15 SEPTEMBER, 2021

Dear Harry,

It took a patient, sweet, kind-hearted, and easily exploited girl—the girlfriend of a friend’s girlfriend, to ease my awkward and self-doubting self out of my virginity. I was 19, nearly 20! From what I hear, that would seem laughably retarded to today’s young people, who apparently “hook up” with random others with barely a second thought. I wish you were around to tell me about your first time! I imagine things were still more restrictive in your day. I could quite imagine, if you shared that reticence I’ve been describing, that you were still inexperienced when you married Peggy. (Okay, I’ll admit this might seem tasteless and intrusive, but frankly I’m long since done with being timid. I’m long since done with being the good boy you brought up!) Was the wedding night the first time for both of you? Were you as clumsy as I was?

You likely would not remember my friend Paul from Venezuela, though I’m pretty sure you met him. Dark hair? Wavy? He was one of those friends I’d bring home with me because he had no family to go home to in England in the shorter holidays. A year behind me at Caius, he was far ahead in the kind of experience I lacked—and sorely needed. His pretty, cheerfully promiscuous girlfriend at the time was Mickey, and on more than one occasion he prevailed on me to help free up the flat she shared with her friend Debbie, to allow him to enjoy an afternoon of undisturbed libidinous pleasure with his inamorata.

So I took Debbie out—to the cinema, perhaps—and we became friends ourselves. Sort of. I’m ashamed to say I may have considered myself a cut above this good person. May have? No, I did. Paul and I were university students, after all, and the girls were town girls, with jobs in local stores. (I’m aware, of course, that attitudes of this kind do not speak well of the privileged young man I was). There came a time, however, when Paul—and Mickey too, I suspect—decided it was time for their friend Peter to grow up and they conspired to invite me over for a cup of tea one afternoon, and shortly afterwards announced they had evening plans, leaving me and Debbie free run of the flat. It was pretty obvious to both of us what was expected.

We sat on Debbie’s bed. I took courage in both hands and began a fumbling exploration of her body. She seemed perfectly willing to allow it, unhitching her bra beneath her blouse and allowing me, too, to kiss her as I fumbled further. Breasts. Had I ever touched a woman’s breasts before? Jeannine’s? Would I have dared? The result of this delight was predictable in my nether regions, Harry, and Debbie’s fingers proved skillful in further stimulating the arousal. Then, with much awkward wriggling and repositioning of bodies, she guided my fingers into the mysterious triangle of silken hair between her thighs and opened herself to a breathless adventure into that unknown territory.

By now a tangle of body parts and half-discarded clothes, we fell back on the bed and Debbie squirmed out of her panties, dumping them over the side of the bed as she spread her legs for me to lie between and slip myself into that now moist and beckoning interior. And I lost it. My recently rampant cock went suddenly limp as a wave of self-doubt and lack of confidence surged up and disempowered me, along with a flood of shame. There she was, this patient, lovely girl, all ready and willing, eager, even, for me to enter into her most private sanctum… and I couldn’t do it.

“Sorry,” I said. “Oh, my God, I’m sorry.”

And Debbie said, “It doesn’t matter. Honestly, it doesn’t matter,” she insisted. “It happens all the time.”

Which was kind of her, but it did nothing to relieve the intensity my embarrassment and shame. What mattered was that it had happened not to other men but to me. Incredibly. I had been so hot with desire, oozing, literally, with the urgency of that long imagined, long craved moment and then… nothing.

Well, Harry, as an old man now myself I can readily imagine that the same thing does happen to a great number of young men on their first attempt. I wonder even, since we’re being totally honest here, if it might have happened to you? I wonder, too—I know, sorry, this is totally inappropriate—if Peggy was your first time? And what had you done with all the sexual urges you must presumably have felt before, since puberty, as I had done?

Might as well say it here. I only ever saw your penis once, by accident. You were standing naked in the caravan and I burst in unexpectedly. I was probably no more than eight or nine years old and I was shocked by the size of it, the dangle, the thicket of hair. The startling image froze inside my mind and haunted me, even though you covered yourself quickly with a towel. So it was no more than a glimpse. But it is strange, isn’t it, that I remember this image so clearly even today?

Anyway, to get back to my story: I’m happy to report that the disaster with Debbie was quickly followed by recovery and triumph. Debbie's kindly ministrations proved exactly what was needed to regenerate what I’d lost, and she managed to guide me gently into that place I had so lusted after for so long. Virility restored, I buried myself joyfully inside that tunnel of love and ploughed away like a real man till I was done. Which was probably much too soon for Debbie—I’m sure I had as yet no idea that a woman, too, could have an orgasm. But I was relieved and grateful beyond words, as you can imagine, to have finally endowed her with my unwanted virginity. The door—if you’ll forgive the rather crude image—was open. It would never close again.

Your son, Peter