Just the Tip is a sex and relationship column hosted by queer non-monogamous kinkster Jera Brown. Here you will find interviews with sexuality researchers and educators as well as smart and compassionate responses to anonymous questions. If you have a sex or love question you’d like Jera to answer, email justthequestions@gmail.com or DM Jera on Instagram or Twitter @thejerabrown.

This article was guest-written by Alex Iantaffi, PhD, MS, SEP, CST, LMFT, a family therapist, WPATH certified gender specialist, AASECT certified sex therapist, Somatic ExperiencingⓇ practitioner, clinical supervisor, and author. 

I am a married man in my mid-30s, head over heels and super happy with my wife and our 2 kids. Lately I have been having intense dreams or thoughts right before waking up about being the bottom in a sexual encounter. It switches between imaging my wife with a strap on and a guy with a big member. The one with men are way more erotic as I can act out my feminine side in my dreams. This has been happening for a couple weeks now. My wife and I have a decent sex life, we are unable to find the time because of a toddler and busy work weeks. When we do, I usually but not always am done pretty quick. 

I remember being little and sneaking into my mom’s room to grab lingerie or undies so I could play wedding day. As I was growing up, I didn’t think much about it because I was busy keeping myself busy with sports and friends. It wasn’t until I was in high school that I got a vibrator and didn’t know what I was supposed to do with it. After high school and a weird year at college, I finally moved to the place I would live for the next 15ish years. I wasn’t the most confident, but I knew I wanted to get laid with hot girls as often as I could, which was rather infrequent to say the least. I never had problems with stamina though. I randomly saw a trans video one day and was super intrigued. I was interested in the woman with both body parts, but I was also very interested in looking like her. I had gotten a hold of some thongs and would masturbate to these beautiful different women. I assumed I was into panties and tgirls. After a few attempts and fails at keeping relationships with women, I thought I would try to find myself a trans woman so I could experiment. I had endless emails back and forth with men, never being able to admit I was interested. One day though, I found her. And whoa was she gifted downstairs! Every so often, we would hook up and I would try things out, we took it slow. When it was over, I was too afraid about social anxiety that I would just leave. Over time though we started to get to know each other. At the same time, I thought more and more about being a woman until one day, I bought some bras and a dress online. 

That feeling was amazing!! I had never known that something I had never experienced before could feel so right and normal. I slowly started adding to my collection and realized, I loved it! Women’s clothes are amazing and the underwear feels lovely on my skin. I decided I wanted to dress more often but I was afraid. What if people I knew found out? What would I do? How could I explain it? So I got rid of everything. Each time I started new, adding more and more, I would purge because of what I was afraid others would say. I started really getting into toys but had the same problem and purged a few times. 

One day though, I decided that I was going to go for it. The people I was afraid of, were slowly leaving out of my life, through mostly my choices. I started buying clothes just to try to see if I could fit. I started understanding sizes and shoe sizes, accessories, how to wear my hair. When I got to my 30’s, I had a closet of boy clothes and a closet of women’s clothes. I had partaken in some exciting flings with men and was starting to find myself.

My lease was up and I needed to find a place. I found a roommate who I wasn’t “afraid” of and we found an awesome duplex. Well the funniest thing happened…

I moved next door to a super hot girl, great body and nice demeanor. She wasn’t mean or promiscuous like the others had been. We eventually met and found out we had lots in common. As the weeks went by, I was trying to be Jenna and trying to get to know this amazing girl at the same time. There came a point where I decided to get rid of all the clothes, make-up, shoes, accessories and anything I had that was feminine. Things were starting to get serious and how could I mess up the best chance I had with a girl?!

We wound up getting married. We have a lovely life together. We have a beautiful toddler who is a bundle of energy and he has invigorated me! I thought nothing of wanting to be Jenna, the thoughts almost never came to me. Then one day, pre-pandemic, I thought about the fun I had with my sex toys. She wouldn’t find out if I had just one right? Well that started to get out of hand. I bought clothes and undies but hid it all from my wife. Covid hits and so I decide it’s as good a time as any to purge and try to forget Jenna. I’m sure you have heard it before, but she never went away. In fact, within the past 3 or 4 months, my feminine side has come back, pulling at me harder than ever before. Never have I had such a strong urge to be who I thought I was becoming, not even then. I am almost 99.9% positive that my wife would not be cool with this. I am 100% positive she doesn’t expect a thing about my girly side. For the past 3 weeks or so, every morning as I am waking up, all I can think about is getting pounded. Like, becoming a slut and getting jackhammered! Like I said earlier, It goes back and forth from men to my wife with a strap on. But it has been consistent. I wake up early enough most days to do something about it in the shower. 

I am starting to worry, what if I was really supposed to be jenna? I love my life with my wife and our little family. My conscience could never forgive myself if I ever did anything to not be able to see my kids. I am worried that I won’t be able to control myself when my feminine side takes over one day. Sometimes when I am Jenna, I think about letting my wife find out. I also worry that I really want to be her but am scared of what my kids and wife and extended family would think. I am at a crossroads and am not sure where to turn because I feel like there are so many variables here and blogs don’t normally address this much baggage.

Any and All Advice is much welcomed!

Sometimes Jenna!

Dear Sometimes Jenna, I am so glad you reached out for advice and support. It sounds like much of your gender journey and explorations have happened in isolation and that fear has been a fairly constant companion. I don’t know what is next for you, as you are the only one who can decide that, but maybe we can look at that ‘baggage’ you mention and unpack those suitcases together for a few moments. I hope this might help you decide what might be next for you and I promise I will include some options that you may or may not have considered.

You mentioned fantasizing about being a girl since a young age, initially playing dress-up and playing ‘wedding day’. Playing dress-up is not uncommon for children but, sadly, when it involves gender play, even young children know that this might often not be welcomed by those around you. This is especially true for people like yourself who are assigned male at birth (AMAB). It sounds like you tried, for most of your life, to leave those desires behind, or keep them separate from your gender identity by focusing them into sexual fantasies and experiences.

This is not uncommon. As we grow up, sexual activities are often the only type of play and creativity that we allow ourselves to engage in, or that those around us view as an acceptable form of ‘play’ for us as adults, especially for people who are AMAB. Sex toys, lingerie, and sexual activities allowed you to play with your gender throughout the years with some degree of safety and comfort, until the fear would get too intense, and you’d ‘purge’ and get rid of the evidence.

Your story is sadly not unusual. Many people are afraid to name their feelings about gender in a world that tells us that gender is supposed to be a rigid binary. If you don’t fit into that binary, in any way, this is often viewed as unacceptable. It’s no wonder that fear ruled so much of your life when the desire to be Jenna would resurface once more. You mention having sex with a trans woman, as well as dressing up and having flings with men. I wonder if you were trying to find a way to make your own desires about gender acceptable by making it about sex. Again, this is not uncommon, and you might be surprised to learn that many other people have experienced this.

One thing I find interesting in your story is that the most joyous expression seems to be not about sex or flings with men, but rather about the first time you bought bras and a dress online. You state, “That feeling was amazing!! I had never known that something I had never experienced before could feel so right and normal.” Dear Sometimes Jenna, I think what you might have been experiencing then is called gender euphoria, and it’s probably the biggest clue your inner compass could give you.

You might have heard people talk about gender dysphoria, which is the feeling of not being at ease with your body and the way the world genders you. This feeling can be more or less intense and focused on specific parts of your body, such as hips, genitals, chest, voice, hair, or other characteristics that people often associate with a specific gender identity. However, there is a counter experience, that is gender euphoria, that is all about how right, comfortable, and wonderful it feels to view yourself, or have others view you, as expressing the gender identity that feels most authentic for you.

You mentioned that, as you were exploring this feeling of gender euphoria, you were also starting to find yourself but it seems that, when you fell in love with the person who is now your spouse, you felt you had to choose between being yourself and having a family with her. I know you think that being yourself and being loved by your wife and children does not seem a possibility right now, but I am here to tell you that it might be. I don’t know for sure, and I cannot make any promises, but I know that many people, myself included, have managed to disclose our gender identities to our spouses without losing them or our children.

I would be disingenuous if I also did not share that many people do sometimes lose their families when they choose to be open about their gender identities. The world likes to put our genders and sexualities in neat boxes, boxes that are simply too small, or just the wrong ones for many of us. I do not know what your gender identity is, or what is next for you, but here are some things for you to consider.

First of all, I would encourage you to no longer make this journey alone. I am so glad you reached out for advice, but one blog post is not enough and you deserve to have ongoing support. As a therapist, I am biased towards the gift that good therapeutic support can be, so I do invite you to consider finding a gender-affirmative therapist in your area. I hope you might also consider finding a peer support group where you can more freely explore your gender identity and expression with other people who are going through, or have gone through, similar journeys. 

I also hope that you will start exploring how ideas of gender and sexuality in dominant culture, that is the ways in which gender is represented on TV, in movies, songs, and books, are influencing the ways in which you think about your own gender and about women in general. In your letter you use words like ‘slut’, ‘promiscuous’, ‘mean’, and ‘hot’ to refer to women, and at times to yourself. Those words seem to indicate a way of thinking about women that is influenced by misogyny or, at the very least, by stereotypical ideas about women. I hope that, as part of your ongoing gender journey, you choose to take time to examine those views and beliefs, no matter where you end up in your own explorations. Dismantling misogyny, and also the fetishizing of trans women, can be powerful steps within your own journey and it might even lead you to better understand your own identity.

This leads me to one more point I want to make about this. I said at the beginning that you seemed to focus many of your gender feelings into sex and that this is not unusual. Is it possible that by doing this, that is focusing all gender exploration into sex and fantasies of ‘becoming a slut’ or ‘getting jack hammered’, you are trying to avoid scary questions about your own gender? Is it possible that sexual fantasies then become a way of dissociating from your discomfort about your gender assigned at birth, and your current gender desires? I don’t know for sure if that’s the case, but I do wonder. If it’s not helpful, feel free to ignore this and any other advice in this blog post, of course. If it’s helpful, I would invite you to notice what happens to these fantasies, if and when you decide to give yourself more permission to explore your gender. 

Finally, I know you are afraid of losing the life you have now with your wife and children. I know you think she will not accept you. However, neither you or I can know the future, which means your certainty that she will react negatively likely comes from fear, as well as all the scary and sensational stories in the media. What if, with support by a gender-affirming family therapist, you were able to navigate this journey with your spouse? What if living a more authentic life, where you don’t have to hide or suppress your gender feelings, could be a gift to your own children as they grow up? What if you gave your wife the chance to truly know you, all of you? I know that it is possible, although I don’t know if it is possible for you because I don’t know your wife, her beliefs, and how she might react. The only way to find out what will happen is to take the next step on your journey, knowing that you are not alone and that you deserve competent and caring support, as well as gender-affirming love.


Book – How To Understand Your Gender by Alex Iantaffi & Meg-John Barker (Find on Amazon | Your Local Independent Bookstore)

Book – Love Lives Here by Amanda Jette Knox (Find on Amazon | Your Local Independent Bookstore)

Podcast – Gender Reveal

Podcast – Gender Stories

Article – How to find an LGBTQ+ Affirming Therapist and Why It Matters

Directory – World Professional Association For Transgender Health Provider Directory

Directory – Inclusive Therapists Directory

Website – What is Marriage and Family Therapy

Alex is Chair of the Trans and Queer interest network of the American Association for Marriage and Family Therapy (AAMFT) and President-Elect of the Minnesota Association for Marriage and Family Therapy (MAMFT). Alex is the author of “Gender Trauma: healing cultural, social, and historical gendered trauma” and co-author of the books “How to Understand Your Gender: a practical guide for exploring who you are“,  “Life Isn’t Binary”, and “Hell Yeah Self-Care: a Trauma-Informed Workbook”. They also host the podcast Gender Stories. You can find out more about them at alexiantaffi.com or follow them on Twitter or Instagram @xtaffi and @genderstories.

Several of our fabulous Rebelles contributed to this piece.