I'll be your tour guide for this evening.
March 10, 2011 8:37 PM   Subscribe

A twist on the "I'm a 30 year old virgin" question. The virgin in question is my girlfriend.

I was a late bloomer. I never kissed a woman until I was 22, although after that we dated for years and had lots of hot sex. I never had another girlfriend for 8 years after we broke up. Although I can sometimes effect the appearance of social competence, I'm shy and it's hard for me to approach people.

Until now. She is sweet and funny and fun. She is also very pretty. We've known each other for three weeks, been out a few times, and made out a few times. I don't know if I'm in love, but I do know that I have been walking around the house smiling all the time. I think she is very much into me as well.

She is even more inexperienced than I am. We are both 32. She had never even made out with a guy before me. I am starting to think about sex. How do I introduce her to sex in a way that is safe, fun, and special? I mean, I've only kissed two women in my life. I'M the experienced one?!?

To be clear, I absolutely want to go at her pace. If she doesn't want it, I don't either. But she has said that she thinks about sex a lot. As far as kissing goes, she has been an exceptionally keen "pupil", which I find, well, touching, really. We have not really discussed sex yet. I'm aware that is probably the first step, but I feel awkward, shy, and am unsure what to say.

Any help, advice, or personal experiences would be great. There is a good chance that I'll just show her this question. To avoid pronoun awkwardness, I am a man and to the best of my knowledge we are both straight.

Anonymous because it's not my story to tell, you know? Throwaway: ill.be.your.tour.guide@gmail.com
posted by anonymous to Human Relations (17 answers total) 11 users marked this as a favorite

I feel like sex is best when it just happens. It's not like something that needs to be taught per se. She might be a virgin, but she is 30, so she can be in control. Just let things take their course like you would and if she's not comfortable with certain things, she can tell you. You can tell her that you just want to do what she finds comfortable and I'd leave it at that. Don't act too much like you're going to be her guide into sex or whatever. I'm not in the same situation, but I'd probably find that kind of annoying and patronizing.
posted by elpea at 8:49 PM on March 10, 2011 [3 favorites]

How do I introduce her to sex in a way that is safe, fun, and special?

Honestly, just your good intentions will mean more than all the experience in the world. Every person is different, so even if you'd been with tons of other women, you'd still have to learn her body, preferences, and responses from scratch.

And it never hurts to do some reading, if you feel like it.
posted by you're a kitty! at 8:51 PM on March 10, 2011 [3 favorites]

I dated a late bloomer, too. There's a lot out there, it's a pretty normal thing. My advice is: don't over-talk this. (I won't say don't overthink this; I don't think there is any way to not do that!) Just don't beat it into the ground and take all the fun out with hashing out details and fantasies and no-go areas before the fact.

That doesn't mean that there aren't things to talk about. Logistics, say. Has she mentioned being on birth control, and/or have you laid in a nice assortment of condoms? Have you told her how you went to the doctor and got a clean bill of health? (In other words: go do this now, before she has to ask you to.) Is your bedroom a nice place where a self-respecting woman wouldn't mind spending time? (New sheets! Let me repeat: new sheets, with high thread counts, and no Star Wars prints.)

And then make it fun. It's embarrassing, fluids get in your eyes, everyone either loses their erections or shoots off too early once in a while, people fart at the wrong moments, and the light is never flattering. So instead of ramping up the tension and making it all about THE MOMENT, make it low key and fun more generally, so that every moment is easy and pleasant.
posted by Forktine at 9:05 PM on March 10, 2011 [16 favorites]

Read some Dan Savage columns or listen to his podcasts. What he would say about this situation is to observe the "campsite rule" which is to "leave her in better condition than you found her in".

By being attentive, communicating well, and going at her pace you can't really go wrong. you sound like the perfect guy for her to experiment and learn with.
posted by saturn~jupiter at 9:14 PM on March 10, 2011 [2 favorites]

Yeah, you're not her "tour guide." You're not "the experienced one." You're equal participants in a new and unique sexual relationship which requires no training or previous experience to fully enjoy. Your pedagogical attitude is frankly condescending, and overestimates the value of your negligible romantic history.
posted by milk white peacock at 9:15 PM on March 10, 2011 [8 favorites]

Just show her this question! You'll end up having a great talk. After all, sex isn't rocket surgery; you'll figure it out together. Showing her this post and going through the answers together will be a great communication tool and bonding device!
posted by goblinbox at 9:43 PM on March 10, 2011

I don't know if it changes when you get older, but it's been my experience that losing one's virginity throws the menstrual cycle out of whack for a bit. Don't panic.
posted by Popular Ethics at 9:50 PM on March 10, 2011

I would let her be the first one to bring it up, or initiate, or whatever.

Like milk white peacock, I also think it's important to remember that sex is more complicated than the binary of Experienced and Not Experienced. I've slept with exponentially more people than you have (heh), of both genders, and have been doing this for quite a while now. Still, every new partner is different. Every relationship is different. The first time having sex with a new person is still a bit of an adventure that we each have to guide each other through via communication, attentiveness, generosity, and all the stuff mentioned above.
posted by Sara C. at 9:53 PM on March 10, 2011 [2 favorites]

I very nearly wrote this question a little while ago but then I remembered that I spent my entire sexless adolescence listening to Loveline and my mid-20s reading AskMe and I already had a pretty good idea of what to do.

First off, don't share this AskMe yet. I'm sure she'll find it endearing in due time, but right now she's probably feeling shy. Let's not bring strangers into the already confusing mix.

Second of all, so far so good! Good kissing is highly correlated with good sex. Garsh. Especially the whole, "let's teach each other,"/copy cat game phase of kissing. So relevant!

Even more important than good kissing is good communicating. Communicate before. Communicate after. Communicate during. Especially during. She might be shy about talking, but do pay attention to how she seems to be reacting (good/bad). In my case, we had to get really good at communicating when she was ready for penetration. Lifting up her pelvis with a pillow or two also helped her open up and feel more comfortable. YMMV.

There's a show on Netflix called Sexual Healing where the camera goes into couples sex therapy sessions. It has some great (explicit but loving) examples of how couples communicate these really sensitive things. Very empowering stuff.
Foreplay is so crazy essential it's not even funny. You might not even get to the Penis-in-Vagina stuff for a while. There's a tendency to want to set a day and have some big romantic date, which isn't a bad idea, per se, but expectations need to be kept realistic. Not every couple can have PIV penetration on the first try. That's okay because foreplay is awesome. In my case we both had jitters and it took many weeks of fooling around. I fished this story with close friends and they helped my confidence by relating similar couplings that were worth some trial and error. If this turns out to be you: Think of it as the best science experiment ever.

A lot of people go by the rule of thumb that PIV sex doesn't get good until at least the third time with someone new. This is an average and you may be an outlier. That's okay. It's not a race.

A half hour of foreplay is maybe a good median to aim for. More is generally better unless you sense she's losing interest. There's a reason why teens play around with gentle fingering -- again, some women tighten up under anxiety. Start with one finger and at least work up to two. Gentle! (At first.) Also: the clit is your best friend. Some women like direct stimulation and some like the general vicinity. Also also: oral. Also also also: mutual masturbation. Wow. There's a whole galaxy of awesome fun stuff to explore that has nothing to do with PIV!

Condom and lube is a no brainer. The Planned Parenthood single serving packets are great because they don't broadcast that you ran out to buy a big ol gallon of lube for the first time.

A little bit of alcohol might help her. (You did communicate before getting intoxicated, I hope.) I find that, as a man, I'd rather not drink so much when getting started with a new partner.

She may or may not know what to do with her body, how to position her legs or when to tighten, relax her pelvic floor/kegel muscles. You might see what she can do while you're using your fingers. These are the same muscles you use when holding in a pee. 

The gentle instruction and feedback you've developed while kissing will help as you figure out how your bodies fit together.

Okay, that might be information overload. The truth is that every new partnership is a learning experience. Skilled lovers know that each partner is a blank slate. That is to say, your inexperience is absolutely *not* a handicap. Everyone who gives a damn starts from step one with a new partner.

There are really only two skills to good sex: 1) two-way communication, 2) the patience of trial and error.

Have fun!
posted by Skwirl at 9:59 PM on March 10, 2011 [10 favorites]

She's 30 and she's enthusiastic about being with you, and, I'm assuming, fully connected to the internet and probably a world of information. I bet she has lots of thoughts on the matter, what she'd like you to do, where she's most nervous and what she's most curious about. You should ask her about them! Late bloomers aren't innocent, they're just inexperienced. That doesn't mean she hasn't had her own sexual experiences and her own desires lined up for a while, now.

Start with asking her what she wants. Let her know that it's not a pressuring situation, just that you want her to be pleased and pleasured and you're totally into trying whatever might interest her. If neither of you are in the clothes-off stage, get comfortable around each others bodies a little bit to begin with.

You should probably start with hands and fingers on each other and work your way to other forms of mutual orgasm. If you've both made each other come in non-penetrative ways, by the time you get to the penis-in-vagina stuff it's less stressful.
posted by Mizu at 10:36 PM on March 10, 2011 [2 favorites]

I agree with elpea. Just take things slow, let her initiate, and things will just happen. I would also be put off if I felt like I was being "taught" how to have sex (not that you'll be doing this, just my opinion). Like others have said, this is a new experience for both of you because you're doing it *together*, so I'd say just enjoy your new relationship and don't get too wrapped up in the tour guiding. Have fun!
posted by sucre at 4:34 AM on March 11, 2011

My first time was with another virgin. We figured things out okay.

Sex isn't really one of those things you need to be taught. When she's ready, get naked and go exploring!
posted by peanut_mcgillicuty at 4:59 AM on March 11, 2011 [1 favorite]

Start with inserting fingers first, for a while -- if you stretch out the opening before the "official" first time it will hurt so, so much less. Let her set the pace-- I don't mean have her do all the moves, since she's (naturally) going to be shy and tentative, but let her reactions and level of excitement set the pace. You'll be fine!
posted by chowflap at 8:42 AM on March 11, 2011 [1 favorite]

Let me repeat: new sheets, with high thread counts, and no Star Wars prints
Some of us would be quite happy with Star Wars prints, thank you very much! But sheets, cleanliness, functional curtains are all important things in making someone relaxed about getting naked and sexy.

Chowflap's comment about finger insertion - this is one of those things where all virgins are not created equal. If she's spent the last ten years using a generously sized rabbit vibrator she may have no problem being penetrated (and main problem may be the human penis' lack of vibrating attachments); if she's nervous about sex it may take some time before she's relaxed enough for any penetration to happen. Aside from condoms, lube, and salubrious surroundings going with the flow and seeing what's good/bad for the both of you is the way to go.
posted by Coobeastie at 10:38 AM on March 11, 2011

I agree that it's absolutely key to drop any "teacher" mentality about this. Remember that you're both consenting adults, and you're not doing something to her, but with. Mutual exploration is exciting. Sex should be fun!

Relax. (Wine might be helpful. I am not suggesting you get drunk, but a glass or two to calm nerves in addition to setting a lovin' glow over an evening.)

Embrace the awkwardness and learn to laugh about it. Really, it's okay, and only temporary.

My first time was forgettable - teenage, frantic, and unsatisfying - and while I don't regret it, I wish I had taken my time instead of trying to "get it over with." Don't get me wrong, I was plenty interested in the guy and wanted to have sex, but I was also very nervous and painfully self-conscious of my inexperience. If I could go back, I'd tell myself to focus on the moment and finding joy in new sensations rather than what it's supposed to be.

If you can, drop your expectations. You like her, she likes you, focus on how her body reacts and keep communication open. An orgasm will probably not happen, and that's completely okay. Lots of kissing, patience and lube! Massage might be nice.

Again: have fun! Also this is a great short that may be of interest:
Never Like the First Time
posted by mellavellum at 8:37 PM on March 11, 2011

Enjoy the slow, looking-in-each-other's-eyes, kissing moments. Touch her skin softly, everywhere. Enjoy her. Smile a lot. Smell her skin and really let it sink in. Let her know you enjoy how she smells, how she feels. Pull her in close and hold her. Draw it out and let the wanting get stronger. Clean room, clean sheets, as much softness as you can manage. Be sweet, be tender, and most of all, be relaxed (so she can feel relaxed too). Don't be too serious, but make sure you let her know how special she is to you.

**A final note: I disagree strongly with the poster above. Avoid Dan Savage.
posted by eleyna at 9:20 PM on March 14, 2011

just a note, I feel like maybe your own old anxieties of when you were a virgin are being transmitted onto her, in what the comments say are "tour guide" or "teacher" like attitudes. I might be wrong, but I feel that you are trying to make things better for her and alleviate the anxieties you remember yourself had, which is a very nice intention, but might be badly interpreted, as you can see with the other comments.

I say that because as a 19 year old virgin (no sex no kiss) I can relate to the pressure you describe. Also, I don't know if I totally agree with hal_c_on's comment: I think a lot of older virgins get stereotyped as being prude or less sexual, which, as Mizu has said, most of the time isn't true. I does get frustrating after a while, though (maybe you experienced that yourself), and we feel like we have to specify that we are NOT, in fact, prude, and I know it took me a while to not feel guilty of knowing I'm a sexual and sensual person even if haven't had sex yet, so maybe she just didn't want you to assume she was a stereotypical virgin. Everything's possible, and everybody's different: your girlfriend (or date?) might be a virgin, but that doesn't mean she hasn't explored her body, masturbated, fantasized, and knows her body and what she likes. The hardest part is probably to have the confidence to trust herself, but your open attitude I think will be encouraging for that.

All this to say: she has probably really wanted to experience sex for a long time now, and maybe (probably) would be willing to do that with you, but the fact that she's been a virgin for a long time might mean that it's even more important to have a meaningful and trusting first sexual relationship for her now that she's "waited" all these years (or maybe the opposite, and she just can't wait). The thing is, you can't really know, so I would definitely continue following her pace, letting her feel that you care for her, and if you feel the need, without making a whole deal out of it or serious discussion, verbally telling her that she shouldn't pressure herself. (And please also be honest about your own experience)

Also, what are you expecting from this first sexual relationship with her, on your part? (if it's not just having sex with her and dumping her, that is (though it doesn't look that way)) making this clearer might be helpful in how you want to act about it, and make her feel more comfortable that way

I was also wondering: how do you know she's a virgin? Has she openly told you so? Was she maybe trying to initiate discussion about it?

That was my over thinking side commenting, also in case if you wanted to hear the opinion of a kind of old (though not same age, so I might be totally off track; plus, attitudes change towards what we think our first sexual encounter should be like, I know mine have, so really hard to evaluate something like that) virgin girl, but: I really think the other posters are right in telling you guys not to over think and giving yourselves a chance

Hope it goes well :)
posted by kitsuloukos at 8:00 PM on March 22, 2011

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