Losing Virginity to an Older Woman

Q: Dear Ava. Hi, I’m an 18-year-old virgin and I want to lose my virginity to an older woman, or milf. But I can’t seem to find any willing to do it, and online sites are expensive. – Jacob

A: Hi Jacob. First off, eighteen isn’t that old to still be a virgin. But… I understand exactly how you feel because I too was a virgin at that age and couldn’t wait to lose mine. I thought everyone around me had already experienced sex, and I just wanted to get it over with. The truth is most kids hadn’t (I found out later) and being in a rush didn’t culminate in anything special.

The first time isn’t always memorable, but if it’s with an older woman it’s more likely to be enjoyable. An experienced older woman will take the reins which can relieve a lot the pressure off any performance anxiety you may have. If you come quickly (and this often does happen the first time), she will understand and probably be able to teach you a few tricks, especially if you see her again. She will be more interested in building your confidence than her own pleasure (at least, that’s how I have felt with virgins.)

Dating sites specific to cougar-cub hookups like MatureKiss.com and MILFdating.com can help you to meet an older woman who you know wants to meet a young man. If money is an issue (as it is for many young people), try a mainstream site like OKCupid, where you can specify the age range you are looking for and even state that you are interested in “casual sex.” I don’t recommend saying that you’re virgin until there is an online connection.

Use these first message tips to increase your chances of getting a reply and once you have a dialogue and are going to meet in person, you can reveal that you’re a virgin. I know this all may sound like it will take a while, but know that even older women want to be treated like ladies.

And one last piece of advice, if you are looking online, I would suggest looking for an older woman under thirty-five. Many of us cougars have an age range we are comfortable with. For me, it’s fifteen years. Although I recently had a short-term fling with someone sixteen years younger, and it was great!

Have a little faith, Jacob… and patience. It may happen when you least expect it.

Need advice on dating, relationships, or sex? SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Cougar World newsletter. -xo Ava

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