Falling

I know at least a good handful of people, both men and women, who would love to be taken care of by a sugar daddy. Prior to falling in love with my fiancé, I would have considered myself open to the idea. It gets tiring busting your ass all day, being undervalued by some corporate entity that sees you as an expendable resource. The American Dream is dead for most of us, but there’s still hope in becoming a spoiled housewife. And although I never advertised myself as looking for a rich man’s attention, I would be confronted with it nonetheless.

I was messaged on Grindr by a small blond man whose age was indistinguishable due to his youthful attire and “alternative” hair style. But I knew he was older than he would ever care to admit. When I showed my best friend his profile picture, he commented that he looked like an anime character. He wasn’t wrong. Avery looked like he just popped out of an episode of “Naruto”.

Our small talk didn’t last too painfully long before we decided to set up a date for brunch. If you don’t already know, gays love brunch. I mean, everyone probably loves brunch, but we really own it. He picked a place I had never been to, and we agreed to meet outside the restaurant the very next day. He was sure to tell me the exact car he would be pulling up in, which ended up being the most expensive Mercedes I’ve ever seen. He zipped past me through the parking lot. I wondered if he was one of those people who lives in some shithole apartment, but makes a concerted effort to afford a sports car.

Avery walked toward me with a practiced swag, his long pointed hair blowing gently in the wind. The sunglasses he was wearing were probably worth more than my entire closet at home. It seemed to take forever for him to finally reach me, but his stride was awfully small.

He greeted me with a smile revealing veneers and the nasally voice of a lifelong smoker – like Macy Gray with a head cold. I wasn’t super thrilled by it, but there we were.
The place was busy, so we were only able to get seating up at the bar. It was a nice distraction though, seeing chefs scramble to put together breakfast pizzas and the like.

We each ordered our own carafe of mimosas, because that’s really what brunch is for – an excuse to drink alcohol before noon. The menu was too expensive, in my opinion, so I ordered the cheapest thing I could find. Avery did just the opposite.

Our conversation turned to work and what we both did for a living. I gave the briefest of histories on my past and current experience in hotel management including my stint in Vegas. His eyes lit up when I mentioned that – The City of Sin.

Avery told me all about his many travels around the country, including Vegas. He only spent a few nights of the week in Austin; the rest were spent in Starwood hotels. He specifically frequented the hotel I used to work for, and it was quite possible we’d been there together at the same time on many occasions. Small world.

He worked for a company that had something to do with saving other companies money on health insurance. I didn’t really care to wrap my head around it beyond that. The car wasn’t just for show, this man made a ton of money.

I hated talking about hotels, but the conversation was careening down that path despite my attempts to derail it. We finally wrapped things up, and I honestly wasn’t sure what to think of him. He was cute in a way, although not my usual type, and walked a fine line between charm and ego. I was pleased he picked up the tab, whether it was out of chivalry or showmanship.

Avery walked me to my car, and we stalled for a bit. There’s just no way to get around the anxiety that builds up to a first kiss. I am typically the one to just pull the trigger to get it over with – such was the case here. His lips and tongue were strangely soft, but he was a good kisser. I felt like a giant next to him.

We parted ways without making any definite future plans, being that his travel schedule was so busy. But it was only later that week I received a text from him asking if I would like to come over and watch a movie. Now this was before the phrase “Netflix and chill” came about, but I figured he was initiating a booty call. In the gay world, that qualifies as a second date anyway.

To my surprise, he mentioned that we would not be having sex in his following message after I agreed to come over. I liked that he was so straight forward and hopefully looking for something more than a hookup. I needed to spend more time with him to really know if he was the right guy for me, though.

Avery didn’t live too far from me, but his neighborhood wasn’t in the ghetto like mine. In fact the houses I was passing by were modern residential marvels. I traversed a maze of roads, losing track of my turns, before finding this man’s house. And what a house it was.

He was waiting for me in the entryway to the garage, perhaps just to casually remind me again of his superior vehicle as we passed by. I followed him inside and had to hold back my awe and wonder as my eyes fell upon the most luxurious home I could imagine.

“Do you like it?” he asked, already knowing damn well that only a jaded fool would be unimpressed.
“Yes, it’s amazing,” I said, thinking of my own miserable little place – embarrassing. His kitchen was larger than my entire apartment.
“Does the theme look familiar?” It did, but I couldn’t quite put my finger on it. “It’s just like the Westin! You should see the bedroom upstairs.”
“I’m sure I will,” I said nonchalantly. This man stayed in Westin hotels so often, he turned his own house into a haunting doppelganger.

Avery directed me to the living room boasting an impossibly large couch and a television that could serve as a wall. I could see dollar signs everywhere I looked. We sat down and agreed to watch an episode of “Nashville”, one of my favorite shows, and his. (don’t judge). Before he settled in, Avery walked back into the kitchen to get a glass of water. I saw him reach into a satchel on the island and somewhat discreetly pull something out. He tilted his head back and threw what I assumed were pills into his mouth before swallowing them down.

I immediately jumped to conclusions. He clearly had a lot of expendable income, it would make sense that he could afford a drug addiction. Or was I just being paranoid? It could have been anything, I assured myself. This was just PTSD from a previous addict I once loved.

He came back to the couch and positioned himself as the small spoon. Being so petite, Avery fit into my body like a puzzle piece. It was relaxing at first, until I noticed something odd as I ran my fingers through his hair. He was sweating profusely.

“Are you okay?” I asked hesitantly.
“Yeah, yeah, I just run hot,” he replied, lying through his teeth. He turned his head to kiss me, and we made out for what seemed like forever. I didn’t like the idea of him being under the influence of a drug, but I caved to temptation. I wanted attention. “You’re not having sex with me tonight,” he said, this time slurring his words together.
“I know, you mentioned that earlier…” I said, wondering what he was really after. He pressed his lips hard against mine looking straight into my eyes.
“Uh oh,” he said almost whimsically.
“What?” I asked hesitantly.
“I think I’m falling. I shouldn’t, but, I’m falling.” He rested his head against my chest. “Your heart is beating so fast…”
“I think you should go to bed, Avery.” It was his own heartbeat that was elevated.
“Yeah, let’s go.” I had no intention of spending the night, but I wanted to make sure I got him to his bed safely. I was hardly able to understand him, and even walking became an issue.

I followed him up the stairs, ready for him to fall backwards at any moment sending us both cascading downward. By some miracle, we advanced into his sprawling bedroom. He stripped down to his underwear and asked me to lay down with him. I weighed my options and decided to stay, despite my gut feeling not to. I have extraordinary intuition and a bad habit of going against it. I removed my clothes and climbed into bed. Using a remote, he turned on extremely loud trance music. I was deafened and lost in a moment of surrealism. What was this?

He rolled toward me to put his hands on my body and struggled to climb on top of me. Clearly he was horny, and his initial notion of us not having sex seemed to have flown out the window.
“You’re not gonna fuck me,” he said. I stared at him silently, though he was obviously waiting for some kind of response. He continued to grind and gyrate against my skin. At some point, he managed to get his underwear off. And then mine. He reached back to grope my balls.

A terrible thought popped into my head: “Thou doth protest too much.”
Was he expecting me to just take and ravage him to fulfill a rape fantasy he’s been after? Or is he just fucked up and trying to push me to some kind of limit? It sure seemed like he wanted to be tossed around, but I knew I couldn’t take that chance. Especially with him being under the influence of some drug that seemed to be affecting him more and more – perhaps his judgment the most.

Before I was able to say anything he rolled off of me and passed out almost immediately. The speakers were still blaring, and yet I could hear bear-like snores erupting out of him. For being so tiny, it was astounding. Is this what Avery wanted? To knock himself out so I could take advantage of him? My mind was racing, unsure of how to get myself out of this situation, this mess.

THUMP – he fell out of the bed onto the floor.

I jumped up expecting to see an awakened, disoriented imp staring up at me. But no, he was knocked out cold. I needed to get out of there. Looking through the darkness, I scanned the room for my clothes. “Where are they?” I said aloud. And then I realized exactly where they were – underneath Avery’s body. Shit.

I knelt down and gently pushed on what felt like a sweaty corpse to gain access to my clothing, not wanting to wake him up. Was it even possible to rouse him in this state? It was. As he began to stir, I grabbed the articles and hastily dressed myself. Avery climbed back up onto the bed like a sloth, looking at me, or perhaps through me.

“What are you doing?” he asked, sounding quietly perplexed.
“I’m sorry, I need to leave. Are you okay? Do you want a glass of water?”
“What? You’re leaving?” he shouted over the blaring beat of some EDM track.
“Yeah, I can’t sleep, I need to go.” My tone was dull and flat.
“No, no, don’t leave me. I’m going to be alone forever!” he pleaded. This was getting worse by the second. I didn’t know what to say, because I suspected he might be right.
“Don’t leave…don’t go…” he slowly trailed off into tearful silence for a moment. “I’m falling for you…I can take care of you…”Avery made more money than I could ever dream of, and this was a pathetic last attempt to keep me from leaving. The broken crutch of a desperate wannabe sugar daddy with a drug addiction.

An older version of myself might have stayed. But I was done being a fool. I was done making sacrifices for people who didn’t deserve it. And I was done with people who had no real sense of what they wanted or needed. It pained me to see him so upset, though I wondered if he would even have memories of this exchange the next day. He wasn’t falling for me, not truly. And I certainly wasn’t falling for him.

“I deserve better than this,” I said more to myself than to him as I exited the room and made my way to the stairs. “And so do you.”

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.