thkdicknu
02-24-2010, 06:09 PM
This story is from years ago when i was very young 20 i think. I was going back down to Florida for the summer to help take care of my grandfather who was in ill health and my grandmother was overwhelmed. They lived in a nice trailer park of senior citizens and i had been there couple times before and met some of the people. A couple had moved or passed away but i had met and become friends with a widower named Helen. She passed away a longtime ago and i thought i would share my memory of her with you. She was a wonderful woman and my experiences with her probably led to one of my favorite sexual habits of liking age differences both older and younger. I am guessing she was in her early 60's and very sweet. Went to church at least twice a week and her husband had been killed in an accident many years before and left her well off financially and she loved this little community. She was not flashy or bold but i remember as thoughtful and caring. She had not changed much over the 5 years since i had first met her and had a youthfull look about her. She was very petite and had ample breasts for her little frame and nice little legs. I loved when she would dress for things like church. She always wore something like a white blouse always buttoned to the top and a nice loose flowing skirt to her knees and modest high heels and being in Florida so long she always had a decent tan. She didn't show alot of leg but her legs from her knees down looked very shapely and she had this snow white short hair and brilliant green eyes that seemed to sparkle when she talked to you. I would help her carry in things like groceries and work in her little garden and we had become real friends despite our age difference and i almost felt guilty when i would see her walking to her car or back from church in one of her sweet little dresses. Seeing her cute little legs and ample tits in her modest blouse would often give me a hard on and i would have to hide it. I don't think she ever noticed it except for one day when we are at the pool. There were a few guys in the clubhouse playing bridge or something and she was sunning. She rarely went swimming and i was enjoying the pool on this hot after noon. She always wore a modest blue one piece bathing suit and this one day as i was coming to the side of the pool and resting before i climbed out she was laying there on a lounge chair flat on her back asleep and her legs were spread and facing me and i got this huge boner. I looked so hard i thought i could even see some very slight pussy hair from the edge. I must have stayed there looking for a minute or so and then dove back into the pool swimming laps and trying to think of something else to loose my boner. When i got out she was awake and sitting up and smiled as i got out and i saw this look on her face. I still had a decent boner and i think she knew why because i was looking right at her trying to make small talk feeling foolish. I gave in and said..i am sorry as i put my hand in front of my swim trunks and she was very sweet saying it's ok sweetie. She wrapped her towel around her and said bye and made no big deal of it. Weeks went by and i was really horny and could not stop thinking about her. She never dated and i never saw her with a man. I thought she was so nice and had no vices other than she did like to drink screwdrivers or gin and tonic. I never saw her drunk or even tipsy though. One Saturday morning i had helped her in with two grocery bags and she asked if i knew anything about fixing a toilet that was running and i took care of it. The chain was just off and she made herself a gin and tonic while i fixed it and after she offered me some lemonade and as i drank it i said is that good i never had one and she gave me a sip and i didn't like it at all. She said your so helpful why don't you come back and i will make you a nice home cooked meal and asked what i liked and i said spaghetti and meatballs was a favorite and she asked if i liked Monopoly. She really liked cards and board games and i said sure and she said we could play Monopoly after dinner. I had a somewhat dirty mind and said sounds good but i was really thinking i would love to play with her. She made me a nice dinner and then we began the game and she gave me iced tea and she was having one of her screwdrivers and then another and i asked to taste it and said mmmm..now i like that and she said ok don't tell ..i will make you one..i don't want your grandmother mad at me.
I was in my shorts and barefoot and she was wearing a nice little dress and also was barefoot and i admired her pink toenails and fingernails. The dress had very modest cleavage she wasn't thinking of seducing me she was just enjoying the companionship. But i would sneek my peaks at her through the evening as she would rise from the table and i could see more leg as she stood and the dress came down and once in awhile she would laugh lightly as we played and a slight lean forward would sho me a little more tit than she realized and i was getting excited. She seemed so vibrant for a woman her age and fun and as we played the game she had a third screwdriver and talking of feeling tipsy and i had one that gave me a bit of courage and we had been talking about lots of things with her asking what my plans for the future were and if i had a girlfriend and i told her i dated but nothing steady and she would talk about missing her husband Joseph and what a wonderful man he was and i would say your still young you will meet a man and probably get married again and she would say no..Joseph was my and only husband but thanked me saying how nice and still very attractive she was. I felt a little sad for her but the conversation always lightened and we laughed alot as we played. Then as she won the game and was laughing and kidding with me she made that comment about being tipsy and got up to go to the kitchen for glass of water but she stumbled a bit and bumped into the corner of the counter and said OWW..Damn and laughed saying that hurt. I never heard her cuss before and i got up to see if she was ok and she was shaking it off but a little wobbly and i said you need to lay down let me help you and i helped he to the back of her double wide trailer to lay down on the bed. She layed back saying eeewww..and laughing saying she should not have had that last screwdriver and laughing lightly. I know she was not aware of how horny i was for her at that moment and not thinking about sex and i went and got a glass of water and gave it to her and then she layed back again kind of closing her eyes and her one leg was kind of crooked and bent to the side and she was not wearing panty hose and i got a great view of her flowered panties and started to get hard standing there silently. She was a little out of it but awake and i knew it was my chance maybe the only one i would ever get so as she layed there with her eyes closed i slipped my t-shirt and shorts off and this amazing wood going on. I wanted her bad. I slipped onto the bed easy and slid up next to her and began to kiss her neck as i slid my hand up her leg under her dress along her inner thigh. Almost immediatley i heard her breathing get faster in my ear as she spoke softly and said no Derek..please..i paid no attention to her as my hand reached her panties and i gently ran my finger over her panties tracing through her pussy lips as i kissed her neck and then put my tongue in her ear. I heard her say softly..Derek..hahaha..Derek..we can't..haha..so i slid down slowly and raised her dress and began to munch on her panties and she moaned and i slipped her panties off and slid them down as she reached downward again saying nooo..Derek...hahaha and then i licked her pussy at first softly and took in her smell which was kind of musky and licked through her pussy lips and then put my tongue in her and wiggled it around and she had put her hands down on my shoulders and was moaning softly but not saying anything anymore but her hips were moving up meeting my mouth she made these short fast movements and her moans were deeper. I slid back up an whispered in her ear that i wanted to make her happy and she put her arms around me and we looked into each others eyes and she looked like she was in such need and i rolled her over on top of me pulling her dress off and working on her bra and she was trying to say noo..sweetie but her body was betraying her as she slid her pussy on my body. I finally had her bra off and pulled her down and kissed her mouth deeply and was running my hands over her back and butt and she was rubbing against me and i turned over with her sideways and pulled her hand down to my dick and at first she didn't want to open her hand but as i suckled at her breasts like a child she opened her hand and gently stroked it saying through heavy breathing..Derek..Derek..OH MY..what are you doing to me. I then started kissing her lips and neck again and said do you like how that feels as i put my hand over hers and she gently stroked my dick and i had moved my head to look in her eyes and she stroked it for a second and with a look of desire in her eyes she said yes...and i said do you want me inside you and went back to kissing her neck and she put her hand on the back of my head and said softly yes..oh..yes..hahaha. So, i rolled her to her back gently and got between her legs and she spread them with her feet on the bed and i gently rubbed my cock through her pussy as we looked at each other and she was so sweet and her voice was like an angel and i felt in control and wanted her and put my hands down to support me to the side of her head and she rolled her hips as i slowly penetrated her. I will always remember seeing her eyes roll back in her head and her moan as i sunk slowly into her. She was much tighter than i would have expected for a woman her age but she loosened up as i began to have sex with her.
I was so young and hard and the expressions her face made were making me feel like a king as i pumped into her faster and her breathing was fast and shallow..hahahahahahaha..and she would at times get louder and sayd..EEEEEEEWWWWWWW....I had to have fucked her for a good 10 minutes or so and was nearing climax and to this day i don't know why but i asked her...can i CUM in you Helen and she said in a shortened breath..yes..oohhh..yes Derek CUM inside me ..i want to feel you CUM IN ME. I was so excited hearing that i pulled her legs back and began to drive into hr hard and fast and she was moaning loud OOOOHHHH..OOOHHHH...and i came and saw stars as i unloaded and she then wrapped her legs around me and squeezed tight and shoved her hips up and hed them and yelled...OOOOHHHHHHH and i knew she had CUM. I was out of breath and sweaty and i saw the sweat glistening off her nice sized tits and i was still hard and pulled out sucking her tits and licking them as she put her hands on my head and slid down and licked her pussy more and her hips were moving up to meet my mouth and she was tossing around and moaning and all at once she sat half up with my face buried in her pussy ans shook and came again. Then she dropped to the bed panting and dry mouthed saying Oh MY..over and over a few times. I crawled up to her wiping off my face and kissed her deeply and she put her hands down and gently ran her fingers on my dick and seemed surprised i was still so hard and had this grin on her face as she slipped down and admired my dick rubbing it and then slowly gently sucking me. I was in heaven watching this sweet older lady with white hair as her eyes were closed and she went down on me purring and i was moaning for her saying..OH HELEN....OOOHHHH...and then i pulled her up i had to fuck her more and i had her get on her stomach and put a pillow under her and layed on top of her and pushed into her again and she winced at first and then started to moan again as i stroked it nice and slow and i tried to place and keep my hands on hers which were gripping the bed as i stroked her and i was saying OH HELEN...OHH..YOU FEEL SO GOODDDDD...HAHAHA and i slowed to a stop and whispered in her ear ..Helen i want to put it i your butt would you like that and she was panting and said go easy ..hahaha and i did and i loved fucking her ass but i was so excited by it i came withing a minute. After that we curled up and fell asleep but she woke me up a couple hours later saying its late you need to go home before your grandparents wake up. I watched her get up and put on a robe and i was getting excited again as she went to the kitchen to make coffee. I came to the kitchen naked and put my arms around her and she pulled them down gently saying Derek..last night was wonderful but it was a mistake. I am an old lady and your just a boy. We can be friends but we can't do this again. I was trying to pursuade her as she walked to the living room and sat on the couch and i went and sat next to her putting my hand through her robe to fondle her tit and she would nicely pull it out saying Derek stop and i would run my hand under her robe and play with her pussy and kiss her and she was putting her hand down and trying to pull mine away but she was breathing heavier as she said we can't Derek in a soft voice and i said just once more..just one more time and the combination of my hands working on her as now i had a couple buttons undone on her robe and her own desires got the best of her and she said..alright..just one more time and she allowed me to open her robe and fondle her and she leaned down and sucked my cock and seemed to enjoy it more than she wanted to and then i put her on top of me and she grabbed the back of the couch as she sunk down on me and was going up and down and faster now and as she did that i put my hands on her hips and helped her go up and down and i could hear her wetness as she rode me fast and was doing this short and rapid hahahahaha..OMG...hahahaaha..i was so fucking HOT i had her by the hips and then she wasn't moving i was ramming into her pushing her down on my shaft and then pulling her up like a doll fucking her fast and her pussy felt and sounded so wet and sloppy and made this kind of popping sound as impaled her repeatedly and i was then saying loudly YEAH..HAHAHA..YEAH...COME ON..COME ON..CUM FOR ME.and shortly after that she squeezed her body together tight on me and clung to me against my body grunting and yelling OOHHHH MYYYY..HAHAHA..OHHH MYYY and she really came hard and as she finished i stood up with her on my dick and layed her down on her back on the carpet as she clung to me and i balled her fast and hard for a couple minute and came again in her as my ass cheeks tightened and i could feel the throbbing of my dick shooting my load in her. We layed there holding each other for a buit and she said she never had been made love to like that before and not to be hurt but i was too young and we shouldn't do this anymore. I agreed and the rest of the summer we were back to the same behavior as before with little smiles for each other sometimes. Just before i was to go home i talked her into letting me take her for a bite to eat to say goodbye and of course i worked on her all through the meal and when we got back in my car i headed back but stopped at this road side fruit stand that was closed and she was saying Derekkkkk.. i laughed and said i need something to remember you by..she said you already have that and i said yeah but i want a little more as i petted her a bit. She looked around and then scooted close and unzipped me and pulled it out and gave me this amazing slow BJ as i rubbed her ass gently. I was so GOOD..after a couple minutes she seemed really into it and i heard the wet sloppy sounds of my cock going into and out of her mouth and she surprised me by getting to the point where she was taking it all in down to my balls and i was ready and she could tell and just as i came she took it deep and held it as i came down her throat. I was panting and doing that OHHHH...OHHHHH...and she milked me good and kept sucking until my cock stopped throbbing and sat up wiping her mouth like a lady and said now you will remember that and smiling. I was still fucking hard..sticking straight up and laughing and she said what are we going to do with you..lol...i was feeling cocky by then and said i think i know what you want to do with me and she gave me this big open mouthed look and said DEREK...she smiled and with that twinkle in her eye she said..well we shouldn't waste that beautiful erection should we and she said your leaving tomorrow soooo..i cut her off..it was almost dark and i looked around and there were no cars so i said lets go and she got out of the car and so did i with this boner hanging out of my pants and she we were laughing at the site of me and hurried around to the back of this fruit stand. Luckily there was this picnic table and she layed down on it for me and i stood there and balled her good. I had orgasmed good from her BJ and i was lasting enjoying every last thrust i would ever get into her and she was making noise with my hands on her hips i was driving it into it and her legs were flopping and she was gripping the sides of the picnic table and doing HAHAHAHA...OOOOHHH...GODDDDDD..DEREK...and she started just saying one word at a time saying...OOOHHHHH...YOUR SO BIG OHHHH I LOVE IT...OOOHHHHH...YEAHHHHH...DEREK and then she sat up fast again with her hands on the table beside and a little behind her and seemed to grind down on my cock and she came..as loud as you can...she said...OOOHHHHH...and her hips twitched and i was ready and put my arms around her above the waist and pulled her to me and pumped into her rapidly grunting and hearing my balls slap against her in her in short spurts of sound do this..UH UH UH UH UH and her pussy was so tight on my shaft i felt her pussy squeeze my dick and pulse as i casme again in her with a loud prolonged groan. I pulled out us both out of breath and held her face and kissed her lips telling her how much i would miss her and she told me the same putting her hand on mine. I will never forget Helen.
I was in my shorts and barefoot and she was wearing a nice little dress and also was barefoot and i admired her pink toenails and fingernails. The dress had very modest cleavage she wasn't thinking of seducing me she was just enjoying the companionship. But i would sneek my peaks at her through the evening as she would rise from the table and i could see more leg as she stood and the dress came down and once in awhile she would laugh lightly as we played and a slight lean forward would sho me a little more tit than she realized and i was getting excited. She seemed so vibrant for a woman her age and fun and as we played the game she had a third screwdriver and talking of feeling tipsy and i had one that gave me a bit of courage and we had been talking about lots of things with her asking what my plans for the future were and if i had a girlfriend and i told her i dated but nothing steady and she would talk about missing her husband Joseph and what a wonderful man he was and i would say your still young you will meet a man and probably get married again and she would say no..Joseph was my and only husband but thanked me saying how nice and still very attractive she was. I felt a little sad for her but the conversation always lightened and we laughed alot as we played. Then as she won the game and was laughing and kidding with me she made that comment about being tipsy and got up to go to the kitchen for glass of water but she stumbled a bit and bumped into the corner of the counter and said OWW..Damn and laughed saying that hurt. I never heard her cuss before and i got up to see if she was ok and she was shaking it off but a little wobbly and i said you need to lay down let me help you and i helped he to the back of her double wide trailer to lay down on the bed. She layed back saying eeewww..and laughing saying she should not have had that last screwdriver and laughing lightly. I know she was not aware of how horny i was for her at that moment and not thinking about sex and i went and got a glass of water and gave it to her and then she layed back again kind of closing her eyes and her one leg was kind of crooked and bent to the side and she was not wearing panty hose and i got a great view of her flowered panties and started to get hard standing there silently. She was a little out of it but awake and i knew it was my chance maybe the only one i would ever get so as she layed there with her eyes closed i slipped my t-shirt and shorts off and this amazing wood going on. I wanted her bad. I slipped onto the bed easy and slid up next to her and began to kiss her neck as i slid my hand up her leg under her dress along her inner thigh. Almost immediatley i heard her breathing get faster in my ear as she spoke softly and said no Derek..please..i paid no attention to her as my hand reached her panties and i gently ran my finger over her panties tracing through her pussy lips as i kissed her neck and then put my tongue in her ear. I heard her say softly..Derek..hahaha..Derek..we can't..haha..so i slid down slowly and raised her dress and began to munch on her panties and she moaned and i slipped her panties off and slid them down as she reached downward again saying nooo..Derek...hahaha and then i licked her pussy at first softly and took in her smell which was kind of musky and licked through her pussy lips and then put my tongue in her and wiggled it around and she had put her hands down on my shoulders and was moaning softly but not saying anything anymore but her hips were moving up meeting my mouth she made these short fast movements and her moans were deeper. I slid back up an whispered in her ear that i wanted to make her happy and she put her arms around me and we looked into each others eyes and she looked like she was in such need and i rolled her over on top of me pulling her dress off and working on her bra and she was trying to say noo..sweetie but her body was betraying her as she slid her pussy on my body. I finally had her bra off and pulled her down and kissed her mouth deeply and was running my hands over her back and butt and she was rubbing against me and i turned over with her sideways and pulled her hand down to my dick and at first she didn't want to open her hand but as i suckled at her breasts like a child she opened her hand and gently stroked it saying through heavy breathing..Derek..Derek..OH MY..what are you doing to me. I then started kissing her lips and neck again and said do you like how that feels as i put my hand over hers and she gently stroked my dick and i had moved my head to look in her eyes and she stroked it for a second and with a look of desire in her eyes she said yes...and i said do you want me inside you and went back to kissing her neck and she put her hand on the back of my head and said softly yes..oh..yes..hahaha. So, i rolled her to her back gently and got between her legs and she spread them with her feet on the bed and i gently rubbed my cock through her pussy as we looked at each other and she was so sweet and her voice was like an angel and i felt in control and wanted her and put my hands down to support me to the side of her head and she rolled her hips as i slowly penetrated her. I will always remember seeing her eyes roll back in her head and her moan as i sunk slowly into her. She was much tighter than i would have expected for a woman her age but she loosened up as i began to have sex with her.
I was so young and hard and the expressions her face made were making me feel like a king as i pumped into her faster and her breathing was fast and shallow..hahahahahahaha..and she would at times get louder and sayd..EEEEEEEWWWWWWW....I had to have fucked her for a good 10 minutes or so and was nearing climax and to this day i don't know why but i asked her...can i CUM in you Helen and she said in a shortened breath..yes..oohhh..yes Derek CUM inside me ..i want to feel you CUM IN ME. I was so excited hearing that i pulled her legs back and began to drive into hr hard and fast and she was moaning loud OOOOHHHH..OOOHHHH...and i came and saw stars as i unloaded and she then wrapped her legs around me and squeezed tight and shoved her hips up and hed them and yelled...OOOOHHHHHHH and i knew she had CUM. I was out of breath and sweaty and i saw the sweat glistening off her nice sized tits and i was still hard and pulled out sucking her tits and licking them as she put her hands on my head and slid down and licked her pussy more and her hips were moving up to meet my mouth and she was tossing around and moaning and all at once she sat half up with my face buried in her pussy ans shook and came again. Then she dropped to the bed panting and dry mouthed saying Oh MY..over and over a few times. I crawled up to her wiping off my face and kissed her deeply and she put her hands down and gently ran her fingers on my dick and seemed surprised i was still so hard and had this grin on her face as she slipped down and admired my dick rubbing it and then slowly gently sucking me. I was in heaven watching this sweet older lady with white hair as her eyes were closed and she went down on me purring and i was moaning for her saying..OH HELEN....OOOHHHH...and then i pulled her up i had to fuck her more and i had her get on her stomach and put a pillow under her and layed on top of her and pushed into her again and she winced at first and then started to moan again as i stroked it nice and slow and i tried to place and keep my hands on hers which were gripping the bed as i stroked her and i was saying OH HELEN...OHH..YOU FEEL SO GOODDDDD...HAHAHA and i slowed to a stop and whispered in her ear ..Helen i want to put it i your butt would you like that and she was panting and said go easy ..hahaha and i did and i loved fucking her ass but i was so excited by it i came withing a minute. After that we curled up and fell asleep but she woke me up a couple hours later saying its late you need to go home before your grandparents wake up. I watched her get up and put on a robe and i was getting excited again as she went to the kitchen to make coffee. I came to the kitchen naked and put my arms around her and she pulled them down gently saying Derek..last night was wonderful but it was a mistake. I am an old lady and your just a boy. We can be friends but we can't do this again. I was trying to pursuade her as she walked to the living room and sat on the couch and i went and sat next to her putting my hand through her robe to fondle her tit and she would nicely pull it out saying Derek stop and i would run my hand under her robe and play with her pussy and kiss her and she was putting her hand down and trying to pull mine away but she was breathing heavier as she said we can't Derek in a soft voice and i said just once more..just one more time and the combination of my hands working on her as now i had a couple buttons undone on her robe and her own desires got the best of her and she said..alright..just one more time and she allowed me to open her robe and fondle her and she leaned down and sucked my cock and seemed to enjoy it more than she wanted to and then i put her on top of me and she grabbed the back of the couch as she sunk down on me and was going up and down and faster now and as she did that i put my hands on her hips and helped her go up and down and i could hear her wetness as she rode me fast and was doing this short and rapid hahahahaha..OMG...hahahaaha..i was so fucking HOT i had her by the hips and then she wasn't moving i was ramming into her pushing her down on my shaft and then pulling her up like a doll fucking her fast and her pussy felt and sounded so wet and sloppy and made this kind of popping sound as impaled her repeatedly and i was then saying loudly YEAH..HAHAHA..YEAH...COME ON..COME ON..CUM FOR ME.and shortly after that she squeezed her body together tight on me and clung to me against my body grunting and yelling OOHHHH MYYYY..HAHAHA..OHHH MYYY and she really came hard and as she finished i stood up with her on my dick and layed her down on her back on the carpet as she clung to me and i balled her fast and hard for a couple minute and came again in her as my ass cheeks tightened and i could feel the throbbing of my dick shooting my load in her. We layed there holding each other for a buit and she said she never had been made love to like that before and not to be hurt but i was too young and we shouldn't do this anymore. I agreed and the rest of the summer we were back to the same behavior as before with little smiles for each other sometimes. Just before i was to go home i talked her into letting me take her for a bite to eat to say goodbye and of course i worked on her all through the meal and when we got back in my car i headed back but stopped at this road side fruit stand that was closed and she was saying Derekkkkk.. i laughed and said i need something to remember you by..she said you already have that and i said yeah but i want a little more as i petted her a bit. She looked around and then scooted close and unzipped me and pulled it out and gave me this amazing slow BJ as i rubbed her ass gently. I was so GOOD..after a couple minutes she seemed really into it and i heard the wet sloppy sounds of my cock going into and out of her mouth and she surprised me by getting to the point where she was taking it all in down to my balls and i was ready and she could tell and just as i came she took it deep and held it as i came down her throat. I was panting and doing that OHHHH...OHHHHH...and she milked me good and kept sucking until my cock stopped throbbing and sat up wiping her mouth like a lady and said now you will remember that and smiling. I was still fucking hard..sticking straight up and laughing and she said what are we going to do with you..lol...i was feeling cocky by then and said i think i know what you want to do with me and she gave me this big open mouthed look and said DEREK...she smiled and with that twinkle in her eye she said..well we shouldn't waste that beautiful erection should we and she said your leaving tomorrow soooo..i cut her off..it was almost dark and i looked around and there were no cars so i said lets go and she got out of the car and so did i with this boner hanging out of my pants and she we were laughing at the site of me and hurried around to the back of this fruit stand. Luckily there was this picnic table and she layed down on it for me and i stood there and balled her good. I had orgasmed good from her BJ and i was lasting enjoying every last thrust i would ever get into her and she was making noise with my hands on her hips i was driving it into it and her legs were flopping and she was gripping the sides of the picnic table and doing HAHAHAHA...OOOOHHH...GODDDDDD..DEREK...and she started just saying one word at a time saying...OOOHHHHH...YOUR SO BIG OHHHH I LOVE IT...OOOHHHHH...YEAHHHHH...DEREK and then she sat up fast again with her hands on the table beside and a little behind her and seemed to grind down on my cock and she came..as loud as you can...she said...OOOHHHHH...and her hips twitched and i was ready and put my arms around her above the waist and pulled her to me and pumped into her rapidly grunting and hearing my balls slap against her in her in short spurts of sound do this..UH UH UH UH UH and her pussy was so tight on my shaft i felt her pussy squeeze my dick and pulse as i casme again in her with a loud prolonged groan. I pulled out us both out of breath and held her face and kissed her lips telling her how much i would miss her and she told me the same putting her hand on mine. I will never forget Helen.