I laid there in a state. His state. Well, it’s his fault I was in this state…Whatever. I was mad at him. Really, I was mad at myself. I could smell the gallon of rum he’d consumed over the night’s train of bars we attended from the other side of the hotel room where I laid. The chasm of space between our double beds seemed farther with every glance at him. Derrick slept exactly in the position I left him. His shins dangled from the bottom of the bed so the soles of his shoes could barely brush the gray off white carpet. Derrick’s black button-down shirt was a wrinkled mess and was untucked from his jeans. I knew Derrick would never sleep like this- especially in front of me. The straight and sturdy, wrinkle free, and articulate monster I knew as my boss had more luggage just to hold and organize his grooming products than I had total for the week’s stay in New York City.
I had always known, of course, that he had a thing for me. Every woman who has her wits about her always knows, at least when it comes to the men whom they have no interest in, unfortunately. It’s a messy pile of awkwardness when the girl works with- for the guy, as well. There’s the ‘subtle’ hints of the over joyful greetings in the morning, followed by the almost forced ‘witty’ banter. Then the moment every woman around a guy she’s trying to friendzone dreads: the awkward-nervous break in the personal space boundaries. It was at this stage that most girls drop the obvious-to-us signs of bringing our boyfriend’s (or fake boyfriend’s) name into the conversation. Or forcing out sentences of ‘how you’re such a good friend,’ into the conversation. Of course, these obvious-to-us signs are usually misinterpreted and twisted in the horny-love struck minds of men as positive attention encouraging him to carry forth.
This conundrum of an awkward love game was ultimately women’s fault, I knew. We were the ones always encouraging men fight for our attention and love and whatever. But… I mean… Couldn’t the guy who fights for my attention at least drink beer and not a long island iced tea?? Don’t get me wrong, Derrick was excruciatingly nice and polite. He probably was the dream guy for most girls and should’ve been mine. He constantly went out of his way to help people with things- and not just me but strangers, too. Once he came into work with his suit drenched from the down pour outside because he decided to pull over and help a broken-down motorist push his car out of the road. Who does that? I don’t even help short people struggling to reach a can of food off the top shelf at the grocery store.
It was my fault, again for what lead to tonight’s transgressions because when Derrick had asked if I was okay with sharing a room on this week-long business trip, I of course said it was fine. In his eyes, it probably looked like I shot a love shaped flare across the starry sky to him. But all went fine during the week of the conference. Better than expected, actually, as we opened several more accounts than what we were marked to open. But it was not until beer number four with shot number two for me tonight, and long island number 5 and shot number 4 for Derrick that I realized this last night of celebratory drinks were supposed to be the lead in for him from business to pleasure.
The realization came not a moment too soon as all the liquor seemed to consume Derrick at once as I thanked him for paying for the drinks and he attempted to make a discombobulated joke about how his need to because of how beautiful I was. He was cute. Falling on each other (mostly me holding him up) I guided us to our uber as we drove back to the hotel room. Before moving to Chicago for a career move I was born and bred in the great state of Tennessee. That is to say, the South had prepared me well for a life of drinking. My college years consisted of many 6 packs hidden in my dorm rooms to be shared between my suite mates, or a cold night huddled beside a warm fire passing a half empty bottle of Tennessee whiskey between each other. Derrick… did not seem to receive the same level of education.
“You know? You have quite the pretty eye,” he said. “Two of thems actually.” His finger bounced towards my nose, maybe, but missed completely and only touched the back of the uber seat.
“Thanks,” I laughed taking his hand and putting it back in his lap.
“Oookay,” he said to himself as he interlocked his fingers in his lap.
Back at the hotel we had shared another whiskey at the mini bar while we laughed sitting on my bed. I’m not exactly sure how it happened. I think I pushed him some when he said something stupid then he pushed me back. I’m not sure but it ended with his lips on mine. I thought I stopped him right away. I swore I did. But now as I lie here thinking about it- remembering his soft hand sliding up the outside of my right bare thigh just inching up under my blue dress’s skirt. His fingers squeezing just at the fold of my ass cheek from my thigh. I think his hand was even down the neck of my dress for a moment- or I just fantasized that?
“Mmmyes- no, Derrick, no,” I said and felt Derrick’s lips and hands fall away instantly even though it took mine a minute to stop unbuttoning his shirt (was I unbuttoning his shirt? Oh god…).
“Mmsorry, I didn’t mean to,” he stumbled to his feet shaking his head. I giggled.
“It’s okay,” I steadied myself to my feet as my heels wobbled beneath me. “I dids it too. Just… you know we works together and all…”
“Right rightssnm,” Derrick nodded as he finished the minibar bottle of whiskey in his hand and looked lost at the ground standing in front of his bed.
“Here,” I giggled more at the cute-lost-puppy-dog look on his face as he swayed with his eyes barely open. I took the bottle from his hand and put it by the TV. I tried to guide him gently to the bed but he sort of just collapsed backwards. His arms going limp in a pile over his head and on his head. Instantly, asleep. I always envied those people who could sleep that hard.
I stared at him for what would have been an awkward minute had either of us been sober. Thick brown hair with just the right amount of premeditated 5 o’clock shadow on his face. He was cute, I admitted. He was skinny and probably 6’1 just taller than me. He never seemed muscular, though I never saw him without a shirt on. I reached down thoughtlessly and felt his chest just below where his shirt V’d and rubbed down to his stomach. He was not muscular, unfortunately, but he was not skin and bones either. Derrick felt toned like maybe a swimmer would feel. My eyes fell down to his lap where his stretched pants revealed something hard. His bulging member pointed at me aggressively. I looked at his eyes and heard his silent snore simultaneously. Looking back at the large bulge I found myself moving my long auburn hair to one side as if I was about to get down on my knees to taste him. I shook my head releasing the thought quickly. But still found myself biting my lip some as my hand reached out and like slowly wrapping my fingers around a door knob I felt his hard dick firm in my grip.
My hand rubbed down as far as his jeans allowed then rubbed back up. Lost in a trans I didn’t wake from until I saw a sleepish hand reach for me. His eyes still closed. He reached for my hips to pull me to him. I blinked as I retreated to my bed his hand staying in the air for a few moments, waiting for me to return. I lied there for a long moment watching his hand as my fingers restlessly played with my crucifix necklace around my neck.
Derrick’s hand finally fell to his lap. I watched his thumb and forefinger intermittently tug on his restrained penis. Every few minutes rounding the head until finally his hand fell to the side. I was a mess. My panties were already glued to my pussy as my thick toned thighs grinded in circles on each other. My bottom lip was getting raw from my teeth dragging over it again and again. My perky nipples pointed out through my white tip and fell to side from side with my breasts as I turned in bed.
I knew I had to take care of this urge if I had a hope of going to sleep tonight, and I thought about what toys, if any, I may have brought with me. But the idea of leaving my warm bed and stepping onto the freezing tile of the bathroom was sobering and nearly drove the horniness from my body. The thought crossed my mind to start touching myself right there. The ghost of a smile creeped onto the corner of my lips as I thought of how hot it would be to cum while my boss slept feet away. The sheer voyeuristic thrill had my heart beating faster.
My right hand slid between my thighs running up to my panties. They were wetter than I imagined. Drenched and stuck to my sex as I peeled them to the side. My fingers making wide messy circles on my lips as I already hear my juices squishing while I stared at Derrick’s hardon. It bobbed up and down flexing in his pants. I imagine his dreams being a hot porno with me being a star in it. My fingers slice into me as I allow one finger to go inside as I picture him waking up to see me fucking myself and my head goes swimming. The allure of him catching me exposed brings me waves of warmth down my spine through the small of my back, around my formed ass cheeks, and deep inside my pussy.
The thought of what would happen next drowned my mind. Images of him releasing his cock from those jeans and coming over here. I knew he wanted me. Two fingers enter my pussy. This body. It would be his fantasy to wake to this. It’s my fantasy right now. I pull my left breast from my already deepening cleavage, circling the nipple as I pump in and out of my pussy. Slight high-pitched moans shoot from my lips as imagine him feeding his cock into my pussy. I think about it stretching me as it pistons in and out. In synch with my fingers. Out of nowhere the thought overwhelms me and instantly I’ve crossed the line of no return. My hips shake and my fingers wiggle inside my lips. The waves start crashing down on me as my eyes roll to the back of my head and a high scream is released from my lips My thighs shudder and shake and my hand is trapped between my thighs. The waves crash again and again as my body shakes periodically with them.
By the time I remember where I am my eyes open in a panic, worried my screams have woken Derrick. But alas, the only part of him that moved was the slight rise and fall of his chest. And of course, the throbbing cock in his jeans. Perhaps it was the alcohol getting the best of me. Or perhaps it was Derrick’s dick refusing to stop teasing me. Staring at it I still felt flush in the face and the warmth irradiating from my chest.
“Hmmmmmm…” I growled a whine like I was a little girl, again. Turning in the bed my thighs swiping past another.
I stood still wearing my one-inch heels and fell from one bed to the other, realizing I might be drunker than I thought and thinking maybe that’s a good thing for when the morning comes. It could be a way out of this potential future relationship. I crawled beside Derrick and instantly felt the heat coming from his body. My hand slid under his shirt and cupped his warm hips as I laid my head down on his chest looking up at him.
“Hey…” I whispered as my left hand rounded his cock then went to his belt undoing it. “Deeerrick…” I said playfully. My lips brushed the patch of hair near his naval. With a clink of his belt my fingers started working on his button and zipper as I inched my face closer to his. “Deeerrick hmhmmm…” I groaned as my left-hand pushed inside his undone pants and wrap around his thick cock through his boxers. My red lips hover over his as I repeat his name again, but receive only the slightest of groans from him. “Derrick?” I said louder with the smallest hint of concern in my voice. My hand ran the length of his cock over his boxers and he still wouldn’t wake. I knew about hard sleepers but this was a new level. My right hand shook his shoulders as I said his name again, but still no response. I sat beside him as he lied there oblivious to the world. My left rested on his thigh as my head slumped to the bed by his hips in defeat.
Short of maybe smacking him or tossing him out of the bed, I knew nothing would wake him from his liquor induced unconsciousness. As I considered these options I laid there listening to his slow deep breaths I stared at his hard cock sticking out from his peeled back jean front. I brought my hand back to his shaft and felt how hard thick he was as I went to the tip and back down. I inched closer, slinging my hair to one side so it flowed over his thighs as I looked up at him. Slowly, I lifted the band of his boxer and stretched them off of his shaft, revealing the wet slick head of his cock.
Maybe I can try to find a different way to wake him, I thought as I took his bare shaft in hand and felt his cock engorge in my hand. “Oh Derrick…” I said eyeing him as I licked from the base of his cock tracing all the way to tip and back down. Pressing his cock down to his belly I licked his shaft over and over as I rolled his balls gently in my warm palm. Slowly, I tongued each ball before wrapping my lips around it. I looked at the tip and saw an ooze of precum that I had to taste. My lips parted and dragged down his foreskin as my tongue circled his hole. Going deeper and deeper I pushed my head down his cock. I felt his shaft grow and harden. It flexed and strained between my lips. I felt a mad rush of adrenaline, the excitement was a new high of anticipation as I watched him still sleep. Knowing any moment, he could wake and fuck my brains out. Knowing he could just cum at any second because the feeling was just too good.
I moaned as my head bobbed on his dick, while my fingers worked wildly on my pussy. Unable to contain my urges I was glad to have his cock between my lips to keep me from moaning like a whore. I felt the juices dribbling down my thigh and knew I couldn’t wait any longer.
Prying my lips from the head of his dick, they made a wet and sweet smacking sound from the suction like I was teasing a lollipop. With a hand on each side of him I crawled up the bed positioning hips over his pulsing dick. My long auburn hair valed my face while the tips kissed his face as I hiked up my skirt. The slickness of my pussy coated the length of Derrick’s shaft as I arched my back dragging my hips down across him in slow motion. The high heels I wore hugged the outside of his legs. My breasts nearly exploded from my top as my arms pressed them together and up.
“Mmmm…” I closed my eyes as I felt his body subconsciously flex against my slit just as my lips reach the head of his dick. I felt his swollen head bulge and begged to enter me. I worked my ass in circles around the tip. “…yess…please…” The faintest words escaped my lips. My hair was strewn a mess across half my face but I no longer cared about any of that. Like a top circling the edges of the drain before falling in, I felt my fingers instinctively palpate the shaft of his engorged cock as I dropped myself on him.
The rush. The feeling. It was too much for the moment as I bent over panting in silence. I felt his cock fill me up and my muscles contract holding him inside me. My hips inched up only to fall again, “oh bab…”
With his eyes still shut I heard soft moans pushed from his lips as I looked down on him. Normally, when I sleep with a guy it’s a mad rush to the finish- mmmm. But now its more like fucking one of my toys- I can take my time. Fuck… I raised my head as I felt him flex inside me. Only better…
Looking down on him I rocked my hips in circles, grinding his flexed thick cock around inside my pussy. I let loose guttural groans when the point of his shaft poked a sensitive place and tried to keep it on there. Instincts took over and before I realized it my hips were riding him. Back and forth, my whole body contorted on his hard cock. I felt a sweat grow on my brow and pulled my shirt off flicking my hair to the side as I braced myself to the left for better leverage. My tan breasts heaved inches above Derrick’s face as I dropped on his cock. “Shit! Aahh!” I moaned as the sound of the working bed and the squishing of my juices filled the room.
My hips jolted back and forth, doing most of the work. “Ohmy- god!” I bit my lips as I made my ass bounce on his shaft. My skirt stretched to the point of tearing over my round ass. I dropped it hard on his cock, punishing my pussy. “Fuck fuck- fuuuuck!” I moaned while my eyes rolled to the back of my head. My right hand ran up my hips to my breast cupping and squeezing my hard nipple.
Then it happened. I felt hands on my hips. Hands that weren’t mine. If I hadn’t been so far gone, I might’ve stopped but I couldn’t. I stole a glance down to see Derrick’s eyes half open. His fingers dug into my ass cheeks as I fell onto him and I felt him push into me. “Oh god.” The words shot from my lips so unexpectedly my hand snapped to cover my mouth. “Oh nahh… Fuck I’msoclose!” The words ran together as one of his hands rose to my tits. I pushed into his grip as my cunt pushed down on his cock. My right hand brushed a handful of my hair from my face. Trapping it against my throat, my fingers wrapped around my neck as my lips opened to scream but no sound came free. Hunched over my thighs I began to spasm. My body froze but Derrick kept pumping his cock inside me. “Oh fuck,” the words jolted out. High pitched and panicked.
Every muscle I owned became dystonic while my eyes clenched shut and went wide at the same time. “Fuck I’m gonna cum! Fuck! Fuckfuckfuckfuckfuck,” I screamed as my pussy spasmed around his shaft. My hips writhed on his shaft. My tits bounced wildly as my fuck toy jammed inside me and I tried to keep control of myself. My hair covered half my face as I cupped his hands tighter to me.
“Oh shhhhhit,” I gasped for air when my head fell to his chest. His dick continued to jam into my pussy as I gripped his neck and whimpered with every thrust. “Oh my god. Oh my…” I panted. “Jesus fucking… ohhh…” I felt the dribble of my milky cum down the crack of my ass to my thigh. After a few moments, Derrick relaxed and fell back in the coma of sleep he was in, and I was fast to follow as I slipped into exhausted unconsciousness on top of his rising and falling chest.
I awoke to the glaring sun jabbing at my eye lids. In a fuzzy haze of a mild hangover I turned to see Derrick asleep in his bed and under the covers. He and I must have woken up sometime during the night as I found myself back in my bed. My pussy still ached from last night’s fucking as I gathered my things for check out. We barely spoke as we finished packing. Me not because I was avoiding awkwardness. Him not because of his constant trips to the toilet to puke every few minutes. Finally, as we rolled our suit cases towards the hotel door, Derrick managed to ask what happened last night.
“Alcohol,” I joked. “What do you remember?” I asked as I tried to probe my mind for the finer details of last night as well.
Derrick rubbed his forehead for a moment, holding the door open for me. “Long islands… bars… more- too many long islands…”
“That’s it?” I asked trying not to give too much away with the tone of my voice. And in that moment, I remember the peacefulness I felt as I slipped away into sleep on his chest after I came. I also remember while falling into sleep his hard cock was still flexing inside me… begging for more…
“Yeah… well…” He started, looking to the floor. “Did we… we didn’t… I mean… Did you sleep okay last night?”
I gave him a devious smile as I walked by him, “I definitely did.”
Still flexing inside me after all last night… Maybe he would make a good fuck toy.
Raven Black’s Erotica Website
(www.ravenblackbooks.com)
Source: reddit.com/r/eroticliterature/comments/e8d29e/my_sleeping_boss_curvy_slutsleeping_sexsleeping