Alex and Jack

All characters are over 18 years old.

***

Anal sex.

My favorite kind of porn actually.

I get it from being a teenager.

My brother and his friends all older than me were very sexually active and anal was one of the things that I was seeing.

The first was my brother Adam with Penny this girl he was seeing a lot and he convinced to have anal sex with him.

I'd watch them the typical too curious brother from the basement window. Long having learned to keep quiet so I wouldn't get caught. It was too good not to watch honestly.

Penny hissed and moaned as Adam stuffed his cock into Penny's ass and she sounded like it hurt her.

And with all the whimpery sounds of them buttfucking it got louder and louder the more she was getting used to it.

"Fuuuuuuuuck that feels so fucking big Adam!"

Which got louder and dirtier worded turning into demands for him to fuck her ass.

And she wasn't the only girl he turned out like that.

I mean pussy is great although it's kind of boring.

Though I think that girl on top is way hotter than missionary and doggy style.

It's always stuck with me.

But not just that.

It was seeing Adam with Jack Tyler.

They were called Apple Jacks.

Jack was part of the football team's offensive line and Adam was the quarterback and they made a good team.

And I saw my brother when I took up my peeking position on his knees sucking Jack's cock which was just honestly huge.

And yeah blowjobs are hot especially if the guy getting blown has a big amazing dick.

Jack had that with a great big cock that must have been ten inches and thick too with great big pulsing veins.

And Adam was sucking it and loving it even gagging on it for a while but happily doing so.

Until they decide to switch ends and Adam climbed onto the basement sofa with his butt up in the air and Jack took some vaseline and fingered Adams ass and i heard Adam hiss and gasp like he made Penny.

Then he moaned and whimpered as Jack's big dick pushed into his ass.

"Fuck, fuck, fuck Jack...so fucking big."

"Oh Drew baby your ass is so tight."

Drew was Adams middle name.

"Oh...deeper Jack, Deeper."

I will never forget the sight of Adam's ass getting filled up and stretched wide by Jacks massive cock.

When Jack bottomed out Adam whined loudly in a sweet high pitch.

"Ohhhhhh...! Good, good, so fucking good!"

Then I watched Jack fuck my brother and my brother cry and whine and beg for it. "Aaaaah so big, so hard! Oh god Jack don't stop, harder, harder baby please harder!"

Jacks cock literally was making Adam's asshole flex in and out as his size pushed and pulled his body.

I watched that cock fucking my brother's ass for what must have been ten minutes.

Adam just started whining and crying out just no words all vocal.

And without having his cock touched he came crying out as his dick fired off in these amazing looking thick bursts of ropey cum.

And wailed and shivered.

And I watched Adam get fucked and fucked into more bliss?

And he had more than one orgasm really close together?

I watched them together a lot and Jack was always the top and he was the only guy Adam was with.

But the sex stuck with me too.

I never busted Adam or Jack for their getting together and as far as I know Adam's married to Sherry and they're happy and stuff.

And I'm older now just getting done my first year out of graduating college and I've only been with girls but while I've had anal sex with a few of them. I've never had it myself, never had anything inside of me and the temptation is finally hitting it's peak.

I've never been interested in guys either.

But I've never been able to get Jack out of the back of my mind either.

And just as I moved and got a good job at the provincial liquor store which is a unionized government job I ran into Jack.

He was looking in my store and I recognized him right way.

Still hot, still ripped and big all over like one of those really cut TV wrestlers in even better shape I think and he was looking for something.

"Hey Jack, I didn't know you were living here now?"

"Alex! Hey how's it going?"

"Good, good just moved into town last month and working here now."

"Cool, good job."

"Great job, all those part times back home at our store and my degree definitely helped."

"I'm glad, I'm a carpenter now."

"Not a pro football player?"

He laughed which actually was deep and sexy.

"No, that died about 3rd year when I realized I wasn't good enough to go pro and I didn't think that going to the other smaller leagues was really a good idea so I took a few other classes to finish my arts degree and then went for broke and got a student loan and went into trade school."

"Work out well?"

"Getting by."

"Married?"

"No, not married."

"Girlfriend?"

"No one steady."

We share eyes contact and it lingers.

I ask quieter. "Boyfriend?"

"No, no one since Drew."

"Doing anything tonight?" My mouth was so dry.

He stared at me and did a slow take that was checking me out and he shook his head but he was smiling as he did. "Not really, when do you get off?"

"Four."

"So how about I come over at eight?"

I smile and take out my card and jot my address down on it. "Eight would be perfect."

Jack left buying a nice bottle of whisky and I finished work and headed from there right to the drug store and bought a couple kinds of lube and a couple boxes of condoms and a bottle of Nair and lotion getting a definite look from the girl at the cash but hey whatever I'm new in town.

People can think whatever they want.

I went from there to the grocery store and bought some good bread and some fixings for making good sandwiches then went to the XXX rated porn store and I bought a cleaning kit and extras and a tip for lube application and then home.

I made a drink and put things away and organized the food for making food later and after my third drink I headed to the bathroom and used the toilet and went through the process of getting really cleaned out inside and I used the lube to get pre-lubed inside.

I felt weird doing that but it also got me horny and hard as hell.

I left it, let it subside and just add to the sexual energy.

Then a shower and me getting rid of my body hair. I shave and use lotion on my skin nothing like girly but nothing teen guy styled either. I like using shea butter when I want to pamper myself and I use one of the light Nivea aftershaves too.

It's not a femmy thing I don't think it's just I've never had the fantasy of me being hairy when I've thought about being with the fantasy men I've been with.

I get dressed.

That was just odd because what do I wear for this sort of thing?

I go with this old work shirt I had a brown flannel number I bought once that was too big by accident but I keep around because it's comfy in the winter with sweats at home.

I wear that with my best black boxer briefs and have it barely buttoned.

Kinda gay, kinda maybe?

I think I look good though.

I mean I've never done this with another guy before.

I was just getting drinks made and I'm going with one of my best whisky bottles and really good mixes and ice when Jack pulls in with a nice SUV and he gets out with a fancy looking box?

I open the door just as he gets there and we share a smile and I let him in and he looks good.

Old faded jeans clean but thinned with age showing off his bulge and the lump that is shifted to one side. A tight black t-shirt and over that a really classic old leather jacket.

My mouth went dry again and I think my insides twitched.

I might just might actually be really actually attracted to Jack.

He passes me the box and it's really nice. It's like a nice slotted box made of wood and stained and definitely one of those fancy things and there's a fresh cup towel over that. The box is heavy too.

Fuck it.

I lean over while holding it and kiss Jack on the lips.

He was surprised but he kissed me back.

Aside from we were both guys it was a hell of a first kiss. Shared, not too soft but it wasn't hard and forced but it was ernest and it went over and over like three times.

"Wow...Alex, that was nice."

"Well we are here and being us and together right? And you brought this gift too. I thought it deserved a kiss."

His smile was pretty great.

Genuine.

He took off his boots which were nice too and he followed me inside and I set the box on the dining/breakfast nook table and looked under the table cloth and it was really nice. A paper bagged loaf of rustic bread and some nice cheeses and there were some jars of pickled things that looked homemade and with it a nice looking bottle of wine and what looked like a really nice looking set of cutting boards.

"This is easily the coolest thing I've ever gotten as a gift."

Again that smile.

"Well you're welcome. Most people I know don't have cutting boards or cheese boards and they make good gifts."

I smile back. "You want a drink?"

"I'd love one."

"Whisky?"

"Sure."

"How do you like it?"

"Surprise me you're literally the professional."

I head over and I make two drinks each with just ice and the best whisky I have and as I'm doing that Jack took off his jacket and he comes over and his fingers trace my sides through the shirt I'm half wearing and when I look at him he's the one that kisses me.

Finger and thumb turning my head and this time i'm definitely the one getting kissed.

It's as good, no better than the last one.

Of course I kiss him back.

And it goes further from there to me touching him, and feeling that thick hard muscles and even down to his crotch and rub his hardening cock.

He does the same and like holy heck that feels amazing and erotic.

Not dirty, not kinky but purely erotic.

I pass him the drink and we don't do the whisky justice as we both down it and go right back to kissing, touching, feeling each other and I walk us backwards down the hall to my bedroom until I get to the bed and sit down and unbuckle his belt and pull down his jeans and briefs freeing that huge cock of his.

He was mostly hard and he was uncut and it was huge, scary, thrilling and actually beautiful.

I stroked Jack's cock as I found the condoms and I took a magnum and dressed him then took him into my mouth. A thick saliva coating lick of my lips to lube them and I pursed them slightly and pushed his cock through my lips like he was penetrating my mouth.

It's just something I came up with there and then but he groans.

"Oh Alex, wow...that feels just so good."

That helps.

I start sucking and it's a big cock, with a big head but it's not impossible either and I concentrate a lot about getting him in deep at times but in pushing my tongue up and flats so the soft flesh caresses the underside of his cock and I really use my lips, to get that seal, be soft yet clinging, to be pussy like.

Jack's gasping. "Oh Alex, wow, oh...god...oh you are so good at this, oh suck me baby, suck me, please...nnn...fuck...take me all the way..."

All the times I watch Adam with Jake I never seen that, never Jack getting off from getting head. I can get why too. Even doing this is pretty challenging. I'm not sure everyone could do this especially if they where trying throat stuff. As it is I've my head tilted back to help me do the thing with pressing my tongue thing which is taking stress from my jaw and letting my neck support more.

I like the fact this might be me being better at this than my brother.

I like the fact Jack's talking dirty but not calling me a fag or a cocksucker. I'm not into hard swearing. It's not sexy to me.

All of it's enough to get me worked up enough to finish the job and get Jack to cum as I take him over the edge.

I stroke him off and feel the hot rushing spurts of him cumming and filling the condom.

"That's a lot of cum."

Jack groans. "It's been a while..."

I pull the condom off and toss it in the trash. "Well we should fix that." I say as I stroke his big cock and already I can feel him recovering. It's not fast but it's steady. And I'm enjoying this, massaging it, running my hands over the skin.

It's really erotic, hypnotic even and soon Jack's rock hard again.

I stand and kiss him again and he kisses me back and I put another condom and the lube in his hands then drop the shirt I was wearing to the floor and slip out of my underwear then I slide onto my bed and get on all fours with my face down and my butt up.

I'm soon not disappointed as Jack's hands are on my hips and he's lubing me more that I am already and he slips a finger inside.

I moan...it went in easy and it actually felt good.

Jack knows what he's doing too as his finger massages my insides and moves in and out then he's rimming my entrance with his finger making my squirm with how delicious and sensitive he's making me feel.

"Oh Jack, that's really good, that's so nice, you're really good at this."

"Well you do have a really nice ass Alex."

I gasp laugh as another finger is added.

"I'm kind of vain, I work out and even have a butt workout."

"It shows, it's a really sexy ass."

"Well it's...oh...it's definitely ready for you Jack."

"It's be my pleasure."

He starts and he starts with kissing the small of my back, making his way up to my neck as he gets into place and he rubs himself against my hole.

"Ready?"

I smile. "I've been thinking about you for a long time Jack, want you so very, very much."

"That's almost romantic Alex."

"Good."

Jack pushed into me and his very large head stretches me and stretches me but it's not horrible or even painful. I want this and between the fingering and being really well lube he's sinking into my ass wonderfully.

It's huge.

It's filling me in ways my imagination never thought of and stretching me deeper inside than ever.

It makes me shiver in a good way.

"Ooooh...oh...oh...of fuck yes Jack, that's huge, that's so huge...god that feels so fucking good, so deep."

"You're so tight Alex, so tight and sweet, you feel so amazing around my cock."

"Fuck me Jack, please fuck me."

He pulls out and sinks back in and I moan. I can't help it it's that massive he's just making me need to be vocal.

I moan with each stroke especially as he sinks in and i'm losing the grip on my composure as it feels far better than I could imagine, better than every fantasy and every dream I've ever had.

I can't be quiet as he fucks me and I get my brother loving this. I get why he was so into this and Jack.

Oh...oh...oh...the pleasure builds as Jack hits my pleasure bump inside of me and the feeling is amazing. There's no real way to describe getting your prostate rubbed the right way but it's amazing and that along with being filled and fucked so sublimely.

The pleasure builds like I'm going to cum but it's sort of deeper than when I have regular sex and since I'm not used to it when the edge comes and I go past and over it I cum hard spurting the most potent orgasm of my life.

And it shakes my body to the core as my body kegels to squirt out my cum but finds Jacks cock inside of me and my insides mold around his cock.

"Oh god! Oh god! Oh god Jack!"

"That's it, that's it Alex cum, cum for me."

As soon as my muscles relax he's moving again almost taking me there again but it's more, better the feelings are fucking perfect...just so fucking perfect as Jack keeps fucking me and they don't get any less as he takes me to this plateau where my cock is leaking this steady stream of pre-cum and he's edging me.

It feels like the most beautiful forever.

This is the best sex I've ever had, this is better than and ass I've been in or any pussy I've been in it's better than every blowjob.

He rocks in and out through me until I cum again and it's so powerful despite all the edging pleasure I was in.

I only spurted a little but this time my body's reaction gets Jack to cum.

Then it's his weight on me as he's buried deep and holding me and we're both breathing.

"Stay the night Jack?" I ask.

"I'd love to Alex."

We pull apart and make our way into the bed properly and under the sheets and end up cuddling and kissing face to face until our sexcapades have caught up with us and we snuggle into sleep.