I’m still not sure how I let my sister talk me into a Halloween cosplay party that particular year, of course. Maybe I was just in a mood to forget my troubles and the recent divorce from Kathy after six years of marriage. Granted, it was stupid to marry my high school sweetheart in the first place without any real grasp of what marriage entailed, but people had kind of built up the pressure until we both foolishly caved and wed without truly knowing each other or what we wanted. If she hadn’t left me first, I probably would have done that to her instead. At least we divorced while still of childbearing age, which was a mercy.
One thing that I could count on Denise for, though, was trying to cheer me up, especially on fun holidays like Halloween. I’m not sure if she was my favorite sister, but she certainly tried her hardest to treat me like her favorite brother. She also seemed to be good at playing my heartstrings, by implying that she lacked a date and that I could pretend to be her boyfriend that night. Her friends wouldn’t know it was me under that mask, anyway, right?
“Now, bro, remember ... just because we’re pretending that we’re supposed to be a couple doesn’t mean that we have to stick together the whole time. We certainly don’t have to pretend to be ... a faithful couple, you know. Nobody knows who anyone else is, anyway. There is a lot of drinking and partying, a lot of goofing off, and you really need to try the cosplay scene before you knock it, bro. Who knows, you might just get hooked, right?
“After all, part of being single again is learning more about yourself and exploring life, seeing what you really want so that you don’t repeat the same old mistakes, wouldn’t you say? Just promise me that you’ll do what comes naturally, okay? Don’t force anything that feels wrong and don’t resist anything that feels good.
“I can guarantee that I plan to have some fun tonight, and since it’s also your birthday as well as Halloween at the stroke of midnight, well, you should totally live it up,” Denise pointed out that I was the birthday boy, so Halloween was a double whammy occasion to kick back and have a good time.
“Okay, sis. I’ll do my best to enjoy myself. I make no promises about success, but what’s the harm in trying?” I reassured Denise, who gave me a very strange look now as we headed to separate dressing areas in her house.
“Do or do not. There is no try,” Denise mimicked Yoda, making me roll my eyes.
“If you dress up as that little green troll, I’m gonna laugh my ass off for sure!” I taunted her, getting a tongue stuck out at me in response.
“No chance of that. He’s a lot shorter than even me, and I’m hardly a giant,” Denise alluded to her own shortness, which always bothered her for some reason.
“Yeah, sis, I suspect that you sometimes let me crash at your place just to have a tall guy to reach things for you. Don’t worry, though. You’re bound to land a giant who’ll do anything for his cute bride. Or hers, if you’re gay,” I winked at my sister, who stuck out her tongue again as we finally closed the doors behind us to dress.
Poor girl, I thought. It wasn’t her fault that she was short. Her mother was an Inuit woman from Alaska, one that Dad had knocked up on his many adventures after Mom kicked him to the curb. My father had been less than faithful to Mom when they were married, but he’d bothered to use protection back then. When he learned that Mom hadn’t returned the favor, he’d really blown up at her. Furious at what she saw as hypocrisy, she kicked him out and had him served divorce papers. Then she proceeded to have the baby with her new beau, thus making one of my brothers, Quincy.
Six months later, she tracked him down and tried to win him back, but the damage was done. Her loser boyfriend was already in the slammer for armed robbery and felony murder, not necessarily in that order. Meanwhile, Dad had married an Inuit woman named Patricia in Fairbanks, Alaska, and they lasted about two months before SHE kicked him out for fucking around on her. Twice unlucky in marriage, Dad fooled around a lot before he tried for the third time and charm after he moved back home.
He just did it with a blonde cutie named Candace. She was actually my favorite stepmother for several years, until she got tired of Dad’s heavy drinking and served him papers, too. It seemed that his straying was tolerable, but she couldn’t stand him being too drunk to clean up after his trysts and too drunk to give his wife her fair share of that dick. That was a dealbreaker. Even now, we’re still friends, hard to believe as that might be. Hell, Dad and she are still friends, the only one of his ex-wives who gets along with him beyond mere civility.
Mind you, Dad is now sober as a judge, thanks to getting help for his alcoholism. He married a fourth time and this one stuck, though I didn’t know the details and I didn’t honestly want to know. I suspected that they have some kind of arrangement to either openly accept each other’s indiscretions or else a tacit understanding to look the other way, because there was no way that ginger vixen Brittany would be satisfied with once or twice per night. She struck me as a raging nymphomaniac unless I miss my guess. Dad was probably okay with it as long as he got his piece of ass.
Anyway, Patricia’s legacy to Denise was dual in nature: her shortness and her low threshold for booze. Denise gets tipsy very fast, and it doesn’t take very long for her to get totally hammered, either. Okay, there was a third inheritance: her short fuse. Denise blew up fast at people, but often returned to normal just as quickly, mending fences a lot better than Patricia did. Come to think of it, Patricia had tried desperately to get back with Dad once she learned that she was pregnant with Denise, but again it was too late. Yeah, there’s a lot of rashness in my family, and it isn’t limited to my sister or stepmothers, or to my Dad, for instance. Hell, I was pretty impulsive by wedding Kathy, wasn’t I? At least I’d learned my lesson, or so I thought.
Anyway, here I was, in a separate bathroom, changing into the Cupid mask and outfit that Denise chose for me and I accepted with resignation, lacking a better option right then. I sometimes wondered at my sister’s sense of humor, of course. Then again, she was always very close to me and went out of her way for me, pranks and teasing aside. She really was the best sister that a brother could have, come to think of it. She had even let me crash now and then for the past several weeks since Kathy ditched me, not pressuring me to find a permanent place instead of switching between her place and Dad’s (and Mom’s sometimes, but that’s a sore spot).
When I exited the bathroom, I noticed that the first guests had arrived and Denise was in her element ... Yeah, I failed to mention that she was the hostess, didn’t I? Dressed like some Hollywood version of Pocahontas (no real need for accuracy on Halloween), I had to admit that my sister was very attractive in her own right. She was also half-naked, which did something to my blood temperature, to put it mildly, seeing those fine buns of hers half-exposed to me under that loincloth. Oh, God, was I that hard up, that I was now reduced to ogling my own sister and having incest fantasies?
I started mixing it up, determined not to be a wallflower this time. I had promised my sweet sister that I’d mix it up, and so I would. Most of the guests reacted favorably to the Cupid costume, much to my surprise. It hadn’t been cool when I was growing up, but tastes were known to change and so were styles. Clearly, that was the case here, and it worked to my benefit, as I didn’t get the brush off that I feared from the ladies. In fact, my clothing, what passed for it, got notes with phone numbers slipped in more than once, evidently due to those women who didn’t mind their Cupids somewhat hairy and less than pudgy.
As the music and the party picked up a bit, more guests streaming in, I found myself the benefit of more than one bit of twerking action. Several pretty college co-eds didn’t seem to mind a man in his mid-twenties, in any case. One was dressed as a nun, which was a real hoot, the other like Catholic schoolgirl, while a third went as Dolly Parton, no joke! The Elvira one, though, really did a number on me, as she had tits to make the Mistress of the Dark green with envy. There was no way that those tits were real, was there? She even rubbed her cleavage against me, which had the more than desired effect. Cupid was very horny!
Being also more than a little sauced, I took Denise’s advice, despite being her older brother, and I soon found myself bumping and grinding in earnest with everyone else. I had some definite fun with a Monica Lewinsky look-a-like, too, and damned if I didn’t have to convince myself that she wasn’t the real McCoy. Of course, that might be a bit of the Chivas in my system, too. I always thought that Bill Clinton showed great taste in women with that intern, being very fond of plump girls, anyway, so she was a real turn-on. Evidently, “Monica” felt the same way, because she lost patience and dragged me to a closet to all but rape me.
“You know what I want, don’t you, Cupid? I didn’t dress like the most famous intern in the world just for the beret, honey. I didn’t wear a blue dress for my health, either. Come on ... and cum on, if you catch my drift,” the sassy brunette told me as she got my lower half naked like my upper body and started inhaling my cock.
I didn’t know if she maybe was getting too much into her role or what, but “Monica” knew her way around a dick for sure. She licked, sucked, kissed, and otherwise tasted my prick every way that she could. She deep-throated me. She fondled my balls and my ass. She rolled me around in her mouth. She let me fuck her face as I wished for a few strokes as if it really were a pussy ... a very wet, warm, and willing pussy. She playfully scraped the head of my cock with her teeth, not enough to draw any blood or break the skin, of course. She made sure that I knew that she was the cat and I was the mouse here. She did everything that she could do to bring me to the edge before she abruptly cut me off.
“Sorry, but I want my cum stain! I’m Monica and I get my cum stained blue dress!” she told me as she jerked me off enough with her hand that I exploded all over the top of her dress, “your cock is yummy as can be, though, and I definitely want more!”
With that, “Monica” went back to work and got her soft, pouty lips wrapped around my dick all over again. I found my hands holding on to her hair and accidentally knocking off her beret to keep from toppling. She shrugged it off, put her beret back on, and got back to work with surprising aplomb. She practically took me in to the root more than once, smelling my pubic hair with not a hint of revulsion. She sucked, licked, and kissed me with the same ardor as before, maybe even more than that. I could feel the silk of her jet-black hair as I stroked it freely. I groaned with every flick of her tongue across the head of my cock.
“Mmmmm ... I think that I’m ready to fuck you now, if that’s alright with you, dear,” the Monica clone told me, bending over and lifting up her blue dress to take me all the way inside her juicy twat with just three thrusts.
“Oh, damn it, woman!” I exclaimed as I began fucking her with my usual vigor.
“Yes, and it’s better bareback, isn’t it?” the faux Monica encouraged me as I slid repeatedly in and out of her cunt.
“Inside your awesome pussy for sure!” I told her, thrusting furiously inside her now.
“Yeah, I knew that you’d enjoy my twat! This pussy is yours now, you know. Anytime that you want this snatch, you can have it. Same goes for my mouth! I refuse to give this up! The only way that I’ll ever refuse you is if you try to put a rubber on it first. No condoms, baby! All bareback for me!” the pseudo-Lewinsky assured me.
“Oh, damn it, girl, those words only make it worse! I’m already faster with a second wind that I normally get when drunk! What did you do, slip me Spanish fly? Essence of mandrake? Fuck, you’re slippery as can be! It’s a lot better than my ex’s for sure!” I declared as I continued pounding the false Monica for several more minutes.
“Yes, and my ass is yours, too! Oh, yes ... fuck me, lick me, spank me! You own every fucking hole on my body and I will service you on demand for life!” the Monicaesque woman informed me that I now had sexual rights to all of her.
“I don’t even know your name and you don’t know mine!” I gasped as she continued taking me deep and spread her cheeks to give me a view of my new property.
“It’s okay, Cupid, because we’ll meet again and I’ll fuck you! I’ll fuck you so much and so hard that you’ll know that I’m your slut! Oh, God, oh ... fuck meeee!” the “Monica” lady let me out of her pussy just long enough to tell me, “did I mention that I’m fertile now?”
I lost it right then, of course, spurting rope after rope into her wonderful pussy, making her cream herself from the knowledge that I filled her with my seed. I started to panic as I realized that I was likely to be a father now, but “Monica” rose with a goofy grin and sucked on my neck for a bit. I started to pull off my mask, but she did it for me. She grew very pale all of the sudden and removed her own disguise, from her beret to her wig.
I’m not one for fainting, but I nearly blacked out as I recognized none other than my boss, Tamar Efremov! She was the daughter of the CEO and primary owner, Yitzhak Efremov. As such, she supervised several of us other truckers with their Israeli shipping company that bought our local firm. Mind you, we got paid pretty well, being Teamsters, and in fact, even more now that Mitzvah Unlimited put us on their payroll. It was a good thing that Israeli companies were used to dealing with trade unions and didn’t sweat such issues, perhaps.
“Charles? Oh, my God! Oh ... my ... God! The best sex that I’ve ever had and it’s from one of my own staff! One of my truckers! Oh, honey ... oh ... fuck ... me!” Tamar reacted with obvious astonishment.
“Will you do me the courtesy of good references if you must fire me?” I asked, assuming that my job was toast now, “At least let me resign and with good references. I’ll go quietly and keep this little tryst our secret, of course. I’ll need a new trucking job with a new firm, after all.”