Part 1: Best Made Plans and Bucket Lists

Sometimes, no matter how well you try to plan an event, life gets in the way and something you hoped to make happen devolves into whatever the universe deems adequate.  Accepting this premise would go a long way towards explaining the last few days of my vacation, following my stop in Eau Claire last Tuesday and the wonderful Janis Ian concert I attended last Wednesday.  Last Thursday was spent prepping for what I had hoped would put to rest, once and for all, an item on my personal sexual bucket list: a gang bang.  Yes, even at my age, I remain fascinated and titillated by the idea of a group of anonymous tops using my holes for their (and my) pleasure, even going so far as to book a hotel in Madison for this specific purpose.

I was doing everything I could think of to ensure success.  Two weeks before the event I had a Craigslist ad out there that I renewed on a regular basis right up until the day of the event (when it suddenly got flagged and removed).  I had a party ad on BBRTS and joined the site for as a full member for the month so I could have unlimited emails, access to all features, etc.  I’m also on A4A working the Madison area.  My pics were current and fairly flattering, my profile to the point and interesting.  Bottom line, I marketed myself as best I could, being explicit regarding what I did want (lots of men stopping by to drop a load or two, good hygiene, discretion), and what I did not want (NO PNP, no alcohol, no hassles, no endless emails).  I set a time, hinted at which hotel I would be hosting this event, and promised that the door would be unlocked (duct tape) for easy access. 

During the two weeks leading up to the event, I started collecting potential sperm donors.  I had enough to pick from that I could afford to be a little picky (no pic/no play, weed out the less appealing dudes) and things looked to be a go.  So excited by the prospect of this event, I would go to bed each night humping the mattress in anticipation.  How did it turn out?  Hey, we’ll get to that, trust me.

As the day approached, four of my most desirable suitors emailed me to let me know that they wouldn’t be able to make it (had to work, forgot they had dinner plans, would be out of town, etc.), but let me know that they would still love to hook-up with me beforehand if possible.  Two of these dudes can only be described as porn-ready hot – perfect gym bods, handsome, kinky as hell, and highly sexual.  So, of course, the universe prevents us from getting together (at one point they proposed a three-way, but I was there on business as well and couldn’t make it happen).  However, one of the dudes on my most wanted list proposed meeting at 4:00 pm, four hours before ‘the event’, promising to help warm me up for what was to cum.  I was impressed enough to consent and Mr. Rock Star and I made plans.

Mr. Rock Star is thin, tall, good-looking, bearded, worked-out, full of tattoos and piercings, and adventuresome as hell.  In fact, other than the tats and piercings and his handsome face, he could be me – as in, once we met, it was a little like making out with myself, something that I have always wanted to do (what narcissist doesn’t?).   He’s a dom, aggressive, versatile top and as we text back and forth during my stay in Madison, I learn a lot more about him – and there’s a lot to like.  He’s upbeat for one.  Lots of energy.  Lots of interests.  Nothing he suggests freaks me out until he brings up sounding, which is something he’d discovered recently.  I know a little about sounding , having done a bit of research about it.  Based on that information, sounding is on my personal ‘no fly’ list, which I mention to Mr. Rock Star, not that it prevented him from talking about it several more times. Turns out that is something Mr. Rock Star likes to do – talk.  Not that there is anything wrong with that.  Traditionally, I am more the silent type, which is why I have frequently found myself paired up with a talker.  This combo is great for social situations – they act as my conversational shield – but privately can be a little irritating (as I prefer silence). 

As Friday approaches, I am pretty psyched to meet this dude, and am also wondering if I’m making a mistake with the whole gang bang thing.  Checking into the hotel is no big deal.  I had requested a room far from the pool and social gathering areas, so end up on the top floor.  Walking into the room, I am initially shocked at how small it is: one bed, and little space, but after settling in, I realize it’s all I need.  I try to imagine a bunch of dudes crowded around the bed and I begin to doubt my vision.  But I don’t have a lot of time to dwell on it, there’s work to do.  Grabbing the duct tape, I secure both sides of the lock mechanism with several layers of tape.  I had already prepped my bod before arriving (shaving, trimming, oiling, cleaning) , but continue to douche my ass.  The last thing I want is the night to be derailed because I didn’t do my due diligence.   I set up my I-Pod, get my tunes on, get out my cock rings and poppers, set the digital camera out, secure all my stuff, and fire up my laptop to check for updates, etc.    

It’s then that I see my ad has been flagged and removed on Craigslist.  I consider placing another ad, but stop short.  The clock is ticking and I am wondering if what I have lined up is more than enough.  At the appointed time, I climb up on the bed, get on all fours, and present my hole.  I imagine myself doing the same thing four hours from now for a mysterious number of anonymous tops and, much to my surprise, the thrill is gone.  I’m getting cold feet. But I don’t have time to dwell on it, for Mr. Rock Star arrives.  

As he walks in, I think about taking a hit of poppers, but resist.  It’s going to be a long night, and I need to conserve my strength.  Now, my balls are stretched with five (five!) steel chrome cock rings – a new record for me.  Ball stretching is something that has intrigued me for a while now and before I left Minneapolis, I stopped into my favorite gay store and purchased two more rings.  They are held in place with a tighter black rubber one.  In the mirror at the foot of the bed, my ass with the stretched balls swinging between my legs looks amazing – like it all belongs to someone other than me.  Mr. Rock Star is suitably impressed.  He’s yanking on those immediately.  Taking me by the balls, he guides me off the bed.  This makes me hard as a fucking rock.  My dick looks good and I force him to suck me.  Returning to his feet, we kiss.  His grasp and yank is fairly aggressive and I reach a point when the sensation goes from pleasure to pain.  He backs off. 

The kissing is passionate, intense.  We get so carried away; he doesn’t even have time to remove his clothing.  He’s dressed to the nines (on his way to some party in honor of his partner), so there is his dress shirt and tie and all that to be removed.  I start helping, but there is always something awkward and a bit comical about sexual partners wrestling out of their clothing.  Soon, however, he’s sitting spread eagle in the arm chair and my mouth is swallowing his dick to the root.  It’s a nice dick: 7”, and nice looking - just like the rest of him.  He’s a striking man.  Think:  Michael Stipe with a punk edge and a worked out bod.  The cocksucking is good, but he wants more right away.   Fully naked, he stands and moves behind me.  Wrapping his necktie around my throat and using it as reins, he gets down on his knees, and, as he enters my ass, he tightens the tie just a bit.  Okay, so I don’t know this dude at all and, while I am a little freaked out from a safety point, the rush this causes is amazing.   I can totally see why people get into auto-erotic asphyxiation.  And I’m sure the danger involved has something to do with the allure of this activity as well. 

His fine dick is hitting me just right from the get go and he’s an aggressive fuck.  Wasting no time, he moves from regular doggy, to pile drive from above doggy.  Good thing I stretched out my hole before he arrived.  After that, we move to the bed. He fucks me every which way we can come up with, to the point that he literally fucks the cock rings right off my balls!  We’re both liking what we see in the mirror at end of the bed: hey, we look good together.  Something about his punk energy lights my fire.  He’s also my height, so looking over my shoulder and kissing is no problem.  It’s a very athletic sparring, and when he fires off his load in my ass I collapse, totally impressed with our dexterity and endurance. 

Cuddling up on the bed, he tells me he didn’t mean to cum so soon (half hour mark).  That’s silly, I tell him, we were totally killing it.  Then Mr. Rock Star proceeds to talk.  He tells me stories about his days as the lead singer of his band and what it was like to be gay and sought after by female groupies.  The stories are entertaining and bittersweet.  The entire time he’s talking, I’m gently toying with his spent dick, fairly certain that, given his previous performance and inclination, there’s another load in the offing.

After about ten minutes of downtime, during which I do not push my own agenda one iota, his dick is up and hard again.  He’s in the middle of a story about a pyrotechnics gone wrong when I go down on him.  The second time around there is less urgency and more technique.  This is true of both of us in relation to all activities.  Even the kissing is better, for it is now less rushed, the energy less scatter.  Moving up for a kiss, I sit on his dick and pound my ass into his pelvis.  Flipping me on my back, he doesn’t miss a stroke.  I concentrate on opening and tightening my hole to great success and he’s very appreciative of my efforts.  I hand him the digital camera, because one of my goals is to get a pic of every dick in my ass the weekend.  He ‘takes’ several shots, but the full flash doesn’t fire and I suspect (correctly) that he’s failed to capture this particular Kodak moment.  I decide not to press the issue.

Things ramp up quickly from there.  The original energy returns and soon we’re like two warriors at battle.   Sweat drips, lips meet, bones grind.  Armpits come into play and it turns out we are both into them.  He loves my funk, fresh and hot from our activities.  We fuck like animals and the fireworks are impressive, as he deposits a second load in my ass.

Lingering, he tells a few more stories before noticing the time (we’re at the two hour mark).  He’s late for his partner’s party.  Without the benefit of a shower, he dresses and exits, leaving me feeling a little like I’ve just been Rhett Butlered – for he is gone with the wind.  I wonder if I would have appreciated it all more if my mind was not filled with thoughts about what was to take place later that night.  It was a great fuck, and I was fully present, bringing my A-game, but still…   I wonder why one is never enough.

I look at the clock.  Time is slipping away.  Checking in with myself, I am filled with doubt.  My resolve slipping, I ask myself…

…am I getting cold feet?

End Part 1