Love + Sex Love

Long before I lost my virginity, I was teaching my friends how to do it

When I first started teaching, I hadn’t even had my first kiss. I joined the Teen Advisory Board (TAB) of my local Planned Parenthood when I was fifteen. We were a group of teenagers dedicated to becoming a safe resource for our peers to talk about sexuality. I taught my peers how to properly put on a condom (pinch the tip, you guys!) but the furthest I’d ever gone with a boy was holding hands in social studies while watching a video about Neanderthals.

I never did the stereotypical things associated with adolescence. My hometown had plenty of John Hughes movie potential, but I was shy, socially anxious and depressed. I’ve since learned that leaving your house is 99% more like to result in smooches than laying in bed re-watching Buffy, but volunteering for Planned Parenthood was the only thing that motivated me to leave my bedroom every week.  

[bctt tweet=”Leaving your house is 99% more likely to result in smooches than re-watching Buffy.” username=”wearethetempest”]

I wouldn’t end up having my first kiss until college, but I spouted off knowledge about every available form of birth control. My friends knew I’d been trained as a peer educator in TAB, so they texted me with questions like where to find Plan B or whether you can get herpes from sharing drinks. Once, in the middle of English class, a male friend asked me “So… where exactly is the clitoris?” I drew him a diagram without hesitation. 

A fellow TAB member joked that when I finally had sex, I would just start yelling facts about sexual health. She imagined my partner climaxing and me shouting “THERE ARE 200 MILLION SPERM IN EVERY EJACULATION!”

As volunteers, we had access to what was known as “the condom closet.” We’d stuff condoms into paper bags to give to our friends. Since most of my friends were just as awkward as I was, the condoms mostly sat in my backpack or room. 

[bctt tweet=”Teaching sex ed made me feel empowered in spite of having no direct experience. ” username=”wearethetempest”]

My Mom would find them and skeptically declare “Why do you have these?” I can assure you, Mom, that as much as I would’ve liked to be A TOTALLY COOL TEEN WHO WAS DEFINITELY HAVING A LOT OF INTERCOURSE WITH ACTUAL HUMANS, I was not using them. 

Except maybe on my thumb in my best friend’s car to test which flavor of a condom was the most disgusting. The answer is definitely banana.

Now that I’m a sexually active adult, I laugh about the fact that I considered myself an expert in sexuality years before I’d come anywhere near another person’s sexy bits. I felt like I could understand everything about the world just by educating myself.

“Communicate with your partner,” is advice I repeated often. It never occurred to me that the shyness that prevented me from going to parties as a teenager would not magically disappear once I started dating.

When I finally had sex at 23, knowing what I “should” do didn’t make it easier for me to communicate. I went from never having been kissed to casually dating in what felt like a heartbeat. Shockingly, my expertise on birth control and STD’s did nothing to alleviate my self-consciousness. Instead of directly discussing my emotions with my partners, I’d text all my friends to tell them what happened. I remember asking my best friend for advice about what I should text the guy I lost my virginity to.

Annoyed with my indirectness, she replied: “Send him an e-card!” Instead, we just sort of ghosted each other after five or six dates. 

[bctt tweet=” Knowing what I ‘should’ do didn’t make it easier for me to communicate.” username=”wearethetempest”]

When I was a teenager, teaching sex ed made me feel empowered in spite of having no direct experience. It turns out that having his information didn’t necessarily help me make perfect decisions as an adult. It also somehow didn’t make me super amazing at sex. Still, my experience in TAB helped me understand how to talk openly with my peers about taboo issues.

By the time I finally started getting my smooches, I knew how to be vulnerable and open about my emotions and curiosity. In TAB, I found a safe space. I learned how to answer questions by first acknowledging their validity. My own questions were just as valid as the ones I had been trained to answer years before.

Love Advice

Do I actually have to try this out in bed, especially if I’m not wild about it?

Dear Madame Lestrange,


WHAT ARE GUYS’ OBSESSIONS WITH IT. WHAT IS THEIR PROBLEM. I’m with a man who’s the love of my life but he keeps pushing me to do anal. I am *tentatively* open to it but also TERRIFIED OUT OF MY MIND because hello.

In the words of Amy Schumer, that’s where my poop comes out.

Do I have to go through with it? And what if I do want to go through with it – what then? I just want to make him happy – but I’m curious, too.


Maysa, 29



Hi Maysa,

Great question. Guys and anal…hah! I’ve heard plenty of my friends talk about their partners requesting to have anal sex, in which they have absolutely no interest. I also know tons of women who loooove anal sex. But do you have to go through with it? NOPE. Absolutely nope. You don’t have to go through with anything that makes you uncomfortable or that you’re not totally into or that you’re even just “meh” about. It doesn’t matter if your partner really wants to – if you don’t, that’s that, right?

Why should what he wants come before what you want?

He shouldn’t be pushing you into it either… I have no issues with a partner asking, suggesting, wondering, but then respectfully dropping the subject at any apprehensive response.

Pushing? Nah—unacceptable. Ask him to leave it alone until you come to your decision!

[bctt tweet=”I get it – anal can be scary, it seems gross and painful, etc.”]

Now, let’s try to alleviate this fear and uncertainty. I get it – anal can be scary, it seems gross and painful, etc. You’ve probably heard a lot of horror stories from people about their mishaps with anal.

But, honestly—if done right, anal sex can be a really enjoyable and intimate experience for you and your partner. I would suggest some anal play to help you decide if it’s something you’re remotely into.

If y’all haven’t done this yet, start with anal sex that doesn’t include a penis: get him to finger you anally or perform analingus. Buy some smaller dildos or vibrators to test how they feel when he puts them in (warning: don’t forget lube with this!). These smaller steps will not only help you figure out if you enjoy anal action, but they’ll also help you put aside some of the fear related to anal sex.

You’ll start feeling much more comfortable with and excited at the idea of putting a full-size dick in there if you end up liking the smaller things!

Here are some tips if you decide you like the play and want to start having full-blown anal:

  1. LOTS of foreplay and some vaginal sex first. Get yourself really wet and really turned on. Especially for your first time, you’ll probably feel a bit nervous! But if you and your partner start out with stuff you’re already comfortable with, you’ll also feel more comfortable once he puts it in your ass.
  2. LOTS of lube. You know this: your vagina creates natural lubricant, especially as you get more turned on, to allow for a penis (or whatever else you’re sticking in there). Your anus and rectum do not. If you don’t use lube, you run the risk of pain, tearing, infection, etc. But with proper lubrication, you should be good. Make sure to take it nice and slow. And if you think you need more lube, reapply it!
  3. Once he’s in there and doing his thing, I suggest one of you manually stimulates your clitoris. Let him finger you or do it yourself. It’ll help you enjoy the experience so much more. This is one of the perks of anal sex! So much stimulation is possible for you.
  4. Let him know beforehand that you might ask him to stop. And know that just because you decided to go for it, doesn’t mean you can’t change your mind right before or even during. Lay down your rules for what is or isn’t okay. Do you want him to ejaculate inside you? Do you want him to use a condom (tip: safe sex is the best sex)? It’s all up to you, girl.
  5. If you’re worried about the whole poop thing, some suggestions: if you feel like you have to poop, don’t have anal sex. You’ll probably freak out and think you’re gonna poop on him (when you first get anally penetrated, it kinda feels like you have to poop. This freak out is real.). Take a shower before you think you’re gonna do it and clean your ass out a little. Honestly, he knows what the anus is for and what it does. Also if he gets grossed out by anything poop-related, that’s on him!
  6. Have fun. Like I said before, many women love anal sex and it can be a really intimate experience. But if you don’t like it, there’s no problem with that either. Just remember that sex (all types) is about two people sharing and enjoying an experience together. And each person has her/his likes and dislikes. So, don’t get too lost in the worries of making him happy with this. A good sex life comes from both partners being happy, not just one!


You’re welcome,

Madame Lestrange


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