I wondered to myself whether it would ever happen. My mind had been open to it for some time now, which it hadn’t been in my youth. In my early 40’s now, still athletically fit, offbeat handsome (so I’ve been told - who knows what the fuck that means), and mostly straight, but quietly willing to bend into the right circumstances, or for the right person. The willingness to bend part is much more recent. But the catch for me seems to be: When and how would the details, this right person, right time and/or place come together for this new desire’s door to swing open, welcoming in a deeply-craved sexual adventure?
Once I opened to the hunger, and dropped the shame part of it, it was always about the right configuration and guy, the latter being the more important issue.
In the arts, I’ve met my fair share of both extremes: the macho posers, hiding what, I’m not sure, but they are never the possibles; nor are the boys who needed to act uber-girlish in every way to feel a part of the gayer world. For my tastes, I needed someone in the middle, perhaps a little like myself, but different. And I wasn’t meeting him anywhere. I used to joke to myself that if I could create a clone, I’d have been sucking cock and fucking man-ass for the last few years at least.
What I imagined in reality was another guy with a similar curiosity, sensitive but masculine; mostly straight or recently “bi”; just someone daring to open himself to pleasure from another man for the sake of the pleasure and for sampling a new flavor of intimacy. Not to join a club or adapt a new sexual support group.
I thought that I’d most likely find him as a part of a steady or married couple, a guy who had been encouraged to open to his other sensibilities by a smart, patient woman longing to be a part of a bisexual mash-up. But no couples had offered to open their doors to me as of yet. I have never lost hope, but often wondered if and when those stars would ever align at last. The longer they took, the more I’ve wanted to make them align.
I had volunteered to host the closing night party of a successful theatrical production I was an integral part of in town. Cast and crew and friends all attended. Food and drink flowed aplenty, fun and song and silliness ensued. Then came the tearful goodbyes of the bonded masses, since the gig was over and the temporary family was disbanding. As always, into the wee hours hung a few stragglers, most of whom I knew.
As those final few gathered their asses and belongings together to leave, a thunderstorm hit and it hurried the group along. One young man from the cast that I knew only a little, was on his phone, madly calling and texting a friend… one who clearly had left without him. He was stranded.
I had happily offered my couch and other sleeping areas to anyone too inebriated to drive, but the last few folks left, offering regrets that they couldn’t take this young man home, since they were headed the opposite direction.
I said to the final party-er, Jack, “No worries. You can stay here. I’d offer you my bike, but you’ll get soaked in a half a block. I can take you home tomorrow, since I’m off.”
Jack thanked me, and in return, eagerly offered to help with the party clean-up which I was incredibly grateful to have. When we finally got the place to a liveable state again, we sat down with a cold beer each to chat away the last hours before sleep set in
As Jack and I began to share some stories and secrets of the stage, the road, and this production, I found myself to be very pleased with his late night company. He was a genuinely good guy. Young, good looking, and eager to make his mark with his craft, not some wanna-be “make me a star” egomaniac. He hung on my every word for a time, when I spoke of my training and how learning things in your head was one thing, but letting them settle into body knowledge and true experience was another.
We moved from topics of work to social life to dating to sex as we sipped and gabbed. The more we talked, the more I liked him. I asked him about one of the girls in the company, who I thought he was seeing. He said he liked her and they hung out, even fooled around a bit, but she had a boyfriend out of town, which as he put it, “sucked the big donkey dick”.
Had Jack not ventured the very next question, I wonder what, if anything, might have happened, or not happened. Thank the stars, he did.
"So," he started haltingly, "Do you only date girls, or have you been with men too?" He saw me raise one eyebrow at the question, and jumped in quickly, "I just mean, lots of people in the arts…. ummm…. try different things."
I smiled. I could see he was curious, not just about me and my leanings, but for himself as well. I think he needed to be given the go-ahead to consider it, without recrimination or shame.
"I haven’t been with men. But I’ve thought about it. Even imagined it." I let that spin in the air, to see if the masturbation hint sunk in. "I might have, if the right thing happened in the right way."
His brow furrowed with the unspoken question of “Why haven’t you. then?”
"Mostly, Jack, I was happy with the women I was with, and then, when I did begin consider and desire a dance with the other side, the right situations didn’t show up for me. I still would, if it felt right."
He tried to suppress a revealing smile. And that shifted me just enough in the right direction. I decided to ask about him, as this suddenly showed some surprising promise.
"And you, Jack? Tried guys?"
He blushed, head down. He had, clearly. I pressed it. “Tell me about it. Anything we share is only between us.”
"Oh, I don’t mind. It was just…odd. I was curious and someone I was in a show with hit on me. I thought it would be cool to try, and I wanted to see how it felt, all of it. It turned out he just wanted to blow me so he could tell his friends he turned me gay."
"Yeah, I’ve seen that happen. There’s always a few bad apples preying on the newbies. I hope the BJ was at least worth it."
He laughed. “It was pretty good. But I can’t think of it that way anymore, since he turned out to be such an asshole. The kind of asshole I don’t wanna fuck.”
We both laughed. Then the silence hit, both of us looking about, until our eyes caught each other. And we stayed there. Longer than expected. I knew. I could feel the sexual tension building, but as always, I second-guessed myself and thought, He doesn’t want an older guy..”. I was wrong.
I offered to get him some sheets etal for sleeping as he took our bottles and a couple of plates into the kitchen. Both of our minds were obviously racing in their own respective, horny spinning worlds. They wouldn’t have to wait long for the answers.
When I finished setting his sleeping corner up, he was busy washing the remains of the dishes. I walked in and quietly watched him, noting the perfect shape of his ass, and I let that take me to places I had yet to dare. I thought, worse case scenario, he’s gone tomorrow if it gets awkward.
I had already seen the bulge rise in his jeans during our last conversation, so I sensed that he was likely game. Not to mention that hopeful, hungry look in his eyes during our shared awkward pause before we broke the last build-up. I decided that the stars had finally aligned for me and I was not about to toss this gift horse out the window.
I walked up close behind him. His taut ass was almost leaning into my hand. “Thank you for doing those. And for all of your help.”
"No problem", Jack said sincerely.
He was drying his hands and hadn’t turned around yet.
"I"m not sure how you feel about this", I said gently, "And you have no obligation here whatsoever, Jack…".
I could see him stop, and breathe in, and wait for the rest of the sentence.
"But if you have any urge to finish that, ummm, unfinished encounter… the part you didn’t have with your friend… well, I’ve always wondered how that would feel. And you just might be the right… configuration."
I let that invitation crackle in the air. His body arched in an unconscious offering, and his ass was so close to my hand, I let myself cup his left cheek for punctuation, and I heard him purr softly. In an instant, i could tell he was mine for the taking.
He still had not turned to face me.
"Like I said, no pressure, no obligation. You can stay no matter…."
He cut me off with his words, “Yes. I want to.”
"Really?", I asked to be sure.
"Really. I almost can’t believe you asked. I was hoping…. it’s kinda why I stayed so late."
"Tell me why, Jack. I sensed something with us, but wasn’t sure what it was about."
He turned and was bushing full-on red. it was rather sweet and truthful. “I… just really want to. With someone like you… especially now.”
"After our talk… you seem… perfect. And your talent and confidence is so… uhh, attractive."
He made me blush this time. But I understood. I have fallen for talent before. Any kind of talent can make someone you already like hyper-desirable.
I smiled, ” And here I thought you only wanted me for my cock.”
We both laughed, then he said, “Well.. there is that.”
A long paused ensued, neither of us sure who should do what next. It felt perfect, really. It told me that this indeed was the right moment and he was definitely the right first-time lover.
I moved in to kiss him, and he readily submitted. As we began tasting one another, opening locked jaws and slipping slithering tongues inside the others’ warmed lips, his hand slid to my denim-wrapped cock’s bulge in the same nano-second that mine gripped his.
We started slowly, studying rather than jockeying for position. But as each of us had allowed the other to dip his tongue deeply into our respective throats, somehow we both knew that we would share the reins, no matter who took them first. Another piece of wet alignment fell into place.
We mirrored each others’ shirt removals and once bare-chested, I pressed him to the sink’s edge and began to grind my bulge into his. Moans erupted on both sides, and soon I found myself nipping at his neck and ear and whispering things to him….
"Your body feels so good, Jack. That shouldn’t surprise me, but it does. Sooo good. I waaannnt it. I want you…". This time I surprised myself more than him, "I want to fuck you, Jack."
That made him push back and grab my ass hard and moan louder. I loved how he wanted me to desire him like this. And fucking hell, the more we played, and traded aggressions back and forth, the more I wanted all of him, in every filthy way under the wicked moon.
We were now instinctively unzipping each other, and as soon as we were bereft of our clothes, I pulled him back and sat myself on the kitchen table, pulling a chair in front of me for him to sit in, as I smirked…
"Isn’t this what you didn’t get to do?"
He must have been wet-dreaming of this forever, because he turned the chair around, and knelt on it like he was on a pew at worship. And at the first touch of his hand, and the first full wrap of his lips on my hard cock, I shivered and my swelling dick’s head wept tears of pre—cum joy.
Here was that very gentle, but very masculine young lover taking his first taste of me, and his touch already had my toes curling and my nipples rock hard.
I let my fingers slide through his short hair as he began to move in closer, then move out again in his long seductive mouth-riding motions. I kept humming about how good he was, not to spur him on so much as, because it kept surprising me that a male was taking me so brilliantly towards unprecedented orgasmic peaks with his lush unstudied mouth.
Once he took me in to balls deep on my shaft, and made me growl out loud, he knew he had me, and he began a deliberate tease like none I’d felt before. It was a steady rising slip-n-slide, base to head and back - never stopping, only intensifying. It felt like a hot, wet half-shaven cunt straddling me and fucking me just enough to take me to the edge, but not let me go over.
He knew the effect he was having on me, though he admitted later it was pure instinct. He was just thrilled it was working.
At one point, things got so intense for me that I pulled him full onto my pubic bone and nearly gagged him completely. I let him loose while still fisting his hair and I looked down to see his eyes watering and his mouth full of my shaft.
"Holy fuck, you look beautiful, Jack!"
He couldn’t speak, but his eyes were begging for me to finish right there and pour my lust down his throat. He would not have to ask twice, even silently.
I stood up and began to fuck his face willfully. We both began to grunt and roar like mating animals. He clawed at my ass and wiggled a finger near to my anal opening when he heard that edge-of-orgasm stream of obscenities spill out of my mouth. That was his cue to open his throat. The fucking flood was cumming..
It was probably from the sheer act of shattering old taboos, but I don’t remember emptying that much seed into anyone’s face before, or perhaps not in a very long time anyway. He took it like a pro, gurgling, gagging a bit, but holding my thundering eruption between his cheeks until the spasms continued, but my creamshot ran low.
I’m sure my eyes were turned about backwards through much of it. but when I looked down at him, I almost started to cum again. Those big, lustful, watery eyes looking up at me with so much satisfaction, his lips still wrapped about the top third of my shaft, and the spillage from the corners of his mouth made my knees weak. Holy fuck, I though, I may have to ask him to do this every day, though I’d save the actual utterance of that thought for later.
"Jesus H. Fucking Unbelievable Christ, Jack!!! You sure you haven’t done this before?"
"Mmmm hmmmm" he answer in the "no", just before he slid off and let the cum from my cock run down his chin.
He fought to swallow enough to speak, then gargled through the sticky cream, “I’ve imagined. And practiced… on things.”
"Yeah, well you could debut at Carnegie Hall already after that kind of practice!" semi-quoting the old joke.
I crumbled to the floor, kissed and licked and tasted his cock, and said, “I hope I’m half as good on my first try.” Then I slid up to his face and we shared the filthiest hottest kiss I could remember in forever.
Here was the boy who just swallowed a huge load from my sex, and now he was painting the inside of my mouth with the leftovers. Fuck! He was not only a hot man-boy, but sensual as hell. ‘I just might have to keep him’, was the newest quiet thought in my head.
I convinced him we should lie down in his newly made couch bed. I led him by the hard cock, stopped by the sofa, then decided, fuck it, I wanted him in my bed. For the rest of the fuck-all-night. I led us there shamelessly and he followed like the happy, horny, hungry boy he was.
I stopped, kissed his cummy mouth again, wrapped my fist around the lush shaft on his perfect dick and locked eyes with him.
"Tell me what you want to do with me. What you want me to do with you."
He blushed again, and all he could muster was a shy “Everything.”
That was all I needed to hear.
"Jack, here’s what I want. To explore and taste every inch of you. To try anything and anything we think of and both want."
I kept stroking his cock as I spoke on…
"I want to fuck you, face to face and feel what it is like to cum deep in that hot tight, gorgeous fucking ass of yours. I want to see how you look when you feel that happen. And I want to see how you look when I make you cum.Do you want that?"
He was flushed full red. He wanted what he said: Everything!
"I want you to fuck me too, however it turns on on the most. I want to ride your cock from above and cum all over your body and face. I want to find what makes you beg me for release and do it until you can’t speak enough to beg… then let you fucking fly. I want us both to be covered in sex and cum and anything else we think of… how’s that?"
He kissed me hard and pushed his hips into mine. I shoved him onto the bed face down, pulled his hips up, and knelt and pressed my face in to his thighs to capture his beautiful balls in my sticky mouth.
My tongue would probe his wicked asshole and my throat would let him drown me in cum, the way I did to him, before I topped him, and lubed him, and worked my joyful thickened cock so far into his spread-eagled body, that I would see him claw the sheets and hear myself actually say “God, I loooove fucking you, Jack. I never want to stop.”
"Don’t", he answered in between heated fuck-grunts, "Don’t ever stop."
The sun would be at high noon before we ceased our first fuckfest. The shower would take another hour of lustful playtime, then I drove him home.
We found a shaded spot to kiss and grope until I said, “Thank you. For all of this. It’s our little secret until we choose to share.”
He agreed wholeheartedly. “First shares”, I added, “Will be with the girls we invite to join us.”
He kissed me dirtily then said “I can’t wait for that!”
Then he got shy again with this, “But first…can I visit again this week?”
"Come to my bed anytime, Jack. Just don’t expect to sleep. Ever. I’m home by 10 tonight. Be there. With more dirty ideas. I might just take you in the back yard, press your face into the dirt and ride you like a rutting beast."
He hissed a wanton “Fuuuuck!” Yeah, he loved that idea. Write that one down in stone, I whispered to myself.
He would be the good boy, waiting for me upon my arrival that evening. We would leave no corner un-fucked at my house in the next few days. We talked about the girls we’d soon invite in, but for now, it was man-to-man fuck week, and no girls allowed… not just yet.