Older For Younger: First Gape

I found someone on the old Craigslist. At the age of eighteen, it was my first experience with meeting someone random online. I was feeling horny and after weeks simmering on the idea of hooking up with someone, I'd spend every night reading ad posts. I found what people were posting so hot, that I would finger my own ass. I'd rub my index finger around my hole, sometimes sliding my finger inside, but I was always so tight, I could never get past my knuckle.

Reading post after post, it all seemed so easy, I craved the touch and feel of an actual man.

I found an ad that said, "Older for younger, seeking under 28, dominant daddy figure looking for cub". It piqued my interest, and I sent him a message. In the message, I said, "I am 18, looking for an older, seeking a good man to experience life's pleasures with."

He ended up being forty years older than me and bi. We messaged back and forth for almost a week, about scenarios, and he shared pictures. I had none to give him, but with every message I got, every picture I looked at, he got deeper in my head. He was white, retired, 210 pounds, six-foot-three-inches, with a seven-and-a-half-inch cut cock, a top. I knew I wanted to make this happen. I knew I wanted to make it happen with him. I am South Asian, brown skin, weighing 180 pounds, a skinny six-feet tall, with a five-and-a-half-inch cut cock, and who was open minded. I just wanted to try a guy.

We decided to meet up, and he'd get us a nice hotel, I didn't have a car, and still lived at home. I agreed to meet him in a Safeway parking lot. I told him I was South Asian, and what I would be wearing-- blue denim jeans, a white t-shirt. Safeway is a grocery store near my parents' place. I told my parents I was going out for a walk, just to get some air and that I may meet up with some friends.

I walked over the few blocks to the parking lot, my knees shaking the entire time, and stood under the street light in the empty parking lot. It was getting dark. A few cars were parked around the empty lot.

My nerves were making me anxious. I couldn't believe what I was doing, but I silenced my doubts and stayed brave. I enjoyed the thrill of it all, and kept thinking of all the Craigslist ad posts I read, and emails and images I had exchanged with him.

A white Escalade pulled up, his window rolled down. "Are you Tony?"

"Yes, I am." I opened his large SUV's door and jumped in.

He was this sexy, grey-haired man, who smelt amazing, was in good shape and had a nice tan; my anxiety went away. We drove down a nearby main road through a business district. I reached over and I placed my hand on his crotch and gave him a squeeze, I could feel a big bulge. We didn't talk much, but my heart was racing, I wanted to show him I was eager to play.

We pulled up to a nice hotel. He went inside, while I waited in the SUV. I could see him talk to the front desk. I could see their lips moving, each nodding, and a minute later, he came out, not saying anything; we kept driving. This time, it was a roadside motel, the 'Algonquin Inn.'

"The other place was full, let's just stay here."

I didn't question him, but I think he didn't want to pay the high rate.

We got out of his vehicle. He held the motel reception door open for me, walked in after me, and we went up to the front desk, where there was an older Asian guy behind the desk.

There was a thrill of being bedside him, as he paid cash, and the clerk slid us a set of metal keys. I kept thinking about the age gap between us, and also what the guy behind the counter must have been thinking, but the thrill of it all excited me more. So I just stood there smiling, playing it cool.

We grabbed the room keys and pulled into a parking stall. My nerves acted up, as I'd never done this before. I placed my hand on his thigh, to let him know I was still eager to play. He reached his hand around the back of my neck and pulled me in closer for a kiss. I could feel his tongue part my lips and slide in my mouth, as we kissed deeply. It was my first kiss. He was so passionate as I melted into him, opened my mouth as our saliva mixed, and I nuzzled in closer to his body.

I kept running my hands along his body, he was strong, but very kind and cordial.

"Let's go inside."

I felt at ease hearing his deep voice. And nodded yes.

We stepped into the motel room, the door shut behind him, as he locked it, and hooked the safety chain.

"I'm excited to finally meet you, Tony."

"Me too, sir." I knew I was all his.

The room was dark, lit by the moonlight and yellow hue of the streetlights shining through the parted curtains of the motel room window. He went over to the lamp in the corner and turned it on.

The room was small, it was just a queen-size bed, a closet next to the bed with a mirror on the doors. A big-box TV was in the corner. A faint smell of cigarettes hit me, which was coming from the stained carpet. The motel was run down and cheap. I could feel the excitement building in me, I just wanted him, and I didn't care where it was, the taboo of the dingy motel, our age gap, the male-male experience, him white, me brown-- it was all so hot.

Opening the bathroom door, he said, "Come in here."

I stepped into the tiny space. I knew what I came to do, so I complied.

We chatted a bit, just small talk, as we took off our shirts. He never asked my age. I was slim, tall, awkward, he was muscular, tall, clean cut. I kept glancing at his bulge in his pants. He asked what I was thinking.

I just came out and said, "I want to suck your cock."

He smiled and said, "Please do."

I got down and kneeled between his legs, the bathroom floor tile was cold and hard on my knees. I unzipped his pants and pulled them down. His large, hard cock flopped before me, pointing between my eyes. The tip of his cock was glistening.

I was a bit at a loss, caught between the feeling of taboo, and the curiosity of his trimmed grey pubic hair, leading to this thick goldenrod. This older, big, white-daddy cock, centimetres away from my face. I reached my hand out, stroked it, rubbing his cock all over my face. I thought about how he'd like to be sucked. I licked the shaft up and down; pulled his cock up with my hand, stuffed my face in his scrotum and gently sucked his balls.

I could hear the moan escape his mouth, which drove me to make him happier. I licked up his shaft, and slipped it into my mouth. All I could think about was sucking his cock and hearing him moan; the rest of the world faded away.

Up and down I sucked, hearing him grunt deeper and louder. I kept putting more and more of him in my mouth. He grabbed the back of my head, swaying his hips back and forth, as he fucked my mouth; I gagged a bit, but eventually got him past my throat. I could feel his entire length inside me.

It was so intense. "Let's stop, you're going to make me cum." He placed his hand on my dark hair, gripping it and pushed my head back, my lips popped off his cock.

"Did I do something wrong?" I asked. I didn't know what to think. Spit and mucus ran down the side of my mouth and also coating his hairy thighs, all the salivating from pounding my throat.

"No." He stood as he led me to the toilet, closed the lid, and sat me down.

He pulled his pants back up, went to his Escalade and grabbed a duffle bag. He placed the bag on the counter, and pulled out an enema bag. "I want to fuck your tight ass, get it ready for me." He handed it to me, and he walked out and sat on the bed.

"Wait, I don't know how to use this," I said, standing there with it dangling from my hands, a dumbfounded look on my face.

"Take your pants off." He smiled. "Bend over."

He squirted some lube on the end of the orange tube, spread my cheeks with one hand, his thumb opening me up, and slid the tube end up my ass. I placed my hands on the counter and bent over as I felt this coldness slither up inside me like a snake. The tube was thicker than my finger, but the lube made it feel nice.

I looked at myself in the bathroom mirror, as he worked on my ass. I was fascinated by the whole scenario, our differences in skin colour, age, experience. I felt so sexy.

He turned on the sink faucet, testing the water with his fingers for temperature, until it was just right. He filled a bag and screwed the lid shut. He lifted the bag above my head, and squeezed the bag, I could feel the warmth flow inside me and fill me up.

Still looking in the mirror, the bag completely emptied inside me, I felt the weight of all that water sloshing around in my belly.

He said, "Sit on the toilet."

He pulled the tube out and water rushed out of my ass. It was a euphoric feeling I'd never felt before. I looked up at him, he looked like a god that had complete control over me. He took his pants off and stuck his cock in my mouth again, pumping my face, as fluid rushed out of my ass into the toilet.

Once the water stopped coming out of my ass, he said, "Good, you're nice and clean."

After my enema, we walked out of the bathroom.

"I hope you fuck as good as you suck." He gave me a reverse bear hug, grabbed my ass pulling me into him. I could feel his hard cock slide between my ass cheeks and press against my asshole.

He laid me face down on the bed and bent my knees, arching my back, exposing my asshole to him. He tossed his duffle bag next to me on the bed. His hands grabbed my cheeks, spreading them apart. I could feel his breath, as he licked around my hole.

"I love the colour of your ass, your hole."

"Fuuuuck," I gasped, as he tongued me. It was so amazing feeling him work around my hole, admiring my ass.

"Please fuck me," I whimpered, wanting to feel him inside me.

I heard him rustle inside the bag, as he slipped a condom on. I felt his lubed finger enter me and prime my ass. I craved to feel him inside me.

He shifted on top and I felt his cock between my cheeks, the weight of his body on me, as he lined up his cockhead against my hole.

As he pushed in, he said, "I'm going to enjoy this." He pushed in with one thrust, I lost my breath as my eyes widened, I tightened.

I felt scared, and nervous. "Oh my god, that hurts."

He stopped, and pulled out. It was just as painful pulling out as it was going in.

"You're not that tight," he replied, in his deep voice.

I lay there, catching my breath, my ass puckering open and closed. I still wanted to feel him inside me. I asked him, "Can you try again? Please, but go slow."

I relaxed my asshole, and opened up. He squirted some more lube, I felt him on top of me, as he slid inside, this time pushing so gently, as he eased his shaft deeper into me. His thick cock still hurt as he split me open; it was a good pain though, it felt painfully amazing.

"You're so fucking tight," he gasped, as he was completely in me.

The feeling of pleasing his huge cock with my ass gave me a rush, I relaxed my ass so I could take him balls deep. I pushed down on his cock, and looked over at him, his eyes were rolling back in his head, as I could see I was satisfying his manhood.

Then he slowly pumped my ass. I was lost in the feeling of him pulling out and pushing in. I could feel every inch of him filling me inside, I synced with his pumps, pushing back to meet his thrusts; his balls smacked against my balls. He'd pull out, my ass would gape, and I'd fart, and he'd slam back in, his cock sliding in me would make a "pfft" noise, and gurgling lube.

I looked in the mirror next to the bed, I could see him fucking me, it was so hot being taken by an older daddy. The white-brown skin-colour difference-- his white veiny cock sliding in and out of my brown ass. With each pump the bed squeaking, the fucking sounds, feeling, room, him, it was all so incredible.

I could hear his heavy breathing get deeper and faster. His sweat was dripping on my back, as he fucked me good for about twenty minutes.

His back arched forward-- pushing my head into the pillow and headboard-- his ass cheeks tightened, as I loosened even more. He was cumming, his cock was spasming; I could feel the throbbing of his cock, unloading all his cum in me, filling the condom. He pounded me a couple more times as he came the last few drops.

It felt so fucking good to be taken, to pleasure him with my ass. He pulled his cock out collapsing on the bed next to me. My asshole stayed open, I felt gaped. He lay down beside me, as his cock went limp, the condom full of cum hanging off the tip.

I still hadn't cum yet, so I was even more sex crazed after satisfying him. I reached my finger back to my asshole, to find that it was wide open-- I could fit my index finger, and three other fingers easily. I felt so sexy, being lubed up and loose.

I kept staring at him in admiration of what we just experienced together. I grabbed his condom, and slid it off his cock. It snapped off his thick cock when I pulled, and I squeezed his hot cum into my mouth. I was in a slutty daze, performing for him as I swallowed, and he grinned at me.

"You're a little whore."

"I'm your little whore." I climbed on top of him, then took his cock and placed the head on the opening of my asshole, and slid it back into my ass as I sat down on him. His entire cock went in me so easily as I rode him bareback like a kid's shopping mall pony ride. We fucked until I made him cum again, my ass was nice and loosened up as I felt him splash inside me. I just laid there with him inside me as his cock went soft, cum dripping out of my hole.

I kissed him passionately on his lips, I didn't want this feeling to end.

He dropped me back off at the Safeway. As I walked home, my ass felt loose, I had a swagger; my underwear drenched in his cum from my leaking asshole. I was on cloud nine, knowing I could please a guy like that.

I knew this was a start to something amazing.

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(Edited by Kenji Sato)