NIGHTCAP

by Holly Rennick

AUTHOR'S NOTES

Nightcap:

   (1) Cloth cap worn in bed, as envisioned in "And mamma in her kerchief, and I in my cap, had just settled down for a long winter's nap" attributed to Clement Clarke Moore.

   (2) Drink taken at bedtime; often alcoholic, but cocoa counts.

   (3) Final game of a double header (baseball).

Synopsis:  Girl overnights at friend's house.  A bit of teasing.  Two visitations to brother's room after lights-out.  The End.  Automatic prose, you complain.  So let's ask our three characters what happened.  (Multiple perspective is old-hat in literature, e.g., Faulkner's "As I Lay Dying".)

And in most literature, the postscript is left to the reader.

KEVIN

It was just Beth spending the night with my sister.  We'd played Monopoly and the two didn't even want to finish because I owned so many hotels.

But I wanted to keep going, lend them money, if that's what it took.  Building hotels means forking over lots of dough.  And the way Beth was sitting (the banker having to lean over to make change), her nightgown top hung lose.  Wasn't my fault.

Maybe her neckline didn't faze her because I was just Andrea's brother.  Besides, the girls weren't even in high school.  What did they care?

Pretty nice tits for a girl her age, I thought.  Like us guys say, "More than a mouthful, less than a handful."  Usually I'd just see one side, but if Beth had a lot of money to count, I'd see all the way to her panties, robin's-egg blue.  Babes in the magazines have big sweet dark areolas, but Beth's weren't much different from her skin.  Nice, still.

I'd always thought 14-year-olds hardly had nipples, but hers I could tell when she'd adjust her ridiculous nightcap, a "Night before Christmas" pointed affair.  My sister's show, on the other hand, just if it's really cold.  (Actually, I guess it was sort of chilly, as Andrea's stood out when she made cocoa with peppermint schnapps, extra for me and Beth.)

I was glad I was still in my Docker cargos, I was so hard.  Girls their age, though, wouldn't be trying to tell.

When I trudged up to bed, Beth waved goodnight with one hand.  With the other, she pulled her gown sideways, nipples standing like eraser heads.  Andrea was pretending to sort the property cards, but checked out the scene.

Teeth brushed, clothes tossed toward the dresser and I was asleep, dreaming about being naked on the basketball court, trying to act natural so nobody would notice.  I suspected that everybody did see, though, the way they were dribbling around me.  Somehow, I didn't mind because the one I was guarding (I guess it must have been a girls' team) kept bumping me with her chest.  Her team wore these silly nightcaps.

But wait!  Something was rubbing and it was for real!  At first, I was still on the court, not in my own bed.  But no, I wasn't shooting hoops and it wasn't my gym shorts that were slipping down.  It was my sheet that was sliding.  And the way it slid, it wasn't gravity

I cracked an eye enough to note that my door was ajar.  The hall light wasn't much, but sufficient to silhouette Beth's nightcap not 18 inches from my chin.  Not a sound, though.  I shut my eye to sort out what was up, but it's hard to track your thought process when you're still half asleep.

I knew it was Beth because of her nightcap and because of how the sheet was sliding, the same way her gown slid when she'd waved goodnight.  I lay there on my back, wondering why was she here?  Did she and my sister sneak in to play some sort of trick?  What should I do?  Wake the folks?

First, figure out what's going on.

Two things seemed certain: Beth's breathing and the sheet still sliding.  No, maybe Andrea wasn't with her, or I'd have heard other noises.  It was just one.

The mattress sagged as she put her weight on the edge.  What's going on?

Probably I'd be scared if it were a stranger, but that might power my punches.  But this was Andrea's best friend, the one I'd beaten in Monopoly, the one... who'd been the banker.  My eyes were shut and I still saw her tits.

I felt the cooler air as the cloth left my knee.  Did she realize I was just in my undershorts?  But that's it!  She's trying to see my shorts to get even!  Holy shit!

The sheet draping my midsection yet afforded some cover, that plus the darkness.  I could feel her leaning over me, testing for a loose corner.  Fortunately, I felt the sheet tighten where it wrapped under me.  As long as I lay flat, she'd not be able to sneak it off.

Sneaking a quick peek, just through the lashes of one eye, Beth's nightgown hung loose the same as when we were downstairs.  It was too dark to look down, but my mind still saw.  A stir between my legs.   Oh, shit!  Beth the banker was giving me another boner!  Or was it something carried over from the dream, Beth guarding me on the basketball court?

A hard-on's not something that you can will back to nothing.  The more you know you've got one, the stiffer it gets.  But surely, she'd not be able to tell, though, the way the fabric bunched.

It seemed several minutes before she again moved, her hand now creeping onto my hip.

Oh, God!  No!

I was an ice statue as she sorted through linen folds until a finger found me through both sheet and shorts.  At first it was but touches, then brushes, then traces, then fingers on either side.  Could she tell I was trembling?

Push her away?  (It never occurred to me to hit her.)  I guess we turn to what seems easiest.  If I never knew she'd done it, it would almost be as if she hadn't.

I lay motionless as the more resolute her rub, the more there was to rub.  Within probably no more than a minute, what had been back and forth drawn fingers was now an up and down grasp.  What had been slide over fabric now drew my hips with it.  Just keep your eyes closed, Kevin, I repeated over and over.  You're asleep.  But as firmly as she commanded, she must have known that I wasn't.

All I could do was to endure.  She only let go long enough to pull away my sheet completely.  Again I felt the cold air, this time on the inside of my thighs.

Her free hand found my cuff and now oblivious to stealth, entered, grazed my balls and moved upward to encircle, emboldened fingers squeezing and stroking my appallingly stiffness.

I wanted nothing less than to disappear forever, to fade into my mattress.  Fingers above the sheet had seemed less immediate.  But now I wanted to answer that hand, to wet between each finger.  Hungry to climax for her, I pressed the back of my knees downward and raised myself higher.

Then the unexpected occurred.  Her grip loosened to that of a cradle.  I felt the tip of her nightcap drag across my thigh, over my erection.  I felt the press of her cheek against my chest as she blanketed me with her warmth, her hands moving to my shoulders.

It was her snuggling into me that did it, that made me come, still in my shorts.  I think that she may have done the same from her little gasps.

Afterwards, she lay still as I adjusted that silly cap of hers.  A little while later, she covered me and left.

Later that night I dreamed of it ending differently, of having sex.  The funny thing about the dream was that it must have made me take off my shorts.  Why else would they be wadded up at the foot of my bed this morning?

Breakfast time.  I hear the two girls already crashing around in the kitchen.

BETH

Sure, I'd known that Andrea had watched me tease.  She and I have been best friends forever.  If she'd been protective, I'd have left Kevin alone.  But the fact is, every girl uses her brother (if she has one) to practice the rudiments of engagement.  Just an example: when those two and I hiked to the top of Bald Butte last summer, Andrea first changed into her pink bra.

Andrea's the one who told me that boys need hardly a minute to masturbate, not like us.  When I asked how she knew that, she dodged answering, but then giggled and pointed to outside of Kevin's door and then to her wristwatch.

So playing Monopoly, Kevin got to look.  (Not that I have that much.)   Kevin might be older than us, but it doesn't mean he's smarter.  Like having me count him ten 100's for a 1,000 about twenty times!  Hey, Kevin?  Want me to lean right or left?  At least I had my panties on, more than Andrea wears under her nightgown.

Well of course Andrea wouldn't say, "Go sneak into my brother's room and tease him some more."  She just conked out too quickly, too convincingly.  (Usually we talk for about three hours.)  It was just better that we didn't discuss Kevin.

I'm totally sure Kevin wasn't expecting anything.  So why was I even doing it?

Good question.  Well, for one, I figured I'd get away with it.  Even if he woke up, Kevin wouldn't do anything except chase me out.

And for two, a cock is kind of cool.  Not that I know a lot, I suppose, but I'd already felt one through a guy's jeans behind my Science Fair exhibit.  The problem was that he was feeling me at the same time, and that wouldn't be a problem except for him planning to make me pregnant.  But if the guy were sleeping, you could check him out more safely.

And for three, if you can make a guy come in his pants, you've bagged him!  "Follow little Bethie to the bathroom, Kevin.  Lie on that laundry pile while Andrea finishes copying my homework and I'll shoot you into her yesterday's panties!  Nice, Kevin!  Just keep your hands behind your head like a good boy."  That's how I'd do it!

Actually, I've seen this video of a couple masturbating each other, except the camera just showed their top halves.  It looked pretty exciting, but I figured that you probably needed to start just doing it to him so you could concentrate better.

So there Kevin was, sound asleep, masturbatable (if that's a word), the hall light to see what I was doing.

The first part was a snap.  Once I'd pulled the sheet part way, I could tell where his ridge got definite.  It looked pretty big for a guy asleep, but sometimes they dream things, I read.

Maybe his nose sensed my estrogen, or whatever it is that helps us develop.  In Girl Scouts we used to say, "The angle of the dangle is proportional to the *** provided that the *** remains constant," where *** could be something like "torque of the pork, heat of the meat, heat of the beat, urge to surge" or "beauty of the cutie".  It's true because the angle of Kevin's steepened, just from the movement of the sheet.

It was instinctive, knowing how to hold it through the fabric.  The way he kept growing, I must have been doing something right.  The Joy of Sex says that boys get erections in their dreams, so wouldn't it be funny if he were dreaming about seeing my boobs?

I just had no idea that it could get so humungous, though.

The Joy of Sex says that sliding the skin is how to do it.  It's rougher than how we take care of our own needs, but males have more to work with, I guess.  The way he was starting to move with me, maybe I'd started him dreaming of some high school girl with D's.  As long as he was doing some of the moving, it wasn't my fault if he came, I figured.

There was no reason for the sheet.  That pulled aside, he was just in his boxers.  Much better.  It was too dim to study the design, but it might have been palm trees, or maybe musical notes.

Reaching inside from both top and bottom came easily.  I wasn't that comfortable handling his balls, but my other hand could feel the slickness around his tip.  The Joy of Sex says that it's just like for us, getting lubricated.

By now, he was doing most of the work against my palm, and I knew he was awake, willfully succumbing.  If I wanted a video of him even, he'd do it.  I wouldn't film just his top half, either.  "Now, Kevin," I imagined ordering, "if you won't play Monopoly in Andrea's panties, I guess I'll have to show the video at school."

Shoot!  I could even have sex with him, here and now!

But a thought hit me, a really strange one.  What's real about making someone do it?  Shoot, Andrea's brother was OK, even played Monopoly and liked spying on me.  Was he still a virgin, too, like his sister claimed?  I'd assumed that a guy his age wouldn't be, but maybe some are.  Maybe they worry about it, just like us.  Almost get there and then decide maybe not quite yet.

I don't know.  I'd really felt him up, but maybe a snuck-up-on guy wouldn't be that much fun.  I mean, sure it would be fun in the way that orgasms are neat, but maybe it wouldn't be much more than that.

It would be better if he'd take off my nightgown and tell me I'm pretty.  He should be the one sneaking into where I was sleeping and waking me with a kiss.  He should be feeling me, rubbing along my stomach until sucked way in.  I'd at first say no, but he'd tell me it was to prove that we loved each other.  I'd pull down my own panties at the very end.

All I'd wanted was to touch him.  I didn't want a windup toy; I just wanted to be sweet.  I hope he knew that when I lay my head against his shoulder, just for that minute, how happy it made me.

I do know that he smoothed my nightcap for that minute.  You don't have to say a word sometimes.  Arranging my hat was exactly right.

I'd bracketed my knees around his hips, my feet turned inward to hook his knees.  He furrowed the crease in my panties into the wetness.  When I pulled up my left hip and then settled it back, I felt his almost-imperceptible throb.  When I did the same with my right hip, I felt it again.  An observer would perhaps have seen nothing, so slight was my smudge.  A near listener might have heard the quietist of rocking.  Only someone placing a hand between us would have sensed the tug of body against body.

His orgasm was quick, wetting my hair through boxers and panties.  It didn't seem icky at all.  Mine was slower, much slower, with the delicacy of a violet.

ANDREA

Might as well call it "Breastopoly", I'd decided.  Did Beth come over to spend the night, or to give my brother a hard-on?  Reaching his hand into his pocket like he was looking for loose change!  Talk about obvious!  You don't grow up with a brother and not know something about his dick.

Same as he doesn't grow up with you and not know when you're having your period.  The thing is, though, he'll never in a hundred years tell his buddies.  After all, you're his sister.

Beth and I have been best friends since we were little, so I didn't mind Beth playing around.  Actually, it was sort of fun, watching Kev getting her to make change.  Even for another girl, it's classy when you get an accidental peek.  Her breasts are the same size as mine, but my middle's darker.

And Kev wasn't exactly an innocent victim.  He's always been one to let someone else take the risks.  He'd never start a wrestling match where Mom might blame him for roughhousing, but if I made the tackle, he'd hold around my chest or work up my shirt or rub my butt.  I'm not talking about nasty things, just brother-sister stuff.

I'd have known if Kev weren't still a virgin, of course, and I'd rather Beth get it than some twelfth-grade girl still taking algebra.  But it was best that I didn't suggest Kev by name when Beth and I discussed growing up.  It seemed pretty obvious that she'd figured it out herself, stealthily sneaking out of my room after keeping him panting all evening.

It's a major event when your brother and your best friend have sex together for their first times.  I wish Beth had a brother.

But Beth would have been away a lot longer if they'd gone all the way.  Probably I'd have had to go in to wake her for breakfast.  But no, back she tiptoed, nightcap and all, far too soon.

But if nothing had happened (say, maybe his door was locked), she'd have returned a lot sooner.  Or if there'd been a confrontation, she wouldn't have been so pixie-quiet in retreat.

So what happened?  As Kev's sister, I had the right to know.  Before I flat out asked Beth, though, I'd at least scope the layout.  You don't want to ask dumb questions.

When Beth was finally asleep, I don't know why I snitched her nightcap, laid so carefully on her pillow.  Maybe it looked fun to wear exploring, hitching my nightgown to my knees so I could take big sneaky steps.

Kev's door wasn't latched and there he was, flat on his back.   But the sheet was tucked about him as if laid from above, too squarely for someone yet in it, so taut that even from the doorway I could see the one-o'clock alignment of his dick.

The story was starting to come together.  Beth would have used the opportunity (same as would any girl) to get even for him looking down her top.  He'd never woken up and she'd covered him up at the end, just like how we used to put our Barbies to bed.  (Playing dolls was more innocent, but I remember once when we were about 12, making Ken lie on top of Barbie naked and pretending that they made a baby.)

Good!  Kev and Beth would have sex the next sleepover.  I'd arrange everything.

But Kev had never looked down my top?  Or at my panties?  Scoping little sis doesn't count?  A friend gets to dish out all the justice?

Actually, wouldn't be cool for little sis to have a little fun, too, while he's sleeping?  He'd gotten me enough times wrestling.

I killed the hall light behind me.

It was so easy, massaging through the bed sheet.  I shouldn't have kept going, but when Mr. Penis started to agree, I couldn't really stop.  It was just so fun getting even, finding out how much bigger he was than I'd imagined.  How I could twitch him side to side.

But if I were going to fondle him heavy-duty, the sheet needed to go.  It just took a few tugs and his big old penis was tenting the middle of his underpants.  I could even feel the ridge around its head and when I lifted him up higher, the front of his balls.

Part of Beth's excursion I figured out from the dampness of his underpants.  Maybe he and Beth had tried to have sex and he'd come too quickly.  (My book Olympic Orgasms tells how to keep this from happening, but I hadn't read Beth that section).  Had that happened, though, I'd have expected her to stomp back to my room in a bad mood.

Or maybe he'd done it himself afterwards.  (Olympic Orgasms has lots of information on male masturbation, useful if you're not protected.)  Made more sense.

In any case, that was then and this was now.  (Olympic Orgasms says that it may take an hour for a male to recover, so Kev was even a little ahead of schedule.)

The only difficulty stripping him was pushing his dick down for the waistband to slide over.  I could have left his underpants at his knees, but I wanted him buck-naked.  It was too dark to see, but I did pretty well for never having stripped anyone before.

A sister can tell things.  His supple yielding so I could feel his balls told me that he was in some sense aware.  I wish I could have seen his public hair to know if we were the same.  When I let the end of Beth's nightcap drag up his thigh and flop against his dick, I swear that he shivered.

By now, I'd climbed up on the bed.  I figured that I was on the right track, just pushing and pulling.  (Olympic Orgasms shows alternative handholds, but I just took it the way that made most sense.)  It would be neat to watch him come, except it was dark.  It would be neat to feel it, anyway.  Maybe I'd be able to get some cum on my front if I straddled him, like Monica got President Clinton to do it on her dress in the Oval Office.  Hillary I didn't really care about, but poor Chelsea!

I guess I was thinking too much about Monica to realize how Kev was guiding my waist.  Or maybe part of me realized it, but didn't guess why.  Anyway, I was wet and he was hard and my slipping down onto him just happened.  It didn't feel like loosing a cherry and it didn't feel all lovey-dovey, at least the way it works in novels.  It just felt like I had something big inside.  It was the sliding that felt sexy, my nightgown pulled up under my armpits.

Who knows what Kev thought, or if he was even awake?  Can you dream and fuck at the same time?  I didn't say anything because I wasn't too sure what to say, actually.  We weren't quiet, though, the way we squeaked his bed, but I knew that such noise doesn't travel much down the hall.

He came super, lots of it, mostly inside me.  I was a little more iffy, trying to keep my balance and everything, but I felt good about it.  Everybody says that the first time is rarely that erotic.  I suspected that I might be sore in the morning and definitely needed to wash up.  I didn't think much about it then, but the cap flopping around must have felt funny to Kev.  (Olympic Orgasms illustrates all sorts of ways, but nothing about costumes.)

I knew I could have screwed better if I'd started out with a real plan, but how many girls pull that one off their first time?  We just sort of get fucked without careful forethought and only later make it cerebral.  Romance novels go on and on about getting there.  Olympic Orgasms rates the positions.  Maybe we need more stories that bridge the gap.

When we finished, who wants to sleep with a brother who's again in dreamland?  Climbing off and pulling down my gown must have been when I lost the nightcap.  Women get elated after sex and can't remember everything, another gap between romance novels and my instruction book.

Kev would sleep in tomorrow, so I'd have time to figure out an explanation about what we'd done.

The more I thought, however, the more I realized that maybe I'd gotten away with it!  If he'd realized what we were doing, his little sister on top, he'd have been more bossy.

*****

Beth and I are eating breakfast when Kev stumbles down the stairs.  At least I have a little warning that he's awake.  Beth too, I can tell, is thinking fast.

The first thing is to sound cheery.  "Mornin', Kev," I volunteer.  "Find your cup from last night and we'll give you some cocoa."

He looks at me, but not really.  In his hand is the nightcap.  Oh, shit!

"Mornin'," looking around.  "Here," he stammers, then manages a bolder smile.  "I guess you forgot something the second visit," as he hands the nightcap to my best friend, Beth.

END

HOLLY ON THE WEB

Wherever you found this story on the web, thank you to the server.  My problem is that I've no systematic way to update the various servers.  As literary errors (or just poor word usages) are made known to me, I'll repair that which is salvageable on http://www.asstr.org/~Holly_Rennick/.  My website's not much graphically, I admit, but HTML isn't my native language.

You can contact me via the site's message form, that HTML code by the smart people at ASSTR.

I won't be changing the story significantly, so if you didn't like it before, that much will remain the same.  But if you did like it, an update may read a bit more cleanly.

   Holly
