First time - need advice

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First time - need advice

Unread postby ExecGuy89 » 10 November 2020, 20:13

Hi, I found this site and hope it can help me navigate what I am about to do.

I’m recently divorced from a woman and late 30s. I’ve decided to explore my sexuality and have a date this weekend with a gay man about my age. He knows that I am new at this.

I have experimented with sucking in college and now now looking at everything. Top and bottom intrigue me sexually. My date and I agreed to dress up in business suits because it has been a desire of mine to hook up in a suit and tie. I have met him in a Starbucks and looking forward to getting to know him better.

I’m looking to make this incredible and want to try new things. My date asked me to wear over the calf socks and I am wearing a sexy new red striped pair with a blue suit.

My question - what style of underwear should I wear? I am pretty boring in that area (tighty whities) and want to expand.

Are there styles and brands that you can recommend? I am planning to do much anything sexually with this guy that feels good in the moment (safely of course).

Thanks
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Re: First time - need advice

Unread postby Jasper1 » 10 November 2020, 22:55

LOL - divorced, first time with a man and you’re worried about what type of underwear to wear!

Since your friend already requested the style of socks he wants you to wear. Why not ask him about his preferences on the underwear also. My preference would be boxer briefs but I’m pretty boring in that area. To be fair, I don’t think you’ll have them on for long.

Overall I think the suit dress code is a great idea!

Let us know how it goes..
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Re: First time - need advice

Unread postby Twilight66 » 15 November 2020, 05:09

What about surprising him with NO
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