This is not my creation, rather it's something that Jack Molay wrote on his blog. It's an awesome piece and I thought it worth re-posting on my blog. The original can be found here.
The Sex Life of Crossdreamers (Autogynephiles)
It will probably take some time before Cosmopolitan writes a "how to" guide on how to cope with a crossdreamer (men who fantasize about having a woman's body, also known as autogynephiliacs). But if the woman's magazine ever does, maybe they would write something like this.
Cosmopolitan June 2025.
My husband is a crossdreamer! How to keep your relationship thriving.
Your boyfriend tells you he is a crossdreamer. He gets turned on by imagining himself being a woman. In bed he wants to take your role. He may even want to borrow your lingerie. So now what do you do?
Know that there are good news as well as bad news.
From Venus and Mars
The good news is that you have found a man that worships you more than most men can do. He admires your looks, your wits and your ways to such an extent that he would like to be like you. Given all the misogynists out there, that is not a bad bargain.
The "inner woman" of a crossdreamer may also make him more sensitive. What some of them lack in testosterone driven masculinity they make up for in their love for you, your family and kids.
Fear and self loathing
The bad news is that he may be slightly traumatized. There are male pop stars and Hollywood actors coming out as metrosexuals and male lesbians, but in small towns a man having feminisation fantasies will still be considered a freak.
This means that he may also think that you consider him a pervert, whatever you tell him. His self-esteem may be low. The fact that crossdreaming was considered a "paraphilia" by the American medical establishment up until 2023 has not helped.
In order to keep your love he might try to hide his dreams. If he is a crossdresser he may hide his feminine clothing out of your sight. This may make him distant and withdrawn. His inner woman becomes your rival instead of your partner. If you want to make this relationship to work, it is therefore important that you help him bring his secret life out in the open.
Do the woman thing: talk about it! The man in him probably hates the idea, but his "inner woman" may become your best ally.
Is he a transsexual?
Many women who love crossdreamers harbor another fear: Is he a transsexual? What if he wants to have an operation? Then what do you do?
Note that the crossdreamers can be put into at least three overlapping groups.
The crossmopolitan identifies as a man, and has a good relationship with his own male body. He thrives in the traditional assertive male role as well as the more feminine caring role. For him his feminization fantasies are sexual spice and a way of getting in touch with his feminine side. He will feel no desire to transition for real.
The transsexual feels a strong gender incongruence. He -- or she, rather -- may have spent a lot of energy to suppress her dreams of becoming a woman, but the fact is that if she does not transition she will probably never find peace with herself. She has reached the tipping point where the sum of various genetic and hormonal causes of crossdreaming equals woman. She is a woman!
There are some relationships that survive a male to female transition, but the process will cost you a lot of suffering. It is a sad fact, but most relationships and marriages of this kind fail. You being bisexual might help, though.
The twilighter gets his name from the twilight zone in between the male identifying crossdreamer and the transsexual. He is in the problematic position of being both male and female in close to equal proportions. In our cultural context there is no role for the twin-spirited, and he may find it extremely hard to make peace with himself and the people around him.
Some of the twilighters become love-shy and introvert geeks, preferring their secret fantasies to the love of a real woman. It is not that they do not want your love. The fact is that they desperately long for it, but they find no way of conceptualizing what kind of life you and his inner woman can share. And if they do, they may imagine themselves as male lesbians. And you are probably not looking for a lesbian, are you?
He may still be a very good catch, though. When he understands that you understand him, his gratitude and love will lead him to make a tremendous effort to make the relationship work. He is very likely to be a faithful and committed husband. The trick is to find room for his inner woman. There are ways of doing that.
Is he gay?
The first suspicion that comes to mind when a girl realizes that her boyfriend and husband has a strong inner woman, is that he is gay. There are a lot of gay men with strong feminine sides. Some of them may even harbor feminisation fantasies and get turned on by crossdressing. Drag queens explore their inner woman in this way. Some of them do get married, although not as many as before, now that male homosexuality has become accepted.
Still, most male to female crossdreamers are actually gynephilic. They want to have sex with girls. Really! Check his web browser history. If you find a lot of pictures of sexy hunks, he is most likely gay. But if he is more into Penthouse and Playboy he is straight or bi.
Note however, that some gynephilic crossdreamers may have erotic fantasies about being banged by men. That could mean he is bisexual. But if the men of his fantasies are faceless, they may also be an expression of his desire to be the bottom in the sexual act, not a real sexual desire for the male body per se. He would rather have a woman penetrate him than a man, which is why some crossdreamers also get into "shemale" porn.
8 ways of making a crossdreaming sex life work
1. Make sure he understands your needs and desires. Some crossexuals have never spoken to anyone about their desires and have become pretty self-obsessed. This is an interesting paradox: In spite of the fact that he has a strong inner woman, he may lack the skills needed to interpret the dreams of a woman. Make sure that he understand that your "inner woman" is as important as his. Most crossdreamers can take the active role when having sex -- he owes you much more than that!
2. All right, so he is willing to please you. What can you do to please him? Take the active role! He will love you to be on top! He may fantasizing about you being the one inside him and not the other way round, but who cares as long as you get turned on together?
3. Talk dirty to his inner girl! That will shock him and delight her.
4. If he is a crossdresser, allow him to wear some lingerie. Borrow him some of yours if it fits. But if it makes you very uncomfortable, don't. Your needs are as important as his!
5. His inner woman may desire penetration. A finger up his anus may drive her wild. You will find that his ecstasy will turn you on as well. But demand proper hygiene!
6. If you are of the daring type, try out a strap-on. Pegging gives you full control and allows for his submission.
7. Most men, including many crossdreamers, do not fully get the bonding part of sex, i.e. that sex is just the natural culmination of friendship and love. Some crossdressers do, however. They would very much like to have a pajamas party for two with you doing girly things together -- like painting your toe nails and talk feelings. If you can live with him dressing up, that can work well. Again, tell him when you need him to be your man and not your girl friend!
8. Some crossdreamers would also like to make some body modifications. Shaving body hairs and electrolysis fit well into the crossdressing category. If you can live with his crossdressing, this should not be much of a burden. If he wants to take hormones, however, you need to have a looooong talk, and seek some counselling. Some wives can live with their man growing breasts. But he may also become non-functional as a man. Know also that if he wants to try out hormones there is a very good chance that he is a transwoman.
The ups and downs of a normal relationship
The relationships between a male crossdreamer and a woman are not that different from "regular" relationships. Or maybe there are no "regular" relationships. Given human diversity, they are all unique exercises in making love grow, and love requires patience, understanding, perseverance as well as a the kind of self-confidence and strong will that protects you from being exploited.
Crossdreamers may be traumatized from their struggle with their dreams and desires, especially if they have never felt acceptance for their secrets. That trauma may be healed by love, but it may also require professional help.