, September 2023

Charles Humphrey was the big dopey kid in Carl’s gym class, only he wasn’t really a kid anymore, having been left back a couple of times on the way to eleventh grade. He was 6’4″ and well over 300 lbs, drove his parents’ old Chevy Caprice Classic, and talked real slow like he was from Kansas, even though he grew up right here in Massapequa.

“Whatcha doin’ for prom?” he asked Carl, both waiting their turn at bat in the area designated as the “dugout” of the gym class “softball field”, which was not at all a proper diamond but just some old bases on an expanse of intramural field dust—

“Prom?” Carl asked.

“Sure. Junior Prom. I should have been more specific.”

“I’m not going.”

“Why not?”

“I don’t have a girlfriend.”

“Neither do I.”



After a brief lull—

“Aren’t you gonna ask me what I’m doing for prom?” Charles asked.

“What are you doing for prom, Charles?”

“Going to a party in the Hamptons.”


“Yep. A lot of people are skipping prom and going right to the Hamptons, where everybody’s going after prom for parties anyway.”

“And there’s more than one party?”

“Well, yeah, but I’m going to one specific party. A bunch of us put in money to get a suite at one of the hotels out there.”

“Who put in money?”

“Me. Some other guys. My brother, who’s 32. Probably a couple of girls, maybe.”

“And where in the Hamptons is this?”

“Just out in the Hamptons, is all I know.”

“And which hotel is this at?”

“I forgot. I have it written down at home.”

“And in which one of the Hamptons is this hotel? East Hampton, Westhampton, Hampton Bays—”

“I forgot. But I have that written down too, I think.”


“Hey, I have an idea.”

“What’s that, Charles?”

“Since you’re not going to prom, why don’t you ride out to the Hamptons with me and my brother? It’ll be a blast. You can just give us a few dollars for gas, and a few dollars for the suite. I’ll pick you up at FoodTown at nine o’clock on Saturday night.”

Carl knew better than to trust Charles Humphrey—not that he was a liar or a bad dude, but he was like a little kid in a grown man’s body—yet, if he was telling the truth, and there really was a party at a hotel somewhere in the Hamptons where there would be girls who didn’t go to the prom—

“Sure, Charles,” Carl said.

“Don’t be late. My older brother will be with me, and he might get mad if we have to wait for you.”

*     *     *

By that afternoon, Carl had forgotten his conversation with Charles until overhearing two girls in math class talking about how the junior prom was lame. Then they asked each other which party they were going to out in the Hamptons, which, apparently, was a difficult decision, as there were “so many good ones to choose from”. As much as Carl wanted to find out the location of even just one of these parties, these were A-list popular girls, both very cute, and he knew that everyone, including the teacher, Mr. Klein, would laugh at him for even attempting to talk to girls so far out of his league, let alone ask them where the after-prom parties were, which, supposedly, everyone but he already knew, so he kept his mouth shut.

*     *     *

Friday morning in gym class, in the softball “dugout”—

“So, are you still going out to the Hamptons tomorrow night?” Carl asked Charles.

“Yep. And so are you, right? I’m picking you up at nine o’clock at FoodTown.”

“Yeah, I’ll be there. Where in the Hamptons are we going again?”

“All’s I know is that we’re going to the Hamptons.”

“Which one?”

“I don’t know. One of them, I guess.”

*     *     *

Knowing it would be far easier to sneak out all night and sneak back in the next morning than trying to convince his mother for permission to get in a car with some guy from school and his 32-year-old brother and go to a hotel out in the Hamptons, where there would quite obviously be alcohol present, Carl devised a plan to make it appear that he was following his usual Saturday night routine of late, which was to stay in his room all night watching TV and speaking to no one, then have light timers shut off the lights and TV at 3:00 am. Then, when he got back the next morning, he would casually stroll back into the house under the premise that he’d just gone out for a minute to drop something in the mailbox at the corner, and they would have no clue that he’d been gone all night.

On Saturday morning, he rode his Centurion Accordo 12-speed up to the Pergament hardware store and purchased two light timers, then went next door to the Genovese drug store and purchased a three-pack of Trojan lubricated condoms, a pack of Marlboros, and an orange Bic lighter. Then he rode up toward the Carman Mill Motel, to the one-aisle liquor store with the steel cage in front of the counter, owned by the old Asian guy who never asked for ID, and bought a four-fifths pint of Southern Comfort.

*     *     *

The first part of the plan worked to perfection. His mother and “stepfather”, Rick “The Dick”, went out at 8:00 and saw him in the kitchen just before they left, and he appeared to be going nowhere. He waited until they were gone before getting in the shower, then, at 8:30, leaving the television and lamp on in his room that the timers would shut off at 3:00, he jumped on the Accordo and rode up to the FoodTown shopping center.

After locking his bike on the rack, he went through the automatic door into the foyer with the gumball and vending machines and bought a can of Coca-Cola Classic, which he cracked open and took a long swig, then refilled with SoCo. Back outside, he sat on the curb, feet in the FIRE LANE, sipping his canned cocktail and smoking Marlboros. By 9:20, he hadn’t seen a single Caprice, and by then he knew that Charles wasn’t going to show.

It had crossed his mind to take the two-hour train ride out there, where the land was narrow and the stations and hotels probably right in town—but there were lots of Hamptons on the L.I.R.R. Montauk branch—Westhampton, Hampton Bays, Southampton, Bridgehampton, East Hampton—and he had not heard where any of these supposed parties were taking place.

After tossing his empty Coke can and buying another from the machine, he rode up to the Massapequa Park train station and locked his bike on the rack. He took the escalator up to the platform, mixing some SoCo into the second can of Coke during the slow ride up, and sat on a bench facing the eastbound tracks that ran all the way out to Montauk.

The headlights of an eastbound train soon appeared in the western darkness. Minutes later it pulled into the station, but, by then, he had already given up the idea of going out east and was content to sit and watch the trains go by with his SoCo, Coke, and Marlboros, imagining the better places these vessels traveled in either direction without having to spend much time here—

The doors slid open. He didn’t look directly at the disembarking passengers, but he saw their shoes pass by on their way to the escalator, until one pair caught his attention—pointy, shiny, black high-heels with a pair of dark-stockinged legs and a leather miniskirt very much like his eighth-grade English teacher used to wear—

“Carl? Is that you?”

“Ms. Orlando?”

She still looked good for a woman in her forties, and sexy as ever. Carl was surprised she even remembered him. He once carried a box of phonics workbooks out to her Corvette after school, an event that fueled a thousand fantasies—

“Why, Carl, it’s so good to see you. How are things? You’re in, what, eleventh grade now?”

“Yeah, just about done with it,” he said.

“Isn’t tonight the junior prom? Why aren’t you there?”

“I didn’t have anyone to ask.”

“Oh, Carl, I’m so sorry.”

“That’s okay, I’m used to it.”

“How old are you now?”


“Are you waiting for a train?”

“No. I was supposed to get a ride out to the Hamptons for a party, but they didn’t show. Then I was thinking about taking a train out there, but at this point it doesn’t seem worth it.”

“Do you mind if I sit?” she asked, the two now alone on the platform—

“Sure,” he said.

She sat close next to him on the bench and retrieved a pack of Parliaments from her Yves Saint Laurent handbag—

“Also,” she said, “if you don’t mind, I’m going to have a cigarette. Would you like one?”

“No, thanks, I’ve got my own.”

They both lit up.

“I didn’t go to my junior prom either,” she said, exhaling, red lipstick on recessed filter—



“Why not?”

“None of the boys asked me.”

“I thought you would be the first girl they asked.”

“Well, I was a bit of a nerdy bookworm back then. I changed my style after that.”

“Did you wear glasses?”

“Big, thick ones, like Coke bottles. Thank God for contact lenses. By the way, I also know that you used to daydream about me in class.”

“How do you know?”

“How do you think I knew?”


“I always thought you were a handsome young man.”


“Of course.”

“I thought you liked T.J. best.”

“He was cute, but you were handsome, and more of a gentleman. And now you are a fully-grown, handsome man.”

“Thanks,” he mumbled—

“I have an idea—why don’t we have our own junior prom back at my place? That is, if there’s nowhere else you have to be—”

*     *     *

She still had the red Corvette, which was parked down in the station lot with a ticket on the windshield that she shoved into her handbag. The vehicle’s interior smelled like stale cigarettes and perfume. She stomped the pedals with her high-heels as the Corvette roared to life—

“Buckle up,” she said, then stick-shifted out of the parking lot and across Sunrise Highway, then down desolate Park Boulevard glowing amber under the yellow streetlights, Phil Collins’ “In the Air Tonight” on the stereo—

“Are you a virgin, Carl?”

“Uh, I got a hand job once, if that counts for anything—”

“You are no longer a virgin when you have made love to someone. Have you ever made love to someone, Carl?”

“No, I guess not, Ms. Or—”

“Carl, you are a man now and my date for the junior prom, so please call me ‘Susan’.”

“Yes, Susan.”

She drove swiftly and skillfully, heading east on Merrick Road towards Nassau Shores, both smoking cigarettes, exhaling into the salty June breeze blowing in through the open windows as they passed John J. Burns Park—

“Don’t you just love smoking?” she asked.

“Yeah,” Carl said, exhaling.

*     *     *

She lived in a bungalow on the Great South Bay with a pool in the yard. The interior was classy, clearly not a house inhabited by children, decorated with big Picasso-like paintings and abstract wood sculptures. The bedroom door was open, and, inside, was a bed large enough to fill with her and several men, covered with sheets of black satin.

“We are going to do this right,” she said, foregoing the tour and instead directing him to move the furniture in the living room out of the way to create a dance floor, offering no assistance with the heavy lifting. He liked her directness, it was so much easier than trying to figure out what was going through the heads of girls his own age. After the leather couch and the teak coffee table were out of the way, she led him to the garage for a folding ladder, then up to the attic for a genuine disco-used mirror ball, which he hung from a hook already on the middle of the living room ceiling. She then dimmed the lights, and the room, with the nice hardwood, had become a dance hall for two—

“Now, let’s get you dressed,” she said. “Into the bedroom and strip down to your underwear. I have some old tuxes in the closet, one of them should fit.”

There was no hiding his boner when he was down to his boxer shorts.

“So adorable,” she laughed. “Now, into the closet.”

The walk-in closet was enormous. There was a small section of men’s suits, tuxedos, jeans, t-shirts, Hawaiian shirts, khaki shorts, leather slacks, and a pair of nunchucks.

“You’re not married, right?” Carl asked.

“Dear God, no,” she laughed. “I was once, when I was nineteen. I had become pregnant, but then I lost the baby. The whole thing didn’t even last a year. Afterwards, I swore I’d never do that again and went to college. But that was all a very long time ago, so you can relax knowing that I am now completely unattached in every way, which is the way I like it, and the way it shall stay.”

She fingered through the tuxes on the rack until picking one—

“Try this one,” she said. “It’s for tall and large.”

“Whose clothes are these?”

“Honestly, I don’t remember who they belong to. They are just things that men have left here over the years and never came back for. I must have scared them away. It sometimes comes in handy to have some extra men’s apparel lying around, this being one such occasion. Now, go out to the bedroom and change. I’ll stay in here and get dressed.”

Staring at himself in the mirror, tux baggy and clip-on bowtie askew, he felt ridiculous and began to worry that this was some sort of gag. He then sat on the black satin sheets and waited until she finally presented herself, looking magnificent like Elizabeth Taylor in her red ball gown, elbow-length gloves, big diamond earrings, dark stockings, and red high heels. She twirled for him, then handed him a box containing a fake corsage—

“Pin me,” she said, holding the box open. He didn’t know how to do this and became nervous—

“Like this,” she said, showing him how, then having him practice it three more times until he had it down.

“These things are important,” she said. “Next year, at the senior prom, your beautiful date will appreciate that her man knows how to pin her corsage. Women appreciate men who know what they’re doing. Confidence, Carl, is the key to unlocking doors. Now, take me to the junior prom.”

Arm-in-arm they proceeded to the living room, where she went over to the turntable and selected the soundtrack to Saturday Night Fever, dropping the needle on the Bee Gees’ “More Than a Woman”, then heading out to the dance floor and waiting—

“Well, aren’t you going to ask me to dance?”

“Sure,” he said, walking up to her and asking, “Would you like to dance?”

“Dear God,” she said, hand on hip. “Is that how you ask a woman to dance? Try it again, but this time look me in the eye. Tell me I look pretty this evening. Then ask me to dance. And say my name. Women like it when men say their name.”

Carl looked up and met her eyes, then started feeling lightheaded. He held out his hand and said, “Susan, you look wonderful tonight. Can I have this dance?”

May I have this dance. Ask again.”

“Susan, you look wonderful tonight. May I have this dance?”

“Why, thank you, Carl. I’d love to.”

Carl, though, held up his hands and said, “I don’t know how to dance.”

“Don’t worry about dancing. Just let go of your inhibitions and let the music flow through your soul.”

“I don’t know how to do that either.”

She took his hands and said, “You are here with me, and your life starts tonight. Hold on to me, Carl, and let go of everything else.”

She leaned backward and he did the same, but not too far since he outweighed her by sixty or so pounds, and together they started spinning to the sweet falsetto harmonies of the brothers Gibb, looking up at the mirror ball, then back at each other, laughing, spinning faster—

“That was wonderful, Carl,” she said as the song faded out. “Let’s take a break, I need a cigarette.”

They smoked overlooking the slow reflections of the mirror ball on the dance floor, Yvonne Elliman’s “If I Can’t Have You” on the hi-fi—

“Pay attention to your date,” she said. “Don’t start drifting away like you used to in class. Talk to her. Let her know you’re having a good time. Show her you’re interested.”

“I’m having a wonderful time, Susan. Are you enjoying yourself, Susan?”

“Don’t overdo it with the name thing. Just relax, look into her eyes, and let your heart speak for you.”

He looked into her eyes and, again, felt lightheaded—

“Susan,” he said, “tonight is very special to me, and I’m honored that you’re my prom date. I’ll never forget this night for the rest of my life.”

“Good, but drop ‘for the rest of my life’. Clear and concise. Economy of words. ‘Susan, this is special to me. I’ll never forget tonight.’ Something like that. Anyway, now it’s time for our special dance, so let me change the record.”

 She put on Bob Seger & The Silver Bullet Band’s “We’ve Got Tonite”—

“This is my song,” she said, then turned towards him and waited, and he offered his hand without saying anything—

“Good, Carl,” she said, allowing him to lead her out to the dance floor, where she positioned his hands on her waist and draped her bare arms around his neck. They swayed to the slow piano chords, butterflies aflutter in Carl’s stomach as he looked into her eyes, and the way she was looking back made him feel like he was about to start crying, which is when she whispered, “Kiss me, Carl—”

He leaned in slowly and met her lips, tasting her lipstick as he slid in his tongue—

“Don’t jab,” she said. “Slide slowly, gently—”

He tried again, and, this time, she didn’t stop him. Slow and passionate they kissed through the song’s building crescendo, and, towards the end, she started kissing more aggressively, positioning his hands on her bottom, leaning into his erection—

“Do you want me, Carl?” she whispered.

“Yes,” he whispered back.

“Tell me you want me.”

“I want you, Susan.”


“I want you, Susan.”


“Susan—I need you—”

“Come with me,” she said as the song ended, leading him to the bedroom, where she ordered him to remove his clothes—

“All of them?” he asked.

“Yes,” she said, then went into the closet and closed the door.

Carl unbuckled and removed the tuxedo pants, then jacket and shirt, and, finally, boxer shorts and socks. Fully erect, he stood at the foot of the bed staring at the doorknob for what seemed an eternity before it finally turned and she emerged wearing a Playboy bunny suit, including puffy white tail, big rabbit ears, collared bowtie, fishnet stockings, and high-heels—

“I used to waitress at the Playboy Club on 59th Street,” she said. “That’s how I paid for my first year at NYU. I only worked there a year, but they let me keep the outfit, and I’m proud to say it still fits.”

“Wow—I mean, you look stunning, Susan.”

“Thank you, Carl,” she said, twirling, then inviting him to sit on the bed, while she remained standing—

“Before we go any further,” she said, “you must understand that when a woman gives a man oral sex, she is doing it to enhance his stimulation prior to intercourse, and not as a finishing act. So, I am going to do this briefly, which is all a man needs, but it is imperative that you do not finish. Is this understood, Carl?”

“Yes, Ms.—Susan—”

“Now, lie back and close your eyes—”

It felt warm, soft, and moist, and made him harder than he’d ever been. It was only a minute before he opened his eyes again—

“Good, Carl,” she said. “Did you bring condoms?”


“Good. A man should always be prepared. And be sure to always wear one, at least until you find that special woman you are going to stay with, if you’re into that sort of thing.” She winked. “Where are they?”

“In my pants.”

“Get them.”

He showed her the strip of Trojans in the apricot-colored wrapping, still connected at the perforations—

“A woman can tell if a man knows what he’s doing by the way he puts on a condom,” she said.

This made him nervous, but he was able to tear one from the strip and get it open without much difficulty, then started rolling it on—

“What are you doing?” she asked.

“Uh, putting the condom on?”

“You didn’t stretch the tip first. You have to make room at the tip or else the fluid has nowhere to go and will spill out the back. And do you have any lubricant?”

“Like Vaseline?”

“No. Like KY jelly. Vaseline, yuck. Really, Carl, you must be prepared at all times. The lubricant on lubricated condoms is never sufficient, especially if it’s been in a guy’s wallet for a while. Buy a small tube. Nothing to worry about this time, though, I have a wide assortment of oils and jellies.”

She showed him how to stretch the tip, then, after rolling it on, he chose a cinnamon oil, some of which rubbed onto his scrotum, making it warm and tingly—

“The man should proceed slowly from here,” she said. “He should kiss her again, tenderly, and allow her the opportunity to insert it for you. If she doesn’t, look into her eyes and tell her you want to make love to her—at this point, we are beyond subtlety and will want to be explicit about our intentions. A more experienced woman will know exactly what she wants; however, many of the young, inexperienced girls you will be with, especially in high school and early college, will not know what they want. They will be confused and conflicted. They will want to, but they won’t want to. Some will change their mind at the last moment. If you hear the word ‘no’, immediately stop whatever it is you are doing. Show concern, ask her if everything is okay. Do not try to convince her to proceed or change her mind if she says ‘no’. Respect her. Now, if you are with a woman who gives consent, look into her eyes one last time, then move slowly to insert. If properly lubricated, it should slide right in. Slowly and gently, go as deep as you can, then, start motioning back and forth—slowly at first, but gradually increasing speed until you establish a comfortable pace for both of you. Don’t go too fast like you’re trying to catch a train. Motion and location have more to do with it than size, as long as it isn’t too small and can’t reach said location. Your penis, Carl, is more than adequate in size, and would make most women happy if used properly. Keep motioning; you will be able to tell from her sounds whether or not you are pleasing her. You should also be able to tell when she is approaching climax, and you should try not to climax until she gets there. Are you ready, Carl?”


“Say my name, Carl.”

“Yes, Susan.”

Gently she lay him down on top of her, the black satin sheets feeling nice against his nudity. She was about to unsnap her bunny suit, but stopped—

“This,” she said, “has come to be known as the ‘missionary position’, which is how some Christian ministries believe is the only proper way to copulate under the eyes of the Lord. Do not buy into this nonsense, Carl. It is a wonderful, classic position, perfect for your first sexual encounter, but there are many great ones, so do not be afraid to experiment, and keep an open mind for things she may suggest that you had never thought about trying.”

He looked into her eyes and she nodded. Slowly he put it in, she not offering assistance but nodding him on, moaning when he was inside her, then whispering, “Make love to me, Carl.”

And he did. She said “slower”, “faster”, “not yet”, and “a little longer”, then, finally, between moans, “Now, Carl, release me, let me go…”

They climaxed together. When both had finished, she nudged him away and reached into the nightstand drawer, retrieving a pack of Parliaments and taking one out for each—

“We’ll spoon after this,” she said, exhaling, both now sitting up, an ashtray on the bed between them—

“I don’t know what that is,” Carl said, examining the recessed filter of his Parliament—

“Most men don’t. We’re just going to kiss and cuddle and touch each other’s bodies, without having sex. Carl, it is important to note that being someone’s lover is more than the main sexual act. There is the before, there is the during, and there is the after. And, Carl, when you do make love to a woman, you stay the night and have breakfast with her in the morning. Do not be one of those jerks who gets dressed and runs out the door as soon as it’s over, even if it is with someone you don’t particularly care for. Don’t ever leave unless she tells you to. Always be a gentleman. Is this understood, Carl?”

“Yes, Susan.”

*     *     *

She awoke at first light and put on a pink satin robe with fuzzy white trim, then went into the bathroom. She was in there for a while, taking a shower and blow-drying her hair, which she set in big hot curlers. She emerged in a pink satin robe with fuzzy white trim, then went into the sitting room just inside the closet, and noticed in the makeup mirror her lover watching through the open door—

“You may enter, Carl,” she said without looking.

He stood in the doorway, naked and erect—

“Some men are turned on watching a woman do her hair and makeup,” she said, penciling her eyebrows. “I see that you are one of these men.”

“Yes,” Carl said.

She stood and turned like she was going to kiss him, but stopped short of his lips—

“Take me, Carl,” she said, “but no kissing or oral, I don’t want to smudge my makeup.”

Carl put on a condom, tip properly stretched, and lubricated himself with a mentholated oil that was cold and tingly, which he liked even better than the warming cinnamon. She lubricated herself with coconut oil, then, still in robe and curlers, bent over in front of the makeup mirror, looking back at him over her shoulder—

*     *     *

A short time later they were back in the Corvette, roaring east on Sunrise Highway, past the shopping mall and the sanitarium into Suffolk County, to the South Bay Diner in Lindenhurst, her favorite breakfast establishment—

“Why is it your favorite?” Carl asked.

“Because I don’t know anyone in Lindenhurst,” she said.

*     *     *

She ordered hard boiled eggs, toast, bacon, and coffee. He ordered the “Full House”—pancakes, waffles, French toast, bacon, hash browns, toast, eggs sunny side up, orange juice, and bottomless coffee. Afterward they lit cigarettes and ashed them on their plates, Carl, not a fan of the recessed Parliament filters, smoking one of his Marlboros—

“So, Carl, what are you going to do with your life?”

“Go to college upstate. Then, I don’t know.”

“After college, I highly recommend experiencing a different part of the world. London. Paris. Bangkok. Seattle. And don’t waste your four years of college dating some sweetheart who still sleeps with stuffed animals. Party hard with your male friends and get it out of your system. Then, after college, see as much of the world as you can. If you are planning on getting married, wait at least until you’re thirty. People who get married in their early twenties usually wind up divorced.”

“Like my parents,” Carl said.

“I am sorry to hear that, Carl.”

“It’s okay, Susan.”

“I have one last reading assignment for you—”

She reached into her handbag and retrieved a pink notepad and a red pen, writing in sexy cursive:

“On the Road”
by Jack Kerouac

“Read it,” she said. “It will change your life.”

*     *     *

With the Montauk sun rising behind them and the Bee Gees’ “How Deep is Your Love” on the stereo, the Corvette roared west on Sunrise Highway, back towards the Greater Massapequas. Both smoked cigarettes, but neither spoke. Carl could feel her and the night drifting away. In a few minutes they would say good-bye, and then he would never see her again. He was in tears by the time she pulled up to the curb at the train station, where the Accordo was still locked to the rack—

“Don’t be sad,” she said. “Your life has just begun.”▪