Jumping Judy

Fred Tomasello Jr.
Guest Contributor

On February 23, 2023, the universe aligned perfectly! I had a wonderful chance to establish a personal goal, a record-setting achievement related to masculinity and sexual performance. 

Years ago, I can’t pinpoint the date or year because it was a slow process, my doctor sadly whispered my testosterone was ebbing. Today, this once private stage of dwindling masculinity is blasted on billboards and TV ads, referred to as the dreaded Low-T, a prelude to ED, better known as erectile dysfunction for those of you who don’t have a 2-year degree in acronyms.. 

My spousal relationship gradually went platonic because of ED.

I don’t know if these two maladies are related but when my you-know-what went down, my snoring went up. Separate rooms and opposing political/covid views finally evolved into separate places to live.

Now, at 78, I’m living in a trailer park called Southern Charm RV Resort in Zephyrhills, FL (God I love that name), alone, with two bad knees and nursing my dead wee-knee.

I was shopping for groceries when I saw a sale for Miller High Life Beer and the name Judy from Plant City, Florida came to mind. She loved what was once called the “Champagne of Bottled Beer.” 

“As soon as I get home,” I thought, I’ll try to call her. She’s gotta be in her mid-80’s now. 

My wife and I were close friends with Judy and her husband Jim. The four of us played cards, shared dinners and took dips in their screened-in pool. Jim was a retired US Navy Captain so we enjoyed talking politics and military matters in between flirting with each others’ wives.

Tomasello signing his memoir.

Judy had a loud infectious laugh, a fit, curvy body, pale, lightly freckled skin, perky breasts and thought nothing of kissing others right on the lips. Every time she did this to me, especially when my wife wasn’t looking, sparks short-circuited my brain and my middle knee immediately showed signs life.

In the back of my mind, like a lion ready to pounce, was the delicious thought: “Someday, Freddy, if you ever get the chance, you gotta jump Judy.” 

Years later, Jim died. 

We, mostly my wife Kathy, helped Judy get through the grief process and the life adjustment of living alone. But then Kathy and I moved further away and, as often happens when one spouse passes away, our contact with each other suddenly evaporated.

Driving back from the grocery store with that cold case of Miller next to my crotch, the thought of jumping Judy had me quivering with excitement!

“Here I am,” I thought, “by myself, in a trailer with a king-sized bed, just 30 minutes away from her. God, I hope she’s still living in that same house with the pool, alone and not shacking up with some bloated beer-drinking Bubba with a .357 magnum.”

Pertinent to this story is that, at the VA clinic in Zephyrhills, my new doctor is a sexually attractive Puerto Rican woman built like a Flamenco dancer, tall and slim with shiny jet black hair pulled back on her head into a taunt bun.

On my first visit, she complimented me on my healthy blood work for a 78-year-old man and laughed when I flirted with her in Spanish. 

Damn, it’s good to know more than one language. 

When she heard I was living by myself in a RV resort, she said in an alluring and seductive voice, “Ooh, I’ll bet you’ve got a lot of women after you, don’t you? I’ve heard about what goes on in those places like The Villages! You better be careful.”

Of course, her bright eyes and lurid smile excited me so I blurted out, “You know, you can see right there on my chart that my testosterone level has been low and I’ve had ED problems for years now. So if there’s anything you can do to help me in that area, I’d be very appreciative.”

She stared into my eyes as I silently prayed, “Please, God, inspire her to take me home as her personal project and personally cure me of this fucking affliction! If anybody could charm my snake, it’d be her!”

For a brief moment, like she read my mind, some sort of red flag fluttered in her brain. Her smile faded, we broke eye contact and she stared at her computer screen, seriously perusing my medical history.

“Well,” she said, “there are no contraindications in your chart precluding me from prescribing Sildenafil Citrate. Would you like that?”

My furrowed brow, along with the confused and shocked look on my face told her I had no idea what the hell she was talking about.

She laughed and said, “Viagra! You know about that, don’t you?”


“Oh yeah! I’ve heard of it. Yeah, write me a prescription for whatever the hell you called it. I’ll definitely try it! Thank you. God, I’m so glad you’re my doctor! Thank you for dedicating your life to healing ALL serious afflictions affecting veterans!”

“Shut the hell up!” the voices in my head screamed. “Don’t hit on her again, dumb-ass. You took your best shot. Quit while you’re ahead. Take the free fucking Viagra and go!”

Within a week, the latest, most potent, scientific secret to sexual success was safely stored in a waterproof ziplock bag in the silverware drawer of my trailer, ready to go. 

To supplement this modern “snake charming” chemistry and to ease penetration, as well as in keeping with the highest standards and traditions that made Plant City famous, I discretely ordered, from Amazon, a large tube of strawberry-flavored lubricant. Also, in case my wee-knee failed and I needed to utilize my talented tongue to help my partner achieve the epitome of sexual satisfaction, a primordial orgasmic scream or two, I made sure the strawberry-flavored lube was edible.

God knows we veterans, hell, all of us, have ingested way too many harmful chemicals in our lives. 

As a side note, and I don’t know if this is true for other males because we don’t talk to each other like women do, even though I suffered from ED for many years, my orgasm blessing still works! It’s just as powerful as it always was. There’s a lot less semen and it doesn’t shoot across the room like it did during puberty, so there’s less of a mess. The fact I could still have orgasms gave me hope that I could stay “in the game” and pleasure myself with a nice big O once in a while until ED cures could be found.

But I digress. Back to jumping Judy.

The phone number I had for her rang and rang and finally the message: “The number you have called does not have voice mail service set up.” So I went on Facebook found Judy’s daughter, Joan, and messaged her. Joan wrote she remembered me well from Jim’s funeral, Judy was in the same house in Plant City, was living alone and would love to hear from me. So she called Judy and told her I would call in a few moments. Joan also mentioned she wanted Judy to move back to Iowa where she would be among her kids and grandkids. 

Judy answered on the second ring and our date was set. We were going to lunch at a new place in Plant City called The Brick House.

At shuffleboard that morning, I was jubilant and couldn’t wait for the two games to finish. I went back to the trailer, shaved, showered and generously spritzed on “Obsession for Men” by Calvin Kline, recommended to me by a dapper-dressed widower at the American Legion who was always stumbling around the dance floor by himself in a drunken stupor. He smelled great and told me in a slurred voice that “Obsession was a chick magnet” so I ordered some on Amazon. 

An hour before noon on the day of our date, I called Judy and she said she had just gotten up and was looking forward to seeing me. I asked if she still flew Jim’s US Navy flag and the American Flag over their garage door, and she said no but gave me the house number in case I needed it.

When I arrived, her garage door was wide open and Judy was sitting in a lawn chair waiting for me. She got up and walked towards my truck so I jumped out and gave her a nice, long, warm embrace. She smelled clean, was sharply dressed as always, wore a little makeup and had on her designer glasses but no sunglasses, something she always wore outside. Her driveway to the truck was slightly downhill and her steps faltered a little on the way down to such an extent I had to grab her arm to steady her, just in case. 

“Wow,” I thought, “she still looks good! She’s so excited to see me, her damn her knees buckled after that hug I gave her.” 

I was hoping she would drive because I didn’t know where the Brick House was located. She directed me to downtown Plant City and we found the restaurant and a parking place. I told her to stay seated until I got around to open her door.

 “Why?” she asked, and I said, “because I don’t want any trouble” as I jumped out and raced around to her side, ever the Southern Gentleman.

“What do you mean, you don’t want any trouble?” she asked again, a slight tone of annoyance in her voice. I was holding her arm as she got down from the truck.

“Well, you know, it’s a high step and I don’t want you to slip and sprain your ankle or have any trouble like that on our first time together after so many years.”

Again, her steps were unsteady as we walked towards the front door of the restaurant. The thought crossed my mind, “Her knees aren’t buckling because you’re some hot Latin lover, Freddy. She’s having a difficult time walking. And she’s sober. Hasn’t even had her first Miller yet.”

I held the door open for her and when she walked past, I could see the hair on the back of her head wasn’t brushed or combed. Her hair looked crushed, like she just got up from sleeping on a pillow all night.

The hostess took us to a table in a large back room of the restaurant and the people seated there curiously stared at us. 

One man even mentioned out loud, “You two aren’t from Plant City, are you?”

“I’ve lived here for more than 20 years,” Judy said and the guy responded, “Well, I’ve lived here all my life and I can also tell ya’ll not from Florida. Where y’all from?”

“From Iowa,” Judy responded.

“Where you from?” He asked me. 

I stared at him for a few beats, trying to calm my temper.

“Why you wanna know, you writing a book or something?” I said in a loud voice.

Several tables laughed and the tension eased so I continued.

“I’m from Tampa FL, born and raised. So was my mom. And I also lived in Plant City for several years. A few years ago. Judy and I were neighbors.”

“This building here used to be the city jail,” he continued, “Only now the food’s much better than when I was here.”

Everyone laughed and suddenly we were all friends.

During our meal, Judy mentioned she was way older than me and wasn’t doing well. She couldn’t recover from a common cold as quickly as she used to. Her regular doctor wouldn’t see her any more because she didn’t get her bloodwork done ahead of time as required. She paid someone to come in twice a week to clean her house and maintain her front yard. 

She also mentioned she was lonely and tired of living alone with her dog Buttercup, who was now 18 years old. They always had two dogs but neither one of us could remember the other dog’s name. All her friends where she once worked had died or moved away to be closer to their kids. Judy did say she was moving to Iowa but still hadn’t called a realtor and a mover. She also wanted to find someone to drive her and Buttercup because she needed her car when she got up there. She wanted to move into one of those places advertised on television called, “A Place for Mom” where they fed you three times a day and if her dementia got worse (she soberly admitted she has dementia) they had a place for that too. And, if you needed nursing home care and then hospice, they could handle that also.

“That sounds like a great plan, Judy. If you need any help with any of that I’ll be glad to help you,” I said.

A voice in my head coached me, “When you get her back to her house, if she invites you in, that’s a green light. Be nice, you’re in public now; make her laugh and have a good time in front of all these local-yokels.”

So I did and when we got back to her house she invited me in. 

Fourth of July fireworks were going off in my head as I helped her down from the truck. 

Walking through her garage, I noticed the work desk and the floor all around her car was littered with clutter. Her trash can was blocking the entrance to her home and as soon as she opened the door, Buttercup, her loyal and tiny little friend was there to greet us, excited as a piddling pup again, wagging her tail and anxious to lick me like we were old friends.

“That damn dog remembers you, Freddy,” a voice in my head said. “But when you get Judy inside the bedroom, lock that four-legged bitch outside.”

Dishes, pots and pans were stacked up on both sides of her double sink and Judy said, “you can tell I haven’t been feeling well. I haven’t washed dishes for a week.”

The TV was on some music channel and I remembered she and Jim always left the TV on for their dogs so they wouldn’t be lonely. As long as we knew them, they always had two dogs to keep each other company. Then, after Jim died, evidently, the other dog died too. 

Judy and I sat side-by-side on their big leather couch. She exhaled deeply, slid down, laid her head back, closed her eyes and listened to the music. 

I lecherously inventoried her body. 

Her tits were no longer perky. In fact they seemed to have disappeared. Her former tight belly now sported a sizable pouch, a pony keg if you will, for the copious amounts of Miller she drank every day of her life. 

Her face was still pretty and one of my voices said, “Ignore that body! When you’re having sex, just look at her face. Maintain eye contact until you both explode. You can do it! Think positive. You’ll both have fun!  And you can tell that hot Flamenco Dancer at the VA her “Viagra” prescription didn’t go to waste so please write me another refill!”

Judy loved watching old romantic, black-and-white movies and another voice in my head whispered, “Now’s the perfect time. Make a soft, slow move. Surprise her with a gentle kiss on the lips, then embrace her and keep going.”

Her lips were slightly open and trembling, like sad thoughts were going through her mind instead of some romantic movie. She seemed ready to cry.

Instead of making a move, I asked, “Judy, you OK?”

“No,” she said. “This is all I do. Sit here with Buttercup and watch TV. I’m so lonely. No one calls or visits. I want to go home, back to Iowa. See my grandkids.”

“Well, Judy, we can make that happen and I’ll try to help you all that I can,” I said as I rested a hand on her shoulder. “Next time I come over, I’ll bring my iPad and we can go online and check out some Continuing Care facilities for you to move into near your daughter.”

Another voice in my head screamed, “Kiss her, you fucking moron! You’ve wanted to jump Judy for years! If she responds, kiss her her some more! Set another date and when you come back, bring the damn Viagra and the strawberry-flavored lube! Tell her that story we all had planned about veterans and blood pressure!”

The “story” me and my battle buddies in my brain had come up with, was to tell a woman that the VA had conducted a study on reducing blood pressure. Evidence showed a strong relationship between orgasms and their effect on lowering high blood pressure. Even if partners didn’t want to have traditional sex, in the patriotic intent of helping veterans improve the quality and longevity of their lives, Judy, or any other volunteer, could help veterans achieve the best orgasms possible, especially including those aided by gentle prostate stimulation. That, or just a quick, simple blowjob, would be a hell of a lot better and more effective than “Thank you for your service!”

“OK, here we go,” the choir in my head commanded in unison.

So I made my move.

“Judy, you know we’ve been friends for years and for every one of those years I’ve been very attracted to you. Before I leave today, I’d like for you and I to stand up so I can give you a big hug and a real kiss.”

I stood up and so did she.

We made warm eye contact and somehow we both felt like we were center stage, being watched – Her husband Jim’s spirit watching us right here in his own house, my wife Kathy watching us telepathically from Naples, Florida, and the damn dog watching us right here on the couch.

“Oh, I’ve got a cold,” she frowned, “and I don’t want to give it to you.”

“Judy, that doesn’t scare me. I’m fearless.”

We hugged. She puckered up and gave me a quick kiss on the lips like I was her son or something.

The sexuality of the moment extinguished, like a Sidewinder missile shooting down a giant Chinese spy balloon. Agape replaced Eros, and the tidal wave of love and caring we all shared for years broke over us, she with her husband Jim and me with my wife Kathy, in that same room, on that same couch, on so many occasions, and in front of that same dog, who just stared up at us, with a puzzled look on her face. 

That powerful moment silenced me, shamed me and shut down all my voices.

After another long, warm hug, I told her I’d call her tomorrow, we’d meet again and work on getting her home to Iowa.

As I drove home, the voices returned.

“Well, you fucked that up, Freddy Boy! There’s still that other woman you met at the poker game, the short one with small hands and big ass; the one who checks off every box in your ‘ideal woman’ list. Work on her next.”

And finally, that one persistent, mean and heartless Drill Instructor voice screamed at me, “You dumb fucking pussy! A real Marine would be fucking her brains out twice a day!”

For two following days I called her home a couple of times a day.

Judy never picked up the phone.

I messaged her daughter and told her that if I could help in any way, to call me, that there were millions of mothers in Florida living alone who needed help. And if Judy ever wanted to go out with me again, to please call me.

No one did.

A week later, I messaged Judy’s daughter.

“What’s the latest on moving Judy home to Iowa?”

“Still working on it,” she replied.

“Aren’t we all?” I thought.

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