Below is a story concocted entirely from the author’s imagination. No person, living or dead, should think the following is factual. When imagining the characters, the author imagined them all to be well over any legal ages of consent, regardless of jurisdiction. The author imagines that, though he has uploaded this story to Literotica, he retains his author’s rights to the copy he wrote, and expects no one to distribute this story beyond Literotica.

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What do you think about when waiting for a strange man to come to your hotel room and fuck you for only the second time ever, 15 years after the first time you let a another stranger stretch your asshole painfully, before breeding you and bringing you to bliss?

Well, I don’t know what you’d be thinking, but I thought about that first time [recounted in the previous story, Anticipation of Penetration 1] and, also, thought about the many things that could go wrong, such as him being a scammer or would-be blackmailer, or a flake, or having a disease he lied about. There was also robbery, or an unexpected third guy, or murder, to consider.

So, I was nervous, again.

The mind can spin like that, but I had taken as many precautions against those scenarios, and my recall of my first time, the time I lost my anal virginity, had my 6 inch, cut cock chubbed up. I gave it a slow stroke and it swelled a bit more. I looked down at it, the purplish, spongy head sticking out past my hand gripping the shaft. At the other end, the heel of my hand pressed lightly against my pubic bone and my bushy pubic hair.

I have all my pubic hair, by the way.

Now, a 6 inch cock, in pornography, is a smallish cock, but, in the real world, in my experience, it’s a fine size. It’s actually very slightly above average. Slightly more than half are smaller.

The man I was waiting for, supposedly, had a 7 inch cock, of average girth. I hadn’t seen his face picture, but he assured me he wasn’t repulsive. He said he was 5’11”, the same as me, and that he weighed about 200 lbs, about 20 pounds more than me.

His body picture showed that he was a bit thicker than I am, and had some brown fur on his chest, a nice trail to adventure, a nice bush and nice sized fuzzy testicles, that hung low in the picture, apparently taken in his bathroom after a shower. His cock was fluffed up nicely, his cockhead flared along the ridge. It was thicker than slim and smaller than “girthy.” A respectable piece of meat.

My mouth watered a bit at the memory of the photo and the anticipation of seeing it up close and personal.

He hadn’t seen my face picture, either. I don’t share face pictures on the internet, so I don’t require them. It’s only fair and responsible. I had sent him a flattering picture of my cock and balls, and one that showed him that I’m in decent shape.

We had hooked up on a free gay hookup app, not Grindr [I hate that app] after I saw his profile and had messaged him. He said he wanted to find a guy around his age and size to get naked with and see where it led us. He indicated he liked to kiss.

“Your profile sounds great, just what I’m looking for,” I wrote in my message. “And your cock looks tasty.”

“Thanks, same here. Your cock looks delicious, and your ass is making my cock throb,” he replied.

“I’m not really a bottom,” I wrote back. “I’ve only been fucked once, 15 years ago. I’m not sure I’m ready to do it again.”

“No pressure,” he replied, “Except you have to be cool with kissing. I love to make out.”

He sent me an instant message with a photo of his cock at full hardness, a drop of precum, gathered at the tip.

I have a weakness: I see a cock, and I want to suck the cock.

My mouth watered, and my cock twitched a little harder, and pulsed to full hardness. I was nude, sitting in a swiveling office chair with my hips forward and my cock and balls hanging loose between my thighs. I scooted forward a bit more, and took a selfie from between my legs below and back at my low hanging balls and swelling cock. Before I snapped it, I pulled my ass cheeks apart, so the picture included a glimpse of my clean, pinkish asshole.

I sent it to him, with the text “We need to meet.”

Usually, that’s when things grind to a halt, but this time I happened to have access to a hotel room for two nights and a day in a town 30 miles from each of our indicated locations.

I told him and he agreed to meet me there, here, in about 10 minutes or so.

It’s a nice hotel room, downtown in the urban center of our mutual greater metropolitan area. I had checked in at 4 p.m., had a drink in the glitzy bar to loosen up a bit, and gone up to the room to prepare myself for whatever might happen.

We’d probably just make out for a bit, then swap sucks until we cum, then he’ll leave hurriedly, I thought, but I’d better be ready for whatever.

Before I got into the shower, I started on the most intimate part of my preparation for our sex session. The fact that I had brought a clean out kit testified to my true objective for the night. “He might want to finger me” I thought, dodging the real, underlying desire for something longer, harder and thicker than his fingers.

So, I used the mineral oil and water enema bottle I’d brought in my bag of tricks. The results indicated more was needed. I had only brought the one bottle, so I refilled it at the sink with plain lukewarm water, cleaning the nozzle a little, and repeated and rinsed, and again, and again until I was as clean as a whistle inside, for several hours, at least.

Then I showered and shaved my face as smooth as I could get it so. I thought about my chin sliding between his ass cheeks, while my tongue searched for his hairy hole. I didn’t want any stubble to irritate him while I rimmed his hole.

That thought kept my cock chubby. I stroked it once or twice, but stopped before I got too into it. I wanted to save all my desire and tension for when we were in bed stroking each other’s meaty rods, and sucking each others’ tongues and cocks.

After I soaped up and made sure I was clean from head to toe, I stepped out and dried myself in the quick manner I’d learned in high school P.E. showers, and pulled on some loose gym shorts and nothing else.

And now here I was, waiting a few more minutes for the knock at the door that meant I’d have the rock hard cock of another man inside my body in a few minutes. My cock throbbed again at that thought, and strained against the thin fabric of the shorts to straighten up. I sort of enjoyed the feeling of it bent and pent up.

I got a beer out of the cooler, popped it open and took a long drink. The earlier cocktail in the hotel bar had done its job relaxing me a bit, but my mouth was dry with tension, anyway, and a cold beer was a comfort.

Then a quiet knock at the door, and I went to it immediately, looked through the peephole and saw the man I was waiting for.

I opened the door and he quickly entered. He stuck his hand out, said “I’m Ron.” I shut the door, and we stood close behind it in the narrow entrance to the room.

I took his hand, shook it, and replied “I’m Carl.” My name is not Carl, but it’s the one I decided to use.

We went toward the main part of the room, near the window overlooking the city.

“Would you like a beer,” I asked. He nodded and I fished a local pale ale out of the cooler, popped the top and handed it to him. He took a swig.

“That’s nice,” he said.

“Let me taste” I replied, and moved in front of him, put my hands on his hips and pulled him in for a kiss. My tongue snaked out of my open mouth and darted between his open lips and teeth, meeting his tongue half way and moving them together.

“You said kissing was mandatory,” I said, when I pulled back for a second.

“It is,” he replied, and moved his lips back to mine and his tongue engaged mine again, this time plunging into my mouth. I sucked on it a bit while he had it there.

We pulled our faces and upper bodies apart for a breath, and we both took drinks of our beers, but his arm around my hips and mine arms his pulled our pelvises together for a grind.

I’m sure he could feel every ridge and bulging vein of my suddenly rock hard cock as I ground it into his rock hard cock, but he was wearing denim jeans and underwear below his polo shirt.

I leaned back in to put my lips against his again and sucked a little to get him to put his tongue back in my mouth. I reached both hands up under his shirt, and ran my fingers over the fur on his chest, seeking out his nipples, which I stroked while his tongue explored my mouth and teeth, which must have tasted like beer and mint from my toothpaste and mouthwash, not unlike his mouth’s flavor.

His hands moved to my buttocks, grasping and kneading them through my thin shorts. In response, I ground my cock harder against his cock, which felt like a bar of steel against me.

He slipped his left hand under the waistband of my shorts and palmed my bare right buttock and squeezed. I ground harder against his raging cock and moaned a little around probing tongue. He withdrew it and I stuck my tongue into his mouth and he sucked on it.

I was in sexual overdrive. My hips were thrusting subconsiously against his rod until they tilted up to bring my asshole closer to his hand squeezing my cheek. He dipped a finger toward my asshole, circling the wrinkly part then pressing slightly inward.

I had lubed myself internally just after my shower, and his finger glided around my hole, circling, pressing.

Suddenly, he pressed his middle finger in up to the first knuckle.

My head tilted back in reaction, breaking off the sloppy tongue kiss we were engaged in, and I moaned.

“I’m going to fuck this tight ass tonight, Carl. I’m going to breed you deep.”

“I’m don’t know if I’m ready for that. I’ve been fucked once before. You’re much bigger than he was.” I ran my hand along his thickened cock over his pants. It was trapped pointing down one leg of his pants, straining to straighten, the shape of his balls visible through the fabric below. I cupped his balls and ran my fingers along the bulging arc of his trapped cock.

I had readied myself physically for the possibility that I’d be fucked tonight, but I wasn’t really totally there mentally.

“You want to put this big thing in my ass? That’s probably going to hurt.”

“I’m going to put this big cock in your ass, because you want it. It will hurt a little,” he said. “You’ll handle it.”

He put another finger against my asshole and pressed it in to the first knuckle. Now I had two fingers up my ass.

I moaned again, pressed my mouth back to his, and moved my hips so his fingers went in a bit deeper.

“I’m nervous about it,’ I said. “I need you to go slow, give me time to adjust, and maybe pull out if it’s unbearable.”

He whispered, softly, lips an inch or so from my ear: “Of course. I want you to love taking me deep in your ass. You know why? Because I want to fuck you and cum in you over and over again.”

We were still standing in the center of the room, me with one hand between us stroking his meaty dick through his pants and another around his neck pulling his mouth toward mine, with two of his fingers inside my asshole, stretching it.

He still had his clothes on! I let go of his neck, pulled my mouth from his, and slid slid my nude body down to my knees on the carpet in front of him.

He took off his shirt, revealing his hairy chest and respectable abs.

I fumbled with his belt, at eye level, got it undone, unbuttoned his pants, lowered his zipper and pulled his pants down, releasing his trapped cock, which snapped against his belly.

He had kicked his shoes off earlier. With his pants around his ankles, he stepped out of them, now wearing only his socks. I pulled them off his feet one at a time. Now he stood naked in front of me.

He was beefy, not fat. He had a layer of thin brown hair over much of his body, his cock was sticking up almost straight up to his abdomen, his cockhead at the height of my mouth. I dipped my head forward and licked from the bottom ridge to the tip of his cock, taking a drop of his pre cum on my tongue and savoring its texture and subtle flavor. I licked again, then formed my lips into an “O” and took his twitching cock inside my wet mouth, pulling it down to a right angle from his abdomen. My tight lips snapped over the ridge of his cock head to slide along his hard shaft, one inch, then another, and another, moving my lips down,feeling the prominent veins slide under them as they reached toward the base of his shaft, until all six inches of his flesh were in my mouth.

Six inches is about all I can take in my mouth until the head of the cock I’m sucking hits the spot in my throat that triggers my gag reflex.

True to his profile, his cock seemed to be just a little over six inches, just a quarter inch or so longer than mine, which was at full length with the mental stimulation of this man’s cock all the way in my throat, my nose in his pubic hair.

His hairy pubic bone reached the front of my face, and his cock head tickled my sensitive throat. I gagged, coughing along his shaft into is pubic bush. I slid back until just the rubbery head of his cock was between my lips, then moved back down, my lips sliding along the cock I had wetted with my saliva on the out stroke. I reached the bottom again, reached around to grab his buttocks, and pulled his cock into the entrance of my throat, again triggering in a gag and cough along his cock’s shaft.

“Are you okay” he said.

I nodded, “Mmmph!” and went back down to his root. This time, I sort of half stifled a cough, pulled back, and went back down on his cock again. I had moved a hand to his ballsack,which I caressed and manipulated. They were wet with my drooled saliva, so my hand became wet while I played with his balls, all the while sucking his cock into my mouth and withdrawing in until just the very tip rested between my lips, then repeated the cocksucking motion.

While I was playing with his balls, I noticed that they were pulling up tight in his wrinkly scrotum.

He was close, but I wasn’t done enjoying his maleness, so I lowered my lips to his tightening hairy ballsack. I sucked a left ball and then his right, then licked his hairy sack and sucked it and both his balls into my mouth, using my tongue inside my mouth to massage and manipulate them.

I shifted my hips so that my bone-hard cock and drooping balls rubbed against the carpet.

I kept that up for a minute or so, grasping and grabbing his tight ass cheeks as I did it. His balls drew up tighter, and I felt him put his hands under my armpits and try to lift me up, so I stood.

“I’m about to cum. I want to save my load for your sweet ass” he gasped, his hands around to my ass cheeks again. He moved in for more kissing and assertively pushed his tongue in, and started tongue-fucking me. My tongue danced around his as I gently sucked it in, letting his tongue have its way with me the way his cock would in a few moments.

“I want your cock in my ass and I want you to pump your semen deep inside me, ” I said, when I came up for air.

He pulled my face to his and we resumed making out for a minute or so. I still had on my shorts. He looked down between our bodies, and my cock head had sneaked up past my the waist of my shorts, a sheen of pre-cum glistening atop my piss hole. He wiped it with a thumb and put his cummy thumb in my mouth, and I sucked it clean.

Then he put his both his hands under my shorts’ waistband and slid them down my legs. I stepped out of them as he held them against the floor, and my cock bounced up, free.

As he stood back up, he stopped and took my twitching, leaking cock in his mouth and took it to the root in one motion. I felt his tongue dancing around my shaft inside his mouth. He didn’t gag, even when he reached around grabbed my ass cheeks and pulled me deeper in. He withdrew from it, grabbed it around the base of my cock, tilted it down a bit, and plunged his mouth back on it to the base, this time putting his fingers back into my asshole, only this time there were three into me up to the first knuckle.

My asshole twinged. I was a bit uncomfortable, but it revved my horniness up another notch, anyway.

He withdrew his fingers for a second, then put two back inside me, deeper this time. The lube I launched up my ass earlier was doing its job. He finger fucked my for a minute or two. I could feel him spreading his fingers as they plunged in and out of my ass, trying to stretch me out, relax my asshole.

It worked a bit, bit because he returned a third finger to the mix, and it was much more comfortable at first, the twinging only returning a bit when he forced the three fingers in deep. He resumed finger fucking me with three fingers, the twinge easing on withdrawal, returning a bit in the instroke, but fading a bit with each stroke.

He stood back up and we made out for another several seconds, with his three fingers still fucking into my ass.

“You’re ready to take my cock in your ass now, Carl,” he stated, turning to stand beside and slightly behind me, his fingers still in my ass. “Let’s get you in bed.”

He had me hooked on his fingers and pulled up until I had to stand a bit on my tip toes. Then he pushed forward, making me take a step forward, and he steered me to the bed with his fingers in my asshole.

He pushed me face down on the bed, with my legs off the sides, then used my finger-hooked ass to guide me up on my hands and knees.

“Put your chest on the bed, pull your legs up to your sides and lower your ass as much as you can.”

I complied. I don’t remember being this submissive before.

I pulled his fingers out of me, and I relaxed into the bed a bit.

His hands went to my hips and I felt his bushy pubic hair against my my buttocks and then his fat, hard cock’s shaft press into my crack. I looked back as best as I could and saw the cockhead, atop his swollen, stiff and veiny shaft, sticking out above my ass, his cock lying there like a fat sausage in a bun. I also noticed that I could see us clearly in the mirror on the closet door.

He moved his hips and his cock slid in the fleshy valley, the veins tantalizing my asshole as they dragged across it. He moved again, and I could feel his cock’s rubbery head squishing against by wrinkled, winking anal ring. He left it there and moved it in and out a little, not trying to penetrate me, just teasing me with the anticipation of him opening me up with his dick.

He pulled back again, and my ass lost contact with the cock it wanted to stretch it and penetrate it.

He sank to his knees behind me, and pulled me by my hips back toward the end of the bed, so my ass was hanging off a bit more. Then he moved his hands to my ass cheeks and pulled them apart.

Then I felt something new, his tongue on my asshole, licking it, licking around it, poking it. He laid it flat and licked from the bottom of my ball sack, across my taint, and across my asshole. It contracted and relaxed, contracted and relaxed as he repeated.

I was in heaven. It was so intimate, taboo, and dangerous. His tongue on my ass made my cock twitch and my asshole clench, and then he poked his tongue into the center again, a little deeper this time, and again, deeper, and deeper, until he was actually inside a little bit.

My asshole was wet, and pre-lubed, and he again put his fingers in to stretch it out. His three fingers went in as deep as they could, and he changed their angle and rubbed in a way that set fireworks off in my head. I moaned deeply into the blanket, and thrashed my head from side to side.

He pulled out, and for a moment I wondered what was going on, but I looked in the mirror to see him going to his pants and getting out a bottle. He returned to the bed, and took up his position, his fucking position, with his along my crack and balls pressed against my, then pulled back again. I heard the bottle snap open and felt a cool liquid poured above my asshole, dripping down across it. Before it dripped down to my balls, he caught the rivulet and smeared ii on my hole, and pushed some into my asshole with his fingers. He added more.