Ask Heather: Topless Text Edition

I have given up on what day of the week the Ask Heather is going to take place on. I can’t handle it. I’m too chaotic and deadlines stress me the fuck out. So, you’ll have to read it when I write it and like it and that’s the way it’s going to be. My apologies.

Here is the question I meant to answer two weeks ago. FYI, it’s from a girl, so this week will be a bit different from the last few weeks…

Dear H,
This guy I’m seeing asked me to send him naked pics of myself. Since we’re long distance, I’m considering doing it. I have a few questions… why does he want them, what should I send, will this make me a whore and should I ask for some in return?
Help!
(Almost) Topless in Europe

Ooooh, goodie. I love questions about being topless. Let’s do this. I’ll answer your questions in order.

1. Why does he want them?
Three reasons, depending on who he is.
A. This applies to any guy ever asking for naked pics…He wants it to jerk off to. No exceptions. This is 100% true of every person with a penis on earth and if they say otherwise, they are fucking liars. Now, I don’t quite get how a still shot, photo or magazine or whatever, does the trick. I’ve always been partial to action shots like movies or Penthouse letters (that shit is great) or fake porn I create in my own head but guys are pretty simple and so are photos. I think that’s the logic.
B. They want to show their friends. This will prove they are at least talking to someone who likes to get naked and will give them something to talk about at the pub on Friday. I am positive whatever they tell said friends about you will be an exaggeration but that’s to be expected. Since you have to prepare to have this picture be seen by others, you better make sure you look good, which we will discuss shortly. And if they say aren’t going to show their friends, they’re probably lying. Just the other day my husband told me some guy showed him a video of some girl doing The Bad stuff to him. Guys.have.no.shame. Remember that.
C. One day, when shit goes wrong, he is going to put your naked ass all over the internet and then call you a skank and an ugly whore. If you send naked pics, I would try to end a relationship nicely, for your sake.

Now. What should you send? Hmmmm….

I’ve mentioned to a couple of guys that this is going to be a post because it’s an actual true story about one of my friends and she tried to take the pictures herself, WHICH I FOUND IN HER PHONE, and I was all, OHMYGOD what are you DOING? She, I think, was drunk off The Wine when she tried taking them of herself so she was like, Ummm, taking naked pictures of myself which led me to shriek, OHMYGODISTHATYOURJAGE???? and so let’s just say we had to have a talk and I am going to be taking the next round of photos of her to send because it is easier to have a buddy do this for you, and more flattering, unless you’re just looking for tit shots, which I assume one can manage themselves. But anyway.

I think tit shots are best. I think most guys would agree that they don’t need an up close shot of your goodies (I do not want a picture of anyone’s axe wound in my phone, as one friend so kindly put it) because jage is not even attractive. Furthermore, if they do want pics up close and personal of your pretty taco, they probably want something going on, like diddling with your hands or toys or something pornographic that I’m sure you’ll feel awkward doing with one hand and taking a pic with another. And for the record, I don’t mind helping a friend with photos of the nudie variety but I’m not doing it if she’s looking at me smiling and is knuckle deep. No thanks, all set. So, moral of story is I think you can stay away from the vagina pics.

BUT REALLY. If you decide to go all Jenna Jameson on us and toss your jage in the shot, make sure you fucking shave and don’t act like a rookie hippie and leaving a crazy mess down there. These photos need to be better than your senior pictures for the love of God.

Also, I think you can leave your ass out of it, but if you want to toss that in, make sure your ass is somewhat decent looking and maybe bend over something. I’ve never met a man who doesn’t like a girl bent over.

Back to the tits. So. Please lotion yourself up first so you’re not all dry skinned and your nipples must be perky. No one needs to go into this with soft saucers so if you aren’t all excited yourself, give them a twist. Soft nipples are not hot. If you could take the photo after getting out of the shower, I assume that would be a bonus because you’ll be wet and everyone loves a nice shot of wet, naked bits.

I think your best bet is the on the bed, on your knees, wearing nice skivs, topless, hair a bit of a mess photo. And maybe make a pouting face. Guys love that stuff. But let’s be honest, exposed nipple and a thong will do the trick every time.

Next question. Are you a whore or skank for doing this?

Well, you’re obviously a bit crazy and somewhat skanky because 100% respectable girls are not going to text a tit shot to anyone. But also, those girls are boring and give bad head too so no one really wants to be 100% respectable, now do they?
Besides, naked pictures are exciting. They spice stuff up. So, if that makes you a whore, so be it. At least you’re an exciting, topless, kinda crazy whore with great photo skills. Could be worse.

Should you ask for one back?

Well, there’s yes and then there’s no. Yes, so you can then email it to yourself and save it so if he ever fucks you over, you have a picture of his dick to do what you please with. Especially if he’s hooked or odd-looking or not as big as you claimed when dating. Then when you go through a bad break-up, you can host a wine night and show all your friends and you can have a good laugh/cry about your ex with the fucked up dick.

But no. Let’s be honest. No one needs a picture of cock and balls in their phone or in their email. As magical as they feel in the jage, no dick is wicked easy on the eyes. I mean they’re fine and all but it’s not like looking at a unicorn or a firework show. So thanks but no thanks, maybe just send a topless pic of you sweating or tanning or walking out of the ocean dripping wet.

And those are my inappropriate thoughts of the day on swapping naked pics.

Oh wait. VERY IMPORTANT. If you send one, you’ll have to send a million. Remember that. It’s like giving a kid a lollipop and then telling him no more sugar will be consumed ever again in life. Meltdowns will ensue. Good luck.

Hope this helps!
xo,
H