Henry

One of the perks of living in southern California and running a vintage clothing and furniture store, is the plethora of retirement communities. I know it sounds mean, but old people die, and their vintage belongings need to go somewhere. On a sunny Sunday morning, I was perusing local online ads when a ridiculously low-priced racing bicycle from the eighties caught my eye. It was turquoise and pink, it would have caught anybody's eye. Judging from the pictures, the seller lived in a senior living community. I messaged the seller on Facebook to see if it was available and we exchanged enough information to get me past the guard gate when I arrived.

Monarch Manor was a smaller community laid out in a grid pattern. I slowly drove along through rows and rows of manufactured homes until I saw the sign for Goldenrod, and turned right, eventually finding number 149. It was an older single-wide trailer painted a garish seafoam trimmed in white with a carport on one side and a screened in porch on the other. I parked in an area clearly marked for visitors in such a way you felt you might be towed if you disobeyed.

Just as I was about to ring the weathered doorbell on the screened porch, a man poked his head around from the other side. "You Tommy?"

"Yeah, you must be Henry."

"Yeah. The bike's in the shed over here."

I went over to the carport and followed Henry to a little shed at the end of the carport, at one point having to squeeze between a set of stairs going into his house and a giant Cadillac collecting dust. He was somewhere around my height of 5'11", while age had taken a lot of his hair, his muscular legs and bubble butt stayed intact, and it was clear he still lifted weights with his upper body on a regular basis. He opened the door and turned on the brightest array of fluorescent lights I'd ever seen. Even compared to the midday sun, they were bright. He wheeled the bike out. "Here she is."

The bicycle was near perfect with only a minor ding on the front fork. "And the price is $150?"

"Yeah, yeah, it's an old bike and you'll probably have to do a little work to get it going again, clean the chain, adjust the derailers, probably needs new tires and brake pads too."

I knelt down and examined the tires, brakes, and drivetrain and couldn't see anything out of place. "You used to ride?"

"Nah, my partner used to, but he died a few years back." Henry's demeanor changed and he started to retreat into himself. His voice lowered into sadness. "Figured it was time to start clearing stuff out and moving on finally."

"Sorry to hear that." I looked up at him and got a good look at his face. Blue eyes, tan skin, silver eyebrows, and thinning silver hair all combined for a very distinguished look.

"Thanks. It's been weird being this old and single."

"I'm twenty-eight, and trust me Henry, it's weird at any age these days."

He smiled and looked over in the direction of my car. "You think you'll be able to get it in your car?"

"Yeah, the seats fold down." I stood up and felt for where my wallet should have been. "Ah shit!"

"What's wrong?"

"I forgot my wallet in the pants I wore last night. Do you have any electronic payment apps?"

He laughed, "Kid, I can make calls, text, and check Facebook, and that's about it. You're talking to someone who still has a yellow wall phone in their kitchen."

It was a longshot; rarely did I find tech savvy seniors. "Would you mind holding it until tomorrow? It's a bit of a drive from my place and I've got an appointment out this way already scheduled."

"Listen, you were the first one to contact me, but there's other people interested."

While I could totally understand his position, I also noticed he said it while looking at the bulge in my pants. I decided to do something I rarely did, try and be sexy to get what I wanted. Besides that, he was kind of cute. I leaned over the bike, trying my best to strike a sexual pose, but fearing I might just look like I had a case of sudden onset scoliosis. "Is there anything I could do to convince you to wait until tomorrow?"

Henry's eyes got wide, but he didn't recoil. He furrowed his brow in confusion, "Are you suggesting what I think you're suggesting?"

I leaned in closer and caught a whiff of his aftershave. I whispered into his ear, "When was the last time you had sex Henry?"

Again, he didn't back away and all the sadness of talking about his partner disappeared, leaving a low husky voice. "Aren't you a little young to be asking me that? I don't even know you."

I kept my position inches from his ear. "You were the one staring at my shorts. If you let me go, all you'll have is regrets and an old bike you don't ride."

He backed up and looked me in the eyes, "If I looked like you, I'm not sure I'd be wasting my body on an old man and an old bike."

The comment caught me off guard. It was both sweet and protective and made my heart beat in a way it hadn't in a while. My original intention had just been to suck him off to get him to hold the bike, but now I really wanted to have sex with him. Maybe even more than once. I leaned the bike against the shed, pushed Henry in, and closed the door behind us. I pinned him between my thickening cock and his meticulously organized workbench. "I don't think it would be a waste at all."

Lightly, I kissed the nape of his neck, worked my way up to his jawline, and then settled on his lips. Little kisses grew into passionate ones until our tongues intertwined. I was not the only one in the shed with a bound erection in my pants.

"Are you sure? I mean, I'm turning seventy next month."

I rubbed my solid bulge back and forth across his solid bulge. "Don't I feel sure?"

We continued to kiss for a while until I just couldn't stop myself and knelt down in front of him. First, I lowered his shorts and nuzzled his hard cock under the front of his navy blue jockey shorts. A little drop of precum soaked through and swiped against my cheek. He smelled of fabric softener and ivory soap with a hint of something wicked. I slid down his underwear and his thick veiny cock slapped my forehead. Tilting my head back, his cock left a trail of cum from my forehead, down the bridge of my nose, and on my upper lip. I engulfed his cock and felt his long pubes against my chin and his balls hanging just below.

He let out an audible gasp and his cock swelled to an even greater girth. I placed my hands on his thighs to steady me and went to work on his cock. His girth made it easy to get a tight seal and I sucked until I could feel my cheeks sink in and rub against the side of his dick. My tongue played with the bulbous vein running along the base and played with the head before I took him in again. Henry just stared down at me and clung to the work bench with all his might. It wasn't long until his breathing became labored, and his expression changed, contorting between the choice of cumming or continuing to enjoy my mouth on his meat. In the end, he chose the former. I was not prepared for how much cum he would produce. Years of no human contact had built up to the point I had swallowed twice, and he was still unloading onto my tongue.

We stayed in this position for a few minutes as his cock went soft in my mouth and his brain processed what had just occurred.

I let it slide out of my mouth and kissed the head. "How was that?"

He smiled broadly, "Yeah kid, I'll hold the bike."

I laughed loudly and rested my head on his thigh for a moment. When I stood up, he noticed the bulge still in my pants.

"I guess it's your turn now. It's been a while since I sucked a dick." He threw down a kneepad used for gardening and looked at my raised eyebrow. "Old knees like a little padding."

"Um, actually, I don't really like getting blow jobs."

Henry didn't say anything, he simply undid my shorts, pushed them and my underwear down, and spun me around to face the wall where rakes and shovels all hung in assigned spaces. Then he pulled my bare ass against his limp cock and whispered in my ear, "But I bet you like that ass eaten."

I answered by pressing my ass into him and placing my hands on the wall for support. Behind me I heard his knee click as he knelt on the pad and then his hands running all over the curvature of my backside. "Fuck, that's a sweet ass Tommy."

"Thank you."

He spread my cheeks. "Mmmm, love that little pink hole and those blonde curls in there. Fuck yeah."

Those would be the last words I would hear from Henry for a while. He was a master at eating ass. I always hate when guys use the end of their tongue and dart in an out like they're trying to make it feel like a dick. Henry knew how to use his lips, his flat broad tongue, and even suction. His tongue explored from the back of my balls to the top of my crack and his deep moan vibrated me to my core. I spat in my hand and stroked my six inches as he worked my ass over. Usually I take forever to cum, but it was mere minutes before I was announcing, "I'm gonna cum!"

Henry spun me around and thrust his face onto my erupting cock with all the gusto of a soldier protecting his platoon from a live grenade. I grabbed his head and held it against me as streams of cum shot from me. I finally relaxed and released him from my groin. He stood up with a shiny spit and cum covered smile.

"Well, that was unexpected," he said pulling himself back together and using a red shop towel to wipe off his face. He took another off the stack and handed it to me.

I dried my ass off and pulled my clothes back up. "Yeah, I didn't have this on the agenda either. How are you feeling? You know, being with someone new."

"Different. Good. Can I ask you a favor though?"

"Sure."

Henry stepped close to me, pinning me between himself and the garden implements on the wall. "When you come with the cash tomorrow, can you be... you know... ready?"

I kissed him on the lips and whispered, "Way ahead of you."

He smiled at me and led me to the end of his driveway, waving as I drove away.

 

The next day, I arrived at nine in the morning with my ass ready to go. I rang the bell on the screened porch and Henry opened the door wearing a robe with the sash tied in a perfect bow.

"I love opening presents," I said before kissing him.

"I love opening asses." He grinned devilishly and gave me a wink. He was clearly ready to go.

He led me into the house and into his bedroom. Judging from the liberal use of maroon, florals, and curtain swags, I'd say it was last decorated in the mid 1990's. As I slipped my shoes off, he lifted my t-shirt over my head and then pulled down my gym shorts, revealing a black jockstrap. The site of my body in only a jockstrap, made his breathing shift. "Damn, you know what I like." He put his arms around me, taking a cheek in either hand, and kissed me. "What's your favorite position?"

"I think you'll find, Henry, I do better with direction. Can you be dominant?"

He cocked an eyebrow and shook his head in the affirmative. "Yeah, if that's what you want."

"Yes sir."

An evil laugh worked its way from the depths of his soul to fill the room. "Doggy style. End of the bed."

I did as he instructed while he slipped off his robe and took something from a drawer behind me. A moment later a light slap of a leather paddle resonated off my right ass cheek. I emitted something between a yelp and a moan, and my cock got rock hard.

"Looks like Tommy likes the paddle."

"Yes sir."

A swat connected with my left cheek. He continued to alternate between my cheeks for a while. "Look at your ass in the mirror."

I turned my head to see my bright red ass reflected in the mirror above his dresser. "Thank you sir," slipped out of my mouth as natural as breathing.

"Good boy." He rubbed my ass and then pressed his face into my crack. The day before had been tame compared to this ravaging. With his tongue pressed against my hole he reached up and twisted my nipples, making my hole clench and grab at him. "Fuck that's hot. Damn, look how much your dick is drooling. Get on your back." Peering between my legs, I could see the front of my jock drooling a long thick string of cum.

I flipped onto my back, and he grabbed my hips, sliding my ass off the end of the bed. The spit on my hole and the cum leaking from his cock slid together while he placed my ankles on his shoulders.

"Here goes nothing." He said, pressing into me.

My giggle at his statement suddenly turned to a gasp as his girth stretched me and the head slipped in. "Doesn't feel like nothing."

He smiled, kissed my calf, and waited a moment for me to relax.

While it was sweet of him to take such care, I much prefer a more forceful approach. "You don't have to be gentle with me. I mean, you have been making my ass look like a baboon's."

"I can do rough. You want a safe word?"

"I'm not restrained, and we're not using toys, so, go ahead and fuck me like a fantasy."

His arms reached around the outside of my legs and his hands pinned my wrists against the bed as the weight of his body pressed into my ass in one fluid movement. A scream left my mouth as he stretched my hole wider than it had been in quite some time. His balls rested briefly against the top of my ass before he started thrusting like a steam engine leaving the station.

I cried and moaned all at once from the pain and the ecstasy while he stared into my eyes with a look of bliss from the feeling of my ass tight around his cock. He stretched his head down and chewed on my left nipple, making my ass squeeze him even harder. He hummed an "Mmmm" into my heart.

We stayed in this position for a while, then he placed me on my side. In this position it was easier for him to cheat the angle and really dig into my prostate. He wiped a gob of cum off the front of my jock and licked it. "Mmmm, sweet."

His pace was quickening. He grabbed my throat with his hands and used my body like a fleshlight for a while. A few times I came close to passing out.

With his cock still in me, he turned me over onto my knees and started going hard on my ass. Occasionally he would pull out his meat and then ram it back into me at full force, our bodies slapping together and his balls swinging into my taint. His pace became animalistic, ­­and I could feel his cock swell slightly more. I thought at any moment I would be filled with cum, but he other plans.

He pulled out of me and got into bed. "Hop on. I want to see how bad you want this cum Tommy."

I straddled his thick wet cock in a squatting position and slowly lowered my aching hole onto him until I was sitting on his thighs. I leaned back onto my hands and started moving my ass up and down his shaft, squeezing it with every upward stroke.

"Love watching you take my cock. So hot seeing your hole stretched and how it pulls out as it grips my dick. Fuck."

A good ten minutes passed as he laid there mesmerized by my magic trick of making his cock disappear.

"Spin around on my dick."

I rotated to a position where I was stretched across his body with his engorged cock still stabbing my insides.

"Now really fuck yourself."

As I started the most intense leg series I'd done since having a trainer at the gym, he kissed the nape of my neck, tweaked my left nipple, pulled my jock to one side and jerked my cock with his right hand. All this sensation made me slow down a bit.

"Come on Tommy, show me how hard you can take a cock."

I gave it my all. The rhythm of my body slamming into his echoed off the walls mixed with the squishy sound of my precum gliding between his hand and my cock. He twisted and pulled on my nipple making me involuntarily milk his cock, while he bit and sucked my neck. It all became too much for me and suddenly I felt the warmth of my cum all over my face, chest, belly. Rope after rope of cum shot out of me, to the point it started running off my stomach and onto him and the bed.

My last squirt was the final clench of my ass to cause him to cum. Hot pulses inside me and his animal groan in my ear inspired me to keep pumping his cock with my ass. Soon, he grabbed my hips and made me stop moving. I could feel his heart beating against my back as more cum ran off my body onto him.

Henry wrapped his arms around my body and turned us both onto our sides. He rubbed my cum all over my body and kissed the back of my neck. His dick slowly slipped out, followed by a torrent of cum. The rhythm of his heart still beating hard alarmed me a bit.

"You okay back there?"

"Yeah, I might need to start doing cardio again if I'm going to do this on a regular basis."

"I'm in this area once or twice a week. I wouldn't mind being a regular fuck buddy for you until you start dating."

"Gosh, the sacrifices you make."

I spun around to face him and kissed him. "Really, that was fun. I know I'm a horrible boyfriend, but I make a great fuck buddy."

"Why are you a horrible boyfriend?"

"I don't like just having one person forever. I usually end up fucking around and then the other person gets all butt hurt, and not in the good way."

Henry smiled. "My partner was the same way."

"Did it make you angry or jealous?"

"No. It took a while, but we eventually got to a point where I didn't care if he fucked around as long as I was a part of it. I used to take him to orgies, bookstores, the occasional repair man and it was so hot to watch him get fucked and then fuck him afterwards. Sometimes I'd fuck him at the beginning of the night, take him somewhere with a group, and then bring him home and fuck him again. It was hot." My sudden erection stabbed him in the balls. "Looks like you might find that hot too."

For some reason I went all coy and shy and squeaked out, "Yeah it is."

He placed a finger under my chin and raised my gaze to meet his then grabbed my cock and balls. "How about next time I put you in a cage, blindfold you, and pimp out that hole online?"

Somehow my body managed to pump even more blood to my cock as I smiled. "That would be fun."

"Cool. I don't want a relationship either, but it would be fun to have a boy under me again."

I kissed him and felt his cock stiffen again. "I think you liked having me on top too."

He smiled and rolled onto his back, "Get up on it. Mind you, you're really gonna have to work for that second load."

I slowly lowered my sore ass onto his cock for the second time. "Yes sir."