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male
age
51-59,
anonymous
writes: I am friends with a woman much older than me. I think she is probably 70. I am early 50's. I am interested in having a NSA sexual relationship with her, but I don't know how to turn the relationship sexual, as we are just friends and walking partners right now.At her age, I don't think she has had sex in years, and I am not even sure if she would be interested.Please help! Reply to this Question
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female
reader, anonymous, writes (21 January 2023): Your other question asked for advice on how to get sex with married women. Please make your mind up. If this woman knew you think it is fine to interfere in another person's marriage and get them to cheat on their husband and lie to him she would not be at all impressed. Either way with your age etc being what it is I cannot see you getting anywhere with either the marrieds of this one. Women who go on walking groups are simply wanting to walk, not end up in bed with a sex starved man who is selfish.
A
female
reader, anonymous, writes (21 January 2023): No matter her age, nothing excites a woman more than a man who is able to make her laugh and doesn’t take himself too seriously.
Teasing has the added bonus of pushing her emotional buttons and stimulating an attraction for you as a result.
Tease her, and smile as if it’s a joke that only you understand.
The better you get at teasing, the stronger the effects will be.
You must build a comfortable connection between you and her to get her to flirt back.
In other words, she must trust you and feel a connection to you. The best way to build rapport is to engage her in lively conversation and show that you’re a man that can be trusted. There’s no need to try and rush a first date or anything thereafter. Allow the chemistry to flourish naturally.
The more you talk, the more you tease, and the stronger her attraction for you becomes, the stronger your bond and the more willing she will be to take things further with you.
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A
male
reader, anonymous, writes (20 January 2023): She may be interested if she shows the following signs…
she looks at you and holds your gaze
She smiles at you warmly and invitingly
She starts conversations and listening to you attentively
flirt through compliments
touches you flirtatiously
She tells you she’s single--a big sign an older woman is flirting with you
She asks you about your love life
She asks you personal questions
I bet she does these if she is your walking partner. If she does these there must be something there.
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A
reader, anonymous, writes (20 January 2023): You're in a reasonable consensual age to date older-women; and your experience level would make it easier to carry-on conversation and relatively little room for nonsense.
You're a mature man, you shouldn't find it that hard to communicate and relate to older-women. You weren't specific how old, but I'd assume a woman in reasonably good health, still somewhat energetic, and looking for more than just friendship.
I think starting out as a friend and slowly working your way towards more is how you might approach it. I don't think the brash or crass approach would come across well with women brought-up in an era where you treat a lady like a lady. Misogyny and sexploitation is a fad these days.
If this isn't a porn-inspired endeavor, I wish you luck. If it's a way to sexually-exploit or scam older vulnerable-women; I hope you're stopped in your tracks.
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A
female
reader, anonymous, writes (19 January 2023): I am a woman in her 70's. I like having a partner with whom I can talk about my feelings, and have fun with outside the bedroom. I think you should start there. When it is natural and right you can move on to more things. For women, the moves that brought the greatest satisfaction included: kissing, cuddling, hugging, mutual whole-body massage, and oral sex. women of all ages enjoy intercourse, especially holding men inside them.
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A
female
reader, anonymous, writes (19 January 2023): I’m 70 and I hAd been widowed for 10 years when I met a new man. Although life was lonely, I wasn’t looking for a relationship and wasn’t interested in sex. We had been friend and started going out. some months ago we started having deeper conversations discussing things like the meaning of life: what’s it all about? These conversations fostered a new intimacy.I had taken it for granted that I was physiologically unfit for a full sexual relationship and was quite unprepared for my physical response to a hug and a chaste kiss. To my surprise, I had few inhibitions and we joyfully embarked on a pleasurable physical relationship. At first, it wasn’t full intercourse. My partner and i enjoyed our relationship as it was. Gradually, we found things changing. Increased confidence, affection and trust resulted in a fuller experience, and success and pleasure created their own virtuous circle. I felt no need to conform to my own, or anyone else’s, ideas of what a successful sexual relationship might be. Giving and receiving love and pleasure were enough. take it from me, sex is like fine wine. It matures with age. And somewhere along the line, I fell in love.My recommendation would be to ask her in person after a walking session. Tell her that you enjoy hanging out and talking with her, and you think there might be something more there, but if she isn't feeling it, no worries. I would also throw in that you don't want to make it awkward and you are ok with just being friends (if you are).
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A
male
reader, kenny  + ♥, writes (18 January 2023):
 I would just be yourself and don't force things, and let things happen easy and naturally.
Keep on doing what your doing, being friends, keep enjoying your walks, and let things materialise over the natural course of time.
You are in your 50's now so i'm sure you have had many experieinces of how the dating game works.
Have you ever asked her if she fancies grabbing a coffee after one of your walks?. If she agree's to this then that's a step in the right direction isen't it.
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A
male
reader, anonymous, writes (18 January 2023): Why don't you ask her if she is interested to take your friendship a step higher and become your girlfriend?
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