Sexual Humor

How Not to Put on a Condom

That first time having sex wasn’t what I had expected.

I attempted to fall in love with “Kathy.” I really wanted to. But if I couldn’t have love, at least I might have sex.

I was a twenty-three-year-old virgin; I’m doubtful Kathy was. It was 1966, and I was in my second year of medical school at the University of Nebraska, where Kathy was a nurse.

We had dated for a couple of months, and our physical intimacy was becoming, well, progressively more physically intimate. I thought We are going to have sex. I am going to have two-person sex.

I wanted to make that first time extraordinary, but how to make that happen stumped me.

The only sex education I had was from an eighth-grade classmate who told me about the movie regarding menstruation the girls in our class had watched in the fifth grade. And then in high school, my mother told me several times, “Don’t go getting some girl pregnant. You’ll have to marry her, and you’ll be miserable the rest of your life.”

That was all the sex education I had except for the bits and pieces of misleading information I overheard in the locker room after football practice.

Photo by Reproductive Health Supplies Coalition on Unsplash

The FDA had approved “the pill” for birth control only a few years before. Although it eventually revolutionized women’s health care, it had not yet transformed it in Omaha, Nebraska.

Kathy’s doctor didn’t buy into the sex-for-pleasure idea, and he would not prescribe the pill for her. But his disapproval was not going to stop me.

It was a different time. No one said the word “pregnancy.” Instead, it was either “in a family way” or only “P. G.” School teachers had to resign at the first sign of a baby bump. The women clerks in the drugstore wrapped Kotex boxes in plain paper in the back of the pharmacy before putting them out on display.

Pharmacists concealed condoms in locked drawers behind the pharmacy counter in the back of the drug store. Only later did “tickler” condoms and “enhance your pleasure” lubricants begin to appear in vending machines in the bathrooms at truck stops.

I knew I had to be prepared for my great sexual awakening. I walked into the small drugstore in the Dundee neighborhood of Omaha. I slowly meandered to the rear of the store to the pharmacy, and I hesitated along the way to examine a few tchotchkes in which I had no real interest.

By my hesitant walk, everyone in the pharmacy must have known why I was there. We all obviously knew what women carried out in those plainly wrapped boxes.

The older, grey-haired pharmacist, in a starched white jacket as stiff as his personality, looked so professional that he could have been in an ad for arthritic pain relievers. I approached him nervously and said quietly, so as not to be overheard, “I need some condoms.”

“I’m sorry. Could you speak up?” I can but I don’t want to.

“I said, ‘I need some condoms.’” I knew he had heard me the first time.

“What size do you want?”

They come in different sizes? Confused about how to answer, I recalled locker room comparisons. I replied, “Average,” although I wanted to add maybe a little more than average.

“Rubber or lambskin?”

They can come in lambskin? I had never heard them called anything but rubbers. I confidently said, “Rubber.”


Again, not knowing how to answer, I responded, “Yes.”

“Reservoir tip?”

“Yes.” If his goal was to make me uncomfortable, he succeeded. Do the tips come in sizes, too? I think I will need a large one.

Kathy shared a one-bedroom, efficiency apartment with another nurse, “Barbara,” in a complex filled with nurses and medical students. The night of the anticipated event, with her roommate safely asleep in their bedroom, Kathy and I lay together on their beaten up couch and began to get intimate. She lay across my right arm, the one I had just started to use to write prescriptions.

I unfastened my belt, unzipped my jeans, and wriggled out of them and kicked them off at the foot of the sofa. By then, because Kathy lay on my right arm, it had gone to sleep and I was unable to move it in any way but to flop it.

Clumsily, I removed my clothes and Kathy’s from the waist down.

I needed to retrieve the condom from a pocket in my Levis. My jeans lay in a pile, just off the end of the narrow couch. I stretched my toes to recover them. My right arm was useless. I fumbled with my left hand — the one I’d learned to call “nondominant,” now quite understandably why — to get the foil package out of my jeans pocket.

Success. I now had the condom in my left hand which was nearly as worthless as my right hand. I could not tear the package one-handed, so I resorted to using my teeth.

I now had the condom secured on my penis that was so hard I hardly recognized it as mine. I think I’ve got it in! Maybe it isn’t. I’m not sure.

Photo by Charles Deluvio on Unsplash

I’d never put a condom on a banana before, much less my penis, but this was no dress rehearsal. It was the main event.

My clumsiness embarrassed me as I struggled to roll the slippery condom onto my erect penis with an untrained left hand. It kept popping off before I could get it unrolled. Perhaps I should have bought one without the lubricant!

I was pretty sure that with all that lubricant on the head of my penis, if I labored much longer I would cum before I got the damn thing on.

“Don’t try this at home” did not apply in this case.

Did all of this come easily to other men? Men fix machines; they should know how to condomize a penis. If only I had jacked off before my date with Kathy.

I now had the condom secured on my penis that was so hard I hardly recognized it as mine. I think I’ve got it in! Maybe it isn’t. I’m not sure.

As I began to move my hips in an often imagined way, Kathy’s roommate, Barbara, walked sleepily out of the bedroom, through the tiny living room where we were and over to the kitchenette. She cracked open a Coke, lit a cigarette, and took several drags before she walked back into the bedroom. She did not acknowledge our presence.

It was all over quickly.

The following morning I stared at myself in the mirror and examined my chest hairs to see if they had grown. I swaggered a smile across my face. I had finally crossed to the other side.

But inside my head, I could hear the haunting voice of Peggy Lee singing, “Is that all there is? Is that all there is, my friend?”

I broke off the relationship with Kathy shortly after that, but my loneliness led me back to her. Was Kathy my default sexual pleasure? The baseline to which I would keep returning?

After a few weeks, I called Kathy once again to ask her out. She resisted, and then made me promise that if she started seeing me that I would not end it as I had before. Desperate to have someone in my life, I agreed. But I immediately realized that I had committed relationship malpractice, and I called it off again. Permanently.

In 1988, a few months after I came out as gay and Doug and I had lived together, I received several phone messages on my answering machine at home from a woman whose name I didn’t recognize.

I disregarded the messages, thinking it was one of my psychiatric patients who ignored my rule: Don’t call me at home. Call me at the office unless it is an emergency.

She persisted in her attempts to reach me. One evening she called while I was home, and I answered.

A young woman asked, “Are you Dr. Olson?”

“I am.”

“Did you graduate from the University of Nebraska Medical School?”


“In 1968?”


“Did you know Barbara?”


“I think you’re my father!”

The list of women with whom I could have fathered a child before I married my wife was very short: Kathy.

Stunned, for a moment, I could say nothing. Then I stuttered, “I don’t think that’s possible.” In fact, I knew it couldn’t be true.

The shock of what had just happened made me sound much more tentative than I actually felt. My uncertainty was a reflection of how to respond to her.

The list of women with whom I could have fathered a child before I married my wife was very short: Kathy.

As we talked, her disappointment grew increasingly evident, and anger impregnated her voice. I knew she thought I was lying. She abruptly hung up without saying goodbye. I never heard from her again.

I knew I’d never fucked Barbara. I had barely fucked Kathy.

The previous story was adapted from outtakes of the first edition of Finally Out: Letting Go of Living Straight with the permission of the publisher.

Available for purchase here.

An excerpt of Finally Out can be found here.

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Gay father; Psychiatrist; Award-winning author FINALLY OUT. Chapter excerpt here: Top writer on Medium. Not medical advice.

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