Seeking

Hey guys! I wanted to post something a little different. This one is a stand-alone entry that recounts me losing my virginity. I changed the names and some minor details for obvious reasons, but other than that, everything you'll read actually happened just as I wrote it. It's a retelling, but also a bit retrospective which you'll see as you read. Let me know what you guys think in the comments.

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May 2015

Today wasn't like most other days.

I woke up horny this morning. Now, that's not something out of the ordinary- being young and closeted will do that to you. But it just felt different this time.

We were finishing up our Junior Year of college and three of my five roommates had already left for home. I was one of the few of us five who didn't live an hour away, so it made sense for them to want to leave whenever they could. I, on the other hand, had to kill a day before I was boarding a plane, headed home for the summer.

I woke up to a mostly empty apartment. My two actual roommates had both left the day before and so there weren't any sounds of my one roommate's alarm blaring, or the sound of a wooden bed frame creaking by the other. Yeah, living in a bedroom with two other guys wasn't the best idea, but we're college kids trying to rent in possibly the most expensive city in the country, so we didn't have many options. Elsewhere in the small apartment was another bedroom with two housemates, bringing us to a total of five. Let's just say any sort of privacy I could get in this cramped place was a blessing.

My hand almost immediately went for my dick. Sometimes it feels like it has a mind of its own- and today was no exception. It's like it knew it didn't have to hide underneath the covers or be paranoid at the slightest sound of a door knob turning. It was unhinged, and spoiler alert, so was I.

I pulled out my laptop and a set of earphones and opened one of my favorite tube sites. It hosted a comical amount of ads and pop-ups, and maybe a dozen or so viruses that would leave my laptop unusable down the road, but it was my vice. I scrolled through, seeing tiles of videos that had been uploaded since the last time I got to watch porn. With classes and a lack of time to myself, that must have been weeks at this point, and so everything I saw was new. I went through the usual sites- seeing every porn studio update on the screen and cherry picking the ones I wanted to jerk off too. Most ended up being pretty meh, but there were a few that looked hot. I loaded them up and gave it a few minutes.

Between my legs, my dick throbbed at the mere thought of cumming. Most jerk off sessions had to be either quick or inconspicuous, and so it was nice to be able to jerk with the cool air coming from my bedside widow hitting my skin- no sheet covering it, no laptop strategically placed on top or me oriented in a specific way so I could watch the door. It was free, and after the stress of finals week, it needed relief.

I spat into my fingers and rubbed it on the head of my dick, working it underneath my foreskin. This felt too fucking good as I rubbed my wet finger tips all over my cockhead that seemed to be covered in a million soft nerve endings, all sending waves of pleasure through my body. I gripped onto my shaft and felt that prominent vein on the side as I started to jerk myself off. I'd become quite efficient, able to crank out a load in a matter of minutes but I was in no rush. It was still mid-morning and, aside from packing, I didn't have anything else to do today. In several hours, I'd likely get a text from my other friends who hadn't left yet to meet up and get some food, but I hoped that by then, I'd be able to get at least a couple loads out.

I jerked myself, feeling my skin roll back over the head until it was fully exposed. I started watching one of the vids I'd queued up- it must have been Sean Cody or Corbin Fisher, one of the standard sites that boasted hot, athletic dudes having sex. Hindsight would tell me that most of the scenes weren't that good, but I didn't know better at the time. Eventually, I got bored of the monotony and moved on to the next video. It was a good change of pace, but still, I found myself rather disappointed. At that point, I'd been pent up for so long that I didn't want to cum to just anything. The porn wasn't doing it and maybe it was my horniness taking over, but I felt more daring.

I walked over naked towards the shared closet that was now two-thirds empty and reached into one of the bins. Underneath pairs of boxers and socks, I unearthed a travel case that looked rather inconspicuous. I'd gotten it on one of my trips back home and had emptied it of the toothbrush and other toiletries it held. I unzipped it, revealing a small flesh colored dildo that managed to fit inside. It was perfect and managed to go unnoticed for the several months I kept it stashed away. Today it was gonna be used and my cock twitched in anticipation as I pulled it out, along with a small bottle of lube I'd kept hidden.

If you thought I didn't have any privacy to jerk off, then using a fucking sex toy was an even rarer occurance. I remember buying it out of desperation, but it hasn't seen much use since. Still, It seemed to give me more stimulation than my two hands could manage. I fished out a clean towel and sat back in bed, spreading my legs so I had perfect access to my ass. I liberally coated both it and the toy in lube and pressed play, watching- though mostly listening- as I slowly pushed the tip past my pucker. I was still very new to this, but I had taken the toy a couple times. After a bit of coaxing, I was able to get it in without alerting the last roommate in this place. I felt my eyes roll back as I settled into the bed, with the suctioned end stopped by the mattress, leaving the toy inside me as I stroked.

I grinded a bit, feeling the head move inside me. This had me leaking even more and I caught myself constantly fingering at that wet tip for more and more of that sweet precum to taste. It felt great for a while and the porn did wonders to keep me hard, but eventually I got tired of it. The toy kept slipping out and there was only so much I could do with my hands to keep it inside while also leaving me stimulated. I caught myself groaning at how much effort all this took- how I was begging for an extra set of hands, a toy that could fuck me on its own and something I could taste that wasn't hard plastic.

I knew what I really wanted- but that was a step I hadn't taken before. It was a line I had yet to cross and I didn't know if I had it in me.

Part of me knew that I should just make myself cum and feel these rash decisions leave my body like the horniness would. But the other part- the one that had been sexually repressed for the past seven or eight years knew that I wouldn't get another opportunity like this. I wouldn't have a mostly empty apartment or nothing to do today or a flight back home should something not work out.

If I wanted to do something, it had to be today. And as I slipped the toy out of me and felt my hole twitching in anticipation, I knew I was ready.

But being closeted had its limitations. Even though I was thousands of miles from home and in arguably the most tolerant city in the world, I still clung onto my straight facade for dear life. I was only twenty, so gay bars were out of the question. I never quite understood the concept of meeting someone organically- I mean part of that meant jumping over the hurdle of asking random guys if they were even interested in guys.

And then there was Grindr.

A few months ago, I let my curiosity take over and I downloaded the app just to see what it was like. I kept everything blank for the most part, wanting only to lurk around and see what this side of life was like. The tiles of men offered a lot of options- a bunch out of my league and still some that were hard to judge off pictures alone. Almost immediately into scrolling, I found a classmate on there- some random gay kid who I'd talked to a few times in class. That one classmate became two and then that became a couple and soon enough, I was hyper-paranoid, thinking that I was exposed. Every person on the spectrum who wanted to satisfy their urges just like me would see me. They'd know my face. They'd know why I was on that app, and what I was looking for. The mere thought of all those eyes on me left me anxious to the point where I deleted it and decided that I wasn't going to risk it.

I needed to find another way.

I'm dating myself by saying that I went on Craigslist and clicked through the channels to find the one I had in mind- "men seeking men." By now, that's become a remnant of the past along with Vine and Tumblr porn, but back then, it seemed like a legitimate way to meet guys in secret. Even writing this all these years later feels so weird- especially with all the countless gay hook up apps and the advent of gay twitter. You guys don't know how easy you have it.

I scrolled through a few posts and soon understood what I was looking at. You look through a couple and it's apparent which ones you should steer clear of. Some guys were overly sketchy and most of the wording in the posts didn't appeal to me whatsoever. I clearly wasn't going to find a needle in a haystack this way. So I needed to make my own post.

I grabbed my phone and stripped a bit, feeling my cock grow even harder, the more naked I became. If I wanted to entice someone, I needed to have pictures. I ended up taking a couple that looked pretty good- some shots of my body, hard cock and plump ass. I'd never done this before, and so the fear of self-consciousness set in. But I needed to get over that. And today was proving to have more than a couple stars aligning for me to finally go through with what I set out to do.

With the pictures uploaded, all I needed now was a description. I figured honesty was the best route to take, since any guy with some experience would see that I was bullshitting. I kept it simple, giving my stats which were average at best. I decided to throw in my Pacific Island ethnicity- to both entice anyone who found that to be of interest, and to ward off any racists as well. Then it became a list of likes and dislikes. Kissing, sucking dick, and getting fucked were all yes's, while pain, scat, blood and anything else my naive porn brain could think of were hard no's. I was sure to highlight a few things that would hopefully catch some dudes' eye- mainly the use of the word "inexperienced", "virgin" and the genius one I came up with, "eager." All of which were true and would hopefully attract someone who was both excited at that, but understanding at the same time.

I clicked post and immediately felt a wave of anxiety. I refreshed the page several times that first minute, hoping to see a response, but it was too soon. Eagerness turned to worry and worry turned to regret. By then, it had only been a few minutes and my brain just assumed that hundreds of guys wereonline and available on a Saturday morning- all of whom wanted to fuck me, but in reality I was overthinking the whole thing.

I scrolled on my phone for a bit, hoping to distract myself but my still hard dick wasn't making it easy. After several minutes, I checked back and was pleased to see at least a couple people had responded. The first few I read were hard passes. The guys just seemed too off for me to want to make anything happen with them. The next one seemed hopeful and we traded a few e-mails back and forth with him seeming interested, but eventually it fizzled and I gave up. I was about to delete the post entirely when I got one e-mail.

This one seemed different- it didn't reek of desperation like the others, which was ironic considering my position. It was a simple message saying his name and that he was older and more experienced. He liked that I was a virgin and asked more about what I had done up to that point- which was honestly next to nothing with someone else. I did mention that I had a toy I played with and that seemed to further pique his interest. Then he sent me a reply with two pictures. The first was a rather generic shot off him with sunglasses. There wasn't much I could make out apart from a broad frame and some salt and pepper hair. Still, he didn't look like a serial killer- based on my own interpretation of what serial killers looked like- so he seemed to pass that test.

The next picture was of his dick and that's really where things started to take shape. It was big- bigger than what I had expected and enough to make my mouth start to water at the sight of it. I had next to no experience whatsoever, so I hadn't even seen a dick outside of porn. But this one exceeded my expectations and honestly, it's what sealed the deal for me. After an eager reply from me, he gave me his phone number so we could chat a bit more freely.

I'd learn that his name was Tim and that he was older, living in a district of the city just across the park. He too was free for the rest of the day and we made plans to meet in the next half hour.

Tim sent a follow up text, saying "Make sure to bring your toy with you." leaving me blushing and even hornier.

Once I set my phone down, panic sunk in. "Fuck" I said to myself. It was real and it was happening and apart from me being a total flake, I was going to go through with it. I hopped out of bed and stuck the dildo back into its inconspicuous case and shoved that into a backpack. I frantically looked through my closet, checking through everything as I tried to find the perfect thing to wear. Sure, I wouldn't be closed for long, but I didn't want to show up in any university attire or clothes that, for whatever reason, would make this take a sharp turn. I settled on a simple t-shirt and sweater, along with a pair of jeans and shoes. All that left was a deep shower and some further preparation.

I got dressed again and slung a clean towel over my shoulder as I left my bedroom and walked to the bathroom. I stepped out into the hallway and saw my last remaining roommate, Jordan, sitting at his desk in the living room. He waved over to me with his large headphones still intact and I gave him the standard nod. Jordan was undoubtedly the roommate I was least closest too, so that was the extent of our interaction.

I went ahead to the bathroom and started prepping. I may be a virgin in all senses of the word, but I wasn't a novice in what to do. Still, the pang of anxiety hit me as I started to shower. My brain was filled with countless scenarios in which things went south- none of which I want to get in much detail about. But that was a part of the process, I felt, and the most I could do was get myself as clean and prepared as I could. I stepped out of the shower and dried off- reminded yet again of my dick that just wouldn't go down.

After getting dressed, I did a final round of everything. I slung the backpack over my shoulders, grinning at the fact that the only thing inside was a sex toy. I checked my phone and sure enough, there was a bus on the way which would drop me to the stop closest to Tim's place. And with that, I took a deep breath and left my room. I waved to Jordan who was still mindlessly on his computer. I don't even think he noticed me leave, and that was for good measure. The short walk to the bus stop was needed, with the cool air hitting my sweater as most of the worries of earlier started to dissipate.

I don't think anyone is prepared for their first time- well not actually. You prepare as much as you can with what you know, and end up going in there blind. That's what I was doing.

The bus ride to the other side of the park was a bit comical. I decided to take one of the last open seats at the back, and when I did, I felt the case pressing against my back. It reminded me of where I was going and what I was about to do, and part of me started to wonder if the faceless strangers on the bus could figure me out. I got off before I was answered.

Next came the waiting game. I stood around the stop, seeing the few cars pass by as I tried to look as normal as possible. Tim had texted just before I got off that he'd leave his house soon, and I found myself looking at every car that drove up, wondering if it was him. The few cars that passed had a couple guys that clearly weren't the man in the pictures I'd seen, and the possibility that I was being catfished started to set in. But then an older model classic car in bright red came right up and stopped in front of me.

"Danny?" He asked, in a deep voice.

"Yeah, you're Tim?" I asked, trying to gain confidence.

He nodded and said "Hop In" as I opened the door and got into a car with a complete stranger.

As he drove, I took the opportunity to examine him as nonchalantly as I could. He indeed matched the pictures- with the same salt and pepper hair that I remembered. It was clear he was decades older than me, yet he still held onto that handsome face and an expression that actually calmed some of my nerves.

Tim weaved us through the smaller neighborhood streets, up along the hills into houses that looked a lot nicer than our shitty apartment complex. We chit-chatted on the way there, and I was thankful to not have to go through a round of twenty questions- most of which would likely psych me out. Tim wasn't trying to know me like a friend, and I held onto the idea that we'd never get to that point. We both were here for one thing, and I wanted to stick to that.

Minutes later we drove up to a bungalow just on the hill with a decent view towards the ocean. I didn't know what Tim did for a living, but it must have been good enough to be able to afford a place like this. He welcomed me inside and placed his keys and wallet on the counter in the kitchen. I followed him timidly- not really sure what to do at this point.

As if he knew, he came up and placed his hands on my shoulders. "Have you ever kissed anyone?" He asked quietly.

I shook my head, managing a simple "no" as he nodded. That question often left me feeling shame- like I'd gone through life having not checked off a list of things people my age should have done already like getting your driver's license or drinking alcohol for the first time. But Tim didn't look at me like a late bloomer who'd left a trail of missed opportunities. Instead, he brought his lips to me and the minute we touched, it felt like he was uncapping a bottle of soda that had been shaken for the past couple years with so much built up pressure that it would explode once it was given the chance. I felt my lips latch onto his, followed by my arms that gripped against his muscled biceps. It felt good to feel someone- to taste his lips and to have his curious tongue sneaking its way into my mouth.

Mentally, I tried to remove any lingering worries as he kissed. But physically, I was a mess of sensations. Between his lips on mine and his tongue pressing against my mouth- to the feeling on his strong hands circling around my waist- it was a lot.

And yet I wanted more.

"You're pretty good at that" he said. Whether or not he was sincere didn't matter to me. I blushed anyway and leaned in for more.

Eventually Tim pulled away and I couldn't help but pout as he did. "Let's go to the bedroom." He told me as he led me through the rest of his house.

I walked closely behind him like a lost puppy until we got to his bedroom. It was simple, with no character whatsoever- no pictures on the walls, no knick knacks, nothing to suggest that he was an actual person beyond a top I'd found on the internet.

Tim sat on the large bed and I walked over to him, noticing the porn that he had playing on the oversized TV behind me. I didn't pay much attention to it, other than the fact that it was a scene of jailbait twinks. He must have liked the whole older-younger scene, and the near twenty five years that separated us made that even more apparent.