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.