How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
I love being penetrated. I have had several partners in the past, some very well-endowed lengthwise, and I have never had any problem having them deep inside me. Recently, my partner and I acquired a very, very generous dildo to play with, and we discovered that we can only get it about halfway inside me before we “hit” the cervix and cannot go deeper. I was surprised—I was not in pain or anything, but we just could not go any further. So how do women take huge dildos inside them in porn movies? Like, literally—where does it go? Am I being silly? And do you have any tips to get it in deeper?
—Into the Deep End
Dear Deep End,
After over a decade in the adult film industry, I wasn’t sure how to answer your question. So I reached out to my colleague Joanna Angel, author of two erotic novels, who recalls doing one single huge toys scene in her extensive career. “There’s one or two directors who specialize in it,” she says. “So have no fear: We are not all sitting around with giant toys inside of our mysteriously elastic holes.”
She points out the same physical limitation you report. “When it comes to the vagina, it does kind of end. I mean, things can only go so deep. With enough dedication the vagina can stretch to handle almost any girth … but as far as the length, sometimes it just can’t go any further,” she says. “Sometimes changing positions helps? Depending on how it’s tilted. Personally, I can get more in me if I’m riding a dick or if I’m on my back.” As context, she adds, “If you look at those giant toy pornos—or really even any porno—it’s rare that the dick goes all the way in.”
Joanna, a notorious anal aficionado, also suggests you try a different hole: “If I was ever asked to get a giant toy all the way in me, I’d definitely use my ass. So, good luck.”
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Dear How to Do It,
I am a single mother in my late 20s of a toddler and an infant. I have only watched lesbian porn for as long as I can remember, yet I’ve never been with a woman, and I’d very much like to. Although I’ve had many male partners, I realize I am not attracted to many people. I may see five strangers a year (when people-watching out in public) who I can actually imagine myself engaging with sexually. Almost all of my previous partners I engaged with were not out of a true sexual desire, but due to my low self-esteem and insecurities.
How can I find out what it’s like to be with a woman? I am petite, athletic, and very feminine. While playing sports in college, a lesbian teammate had a crush on me (that I never reciprocated) and attacked my roommate out of irrational jealousy. Since then I’ve been a bit fearful of masculine women, who I am not attracted to. But I live in a progressive and very gay-friendly city, and I go out all the time, and any time I have been obviously hit on my women it has been this “type” of masculine woman. On the rare chance I finally spot a woman I am attracted to, I know I would never ever make the first move out of fear of offending or ostracizing her in case she isn’t into women sexually, and none have ever obviously pursued me. I tried going on lesbian dating apps and found it didn’t work for me. I’ve given my number out to a few women in the past six or so years who I was attracted to, but couldn’t bring myself to initiate anything sexually and they didn’t either. Am I missing something? Is there a code word?
I’ve had this desire since I was 14, and I can’t believe I haven’t fulfilled it yet. I’m beginning to feel hopeless. I no longer feel any attraction to men whatsoever. Which raises a lot of fears—what if this lesbian attraction is just meant to be an unfulfilled fantasy and I get scared or turned off during sex and offend the other woman? What woman would pursue a newbie with baggage like me? I’d like to have an exciting sex life and a relationship with a woman, and I just don’t know how it’s going to happen.
I should also mention I’m in therapy and on antidepressants and feel quite good emotionally, all things considered.
—I’m Staring Because You’re Gorgeous
Dear Gorgeous,
You’re an adult. Like most adults, you’ve been through some experiences that were negative or painful. Plenty of your peers will have experiences of their own that are similar in impact or emotional weight. Working with your therapist to feel less like these experiences are baggage and more like they’re a part of your past is likely to help.
Everybody starts somewhere. As much as there will be women who prefer to avoid the new and curious in their community, there will be others happy to show you around. And remember, we all have to learn every new partner’s body from scratch, no matter how experienced we are and regardless of gender. This is where good listening skills, body language awareness, and ability to communicate our own preferences are crucial.
What if you change your mind during sex? That happens. It happens to people who are trying things for the first time, it happens to people who are trying something with a new partner, and it happens to people who are doing the same thing they’ve been doing every Tuesday since the Obama era with the same partner. When it happens, you should communicate that, and sex should come to an end.
Have you spoken with your therapist about your feelings around the early negative event with your teammate? The effect that’s had on your experience of butch women moving forward, and the permanence of that, feel like something they should know about. Regardless, you aren’t attracted to masc-of-center women and that’s 100 percent OK. When you do find women you’re attracted to, you absolutely might offend a woman by expressing a sexual interest in them. They also might be uninterested but flattered. They might be straight, or lesbian, or just not find you to be their type. Dating is a process of giving and receiving rejection until we find a match.
Complicating all of this further is the fact that we’re in the middle of a global pandemic. You can’t spend more time at a lesbian-friendly bar or go to community events. If you haven’t tried OkCupid and Feeld, I think they’re worth a shot, as they tend to skew more queer and LGBT-friendly. In the meantime, you can keep working on yourself so you’re that much more ready when you do meet someone. Good luck.
Did you write this or another letter we answered this year? Tell us what happened at howtodoit@slate.com.
Dear How to Do It,
I’m a man in my 30s who’s been with my wife for about seven years, married for three. I’ve always had a higher sex drive than her, which generally hasn’t been much of a problem, but recently we’ve hit a bit of a snag. My wife has never been “thin,” but a combination of issues (an injury, a global pandemic, new meds) has caused her to gain a fair amount of weight. She’s become very self-conscious about her body while I, on the other hand, have never been more turned on by her new curves!
I keep telling her that she’s more beautiful now than the day we met, which is absolutely true, but she seems to think that it’s just me being generally horny rather than actually loving her and her body. She now pretty strongly prefers sex with lights off and under covers and asks me to avoid her “problem areas” when we have sex. Possibly complicating her feelings, I’ve been staying very active this pandemic (which helps me with my brain chemistry more than anything) and have personally lost some weight. Of course I’ll be supportive of any exercise and diet if or when she’s fully ready, but in the meantime, how do I convince my incredible wife that her “new” body is nothing to be ashamed of without treating her like an object during what is a pretty stressful time?
—I Love My Curvy Wife
Dear Curvy,
Your wife’s relationship to her body is hers to handle. You can offer support—you can listen to her if she feels like expressing herself verbally. You can respect her wishes by leaving the lights off and avoiding the parts of her body she’s asked you not to touch. Absolutely support any diet or exercise changes she wants to make, but let her have all the initiative there. The next time your wife brings up her weight on her own, you might state what you’ve said here—that you think she’s beautiful but are happy to support her if she chooses to make changes.
It might be wise to reduce the amount of physically specific appreciative comments you make, as the side effect of generally reminding her of her body may be exacerbating the issue. Stick to general and emotional comments: “You look gorgeous,” “I’m so aroused by you,” or “You make my heart so happy.” You might also channel that desire to praise into specific comments on the care she extends toward you, her wit or charm, and other nonphysical attributes.
Dear How to Do It,
I’m a female teenager. I hate shaving my legs. It takes forever, I’m not good at it, it dries my skin out, and I’m aware that the social norm of women shaving their legs was started by Gillette in the 1920s to sell more razors. For these reasons, I decided to stop shaving my legs. My mother apparently thinks I am ruining my life by making this decision. At first, she told me that I’d be made fun of by all the girls at school (this hasn’t happened). Now, she’s switched to telling me that guys find girls with hairy legs unattractive and that I’ll never find a husband. She’s usually pretty nonjudgmental, and I have no idea where this attitude is coming from. How do I get her to stop?
—Too Young to Worry About Marriage Anyway
Dear Too Young,
“Mom, you seem really upset about my leg hair. I’d love to understand what’s going on. Can you fill me in?”
It might not work. Prepare yourself for that possibility now. You might get another “men don’t like it” or something else just as odd. She may not feel it’s appropriate to share. She may not want to share. She may not even understand herself and therefore be unable to share. But it’s worth a try. Pick a calm moment—definitely not when you’re in the middle of an argument about this subject, more after she’s had half a cup of tea or whatever relaxes her. Take a deep breath beforehand. Use your most calm tone of voice.
If you can get insight, you’ll have a lot better chance of answering the question of how to get her to stop. If you can’t, you can try the direct approach: “My body hair is my choice, I want to understand why this is affecting you so much, and I’m asking you to drop the subject until we can have a more productive conversation.” If it continues to be a point of contention, work on constructively changing the subject. It’s a skill that will serve you well in life.
Moms are humans. Sometimes they get stressed out by other stuff and act weird. Sometimes they get hung up on details for reasons none of us understand. Sometimes they’re right, and sometimes they’re wrong. But like in any relationship, a conversation is always a good place to start.
—Stoya
More How to Do ItI’m getting divorced from my second husband and remain friendly with my first. While babysitting my granddaughter and having my ex over for dinner, the subject of getting naked came up. He knows how miserable I am, and his wife has lived several states away for years. Both of us could seriously use a good roll in the hay. Fast-forward to a couple nights later when we tried. Let’s say Mr. Johnson did not show up for work. I was very understanding: He is of the age where that could happen. I finally convinced him to get some little blue pills to see what comes up, so to speak.
What I want to know is what can I do to help wake things up, if you will? He is very afraid that the pills won’t work (it turns out he took one he got from a friend the one time we did try, and nothing happened). I understand not wanting to be embarrassed again, but I would never humiliate him as I know he can’t help it. I just want to know if there’s anything I can do to facilitate things. Sure, I have an ulterior motive, but we’d both be the beneficiary if we get things going. Any suggestions?
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