Wing-Woman Wardrobe

Wing-Woman Wardrobe



            What is it with these academic types?  By now I’m sure you’re familiar with our friend, Dr. Smith – divorced, hard-up, and struggling to make a relationship happen.  Allow me to introduce you to another academic divorcee, Dr. Jeremy Wrigley.  Jeremy has been a friend of mine for over a decade.  I knew his wife and his kids, but when I got divorced we drifted apart.  Some people, particularly couples, and even more particularly insecure couples, prefer to keep away from relationships on the rocks rather than stick around.  He was of that ilk.  He knew things weren’t going well in his own marriage and so he was almost allergic to my situation.   

            But his precautions couldn’t prevent the inevitable.  His wife ran off with the plumber.  This was particularly painful to Dr. Wrigley because, of all my intellectual friends, he was by far the most cerebral.  And that is saying a lot!!!  Dr. Wrigley, bespectacled, mild-mannered, and shy is the leading researcher in the philosophy of science, focusing particularly on A.I. and the interface of humans and robots.  As you can imagine, this field that he entered twenty years ago, has taken off, as has his career.  Thus, for his wife – a beautiful sandy haired blonde whom he had met at a bar while in grad school and who was content to be a stay-at-home mom – to leave him for the plumber was a kick in the gut. 

            During the divorce he called me for advice, leaned on me for support, and frequently remarked about how he hopes things turn out for him as well as they turned out for me, that is, Lola. 

            The painful, costly, and messy phase of the divorce was now behind him.  He was interested in meeting someone new.  As he put it, “I may be hyper-intellectual, but I’m also a biological being.”

            Lola suggested dating apps, but he, being a man of a certain age (like my age), felt uneasy about that.  “Everyone on there is young, pretty, unencumbered, and just looking for a hook-up, not a relationship,” he protested.

            “You’d be surprised,” remarked Lo. 

            “You’re just looking for a hook-up,” I reminded him. 

            “Maybe, but that feels sleazy to me.”

            “It feels sleazy to put yourself out there in a way that is honest?”

            “I know that doesn’t make sense, but yeah.”

            “I think you’re afraid of rejection,” countered Lo.  “You’re afraid that the young women will see you and think, ‘Old, divorced, has kids – swipe left.’  But they’re more likely to think, ‘Handsome, fatherly, stable, available – swipe right!’” 

            “You flatter, Lo.  But I’d rather at least try to meet people the old fashioned way – by going to a bar.”

            “You’re out of practice,” said Lo.  “You could use some help.”


            “Yeah, like a wing-woman.”

            “A wing-woman?”

            “Someone to be by your side at the bar so you don’t look desperate.  Someone to laugh and flirt with you to attract the attention of other women.  A single guy at a bar has to be drop-dead gorgeous to attract a woman – no offense.  Women are incredibly competitive and if they see you there with someone, well, with someone hot, then they immediately think you’re hot and want to prove to themselves that they are worthy of you.”

            “Is that so, Lo?” I said snidely.  “Quite the insight into female psychology.  You know this from first-hand experience?”

            “From keen observation.”

            “And whom did you have in mind to be Jeremy’s wing-woman?  It would have to be someone very hot, very sexy, very flirty.  Someone who is in on the scheme and someone who knows what she’s doing.  Hmmmm,” I gestured to rub my chin in deep thought, “I cannot imagine anyone who fits the bill.”

            “Very funny.  You know exactly who!”

            “Who?” asked Jeremy, naively. 

            “Who do you think?” I said to him, “Lola!”

            “Lo?!  You?  Oh no, I couldn’t.”

            “Yes you can,” she said, flirtatiously grabbing his tie and pulling him close. 

            “But, but, HH, it wouldn’t be right.”

            Lo ran her tongue over her sparkling white teeth and, her face very close to Jeremy’s, said, “when they see you and me in the bar, you will have a gaggle of women following you.”

            Jeremy was very nervous.  He hadn’t been this close to any female other than his now ex-wife in a long, long time. 

            “But first we should rehearse a bit,” said Lo, releasing him.


            “Yeah.  Put your right hand on my hip.”

            Jeremy stiffly moved his right hand to Lo’s side. 

            “I said my hip,” said Lo, moving his hand lower, close to her ass.  “That’s it.  Now, look deeply into my eyes as if no one else was here.”

            Instinctively, Jeremy gave a look right at me.

            “I said into my eyes as if no one else was here,” repeated Lo. 

            Jeremy looked at Lo nervously. 

            “You and I will be talking like this,” said Lo in a sexy whisper, “and it will drive the women crazy.  I’ll move close to you, like this,” she said as she practically was touching him with her breasts.  She ran her hand over his forearm and let only the fingertips ever-so-lightly hover over his skin.  “You’ll grab my ass like you own it.”  Lo had to physically place his hand on her ass because he was reluctant to do so. 

            I laughed and said, “It’s ok, Jeremy.  She’s a flirt.”

            “Flirt, slut, hotwife, call me whatever you like.”

            “I’m sorry,” said Jeremy, “I’m just not comfortable with this.”

            Lo broke the spell and pulled back.  “Well, do you want me as your wing-woman or not?”

            “I mean, yes.  It’s very nice of you.  I can see that it would be better to go to a bar with you than alone.  I mean, not even to pick up women – just to go to a bar is always better with someone than alone.  But, I get what you’re saying.  You totally would cause my stock to go up.”

            “Not just your stock,” said Lo under her breath.



            “But Lo, I’ve known you a long time.  And I’m HH’s good friend.  This just doesn’t seem right.”

            “So you do want to do it?” asked Lo again.


            “Then follow me,” she said, walking towards the bedroom. 

            Jeremy turned to me and shrugged his shoulders indicating that this is not his fault, he doesn’t understand what’s happening, and he doesn’t know what to do, all in one gesture. 

            “Look,” I said compassionately, “Lola’s not like other women.  We are not like most couples.  We have an understanding.  I’m not going to get jealous.  She has her own mind, her own body.  Just go with it.  She’s trying to help you out.  Believe me, she enjoys this.”

            “And you?”

            I chuckled at his innocent question.  “It’s all good,” I said with a smile. 

            “Are you coming?” called Lo from down the hallway.

            Jeremy followed Lo and entered the bedroom.  I followed him.

            Lo was enthusiastically laying out her clothes on the bed. 

            “What outfit do you think I should wear?”

            On the bed was a pair of jeans, her black-and-white “jackpot” top, a short skirt, a red dress, a sleeveless t-shirt, and a pair of faux leather pants.  She was holding up her denim mini-skirt. 

            Jeremy paused a moment and surveyed the panoply of options on the bed.  I couldn’t help but recall the iconic scene in The Great Gatsby when the titular character tosses shirt after expensive shirt before dazzled Daisy to impress her.

            In reaction to Jeremy’s dumbfounded silence, Lola ebulliently said, “Oh, I know.  You can’t picture it.  Here, let me help.”  She then pulled off the sweater she was wearing, revealing her lacy pink bra underneath it.  She slid into the jackpot top and then slid out of the jeans she was wearing, revealing her matching pink thong, and put on the black latex pants. 

            “What do you think now?” she asked, pushing her bum out for him to see just how tight the pants were over her rounded rump. 

            “Uh, um, I don’t know what to think.”

            “Maybe something a little more, let’s see, revealing?”

            Lo slipped out of the latex pants and put the denim skirt on instead.  She removed the tight, striped top and took off her bra, exposing her perky breasts in front of my hard-up friend and then put on just the tank-top tee.  There was a lot of side-boob action to be seen. 

            “I’d wear this if we go to a fun bar, not a classy place.  What sort of place did you have in mind?”

            Before Jeremy could answer, Lo removed her outfit once more and she slid into the sleek red dress. 

            “If we go someplace fancy, then I could wear this.”

            She looked at herself in the full-length mirror and frowned.  “I hate the panty lines!” she said and she hiked up the front of the dress, slid her thumb up, hooked the panties and pulled them down, passing them to Jeremy to hold, for no apparent reason.  “That’s better,” she said, admiring herself in the mirror, running her hands over her smooth hips and round rear.  “What do you think?  Should I go commando?”

            “Commando?” asked Jeremy. 

            “Yeah, you know, ready for anything.”

    What do you think?


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    1. This is fab, and you’re an excellent writer. Very intellectual – and this is an intellectual piece with intellectual characters. I get the swinger/cuck vibe from the narrator (Lola’s husband).

      Like Isla, I went back to read again – mainly to clarify the narrator verses Lola, because that wasn’t very clear on my first reading. To make that more crystal, you might insert an early paragraph where the narrator talks about his new wife more distinctly and establishes her as a separate character from himself. That just seemed foggy to me during my first pass.

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