Nick - A Transgender Woman's First

It is surprisingly complicated for an attractive transgender woman to find a man to fuck.

At a singles bar, that mainstay of late 20th-century anonymous hedonism, a potential lover could take violent exception to having his heteronormative worldview challenged after he realizes he's been flirting with a woman who has a penis. Or, put another way, I feel that it's dangerous for me to flirt with men at a bar, because the worst-case scenario involves me winding up face-down in a pool of my own blood. As a transgender woman, that's more than just an abstract hypothetical. So no singles bar hookups for me.

Traditional matchmaking involving setups arranged by friends and family doesn't quite work when you're been married to a woman and just really want to feel a real live hard cock in you.

So that was why, shortly after my 40th birthday, I turned to that mainstay of early 21st-century anonymous hedonism, the pseudonymous Internet message board.

My 40th birthday had laid me out me harder than a 2x4 to the face, sending me into a spiral of self-doubt and angst. Even before my passage into unquestionable chronological middle age, I knew I was the unexpected beneficiary of genetic fortune, having transitioned from an awkward nerdy guy into a classically beautiful transgender woman. Hormone therapy and genetics had been kind to me.

Or, as a female friend jealously observed, "You may be middle-aged, but your boobs are as perky as a teenager's. They've only been around for a few years."

It had taken me time to believe these compliments about my attractiveness. One of the "Aha!" moments during my transition was when, after a late night, I went to a bar for food. I told myself I was going to that bar because it was the only nearby place that served non-diner food at 11pm. And in fact, the wings and stuffed mushrooms were pretty tasty, which is why I had occasionally frequented the bar as a late-night patron back when I had a credible "guy mode".

That night, I fended off an earnest business traveler who simply would not take "no" -- or my repeated observations about my wedding ring, my spouse, or my family -- as a final answer. He flirted, he flattered, he flitted around my deflections. But I was firm in my refusals, feeling an acute sense of danger that things could turn ugly if he realized what extra unwelcome part lurked underneath my clothes.

But at the same time, I felt flattered. Until then, I had regarded passing comments from friends about my newly discovered "hotness" as mere politeness or stroking of my ego. And, after all, doesn't every woman suffer the indignities of harassment on the street or the occasional grope on the train?

By my 40th birthday, I had slowly become more secure in believing others when they told me I was beautiful. I managed to remove all the doubts in my mind about the sincerity of these compliments on my 40th birthday, a day which, due to the vagaries of my unique living arrangements, business schedule, and lack of truly close friends in town, I spent alone in my apartment.

As the evening hours ticked down, I reflected on my entry into middle age, and what might have been had I come out of the closet and transitioned earlier. What might have been had I taken my father's advice and dated other women in college. Or men.

And reflecting on opportunities lost and wild oats not sown, I did what women seeking validation do nowadays. I took pictures of my tits and ass and posted them on the Internet for random people to comment on and masturbate to.

Wait, people don't commonly do that? Or if they do, they don't post them publicly? Yeah.

I sucked in my gut, mashed my boobs together and did my best to take flattering cleavage-and-ass shots. I posted some of the milder ones and received enthusiastic feedback. I didn't intend to post the fully topless pictures at first, but egged on by horny well-wishers, I did, and the rate-of-feedback increased.

"Stunning!" "Sexy as hell!" "Would really love to spend the night with you."

Those were just the start. But the private messages. Oh, the private messages. Some were simple flirty notes of thanks and appreciation and lust. Others were explicit come-ons and not-subtle-at-all statements of what they'd like to do to me. There were notes from women praising me for being confident enough to post, and complimenting me on my beauty and desirability.

There was even a note from a woman who told me, "You're just the kind of woman I think about my husband meeting at a bar and fucking while I watch."

And of course, there were the dick pics. Penises! Cocks and dicks, crotch selfies taken in the spur of the moment, their senders telling me that this is the effect I had on them.

I spent the evening at my computer, sexting with the people who were willing, furiously masturbating until I could take it no more. And through it all, my transgender status was left unstated.

The next day at work was a bust. Discretion -- not to mention aggressive blocking and network monitoring -- prevented me from accessing the site during the day, and my mind wandered. I raced home early that evening, hoping to take advantage of the fading sunlight. I put on a pair of fuck-me-heels and some of my best lingerie, and started another photo set.

I had not shown my face in my previous pictures, and I didn't intend to do that in my second set. But thinking about the people lustfully viewing me, masturbating to me, validating me -- it was intoxicating. I was stimulated, but as I shrugged off the straps of my satin-and-lace teddy to reveal my breasts and nipples to the fisheye of my cellphone camera, I realized that my arousal wasn't visible in the pictures.

I rummaged around in my nightstand drawer and pulled out one of my favorite toys, a stainless steel butt plug. I warmed the plug up, tugged aside the teddy, and gingerly inserted the plug. Sitting in front of a full-length mirror, I teased my own nipples and clenched down on the plug, revelling in the sensation of fullness. As I rocked back-and-forth, feeling the plug shifting inside of me, I felt the start of my orgasm hitting me.

I shuddered and raised up my smartphone, snapping pictures of myself in the mirror, my nipples pert in anticipation, my lips pursed apart in the "O" of the intensity of it all.

The pictures came out wonderfully. On the final pictures of the series, I was able to crop out the top of my face so that my pursed lips, flinching in the waves of my orgasm, could be seen. I also had taken the picture so that my crotch was out-of-frame, although I did tease with a final picture of my ass showing the silver of the end of the plug peeking out.

I edited and posted the second set of pictures that night, and spent that night, too, in a haze of lascivious chatting with suitors willing to describe in detail what they wanted to do to my body.

By the next morning, the pictures of my tits and ass -- not to mention the last pictures of my body in the throes of an about-to-hit orgasm -- had been viewed several thousand times. Mind you, it wasn't the volume of attention that younger, more-popular women tended to receive. But still, enough attention to make me feel empowered.

The next morning during my commute, I looked over the crowd of commuters and idly wondered if any had jacked off to my pictures the night before.

Life intruded on my online exhibition, though. The press of work and family and other obligations, not to mention frustration with lighting and the quality of pictures I could take with my smartphone -- it all prevented me from taking and posting more pictures.

But a month later, my mind wandered again to the net, and to desires.

Pre-transition, I was a shy, awkward and scrawny guy. I married a woman who was not threatened by my lack-of-masculinity, and our sex life was, well, familiar. From an early age, I had identified as bisexual, but I never found it in myself to do more than look at men. With middle-age now hitting me square between the eyes, I felt an acute sense of the fleetingness of my own newly attained beauty, combined with a tinge of despair that by delaying transition until a few years ago, I had frittered away my youth fighting a futile battle trying to be more masculine.

Or maybe that's all just a bunch of self-justifying philosophical bullshit. Maybe after turning 40 I just realized that I wanted to feel young again, and that sucking a cock and getting fucked by a man might somehow help me regain some of that lost time.

So I did what I have done in many other facets of my life. I meticulously researched, considered my options, and then carefully composed a note to random strangers on the Internet, posting pseudonymously on a hookup board:

tl;dr right at the top: I am an attractive, confident trans woman. I haz a penis. Straight men find me attractive until they learn I'm trans. I've never had sex with a man and at this point in my life, I want it. I think my body is telling me that I need it.

So...the details.

I'd like to hear how making my own fantasies come to reality might mesh with your own fantasies. Scenes with older men intrigue me, as do scenes with much younger men. Is it weird for me to come out and say that, and then say that being someone's fetish because I'm trans kind of creeps me out?

I think I want more than just a one-night-fuck out of this, although after the frustrations I've had already, that might be ok, too. Friends-with-benefits sounds great in theory, but I'm not sure how exactly it would work.

Help me unpack all of that, and you can pack....No, I'm not going to go there. (Oh, wait, I just did.)

The initial responses were intoxicating -- potential lovers lining up in my Inbox, presenting themselves to me for my approval. Some I rejected offhand without even responding; others went silent after I sent my own pictures. Others, initially promising, went silent when I proposed an in-person meeting.

Nick's initial message to me came on Monday, well after the flood of initial replies had ceased. I suspect that had he responded to me immediately after my initial post, I may very well have ignored him. He wasn't particularly charming in his messages, and his picture wasn't particularly hot. He was simply...there. And willing (and a touch earnest in his desire to please me).

I sent him links to my topless pictures and he complimented me more. We flirted and I suggested that Thursday or Friday night were a possibility for some sexy fun.

I cannot pretend that this assignation wasn't planned. Looking up the cost of a convenient hotel could be regarded as a flight of fancy. Booking a cancelable reservation -- well, that's certainly a big step that leaves an electronic trail. Packing an overnight bag with condoms, lube and lingerie -- that ventures far into the realm of premeditation.

But I'm getting ahead of myself. In response to Nick's enthusiasm on Monday, I did book a cancelable reservation and wrote:

I'm glad you like my pictures.;) I can tease some more if that's what you want.

Let's plunge into this. (Haha, I didn't mean to do that.) (Maybe I did.)

Thursday night or Friday night are options.

How do you see this going down? (Oops.) I think there's some inherent tension between wanting something fairly NSA but also needing to make sure (for both of us) that we're clicking before getting down to it. I think I'd like to have dinner with you beforehand -- is that heading too far into "date" territory for you?

How poorly did my awkward joking and double entendres hide my physical cravings? I was anxious, and Nick's lack-of-immediate-response was a bit unnerving. The day stretched on with no answer. Tuesday night, after a furious just-before-falling-asleep masturbation session, I wrote him with what I thought was me trying to be not-so-pushy-but-still insistent: "Hi, there. Just dropping you a note to let you know I'm still interested. Let me know what's up." I fell asleep, wondering what my next steps would be, wondering if this was really unattainable for me.

Wednesday morning, I awoke to a positive, albeit brief response: "I'm still interested." Certainly not the most overwhelming indication of interest and lust. I responded with a few questions about logistics, suggesting we meet for dinner at a quiet French restaurant, and indicating that I was serious enough about all of this to book a hotel for the evening. All day Wednesday, I waited for a response. Nothing. Had he gotten cold feet? My ego had survived the initial round of potential fuckbuddies going silent, but coming this close to a carnal encounter only to be faced with uncertainty was nervewracking. Unable to concentrate at work, I spent Wednesday evening pampering myself, getting my eyebrows threaded and shopping for perfume -- something light and youthful, I thought.

Wednesday night I fell asleep again, trying not to wallow in self-doubt. I awoke on Thursday morning to a note: "Looking forward to tonight, go ahead and book the hotel."

Well, now.

I threw together an overnight bag.

Work emergencies on Thursday proved a helpful distraction, and people in my office frequently travel so no one batted an eye at the overnight bag in my office. A 5pm conference call unexpectedly popped up on my calendar, and I invoked my seniority to drop off the hour-long call early.

I took a brief ride on the Metro to my hotel, checked in and took a shower. Recalling Coco Chanel's advice that a woman should wear perfume where she wants to be kissed, I dabbed perfume on my inner thighs as well as behind my ears and in my cleavage. And for good measure, a dab in the crack of my ass. I pulled on a bra and panty set that matched my sheath dress and glanced at the time.

Uncharacteristically for the season, it was a rainy and bleak day. No rain, but the gusts of wind would make it unpleasant without another layer. I shrugged and put my black suit jacket over my sheath dress. Yes, a sweater would definitely be too frumpy for what I was planning.

I walked down the street towards the restaurant, thinking I'd be early. Outside the door of the restaurant, I saw a lone tall, young guy in a suit waiting outside the restaurant.

Sizing someone up on first glance is something we do all the time. I realized that I had crossed into new territory: Sizing someone up to determine if I was going to fuck them. I felt a jolt of electricity race across my skin realizing that he was doing the same to me.

In our correspondence, Nick had identified himself as 24-years old and tall. The picture he sent me was a casual selfie. But outside the restaurant, he was dressed sharpy in a light grey suit and purple striped tie.

Awkward introductions. "You cleaned up nice," I observed.

"I came straight from work."

I gestured at the restaurant. "Shall we?"

Nick charged ahead of me into the crowded restaurant. I shrugged. Perhaps a sign of the exuberance of youth?

The maitre'd seated us at the back of the restaurant. As I set down my purse, I noticed that my date's hand was shaking.

The waiter smiled at me. "Welcome back, madame." Interesting, as it had been almost half a year since I had been there. I suppose I'm memorable?

We make small talk, discussing the mundanities of our respective jobs without divulging too much personally identifiable information. Our waiter takes our wine orders, and I order an unpretentious Riesling. Nick attempts to order a "house white" and is forced to stumble through identifying a suitable alternative.

We gently interrogate each other some more. Nick is not gregarious. Not worldly. He's spent his entire life here in the area -- high school, college, now work. "But I've traveled a lot!" he protests, citing his month-long exchange program trips to China and Japan.

We continue eating our meal, with a moment of silence. "Care to share your thoughts?" I ask. "You've gone silent again."

"I'm thinking about how the rest of the night will go down."

"I've been very direct about what I want. How do you feel about that?"

"Excited."

At what point in the meal did I decide that, yes, I would indeed be fucking this boy? I'm not sure. Perhaps I went into the dinner knowing I wanted to fuck him, with the only question being whether he would back off. And perhaps upon seeing me and seeing that I did indeed match my pictures -- I suspect that he made that decision fairly early-on, too.

What I do know, with a little hindsight, is that by the middle of the meal we were no longer two strangers sitting across from each other. We had both made up our minds that, yes, after this dinner, we would indeed be going back to my hotel room and fucking. With that realization, I regarded him lustfully, and at times he had trouble meeting my gaze.

"Does it bother you when I look at you that way?"

"No, well, not really. It's just that I'm not used to it."

The waiter clears away our plates. I dismissively pass on dessert.

"The waiter. He knows exactly what's going on. He sees the way I'm looking at you. He's thinking about what we're going to do later on. How does that make you feel?

He is silent, but his eyes nervously flick to the side.

The waiter drops off the bill, and Nick fumbles for his wallet.

"Absolutely not," I remonstrate, and reach for the folio. We finish the ritual quickly, and I stand up and give our waiter a knowing nod. I lead out of the restaurant, pushing through the crowd that's standing by the door.

Outside, I grab Nick's hand. It's the first physical contact we've had all night. He shudders a bit. We walk down the street further, awkwardly holding hands, then tracing figures in each others' palms. The wind is brisk; am I shivering from the cold, or from anticipation?

I feel a renewed stirring in my crotch, an erection marring the smooth line of the front of my dress. I readjust my purse to the front.

I cannot skip in high heels but I breathe in the air. I feel alive. Nick walks quickly; me less so, in heels.

"Have you ever watched Buffy the Vampire Slayer?" I randomly ask. He startles and looks at me quizzically. "There was an episode where Buffy became able to hear the thoughts of her friends. One of her friends was a real quiet type, but in his mind, she heard all kinds of..." I stopped as I realized I was babbling, channeling my inner (early) Cordelia Chase.

I smile and stride confidently into the hotel and we enter the elevator. An African-American woman with a young child and a man in a pilot's uniform follow us in. The child squeals at the buttons. I insert my hotel keycard and press the button for the top floor. Mother and child exit at the fourth floor. Captain exits on 8.

The elevator door closes, and I turn and face Nick. On my tip-toes, I press my body against him and kiss him, my tongue probing into his mouth. I feel his hardness as I grind into him, and I realize he has now felt mine, too. "My fantasy," I declare. I savor the feeling of his rough face, the newness of his scent and taste. The elevator doors open and I motion to the proper all. "All the way to the end," I instruct.

I stride confidently into my room. I am still cold from the walk outside, and the room's air conditioning has made it a bit chilly. I adjust the temperature and look out the window, seeing the last bit of fading sunlight.

"I should close the blinds," I say. I walk to the window and gaze out, leaning onto the windowsill. I present my rear to my lover-to-be, waiting. I feel his presence behind me, his gaze alternating between my body and the view outside.

"You don't have to ask for permission to touch me," I say. "I hope I've made my intentions clear tonight."

"You've been .... very clear."

I feel him cup my breasts, still hesitatingly. I lean back into him and tug at the blinds. He helps and we move away from the window. We both unbutton his shirt, me fumbling at the buttons as much as him.