Help, I Fucked My Best Friend’s Son

Him: Hello

Me: Hi. Is this Rick?

Him: Yes it is, who's this?

Me: Ricky Rick Dees! It's uncle Joe. Your dad's friend. Remember me?

Him. Uncle Joe, Blackeye Joe?

Me: Dear god, you still remember that? Hahahahaha

Him: I'll always remember that hahahaha

Him. How you doing? What a pleasant surprise?

doing very good actually. Business is good at the moment. You? How are you?

Him: I'm doing great. What a surprise! A pleasant surprise

Me: I was with your folks last weekend. I got your number from your mum, I told her I'm coming down here for a couple of days for work. Let's hook up I buy you a couple of beers now that you're old enough to drink hahaha

Him: I will so outdrink you but I'll make sure you don't get into fights this time hahaha

Me: I learnt my lesson, these days I'm a lover not a fighter hahaha

Him: Hahaha. I'd really love to meet you. Tell me where you are and we can make a plan for the evening.

We work out details for an evening drink at a pub close to the hotel I'm staying at.

As you can see, it started off very innocently. I had absolutely no intention of sleeping with this kid. I know, he's a man now. He's 28, working as a graduate trainee for some big telecoms company. Sharp kid, done very well for himself and really progressing well in his career.

I'm very proud of him.

I've known him since he was 3 days old. His father is one of my best friends. We've known each since we were teenagers. We grew up in the same hood, took our first steps into manhood together, started our careers around the same time. We'd partied together, drunk copious amounts of alcohol together, fucked girls, swapped girls. Gone on holiday together, invested together. Basically, we grew up together.

I was delighted when Rick was born. Dan, my friend, settled with the first good woman that he met, very good choice, still together 30 years later.

I, on the other hand, stayed single for a while. A long while. I had my childhood trauma and it took me a long time to get over it. I eventually had a kid from a woman I was dating but I never settled down. I figured something in me was broken, I feared being like my old man, actually.. I was petrified of being like my father and by the time I got over that fear, it was too late. I am now a middle aged white man and the opportunity to get a decent woman and start a family has passed me. I take care of my kid but I've resigned myself to the fact that I'll probably never have a close relationship with her. I regret that. Sometimes when I can't sleep at night I reminisce on what could have been, what kind of life I'd have led, if if if, just if... sigh.

I'm in my early 50s. Decent-looking, dark haired white man, increasingly getting white flecks, just about 6 feet, in good shape, I gym and jog regularly. I've worked hard in the last ten years to get into better shape after I had a health scare in my early 40s. Cut down on the booze, junk food and all and I started taking my health seriously.

I live with my 2 dogs, make a decent living as an IT consultant. Paid off my mortgage and my car.

I've accepted there's always gonna be multiple paths I'd have taken but I took one path and now finally, at the ripe old age of 52, I'm at peace with the man I've become and the path that I took.

As for women and dating. I've taken a break from all that and it's so fucking liberating. Getting laid is not a problem at all. When you're a decent looking, well maintained, well groomed single guy in your 50s with a bit of money and driving a decent car... women aren't the problem. Young, not so young, middle aged.... doesn't matter.

They all want something though. Either money or I'm a project to fix or status or worst of all, my freedom.

Naa, I'll pass.

I have a client who's been bugging me to come down to this town, there's a project they want to do and they need a consultant to work out the details. To be honest, 'they' was actually him, my contact. A mid level manager is a guy I was a few years ahead of in college. He's a few years younger than me with 3 kids, one going to college in a couple of years. He's seen the writing on the wall, we all have. AI is gonna have our jobs in a few years time, we are living on borrowed time.

So what he's trying to do is get approval for this estimated 5 year project, get one of his golf buddies onto the project in exchange for a few envelopes under the table. I've seen it before multiple times. Corporate corruption is something no one talks about but everyone engages in. I tend to steer away from such projects, they can get very messy when they blow up.

I hate corporate life

But man, I'm scared.

Winter is coming.

I don't know how this AI thing is gonna roll but I know there's a storm coming and I'm trying to make as much money as I can before the storm finally arrives so fuck my feelings.

Here I am in this bum-fuck boring medium-sized city that I particularly don't care for writing a report that tells the client exactly what he wants to hear in the hope that this will bring me some work for the next couple of years.

At least I'm gonna catch up with Ricky later.

The day went along pretty well. My client actually had a strong case for his project. I could see a way to write a report that would validate his project and get me some extra work in the process.

Nice.

I'm done by 4.00pm. Head over to the hotel, take a shower and then a nap. I'm meeting Ricky at 8.00pm so I'm not stressed for time. 7.00pm I'm up, a quick shower, freshen up, polo shirt and jeans and boots.

The modern informal independent consultant uniform!

8.00pm sharp and I'm having my first cold beer of the day at the pub as I wait for Ricky.

He's gay and I know he's gay. He came out to his family like ten years ago. His folks handled it well, Ricky's a great kid, well mannered, warm heart. That's all that matters, the rest are details.

I've kinda dabbled on the gay side myself... ok, more than dabbled but who's counting?

I haven't seen Ricky in a while, last time was five years ago at his college graduation party so I was surprised when I saw someone looking like him walk into the busy pub looking very very trim and dapper. He was simply dressed in a white shirt and jeans but it's the way they fit him and the way he carried himself revealed a confidence in himself I'd never seen before. The gangly, lovable, energetic kid had grown into a handsome young man, with a model's blemishless face, a light tan, and a lean build. His slightly long hair gave him an exotic, almost Mediterranean look.

He smiled warmly when he saw me waving at him from the bar. I stood up to shake his hand and he surprised me with a bear hug.

We started chatting excitedly as I ordered more drinks. And more drinks. And more drinks. I was heading out the next day on the mid-morning flight so I wasn't worried about work or meetings. The client wanted me to stay an extra couple of days at his expense but I wasn't having it.

So I'm getting hammered and so is he. We've ordered food, he's telling me about work and what he's doing and how he's adjusting to corporate life in these turbulent times. I'm telling him about what I'm doing, my fears about the future and how I'm taking on any project that comes my way.

I don't ask if he's in a relationship, he doesn't volunteer.

Perfect.

I'm playing the role of the uncle, the older man advising him on how to handle corporate life and its incessant bullshit, giving my opinion about the economy, politics, finances as he educates me on the challenges he's facing, his generation is facing. I can sense the uncertainty in his voice, how does one prepare for this new exciting but uncertain future?

I really fear for his generation. I'm glad I'm not young and starting out again.

He's talking to me about his work and his generation and money and trying to figure out the next few years, where to settle, the property market, career progression.

Anyway we went at it for hours. Some point during the evening we got a few shots. Now, I've eased off drinking as I've gotten older but I can still handle my drink.

Or so I thought.

I'm trying to be the hip uncle, show him that I still got it, bad mistake.

The kid is knocking off those shits and ordering more all while mocking and cajoling me, challenging me. He's telling me he's punishing me for all those pranks I used to pull on him when he was a kid!

"The future is now, old man", he says with a hearty laugh.

I felt my age at the end of the night as we, no, I, staggered out of the bar with him holding me up.

I could barely walk but I had a great evening. There's something about getting older and having so much pent up knowledge and painful life lessons you want to pass on to someone else. Sigh, anyway I want this fine young man not to make the same mistakes I did. I want him to succeed beyond what his father and I could ever have become. He listens attentively as I speak, almost eagerly. It feels good to have someone young to talk to and advice, the youth think they know it all, just like I once did.

He insisted on taking me to my hotel room, very necessary for him coz I was bloody high. It was a struggle getting the hotel room card in the slot, figuring out how the damn switch worked, giggling like two idiots on the hallway, me leaning on him as he patiently waited for my drunk ass to coordinate itself and open the door.

Finally, we are in the room and he's carried me to an armchair and plunked me down. I pull off my shoes and socks, already dozing on the seat.

"Let me take a pee and then I'm off," he says.

I mumble in agreement and then I nod off.

I was woken up by an incredibly warm delicious not so unfamiliar sensation, coming from my nether regions.

I opened my eyes to see the warm mouth of a familiar head slowly coaxing my cock to full attention. It took a few seconds for my alcohol-fogged brain to adjust to the unfamiliar room and settings. And to realize my pants including my briefs were lying on the floor and Ricky was on his knees giving me this incredible blowjob.

And then I realized what was happening.

"Jesus Christ! No no no... Ricky, this is wrong. We can't do this," I begged as I shot up and started pushing him away.

"Please please please. Just let me. Relax," he said. "No one will ever know."

"Please Ricky. I'm old enough to be your father. Your father is my best friend!."

He stopped and looked up at me. There was something different about him, his aura. The confidence was still there but now there was something else, the hint of a smirk maybe?

God he's so hot.

His blonde hair falling all over his face, his signature move to push them back in a manner that was both seductive and feminine.

And dangerous.

He's seducing me. I'm being seduced by my best friend's son.

FUCK!!

I wanted to kiss him so bad. He's so lovely. That's the word, not even handsome. He's lovely. A lovely man who's giving me a five-star blowjob in my hotel room in this irrelevant city where nobody knows us.

And he wants me. When's the last time somebody actually wanted me and didn't want something in return?

"What am I doing?" I'm thinking to myself as he continued with the blowjob.

He was slow and deliberate.

I want to touch his hair, his head. I want to shove his face down on my cock. I want to choke him with my cock.

But I'm the elder here, the sage.

Sages don't fuck their fucking students for fucks sake!

FUCK!

I'm watching the expression on his face. It's so hot to see him working on my cock. My resistance is fading, that warm mouth, that tongue, they're all doing tricks to me, they're like stirring something in my soul, waking up a deeply hidden demon.

And then he looks up to me as he blows me. He has a cute-twisted-playful kinda look on his face.

Resistance is futile gentleman!

Let the die be cast.

My 8 inch cock is now fully erect, angrily straining, veins bulging.

He takes my acceptance for granted. He knew all along I'd never be able to resist his charms.

He smiles at me and warms my heart.

He's so fucking gorgeous.

He seems fascinated by my cock. He knows just what to do as he sucks me. Slowly and slowly, I felt like a fly unable to untangle itself from the spider's web as the spider closed in for the final kill.

It happened when he suddenly swallowed me whole.

I've been sucked well before, I know how it feels to get a good cock sucker working on you. Ricky wasn't good, he was more than an expert.

He was a craftsman.

Sucking dick was his craft,

He was a I-am-good-because-I-love-it craftsman. He had me squirming in my seat, switching positions, twisting and turning as he showed me his full oral skills.

At some point he's looking directly at me as he swallows my cock. We're staring at each other knowing fully well, we've crossed a line we shouldn't have crossed. And we don't care.

He's lavishing my balls with saliva, sucking them, twirling them in his mouth. Spitting on my cock and then wanking me and then sucking my soul out of me.

He likes looking at me when he's doing all this. And then closing his eyes and sighing, like he's in heaven.

He loves doing this. He's always wanted to do this. He's gonna do it.

"I'm gonna cum," I yell.

He's done it.

And then he took it a step further. He was challenging me to see the man he'd become, the man he now was.

We'd spent a whole evening talking about everything and anything but his sexuality.

Now here he was demonstrating to me his sexuality.

He's continuing to suck my cock despite my warning. He's sucking the soul out of my cock and it explodes finally and he jerks out, the hot cum splashes on his face and he's rubbing it all over his face while tasting it, savouring it.

Cum and saliva dripping down his face and onto his shirt.

His eyes closed like in a trance.

Like he's finally fulfilled a dream.

He opens his eyes and looks at me and I know, he's gonna devour me if he gets the chance, if I can give him the chance. He's staring at me, daring me to say anything as my cum drips down his face and his tongue snakes out to catch drops.

This is better than any porn I've ever seen and I've petabytes of porn.

The young lion finally coming off age and challenging the older lion.

What is he challenging me for? Acceptance? My soul? My dick?

I don't care coz that's the most amazing blowjob I've had in such a long time. Not those half hearted three licks of tongue I get from horny middle aged women

He's promising me an experience.

He's laying down a challenge!

I'm half drunk and stunned and lost in my thoughts as he stands up. He doesn't speak a word. I watch as he walks to the tiny hotel room shower, moments later I hear the water running.

I can see him from the glazed window as he washes his face and cleans up his shirt.

He comes back with a wet wash cloth and silently cleans me up.

We don't say a word until he's almost finished.

"Don't say anything," he says. "I wanted this for a long long time."

"You're such an attractive man," he says simply.

I'm touched.

It's been such a long long time since anybody paid me a compliment. As a middle-aged man, you get used to being almost anonymous.

It's nice to be complimented, to feel wanted again.

He notices the effect his words have had on me and he smiles.

"You're a very handsome man, Uncle Joe."

I don't respond. I'm almost blushing. I'm acting like a smitten maiden. Is this how women feel when they're smitten?

I don't know what to say anymore. I'm overwhelmed. He smiles and continues cleaning me up.

He finishes, goes back to the washroom, rinses the cloth and hangs it. Comes out of the washroom and he looks at me.

I look fucking ridiculous.

Half naked, drunk, groggy, satiated... horny.

Still wearing socks!

He comes to me and gives me a peck on the forehead... same thing I used to do to him many years ago when he was a kid.

"Thanks for everything," he says. "I really enjoyed it and I really had a great time. I'll talk to you in the morning."

"Ok," is all I can mumble back as he looks at me, smiles and then walks out of the room.

I'm left stunned. Disbelieving. Dishevelled. Wondering whether I'm dreaming, whether this just happened.

What just happened?

Oh god, what will I tell Mary (Ricky's mum) next time I meet her? And I'm supposed to go to their place for a birthday party next weekend after what I've done?

I'm so mixed up in my feelings. I honestly enjoyed it. A lot. There's something about his attitude, the look on his face as my cock spewed cum, that hungry hedonistic feral look. I'd missed it. So easy to get that look when your fucking a man. So easy to just stop thinking about everything but just being feral, being horny and hedonistic.

Being a slut, bringing out a slut.

I'm lost in my thoughts for a while. I don't move. I'm remembering all the things I love about man-to-man sex. It's been such a long fucking time.

But then the conflict checks in. It's Ricky. I've known him since he was a baby, carried him, played with him, brought him birthday presents.

What the fuck I'm I doing? I can't really be thinking of him in that way? I'm so ashamed of myself.

And then the phone chimes in. A message.

Him: Hi. Look, I'm really sorry for what I've done. I'm feeling so guilty now and I'm really sorry if I took advantage of you."

Him: I'll never mention this to anyone, you have my word.

Him: And maybe if you want to continue, I'm in room 202. Gonna be there till 6 in the morning. It's ok if you don't come.

Pause

Him: I love you Uncle Blackeye Joe :-)

I stare at the phone, processing the messages. Wondering how to reply, what to reply. And then common sense gets a grip on me.

This isn't right. I'm the older mature one here.

Just as I'm about to write a message apologizing and promising never to do this again... fate intervenes.

Another message pops. This time it's an image. I open it and gasp.

It's him.

Butt naked.

In a lewd position, legs spread wide showing me his shaved crotch. A delicious semi-erect cock, at least 7 inches, in full display. He's lying on his back, legs spread open, spreading his thighs and showing me his hole, his puckered brown hole, winking invitingly at me.

Like a moth to a flame drawn by the fire.

That's not even the shocking part.

He's wearing black stocking, a black thong. He's wearing make-up. Hair has been rearranged, fluffed out.

He's transitioned to something else. He's not a him anymore.

It gets worse.

I know him. Her.

The femboy.

She's on one of those adult content creation sites.

Astleyicious.

Yes. I know her. Very well.

It gets even worse!

I'm her biggest fan.

I've spent over a thousand dollars on her. Tips, gifts, subscriptions. You name it.

I'm her fucking biggest fan.

Does she know? No one knows. No one knows that when I'm at home on the few days I'm not chasing up some client, I'm wanking to some of the hottest fem-boys and trans women on the internet.

She's my favorite.

I've chatted to her a number of times. Telling her my deepest darkest most depraved fantasies as she encourages me to fuck myself harder with that dildo that's deep in my ass.

We've video called each other. That cost me 200 dollars!

I'm in my home, it's dark. I'm huffing at the poppers like a man in heat as the heat in stuck-on dildo sends waves of pleasure coursing through me. I'm dressed like a two-bit whore. Gaudy makeup, wig, g-string. I've got another plastic cock in my mouth, sucking it as she tells me to suck it harder, fucking faggot.

Oh the thing's I've told her. The depraved fantasies I've told her.

Oh my fucking god!

She's sent me videos of her sucking cocks. She's sent me audio notes of her moans as she gets fucked up her ass by a fan. Her grunts as she fucks some nameless pathetic grunt and then comes all over his face and makes him lap it up.

I love it.

I never see her. Always wearing a mask or in the shadows.

I've never seen her face. Till now.

I can't be found out though. This would be so embarrassing. What would I tell my friends? How? She can't know it's me. Does she know it's me? No, this is not possible.

Or is it? It can't be possible. Please god no!

Another message chimes in.

Her: I know you want me. Blackeyejonn right? I'm waiting for you. I'm your biggest fan you know ????

She knows!

To be continued...