I walked out my apartment door to find a man on a ladder leaned against the front of the building. It was a small complex of seven units that used to be a motor court in the fifties and now catered to queer people. He wore a pair of painters overalls and, from the way the outline of his cock stood out as he pressed his hips against one of the rungs, not much else. I couldn’t help but walk under the ladder and get a better look. For a Monday morning, it wasn’t a bad start to the day.
I was twenty-six and very into yoga at the time. I was wearing my usual outfit of a loose gauzy oatmeal colored top with almost sheer pants of the same color that showed off whatever underwear I’d chosen for the day. Today was a white thong. At 5’11” I weighed 140 pounds and would best be described as wiry.
“Hey, don’t you know that’s bad luck,” the voice asked as I unlocked my car.
“For me or for you?” I gave him a wink and shut the car door.
He smiled at me as I backed out of my carport. He wasn’t traditionally attractive. He’d clearly spent too many hours baking in the Arizona sun judging from the deep permanent tan with so many deep wrinkles he looked like an east coast road map. His smile was framed by a white mustache and goatee. There was something cute and innately sexual about him. Perhaps I was just longing for a man who had the experience to show me some new tricks.
When I came back from grocery shopping he’d moved on to the next building. I’d finished putting away groceries when there was a knock at the door. There stood the painter in his overalls with the zipper pulled down to his navel. It was a hot day, nobody could blame him for wanting to be comfortable. I, for one, wished he’d pull it down a bit more so I could get a better look at what was making the bulge that pushed the center seam so far to the right.
“Hey, I’m Nick. Just letting you know we’re going to be painting the buildings. Probably start with your building tomorrow morning. Your neighbor said she’s up by five, was wondering how early you get up. Trying to see if we can start early to beat the heat.”
“Usually I’m up with the sun since the bedroom window faces east.”
“So you’re okay with five then.”
“Yeah, that’s fine. I’m Eric by the way.”
“Also, we use a sprayer, so we’ll be covering the windows and doors. We can either cover your car or you can move it.” He adjusted the bulge and I for a moment my eyes took a rather long gander consuming most of my brain power needed to respond. He tapped on the screen between us. “So…you gonna move it?”
The metallic echo of the screen brought me back to the moment and I opened the door. “Sorry. Yeah, you can cover it. I don’t have any appointments until tomorrow afternoon. You’ll probably be moved on by then.”
He grabbed a rag out of his pocket and wiped off the sweat running from his head and down his chest. “Cool, cool.” He took a moment and then leaned on the frame. “Can I ask you a question?”
“Sure.”
“What’s up with this complex? All the guys I’ve met have all looked like they came out of a catalogue.”
“It’s a gay complex and don’t tell Cheryl she looks like a male model or she’ll kick your ass.”
He laughed at my warning. “Ah, that would explain it. Okay, I’ll see you in the morning.”
He walked away and I closed my door. It was one of those times in my life where I wished I’d been like my friend Tim and been a total whore and fucked that painter. An hour later I was vacuuming and saw him and his assistant, a short stocky black kid, probably younger than me. My regret from earlier compounded exponentially. The afternoon ended up being two jack-off sessions with very different searches than I usually use.
I fell asleep like I do most nights, wearing only earplugs. The next morning I woke to two shadows moving across my bed. I’d forgotten to close the shade facing my little back yard as I usually just use the rising sun as an alarm clock. Also, at some point in the night, I’d thought the thin sheet had become too much and kicked it off the side of the bed. Quickly, I jumped out of bed and made my way into the bathroom. Had they seen me? Surely they had seen me laying on my stomach bare ass naked. Maybe the glare from the sun on the window blocked their view? Ooh, wait, there was supposed to be plastic. I threw on my short little silk robe I’d gotten in Japan a few years prior and peeked my head around the corner.
There was no plastic. Just the two of them in their white overalls with their crotches at the height of my window. I slid the window open. “Good morning! I thought you were going to put plastic up.”
Nick crouched down on the small ladder he stood atop, “Plastic gets put up when we start spraying. Just scraping the trim and repairing some of this flashing. Probably start spraying in a couple of hours.” His benign delivery of facts had a calming effect on me. Clearly they hadn’t seen me.
The calm was shattered when his young assistant squatted down. “Probably would have been done with this part by now if we hadn’t spent all that time staring at your ass. Damn, that’s nice!”
I could feel myself turning red as I eked out, “Thanks,” then slowly slid the window closed.
I walked into the kitchen to start my coffee when a feeling of anger overtook me. “What the fuck is wrong with you? Two men have flirted with you and you’ve shut them both down. Are you not interested in them? Are you not interested in sex? You’re a single gay man in your mid-twenties with an ass that was just described as ‘nice’ by a very cute young black man for fuck sakes.” Internally I answered my own questions and decided I wouldn’t mind either one of them. I also reminded myself that this was the year I had set for myself to stop dating toxic white guys my age that are only interested in their ejaculations and their spot on the corporate ladder.
Speaking of ladder, there were two men who might want a cup of coffee on ladders. I loosened the sash on my robe so there was a chance I might turn suddenly and my soft six inches could perform a little peek-a-boo routine for them and went back into the bedroom. This time I opened the back door onto my little patio area, sticking my leg out of what little slit the robe created. “Would either of you like a cup of coffee?”
They froze, exchanged a look, and then the assistant jumped down. “You need something to wake that ass up, I got it right here.” He grabbed his half hard cock through his overalls.
Internally my libido drop-kicked the religious-based-guilt in me as it tried running to my mouth. “I’ve always put cream in my coffee, never gotten it out of coffee.”
He smiled at my lame little joke. “Fuck yeah, I love breaking in newbies.” He looked over at Nick, “You okay if I take a quick break?”
“Next job we do I’m adding an extra charge for you fucking. Probably double the bill.”
My libido had clearly taken my mouth hostage, it was the only way I can excuse what came out of my mouth next, “You’ll probably need a break too at some point.”
He climbed down from the ladder with hammer in one hand and a look of confusion on his face. “Really?”
The confused look jumped to my face, “What do you mean? Like you weren’t flirting with me yesterday?”
“Yeah, but I didn’t figure I had a shot. I mean look at me? Especially next to him.”
I kissed him on the cheek and ran my hand over his bulge as I offered what could best be described as a pick-up line from a fortune cookie, “When I go to a Chinese restaurant I often can’t decide between the beef and broccoli or the orange chicken. A lot of times I order both and take one home.”
“Robbie, scrape the rest of this building and replace any of this bent flashing. I’ll let you know when he’s ready for some orange chicken.”
Nick and I went into the bedroom. I jettisoned my robe as he pulled the shade down and Robbie’s shadow disappeared into the deco inspired wallpaper I put up a month prior. I stretched out across my bed and Nick stopped midway through the process of getting naked. “Are you sure about this? I mean, I’m sixty. I gotta be about three times your age.”
“I’m twenty-six, so you’re only about double.” I turned over onto my hands and knees and raised my ass covered in a light dusting of blonde hair in the air, shaking it like a puppy. Twisting my head around to meet his gaze and winked my hole at him, “I’ve heard that eating ass makes you feel younger.”
In a flash he was completely naked. His body was toned, but with a little gut. His chest hair had yet to go grey like his facial hair. I scanned down his body as he walked over to me. His cock and balls made me rock hard in an instant. A big fat floppy cock swayed in unison with his heavy sack like a singing trio from the sixties dancing to choreography.
His oral skills were second to none. This man loved eating ass. Up until now I had clearly only been with men who did it out of a sense of duty. His flat rough tongue ran from the base of my balls, up my crack, and the smooth back of his tongue took the same journey back. At the end of this motion, the tip would uncurl and flick the back of my balls, making me moan every time. I’m not normally a selfish person in bed, but I honestly think Nick somehow hypnotized me through my asshole with his amazing tongue. I didn’t move or make any attempt to switch to a position where I could pleasure him. I just stayed there with my ass open wide and enjoyed this man eating my hole.
I think the muscles in his jaw must have started to cramp because his hot breath left my body and his rough thumb began to explore me. I looked back to see his cock slightly hard, but not yet to full-mast. “Can I help you with that?”
“Fuck yeah, get that pretty mouth on my dick.” I positioned my head so it hung off the side of the bed and eagerly gobbled up his cock while he bent my body in two and went back to work eating my ass. His cock swelled in thickness until I was pretty sure I could swallow a Foster’s can if anyone ever made such a bet. He moaned into my ass and I moaned into his cock.
“Holy shit!”
I craned my neck to extract his cock from my mouth, “What’s wrong?”
“We’ve been in here for forty-five minutes already.”
I stood on my knees on the bed as he stood by the bed with his cock drooling pre-cum. “Well, I can’t let you leave like that.” I turned my ass to him. “Come on, show me how many times sixty can go into twenty-six.”
He wasted no time inserting himself in the middle of my everything. “Fucking hell! Maybe it’s because it’s been a while, but your ass feels amazing.”
I looked back at him, “No, it’s definitely my ass.” My wink was rebutted with a slap on my ass as Nick started fucking me.
At first his pace was nice and steady like an oil well churning away in the earth, but it wasn’t long until all the excitement of the moment had him pounding me until he came. He collapsed on my back and my body gave way under his weight. We laid on my bed for a few minutes as the ceiling fan made all the sweat on the sheets turn chilly to the touch.
He lifted himself off me and I watched as he got redressed. His eyes widened, “Oh fuck, you didn’t cum. I was so worried about time and everything. What can I do to get you there?”
I smiled, “I still got orange chicken.”
He smiled and nodded his head, “Once you see Robbie’s dick, I think you’ll call him beef and broccoli for sure.” He started to leave the room and then he paused, “I know I’m too old for you and this is maybe a weird time to ask this, but are you dating anybody?”
“The answer to that question is a definite no, I am not dating anybody.” He understood what I meant and his chest deflated a bit. I continued, “What’s your favorite movie?”
He furrowed his brow even deeper than it was naturally, “To Catch A Thief, why?”
“I’ve never seen that movie. How about you come over, we get naked, and we watch it together? Just a friendly movie night.” I stressed the ‘friend’ part.
“I think I’d be too distracted to watch it.”
“That’s what pause buttons are for.”
“Tomorrow?”
“Sure. Now send in my next dish.”
A few minutes later, Robbie stumbled through my back door. He was stripped clean by the time he found me in my bed and plopped down beside me with his ten inch cock and big balls swinging all over the place. He reminded me of a Mastiff puppy I had once who didn’t understand how big he was growing. “Suck my dick.”
The directness was fresh, if not a little jarring after my tête-à-tête with Nick. All my fellatio skills came into play wrangling his thick cock down my throat, but eventually I got my saliva at the right level and my breathing rhythm at the right pace and deep throated that fucker like a champ. I was feeling victorious until Robbie said something that felt like a gut punch, “You older bitches sure know how to suck a dick.”
I may have taken his cock out of my mouth, but it was no less agape, “Older? I’m only twenty-six fucker. How old are you?”
“I’m eighteen and a half.”
AND A FUCKING HALF!?!?!? With nothing to add to the conversation I reinserted his cock in my mouth. His cock that was so young it still used decimals to express its age. All I could think was, “This motherfucker better throw the best fucking dick ever!” Although, experience would tell me that was a tall ask for a man of his age.
Robbie too had a habit of checking the time. At the twenty minute mark he performed some magical gymnastic trick leveraging the bounce of my bed and my limbs and had me on my back with my ankles on his shoulders. He spit on my hole and we both hoped Nick left enough lube in me to handle his cock, although I bet I was saying a prayer with more conviction than he.
Slowly, thankfully, he pushed his cock into me until his weight pressed against my ass and my knees pressed against my chest. This is where his sexual maturity would end as he bounced his dick in and out of me, using my curved spine and taut hamstrings as his suspension. In all of two minutes he unloaded a nice large nut into me.
With his mission complete, he got up, redressed, wiped his dick off with a rag in his pocket, put the rag back in his pocket, gave me an odd Boy Scout salute, and walked out the door. I flopped back onto the bed and thought about the last hour and the vast difference between the two men. The heat from my throbbing cock brought to my attention the fact I still had not cum. I looked down to see my pink dick drooling pre-cum all over my light blonde treasure trail. A knock on my back door startled me.
I opened the door to see Nick standing in the morning light with his hard dick hanging out the zipper of his overalls. “Don’t suppose we could go again? You must really excite me, because it’s been a while for me to recover this quickly.”
“Come on in.”
This time I took no chances. I didn’t even undress Nick. I pushed him back on my bed in his dirty overalls, mounted his thick cock, and used him like a sex toy. He looked startled as I rode him like a possessed whore while I stroked my cock. “Work my nipples,” I commanded.
He did as instructed and found that he enjoyed the feeling of my ass on his cock whenever he twisted and pulled one of my nipples. “Fuck yeah, ride daddy’s cock. Milk daddy’s cock with that little boy hole.”
“Boy hole. That’s right fucker, I’m only twenty-six and it’s still boy hole,” ran through my head. Fuck that ‘older’ shit, this man had a thicker cock and more appreciation for being inside my ass.
“Pinch them harder daddy!”
Calling him ‘daddy’ was too much for him, he started giving the orders. He batted my hands away from my cock and started stroking me with his rough hands, “Work your nipples for daddy. Show me how much you can hurt yourself.”
Two seconds later my load was shooting all over him, my bed, the night stand, and even the wall. My ass spasming around his cock caused him to unload in me again.
I was drained, and not just my balls. I slumped over him with my chin in the crook of his neck. His hand ran up and down the small of my back as my heart rate slowly declined to a more regular rate. I could feel my cum dribbling out from between us.
“I know you don’t want to date anyone right now, but could I get a kiss?”
I lifted myself up with his cock stick slipping around in my hole, smiled, and kissed him. At first, it was just light kissing, but it soon evolved into something thick with passion. Speaking of thick with passion, I soon felt him hard again in me.
“Damn daddy, you’re hard again.”
“Yeah, but I got to get back to work and experience tells me this one would take a while.” He kissed me again, “If you want, we can watch that movie tonight.”
He’s been over three nights in a row and I’ve still yet to see much more than the opening car chase.
