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Caroline Surprise

By: Hornyman69WithU



Looking at a good-looking naked girl is always exciting, but even more so when it happens completely unexpectedly. Add to that her being a truly awesome woman with a "goody-two-shoes" reputation, and you have the formula for the very best voyeuring possible. Such was the case with Caroline, the younger sister of my good buddy, Hugh.

To put things in perspective, let me start from the beginning.

Some of you may have read my story, "First Orgy," which tells in excruciating detail the spontaneous group sex I had in the Tulane dorm with high school girlfriend Leigh, her roommate, Lisa, and the floor resident advisor, Pat. That happened when I hitchhiked from where I went to college in Atlanta to New Orleans to visit Leigh for Mardis Gras in February, 1978. 

That was an incredible sexual experience, but perhaps more incredible was that the orgy paired up me and Lisa—Leigh's best friend—and Leigh was totally OK with the new order. She not only remained friends and roommates with Lisa, but also continued to regularly have sex with me back in our home town, as Lisa's home was way the hell up in Casper, WY. 

However, when Lisa was in town visiting Leigh, like for Spring Break or over the summer, Lisa and I were a standing item. Nevertheless, the three us, sometimes inviting another lucky guy, would often pile into bed for a group romp.

It was the end of summer, and Lisa was in town for a visit. I kind of felt bad for Leigh, since she did not have a date on such occasions, so I picked up Hugh before driving over to Leigh's parent's house to get the girls. Leigh and Hugh had been friends—nothing more—since high school, and I figured he'd wind up being one of those "lucky guys" in an orgy with her, Lisa, and me before the evening was done. 

While we were still parked in the driveway trying to decide where to go, Hugh casually mentioned that his parents were out of town. That was his subtle way of saying he was short of cash and had nothing to contribute towards an evening of barhopping, and so we should party at his folks'. As he said this, he was also staring at Leigh with a how-'bout-you-and-me-tonight look. Apparently, she was thinking the same thing and slid over beside him in the back seat.

So we picked up a big bottle of cheap wine and drove back over to Hugh's house. We got blitzed there, and I was expecting us to wind up in an MFMF, Hugh being a new guy in the mix and all. But after all the group sex we'd had that summer, the girls were apparently orgied out, and Lisa and I, and Hugh and Leigh, respectively, wound up pairing off, instead. They went up to his bedroom, and so there Lisa and I were downstairs, left alone to our own devices in the big house devoid of parental units. 

While the perpetually horny Lisa dug out my cock and hungrily sucked it up to size on the living room couch, I considered where we should fuck. Right there? Nah, too ordinary. There were two spare bedrooms, but doing it in one of those would be nothing special, either. We peered into the downstairs master bedroom—Hugh's parent's—which was a titillating notion, considering that this was their private boudoir and that his mom was quite attractive and some twenty to twenty-five years his father's junior. But their bedroom was a veritable museum--everything perfect and perfectly in place--and it would be impossible to get the dozen or so silk pillows back on the bed exactly as his mom had carefully arranged them, and, of course, we'd have to wash the sheets and all. So, I ruled that out. 

Then it hit me, Caroline's bedroom. Hugh's only sibling and a year younger, Caroline was a super-straight goody-two-shoes who'd just graduated that spring—from the same hoity-toity girl's prep school from which Leigh had graduated the year before. I'd heard Hugh mention that his sister was leaving town early for college, and since it was mid-August and I hadn't seen her around lately, I figured she'd already left.

So, we went upstairs to her bedroom, where we could hear Leigh and Hugh going at it in his own room just down the hall. There was Caroline's perfect little twin bed, with an ornate floral bedspread and clean, crisp linens. Oh, my, would it be fun to de-virginize that bed by screwing my little slut Lisa as lewdly as possible in it! And so that's precisely what we did for the next two hours, so vigorously that the slats rattled free and the mattress went crashing to the floor. 

That was funny as hell, but, even so, we never broke sexual stride. I eventually blasted a big wad in her pussy, and I will never forget Lisa wedging the pillow between her thighs as I squeezed her abdomen to force out prodigious amounts of a pussy-juice-and-cum cocktail onto Caroline's perfect pink pillowcase. She'd come home for Thanksgiving break, maybe earlier, and lay her head right on it!

The next morning, as usual, I awoke early, with a hard-on. Lisa was sawing logs, face down, her legs splayed wide revealing a pussy still flared out from the pounding the night before. I almost stuck my cock in it, but I had to piss badly, so I went down the hall to the bathroom, where I took a long leak and found some Tylenol to treat my pounding head. Note to self: When you buy cheap wine, you get what you pay for. The house was quiet as a mouse, perfect for sleeping in, but when I'm awake, I'm awake for good, so I just went back to the bedroom, intending to wank myself back up to size and poke it into Lisa.

But upon entering, I was distracted by the framed photographs on Caroline's dresser. The ones that really caught my eye were of her in a revealing swimsuit on the beach, probably taken during the previous Spring Break. It was apparent to anyone that she had a beautiful face and hair, and I always knew she had a nice physique somewhere beneath the layers of conservative clothes she wore. In contrast, the skimpy bikini barely covered her goodies. WOW, never did I imagine that she had a knockout body like that! 

Flawlessly smooth, dark-tanned skin? Check.

Long, slender legs and arms? Check.

Firm, heart-shaped ass? Check.

Slim, hourglass waist punctuated with a sexy round navel? Check.

Big, firm tits, close together making deep cleavage? Check.

Hard nipples printing prominently through the fabric? Check.

Now, I'm not ordinarily a snoop, but seeing her theretofore hidden, surprisingly large boobs in the photos, I had to conduct an investigation.

So, I checked the dresser, finding bras and panties in the very first, top drawer. All her bras were what I would classify as the industrial-strength type—stoutly constructed, with 3 or 4 hooks, designed to give maximum support to a hefty pair of breasts, yet still feminine and pretty with decorative lace. Hmmm, 34D. Based on the photos, I would have guessed even bigger but, on second thought, Caroline was tall, maybe 5' 8" or 9", yet was slender, so D-cups on her slim upper torso appeared comparatively large.

All right, so I'd found out what I wanted about her breast size, but there were her panties, as well, so, might as well check those out, too. They were all the same bikini style, and, like her bras, only in black, white, and beige. She was conservative, no hot pink or red undies here. Even so, my dick was rock-hard again. Staring at her bikini-clad body in the pictures, I found my hand using a pair of slick black panties to stroke myself up to size. OK, so here I am beating off to a photograph of my buddy's little sister when I have a perfectly willing, sexy and buck naked live chick available not ten feet away. But Caroline was novel, and Lisa was familiar. Such is the nature of the human male.

I was hung over, and it took a few minutes to put two and two together—why would Caroline leave a drawer full of underwear if she'd already left for college?—when I heard voices approaching from down the hall. 

Shit! Even if Hugh was my good buddy and Leigh my good friend/occasional lover, I would die if either of them knew I was rifling through his sister's under clothes. So I eased the drawer shut, leaped back into the broken-down bed, snatched the bedspread over me, and pretended I was asleep. Lisa was still snoring loudly, a good thing under these circumstances.

I heard someone enter, and a drawer slide open. Then I heard an unfamiliar voice, a male.

"Hey, Caroline, there's a nekkid girl in your bed!" he announced in a none-too-hushed tone."

"Shhhhh. Keep your voice down. Like I didn't notice. That's Lisa, a friend of Leigh K's from Tulane. You know I told you about Leigh, the super-smart girl who was the valedictorian last year, the daughter of Mr. K, THE Mr. K. She must be in Hugh's room behind closed doors with him. I'm surprised Lisa's alone. She's a little slut.

"You're a slut, too, when you wanna be," the dude said. "That was a great idea screwing in your folk's bed last night. Come to think of it, the way you swallow every drop of sperm, that has a side benefit—we don't have to wash the sheets."

"Yep, no spill, no mess. That's me, good girl by day, slut by night," she proudly asserted.

Well, sonofabitch! In less than half a minute, I had just learned that Caroline was not the goody-two-shoes I thought she was. She'd sucked her boyfriend dry in her mom and dad's bed, same place I'd wanted to do Lisa. I guess Caroline knew exactly how to replace the pillows! And, since I was down in the well of the broken-down bed, covered completely up by her billowy bedspread, thankfully neither she nor her boyfriend could tell I was right there, much less that I was wide awake. 

Caroline shuffled to the other end of the dresser. Now, through the narrow crack between bedspread and frame, I could see her bare calves and feet. Then she stooped down and opened the bottom drawer. OhMyGod, she was naked!

I could see her lower back and ass, which was perfect, just perfect. Then she leaned forward to fish something from the drawer. Her crack spread, and for just a moment, I caught a glimpse of her asshole, pubic hair, and the nippley tip of one dangling boob before she stood up again. Wow!

"You have an erection AGAIN, Robert, so soon?" Hugh's sister whispered, obviously pleasantly surprised.

"Watching you walk around naked makes me hard as a bat, and that snoring slut's open pussy doesn't help," he admitted.

"I see. Well, you can look at her all you want, but no touching."

I shifted my gaze over to where his voice was coming from. He was standing in the doorway, farther away than Caroline, so I could see him from the waist down. He had a hard-on all right. My Lord his cock was enormous, as long and thick as the Everyready 3 D-cell flashlight out in my car.

"That looks terribly inviting, Robert. You wouldn't mind if I sucked on it, now would you?" Caroline offered.

"Right here?" 

"Why not? It's just a little past seven, and Lisa's obviously down for the count. Besides, my folks are out of town, and this is the first opportunity we've ever had to do it in my OWN bedroom before. Just remember to keep your voice down, and quietly pull the door shut in case my brother or Leigh comes down the hall," she reasoned.

Then Caroline came into view, and they embraced. I couldn't see the top half of either of them, but it sounded like they were kissing. I had a great view of her divine butt, which got even better when he kneaded her buns to reveal a teeny wrinkled pooper and barely visible pussy lips dangling beneath her light brown pubes.

That was good, but what I really wanted to see were those tits, yet they were just out of my line of sight, and I dared not risk lifting the bedspread to bring them into view. Anyway, she'd promised a blow-job, so I looked forward to that and waited. And waited. And waited. I don't think two people have ever stayed on first and second base so long before moving along to third as that couple.

I could tell he was fondling her boobs, but again, that part of her body was out of view, and I was not about to take the chance of being discovered. They backed away from the door a few feet, and he began to suck her tits, but as they did so, she got turned so that her back was to me, so I could not see one bit of them. Awfully frustrating, but I could certainly hear his slurping and her pleasure!

"Oh, Robert, I just love the way you suck my nipple. Yeah, nibble on it. Twist it. Now do the other one. That's it. Get 'em both in your mouth at the same time. See how long and hard you've made them. Feels wonderful! Good boy!!"

After at least ten minutes of that, she suddenly dropped to her knees. For a nanosecond, I saw the side of her right boob and its dark red, bullet-like nipple, but then her arm blocked the view as she grasped his cock firmly at the base and began to lick it like a lollipop. Up and down and up and down she licked, getting the whole monstrosity wet with saliva before she circled the oversize head with her agile tongue, first one direction, then the other. 

Then Caroline went to work on his balls, licking them all over and sucking first one, then the other, and then both at the same time, loudly slurping as she went, all the while making little circles with the pad of her thumb on the extra-sensitive spot on the underneath side of his big dick. With slobber all over, she slathered it back and forth over her chin, cheeks, and nose, batting it smartly on her face and extended tongue. 

Finally, she slurped her way up to the head and sucked it into her mouth, bobbing up and down. Each time she did, she went down a bit farther, until she eventually had 2/3 of his gigantic shlong in her mouth, cheeks concave with suction. Occasionally, Caroline would pull it all the way out with a "pop" and wank and stare at it before gulping back into her pretty mouth again to resume full blow-job duty. Caroline had always had a gorgeous face, but with a dick in her mouth, it was even more beautiful.

And she kept her hands busy, too, tickling his scrotum with the tips of her perfectly manicured nails. Every once in a while, she'd tightly encircle a hand at the base of his shaft beneath his testicles and pull them up towards her lips as she sucked down his cock, pausing to stick her tongue way out and lick his balls. Caroline was quite obviously an expert at giving head, and she appeared to be greatly enjoying every second of it.

That blow-job must have lasted a half hour, which was great for Robert, and a real turn-on for me to watch. However, the problem was, she was right-handed, and so with it busy tickling his balls or wanking his shaft in tandem with her sucking, the upper part of her right arm completely blocked the view of her boobs. Otherwise, she was kneeling juxtaposed to him in a way that would have given me a perfect breastial sight line. Had she been a southpaw like her brother, I could have easily seen those yabbahoes.

Well, my wish finally came true when she popped her mouth off him, reared back, and shook them back and forth burlesque style. Oh my God, her tits were stupendous! Though they were about the size of small grapefruits, they were not round, but rather shaped like bullets--make that artillery shells—that stuck straight out from her lithe rib cage. Close together and very firm, they made deep, natural cleavage. Long, dark red nipples projected out from the very center of each one. 

Simultaneously with both hands, she pulled and twiddled them vigorously between thumbs and index fingers, then used them to forcefully waggle her boobs every which way. Even for an 18-year-old like Caroline, they were extraordinarily firm and taut. These days, you'd swear they were fresh implants, but I could tell by the way they moved they were the real deal. I've never seen another set of natural breasts like those.

Next thing she did was hike them up, slobber saliva between them, and wrap them around Robert's massive member, sliding them up and down and enjoying the pleasure as much as he. Ah, titty-fucks, I love 'em! Lisa had small, delicious boobs. Leigh's were on the near side of medium-sized and very pretty. The chicks at college I'd been to bed with that spring all had hot bodies, but none had big tits. In fact, the last gal I'd titty-fucked was Pat, the ample-breasted RA in Leigh and Lisa's Tulane dorm who took part in our first orgy. That had been over six months before. No wonder I was so fixated on Caroline's hooters—big, firm, close together, and projecting straight out, they were ideal titty-fuck material.

I realized I still had her black panties balled up in my hand, and naturally, I was stiff as a brick. No telling how long it would be until I'd encounter a suitable pair of breasts, so I placed the slick panties between my upper thighs, and slid my cock between them, for a faux titty-fuck. Not as good as the real thing, but pretty damn good while watching them from 10 feet. 

The sun was up by then, and, though the shades were down, it was plenty bright enough in her upstairs east-side bedroom to see very well. Of course, the better I could see them, the better they might be able to see me. But weenie-wiggling there wasn't as risky as it sounds, for Caroline's pillowed bedspread was rather stiff and remained tented up over me.

They took their sweet time with the titty-fuck, Caroline occasionally breaking it off to swab his humonga-cock across her big, rubbery nipples and suck it a bit before resuming the back-and-forth slide in her canyon of cleavage. With her panties between my thighs, I was with them stroke for stroke.

At long last, she gazed up into his eyes and softly said, "I really want you to eat me now."

Using his cock like a leash, Caroline lead him a few feet to the left over to her dresser, leaned forward across the top of it, and pooched her perfect ass out. Oh my Lord, what a beautiful pussy! Big, dark lips surrounding a juicy red interior over a thick, half-hooded clit. He pulled her buns apart and stared at her genitals, giving me an unobstructed view.

From where I was hidden, she could not have been in a better location and position had I had the option of instructing her exactly where to be. I not only had an ideal view of her bottom, but I could also see her tits, dangling down alluringly. Further, in the reflection of the mirror atop the dresser, I could see her tats from another angle, and her face, as well. 

Starting at her nubbin, he gave her a long, slow lick up through her prodigious labia to and across her tiny anus. The look on her face was simply priceless, a mesmerized, drunken expression. Over and over he'd lick, all the way up, all the way down, lingering to suck her clit or pull those large lips through his or make little circles with the tip of his tongue on her pooper. Then, he'd just stare at it all for a bit while friggin' her puss with first two, then three, then four fingers.

The whole time, Caroline was whimpering with pleasure, cumming, I counted, three times. You could tell she was suppressing her moans so as not to wake up Lisa. 

Finally, he stood up and peeled her butt cheeks so wide apart that her vagina actually opened. Placing the bulbous head of his enormous cock right there, he swabbed it back and forth several times to get it wet with pussy juice, then parked it for what seemed like minutes between Caroline's large, dark labia. What the hell was he waiting for? I mean, fuck the girl. Fuck her!

Her pussy was so wet that it's juice ran down his shaft and dripped off his balls. OK, I got it; he's waiting for full lube before plunging in. Even when he finally did, her pussy lips completely disappeared as he gradually slid it all the way in to the hilt, when he froze completely still. I could tell by her bugged-out eyes why: It was going to take a while for her to adjust to his massive member inside her. They'd done this many times before and had the routine down pat.

Very slowly, he pulled back. Out folded her pussy lips, then, tightly hugging his turgid tee-tee, the walls of her pussy turned wrong-side-out until he pulled himself completely out. Just as slowly, he pushed it all the way back in again. I don't think I could have ever screwed her so slowly as he did, but she remained sopping wet as he ever-so-gradually picked up a little speed, yet never exceeding a one thousand one, one thousand two, one thousand three pace. With each methodical thrust, her dangling breasts would wobble, wobble, wobble, their pencil eraser nips folding forward and back on the top of the dresser.


Caroline Surprise



From the way her pussy was turning wrong side out when he withdrew, Caroline must have had a tight pussy, but, then again, maybe not--this dude had a giant prick. Wouldn't I like to trade places with him to find out!

Caroline's whimpers, in time to his thrusts, became increasingly intense. After what seemed an eternity, she bit her lower lip, and her face flushed. She was cumming again, and this was quite obviously The Big O. Rapidly ramping up to a fast fuck, he squeezed his buns tightly together, and—just as obviously—had his own orgasm. 

Bending forward to seize her boobs, I could now see his climax-contorted face and noticed he was looking down towards where my feet were. Still sliding my cock across her panties between my thighs, I was on the brink of cumming, too, but--oh shit!--had he seen me move? 

I froze, too scared to even breath or, of course, cum. His pounding gradually slowed to a stop, with his dick buried deep in Caroline's sex but his eyes still trained on something at the foot of her bed. Then, I realized it wasn't my feet he was staring at, but the snoring Lisa. 

This guy had his cock in one of the best-looking, sexiest chicks ever, yet, to take himself over the edge, he'd been gazing at Lisa's flared-open pussy!!! If I could, I would have burst out laughing. Like any perfectly normal male, he was more interested in the strange stuff than the same ol' same ol'!

Slowly, he withdrew from her hole and knelt down, pulling her buns apart. My, oh my, what a gorgeous pussy Caroline had--those dark, flappy labia, that big, hard clit sticking out from its meaty hood. A river of spooge began to ooze from it, and, surprisingly, he sucked and licked every drop of it up. She wheeled around and dropped to her knees, embraced him, and they French-kissed passionately. 

I didn't realize at first what was going on, but Caroline swallowed and said, softly, "I just love the taste of cum in the morning, or afternoon, or evening, or anytime, really. I'm starved! Let's go down to the kitchen and make a big breakfast."

And with that, she brushed her hair, gathered up the bra, panties, shorts, and polo shirt she'd selected, and wiggled her feet into a pair of white K-Swiss tennis shoes. Checking to ensure the coast was clear, they slipped out the door into the hallway.  

Well, son of a bitch. Caroline had come to her room to fetch clean clothes. Her boyfriend had followed, seen Lisa nude, and got turned on. Since she was obviously asleep, they decided to do the nasty in Caroline's bedroom for the first time. Had Lisa not been there--buck nekkid with her splayed pussy on parade, no less--and I awake with just enough time to dive under the bedspread, none of it would have ever happened. Sometimes, Murphy's Law is suspended and things actually work out!

At any rate, I was hard as steel and horny as the devil. So, I picked up the diminutive Lisa and draped her doggie over the dresser to "re-enact the crime." She awoke, or should I say, "came to," as I licked and fingered her pussy just like Caroline's boyfriend had done her minutes before. Slutty Lisa was always up for sex. It didn't matter when or where, or even who.

For an extra kick, I draped Caroline's panties over my rod then slowly eased my much-smaller-than-her-boyfriend's dick into Lisa's just-as-wet pussy. I didn't realize until then how much Lisa resembled Caroline, from the rear, at least. Like her, Lisa had a dark complexion, about the same color and length of hair, a smaller but nearly identically-shaped butt, and similarly generous genitalia. Staring over her shoulder at the largest bikini photo of Caroline there on the dresser, it was quite easy to imagine myself fucking her, so that's just what I did. I even fantasized that her boyfriend was voyeuring us from the cover of her bedspread!

With that in mind, I blasted a huge wad into Caroline, er, Lisa. Of course, to complete the re-enactment, I sucked my sperm from her cunt and fed it into her mouth. Like all good girls, she swallowed every drop, though not with quite the same glee as Caroline.

Lisa and I crashed big time and didn't awake until after noon. Leigh and Hugh were behind a locked door in the shower together, so needing to piss, I quickly dressed and ran downstairs. There was absolutely no sign of Caroline or her boyfriend. Although I could smell bacon, there were no dirty dishes or spatter of grease from their big breakfast, and the master bedroom was pristine. Taking a leak in the master bath, I did notice the shower was moist, so they must have gotten cleaned up in there.

When I went back up to Caroline's bedroom, it occurred to me to take those black panties as a souvenir, but I could not find them anywhere. So, I looked in the top dresser drawer for another pair, but all her underclothes were gone! What? Opening the other drawers, and checking the closets, too, I discovered that almost all her clothes were gone. 

She had come in there while we were sleeping, got all the things she needed for college, packed, and apparently left for Vanderbilt. I had fallen asleep in her bed on top of the bedspread without a stitch of clothes on, so Caroline must have seen me completely nude. What's more, the last place her black panties had been were hanging on my prick, and I could not find them anywhere among the sheets and bedspread, so she must have fished around in the bed to retrieve them. Might she have also fished around with my cock, too? I had a faint recollection of someone playing with it, but with Lisa right there, I never opened my sleepy eyes or gave it a second thought at the time. Interesting. Very interesting!

In another week, Leigh and Lisa were back for their sophomore year at Tulane, and Hugh and I were back at our college. I was dying to tell him what had happened, but though ultra-liberal, he had a bit of an older, protective brother attitude about his sister, so I didn't. In fact, I never told anyone until I wrote this story 30 years later. It's not nearly so shocking to anyone who does not know Caroline, and she was such a goody-two-shoes that those who do know her would simply never believe it. 

I saw Caroline several times when she paid Hugh a visit while we were in college. When she came, though beautiful as ever, she always wore conservative, preppy dresses with hose that reinforced her upstanding, good-little-sorority-girl image. Of course, having been witness to her hot naked body and sexual tigress ways, I no longer saw her that way at all. I looked hard for any sign that she saw me naked and might have even copped a feel that August morning in '78, but she never let on she'd done either. 

On the other hand, she seemed ever so slightly flirtatious toward me, but I figured that was just my testosterone talking. Aside from my sexual attraction, I honestly did like Caroline a lot. She was very smart, refined, and a great conversationalist with an easy laugh. But, with Hugh always there and usually a bunch of other people, as well, there was never an opportunity to make a move, even if I had gotten my gumption up.

The last time I saw her was in the late '80s when she was in town for her father's funeral. A hard-drinking Type-A retired bank president by then in his late 70s, he had been in poor health for years, so it was not his passing that was a surprise but rather that he'd somehow lived so long. No one was exactly happy, but his death was something of a relief, and the family and friends were in relatively good spirits.

A close, lifelong friend of the family, I arrived at his widow's place on the morning before the funeral to help make arrangements. Good thing, too, because Hugh, like his dad, had developed a serious drinking problem. He'd gotten trashed on his flight in from New York City and was already well into a 12-pack of Bud tall boys. Unable to get a plane right away, Caroline, according to her mom, had driven through the night non-stop all the way from her home in South Carolina and was upstairs catching a few winks.

With the two children having long ago moved out, the parents had sold the big house and downsized into a condominium. It was very nice, but much smaller. At the time, what they really needed was the big old house back, as the mom was busy answering the door with a seemingly endless stream of people stopping by to express their sympathy. While that may seem kind, it's actually a pesky interruption, for dealing with a funeral takes a lot of focus and work. Of course, it would be rude to be terse with such visitors—mostly colleagues of the deceased high-powered executive and their country club friends—so the mom really had no choice but to invite them in the living room, offer coffee, and chat pleasantly.

Meanwhile, I made phone calls and plans back in the kitchen/great room area. I had recently handled my Great Uncle's funeral there in town at the same funeral home and cemetery, so I knew what I was doing and was glad I could help. Grateful for my assistance and distracted by a living room full of people, the mom finally just asked me to handle the whole thing and to "spare no expense." Do you know how easy it is to drop $50,000 on a funeral? 

Of course, Hugh, wasted there on the couch, was no help at all.

Gulping black coffee, I had to pee, so, seeing several guests waiting at the door of the downstairs half bath, I trotted upstairs, first time I'd ever been on the second level. The door to the bath up there was slightly ajar, and I could see the light shining through the crack, so I knocked.

"Come in," I heard the unmistakable voice of Caroline say. "Oh, hi, I thought it was Mom. I didn't know you were here. What a pleasant surprise. Great to see you. It's been a really long time."

Applying make-up, she was wearing a long, simple nightgown. In the bright light of the bulbs surrounding the vanity, I could see right through the thin white cotton garment, and it was obvious she had on nothing beneath, no bra, no panties, nothing at all. Day-um! Those football-shaped tits, their long, dark nipples pointing straight out, that light brown bush, those long, slender, tan legs. Pleasant surprise—indeed! Caroline looked even more smashing than I'd remembered. Significantly, she made no effort whatsoever to cover herself.

"I'm so sorry about your dad, Caroline," I offered, embracing her. 

Hugging me back, she pressed her breasts into my rib cage. Oh my God, they were so firm! I could even feel her nipples poking me, and in the reflection of the mirror, I could see her ass—still perfect as ever. 

"It's sad, but, you know, we'd all been holding our breaths for years for Dad to go. I'll miss him with all my being, but it's actually a relief," she said, straight from the heart.

"He'll be missed by many. Hey, mind if I take a leak?" I asked, unable to wait another moment yet wondering if urine would flow through my penis that had suddenly grown rigid.

"Oh, no, not at all. Please, step into my office," she kidded, opening the door to the adjoining toilet room. 

Caroline had such an easy, comfortable laugh. I liked her. I really liked that girl. Bladder full, I pointed my half-hard dick down at the water and let her rip into the commode. I knew that, standing just on the other side of the door, she could hear. 

I came out and watched her carefully apply eyeliner. Leaning forward near the vanity bulbs, I could see her body through the wispy gown better than ever. She was, essentially, naked, and totally casual about it. Memory refreshed, I replayed the decade-old scene of her sucking and titty-fucking her boyfriend. In no time, I was hard as a rock. 

What should I do? Her dear old dad had just expired the day before. This was not exactly an ideal time to make a move, yet, that she was standing, for all intents and purposes, nude, right there in front of me, and utterly insouciant about it, was tantamount to a come-on. I'm seldom at a loss for words, but what should I say? As a lead-in, I decided to go with an apology for screwing in her bed; that would get us on the topic of sex and hopefully segue into something between the two of us.

"Caroline," I fumbled, "you know the day you left for your freshman year at Vanderbilt, well, I spent the night at your house."

"Yeah, I remember. I knew you were there because your unmistakable black convertible was parked in front."

"Of course, how could anyone miss that car?" I asked rhetorically, suddenly coming to terms with the obvious. "Well, I must confess that Leigh's friend Lisa and I spent the night in your bed."

"I know. Not a problem. And Hugh and Leigh spent the night together in his bedroom."

"Wait a minute, how'd you know who was sleeping with who and where everyone was?" I gulped, realizing she was light-years ahead of me.

"Well, first of all, I saw four dirty wine glasses left downstairs, so, with your car out front and your being a buddy of Hugh's, I knew two of them belonged to you and him. Robert, my boyfriend who was also going to Vandy, couldn't get his Bronco around back to load up my stuff because Mom's Monte Carlo was blocking the drive. When I heard the upstairs toilet flush, I knew someone was awake, hopefully Hugh, and came up to get the spare set of keys from him to move her car out of the way. I tapped on his bedroom door several times, but when he didn't answer, I tried the door, found it unlocked, and went in and got the keys out of his jeans. That's when I saw he and Leigh sleeping together naked, surprising because I thought she was YOUR girlfriend."

"And then?" I prompted, wanting to avoid the Leigh/Lisa explanation.

"Well, on the way back down the hall, I heard loud snoring coming from my room and figured it was you. The door was open, so I peeked around the facing and saw that it was Lisa making all the racket, and you, wide awake, first gawking at my bikini photos on the dresser, then checking out my undies. All four wine glasses accounted for."

Uh-oh. I was suddenly extremely embarrassed. Caroline had seen me rifling through her intimate apparel.

Attempting the impossible apology, I said, "Listen, about your underwear, that was completely out of order, and I'm really sorry..."

"Not a problem," she interrupted, "Don't think for a moment I'd not noticed your lascivious stares at me and was, frankly, turned on that you were inspecting my private things, which gave me an idea. I really did need to get my clothes for college, so I tip-toed downstairs and asked Robert to come back up with me to help pack. I stripped off my nightgown to ensure he'd follow immediately. I was purposefully chatty with him on the way up so you'd surely hear us coming in time to take evasive action. As I expected, you'd hidden under my bedspread and were pretending to be asleep."

"You mean to tell me that what I saw that morning was not an accident, but an intentional sexual show?" I asked, incredulous.

"Yep. Pretty kinky, huh? That cute little Lisa sleeping nude with her legs wide open was just extra insurance—there was NO WAY Robert would not want to have sex with me in my bedroom with her to gawk at. I know how guys always think the grass is greener on the other side of the fence. Of course, I never told Robert what was going on for two reasons: First, he likes slutty sex, but probably not THAT slutty. Second, if he knew he was being watched, he very well might develop 'performance anxiety' and ruin it for everyone."

"Caroline, all these years I've thought that voyeuring you and Robert that morning was just pure luck, an incredible coincidence of right time and right place, and now I learn that you engineered the whole thing!"

"Well, as you know, I DID major in Engineering; now I have an ME," she quipped. "Why do you think I've been parading around in front of you in this see-through gown for the last fifteen minutes, anyway?"

And with that, she slowly pulled it off over her head, revealing her awesome, jaw-dropping beauty to me in all its completely bare glory. In seconds, I stripped naked, also. Grasping my cock in one hand, bun in the other as I latched on to a boob and her bun, she planted her moist lips against mine and proceeded with a deep French kiss that ranks with the very best of all time.

Suddenly, she broke the kiss and said, "Wait a minute. I haven't finished the story of what happened that morning. After breakfast, I put Robert to work cleaning up the kitchen while I went back up to my room to pack. Lisa was still snoring and obviously asleep, and there you were, too, snoozing buck naked on top of my wrecked bed. Of course, the first place my eyes went was your penis, only to see that my black satin panties were wrapped around it!"

"Again, Caroline, I'm really sorry about that, but I just..."

"Let me finish," she continued. Anyway, your cock looked so cute all cuddled up in my panties, but I really did want them back. So, after I quietly packed everything else, I tried to get them, but they were so smashed into the folds of your scrotum that it wasn't easy. In trying to extract my undies, your dick began to grow, which was very helpful because the more erect you got, the better I could get my panties loose. It only took a little bit of caressing to make you really hard and slip them right off. It looked so handsome and tempting, especially with the little drop of jellied semen on the tip that had been there all along, so I couldn't help but suck on it. I could get every bit of it in my mouth, which was extremely rewarding because I've never been able to do that with Robert's. Anyway, you began to shift and mumble, and I chickened out, afraid Robert would come looking for me, so I got my bags and bolted."

"Yes, I recall in my half-asleep state being fondled. I figured it was Lisa; never in my wildest dreams did I think it might be you! And you mean to tell me, Caroline, that you actually prefer a smaller dick?"

"Well, in a way, yes, but yours is by no means small, only smaller than Robert's. No matter what I do, I have this thing about completion. You know, finish the SAT; get the cock ALL the way in my mouth; complete the term paper; make sure the man CUMS in my mouth; finish the engineering project on time within budget; SWALLOW every drop of sperm. 

Of course, a great big dick in my pussy feels great, though it does take a few minutes to get past the initial discomfort, but the way a man works it has a lot more to do with my pleasure than his size. And, even though I love to have my poop shoot tongue-fucked and fingered, it'd be impossible to get a cock as big as Robert's in there, so a smaller one would be welcome, as I've always wanted to do anal sex. Now, let me finish what I started with you so many years ago."

And with that, Caroline dropped to her knees, licked my balls and dick all over, and sucked it from head all the way down to the base over and over and over as she tickled my testicles, taking the occasional breather to visually worship and wank my manhood. Just as I'd watched her do to Robert, Caroline gave me fantastic head! Un-fucking-believable!!!

Then came the titty-fuck, a tremendous titty-fuck between her magnificent mammaries onto which Caroline drooled slippery saliva. I just dug the hell out of the way she'd squeeze them together, look up into my eyes, and then down at my plunging prick to suck the tip or swab it around on those rubbery projecting points. It was quite obvious she got at least as much pleasure out of it as I. Of course, my big toe wiggling around in her pussy helped!

I was on the brink of spewing the whole time, and was just about to blow when she held me in check with a vice grip at the base of my shaft, then stood up and bent forward over the basin. With ass pooching out to make her genitals so readily accessible, no words were needed, and I dove face-first into that gushing gash, pulling her big, dark labia through my lips and lick-sucking her rigid clit like a man possessed. Caroline shuddered with pleasure, making her dangling tits dance, and I reached around to twiddle her nips. In no time, she came, then again and again and again. It was easy to tell, for she'd bite her lips and her pussy would turn almost purple each time. 




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.