Part One
Growing up in the 1950s, there were certain moral expectations that applied to teenagers—especially girls. Although they were chased, they were supposed to be chaste. (That was a pun that Dad like to repeat.) Sex before marriage was considered irresponsible and shameful for girls—but not necessarily for boys. It was a blatant double standard, of course, but it served society well. Unwed motherhood and single-parent homes were rare in those days.
I, Warner Prince, was born in Canada in 1939, just a few months before the Second World War began. My father was a skilled machinist, a job that was deemed so valuable that it exempted him from military service. Three of his brothers took up arms in the fighting, however. Two made it home safely; the other, Michael, was killed on the stony beach in Dieppe in August 1942. Dad seldom talked about Michael or about the war in general. I think he resented losing a beloved sibling in an ill-planned raid that had little chance of succeeding. Anyway, Dad got on with his life and instilled into his three children the values that he had been taught by his parents. One of them was directed at his lone son—me—which insisted that I respect all females regardless of their age—especially once they and I reached adolescence.
In the spring of 1951, when I was in the sixth grade at Sir Arthur Currie Elementary School, I did my best to abide by these ideals. There was a pretty, slender, towheaded girl in my classroom named Jennifer Barrett. To put it politely, she was ahead of all of her peers in the puberty department. One day, completely out of the blue, Jennifer approached me at afternoon recess and asked me some blunt questions. “Do you like me, Warner? I like you very much. You are such a smart and handsome boy. I want to have a boyfriend—and I want it to be you! Would you like me to be your girlfriend?”
That revelation was more than stunning to me. Jennifer had been a classmate of mine since the second grade. Apart from the normal verbal interaction one would expect between two schoolmates, I could not remember even a single, long conversation I had ever had with her. Nevertheless, I eyed this pretty girl and determined I would have to be a fool to turn down her request, so I happily said, “Certainly, Jennifer. I like you, too. I think I would enjoy being your boyfriend. I agree.”
Jennifer smiled. She promptly gave me a long and affectionate hug, which startled a few of my classmates who were standing nearby. Nobody else my age, as far as I could tell, was particularly interested in the opposite sex quite yet. (Of course, that would change in a hurry as all my classmates were either 12 years old or would be that age by the end of 1951.) I got into the spirit of things by hugging Jennifer in return. I liked the personal contact very much. I took the liberty of kissing Jennifer’s left cheek. She upped that gesture of fondness by giving me a quick kiss on the lips. This was undoubtedly the best recess I had ever had in all the years I’d attended school!
When our kiss stopped, Jennifer cautioned me. “Warner, please remember I have to be a good girl. My mother insists on that. I spoke to her last night. I told her what I was going to ask you. She is okay with me having a boyfriend, and I’m allowed to hug and kiss him, but nothing more. She says I absolutely have to be a good girl. She was only 17 years old when she had me. She doesn’t want me to make the same mistake in my life that she did with hers. Do you understand what I’m saying, Warner?”
I lied. I said I understood perfectly. Actually, I didn’t understand very much of what she had said at all. Twelve-year-old boys were not necessarily a worldly bunch in 1951. I got the talk—from both my parents—later that night after they asked me at the dinner table if anything new and exciting had happened at school that day, and I told them what had occurred at recess. That certainly was an eye-opening discussion I had with Mom and Dad. I also suddenly found it very flattering that pretty Jennifer Barrett thought so highly of me.
Being a boyfriend to a sixth-grade girl in 1951 consisted of plenty of hugging and kissing whenever we could do it. (We had to be quite secretive about it at school. Overt displays of affection between boys and girls were frowned upon by the staff. Holding hands seemed to be the absolute limit.) Jennifer and I had been an item for about three weeks before I even invited her to come to my house. We were one of the rare families who had purchased a television set. I was proud that my family was a trend-setter, so I wanted to show off a bit. My parents also wanted to meet Jennifer, too. Therefore, it was arranged that Jennifer would join us for dinner one evening in late April.
Upon seeing her for the first time, Dad was surprised that Jennifer, at age 12, possessed more than a bit of a womanly figure. (After Jennifer had left our house, he took me aside and quietly reminded me about the qualities of a gentleman and how respecting girls was a big part of it, “despite the obvious temptations that Jennifer presents.” I understood the subtle message: I was to keep my hands to myself as far as certain areas of Jennifer’s torso were concerned.
Remarkably, I had managed to do that for the first few weeks. Our hugs were wonderful, but I remembered Jennifer’s “good girl” warning and I always respected it. Whenever we embraced, my hands never got higher than the bottom of her ribcage. However, about a week later during recess, when Jennifer and I were hugging and kissing rather passionately under a staircase in a secluded part of our school, she herself lifted my hands a few inches upward and placed them on her young, soft breasts.
“I know you’ve wanted to do this for a while, Warner,” she said with a smile. “I respect you for respecting me, but I have desires, too, and I want to know what this feels like." Then she put her hand in a strategic spot below my beltline and explored my anatomy. Let’s just say her deft and sexy touches affected my self-control. After about 90 seconds of being groped, I had to excuse myself, rush to the boys’ washroom, and tidy up my lower regions and my underwear the best I could under less than ideal circumstances. I got back to my classroom just in time and saw Jennifer grinning at me with an air of achievement. I think she was proud of what she had accomplished.
After school, Jennifer said to me, “I know what happened to you at recess. I still think I’m a good girl, though, as we haven’t fucked yet.”
In 1951, the verb Jennifer used in that sentence was rarely heard in public—even in schoolyards. My father said such language was only uttered “by the dregs of society”. Therefore, I was taken aback when Jennifer—a 12-year-old girl—said it aloud to me. I didn’t dwell on it, but I did tell Jennifer that I had enjoyed the sensation and intimate experience of her touching me “down there” until I lost control of myself. She shrugged her shoulders as if to indicate it was no big deal. It had been a big deal to me, however—a very big deal.
Part Two
Jennifer remained my steady girlfriend almost all the way through high school. That was nearly a unique achievement among my peers who tended to “play the field” and who wondered why I wasn’t doing the same thing. Many of them suspected that Jennifer and I had an unusually intimate relationship for a high school couple in 1957. I wished it had been the case, but it absolutely was not. Although we had engaged in plenty of pawing, fondling and groping, Jennifer was still completely a “good girl” by how she defined that term as a sixth-grader back in 1951. In our ongoing six years together as a couple, we had never had sexual intercourse and neither one of us had even glimpsed the other’s private parts. Those were pleasures reserved for married folks, we had been told by our elders who supposedly knew what was best for us.
Then, one Friday in the spring of 1957, when Jennifer and I were both 18 years old, she approached me after school to tell me something of great importance. We went through the usual hug with our hands subtly drifting to forbidden places when Jennifer suddenly stated, “I think I know a way of getting around the rules.”
“Rules?” I asked her. “What rules?”
“You know, Warner! The rules I told you when I was 12 years old, about what my mom would allow me to do and not do if I had a boyfriend.”
“Oh, yeah: No fucking allowed because good girls don’t do that sort of thing before marriage,” I whispered to her while rolling my eyes.
“It’s still a good rule, Warner,” Jennifer insisted. “By the time my mother was the age I am now, she had a one-year-old daughter—me! Anyway, I think I've spotted a loophole so we could be very intimate without breaking the rules.”
“I’m all ears,” I noted. “What’s your idea?”
Jennifer took a noticeable deep breath before giving her startling answer. It was, “You could fuck me up my bum, Warner.”
This came as a complete surprise to me. Even within the puritanical society of the late 1950s, I had heard of such a bizarre practice, but I thought it was downright weird and highly unnatural. I also knew it was mostly done by homosexual men—and not heterosexual couples.
“How did you come up with that idea?” I asked Jennifer.
She began, “I was speaking to a classmate of mine, Eva Whitehead. Her boyfriend is 20. He’s in the army. That’s how the two of them fuck without fucking in the traditional way. He likes it and she likes it, too. Best of all, there’s no chance of pregnancy occurring. It’s the best of both worlds. I’m willing to give it a try. Do you want to try it, Warner?”
I did not have to think too long about it. “It beats infinite celibacy,” I said. “When and where do you want to do this?”
“I hadn’t thought about that yet,” Jennifer informed me.
I had a eureka moment. “Hey, I have the right place and time,” I told Jennifer. “Let’s return to our old school tonight. My friend Philip is a volleyball referee. I know he is officiating a tournament at Sir Arthur Currie Elementary School this weekend starting tonight. The school will be open for spectators. It’s free admission. We’ll pretend we’ve come to watch the tournament, but we can sneak out of the gym anytime we please and find a vacant classroom or some other place to do our bum-fucking. We’ll have plenty of privacy. No one beside the two of us will be in any part of the school other than the gymnasium.”
Jennifer laughed, but agreed. “Good choice, Warner! That’s really a fitting site—the place where we became a couple. I’ll meet you there, near the front door, at about 7 o’clock.”
Part Three
At the appointed hour, I met Jennifer at the spot she dictated. She seemed more eager than I was to engage in what the law still considered “an unnatural sexual act” and “sodomy.” Before we went inside, Jennifer opened her purse to show me she had come prepared. She had picked up a few items based on her friend Eva’s advice and experience: Vaseline and other lubricants. I gave her a slightly quizzical look. I didn’t even ask the question, but she poetically answered what their purpose was. “It doesn’t matter if it’s thick or thin. Vaseline will get it in! Hey, that’s what Eva says. I suppose we’ll find out very soon.”
To make our ruse somewhat believable, we watched about ten minutes of a volleyball game featuring 12-year-old girls. It had already started when we found a place to sit. Jennifer was obviously restless. She said to me, “Warner, I think we’ve made our presence known long enough. Let’s see if our old sixth-grade classroom is open.” She led the way, remembering the route easily, as if it were still 1951. Sure enough, the door was closed but not locked. We opened the door and flicked on the lights. It hadn’t changed much in six years. The best part was that there was still a fairly large but secluded vacant spot to conduct our private business. It was located between a wall and the end of the row of closets where students hung their jackets and stored their lunches. In order for us to be seen, someone would have to enter the classroom, walk 15 feet and look to his/her left. That was unlikely to happen with school having ended three hours earlier. We turned off the classroom’s lights except for one that illuminated the approximate area where I would be penetrating Jennifer’s anus.
We moved to the hard-to-find area. To begin our fun, we hugged and groped a little more thoroughly than usual. For the first time in my relationship with Jennifer, she was able to see my penis as I swiftly stepped out of my trousers and underwear. It was semi-erect. “Finally, Warner, I get to see your dick!” Jennifer said excitedly. “I really want to play with it!”
“Be careful!” I warned her. “Remember what happened six years ago! I don’t want a repeat occurrence!” Jennifer heeded my warning, somewhat at least. She tugged my shaft and caressed my testicles for only about 30 seconds. My rod was no longer semi-erect; it was completely stiff.
“Your turn to disrobe, Jennifer,” I told her. I was hoping that I’d get a complete look at Jennifer in the nude, but she only removed her skirt and her panties. Her tits would remain a concealed mystery. She had a hairy vagina that I moved forward to stroke. Jennifer balked for a moment until I said to her, “You played with my private area, so I get to play with yours.” I caressed her pussy for about half a minute as well—just to make things even.
Jennifer then opened her purse and took out the jar of Vaseline. She scooped out a sizable wad and spread it over the shaft of my penis. I wasn’t expecting that at all—but I liked her touch. Then she handed me the jar. She instructed me to spread an equal amount on and around her butt hole. I was quite happy to do that for her. I felt my penis get even harder—which I thought was impossible a minute earlier. We borrowed the teacher’s chair so Jennifer could hold onto its arms while she bent over in something close to a 90-degree angle. Somehow it worked out perfectly. I could stand comfortably while shoving my phallus into my longtime girlfriend’s presumably tight bum. It wasn’t her desired vagina—but it was close enough.
I guided the head of my Vaseline-covered dick towards her Vaseline-covered anus. “Here goes!” I warned her. “This is new to both of us, so I’ll begin gradually.”
I pushed slowly. Her anus opened wide enough to accept my stiff penis. I could hear Jennifer groan slightly. It was difficult to ascertain whether this experience was pleasurable or painful for her, or perhaps both. It was pleasurable for me, without a doubt, so I shoved more of my six-inch manhood into her bum. I grasped Jennifer’s hips to give myself more leverage to thrust deeper until I was inside her as far as my dick could reach. Then I started to move it forward and backward. Twenty-four hours earlier, I would have thought that this type of intercourse was strange and somewhat disgusting. However, the pleasure I was deriving from bum-fucking Jennifer Barrett was off the charts. Jennifer indeed had a tight bum, so the application of Vaseline certainly helped me take her anal virginity—if there was such a thing. I only lasted about three minutes before I fired a large dollop of warm goo inside Jennifer’s beautiful behind. It must have been a substantial amount, because some of it trickled onto the classroom floor when I pulled out of her. (Before we vacated the room, we made sure we tidied up that mess with several tissues taken from the teacher’s desk.) For fun, I also groped Jennifer’s tits. As usual, they were still well hidden under her brassiere, a white blouse, and a pink sweater.
“Warner,” Jennifer said with a tone of disappointment, “I think you are stretching the boundaries of what we came here to do.”
“Oh, I figured giving your tits a good feel was part of the deal,” I said. “Sorry if I misunderstood. Nevertheless, you have great breasts, honey.”
About 15 minutes had elapsed. We had started and finished the most exciting sexual adventure in our lives thus far during that brief time. We restored the classroom to how it looked before we entered. We returned to the gym to watch more volleyball. It was hardly a world-class sporting event, but it was free entertainment.
We sat in the small area of bleachers amongst the players’ friends and family for about an hour. By that time, I was completely revived from my ejaculation—and I wanted more anal sex from Jennifer. “How about another bum-fuck?” I whispered into her left ear.
“Okay, if you insist,” she replied. I got the distinct impression that I was more enthusiastic about our second frolic of the evening than Jennifer was.
We discovered that all the classrooms were now locked, thanks to the school’s custodian having finished his janitorial tasks. It occurred to me that we could have easily been caught by him; we must have timed our romp just right. “No matter,” I said. “Let’s go under the staircase where we used to make out together in the old days.” We did. The area was dimly lit, but there was enough daylight coming in through the window to allow me to see what I was doing. Jennifer just had to get on her knees and raise her derriere upward. I lubed up my dick and Jennifer’s anus and gave her a more intense bum-fuck than the first one. It was thoroughly enjoyable. This time I lasted about eight minutes before launching more of my semen into a bodily crevice where it wasn’t going to do what it was designed to do.
Over the next dozen days, I penetrated Jennifer with the “anal alternative” three further times. Once it was when we were alone at my house, once it was when we were alone at her house. The last—and final time—was at a vacated playground just after dusk. There, beside the swing set, I figured I gave Jennifer the best ass-fucking she had gotten in my five romps with her since the night of the volleyball tournament. I lasted the longest and undoubtedly fired the biggest load of cum into her butt. I was quite happy with myself and was willing to keep doing this indefinitely.
Jennifer had other ideas, though. “I’m putting an end to this, Warner,” she said as we got dressed. “It’s nothing personal; I just don’t especially like anal sex. I was hoping to grow to enjoy it like Eva does, but I don’t. Let’s just go back to being celibate, okay?”
To me, there was no going back. I wanted to be a sexually active male. Jennifer was beholden to her beliefs about celibacy and virginity. There was no room for negotiation or compromise, so we stopped seeing each other about a week later. Amazingly, in six years of dating, I never did actually see Jennifer's tits.
When one door closes, another one often opens. It didn’t take long for me to find a girl who was more open-minded about sexual things—especially anal sex. I hooked up with Eva Whitehead who had recently split up with her boyfriend from the army. We both enjoyed frequent anal fucking. In fact, it became an important part of our relationship.