Sleeping with Strangers

A lot of people will tell you they need a certain level of emotional intimacy in order to have a good sexual connection. This is not always the case.

After I have been with someone long enough to let them see me without makeup, on fat days, after I get back from the gym but before the shower, when I'm sick and coughing up mucus, etc etc etc, then I am able to be entirely open during sex.

However, in the beginning of a new relationship, one where I really like the person but we haven't been going out that long, I find it hard to open up. In fact, I find it easier to have sex with someone I hardly know or barely like than someone I really like but have only been dating for a couple of months. Maybe this is why I have so many meaningless flings.

The Fun of a Fling:
- It doesn't matter what you say or do in bed. If they don't like it, you'll never know because most times you don't stick around much longer than it takes to wiggle back into your clothes.

- You can be as selfish as you want. Hey, who are they to complain? They are getting random sex. The least they can do is shut up, enjoy it and let you do your thing.

- You can spend a lot less time worrying about what your body looks like and if they other person likes what they see. They should just be happy they get to see it at all.

- If something awkward does happen, end the fling. Just walk away from it and never think about that horrible incident again.

- Here I like to enforce the "if we have sex, we both get an orgasm" policy.


Dating and the Awkward Initial Sexual Encounters:
- You like this guy. You want him to like you too. It's not always easy to feel confident in your body, sexual ability and sexual preferences once you being to worry about what he thinks. It's worse that since you like him, what he thinks actually matters to you.

- You need to be less selfish and actually spend time making sure both people are happy.

- Since you are in a relationship, this implies you will be having sex many more times. This means you have to put in the time and effort to teach him what to do and explain what works well for you. For me this is always hard to do.

- Here, at least at first, I find it hard to communicate what I want and thus the mandatory orgasm policy goes out the window.


This blog is all about trying to be less intimidated by sex and learning to be open and enjoy the experience more. So I am going to propose and action plan to change the awkward new dating sex into the amazing I don't care because I won't see you in the morning  (expect for in this case you will) variety.

How to Make Early Dating Sex Better:
1. Guide his hands- If you need clitoral stimulation, like many women do, and your guy is either not touching you at all or not touching you in exactly the right place, move his hand to where you want it and help him out.

2. If this doesn't work, stop whatever you are doing (don't feel bad- not your fault he's taking so long to catch on!) and show him what you want via a demo. Then let him try again. Don't continue the sex til he gets it.

3. Use the breathy request. This is when you pretend you are really into whatever is going on, so into it in fact that you mix breathing and moaning with talking and whisper what you want him to do. (Really you've been sitting there for 5 minutes thinking about how bad this is and how much you wish he'd do something else...but he doesn't need to know this). Because you seem so turned on and in the moment, he really has no choice but to oblige. He's not going to want to break your focus plus seeing you so turned on will turn him on. This means you don't have to worry he'll think that you giving him directions is code for he's doing it wrong (even though it is).

4. If this still doesn't work, talk to him about it. Explain what you want him to do. If you feel uncomfortable about it, tell  him. I find that saying I feel stupid often makes me feel less stupid since it usually prompts the guy to reassure me and encourage me to be open.