My First Time but Not My Last

Let me start by saying: I'd never been with another man before this.

All my life, I'd thought of myself as obviously straight. But if that was the case, then why did I love watching gay porn and imagining myself as the bottom? Why did I buy a range of prostate toys and dildos, and why was that my preferred manner of masturbation? Why did I have a Grindr profile and why was I waiting in the Airport Hilton bar for my date -- another man, mind you -- to arrive? Why was I furiously aroused at the idea of him coming back to my room?

When Michael arrived at the bar, I was not only relieved to see that he looked better than his photos, but that he had a charming personality to boot. He was thin but muscular and a little over six foot tall, just like me. He wore trendy round clear plastic frames and had a simple but stylish haircut that suited him well. He had a smile that made me melt and when combined with his endearing laugh, I instantly felt different about him than I had any other man before.

The conversation flowed nicely. We started by talking about hobbies and preferences, but we didn't use Grindr at the Airport Hilton to talk about how we spent our free time. I told him about my as of yet solo journey of sexual exploration, and how I always chickened out from meeting people. Michael listened without judgement and understood how it felt to question something so fundamental as my orientation.

After the second round of drinks, I couldn't contain myself anymore. I told him that I had come from my family's house in the north country, and it'd been ten days since I'd had any... "me" time. I awkwardly put my hand on his thigh, and asked if he wanted to come see the suite that I'd been upgraded to. He smiled and softly touched my shoulder, then we headed upstairs to my room.

In someone else's experience, this would be a tale of unbridled passion, but I had no idea how to proceed like that. Even with girls, my charm comes from my awkward demeanor; with another man, I was in uncharted waters. Michael found my bumbling nature endearing and kept the mood light. I let him in, and gave him the grand tour of the place.

"Your TV is so much bigger than the one in my room," he said.

I nervously made a joke about it not being the only thing that was bigger up here, but immediately apologized. Michael laughed, and while I felt dumb for making the joke, my heart melted. I'm straight, but damn this man was my kryptonite.

"Come sit on the couch with me," he said, turning on the TV and flipping through the channels. As he flipped through the TV guide, we talked about what was showing on each channel. "I've seen that, it's funny," one of us would say, and the other would lie and say we'd add it to our list of things to watch. Eventually, we settled on watching The Matrix since we'd both seen it before, and it's a classic. I nervously snuggled up against Michael and watched the scene where Neo sees how deep the rabbit hole goes.

After that scene is a lot of plot-related talking, but I was beginning to feel so horny that I couldn't bear it anymore. He said something, to which I chuckled and placed my hand on Michael's thigh again. He looked me dead in the eyes, and leaned in for a kiss. One kiss turned into a make out session, only stopping to turn the TV off since Morpheus explaining how humanity and machines went to war was putting a damper on the mood.

Micheal smelled like aftershave and kissed with the expertise and grace of a ballet dancer. His hands, while wiry and thin, were dexterous and steady, and it didn't take him long to discover how aroused I already was. When his hands caressed my cock, I had to stop and gather myself but he smiled again. I felt immense (yet expected) repressed shame that I just needed a second to process. I took a deep breath, and smiled at Michael. "Sorry," I said. "A 34 year old virgin is a bad look, huh?"

"Nonsense," Michael replied with his comforting smirk, and stroked the side of my face. "We can go at your pace."

After a second, I leaned back into kiss him again. I felt his body, and he felt mine. Not long after, our shirts came off, and I noticed that both of us had erections peeking over the top of our pants. I firmly yet awkwardly pushed Michael back into the sofa, and unzipped his pants to reveal his cock.

Again, I stopped and caught my breath. Nothing from my porn watching prepared me for this moment. This wasn't a well-framed image of a cock; this was mine for the evening. It wasn't huge, but he was well-groomed with a larger circumference than me, and was still only semi-hard.

"You can touch it if you'd like," Michael smiled. That first touch was something I'll remember forever; the feeling of the warm, soft cock shot up my arm like static shock. When I first wrapped my trembling hand around it, I knew it was a natural fit. His girth fit the curvature of my hand perfectly. I then slid my hand up and down his shaft, waking his cock from its slumber -- all the while I stared in amazement at his perfect tool.

Again reading my thoughts, Micheal encouraged me to try it in my mouth. "I can tell you're curious."

I took a second; this was a moment of no return for me. I was knew I couldn't be this excited to taste his cock yet still be 100% straight. There was no going back once this was in my mouth.

But I pushed those thoughts down and focused on the moment. I moved from the sofa next to him down to the floor, and drew a deep yet shaky breath. Slowly, I licked the tip, leaving a trail of precum on my tongue. I paused to evaluate the flavor: it tasted like nothing, but it had a warm and slippery texture. I went back in for second taste, but this time I closed my mouth around it, and experienced sucking a cock for the first time.

Inside my mouth, I moved my tongue around the tip. His precum mixed with my saliva in my mouth. Next time I took his cock out of my mouth, small wet strings fell out of my mouth with it. I wasn't expecting this, and somehow it aroused me even more.

Soon, just tonguing the tip was no longer enough and I took more of his cock into my mouth. I relaxed my jaw, stuck my tongue out, and took him to the back of my mouth which was only about two thirds down the way of his shaft. I wrapped my hand around his base to cover what I hadn't fit in my mouth. As I bobbed my head on his cock, he made more noises that encouraged me to do more.

"You sure you're new to this?" he asked. "If you are, you've clearly been studying some techniques." I couldn't tell him because my mouth was full, but I'd practiced sucking on my dildo at home, though the dildo never made noises like he did. I loved that something as small as my tongue could make such a big impact on him. I loved being subservient to him. I loved that he was making a mess of my mouth. Doing the real thing was hotter than any practice session I'd ever had alone.

His noises gave me confidence to try harder. I wanted him to know that despite my rocky start, I wanted this badly. Slowly but surely, I took more of him into my mouth, sticking my tongue out like I'd seen in videos as he went deeper into my mouth until my nose eventually touched his pelvis. I couldn't hold him there for more than a second, but I'd made it all the way down. All of my dildo practice and gag reflex training was paying off.

I backed his cock out of my throat to catch my breath, and was surprised at how much I needed to do that again. It had unlocked something inside of me, and I needed him back in my mouth. I decided to stop thinking about what I was doing, and just do what felt right. I was no longer a casual cock sucker; I was getting 'cock hungry', as the internet would say.

Without hesitation, I went down to the base of his cock again, this time holding it in my throat for a few seconds and wiggling my tongue at the base of his cock. From there, I went back to the tip, gave it a swirl like I had before, then took him all the way back down to the base. His cock was now completely wet and the strings of fluids from before were now running down my chin. This gave my blowjob a decidedly wet, slurpy noise which only made me more aroused.

Using my tongue to stroke the entirety of his cock made me feel so slutty that I now made a point to put my arms behind my back. If Michael was going to cum, he was going to cum using my mouth only.

All while this was going on, Michael was enjoying this more than I ever had enjoyed a blowjob. He groaned each time I went down on his cock, but soon I noticed that I was groaning too. And it was only now that I noticed that I was fully erect.

For the next few minutes, I maintained my steady pace of tip to base then tip again, all the while moaning as much as Michael did. The pressure of his cock on the back of my throat made me so unbelievably aroused that I didn't want it to end.

Michael suddenly let out an open-throated moan. "Oh god," he said. "I'm gonna cum..."

When he said that, something came over me. Up until now, I was enjoying the taste of his cock and how much pleasure I was giving him, but now I wanted more. I wanted to be at his mercy. I put his hand on the back of my head, and went as deep as I could. Without hesitation, Michael gently wove his fingers into the hair on the back of my head and took over moving my head up and down his shaft, jerking himself off with my throat.

As his breath became shorter, I felt his cock swell. It got bigger and bigger until he held my head down and erupted with all his might. I tried to relax and let it go down my throat, but this was something that no amount of dildo practice could prepare me for.

After his pumps of cum filled my mouth and throat, Michael pulled my head off his cock and I coughed a little as I struggled to handle his cum. It flowed out of my mouth and down my chin as the reality of what I'd done set in.

"I refuse to believe you've never done that before," he joked with his eyes half-open, leaning back on the sofa. "You look like a natural with my cum on your face." I fell backward into a sitting position on the floor, once again trembling and using my shaking hands to wipe my chin clean. I blinked like I'd had a factory reset as the cum dribbled off my chin and onto my chest. "Lemme get you a towel."

I was too shell-shocked to move until he returned. While wiping the cum off my face, questions began to filter into my mind. How did I go from a hesitant but eager straight man to an absolute blow queen so quickly? I felt like I'd been possessed, and was now trying to make sense of what my alter ego had done.

But as I sat there, I couldn't ignore that I was still harder than I'd ever been before. I felt like such a good slut letting him make a mess of me, but I still wanted more. I needed him to fuck me.

Again, Micheal read my expression, and beat me to the punch. "We can go again," Michael added. "But I'll need a few minutes to recover. That'll give us time to warm you up."

I had no idea what he meant by warming me up; I was so horny I could hardly think clearly. What else needed to be done?

Michael pulled me up onto the sofa towards him. When I climbed up, I found a seat on his lap and began to make out with him.

I was no longer acting consciously, but instead mimicking every girl who'd ever done this to me; I put both of my hands behind his head on the sofa, and kissed him as hard as I could and started grinding on him. I wanted to make it clear that I wanted him to fuck me as soon as he was ready.

He broke off from kissing me to suggest that we move to the bed. It was only a few feet away, but in the distance between, we both quickly shed our remaining articles of clothing. I sat on the bed and bit my lip while waiting for him to get his jeans off. When we were both naked, he pushed me onto the bed and I fell back like a rag doll, blissed out at what had transpired and anxiously anticipating what was going to happen next.

I told Micheal there was a condom as well as a few packets of lube on the nightstand. He grabbed them and placed them down by my hips. "While I'm reloading", he sneered, "let's make sure you're ready for me." He opened one the packets of lube and covered his fingers in it. He started slowly with one finger softly rubbing my anus, gradually entering me. I immediately let out a soft moan. I'd never been touched in this way before, but one knuckle sent a shiver through my body. Soon, he had his whole finger inside of me and began to explore.

"How does that feel?" he asked with a smirk. My face said more than I could possible have strung together, and he knew I was putty in his hands. I wanted him to break me, make me his, and change my world in a way that couldn't be undone. When he found my prostate, I let out a moan that's only made by someone who was completely at the mercy of another man; it was the moan of a whore.

The moaning only became louder when one finger beget another with the intent of preparing me for his arrival. As he fingered me, I ached to know what his cock would feel like in its place. I was hungry, with every part of my body screaming for him to fuck me.

I was now breathing like I'd run 5K, and I could hardly take it anymore. I reached down to feel his once again erect cock, and stroked him. "Fuck me." I said between panting breaths. "I can't wait to feel your cock."

But still his fingers slowly went in then out; the entire time, Michael softly kissing me and chuckling to himself. I would have hit him for being so smug if I weren't dying for his cock inside of me. He loomed over me while working his fingers in and out of me, and asked "Are you sure you want me inside of you? You need to convince me."

I laughed in a mix of disbelief and despair. I'd just sucked his cock to Kingdom Come then asked him to fuck me. What else does he want?

I did the only thing my blood-starved brain could think of: "Please," I whined. "Please fuck me. If you don't, I feel like I might burst. I want to cum, and I want you to make me do it. I promise I'll enjoy it. Empty your balls into me again, please."

I hated myself for begging. I hated that I said 'please' and begged to be violated. I hate that I had to plead with a man to take control, even though he knew he could take it whenever he wanted. At the same time, it's hard to be bashful when you can still taste another man's semen and you're begging for his cock.

Mercifully, I'd convinced him. He unwrapped and donned the condom, unrolling it down the length of his still-damp cock. I looked up at him and made eye contact. "Now please fuck me?"

Michael now climbed forward, placing his hand firmly in the middle of my chest, and pushed me back into the bed. He then raised my legs in a way that made me feel defenseless. I was totally open to him as he aligned himself with my anus.

As he slowly pushed in, he leaned forward and held me down using his bodyweight. At first, he just put the tip in and waited. I tried my best to relax, pushing down like I'd done with my toys so many times before. However, playing it cool wasn't something I was able to do right now. Instead, I wrapped my legs around his waist, and tried to pull him in, but he resisted. "We're going to go slow."

He took the tip of his cock out of me, then reinserted it for a bit, giggling when I resumed begging him to "please do it already" out of anguish. After what felt like an eternity, he began to force himself deeper into my trembling body. Each time that he thrust into me, he'd go just a tiny bit further than he had before which was welcome but the pace was still agonizing. I felt like I was going to burst.

At first, I only made light and soft noises when he thrust into me (aside from my begging), but when he bottomed out inside of me, I let out a relieved sigh and thanked him.

But just because he was all the way in didn't mean that he was ready to make me scream. No, in fact that opposite. He seemed to be enjoying my torment, slowly fucking me from base to tip, with me cursing him and moaning at the same time. When he went slowly like this, I could feel every ridge, every feature on his cock as it passed my prostate. By this point, my cock was helplessly leaking like a broken faucet.

When I began to tremble from the built-up tension, Michael picked up the tempo still using the full length of his cock. As he did, my frustration turned to praise and my moans became less pained but louder.

With the faster fucking came the pleasure I so desperately wanted. The dull ache from before was replaced with a slow-burning pleasure centered at the bottom of my pelvis that slowly rose through my body. As it reached my chest, it'd steal my breath for a second before cresting over me like a wave on a calm shore. I closed my eyes and rode the tides of Michael's rhythm, all the while moaning and encouraging him to fuck me. I only became quiet when the waves crested.

At first, the waves from my prostate were small and manageable. I could crest one, and then wait for the next one to build. These waves felt like that light stomach feeling you get when reaching the top of a rollercoaster incline. But after a few minutes of methodically giving me the entirety of his sexual muster, the waves started coming in quicker succession. No sooner was I over one wave when the next one approached. More to the point, the crests and troughs were getting higher and lower respectively, and what was manageable calm waves quickly became rough seas inside of me.

Micheal noticed that my ascent into near-delirium and picked up speed more. Much to my dismay, I could still feel every feature of his cock but now more frequently. What was a pleasurable experience was quickly becoming too much, and my moans of ecstasy became more frenzied, at least when I could manage to form noises at all.

Finally, I felt what seemed like a tidal wave within my stomach brewing. My eyes shot open, and I could no longer catch my breath. Instead of moaning, I was now hyperventilating and pleading. "Wait, please," I said as I tried to catch my breath. "It's -- too much -- I feel like -- oh god -- please no --"

Without breaking his stride, Michael grabbed my hands from around his neck and held them on the bed above my head with both of his hands. I couldn't stop what he was about to do to me if I wanted to, though if he did, I would have immediately begged him to continue.

In the space of six thrusts, I arched my back and let out six progressively louder moans. Each thrust pushed me closer to an edge I'd never been over before. At the same time, Micheal's cock once again swelled inside of me. His strokes became shorter, partially because of my clenching, but also as he drove himself to a climax of his own.

With the last thrust, I felt Michael's cock pulse and throb, which only added to the feeling. When the full wave landed on me, it was like touching a live wire: my body tensed, amplifying the sensation of Michael's orgasm inside me; semen shot from my cock, seemingly beyond my control; I let out one long, loud moan that the next room over surely heard; and my body violently shook, save for my arms which were firmly held above my head.

After it passed, I laid on the bed whimpering, my breath quivering from the ride. Michael released my hands from above my head, and they limply fell to my sides while I short-circuited from the aftershocks. I think Micheal said something, but I couldn't hear him over the sensations he'd given me. I just remember shaking my head and stammering as he pulled out and laid down next to me. He ran his fingernails up my thigh, and a trail of shocks followed, again making me shiver and whimper.

I don't know how much time passed. I could barely tell you my name at the time, let alone what was going on around me. But when I came to, Michael was lying next to me with a grin on his face, and pulled me into his chest. He called me his 'baby boy', and stroked my hair.