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Deafening Tampons, Spring Breakers, and the 26-Year-Old Virgin

I’m a 26-year-old virgin. I’ve never had a boyfriend. I’ve only kissed one person, a stranger, drunk at a bar. I missed out completely on teenage fumbling, college experimentation, post-college mastery, etc. Now, here I am in my late twenties, having led a mostly sexless existence (I say mostly because, despite my lack of partnered experience, I’m really good at getting myself off. Thank god). Thing is, I think I might have a chance to mess around with a dude in the near future. I like a guy, I know he likes me back, we live in different places, but we’ll be in the same place soon.

So, the question: How do I do this?! I mean, I know how the parts work. But I’m nervous about the act itself, from first kiss to bases 2 and 3 to fully gettin’ down. Should I just say something? Like, “I haven’t done much of this, so please be patient?” That sounds so unsexy. I’ve never even touched a penis, so how do I proceed? Do I just hope that instinct will take over? Because I’ve never been in a situation to read signs, I’m afraid I’ll miss them and mess something up, or do something wrong, or, or, or… Oh, and how do I, like, kiss good (and by extension I guess I want to know how to fuck good, too)? 
I really need some woman-to-woman advice on this, and while I have lovely, supportive friends, it’s not something I feel comfortable asking them about. Because it’s weird, right? It’s weird to be 26 and mostly well-adjusted and a virgin who’s never even made out with someone. In the past I’ve considered asking a male friend, or finding someone on Craigslist, to fool around with me just for practice. But even typing that sentence out makes me feel sad and desperate. It’s not like, at this point, I hold any “the first time is special and sacred” illusions. I just want it to be FUN. I expect some awkwardness, but the less the better. 
Help!

Being a 26-year-old virgin isn’t weird. Why would it be objectively weirder than if you were 25? Or 24? 23? 22, 21, 20, 19, 18, 17, 16, 15, … ? Does one of those stand out as the “normal” age to start having sex? Probably not, right? So no, it’s not weird that a girl who’s never had a boyfriend, never touched a penis, and only ever kissed someone once is still a virgin. Makes perfect sense! Having sex before you’re ready to just because you think it’ll be weird if you don’t, or because you feel some other pressure to is super-weird and doesn’t make a lot of sense, and you’re smart to not have learned that firsthand. You considered fooling around with a friend or a Craigslist stranger (@$$%#$!), but then you didn’t, probably because some part of you realized that that isn’t what you actually wanted and stopped you from doing that. That’s great. You’re great. Get it out of your head that you’re a weirdo, and get it in with this kid you like who likes you, already, if that’s what you want to do.

It might make you less nervous to tell whoever you decide to have sex with that you’re a virgin ahead of time. I don’t know about “I haven’t done much of this, so please be patient,” ’cause girl you ain’t done NONE of it (ohhh!) and ’cause yeah, I don’t have a dick but “please be patient” definitely sounds like a boner-killer. “I’m gonna cuuummm, please be patient!” AaahahahHAha oh my god. Anyway, it’ll be out in the open and off your mind if you just put it out there, and hopefully alleviate some of the pressure you’re putting on yourself to Perform, which should free up some headspace for just enjoying the thing. Make sure you’re super comfortable with the guy you choose to make it with, ’cause if everything works out you’re gonna end up saying way crazier things to him than “ur abt 2 b the 1st guy I fuck,” once you get going. Just think of it as the first of many things you tell him that make sex as fun as you want it to be. That’s if you feel like telling him. You definitely don’t have to tell him, especially if you think it’ll stress you out even more. Just remember that there’s no right way to do this, and that it’s going to be weird and new and maybe kind of funny, so relax and get on with it. ‘Cause seriously, the only way to do this is to just. do. it.

How do you kiss good? Tilt your head 45°, open your mouth three-quarters of the way and make an infinity loop with your tongue until one of you chokes? Please be patient. JK, just kiss him! Think of the “bases” as two blind people trying to figure out exactly what the other person’s entire body looks like. Fumble around kissing for however long, and then just fuck him. How do you get to Sex Carnegie Hall? Sex practice. Remember how you got to be really good at getting yourself off? Do whatever you did then, just with this other person. If he does something you like, tell him. If he’s doing something you don’t like, tell him. Get him to tell you what he likes and doesn’t like. You want a sign? His dick will get hard when it likes what’s happening to it. Don’t let your overactive brain ruin this for you and don’t underestimate your instincts. Humans have literally been fucking longer than they’ve been doing anything else. So, you’ll figure it out. Do you like dancing? When a song comes on that you like, do you stand there thinking “omg what if I DANCE WRONG?!!?” or do you just dance. Just dance! It’s gonna be OK. Doo da dum doo doo, you know?

Anyway, I hope that helps. I think you’re gonna be great! Just chill out — it’s only gonna be as big of a deal as you make it. And it’s the first time you’re doing a new thing, so cut yourself some slack, get your confidence up, and just get in there. If you want more specific ideas, or just to get a general sense of the way things go, maybe watch some porn? Oh, and please be patient with his balls. That’s the only @sextip you’re getting. Oh, and be safe, duh. Pretend that’s the first thing I said.

Why is it such a big deal that that biodegradable Sun Chips bag was noisy when tampon wrappers are SO LOUD, especially in a dead-silent office when I’m trying to move a tampon from my desk drawer full of tampons into my cardigan pocket to take with me to the bathroom and I think I am being sneaky by NOT doing the so-obvious “carrying my purse with me 10 yards to the bathroom and back, just carrying my purse, no big deal, no reason, nothing in this purse I particularly need to use/unwrap in the bathroom” thing. 

I guess I just feel like you guys should start some movement that ends with tampons wrapped in mesh or silk or something.

I’m not at all on board with that movement for a zillion reasons, but I do propose a movement that you stop being sneaky about your tampons and get real. I mean you’re old enough to make a baby and work in an office, so yeah, you can handle the truth. Also, the idea that your coworkers are like “there she goes again with the period stuff” is great. They’re not like that. They’re probably like “there she goes again looking all nervous-y, rustling around in her drawer to find the drugs before running to the bathroom to do the drugs again, just like she did 4-6 hours ago.” Or they probably don’t even notice because they’re all so focused on the completely normal bodily functions they’re hiding from you? Also what tampons are you using that are so loud? I thought the Great Tampon Caper of early 2011 established that every living, bleeding woman with internet access uses O.B.s (ninja-silent). Anyway, fun office.

I think it’s cool to be all “TAAAMPONNNS!!!” whenever you can. Sometimes I’ll just drop one on purpose on the bus and then play dumb, waiting for as many people as possible to notice, then pretend I just noticed and ask one of them to go up and ask the bus driver to stop so I can pick it up. Or I’ll keep one tucked behind my ear like a pencil for a few weeks, just in case, until it’s time to use it. Anyway, I think you should free up that drawer space for actual work stuff and get one of those test tube racks from science class and arrange your tampons on your desk in order of absorbency, next to the pens. Or do whatever it is that you have to do to stop worrying about this right now.

I guess if you find that you really can’t get over the walk of shame, you could put your tampons in a vintage Sun Chips bag to drown out the wrappers and make a whole thing of how you’re just taking a normal bag of chips with you to the bathroom, nothing to see here, and no one will suspect at all that you’re a fully grown woman.

I’m a guy living in a big Spring Break hot spot. During this time, one question always come up between my friends and I, why do women get into cars with strange guys? In my experience this isn’t rare and it isn’t limited to drunk college girls. So, whats up with that? It seems like a bad idea.

Spring Breeeaaak!!!!

What’s up with the fact that you and your friends probably also see women binge drinking, smoking cigarettes, blowing coke, eating Red #5, TANNING WITHOUT SUNSCREEN, and all sorts of other dumb things and aren’t at all phased? But when they pile limitlessly into cars with dudes they just met, you’re all, “Somebody save the womennn!” Or that you don’t think it’s a bad idea for the guys in this story to let strange women into their cars? Hmmm? You and your friends are very nice, and it’s very nice that you’re concerned, but also any place that can be described as “a big Spring Break hot spot” sounds like Bad Idea Town, Population : D so it’s interesting that you think the riding in cars with boys thing is a worse idea than all of the other things that probably go on, is all.

Since you’re basically asking why women sometimes do risky things, I guess the answer is because women are human. Girls just wanna have fun. Sometimes it’s fun to get in a car with a strange guy, ’cause cars are awesome, guys are cool, and strangers are exciting. And sometimes it’s a bad idea to get in a car with a strange guy, ’cause cars are dangerous, guys are jerks, and strangers are terrible. No real way of knowing, other than to trust your instincts. You’re way more likely to hear about the times a woman did something that turned out to be a bad idea, because Law & Order: It Worked Out doesn’t air 25 times a day, and the 10 o’clock news is never like, “Coming up after the break, another wanton slut gets her shit banged out vacation-style by a guy she met in the parking lot, describes the entire ordeal as ‘fucking incredible.'” Doesn’t mean those things don’t happen too. Not all men are predators on the hunt, and not all women are victims-in-waiting. Sometimes people are just people, tryna get they party on, you know? You know. Spring Breeeaaak!!!!

Previously: Small Tongues, Large Other Things, and How to Go to a Bar by Yourself.

A Lady is one of several rotating ladies who know everything. Do you have any questions for A Lady?

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