Clearing up Confusion

"You simply have options that I don't!" I protested, as my friend Meredith and I continued marinating ourselves in the hotel spa. I waved my hand dismissively at her from across the jacuzzi, shouting through the steam and noise of the spa jets. "You have so much more sexual capital than I do. The guys are falling over themselves to talk to you, and your breasts" -- I mimed cupping and squeezing her ample D-cups -- "they're like beacons to horny guys."

Meredith giggled. "You're not giving yourself enough credit," she said. "I see guys totally into you but you're shutting them out. And don't talk to me about sexual capital. You're so much thinner than I am. Your boobs are amazing, and I caught a glimpse of your butt as we were changing and it's just begging to be spanked!"

"Perv!" I protested, languidly splashing some water in her general direction.

And she was a perv and she knew it. Meredith was the unabashed libertine within my circle of close work friends. The night before, as we noshed on sushi at a downtown restaurant, Meredith caught the eye of a swarthy Arab businessman. Or maybe he caught her eye. Knowing Meredith, it was usually a combination of both. Her current beau was apparently a Qatari something-or-other muckety muck, and Meredith had latched onto his good looks along with his swagger and hoped-for ability to shower her with totally impractical expensive gifts.

"I'm so jealous of you," I whined, as Meredith finished luridly describing the loud and acrobatic sex they had back in the Qatari's hotel room.

"You shouldn't be jealous," Meredith concluded. "Because I don't understand why you can't just loosen up and take what you want, too. The good ones are out there!"

But Meredith was missing the point. Perhaps it was a testament to our friendship that she sometimes forgot that I was different from just "one of the girls". My dating and hookup life wasn't limited by my confidence (or lack thereof), or the size of my boobs or spank-ability of my ass. It was my penis. Despite our friendship, Meredith still didn't understand the balancing act that transgender women like me went through.

My entry into middle age had heralded in a new chapter in my journey of sexual self-discovery. I had moved on from anonymous "fuck me" hookups fueled by Internet message boards to slightly-less-anonymous encounters via online dating sites. It had been months since I had run away from that swamp, tired of the constant "Transgender 101" I found myself teaching, my ego bruised and battered from men who abruptly went silent on me the minute they discovered I was trans. As I mentally ticked off some of the more-unpleasant rejections, my inner monologue grumbled that the hassle simply wasn't worth my time.

And yes, I was jealous of Meredith, not just of her looks, but of the ease with which she satisfied her lascivious desires and racked up her romantic conquests.

Meredith interrupted my reverie by splashing me as she pulled herself out of the spa. "I'm meeting my guy from last night in a few hours. Go out and have some fun! You deserve it." She padded away, leaving me to marinate further.

But after a few minutes more, I realized I had stayed in the spa for too long already, and wasn't in the mood to stew alone. I stepped out of the spa and wrapped my towel around my waist. I was wearing a bikini top with a skirted bottom; the extra layers on the bottom prevented any telltale bulges from showing. Years of hormone therapy meant that I no longer had spontaneous erections, but there was no sense in taking the chance.

I entered the women's locker room and breathed a sigh of relief when I saw it was empty. Having transitioned many years ago, showering and changing in a locker room was not new to me, but it still was a stressful affair, especially given the recent political hyperbole about trans people. So even in a cosmopolitan city, there were just too many people who would frown at the thought of a trans woman with a penis in the women's locker room. Pushing those thoughts out of my mind, I closed the shower door and luxuriated in the minty freshness of the spa toiletries as I scrubbed and wrung the chlorine out of my hair.

I retrieved my clothes from the locker and quickly got dressed. My skirt suit was well-tailored to my body. My above-the-knee miniskirt was long enough to be appropriate for a businesswoman of my age and corporate seniority, but was short enough to show off my legs and tailored enough to do more than hint at the curve of my butt. I walked confidently past the spa's front-desk attendant who happily chirped out "Thank you, ma'am, for coming!" as I made my way to the elevator.

Unable to muster the energy to head farther out into the city, I decided to get a quick bite at the hotel restaurant. The bar was cozy, with couples and small groups in hushed conversations sitting in Eero Saarinen-esque, brightly colored furniture scattered non-orthogonally throughout the space. I planted myself in the middle of the bar and surveyed my options. Two seats to my left, a scruffy man in a plaid shirt intensely stared at his phone. Further to my right, a group of four men giving off a strong whiff of Axe bodyspray regaled each other with tales of their latest sales conquests.

I shuddered, wondering what Meredith would do. Squinting at the small type on the bar menu, I cursed the onset of middle age and eventually deciphered the miniscule italic type into a list of whiskies, ryes and bourbons mixed in with fancier concoctions. My inner monologue railed at how the typography was intended to drive away old fuddy-duddies like myself, in order to maintain a more-youthful vibe. I caught the eye of the bartender, a tall and athletic brunette with wavy, close-cropped hair, wearing slacks and a gray vest accompanied by a thin gray tie sloppily looped into a loose Windsor knot.

Hesitatingly, I smiled and said, "If I asked for an Old Fashioned, what would you make it with?"

She rattled off a few high-priced options, but seeing my frown, she offered, "But our house bourbon is the Buffalo Trace. It's from the same distillery that makes Pappy Van Winkle." I nodded my assent and watched her mix her magic.

I took a sip of the offered concoction and sighed contentedly. It wasn't a bad night, exactly.

My phone in my purse chimed. It was Meredith.

"Please tell me you're doing something fun tonight!" she texted.

"Well, I'm at the bar. It's full of dudebros, but I'd do the dyke-y bartender in a heartbeat."

"Pics, please. Wait, since when are you into girls again?"

"Lol. You are such a bad influence. I've always been into girls, just been craving cock lately. Not like I've gotten either lately."

My texting spree was interrupted by a bump on my right elbow from a muscular man with a shock of white hair, wearing a well-tailored suit and slightly loosened tie. I moved my purse and offered the bar chair to him, but he remained standing. He squinted at the whiskey menu, and exclaimed, "Oh my God, they have Pappy Van Winkle here! Look at that price!" He excitedly pushed the menu towards his companion, a blue-eyed shorter man in a checkered shirt and blue blazer.

"Let's have another round of Bud Lites!" one of the dudebros to my right yelled out.

I groaned and yelled across the bar, "You're here at a bar with a huge selection of great whiskey and you're drinking Bud Lite?"

The dudebro glared at me. "Hey, it's on the menu!" he protested. The bartender chuckled as she pulled the pints.

"Sorry," I muttered to her. "It seems like an odd choice here."

The silver fox and his companion frowned some more at the menu. "What are you having, there?" he asked me. "Because I'm not going to draw your ire by ordering a Bud Lite."

I smiled. "I'm having a Buffalo Trace Old Fashioned." I pointed out the bourbon on the microscopically printed menu. "It's from the same distillery that makes Pappy Van Winkle. It's good!"

He nodded. "That does sound good."

His shorter companion shook his head. "I've been drinking too much already. Hopefully if I order a Stella the lady over there won't think less of me."

I shrugged, smiling. "I think you'll be fine."

The scruffy man to my left closed out his tab and was soon replaced by a couple young enough to be my children. The woman was heavyset and was wearing a bright pink dress, and was busily making googly eyes at her equally young, but thinner, male companion.

The conversation to my right between the dudebros, the silver fox and the shorter blue-eyed man with the Stella had something to do about an early meeting the next morning, and a crowd of dudebros soon formed around the two gentlemen. The blue-eyed man seemed to be directing the younger ones, who soon dispersed.

He signaled for another Stella, and after it arrived he smiled at me. "They are enthusiastic, aren't they? It's all about channeling that energy, sometimes."

I chuckled. "Corporate leadership can be similar to herding teenagers around, I think."

He shook his fist playfully. "Don't make me turn this van around!" He smiled. "You have teenagers? I'd have never guessed. I'm Tim, by the way," he said, offering his hand.

I shook his hand, feeling a jolt of excitement well up in my gut as I introduced myself further. "I have two teenagers, and two younger ones. They can certainly be a handful."

"Teenagers and four kids. Wow." He lost valiantly against his initial impulse to avoid overtly checking me out, up-and-down.

"I have good genetics and I take care of myself," I said, smiling as I idly ran my fingers through my hair.

"Your husband's a lucky man," Tim observed with a hint of a question as he glanced down at my bare hand.

I paused. "My ex does keep the kids in line. Marriage while being on the road all the time, billing all the hours, it can be difficult, right?" I paused again and chose my words carefully. "Mine didn't work out, for lots of reasons. I'm grateful my ex is good with our kids."

Tim nodded again. As the bartender approached, he leaned in slightly. "May I buy you another round? I promise I won't try to order a Bud Light."

I smiled in assent. As I nursed my Old Fashioned, our conversation meandered through the challenges of corporate life and consulting, the sorry state of business travel, and then back to Tim's own teenagers.

"My boys play lacrosse, and they both wound up at Duke."

"Ah," I observed. "The infamous Duke lacrosse team! Was it as bad as they say it was?"

Our conversation meandered further through the Duke lacrosse scandal of over a decade ago and branched off into the current state of political affairs.

"Can I buy you another drink?" Tim asked, as the noise level in the bar gradually got lower.

I smiled. "Are you sure you don't want to try the bourbon? It's quite good."

"I'm already ahead of you," he said, shaking his head. "You're still judging me for the beer here, aren't you?"

"If I have, it certainly hasn't stopped me from staying," I said, smiling as I patted his hand. He paused at the touch, his forehead wrinkling.

As the bartender slid another Old Fashioned towards me, I noticed my phone blinking at me. When I unlocked it and opened my messaging app, I was greeted with a smirking picture of Meredith, her ample bosom fully exposed, nipples erect, with a bottle of Champagne nestled in between them. I coughed and sputtered, droplets of cocktail spraying slightly onto my phone.

"Whoa! Excuse me!" I said, my eyes widening and blinking rapidly..

"Some sort of emergency?" Tim asked.

"No," I said. "It's my girlfriend. She's...." I pursed my lips together, considering further. "She's clearly having a good time tonight. She's trying to get me into trouble."

"You don't seem to be the type to get into trouble," Tim said.

"Oh really?" I asked. "I might surprise you with how much trouble I've gotten myself into in the past."

I saw the light on my phone blinking again and shoved my phone into my purse.

"Don't let me keep you here if your friend needs you," Tim said apologetically.

"Oh, no. She doesn't need me. I think her needs are being met just fine."

Tim nodded and finished off his Stella. He leaned closer towards me. "I can't believe how late it's gotten and my meeting is starting way too early tomorrow morning. How would you feel about coming up to my room?"

My eyes widened. "I...Well... I mean... You haven't read me, have you?" I blurted out.

"Read you?" he asked. "I'm not sure I understand what you mean." Lowering his voice further, almost to himself, he muttered, "You're not interested, that's ok."

"No!" I objected quickly. "Ok. Wow. No, no, no. I'm interested. It's just. Look. Earlier we were talking about our kids, right? And you asked about my husband. The thing is, I don't have a husband. Or didn't. I had a wife."

Tim leaned back in his chair and frowned. "Ah. You were texting your girlfriend. You're into girls instead of guys. I get it."

"No! No, that's not it, either. I mean, no! Or yes. Yes. I'm into girls, yes. But guys, too! I'm doing a horrible job here. Look. I'm trans." I flinched, waiting for rejection.

Tim frowned and spoke slowly. "I'm confused. I'm not sure what you mean."

I took a deep breath. I met his gaze and realized that he really did seem to be confused. "I'm transgender," I said, almost whispering the word.

He paused and then nodded. "I'm still confused." He pressed something into my hand. It was a hotel keycard. Continuing to meet my gaze, he said, "How would you feel about coming up to my room and helping me to figure this all out. I'm in Room 1410. Some of the people I'm meeting with are staying in this hotel, so give me a few minutes, ok?"

I nodded mutely as I took the keycard, and watched him stride towards the hotel elevators without looking back.

I swirled the last dregs of ice in my glass and pondered my next move, fiddling idly with the keycard. "What would Meredith do?" I asked myself. I smiled, and pulled out my phone and snapped a picture of the keycard in my hand and sent it to her.

"I've flirted my way into a hotel key and am heading up to 1410. I'll be safe, but find me if I don't text you by 1am, ok?"

I dropped the phone back into my purse without waiting to see the response and nodded to the bartender. Was that a knowing smile she was giving me? I strode purposefully towards the elevators, the click of my heels tapping out a steady, deliberate cadence that offered a marked contrast to my quickening heartbeat. I swiped the keycard over the elevator sensor, and before I had time to think more I found myself in front of Room 1410.

I took a deep breath and opened the door to a suite with dimmed lights. Tim stood by the couch, sipping a cocktail, his back to me, gazing out the window over the silhouette of the river and the city skyline.

"Hello, again," I said quietly, cursing that my unintentionally breathy voice reflected too much nervousness, or perhaps a too-deep resonance.

He turned around. "I'm really glad you came up," he said, smiling.

I dropped my bag by the coffee table and walked towards him. "It's a wonderful view," I observed, as I stood next to him. "So many historic buildings." I rattled off a few tourist-friendly facts as we watched the city lights twinkling below, conscious of his closeness.

A few seconds of silence hung in the air despite the screaming of my inner monologue. "So about that confusion..."

"You're...." He paused, meeting my gaze.. "You're beautiful."

I looked away. "Thank you," I said.

"So what I think you're telling me is that you were once a guy? And married? This is really quite confusing."

"Maybe we could sit down?" I asked. We sat on the couch, facing away from the window. I nestled against him and felt the warmth of his body against my back. "Yes. For the first decade or so of my adult life, I did a really horrible job of pretending that I was a guy."

"Wait, so you were born..."

"A guy."

By this point, my inner monologue was screaming at me to make sure I had a clear path to the doorway. But the warmth of his body against mine was alluring.

"You really didn't know?" I whispered.

"No," he said. "This is so confusing."

"I came out almost a decade ago," I said. "Hormone therapy has been good to me." I let that sink in and realized he didn't understand. "Would it be ok if I kissed you?" I asked, shouting over the protests of my inner monologue.

"That would," Tim said, trailing off and pausing. "Yes. Yes, that would be wonderful."

I leaned in and took the lead, pressing my lips against his. His initial hesitation gave way to something more hungry as our tongues intertwined. My hands traced patterns over his back as I felt him pull me closer. I touched the scruff of his chin and reflected that it had been far too long for me.

I pulled away briefly and tugged off my blouse and quickly shrugged out of my bra. Tim's eyes widened as he took in the sight. I sat up straight and arched my back, and pulled his head down to the fullness of my left breast. He lightly ran his tongue over my nipple and then gently sucked on it. I pulled his head down into my breast and moaned as he continued his attention.

"Harder," I moaned. I felt a jolt of pleasure radiate into my body as he nibbled in response to my command.

"Please," I said. "Harder." His deep breathing momentarily paused and I soon felt more of a pinch. I squealed in pleasure, arching my back further. I nestled down further on the couch and pulled him towards me, my own hand running across his chest and over his pants. He was rock-hard and I traced the outline of his cock and stroked him through his pants, all while guiding his hand to my other breast. Soon, through the ministrations of his mouth and his hands on my breasts, it was all too easy for me to lose myself in the sharp sensations of pleasure radiating outwards from them.

I felt other parts of my body begin to react, too. I grabbed his hand from my breast, mid-squeeze, and he startled, afraid that he had done something wrong. I smiled and guided his hand down to my skirt and my own now-erect firmness underneath. His eyes widened yet again.

"This is so confusing," he muttered.

"Ssssh," I said, silencing him with another deep kiss. He leaned into my kiss, our tongues touching further. "Let's move to the bedroom?"

He nodded mutely. I grabbed my purse from the coffee table and stretched, my back arched, my breasts jutting out with my nipples perky from his recent attention, the bulge of my own hard cock breaking the smooth lines of my miniskirt.

I fiddled with the lamp by the bed to adjust the lighting, and, standing by the bedside, I helped him unbutton his shirt and began to tug at his pants. I looked straight into his eyes and, pointing at his erect cock, I observed, "This part of you doesn't seem confused at all, does it?"

I dropped to my knees and rubbed the drop of pre-cum oozing out from his cock. I hefted his balls and stroked them lightly, inspecting the hardness and shape of his cock. He was girthy but not unpleasantly so, and smelled of soap over a hint of musk that made my pulse race. I shushed my inner monologue's comparisons to Goldilocks and musings about pheromones, and, licking my lips slightly, I again met his gaze and whispered, "May I?"

He nodded, and I lapped the pre-cum off of the tip of his cock, savoring the musky saltiness. Greedily, I deep-throated his entire cock and slowly applied pressure with my lips, drawing up in a single stroke. I blew cold air on the tip of his cock and went down for another pull, breathing in deeply to take in his scent and while taking in his thickness.

"Oh, dear God!" he exclaimed. He backed onto the bed, losing himself in the sensation of my oral efforts.

I followed him onto the bed and as I increased the pace of my blowjob, I reflected that my inner monologue was much less annoying when she had her mouth full of a nice hard cock. Sensing that I was in danger of the evening coming to a premature conclusion, I bounced onto the bed and laid next to him.