Blessed with Insomnia

You know when you can't sleep? For no reason?

Insomnia with an unknown cause. Work's fine, kid's doing well, financially... as good as can be expected, comfortable. There's the basic nitty-gritty, but for the most part, there's nothing grinding my ass to the bone on a daily basis, I just can't sleep.

Tired of tossing from side to side, at 2:14am, I get up. I have no intention of staying up mind you, so I go in search of a nightcap. I throw on a bathrobe and some slippers, and head out of my room. The floor boards' creak and I choose my steps wisely. My son Jason is asleep down the hall and I... I hear the sound of bumping against a wall, and a faint mattress squeak. Shaking off the concern that my squeaky floorboards might wake my son, who's apparently putting his girlfriend through the throws of passion, I round the corner of the hallway, and head downstairs.

I pass the entrance to the kitchen, take the first left, "Damn!" and stub my toe into that stupid, stupid hall table. Pass the downstairs bathroom, I move the left side of the slide doors to my study, walk in, and slide it closed behind me. The pale moon light shining through the windows gives off enough to let me navigate the room to my destination, the bar. I open the mini fridge, plunk to ice cubes into a glass, 2 shots of Glenlivet, a nice 18 yr, and a splash of water.

I take the first sip, mull it over, and mosey over to my desk. Butt firmly planted in the soft leather seat of my desk chair, I reach over my desk, open the cigar box on the side of my desk, and pull out a Montecristo. 2am's a bit late for a cigar, but I've already got the scotch, and as my throbbing left pinky toe reminds me, I won't be falling asleep for another hour or so anyway, so why not? Clipped cigar and matches in hand, I lean back in my seat, take a deep sigh, and for a brief moment, inspect the inside of my eyelids.

The stillness of the night, and my assumption that I'm the only one downstairs, are both broken by the sound of my den doors sliding open. I open my eyes to see the doors close together, while a shadowy and chesty figure, and slide in. My desk and chair face the sliding doors, and the windows that light the room are on the wall behind me, 2 long windows, evenly spaced, set on either side of my chair. The resulting effect is that I am completely draped in shadow, and apparently unnoticed by my late night guest. The young woman quietly slinks off to the right side of the room (her left, my right), where the bar is. The patter of her bare feet stop in front of the bar, and on tip toes, she closely examines the bottles. It's difficult for me to see her, so I know it's difficult for her to see the bottles, as I assume she's squinting to identify her intended alcohol of choice. Dark as it is, I can tell she's wearing a baggy shirt which hangs very loosely on her, and I also don't believe she's wearing night pants, as I think I can see her bare legs reflecting in the soft light. I also don't think this is my son's girlfriend, remembering that Jason said she's not a drinker. Granted he's 20, and she's 19, but my son knows I'm no idiot, and tells me these things so I know he'll have a designated driver, should the need arise. My curiosity peaked; I make her aware that I'm in the room, by striking my matches, and lightly puffing on my cigar to light it.

"Sweet Jesus!" she yelps. Taken aback and startled, she puts one hand over her chest, while her other hand braces herself on the bar. I lean over to the right side of my desk, and click my lamp onto its lowest setting. She doesn't move at all. I almost wonder if she thinks that if she doesn't move, I won't see her – like I'm a Tyrannosaurs Rex. With my eyes adjusted to the light, I realize that the young woman in front of me is Jenna, the best friend of my son's longtime girlfriend.

"Looking for something, Jenna?" I ask. I know what she's looking for of course, but I have to say something.

"Mr. McDougal?" she replies. She starts to move out of the corner, and into the light. As she does, I realize the shirt she's wearing is a man's white dress shirt, and nothing else. At least nothing else that I can see. Suddenly my mind races to that scene from, "American Beauty" where rose petals swirl around a naked Mena Survari. I've known Jenna for 2 years now, and she's always been very attractive. I hadn't given it any thought before, alright, much thought before, but here she was standing half naked before me, at 2 o'clock in the morning, while I suddenly contemplate where the boundary between, "friend's dad," and "skeevey old man" is drawn. She is after all 19 years old, which either complicates things, or simplifies them.

I draw on the cigar and take a sip of my scotch. "You were looking for something."

"No, no, I mean, um," suddenly lost for a legitimate reason to be perusing my liquor cabinet at 2 in the morning, she stammered into, "I was going to get a glass of water."

"Uh huh." I reply. I pause for a moment and say, "It's okay if you want to fix yourself a drink. What were you looking for?" I have no problem with drinking over the age of 18, as long as you're not driving (obviously).

Taken back by the statement, and possibly worried by the thought that denying she was in search of alcohol might rescind my offer she softly asks, "Rum and coke?" I tell her there's a bottle of coke in the mini fridge, and direct her to the bottle of Captain Morgan sitting on the far right of the middle shelf. She pours herself her drink, quickly mops up her slight spillage with a paper towel, and awkwardly slurps off the excess from her glass. If it weren't for her puttering, the silence would be deafening. I quietly smoke my cigar and watch her, and in this short time my mind wanders into bending her over the desk – fucking her from behind, cumming all over tits, and has already chastised me because I'm 40, she's 19, and a year and half ago, that would have been illegal.

With drink in hand, and unsure of how to proceed, she eventually faces the door, thinking, hoping, praying, that there would be nothing else to say. "Did I wake you?" I ask.

"No! I... um..." I extend my right hand towards one of the two chairs in front of the desk, inviting her to sit. "I um, just couldn't sleep." she said as she made her way to the big brown leather chair. She sat down in the chair, and brought her knees and legs up to her chest, balled up. The soft glow of the desk lamp fell on her more clearly now, and I could see her red hair, tousled from what sleep she did get, hanging down behind her back, except for certain wisps which fell in the front. Her breasts, which I couldn't see as they were hidden by her knees, I could tell were free from the constrictions of a bra, as I could see through the top of her shirt which was unbuttoned. The tail of her shirt, which I assumed was my son's, curled along and disappeared under her bottom. Why she was wearing my son's dress shirt was not as interesting as whether or not she was wearing underwear, a fact I could not determine because of the way her feet sat crossed, in front of her. Not choking on my scotch was about as hard as not gawking at the fantasy girl sitting before me.

"Liar." I said. "Jason and Amber were keeping you up. The guest bedroom's right next to his bedroom, and let's face it, they're going at it." Jenna flushed at my bluntness, and took a large sip of her drink. Not sure what to say next, she took two more large sips of her drink.

"It's ok, they woke me up too." Whether they did or not, I don't know, nor do I care. It seemed like the right thing to say. She took another sip of her drink.

"So you decided to come down here, get a little buzzed, and go back to bed." I suggested, and waited for a response. Instead she just took another sip of her drink, this time, finishing it off.

I took my glass, which was almost empty, reached over, and placed it on the edge of the desk, close to her. "I'll tell you what, you go make yourself a second, and top mine off while you're at it – Scotch on the rocks, more scotch than water (in case she had never made one before). Eyes wide open and unsure, she delicately grabbed my glass, stood up, and walked back over the bar. Jenna made her drink first, and I directed her where the bottle of scotch was for my drink. After everything was cleaned up, she walked back over, and rounded the desk so she was standing next to me so she could hand me my drink. I swiveled my chair to the right, and took the glass from her, took a sip, and placed it on the desk. It was good, strong. Judging by the look of her drink, which was definitely more Captain than Coke, I was betting she had been around a bar before.

I don't know why it is that a woman draped in a man's dress shirt is so damn sexy, but it caused me to lose control of my tongue, and I blurted out, "Damn you are beautiful." She looked almost nervous, and averted her eyes to my crotch, which caused me to do the same. My semi-hard cock had tented my bathrobe, causing the robe to part and my balls to be somewhat visible. I started to move my hand to adjust myself, and my robe, but before I could really do anything, Jenna had already taken a swig of her drink, put it down on the corner of the desk, and was already sinking to her knees. Before I knew it she had her hands on my legs, lightly pushing them apart. My mouth opened, a fake protest half developed, but the look in her eyes told me I shouldn't say anything.

I don't know why she decided to do this, I'm just glad she did. Her motivations were unknown, but were as steadfast as her hands as she brushed my robe aside, cupped my balls, and took my cock between her lips, between those soft, slightly pouty lips. My head jerked back to my chair, eyes wide open, and I swear to God I saw fireworks. Tiny multi colored shooting stars celebrating the party going on in her mouth. The initial shock subsiding, I closed my eyes, relished her tonguing, and enjoyed what I decided was the greatest cigar I would ever smoke.

For near on ten minutes her head bobbed up and down on my cock, her red hair thrashing lightly, covering her face, until occasionally when she would arch back, and look at me with those beautiful green eyes. Every so often she would remove my cock from her mouth with a soft slurp, grab it with her full fist, and then turn the attention of her tongue to my nuts, while she lightly pumped my cock. Her tongue would swirl around one testicle, then the other, before going back to the first where she would lightly suck it into her mouth, the beautiful feeling counterpointed by the butterflies in my stomach. Then she would get daring, and try get both of my balls in her mouth. Sadly, and proudly, they were just too big to both fit, which is when she would swap her fist back for her mouth and go back to sucking my cock for all it was worth.

I enjoyed her ministrations, with the full control of my left hand's fingers entwined in her hair, holding her head, until my cigar was nothing but a nub. I tossed it in the ashtray to burn out, took a large swig of my scotch, and put both of my hands around her shoulders, and eased her off of my cock. Sweeping a few unbreakable items from my desk, I stood from my chair turned to her, grabbed her around the waste, and lifted her onto the desk. She sat in front of me with her hair hanging in front of her eyes, those once nervous eyes – now so sultry, and her bare, beautiful legs draped over my desk. I grabbed the bottom of her shirt and started to raise it over her head. She raised her arms to make it easier, and when I was done she sat in front of me, stark naked. I took in this heavenly sight, mesmerized and enchanted by her B cup breasts, smooth stomach, and the fact that in her state of excitedness, she had left a small wet mark on the side of my desk with her womanhood.

I untied my robe, and let it fall to the floor. I cupped my right hand around her left breast, and moved in to kiss her, very softly. I broke the kiss, leaned over her left side, opened, and removed another cigar from my small humidor. Sitting back in the chair I spread her legs apart, and with her eyes locked on mine, I slowly moved the cigar down to her pussy. First lightly rubbing it across her lips, then her clit, before pushing my way through, until the whole thing was almost buried. I almost regret doing something so cliché, "pulling a Clinton," but rationalized, how often would I get that chance, and was pleased that afterwards, THAT would probably be the best cigar I ever smoked.

I withdrew the cigar from her pussy, and placed it back in the box, sitting horizontally across its peers for easy identification. Resuming my seat, I gazed happily at the soft wet folds of one of the most beautiful pussies I had ever seen. I started to kiss her stomach while my hands slowly went up and down her legs. As my head started to lower, she started to put her hands on my shoulders, pushing me down faster. My concern for my beard being abrasive was dashed away by her hands on the back of my head, pushing my face between her legs. I started to lick her outer lips at first, then her clit before parting her lips with my tongue. As she started to moan loader, I started to involve my fingers – first the one, then a second, until my tongue was a frenzy on her clit, and my fingers were furiously fucking her pussy. One after another, her orgasms rolled through her body and down my tongue, her muscles clenching my fingers, her deliciously salty wetness running down my wrist. When the third orgasm overtook her, her legs clenched and seized on my arms, and she started screaming name.

"Oh God, Mr. McDougal, fuck yeah! Mr. McDougal just, oh yeah, just like that, ooohhhh god." Her voice cracked and her pitch waivered. I slowly stopped what I was doing and stood up. I took my hands and ran them down her sides, across her soft breasts and down her flat stomach, before moving my hands back up to her breasts, lightly pinching her nipples.

"If you're going to scream my name," I started to say, in a low, calm voice, "It's 'Commander McDougal.'" With that I bent my head down, and quickly licked and bit down on her left nipple. I straightened up again, cupped her face in my left hand, and brought her face to mine to kiss her. It was deep and as our tongues danced; my right hand slid my cock deep within her pussy. She was so wet I slid right in, and within a second my 10 inches were balls-deep, forcing a groan out of her lips, breaking our kiss. Her face was frozen for a couple of seconds as I slowly worked my shaft in and out of her. When she finally opened her eyes again, they briefly caught mine, before exploring my body. She brought both hands up to my face and ran her fingers through my short cut salt and pepper hair, across my full beard before planting on my chest. As she ran her fingers through my hairy chest, her legs wrapped around mine, stabilizing her as I slowly fucked her.

She pinched my nipples lightly at first, and then harder, which turned me on even more. She moved her hands down my stomach to our groins, where my cock was methodically fucking her, my balls lightly slapping against her ass. I watched her enjoy herself; enjoy what I was doing to her, in what seemed like slow motion. My thrusts causing small whelps to escape her lips. She moved her right hand down to my cock. She ran her fingers on my shaft as I thrust in and out of her, before she moved to her clit, lightly rubbing it in rhythm with my fucking. She hooked her left arm around my neck and pulled her self closer to me, her fingers working her clit furiously. I put my hands down on the desk to stabilize my self as I increased my speed, fucking her. As I sped up, she got louder, until finally she climaxed on my cock; the pulses from her pussy came in rushing waves over my cock, testing my limits of control.

She held on to me tighter. I took her right hand and arm, and repositioned it around my neck with her left. Moving both of my arms below her legs, I took a firm grasp of her ass, and leaning back, lifted her off the desk. I took a small step backwards, pushing the chair behind me back on its rollers. I kissed her again, and as she kissed me back, I started to raise and slam that tight little pussy of hers back on my cock, burying me as deep as I could go.

"OH FUCK! COMMANDER McDOUGAL! OH SWEET FUCK! OH GOD FUCK ME, JUST FUCK ME! JUST FUCK ME!" she screamed as we went at it, hammering her pussy down like I was trying to permanently glue it to my crotch – and believe me, if that was an option I would have gone for it. Knees bent, thighs burning, I fucked her for all I was worth, the sound of my panting drowned by her screaming. Her breasts bouncing wildly before being briefly pinned down by my chest, all so my next thrust could send them flying once again. Her left hand wrapped around the back of my head, her nails in my scalp, her right hand down my back, nails dug into my shoulder blade, my fingers digging into her ass cheeks, I fucked her like it was going out of style. And as her screams got louder, I started to moan, a low guttural growl which seemed to excite her even more. Our volume increasing with the onset of our respective orgasms, first her explosion and then mine, her quaking pussy walls eagerly accepting the flood of cum I happily gave her.

As I slowed down my thrusting, we both started to relax our limbs, until she was barely holding on, and I had no choice but to put her down on the desk. Taking deep breaths, my half-limp cocked plopped out of her, connected temporarily by a thin thread of cum. I flopped back in my chair and enjoyed the act of breathing, the air never having tasted quite this sweet. When I opened my eyes she was already using a tissue to clean herself up, lightly wiping around her pussy which was reddened by enthusiastic humping. She stood and looked briefly around before spotting her shirt. As she pulled it back over her head, her eyes suddenly opened wide with alarm and she looked at me. Her mouth started to open, and a look of panic spread across her face.

"Don't worry. Had a vasectomy 5 years ago, and I'm clean. Military tested and approved." Her eyes returned to normal, and she started to nod her head in understanding, and a beautiful but dopey grin came across her lips.

She didn't say anything, only looked around briefly, wondering if she was forgetting something. Realizing she didn't bring in anything other than her shirt, she looked me in the eyes, gave me a soft, open mouthed kiss, and quietly scampered back to the door. She turned and looked at me once more, slid the doors open, and closed them behind her.

I enjoyed the immediate memory of what had just happened for 5-10 minutes, collected our glasses, placed them in the sink, and made my way back up to bed. Within seconds of my head hitting the pillow, I was out. Babies don't sleep this well.