Fifty Shades of Gay

Being stood-up by someone is probably the most humiliating and defeating experience one can experience in the dating world. It had happened to me several times before, but this time hurt the most.

I had been chatting with a man named Roberto through Growlr, and I ended the conversation by giving him my number. I did this, because it’s much easier to text people than to continue communicating through an app that kills your phone battery. Much to my surprise, though, he called me later that evening. To be fair, he wasn’t a Millennial like me. Roberto was comfortable with calling a stranger rather than hiding behind a screen.

We didn’t talk for long. Honestly, he probably just wanted to hear my voice to make sure I didn’t sound like a psychopath. And when we wrapped up the conversation, he mentioned that he had to turn in early to get up early for a conference in the morning. I asked him where the conference was being held, because I work in corporate meeting planning and care about stuff like that.

As fate would have it, the conference was being held at the very hotel I work at. Romantic images from the movie “Serendipity” flooded my imagination. This had to be a sign! We were mutually excited that we would actually be seeing each other in person the very next day.

I texted him in the morning, and we set up a little rendezvous on property to officially meet.

“You’re even more handsome than I thought you would be,” he said, charmingly.
“Oh, no, it’s just the suit,” I said, unable to take a compliment. He looked amazing, mostly because he was one of those people who actually enjoys working out and lifting heavy things. His muscles were barely contained by his dress shirt.

We chatted and flirted lightly for a little while before he had to return to session. And we agreed to head out for lunch together later to get some privacy.

I drove him to one of my favorite cafés, and we had an absolutely perfect time getting to know each other better. We cut right to the chase and discussed what we were looking for in a significant other. It was a match made in heaven, or so it seemed.

Roberto placed his hand on my thigh as we drove back to the hotel. I purposely pulled into a parking spot in the corner of our lot that was somewhat out of view. I moved his hand to my crotch and made out with him shamelessly until he had to return to his colleagues.

We continued to text each other throughout the day, both half-assing our way through work responsibilities. I wanted more time with him, so I asked if he would be interested in meeting me out for a drink later that night. People often say “a drink” when they really mean “many drinks”, I’ve come to find. I had fallen into the same habit.

I beautified myself at home and headed out to my favorite gay bar. It was relatively quiet in there, being that it was a weeknight. I think it’s rude to invite a date out to someplace loud where you can’t even hear each other. Maybe I’m just getting old. But, ultimately, it would not matter. Roberto never showed up.

When I came to realize the fate of my evening, the bartender couldn’t help but notice my sorrow. He poured me my usual drink – a double vodka soda. An older transgender woman next to me somehow knew my plight.

“What’s the matter, honey, get stood up?” she asked sympathetically.
“Yep…”
“Don’t worry about it, he was going to drop you like a rock anyway. He’s not the right guy for you. You haven’t met him yet, but you will be much more domesticated by this time next year. You’ll see.”

I kept my head down, unsure of how to respond. She was spouting out some kind of intuitive bullshit I wasn’t in the mood to hear. She may have been right, but it didn’t matter to me in that moment. I thanked her politely and moved to a small table to be left alone with my thoughts.

My pity party for one was quickly interrupted by a boisterous woman – a butch lesbian.
“You got quarters for pool?” she asked loudly.
“Yeah, sure.” I grabbed a dollar out of my wallet. “The bartender will give you change.”
“Thanks! You wanna play?”

I didn’t want to play, really, but I thought it might make me feel better. I used to be quite the billiards man back in Vegas. Maybe it would take my mind off of the rejection I would otherwise continue to dwell on.

We got the balls rolling, so to speak, and it didn’t take long for me to realize she was far too drunk to accomplish much of anything on the table. Yet she somehow felt it necessary to critique every single shot of mine and even endeavored to make herself my coach. She lost, of course, and insisted on playing another round.

“I’m gonna go outside and find someone with a cigarette,” I said, hoping it would steer her away from me. Much to my chagrin, she followed me out to the patio and waved down a group of her supposed friends.
“Let’s just sit with them!” she shouted. Volume control was lost to her, though I wasn’t entirely convinced she sounded any differently sober.

I was reluctant to sit down at first until my eyes fell upon a handsome bearded Mexican man that was right up my alley. He gave me the seductive eye as I strategically placed myself next to him.

“What’s your name?” he asked, curling his upper lip. His eyes sparkled like diamonds through a cloud of smoke. The rest of the table disappeared to us as we had our sights locked onto each other like targets.

“You doing anything tonight? You wanna come over to my place?” he asked.
“Uh, yeah, sure, that would be great.” I wasn’t quite as cool and collected.
“Oh, it’s just so easy for you gays, isn’t it?” the lesbian girl blurted out, perhaps attempting to ruin the moment – a failed wedge.

I followed Alex back to his place where he would introduce me to the duplex he shared with his brother. Although we were both intoxicated, he poured us a round of drinks – strong drinks. We sat on the front patio shooting the breeze, joined by Alex’s brother, his wife, and a group of raucous dogs. Indistinguishable music played quietly in the background as we all slipped further down the rabbit hole of inebriation.

Alex stood up suddenly, as if something had just occurred to him. He walked through the door leading to his side of the house.

“Is he going to bed?” I asked Alex’s brother.
“Probably. You should too,” he said, winking.

I hadn’t yet been shown this side of the home, so I wandered aimlessly for a bit before finding Alex naked on a bed. His eyes followed me as I approached him, and with a silent nod he commanded me to remove my own clothing – I did not disobey.

He passed me a bottle of poppers, and I inhaled liberally. A familiar buzz filled my head as I brought my lips to his. We made out intensely, his teeth biting me every so often. I could feel his erection throbbing against me. I thirsted for it to be in my mouth. He stood up and I ran my tongue down his body.

“Yeah, suck it,” he said, pushing his cock to the back of my throat. He had a firm grip on my hair to the point where I worried he might rip it out. I tried to pull back to get some air, but he shoved my head down mercilessly. My vision started to tunnel and blacken.

“This is it,” I thought to myself. “This is what I get for going home to a stranger. No one knows where I am. I’ve messed up. He’s going to choke me to death.” Adrenaline pumped through my veins, but he was just too strong for me to overcome.
But suddenly, he stopped. I gasped for oxygen to fill my innocent lungs.

“Are you okay?” he asked, concerned. The game had changed. He wasn’t trying to kill me after all; he was just into some kinky shit. I got up and wrestled him down onto his bed. Herculean strength surged through me as we rolled around naked fighting each other. It was more a competition than a sexual encounter. I managed to flip him onto his stomach and held him down by the back of his neck.

“Oh, yeah?” he said, trying to squirm out of my grip. I pushed down harder.
“Yeah.” I spit into my free hand and lubricated us both. I penetrated him deeply on the first thrust, and the fight was over. Alex surrendered to his submissive side and positioned his ass upward to be fucked forcefully while he jerked off. The sound of our flesh colliding echoed against the walls.

“Fuck the cum out of me!” he screamed, placing his hands to reach a push-up position. I was surprised how naturally this role came to me, as I had never been so sexually aggressive in my life. It felt good to hold power over someone, while knowing they were in ecstasy. I pounded him harder until he had no choice but to orgasm, hands-free.

Alex collapsed onto the bed, and I stood up, panting like a beast. I didn’t feel like myself, but this was exactly what I needed after being stood up by Roberto. Alex closed his eyes, and I laid down to hold him in my arms.

He fell asleep almost immediately, snoring softly. It was a moment of serenity after the preceding chaos. This mysterious man of rage was now filled with peace. I fucked him into a coma, I decided. And with that, I quietly dressed myself and left. It didn’t seem right to stay – my work there was done.

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Third Leg

Browsing dating apps can be tedious and overwhelming, especially if you’re looking for someone of substance. I’ve had more penis pictures sent to me than I could count. Don’t get me wrong, I do love a well photographed package, but it doesn’t exactly set the tone for relationship goals.

I found a man named Anthony online who looked very presentable and had a well-written profile biography. More often than not, guys don’t even bother to fill them out. Or they will simply put in some sexual bullshit with improper grammar and odd symbols.

Speaking of symbols, can we just take a moment to figure out how an eggplant is supposed to represent a dick? If my dick were shaped like an eggplant, I would have some concerns. Cucumbers? Sure. Even a banana. I’ve seen a lot of cocks in my day, and I can’t say any one of them remind me of a bulbous vegetable of uneven proportions. I digress…

After some small talk, Anthony and I began sharing our passions, hobbies, favorite things, etc. He used to work for Disney, and he was obsessed with Harry Potter. What more could I want in a man?

He lived in up in Leander, which is a suburb of Austin no one cares about. We decided to meet for a date in Cedar Park, which is a slightly closer suburb of Austin no one cares about.

I dressed to impress and headed up to the sports bar he suggested. Ironically, we’d soon find out that neither of us cared much for sports. But it was a good location all the same, and we were able to sit down and get to know each other better.

Neither of us ordered any food, or even beer – just water. I’m not sure what his reasons were, but I didn’t want to be the only one digging into a greasy basket of cheese sticks and chugging down cheap booze.

We spent several hours together before deciding to wrap it up. I knew we wouldn’t be spending the night together, which is the most common fairy tale ending to first dates in the gay world. He still lived with his parents, because he had just moved back from Florida. As it would turn out, they were Pentecostal Bible thumpers who disapproved of homosexuality. His mother was sleeping with two men at the time of Anthony’s conception, because adultery is apparently not sinful. This resulted in him having an estranged biological father than he never got to meet. He was raised instead by his mother’s husband, and he was often reminded of it during arguments. Anthony’s biological father was black, and being the only biracial member of his white family did not make matters any better.

He walked me to my car, and we both hesitated in that awkward time warp trying to decide if we should kiss and who should initiate. I get uncomfortable and impatient in that situation pretty quickly, so I got up on the tip of my toes to reach his lips. I’m above average in height, but Anthony loomed over me. A parking lot isn’t very romantic, so we didn’t kiss for long. And before parting ways, we made plans to see each other again soon to do karaoke.

Before driving away, I texted a couple of my friends who wanted to know how the evening went. I filled them in on the details, and they were all happy to hear the good report. One of my friends jested about him being half black and accused me of being a size queen. Because all black men have to have giant dicks, right? I’m not a fan of stereotypes, but at least that one is somewhat complimentary.

The night of our karaoke date came quickly, and he drove all the way into downtown Austin to meet me at my favorite spot. Unlike last time, we both decided to indulge in rounds of beer. I justified it would make our voices sound “better” while performing songs. He was too intimidated to sing in front of people, unfortunately. But I did lure him into my clutches with my own siren songs.

I returned to our table and suggested he stay with me overnight instead of driving all the way back to Leander, especially after drinking. I’m pretty sure he was planning on that already, but I extended the invitation anyway. And, of course, he obliged.

When we got to my apartment, there was no time wasted in pawing at each other’s clothes and throwing them around. There was a path of debris heading right to my bed.
He hit the lights before I got to see him naked, but he certainly felt good. He had a large, sturdy build with a well defined chest and unbelievable biceps.

We laid in bed making out for a while, running our hands down each other’s bodies. I wasn’t in the mood to invest much more time into foreplay, so I climbed on top of him. My hand reached back for that moment of truth, because size does matter to a degree. Anyone who says otherwise is either ashamed or being polite. But something didn’t feel right.
I wasn’t able to process what my hand was grasping at first. “What is that?” I thought to myself. I finally realized I was, in fact, touching his penis. It was so gigantic in both girth and length, it felt like an actual third leg.

“Holy shit, Anthony!” I shouted, dismounting from my straddled position.
“I know, I know, I should have told you, I’m so sorry!” he pleaded.
“No, no… it’s okay, just…”

Just what? I didn’t know what to say. I reached for it again to measure for size. It was monstrous and fascinating. Certainly larger than any phallic fruit or vegetable I had ever seen. It was like holding onto a burly man’s forearm. I wanted him to have a big dick, but this was outrageous. I’d never even seen a porn star be so well endowed. Was there a such thing as gigantism of the genitals?

“Wow, what do you feed that thing?” I said, stupidly.
“It’s always been this way,” he said, defeated. I felt terrible for him. This man seriously had such a large penis, he was hardly ever able to use it. I’ve pitied men born with little willies, but had never even considered the other extreme.

I decided I would try to at least give him a blowjob. But when I tried to put his wiener in my mouth, it wouldn’t fit. I was trying to unhinge my jaw like a snake. It was the most pathetic attempt at oral sex I could fathom. I stayed down there for a while trying my best, but ultimately it was a fruitless endeavor.

He returned the favor before grinding himself on top of me. I realized that it was the only way he could really get sexual pleasure without having to ask his partner to prepare himself by carrying a wine bottle around in his ass.

“What’s your wildest fantasy?” he asked me. It was a terrible question that I hated being presented with. My brain went completely blank. I felt so vanilla in that moment.
“I don’t know, what about you?” I pivoted.
“Pinch my nipples!” he shouted. “Harder!”

Nipple play is nothing new to me, but this guy was seriously into it. I worried that I was going to twist them right off if I squeezed any harder. Instead, he unleashed a fire hose of cum onto my body that splashed onto my sheets as well.

He collapsed onto the pillows, exhausted. I cleaned myself off with a towel and rested my head on his chest, listening to his heart beat. It was then that a sickening thought crossed my mind. I realized there was no hope in continuing to date Anthony. I wanted to be able to have penetrative sex with my partner. I felt selfish for having to admit that to myself, but I knew I wouldn’t be physically satisfied with this otherwise perfect man.

We woke up together the next morning and said our goodbyes. He mentioned our next date, and I was careful not to lead him on or hurt his feelings. It wasn’t his fault, after all. I sulked back to my bed and laid there, trapped with my own battling thoughts. How was I going to explain to everyone that I couldn’t date Anthony? Because his penis is too big? What a problem to have…

Behind Closed Doors

Some of my greatest misadventures in dating have occurred while living in Austin, prior to meeting my now fiancé. Meeting someone in person is considered old fashioned at this point, so most of those who are fishing for attention and affection must turn to “the apps”. In the gay world that means: Grindr, Scruff, Growlr, etc. I had an active profile on all of them at one point with the intention to either find a boyfriend or at least get laid.

While browsing the man-buffet of pictures on my phone, I stumbled across a gent I found to be rather attractive. He was a bit older than me, well proportioned, and had intense eyes that somehow complemented a large, genuine smile. His name was Trevor, according to his profile, and I decided it was worth a shot to send him a message.

It’s always awkward trying to start conversations with a stranger whether you are in person or have a screen barrier. If you’re looking to seem date-worthy you have to start with something better than “Hey, what’s up?” And if you’re looking to get your dick wet, you have to decide ahead of time how long you should engage in pointless small talk before sending nudes.

I managed to initiate a conversation that eventually resulted in us agreeing to meet at my favorite watering hole for drinks and karaoke. Although, I should mention, we did unlock our “private” collection of photos for each other. With that said, I wasn’t really sure what to expect for the evening.

When I arrived at the bar I recognized him almost immediately. He was sitting with another gentleman who was probably twice my age and quite spindly. His face seemed to have only one expression – a look of both constipation and confusion.

I grabbed a drink before approaching him and the man sharing his table.
“Trevor, right?”
“Travis? Take a seat.” I did. He went on to introduce his friend Pete.

Trevor and I hit it off immediately, and he even complimented me on my singing voice when I would return from the microphone. He was speaking my language with a dry sense of humor and constant use of sarcasm. Even flirting. However, I noticed a closeness between him and Pete that went well beyond friendship. Perhaps I was being paranoid.

Pete got up to sing a pitchy rendition of a song no one else knew as Trevor and I stood and watched. “How do you know him, again?” I asked.
“He’s my boyfriend,” he replied. I laughed involuntarily, completely unsure of whether or not he was messing with me or being serious. I decided not to press forward with any more questions at the risk of embarrassing myself. Instead, I was left wondering whether or not I was invited to a date with two men instead of one. Or maybe it wasn’t a date at all. The mystery wouldn’t solve itself that night, because Trevor ended up getting too drunk and left without saying goodbye. My pride and ego gasped for air before perishing together in a romantic tragedy. I imbibed a while longer to drown my sorrows.

Some months later I ran into Trevor again at that same bar, this time without Pete around to spoil the environment. He greeted me with a tight bear hug, and I immediately dropped any sense of resentment I had been holding against him. Trevor had a quality that I can only describe as mesmerizing, for better or worse.

We shared a pitcher of beer together and spent most of the evening making fun of the poor karaoke performances that night. As it would turn out he didn’t care much for karaoke to begin with and only went for Pete’s sake.
“So if you don’t like karaoke, why are you here without your boyfriend?” I asked, tripping over the last word a bit too noticeably.
“I dunno, I can’t resist the cheap PBRs, I guess,” he joked. “We’re open, ya know, me and Pete.”
“Oh?” My eyebrows raised with suspicion and intrigue. The game had changed.
“Yeah, you want another beer?”

My sides and cheeks were aching from laughter the more time we spent together self-medicating on piss-colored beer.
“Wanna go down to 4th Street?” he asked. This is an area in town where there is a cluster of gay bars. Although most of the patrons of these establishments are young twinks and witless jocks, I didn’t want to reject his suggestion. I wanted my evening with him to continue, regardless of where it was.

We walked and stumbled for a few blocks before entering a nightclub buzzing with effeminate young men, drag queens, and go-go boys. It wasn’t my scene, and I didn’t expect it was Trevor’s either. However, there was a nice patio in the back that provided cabana like structures with an arrangement of couches and chairs. We got our drinks and found a place to get comfortable.

Our conversation shifted from poking fun at karaoke singers to judging the shameless boys prancing around in their underwear belting out Katy Perry lyrics between shots of some green-colored concoction. Our chuckling subsided into a silence that transitioned into very direct eye contact – the kind that signals for action. We began to make out, and everything else disappeared. Trevor was a damn good kisser, and as I said before, mesmerizing.

We broke for a moment and he asked if I wanted to go back to the bar where we started. When I asked why he said, “Because I want to see you try to walk with that!” I followed his eyes to my crotch which I had somehow neglected to notice during our public displays of affection. I reached into my shorts and readjusted myself in one of the few ways us men can really manage. We’re limited to pushing it down to be held poorly by the elastic of our underwear, or flipping it up into the waistband of our pants. You have to be careful not to let your shirt lift up once you’ve committed to the latter, lest you reveal the top half of your schlong. We’ve all been there, men. You’d think it would get easier to play the “How Do I Hide My Boner?” game after surviving puberty, but that’s not really the case. I digress…

Trevor and I did indeed return to the first bar which was now considerably more crowded than before. The night owls had come out to play.
“I’m going to the bathroom,” he said to me.
“Okay.” My eyes were wandering around the room, analyzing new bodies and faces.
“No, I mean, I’m going to the bathroom…” he said again, this time with a mischievous grin and a no-longer disguised agenda.
“Oh!” He walked away leaving me with a difficult decision. Do I follow him and risk getting caught having sex in a public restroom? Should I stay? Should I go? Am I really about to do this?

Perhaps it was the alcohol thinking for me, but I ended up casually wandering into the men’s bathroom. I found him waiting there in an open handicap stall with the shit-eating grin of a champion spread across his face. He pulled me in and locked the door.

Now having sex in a gay bar’s facilities doesn’t sound very appealing, but it’s actually more thrilling than I had previously thought. And kudos to him for picking a handicap stall that had convenient metal bars around to hold on to. This probably wasn’t his first rodeo.

We made no attempt to be quiet in any way. My worry about being caught flew out the window, replaced by primal lust and reckless indiscretion. We heard other men coming in and out of the restroom, carrying on conversations and seemingly ignoring the distinct sound of sex. Perhaps this was more common than I thought. Now it had become an auditory performance.

I have no idea how long we fucked, but at some point after climaxing we both realized that the bar would be closing soon. We dressed ourselves and peered out the stall door. The garbage had already been bagged up and tied by some poor barback who most likely experienced a symphony of our moans.

Trevor and I made our way out of the bathroom and found a backdoor to sneak out of. I’m not sure what the point of protecting our identities was at that point, but it felt like the right thing to do.

“Well that was fun,” I said, still somewhat out of breath.
“Yeah, we should do it again sometime,” he said with a nod.
“Maybe even in a bed?”
“You’re not that boring, Travis,” he joked.