Sex advice?

June 3, 2012 3:06 PM

I'm in my mid to late 20's, and am about to have sex for the first time in nearly a decade. And could use some advice.

First thing first, I'm a male, mid to late 20s, and I'm about to have sex for the first time in about a decade. I guess I'm just going to quote Joe Miller; "Now, explain it to me like I'm a four-year-old." I'm nervous about the fumbling around in the dark and the actual penetration. Previous sex has all occurred with an equally inexperienced individual so she "led me in" so to speak. Recently I reached this point with an individual but I couldn't go through with it because I honestly do not know what's standard practice, and/or how to proceed. We can skip the answers about using protection, I've got that covered. I'm really a pretty well-rounded individual but this area of my life just never evolved. Also, I'm sure I'll get the responses stating to just be honest; I have told her of my lack of experience, I just don't want to seem like a complete rube.

I set up a throwaway email if anyone wishes to reply directly: [e-mail]
To clarify, email was made with a sense of levity. I am not technically a virgin.

posted by anonymous to Human Relations (32 answers total)

Foreplay is where you make your money. Warm your lady up first, and it's hard to go wrong from there.

The key to foreplay: the clitoris. Find it. Make it your friend. You will be a winner.
posted by Fister Roboto at 3:16 PM on June 3, 2012 [1 favorite]

So, what's your question young man? How to have sex?
Everyone does it their own way, but basically you start out with kisses/nibbles/caresses moving into foreplay however you may conceive it - peeling off the clothes, touching, licking, rubbing, kissing her breasts and privates - then when you feel she is very moist and/or she indicates that she wants to be penetrated (by a thousand and one ways: like moving her hips, "leading you in", saying it outloud, etc..) then you penetrate her. Once she is penetrated, you start the back and forth movement while keeping on kissing/caressing her until you climax. That's basically it.
Keep an open mind, be willing to be playful and take your time. And maybe go watch some tasteful porn for variations on the theme. Practice makes perfect.
posted by ruelle at 3:26 PM on June 3, 2012

This might sound stupid, but have you considered reading at Scarleteen? I know it's aimed at younger people, but possibly the clear explanations/suggestions will be helpful for you? They even have a First Intercourse 101 that looks all right, but I think there's a lot of helpful stuff there. Good luck, and have fun!
posted by thylacinthine at 3:27 PM on June 3, 2012 [4 favorites]

Breathe deeply.
Start slowly and
work
your
way
towards
erogenous zones.
Don't linger anywhere for too long.
NIPPLES
love tweaking.
posted by sibboleth at 3:28 PM on June 3, 2012 [2 favorites]

Yeah, finding the clitoris is a step. But for the love of all things holy, please be gentle with it unless you're told otherwise. And don't start there.

Kissing, touching, appreciating is part of it to. A lot more than wham bam bang on the clitoris.

I can't think of one right now but a good European film love scene might help with the introduction. Then the actual intercourse is led by your partner.

I've slept with more than one person and each one has had their own preferences, styles and habits. To be honest, it's like having a new favourite restaurant each time. So long as I get an orgasm, I don't really have any strong preferences for the rest of it. BUT I'm a 50% partner in the responsibility for my own orgasm which means I have to communicate what I want. And I'm also a 50% partner in my partner's orgasm. So he has to communicate what he wants.

But, that said, orgasms are great but not common the first time a couple gets together.

Good luck possum, I'm sure you're terrified. But if you can go slow and gently till you're given orders to do otherwise, you'll be great.

(If you want some more big sisterly frank advice, you're welcome to email me. I'm a very old, married lady over 40 but I remember this all to well. Hugs for you!)
posted by taff at 3:30 PM on June 3, 2012 [5 favorites]

Remember, it's all fine. Sometimes, even experienced people will fumble, miss the target, have performance issues. Just be sweet with each other, and open (so to speak), caress, kiss, smile, look into each other's eyes.

In terms of finding the spot, might I suggest, after foreplay has ensured a sufficient level of wetness, continue to caress the area with your fingers so that when you aim your penis, it'll be in the right direction. Don't feel bad if she helps to guide you. Missionary is probably the best/easiest for a beginner.
posted by b33j at 3:35 PM on June 3, 2012

Go slow. Relax.

Please remember that your partner is a person and not a cum receptacle. The only time I've ever had bad sex was the time I felt like I might as well not have been in the room. This goes for foreplay and all, but also just the notion that sex is something two people who actually like each other do together.
posted by Sara C. at 3:36 PM on June 3, 2012 [7 favorites]

Spend as much time as you need getting into each other's physical and mental space by talking about it. Pre-sex talk isn't just about protection and general expectations for the relationship--talking about what both of you like or think you would like when you're touching each other and completely in the other's space gives you lots of information and turns you both on and establishes communication as a part of your sex life. Directly ask where she likes to be touched and how, if she wants to hold you and guide you in during penetration or if she wants to touch herself while you do it. Ask her what helps her recapture the moment if you lose sight of it and it gets awkward somewhere in the middle (it's normal for that to happen, btw)--kissing? humor? a change of position? more explicit touching? Ask her what makes her really hot above all else and tell her what that is for you. Dig into your eye contact and incidental touching while you talk and tell her why you want her as directly as you can manage, and let it get dirty if that feels right.

When you start this way it makes it easier and easier for both of you to learn how to get what you want and need from each other in your sex life and to get into an ask culture place with each other. It's so much less about what and where and a lot more about learning how to be comfortable with what is a lot of physical and mental intimacy. The sex you'll have with this woman belongs only to the two of you and can be anything you both want as long as you take a minute to ask what it is you want in the clearest terms you can manage in as comfortable a context as possible. So get into bed, sure, and touch her, absolutely, but pillow talk should really be the thing before and during and should feel as good. If you figure out what to do because she has told you and you have told her you'll be so revved up at that point that the last thought anyone will be having is about logistics. I'm always amazed at how hot it is to have my partner ask me explicitly if I want something in explicit language--once it's out there like that, out loud, whether or not whatever it is gets done 'right' doesn't even matter because I'll get there.
posted by rumposinc at 3:43 PM on June 3, 2012 [1 favorite]

If it were me, I'd give my partner a heads up that it's been a while for me. I wouldn't go on about the how or why or when, just something like "just FYI this is my first time in a little while". No one's going to think less of you -- on the contrary, it might be flattering to your partner -- and it would help to temper expectations for the both of you.
posted by no regrets, coyote at 3:56 PM on June 3, 2012 [1 favorite]

All nipples DO NOT love tweaking. I'm constantly having to shove people away from my nipples, because of this sort of preconception.

Ask what she likes. She may not say "yes, this" but it shows that you're willing to go with what she does, or doesn't; eg. me and not being anywhere near my nipples, thanks.

Re: the clitoris, some ladies like a lot of attention, some not; some are highly sensitive and need only the barest of pressures, and some a bit more. Asking is a great way to find this out--start off gentle, and then ask, more? if she shoves your hand away, then it's a good sign that you're not doing it how she likes. Ask her to show you, by putting her hand upon her clitoris, and then following the movement she makes.

Talking relieves some of the pressure of performance, and can generate some playfulness, so that when someone gets a cramp (it happens!) it becomes an amusing thing. Also, what coyote said, re the FYI.

Putting it in can be just a matter of putting her hand upon you, and then say, "put me in" if you like :)
posted by owlrigh at 4:07 PM on June 3, 2012 [1 favorite]

A woman once wrote, "A few times in my life, I've had the pleasure of a lover who understood it's a game to play instead of a project to be accomplished."
posted by Trurl at 4:10 PM on June 3, 2012 [35 favorites]

INTRO
-Hugging & Kissing (Lips [mouth], neck, ears, stomach, between the breasts)
-LIGHTLY touch her cheek (face)
-Focus on how enjoyable this is

SECOND MOVEMENT
-Take off the rest of their clothing (if necessary at this point AND if he / she is okay with it, and take your TIME dammit)
-Take your time
-Take your time
-Hey, this is a good time to rub the thighs. LISTEN: Don't get crazy here. And I strictly mean the thighs. Don't get greedy. Your patience will pay off
-Rub the small of the back - it's right above the buttocks (fun fact)

THIRD MOVEMENT
-Yer naked, right? Like, really naked? Good. Now you are both ready.
-Focus on her
-Go for some rubbing of the vagina, around the clit but not the clit. Spend some time there and get familiar with it, but don't rub around like it's a dry erase board with your worst secrets written on it. Gentle, my good man, is key here.
-Keep your attention on her. Make sure she's enjoying herself!

FOURTH MOVEMENT
-Let nature run it's course. Take your time.
-Take it slow at first, though. Again, don't go crazy (i.e. you should not feel like you are reenacting an online video. You know what I mean)

GRAND FINALE
-Well, now you just need to go with the flow. Things are getting a bit wild now, right? The neighbors might call the cops? That's good!
-If she seems like she's close to finishing, cross the finish line.
-If she hasn't, be a man and help her out (see the third movement - you might need to backtrack here)

ENCORE
-Cigarette

AND/OR

-Shower
posted by glaucon at 4:23 PM on June 3, 2012 [5 favorites]

I think you should go about it like you probably did the first time and like the way probably many people started out- just slowly, like you're still in high school or whatever. Focus on everything else first and don't make 'having sex' the goal. In fact isn't that what happened on the 40 year old virgin? That they 'couldn't' have sex for the first month or so? All of the foreplay stuff is very exciting and sometimes gets lost a bit later on. Enjoy this part. If she cares about you and wants this to happen as well then you are going to be fine.
posted by bquarters at 4:25 PM on June 3, 2012

I think one of the sexiest things that a guy has ever done with me was whisper in my ear, "This is what I've been waiting for all week." and then just start exploring. For me, knowing that my partner was so excited to do this with me and that he was pretty much just drinking the whole experience in was freaking awesome. Talk with her. Ask her questions. Tell her to guide you. Issue compliments. Don't be afraid to swear -- or laugh. Whatever you do, just have fun. Enjoy yourself, enjoy her, and don't get all fussy over making her come.

Sex is awesome.
posted by These Birds of a Feather at 4:28 PM on June 3, 2012 [1 favorite]

There is actually really no standard practice here. It sounds like for instance you're wondering "Okay, does she grab it and put it in? Or do I grab it and put it in? Or do I just sort of thrust in that direction and hope it goes in on its own?" And the answer is, yes, all of those are viable options.

There is sometimes fumbling. My wife and I still have our comically awkard moments and we've been doing this on and off for over a decade. Oh well.

Honestly, as long as you keep your cool and don't completely flip out, you'll be fine. Nobody is going to be like "Well, I thought I wanted to sleep with you, but you favor the Overhand Snozzwangler penis insertion technique and I only like men who use the Inverse Trombone penis insertion technique, so you'd better put your pants on and leave right now."

Admitting it's been a little while — in a "oh hey I'm glad my life is improving and I've met you" way, not in a self-flagellating or shame-ridden way — is also a good idea.
posted by nebulawindphone at 4:28 PM on June 3, 2012 [17 favorites]

There is no standard practice. Think sexy thoughts and go exploring.
posted by mleigh at 4:38 PM on June 3, 2012

The majority part of her body is similar to your own. For those parts, try touches that you can imagine would feel good on yourself, be that grabbing the muscles of a leg or tickling the skin of her belly. With everything you do, it's nicer for her to say "harder" and push herself close than to say "that hurts" and pull away.

If she is more experienced and not too shy, let her be the one to take initiative for actual intercourse. Start missionary or, if she's ok with taking the lead, her on top. If you end up in charge of the actual penetration, be slow enough that she can correct with her hand if you're heading off course. Especially with a condom on, it's quite normal to not be able to navigate by touch.

Your fucking movements don't have to be big. You can stay pretty far inside until you have some hang of it and a rhythm so you don't accidentally slip out. If you do, no big deal though. Many things can go wrong and it's always no big deal.

Try to arrange the lighting so it's comfortably mellow but not pitch dark. You want to see what you're both doing and also what her face expresses.

And keep in mind that it's as important to her that you enjoy as it is to you that she does. Give her some feedback and improvise together.
posted by springload at 4:43 PM on June 3, 2012 [1 favorite]

As a way into middle age lady with a fair amount of experience in this arena I would say first of all remember that each experience is different. Anticipation is nice, but sex doesn't really happen according to "a plan".
Making out first- the foreplay part, including kissing, hugging, sucking, caressing is important for both participants. I am betting that your lady partner will be able to help more than you think. There is NO standard practice as far as I have ever been able to tell, other than caring that both of you are having a good time.
Just try to relax as much as you can and know that you really do learn more with practice. You have many years ahead of you to practice and learn and love ,okay?
posted by Isadorady at 4:49 PM on June 3, 2012

"A few times in my life, I've had the pleasure of a lover who understood it's a game to play instead of a project to be accomplished."

QFT!
posted by PlantGoddess at 5:08 PM on June 3, 2012

You've had some good tips so far. Other things to remember, everyone fumbles around a bit, things go wrong it is normal do not start panicking. The correct response is to ignore super embarrassing things like body noises, apologize for anything that might hurt but keep going say getting their hair caught under your hand or an elbow to the nose and not laughing if one of you falls out of bed. I have done all those things, in the past few weeks, with a partner I've been with for 7 years.

As you asked directly about it, if by the penetration bit you mean lining up things down below so you can get to the actual sex act. If your partner is reasonably experienced if you are fumbling a bit she will probably reach down and help you guide things to where they are supposed to be. More guys than you think need a hand getting things lined up. Getting her nice and excited before hand really helps make entry easier for everyone.

Also don't head straight to maximum velocity once you get started, move along slowly so things can stretch down there to accommodate you so it's more comfortable for her and for you to get an idea of how deep you can go, nothing can kill an erection faster than thrusting away and accidentally pulling out and jamming your willy full bore into a pelvic bone, like my now husband did the first time.
posted by wwax at 5:29 PM on June 3, 2012 [1 favorite]

The correct response is to ignore super embarrassing things like body noises, apologize for anything that might hurt but keep going say getting their hair caught under your hand or an elbow to the nose and not laughing if one of you falls out of bed.

Conversely, you could take the approach that it's all pretty dang funny when you really think about it, and laugh at it together. But I'm guilty of having had to call a temporary halt to the action more than once to recompose myself after a giggle fit.

And even having a few notches in my lipstick case, I still find that the first time with any new partner, no matter the experience level, tends to be lots of elbows in the wrong place and "Oops, sorry!" and general fumbling and bumbling. I find it very sweet, actually, and sort of miss the awkward early trysts once we've gotten our groove dialed in in later days.
posted by quivering_fantods at 7:25 PM on June 3, 2012 [1 favorite]

Also: bring lube.

(Not sure if that falls under your "got protection covered" heading, but just in case it doesn't...)
posted by quivering_fantods at 7:31 PM on June 3, 2012 [1 favorite]

I've heard advice that says you should ask the woman to show you how she masturbates (assuming she does, of course), and then (gently) start doing what she just demonstrated.

(Then again, I can't really vouch for the efficacy of that advice from personal experience, as it has been nearly two years since the last time I had sex.)
posted by AMSBoethius at 7:36 PM on June 3, 2012

I am only one datapoint, but being asked how I masturbate would ick me out beyond words. Being asked what I like is just fine.

Also, don't imitate porn, please.
posted by Sidhedevil at 9:13 PM on June 3, 2012 [2 favorites]

As an addition to what quivering_fantods said, if you can, bring two types of lube: regular lube, and glycerin-free lube.
posted by These Birds of a Feather at 10:52 PM on June 3, 2012

Just get glycerin-free lube. Don't use condoms with spermicide as they frequently cause MASSIVE irritation of woman-bits. Let go of embarrassment about squelchy-noises, any insecurity over your own flabby or chubby body parts, or any expectations about sex garnered from any sort of film, mainstream or porn.

Sex is intimacy. Intimacy is the giddiest, most lovely secret because you get to define it as you go. It also means you're both experiencing and acting stuff that is eye-rollingly funny, as long as you remember that no-one else can see you. There's no reason to suppress that giggling and joy and curiosity and wonder; you're the only ones in that moment.
posted by desuetude at 12:07 AM on June 4, 2012 [1 favorite]

Seconding to make sure your condoms are spermicide-free. I've gotten many an unpleasant UTI from spermicide and no one wants that kind of a party favor.

My own partner's advice to me when I was getting stressed out about sexy-times post-baby: "Hey, just have fun. It's a party! Stop thinking so much about it." Dude was right.
posted by sonika at 6:07 AM on June 4, 2012

Someone on reddit made an epic comment about this very thing. Lots of ladies approved of his advice!
posted by frecklefaerie at 7:44 AM on June 4, 2012 [7 favorites]

Take your time and FOCUS - don't let outside distractions or thoughts get between the two of you or the enjoyment of what you're doing together. Watch her face, her eyes, her body as you touch her, see and feel how she responds and act accordingly.

Don't be self conscious. Ask for what you want. Ask her what she wants. When she does something that feels good, say so. Doesn't have to be weird; it's one of the most intimate and wonderful conversations you can have!

Think of it as a journey, not a destination. Enjoy the whole thing. Penis-in-vagina doesn't have to even happen for you both to have an amazing, satisfying experience - and as a matter of fact, endless teasing can be incredibly rewarding.
posted by thrasher at 8:48 AM on June 4, 2012

The hottest thing a man has ever said to me in bed was "What do you need?"

What made it hot was that he didn't assume that he knew already.
posted by griselda at 10:12 AM on June 4, 2012 [2 favorites]

If there's even the slightest doubt that she's ready for insertion, be sure to confirm with her before you stick it in. A simple "ready?" could help avoid discomfort/awkwardness if she needs a little more foreplay time.
posted by delight at 3:28 PM on June 4, 2012

I'd prefer, "Shall we?"
posted by taff at 3:29 AM on June 5, 2012 [1 favorite]