Caroline Surprise

I could have done that 'til kingdom come, but she whipped around to suck my I-didn't-think-it-could-get-any-stiffer dick with maximum suction to make it even harder, then turned back around forward again and guided me right into her tunnel of love. Remarkably, her pussy was not reamed out by Robert The Monster Cock and was just the right size for me—not too tight, not too loose.

She felt absolutely fantastic, and I must have been doing pretty good myself, for every few minutes, she'd grind down hard in little circles, come to a halt, and have a face-flushing orgasm before gradually picking up speed for a repeat. I wasn't exactly counting, but this must have happened at least half a dozen times, and every time just moments before I was about to cum. When that occurs, it raises my ejaculation threshold, and that, combined with her pussy juice being the all-time slipperiest, meant I just was not going to blow.

Of course, when I hadn't been looking at her beautiful face or world-class tits jiggling in the vanity mirror, I was staring at her little wrinkled brown anus. So I pulled out, dropped to my knees, and went to town on it, first rimming, then tongue-fucking it, all the while keeping my thumb busy on her nubbin'. Her pooper was simply delicious, so clean, so tasty, so round, its teeny wrinkles extending straight away from the orifice to make a perfect, multi-pointed star. Her sphincter was relaxed, and when my tongue wedged it as far open as it would, I replaced it with a finger, then two, while lick-sucking her clit. Caroline was in high heaven, cumming yet several more times.

For butt-fucking lubrication, I stood up and plunged my cock back into her sopping-wet pussy as I simultaneously pried both thumbs up to the second knuckle into her bum. She reached around to grasp the base of my raging-hard dick in a death grip, pulled it out of her vagina, and pointed it like a gun right on her primed butthole. In a pretty damn good impression of Clint Eastwood's Dirty Harry character, Caroline looked over her shoulder straight into my eyes and said, "Go ahead. Make my day."

And so I did, gradually easing myself inch by inch by inch all the way into her virgin anal cavity. Oh yeah!!! It felt great, all right--so tight, so warm, quivering.

"Oh my God!" Caroline gasped. "I've wanted to do this for years. The all-filled-up feeling is amazing, even better than I'd imagined."

I held still for a few minutes, then slowly pulled back and gently pushed back in to the hilt. If there was a question of my being able to cum before, it was now a matter of spewing too soon. So I CAREFULLY pulled all the way out and watched her bad hole close, assuming the perfect little star of wrinkles once again. For more lubrication and her pleasure, I bored my shaft up and back through her prodigious, literally dripping wet pussy lips, waggled it back and forth across her big, rigid clit, then punched back through her sphincter.

While the tactile sensation was incomparable, so was the view. There was my trusty cock plunging in the prettiest little butthole of all time. Every once in a while, I'd pull all the way out to watch it close up, re-lube as above, pull apart those perfect ass cheeks, and bore back in.

When I could hold back no longer, I announced, "I'm cumming," but before I could squirt, she wheeled around, choked my chicken, and sucked me all the way down to my balls, swallowing volley after volley after volley of ejaculate as I forcefully grasped her terrific tits and she looked up into my eyes. It was one of the best orgasms ever, and there was not even a vestige of semen left in my tube—she'd sucked every last drop out.

"Mmmmm. That was sooooo good. Your sperm is quite tasty. Should tide me over until lunch," she giggled, before standing up to give me a long, sensuous French kiss.

Naked there in the bright light of the bathroom, we just stared at each other for what must have been five minutes without saying a word. My 2/3 erection would not deflate, and I just kept saying to myself over and over, "I just had sex with Caroline, Hugh's awesome sister Caroline," as my eyes roamed all over her perfect body and face. From the look on her face, I suspect she was thinking similarly: "I just fucked my brother's best friend (Hornyman), something I've wanted to do for years."

Finally, she broke the silence. "Listen, I'd love you to stay, but you better get back downstairs before Mom comes looking for you."

I slinked back down the stairs to find Hugh three sheets to the wind swilling Bud and watching General Hospital. Though I'd been upstairs for over an hour, thankfully, he was in no shape to notice I'd been absent for more than a few minutes, which was confirmed when he slurred, "Didju haf a nithe pith?"

I picked up my notes and made a few more calls to put the finishing touches on the funeral, which by then had ballooned into a Cecil B. De Mille production. Shortly, I heard the front door slam shut, and his mom walked in, behaving in a way that was anything but that of a woman just widowed.

With an exasperated, pull-your-hair-out gesture, she huffed, "Sheesh! I haven't seen some of those people since our wedding. I mean, I appreciate friends expressing their sympathy and all, but popping in on me unexpectedly is NOT the way to do it—isn't that what the funeral's for? I'm really grateful for all your help in making the arrangements; with a house full of people, I don't know what I would have done without you. Sorry about slamming the door so hard, but I finally got rid of the last visitor, my husband's closest friend. Can you believe he was hitting on me?!!! I need one of those cold beers!"

Though his timing was clearly inappropriate, actually, it was easy to believe. Only in her mid-50s and looking ten years younger, the widow was still quite the babe. I'd always thought her very attractive, but until then—right after I had mind-blowing sex with her daughter—I'd never realized just how. Take Caroline, shave off four or five inches of height, add twenty-five years, and you have her mom. Why she was wearing tennis whites that morning, I can only guess—something quick and easy to throw on when people suddenly started knocking—but she looked fantastic. The mid-thigh-length skirt showed off a spectacular pair of slim, tan legs, and, above a slender waist, the tight halter-top left little doubt what her bountiful breasts looked like. They were the mirror image of Caroline's, complete with dark, rigid nipples printing visibly through the white bra and tennis top. Damn!

She got one of Hugh's Budweisers, brought me one, too, and sat down close beside me on the couch to review the funeral arrangements I'd made. Her bare leg was against my bare leg, and, yes, it felt good. Her hand made frequent contact with my knee and thigh, and, yes, it felt good. When she'd lean forward, which was often, her left boob would punch into the back of my right upper arm, and, yes, it felt good. Though I'd just blasted a huge wad into Caroline's luscious mouth not fifteen minutes before, I was already feeling really horny again, and Mom would have had to be blind not to notice my erection. All the while, Hugh was glued to the soap opera, sipping beer, oblivious.

From the corner, footsteps clacked down the stairs. It was Caroline, all fresh and dressed, flashing a bright smile. She was, of course, ravishing.

"Hey, y'all. Oh, hi, (Hornyman). I didn't know you were here. What a pleasant surprise. Great to see you. It's been a really long time."

She was playing her part so very well. Those were the exact same words she'd used when I'd actually seen her an hour or so earlier, so I did likewise, embracing her and saying, "I'm so sorry about your dad, Caroline."

There was a knock at the front door, her mom rolled her eyes, and Caroline said she'd get it.

I heard voices but couldn't make out what was being said. Shortly, Caroline returned with her arm around an athletically built man who looked familiar but I couldn't place at first.

Always well-mannered, Caroline immediately introduced him. "(Hornyman), I'd like you to meet my fiancé, Robert. Robert, this is (Hornyman), an old friend of Hugh's and the entire family."

"Of course, Robert, it's been years, but I remember you from prep school. You were one year behind Hugh and me. All-city running back and National Honor Society, if I recall correctly. So pleased to 're-meet' you." I said ever-so-politely, repressing the shock of having just learned that he was no less than engaged to Caroline who had just fucked and sucked me silly 20 minutes ago.

"Quite a good memory," he said. "You dated Leigh K, right?"

Before I could respond, the totally drunk Hugh chimed in, "Yeah, she wath hith girlfriend, but everybody pretty mush screwed everybody's else's girl in those days, 'cept Caroline. She's always been sush a good girl."

Good girl, my foot!!!

Caroline steered the conversation politely back on track, "Robert and I are having a big wedding in June—which is just around the corner—and, naturally, you're invited to all the festivities, so make sure we've got your current address for invitations. Since Mom's the only family either of us have here now, and our friends and other family members are scattered all over, we've decided to have it in Columbia, South Carolina, where we live now."

"Oh, yes, you absolutely must come. I'll have to have someone to dance with, and I can think of no one better than you," her mom pleaded, patting my knee and poking her boob into my arm. "Robert and Caroline have plenty of room and will be glad to put you up at their house. I'll be staying there, of course."

"You'll have to share a bathroom, though, but I'm sure that won't be a problem," Caroline added, knowing only she and I knew the real meaning of that comment and, at the same time, slyly giving her full approval for whatever might happen between her mom and me

I knew the wedding and parties before would be first-class productions, and there was sure to be a few cute unattached bridesmaids in the offing. But, as far as Caroline's mom was concerned, she was right there in town, so why would I travel all the way to Columbia to hook up with her?

But that's another story.