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.
