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Five Things I Learned Dating a Girl

Dating this wonderful person pushed me to think about some things in new and challenging ways. Here are some of my favorite lessons that I learned when I dated a woman.

How do I keep him from going in the wrong hole?

totallyconfused19 asks:

I am 23, so this will probably sound silly and foolish but I don't have anyone else to ask these things so here goes: First off, how do you know it's in the right hole? My boyfriend and I were getting involved last night for the first time, and at first it hurt horribly like I was being ripped apart.

He re-adjusted and it still hurt a little but nothing like before, it was mostly just a lot of pressure. Was he in the wrong hole before? How do I keep that from happening? Also his penis is BIG and my vagina is not. How far in should he go? Can he cause damage by going too far? Thanks for the advice.

Figuring Out How to be a Lesbian Safer Sexpert

When I started having sex with girls, there was no one cheering, especially not encouraging me to have safer sex. But over the last few years, I’ve finally begun to feel confident with safer sex, and it’s improved my sex life a million percent. I wish I’d gotten comfortable with it sooner.

I trust him and I want him, but things are moving WAY too fast!

Emme6678 asks:

I'm only 14 and a freshmen and I've only been dating my boyfriend for about two weeks and we have been moving pretty quickly. We have been friends for a really long time and I really like and trust him but I feel like we are moving too quickly. He has already fingered me and I've given him a handjob, and he's been talking about sex. I think I am way too young and I definitely dont feel ready but when we're doing things and I'm really turned on I sometimes actually want to have sex. I am really curious what actual sex is like, and I want to try it. But I know in the long run I will regret it. How do I stop myself from doing something solely based off of my hormones? How do I explain to my boyfriend that I dont want to have sex?

Risky Business: Learning to Consider Risk and Make Sound Sexual Choices

Choices about sex and intimacy will always involve some risks, and making sound choices when risks, emotions and social high stakes are involved isn't something anyone is magically expert at. How can we learn to do it well, and what are some common things that trip us up?

I grew up told sex like I just had was absolutely off-limits: what now?

smf asks:

Hey! I'm 19, and from a very conservative background-Republic, Christian, the whole shebang. I'm a freshman at a pretty liberal college now, and I admit that I've gone the tiniest bit nuts with my newfound freedom. Before coming to college, I'd only made out with three guys - all of whom were Christian, all of whom I was dating at the time. But last weekend, I went home with a guy I didn't know, and I gave him a blow job and he fingered me. I was very adamant about NOT having sex, because I know I want that to be with someone I love.

I'm feeling pretty guilty now, though. Everyone would be so disappointed back home, because it was made clear to me that EVERYTHING is off limits till marriage. It felt great at the time, but do you think it's bad because I didn't know him at all?

He (mostly) seems nice online: should I meet him in person?

simonewheat asks:

I'm 13 and I really need some help. I have been talking to this guy for ages on my phone and texting him. We have Skyped, and I know he might be 'one of those older people who have random children acting for them and they have voice filters' etc, but he has Facebook and I know loads of people who know him, but I just haven't met him. He is really nice and we both wanna meet each other... We decided we were gonna meet and I'm really excited. He says he wants to finger me, and he want me to give him head, that's fine because I have done it before so all's cool. Then when he asked if I wanted to have sex with him, I got creeped. Just need someone to say if I'm doing the right thing or not.

Why Does Masturbation Feel Weird?

simplysarah asks:

I'm 16 years old and a virgin and I'm not exactly sure how to masturbate? That might sound weird but I'm just not sure how I'm supposed to do it. I've tried fingering myself but it always kind of freaks me out and I stop and it never felt that good anyway. The thought of my fingers being inside myself just weirds me out, even though I know it's not weird but it is for me. I guess what I'm wondering is, is this normal? And how am I "supposed" to masturbate if it all seems weird to me?

Am I right to feel like a slag?

BellBrand asks:

Heya: so I have always had really strong principles when it comes to sex and relationships. I always envisioned myself with a nice, steady boyfriend before I would do any more than just kissing. About a month ago I was at a party and out of pure curiosity (not drunkeness) I made the decision to let a boy finger me, but I didn't really know him very well. At Christmas I let another boy finger me who I didn't know (again this was a conscious decision I wasn't drunk). But now I just feel sooo slaggy because it is against what I believe in and I feel so awful in myself. Am I right to feel like this, where should I go from here?

Condoms Breaking? Ur Probably Doin It Wrong.

As we've explained in the past, like here, with proper use, condoms actually break very rarely. The common mythology that condoms are flimsy and break all the time is just that: mythology, not reality. Different studies on latex condom breakage tend to reflect a breakage rate of around .4%, or only 4 breaks in every 1,000 uses. So, if you're having condoms break often, especially before you've even used them a few hundred times, it's not likely something is wrong with condoms, but that something is wrong with the way you're using them. That's not surprising, since a lot of people don't get good information about how to use condoms correctly, or ever see clear, slow demonstrations of proper use where they also get the chance to ask questions.

Since we've been having some users lately reporting patterns of breakage, we thought we'd take a few minutes to walk you through a review of some common issues that tend to make breakage more likely, so that those of you using condoms can avoid br

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Information on this site is provided for educational purposes. It is not meant to and cannot substitute for advice or care provided by an in-person medical professional. The information contained herein is not meant to be used to diagnose or treat a health problem or disease, or for prescribing any medication. You should always consult your own healthcare provider if you have a health problem or medical condition.