Decisions

Cherry Boys
June 2001
Barry had more than one decision to make.
Zac was more than willing to help.
Grand Road is thick with adult entertainment and seedy-if-nonsexual
enterprises of various sorts--there are bars, two adult toy stores, a couple of peep
show emporia, and sundry other entertainments for those who don't think
reading a good book or doing the crossword are the only ways to spend an
evening... or an afternoon.
Just off one corner of Grand Road, three bars line up in a row like shoulderto-shoulder soldiers. The easternmost bar of the three is rowdy, favored by the
local bikers and a cadre of serious drinkers. Fights, and the necessity for
appearances by the local constabulary, are not exactly newsworthy occurrences
there. Directly west of that bar stands another, a locally well-known watering hole
in fact, that's the name of the joint: The Watering Hole. There men and women go
in eager if not desperate hope of meeting each other. And often they're
successful... even if the liaison lasts for only a night.
And then there's Guy's Place. Supposedly at one time there actually was an
owner named Guido, who was popularly known as Guy, and supposedly in those
days, too, the clientele was straight. But the times have changed, and so have the
owner and the patrons. You might call it "Guys' Place" now, moving the
apostrophe over, for it's frequented only by guys. Gay guys.
It was out on the sidewalk at a midpoint between The Watering Hole and
Guy's Place that Barry was standing when I first noticed him. He seemed to be
having some trouble making up his mind which bar to go . into. It seemed to me
an odd dilemma. If he was straight, he'd clearly want The Watering Hole. If he was
gay, he'd just as unquestionably want Guy's Place. A real no-brainer, you know?

Then it occurred to me that maybe he was a tourist, someone who didn't

know what each bar specialized in. From the rear, which was the view I had (and
what a view!), I couldn't see if this was anyone I knew, or if he had a camera in his
hand or anything else that might have screamed tourist. I could sure see a
deliciously obscene pair of buns, though!
Those buns jutted out firm and strong, high and proud, round and ripe and
ready. They were a perfect set of globes, not too big but plenty meaty and
muscular. I watched as he took a step toward Guy's, retreated, hesitantly stepped
toward The Watering Hole, wavered, veered toward Guy's, stopped himself...
"Is that a new dance step?" I said, approaching him. I'd used a very soft
voice, but he still jumped out of his skin when I spoke. And blushed. Blushed a
deep, bright red.
"You seem to be unfamiliar with the two drinking establishments and
having trouble making up your mind. I thought you might need enlightenment."
But even as I was halfway through my sentence, I had an insight: He wasn't confused about what the two bars contained at all. He knew damn well... and was
still having trouble making up his mind. The bars were a metaphor for his life.
I was willing to bet dollars to pennies that this guy was a gay cherry.
"That's okay ... thanks anyhow," he said, starting to edge away from me.
"Wait!" I said, putting a hand on his arm.
''You know what the bars are, then?" He didn't answer me. I went on.
"C'mon ... I'll go with you into Guy's. Nobody's going to bother you... except
maybe me. And then only if you want me to. Let's just go have a couple of beers
and talk. You strike me as someone who has a lot to talk about. Unless you'd
rather just listen. In that case, I'll do all the talking."
He still didn't answer me, but he was no longer trying to bolt. Taking
matters firmly in control, I put a hand in the middle of his shoulders-touching him
just enough to guide him, and in a buddy like, nonthreatening way--- and steered
him into Guy's. Deliberately heading for a quiet, corner table, away from the

action, I got us a couple of beers and, true to my word, started doing all the
talking.
I told him what I'd guessed about him. I told him I was gay. I told him that
being gay was fine, but that not being true to yourself wasn't. I told him ... well,
you surely know the speech. You've probably either given that same speech or
heard it yourself-if not both-at some time or another in your life.

Finally he started talking. That's when I found out his name was Barry,
heard him confirm my guesses, and learned a few more facts about him that
aren't relevant to the story I'm telling you, so I'll skip them.
I told him, "If you're thinking about trading in your cherry status for
something more satisfying, I'm your guy. Unless I'm not your type, in which case
I'll be a good buddy and help you hook up with someone here who's more to your
liking. Just don't walk out of here alone tonight. You'll always regret it ... and you'll
still be wondering what gay sex is like and what you're missing."
"No-you're fine. It's just... I'm... I've never... I don't know... "
"You've never... but you're going to. You don't know if you want to, or how
to... but deep down you know you do want to, or you wouldn't have come this
far. And you'll find out how. Let's have another beer-for your nerves-and go back
to my place. Unless you'd be more comfortable at your own house." I downed the
rest of my beer quickly.
"Your place is fine... and let's not have another beer. Let's go now before I
lose my nerve." Barry downed the rest of his beer in a single long chug.
He grew nervous again at my house, though, and froze next to the bed, not
taking his clothes off, so I did it for him, paying attention to each spot I
uncovered. After slipping his shirt over his head, I licked his exposed nipples and
nipped at a few of the hairs that sparsely grew out of his well-defined chest.
Tracing a path across the striated planes of his chest, I slid my hand down to his

stilI - covered crotch and grabbed myself a handful of his hugely swollen man
meat.
Barry shivered at the contact, then stopped me. I thought he was
chickening out, till- he explained, "I almost went off in my pants. I don't want to
waste it."
"No you don't," I chuckled, unbuckling his belt and tugging these pants
down impatiently, "but I bet you're going to jizz pretty quickly no matter what I
do... and I bet there's more in those balls than just one load anyhow."
I impatiently yanked his briefs down, and the balls in question were
exposed to my view. His nutsac hung low and tempting me. I never was good at
avoiding temptation, so I ducked down into a crouch and quickly wrapped my lips
around his huge, hefty, hairless gonad filled my mouth to overflowing.
Prodding his ball with my tongue, I stirred the creamy contents. Barry
groaned, and his legs sagged. I half-guided, half-pushed him backward, and he
plopped heavily down onto the bed. I took the opportunity to open my night table
drawer and fish out a condom, which I expertly snugged onto Barry's throbber...
and it was throbbing, palpably, as l held it.
"Oh ... god, I almost came again!" he exclaimed.
"Give me a minute, and I'll give you a real reason to come," I laughed, and
then my lips followed the path of the rubber. Fearful that he really would come
off instantaneously, I took his whole shaft in my mouth in one deep gulp and then
tightened my mouth grip on his meat.
For a minute I simply sucked and released without moving up and down.
Barry's whole body tensed, not ill a pre-orgasmic manner, and l sensed that he
was using every inch of willpower to stave off his impending climax. Apparently it
worked, as he remained tensed but didn't spurt.
When I saw that he was keeping control, I clenched my lips tight and
dragged them up his quivering stalk. At the tip, I took a deep breath, dipped my

tongue in his piss-hole, through the rubber, and then started down again. Down
and down and down until my nose was buried in his curly pubes.
Inhaling the musky man scent, I held the position as long as I could,
alternately sucking hard and releasing, but not moving my lips. Finally in need of
air, I sucked my way back up, dragging my tongue along the flat underside as I slid
tightly upward.
But at about the midpoint, I felt Barry's body tighten in a different way and
realized his self-control had gone to hell, and he was about to shoot off. Sure
enough, his rigid, swollen dick shaft grew even larger and. harder, then quivered
and powered out a stream of hot man sauce, filling the condom's receptacle end
and warming my mouth.
"Good grief!" Barry exclaimed. "That was ... that was ... wow!"
"Feel like treating me to some 'wow' in return?" I asked. "Your initiation
into gay sex isn't complete till you've done to me what I did to you." And been
fucked, too, I added silently. But I didn't say it aloud. I didn't want to spook the
guy. Let him take it a step at a time.
"I-I can try. Sure!"
I snapped another condom into place, this time on my own dick, and
stretched out expectantly.
Barry licked my scrotum first. Lapping across the wrinkled surface of my
sac, he scraped delightfully on my leathery skin. Then he wrapped his hand
around my stiffy and began jacking it up and down. At that, at least, he was good.
He'd had enough practice on his own tool, I guessed, to be proficient at jacking a
dick. But when it came time to suck on it, that was a different story.
He first tried to simply lick the dickhead. While continuing to jack me, he
licked and swabbed and swirled. It was enjoyable for the first couple of minutes,
but I soon wanted more. "Suck it," I coached. I could feel him tense up at the
words.

He wrapped his lips around the glans and sucked-hard too hard-as if trying
to pull my cum out by sheer force. And he still barely had my dick in his mouth.
But if his ineptitude was frustrating, it was exciting, too. Knowing mine was the
first dick those lips had touched, knowing I was the first guy to suck, to be sucked
by, and-I hoped it would happen before the evening was over to fuck Barry was a
huge thrill. I had myself a virgin! My first. And I was enjoying the hell out of it.
But I knew I would enjoy it a lot more if he were doing it right. So I gently
coached him: "Take your hand out of the way and sliiiiide your lips down my
shaft. Don't try to take too much at one time. Just take what you're comfortable
with. But I know you can take more than that."
His eyes reflected skepticism, but he manfully tried to swallow more of my
shaft. Carefully sliding down, he took in a little more... a little more ... and still a
little more. When he was halfway down, he stopped.
"Now slide back up and keep a steady suction."
"But you didn't keep a steady suction."
"You'll learn to get fancy later. For now, master the art of a basic blowjob."
He returned his lips to my dick and resumed sucking. He sucked harder but
not too hard, and this time, when he worked his cautious way down, he managed
to take just a little bit more of my dick into his mouth. Soon he was speeding up
and down my shaft with precision... though he still wasn't taking much more than
half in at a time. And though I'm a respectable six-and-a-half inches, I'm certainly
not possessed of any hard-to-swallow whopper.
"Try to take a little more ... if you can," I encouraged him.
He tried. He could.
He got about three-quarters of my dick shaft into his mouth. I began to
wonder how much more he could take. But the concept that I was fucking virgin
lips proved to be too much for me. My balls were fired by the knowledge that my
dick was lodged in a cherry mouth, and I realized I was nearing the point of no

return. Rather than fight it, I went along with it. Feeling my balls scrunch up into
my body, I gave a sudden, violent, upward lunge and spewed my seed into the
rubber in his mouth.
The same knowledge that had gotten me off too quickly the knowledge
that Barry was, or had been till now, a virginal so got me hard again quickly. I was
going to fuck his virgin ass! I was going to skewer those guts that had never
before been invaded. As my half-flaccid dick began to re-inflate, Barry askedeagerly, I thought-"Do you want me to suck you again?"
"No. I want something else," I answered, feeling a wicked smile twist my
mouth up.
Barry looked at me dumbly for a minute. Then slow realization spread
across his face. And fear. Definite fear. "Oh... no... you don't want... ?"
"I want your ass, baby. I want that cherry butt-hole. I want to feel your
tight, tight rectum gripping my dick while I plow... well, you get my drift."
Clearly he did. It showed in his face... and in the way his muscles tightened
up. He looked ready to back out, to turn tail and flee. I had to move quickly.
Spitting on my finger this was no time to go hunting for the lube-I squirmed it into
his asshole, thrusting inward with a quick twist.
As I'd hoped, it felt good even more than it hurt. His cherry bung was tight,
and I'm sure my finger burned him, but it also felt good. Great! His eyes went
wide with wonder and revelation. I followed the finger with a second one and
began driving the two fingers rapidly, in and out. Thrusting quickly, I plunged in
and out of his never-breached bung, then said in a low, compelling voice, "Lie
down. On your back. And Raise your legs up. That way you can see me while I'm
fucking you... and I can see your face when I'm first fucking you."
Barry complied. Slowly, to be sure, as if in a dream, but without protest or
hesitation. I opened a drawer, got out the lube and a fresh rubber, and made
myself ready hastily. I, slathered gobs and gobs of goo on the rubber. Then I put

my rubbered dick up to Barry's bung and warned him, "It will hurt for a minute...
but the pain. will go away quickly, I promise."
And then I drove in fast before he could freak and change his mind.
"Yow!" But he didn't try to stop me. "Oh! Ow!" And then, "Ohhhh." Not an
"Ohhh" of pain this time.
I had driven about a quarter of my dick into him and stopped. Now I
cautiously but determinedly shoved in farther.
"Mmmmm."
"Mmmmm," I echoed. And thrust the rest of my dick into his receptive
bowels. The tight tissues wrapped around me. And then I began sawing back and
forth. In and out. Plundering his guts recklessly, I speeded up and really slammed
it to him.
Of course, now that it felt good to Barry, it felt spectacular. He'd never felt
such a thing. And, of course, his sex nerves overreacted. Splat. He was shooting
off, decorating my neck with a hefty helping of spermy spray. Feeling his cummy
mess all over my neck, dripping down my chest, set me off. Five more strokes, in
which I held back nothing, and suddenly I too was shooting off.
Barry and I spent the night together, and we really made a night of it,
though I never saw him again after that. Still, to me the story has a happy ending
... after all, I'd gotten his cherry, and he'd finally made the decision that had been
bothering him for so terribly long.
We were two very contented guys.
What could be happier than that?