Caroline Surprise

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.