So, there I was, 20, freshly dumped by a cheating bitch of a woman, drinking away my problems with friends before a drunken walk home to my mother's house in the cold January night. A normal Thursday, basically.

As always, we gradually went our separate ways, but unlike normal, when I was the first home, my destination was my dad's house; I had to crash there that night due to losing one of my keys earlier that day. So I ended up walking a bit further, and was accompanied by my friend who lived near my dad's; we'll call him Liam.

Liam and I had been friends since the early days of high school. He was never much fun to drink with, always far too overbearing and responsible, but occasionally he got a bit loose and wound up the worst of us all.

Following this, as expected, was him constantly attempting to have deep, emotional conversations, with repeated assertions about how good a friend I am, and all that typical sappiness.

The route to Liam's house was marked by a very steep, very long hill; now covered in ice due to the joys of January's weather. And so, I offered him to just crash at my house, and get a lift home the day after. We got back to mine and stuck on a horror film, one of our few shared interests, and lay down on my bed, each having plenty of space due to the, honestly, absurd width of the mattress.

We drank while we watched, of course, and continued our slurred conversation while we struggled to watch the movie. As men that age tend to, we eventually landed on the conversation of our sex lives.

Despite having just been dumped, I was pretty well known for my promiscuity, often looking to sleep with at least two new women every week. It was old news that I was doing just that, at least the week prior, I was 'resting' that week. Liam, however, was another manner.

He was always very reserved when it came to conversations about sex, and it was a pretty open secret he was a virgin. The reason for this, also an open secret, was that Liam was gay.

Now, he wasn't closeted; he had came out around six years prior. It seemed obvious, in a way, when one observed him after finding out, but he was far from a stereotype. He was tall, of average build, deep voice, usually clean-shaven, and was always still game to discuss women. His issue in losing his virginity, however, lay in three key problems:

1. Liam was fussy. He didn't want to just have sex with a stranger and move on - baffling to me, at the time, though I understand a little better now that I've found a good woman to settle down with.

2. Liam was awkward. He was very perceptive and a good person to talk to, once he got to know someone. But, to strangers, he just appeared to have a, frankly, cringeworthy sense of humour, and very little charisma.

3. Liam was a top. Anyone he got along with, and shared attraction with, always seemed to have absolutely no intention of being a bottom in any encounter they had. So, he had a few experiences with oral sex, but never got to the final step.

So, when Liam started discussing his own sex life, I grit my teeth, opened another beer, and decided that I would listen, attempt not to show discomfort, and get so drunk I wouldn't remember anything too vulgar he said.

He poured on-and-on about how frustrated he was, how he was sick of getting to know someone only to have things fall apart once their association heated up, and how he just wanted the chance to feel like everybody else.

I tried offering comfort, though I struggled with empathy already, and my being drunk made that worse; needless to say I didn't help much. We just kept drinking as he carried on, clearly getting more focused on his sexual frustration and less on his emotional frustration as he got drunker.

It was probably four beers later when I, in what had to be a sudden flight of insanity, wound up telling him, in mildly excruciating detail, about my one-night stand from around half a year prior. For those unfamiliar with my other tales: it was the one-night stand in which, I, in an attempt to bed the friend of another ex, discovered my intended target was a transgender woman. A gorgeous, intelligent, funny transgender woman, who fucked me in the ass, came over my back, fell asleep beside me, woke up, and then proceeded to, quite literally, fuck the cum out of me.

I was incredibly drunk, and still watching the movie, which had changed since our arrival, since our drinking had gone on for far longer than I meant. If I had paid attention, or been less drunk, I might have noticed the effect the story had on Liam. I can't say for sure, but my inclination is to say that he likely had his mouth a little agape, his eyes focused, and a tent forming under our blanket.

I went back to just watching the movie, though, as if I hadn't just revealed a huge secret, equal parts embarrassing and erotic. Liam started drinking more, at this point, I thought nothing of it.

As we started a third movie, he began speaking to me in a voice I hadn't hear that night. It was quieter, almost nervous, but deeper than usual, betraying somewhat of a confidence.

Liam asked me about the story I just told; I was unsurprised, I had kinda expected questions after dropping a bombshell like that. He wanted to know things I thought relatively innocuous. Did I enjoy it? Did I ever see her again? Would I ever try to do it again with another partner.

I tried to think through my answers clearly, aware that, despite his attempt at subtlety, Liam had edged a little closer to me. I explained that, yes I had enjoyed it, though I had thought, for most of the first round, that she was wearing a strap-on rather than that she had a cock. I explained that, for many reasons, I hadn't seen her again, nor did either of us attempt to contact one another. I explained that - nervously, and kind of shocked by my own honesty - I had tried to recreate the experience with other transgender women over the months since, but had had no luck and pretty much moved on, happy with it being a one-time thing.

I hoped that would let him down easy from any flights of fancy he was currently debating, but he was very drunk, and very confident.

He made an uncharacteristic remark which bordered on transphobic, attempting to say that sex with a man was equivalent. I rebuffed that with a soft but firm no, and he moved away with a sad smile and a nod. We resumed watching the movie in silence, slowly finishing these drinks.

I looked over to him at one point, and was struck by what I saw. Liam looked devastated. His eyes were visibly watery, his shoulders were slumped, his neck barely holding up his face to the TV.

I sighed quietly, and reached over to pat his shoulder in an attempt at comfort, offering a few words of apology. He sobbed when I did that and shook his head, then looked at me and tried to stammer out that I had no reason to apologise, even though his voice cracked.

In a rare move for me, I leaned forward and gave him a tentative hug, letting him put his face on my bare shoulder and cry himself out. Drunkenly, my own head slumped onto his shoulder, and we stayed like that for a few minutes. His breathing evened out, and he calmed a little, though I could still feel tears on my shoulder.

Now, women crying always broke me. I never felt the same sympathy for men. The kind of sympathy that led me to do anything to make their sadness stop. In this mix of care for one of my oldest friends, combined with a heavy dose of drunkenness, I felt that sympathy.

And so, I turned my head on his shoulder, and pressed a soft kiss to the side of his neck. Then another. And then another.

By the time I was up to a dozen, I had moved to kiss up behind Liam's ear, and sucked gently on his earlobe. He let out a soft moan - one unlike any I'd heard before - deep and, unfortunately, masculine. I had set myself down this path, though, and steeled myself to see it through.

My hand reached up to cup his head behind his other ear, and resumed my kissing his neck as I fell to my back, hoping he would take the hint and position himself over me. He did, thankfully, and I soon felt his surprisingly soft hands run over my chest and abs tentatively. I also felt the foreign, but unmistakable, feeling of a throbbing erection pressed against my, comparatively, flaccid cock.

I reached down, sensing I would have to guide this encounter for my inexperienced friend, and slid my thumbs into the waistband of the pyjama bottoms I had lent Liam for his stay, and attempted to push them down. He was absentmindedly uncooperative, though, and so I pushed him backwards to his knees. He gave me a confused and disappointed look, clearly thinking I had thought better of my plan, and so I moved quickly toward him, offering a reassuring smile, and tugged at his t-shirt.

He raised his arms, and let out a shiver of excitement, which I found amusing, as I pulled the shirt over his head. I stood and pulled him to his feet, and gracefully dodged his attempt to kiss me on the lips; I had no interest in that, which I did, and still do, consider far more intimate than sex itself. Instead, I planted soft kisses on his collarbone, and pushed his bottoms down before allowing him to step out of them.

I took a quick glance down to look at his erection, which was thankfully not too intimidating, though far from small; it was slightly bigger than that of my transgender partner, a little smaller than mine. I could have, but thankfully abstained from, breathed a sigh of relief as I was assured that I would be able to go through with this.

I pulled him with me as I lifted myself back onto the bed, resting on my knees, while Liam remained standing. I pushed my own bottoms off, revealing a nearly erect cock, and allowed my mind to race. I had never given a blowjob before, not to an actual cock anyway; an old fling had a strong dominant streak, and would often have me suck the strap-on she favoured wearing. Through that, I discovered I had a very bad, or very good in this situation, gag reflex. But could I do it when I would have to taste an actual cock, rather than rubber?

I went for boldness, and leaned forward on all fours, arching my back deliberately, and licked the already leaking tip of Liam's cock. He shuddered, and placed a hand on my head tentatively, the other on my shoulder blades.

I gave it a few licks, making sure the taste wasn't too unappealing, then carefully took the head into my mouth.

I wasn't sucking for long, and never got far past the head, though Liam's deep groans seemed to indicate he was enjoying my efforts. He lifted my head with a surprising force, for the first time showing me any strength, and let out a growl. With one hand on my shoulder, he guided me to turn around, leaving him standing at the foot of the bed, with me before him on all fours, suddenly feeling very exposed.

Before I was able to find out if Liam, in his inexperience and eagerness, had actually intended to force his way into my ass without a hint of preparation or lube, or even my permission to go bareback, I was already repeating 'no' in an exasperated but not angry tone.

I turned my head, and as gently as I could, gave him a reminder that, to all of my friend's amusement, I regularly gave myself an enema for hygienic purposes, followed by firm orders to walk to my drawers and open the bottom one, where he would find different bottles of lube. He withdrew the water-based one, and a condom, and made to sheathe himself. I gave another 'no', and another firm order to lube his fingers, and gently give me some preparation.

Liam did as told, sliding one extremely slicked finger into my ass, causing me to let out a silent gasp and smirk as I remembered how much I, to my chagrin, loved having my ass played with.

For the next few minutes, Liam fingered my ass and audibly moaned whenever I let my head flop back with a hiss or a gasp; he added his fingers at my instruction, eventually having three moving, if a little slowly and carefully, in and out of me with regular touches to my prostate.

When I reached back to touch his wrist, and gave a nod that he had done enough, I saw a smile light up his face. He stepped away to pull on the condom, which he coated in an absurd amount of lube. While he was occupied, I reached under myself to confirm that, in fact, I now bore a full erection.

Liam returned and I looked forward, arching my back to accentuate my ass again, and breathed deep. He assumed position, quickly placing his cock at my entrance, and pushed in a little bit roughly, though not enough for me to force a stoppage. He realised his over-eagerness, thankfully, and placed one hand on my hip and the other on my ass, and pushed in at a much more gentle pace.

Though I took pleasure from his initial entrance, I soon frowned as I noted a strange sensation; one that I had never felt during a pegging or during my prior time bottoming. It just didn't feel as good. Not really as smooth, with much more friction. It was really distracting, even given his quick finding my prostate.

His hips touched my ass eventually, and I was a little surprised to note how little noise he had made as he bottomed out. I remembered the last time I let a cock in my ass; she had moaned like she had found heaven. Liam was much quieter, his face, when I turned, still showed pleasure, but not what I expected.

I stopped him for a second and asked him to pull out gently, then reached back, ignoring his question of what was wrong and the concerned look on his face, pulling at the end of the condom until it slid off of his cock. I asked him to return to the lube drawer, and use, instead, the silicone based bottle. It was unsuitable for use with condoms, but worked far better for anal sex.

He pushed back in once lubed, again gently. This time he moaned, as, to my satisfaction, did I. It was official. Necessary as they often are; condoms suck.

Again, quicker this time, Liam bottomed out, and slowly withdrew for a shallow thrust. I was pleased, and showed it with an embarrassing and seemingly dramatised moan and jerk back of my head.

Liam's thrusts sped up, though still remained slow, clearly wanting to pace himself, and he moaned softly each time I unwittingly clenched around his cock.

He rocked back and forth like that for a minute or two, his hands grabbing my hips more strongly as time went on, before I grew aggravated.

This was supposed to be a quick fuck to help Liam feel better, to help him feel more like a typical guy, and to get him over his hangups. But more than that, I was enjoying myself when I hadn't expected to, and I wanted a good fucking.

I crawled forward as Liam pulled back, and he popped out of my ass. I looked back and tilted my head to tell him to follow. He did, and I felt the bed shift under his weight as I put my head down on my pillows, lowered my chest as much as I could, and lifted my ass. My hands gripped the sheets and, this time less tentatively, Liam claimed my ass with a guttural grunt.

I rocked my hips back now, as he fucked me hard. He let out deep moans in rhythm with his thrusts, though they seemed to get a little higher every time.

Content my idea was working, I allowed myself to get lost. I gripped at the sheets with white knuckles as I moaned. My cock bounced between my thighs and stomach every time he crashed his hips against my ass.

I felt myself leak, and smiled through my moans as I realised he was fucking my prostate every single time, and I would probably get to cum just from being fucked.

The gods of irony struck me down then, though, and he let out a bit of a yelp, roughly withdrew from my ass, and grunted with a whimper. I looked back to him, and saw that he had finished onto his hand, and his legs trembled as he sat down on the bed.

I sighed, not hiding my disappointment, and kneeled in front of him. I remember my next words very well, to this day, and in spite of my intoxication. I remember so well because of how troubled I was to say them.

"Look, mate: I don't need to clarify that this is a one-time only thing that we'll never ever discuss. You know that this never leaves this room. But I really want to cum, so do you wanna go again?"

He seemed a little shocked at the offer, but nodded all the same, clearly still hard and horny. I nodded, pleased, and lay flat on my stomach with my legs spread, and reached behind me to pull my asscheeks apart.

I heard a quick squelch as he added more lube, and then his hand pressed on my back to steady himself as he pushed himself back into my eager hole.

He moaned, though less intensely, especially compared to my own moan into the pillow. Both of Liam's hands propped him up on my shoulders, and he began deep but erratic strokes in and out of my ass.

My cock now sandwiched between my stomach and the bed, leaking heavily, I started getting a little desperate, and turned my face on the pillow to look at him out of the corner of my eye.

He was fucking me harder like I wanted, but not quite how I knew would make me cum. So I shrugged in my mind, and started to talk dirty. I honestly can't remember exactly what I said, or tried to say through whimpers as my friend drove his cock into my prostate, but he definitely got rougher, so I imagine I would have went along the lines of:

"You like fucking my tight ass?" "Yeah, fuck this ass." "I want you to make me your little slut." "I'm gonna cum on that cock." etc.

As I said, whatever I said worked, and Liam started growling and fucking my ass like he was just using a fleshlight.

I smiled and let out a constant string of shallow moans, then my eyes went wide, my hands gripped my asscheeks painfully, and I gasped. I felt my cum burst in one rope, and a few weak spurts, from my cock, and my stomach smeared it across the bed. Liam was still fucking me with abandon.

His inexperience meant he never realised I had already came. And it also meant he was totally unprepared for my ass to clench around him when I did. And that was how I, being drunkenly fucked in the ass by an equally drunk friend, got my first creampie.