Purple Hats and Caftans

I live in a 50 story tower in downtown Manhattan, in one of the 500 tiny apartments in the building that stacked up one on top of the other. That forced closeness leads us to keep a respectful distance -- just a polite "hello" while on the way to the trash chute, or while in the laundry room, and seldom anything more.

When the pandemic hit we all hunkered down in our little cells -- umm, apartments - listening to the sirens wail all night. Paranoia set in, and almost all interactions were avoided.

The only other person in the building who I knew was the retired schoolteacher across the hall in 15G, Laurie Robertson. She was thin, kept herself in shape with yoga, and looked more like she was 65 than the 70-something that was her true age.

I'd help her out with her groceries and packaged, and in return she'd bake cookies or muffins as a "thank you," which she didn't eat many of herself -- "would ruin my figure" she'd say, although she was flat-chested and didn't have much shape at all, to be honest. I kept an eye on her as the pandemic raged, picked up groceries for her, dragged in heavy cases of cat litter, and she kept baking for me.

I liked Laurie. She had an irreverent sense of humor that surfaced after her second glass of wine during our pandemic get-togethers -- we'd each sit just inside our apartment doors, each with our own bottle of wine, and talk about anything and everything.

I liked her despite the fact that she was opinionated and bossy -- probably from years of teaching kids, when she had to take charge of a classroom - but being opinionated in New York is obligatory, or you get eaten alive.

One day, as the pandemic was waning, she told me she was moving to "a new facility." I was more disappointed than I would have expected, and told her so. My reflexive remark would have been "Hey Laurie, WTF, huh?" but I kept it civil.

"I'm not getting any younger!" she said with a chuckle. "I found a nice 'transitional living' place on the New Jersey shore called 'Greystone'. They probably should call it 'Greystroke' -- or maybe 'End of The Line' " she said with another laugh, but her new place sounded nice.

I helped her move out, gave her a strong hug goodbye, and wished her well. I told myself that people come and go in New York all the time, and once again immersed myself in my work, living alone in my apartment.

It was about four months later that her email popped into my inbox with pictures of her townhouse, a breezy update on her life, and an invitation -- of sorts. She was loving her new place, her new freinds -- but needed some things done, pictures hung, a bit of painting, some hinges tightened.

"Hiring a strange handyman gives me a bit of the creeps - bring your tools, and I'll bake some muffins" she wrote, more of a command than an invitation -- typical of Laurie.

I booked a train for later in the week, and that Thursday was pulling out of Penn Station on New Jersey Transit's 6:15pm to Bay Head Junction.

I had expected a dreary place full of doddering old people -- but it was the complete opposite. "Greystone" was nice, safe and neat behind gates, on a section of the New Jersey Coast that wasn't overrun by cheap motels, arcades, day trippers, dive bars and college students.

Her section of the development, for people who were still completely independent, was a cluster of tidy, tiny cottages on a rise overlooking some dunes and the beach. Each unit had a small yard surrounded by a privacy wall, a two car garage, and interior layouts with everything you'd want and then some, like emergency call buttons for assistance. Laurie had upgraded her unit with a small heated pool in her tiny yard.

She welcomed me with a smile and a hug. "Nicer than my apartment in New York, no? And you can't beat the view!" She got me settled me into the guest room, gave me a list -- she was very well organized -- and asked me "what the plan was," more like a command to "get going."

That night I took an Uber to the closest Home Depot to get the stuff I'd need - hooks and screws and spackle and the like - and when we got up Friday I started working through the list. By late afternoon I was done.

I thought I might hit the beach for a bit before heading back to the concrete canyons of Manhattan, but to my surprise she told me that she was having a few friends over for an after-dinner cocktail hour. "Barb and Sally are coming over -- we do this once a week. We've become great friends since I moved in."

"And their husbands don't mind them coming over?"

Laurie laughed, a bit wryly.

"Sweetie, bad news for you -- you're a youngster at 62. By my age we've either buried our men -- sometimes more than one - have them in wheelchairs, or, well, they're just useless, sitting in a shapeless lump with sports on the headphones as they watch old World Series games that they've forgotten. Barb's second husband died five years ago, and Sally's has been in the 'memory care' wing here at Greystone for nearly four years. 'Memory care' my ass - he can't remember a darn thing, let alone her name. So much for caring for his memory!"

Her friends were scheduled to show up at 6:30 -- not quite the "after dinner" slot that I had imagined, but eating early, as in the 4pm "Senior Citizens' Special," seemed to be a real thing here at Greystone.

"I've got to change for the cocktail -- be right back" said Laurie, as she disappeared into the master bedroom, only to emerge five minutes later in a tie-dyed caftan -- a big, shapeless thing that swam all around her thin frame like a sheet billowing in the wind.

"That looks...comfy" I said. "If I knew I would have...well, I don't know, I don't have a caftan."

"Of course you don't. Men don't wear caftans. But my friends and I have reached an age when we can do what we want. Have you ever read that poem about purple hats?"

"Purple hats?" I asked. "No, can't say that I have."

"It's about a woman of 'a certain age' deciding she will wear a purple hat to express her freedom."

"Oh. OK...sounds...different" I said flatly.

"Different?! Stupidest thing I've ever read" said Laurie. "Who wears hats any more? And purple, for God's sake? Please, who looks good in purple? We decided that purple hats were ridiculous. So we wear colorful caftans at happy hour. That's MUCH more practical than a silly purple hat. I might want to be buried in mine. It makes me happy. And is easy to wash. And it was cheap, too!"

That seemed very much in character with the Laurie I knew. Practical, no b.s. I made one of those "hmmm" sounds and was nodding, as if that all made perfect sense, when the doorbell rang.

Two older women came in without waiting for Laurie to open the door, entering in a swoosh of perfume, laughter, simultaneous "hellos," air kisses, and clinking wine bottles as multi-colored caftans billowed around them.

Sally had been there for five years, and Barb was a newcomer like Laurie, having moved in three months ago. They had a routine -- Barb opened the wine, Laurie set out the snacks, and Sally passed around napkins, forks and coasters. They seemed to all be talking at once, not that I had any reason to try to get a word in.

We polished off the first two bottles of Chablis pretty quickly, and by 8pm, when Laurie's grandfather clock chimed on the hour, the third bottle was half empty. On cue they all stood up as the clock chimed, their caftans flouncing around them. I sat there quietly waiting to see what was next - It seemed early to turn in, but since dinner had been at 4pm I wasn't too sure.

Laurie gestured to me. "C'mon." They all started walking to the rear of her condo. It didn't seem like the moment to ask a lot of questions, so I just followed as Barb led the way. She opened the rear sliding door, flipped a couple of switches on the wall, and the small pool in Laurie's back yard lit up and started to bubble as the heater kicked on.

Laurie looked at me - "We didn't have this in New York, did we?"

"We sure didn't. And now that I think of it, my shoulder has been aching from that train ride down here and carrying my shoulder bag."

"Then this will be just right. Make sure you lean up against one of the jets -- it's like a tiny massage from a masseuse that never tires!" And as Laurie was telling me about the jets in the hot tub, out of the corner of my eye I saw Barb and Sally pulling their caftans over their heads. I didn't want to stare, but I was pretty sure they were stark naked, especially since they were stepping into the hot tub.

"I didn't bring a bathing suit Laurie."

She laughed. "Nobody did. Purple hats my butt -- at our age we can skinny dip together in the hot tub whenever we want, and caftans make it easier. Consider yourself a member of the club and get in!"

So I did.

They all pretended not to pay any attention to me as I peeled off my shirt, shoes, socks, pants, and underwear and stepped into the pool. I wasn't too sure where to look -- I mean, I wanted to look at their breasts, bobbing in the water, and everything else, but it just didn't seem...the thing to do. The pool was small, and the three of us were shoulder-to-shoulder, our feet touching, and I was afraid the half-an-erection I felt between my legs would go full mast if I let my imagination -- or eyes -- roam too far.

Of course they started teasing me, Laurie first. "Too bad you had to wait for 45 years for your teenage fantasy to come true, huh? Being in a hot tub naked with a bunch of old ladies, right -- or was it cheerleaders?! We can do that." She put her arms up over her head, her tiny breasts breaking the surface of the water in the pool -- "RAH RAH RAH -- how's that?" They all laughed hysterically.

As awkward as it was, the jets on my back felt good, the warm water was soothing, and I began to relax. It was a little odd anytime anybody moved, everyone bumping into each other with a lot of jiggling, but they were all laughing about it and it seemed like harmless fun.

Barb was sitting next to me and the water jets kept making her breasts bob and shimmer, which I couldn't ignore. In fact, after I started to relax it was almost all I could think about as I multi-tasked, part of my brain half following the conversation, half of my brain following the bobbing boobs with my peripheral vision.

Which is why, when we all climbed out of the pool twenty minutes later, I was mostly hard and bobbing in my own way, attracting sideways glances from them all. They toweled off and pulled their caftans over their heads. I wrapped a towel around my waist, and we went back inside to finish the wine.

"You know Laurie," said Sally, "I think your friend Jim here looks like that stripper we saw in Vegas."

I almost snorted wine through my nose. "Stripper? Vegas?"

They all started laughing. "For Sally's birthday. She had always wanted to go" said Barb.

"I don't think Jim looks like that stripper -- he looks more like my Harold" said Laurie.

"Your 'Harold'? I thought your late husband's name was Sheldon" said Sally.

"Oh, it was. Jim looks nothing like him."

"Well then who the hell is 'Harold'?" Sally was slurring her words a tiny bit.

"He's in the drawer next to you."

Sally turned, opened the drawer in the end table, and let out a whoop as she reached in and pulled out an 8" long, lifelike vibrator shaped like a big dong. "Laurie, you insatiable slut, this thing is a monster!" Sally had a grin on her face.

"Hey, watch what you say about my Harold. He's faithful, HIGHLY reliable, and never complains no matter how hard I make him work! Feed him a couple of batteries and he's content!" Sally and Barb were laughing so hard I thought they might choke, or wet themselves.

"There's a switch at the bottom, right behind his balls -- same as every other man!" That seemed to set them off again, laughing, although when Harold started buzzing they got a bit quieter, as impressed as they were amused.

"He's quite the good friend" said Laurie. Sally ran her hand up and down the vibrator, as if she were contemplating giving Harold a hand job.

"He's kind of nice" she said, "I like the way he feels. Not plasticky."

Laurie's grin turned a bit wicked. "Rub him on your boobs -- he's even nicer!"

"Laurie!" Barb called out, but that didn't matter -- Sally pressed the head of the big rubber cock to her caftan, on the tips of her breasts -- first one, then the other.

"Oh my god, that is great" Sally said. Instantly her nipples were poking through her caftan like little pinkies.

It was right about now that the towel I was wearing became completely inadequate.

My cock was poking straight up and tenting it. The ladies could easily look underneath, as if I were wearing a kilt with nothing underneath.

"Sally, Harold is even better -- you know." Laurie pointed in the general direction of Sally's crotch. "Lick him a bit -- that's what I do. He does his best work down there."

And Sally did. She took the big rubber dong into her mouth, as if she were giving Harold a blowjob, working him in and out a few times until he was nice and shiny.

"That's it" Laurie said. "He should be ready for you now."

I looked over at Barb and saw her squeezing her boob and tugging her nipple gently as she watched Sally. My cock was aching.

Sally leaned back on the couch, spread her knees, and then the hand holding Harold disappeared up between her legs and under her caftan as we all watched. Laurie urged her on. 'Rub him up and down on the outside first -- he can be kind of intense, my Harold can."

It seemed like Sally did exactly that -- and let out a long exhale, a cross between a sigh and a long "ooohhhh." We could see her arm moving, her nipples poking through the fabric, hear the buzzing of the toy -- and I was throbbing, imagining her pussy lips, which I had seen in the pool, glistening wet and puffy with excitement.

"And this is why I said that Jim looks like Harold. Jim, take off that annoying towel -- it isn't hiding anything anyway."

I didn't need any further urging, even though I wasn't quite as impressive as Harold. I untucked the towel and pulled it back, my cock bobbing free. "Sally, doesn't he look like Harold?" Laurie said.

Sally looked right at my cock, then at me as her arm moved back and forth. "Put Harold inside Sally -- that's where he really belongs" Laurie almost whispered.

Sally's arm moved sharply and she groaned, her eyes still fixed on my cock.

I wondered if Sally was thinking what I was thinking -- I was thinking that it was my cock that should have been in her, not a battery powered toy, and when she looked at me again I licked my lips and raised my hips off the couch a few inches.

Above all, I couldn't stand the ache.

I reached down and grabbed my cock, that familiar grip, right hand around the shaft, and slowly stroked it as I looked at Sally -- who's mouth had fallen open slightly as she watched me stroke my dick and fucked herself at the same time with Laurie's toy. In for a penny, I thought, and with my other hand I reached down and started rubbing my balls.

"Barb, don't be rude -- help our guest out!" Laurie almost barked at her. I looked at Barb and nodded, and Barb, sitting next to me, was looking back and forth, watching Sally masturbate, and then down at my cock.

Laurie pushed her further: "Barb, you haven't forgot how to treat a man, have you? I mean I know you are getting old and wrinkly, but you aren't giving up on it, are you..."

I was almost shocked when Barb hissed at her - "Fuck you Laurie, I haven't forgotten and I'm not too old" and she reached across the couch to grab my cock and started tugging.

"He'd prefer your mouth Barb, any man would." Laurie was right -- and Barb, not about stand down, leaned over and took my cock in her mouth -- releasing me for a gulp of wine -- and then went back down on me.

I could feel her breasts under her caftan -- with no bra they hung down on my thigh, the nipples poking into my legs, and I reached down to cup her soft mounds and pinch her tiny buds, making her groan even with her mouth full.

Sally's caftan was now up around her waist, and I could see her curly bush and the toy disappearing between her swollen lips as she slid it in and out of her pussy under her thatch of hair. She was watching Barb suck my cock, and looking at me, and the sight of Barb's lips around my cock seemed to make her fuck herself harder, as if she were watching porn at home in bed.

Laurie's eyes were big -- she seemed to be getting off on directing her friends, and was rubbing her own pussy under her caftan, her voice strained and almost hoarse.

"Rub his balls Barb -- didn't you see him doing that earlier? Every man likes that, too -- they're all the same."

And now Laurie wasn't even pretending to hide the fact that she was masturbating intensely. Sally was whimpering, her hips coming up to meet the toy when she pushed it into her dripping pussy. I could hear her wetness, the squishing when she pulled Harold back and forth, the suction of her hungry wet cunt as it gripped Harold and didn't want to let him go.

Barb was rubbing my balls as Laurie directed, and licking and slurping on my cock. Sally was watching her, looking down at my cock, then at me, into my eyes, trying to take it all in as she shoved Harold into her pussy over and over.

I was going to lose it. Laurie was the ringmaster -- so I addressed her -- "Laurie, I'm going to cum...a lot."

And ringmaster she was. "Barb, swallow it -- you don't know when you'll get another chance. Watch him Sally -- see, I told you he looked like Harold -- here he comes -- feel him inside..." and Laurie herself started to cum, excited by the show she was stage-managing, maybe the power of it all -- "YES, Jim, cum in her mouth, shoot it, let's see it, feed it to her..."

I felt my balls tighten, that surge from deep inside, and I put my hand on the back of Barb's head while I looked at Sally and started to cum, spurting into Barb's mouth once, twice, and a third time. Barb swallowed the first shot, and even the second, but couldn't keep up and the cum started to run out of her mouth and chin and down my shaft into a puddle.

Sally's eyes got big and she started to cum as she watched my cum drip out of her friends mouth, first a shuddering spasm as she clamped down on Harold, then slapping her knees together to hold him tight as the waves of pleasure washed over her, moaning in sharp gasps over and over.

And then Laurie had a second orgams -- as if, now that her class has finished its project, it was teacher's turn to really let herself go. She reached up under her caftan and pinched one of her tiny breasts, worked four fingers in and out of her cunt, and then used her thumb to rub her clit -- her eyes rolling back as she moaned loudly through her orgasm, her toes curling as she drew up her legs.

We all sat there, spent, the sound of heavy breathing filling the air as we all recovered. Laurie slowly took her hand out from between her legs, smoothed her caftan, and licked her fingers, one by one.

"Clean him up Barb. With your tongue. Use the wine." Laurie was still in charge.

Barb poured some wine on me from her glass and licked it off my cock. I thought I saw another shudder pass through Sally, an aftershock that made her nipples even harder, as she watched Barb cleaning me.

We all sat in a daze, the only sounds those Barb was making with her tongue and her small slurps and kisses as she worked on my shrinking cock. Just as she seemed to be finishing the grandfather clock chimed 9 o'clock, breaking the spell, and Laurie decided to bring us all back with a wisecrack.

"Purple hats -- screw the purple hats. Better that we screw each other!" Everyone laughed, more like a bunch of giggling naughty girls this time.

We eventually found our way back into the pool to finish the wine before the evening ended, a lazy, languid end to the night.