My ex-wife and I had a pretty tepid sex life for the most part. She came when I ate her, but didn't seem to care whether or not I did eat her. She hated swallowing cum, so the blowjobs were infrequent and far from perfect. Fucking was not really of much interest to her.
She did have nice tits which she would let me fuck. She would hold them together with my cock in between. The pre-cum from my cock has always flowed plentifully, and that was all the lube I needed. When I came I would shove forward as far as I could, the way you do when you cum into a cunt, pressing hard to bury it deep. The head of my cock would appear between the top of her tits and my cum would splash on the underside of her chin, pooling in the crease of throat and shoulders, overflowing around the sides of her neck as my cock softened between her full tits.
Her cunt was tight, I'll say that. I could barely squeeze it all the way in before I was ready to shoot my load. My cock is about average length, but pretty thick. I could always hit bottom with her, and could feel the tip of my cock pushing into the folds of her cervix.
Partly because of my cock's girth and partly because of the same Catholic inhibitions that kept her from swallowing, she wouldn't consider anal. For years, I tried everything to talk her into it. One time, though, I squeezed into her ass. This is the story of that occasion.
We were on vacation in the Caribbean. There were lots of hot women in small suits on the beaches. I was constantly overheated and on the verge of springing an embarrassing boner while we strolled along the beach.
One afternoon we were walking along the edge of the beach and passed a couple lying naked on a blanket. The woman had long black hair and a smooth, tanned back. Her waist was narrow and her legs long and slim. She was on her stomach, with her legs together. You couldn't really see much, except her heart-shaped ass and the sides of her tits. He was on his back, fully exposed to the sun, sleeping. His cock was more than half erect, long and thin, with a foreskin that partially covered the head.
I quietly indicated their exposure to my wife, who tried to ignore the sight. As we passed I whispered about them, verbalizing the fantasies in my own head. I suggested that the state of his cock looked like they might have just had sex or might be about to. She seemed somewhat receptive to my idle speculation, so I kept going. I had a hard-on, thinking about the two of them fucking.
I surmised that if he rolled over he might roll on top of her and that his cock might slide into her ass before she even knew it was happening. I noted that his cock was thin and might fit just fine. She laughed and told me I was crazy, but I glanced back over my shoulder, half expecting to see him sodomizing her on the beach.
We had dinner and a few drinks that night and went to bed at a reasonable hour. My wife slept naked, which drove me crazy when I was horny, as I was that night. I fell asleep with a hard-on and my sleep was occupied with sex dreams.
I dreamt about the couple on the beach. I was that guy. The dream was really vivid. I was lying next to the naked woman with the long dark hair and I was half asleep. My earlier fantasy of him rolling over and fucking her in the ass was a real possibility in my dream. In my dream I knew that my fantasy partner wouldn't mind. All that afternoon, I had imagined that the two of them had done that many times and that she liked his cock in her ass.
So, in my dream, I rolled over so that my cock nudged between the buttocks of my dream babe. I pushed forward and hit solid flesh. I dreamt of sliding my cock between the sun-lotioned cheeks of her ass until it was pointed at her tight opening. I got it squared to the hole and then slid forward. I dreamt of the taut muscles stretching open.
My black-haired beauty squirmed and protested a little as I pushed forward. The head popped past the sphincter and she squealed and then lay still. I fucked the head of my cock through the ring. The tightness was exquisite on the head of my cock. I didn't go very deep before my cock started pumping jizz into her skintight ass. Two, three, close to ten spurts fired into her hot, snug butt before my dream cock wilted and I rolled back onto the beach in a contented sleep.
When I woke up in the morning I noticed that my cock was sore and that there was dried cum on my stomach. I figured I'd had a nocturnal emission. I remembered my dream and how vivid it was. My cock started hardening. I reached over and touched my wife's naked ass. As I did, she said, somewhat curtly, "You did a number on that last night."
I thought about my dream, it had seemed so real. Had I?
I told her about my dream and she said, "That wasn't a dream. I tried to stop you but you just kept going."
I was stunned; I had cum in my wife's ass and had slept through it. My cock was hard as a rock as I reached between her ass cheeks and felt the distinctive texture of cum on the tight opening of her ass.
"Are you okay," I asked.
"I was pretty pissed off at first, but it wasn't so bad since you didn't go in very far and you didn't last very long."
I rolled over on top of her, my cock nestling between her ass cheeks.
"What the hell do you think you're doing?" she asked.
"I want to try it again, while I'm awake," I said. I slid the tip of my cock, already dripping with pre-cum, against the tiny opening of her ass.
"I don't think you..." she managed to say before I slid my cock forward and started to stretch her opening a little.
I pressed harder, but my cock didn't slide in, it only indented the flesh of around her anus. My cock oozed pre-cum which spread out over the tip of my cock and into the pore of her asshole.
"Seriously, Joe, stop it."
I was hard as a rock, remembering the feeling of her asshole, stretched like a doubled-over rubber band around the head of my cock. I was horny to the exclusion of all else. I kept pressing and the ring started stretching over the spongy wet tip of my dick.
She started to squirm and to grunt in outrage. I pressed a little harder and her wiggling twisted her ass-ring over the tip of my dick, the pre-cum and last night's jizz helping my cock slide in just a bit.
She screamed and struggled again, this time her movements were enough so that the head of my cock wedged open her hole. The swollen head of my cock popped all the way in, her anal ring stretched over the crown and ended up clamped behind the corona of my cock.
She froze and groaned. I held still. I was near shooting my load already. She moaned, "Get it over with" in resignation. I was happy to accept that half- serious invitation.
I slid back slightly, pulling some pre-cum and jizm along with me. With that extra lube on the outside of her hole I was able to push forward a little further on the in-stroke. I was now about an inch past the crown and about a third of my cock was in her ass.
This was as far as I'd gotten in my dream. In the dream I'd ridden the sensitive part of my cock in and out of the super tight opening of her ass which brought my anxious cock to a fast ejaculation. I wanted to see what it was like in deep while I had the chance, so I pushed my luck.
I slowly wiggled my cock in and out, bringing cum from last night further up my shaft so that more and more of my cock could squeeze through the opening. Pre-cum was pouring out of the tip of my cock, providing ample lube for my cock head to push forward as the pumping wet more of the shaft of my cock with last night's fountain of jizm.
I wiggled my dick forward an eighth inch at a time. She groaned as I slowly slid my cock two inches, three inches, four inches into her ass. I felt the ring of her anus approach my pubes a little at a time as the head of my cock explored the hot, soft insides of her ass. Finally, I felt her lower ass-cheeks squashed against my balls as the ring of her ass pinched the base of my cock.
I had almost come when I was driving into her asshole, but the inner depths weren't as tight around my cock- head. They felt loose and hot while her asshole acted like a cock-ring around the base of my cock, causing it to swell to painful hardness and size deep in her ass.
I began to fuck her in short, one-inch strokes. The light friction of her loose inner ass, slick from last night's huge load and my free flowing pre-cum were enough to keep me on the edge without triggering my spasms.
I kept a slow in-out rhythm, lengthening my strokes. She whimpered and occasionally said "ouch, oh, Jesus" as I fucked her. My strokes lengthened to the point where the flange of my cock grabbed her anal ring and pulled it back on the outstroke. On the in strokes I could feel the hotness of her inner ass on my cock-head as her asshole pressed against my pubic hair and my balls which were retracting in preparation for delivery of another record cum load.
I was getting near the point of no return. I continued the long slow strokes. Once I pulled back too far and the flange of my cock went past her sphincter. The slickness squeezed my cock-head out of her ass for a second before I slowly slid it back through the ring of her ass. It wasn't quite as hard to slide in now, but it was still dammed tight.
I sped up my fucking until I could feel my climax start, I slid into her ass as far as I could go as my cock swelled with a first dry spasm and my balls tightened to delivery the first wad of jizz.
My cock-head must have really swelled up because she exclaimed "Ouch," with each spurt of my cock. In spite of my load the night before, I pumped a pint of sperm up her ass. Ten times my cock swelled and fired deep into her butt. Ten times she squeaked, "Ow," as the cock-head stretched her rectum and squirted hard spurts of cream deep into her colon.
I lay on top of her as my cock shrunk, slimy with two loads of jizz. Her ass was still tight, in spite of the stretching, and spit my cock out as it lost all its hardness, completely sated.