A Late Starter Ch. 02

Story Info
30-something married guy finishes what he started.
976 words
4.42
48.5k
6

Part 2 of the 2 part series

Updated 10/29/2022
Created 09/14/2004
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Misgivings shot through me as I folded helplessly over the couch, Aron's hand effortlessly holding me in place. My own body weight worked against me in this position- basically he could keep me from shifting as was necessary to get up off the couch with his one hand. His other hand was on his well lubed cock, spiraling it against my slick, virgin ass. He wasn't shoving, but each rotation it went a little deeper, wallowing the outside of my asshole but not straining the tight ring of muscle that would be the cause of any pain I'd feel.

I started believing in his gentleness again, that flash of surrender I'd felt when I'd wanted to accept him wholly; allow him to take me for his own pleasure while easing me into this new experience in easy stages I could handle. His words were an echo to my thoughts. Never ceasing his massage of my tight hole, he leaned forward a bit (Not removing that controlling hand on my back, the still terrified part of my mind reported), and asked if I was still sure that I wanted to do this.

Against the couch's back my cock was harder than I could ever remember- the skin stretched so tight it hurt- and I was feeling things from my asshole I never had before. I heard my voice, shaky and a little scared, saying, "Yeah... just...take it easy at first, OK?". The pressure from his prick on my ass ring increased a bit- not enough to force itself in but enough so that my muscles were forced to tighten to keep the invader out. "Alright, I need you to try to relax for me then. This is going to hurt at first, and you might want me to stop. Will you give me 10 minutes, and if you want me to stop then, I will...?". I now know what he was saying, but at that moment I was just overcome with gratitude over his understanding. "Sure".

The tip of Aron's cock started pushing hard against my rear hole. One hand, no longer needed to guide his tool, came down to grip my hipbone while that unnerving other hand on my back kept me from standing up. With all the lubricant and my current position, I was no match for THIS assault, and that purple strawberry I'd so lovingly sucked started to stretch me open. I'm pretty sure the pain started when I was stretched just past 2 fingers worth- a hard and bright circle of agony that burned white hot. I couldn't take this- I was convinced no one could. I made some kind of noise and tried to get away... and of course I couldn't.

Agonizingly I was stretched wider, and I finally remembered how to make words. "STOP! YOU'RE KILLING ME!". Even as more and more of that damned ever widening head split me open, I heard Aron say "uh...You promised me 10 minutes...uh... are you welching?" I tried to catch my breath, to say fuck yes, You win, I can't take anymore, and the pain hit a new level as my screaming rectal ring snapped over the head of his cock. It wasn't much release, but the pain dropped a bit, allowing some part of my mind to remember my promise.

Aron stopped pushing once the head was lodged in, to give me adjustment time, and probably time for him to enjoy my twitching anus, milking him. Had my calves, holding me on tiptoe, not decided to give out right then, I don't know what would of happened. Give out they did, however, and I sank back a full 2 inches, which meant I took 2 inches of his manhood beyond the head right up my ass.

I was shocked to discover it didn't increase the pain too much, beyond a slight burning at my asshole from the friction. I started to feel a wonderful feeling of fullness, or completion, or something, just above the pain. I desperately tried to get more, but the damned position I was in- or blessed position as it forced me to get to this point- wouldn't let me. Aron, as usual, was ahead of me and started a slow yet unstoppable push that ceased only when his balls made him stop. The pain was still there, but now I was willing to take it for the fullness I felt, and I groaned something like "God yessss ".

He had me and he knew it, and started pulling that incredible cock out of me like a King pulling a sword from a stone, leaving me incomplete and empty. He stopped mercifully at the crown of the head, and sawed that slickened saber back in with an easy strong stroke that snapped my head back. It's a blur after that- the quickening pace, the mix of pain and pleasure. I'm sure it was Aron that changed the tableau, as I found myself on my back on the couch with my legs wrapped around his waist as he pounded out the end of our night. The pain never really stopped, but drifted into the background as he tattooed something in my ass, making my cock throb in time to his thrusts. I finally couldn't take it and reached down for my cock, and after two quick strokes exploded all over my stomach. My asshole cinched tight as I came, and it was too much for Aron. He went up on his arms and went stiff, and though I didn't think it possible, that miracle cock swelled larger inside me as he shot the load my mouth had looked forward to earlier up my aching but eager ass.... I didn't mind a bit.

I have this fantasy frequently, and will soon make it come true. Your comments and suggestions are certainly welcome.

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 8 years ago
please continue

This was a great 2nd chapter. It's similar to the first time I got fucked (about 3 years ago) except that I didn't really feel much pain. It was tight for sure but not really painful. Once the cock goes in it's a wonderful feeling. The key is to use lots of lube. I'm surprised this is just a fantasy of yours. You really have to experience it in reality. Once I started getting fucked by men, I now truly enjoy giving myself completely to a man in every way. Please continue - I can't wait to read chapter 3 and 4 and 5 etc.

AnonymousAnonymousalmost 18 years ago
GOOD

another first timer enjoying

my dick is hard

oops was hard

AnonymousAnonymousabout 18 years ago
Good fantasy, real life needs protection

Good story - like the gradual progression and the gentleness shown....It wouldbe even better if the safety rule of "no fucking without a condom" was followed .... I hope the real life follow-up was safer .. Hooking up on-line has a really high risk of getting HIV or an STI

justagirlathartjustagirlathartover 19 years ago
Nice story

I could certainly relate to the feeling of fullness, but fortunately my first time at 21 was perhaps even luckier than yours; I experienced no pain at all.

norbert7norbert7over 19 years ago
wish i found a stud like this

wish i received this treatment .

Share this Story

READ MORE OF THIS SERIES

A Late Starter Previous Part

Similar Stories

A Video Store Visit A bi-bottom hooks-up at a video store.in Gay Male
A Fantasy Fulfilled A blind date escalates into a gang bang.in Gay Male
A Run to the Restroom Straight guy gets his cherry popped at restaurant.in Gay Male
A Hard Ride Hitchiker services truck driver and friends.in Gay Male
A Moment of Weakness Taken by a stronger male.in Gay Male
More Stories