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By (user no longer on site)
over a year ago
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"I'm going to try my hardest but know I'll be shy! What if she feels the same?! I wouldn't know what to do lmao. I definitely would  "
chat casually to her say u have a thing for older ladies one in particular ask how you should approach her then when she tells u say if that was you would you be interested lol |
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By (user no longer on site)
over a year ago
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Definitely go for it. No need to be crude, just be nice to her. You could tell her that you so wished you weren't so young and could have asked her out a long time ago. Tell her you don't want to embarass her, but you just had to let her know. If she doesn't slap you down immediately, you will be fine.
Oh, and you're old enough not to worry what your mum thinks. None of her business - tell her politely but firmly. |
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By (user no longer on site)
over a year ago
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"Man up and do it. Your only gonna get jealous if dont"
Don't be like that- not an easy thing in the real world to come onto yr mums mate. Also it don't matter how old u are - if yr a decent person yr mums feelings should be considered |
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By (user no longer on site)
over a year ago
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I'm not saying his mum's feelings don't matter, but Calvin is a grown man, and his mum shouldn't interfere in things like that. Really I'm sure she wouldn't.
I know a lot how OP feels, and I wish I'd had more courage myself. |
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"Man up and do it. Your only gonna get jealous if dont
Don't be like that- not an easy thing in the real world to come onto yr mums mate. Also it don't matter how old u are - if yr a decent person yr mums feelings should be considered "
I know i couldnt such a shy person didnt mean it in a bad way |
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"Definitely go for it. No need to be crude, just be nice to her. You could tell her that you so wished you weren't so young and could have asked her out a long time ago. Tell her you don't want to embarass her, but you just had to let her know. If she doesn't slap you down immediately, you will be fine.
Oh, and you're old enough not to worry what your mum thinks. None of her business - tell her politely but firmly."
Alternatively stand with your cock out rubbing furiously at your bellend while she's measuring up  |
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By (user no longer on site)
over a year ago
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Seriously, tread cautiously, firstly, flirt, then plant the seed in her mind that you would, over time she will be thinking about it. And if she is willing, she will let you know, This is a no pressure situation.  |
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Take it slow and watch how she behaves around you. Her body language is always a give away. Best thing I look for is body mirroring. This works best if your sitting opposite her. If she starts copying your posture sub consciously, like if you're leaning your face on your hand and she does the same. Change positions and watch what she does. I do this alot and you'd be surprised how well it works. Best of luck and keep us updated |
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By (user no longer on site)
over a year ago
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Lots of good advice here... take it slowly. She will know what a nice guy you are. Be yourself and let her know how much you feel attracted to her. I can tell from the thread how much everyone is rooting for you. A beautiful thing could happen. |
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There is some good advice on here.
Having had both relationships and brief encounters with a few older ladies in my younger days...
I agree - take it slow.
The curtains idea is a good opportunity to chat with her 1-on-1.
Women are more open to sexual advances if you can make them laugh and have a fun time in your company... so flirt and joke, and don't be affraid to be a little cheeky !
Introduce a little body contact but in a fun way. When you're talking to her... HOLD her gaze for a few seconds longer than normal... SMILE at her in a mischievous way and if you feel confident enough, give her a wink !
If she is interested, and you flirt with her, she may well seduce YOU, if she knows you wouldn't tell your mum.
Good luck - don't rush things...
And enjoy the experience !
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By (user no longer on site)
over a year ago
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Years ago i had a crush on my mums best friend. She used to tease me, sit with her legs parted opposite me and flash me her knickers. This went on for a couple of years. Then on my mums 50th we had a party, it was icey outside so i offered to walk he home. He had heels on and would have probably fallen. She linked my arm and i walked her home. She invited me in and offered me a drink. We sat chatting and as we usually did we sat in the kitchen, she sat on the worktop and i was sat on a chair. Her kegs started to part and i couldnt help but look, she just grinned and said ' you like that dont you ' i blushed like hell and tried to deny it but she laughed and parted her legs wider ' you always look when you are here '
I tries to deny it but she was having non of it. She jumped off the counter and poured us another drink and vanished. She came back in just her dressing gown and sat bach on the counter, this time when her legs opened she had no knickers on ' thought you may want a better view '
Lets just say things progressed well from there |
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By (user no longer on site)
over a year ago
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"Years ago i had a crush on my mums best friend. She used to tease me, sit with her legs parted opposite me and flash me her knickers. This went on for a couple of years. Then on my mums 50th we had a party, it was icey outside so i offered to walk he home. He had heels on and would have probably fallen. She linked my arm and i walked her home. She invited me in and offered me a drink. We sat chatting and as we usually did we sat in the kitchen, she sat on the worktop and i was sat on a chair. Her kegs started to part and i couldnt help but look, she just grinned and said ' you like that dont you ' i blushed like hell and tried to deny it but she laughed and parted her legs wider ' you always look when you are here '
I tries to deny it but she was having non of it. She jumped off the counter and poured us another drink and vanished. She came back in just her dressing gown and sat bach on the counter, this time when her legs opened she had no knickers on ' thought you may want a better view '
Lets just say things progressed well from there"
tell us more with your own post |
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"Years ago i had a crush on my mums best friend. She used to tease me, sit with her legs parted opposite me and flash me her knickers. This went on for a couple of years. Then on my mums 50th we had a party, it was icey outside so i offered to walk he home. He had heels on and would have probably fallen. She linked my arm and i walked her home. She invited me in and offered me a drink. We sat chatting and as we usually did we sat in the kitchen, she sat on the worktop and i was sat on a chair. Her kegs started to part and i couldnt help but look, she just grinned and said ' you like that dont you ' i blushed like hell and tried to deny it but she laughed and parted her legs wider ' you always look when you are here '
I tries to deny it but she was having non of it. She jumped off the counter and poured us another drink and vanished. She came back in just her dressing gown and sat bach on the counter, this time when her legs opened she had no knickers on ' thought you may want a better view '
Lets just say things progressed well from there"
OMG don't leave it there!
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By (user no longer on site)
over a year ago
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"Years ago i had a crush on my mums best friend. She used to tease me, sit with her legs parted opposite me and flash me her knickers. This went on for a couple of years. Then on my mums 50th we had a party, it was icey outside so i offered to walk he home. He had heels on and would have probably fallen. She linked my arm and i walked her home. She invited me in and offered me a drink. We sat chatting and as we usually did we sat in the kitchen, she sat on the worktop and i was sat on a chair. Her kegs started to part and i couldnt help but look, she just grinned and said ' you like that dont you ' i blushed like hell and tried to deny it but she laughed and parted her legs wider ' you always look when you are here '
I tries to deny it but she was having non of it. She jumped off the counter and poured us another drink and vanished. She came back in just her dressing gown and sat bach on the counter, this time when her legs opened she had no knickers on ' thought you may want a better view '
Lets just say things progressed well from there
OMG don't leave it there!
"
hes sttarted his own thread called My Mother's Friend |
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