AdviceNew YorkSan FranciscoSex and Dating

My First Real Date as a Transwoman

Updated: Jan 22, 2016 10:59
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In my last BrokeAssStuart blog I wrote about the lack of mediatized representations of transgender people as complex, loving, sexual, and emotional beings. I also wrote that all the guys I had met online were interested in sex but not interested in taking me on an actual date. In what follows, I’m happy to prove myself wrong on both counts.

The Lost Art of Taking a Lover

photo from tumblr


“I hope you don’t think it’s weird that I Googled you.”

I didn’t. In fact I suggest it in my profile, it gets a lot of questions out of the way.

“I think you do a lot of good for people,” he tells me, “probably more than you know.”

We sit in the restaurant and talk about our lives. He tells me how he grew up being bullied as the only Latino kid in his neighborhood, and how he started wresting and boxing because he had to be a fighter. We talk about our families, about moving across the country, about working 80 hours a week, me in theatre, him in sales, about reframing our priorities. Real first date things. And then he asks me the most amazing question: “So, who are you?”

I think the last time I had to answer that question, like really answer that question, was for my final exam in Humanistic Psychology, sophomore year at UC Santa Cruz. It was the spring of 2000, I had just come out to the entire lecture class as transgender. 16 years later, and here I am with this beautiful man, on my first real date as a transwoman.

Fragments of my life story spill out in random order, all tangents. High school riots and dancing in Mexico, musicals in New York, a sex change in Thailand.

The food arrives. He eats meat but ordered vegan fajitas so we could share. We laugh, we make eye contact, we flirt…

We’d been texting since the previous day, and given that we met on the infamous hookup app that had so egregiously blocked me, our mutual desires (and my sexual propriety) had already been discussed. Boundaries predefined, we evaluated our options. He lives with his younger brother, I was staying with mine. We decided it was best to get a room.

He reached across the table and took my hands in his. “You seem nervous”

“You’re gonna make me come,” I say, “and then I’m gonna get emotional. That’s just how this night’s gonna work.”

He looks deep into my eyes. “I am gonna make you come,” he tells me. “I’m gonna make you come hard.”

“Use your words.”

We kiss, we tumble, we sweat, we explore.

In true Sex In the City fashion we lay in bed together naked while I read him the draft of my first BrokeAssStewart blog, the one about all the guys who were afraid to take me out in public.

“It makes me so angry,” he says, “who wouldn’t want to be seen with you? You’re beautiful”

We kiss, we tumble, we sweat, we explore.

We talk about our first times, how they lacked the tenderness and romance we wished they could have had. How he also knew what it felt like to be used for sex, and how he’d never want to make anyone feel that way. How he learned from his previous partners that communication is the most important thing.

“Communication is the most important thing,” he said.


“Tell me what you’re doing,” I ask him, “so I understand what’s going on.”

“Well, right now I’m using my finger to feel around the edges, on the sides, but if I curve up like this—” I gasp and laugh, my torso arches uncontrollably, my arm swinging behind to grab the corner of the bed.

I ask him if it’s different, my new vagina, from the organic ones he’s known. “No two are the same,” he smiles, one hand on my stomach to guide my breath. “Breathe for me.”

And I’m lost.

It’s 5am when we finally settle down, and now I’m living my little spoon dreams. There was no figuring out what to do with the phantom arm, no question about wrapping the leg, we just fell into place. And when I shifted in the night he responded immediately, effortlessly, always connected but never confining. My eyes stayed open long after his. This sleeping man had awakened something within me.

The next day, as predicted, I was a weepy mess. I’ve read Naomi Wolf, I’ve learned about the vagina-brain connection, I knew the chemicals unleashed in last night’s thunderous orgasms had me bonding and craving on a primal level. I tried to prepare myself mentally, but my emotions didn’t care. The comedown (come-down?) was real.

Time moved slowly. Grey skies stretched out with unspeakable melancholy, reflecting my longing in thoughts clouded by flashes of his perfect smile, his sensitive words, his dark eyes looking up at me from between my thighs.

My Sex For Smart People video had just gone live. I send him the link, he calls me a prophet.

We make plans to see each other again.


Our second date started later. It was already 10 by the time I got to his house. This time we booked a hotel room in advance.

Balboa Park, coffees in hand, we stop in the middle of the plaza. He turns toward me and puts his hands around my waist. “To be honest, I didn’t know what to expect. When I saw your profile and that picture of you on stage I just thought, ‘wow, she’s so beautiful and brave.’ I read that you were Trans but didn’t really take notice, like it didn’t make a difference to me, I just had to send you a message.”

My hands moved to his shoulders, fingers wrapping around his arms. I noticed a few other people walking in the plaza, a couple with their dog, three friends strolling with heavy coats. It was a quiet night beneath a starless sky, one small park in one small city on one small planet. And there we were, two lovers embracing in the break of a storm.

“I feel like I prayed you into existence” I say to him, laying my cheek against his chest.

We stood there, hugging in the rain, and under my breath I whispered a soft and ancient sigh. “Thank you, Jesus.”

At the fountain I pulled two nickels from my purse. “These are worth five times as much as regular wishes,” I told him, “so make it count.”

Once more we stood in silence, this time gazing at the water. He took a knee before making his wish. Gave it serious thought, made it meaningful.

“I can’t tell you mine, right?” I ask.

“No,” he laughs, “of course not!”

I held the coin in my hand and wished that this night would last forever, symbolically speaking. I mean, I knew it couldn’t, I knew that 12 hours from now I’d be at the airport headed back to New York, but if I could have stopped time I think I would have lived in that moment forever. Writing about it now is the only way I have to make that wish come true.

“Slow Down.”

This time we ask the hotel clerk for a room with no neighbors. He wants me to be loud. I want to take my time undressing him, I want to relish the unveiling of his beautiful body, but I can’t hold back. We stumble onto the bed, lips locked, his hands holding my face as we stare into each other’s eyes with hunger and affection.

We kiss, we tumble, we sweat, we explore.

And now the hours pass like seconds. We’ve learned each other’s bodies–started to at least–and there are tricks we play to tease and lead. I taste myself on his lips, his fingers. He presses against me, grinding while we kiss, mindful of my only rule.

And it could have been so easy, to take that step, to let him in, but then I’d find myself on an airplane, longing for a follow-through that could never be expected. I know myself well enough; the quick high of fleeting penetration isn’t worth the come-down of a once filled vessel left empty.

We fall asleep listening to Des’ree. I nuzzle into the nook and close my eyes. I want to breathe all of him in, memorize his smell and the feeling of his face pressed against mine, the weight and architecture of his body wrapped around me.

I have never felt so safe.

The alarm goes off 2 hours later. We awake in that gentle undulation of two bodies that aren’t finished connecting. Moments later the pace unfurls, flinging us into frantic immersion, grasping at our last chance to become one. The climax leaves us drenched and breathless.

I lay back in his arms, and he starts humming, a simple buh-da-duh.

“What are you singing?” I ask.

“I don’t know what’s it called,” he mutters, nearly asleep again, “A Thousand Years?”

I roll over and grab my phone, scrolling to my Twilight playlist (yeah, I’m a teenage girl). “You mean this?”

We lay there in each other’s arms while Christina Perri sings:

“…Time stands still
Beauty in all she is
I will be brave
I will not let anything take away
What’s standing in front of me
Every breath
Every hour has come to this
One step closer

 I have died every day waiting for you
Darling, don’t be afraid I have loved you
For a thousand years
I’ll love you for a thousand more

 And all along I believed I would find you
Time has brought your heart to me
I have loved you for a thousand years
I’ll love you for a thousand more…”

He squeezes me tightly, “This song is so on point right now.”

And my mind is racing. I know this moment is ending. We have actual minutes left. And this is all I want. All I’ve ever wanted. To feel real, to feel loved, to feel seen, desired, protected, respected.

My breath shakes and tears well up in my eyes.

He kisses my forehead. “Cry,” he says. And again, softly, “Cry.”

And I do. Freely, sweetly, sadly, hiding my face at first. But then I look up at him, smiling though tears. I can’t help but laugh, the entire situation is too real and too ridiculous. He kisses my eyelids and holds me tighter.

We get dressed quickly. Work in 10 minutes. Run to the car, still raining. Pull over, flashers. Words not good enough.

“Thank you for letting me learn with you, and for letting me teach you about yourself.” He breathes. I try.

I can’t bring myself to say goodbye, even if that’s what this is.

“And you,” I tell him, “You’re an angel. Please, follow your heart, find your fight, and be remarkably successful in whatever you do.”

There’s no last great kiss, no final marker. I watch him through the rain-streaked windshield, rushing into work. The back of a beautiful boy with the whole world ahead of him.

And what would the camera see it if were turned on me, I wonder. A woman behind the wheel, wiping tears from her eyes, quivering from the echoes of a whirlwind affair, reaching from her heart for a lover she just released to the rain.



Somewhere in our culture of intimacy—beyond the hook-up and the booty call, outside of commitment, more contained than dating, and rooted deeper than any one-night stand—resides the glorious tradition of taking a lover. Here are a few things to keep in mind when venturing down that road:

? Remember, your lover’s body is new to you. Enjoy the exploration, pay attention to their breath, to tension and release. The most intimate playfulness comes from responding to these subtle cues.

?  Give of yourself freely, and rejoice in everything your lover shares with you. Recognize your participation in the joint creation of momentary bliss.

? Try something you’ve always wanted to try, and invite your lover to do the same.

? Be grateful for and mindful of the force that brings you together. Opening your heart to the spiritual aspect of taking a lover elevates your connection from one of worldly eroticism to one of celestial ecstasy.

? Don’t waste any time. Let every passing moment overflow with passion and enthusiasm, whether in conversation, sex, or snuggling.

? Try to hold on, but know that you can’t. Still, try. Allowing your heart to want is key to expanding its capacity to receive.

? Will it ever get easier to love and let go? Probably not. You heart is a muscle, you work it out and it gets stronger, but the training is always a challenge.

? Sex is a way for us to learn more about ourselves, love is how we celebrate what we’ve learned.

? It’s more delicious to feel everything.



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Shakina Nayfack

Shakina Nayfack

Shakina Nayfack is writer, director, actor, and performance artist based in New York City.