How to Do It

I’m a Beautiful, Accomplished 28-Year-Old Female Virgin—With One Huge Hang-Up

A young woman with a pensive look on her face, with part of her missing, outlined in neon pink.
Photo illustration by Slate. Photo by Honored_Member/iStock/Getty Images Plus.

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’m 28 years old and still a virgin. I’m beautiful, smart, fun, and have an awesome career. I’ve had boyfriends that I’ve been honest with. I tell them, and either they will work with me or they won’t. The reason it never works is because I am literally scared of penetration. Sex looks good—I can fantasize, no problem with getting wet, oral sex, it’s all fine. But when he tries to insert it, I lose my shit and feel like I’m about to pass out. I don’t wear tampons. I barely touch myself. I’m getting older now, and I want to settle down. I want to have kids. I just can’t wrap my head around how I’m going to take a dick.

—No Entry

Dear No Entry,

This is a doctor-level problem. Specifically, a gynecologist or a pelvic floor specialist. Maybe both, in the end. There are many possibilities, like vaginismus or “vaginal penetration phobia,” a subcategory some researchers proposed in a recent paper. But this isn’t immediately life-threatening, and we’re living in a global pandemic, so let’s focus on what you can do in the meantime.

Touch yourself. Get highly aroused and see if you can put one finger inside yourself up to the first joint. If that goes well, proceed to the second joint. Then all the way in. Feel around and see if there are any points of pain. If everything is still feeling fine—stop if it’s not—try a second finger and then try spreading them apart. Wiggle with medium abandon. See what happens.

Take notes—for your doctor, for when it makes sense to see one. Since you’ve probably got the time right now, you might as well repeat this experiment a few times on different days. Track all this data. If you’re consistently feeling no pain when you’re touching yourself, you might try a tampon the next time you get your period. Just to see what happens. (Do not put a tampon in when you aren’t bleeding. Getting it back out when it isn’t soaked with menstrual fluid is either an abrasion nightmare or a long soak in a bathtub.)

If tampons are also fine, you might want a trip to a sex-positive therapist instead. The good news about that is many therapists are offering telemedicine right now, and you may be able to see one soon.

Dear How to Do It,

As out-of-work young people turn to camming, and the rest of us try out being customers, we’d appreciate tips on camming etiquette for both ends of the camera.

—Kodak Moment

Dear Kodak Moment,

My experience with camming is limited. I’ve toyed around with it through ManyVids a few times over the past few months, but only started camming in earnest a few days ago. So I reached out to a few of my more experienced colleagues. (I should note I work with some of these people, or work with other people who do.)

Bella French, CEO and founder of ManyVids, had some advice for consumers. “Like any social setting you find yourself in for the first time, no one enters a cam room for the first time and automatically knows how to act,” she said. “Cam models feed off the energy from their fans.” She added, “We want to please our audience and that works both ways: models want to give their audience the fantasy they’re looking for, and audience reaction can definitely influence the show. If you’re not sure how to behave in a cam room, simply follow the same social rules you observe in daily life: be polite, be respectful of one another, and show gratitude. Don’t be rude or offensive. Don’t ask for anything that is out of bounds, and always show your appreciation through tips.”

Amberly Rothfield has written two whole guides on online sex work, and she said professionals are well aware people are getting cabin fever while social isolating. “Choosing a cam show to relieve some of that pressure is not only wise but will be a popular choice,” she told me. “Just remember to keep it upbeat and happy when you do so. It can be easy to pass some of those negative feelings at first onto the cam model you are interacting with if you aren’t thinking about it. Be extra courteous, and watch as the model you have in mind returns it in kind.”

Go Ask Alex, a frequent MyFreeCams user, had some more detailed guidelines.* She said “generally, webcam models will have a profile or list of ‘rules’ to abide by in their chatrooms. The rules will change depending on who you’re watching, so I can’t speak for all streamers. I can, however, draw from my own experience. Two of the important rules in my chatroom are as follows: Dirty talk should always be accompanied by a tip, and must be shared privately. If you have a request, preface it with a tip or wait for an appropriate moment to ask what the cost would be. For instance, joining a show midway through and insisting ‘show us your ___!’ may not get the reaction you were hoping for.”

Alice said patience is key: “The most important thing to remember is to be respectful and patient. Streamers are often managing multiple programs as well as public and private conversations, and may not be able to respond instantly—but if you are talking and tipping, know that they are grateful for your presence.”

For people who are considering performing, French, the ManyVids founder, also has some advice: “The No. 1 most important rule is to always respect yourself. Listen to your heart and never be afraid of saying no.  Surround yourself with positive people that truly respect you and want the best for you. If you feel that a specific opportunity is not something that matches your values, you simply pass on it.”

She went on, “For camgirls and camboys, this principle is very true: Only offer cam shows that you want to do. It’s OK to decide not to do any sexually explicit cam performances. Actually, most of the most successful cam artists don’t offer sexual shows. They are beautiful, smart, and interesting entertainers. Webcamming should be a safe space from the safety of your own home where you have the liberty to express yourself however you wish to do it. You are in control. You decide the topic of your show. You decide how long your show will last, what you will wear, and so much more.”

Thanks to these ladies who took time out of their very busy days right now to give us some insight into camming. I couldn’t have said it better.

Dear How to Do It,

I have a boundary with my husband visiting strip clubs and other places he may encounter a sex worker. For example, one of his friends hired topless entertainment at a fantasy football draft, and some of the other people there paid for lap dances. I don’t want him there in those situations. I truly don’t care if in a professional, transactional situation, he partakes in a lap dance or even more, but my concern is that I want to make sure the worker is there consensually and isn’t a victim of trafficking or abuse. Given this, he’s wondering if there’s some way he can assess these situations. How can he politely inquire about her status, so to speak?

—Verification Check

Dear VC,

Let’s talk about consent. Mimi Mercedez, a Serbian rapper and music producer, has a really great quote: “Can there be feminism under capitalism?” The point is that we’re all—yes, even those of you who don’t deal with sex professionally—in a position where we do things we don’t want to do, or are only doing for money, as part of our jobs.

I speak from moderate experience here: One lap dance is fun! The second is great! The 10th lap dance in a row is grueling and painful. Maybe the pain is just my arthritis. On my 10th lap dance, the first—and only—time I gave them, I wanted to stop, but I didn’t want to disappoint my customers. I knew, like all gig economy workers know, that lean times would come, and I would regret turning down that money. Most of us didn’t consent to living in a system where a few missed paychecks could ruin us.

The U.S. Department of Homeland Security defines trafficking as “the use of force, fraud, or coercion to obtain some type of labor or commercial sex act.” There are people who likely serve you in many contexts outside the sex industry who might fit some form of this definition. Are you also asking who works in the kitchen at your favorite restaurant? Do you inquire about who peels the shrimp before you down that delicious shrimp cocktail? Maybe you don’t eat shellfish, but you get what I’m saying. I’m not sure why you’d assume the worst only in this context.

As for inquiring about status, your husband should understand that some consensual sex workers will be offended and feel as though their autonomy is being undermined or called into question. He can keep an eye out for women who look cowed, scared, heavily bruised (not the normal knee and shin bruises, but like fingerprints on arms), but mostly he’ll want to inquire about the hiring process to his friends. How did they find this worker? Did she handle the booking herself? Did they try to negotiate her rate down? Did they pay her promptly and fully? Is anyone in the room trying to use force or coercion to get more out of the worker than she is willing to give?

Bottom line: We’re all a little coerced, and inquiries about hiring practices are superior to badgering a woman who is probably just trying to work with questions about whether she’s being trafficked.

Dear How to Do It,

I am a woman in her mid-20s with a boyfriend of five years. Recently, he’s opened up about being into BDSM, which is great, because I think I want to explore that too, and we’re natural counterparts. He is into me removing all of my pubic hair, me wearing a collar, choking me with his dick, and “using me” generally. These acts feel toxic, but also turn me on. I want to be sex positive and get over my feelings, but I haven’t been able to, and I also can’t help but feel resentment that he hasn’t grappled with the misogynistic roots/consequences of his preferences or looked at them critically. He seems exasperated because I want to challenge them—even though my motivation to do so is rooted in my experience as a woman. I feel like he should be interested in empathizing with where I’m coming from as my partner.

Now he won’t bring it up or try anything out of the ordinary—he doesn’t want to because he’s afraid of pressuring me and making me feel bad. I want to explore together and don’t want to shy away from something that makes me uncomfortable, but I also have been unable to accept this part of myself fully. How can I move past this?

—BDSMaybe

Dear BDSMaybe,

Are you sure you want to engage in BDSM play—specifically BDSM play with heteronormative gender roles—with a man who refuses to interrogate that? Who’d rather just not do it than do some introspection?

I’m seeing a red flag.

Sex positivity gets skewed to mean “positive about all sex” instead of “positive about people doing what feels right for them with people who also feel right about their part in the activity, under the guiding principles of safe, sane, and consensual.” Sex positivity does not mean you ever have to engage in a particular act. Thoroughly asexual people can be sex positive without ever engaging in a sexual act.

Don’t put pressure on yourself to engage in activities that make you uncomfortable, or under conditions that make you uncomfortable—such as your partner avoiding deep communication about the acts you’d like to do together. To explore this side of yourself, you’ll need to find a partner who can give you everything you need to think it through, and it doesn’t seem like you have that here.

Before you go, for the future, a word about aftercare. After an intense BDSM session, it’s common—and recommended!—to take some time to process what just happened together and share feelings and responses. Kink.com has some great examples of professional sex havers engaging in aftercare. Keep that in mind if this does become a reality.

—Stoya

More How to Do It

I never thought I’d be in this position. I am married and love my wife. A gorgeous woman from my office struck up a conversation with me one day at an after-work event, and she later added me on social media. She’s married, but she flirtatiously DMed me. She kept it up, and I barely responded, but then yesterday, she straight-up propositioned me for sex. No strings. I am an average guy, and women haven’t come on to me like this since I was in my late teens and early 20s. I don’t think I’ll get this opportunity again while I’m still young. Is there any way I could do this, be happy it happened, and then move on, or am I kidding myself?

Correction, March 26, 2020: This post originally misidentified Go Ask Alex as Go Ask Alice.