When Alien Worlds Collide

It sounded like the ideal marriage of family and fun.

My sister and her husband, high school sweethearts and five years my junior, had rented a nice condo by the beach just north of Tampa for a three week winter getaway from Long Island. The plan was for me to drive to St Pete’s, four hours from Lauderdale and just south of where they were, spend a Wednesday night at the gay guesthouse where I had been before and hopefully play with some pre-arranged web dates; and then go over to my sister’s place, an hour way, the following day, and spend Thursday night with them. Friday A.M., the three of us would drive in one car the monotonous seven hour trip to Pensacola to visit their daughter, my niece, and her husband to celebrate my grandniece’s – their granddaughter’s – fourth birthday. On our way back home that Sunday, I’d drop my sister and hubby off at their place in Tampa, then spend another night in St Pete’s on my own where I ideally would have some more dick and ass, before I headed home to Lauderdale Monday morning.

P.S. I had never told my sister I was gay; if she had figured it all out after all these years, she never brought it up and neither did I.

So my little getaway sounded like the perfect plan, right? Well…

Glitch #1:

I had spent a few weekends in St. Pete’s over the past year or so and had had my share of fun with some web buddies, mostly lined up in advance. This time, though, wooing guys was harder than cumming on meth, to the point that I thought maybe I had outworn my welcome and had made all the guys in town who would ever have been interested in me. There were a few newbies who had hit me up in recent months out of the blue and sounded like they’d play my sex slaves but when I told them I’d be in town that Wednesday and Sunday evenings, the silence of their non-replies was deafening. I did manage to line up two regulars for that Wednesday. Troy, a victim of AIDS, was thirty pounds thinner than when we had last played, and could neither shut up or get it up; but thankfully, the second, my good old boy, Steve, a tall lanky, hairy, pleasant enough looking guy, made up for it with his cocksucking expertise. And, as luck and timing would have it, I was able to snarl a burly, humpy football player type visiting from upstate New York late Wednesday night who came over Thursday morning before I hit the road for my sister’s where we sucked one another’s tools and I raped his furry manhole. But ever the practical pig, I was still concerned about how light my dance card was for that Sunday night on my return.

Glitch #2

My sister, brother-in-law and I were to drive together to my niece’s which would save some gas but, even more importantly, break up a very long and boring ride with some conversation. But, at the last minute, they decided that they wanted to stay through the middle of the following week, and months earlier I had booked Key West for other my other half George and me. By the time my visit in Pensacola was over, I was supremely happy I had an excuse for not being able to hang around longer.

And since I would be traveling back on my own, it quickly dawned on me that I might be able to make a few Pensacola boys after I left my niece’s before heading back to St Pete’s, kind of an insurance policy just in case I came up dry for Sunday evening.

Glitch #3

Gays can be silly or caustic, but str8’s, well str8’s are just boring. Thursday at my sister’s rented condo in Tampa, we talked about a lot of things facing us as fellow retirees-to-be, but somehow their excitement over a retirement community “where everyone has their own golf cart!” which my brother-in-law’s older brother was contemplating not far from Tampa where he lived with his wife of 30 years was not something I, a man of the world whose Saturday night didn’t begin until midnight, could share. In fact, when all of us went to the Olive Garden for dinner that Thursday evening, I, the oldest fuck at the table, looked 20 years everybody’s junior. Maybe staying active in the hunt forces you to try to keep your shit together – who knows?

That night, with my sister and brother-in-law asleep, I canvassed the search engines on my ipad and lined up a trio of Pensacola men, none online at the time, who I hit up for a possible Sunday morning rendezvous.

My boredom with the other side of the social spectrum only worsened once we were at my niece’s though, being a frustrated actor, I put on a good front. It seemed like everybody was talking down so little Sydney, my grandniece, could remain entertained (My sister, the archetypal grandmother, also bought enough birthday gifts to open a branch of Toys Are Us). About the only half-ass adult conversation we had was which cars we’d be taking to the jump center on Saturday afternoon where, for two hundred bucks, my niece had arranged for a birthday party for Sydney and her pre-school cohorts, including Sydney’s towheaded “boyfriend,” Timmy.

Hey, you know I like guys over 35, but I could see how a pedophile would love to defile those innocent, wide-eyed little four year olds who jumped on the trampolines for a good hour without a care in the world. One little girl who caught my attention wore big, weighty glasses and a colorless expression for most of the afternoon. I later learned from my sister that she had had three brain surgeries so far in her little life. Yet her parents were upbeat and smiling, happy I guess that their little Cindy was beginning to fit in.

And for the closeted homo still lurking in me, there were a few cute daddies I was able to strike up a conversation or two with. Their hot bods and tight asses, together with the birthday cake we all devoured later somehow compensated for the lack of leather, hairy chests and rum and cokes, my usual weekend fare.

Two years before, when the last of my nephews was getting married, my niece’s husband had strangely confided in me, maybe because he viewed me as a neutral member of the family, that he wasn’t getting any more action at home, and that my niece had apparently acquiesced her role as a wife to be the doting mother of their little girl. Not good for two thirty somethings. That secret resurfaced in my mind as I watched him fiddle most of the night with his ipad as we sat through one mind-numbing kiddy flick after the next on their 46 inch flat screen to the endless delight of my grand-niece. Was he combing hook-up sites for str8’s just as I did for us gay boys? Was he even carrying on an affair and texting some chick, right there while his wife was gathering up all of Sydney’s new toys courtesy of Grandma and Uncle Ray?

Could you blame him?

Later, in the sanctuary of my guestroom, I checked to see if any of the three Pensacola men worth jerking off over whom I had hit up Thursday night had come through. No, “No messages.”

So that Sunday morning, while everybody regurgitated every last boring tidbit of Saturday’s jump party, I, who felt more disconnected than I had ever felt from family before, bid my fond – and relieved – farewells and headed back to St Pete’s, seven hours away.

“Watch your speed,” my niece’s husband cautioned as I rolled out the driveway. “The cops are out like roaches.”

“Don’t worry, I never go under 80,” I quipped back.

Just like my life versus theirs.

Glitch #4:

I had the numbers of three guys who said they might, maybe, could be, sort of, kinda free that Sunday night. On two, I got voice mail that predictably went nowhere; the third actually picked up, but said he thought I had meant Saturday, not Sunday and that he would be working. (I don’t think I talk in Korean, do I?) That left me high and dry and at the mercy of the “I want it now” boys once I got into St Pete’s.

While pondering my potentially sexless fate for the night, I’m remembered one guy, “Big Billy,” a huge, lumbering six footer, who said he loved to suck my cock, had hit me up Wednesday night late. I had replied non-committally at the time, but after a quick beer back in St. Pete’s at the Flamingo’s tea dance which sported no cruising hotties, I checked and saw he was online. He was receptive and was free around 9. Great.

Just then, just as I sealed the deal with Billy, I got a hit from a slight, hairy thirty something bottom who wanted my cock up his ass bad. Real bad.

How bad?

Well, when I asked him when he might be free later, figuring I needed sometime between tricks to recharge, he replied – on his smartphone – that he was free NOW. In fact, he was waiting in the parking lot downstairs!

I quick munched down a Viagra, but while I tried to stall things a bit by taking a shower as he lay on my bed butt naked, waiting patiently for my hard cock, Mr. Peter and I were too strung out from that boring seven hour ride from Pensacola to do his hot, hairy boy butthole justice. He understood, even apologized for springing up on me, and said he was still interested in connecting the next time I was in town. He gave my soft cock a slow but hopeless farewell suck to show he meant it.

Fortunately, by the time Big Billy, who barely fit through my door, arrived ten after nine, Big V had kicked in, and the pharms together with Billy’s hot, patient mouth and long furry beard he kept stroking against my cock finally awakened Mr. Peter to his full glory. An hour and half later, at least physiologically satisfied, I visited my favorite 24/7 diner a few blocks away for a very late dinner, served by my favorite retro-1957 waitress. Besides two guys at the counter munching sandwiches who looked like they belonged in a homeless shelter, I was the only customer in the place.

Ever the horny beast, I checked the websites one last time Monday morning before my planned departure for Haughty Lauderdale when, lo and behold, Jim, a heavy set but Matinee handsome hairy chested guy who was looking for a quick morning fuck before he left for work, hit me up on adam4adam. A half hour later, he was on my bed, primping my cock for his butt with his tongue (seeing his real tiny penis made me understand why he was not a bottom by choice), and I screwed him good and shot my load, all before 10 a.m.

And when I got home that afternoon, still a bit dazed by my whirlwind, funky, somewhat fucked-up sojourn, who should be sitting proudly with a hard dick pic on my pc screen than one of my Pensacola boys, complete with his address and cell number, wondering when I would be “cumming” over.

As they say, timing’s everything in life.

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