Dear Liara,

I’m a virgin and have never been able to take anything further than kissing. I’m going to be turning 30 soon, and I’m worried that I’m getting so neurotic about sex that I’ll never be able to actually do it. To be clear, I’ve had women who were interested in having sex with me, and who have even come on to me, but I couldn’t get hard when it came down to it. I was so soft I couldn’t even put the condom on.

I have no issue masturbating, so I know it’s a psychological thing. It’s really hard, because the women I’ve been with have taken it personally and believe I am not attracted to them, even though I am. I actively avoid flirting or going on dates with people because it’s just been so hard to make this work.

What should I do? I’m thinking about hiring an escort to help, but I’m worried she’ll just laugh at me if I’m bad at sex.

Feeling hopeless,
D

Hey D,

When I was an escort, I saw quite a few virgins in my time. In fact, I was somewhat infamous for my active preference for virgins. A lot of my favorite clients have never had sex before, for a variety of reasons!

I actually once had a client with a very similar plight to you, although he was in his mid-fifties! He had had multiple girlfriends, even tried hiring three different escorts, and it had just never worked. He saw me shitposting on Twitter about how I love virgins, and decided to reach out and see if I thought I could help.

I told him I was happy to try my best, so we soon had a date. He was incredibly nervous, sweating and talking nonstop as soon as he walked in. He told me he really wanted to make sure I had a good time, and that I wasn’t disappointed in him. I sat him down on the bed, covered his mouth so that he’d stop talking and said: Look. I’m the professional here. You hired me for a service; let me do my job. Stop stressing about what’s going on in my mind and let me take care of you!

He nodded, but when I took my hand off his mouth he was chattering nervously again. I told him not to talk unless it was to give me feedback on sensations like That feels good, or That feels bad. I straddled him and kissed him, clothes still on. He started to get hard in his pants. We kept kissing as I took our clothes off. When the time came for his undies to come off, he went soft again. He started trying to talk to me again, telling me to switch positions or try this or that, and again I shushed him and told him to just lay back and let me do my job.

I take a multi-pronged approach with people who are having difficulties getting hard. One: Get them out of their heads (and their mouths) and into their bodies. It’s hard to get hard if you’re not present! Often, this means telling them to stop talking. Two: If they get very nervous, I often retreat for a bit, cuddle naked, and talk about other things with them. Taking their mind off sex and just having a pleasant time being naked together can often do wonders for getting people comfy. A little counterintuitive, but it works! Three: Blowjobs, coupled with either a cock ring—or even better, using my thumb and index finger as a makeshift cock ring—are the easiest way to “force” someone to get hard. Unless they are super old, using your thumb and index finger to restrict blood flow through the base of the cock while you suck them off will usually result in someone getting hard, even if it takes a bit.

These techniques eventually were effective on him! The look on his face when I got the condom on and stuck him inside me was hysterical! He looked very shocked, but very happy. Virginity demolished! He finished after a bit and seemed almost bemused that he had actually had his penis inside a vagina. A few months later, he sent me a very sweet email about how he had used these techniques successfully with his new girlfriend, and they now had a very satisfying sex life.

All that to say: If you can afford it and feel comfortable with the idea, absolutely hire an escort. Put a little effort into finding someone who seems like they’ll be patient and happy to walk a newbie through. Don’t ask explicitly over email if your provider of choice is willing to help virgins, unless you live somewhere sex work is legal, as she may not be able to answer. Many escorts have FAQ pages on their website, and mine specifically said I was quite eager to work with those who were inexperienced or who struggled with intimacy, so that can be a good place to check. Also, if like me, they are shitposting on Twitter about loving virgins… another good sign.

Good luck!
Liara

Dear Liara,

I listened to the podcast where you talked about your relationship with your trans client, and I have a question for you. I am a 56-year-old man who has always been a bit feminine. I used to be very fascinated with my mother’s dresses as a child. I never quite felt comfortable being masculine. But I never felt like being a woman either. I don’t feel like a woman on the inside. I have two children; I enjoy being their father; I am very attracted to women. I don’t feel any desire to transition (and to be honest, I think it would be too late for me anyways) but I don’t feel comfortable in my skin.

Do you think I might be trans, and should explore my feelings more? Or should I avoid upending my life?

Best,
N

Dear N,

To be honest, your gender sounds quite a lot like mine—not quite a man, not quite a woman. My conception of myself, in my head, is that I am sort of like a very greasy, very pretty teenage boy. But I also love being a woman, or at least playing one! Dressing up in heels and makeup is so fun—but it also doesn’t feel like me.

When I was younger, I thought about getting top surgery. I thought I would go on testosterone and do a complete transition. Especially when I was a teenager, the fact that I was a “girl”—perceived and treated as such, at least, felt horrible and horrifying. As an adult with some distance, I’ve been able to tease out a few different threads that tied into my intense desire to transition: hating misogyny (being told that because I was a girl, I was ill-suited for computer science), queerness (my attraction to women, feeling more like a boy than a girl), and trauma.

I hated my body. I hated the fact that my body made people perceive me in a certain way, that I was treated differently than other boys, and that all I could aspire to was being a good, obedient wife, and nothing more. I was greedy and ambitious for life. I thought that if I was able to control and change my body, the way people would treat me would change accordingly.

Instead, as I grew older, moved out of my parents home, and found my queer family, I discovered that I no longer felt any desire to get top surgery. The people around me saw that greasy teenage boy inside me, even with my beautiful tits intact. In fact, I’ve grown to love being a hot boy with massive knockers. Isn’t that every teenage boy’s dream, deep down? I do sometimes think about going on testosterone (I think I would be very cute with a mustache and a hairy chest) but it no longer feels like something I need for survival. Because I am seen.

I would suggest that you hang out with some queer community. Maybe try seeing a dominatrix who does a lot of gender play—a lot of pro dommes I know are extremely skilled at helping people navigate complex gender feelings!

It sounds to me like you might be the type of person who just wants to be seen for who you are—a complex person, as opposed to a “man” or a “woman.” You don’t need to physically transition to be trans. Also, FYI, there are a ton of women who aren’t particularly feminine and love women—we call ‘em butch dykes. Perhaps trying on that identity might make sense.

At the end of the day, though, perhaps you are just you! And that’s okay. Maybe there is no label that feels perfect. That’s absolutely fine. Language is such an imperfect tool. Labels should be fun, like trying on a new outfit. If you don’t like how it looks or feels, you can take it right off in the dressing room, no shame in that. You can be a father and a butchy lesbian! You can be a woman who only wears jeans and leather jackets! You can be whatever you want, and the right people will see it clearly, no matter what you look like on the outside.

Love,
Liara

“Language is such an imperfect tool. Labels should be fun, like trying on a new outfit. If you don’t like how it looks or feels, you can take it right off in the dressing room.”

Dear Liara,

I used to take the subway to work every day, which must have been more of a workout than I knew, because I’ve put on a ton of weight since the pandemic. My boss said the company is not going to be reopening the office, and I’m really worried about how I will get all this weight off if I’m not commuting every day! I’m trying to go to the gym and to diet, but I’m really struggling. I just feel miserable about my body and more and more ashamed to be seen.

Help!
O

Dear O,

I think because I’m skinny, people often think I have some secret, magical trick for staying slender. The truth is, it’s just genetic! All my siblings and most of my cousins are also rail thin, no matter how much we eat. People conflate weighing less with “being healthy”—also something that isn’t true! That being said, eating healthy and getting your exercise can be good purely because of the benefits they can have for your happiness and your health!

Personally, I only really ended up getting into working out because I had to. For years, I was a sedentary nerd, preferring to hang out at home playing my video games to getting outdoors and getting exercise. I always thought it was fine, because I was skinny, and my doctor at the time reinforced this belief. It wasn’t until I got a diagnosis of EDS (Ehlers-Danlos Syndrome) that I started working out; my joints doctor told me that unless I strengthen my core and muscles, I could end up in even worse pain, and might need to use a cane, wheelchair, or other mobility assistance to get around.

I initially hated going to work out at the gym. I felt a ton of shame about how weak I was. I couldn’t even lift the smallest weight on most of the machines. This is really embarrassing, but often I would cry on the car ride home! My physical therapist recommended pilates, as it would only use the weight of my body. I hated the idea—I didn’t want to go hang out with a bunch of basic white girls in yoga pants for an hour multiple times a week! But faced with the alternative of increasingly unbearable physical pain, I decided to finally do it. After class, I was shocked by how happy I felt. The workout had gotten my endorphins moving!

I had gone to pilates for my body, but it also helped a ton with my mental health. When I started working out consistently, my anxiety didn’t vanish, but suddenly became a lot more tolerable. I also started to really, truly love my body—not because the shape of it was changing, but because I could properly appreciate it. It felt so good to be in my body, to feel it move and stretch and slowly grow stronger.

And to comment on diet: When I went to the doctor a few years ago, she told me I had dangerously high cholesterol, and that there were numerous other issues, and that she recommended that I cut out sugar, at least temporarily. At first I rebelled—I love my sweets! But eventually, the issues I was experiencing outweighed the yummy, fleeting delight of dessert.

Cutting out sugar essentially means you need to start cooking most of your own meals. From scratch. And forget most snacks—I was shocked reading the backs of most “savory” delights, like Cheez-Its, to find that they were, in fact, stuffed with sugar. Even sushi, which I thought would be totally safe, would take me out; sugar, apparently, is frequently added to rice vinegar, which is used to make sushi rice more sticky.

I was miserable and went through a hardcore sugar withdrawal. I was seriously addicted. If you’re thinking of cutting out sugar, please do it during a time when you can afford to basically experience the equivalent of horrible PMS symptoms for a week.

Once I got through to the other side, I started to love cooking. It felt like a meditation exercise. I felt calm, grounded, peaceful… And honestly, there’s nothing like the warm, fuzzy feeling of knowing you just made yourself a delicious meal. That’s the ultimate care!

This is just to say: Look, your body is fine. Tummies are really cute. I personally think it’s a little more healthy to have a lil’ chub, and personally, I actually find people with a lil’ bit of a tummy to be much cuter than someone who has a six pack. Please don’t punish yourself for the changes you’re going through!

If you’re not getting the exercise you need from your commute, though, you should probably find a workout that works for you. There are a ton of cool workout videos on YouTube that are easy to do from home. If you’re looking for an excuse to get out of your apartment, I recommend going to a nearby park or finding a cute studio near you that does pilates, or dance, or whatever kind of workout seems the most fun! Because exercise should make you feel good.

I do think most Americans could do with a change in their diet, but not to lose weight—just to be a little healthier, to get a little more grounded and in touch with what they’re putting into their body and what is best for them. It’s definitely hard to get in the habit of cooking, though, especially when you’re living in New York, where groceries are crazy expensive and kitchens are punishingly small. But it’s possible, and once you’ve gotten in the groove it can be incredibly rewarding.

Love,
L

Send your questions for Liara to advice@documentjournal.com to have them answered in the next column. They can also be found on Instagram, Twitter, and OnlyFans.