Sweeter (And Deeper), The Second Time Around

In the world of on-line hook-ups and anonymous sex, second chances are somewhat of a rarity; especially if the first time around was not the rock-your-world experience promised.  Such is the case with my Mr. Pitbull – the vaguely Latin, very handsome, cue-ball bald hunk I wrote about back on 12/12/12, as part of Acquired Tastes XXIV: Bald Men.

It wasn’t that we didn’t get off; we did.  It wasn’t that our encounter lacked excitement; I was plenty excited.  It wasn’t that he wasn’t all he’d promised; he was all that and more.  In fact, maybe too much more.  His dick was so wide at the base that I struggled quite a bit with it.  It was that I left knowing that I had not brought my A-game.  After months and months and months of trying to get together, with me proclaiming just how highly skilled I was; the experience left me wanting.  I vowed that if I ever got another chance I would be better prepared to do justice to his incredible cock. 

That second chance did not appear to be coming any too soon.  I texted him after our encounter to thank him and tell him I’d be happy to accommodate any time.  I heard nothing.  After a week I deleted his number from my phone and thought, oh, well, at least I got a shot at it.  I then went through a two month period where being on-line, trolling for sex, simply did not appeal to me.  So it would prove unlikely that I would ever happen across him during that time period.

As the start date for my upcoming vacation approached, I felt myself gearing up for some hot encounters; in the mood, so to speak.  So, after work last Wednesday, while updating my profiles with new pics and a little more graphic information (typically I keep my profiles pretty upbeat and a tad generic), I open up Manhunt, which I had not been on in eons, and low and behold, there is an email from Mr. Pitbull.  Turns out he hit me up a week earlier.  When this happens I always respond with:  ‘Sorry I missed you.  Please hit me up again.’  So, I do, and then go about the business of updating my profile.  About a minute later, much to my surprise and delight, Mr. Pitbull emails me back.  He wants my ass.  Am I available?

You know the answer to that.

He was hosting and wanted to know how long it would take me to get there.  I told him to send me the address again and that once I was cleaned up and ready, it would take me less than twenty minutes.  I didn’t wait for a reply.  I had to feed my dogs, get them outside to do their business, douche my ass, shave my ass, gargle and brush.  As I await his answer, I get started on the dog’s food; a more complex task than one might think. 

I have three dogs, each with a specific special need and a special diet.  I have their food prep down to a science.  In all, it takes me about ten minutes start to finish, including microwave time.  I get their bowls set down in front of them and check back.  No reply and I’m thinking – oh, he was just testing the waters – he’s not really serious about hooking up.  No problem.  Other fish, blah, blah.  Dogs finish eating and I take them out to do their business.   When I come back in, there is a reply from him, only it’s not what I’d hoped.  His ‘roomie’ has come home.  Can I host?

I rarely do. 

The dogs.  They get super upset when strangers are in the house.  But… I am thinking, hey, this is something I really want, so I have to be willing to make it happen.  I tell him sure thing, as long as he’s willing to drive down the alley, park in my driveway, come in the side gate, enter the back door, walk down the steps and find me naked and ready to go to work on that magnificent cock of his – in my basement.   He’s game.  I tell him I need a half hour to get ready.  He writes back and tells me that his GPS is on the fritz; could I please text him directions.  I do.  I head down the basement to get ready.

My bathroom is in the basement.  I leave the upstairs one for guests.  All my clothes are also in the basement.  So, is the laundry and this huge work room where I used to have rehearsals back when I did music and theatre.  Now it is filled with cast off furniture, a computer, lots of books, storage cabinets full of collectibles, and file cabinets full of documents that have to do with my rental properties. 

First thing, I straighten up.  The place can look pretty decent – like a 1950’s version of the basement where high schoolers would have parties and make out.  Once that’s done, I go to work on myself.  Shaving the ass, no problem.  Douching?  Not so simple.  It remains one of the great mysteries in my life; douching; sometimes there is no problem, other times it is fraught with issues.  Maybe I over rinse?  Is that possible?  But I usually keep working at it until the water flows clear.  Of course, I’m in a hurry and so, in this instance, with my luck, things do not go smoothly.

In between flushes I’m getting Fusion Radio Chicago to play on my laptop, setting out supplies (including big boy condoms, because Mr. Pitbull played covered last time), covering the furniture with large towels, the floor with blankets.  The heater is on full blast, the lighting is set (low, but not as low as Mr. Pitbull had it at his place -  I want to see what I’m working on), and I have vintage porn playing on the television minus sound.  So, as we reach that critical time, everything is as it should be… except my ass.  The water is not clear – it’s pretty clear, but not perfect. 

As I’m douching, I’m also prepping my ass for Mr. Pitbull.  See, the dude is 8.5 inches – not a problem – but thick, and really, really thick by the time he’s rock hard and you’re nearing the base.  I had a lot of trouble accommodating him last time and I don’t want to be sore or have to beg off, so I am lubing and stretching my hole as much as possible.   Once I am able to comfortably accommodate three fingers, I feel ready.  And clean. 

I check my phone.  He’s texted me.  He’s just taken the exit to my house.  Yay.  Then he questions my directions.  At this point he’s less than five minutes away from my house.  I give my ass one more flush, check it with my fingers and tell myself that I will just have to take my chances.  I walk up the steps, closing the door to the kitchen and the upstairs.  The dogs are now in post-dinner nap mode, so if Mr. Pitbull enters quietly, we will probably not disturb the dogs. 

I prop open the inside door and look out the window in the door.  I can see the alley and my drive from here.  One of my neighbors is pulling out of his drive from across the alley just as a white four-door is coming down the alley.  It’s a stand-off.  A minute goes by before the neighbor finally does the right thing and pulls back into his drive so the car can pass.  As the white car goes by I’m thinking… that could be Mr. Pitbull.  The little stand-off must have threw him off his game and he forgot to look for the house number on my garage.  Sure enough… moments later I get a text.  Now he believes he is in the wrong part of the city.  Heading back into the basement to apply some lip balm, I explain where I am again.  He keeps texting and I keep replying.  I am thinking, why can’t things be simple?

I am texting and heading back up the steps when I hear what used to be (pre-special needs dogs) my favorite sound in the world: the sound of my back screen door opening and a trick entering my house!  I reverse direction and assume what I hope my tricks feel is a sexy greeting; me, with my back to the entrance of the room, kneeling on an oversized arm chair with my ass in the air.  He enters and briefly chuckles.  He’s pleased.  As he’s taking in the view, I’m taking a hit of poppers, just one, because I want to be relaxed.  It also adds to the heightened atmosphere. 

I turn around.  He’s removed his shoes and coat.  His perfect b-ball cap is still on, along with his jeans, socks, and t-shirt.  I move to kneel before him, reaching up to caress his impressive package through the jeans.  The man has an amazing pouch.  I remember what it looked like in a pair of Calvin Klein underwear and am already savoring the thought of deepthroating that fucker for all I’m worth.

In this light, he’s taller and thinner than I remember, not as stocky.  In his mid-thirties, he’s as handsome as ever.  I love his wry, masculine smile, his beautiful eyes, and his deep voice; it’s the voice that has probably launched a thousand orgasms.  He’s not one for small talk or any talk, really, other than, ‘suck my dick’.  His jeans fall to his ankles.  He’s wearing black, Calvin Klein briefs, cut just right.  His pouch is awe inspiring.  He drops the underwear before I can get my mouth on them and presents his cock.  It’s soft.  I think he’s a tad nervous (out of his element).  I take him in my mouth and moan.  I love his smell – always fresh, powdery with just a hint of man musk.  Wrapping my hands around his ball sack, I give them a slight tug.  Now it’s his turn to moan. 

In no time at all, he’s up and hard.  I love taking a soft dick in my throat and feel it as it pulsates to life.  There’s always that ‘oh-yeah’ moment when the shaft flexes and expands and you know there’s no turning back.  I take my time.  Mainly because I know there are only two things on the menu:  I suck his dick, he fucks my ass.  No kissing.  No playing.  Ten minutes go by and I realize he’s still standing with his jeans and underwear around his ankles.  Where are my manners?  I instruct him to take a seat in the big chair where I was kneeling, presenting my hole for him earlier.  He does and I start removing his jeans and underwear so he can spread his legs.  Fucker looks good like this.  That cap, that face, that incredible bod – he’s hiked his t-shirt past his pecs so we can play with his nips.  Taking his dick in my mouth, I reach up and tweak ‘em and he reaches down and does the same to me. 

I’m doing my best to get to the base of that dick, but I also do not want to scrape him with my teeth, so I know not to push beyond a certain point.  Sucker is so fat, I cannot do it.  I take it to the point of gagging several times, while changing it up, playfully tonguing the massive head, running my lips along the fat vein of the shaft.  He likes that, but always redirects my mouth, forcing me down on his cock.  At some point, I straddle his right leg and hump it ever so slightly.  Dude has awesome calves.  Instinctively, he raises his socked foot and rubs my nuts with it, eventually reaching back and pressing a toe into my hole.  I moan and hump.  I love being dommed this way.   It’s like being under a man’s boot.

I continue to mouth his cock.  He’s obviously enjoying it, though he’s not verbal.  His face is always very serious and aloof, as if, if I suddenly announced I was done, he’d just walk away and find another willing cocksucker.  He’s also watching the vid on the television, as if the work I’m doing is not enough to keep his interest.  We’re now well over the twenty minute mark.  And suddenly, the music dies.  I leap up and try to get it back, but for some reason it is playing through I-Tunes and I am flummoxed.  

Giving up, I return to my knees.  He presses his foot into my balls again, as if to say, this is where you belong, faggot.  The room is silent, except for the noises I make slurping his manhood.  He reaches over and starts playing with my ass.  Also, when I was trying to fix the music, he found my poppers.  He takes a hit.  I love a top that does poppers.  So powerful and sexy.  He holds the bottle down to my level.  I take them and inhale.  Sweet.  They invigorate me.  I am more determined to get the whole of his cock in my mouth… and I come damn close before I pull back for fear of causing him pain.  He takes another hit and plays some more with my hole.  Obligingly, I turn so that I’m on all fours and he can have easy access to it with his left hand.  That does it for him.  He pushes me off his dick, stands, and says the words I’ve longed to hear: ‘I want that ass now.”  He is a man of few words and a deep, rich, wonderful voice.  It’s enough to make me squeal like a total pig.

I decide to resume my position on the chair, on my knees, my back to him, my ass curved up and out.  I’ve tried this with tops in the past and, for some reason, it has not worked wel.  Fortunately he is the perfect height.  It may also have to do with just how heavy his cock is; It sticks straight out, not up… so he is like an arrow pointed at my pucker… a big, fat, thick arrow. 

I grab this huge tube of lube, grease up my hole and his cock. He doesn’t reach for the big boy condoms I have provided.  Then, as I assume the position, I reach back and stretch out my hole.  This is awkward and probably does nothing for him, but, in the long run, I know it will pay big dividends in my pleasure dome.  Grabbing the poppers, I take a massive, massive hit.  Like a forever hit.  Like I know that an atomic bomb is about to pierce my atmosphere and I must be prepared hit.  He lines up and eases in.  Just the head.  Then an inch or so.  My hole is already feeling the stretch and I back off slightly.  

We’re in tune.  I pass him the poppers and he takes a hit.  As he’s doing this, I adjust and start easing my way onto his cock.  This is working better.  He passes the poppers back.  I am almost to home base, but there is another two inches, two really fucking thick inches, to go.  One more hit and pop!  Dude is in.  I let him flex in there and get comfortable. This is not a man who does not know the value of taking his time.  Feeling the full width and breadth of him, I know I am one lucky man. 

He starts slow… very slow.   Easing out and easing in.  There is a kind of pain, but more pleasure.  He builds momentum and I stay with it.  Soon, he’s at mid-tempo; my fuck back kicks in – I start meeting him thrust for thrust.  We keep working it up, faster and faster.  Letting him drive, I take another hit of poppers and pass them back for him.  As he’s taking a hit, I pick up the slack.  Then, something goes animal inside of me.  It’s the two of us, slamming into one another full force, full speed… and then, after about five minutes, it’s all me!  I’m in control.  I am fucking back on him like he is merely this giant dick connected to a wall or something.  A total ass freak, I pound on his dick like I know what I want, and I want it now.  Basically, I’m raping his cock.  I tell him I want his load, in my ass, deep.  I keep talking shit until we reach a point where motion blurs, in a total frenzy, when cocks explode.

He warns me.  I ignore it.  It makes me want it more.  I intensify my efforts.  Must not let him down.

He shoots, grabbing my ass, stilling me.  I relax.  He spasms inside me.  We’re both moaning.  It is sweet.  We freeze, his dick unloading in my well-fucked hole, and remain in that position long after his dick is spent.

Still buzzed on the poppers and the high of his ejaculation, we are both a bit giddy.  I whip around, get down on my knees, and clean his cock.  No worries.  My ass was clean.  All he smells of is hot, fresh cum.

He dresses; a grin on his face.  At that moment, I realize that perfectly curved b-ball cap never came off the entire time and that I never touched his face or got to caress his sweet bald head.  I hand him a hand towel and explain that he’s welcome to shower or whatever.  He uses the towel, declines the shower, slipping back into his jeans and underwear.  I apologize for the music.  Small talk is brief.  Shoes on.  I check in to see if he had a good time.  He grins and lets me know he did.  

Good-byes.  Up the stairs.  Out the door. 

I am elated.  That was A-game fucking.  I did myself proud.  I go clean up thinking…

…if that doesn’t bring him back for another round, then I don’t know what will. 

Your Boyfriend Fucks Me, Too: A Sex Trilogy, Pt. 3

I arrive at his apartment building in record time, still buzzed from my recent brush with the law.  Pumped and feeling good, it makes me wanna have sex!  He buzzes me in and I head down a very familiar hallway. In fact, I have been to this apartment before.

There’s a twenty-something that lives there.  He frequently hits me up on-line and tells me to get my ass over to his apartment so he can fuck it.  He’s blonde, tall, thin, with a couple of nice tats.  Great bod.  Cute as hell.  Could do way better than my ass.  Always very much on the down low. 

The scenario is always the same:  I enter, strip, get on my knees as he poppers up.  I suck him hard, though usually he’s already hard when I get there.  He’s always nude when I walk in, too.  The lights are off, with the television providing the only light.  He usually has some stupid reality competition on, which I think he may actually watch as we fuck. 

The scene is all about the poppers; he pushes them under my nose, he takes giant hits.  They are always good, fresh, powerful.  Maybe I tweak his nips.  Maybe I squeeze his ass as I suck him.  But after that it’s all about the fucking.  Me on all fours or standing, bent over in front of him.  He likes it raw and intense, as do I.  We are usually done in twenty minutes.  I rarely cum, and he could care less.  Don’t get me wrong – he’s a nice guy, just not looking for friendship.  He wants me to grab my shit and get out as soon as possible.  I’m cool with that; it’s what I signed up for.

I knock, and this time, a tall, thin dude a few years my junior opens the door.  He’s wearing sweat pants and showing hard.  From the get go, he’s friendly, talkative, sweet.  The lights are on and the television is off.  He’s in great shape and his tats are out of this world; giant tribal tats caressing the curves of his body.  He strikes me as a former circuit boy. 

I do what I always do when I get to this apartment.  I set my stuff down – cock rings, lube, and poppers – and then start to strip.  He laughs and suggests we head back to the bedroom.

Huh?

Wow.  Am I stepping in something?  Is this cool?  I want to ask, but decide that maybe now is not the time.  Hell, I want my nut, so I push all concerns off to the side and follow him back to the bedroom.  Music is playing, the lighting is nice.  This is so not the cum and go scene I thought it would be.  

He kisses me.  Deep.  Full.  It’s like sinking into a nice glass of merlot.  I wallow in the richness, the warmth.  Clothes fall off, his lips never leaving mine.  He pushes me toward the bed and I excuse myself for a moment.  My dick is already hard, but I want my cock rings.  With great effort, I manage to get them on.  He’s never played with cock rings and is kind of fascinated. 

He slides back on the bed and I get between his legs and take his stiff dick in my mouth.  It’s nice.  Seven and half inches with nice low hangers.  I take those suckers in hand and give ‘em a twist and a tug.  He moans.  He’s my kind of man.   I look up and take in his face; rugged, cute/handsome, charming.  A little on the boyish side, but that is also because he’s so wiry, so thin.  His body is nice… taut muscles and I am guessing zero percent body fat.  I return my focus to his dick, which he appreciates. 

Soon we’re 69ing it.  I like his technique.  Good kissers typically make for excellent cock suckers.  In this position, I start playing with his ass.  He doesn’t protest, so I figure it’s on the table.  I reverse the 69, so we can kiss again before getting on top of him in order to grind my dick into his.  Then I slip my cock down and slide it between his ass cheeks.  I playfully rub my dick along his taint, checking in with him to make sure it’s coo.  

Now, keep in mind, the original intent of this get together was for him to fuck me… but suddenly, I don’t see it that way.  I work my way down and start sucking his dick again.  Then his balls.  Then his hole.  It’s nice and clean.  Dude has excellent hygiene.  He’s also into it.  I eat that motherfucker like it was pussy and I’m a porn star.  Lavishing some serious attention on that pucker, I have him rolling up and offering his ass up on a platter.   I tongue it and suck it and deep kiss it like I own it.

So, you know I’mma gonna wanna fuck it.

It’s his body.  Despite his height, he’s so wiry, so thin, so boyish that I just want to dom him.  It always starts with that damn first kiss.  If it’s good, it lights a certain fire in me.  I don’t top, but I’mma gonna wanna fuck him.

And I do.  He’s so fucking tight.  Lots of lube.  With my cock rings on, including one around my balls, my dick is like a fucking baseball bat – all veins and muscle.  It takes a bit, but once I’m in I’m pounding hard.  Why?  Because I know I am not gonna last long.  These days, I never do.  I don’t know why.  And sure enough, I’m squirting my jizz down his chute in no time with little warning.  Fortunately my dick remains hard and with the cum making his hole even slicker, I just keep fucking his ass.  Yeah, not a lot of variation here, but it was a decent fuck.

My dick starts to lose that drive.  I bend in and kiss him.  He’s talkative.  Playful.  The heat remains between us; an intimacy that is as exciting as it is unexpected.  I am having a good time.  And I know full well our good time is far from over.

Now he’s on top of me, and then down between my legs.  He doesn’t eat my ass.  He just plugs it with his cock.  And it feels good.   Lots of lube.  Unlike me, he changes it up, twisting my body this way and that way, kissing me on and off the whole time.  Soon we’re spooning sideways, his dick still inside me, the two of us in sync with one another perfectly.   I love the way it feels.  Tightening up my hole, I milk his dick. He moans, loving it, and responds by rapid bunny fucking me.

The heat remains.  The heat builds.  Me flat with him on my back.  Me on all fours with him pounding my ass full force.  But this dude knows how he wants it to end; me on my back with my legs up in the air as he leans in for that big, final, deep kiss.

This is my favorite way to take a load.  And I do.  Deep in my gut.  Our lips locked onto one another’s. 

So, I am totally rocked.  My bod is spent in the best way possible.  He’s happy, too.  We embrace and stay that way for a bit.  And he’s talkative.  He’s playful.  In no rush to get me out.  He offers me towels to clean up.  We talk about past experiences and partners and the cock rings.  We talk about poppers and that stuff dude’s spray into a towels and then put in their mouth.  We laugh at how stupid that can get.  We laugh at how old we are.  This is a really nice guy…

…whose boyfriend fucks me, too.

I don’t say anything.  I leave it as is.  Four days later he hits me up on-line.  He wants to fuck me again.  I tell him I have an early day and have to hit the sack… otherwise I would so be there.  And that was not a lie.  I would love to get together with him again, despite the weird situation. I mean, I assume he knows his boyfriend fools around on the side.  Obviously HE’S fooling around on the side.  So why do I think this is a dilemma? Do I keep my mouth shut?  Do I now have to choose one over the other?  Or can I keep fucking them both?

What do you think?

I don’t have an answer right now.  I will work on it during my upcoming vacation.  I am getting out of Minneapolis for an entire week; away from all these men I know a little too well; kind of a cleansing of the palette, if you will. This is an opportunity to be a stranger in a strange town which translates into me getting it on with plenty of strange.

I’ll let you all know how it all goes down. 

You know I always do…