Part 2: Best Made Plans and Bucket Lists

My relationship with sex is a lot like my relationship with food.  Deprived of it for any amount of time and my eyes automatically become too big for my stomach.  In other words, when I am not sexually active, my mind tends to work overtime, creating fantastical situations that frequently write checks my reality cannot cash.  This would explain my desire to have a gang bang where multiple anonymous tops use my ass as a cum dump and other such nonsense.  This type of gluttony?  Good in theory, difficult in reality.

The previous Tuesday I had some great sex in Eau Claire.  I had to concern myself with other things on Wednesday and Thursday.  Friday was to be the ‘big day’.  Mr. Rock Star showed up at my hotel as planned.  The sex was great.  He really wanted to be part of the gang bang, but had a previous commitment.  This was true of three other really hot guys who had signed on early in the planning of my little event; however, meeting them at another time was not in the cards. 

It was now 6:00 pm.  Mr. Rock Star had just left; two loads lighter.  I sit down in front of my laptop and contemplate: what is it I want?  The gang bang is to begin in two hours.  I have eight guys that have committed, plus three new dudes who want in, and one really nicely dicked dude who wants to watch and then fuck me with a condom.  Also, in the que for the BBRTs ad, are six dudes that I, for one reason or another, am reluctant to include (no pic, sketchy emails, suspicious profiles, bottoms).  On top of that, I have two dudes who have expressed interest in dropping by my hotel after 10:00 pm to use my ass.  One wants me to wear a blindfold. 

Looking at my options, I begin to question if this is a case where less is more and whether a little quality control isn’t also in order.   I’m not going to lie – the whole STD thing keeps nagging at me.  I expressed my sudden reticent bent, not only to Mr. Rock Star, but also to one of the upcoming participants who has been consistently enthusiastic about the event and the prospect of breeding my hole.  We begin texting back and forth.  He now wants to come over early.  I tell him I am working on stuff and that the 8:00 pm time still stands.  Then I begin reviewing my scheduled attendees and activities. 

First off, I contact the two dudes who want to show up after 10:00 pm and tell them I will not be available.  The thought of being wiped out from the gang bang and then having another couple of dudes come in, subjecting my ass to more abuse and sex is something I decide I do not want.  Sex out of obligation or sex that is merely tolerated because of having made an obligation?  That never feels right to me, and rather than risk it, I decide to bail early – early enough that they can make other plans.   They are disappointed.  I can live with that.  One is super hot.  The other?  It’s hard to tell; the stats are okay, but suddenly I am starting to really pay attention to height/weight proportion and waist size – the second dude definitely fails that measure.

So, too, do two other dudes who are invited to the gang bang via BBRTs.  I noticed that they have failed to read the email I sent out with the room number, so, I simply ‘unsend’ the emails and cancel their invitations.  I also contact the dude with the big dick who wants to watch and fuck me with a condom and tell him that I am getting cold feet and that the event will most likely be canceled.  He understands.  That brings me down to nine dudes: four from the craigslist ads, one from A4A, and four from BBRTS.  I still have my doubts about one dude’s stats from the craigslist ads, but decide to let it roll.  The other three have great stats and nice dicks.  The dude from A4A seems really enthusiastic about the event.  He also has a 31” waist and his stats are good.  He is Hispanic, I think… not sure, but English is definitely not his primary language; that I can tell from his emails.  The four dudes from BBRTS include the super nice dude who is encouraging me to go through with the event and three others that I think are pretty damn hot. 

How are things looking?  Age range: 24-48.  8 Caucasian, 1 Other.  Waist Size: 31-33”.  Dick Size: 7-9”.  The pig in me can’t help but wonder where all the black dudes are.  The ones I have spoken with on A4A all seem a touch on the prudish side, so I never push the whole ‘group’ thing with them.  I totally understand why dudes prefer one-on-one; normally, I am one of those guys.  But not this night.  This is on my sexual bucket list and, ultimately, that weighs into my decision to go through with the event: I want to cross it off, once and for all.  So, I figure, it’s now or never.

I am pretty sure that fifty percent of the dudes will flake.  That will mean a party of four or five dudes.  That, I decide, I can handle and will prove exciting enough.  As the time approaches, I check my ass (I douched and cleaned out again – not wanting to carry Mr. Rock Star’s butt babies longer than necessary), shower, check my supplies, hydrate, and turn back on my I-Pod.  At 7:58 pm, I assume my position on the bed, poppers in hand, and wait.

I didn’t wait long.

At 8:02, the door creaks open.  I hold off on the poppers and keep facing the headboard of the bed.  I love this moment; when a top enters the room and I have no idea what he looks like.  Will he be the love of my life?  A great fuck?  A serial killer?  Only time will tell.

I feel the cheeks of my ass pull apart and as a mouth plants itself firmly on my hole.  Dude knows how to eat ass.  I sneak a peek.  It’s the dude from A4A.  Short, squat, Asian, dressed to kill.  And my immediate thought is: 31” waist, my ass!  He’s not run-from-the-room bad, but he is not what he sold me on the internet.  If this was Ebay, I would be leaving him some really negative feedback regarding misrepresentation of product.  Still.  He showed up.  And he’s doing a good job eating my ass.

Soon he strips, and as he is doing this, I reposition myself so I can suck his dick.  His dick is… about six inches, on the thin side, and uncut.  What the hell, I figure.  He’s here.  Where is everybody else?   

As we play, I try to find things to like about the Asian dude.  His skin is soft.  His body, though thick and squat, is super solid.  He has a nice ass.  The sucking leads to kissing and he’s good at it.  Pulling my ass to the edge of the bed, he tells me to get on my back.   Without the courtesy of lubing up, he plunges in.  His dick is on the thin side, like I said, so, while I feel it, he’s not at risk of doing me any damage.  He’s an enthusiastic little fucker.  It’s not bad.  He pounds away for about ten minutes or so, kissing me on occasion. 

Then, there’s a knock on the door; which is weird.  I made a point of telling everyone the door would be open and to simply walk in.  The Asian dude stops fucking me and goes to open the door.  He comes back and picks up right where he left off.  Pound, pound, pound.  Based on the way he was dressed when he arrived, I am thinking he has someplace else to be.  Our new arrival approaches the bed.  Tall, thin, scruffy, young, with a sweet, sweet smile and a light in his eyes that would make one think he’s part leprechaun. There is something about his smile that rings a bell, but I can’t place it, and, as I currently have a dick up my ass, I put it out of my head.  Based on how the new dude is dressed – sweat pants, baggy pullover shirt, trucker cap, sneakers – I am guessing he’s something of a slacker, or, at least, of that generation.  He’s eyeing the Asian dude and giving me pointed smiles, as if to tell me that he is not digging the Asian dude.  I just say ‘hi’, nothing else I can do about any of it now. 

The Slacker dude strips and moves to the left side of the bed.  He has a really nice nine inch dick.  Thick.  And it curves…. Downward!  He slips it in my mouth and starts talking shit, asking me how much I like sucking his big, fat dick.  This never fails to make me laugh inside – when tops stuff your mouth full of dick and then ask you questions?  What is that about?   I have come to realize that their questions are, in fact, rhetorical and I needn’t answer, but I was raised a certain way, and when someone asks me a question, I always feel the need to supply an answer. 

Taking a read on the energy in the room, I can tell one thing: the Slacker and The Asian dude?  They don’t much care for each other.  Do they know each other?  What is it? 

In my current position, I am not able to fully deepthroat the Slacker’s cock.   This is rectified once the Asian dude takes a fuck break.  Initially, I roll up on all fours and face the Slacker dude straight on, but his dick curves down, so this is not a great angle, and I worry about hurting him – his dick is rock hard.  No worries, I know just what to do.  I roll on my back, with my head hanging off the side of the bed.  Bingo!  He’s tall, and he needs to bend at the knees a bit to accommodate, but soon, all nine inches of that fine, fat fucker is sliding in and out of my throat with relative ease.  And no gagging!

Slacker dude continues to talk shit to me, and this is something that must be a regular feature of any fuck he participates in.  I like verbal tops.  I like dom tops.  But, while verbal, Mr. Slacker is not all that dom.  He’s a kid.  It’s that leprechaun twinkle in his eyes.  He’s a sweet kid, reciting dialogue he’s picked up from watching porn.  The give away?  That slight adolescent squeak to his voice and the fact he can’t keep a straight face when telling me that I’m ‘nothing more than a cup dumpster, made for sucking dick and taking loads’.  Like any good actor, I don’t tip wise.  I know better: one works with what one is given.  And really?  His shtick is kind of endearing.

The Asian dude has now crawled up on the bed and is really into watching.  The Slacker dude is paying him no attention and moves me around before crawling up on top of me.  I think he’s coming in for a kiss, but no.  I move in for a kiss and am rebuffed.  He moves his face away from mine just slightly and talks into my neck.  Am I ready to take his big cock up my ass?  Fuck yeah.  I tilt my pelvis up and wait for entry.  I look over at the Asian dude, thinking he is probably going to want to stick his dick in my mouth, but nope, he’s intent on watching Slacker dude enter my hole. 

So, again, the downward curve of his dick is a little problematic, requiring a lot of assist on my part.  But soon enough, dude is in and taking his time with my hole, allowing me to feel the full length and width of his mighty sword.  It feels awesome and I let him know.  Before long, he asks me if I’m ready to get pounded.  Fuck yeah!  Only… his idea of pounding?  Not all that violent.  More like a steady fuck.  That figures.  He’s a sweet man.  His fucking technique is pretty much like his approximation of the sex talk he’s learned from porn; more of an homage than the genuine article.  That’s cool with me.  With a dick like his, he can homage me all day if he likes. 

He’s fucking me for like ten minutes, talking shit, leaning in and not kissing.  Then he leans in and says something that surprises me: Am I ready to take his load!  Really?  It feels a little out of left field, but I’m in the moment and respond enthusiastically.  He does that freeze in place, shudder thing some tops do, demanding to know if I can ‘feel his seed’.  Honestly?  I rarely can, but always tell them yes, that I can feel them white washing my hole. 

He stays on top of me for a bit, his face so close to mine that we could kiss, except we don’t.  He apologizes for cumming so soon, but explains that he held his load for me since Monday and was so excited to finally meet me.  Again, I think, sweet.   And, dude?  You came in my ass – nothing to apologize for.   We breathe the same air for a bit more, but my idle is short lived, for the Slacker’s recent deposit lights a fire in the Asian dude’s loins.  He yanks my ass to the end of the bed and resumes pounding my hole.  Something in his demeanor tells me that he is ready to join the ‘deposit a load’ club.  It gives me the opportunity to appreciate his efforts.  I also know that as soon as he leaves I am going to spill the beans about his 31” waist.  Dude shoots and scores.  He dresses and leaves quickly.  And it turns out I am not the only one that wants to talk about him once he leaves.

The Slacker dude is yet another trick that likes to talk.  A lot.  I learn he doesn’t know the Asian dude and that he didn’t feel very welcome.  I tell him that last part can’t be true, because, on-line, the Asian dude was super excited about the whole gang bang thing, as in sharing.  Turns out the Asian dude gave the Slacker dude a dirty look when he opened the door.  I do the math on that one and realize what that was about; he was annoyed.  The Asian dude was fucking my ass, had to stop, and go open the door, even though the door was unlocked.  I tell the Slacker that all he had to do was push on it.  This makes sense to the Slacker, and I share a bit more about the Asian dude’s profile (rife with inaccuracies), all the dudes who flaked, and the one’s I turned down.   He knows a few of the dude’s, including the dude with the big cock that wanted to fuck with a condom.  He tells me he throws a hell of a fuck, and then asks me if I’m ready to get fucked some more.

Cool.

It’s pretty much a repeat of load one: no kissing, face close to mine, talking dirty into my neck.  We change it up a bit (doggy on the bed, then me bent over the end of the bed), but all in all, it’s a meat and potatoes fuck.  Added bonus?  He makes a video of it with his camera. Me?  I gave up getting pics when the Asian dude walked in.  He ends up on top of me, my legs in the air, firing off another load.  And I think that’s the end of it.  He pulls out and tells me to get ready for it.  He’s jerking his cock and… shoots a third time (!), hitting me in the face and coating my whole torso in cum!  I am in awe, and tell him so.  Dude shoots massive loads.

We relax; me on the bed, him in the arm chair, and I learn a whole bunch about Madison.   I learn about local HIV funding. We talk about housing. I learn there’s a serious syphilis outbreak in Madison (isn’t that true everywhere?).  I learn about the bareback sex parties that one of the local bars hosts, the money of which is then donated to one of the local HIV non-profits (is that irony?)  I learn that the Slacker used to live in my current neighborhood at the same time I did (and I am thinking we probably fucked before). 

The one thing I don’t learn?  Why won’t he kiss me?  I don’t ask because I think I remember the answer.  It’s a standard for dudes who mimic porn without getting the full gist of what it is to be a porn star.  Most likely?  Kissing is reserved for boyfriends and partners, not tricks.   Yeah, okay, whatever.

Eventually the conversation winds down.  The Slacker is off to a bar downtown to meet friends.  It’s 10:00 pm.  So much for my gang bang.  A lopsided three-way does not a gang bang make and it remains on the bucket list.  I proffer to the Slacker that perhaps gang bangs are too crude for Madison.  Or maybe I’m just too fucking old.  He tells me that’s not true; that if I tried this in Chicago, they would be lined up around the block.  He leaves and I consider turning in.   But I haven’t eaten.  And I want a drink.

I drive over to Club Five – or whatever they are calling it now.  I am wearing my tightest jeans, a Harley Davidson cap with a skull on it, my kick ass boots, and a black Piggly Wiggley T-shirt.  It has the familiar logo on the front in white with the word ‘Piggly’ on it and on the back a pig’s butt, complete with corkscrew tail and the word “Wiggley”.  I look good.  And the giant, rather tragic drag queen that spies me as I enter the bar is all over me in a flash.  She’s drunk and soooo not my thing.  I am polite, but play shy and make my way to The Barracks; the back room where they used to play porn and dudes were kind of cruisy.  But no more.  They opened up the wall and porn is now played only a few nights a month.   The bartender is older, sweet, and nice.  He ends up being my one real conversation of the evening.  I order a gin and tonic.

I check Grndr.  It’s college night.  So there are 19 year olds running around.  Drunken college kids?  Not my thing.  A few make eyes at me, a few hit me up on Scruff and Grndr.  I am polite.  I am not interested.  I am… disappointed.   I’ve had a lot of fun at this bar in the past, but not tonight.   Three bowls of popcorn and one more gin and tonic later, I am out of there.  I hit a nearby Perkins and have some soup and salad. 

It’s now 2:00 am.  I am to be on the road and on my way to Duluth by 7 am, which means I have to be up by 6:00 am.  Lights out.  I sleep heavy.  Disappointed?  Sort of, but there was a lot to like, too. 

Maybe Duluth will be better…

End Part 2