Six Things Every Man Who Dates Transgender Women Needs To Know

We’ve brought in a guest writer to address this subject. I’d like to invite more people from the LGBT community to guest post on phicklephilly.

Dear Boyfriends,

This is a love letter to each and every one of you.

This is a letter to let you know that I still think about everything we did and will do together, everything we’ve talked about, every fight we had, and every tender moment we’re going to share.

This is a letter to P, who was always gentle. It’s a letter to M, so curious and kind, if occasionally thoughtless. To S – with whom the sex was freaking unbelievable. To J, always punning and making me laugh; and to E, who is always truthful.

This is a letter to all the men, both cisgender and transgender, who have ever loved me, and to all the men I will ever love.

I want you to know that you change my life and give me strength – even when things between us were/are hard. I want you to know that I see you, I appreciate you, even when I am challenging you to treat women like me – trans women and women of color – better than men in this society are taught to.

I know that being a man who is dating a trans woman (who is outspoken and only sometimes passes) is not always an easy thing. Let’s also take as a given the fact that being a trans woman who is outspoken and only sometimes passes is pretty much never easy thing.

Both of these things are true because of the transmisogyny that still runs rampant in our society and the communities we live in. And while this discrimination and hatred is mainly leveled toward girls like me, I know that some of it is reflected onto you as well.

This is something that is so, so hard to talk about. It’s something has remained unspoken, yet incredibly real, between us, as it does between so many trans women and the men they date.

Part of the difficulty, I know, is that you may not want to admit that being attracted to, going out with, and having sex with trans women comes with intense social stigma.

Another part is that trans feminists like myself believe that any discussion of transmisogyny must center around trans women ourselves. I don’t agree with Laverne Cox (for once in my life) when she says that men who date trans women “are probably more stigmatized than trans women.”

Because that is blatantly untrue.

Men who date trans women are not murdered regularly the way that we are. You don’t experience employment and housing discrimination or exclusion from social spaces in the way that we do.

But neither can I pretend that you live your life totally free from the violence and humiliation that a transmisogynistic culture attaches to my body – a body that you have touched and held and become associated with.

And as much as we may wish that things were different, you and I know that there are so many walls that lie in the way of our loving each other. These barriers have caused us to question ourselves, and our relationships.

Often, we fought about them. Sometimes, we broke up because of them.

You shouldn’t have to learn how to fight transphobia and shaming in order to be with me. I shouldn’t have to teach you how. But the truth is, this is world that often necessitates both.

Whether I like it or not, I am in this fight to the end. I have to be.

You, however, have a choice: your privilege allows you to choose whether you want to walk away from the struggle that is loving trans women, or stay fighting with us.

And if you should choose the latter – and I hope you do – then there are a few things I need you to know about shame, loving trans women, and loving yourself.

1. Dating Me Doesn’t Change Your Sexual Orientation

A huge amount of the stigma around straight men who date trans women is actually based in homophobia. Straight men who are attracted to us are called “f*ggots” and “h*mos,” and may have their heterosexuality called into question.

The implication here being that trans women aren’t really women, so if a man dates us, that means he’s gay.

Conversely, gay men often shy away from dating us – even if they want to – because they “aren’t supposed to be into women.”

And most anyone who dates trans women is at least occasionally subjected to the notion that they’re “into freaky stuff.”

Freaky stuff meaning, of course, women like me.

Past, present, and future boyfriends, I need to tell you something: If you identify as straight, then you can date trans women. If you are bisexual, you can date trans women. If you are gay, pansexual, omnisexual, or asexual, you can date trans women, and it doesn’t change your identity one little bit unless you want it to, because you know what?

You and only you get to decide how to define your sexual orientation.

2. Dating Me Doesn’t Make You ‘Abnormal’

I sometimes meet men who believe (or have been told) that their being attracted to trans women is a form of mental illness. Some of you are, or have been, those men.

Most often, you have absorbed this message from the media: How many Hollywood comedies feature jokes where a straight man finds out that he’s been dating or having sex with a trans woman and flat-out vomits? How many tabloid stories proclaim that a male celebrity has been caught with a trans woman as though this were shocking, sensational news?

More rarely, though still frighteningly often, they have been explicitly told this by a religious/spiritual leader or a health professional.

The implication here is that trans women are so repulsive that you would have to be “crazy” to want to be with us – which bears a striking resemblance to the idea that a person must be mentally ill if they identify with a gender different from the one they were assigned at birth.

But neither my body nor your attraction to it is disgusting or sensational or ill. My body is beautiful, and so is your love. If we are abnormal, that means only that our relationship is different from the one prescribed to us by society.

And there is nothing repulsive about that.

3. Dating Me Doesn’t Make You Less of a Man

As men who are attracted to trans women, you already know that one of most intense forms of transphobia that you will experience is an attack against your own gender identity.

Ignorant people – mostly other men – may insult your masculinity, questioning your ability to attract “real women,” and insult that ways that you have sex.


Cis men are not alone in this – trans men, too, are affected by the backlash that comes from dating trans women.

What you have to understand is that these attacks come from a place of fear. You, me, and our relationships are all very frightening to men whose sense of confidence and power come from reinforcing patriarchy.

The existence of romance and sexuality between a man and a transwoman is a challenge to the invisible rule stating that in order to be a “real” man, you have to “win” a cisgender woman’s companionship and sexually dominate her body.

It forces all men to question their belief in the foundations of their identity and privilege.

Remember this: Their masculinity is weak, because it relies on the subjugation of other’s bodies in order to exist. Yours is, or will be, strong, because it is learning how to stand on its own.

4. Having Sex with Me Isn’t a Fetish (Or It Shouldn’t Be)

Conventional straight couples have many love stories written about them: the prince and princess, the beauty and the beast, the hero and the damsel in distress. You and I have only one: the “tranny-chaser” and the “she-male/chick-with-a-dick.”

This story reduces us and the entirety of our relationships to nothing more than a tired old sex joke, a pornographic trope, an offensive cliché.

As trans activist/author/scientist Julia Serano writes, “People automatically presume that any person who is attracted to, or has sex with, a trans person must automatically have some kind of ‘fetish.’”

It’s true, of course, that there are some men who fetishize trans women – who want us only to fuel transmisogynist sex fantasies. I come across them all the time on OKCupid.

But you and I are much more than that. Our relationships have been deeper and more complex than any cliché could ever hope to contain.

And no amount of ridiculous jokes can ever take that from us.

5. You Don’t Have to Pity Me to Love Me

You may hear from people trying to patronize or subtly insult you that you’re “such a good person” for bearing through the difficulties of dating a trans woman.

It’s possible that you’ve received backhanded compliments on how progressive you are, since you’re willing to put up with the burden of my gender identity.

This is insulting to you and me. I am not something you have to pity in order to love. You’re not doing charity work by going out with or sleeping with me.

Our relationship is not defined by the judgments of others, or even by the violence that I – and by extension, you – experience in the world.

It’s true that you, as men, have privileges and power that I don’t. It’s true that this is something that comes between us from time to time.

But real relationships – like ours – are dynamic and transforming, constantly opening up into new dimensions. At our best, I learn from you and you, from me. We fight, we hurt each other, we heal, we grow. We leave and come back together and leave once again.


It isn’t your job to “save” me from transphobia. I’m doing that already.

The only person you need to save is yourself.

6. Loving Me Doesn’t Define You

Transphobia is greedy. It wants to swallow everyone and everything.

Because of this, whenever people talk about me, they usually refer to me in terms of my gender identity. I’m not a writer or a therapist or an artist. I’m “that Asian trans woman.”

And when we are dating and people talk about you, they may refer to you “that guy who’s into trans woman.”

It’s easy to be consumed by thoughts about the ignorance and hatred of the society that surrounds us.

How can we not be anxious and angry, when your families get uncomfortable when they find out who your partner is, when your friends snicker at us behind your back, when we have to be wary of violence when we go out at night?

But just as I am more than a trans woman, you are more than someone who loves trans women.

It’s your right and responsibility to decide what that means to you, what it means for your identities as men, and how you will explain (or refuse to explain) it to the people around you.

Choices like this are never easy.

But in the process of making them, you just might find a whole new truth about who you are.

This Is How You Love a Trans Woman

Dear boyfriends past and present: Thank you for being with me.

Please know that I’m not trying to either scare you off (!) of dating trans women or “sell” dating us. As you’re probably already aware (it’s not like I let you forget these things), trans women don’t need to beg men to be into us.

We really don’t.

But some trans women – like me – do want to be with men who know how to do the thing, and do it well. Which is not to say that you can’t make mistakes, or feel confused, or get overwhelmed.

We live in a world that says trans women don’t deserve love, and it will try to stop you from loving us.

Knowing how to love a trans woman is simple. You do it the way you ought to love anybody else: not fearlessly, but courageously.



Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

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The Beach House – Chapter 15



Oh, could we?” Mia was getting excited. Almost a bit bouncy which was more attractive than she knew.

We hit the internet and spent some time on Gem Works. There wasn’t a lot of information on the small company, but we found enough. A local business journal article talked about them trying to expand into a specialized phosphorus product. They were having trouble getting the necessary funding due to their lack of historical profits. Chemicals were just not on the love list for venture capital firms these days. Their President and CEO was Brian Fitzgerald. I knew exactly what to do first thing in the morning.

Mia wasn’t that crazy about the plan. She was concerned about the money I was spending. Wives are always trying reign in their husbands’ spending. I kissed her and chuckled at her concern. I got a couple of hands on the hips and a cross look. “What’s so funny about saving money?” I could have told her, but I wanted to cherish the look on her face. I fired up my laptop and logged into the brokerage account. I went to the aggregate page and spun it around so she could look.

“Our main account, Mrs. Tomlinson.” I was smiling as her eyes found the total. Her mouth fell open, and I watched her eyes go back and forth over the total. I noticed she had stopped breathing. “You have to breathe sweetie.” I chuckled as she reread the number for the tenth time.

“You are rich-rich!” She looked up at me with wide eyes. She was still processing how much was there.

“We are rich.” I corrected.

“I can’t even fathom what to do with that kind of money.” She was still in shock.

“Putting an end to water bang parties might be a good start.” She smiled and scooted next me on the couch.

“Did I ever tell you how sexy I find rich men.” She was stroking my inner thigh. I felt my blood begin to move. I pushed an errant hair back behind her ear.

“I have always kind of had a thing for rich women.” She smiled into my eyes and leaned in for a kiss. I felt her hand move higher as my arousal increased. I reached out and stilled her hand.

“I want you to teach me how to love you.” It came out kind of wrong. I knew what I meant, but I was sure Mia was confused.

“I think you did pretty damn well in the pool a few hours ago.” She smiled at me, thinking I might need an ego boost. I gave her a quick kiss.

“I want you to teach me about you. I want you to show me where I should kiss, where I should touch, and where I should lick.” I was turning a bit red at the last part. “I want to know how to please you.”

“Was that your first time?” I knew she meant in the pool.

“Sort of. I paid for it a couple of times, but it never felt like it did in the pool.” I looked up into her eyes. I felt kind of exposed, but I really wanted to know how her body worked.

“Well, as your first and last girlfriend, I feel it is my duty to let you pleasure me.” She caressed my cheek with a smile. She got up and hurried me along to the bedroom. “God, this is going to be fun!” Her enthusiasm was making me horny.

Mia stripped as soon as we arrived at the bed. “Different things turn on different women. Lucky for you, you only have to learn about one woman.” She began undressing me. “I love being touched everywhere. Don’t waste your time staying in one place. My nerve endings kind of get bored if you stay anywhere too long.” She undid my belt buckle why I was making mental notes. “If you want to get me going, start with my joints.” She smiled up at me as she lowering my shorts. “My neck, the inside of my elbow, behind the knees and, for some reason, my ankles.” My dick bounced up as my shorts dropped. “Just light kisses, butterfly kisses and little licks. Nothing too sloppy though.” She hopped on the bed and spread herself out. She was grinning ear to ear. I gave her a curious look.

“What about your breasts?” I really liked the idea of playing with those. Mia chuckled.

“Those are all for you and feeding babies. Don’t get me wrong; it feels nice when you play with them. Mine just aren’t super sensitive.” I was slightly disappointed. “Don’t worry, I’ll show you other things titties are good for later.” Her smile held promise that eased my concern. I climb into the bed next to her. She giggled and rolled me on top of her. “When it’s your turn, I own you. Right now it’s my turn so you own me. I am your prized possession, and I have no choice but to submit to your control.” God, I liked the sound of that. Her body was my plaything and I was getting really excited.

I covered her body with mine and allowed an elbow and my knees to take the weight. My lips found the base of her neck, and I began lightly kissing and teasing it with my tongue. I felt involuntary shivers run through her body as my free hand lightly caressed her side. I kissed up to her ear and remembered the pool. “I love that you’re mine.” I whispered softly to her as my lips began to descend again.

“Yes, and words like that.” She said as my hand lightly caressed her side and my lips followed the contours of her shoulder. She was cooing as I kissed down her arm and tickled the crook of her elbow with my tongue. I slowly moved back up to the other side of her neck.

“You taste delicious,” I whispered, and another shiver ran through her body. I ran down her other arm and lightly tortured the inside of her elbow to a few quiet moans. I could feel the muscles in her body contracting in response to the tickling sensation.

I shifted my weight to my knees and moved my lips to her breasts. She told me they weren’t a big turn-on, but they were too wonderful to ignore. I gave the left nipple a little lick and gently blew on it. A forest of goose bumps appeared. I smiled and repeated the process on the right nipple. I got a giggle out of Mia and a whispered “Men!” said with humorous contempt.

I kissed a wet trail down her chest across her tummy. With both hands now free, my fingers were exploring her sides and running down her thighs. As my kisses reached her thighs, a wonderful musky aroma inflamed my nose. I carefully lifted her leg as I slowly moved to her knee, my eyes never leaving the adorable womanhood between her legs. The lips were shaded both lighter and darker than the surrounding skin. When I lifted her leg higher to access behind her knee the slit glistened. It looked as wonderful as it had felt in the pool. I caressed her thigh with both hands and kissed the crook of her knee. I pushed Mia’s knee back toward her as I massaged her calf. Her pussy opened slightly to reveal its wetness. It looked so warm, it had me entranced.

I reached her ankle and made love to it with my tongue as I massaged the bottom of her foot. I started hearing a constant low moan from Mia. I knew I was doing well. I raised the other foot to my lips and reversed the process I had used on her left leg. I was slowly descending back toward her intoxicating scent. As I approached, more of her muscles were responding involuntarily.

I pushed both of her thighs back toward her. I was desperate to see her. My face was only inches away from that precious opening as I ran my fingers along it. I opened her flower slightly and examined the multiple folds and the wetness that was flooding the sides. Mia moaned louder as I lightly touched her clit which had emerged from its hiding place. I was mesmerized by the beauty of it all. I loved her for letting me explore. Mia misinterpreted my exploration as hesitation. She spoke softly to me.

“Not every guy likes to…” I never let her finish. I dragged my tongue from the bottom of her slit deep inside tasting a woman for the first time. “Oh God!” she groaned. Both her hands wrapped around my head, and I felt her hips begin to move. She tasted like a soft honey, sweet but more delicate. My hands were holding her thighs wide as I went deeper and dragged out along her little nub. Mia tilted her hips into my face and was holding my head like I might want to leave. I began tickling her clit with the tip of my tongue, and I saw her back arch and her neck tense. Her whole body was shaking as she forced my mouth to drag along her clit. I lost my grip on her thighs as she straightened her legs to force her hips off the bed. She stayed that way for half a minute before her hips fell back, and a loud sexy groan escaped her lips.

I smiled at what I had done and lightly caressed her gorgeous pussy with two of my fingers. It was practically pulsing behind my hand. I was able to generate little involuntary jerks as I lightly moved them across her little nub. I have no idea why I was having so much fun watching her squirm under my fingers.

Mia sat up and then coaxed me back on top of her. “That was simply incredible.” She sighed as she pulled me into her bosom. “I didn’t think you were going to go that far.” I gave her a loving smile.

“I’d never seen one up close in real life. I just had to know everything about it.” I caressed her breast as I explained my actions. “It was really quite amazing. Everything about you is amazing.” I looked up to kiss her and I saw a tear in her eye. “Mia?”

“I love you so much.” She squeezed me tight and more tears appeared. “I get kind of emotional after I cum like that.” Her voice was a bit halting, and her expression was all screwed up with tears and a smile. I scooted up a bit more, gave her a kiss, and wiped the tears from her eyes. I was relieved that they were happy tears. She ran her hand down my side and felt my arousal.

“It feels like you are ready to explode.” Watching her throes of ecstasy made me hard. Knowing that I caused it had made me really hard. Mia sat up and pushed me flat on the bed. She moved between my legs and gave me an evil smile. “You like these don’t you.” She was holding her breasts and added a little wiggle for emphasis.

“I kind of love them.” I was smiling, not really knowing where this was going.

“They’re kind of soft and firm at the same time.” She was examining them, tilting them back and forth. “They feel so warm right now.” She looked back into my eyes. “I wonder what it would feel like if I wrapped them around your cock.” My hips jerked a bit as I realized where this was going. I had no idea what it was going to feel like, but God, I wanted to know! “First we have to make sure it will slide really well.” Without warning Mia dropped her lips over my manhood and took me half way into her mouth. Both of my hands squeezed a fist full of sheet as I strained not to cum under the surprise attack. I felt her tongue coat the underside of my shaft. I locked my legs, trying my best to hold off and wait for the breasts. She slowly raised off my tool, swirling her tongue around the crown. She drooled down the shaft, and her lips left the tip.

“Oh, I think it will slide real well now.” She looked me in the eye and lowered her breasts over my groin. I could have cum right there. I felt a tinge of release, and I knew if I let it go, it was all over. Just the thought of what was about to happen was becoming too much. She smiled at me. “I think you’re going to like this.” Mia squeezed her breast together and enveloped my rod in feminine warmth. I was in heaven. The sensation was so visually stimulating I wasn’t sure I could take any movement at all.

Mia began to massage my cock with her breasts. On every down-stroke, the head would poke up under her chin, and I would grunt. I gripped the sheets harder, and my neck was straining. I was trying desperately not to move my hips. I wanted it to last longer. Mia ended it. In a soft sultry voice I could barely hear, she said, “Cum for me.” My hips started jerking, and I watch my cock explode cum under her chin. The head disappeared between her tits, and I felt myself fill her cleavage. My whole body felt like it was part of the climax. Every cell was happy at that exact moment. When the crown reappeared, it was a glistening mess, and I pulsed another, smaller shot under her neck.

My spasms slowly wound down, and Mia unwrapped my manhood. Her neck and cleavage were covered in jism. My cock was a happy drippy mess. Mia started laughing as she looked down at her chest. God, I loved that laugh. “Someone really likes my titties.” she said as she wiggled them at me. I pulled her down to me. I didn’t care how messy she was, I needed to give my future wife a kiss.

“You are by far the best thing to ever happen to me.” I slid her lips up to mine for a short peck. “How about a shower? We have a lot of work tomorrow.” I was playing with her hair as I talked. She raised herself up on her elbows and looked at the walls.

“Can I redecorate? Monica’s color pallet is a bit boring.” She smiled at me. I liked the idea of her taking ownership of the place.

“Mrs. Tomlinson, it’s your house, and you can have it any way you want.” I reached down and squeezed her butt for emphasis. “We can call painters tomorrow.”

“I just thought we could go to the hardware store and paint it ourselves.” She was looking thoughtful. “Kind of makes it more ours when we do it ourselves.” A wonderful vision suddenly appeared in my head.

“If we were naked, we wouldn’t ruin have to ruin any clothes.” I was imagining her climbing ladders as I tried to hold back a smile.

“Well aren’t you the kinky one.” She poked me in the ribs. “But no sex until the room is done.” She didn’t hold back her smile. She seemed to like the idea. I was hoping it didn’t take too long to paint a room. “Let’s take that shower stud. You’re as sloppy as I am now.”


Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

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