as I stood by her booth. “May I “I said as I slid in the booth across from her.

“Well Hello Quincy. How are you? “Her smile was one that was honest and from the heart.

I did not answer her question. I said “You are looking very lovely tonight. How have you been?”

I think she may have blushed just a bit. “I am fine Quincy. What are you doing this summer?”

I smelled an invitation in the wind and said “Mrs. Verling I was hoping you may have some work for me.”

I think her smile got bigger and there was a sparkle in her eye I had not noticed before. “Quincy, as a matter of fact I do have a few projects I need some one to help me with.” I told her I was in need of work and I would love to help her out. She said there were a few things she could use help with and we talked about then for a few minutes. She finished her soda and I asked her if I could come home with her and see what she had to do. She said it was late but I told her it was Ok and I would be happy to look at what she has. To me that was one of those statements that can be taken two ways and I felt she was fully conscious of my double meaning.

She drove slowly up the hill pulling way to the rear of her drive where we were in the dark. I got out and came around to open her door. She took my hand and stepped from the car. I did not release her hand but held her close in the dark shadows. She did not seem to mind as I slipped an arm around her waist. The thin blouse felt so smooth as I pulled her closer. She tilted her head up, maybe to say something maybe not. I didn’t give her a chance. I covered her mouth with my open mouth. Her lips parted allowing my tongue to enter and taste her. I felt her press into me. I pulled her even closer. With my right hand I held her head so I could kiss her hard. With my left I cupped her plump round ass. I let my fingers dig into her crack through her thin skirt. She stiffened and gasped but did not pull away. Her arms came up and locked around my neck. She opened her mouth and forced her tongue into my mouth.

I forced her back against the side of the car. My cock was hard and it came up between her legs hitting the soft mound just above her cunt. I pushed and she wiggled till we both needed to come up for air. “Oh, Quincy don’t do this I am too old for you.” She said in a deep raspy voice.

I smelled the passion, her breathing was irregular her wavering voice gave her away. She was hot as a fire cracker so I told her to let me be the judge of want I needed and wanted. I told her I wanted her then. I asked her “Can’t you feel how much I need you?” My cock was rubbing her clitoris.

She said “Oh, my yes I feel it.”

I said “Then let me give it too you. Let me make love to you. Let me set you on fire so I can put out the flames with a flood of passion” Where these words were coming from I had no idea. But they seem to hit the mark because a minute later we were in the back door headed up the stairs to her bedroom.

She pulled at my t-shirt and jeans while I found buttons and hooks on her. We stood there naked in the shadows of her bedroom. There was just enough light to see her plump round body really did look pretty darn good.

Kissing her I pushed her back on the bed. I fell a second later with my face coming to rest between her legs. She said “Oh, God Quincy Oh god it has been so long.” I parted her legs wide and pressed the attack. She screamed out load at the first touch of my tongue to her wet pussy. Hooking a finger in the pussy I pulled it wide licking deep inside. I ran my tongue up till it touched her clitoris and I pressed hard wiggling my tongue across it several times before moving back down to lick up her pussy and rub the clitoris again and again. It did not take long before she cried out and stiffened bouncing her hips up and down as she whimpered words known only to her. Then she pushed me away and said “No more, my God no more you’re killing me.” I rested my head on her chubby thigh and waited for her to make the next move.

She did not move for a long time. So I slipped a hand up between her thighs placing a finger tip tight upon her tiny rear orifice. There was plenty of juice that had run down there. I rubbed my finger tip over her ass several times before I pushed one finger tip into her tight ass. I caught her taking in a deep breath but she did not move. I slowly pushed my finger into her until my finger was all the way up her chubby butt. Still no reaction from her that she wanted me to stop. I moved my finger in and out a few times. Still no response except for a sharp increase in her breathing. A moment later I placed two fingers at the point of entry. Two worked in as easy as one. A moment later three fingers seem to make her get very excited all over again. With three fingers embedded in her ass I moved around so my cock was available to her. She was quick to take advantage of this and my cock was as deep in her mouth as my fingers were in her ass. We wiggled and moved around until she was up on her knees bending over my cock, my fingers still working in her ass.

My hips bounced up to meet her mouth on the way down. I tried to keep in rhythm with my fingers but after a while we were going to fast and wild to keep sync. I cried “Oh Fuck” and came filing her mouth with my sperm. She never took her mouth off my cock but she made a sound before she came with my fingers ramming up her ass. I worked my head up between her legs and licked her pussy juice the best I could at this crazy angle. She was an excellent cocksucker and I knew she also was going to be a willing anal sex partner the next time. It was gong to be my cock up her ass next time not my fingers. We slowed down falling over she came loose from me as my hand came free of her. We rested in the dark for a long time. I got up and went into her bathroom to wash up. She followed a minute later.

She came in stepped around me and opened the shower door. She did not say a word as I stepped in with her. The water beat down on us as we just stood there in the dark. I took her in my arms and kissed her. I tasted my own sperm as we traded tongues. I got out first and lay on the bed. She came to lay next me still dripping wet.

The next thing I knew there was a soft glow in the bedroom window. The sun was not up yet but it soon would be. I looked to see her lying on her back one arm above her head sleeping soundly. She looked all together different this morning. She was whiter and smoother than she had looked in the dark. She breasts were plump and round sliding off to the side. Her belly was not flat, but not too large either. Her pussy hair was light and I could see her crack of her pussy gaped open. I had not fucked her last night but I sure as hell wanted to. I may have to wait on that as I had something I needed to do this morning. So I left her sleeping and headed home on foot.

A change of cloths and I was headed for my part time job at the market. Mr. Hooper was a nice old man that had this store for many years. He raised his family and took care of his wife for many years from this old store. He was over weight and wanted to retire but there were no takers for the store. I would have bought it except for my age and the fact I had no money.

Working through lunch I got all the stock up and the store clean and straight. At ten minutes till six he said he had a letter for me. Handing me a sealed envelope he sadly said he was closing the store.

I waited till I was standing next to my old truck to open the envelope. Just then a long dark car pulls up, the window went down and the smiling face of Mrs. Verling appeared. I smiled back and approached her car. “Hi Quincy” she mused. Her voice was soft, her eyes were almost glazed over and I knew she was reliving last night. Leaning in the window I said “Tonight about eight, OK?” She said “Or sooner if you can make it.”

I showered laid on my bed and slipped off into a dream of sex with older ladies. I was surrounded by naked ladies all older wanting to have sex. But after forcing my way passed the mob of bodies. I saw Sherry Black she was standing next to her mother. Her mother was naked and Sherry was pointing at me and at her mother’s bulging belly. I jerked awake and sat up sweating.

Another shower and I joined my Dad in the kitchen. He said, “HI” and said I was not spending much time at home these days.

I knew he was asking a question not making a statement. So I told him about Mrs. Black not all we did or her drinking just that she had been very interested in me and I showered her a good time. He smiled and asked “What about last night?” So I told him that was all together a different lady. But I did not tell him who. He did ask if it was also an older lady and I told him it was. He said to watch out for the older ones sometimes they can get very attached. I promised to be on the look out and to not get too involved.

I parked my truck in he shadows at the back of the house. Walking across the yard I came up on the back porch. The back door was open and Mrs. Verling was on the phone. I was about to knock when I heard her say “He is so strong and virile, it just happened and he is coming over again tonight. Oh, don’t ask again, I will work it into our conversation. But I got the feeling he would l love to have two ladies in one bed. Yes, yes I remember how it was that summer long ago. We did a double then and now that we are both single again we may as well have some fun. But Marge, you have never seen a cock so big of so thick. I could hardly get into my mouth.” She laughed and said “It is a good thing my husband is dead because if I had met him before I would have fucked him any way husband or not.” She hung up and I moved back to wait a few minutes.

I knocked and entered without waiting. She turned to face me letting her gown part reveling her large tits and little pot belly. She had shaved her pussy of the fine veil of hair. It was puffy and looked as if it needed a good fucking. I told her so. She laughed and said I was “so bad” but she came into my arms and did not mind my hand closing over her little mound.

I got excited and said close to her ear as if there might be someone listening. “Mrs. V; you’re one hell of a cocksucker, and you got a fine ass too. But how about we go to bed and I check out this hairless pussy.” She slapped my face softly and blushed as she turned and headed for her bedroom. We entered a near dark room there was a dim light in one corner that gave the room a ghostly gray cast.

She stopped by the bed turning into my arms. We kissed; I cupped a cheek in my hand and took a large soft tit in the other. “Nice fucking tits,” I told her. She said I was so bad talking like that. I laughed and said I knew she liked it and I thought she was turned on by it. She did not deny it she only pulled at my belt.

There were no foreplay, I put her on her back and was between her legs driving my cock to the hilt. She screamed as I pounded her tight pussy.

She came in a flood and I joined her just after ten minutes of fucking. We rested but that was OK because that quickie was only a warm up for the rest of the night.

A few minutes later I was on my back and she was playing with my cock. She was just pulling it up and down slowly. “It is so big” she said.

“Not too big for your fine plump ass.” I said. Then I said “May I call you Regina I know that is your name.

“Oh, Quincy; please do. I would like that.” She answered.

“Well Regina would you like to suck on that young cock for a few minutes or are you ready for a royal ass fucking?” I asked.

“Wow what a great cocksucker you are. Don’t make me cum again I want to take it slow and enjoy this delightful cocksucking.” I said in a low husky voice.

She was good she was very good and I would have loved to fill her mouth with a load but my thoughts were about an ass that took three fingers up it.

She got up on all fours. Her ass was plump round and soft. There were little dimples in the cheeks and the back of her legs showed the years of eating well. But I thought it was a beautiful ass as I applied the K-Y jelly.

Thank God we were on the second floor and this old house was built well or the neighbors would have called the cops. She screamed and raved and cause me to slow down. But she only yelled louder for me to “Fuck My Ass” What a great lady she was out side the bedroom. But what a great fucking whore she was in the bedroom. I wondered what had killed her husband.

After a shower she sucked me hard and we danced this time with me between her legs. Again she came quickly and I followed her lead.

An hour and a half after I had arrived we were in the kitchen having a drink. I had a beer and she a mixed drink. We were naked and the only light was a bright glow from the security light. It made strange shadows as we moved around the room. She stopped to look out the rear window. I was close behind her my cock limp but pressed to her chubby ass.

“Quincy I have a friend near my age who is also a widow and she is in need of some sexual attention.

How would you feel about me inviting her over the next time you stop by? Do you think you might enjoy two old ladies?” I did not answer right away making her think I was thinking it over. In my head I was yelling”Yes, yes, yes”

I said “My love I think that might be very nice. I am sure we could all be well entertained if she is as sexy as you are. It would be fun to have one of you sucked my cock while I licked the others pussy. What do you think of that idea?”

She laughed and said “I knew you were just the perfect man for the job.” Regina waited for a few seconds before going on. “Quincy Please don’t get mad at me but I have enjoyed you so much I want to give you a reward for a job well done. How can pay you for all the wonderful pleasure you have given me?”

I had never thought of being paid for my services because to me I was getting the best part of the deal. If any thing was owed it was I that owed this ladies. Hell how many guys my age got sucked and fucked so very well with no serious attachments. I was thinking of Mrs. Black as I said

“Really are you sure you want to do this. I don’ want to make it feel as if I am getting paid for having the best sex in town.”

“Don’t think of it as being paid for sex, please. No don’t think of it as that. I want you to think of me as maybe paying you a little extra for the chores I want you to do around here.” It seemed to me she was upset and maybe afraid I would not want to come by any more if she offended me.

So jokingly I hugged her and said “Well, OK if that is the case I need a new truck? But first I better work on some more chores.” Reaching around I took a soft tit in each hand and asked. “You do enjoy me talking sexy to you don’t you? I get a kick out of talking to you kind of dirty. From what I have seen I think it turns you on too. So be sure to tell your friend I am kind of crude in my speech.”

Turning in my arms as she felt my cock come alive again. She said “Why you big dick fucker what the fuck do you mean talking dirty to me. Can’t you see I am a real ass fucked, cocksucking lady that can not get enough of your raw young cock.” She said laughing so hard she could almost not get the words out.

“Well that answers my question.” I laughed along with her. After wiping away the tears I asked “What is your friend’s name?”

Regina sobered up and looked at me smiling and said “Marge. She is two years younger than me. She is slim, busty and pretty as they come.”

”How do you know her and how do you know she wants to join us for fun and games?” I asked.

“I have known Margaret for many years since we went to college together. We are still good friends and we have shard each other grief when our husbands died. Plus we do talk about things. “She kind of shied off and I pointed a finger at her. She blushed and went on. “Well we have talked about having sex at our age. We have even touched one another.”

I laughed out loud and cried you “You to had a lesbian things a few times is that it? God I do want to see that. Where does she live I do want to meet her.”

Regina giggled saying she lived only a few houses down. I said to call her and invite her up or drinks. Regina said it was late and I reminded her there was no time like the present to have fun.

We were in the kitchen when Marge arrived at the back door. She was wrapped up in a cotton robe over a nightgown. As predicted she was pretty and very sexy I thought even for someone we got out of bed. She smiled as I held out my hand. Regina was introducing us as I pulled her to me and said “Marge you’re lovely. I am so happy to meet Regina’s dearest friend.”

Regina said “See he is so sweet you’ll love him as I do.” But Marge could not answer as I was kissing her. Coming up for air Regina said “Why don’t we go upstairs have our drinks up in the bedroom.”

The ladies walked together ahead of me. They entered the bedroom laughing holding a drink in one hand and holding each other with the other. I stopped inside the door dropped my shorts and waited for my sweet ladies to see what I had in store for them.

Marge turned around first and said “Oh, my God Regina it is even larger than I would have guessed.”

Regina said “Go touch it feel how hard it is, play with it he loves that and then if you really want to feel the strength of it suck it. Taste his sweetness beside I told him you were a better cocksucker than I am.”

I did not remember anything like that but it was enough to prompt Marge to set aside her drink and walked toward me. Marge magically dropped her robe and nightgown as she moved to me. I was pleased with what I saw and my cock bounced up, down, up, up and up showing its approval as well.

I reached for Marge but she slipped below my arms and ended up on her knees with my cock in her mouth. Regina was right Marge was a better cocksucker than she was. But God knows I would never say so for her to hear.

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