Part One
My name is James O’Callahan. As I am writing this memoir, it is November 2025 and I am an 89-year-old man. I will celebrate my 90th birthday in May 2026, God willing. No day is ever guaranteed, but once you hit 80, every sunrise that follows is a bonus. That is especially true in my family. Longevity is a rarity. My father died in his early sixties. My mother made it to 71. My lone sibling, an older brother named Alvin, reached the ripe old age of 73. Becoming an octogenarian was therefore a major feat for me, given my family’s history. Attaining 90 would be absolutely extraordinary.
Simple arithmetic ought to tell you that I was born in 1936. Alvin was born in 1933. We had no sisters, so I grew up in a male-dominated household. Our father was an outgoing, alpha-male type. He enjoyed doing manly things and engaging in masculine pastimes. He hunted and fished and tinkered with cars. He also played high-level amateur baseball until he was into his late thirties. After he died, I found an old scrapbook of his. It contained a newspaper clipping that said he was such a good first baseman that he had once been scouted by the Brooklyn Dodgers. My uncle once told me that Dad “was a flawless fielder but struggled to raise his batting average above .200.” That glaring offensive weakness killed any professional baseball aspirations he may have had.
In contrast, my mother was the quiet and studious type. She always had a book nearby and read our small city’s daily newspaper quite thoroughly from the front page to the back page. She retained plenty of what she read. I was always impressed with her broad-based knowledge. I learned very early on that if you wanted to know something, my mother was the parent to ask. If you needed something built or fixed, Dad was the go-to person. I often wondered how my parents ever got together, but I never asked them. They seemed so different, yet they loved each other deeply.
My brother, Alvin, took after Dad in virtually every way while I inherited my mother’s traits. Alvin struggled to get Cs in school, but he was quite handy with tools. Me, on a good day, I might be able to successfully change a light bulb, but school was as much as a breeze for me as it had been for Mom. Alvin also was socially prominent—especially with the females at his school. He had rugged good looks that I envied. Alvin, as my father often observed, “had smitten girls crawling all over him.” I was okay-looking, but I was definitely not a social butterfly. I had plenty of friends—mostly high-achieving, academic types. All the way through high school I never had a single serious girlfriend until I met Maxine a couple of months before I graduated. Alvin and I were very close despite our differences. He envied my book smarts. I was jealous of his practical skills—and his unrivaled ability to attract pretty girls.
In an era when young people were not openly promiscuous, Alvin was getting more than his fair share of sexual experiences. When he was 12 and I was nine, I accidentally interrupted Alvin and his 11-year-old girlfriend passionately groping each other while sitting on the couch listening to a radio drama. Alvin incorrectly believed I was out of the house, so when I casually walked into the living room, I got an eyeful. Carolyn’s blouse was more off than on while Alvin’s trousers were at his ankles. Embarrassed, he ordered me out of the room quickly while Carolyn tried to cover up her burgeoning feminine possessions. She eventually did, but it was too late: I had already gotten a good look at them. I liked what I saw!
Another time, when Alvin was 16 years old, I looked out my bedroom window into our back yard. I saw Alvin receiving a sexual service from a half-dressed girl whom I’d never seen before. I witnessed the carnal fun long enough to see Alvin experience an orgasm. Moment later, the girl spotted me spying on them. She scampered away quickly, frantically trying to button her blouse as she ran. When Alvin pulled up his pants and entered the house, I expected him to be furious at me. He was the exact opposite. He was smiling.
“That little show was for your benefit, James,” I was informed. “I purposely told Cathy no one was in the house, but I knew you were in your bedroom. I wanted to show you what you’ve been missing by being a bookworm your entire life. You’re 13 years old now, James. By the time I was your age, I’d had fun with at least 10 girls from school.” He paused for a moment and then elaborated, “I mean lots of naughty fun! Do you understand?” I got his drift.
I quietly admired Alvin’s success with females. I heard through the grapevine that Alvin was well known among high school girls for his sexual prowess. I knew for a fact that he had bedded a pretty brunette girl in my class named Janice Schmidt because she often gave me sexy notes to forward to him. They were never sealed in envelopes, so I couldn’t help but read them. Janice often complimented my brother on his “beautiful big dick.” I sincerely worried that Alvin would become an accidental father before he graduated high school.
By the time I was 18 in 1954 and in my final year of high school, Alvin was 21 and happily finished with his formal education. Literally the day after his graduation, Alvin had walked into a local garage—where he knew the head mechanic—and was hired on the spot. He enjoyed the work and was well regarded by everyone he knew. One Saturday, he surprisingly asked me to meet him at the garage during his lunch hour.
He greeted me warmly and got right to why he wanted to see me. “James,” he said. “What do you think of Joyce Carling, the girl I’m presently dating?”
I had only seen her briefly on perhaps three occasions. She was an attractive, 20-year-old black-haired girl who was about 5’6”. I couldn’t help but notice she had a better-than-average figure. That was typical of Alvin. He liked busty girls. Who could fault him for that? She was also a Catholic. My family were Methodists. An inter-religious couple was a little bit unusual for 1954. (Nobody would think anything negative about such a thing these days.) I told Alvin, based on the few times I’d seen Joyce, that I considered her to be quite fetching. I knew nothing about her personality, however, since we had never talked.
Alvin nodded and said to me, “Joyce and I were having a chat last night. She’s concerned that her sister, Maxine, is a wallflower. She’s very bookish and doesn’t socialize much. I told Joyce I had an 18-year-old brother who was the same way. Joyce said that Maxine is 18, too. We figured the two of you ought to get together. Would this interest you, James?”
Actually, the idea did interest me, and I said so. I had given up on dating any of the 17- and 18-year-old girls at my school as they all had characterized me as the equivalent of what would be called a nerd today. I asked Alvin what Maxine looked like.
Alvin was honest in his reply. “Joyce is certainly prettier than her younger sister, but Maxine isn’t too shabby. In fact, I’d say she’s quite appealing. I wouldn’t kick her out of bed, that’s for sure!”
“When have you ever kicked a girl out of bed, Alvin?” I joked.
“I see your point, James,” Alvin conceded with a smile. “Anyway, Maxine seems to be a female version of you. James, she is so focused on academics that she’s never really mingled much with boys. Both Joyce and I think you two would hit it off. You’d certainly have plenty to talk about because you’re both so brainy.”
“Thanks,” I said with a laugh. “There’s a compliment in there somewhere.”
“Of course there is!” Alvin insisted. Then he said something enigmatic. “Okay. That’s part one of the plan achieved.”
“Plan? What plan?” I asked.
“Joyce and I think we should go on a double-date with you and Maxine. Despite you both being excellent scholars, we still think you could learn some things from us.”
“What are you talking about, Alvin?” I asked him. “Courtship techniques, maybe?”
“Well, that’s an extremely polite way of describing fucking,” Alvin said as a big grin overtook his face.
I did not know how to respond to that totally unexpected statement. I just stared blankly at my brother until he offered an explanation.
“You know I’ve been screwing girls since I was 12, right?”
“Based on peripheral evidence, I’ve long suspected it,” I told him.
“Well, it’s true—and it’s fun. It’s the most natural thing in the world. Males and females were designed to complement each other physically. Joyce and I have known each other for four months. We’ve had sex at least a dozen times. It’s very enjoyable, James. You ought to try it.”
“Joyce is a Catholic, isn’t she?” I asked. “I thought the stereotype of a Catholic girl was one who suppressed all sexual desires until she was married.”
“Yeah, that’s the stereotype, but that’s not how Joyce operates at all,” Alvin stated. “She is the most sexually aggressive female I’ve ever known. Normally I have to carefully sweet-talk girls into having sex. Not Joyce, though. It was Joyce who propositioned me about ten minutes after we met!”
“Okay, so Joyce has loose morals,” I concluded. “How does that affect Maxine and me?”
Alvin explained, “Joyce and I were planning one of our regular romantic trysts tonight at a motel we often use for fucking. I jokingly suggested we get a room with two beds and, as a service to our virgin siblings, we could coach them through a sexual encounter. It wasn’t really a serious idea, but Joyce thought it was a wonderful suggestion.”
I just shook my head. It wasn’t a negative reply; it was a signal of utter amazement. I wondered, “Am I to believe that a fairly attractive 18-year-old Catholic girl—whom I’ve never met nor even heard of until five minutes ago—will jump into bed with me tonight while her sister and my brother look on and provide sexual tips and suggestions?”
“Yeah, that’s about the size of it,” Alvin confirmed.
I began to laugh. “So, what’s next? Am I supposed to telephone Maxine out of the blue and ask her to go on a fucking double-date with me, you, and Joyce?”
“Nope,” Alvin said rather smugly. “That’s been taken care of already. Maxine agreed to the plan about an hour ago when Joyce suggested it. The only uncertainty was your participation, James. Would you like to participate? Joyce and Maxine await your reply—Maxine especially.”
“I guess I’d be a damn fool to say no,” I said. “Count me in.”
Part Two
My parents thought it was a wonderful gesture of kindness and family solidarity when Alvin said he and I were double-dating that night with Joyce and her younger sister. (Of course, Alvin mentioned nothing to them about sexual romps in a motel room. He instead told them an outright lie about the four of us all going to a movie together.) My parents were silently fearful that because of my introverted nature I would never find a girl to marry.
Alvin drove himself and me to the Carlings’ house. We arrived at 7 p.m. Maxine was waiting anxiously to meet me. She was all smiles when she saw me. Alvin’s description of Maxine was fairly accurate. In her pale blue blouse and matching skirt, Maxine was actually better looking than I was expecting her to be. Her face was especially pretty. She had a cute button nose, which I found endearing. We politely shook hands. I subtly looked her over from head to toe. To my great delight, I didn’t think there was much difference between Joyce and Maxine at all. I was quite happy with this arrangement. I never expected bedding such a pretty girl would be so easy! It amused me that Maxine’s parents seemed just as thrilled about the double-date as my parents were, and for the same reason: They feared Maxine would never find a husband. (Of course, Joyce had told them Alvin’s lie about the four of us going to an unspecified movie.) By 7:10 p.m., we were headed to the Starlight Motor Hotel in Alvin's car. That afternoon, he had reserved a room there with two beds.
Upon our arrival, Alvin got out of the car alone, got our room key from the front desk, and paid for a two-hour rental. I offered to pay half, but Alvin refused my money. “My treat,” he said with a smile. During the ride to the motel, I sat in the back seat with Maxine. She had slipped her left hand into my right one. She had a sweaty palm—and so did I. “Hey, I’m likely as nervous about this as you are, Maxine.” That comment seemed to relax her somewhat, which, in turn, relaxed me.
When we entered the room, Alvin and Joyce headed toward the far bed, the one closer to the bathroom. By default, Maxine and I cautiously moved towards the bed nearer the door. We had rejoined hands. Alvin and Joyce were embracing each other. Alvin noticed Maxine and me and that we seemed to be awaiting his and Joyce’s instructions.
Alvin separated himself from Joyce for a moment to say, “I find it helpful that before I have sex with a girl that we engage in at least a little bit of romantic activity. Would you agree, Joyce?”
“Yes, absolutely!” Joyce replied. “Kissing is always a good start. I highly recommend it.”
Maxine and I took their advice. We sat on the end of our bed and embraced. I found the warmth of Maxine’s body to be wonderfully sensual. We began with quick kisses that grew longer and longer with each one. Maxine also smelled terrific. She was wearing some type of scent that vaguely smelled of strawberries. I found it very appealing and feminine. We kissed for several minutes.
Eventually we realized that we wouldn’t be getting much in the way of coaching from our respective siblings. Alvin and Joyce were already undressed and lying atop their bed. They too were kissing, but they had their hands occupied with other things. Alvin was fondling Joyce’s breasts—she indeed had a lovely set—while Joyce was busily stroking Alvin’s rising penis.
“I think we’re on our own, Maxine,” I whispered to her. “I have a pretty good idea about what to do. How about you?”
“I think I have the general idea what goes on when a male and a female copulate,” she said. I realized Alvin was right. By the way Maxine phrased her sentences, she was definitely a female version of me. I loved it!
We both undressed quickly and moved to the center of the bed to begin our carnal pleasures. I quickly re-evaluated Maxine’s body. It was considerably better than how Alvin had described it—and even better than I perceived it a first glance! I concluded that a naked girl waiting to be fucked always looks better than a clothed one. Somehow that was a revelation to me.
I took the initiative. With Maxine on her back, I began kissing every possible inch of this 18-year-old virgin, starting at her forehead and finishing with her toes. Maxine giggled approvingly. I was interrupted momentarily when Alvin said, “Hey, you two were supposed to wait for our instructions about this!”
“You both seemed to be busy, so we just began without any coaching,” I noted.
Joyce got to a sitting position on the bed to look us over. She declared, “Yeah, they seem to be on the right track!”
I took a couple of seconds to visually admire my brother’s sexy, nude girlfriend. She gave me an approving smile. Alvin said, “James, let’s make a deal: If you stop eying my girlfriend, I’ll stop eying yours. Okay?”
That remark seemed to startle Maxine who modestly tried to cover her breasts and vagina with her two hands. I laughed and said, “Maxine, this is neither the time nor the place to expect any degree of modesty!”
“My brother’s a smart guy, Maxine,” Alvin said. “He speaks the truth. By the way, I liked what I saw when I was eying you. You’re gorgeous—just like your big sister.” The compliment caused Maxine to blush and smile.
I felt compelled to add, “I enjoyed looking at you, Joyce. Your breasts are especially attractive.”
“Thank you, James,” Joyce replied. “Now please screw my sister. It’s the reason we came here—so you two sexual newcomers could get together for a fuck!”
There were no verbal exchanges between the two beds for the next 90 minutes. I resumed my kissing spree across Maxine’s alluring body. When I got to her vagina, I made a point of fondling it with my fingers and licking it thoroughly. My school chums who claimed to have had sexual experience were divided on whether it was manly or not to provide cunnilingus. Personally, I found it to be both fun and surprisingly tasty! I thoroughly enjoyed the delights of Maxine’s tits when I got to them. After just a couple of gentle sucks on her nipples, I was envying her future babies who would be fed from them. They really were wonderful and incredibly sexy things for me to treasure.
After I had completed my sensual tour of her entire body, Maxine and I kissed some more. Each kiss seemed more passionate than the one before it. Without saying a word, Maxine reached down to my crotch and began exploring my penis. I rolled onto my back to allow her the greatest possible access to it. She treated it like a new and exciting toy, which, I suppose, it was to her.
“I really like your balls, James. I honestly didn’t expect them to feel that way,” Maxine declared. Then she praised my “long, stiff shaft” and the “cute head” atop my dick. When she gave it a quick kiss, I knew the countdown to an ejaculation was under way. I slightly panicked.
“Maxine, I’d better fuck you right now,” I announced. I didn’t explain why, but I suspect Maxine knew without me telling her. I quickly mounted her and shoved my throbbing manhood inside her hairy vagina. Maxine moaned from the sensation of being penetrated by a penis for the first time in her life. I gave her about six rapid thrusts, driving the head of my dick as deeply inside Maxine as I could.
The big moment came—and so did I. For the first time in my life, I ejaculated inside a girl. It was not a little squirt, either. I fired a large load divided into about five spurts. Frankly, I was so overcome with pleasure that I lost track of the total. It was a marvelous feeling. I laid on top of my bedmate for about two minutes. We both were breathing heavily. I didn’t understand why Maxine was. I had done practically all the work—and I felt exhausted.
Seconds later, I heard Alvin let out a groan. He had been fucking Joyce doggy style, which brought to an excellent orgasm. (That position looked like something I’d like to try sometime with Maxine!) I could see the result as he apparently pulled out of Joyce’s pussy just in time to fire his jism on her bum and lower back. Joyce wasn’t so sure, though. “Did you avoid coming inside me, Alvin?” she asked him.
“I think I pulled out in time,” was his uncertain reply.
“I hope so!” was Joyce’s reply to that.
Maxine and I just looked at each other. “Was I supposed to pull out?” I asked her with concern etched on my face. “I did just the opposite. I filled you with my sperm, Maxine. It felt great!”
“Nah, it’s okay, James,” she insisted. “Everyone I know says it’s almost impossible for a girl to lose her virginity and become pregnant from the same sex act. Don’t you worry about it. We’re okay.”
Part Three
Eight weeks later the O’Callahan and Carling families received the startling news that their combined four children would be parents in about seven months. They were flabbergasted, especially the Carlings. They had taught their beautiful daughters the perils of sex before marriage, but their advice had obviously gone unheeded. They risked being scorned at their church because of the promiscuity of their girls—who had been impregnated by non-Catholic males.
At the O’Callahan house, it was a complicated issue. Alvin had recently moved into an apartment. He was earning a good salary as a mechanic, so his situation was simple: Marry Joyce, jointly raise their child, and continue with life. For me, a shotgun marriage at age 18 to a girl I impregnated but barely knew, was not an ideal solution. But this was 1954, not 2024. It was the only solution. Still, it was very odd that my brother’s wife was also my sister-in-law from my marriage, making Joyce my double sister-in-law, I suppose,. The same went for my brother's connection to Maxine, of course. That often required some slow and careful explaining to people whom we met for the first time.
After the double wedding at city hall, Joyce moved in with Alvin. Maxine moved in with me and my family. It was tough for a while on everyone at my house. Maxine and I relied on the generosity of my parents for many necessities. My new bride and I occupied Alvin’s old bedroom. My old room was eventually turned into a nursery for Debbie, who was an absolutely beautiful little girl. My parents and in-laws all adored her. Of course, I loved Debbie from the moment I first set my eyes on her. Maxine and I quickly fell in love, too, which helped our situation considerably.
Maxine and I both finished the final few months of high school so we each earned a diploma. Maxine got a job writing about women’s issues for the local newspaper. She seldom had to venture out of the house, which was a blessing. She became a great mom to Debbie. We eventually had four children together. (Whenever Maxine became pregnant, I’d cheerfully tell my brother, “You were right, Alvin: fucking is fun! Fucking a Catholic girl is especially fun. They’re wild in bed.”) Maxine and I were true soulmates until she died in 2015 from heart disease shortly after her 79th birthday. We had been married for more than 60 years.
I moved into the teaching profession. It was a swift transition from student to teacher in 1954. All you needed was a year at “normal school”—what teachers’ college was known as for decades—and you earned a teaching license. I started teaching a sixth-grade class in a neighboring city when I was just 21. That would be unheard of today. I retired in 1994, at age 58, with a good pension.
Alvin and Joyce’s child was a strapping boy named William. He and Debbie were frequent playmates and became great friends. The Carlings, to their credit, eagerly and immediately befriended the O’Callahans despite the awkward way they met in the middle of 1954. After all, they were all in the same boat.
Oddly, even though Joyce and Maxine became pregnant literally minutes apart, no one ever seemed to think the timing of their pregnancies was somehow connected. At a family function about a decade later, the truth was finally revealed to the four grandparents that their two grandchildren were both conceived just a few feet apart in the same motel room. They were all stunned, especially Mr. and Mrs. Carling, who had a hard time processing the details of a raunchy double sex date—especially one where their shy, virgin girl Maxine had been a very willing participant.
Joyce, Maxine and I had been anticipating the day when the truth would come out. When it did, we were prepared. I gave the signal: “Maxine, Joyce...on the count of three. One, two, three...”
The three of us stood and pointed accusing fingers at my brother as we all shouted, “It was Alvin’s idea!”