Sex with an older woman
24-Jun-22 09:14
I’ve always chatted with Eileen ever since I started delivering her milk in 1990. She was always pleasant and well turned out. I always call every other Thursday and that was the day she went out for lunch with her husband George.
When I called she usually had just returned. In the summer she would wear a blouse that would show a sneaky bit of cleavage. Also a nice smell of perfume. I would always ask where they had been and what they had done. It was usually a visit to a garden centre then lunch either there or some pub in the area.
As the years passed Eileen and George were still in this routine. Her appearance didn’t change much although she had put on a little weight around her bum and tits looked a little bigger.
Their next door neighbour was an single mother with two kids who enjoyed regular visitors, being told by Eileen, that many stayed all night and departed early in the morning. She had asked me if I ever saw any movement at the house. I told her I would see the curtains move sometimes when I called to deliver and that there was alway a light on in the bedroom window.
This always made me look up with the chance of seeing anything and she was not one to disappoint. Many a time I’ve seen her just in a bra looking out of the window but since her visitors made a showing, I’ve seen her topless with her pert little tits peering out out a gap in the curtains.
Eileen was quite amused by this but gave the “Tut Tut”view of things. George never said much and his health was detetiorating slowly.
Over the weeks, Eileen was ever more interested in the activities of their neighbours. I didn’t have too much to tell her, a bit of tit now and again.
One Thursday when I called Eileen couldn’t wait to tell me that she’d had a restless nights sleep and heard noises outside. She went into her bathroom which has a window on the side next to the neighbour and all she could here was “yes yes yes” It was HER having sex she told me.
I smiled and said that people do you know. She replied “well not everyone does you know” I said to her “I bet you used to be like that” Eileen was shocked a little and a faint blush came over her face.
She also was wearing a thin figure hugging sweater with a v-neck showing her usual cleavage. However, this time her nipples were clearly erect underneath the thin material.
She caught me looking at her nipples and said “EEE Peter, George and I would only “do it” usually on a Friday night after a trip to the club. “It was lights out,nightie up,in out in out then grunt, roll over,sleep”
Oh Peter,I can’t believe I’ve just told you that.
We were standing inside the front porch with the front door shut behind me. I put my arm around her and gave her a big hug and said “Oh. Eileen” She was hugging me really hard and I could feel her boobs squashing up against my chest.
She released her hold and held my hand and said “George is in the back room” “I don’t want to upset him”.
We stood apart and carried on with me taking her milk money. Eileen had always,for years, shouted through to George that “it’s only the milkman pet”.
She did this today as usual. She told me that I was the first person who knew anything about her “wham bam, thank you mam” sex life. These was her exact words. George was busy watching “The Chase” on the tv and Eileen closed the lounge door so we were still in the hall and she took hold of my hand,squeezing it and said she was sorry for telling me her sad story.
I reacted by squeezing her hands and giving her a bit of a sloppy kiss to which she responded.Her boobs were pushing out towards me and I released my hold on her hands and slipped them around her bum and pulled her towards me. I was starting to get a hard-on and slowly ground my hips with hers.
There was no opposition to any of this. She suddenly stopped and pushed me away saying “we can’t do this, well not here anyway”.
This made me think she was up for some serious sex.
She asked if I was busy on a Saturday morning because George always went to town and met a couple of old pals for a lunchtime drink then home for a sleep in the chair. Regular as clockwork.
I told her that after I had delivered the milk I was free. Good, she said. Come round when George’s car isn’t there. Don’t knock. Just come in. The door will be open and go straight upstairs.
I can’t wait. I shouted through to George that I was going as I alway did and he replied “see you son”
Saturday arrived and I rushed to finish my deliveries, unloaded,quick shower and drove my car to Eileen’s. George’s car had gone.
I walked with confidence up the drive to the front door,opened the door and stood inside. “I’m up here Peter.”Eileen called. I went straight upstairs into the front bedroom.
Eileen was lying on top of the bed in a black silky dressing gown. .” Lovely to see you,wasn’t sure you would show up.” I slipped off my shoes and leaned over her holding her face and gave her a slow lingering kiss on her lips.
At the same time positioning myself next to her on top of the bed. Without saying anything I pulled the cord on her gown and it fell open revealing a lovely black bra and a full cut pair of matching panties with a lacy front panel.
I stood back pulling my shirt over my head and admiring the view. Eileen was a little shy but I undid my jeans and dropped them to the floor. I knelt down on the floor beside her and gently caressed here amazing boobs over the material of her bra. Her nipples were rock hard and I twiddled them with my finger and thumb. I then began kissing the deep valley between her boobs and the overflowing flesh above the bra cup.
I then moved down to her tummy. A few wrinkles here but still reasonably firm. Then I probed my tongue into her tummy button while playing with the waist band of her sexy panties.
I then kissed her fanny lips through the see through panel of her panties. I glanced up and saw her head tilted back and her eyes,moaning slightly,hopefully with pleasure. I then got my fingers inside the waist band of her panties and slowly began to slip them over her bum. She voluntarily raised her bum to get them off.
She had just a thin covering of hair over her fanny lips and the surrounding area neatly shaved. I lowered myself so I could gently kiss and lick her neat slit.
As I did she gave a soft whimper and slightly opened her legs so I slowly parted her fanny lips to give her clit a good sucking.
At the same time I got my middle finger searching deep inside her nice moist fanny. Eileen looks down and asks me to join her on the bed. As I stand up she smiles a says to take off my pants.
As I do my cock is not fully erect but it’s well on the way. Eileen looks at it and say “I believe you men like a girl to suck your willy, I do it to George now and then but I never know if I do it correct but he soon cums and then falls asleep so I miss out on my quick in and out so I have to finish it off with my vibrator” “
“Don’t worry about that today Eileen, do you like sucking cock?.” “I’ve only ever sucked George off”
Without saying anything else she slides down the bed a bit so she’s in line with my cock. Gently holding it she slowly slips down my foreskin revealing my shiny bell end. She then slowly licks it with the tip of her tongue before sliding it deeper and deeper down her throat. This is fantastic. You would have thought she did it everyday.
“Peter, is it ok if we do “it” with me on top” “ George always used to try to get it in with me on my back.
Many a time he’d cum after two humps,roll off then go to sleep”
“Of course Eileen,that would be great”
I position myself in the middle of the bed on my back. My cock is now rock hard and Eileen kneels over me and parts her fanny and I hold my cock between her slit and slowly it slides right up.
She then rhythmly moves up and down.
I’ve got my hands over her boobs still in her bra and gently kissing her.
I eventually start to cum and Eileen increases her muscle grip in her fanny till I ejaculate deep inside her. We both lay motionless for a while then Eileen slowly slips off my cock but unexpectedly begins to suck my cock clean and it slowly begins to get hard again.
I ask Eileen to go on all fours near the end of the bed. She does,but turns and says that she doesn’t want it up the bum. Fanny yes,bum no “of course”I tell her and slowly guide my cock up her fanny, in and out till I cum again.
We both then lay side by side on the bed gently caressing each other.
Me gently playing with her clit, her slowly wanking my re-hardening cock.
I look at her with her head on the pillow and a contented smile on her face.
She says to me .”that’s the best fuck I’ve ever had and I never use words like that but that was a fuck” “can we do it again.? Now? “ “Of course we can”
This time Eileen stays on her back with her knees bent and parted. What a great view of all her intimate bits including her rosebud bum hole.
I knelt between her legs and softly explored her fanny with my index finger and letting my thumb brush over her bum. There was no resistance to this so I slowly worked my thumb a little deeper up her bum.
I now had my finger deep up her fanny and thumb deep up her bum. “Oh that feels so different,I’ve never enjoyed anything like it before and that’s in 76 years”
George has never touched my arse never mind put a finger up it” “in fact it’s always dark when he tries his Friday night ‘shag’ and I don’t think he’s ever seen my naked bum or fanny,
He has seen my boobs and he does sometimes play with them when I’ve had a shower,but nothing else!”
I get the tip of my cock just at the opening of her fanny and tease it,slowly inserting the head in and out. “ not like George “ I say to her with a smile, I then push my cock deep up her fanny and my balls are smacking her bum.
I then pump it rhythmically until Eileen is on the brink of an orgasm. She raises her legs and locks them round my back, she then shudders a bit before releasing her grip and relaxing back on the bed.
I slowly slip my cock out from her fanny and place it over her small rosebud bum hole. My spunk is all over my cock so when I try to enter her bum it slides in so easily. “Just put the tip in at first Peter” Eileen said. I only let my bell end enter and slowly slip it in and out.
Eileen moves in time with me then says “try a bit more, I love this”This is real shagging and I never use language like that but I love it”
Very slowly I insert my cock all the way in, her bum is nice and tight. This lasts for about five minutes when I cum deep up her bum then I slip it out slowly with my spunk ouseing down her crack.
We are both on our backs lying side by side with knees bent up and slightly parted. I put my hand over her fanny and slip my index finger inside her.
She is gently playing with my now flaccid foreskin pulling it back and forth over the tip and exploring the slit at the top.
I said to her that she knows how to please someone seeing that her and George are very limited in their activities.
She said that her sister and her, when the were teenagers, would talk about what they would do while having sex.
She did try some things out with George when they first got married but he wasn’t very interested in adventure so she put up with it.
She told me I was only the second person ever to see her naked.
After a little while Eileen got up and took a look out of the window. She said that the girl next door was just there getting into a car. “I bet she hasn’t had a good fucking this morning like I have” with a giggle in her voice.
“I could get quite used to this” she said. “are we going to do this again,Peter?” Her voice had a sound of anticipation in it.
“Of course we will”.
“Same again next Saturday I hope”
When I called she usually had just returned. In the summer she would wear a blouse that would show a sneaky bit of cleavage. Also a nice smell of perfume. I would always ask where they had been and what they had done. It was usually a visit to a garden centre then lunch either there or some pub in the area.
As the years passed Eileen and George were still in this routine. Her appearance didn’t change much although she had put on a little weight around her bum and tits looked a little bigger.
Their next door neighbour was an single mother with two kids who enjoyed regular visitors, being told by Eileen, that many stayed all night and departed early in the morning. She had asked me if I ever saw any movement at the house. I told her I would see the curtains move sometimes when I called to deliver and that there was alway a light on in the bedroom window.
This always made me look up with the chance of seeing anything and she was not one to disappoint. Many a time I’ve seen her just in a bra looking out of the window but since her visitors made a showing, I’ve seen her topless with her pert little tits peering out out a gap in the curtains.
Eileen was quite amused by this but gave the “Tut Tut”view of things. George never said much and his health was detetiorating slowly.
Over the weeks, Eileen was ever more interested in the activities of their neighbours. I didn’t have too much to tell her, a bit of tit now and again.
One Thursday when I called Eileen couldn’t wait to tell me that she’d had a restless nights sleep and heard noises outside. She went into her bathroom which has a window on the side next to the neighbour and all she could here was “yes yes yes” It was HER having sex she told me.
I smiled and said that people do you know. She replied “well not everyone does you know” I said to her “I bet you used to be like that” Eileen was shocked a little and a faint blush came over her face.
She also was wearing a thin figure hugging sweater with a v-neck showing her usual cleavage. However, this time her nipples were clearly erect underneath the thin material.
She caught me looking at her nipples and said “EEE Peter, George and I would only “do it” usually on a Friday night after a trip to the club. “It was lights out,nightie up,in out in out then grunt, roll over,sleep”
Oh Peter,I can’t believe I’ve just told you that.
We were standing inside the front porch with the front door shut behind me. I put my arm around her and gave her a big hug and said “Oh. Eileen” She was hugging me really hard and I could feel her boobs squashing up against my chest.
She released her hold and held my hand and said “George is in the back room” “I don’t want to upset him”.
We stood apart and carried on with me taking her milk money. Eileen had always,for years, shouted through to George that “it’s only the milkman pet”.
She did this today as usual. She told me that I was the first person who knew anything about her “wham bam, thank you mam” sex life. These was her exact words. George was busy watching “The Chase” on the tv and Eileen closed the lounge door so we were still in the hall and she took hold of my hand,squeezing it and said she was sorry for telling me her sad story.
I reacted by squeezing her hands and giving her a bit of a sloppy kiss to which she responded.Her boobs were pushing out towards me and I released my hold on her hands and slipped them around her bum and pulled her towards me. I was starting to get a hard-on and slowly ground my hips with hers.
There was no opposition to any of this. She suddenly stopped and pushed me away saying “we can’t do this, well not here anyway”.
This made me think she was up for some serious sex.
She asked if I was busy on a Saturday morning because George always went to town and met a couple of old pals for a lunchtime drink then home for a sleep in the chair. Regular as clockwork.
I told her that after I had delivered the milk I was free. Good, she said. Come round when George’s car isn’t there. Don’t knock. Just come in. The door will be open and go straight upstairs.
I can’t wait. I shouted through to George that I was going as I alway did and he replied “see you son”
Saturday arrived and I rushed to finish my deliveries, unloaded,quick shower and drove my car to Eileen’s. George’s car had gone.
I walked with confidence up the drive to the front door,opened the door and stood inside. “I’m up here Peter.”Eileen called. I went straight upstairs into the front bedroom.
Eileen was lying on top of the bed in a black silky dressing gown. .” Lovely to see you,wasn’t sure you would show up.” I slipped off my shoes and leaned over her holding her face and gave her a slow lingering kiss on her lips.
At the same time positioning myself next to her on top of the bed. Without saying anything I pulled the cord on her gown and it fell open revealing a lovely black bra and a full cut pair of matching panties with a lacy front panel.
I stood back pulling my shirt over my head and admiring the view. Eileen was a little shy but I undid my jeans and dropped them to the floor. I knelt down on the floor beside her and gently caressed here amazing boobs over the material of her bra. Her nipples were rock hard and I twiddled them with my finger and thumb. I then began kissing the deep valley between her boobs and the overflowing flesh above the bra cup.
I then moved down to her tummy. A few wrinkles here but still reasonably firm. Then I probed my tongue into her tummy button while playing with the waist band of her sexy panties.
I then kissed her fanny lips through the see through panel of her panties. I glanced up and saw her head tilted back and her eyes,moaning slightly,hopefully with pleasure. I then got my fingers inside the waist band of her panties and slowly began to slip them over her bum. She voluntarily raised her bum to get them off.
She had just a thin covering of hair over her fanny lips and the surrounding area neatly shaved. I lowered myself so I could gently kiss and lick her neat slit.
As I did she gave a soft whimper and slightly opened her legs so I slowly parted her fanny lips to give her clit a good sucking.
At the same time I got my middle finger searching deep inside her nice moist fanny. Eileen looks down and asks me to join her on the bed. As I stand up she smiles a says to take off my pants.
As I do my cock is not fully erect but it’s well on the way. Eileen looks at it and say “I believe you men like a girl to suck your willy, I do it to George now and then but I never know if I do it correct but he soon cums and then falls asleep so I miss out on my quick in and out so I have to finish it off with my vibrator” “
“Don’t worry about that today Eileen, do you like sucking cock?.” “I’ve only ever sucked George off”
Without saying anything else she slides down the bed a bit so she’s in line with my cock. Gently holding it she slowly slips down my foreskin revealing my shiny bell end. She then slowly licks it with the tip of her tongue before sliding it deeper and deeper down her throat. This is fantastic. You would have thought she did it everyday.
“Peter, is it ok if we do “it” with me on top” “ George always used to try to get it in with me on my back.
Many a time he’d cum after two humps,roll off then go to sleep”
“Of course Eileen,that would be great”
I position myself in the middle of the bed on my back. My cock is now rock hard and Eileen kneels over me and parts her fanny and I hold my cock between her slit and slowly it slides right up.
She then rhythmly moves up and down.
I’ve got my hands over her boobs still in her bra and gently kissing her.
I eventually start to cum and Eileen increases her muscle grip in her fanny till I ejaculate deep inside her. We both lay motionless for a while then Eileen slowly slips off my cock but unexpectedly begins to suck my cock clean and it slowly begins to get hard again.
I ask Eileen to go on all fours near the end of the bed. She does,but turns and says that she doesn’t want it up the bum. Fanny yes,bum no “of course”I tell her and slowly guide my cock up her fanny, in and out till I cum again.
We both then lay side by side on the bed gently caressing each other.
Me gently playing with her clit, her slowly wanking my re-hardening cock.
I look at her with her head on the pillow and a contented smile on her face.
She says to me .”that’s the best fuck I’ve ever had and I never use words like that but that was a fuck” “can we do it again.? Now? “ “Of course we can”
This time Eileen stays on her back with her knees bent and parted. What a great view of all her intimate bits including her rosebud bum hole.
I knelt between her legs and softly explored her fanny with my index finger and letting my thumb brush over her bum. There was no resistance to this so I slowly worked my thumb a little deeper up her bum.
I now had my finger deep up her fanny and thumb deep up her bum. “Oh that feels so different,I’ve never enjoyed anything like it before and that’s in 76 years”
George has never touched my arse never mind put a finger up it” “in fact it’s always dark when he tries his Friday night ‘shag’ and I don’t think he’s ever seen my naked bum or fanny,
He has seen my boobs and he does sometimes play with them when I’ve had a shower,but nothing else!”
I get the tip of my cock just at the opening of her fanny and tease it,slowly inserting the head in and out. “ not like George “ I say to her with a smile, I then push my cock deep up her fanny and my balls are smacking her bum.
I then pump it rhythmically until Eileen is on the brink of an orgasm. She raises her legs and locks them round my back, she then shudders a bit before releasing her grip and relaxing back on the bed.
I slowly slip my cock out from her fanny and place it over her small rosebud bum hole. My spunk is all over my cock so when I try to enter her bum it slides in so easily. “Just put the tip in at first Peter” Eileen said. I only let my bell end enter and slowly slip it in and out.
Eileen moves in time with me then says “try a bit more, I love this”This is real shagging and I never use language like that but I love it”
Very slowly I insert my cock all the way in, her bum is nice and tight. This lasts for about five minutes when I cum deep up her bum then I slip it out slowly with my spunk ouseing down her crack.
We are both on our backs lying side by side with knees bent up and slightly parted. I put my hand over her fanny and slip my index finger inside her.
She is gently playing with my now flaccid foreskin pulling it back and forth over the tip and exploring the slit at the top.
I said to her that she knows how to please someone seeing that her and George are very limited in their activities.
She said that her sister and her, when the were teenagers, would talk about what they would do while having sex.
She did try some things out with George when they first got married but he wasn’t very interested in adventure so she put up with it.
She told me I was only the second person ever to see her naked.
After a little while Eileen got up and took a look out of the window. She said that the girl next door was just there getting into a car. “I bet she hasn’t had a good fucking this morning like I have” with a giggle in her voice.
“I could get quite used to this” she said. “are we going to do this again,Peter?” Her voice had a sound of anticipation in it.
“Of course we will”.
“Same again next Saturday I hope”
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