“How To Talk To A Newly Separated Cougar” is an excerpt from Jimmy Gleacher’s latest book, a collection of erotic short stories called COUGARS ARE MY WEAKNESS. This story was inspired by, and modeled after Pam Houston’s short story, “How to Talk to a Hunter.”
When she says “Black or white?” it will take you a moment to realize she’s asking which color lingerie you want her to wear.
And in your hesitation she’ll decide to wear black because the blouse she plans on wearing will be sheer enough to reveal the dark silhouette of her bra. She is yours for that night, but the town is full of men your age, men who like you, will watch her every move despite being ten years her junior. When she was a younger woman, trying to raise a family and preserve her marriage, she didn’t like all those hungry eyes tracking her through the restaurant, because sometimes they served as a reminder of all she was forsaking. She is separated now, and free to make eye contact with anyone who looks her way. As you watch her thumb the bra straps over her shoulders and reach her arms behind her back to clasp the lacy silk contraption together you realize she can pretty much have her pick of the town, and that she knows this better than anyone.
You didn’t know this woman before her separation, but you know she is the mother of two daughters, owns an art gallery, and spent twenty years building a hard-earned comfortable life with the man who is still her husband by law. She talks about her children often but has failed to ever mention her husband’s name. Try not to wonder how she can wipe out the existence of someone so entwined in her life, because doing so will make you realize how easily she can do the same to you. Don’t ask her why she got separated, or how long the separation will last. You’re there to make her forget about her husband, mostly by having sex with her. You are the surrogate for all the young men she disregarded during her marriage.
Remember this as you watch her clasp her black bra on for the evening. Walk up behind her and undo her clothing. She’ll squint at you suspiciously and ask, “What do you think you’re doing?” A sly curve in her smile will indicate she would’ve been disappointed if you’d sat there and done nothing. She’ll let the bra fall and wrap her arms around your neck and kiss you like it’s midnight on New Year’s Eve as she hops into the air and deftly wrap her legs around your waist. Carry her to the bed and lay her down across the mattress with her legs dangling off the edge. Drop to your knees and pull off the black underwear that match the discarded bra on the floor and devote the next twenty minutes to pleasuring her with your mouth. She’ll try to pull you up. She’ll tell you she needs you inside of her. Rise up between her legs. Give her just the tip of your penis. She’ll grip your ass to pull you in deeper. Brace your legs and hold your ground. Tell her she’ll have to wait. Then step away and hand her her panties. She’ll pretend to be pissed. She’ll call you a tease. But she won’t take her eyes off of you at dinner.
You weren’t supposed to fall for her. She was supposed to have been your conquest, but one Sunday morning you will share a series of tender, intimate moments with her in your bed that don’t involve sex, and you’ll realize then and there those are the moments you’ll remember, and you’ll know deep in your heart you’ll miss those moments more than she will.
Your best female friend will explain, “The problem is your heart is open and her heart is still closed.”
Your best male friend will say, “Dude, why buy the cow when you can get the MILF for free?”
The irony is you’re the cow, and it’s your milk the separated cougar is drinking for free. You’re not even her only cow. She uses her daughters as an excuse not to see you during the week, but her car has been parked downtown on nights when she claimed to be home doing science projects and history reports. Wisely, you never say a word.
The fastest way to a newly separated cougar’s heart is between her legs, so this is where you focus your energy. After one extremely successful romp she lets her guard down enough to mention her children’s upcoming Spring vacation. They are leaving town with their father for seven days. She says she wants to get out of town too. You’re pretty sure she’s inviting you to go somewhere with her, but she doesn’t actually come out and say it. Kiss your way down her stomach to between her legs, and flip her on to her hands and knees because this is how she likes it most, to be taken forcefully from behind, like it’s her who’s the object, like fucking her is all your idea, like she means less to you than she already knows to be true. This is how you’ll get invited to go away with her.
Your best female friend says, “The only reason you’re in love with her is because you know you can’t have her.”
Your best male friend says, “The day she gets divorced will be the day you lose interest.”
You consider getting new friends, but they both know you so well.
You end up with her in Hawaii for a week. You stay at a timeshare she bought with her husband three years earlier, when the marriage was failing and they were lurching for remedies. She’s been to the condo twice, once with her husband, and once alone, right after she got separated. She’ll talk about the ocean’s soothing qualities, and how she had needed some time alone to clear her mind. But then your first day on the island she takes you for a walk on the beach and you run into a surf instructor named Kai. They hug, for far too long, and when Kai mentions the week they spent surfing together on her last visit, you’ll wonder just how much of it she actually spent alone. Kai has shaggy blond hair, is tanned to perfection, and has muscles in places you didn’t know muscles existed. Your cougar asks him how his painting is coming along, and tells him to reach out if he ever needs help with any galleries on the mainland.
For the rest of the trip you bite your tongue every time you feel the urge to ask about Kai. By the end of the week your tongue is so swollen you can barely speak.
Your best male friend asks, “Kai? What does he paint, stick figures?”
Your best female friend asks, “Do you think he’s on Instagram?”
Your week in Hawaii brings you and the separated cougar closer. She makes arrangements to see you on weeknights. She hires babysitters, cooks you dinners, decorates your house with paintings from her gallery. During sex she tells you you’re the best thing to ever happen to her, and that you made her remember what it feels like to be wanted again. Resist the urge to say anything back. She is walking a tightrope of falling for you or returning to her real life. Vocalizing any kind of attachment could make her fall in either direction. Instead, kiss her slowly, fuck her softly, and look into her eyes as she orgasms.
When her children finish school for the year they’re sent away for a month to visit their grandparents. She tells you this the day after they’re gone. You’re having dinner at her house, you’ve only been there once in all the months you’ve been together. You grill a steak and she makes a salad full of fresh vegetables. She teaches you how to make a simple vinaigrette using only lemon, mustard, olive oil and vinegar made from apple cider. After the meal you lie on a blanket in her backyard and watch for shooting stars. She lives on three acres. You can’t hear a single car, or any ambient noise. The two of you share a silence that is intimate and startlingly comfortable. You make the mistake of saying you could stay there forever, and she laughs and replies, “We both know that isn’t true.”
Your best female friend will say, “Are you guys using the L word?” You tell her absolutely not, but the truth is the separated cougar tells you she loves you all the time, but only while you’re having sex.
Your best male friend will say, “If there’s anything a woman can’t stand, it’s an empty promise.”
Kai visits from Hawaii during the month her children are gone. The timing seems too coincidental not to be planned by her. She tells you it’s a business trip, that it’s only for the weekend. She’s taking him to all the local galleries, and hosting a show for him as well. She doesn’t tell you not to come to Kai’s show, but she doesn’t invite you either.
You suddenly taste blood and realize you’ve nearly bit your tongue in half.
Your best male friend says, “The best way to get over an old love is to find a new one.”
Your best female friend says, “Where’s her gallery again?” casually, like you don’t already know the reason why she wants to go.
Is that really all women care about? Six pack abs?
She’ll say, “If it’s only for the weekend, abs…solutely.”
On the morning of Kai’s show you find a bouquet of flowers and a jar of home made apple cider vinaigrette on your door step. You give the flowers to the cute college girl who works at your favorite coffee shop. You pour the salad dressing down your disposal and toss the jar in your recycling bin hard enough to make it shatter.
Your best female friend will say, “I don’t mean to be heartless, but your relationship was never real to begin with.”
Your best male friend will ask, “Did you at least get a phone number from the girl at the coffee shop?”
Later that day, near the end of the afternoon, the separated cougar will show up at your house, dressed to the nines for Kai and his show. Tell her she looks nice, but pretend to be distracted. Watch her scan your living room and kitchen for the flowers she left on your doorstep that morning, and enjoy her not seeing them. Pretend like you have no idea why she’s there. Eventually she will frown and then reach her arms out to hug you.
Listen to her story. First she will say it was only supposed to be about work. Then she will say they’re really just friends. Then she’ll use her separation as her reason. She’ll say she panicked because she started feeling committed to you. She’ll tell you she’s scared to have such deep feelings again. She’ll tell you it had been so long since her husband loved her that she forgot how frightening opening herself up would feel. Let her talk, don’t say anything, and just nod your head slowly. The longer you stay silent the worse she will feel, so look her in the eyes, smile warmly, but don’t say a word, especially one that rhymes with Kai. When she runs out of things to say she’ll tear up. This is your crossroads. Remember that at the end of the day she belongs to no man, not you, not Kai, not even her husband.
Lie her down on the kitchen floor and push her skirt up above her waist. Pull her underwear to the side and lick her between the legs. Soak her panties with your saliva so they’re wet long after she arrives at Kai’s show. Fuck her hard at first. Press her face against the floor as you slam your hips between her thighs. This will be her punishment, but also her reward, to know you care enough to be hurt. She’ll tell you to fuck her harder. Be careful not to rip her dress. Then shift gears and make love to her with all the devotion in your heart. Fuck her long enough to make her late for the show, then pull out right before you climax so you soil her stomach and skirt. She’ll know why you did it. She may even pretend to be frustrated, but deep down she’ll be happy you wanted to leave your mark.
Your best female friend will say, “He’s definitely hot, but his paintings made me seasick.”
Your best male friend will say, “I can’t believe you came all over her dress,” and give you a high five.
The next morning you’ll hear from the separated cougar as she’s driving back from dropping Kai off at the airport. Let her call go to voicemail. Don’t call her back until dinnertime. She’ll invite you over to eat a meal she’s been preparing for the past few hours. The ingredients are specific and expensive, and not ones she usually keeps in her pantry. Go to her house. Compliment her cooking. Try to be distant without being rude. As soon as she clears your plate prepare for her to start the conversation. She’ll apologize, but she won’t be apologetic. Aloofly reply you don’t feel like being tied down either. Notice her frown. Smile at her and ask, “Isn’t that what you want to hear?”
She’ll say she doesn’t know what she wants from you, but she knows she doesn’t want to share you with anyone.
Ask her how Kai’s show went.
She’ll say the weekend was a disaster. She’ll say she wanted to be with you the entire time. She’ll say she was confused. She’ll say she doesn’t expect you to understand. When the kitchen is clean and the counters are spotless she will ask you to stay the night. Go home. Let her toss and turn on the clean sheets she put on the bed anticipating your return.
Your best female friend will say, “If I ever get married and then divorced I’m definitely finding a Kai. It’s part of the process. You can either accept that or not.”
Your best male friend will say, “You ought to know this by now: Rules don’t apply to a newly separated cougar.”
The next morning surprise your cougar by picking her up early and taking her out for coffee. When she spots the flowers she gave you behind the counter as the cute college girl smiles at you while making your latte, the newly separated cougar will pretend not to notice. This is how you know she doesn’t love you. If she cared she’d be hurt, but instead she makes dumb jokes and laughs too hard and tries to pretend her jaunt with Kai never happened. Tell her it’s over. She won’t cause a scene or try to change your mind because you’re just as interchangeable to her as Kai. If this makes you sad the fault is all yours. You were never supposed to fall in love with her. She was never even yours to begin with.
Author: Jimmy Gleacher
Editor: Emily Bartran