Computer Snooping, Virginity Losing, and STD Testing

Much to my own disgust, I am a 16-year-old virgin. I do, however, have this person of the opposite gender with whom I makeout on weekends and at parties (and tactlessly ignore out of awkwardness at school). So yesterday, we were hooking up naked in the backseat of his car and he was fingering me. And, in the midst of his heavy breathing and inept poking, I had an amazing epiphany: I had no idea if I was actually enjoying myself. I have never had an orgasm, have no idea how to masturbate (despite pathetic attempts) and have really no inkling of how my own sexuality works. I don’t consider myself repressed and I’m really planning on losing my virginity soon. But I really don’t want to buy into the ridiculous myth that a girl’s first time has to hurt; I want to have fun. And if being fingered really doesn’t do that much, how will sex be any different?

Essentially, I’m terrified of having Female Sexual Dysfunction. I’m into this guy and I know what being horny feels like, but that’s about it. Any advice?

I don’t pretend to fully comprehend the hyper-sexualized culture of today’s teenager, what with the cuddle puddles, rainbow parties, and jelly bracelets, but if I have to read, “Much to my own disgust, I am a 16-year-old virgin” from any young woman ever again I’m going to firebomb Viacom, Wenner Media, and any other corporation feeding off the emotional insecurities of the teenage girl.

While I’m upset and concerned about the pressure put on today’s young girls I’m going to try to put aside my anger at the moment (as I try not to think about my niece and young cousins) and endeavor to address your questions as best I can.

The first time I had sex was in the backseat of a used 1990 Nissan Pathfinder I had purchased with my Bar Mitzvah money. Ten minutes into our condom-sex she asked if I could hurry up. When I asked why, she informed me that she has a “misshapen canal” and if I could finish already “that would be great.” While I had no fucking idea what these words meant at the idiot-age of 17 (“canal? Like the Suez?”) they did not prevent me from paging my best friend to excitedly tell him I had lost my virginity. Yes, I felt ebullient and very American, but I mention this because this ridiculous farce of my first time had absolutely zero bearing on my sexual maturation.

I wouldn’t dream of passing judgement and saying when it’s right or when it’s wrong to lose your virginity, but I will say that fingering is absolutely nothing like sex. Not even close. You’re clearly a smart girl, so you’re right not to assume anything about how your sexuality works at the moment. But I’d ask if there’s any way you could apply your obvious intelligence to your fears and to ask yourself whether they truly have any basis, ya know? It’s just that in my experience it’s easy to be fearful of things we haven’t realized yet. I was scared my entire adolescence I would never grow beyond my then small stature and that for the rest of my life I would always lose out to everyone taller in everything. I wouldn’t want to diminish your fears — they shape who we are, one way or another — but it’s very, very important to at least recognize that at this point they remain only that, fears and not reality.

Alas, as mostly everyone in the room will agree, sex probably won’t feel good for quite some time. You simply don’t know your body fully and truly yet and MORETHANANYTHING no guy your age will be the least bit competent for the next five to six years, IF EVER. The vast majority of guys who are good in bed each had a girl to teach them how with the ever-present assistance of Professors Trial and Error. Ideally this takes the form of a long term (1-2 year) relationship in college wherein after a lot of fumbling a guy learns how to please a woman and also learns that none of this entails the porn-based assumptions he entered into the sexual relationship with. It’s almost comedic. They learn how to use their hands, their fingers, where the clitoris is, how to go down on their girlfriends, the power of slow-teasing and to remember to actually kiss their girlfriend during sex. Any single person you go to school with who says they are having great sex isn’t lying necessarily — they simply don’t know any better.

And I want to briefly touch upon “planning to lose my virginity soon.” No bullshit (and this is anonymous, so I have no reason to say any kind of bullshit), but some of the fucking coolest girls I know to this very day didn’t lose their virginity when they were in high school. Many were in college, some even after, and you wouldn’t know it from meeting them. (Or, umm, from having sex with them.)

I’m a single, 24-year-old woman with limited dating experience. I’m attractive enough, intelligent, and generally an interesting and nice enough person, and usually have high standards for the guys that I date. Up until now, I haven’t wanted to have sex outside of a committed relationship; it wasn’t a moral issue, it was more of a I’m-not-comfortable-being-that-intimate-with-someone-whose-last-name-I-don’t-know issue. Given that I broke up with my last boyfriend in August, I started thinking about loosening my self-imposed restrictions on physical intimacy.

Last week, I went out on a first date with a seemingly nice guy and proceeded to take him home with me. Before getting too deep (ahem) into things, I asked him when the last time he got checked for STDs was; he said it was two partners ago. I told him that in that case, though I would like to have sex with him, I just wasn’t comfortable until he got tested; he said he had been thinking about doing that on his own lately, and would probably do it soon. Flash forward to date number three, a mere week and change later. After starting to get hot and heavy, the guy said that my comments about getting tested for STDs made him uncomfortable; he felt that if he acquiesced, he would be giving me the idea that we were further along in a relationship than he was comfortable being. This is after I made it clear that I was looking for a fun, casual dating situation, no real relationship required. Apparently having sex on the first date would have been no big deal, but having safe sex on the third date would be akin to an engagement ring?

Am I wrong in wanting sex but also wanting to make sure I’m not going to contract any life- or fertility-threatening infections along the way? Or can a girl only get safe sex in a relationship these days? I was proud of myself for being both honest about what I wanted (sex) while also being empowered enough to protect myself, but now I’m not so sure. I understand that condoms can go a long way towards preventing the transmission of many diseases, but I’m not comfortable with the risks that come along with condoms breaking, infections that can be transmitted in ways other than through sexual fluids, and other non-zero-risk situations.

Real easy — don’t do anything you don’t want to do! If you don’t feel comfortable having sex until someone has been tested at the start of your relationship, so be it. Some guys will be cool, some won’t! But that’s with everything!

I’m a little unclear about the “a fun, casual dating situation” you seek, but I still stick with the above. About this particular guy, however? WOW what he said was super, super lame. What bad Chuck Palahniuk book are these guys stealing their lines from? My advice would be to stop seeing him and find someone who’s respectful of your concerns regardless of what date number it may be.

However I’d be remiss not to mention that using newly purchased condoms (ideally that are away from direct sunlight in the store they are purchased in) that contain spermicidal lubricant in conjunction with a water-based lubricant is a highly, highly effective way to prevent pregnancies and STDs and is unlikely to break. If he uses two condoms (the friction will cause breaking) or there is not proper lubrication then you run this risk of them breaking, but should you want to have casual sex I would recommend this regimen here.

In all of my years of having sex with ex-boyfriends and guys I dated, I have never been able to orgasm without a toy. In fact, I bought a Bullet for the first time 4 years ago just so that I could orgasm while having sex. Actually, I take that back — there was one time that I almost came without the use of a toy, but it was a hot and steamy nearly-two-hours of raw and mindless fucking with my ex, but his housemate came home and the feeling just died. So no, I’ve never orgasmed without one, and I don’t mind not orgasming, but the guy I’m dating right now wants so much for me to be able to orgasm, preferably with him inside me; but if not, that’s OK as long as he can shove it in there while I orgasm from my Bullet.

So here’s the problem: it takes forever for me to be able to orgasm with another person next to me, because I do get self-conscious and I have to position myself certain ways to get that feeling. But he insists on me getting there anyway because it turns him on a lot to hear my O, and something about if I don’t orgasm, it makes him feel like he’s not satisfying me enough so he’s unable to finish himself in the end. The few times that I agreed to use the Bullet took a long time for me to orgasm, and I feel like this might become a problem as I feel like he is going to get tired eventually of waiting around for my O. But anyway, I don’t know what to do. I like the guy a lot, he is wonderful and caring, and the sex and fucking is great when I don’t have to orgasm. Could it be because of our age difference — he’s in his mid-30s so maybe his take/goal in sex is a bit different than mine? Is there any other way to tell the guy “Please, just pretend I’m a rag doll and fuck the shit out of me without caring about my orgasm”? Because everything I’ve said hasn’t worked!

Every vagina was not made equal. (Here is a handy and NSFW chart.) I have dated the girl (uncannily exactly like you) who needs to use a toy (uncannily exactly a bullet) during sex to get off, and the girl who only gets off when I use my fingers, and the girl who has to hold back on all three of her orgasms because they happen too quickly. Alex Baldwin’s paterfamilias in Outside Providence was plain wrong when he said, “Sex is like Chinese food, it ain’t over to both of you get your cookies.”

So my initial reaction to you (my possible ex-girlfriend you) was to simply respond with, “What do you want me to say? As even you explicitly say yourself above — there are some of us guys who have realized that sex for women can feel incredible regardless of whether it culminates in an orgasm for them or not, and there are some guys who haven’t realized this and take it personally when the girl can’t because they’re insecure. Just be open and tell him how you feel. Sure. Say the above. Done n’ done.” And while this still remains my reaction I’m gonna take a step back and do a little deeper dive into the issue at large.

I hope you have all had the opportunity to read some of the women’s questions over the past few months that myself and the other intelligent handsomes that comprise this A Dude Squad receive and answer. I’ve read a lot of them. So much so that I fear even I’ve never had an orgasm and that my vagina tastes like pennies. And as you read them more and more you see some consistencies emerge. While not all women have had EXACTLY the same experience, the majority of the questions seek simple elucidation on the typically selfish, put-upon expectations/assumptions from the men in their lives. This is very upsetting to me. Selfishly, because a lot of these guys are boat-shoe-shuffling detriments to my gender who still get to have sex with awesome girls, thus perpetuating and reinforcing their behaviors. Less selfishly, because everyone deserves true and unfettered happiness. And there is never any reason why someone’s expectations (and not the realities) should encumber this. He expects you to have an orgasm? He expects you to have a threesome? He expects that you should just simply buy his bullshit logic on concerns of yours? Sorry, all that’s on HIM. It’s not on you. It’s NOT on you to have to SAY SOMETHING. It’s NOT on you to have to DO SOMETHING. It’s on THEM to realize that it’s not about THEM.

Sometimes I wish you guys could put you and your boyfriends on the phone with me. I can also invite my cool-as-hell girlfriend and my probably-once-cool mom (who both read this!) if you would like. But someone’s gonna have to walk moms through how to use conference call and I can tell you right now it ain’t gonna be me.

Is stress a viable excuse for no sex? I’ve been with my boyfriend for three years and at the beginning whenever we were alone, we were very sexual. Now that I’ve moved in, he says stress or being tired just isn’t letting him in the mood. I’ve dressed up, I’ve talked dirty, but he chuckles and kisses my forehead. Ill say I get laid maybe once a month. That just into enough for me. Thoughts? He is 24, I’m 25 so age can’t possibly be it! I’ve told him I want more sex, I’ve told him I’m open to anything he wants. Communication isn’t it either. Other than sex we have an all right relationship. Should it matter so much to me? He says he is trying. Shouldnt it come naturally? Literally.

Crap. So, normally my answers are couched in a certain positivity and hopefulness (’cause I like to think good things happen to good folks), but, yeah, this sounds like you’re nearing the end of the relationship. I could be wrong! A Dude isn’t infallible! BUT I’m a super, super sexual guy, and even I did this kind of thing to a girlfriend once (interestingly enough, at the age of 24 also). Alas, the sad, sad reason was that I fell out of Like with her. And clearly my immature self was playing architect to somewhat gird us for our inevitable demise. Also, the misguided and immature mind of a 24-year-old (I don’t care how seemingly mature they think they are at that age, they’re not!) thinks that planting the seeds of concern will grow into sprigs of resentment and that this will somehow make it easier for you when the relationship sours past the point of reconciliation. It’s the fucking dumbest, most self-concerned delusion of “being a good guy” EVER. And I’m incredibly embarrassed to admit it’s something I’ve done.

AND! I’ve also been on the other side. Long term relationship. Hung out seven days a week. But regardless of our proximity she just stopped having sex with me. I would masturbate in the shower every morning. (And I hate doing that standing up.) I said the exact same thing you did, “Should it matter so much?” I told myself that she’s not really an affectionate person in the first place and I’ve had enough sexual experiences to last me a lifetime and so what if that’s my only complaint. Then she broke up with me, crushed me, within a few weeks time. As I expected in the back of my mind she would.

Don’t get it twisted. Sex is very important to a relationship. Physicality, closeness, affection, all that.

I hope that I’m wrong about where your relationship is heading, but I fear that I’m not.

OK. Let me preface this by saying that I know it is wrong to snoop — WRONG!

Now: a couple months ago, I received an anonymous email from someone saying that my boyfriend had replied to her personal ad on craigslist. This person didn’t specify the type of relationship that she was seeking, but she did include the text of my boyfriend’s response to her ad. His response consisted exclusively of his “stats” and the typical “are you for real?” inquiry … it makes me think it was about sex. Anyway, he denied doing it but he seemed twitchy, and he did admit that sometimes he longs for the single life (we’ve been together for about a year and a half). So already I’m … somewhat distrustful.

(Side note: I don’t know how this person even figured out that I was the one to email about this: the boyfriend and I aren’t even “Facebook official.”)

Then I went to check my email on his computer a while ago and it automatically logged me into his account. I don’t even know the password. I was moving the mouse to click “sign out” and my eyes fell on a chat he’d had with his ex. I opened it (I KNOW!). He instigated the chat by saying “get out of my dreams!” she said something like “what did i do now?” (it was obvious to me that she wasn’t flirting back), and he said “i had a dream about you, and you were so hot and being mean to me.” Which in his language means she was dominating him. In bed. Then I flipped through his chats looking for other stuff he said to her (I KNOW!!) and his outbox is basically full of him trying to get in touch with her and her ignoring him or blowing him off. This makes me feel somewhat OK since he’s getting nowhere with her, but clearly … he’s TRYING to get somewhere with her, right? UGH! So now I REALLY want to ask him WTF and flip out, but I came by this information completely “illegally” and so have no right to use it. Right? My question is: do I just have to sit on this until he slips up for real? Or can I bring it up (in a direct way, since I’ve already tried the “do you think guys can get over their exes?!?” line of questioning and he’s having none of it)?

Sorry for going on and on but … I guess I didn’t know how to boil it down. This episode happened a while ago and I’ve been mulling in silence since then — I just don’t even know where to begin and I’d rather have a good, well-thought-out argument for my feelings than blow up right away and look stupid in the end.

After reading the above account there’s little regard I’m going to give to your boyfriend. SORRY! FUCK THAT JERKFACE! While I’ll refrain from making too much fun of his dated online proclivities (60 Minutes II called, they want him to come in to re-tape a lost interview from 2002 for their archives), the dude cheated on you. Who gives a shit about what cheating actually means? “Welllllllllll, I mean they did only kiss.” “Welllllllllll she’s an ex-girlfriend and she’s still in love with him so I understand if…” If anyone in a committed relationship attempts to fuck or kiss someone else, then what’s the difference? Let’s even forego de facto and go straight to de jure — according to the law, “ATTEMPTED” is still lawful grounds for wrongdoing.

Why must so many people sully the good names of awesome relationships!? It’s simple, man. Be honest and kind, make her come and make her laugh. Everything is easier when you’re honest! When I once asked this guy I knew why he locked his phone he responded with, “’Cause I have a girlfriend.” COOL ANSWER YOU RIDICULOUS IDIOT. It would appear that you’re dating this kind of person. He always takes his phone with him to the bathroom and sometimes checks his texts in the middle of a mealtime conversation with this weird half-in-pocket-half-out move as he phumphers, “yeah, uh, huh.” It’s not cool to tell an ex “you were so hot and being mean to me.” Running into an ex and saying, “hey! you look great! How are you?” is one thing, “you were so hot in my dream” quite another.

Yeah, sure, you shouldn’t snoop. A girl once went through some old writings while I was out buying us dinner. She read a bad short story I wrote a full two tears prior (fictional, mind you) where I describe a makeout scene and for the girl I used an actual girl friend of mine’s name (Aleema. Cool fucking name, right??). She thought it was non-fiction, that I had just written it, and she interpreted it as depicting me cheating on her with Aleema and proceeded to smack the pizza out of my arms (pepper flakes everywhere!) as I entered the door. I broke up with her right there.

But you did find something, so let’s move past the whole “but I found out through ill-gotten means” part. He’s actively trying to cheat on you and you will need to have the conversation. I’m sorry, but I can’t NOT recommend breaking up with him. Every time that I write these columns I answer your questions as if you guys are one of my closest girl friends (who also ask me these kind of questions too! IRL!) and I will only give you the same advice I’d give them. And right now I’d tell them to break up with this wondrously gaping asshole of a boyfriend immediately and then to keep him the fuck away from me. ‘Cause my friend is bartending, and getting into fights is sooo 2010.

Previously: Cheating, Pregnancy Terror, and the Pot Belly.

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

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