Freaky Times

A gay, transgender teen asks about sex with his boyfriend

James Finn
May 21 · 6 min read

Dear Aunty Jimothy,

How do you ask for ‘freaky times?’

My boyfriend and I are both 17. We’re going to be living together in a rented house our last year of high school. His parents want him to get independent living experience before he goes out of state for college. We’re working part time and our families are chipping in.

But! We’ve been a couple for three years, we’re both sexually repressed as hell, and we’ve never done anything sexual. We had the ‘excuse’ of no privacy, but now … What if he doesn’t want to? I’m afraid I’m gonna just be horny-crying for a year until he goes off to college.

By the way, my parents are very supportive and happy that we’re together. His are in denial and kind of ignore that he came out as gay. I’m trans, and they think I’m a very butch lesbian.

Really needing advice in Roseville

Dear Really,

First, can I just say congratulations? You’ve been together all this time, and now you get to live together. How exciting! I think your boyfriend’s parents are very wise to want him to get some life skills experience.

And relationship experience! When this old Aunty was still young and pretty (back when velociraptors whirled about the sky) LGBTQ teens mostly kept their heads down and their identities a deep secret.

We were usually late experiencing dating and relationships. Sex was often available, but it was kind of dirty and sordid. Or at least that’s how people made us feel about it.

How times have changed!

Your boyfriend is out as gay, and you’re out as gay and transgender. You’ve been together for three years and now you’re taking the next step. Good for you!

Being nervous is natural.

Honey, you should have seen me with my first boyfriend. I was a mess! I worried about every little thing I did, scared to death I’d scare him off. I worried a LOT about sex. I didn’t know how to TALK about sex because it felt shameful to me. So, usually, I just kept quiet and let things happen. Or not happen.

Results? Sometimes I got really pissed at him because he did things I didn’t want. Sometimes he got pissed at me. We hurt each other’s feelings a LOT.

Remember: Mutually pleasing sex is all about communication —

What IS sex, anyway? We queer people don’t fit (and shouldn’t fit) into hetero and cis normative sexual boxes. I mean we have sex differently from the models we grow up learning about. Often, we don’t have a road map.

We have to explore!

You say you’re both inhibited. I think can you have fun exploring your sexuality with someone as worried as you are. As long as you both communicate frankly and don’t put pressure on each other, you can learn gradually and build a healthy intimate relationship.

No goals, no end posts. I mean, you could spend the year kissing on the couch, and if that made you both happy, great. But USUALLY what happens when you start kissing on the couch is that things move along. As long as you respect one another’s pace and limits, then everything is cool.

Trans guys have some challenges —

According to transman Mitch Kellaway writing in Everyday Feminism, you should have a frank talk with YOURSELF before your first sexual experience. Here’s what Mitch says trans guys need to ask themselves:

  • What words for my body parts feel good?
  • What feels invalidating?
  • What parts of my body am I OK with my partner seeing?
  • What parts of my body am I OK with my partner touching?
  • What sexual acts am I OK with doing?
  • What sexual acts would make me feel bad or trigger dysphoria?

After you do this thinking, you need to communicate it to your boyfriend. And you need to ask him to do the same! What are his issues and boundaries?

All that talk might be difficult —

But it’s worth it! Overcoming embarrassment is part of true intimacy. Learning to TALK about sex can make sex less fraught and more pleasurable. Once you’ve talked for a while — hours, days, weeks, whatever works best— then you may find that kissing and making out moves very naturally and organically into something more.

If it doesn’t, if your expectations and desires don’t match up, then you’ll need to ask yourselves if you’re truly sexually compatible. Often, deep love and intimacy are enough for compatibility, but not always. You might want to keep that idea in the back of your mind.

But if everything DOES work out?

OK, buddy, Aunty raised a kid who happened to be straight and cis, but I’m gonna have the same talk with you I had with him. You probably don’t wanna hear it, but here goes. Because I care.


Yes, of course you don’t plan to, my dear. But passion can progress super fast, and people get carried away without meaning to. Such a common story! A 17 or 18-year-old is in no position to be having a child. If you end up pregnant, you could face some seriously rough choices, and both of your futures could get really messed up. I’m sure you know that, but it’s worth mentioning.

Did you know trans men can get pregnant even if they’re on T?

Here’s what Dr. Maddie Deutsch, Director of Clinical Services at the UCSF Center of Excellence for Transgender Health, has to say:

Testosterone greatly reduces your ability to become pregnant but it does not completely eliminate the risk of pregnancy. Transgender men can become pregnant while on testosterone, so if you remain sexually active with a non-transgender man, you should always use a method of birth control to prevent unwanted pregnancy.

If you suspect you may have become pregnant, discontinue testosterone treatment and see your provider as soon as possible, as testosterone can endanger the fetus.

Also, as long as I’m being a boring old person, let’s talk safety —

Barrier protection (condoms) may be your best bet to prevent pregnancy. If you’re on T, you probably can’t take the Pill. That’s between you and your health care provider, but most trans men don’t.

Barrier protection is great even if you are on the Pill, because it also prevents sexually transmitted infections (STIs). You might think you don’t need to worry about that with your boyfriend, and I won’t preach, but please do think about it.

Here’s some really solid information for you —

Sex as a Trans Man is a guide to safer sex for trans men published by the Terrence Higgins Trust. You can click and read to learn about:

  • Trans men and condoms
  • Internal condoms
  • Dental dams
  • Lubricants
  • Safer sex and testosterone
  • Types of (safer) sex
  • Care and cleaning of sex toys

Now that we’ve got that out of the way, let get back to your question, shall we?

How do you ask for ‘freaky times?’

You start by talking openly about sexuality. You guys are really close already, and you mean a lot to each other, so even though you’ll be embarrassed at first, you’ll get used to talking.

Then you ask questions. You listen very carefully to HIS questions. You answer very honestly. You tell him clearly and lovingly what’s in your heart.

You start slow and keep it slow for a while. You kiss, you make out, you get really comfortable with each other. Ask permission each step of the way. Can I touch you there? Can I kiss you there? Does this feel good?

Be prepared to be safe —

Then, honey, you let nature take its course. Respect yourself, respect your boyfriend, and let it all come together, as slowly or as quickly as feels right for each of you.

When you really love and care about somebody, sex and intimacy are wonderful parts of a relationship. You’ll see.

That’s another Aunty Jimothy column on Medium, guys and girls. Got a question? Post it under this story or email and she’ll do her best to crank out some pearlescent balls of wisdom.

By the way, I’ve got a whole bat cave full of lesbians, trans guys and girls, and kinky polyamorous bisexual chicks. So when you ask Aunty Jimothy, you’re tapping into a lot more than one cranky old kween.

Ask anything! Love, sex, dating, hooking up, Tinder and Grindr culture, and HIV/STD concerns. Life with your straight family. Coming out. Or not.

This Old Aunty has the Answers. Somewhere. If I can just remember where I left my purse.

Want more Aunty Jimothy? Read all her columns!

James Finn - The Blog

Collected Writings. Stories and ramblings from a long-time LGBTQ thinker and activist.

James Finn

Written by

Writer. Runner. Marine. Airman. Former LGBTQ and HIV activist. Former ActUpNY and Queer Nation. Polyglot. Middle-aged, uppity faggot.

James Finn - The Blog

Collected Writings. Stories and ramblings from a long-time LGBTQ thinker and activist.