Has anyone had the experience of having any form of sexual activity while (say) 14 to 16 years old with a woman aged 50 or even more? The reason I ask is not because I have, but because I may have missed an opportunity when I was that age and it has been a what if of mine ever since.
I grew up in the 1960s (long before the internet and when even top shelf magazines could not show a womans sexual parts) and so opportunities to see the opposite sex naked were very limited. When I was 15, both my parents worked full time and so they employed a cleaner who came in for a couple of hours twice a week. She was 60, short and a little dumpy, and with a face that was not even attractive - but she did have large breasts and, when she leant forward, a glimpse down her blouse revealed a deep cleavage. For a 15 year old full of testosterone in those prim days, this was dynamite and she became a regular wank fantasy. I knew that her husband was a lot older than her, and a semi-invalid, and so, in my wank fantasies, I reasoned that she was not getting any sex and I fucked her in the safe knowledge that she was too old to become pregnant.
One day when I was on school holiday and my parents were at work, she let herself in with her key to do the cleaning. She put her head around the downstairs lounge door to say hello to me and then set off to work. A while later I came out of the lounge and saw that she was kneeling half way up the stairs vacuuming the stair carpet with an extension tube on the vacuum cleaner. As I watched, she pulled up the tube to start working on the next stair and, as the tube rubbed past her skirt, it lifted it up and laid it neatly onto her back. This not only presented me with a perfect view of her (unfortunately non-revealing) knickers, but also her stocking tops and tightly stretched suspender straps, topped by an expanse of white cellulite thigh. At first I thought that she had done it because she knew I was watching, but I knew that it was a fluke - there is no way she could have repeated the trick now matter how hard she tried. I watched for a minute or so until she realised - perhaps she felt cold - and she reached back to straighten it out. I thought that she might look around and so I quickly stepped back into the lounge.
During that minute, I had wondered whether I dared to walk up the stairs and lay my hand on her thighs. Could it be that she really was sex starved and would have liked a willing young lad with powers of recovery (just as well because I would have shot my bolt the moment she touched me). However, the thought of getting it wrong - after all I was still legally a minor - and her telling my parents that I had fondled her was too strong and I didnt make a move. In the months that followed there were occasions where I felt that there was an opportunity to say something to test her out her willingness, but I could never think of how I could put forward an innocent explanation for what I had said if she took offence. So I never made a move and then she stopped working to look after her husband full time. Strange to think that she must be now long dead.
Over the years I have wondered whether I missed the chance of losing my virginity to a much older married woman and over the years it has continued to be an occasional wank fantasy. In my favourite fantasy, I walk up the stairs and fondle her and she just carries on working; she doesnt encourage me or discourage me. I continue to fondle her stocking tops and thighs before pulling down her knickers and entering her wet pussy from behind. As I fuck her, I reach around her, slide my hands under her blouse, upclip her bra and fondle her pendulous breasts.
Of course, I could have lied and said it really happened, but it didnt. However, someone else may have had more courage and gone for it. If so, please let me know know the scenario and what happened. Even if you missed out like me, it would still be interesting to hear.
I grew up in the 1960s (long before the internet and when even top shelf magazines could not show a womans sexual parts) and so opportunities to see the opposite sex naked were very limited. When I was 15, both my parents worked full time and so they employed a cleaner who came in for a couple of hours twice a week. She was 60, short and a little dumpy, and with a face that was not even attractive - but she did have large breasts and, when she leant forward, a glimpse down her blouse revealed a deep cleavage. For a 15 year old full of testosterone in those prim days, this was dynamite and she became a regular wank fantasy. I knew that her husband was a lot older than her, and a semi-invalid, and so, in my wank fantasies, I reasoned that she was not getting any sex and I fucked her in the safe knowledge that she was too old to become pregnant.
One day when I was on school holiday and my parents were at work, she let herself in with her key to do the cleaning. She put her head around the downstairs lounge door to say hello to me and then set off to work. A while later I came out of the lounge and saw that she was kneeling half way up the stairs vacuuming the stair carpet with an extension tube on the vacuum cleaner. As I watched, she pulled up the tube to start working on the next stair and, as the tube rubbed past her skirt, it lifted it up and laid it neatly onto her back. This not only presented me with a perfect view of her (unfortunately non-revealing) knickers, but also her stocking tops and tightly stretched suspender straps, topped by an expanse of white cellulite thigh. At first I thought that she had done it because she knew I was watching, but I knew that it was a fluke - there is no way she could have repeated the trick now matter how hard she tried. I watched for a minute or so until she realised - perhaps she felt cold - and she reached back to straighten it out. I thought that she might look around and so I quickly stepped back into the lounge.
During that minute, I had wondered whether I dared to walk up the stairs and lay my hand on her thighs. Could it be that she really was sex starved and would have liked a willing young lad with powers of recovery (just as well because I would have shot my bolt the moment she touched me). However, the thought of getting it wrong - after all I was still legally a minor - and her telling my parents that I had fondled her was too strong and I didnt make a move. In the months that followed there were occasions where I felt that there was an opportunity to say something to test her out her willingness, but I could never think of how I could put forward an innocent explanation for what I had said if she took offence. So I never made a move and then she stopped working to look after her husband full time. Strange to think that she must be now long dead.
Over the years I have wondered whether I missed the chance of losing my virginity to a much older married woman and over the years it has continued to be an occasional wank fantasy. In my favourite fantasy, I walk up the stairs and fondle her and she just carries on working; she doesnt encourage me or discourage me. I continue to fondle her stocking tops and thighs before pulling down her knickers and entering her wet pussy from behind. As I fuck her, I reach around her, slide my hands under her blouse, upclip her bra and fondle her pendulous breasts.
Of course, I could have lied and said it really happened, but it didnt. However, someone else may have had more courage and gone for it. If so, please let me know know the scenario and what happened. Even if you missed out like me, it would still be interesting to hear.