First Time with an Older Man

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First Time with an Older Man

Unread postby fabiangb » 6 September 2020, 03:31

So I am in my mid 20's, and for about the past 2 years, I've been corresponding with a gentleman in his late 50's early 60's. I'm super attracted to him (he's in great shape, great personality, good values, avid traveler, and super energetic) and we've had a ton of conversations about finally meeting up and seeing if there's any chemistry and what not. He's been super sweet and we've talked and video called many times, so I know he's who he says he is. (He's also published in the press.)

I think it's finally time to physically meet up and I just wanted to get people's input or any tips on physical intimacy with someone twice my age...I'm fairly nervous b/c I've only been with people my age. He's a bottom and I'm a vers-top (he's more masculine and I'm a tad more feminine).

For context, there have been a few times in the past where we were about to meet up, and I backed out last minute. He was super understanding about my fears/reservations those times, and he's still been a friend and always kept the door open to meet up. By now I've resolved those issues so I'm ready, and we've set a date to meet up.

We plan on getting coffee first and then going to his condo near our downtown area.

When we've spoken about intimacy and sex, I haven't had the nerve to ask if he wants to roleplay daddy/son type of thing, or if he just wants it to be a different dynamic. He has been vague on that, but he has said that he's very laid back and as a bottom, he will let me make the moves (he just asks that I go slow).

Anything I should think, be aware of, or ask about or do? I want him to really enjoy our time together :) I do think there's the chemistry for this to turn into a romantic relationship, but I'm just scared on the physical side if I might mess up.

Thanks for the help gents!
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Re: First Time with an Older Man

Unread postby Jasper1 » 6 September 2020, 17:55

There’s nothing wrong with the age gap. Lots of young guys like an older man and if that’s what you are attracted to and you have others things in common then that’s all that matters.

The Dad/son role play is an odd one for me. Not sure why anyone would find it horny to pretend you’re shagging your dad, or vice versa. It would have the opposite effect on me. Unless it’s something you’ve both spoken about I would not approach this subject.

If you’re physically attracted to each other then I’m sure you can have an active sex life without this type of role play. Maybe it something you introduce later if things are starting to get a bit stale but for sure I don’t think I would need this thought in my head for me to enjoy sex.

Each to their own though :D
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Re: First Time with an Older Man

Unread postby weedan » 6 September 2020, 22:29

Take it a bit at a time. meet him first for the coffee and have sex if you comfortable with him. Just have fun, im sure he will soon tell you if your doing something he is not comfortable with.
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Re: First Time with an Older Man

Unread postby Jzone » 7 September 2020, 04:25

It sounds to me as if you have put plenty of thought into the situation. It's actually great that you have called things off before and he has been patient and willing to stand by until you feel good about it. By this time you should have a good idea of who he is. Of course, things can always be a bit different in person. Meeting for coffee first is great, just know that you are not obligated to follow through if you have any hesitation after meeting.

I suggest you also put some thought into your long range plans and expectations. Other couples (gay and straight) have been successful with a big age gap. Just be real that when you are 40, he will be around 75. That's not necessarily a problem, but it will be a challenge. People in different stages of life tend to have different needs and priorities. If you are both happy with a friends with benefit situation, that is much less of a concern.

When I was active on grinder a few years ago, I hooked up with a few guys half my age. They seemed happy with my patience and approval. I was happy to know I was attractive to guys that age. I kept in contact with a couple of them for a while. I don't think you need to stress about messing up physically.

Relax. Enjoy.
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Re: First Time with an Older Man

Unread postby Eryx » 8 September 2020, 21:21

Seems fine... Go for it, and good luck!

My uncle is 60-something and also very active, fun to be around. He's been dating a guy who's my age (28) for a few years now, and his boyfriend is an absolute delight. We've hung out together a couple of times by now and it's really cool to see people from different generations completing each other so well.
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Re: First Time with an Older Man

Unread postby poolerboy0077 » 8 September 2020, 21:24

Eryx wrote:Seems fine... Go for it, and good luck!

My uncle is 60-something and also very active, fun to be around. He's been dating a guy who's my age (28) for a few years now, and his boyfriend is an absolute delight. We've hung out together a couple of times by now and it's really cool to see people from different generations completing each other so well.

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Re: First Time with an Older Man

Unread postby uncut7in » 9 September 2020, 15:41

I can speak from considerable experience of both casual contacts and a lasting relationship, where there was a large age gap - 54 years for the former and 25 years for the latter. There was never any thought of Dad/Son role play, just two people of very different ages who happened to enjoy each other sexually. So I'd go for it!
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