I Can't Believe I Waited so Long

For days, I was wrecked with guilt, struggling to comprehend that I'd slept with a man, and worse, that I'd enjoyed it. I'd always considered myself straight, and in many ways, I still see myself that way. But I couldn't ignore the reality of what had happened, no matter how much I tried to justify it or push it aside.

For days I questioned everything. Whether I was watching TV, out with friends, or playing football, my mind was consumed. I'd catch myself looking at men, checking them out, while reassuring myself that I didn't find any of them attractive, whereas on the flip side I still found women attractive.

None of this stopped me from going back to see Pete the next week. Or the week after that. Or the one after that and each time I did, I enjoyed the sex a little more and felt the guilt a little less. I went back again and again, once, twice, sometimes three times a week and had a great time every time.

It was my dirty little secret, something only me and Pete knew about which suited me perfectly. I did worry from time to time that spending so much time together that he might eventually want more than being fuck buddies but he never brought it up.

Although I was always the bottom, I did ask Pete if he'd ever let me top him. I was curious, about how it might feel to take control and how it would feel to penetrate him. All I got in response was a very firm "I'm top only".

At first, I wasn't sure how to feel about it, but the more I thought about it, the more I realised I was okay with it. The truth is, I really enjoy being the bottom, there's something liberating about just letting go and letting him take control.

Everything was going great, until just after Christmas. It was a Sunday afternoon, and I'd just woken up from a nap. I'd stayed over at Pete's the night before, and I'd come home feeling exhausted, needing to catch up on some much-needed sleep.

I rolled over in bed and grabbed my phone off my bedside table and saw a message from Pete. I was hoping that he was going to invite me to go back to his that night so I couldn't wait to open it.

But as I opened the message, my stomach dropped.

"Sorry to do this to you, Simon, but I can't see you anymore. I've just got back together with my ex. I had fun. Go get as much cock as you can handle."

It felt like a kick in the guts. I stared at the screen, reading the words over and over. My excitement for another round with Pete replaced by a wave of anger, disappointment, and something else I couldn't quite name.

Desperate to save face I quickly type "No worries. Good luck to the pair of you," and pressed send before I could second-guess myself.

Minutes later, another message came through from Pete, simply saying, "Thanks, mate." Both his messages stung, but it wasn't an immediate, sharp pain and as time passed, I soon found that it was a slow burn. At first, I tried to shrug it off, telling myself it didn't matter, that it wasn't serious and that I'd find another dick to fuck. But as the hours dragged on and the days rolled by Pete's rejection only hurt more.

I tried to distract myself by throwing myself into work and hanging out with friends, but after a week of checking my phone, hoping Pete had messaged me, something snapped inside me. I do a complete about turn. I threw out all my toys and dove headfirst back into women.

For weeks, I reached out to every single woman I knew. Every casual hookup, every fuck buddy, every person who had ever shown even the faintest interest in me, I contacted them all. I messaged exes I was still on speaking terms with, and when that didn't work, I swallowed my pride and begged my friends to set me up on blind dates.

But it didn't stop there. Desperation drove me to download every dating app I could think of. I set up profiles and began swiping with reckless abandon. If I found someone even remotely attractive, even just barely, I swiped right or hit "like" without any hesitation.

My scatter gun approach worked. For weeks on end, I was constantly out on dates. Dinner here, drinks there, and quite a few times, the nights ended in bed whether it was mine or someone else's it didn't matter. It didn't matter if there wasn't any chemistry or even if I was interested or not, I just needed to fuck.

I was relentless, moving from one date to the next without a second thought, and it wasn't long before I'd burned through all my savings. So, I turned to my credit card, piling myself into debt with every fancy dinner, overpriced drinks and small gifts. I knew I was spiralling, but I didn't care.

That was until tonight where I find myself on my knees the floor in my living room behind my date for the evening, my hands on her hips pulling her back onto me as I pound her as hard as I can, panting, out of breath, sweat pissing down my face while desperately trying to finish off.

Only no matter how hard I try, I just can't get there. We've been at it for what feels like forever and she came ages ago, but I'm still nowhere close, not even the faintest hint of even a little a tingle. She's also started drying up and I'm beginning to chafe bad. Each thrust becoming more uncomfortable, but I keep going, stubbornly refusing to admit defeat.

In the back of my mind, the frustration builds. It's not her. I got lucky for a change, she's beautiful, sexy, big tits, big round ass, everything anyone could want, but there's something that's not quite right. Then, like a bolt of lightning, it hits me. It should be me, on my hands and knees, being pulled back onto a hard cock as it thrusts into me. The realisation punches me square in the gut, knocking the wind out of me.

Admitting defeat, I slow down and finally stop, resting my forehead against her back as I try to catch my breath.

"I'm sorry," I mumble.

I don't really know the reason I'm apologising for, not being able to cum, not being attracted to her, the whole damn situation. All I know is that I can't keep pretending anymore.

"Did you cum?" She asks in a confused tone.

"No sorry, I can't," I pant.

She shifts beneath me turning her head slightly to look back at me as he slides forward off my cock.

"It's okay," she says softly. "Maybe it's just an off night."

I nod mutely, forcing a tight-lipped smile as I collapse onto the sofa behind me. She adjusts her clothes, and smooths down her hair. The room goes quite as we both wait awkwardly for the other to speak first.

"I think I should go," she says finally.

"Yeah," I reply, barely above a whisper, while staring at the blank TV screen. "That's probably for the best."

From her tone, it's clear she knows I'm not truly interested. As she gathers her things, the tension is palpable, she move's quick, like she can't get out of here fast enough. Just as she finishes, she pauses for the briefest moment, her eyes flicking to me.

"I'll see you again," I say, although I don't really mean it, I don't even stand up.

"Yeah," is all I get in return and I can tell she's being just as insincere as me.

She quickly looks around as she checks she has everything, walks over to the door and leaves. As soon as she's gone, I bury my face in my hands. I sit back and allow my head to flop back onto the cushion as I look up at the ceiling.

I rub my face as I try to calm myself. I let out a big sigh and drop my head forward and as I do out of the corner of my eye something catches my attention. I turn my head and see me laptop sitting on my TV stand.

For a moment, I hesitate, but the pull is too strong. I stand up, walk over to the laptop before taking it and carrying it back to the sofa. Sitting down, I open the lid, and the screen immediately wakes up to my desktop. For a moment I pause, my fingers hovering inches from the keyboard as I feel my pulse quicken.

A few clicks and keystrokes later I've logged in and I'm instantly hit with message after message as bots flood the chat, but I don't care. As I start skimming through the chat, scanning for someone local I can't help but think about how I met Pete, and although the chat is filled with spam it gives me hope that if I did it once I could do it again.

I feel alive again, it's as if a switch has been flicked back on inside my head. I have no doubt that I'm doing the right thing my only problem now is finding someone.

I sift through the chatroom, ignoring the endless stream of spam. My eyes skimming over usernames, searching any sign that tells me they're close by. Every so often, a profile catches my attention but within a few messages I quickly realise that their location isn't the one I was thinking it was.

As the minutes tick by, my frustration begins to creep in. I knew it wasn't going to be easy, but the rush of the moment keeps me glued to the screen.

At least it does for an hour or so when after admitting defeat I close down the webpage. Slightly irritated, I turn my attention to preparing myself for what's to come. I go to my favourite toy website and begin filling the basket. I start by replacing all the toy's I'd thrown out and then turned my attention to something new. Then, I click on the "New Arrivals" tab, and there it is, a beast of a toy, 8.5 inches long and 4.1 inches wide. It's intimidating, almost comical in size, but something about it speaks to me. I know I'll never manage to take the whole thing, but that isn't the point. I know If I use it regularly, I'll be ready for anything and anyone.

Without a second thought, I add it to my basket and proceed to checkout. I glance at the total, wincing at how much I'm about to spend before clicking pay. Once again, I've splurged money I don't really have, but for now, I push the guilt aside as I know this time its money well spent.

Sadly, I have to wait until Tuesday for my package to arrive. I sit at my desk staring out of my window as I look out for the courier with my parcel. I'm meant to be working, but I'm too excited. I repeatedly check the courier website for updates to the delivery time. Then I get a window 12:34 to 13:34, for an hour I wait like a coiled spring, ready to jump up to answer the door when he arrives.

13:34 comes and goes with no parcel. Then ten minutes late I see a van round the corner. It's unmarked, no logos or writing to indicate that it's the courier but I just know. I watch as it pulls up outside my house and I leap out of my chair and rush to the front door. As I open it, the courier steps onto my garden path, balancing my parcel in one hand and his phone in the other. Without a word, he places the box on the step with a dull thud, snaps a photo for proof of delivery, and walks away without so much as a glance in my direction.

I barely notice his lack of acknowledgment as all my attention is on the package. I pick it up and am immediately surprised by its weight, its way heavier than I'd ever expected. My heart pounds as I shut the door behind me and hurry into the living room, setting the box on the coffee table. My hands tremble as I tear through the packaging, ripping into the cardboard like a man possessed.

When I finally pull the plug out of the box, I'm momentarily stunned. Even though I knew its dimensions, seeing it in person is a completely different experience. It looks massive, far bigger than I thought it was and what surprises me more is the weight of it.

For a moment, I just stare at it, examining every inch of it, my excitement mingling with a twinge of nervousness. This isn't just a toy, it's a challenge. Just the tip alone is as thick as my next biggest toy.

I can't help but smile as I place it down, but I can't wait any longer. I rush to my laptop, clock off for lunch before grabbing the plug and rushing into the kitchen to wash it.

Minutes later I'm back in my living room, standing over the plug on the floor, smeared in lube ready for insertion. I reach back and rub some lube into my hole before slipping in a finger, then a second, which is quickly followed by a third. I know I'm rushing but I can barely wait.

With a deep breath I squat down and feel the firm tip press against me. I immediately feel resistance as I begin to stretch as very little of the plug if any squeezes up into me. It hurts but I carefully manage the pain as I try to find the balance between pleasure and pain while continuing to stretch myself.

I don't stop and over the next half hour I slowly edge the tip inside me as I stroke my hard cock. I love the feeling of being stretched out, and I already know this is the furthest I've ever been stretched. Then, suddenly, I feel it, a tingle that starts deep within my groin and spreads through my entire body as my orgasm quickly builds then explodes. The feeling is intense, almost overwhelmingly so, my hole spasms squeezing against the plug as it tries to close, but it can't go anywhere which heightens the intensity even more as I push myself down even harder which causes my whole body to tremble.

After a while the euphoria begins to fade and I prepare to lift off the plug, but before I do press my fingers against my hole to mark just how much of it, I've managed to take. I lift myself up and climb down onto my knees to inspect. As I do, I can't believe how little I'd managed to do. After more than half an hour of effort, I've only managed to take in about three-quarters of an inch. That said even at that shallow depth, its size is incredible, so much so that I can't even wrap my fingers around it.

Feeling somewhat satisfied and a sense of accomplishment, I quickly tidy up before returning to my desk to finish my shift.

The rest of the workday passes in a blur. All I can think about is the plug, and as soon as my shift is over, I'm back on it again. Then the next day, and the day after that. By Friday, although I haven't made much progress down its length, I notice a notable difference. My hole feels softer, more pliable, and much more accepting.

As far as I'm concerned, I'm ready for the real thing and when work ends, I head straight to the shower to prepare for the evening. Once out I head into my bedroom open my laptop, and log into the chatroom.

I make my presence known immediately, flying my flag high for everyone to see, while trying to beat out the bots. As I do I scan the usernames. But after going through the list multiple times and drawing a blank in the chat, my initial excitement starts to wane.

"There has to be a better way," I say to myself.

I open a new tab leaving the chatroom open and start searching for gay hook-ups. I'm aware of the apps I can use, but not being out I figured that I'm more likely to be outed if I us them and I'm not ready for that.

Website after website flashes across my screen as I search for the best way to hook up with guys discreetly. One by one, I create account after account, creating profiles for others to see. Then I stumble upon a site under the term "Cottaging." Curious, I click on it, quickly sign up, set a distance filter, and hit search.

The site's layout is basic, just rows of pictures with usernames above them. Scrolling through the profiles, I realise that if I'm going to be taken seriously, I need to upload a picture of my own. Without hesitation, I stand up, rush to the bathroom, and snap a naked frontal shot of myself from the neck down, and then one from the rear. I send them over to my laptop and within minutes I've uploaded them to my profile.

Thirty-six profiles appear, all within a 5-10 mile radius of me, with ages ranging from eighteen to seventy-two, I know I could've selected those closer to home but decide against it.

Excited I meticulously work my way through every profile, sending each one a simple message: "Hi [username], I'm new and looking for some fun."

It takes a bit of time, but when I'm done, I eagerly check my inbox. It's Friday night, I figure there has to be someone online looking for some fun. But to my disappointment, there's nothing. Not a single reply. I'd hoped for at least one reply, but my inbox is barren.

Frustrated but determined, I move on to the next website. Over the next four hours, I sign up for well over a dozen websites and forums, messaging dozens of guys, swiping and liking as I try to get something started. Each time however, the result is the same, nothing.

By the end of the night, I'm completely demoralised. I close my laptop, not even bothering to try anything else. Feeling defeated, I head to bed.

The next day, I wake up just after lunchtime and immediately begin checking all my accounts for replies. Website after website, account after account, I draw a blank. I know it's still early days, but I can't believe how little activity there's been.

Then, I log into the "Cottaging" website and notice a small "2" in the top right corner next to the inbox. My heart skips a beat as I quickly click on it. Inside, there's only one message thread, from someone named Charlie59. I open it to find two messages:

"Hey, how are you?" and "Are you free tonight?"

I pause for a second, as I notice that he wasn't one of the original guys I'd messaged. Curious, I click on his profile and begin scrolling through his pictures. I immediately realise why I'd skipped over him before. He's older than I'd considered, heavier too, and has a very hairy, prominent potbelly that's seemingly out of proportion with the rest of his body. He has the stereotypical "middle aged dad bod," and at first glance, I'm not interested.

As I click through further, I come across the pictures of his cock. It's not particularly long, probably six, maybe six and a half inches and it juts straight out from a thick tangle of pubic hair, though his potbelly still sticks out further.

However, it's the girth, that grabs my attention. It's almost shockingly thick, to the point where it makes his cock look shorter than it is, stout and almost stubby, just like him.

The more I stare at it, the more I want it. I just can't take my eyes off it. There's something about its size and shape that draws me in and I find myself seriously contemplating replying to him.

I flick back to find a face picture of him. There's nothing bad about him, he's just an average-looking middle aged, balding man. Although there's nothing particularly appealing about him either, but something about his thick cock draws me in.

I know I'm not attracted to him not even a little, but the thought of having that cock in my ass still tempts me. I consider holding off, after all, he's just the first response. But something inside keeps pulling me back to the pictures of his cock, which has me rock hard.

"Fuck it!" I exclaim as I click reply. "I could always not go."

I quickly type, "Hi, yeah, I'm free. Can you accom?"

I hit send, lean back and wait. I quickly decide that since it's not a live chatroom, it's probably best to make use of the time and get myself ready. Around half hour later I sit myself back down in front of the website and refresh the page and the number "4" appears next to the inbox icon. My pulse quickens. I can't click it fast enough, my fingers almost fumbling as I open his messages.

"Yes, I can accom."

"My wife is out for the evening so we will have plenty of time."

"You have to be discreet."

"Can you do that?"

I don't hesitate. I type a simple, "Of course," and hit send.

I click send before making my way to the kitchen for a drink. When I get back, I see another two messages. The first is his address which was a little closer than I expected and the second is "come after six and go to the back door."

I reply with "Okay, see you then," before closing down the page.

Feeling the need to distract myself, I head to the kitchen for a drink. When I return, two new messages are waiting for me. The first is his address, which is surprisingly closer than I expected. The second reads, "Come after six and go to the back door."

I reply with, "Okay, see you then," and log out, closing the laptop.