Double Trouble

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Role-playing adventure gone awry leads to (double) trouble.
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CalMaple
CalMaple
295 Followers

The bitter air bombarded me as I exited my car and made my way towards to door. I walked into the small gay bar; it was the only one in town. Most of the patrons were young people who moved to the area long enough to attend its one liberal arts college before moving to somewhere more urban. It was unfair, I supposed, to equate 'one college and one gay bar' to 'one horse,' but that's what it felt like to me most of the time.

The bar was an interesting place, at least. It had previously catered to veterans before the owner had sold it several years earlier. It tried to fly under the radar so as not to provoke the more conservative residents in the town. One wouldn't even have been able to tell it was a gay bar from the outside.

I found a table near the door, where I tossed my heavy jacket on the back of a chair. The décor was vaguely depressing. The laminate floors were peeling away at the corners of the room, the fabric on the chairs were covered in stains, and the lighting was so dim it was hard to see anything clearly past ten feet.

It was a Thursday evening. There were only about fifteen people in the place. I didn't recognize anyone I knew well enough to feel compelled to say hello. Fridays and Saturdays were far more popular; it was common for there to be fifty people packed into the small venue on weekends.

I ambled up to the bar and ordered a Budweiser. The bartender was an older, friendly lesbian named Marta. She asked me a few obligatory questions about how I was doing before journeying down to the other end of the bar to help another customer.

I returned to my seat, settling into the well-worn cushion. Some queer anthem from thirty years ago was blasting away, and a few people were grinding against one another on the small dance floor. I looked at my phone; the screen informed me that it was 11:23 p.m. I had been hoping that Theo had texted.

I had met Theo a few weeks earlier through a friend of a friend. Even thinking about him stirred the butterflies in my stomach. At six-foot-two and packed with muscle, he was the kind of guy I always wanted to be with but never seemed to get. I had invited him out for the evening, but he'd declined, citing a family dinner and the need to study for a midterm.

Theo and I had a conventional relationship for two twenty-two-year-old gay guys. We'd dived right into hooking up, and now we were exploring if we wanted something deeper. I already knew I did, and that made me anxious. I didn't know where Theo was at, and I was worried that I might be sending out desperate, clingy vibes.

Still, I was also hopeful - possibly against all reason. The truth was that we barely knew each other. I had only heard the basics about his life: what he was majoring in, that he'd lived in this small college town his entire life, that he had a brother and a sister, and that he wanted to become a pharmacist.

I returned to my beer, trying to drown my sorrows. I texted a few friends, attempting to convince them to come join me at the bar. Nobody was responding to my messages.

I eavesdropped on the conservation of the two guys at the table next to me. They were discussing how one of them was attracted to his TA. He was trying to get his friend to reassure him that it wouldn't be inappropriate to ask him to hook up after the semester came to an end.

Bing!

'I might take a break later tonight and pop by your place,' Theo's message began. 'Not sure when though. Let me know if you don't want me to come over if it's too late.'

'I'll be around all night,' I texted back.

I felt the immediate urge to down the rest of my beer and race back to my apartment. I really wanted to feel Theo's muscular arms wrapped around my smaller frame. God, that's sad, I thought. I didn't think it was sad to want to be held by him - more that it was pathetic that I would run home to just wait around when I didn't even know when - or even if - he was going to come.

I made myself promise that I wasn't going to leave for another twenty minutes to prove to myself that I wasn't what my friends referred to as "dick-matized." I relocated to a stool at the bar, thinking that idle chit-chat with Marta would help pass the time. I quickly realized that that was a mistake; she seemed to be in a world of her own when she wasn't pouring drinks.

I pulled out my phone - only five more minutes until I could leave. I heard rustling beside me as someone settled onto a stool.

"Can I get a beer?" a familiar man's voice from the stool next to me called out to Marta.

"You got it, hun," she replied.

It was Theo sitting next to me. My heart began to beat a little more quickly realizing that he had completely blown off his studying to come meet me at the bar; it made me feel special. I had been certain that, at best, he would crawl into my bed at 2 a.m. hoping for some head.

He looked great. It felt as if I was seeing him for the first time, even though we had just spent the night together three days earlier. I noticed that he had grown out his sandy brown stubble, which looked incredibly hot. I remained as mesmerized by his sharp jawline, icy blue eyes, and spiky blond hair as when we had first met. I couldn't believe I had been fucking this Adonis for the past three weeks.

I sat, staring at him, waiting for him to say something. As soon as Marta handed him his beer, he looked down at his phone. I knew he must have seen me when he took the stool right next to me. What game is he playing? I wondered.

"Hey," I said, as I pivoted in his direction.

"Hey," he replied in a blasé manner.

The alcohol wafted into my face as he spoke that one word. He must have been drinking a lot during dinner. I didn't really know much about his relationship with his parents, but I was surprised that he would get that loaded at a family event. In addition to being quite tipsy, he also seemed a little off in some other way as well, but I couldn't quite put my finger on it.

"Do I know you?" he asked.

I reflexively chuckled, feeling a mix of confusion and annoyance. I looked at him, waiting for him to say "just kidding" or something of that nature. He just sat there silently with a polite smile on his face.

Oh, I thought to myself, he's buzzed and wants to play some kind of game. It was weird, but it wasn't that weird. We'd been having sex for three weeks. He was sending out the feelers in a public place. I wasn't in any danger of getting roped into anything I didn't want - not like waking up hogtied to my own bed for some surprise BDSM.

I figured that if he wanted to play a game, I would play another. I hoped that it might actually be a fun time for both of us.

"Sorry," I said, joining the conceit. "I thought you were someone else."

"No worries," he said. "How's your night going, bro?"

"Not too bad," I said. "Could be better, though. I was supposed to meet up with this hot guy I've been seeing, but I guess he isn't coming."

"That sucks," he said.

Theo went quiet again as he stared at the bottles of liquor behind the bar. I wondered if I had done something wrong. I had never done any spontaneous "stranger" role-play before. I worried that I was failing some kind of test he was giving me.

"How's your night going?" I asked.

"Not great," he said. "I had this family dinner thing. My parents are total assholes. They're always getting on my case about the smallest things."

"I'm sorry," I said. "I hate how parents think we are still little kids even though we're grown men."

"Totally," he said, his face lighting up from my validation.

It appeared that joining in on the parent-bashing was what he needed in that moment. He talked about how his parents had always made him feel like he wasn't good enough. Specifically, he spoke about how they always bragged about his siblings' accomplishments while seeming to overlook everything he had done.

I hadn't known that Theo's parents were that judgmental. Then again, I hadn't known much of anything about his family before that night. I tried to convey empathy and warmth with my facial expression to show him how much I cared.

"I'm Leo," he said, extending his hand. "What's your name?"

I had to force myself to stifle a laugh that was trying to make its way up from my belly. I smirked; he was really committing to the bit, and rhyming the names was undercutting it just enough to make it playful and fun. It put me at ease. It let me know everything was going smoothly.

"I'm Parker," I said. I could lie to you and say that I resisted the temptation to offer up a rhyme of my own, but the truth is that I just couldn't think of one. I still can't, honestly - not one that passes the laugh test as a first name.

"Nice to meet you, Parker. So, what's the deal with this guy who's standing you up? You seem like decent, nice-looking guy."

"Nice-looking? Wow, that's an underwhelming compliment."

'Leo' chortled and beer almost shot out of his nose. He spent a few moments steadying himself and catching his breath. He swiftly placed his left hand on my shoulder, giving it a friendly squeeze.

"Yeah, that didn't sound too great, did it? I can tell that you're really fit guy. Totally fuckable!"

Leo winked before tossing back the remained of the beer in his glass. He motioned to Marta that he wanted a refill. His fingers were massaging into my shoulder through my sweater.

Once Leo had his second beer, we continued to make conversation, but it veered to more banal topics. We talked about the struggling local economy and sports. It felt as if we had taken a step backwards again. I wondered if opening up about his family issues had soured the game for him. I had been starting to enjoy it myself; something about it was sensual and exhilarating.

I decided to push us back into the direction we had been headed twenty minutes earlier. I wanted the rush of hearing Theo say sexy things to me, even if he was doing it as Leo.

"I know we just met, but can I say something that might be a bit forward?"

"Go for it."

"You're really fucking hot, Leo. There are so many things I'd love to do to your body."

Leo's face turned bright pink; he looked down at the bar. I reached over and placed my hand on his thigh. Its defined musculature was warm beneath my large hand. He looked up at me with a smirk on his face.

"You're really going for it."

I nodded; I massaged my fingers into the worn denim of his jeans. I thought I could see a bulge beginning to form in his crotch area, which reassured me that the bizarre role-playing must be working for the both of us.

"I'm flattered," he said, "but I'm straight."

He's 'straight?' I thought to myself. What the fuck am I supposed to do with that? There was one obvious possibility: the fantasy of a gay guy 'turning' a straight guy, or at least one in deep denial. I wondered if he thought that would turn me on. I wasn't ready to say it didn't at all, but it felt like a strange twist on our dynamic. He was the big, beefy, muscly guy in the relationship, and we hadn't exactly defied any of the usual cliches. Then I wondered if he was being especially vulnerable with me in a roundabout way: begging me to take charge for once.

Suddenly, I wasn't feeling adventurous. I decided to play it safe - straight, you might even say.

"So... why are you in a gay bar if you're straight?"

"Kind of a funny story," he replied. "I've been coming here since high school. I knew that the bar had been sold to a new owner, but I hadn't heard more than that. It took me a few moments after ordering my beer to register that it was a gay bar. It may have even taken longer if 'It's Raining Men' hadn't started playing."

"Well, the humidity is rising and the barometer is getting low..."

"It's raining men, hallelujah!"

We both burst out laughing. I was letting myself lean into the absurdity of the situation; he seemed to have imbibed enough that most things seemed funnier to him than they probably should have.

"Straight, huh?" I pressed playfully. "Like...how straight?"

Leo blushed and bit his lower lip. It was endearing; it felt as if he was genuinely shy. He was really committing to the character. Meryl Streep had some competition.

I pushed again. "So...you've never kissed a guy?"

"Of course, I've kissed a guy," he replied. "I'm straight, not middle-aged."

I continued to massage his thigh with my fingers. I slid my hand a little closer to his crotch. He didn't startle or pull back.

"I think that's bullshit!" I teased. "You've definitely never kissed a guy!"

I wasn't really thinking about what he wanted anymore. I was increasingly focused on what I wanted - which I supposed was a good thing. I could admit that we were engaging in a novel, amusing kind of foreplay, but that's what it was for me. I wanted it to lead to the real action.

"You're an idiot," he smirked.

"Prove it," I said. "Give me a kiss."

I stared directly into his sparkling eyes. I was challenging him to do something that he had already done many times, but now there was an underlying power dynamic at play. Ironically, my own growing need was what finally empowered me to do what I'd guessed he'd wanted all along: take charge of the situation, and maybe even of him. The latter was still up in the air; I could picture 'Leo' getting a taste of me and going a bit crazy, and that thought turned me on quite a lot.

We gazed at one another for a solid thirty seconds. I could see the gears turning behind his eyes; it was uncanny. It was masterful. I got genuinely frustrated with Leo, not 'Leo,' and that's how I reacted.

"I knew you weren't..." I began.

Leo lunged forward and started making out with me. His breath was hot and tasted of alcohol. He placed his hand on the back of my head, smashing our lips together. It only took me a second to reciprocate fully. I quickly began to explore his mouth with my warm, velvety tongue.

I noticed that he had his eyes closed; he was really getting into it. His stubble rubbing against my face was a huge turn-on. My heart began to speed up as the prickly hair scratched and teased my soft skin. I slid my hand up so that it was cupping Leo's package. I began to rub it through his jeans. I could feel him getting hard beneath the thick denim.

Leo stopped kissing my lips and gently pulled his mouth away from mine. His eyes were beaming with a sense of victory. I stopped rubbing him, but I kept my adventurous hand where it was. I wasn't going to cede any ground in the sexual tug-o-war.

Leo took a massive drink of his beer. I noticed Marta looking at us from the other end of the bar. She had a look that seemed to indicate that she was not enjoying watching two buzzed young people going at it in front of her.

"I told you I'd kissed a guy," Leo said, pride resounding in his voice.

I still didn't understand what we were doing, exactly, but I was ready to head back to my place. If Theo wanted to keep on exploring the fantasy, I was more than willing to do so in the comfort of my apartment.

"Why don't I help you with this?" I offered, squeezing Leo's hard cock.

Leo looked hesitant. He scanned the room like he was looking to someone else for guidance. He bit his pouty lower lip again. I found it incredibly endearing that he suddenly appeared very nervous.

"I really haven't done this before," he whispered, "but I guess there's a first time for everything."

Leo reached down and placed his hand on top on mine. He pressed it deeper into his crotch. I wanted his cock in my mouth in that very moment. Better still, I was reasonably certain I was going to get it very soon. That changed the whole game - retroactively, even. It was, and always had been, hot as fuck.

"Let's go back to my place," I said while placing enough cash on the bar to cover our drinks, plus a hefty tip.

Leo and I exited the bar, braving the nigh-arctic temperatures to get to my car. We both hopped in, and I cranked the temperature to the maximum setting. The heated air washing over Leo's face, combined with the warmth of the booze, seemed to make him tired. He leaned his head on my shoulder.

"You make a nice pillow," he said in a soft voice.

He looked so sweet that I didn't want to disturb him. It only took a few minutes to drive to my apartment. He straightened himself up as we parked in front of the building.

"Is this it?"

Okay, I guess this is going to be an all-night thing, I thought to myself. I wasn't frustrated, though. I told myself that it was good that he trusted me enough to play with me - especially since he'd let me take the lead; that had to mean that he was hoping for a deeper relationship.

"It's unit forty-one. My roommate is staying with his girlfriend tonight, so we won't have to worry about being interrupted."

Leo glanced at his phone in a concerned manner, then he looked back at me. I looked down at his crotch; his package had shifted so that his thick tool was plastered against his thigh. I reached down and wrapped my fist around its denim-covered shape.

"I really shouldn't stay too long," he said.

"I'm just happy for any time we have together," I said.

I was talking to Theo in that moment, but it worked for his alter ego too. I just wanted give 'Leo' what he wanted. If that was a quick hookup before he returned home to study, that would have to be enough. I honestly couldn't imagine him studying, though. He was going to have one hell of a hangover.

Leo and I bolted from my car to my apartment, limiting our time in the bitter cold. I hurriedly unlocked the door and ushered him inside. I scanned the room to make sure I hadn't left anything too disheveled.

The living area looked the same as it had a few hours earlier. A small navy sofa, a leather recliner, a large television, and a coffee table filled the cramped room. There were a few textbooks piled on the table that I had been reading that afternoon.

"Have a seat," I said, motioning towards the couch. "Feel free to help yourself to a water in the fridge. I'm going to freshen up really quick."

Leo continued to stand there; it wasn't as if he hadn't been to my apartment before. I swiftly turned the corner and made my way back to the shared bathroom.

I gazed at my reflection in the mirror. I was still looking good - not as good as Theo/Leo, but good nonetheless. I splashed a little cold water on my face. I didn't want to take so long that Leo would lose interest and leave but, I still needed to prepare. I gurgled some mouthwash, as I debated whether I wanted to douche. I decided against it since it would take too long, and all I had eaten was a light salad earlier that day.

My reflection gazed back at me - hazel eyes, wavy black hair, and alabaster skin. At five-foot-seven with a lean swimmer's body, I didn't have the same muscular build as Theo. I still felt pretty proud of where I ranked in the twink community.

I wondered if 'Leo' had any more surprises in store for me. Maybe he'll want to play up the reluctance and I'll have to persuade him, I thought. Shit... maybe he actually wants me to top him. Holy shit.

I finished up and left the bathroom. It was only about ten feet from the entryway to the living area.

"Sorry, that took so..." I began to say as I re-entered the room.

I heard myself gasp instead of finishing my sentence. Leo/Theo was sitting on the couch with his zipper undone; his rock-hard nine-inch cock was pointing into the air. He held a bottle of beer in his right hand.

I stood, frozen. He had never been so 'to the point' when it had come to sex. We normally made out for a while and progressed from there. It was slightly shocking to see him get right down to business.

"I hope this is okay," he said. "I made myself comfortable."

"Sure," I mumbled.

CalMaple
CalMaple
295 Followers