Monday, April 11, 2011


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. 

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?

Photo via Flickr

117 Comments / Post A Comment


For the virgin: believe me, just because your dude is your age does NOT mean he'll be good, or even realize that you're a virgin. He could have slept with handfuls of ladies and not be a good kisser. Or know how to get you off. Or whatever. That sounds negative, but it might help you be less nervous.


Virgin, I concur, nothing to be ashamed of.

One idea you can try, before or after the experience you mention here, is asking an experienced, nonjudgemental friend to recommend a "good" man. Some of us do this. My friend asked me, should I bang S? I said Absolutely. But do not bang T., he is a waste of time. A good referral or two can help you gauge what "skillz" might look like for future reference.

Also, those "getting yourself off" skillz are totally relevant to sex with a partner. Dudes actually pay to see that. Show what you know!

P.S. Sex hormones can trick you into thinking you're more into a guy you've slept with than you really are. Keep this in mind, though most of us have to learn the hard way.


@lafleur SO true. I've been with a 28-year-old who was horrible at sex, and a 20-year-old who was pretty good. Also, the first time I had intercourse, I didn't tell the guy it was my first time. I think he assumed I'd done it with my ex-boyfriend. (My ex and I had done a lot of manual and oral stuff, but no P-in-the-V.) I didn't want him to know- I just wanted to have fun. He'd been with a lot of other girls and had liked me for many, many years, so if he knew I chose him as my first intercourse partner, I think he would have felt too smug about the whole thing, and I didn't want that. I don't think he ever suspected it was my first time. However, unlike the letter writer, I had some experience with all the things leading up to P-in-the-V.

My point being, he might not be that experienced or good, and he might not suspect you're new to it. But don't be afraid to tell him, if you want to!!!


Oh, Lady. I'm dying from the smuggling tampons in a Sun Chips bag.


I know! "Doo doo doo, headed off to the bathroom, with my Sun Chips, again! Just another average day!"


Just snorted with laughter at the tampons in a sun chips bag and had to pretend that I was coughing or something because bursting out laughing at my work desk is "not normal".


@applestoapples: She makes me want so badly to DO THIS. And I work in an office with a staff of five+me, so it would be such a waste of perfectly insane behavior!

Mike Barthel

Just carry your purse to the bathroom. Dudes are too dumb about how ladies work to realize that's weird (we think ladies always need to carry their purses, like they have an oxygen tank in there or something), and the women shouldn't care.


does *anyone* care? i don't think i've thought twice about tampon transport since 8th grade.


I have literally never thought about some girl carrying a purse to the bathroom as a sign of tampon transport. Now I will, but I also will not care. So, yeah.


@vvv umm..THIS! im thinkin this asker has to be incredibly young..who worries about this??


Lady, you posted some rocking answers. I really enjoyed that last one. Hm, why does anyone do stupid things? Because they're people? Also, carrying a tampon behind your ear "just in case." You should rock that look at the club. You'd make friends in the bathroom! And seriously, lady who wrote in about noisy tampons, take your purse to the bathroom if you're so worried. No one will notice.

Jaime Green

Sex Carnegie Hall!

I'm firmly in the camp that it's worth the awkward inner horror to tell the person that you're losing your virginity to that you're losing your virginity to them. They should know the full situation, but mostly, this will change how they go about boning you, FOR THE BETTER. They will be more careful, they will go more slowly, and they will not expect any mad charge-taking or skill-having from you. I think taking those pressures off of yourself is worth the literal five minutes you may spend trying to get out the words, "I haven't had sex before."

And also, you are not a freak, and anyone who wants to bone you or love you would not even care if you were.


@jaimealyse: I completely agree. If you like him enough to make him your first, chances are he likes you enough to both appreciate and take great care with BEING your first. And, having NOT done this myself the first time, with a much older dude who was into being, ahem, ROUGH, I speak from experience. Bloody, painful experience.


@jaimealyse Can I also please say that I have been on the other side of this, in that a cute 19-year-old boy I shagged in my dorm after some drinks and poor decision-making revealed after the fact that it was actually his first time? Now, I'm not saying that he HAD to tell me, but it felt pretty deceptive. I would have handled it differently (PS: I could totally tell he wasn't very experienced. Unless you are an utterly oblivious asshole, it becomes pretty clear).

Because, let's be realistic: Sex is a big deal to Virgin. Which is cool! For some people, it's not, but it clearly is for her, else she would have done it before now. So I think she owes it to her first partner and herself to be honest, because it MIGHT be a significant emotional event for her, and she should be with someone who is both capable of managing that possibility and open to it. Potential damage limitation.

Finally, as you've both rightly pointed out, the first time can be physically uncomfortable (CAN be - not always - but it will feel weird at the very least!). Far better that Virgin's partner is aware of this fact and can be sensitive to it, with lots of communication. If something hurts or she doesn't like it, she can tell him. JUST TALK TO HIM. If he can't deal with the ish, he's not the right one.

Jaime Green

Oh, also, if you're scared of what to do with penises, read this: http://bit.ly/2CehJ5

(My mom doesn't read the comments here, right?)


@Jaime Green As much as I'd like to read this, it's invite only >.O


This Lady is killing it. Sun Chips bag! Red #5! Law & Order: It Worked Out!

Tampon lady, seriously? Nobody cares that you're putting a tampon in your pocket.


Love this Lady. Getting a Choi vibe, especially re: tampon/Sun Chips and Spring Breeeaaakkk!!!!

Daisy Razor

When I told my then-boyfriend-now-husband that I was an old-lady virgin, his response was, "That's cool." Then he politely asked if I wanted to remain a virgin. I said no. The whole thing was way less painful, if much more silly, than I thought it was going to be.

The tampon lady should just stick them in her bra. Unless she's worried that her coworkers will then notice that she has boobs.


This is what I do! Stick tampons in my bra, I mean. Mostly because most of my work clothes don't have pockets, and it's an easy way to have one on me.


I was also very self-conscious about carrying the purse to the bathroom with me, so-- since about seventh grade, and because I always wear jeans, I stick a couple in my socks. No bending involved on that body part, so they don't get broken. One of these days, though, I'm gonna start wearing girl clothes, and stop doing the manual labor thing. I won't be able to stick them in my bra-- not enough camoflauge! A piece of gum would show against my itty-bitties.


I often use this purse where my tampons find their way into the nook of my wallet, so when I want to pay for something it's like, "Here you go cashier, TAMPON SURPRISE!"


@magnificentjane I was unaware we shared a wallet!


Wait, first lady--you're 26 do not say 'late twenties'! Mid-twenties! Sorry I'm fixated on my age so I am jealous.

And what's wrong with asking someone you're about to get down with to be patient? If you're going to go there you should be able to say whatever you'd like if that's how you actually feel.

Hot mayonnaise

@shenannies: Good point. Late 20s = 28+


I almost died trying not the laugh to hard at the tampon thing, but also---

1) tampax pearl (yes, very plastic and bad for the world) are actually wrapped in pretty quiet plastic/

2) at my work we have a community supply of tampons in the bathroom so ladies don't have to worry about sneaking around, and I love it.


The kind you push in with your thumb, or the kind you pound in with a hammer?



@atipofthehat: "Pound in with a hammer". I think I love you for this!


For the virgin, yes - totally get it out of your head that you're a weirdo. Having been there (hadn't done that) not so long ago, I know what it's like to be walking around with this awkward secret in your late 20s. But who cares? Really, who cares? No one cares. And if the person you want to sleep with cares, well, then, he's not worth sleeping with. Which I'm sure you've figured out b/c you haven't had sex yet - haven't fucked just anyone just because. I was totally upfront with the first guy and it was awesome. Fumbly, but awesome. Confidence is the great equalizer. Be honest, be yourself, and have fun.


Last line: This advice applies to many, many things.


True everywhere except for jury duty.


O.B. tampons are still M.I.A. in NYC! This is horrible I've been wandering forlornly in the Duane Reades, hoping they'll magically appear.


There was one box of OB at the store last week when I went. I usually go for super plus, but they only had regular. You know I almost accidentally slapped the stockboy grabbing them. I'm safe for now.


They were back at my local Brooklyn Walgreens the last time I needed them! I was so excited, because suffering through using Tampax or whatever was the suck. I think they even had all of the different varieties, albeit in limited quantities. It seems like the end to our national nightmare is finally in sight!

Tammy Pajamas

The Super Plus have been discontinued, but the other ones should be available. They are in LA, anyway.


Nope, they are back. I bought two boxes a few weeks ago at the Duane Reade on Court & Montague in Brooklyn.


@shenannies bedford avenue duane reade! and while you're there stocking up on 'pons, you can get a delicious growler of beer.


What I hate is when a rogue tampon slips free from its wrapper and lurks at the bottom of your bag like a U-boat, just waiting for someone to ask for a pen.


@MollyculeTheory: I hate it when the wrapper secretly breaks, and then I need one, and am all, good thing I am so smart as to carry a tampon! Then I fish it out, and it is covered in lint and tobacco flakes with a gum wrapper stuck to the side.


You two need purses with little zip pockets on the inside, for Guaranteed Tampon Discretion (plus protection from gum wrappers and tobacco).


Eh I get the tampon shame. My solution is to keep them in a pouch that muffles the sound but is small enough that I can slip it into my pocket. Vintage cigarette cases work great.


when i was a wee slip of a girl, the tampax lady came to our school and we all got a goodie bag with some free tampons, a leaflet on the menstrual cycle & toxic shock syndrome, and little blue plastic cases we could carry our future tampons in! ...which i and my friends then used in order to smuggle cigarettes into school, safe in the knowledge that no teacher would ever be so shaming as to check.


This is genius, Cee.


For all of you being cavalier about tampon transport, here's a scenario: You calmly extract a tampax from your desk and stride to the restroom. On the way you are accosted by boss who wants to introduce you to new employee - your tampon is in your right hand. What to do? Even if they are chicks it's weird to be blithely switching sanitary products to the other hand for a quick shake. It's even weirder if they are dudes (yes it is).
Just saying that even if you are a bold and proud menstruater, the office can be rife with situations where you don't want to be caught with a pad in your hand.


Just tell them you cut your finger.


@Kneetoe lmaaooooooo!!


@scully Maybe you could put them in the waistband of your pants or skirt. Or in your bra. Or, if all else fails, carry them in your left hand?

simone eastbro

dear 26 year old virgin,

darling, you are not mostly sexless. you've had a rich sex life. you are a sexual person. it just hasn't happened to involve anyone else.



@listen, lady Thank you! This is exactly the line this late-bloomer used for many a year til it wasn't needed anymore.

Virgin, I went from exactly where you are to everything-but-p-in-v, technically-still-a-V-but-not-really in a matter of days with a great guy, so rest assured that it really, really doesn't take long to "catch up" and get the hang of the basics.


Thank you, A Lady! Love all the musical references.

For the 26-year-old virgin: When my first time happened, the words "It's my first time, so be gentle!" actually came out of my mouth! Yikes. Good thing English wasn't his first language or cultural reference. But if it had been, I guess it had the potential to be funny, as long as I didn't beat myself up over saying the wrong/right thing. So I guess where I'm going is, it's not so much about what you say as conveying your feelings/needs, and how the dude reacts. If he's cool with it, everything'll be all right. If he's not, then he's not worth your (first) time.

Oh and perhaps more embarassing: I was wearing Victoria's Secret puppy-printed boy shorts. Out of ALL the sexy underthings I owned and had waiting for My First Time, it happened the day of the puppy panties. Sigh.


Tampon noise? I mean, compared to PAD NOISE?


I know! I feel like it'd be the sound the organist made when she walked out of the church at the end of Sixteen Candles!



Right this way!



Why are we pretending we don't have periods?? Unless - are we disguised as a boy in order to complete our study of the Talmud?


@TrilbyLane or to fight in the French revolution!!


I think this is my favorite lady to date. Law & Order: It Worked Out. HAAAAAAAAA

Leila Jane

Tampon Lady... it is highly likely that all of the other ladies in your office are on the rag at the same time so Ditto on that community tampons in the bathroom idea. Also, the dudes are not thinking about you and your period.

Legs Battaglia

A Lady, your tampon advice makes me think about how I went through a phase of wanting to very publicly take my birth control pill - on the subway, in an elevator, on line at the grocery store - sort of just to prove that there was no shame in my game.


There's no shame in that game, but there is a lot of accidentally popping your pill out of its case a little too vehemently, only to see it land on the PUBLIC ground and roll away under something dusty. :(


Loved the entire tampon response. Cracked. Me. Up. I must have a test tube display for my desk at work.

I call them 'Pons.


I work for an airline and let me tell you, airline passengers are impossible to get away from. Once my co worker was rushing to a public loo in the airport with tampon concealed in hand. Inevitably a passenger stopped her being all "Excuse me but where is my brain, I seem to have left it behind when I came to the airport etc". She had had enough that day and was all "I have a freakin tampon here, work it out". He was too bewildered to complain.


Here is my specific virginity-losing question as long as we are on the subject: I am aware that telling the guy who I will possibly be boning down with that I am a virgin is probably a good idea, but when exactly do I do this? Like, before the fact? Can I just drop it in the middle of a totally unrelated conversation? Should I do it in the heat of the moment, or is that a total boner-killer?

(Also I am slightly embarassed to be posting this under my own name, but going through the trouble of posting anon or under another name seems like a lot of work, and also I <3 everyone who writes/comments here, so it's kind of cool? Aaaaaaaah, talking about my v-card freaks me out.)


This is going to sound lame, but...when it feels right. After a glass or two of wine, after a good night of talking and flirting. Preferably when clothes are still on, in case there are follow-up questions or discussions. Maybe not right before the fact, but when it has been mutually agreed upon that the fact is about to happen. And that could be hours before you get into bed.


I feel like the hymen whisperer.


@Whitmans: But, wait, how many times have you had this conversation :)

Whitmans Sampler

More than once. Do de do do.


I also lost my virginity in my late 20s, and definitely agree with the "when it feels right" comment. For me, the guy noticed that I seemed interested but was kind of holding back, and subtly asked how I felt about the prospect of our having sex...telling him was nerve-wracking for a couple of seconds, but once I told him it wasn't embarrassing at all.

Whitmans Sampler

As a fellow v-card holder (by some standards... gah! what does that even mean???), I get it. And in my own, personal experience, it NEVER feels like the right time to say, "oh hey, btw, I've never had sex." But the times that I have done this (which granted, isn't many many), the dude has been very cool about it and everything's fine and I realize I was freaking out for nothing. But yeah, my advice is the same: make sure you tell him sometime before the fact is about to go down. I figure it's just respectful to let a dude know, so take a deep breath, fill him in, and then feel great realizing that it really isn't that big of a deal.

Jaime Green

It can be kinda a boner-killer, but also, you want to give him a chance to think about it - to sort of reconfigure his plan, and also to make sure he's down. I don't think it's a big deal - just a first thing in a sequence of first things, like no guy's ever been like, "I think it's too much of a big deal for me to be your first blowjob" - but some guys do, and they should be allowed to decide if they're up for whatever responsibility they feel it is.

The trick is not saying it before it's clear that you both want to bone, but not so far into things that it ruins the mood. It depends how you feel about it - does it feel like a confession, or like a hey, btw? Also, it might ruin one sexy sesh, but there's always the next night to put the plan into action, so to speak.


@sophi To play Devil's Advocate, I didn't tell the guy the first time. I knew he wasn't a virgin and I just didn't want to deal with explaining anything. We both had a few drinks and went at it. He was a gentle guy so I wasn't worried about it. No regrets whatsoever. If you don't want to tell, you don't have to.


@Whitmans Sampler: I don't understand the term "v-card". It's not an actual card, is it? Like, a Pokemon card (Don't Poke-meeee), or is it more of a trading card (I'll take yours if you take mine)?

Jen Alien-Spouse@twitter

@sophi I felt like the very last virgin at University - So I just wore that information on my sleeve, and told people quite bluntly if they asked me anything related to my sex life. It was embarrassing as hell at first, but that meant when I actually needed to tell the guy I eventually had sex with, well, I was just totally blasé about it.


@sophi While making out? (People other than teenagers make-out before sex, right?) Like before clothes come off, but when it's clear you're going somewhere? I don't know, that's what I did, it worked out all right, he didn't expect sex that night (I basically told him I had no experience beyond making out), and all was actually pretty awesome. And he knew to tell me what was good and what was not so good. That was really helpful. Communication! It's fantastic!

peachy lefever

oh man. so, I work in a relatively small room with 6 other people (male and female). Once, a female coworker emailed me asking if I had a tampon. I proceeded to create this COMPLETELY idiotic scenario in which I found a 3 ring binder, put said tampon in the binder with some random sheets of paper and then loudly announced to the room "here are those FILES you wanted" while handing the folder to the poor bewildered girl who had asked me for the tampon. WHY?? I'm still embarrassed that I didn't have the balls to just hand her the freaking tampon.

also, what's so great about OBs? I've always been afraid of them!

Paige Colbert Van Otten

@peachy lefever They're teeny and have the least waste, and they're super comfy and...I don't know, don't be afraid! When you unwrap it you're supposed to take the strings and sort of circle them around to widen the base so you have something bigger to push on. I never do this though. But that's probably a good tip for those used to applicator tampons?

peachy lefever

@royalpigeon THANKS! I'll summon my courage and give 'em a try!


@peachy lefever: I am so glad other women love the OB due to the environmental factor, but for me, it is akin to shoving a cactus up my cooch. I used them as my first tampon when I was 12, and my MOM had to insert them for me because I would cry every time. (So not only physically painful, but now connected to deep, deep psychological shame). We gave up and I switched to pads until I discovered applicators at 14, and realized that using tampons didn't have to involve hyperventilation and muffled squeals of agony.


@peachy lefever I also like them because they fit in your pocket and almost look like chapstick, so no one needs to know (I call them pocket rockets. LOL). Unless, of course, your pockets are tight and you're trying to get out the actual chapstick and fish out the OB instead. I'm a diehard OB girl. And @Tailfeather, the cover has changed a bit since then and they are much easier to insert.

Sorry For Partying

I can't get over how magical this A Lady's picture is. Just perfection.


I highly recommend using a Diva Cup. You can leave it in the whole time you are at work and it is like you don't even have your period.

How come no one seems to know about these? Is it just too weird?

simone eastbro



my flow is too crazy for the diva cup. sad face. because i'd really like to use it for that getting-rid-of-debilitating-cramps reason you cited, but it is not to be.

simone eastbro

like, so crazy you couldn't empty it every couple of hours? girl, that is rough. i mean, theoretically you could just empty it as often as you change tampons.


well, i tried to wear it overnight, and that ended badly. like, horror movie bad. but maybe it wasn't in place properly? i don't know. but yeah, rough.

simone eastbro

it might not have been! there's, like, a whole world out there devoted to how to fold it in order to insert it.

Paige Colbert Van Otten

@alpelican The Diva Cup in particular also doesn't work for everyone. There is some serious knowledge about these subjects here: http://community.livejournal.com/menstrual_cups


Yes! I was scrolling through wondering what the hell. Thoroughly recommended. (For British people, go here http://www.mooncup.co.uk)

Paige Colbert Van Otten

@raquel YESSSS! I'm back to my Diva cup after a brief time without it (used it with an IUD for 2.5 years, got pregnant with the IUD, doctor said I should probably not use it with my second IUD just to be safe, IUD expelled, PILLS. I'm sad to be IUD-less now, but I <3333 my Diva cup, possibly more than I dislike the pill. Because pads make things kinda gross, and tampons dry me out?


menstrual cups for all! they really are the best. and they save you a ton of fucking money. if the name diva cup puts anyone off, try the keeper. http://www.keeper.com/


I keep tampons in an eyeglasses case...it's the perfect size!

Also, "Bad Idea Town, Population : D" made me actually laugh out loud.


man PAD WRAPPERS were the worst when I was thirteen and trying to hide my period in a k-8 Catholic school, and from my little brother. if I were a scientist I would invent less crinkly pad wrappers.


If I may, a couple way too specific things about punching one's V card: it's totally OK to decide not to close the deal, even if clothes are off, etc. It seems to me that it might be kind of a big deal to go from one drunken-bar-stranger kiss to full on P/V in one go. YMMV, but it's important to do it because you want to, not because you feel obligated, even if he's ready to go. Sometimes it's the price a man pays for getting to touch your boobs.

Lubrication is your friend, *especially for first timers*. The natural, spontaneous form can be elusive, in my experience, if one is nervous or badly drunk; condoms can make it worse. Do what you need to do--take care of business yourself to get things going? Top things up before you go out with a purpose-specific product? Saliva can make a huge difference (dudes, help a lady out!). I've used olive oil (I know!)--but don't do it dry. It will hurt unnecessarily.

Finally, even if you don't go all the way ('can't believe I just wrote that) do yourself (and him) a favor and get your hand around his throbbing manhood(!). They are fascinating creatures, at once totally foreign and profoundly familiar, and it's a privilege to hold one in your hand. Trust me, he will be delighted by your interest.


Love Sex Carnegie Hall! Though now I kind of want to have sex at Carnegie Hall...

I had to sign up just to comment on this one: Dear virgin, take it from a formerly 27-year-old one - chill! You are not weird and there's no shame in being where you are, experience-wise, and any guy who's worth it will be cool and understanding about it. Maybe the difference was my super-awesome friends? Not that your friends aren't great, it's just that mine were crazy supportive and I was pretty open about still being a virgin - if anything my guy friends were most supportive (and probably only half-joking when saying I was saving myself for them...). And I'm not talking open like, "Hi, nice to meet you, I'm a Virgin", but all my friends knew and they were cool about it, and there were high-fives going around when I finally got some. I guess I just figured if that's something that people were gonna use to define me, I'd just own it. So maybe just some thoughts from someone who's been there?

1) Yes, tell them - I know, I debated just not saying anything at all and hoping it wouldn't come up 'cause it still does feel like this stigma, right? Thing is, when I was with the guy, I knew I wanted him and I just wanted to be honest(yes, just not saying anything is a type of lying), so yeah, it was hard to say, but he was amazing about it and actually made me laugh. I'd had guys freak out on me before when I'd told them, and I'm glad I didn't sleep with them because they obviously didn't deserve me. You'll feel like the time is right to bring it up, just like you'll feel when the time is right to transition from make-out to ripping each others' clothes off. That part does seem to be instinct. Like a few have mentioned before me, the good ones will be fine with it, they won't pressure you, and you can tell them when you feel ready. Communication is important.

2) Get educated! Whether it's porn, or asking friends (or websites full of awesome people), or books, or what I loved - educational sex shows! Not porn, but informational, like the sex ed class you only dreamed about; maybe they were a Canadian thing? We had The Sex Files on Discovery Channel and the perennial Sunday Night Sex Show. Get ideas ahead of time so you know what you'd like to practice once you get a chance to. To pick up on the music theme, it's like listening to music and deciding what kind of songs you'd like to learn before you start playing your instrument. You already know what gets you off & that's a great start - and being curious about sex kind of makes it more fun; and how is it not an ego boost to ask him to teach you stuff? You know what you like, he knows what he likes - share info. And being safe is part of it; pretend I said that first too.

3) Don't give it more weight than it needs to have. Society has put it up on this pedestal that it's this BIG THING with so much tied to it, when really it only has as much importance as you give it. Sex is awesome, but it's also awkward and hilarious, both just thinking about the mechanics and in practice. I know it kind of feels like this albatross around your neck that you just want to get rid of so it isn't even an issue or something you think of anymore, but you respect yourself enough not to just throw it away. And that's fine. And you're going to be super nervous the first time. And that's fine. But between the stigma virginity's had attached to it and the way our lady brains love to blow things out of proportion to crazy levels, it can make something that should be super fun into something that feels like a chore we just want to be over. And that's not fine. What should happen is that two people who (hopefully) like each other as people and have a physical connection want to get together and do something fun that feels good. Go at your own pace, and know that afterward, the Earth will not have spun off its axis, the sun will rise in the morning, and with the exception of some probable soreness, you will more than likely feel almost exactly the same as a person as you did before - same family, friends, school/job, favorite colour, etc. And hopefully you'll want to do it again; if you're anything like me, as often as possible 'cause now you know what it was you were missing out on (but you're already getting yourself off, so believe me, that gets you through the dry spells).

I hope that helped a bit - from someone who was in the trenches not that long ago herself. Lots o' Love to you babe <3


YES to society putting virginity on a pedestal. I never cared about "waiting for the perfect moment for my one special gift" bullshit. It wasn't a big deal to me. It was more of a big deal to other people who felt the need to judge my lack of partnered action b/c of whatever bullshit they believed in. Sue me for wanting to actually like the guy I chose to fuck and for not believing the age hype/expiration date hysteria of leaving college (and then some) a virgin. In short, your own sexuality is just that - your own.


A Lady, you are killing it! "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."


As for the virgin, just don't tell him while you're actually doing it. A guy friend of mine had that happen to him and it was a major boner killer for him. He was just upset she hadn't told him before since they had been dating for a little bit. (And of course, getting told "I'm a virgin" mid-doing it is kind of weird.) But he wasn't so upset that he didn't end up doing it with her again. (And again.)

Hot mayonnaise

@olivia: "You're not any more!"


Virgin, I ran out and impulsively lost my virginity with a stranger because I was sick of being a virgin, and it was the stupidest/most shameful thing I have ever done. You have nothing to be ashamed of, and you're incredibly smart for waiting.

Don't stress about the sex stuff - everyone is kind of...born knowing how to do it, it's in our nature. Just relax and go with whatever feels right at the time. :)

Lily Rowan

@D@twitter: Well, everyone is kind of born knowing how to do it. I'm 99% sure I have gotten much better at Doing Sex with practice and varied partners.


Dear The Hairpin,

Will you marry me? Because this:
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.'"

is GOLD.
t.t. mammal

Lily Rowan

@tiptoemammal: That is seriously the best.


@tiptoemammal AGREED! i think easily the best sentence ever, ever written!!


1st time to this site...and your post goes straight to my heart. I'm a convert for life. I'm a 28 year old virgin. I was all books, TV and Movies growing up..now I feel uncomfortable letting guys know my lil secret. But this was byfar the best advice and insight on the topic. There just seems a lack of people around to talk to this stuff about. Thank you thank you thank you!


1. Lady! Flawless advice victory! "Law and Order it Worked Out..."

2. Lady Virgin,

Variations on your question have popped up on the ask a dude side of this site, yielding answers both wise and well-considered. I figured you should have access to those pages. URLs pasted below.



My own two cents are that if you're sweating the seductive progression of sex, maybe porn isn't the most realistic resource. (Unless your gentleman caller is a cable guy?)

In my experience, if the topic has yet to arise, some ladies introduce last ditch "before we do this" warnings during the clothes-on-but-making out-in-bed stage.

Also, I know in movies there's a ten second window between a first kiss and tearing the sheets off the bed, but ain't nothing unusual about a whole bunch of eighth grade make-out sessions. So his expectations may be less ambitious than your own.

And to crib from a comment of mine elsewhere:

Let me betray the secrets of the underground brotherhood of non-virgins. The only secret you discover when you cross the boning threshold is that “THERE IS NO SECRET.” You’re like, shit, that’s it? I could do that. Minute to learn, lifetime to master.

Turns out there is no normal. Everyone is making this up as they go along.


Okay, I'm only wee so I'm not sure how much this counts, but in my years of wanton sluttery so far I have had occasion to deflower a handful of guys. Now, maybe the variables change once all the guys involved aren't similarly young, but I'll tell you for free that there wasn't a clear 'experienced guys are better' trend in evidence. The guys who are good are people who are empathic, patient, good listeners and committed to someone's pleasure. Those traits do not take experience. Sure, knowing the lay of the land (as it were) helps, but it's not the be-all and end-all. Virgin girls and dudes both should relax a little in the knowledge that they quite probably already possess the traits that make a good lover, and for everything else there's google.


Late to this post, but it made for a hilarious read over morning coffee. (except snort-LOLing coffee, not so good.) Thank you hairpin.


OMG Hairpin. You made my day. I too am a well-adjusted and (ahem) mostly sexless virgin in my 20s. And I'm not a total freak, according to you all! AND I am facing the near-future possibility of intimacy with a dude who digs me. Excellent advice from A Lady and all the Ladies in the comments. Fanks much.

anna to the infinite power

Just stopping by to say a huge AMEN to this lady. Top tier and you really, truly hit it outta the park my darlin' but your wisdom on tampons & spring break: both revelations.


@vvv umm..THIS! im thinkin this asker has to be incredibly young..who worries about this??

Between being a queer chick and the daughter of a bra-burning hippie radiologist, I think I missed the "periods are gross" message. Take your ridiculous purse -- maybe they think you need tylenol, or that you need to make a phone call or whatever else a lady could do with her purse. Or seriously, just own it. Nobody (nobody, seriously) old enough to work in an office is unaware that your uterine lining comes out your vadge every 28 days. Seriously, what is with this period shame?

Also, the diva cup. It is awesome and amazing, and you never have to carry anything EVER.

Anna Marquardt

I like this lady.

_Law & Order: It Worked Out_


*Two FEMALE JOGGERS run around the reservoir in Central Park*

JOGGER 1: ...and I was just like, "ugh, forget it, I don't even want nachos anymore."
JOGGER 2: Oh boy! What a jerk!

*There is a rustling in the bushes*

JOGGER 1: Oh my god, what was that?
JOGGER 2: It's...oh, it's a squirrel.



@Anna Marquardt : THIS. THIS times Absolutely ONE BAJILLION!



I feel like that last guy was not really asking "why do ladies get in cars with strange men" but rather "how can I get ladies to get in my car". Lady's answer was perfect.

Erin Thompson

Hilarious! I give this week's column five stars.


To the 26 year-old virgin:
I really feel for you. Although I'm 25 with a tad more experience, I was still a member of the V-club at the time I first read your question. I also have never had a boyfriend. But then one night, my friend introduced me to a guy at a bar a month or so ago and we hit it off. I invited him over and we hooked up (something I never do, but I was really yearning for it) and I knew that I wanted to lose my virginity to him. I knew because he was the first guy I had been with who was respectful, caring, and I was just instantly super comfortable with him (and super attracted to!).

I wasn't comfortable losing it to him that night, but we went out on a date the following week and had an amazing time. He didn't know for sure the first time, but the second time I told him (right when we were beginning to hook up too, so don't worry! timing isn't everything). I figured it was only fair and I asked him if that was ok and he was absolutely fine with it. He was sweet, gentle, and loved teaching me new things. I felt so comfortable that I could go from moaning to giggling. It was a fun experience! I realized that even though I waited longer than the average person, it was worth it to have that great of an experience. This is just me speaking personally, but I feel that since I was mature enough and more confident so that I knew what I wanted and knew what I deserved, it made the experience much more satisfying than if I had lost it to one of the douche-Tucker Max like fellows I had found myself hooking up with during college. Also, it was much less stressful that he was kind of a stranger, and not someone I would have to see everyday.

I'm relieved. It's over with and I can stop torturing myself with putdowns. But just like when I lost weight, I realized that my putdowns before were irrational and undeserving. It's not weird to be a 26 year old virgin and don't let the guy you're with make you feel weird at all. You deserve better.

I wish you luck and my only advice is to be open to meeting new people and find someone who you know is respectful and someone you know you can be comfortable with. While I'm still dating the guy, I honestly hooked up with him because he was someone I could see never seeing again, and I was completely fine with that. I even wanted it! But it's working out! I hope it does for you too!

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