Our Dalliances with Deborah

Forty years after their school days ended, four friends reunite. By chance, they discover they've each kept a sexy secret about a certain female classmate.

Every school day for five years, I began my 25-minute journey on foot. Halfway up a steep hill, I met my chum Mickey at his house where his mother always greeted me at the door. We walked the rest of the way to Fountain Park High School together. We frequently passed the time by discussing the recent results of our favorite sports teams. It was a pleasant ritual that abruptly ended on the last day of classes in June 1983. Our paths diverged upon graduation. I saw Mickey exactly three times between 1983 and 2023—although once was at his wedding in 1987. He hadn’t forgotten his old school buddy and sent me an invitation.

Mickey and I, Marvin Ellis, had first met when we were in the same fifth-grade class, but we became close friends in the seventh grade at Cooper Street Middle School. Somehow, we both discovered we had the same interests: sports, military history, and oldies music. We also shared these hobbies with two other friends of the same age, Barry and William. We almost always dined together during lunch periods all the way through high school. I also lost track of those two friends upon graduation.

In 2023, I discovered that Mickey had become rather prominent as an organizer of minor hockey in my Canadian hometown. By chance, the local weekly newspaper, which I seldom read, ran a story about several prominent sports volunteers in our community—and the article mentioned Mickey. There was no way I would have recognized him by his photograph. He was now balding, bearded, and had added about 200 pounds to his 5’10” frame since I last saw him. I made contact with Mickey through the minor hockey association to see if he wanted to reconnect with me. He was delighted that I had tracked him down. We immediately arranged to meet for lunch that Friday. In fact, we had lunch on five consecutive Fridays to happily reminisce and catch up on each other’s life. It was wonderful to do so nearly 40 years after high school ended.

During our fifth lunch, Mickey mentioned that he was fairly certain that Barry still lived in town. He didn’t know about William, though. Anyway, he suggested that the four of us try to get together for lunch some Friday for old times’ sake. I concurred. Mickey called me about two days later to inform me that he had been in touch with Barry who was all in favor of such a reunion. As a bonus, Barry knew where William was now living. Barry got ahold of him. It was arranged that all four of us would meet at a prominent diner for lunch at 12:30 p.m. on the third Friday in May of 2023.

We all arrived at the appointed destination within a few minutes of each other. Smiles and handshakes followed as we waited to be seated. “Aw, what the hell!” I said, and I hugged my old friends, one by one. To the best of my recollection, it was the first time I had ever embraced any of these guys.

“Hey, it’s amazing that none of us has changed; we all look the same as we did on the last day of high school, ” joked Barry, who was still a great kidder. That was pure sarcasm, of course. All four of us 59-year-olds showed the ravages of nearly six decades of life: paunches, wrinkles, receding hairlines, and slowness afoot. William, who had once been a linebacker on the high school football team, was walking with the assistance of a cane. “Bad right knee, ” he explained. “The whole joint is going to be replaced in a few months.”

We were both seated at a table that could hold six people, so we had lots of elbow room. Within seconds, we were rehashing old times and mentioning teachers and classmates whom we had seldom thought about since the 1980s. The waitress surprised us by bringing us a free round of appetizers courtesy of the manager. Mickey and the manager were friends and neighbors, so the latter knew this lunch get-together was a special reunion of old high school buddies.

None of us had been active skirt chasers during our teen years, but Mickey had gotten married fairly young at 23. Barry had been wed a year earlier. Barry’s nuptials had been the shotgun variety. He had impregnated a girl named Norma. They had been forced to tie the knot about a year before Mickey’s wedding because of Norma’s religious upbringing. Barry and Norma were guests at Mickey’s wedding. I couldn’t help but notice that Norma was one of the homeliest females I had ever seen in my life. Their marriage didn’t last long; Barry had been single ever since his divorce. William and I had never been married to anyone. Surprisingly, the group’s discussion diverted to the various female classmates whom we remembered fondly but did not pursue romantically during all those years.

We all seemed to have our individual favorites, but there was some general agreement. We unanimously declared that Sandra Quigley was the best-built girl during our time at middle school while Marissa Ireland held that title in high school. None of us knew what had become of either of those teenage beauties.

“None of us were exactly Cassanovas in those days, were we?” noted Mickey.

We all agreed. “I think we were having too much fun following the NHL, NFL, Major League Baseball, and discussing Second World War campaigns to be interested in girls, ” suggested William. “Silly us!”

“I thought of all you guys when the Boston Red Sox won the World Series in 2004, ” I noted. “We should have celebrated that triumph together.” Indeed, we had all become fans of the Red Sox in middle school. We were all crestfallen to the point of tears when they blew their huge lead in the standings in 1978.

“I don’t want to talk about the ’78 Red Sox, ” Mickey insisted. “That’s a depressing topic. Let’s go back to the previous subject: Pretty schoolmates we should have dated.”

A few more names were quickly put up for discussion. I mentioned Cindy Carpenter, a small blonde girl with a dazzling smile. Oddly, I was the only one of us who even remembered her. It was strange to see that we all mentioned one or two names that none of the other guys at the table could recall. Then I innocently said, “Do any of you remember Deborah Vickers?” The table became very quiet very quickly.

“Wow!” I said, noting the recognition factor in my old friends’ faces, but the sudden silence, too. “That name seems to ring a bell with everyone.” We all sort of glanced at one another not knowing what to say next.

“Maybe we’ve hit upon a common experience, ” Barry suggested. We all started to giggle as if we were 12-year-old girls rather than men about to turn 60.

“I promised Deborah I would never say anything about this, ” I began, “but it’s been 45 years...and I think that Deborah passed away quite a long time ago...”

“What?” my three friends all said in unison.

“I could be wrong about this, but sometime in the early 1990s I saw an obituary in the local daily that said Deborah Vickers had died suddenly in one of the suburbs in Toronto; it might have been Pickering. There was no photo in the obit, but that’s not a common name. If her obituary ran in our paper, she had a local connection. I figured it had to be her.”

“Be that as it may, ” William interrupted, “Marvin, please continue with your personal story about Deborah. I suspect it might be a familiar one for all of us.”

“Okay, ” I agreed. “Here’s what I recall: One day I was at my locker putting away my books when Deborah approached me and asked If I wanted to come to her house to do our math homework together and watch TV. Girls didn’t generally initiate too much contact with me in those days, so I was happy to say yes. I’m sure you all remember that Deborah was a well-put-together girl. I liked to watch her whenever she walked down the hallway...”

My monologue was interrupted by three voices. One said, “Me, too!” A second said, “Yes, indeed!” A third said, “Oh, yeah!”

“Anyway, ” I continued, “Deborah only lived half a block from the school.”

“It was 19 Kensington Avenue, ” Mickey recalled. Barry and William both remembered the address, too. We sensed where this story was headed, so we all started to laugh.

I resumed my story. “When we got to her place and we were alone there, she offered me a cold root beer from the fridge. I accepted. We took our drinks to the downstairs family room and sat together on the couch. Deborah sat so close to me that our hips touched. Then she snuggled up to me and said, ‘I don’t have any math homework and there’s nothing worth watching on TV. Let’s just fuck for fun.’ I was no fool. Of course, I said yes!”

All three of my companions laughed out loud.

I continued my tale. “This was a totally new experience for me. I was horribly afraid I might get Deborah pregnant, so I delayed the actual intercourse for a little while. I insisted that we at least do some kissing and fondling first. We did...and I loved it! When I mustered the courage to feel Deborah’s breasts, she unbuttoned her blouse right away and removed her bra. She had a great set for her age. Deborah said, ‘Here they are, Marvin! I hope you like them!’ I certainly did.”

“Attaboy, Marvin!” exclaimed Brian decades after the fact.

“Over the next few minutes, I had the time of my life licking and sucking on Deborah’s pair of scrumptious goodies. When she started to unbuckle my belt, I knew that the next obvious step was coming. I disrobed in about five seconds. Deborah peeled her slacks off. She gave me a sexy smile—I’ll always remember that—before removing her light-blue panties. Deborah wasted no time spreading her legs for me. I was as stiff as a steel rod, of course. Wasn’t it great to be a teenage boy? I mounted her, slid my dick into her box and pounded away with gusto! I think I lasted 30 seconds. I was so scared of coming inside her pussy that I pulled out way too quickly. I probably could have lasted 40 seconds!”

My lunch companions laughed loudly again at my humble honesty.

“Anyway, I blew quite a large load of semen. I ejaculated all over Deborah’s stomach and her tits. It was the best feeling I had had in my life to that point. I wanted to do it again, right away. I learned that day that a male was not built the same as a repeating rifle.”

“That’s a unique way of putting it, ” Mickey declared.

“Guys, ” I stated, “for a moment, I was afraid that our brief sexual experience had disappointed Deborah. She instead insisted that she had enjoyed it very much. I told her I had likely enjoyed it more than she had.

“We quickly cleaned ourselves up in the small washroom in the basement. While we were gently applying towels to each other’s private parts—a lovely way to conclude things--she asked me to never tell anyone what we had done. She explained that virginity before marriage was a big deal for the girls in her family. She didn’t want anyone to know that she had fucked a longtime classmate one afternoon for nothing more than a bit of off-the-cuff fun.”

I paused slightly and then I said. “I remember one more thing about that day. Once we had gotten our clothing back on, Deborah said to me, ‘Marvin, I actually do have some math homework, but I wanted to fuck you first before my parents got home. Can you stay and help me with it?’ Of course, I stayed.”

William stated, “You are a true gentleman, Marvin.”

“Yeah, I suppose I am, ” I said. “To this day I can’t divide fractions without thinking of dear Deborah Vickers, the first girl I ever screwed. What a sweetheart she was.”

There was another long silence before Barry added, “Guys, I had the exact same experience with Deborah. The only difference was that I was offered a cola by Deborah rather than a root beer and she told me at school that she wanted to work on geography homework! I know Marvin’s story is truthful because that was almost exactly what happened to me, too.”

Mickey raised his hand and announced, “I guess it’s my turn to reminisce about Deborah Vickers! With me it was grape soda and history homework. Other than those two minor differences, I had the same experiences as you two. After all these years, I’d say that Deborah had the nicest tits I ever fondled! They were beautiful, firm jugs...just lovely things to grope! Don’t tell my wife I said that, of course. As a matter of fact, don’t tell my wife any part of this story!”

We all quickly agreed to keep the entire topic of Deborah Vickers to ourselves.

William had not spoken, but he was grinning. He did not volunteer anything at first, but we finally pried the truth from him. “Pink lemonade and grammar homework, ” he admitted. “My story differs from the three of yours in one major way. I did come inside her! That’s how sexually naïve I was in those days. I didn’t consider the option of pulling out of Deborah’s pussy. I certainly didn’t want to pull out; it felt so wonderful having my throbbing dick inside her. Looking back at those days, I suspect Deborah was likely taking a certain important pill to stop her from becoming a teenage mother.”

We all agreed that was a possibility—and probably a likelihood.

I openly wondered how close together our romps with Deborah had taken place. That prompted more discussion. None of us could remember the exact date we each had sampled Deborah’s carnal delights, although I was fairly certain that my romp with her had occurred on a Thursday. (Why I remembered that bit of trivia, who knows?) However, from various peripheral things, we concluded they all must have occurred within the same month—perhaps within the same two-week period! There was only one conclusion to be drawn: Our sweet Deborah, who was apparently overly concerned about virginity, was actually a junior sex fiend!

The Deborah Vickers sex stories were the highlight of that lunchtime get-together. The manager of the restaurant brought out a second complimentary surprise for us: It was a small black forest cake, cut into four sections, to conclude our meal. It had been a bit of a celebration of our lost youth, so a cake was rather fitting for the occasion. We happily told him we’d be back as regular customers to have reunions, at least once per year, as long as we were still breathing.

I was asked by Mickey about Deborah’s obituary. Of course, I replied based on a vague memory, but I recalled it offered few details, other than it said she had passed away suddenly. I solemnly said, “When that phrase appears in an obit, it often means suicide. I surely hope that wasn’t the case for Deborah.” We all nodded our silent agreement.

Then William offered a toast. Together we raised our glasses of ice water as he said, “To the cherished memory of our lovely and promiscuous classmate, Miss Deborah Vickers. We kept our mouths shut until May 2023. We hope you are not disappointed that it is no longer a secret. Thank you from William, Barry, Marvin and Mickey. Rest in peace.”