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Virgin Territory: 7 Tips for Cubs to Make the First Time a Good Time

It's not like anything you've seen or heard about and it's not as though you'll ever be able to experience it again. Your virginity. And then there's the issue of those hot older women you've been watching.

cub with his cougar kissing on the beach
Relax, be confident and let her guide you while you enjoy.

Maybe one or two of your mates have actually hooked up a smokin' sugar mummy or you've read enough reddit threads to realize that interracial MILFs will try just about anything once.

Sound too good to be true? Well, you'll only know if you try. Don't let your lack of experience intimidate you. After all, everyone has to have a first time, the first time. And, contrary to what you may think, having an older woman pop your cherry may be making the best of a situation, if you get our drift.

Here's how you enjoy the cougar life for your first time.

1. Go Where The Cougar Hunts

The first step to being with a cougar is to go where a cougar will be. Though many older women like to hang out in pubs, clubs and bars, even that scene is getting a bit stale an dated.

The truth is that there are many cougars who are on the prowl -- and not just during the twilight hours. Because older women these days usually have their own businesses to run or they're heavily involved in their family's social lives, they generally don't have much time to head to social spaces like clubs every night.

Let's Be Clear:

We're not saying skip the trip. We're saying, you should consider adding to your arsenal and your chances of landing an older woman for mature dating by making sure you have an online profile on a site dedicated to cougar dating.

2. Find Out What She's Into

The next part of the cougar mating dance is to approach her and make conversation. Don't be intimidated and don't think too much about the gap in your age. After all, she's into younger men so you've already got that working for you.

You want to ease into the conversation. If you're seeing her in person, buy her a drink or smile at her from across the room. If she's with friends, go head and approach her, but do it solo. If you're starting a conversation online, read her profile carefully and use something interesting as a starting point. She'll be impressed at your observation.

3. Do Your Homework

Think of it this Way:

When you're sizing her up, she is too. You don't have to do all the work - your older woman may seem more sophisticated to you (and, honestly, that's half the turn-on, right?) but she's also trying to impress you - in her own way.

You can try and get a sense of how many previous lovers she's been with or relationships she's had but don't bother going through this. If she asks you, you can choose to be upfront, if your MO is to be disarming and earnest. There's something that women love about that.

But you can hold off on sharing this very private tidbit until you're actually between the sheets. Go slow, not fast and don't lead with this fact. Just treat it casually and she will too.

4. Leave Your Expectations At The Door

There are some older women committed to the cougar life that simply want to be with younger men who are experienced but to quite as much as they are.

But there are other older women who delight in the tough of being with a young cub who's a virgin because he represents the chance to show him what sex is all about. She knows she has the ability to make his first time a memorable one and that's exactly what turns her on.

older woman smiling at a young man
Use the right way to approach and talk to her.

So it's really important to be in the moment, do your homework to find out if this is what she's looking for, not allow your virginity to feel like a "liability" but, rather, an endearing state of being - one that she'll relish terminating.

Also, keep in mind that all those rumours you hear about your first time being not as "fun"? Yeah, those are cliches for a reason. More likely than not, just touching and kissing will make you rock hard. Don't feel weird if you come right away

5. Let The Master Guide

Your know that older woman like to take the lead - and with their skill-set, are you really going to protest?

Just relax and let her guide you through the whole experience. With her, it truly is an experience so you can play the good and eager student. She'll teach you how to pleasure her as well as learn what you can and can't tolerate when you're first, ahem, getting it on.

6. Sexy Talk

It's not at all taboo to express yourself to the woman you're going to be having sex with for the first time. Don't assume automatically that simply because she's older, she'll want to keep things quiet or stoic.

In fact, this is one of the ways that you can show her what you do and don't like and, for bonus points, you can ask her to show you what she likes. There's no such thing as a dumb question, right? Especially not when you're doing it for the first time.

very seductive red hair cougar on the bed
An older woman will show you what SEX is about.

7. It's All Uphill From Here

Consider this:

Barely anyone's "first time" is as rewarding or sexy as they show in pornos and television. Real life sex can be funny, sexy, awkward and intimate - all in one night.

So it's best to skip any idealized notions of what your first time will look like.

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Image source: (1) Artem Merzlenko | (2) Martinan | (3) Harris Shiffman | Fotolia.com