A First Time Story

Shortly after my 16th birthday, my girlfriend of about 6 months invited me over for the day.

We had up until that time been sexually active in every way except for actual intercourse. We had traded pictures, I had fingered her, eaten her out, received head, as well as hand jobs but neither of us had really broached the subject of sex.

In retrospect I probably should have pushed the subject a little more, but in all honesty had been fine as long as I came. So it didn’t matter as long as she was the one to provide it, for it did heighten the experience to have another do it instead of oneself. I saw sex just as another form of this and nothing more.

Anyway the day I went over her mom was out at work and we had the place to ourselves, so naturally as we had done many times before we began playing truth or dare. Each dare getting a little bit raunchier. The excitement was building; each of us had been pushing our boundaries and feeling one another out. Finally she told me that she had wanted to have sex for awhile and had specifically chosen for me to come over that day because her mom was out. So we went into the bedroom, all of our earlier excitement and energy having faded we undressed, and got into bed.

She got on top of me, put a condom on, and pulled the covers over us. I slid in and we began slowly to rise up and down. She grimaced a bit and we took it slow; it ended up lasting about 10 minutes. I remember thinking I would rather get head than this as it provides a lot more pleasure; because it was so tight it hurt her so we went really slow.

But we ended up doing it a second and a third time and a fourth time and jesus christ did I like it after the initial hesitation.

—M.O, male, 21 years old

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Bros Give Advice for First Timers

I asked a bunch of men, friends and otherwise, to share with me the most important piece of information they wish they had known before having sex for the first time. Here’s what they said:

-The vaginal opening is a lot closer to the anus than you think. Most guys think it’s right up front, like their dicks, but that isn’t the case

-Your expectations probably won’t be met the first time – it’s rarely “magical”

-Try to be in a relationship because it’s easier to say if you’re uncomfortable with something

-If you don’t stimulate her before deep penetration, you’re going to have a bad time

-Foreplay and making out makes sex feel better and last longer – don’t just “stick it in”

-Even if your first time is with someone you’re close to (mine was with a gf at the time) the fact that no one knows what they’re doing just makes it an awkward experience. You can visualize and plan it all you want but there’s no way to imagine that

-Foreplay can matter for the guys too, and girls CAN climax so much that it becomes painful

-It’s never perfect – don’t put pressure on yourself, just have fun and enjoy the ride

-The definition of sex is broader than just penetration, so don’t put so much pressure on that one act

-Try to communicate more with your partners from the start, take everything slow, ask them what they like and be open to criticism

-Take the time to make it meaningful and don’t rush

-Don’t rush it. Make sure you’re ready. It’s OK not to be “in love” but just make sure it’s really what you want

-It really does matter who it’s with and not just something to get over and done with

-Girls are sometimes more worried about themselves than what they think of the guy

-I wish I’d known how to get a girl to have sex with me

-Wear a condom