In or Out?

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
timmywells
timmywells
1,744 Followers

"Just relax Jimmy. Doesn't that feel good?"

Not really. The tongue, now that felt good. This? Well, it wasn't as bad now as it was in the beginning but it still hurt, and I was glad when his fingers came out. Only for a second.

"You've never played around back here have you? Boy, you're as tight as a vice," Larry exclaimed while I tried not to cry for the brief seconds that he had tried unsuccessfully to put an additional finger in me before mercifully pulling them all out.

"So nice - you look so good," Larry was saying, and then he took my hair in his hand and raised my face up so I could see us in the mirror; a skinny nerd on his hands and knees and Sasquatch kneeling behind preparing to...

"You need to watch, Jimmy," Larry said. "It's not going to hurt. I swear. You want to watch because you'll remember this all your life."

"Please don't," I remember saying, although I don't know if Larry heard me.

All I do know his that I remember feeling the head of Larry's cock pushing against my anus for a second before it started to slip inside. Relax he kept saying, and I tried but it was easier said than done. In my reflection I looked like that face in the painting "The Scream" and that was just before the ridge of his cock head popped into me, and if there were other people in the motel their sleep got interrupted by what came out of my mouth.

"I beg of you," I recall dramatically saying after screaming. "It's too big."

"It's okay - that's it - worst is over," Larry was saying as he massaged my shoulders, only while he was saying that his cock kept sliding deeper and deeper into me.

Larry took a hand off of my shoulder to fiddle with the tube of gel, and then I felt some more coolness, followed by deeper probing of my virgin ass with his veiny monster until he retracted most of it.

"There," Larry was saying behind me as he began to make long and slow thrusts into me, and as the bed rocked the pain began to ease.

The rhythm was steady and I found myself rocking along with it, and when Larry leaned over me and wrapped his arm around my waist the feel of his hairy body on my sweaty back was soothing.

"Knew you'd like it," Larry said as he reached around and grabbed my dick, which was limp but at least had stopped trying to crawl into my intestines from the pain. "Don't you Jimmy?"

I did. Maybe my ass was numb from the pain, but the feeling of Larry's cock sliding in and out of my ass was becoming really good, and it kept getting better as he went faster and deeper.

That slapping sound - it was our bodies coming together. two increasingly sweaty bodies making that sound - and I heard and saw Larry chuckle as he held onto my hips like the captain of the ship.

"That's it Jimmy," Larry chortled when it became obvious that I was pushing back into him now each time he slammed forward. "You want it all, don't you?"

"Yes."

"Tell me babe," Larry asked as he pulled my head backward playfully. "Is it still too big?"

"No - want all of your big cock!" I snapped back.

I did. I wanted it all, harder and faster. That vein riddled shaft and the base that my hand couldn't get around? I wanted it all.

The end was a blur. Larry was pounding into me so hard that the bed was inching toward the mirror and he looked liked a madman - his face beet-red and his neck muscles bulging while sweat flew off of his bald skull.

His hand was down on my cock - my hard cock - and he was yanking on it like he was trying to pull it off me - and my response was to cum. While my dick spurted all over the sheets Larry let out a bellow and then I felt my insides being soothed by his warm seed.

Larry stayed inside me as long as he could until his deflated snake finally slithered out of me, and with that we collapsed onto the bedding.

"Hope it was half as good for you as it was for me," Larry whispered as he cuddled up next to me.

"It was great," I said, and then got him to laugh when I added, "I want to do it again."

Eventually I got up, my butt now remembering what had happened, but when I looked in fear at the bedding there was no sign of much of anything on what was left of the sheets on the bed.

I waddled into the bathroom, feeling Larry's gift oozing out of me, and while inside I tried to remember everything that had happened.

Out in the motel room itself, I heard loud knocking at the door and at first I figured it had to be a pizza getting delivered since Larry had suggested that back in the car, but there hadn't been any phone calls made.

It was the police. When I peeked out there was Larry at the door, a sheet wrapped around him like a toga while two policemen were inside the room. At least Larry had a sheet. I had nothing.

"Come out here son," the one cop said when he saw me.

I looked over and saw Larry's pants hanging on the hook so after I told the cop I'd be right out I grabbed them and put them on, holding up the trousers that were at least 6" too big in the waist while I made my way out.

The one cop put me in the corner and kept asking me what was going on and whether I was there of my own choice. I assured him I was and after showing him my wallet and proving I was 18 they left, telling us to keep it down for the rest of the night.

"Something else to remember," Larry said with a grin. "How about a shower?"

"Yeah, I need one," I admitted.

"We," Larry amended, and with that I took my first shower with another guy.

It was nice, soaping and getting soaped. Larry was so gently and loving as he cleaned my savaged bits, and I just thought it was nice that our bodies felt so good against each other.

Even the sight of our dicks having this kind of sword fight, a mismatched battle if there ever was on, was erotic to me. So erotic that I got hard again, at which point Larry took it upon himself to kneel down to take care of that situation.

Fortunately there was another bed so we retreated to that. To rest, Larry made clear, because while he had the urge and was excited as could be to be with a guy that turned him on so, he was not a kid any more.

"63?" I said when he warned me that when I got to be 63 I would know what he meant. "Wow. I didn't know."

"You thought I was older?" he asked with a grin.

"No, I figured, I mean maybe late 40's," I said.

"Does that bother you?"

"No," I said, although knowing that Larry was as old as my grandfather was a bit off setting. My grandfather had enough trouble getting up out his chair, much less doing what Larry had done to me, so there was little they had in common.

We decided that since it was late and I didn't have to be home, we would spent the night.

"Would you mind if I played around?" I asked after my eyes kept going down to the limp tool resting on Larry's hip.

"As long as you don't expect anything," Larry said. "And don't be offended if I fall asleep because you wore me out. Maybe in the morning."

"Okay," I said, getting a laugh out of him when I added while sliding down the bed, "Just relax."

I made love to Larry's cock, lavishing affection on his flaccid organ while he rested on his back. I licked the undercarriage of his weapon, tonguing the roots and the space between his cock and his balls before working my way up the shaft.

I skinned the foreskin back and sucked on the crimson plum like it was a tootsie pop and then took as much of his cock in my mouth as I could, almost managing to take all of him in at one point before I got up for a second to take a drink of water.

Back I went, and this went on for at least an hour. I was in heaven, and despite Larry suggestion that he might fall asleep, he was still awake. I could tell that when he reached over my hip and grabbed my dick and stroked it while I slobbered over his cock.

A cock that was getting harder. Not hard, but I could feel it getting longer, thicker and firmer as I kept sucking and rubbing him.

"Damn," I heard Larry mutter, and his pulling on my dick got more excited before he muttered, "Jimmy."

My mouth was just coming off the tip when a spurt of semen squirted out of Larry's half-turgid dick. I slipped my mouth back on his cock and started jerking the shaft, coaxing out an orgasm that neither of us expected.

"That was - really good," Larry admitted after I finally let go of his dick. "Unreal. Well, that might have killed the chance for a morning event."

"That's okay," I said, and fell asleep in his arms, experiencing a great night's sleep.

For the record, Larry was more than up to the prospect of a morning romp, and when I saw how hard he got I asked him whether or not he wanted me again.

"You sure?" he asked, and while I was sore I wanted it bad, and despite his fears Larry was more that able to get hard enough to take me anally.

It wasn't like it had been the night before though. This time Larry was gentle, and he moved me around into various positions, all the time his cock sliding into me slowly and lovingly. My favorite position was when we went over to the dresser and I leaned over when he lifted me up and slid into me.

"I'm going to cum soon," Larry said as we looked at ourselves in the mirror with my boner comically bouncing around. "You look to good to me."

"Wait," I said as i took one hand off the wood and used it to squeeze my balls. "Just a second... okay. Cum!"

I started spurting a load all over the knotty pine, and then Larry was cumming too, filling my bowels with his seed just in time before our bizarre coupling became undone.

"Oh brother," Larry said as we laughed while cleaning my cum off the furniture. "I'm glad it's check out time soon. Who knows what we'd be doing?"

I didn't want to say goodbye, but the time had come. Larry lived quite a distance away and was just passing through the area when we found each other, but as he dropped me off near my house he asked if I would like to get together again some time.

"Sure!" I said, and with that he wrote his number on a piece of paper. "I will call you."

I would have, but like an idiot by mistake I left my wallet in my jeans when I washed them a few months later at college. Almost all of the number was obliterated, and after trying a few combinations of the readable numbers with others and failing, I gave up.

Too bad. Larry probably thought that I didn't want to meet up with him again, but he was wrong because he was great. Larry, if you happen to read this and you liked my telling of our night together, leave me a comment.

***

thank you for reading

timmywells
timmywells
1,744 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymousabout 2 months ago

This is Larry. What up lil stanky?

AnonymousAnonymousabout 1 year ago

Magnificently erotic. Loved the uncut big cock, the arpit hair kissing, just very erotic and I have always loved your stories.

Thank you.

AnonymousAnonymousover 10 years ago
Loved It!

Got fucker for the first time when I was 40. He was older and so experienced. It was fantastic! He lubed me well and took his time. I had his solver bullet vibe all the way in before he fucked me. I took it by riding him first. After that I let him use me. I felt like such a little bitch, whe I came just from the fucking he gave me. More!!!

AnonymousAnonymousover 10 years ago
Loved it,

Must be many of us who were just as naive when young and inexperienced, but did we wise up fast.

I always loved the older men, especially the well hung ones who could fill my bum with big loads (and still do) if given the chance, they are less rushed and more experienced and some of them can fuck you for hours.

AnonymousAnonymousover 10 years ago
Love the mirror

The idea of being deflowered while looking at the mirror of the two of you there on the bed is smoking hot. Wish I was Larry too.

Share this Story

Similar Stories

Steam Room Daddy A young straight guy is forced to obey him.in Gay Male
Straight Turnout Strait guy is turned out by an experienced man.in Gay Male
First Time with Neighbor Daddy 18-year-old boy is taken by older neighbor.in Gay Male
How I Became A Gay Cock Slut Young married man is seduced at a resort.in Gay Male
The Toyboy Experiment A young straight guy submits to an older man.in Gay Male
More Stories