I’m a 39 year old guy who’s never had a serious relationship. All my life it’s either one offs from a night out or me paying. I lack the confidence of what to do and the thought of the embarrassment is in my head of being seen as a loser amateur by a girl if trying to start a serious relationship. How do I find someone who will actually be cool with “teaching me”, rather than me treating everything as a wham bam thank you ma’am experience.  I have no idea if I’m a good kisser or what else I am good/bad in because like I said no one has been around long enough to tell me.

-- Modified on 10/7/2025 1:42:45 AM

I can teach you anything you’d like. I’d love to be your teacher (or your personal dictionary 😉). I’m patient, sweet, and already have plenty of experience. It would be my pleasure to be there for you. I’ll be back in Chicago 10/13–10/18.

I can teach you. Don't worry. I have worked with many men who have been shy or lacked confidence in bed, and truly that is okay and more common than you think. PM me or email to talk more.

I live in Chicago, I’m in your age range, and it would be my genuine pleasure to help you get “up to speed.” I love to guide, give feedback, and explore without judgment or direction.

Let’s share some quality time together! I offer specials for those who need extra TLC. Look at my website. The more time the more you save $ and the greater lover you will be with the help of my expertise. I just turned 47 and I feel like primetime!

It’s actually more in your head than you think so you need to get to the root of the problem before you can move on with the rest .