My Worst Valentine’s Day Ever
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NOTE: All rights are reserved by author Zack Love but this story may be freely posted anywhere with this notice and link sexinthetitlebookdotcom. This story contains profanity and adult content.

New York City is legendary for sleeping around. There’s hot tail everywhere and it’s such a big city that two-timing or even three-timing is very doable, if you plan it right.

I generally like to have at least two, if not three, girls on rotation. It makes it that much easier to get laid on any particular night. And you’re more relaxed about any given girl-situation: if it becomes too much of a hassle, you’ve got plenty of alternatives.

And I’m not gonna lie – I LOVE women: their soft skin, the way they smell, how they laugh, their curves, their moans when you touch them right. Sometimes I wish I could just devote my entire life to the pursuit of pussy but I can’t figure out how to put that on my resume. Although I do have a spreadsheet that I started a few years ago, just to keep a scorecard. This became necessary in my mid-20s, when I was in my last year at Columbia Law School and hit a personal record of dating six women at the same time: Colette, Heidi, Soleil, Lori, Jo, and Isa. I managed to keep all of their names straight but I started confusing the details of their biographies (giving them brothers they didn’t have, diplomas they hadn’t earned, divorces they hadn’t been through, etc.). So I realized that I needed a spreadsheet system to keep it all straight in my head.

You probably think I’m a sleazy asshole by now, but I’m just being real with you. I’d say at least half of the unmarried men in NYC have the same view of things but just package it more diplomatically. Or they flat out lie about it. Hell, half of the married men probably have that view too – especially if they’re politicians or tycoons. Open up the NY Post on any given day and see for yourself.

Oh, and Manhattan women aren’t much better. They sleep around plenty. Maybe they’re social climbers trying to fu*k all of the right people to get to the top. Or they’re busy career women who just want some occasional NSA sex. Or they’re impossibly picky in a city of endless choice.

Anyway, you can still judge me, but my disclaimer is over. Time for the story called “My Worst Valentine’s Ever.” And the funny thing is, it really should have been my best Valentine’s ever, had things gone according to plan.

My goal was epic, so the unexpected crash and burn would end up being even more so. I wanted to have a “Celebrating Diversity Valentine’s” where I manage to fu*k three different races on February 14th. I mean, what better day to schedule some United Nations-style love-making than on the official Love Day itself, which is an internationally celebrated day?

And I like this sort of multi-culti approach to sex because I’m a man who loves variety, and I’ve got street cred in a few different worlds. And at the time, I was dating someone from each of those worlds: Lisa, Cassandra, and Ashley.

Lisa was a sexy, 29-year old Chinese-American girl I knew from high school. She worked in retail and still lived in the Newark, NJ neighborhood where we had grown up. To her, I was “Yi Wang” and spoke a mixture of Cantonese and English, and she understood the whole traditional family thing and why I used so much of my free time to help out my parents with their Newark laundry business.

Cassandra was an East Harlem, African-American girl with a booming system and sick dance skills, which of course carried over into the sack. She worked as a janitor at a rival corporate firm, where I met her while doing diligence on an M&A transaction (this was a few years after I got my JD and joined one of those miserably large, NY corporate law firms). Cassandra knew me by my street nickname (“Narc”) and we basically talked in ghetto-speak and cracked each other up with our stories from corporate hell. She was also good with basketball statistics – I guess because her brothers were as obsessed with the game as I am. But mostly we fu*ked, and it was always good.

Speaking of that, Ashley was a boring fu*k. Literally. And her conversational skills were just as lacking. She was basically just a smoking hot body. It’s amazing how much a man can forgive when there’s bootyliciousness involved. I guess my buddy Sammy is right with his whole theory about calculating SQ and how top looks mean people cut you slack when they probably shouldn’t. Anyway, Ashley was one of these pampered, poodle-owning, Fifth Avenue chicks who never had to work a day in her life and would have never been admitted to even a third-tier college without her family’s connections and money. But it was a challenge for a half-ghetto-first-generation-Asian-American guy like me to nail a rich blonde like her, so maybe that was part of the appeal. But she was less interesting than my aging goldfish and I was planning to dump her after my multi-culti Valentine’s exploit. With her, I spoke normal, proper English but usually had to dumb things down a bit. She knew me as “Yi” but I think the only thing she really cared about were my credentials: an alumni of Brown and Columbia Law School, and an associate at the prestigious firm of White, Schue, & Krep. I was probably the first non-white and non-born-rich guy she’d ever associated with, and it was only because of the brand names on my resume that she let me get past “hello.” I’m amazed we lasted even two weeks, but I needed her blonde hotness for my epic Love Day celebration of New York diversity.

Yes, I’m a chauvinist pig. But I’m also in my twenties and living in New York, which doesn’t help. And if you ever disrespect one of my sisters, I will break your jaw.

Anyway, now that you have the cast of characters, I can give you the scheme for what should have been my best Valentine’s ever. I was going to call in sick and spend the day in Newark helping my parents with their laundry business. I would take a 1 p.m. break to go to Lisa’s place, since she lived and worked nearby and could use her lunch hour for a quickie at her apartment. So that would be Lay #1 (Asian). After that, I’d go back to my parents' laundry business, and finish helping them until about 7 p.m. Then I’d head back to my studio in Murray Hill, where I’d change into my Armani suit, so that Lay #2 would think that I had just arrived from the office.

Lay #2 would be Ashley (the blonde but boring hottie) and I’d have to wine and dine her at her favorite fancy restaurant (as usual). Late into dinner, I would look at an “urgent email” on my “Crackberry” and apologize about having an unexpected conference call with a Hong-Kong-based client in 90 minutes, which would force me to go back to the office after dinner. By then, she would have had enough alcohol and romantic V-Day talk for her to go along with my “plan B” for consummating Cupid Day together: I’d take her into the restaurant’s perfectly private and swanky unisex bathroom and fu*k her between dinner and dessert. With enough wine and charm, by that point I’d probably have a 60-70% chance of scoring Lay #2. She would definitely be the toughest part of my International Love Day, but I relished the challenge.

Lay #3 was going to be ghetto-girl Cassandra. After fu*king Ashley, who thought I was going back to the office (where I had already called in sick), I would take a cab to East Harlem, pick up some flowers, wine, and chocolates near Cassandra’s place, and then knock on her door at around 10:30 or 11 p.m. (I told her that I wasn’t sure when my Lay #2 – I mean my conference call at the office – would end).

Having sex with three different women, races, income classes, cultures, and worlds – all on Love Day – would be EPIC. To make it even more of a historic Valentine’s Victory, I was going to get anal from Lisa and Cassandra (whom I had trained and charmed into giving it on a regular basis) and at least doggie from Ashley (who was finally coming around to my favorite position). If I could do all of that on February 14th, it would be a personal best for me. Something to share with my crew for the glory and the laughs, or to cheer up the next buddy of mine to get dumped or cheated on.

So that was the V-Day dream. Now here’s the nightmare that ensued. Lay #1 goes according to plan and I even get Lisa to talk dirty to me in Cantonese during anal, which was a first for me, and a bit weird – maybe because I normally speak Cantonese only with my relatives. Not doing that again. Anyway, Lay #1 was an otherwise awesome start to what promised to be my best Valentine’s ever.

But Lay #2 is where it became my worst Valentine’s ever. I shower from Lay #1, put on my Armani suit, and take a cab from my apartment to the fancy restaurant to meet Lay #2.

Everything is going as planned until I notice that Ashley has barely touched her wine glass or food after ordering the priciest bottle and several of the most expensive dishes on the menu. As I’m doing the math and realizing that I’m probably going to be stuck with a $400 tab for this dinner date, I’m trying to play it cool and figure out how and when to suggest we go to the bathroom. And just as I’m about to lay on the Yi-Wang-Smooth, I see Lay #1 and Lay #3 show up to our table and take the two empty seats nearby.

Yes, you read that correctly: Lisa and Cassandra have shown up to my dinner date with Ashley. There’s really no way to sum up what happened next except to give you the dialogue.

“Wh-what are you two doing here?” I stammered in confused shock.

“We sistah’s was havin’ a lil’ fantasy goin’ on. And we was talkin’ about our ideal Valentine’s, thinkin’ we’d all like to get a piece of you on V-Day,” Cassandra said, with sadistic swagger.

“Bu-But how do you…How do you even know each other?” I was really perplexed by this most unfortunate coincidence.

“Now, Narc, I know you is the lawyer here. But we goin’ do the deposition this time. Then you can ask yo’ dumbass questions.”

“Yes,” Lisa chimed in. “We’re asking the questions first. What does the word ‘anal’ mean to you?”

This was getting uglier by the minute, I thought. There really was no easy escape, since we were sitting far from the exit and the waiters knew me from prior dinner dates with Ashley and I hadn’t paid the tab yet. Why the hell was Lisa asking what the word “anal” means to me?

“Um, well, I’m a pretty anal guy – I guess that’s why I work as a lawyer. You know, you have to be really anal to chase commas all day in different drafts of a corporate spin-off agreement.”

Lisa continued: “To me, anal means a certain degree of intimacy and exclusivity. How about you, Cassandra?”

“Damn straight. Narc should know about exclusivity. ‘Cuz I know some of ’dem contracts you writin’ be all about that shit.”

Ashley then joined the fray: “And what does the word ‘doggie’ mean to you?”

Like a driver who has lost control of his vehicle, I was bracing for the impending crash. “Well, I’ve told you that I was never a big fan of dogs, but I did try to make an exception for your poodle.”

“Yes, and I was never a big fan of doggie, but I made an exception for you too. Somehow you made me feel special – like you were worth it.”

Lisa continued but this time in a sexy and suggestive voice that almost gave me a moment of hope: “After you left my place this afternoon, Cassandra gave me a call, and we started talking about how our fantasy for Valentine’s Day was to give a whole new meaning to the words ‘anal’ and ‘doggie’ – you know, just to take these things to another level that none of us has ever experienced.”

If it weren’t for the fact that Cassandra should have never had Lisa’s phone number, that could have sounded like an invitation to have a kinky foursome after this disastrous dinner I needed to escape. I knew that I was heading into some kind of terrible trap but I couldn’t resist the curiosity they had provoked in me. So I asked Lisa, “What do you mean, take anal and doggie to another level that none of us has ever experienced?”

Lisa replied, “Well, this wasn’t so easy to set up. And – as in the sexual context – the anal part was actually a bit trickier than the doggie part, right Ashley?”

“Yeah, I have to pick up after Jennifer anyway,” Ashley agreed, referring to her annoyingly barky white poodle.

“What do you mean?” I asked in dread.

Ashley pulled her hand out of her purse, holding a plastic bag of Jennifer’s poo. “This is doggie!” she said, hurling the bag of dog shit all over the torso of my Armani suit.

“And this is anal,” Lisa added, throwing her own plastic bag of crap and hitting the side of my face. “It’s a bit harder to get than doggie, as you know,” she added.

Cassandra added the coup de grace: “And here’s yo’ second anal, Narc. ‘Cuz I was thinkin’ two anals and a doggie on Valentine’s would be the SH*T.” And her bag of sh*t landed smack in my face.

After I took a 20-minute-dung-removal bird bath in the restaurant bathroom, paid the $400 dinner bill, and walked out as embarrassingly red as an Asian face can get, I get a text message from Cassandra. “4 a well-educated lwyer u sure is a dumbass, plannin VDay on ur fone in my bthrm after u was gettin herbal.”

And then the full extent of my cocky dumbassness hit me. I had scheduled UN Love Day with Lay #1 and Lay #2 a few days earlier, while I was taking a dump in the bathroom of Lay #3. I did this with my personal cell phone, which – unlike my work Blackberry – had no password on it. I was a bit stoned and sleepy at the time, and forgot my phone in the bathroom before Cassandra and I had one more round of sex. Then I was down for the count. But not the girl. And girls go to the bathroom. And if your phone is sitting there in the bathroom without you and a text message arrives, they will read it, along with all of the other text messages. And then you’re really fu*ked.

After reading Cassandra’s text, the full extent of her revenge-seeking, diabolical genius dawned upon me. She purposely planned to sabotage everything AFTER Lay #1 (Lisa, in Newark) so that I’d suspect nothing and think V-Day was going as smoothly as planned. Cassandra shrewdly waited until after Lay #1 happened before telling Lisa what she had found on my phone. And then the two of them clearly conspired with Ashley over all of the details of their shitty revenge.

The next night, my buddy Sammy (aka “Heeb”) stopped by my office to tell me all about his best Valentine’s Day ever. After he closed the door, he detailed how he had transformed a sh*t sandwich into an epic score that left him totally triumphant. When I then told him about my actual sh*t sandwich, he fell to the floor laughing in uncontrolled hysteria. So for about 15 minutes, I had this short, pudgy, balding guy on the carpet of my office convulsing in violent laughter and desperately gasping for air. And then he was gloating about the whole thing for weeks after that.

Whatever. I had to let him savor the one time that he trounced me in a sex smackdown – on V-day no less. Granted, I did get some anal but I experienced it as no man ever should. The whole thing made me religiously embrace monogamy. For about a week.

Needless to say, that was the shittiest Valentine’s Day of my life. Literally.

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