DES and Male Femininity

As best as I can recall, I started crossdressing 70 years ago and have spent 70 years trying to figure out why. I have read a few theories, but none of them were an exact fit for me except the DES theory, which I have written about here on a few occasions.

Exploring AI, I asked about the connection between DES and male femininity and it returned an excellent summary on the topic including some information that I was unaware of. I think you will find it interesting especially if you are a Baby Boomer, so I am posting AI’s thoughts about DES and us. 

1. What DES Is

Diethylstilbestrol (DES) is a synthetic estrogen first developed in 1938. From the 1940s to the early 1970s, it was prescribed to millions of pregnant women worldwide under the mistaken belief that it would prevent miscarriage and complications. It did not work — and, worse, it caused long-term health issues in those exposed in utero (before birth).

2. DES Sons and Feminization

When a pregnant woman took DES, the fetus — whether male or female — was exposed to very high levels of estrogen.

For males exposed prenatally, researchers later found a number of effects that could be considered feminizing or endocrine-disruptive:

Physical and anatomical effects: smaller genitalia, undescended testes, structural anomalies in the reproductive tract.

Hormonal and developmental effects: evidence suggests some experienced altered hormone sensitivity or differences in secondary sex characteristics.

Psychological and identity aspects: a number of adult “DES sons” have reported increased feelings of gender variance or feminine identity traits, though this is not universal. Some of these reports have been collected in support groups and academic surveys since the 1990s.

These outcomes align with what’s known about estrogen’s role in brain sexual differentiation — meaning that exposure during key fetal periods can influence later gender expression or identity.

3. Social and Psychological Dimensions

In the 1980s–2000s, some men who discovered they were “DES sons” began reflecting on their lifelong sense of being more sensitive, gentle, or even feminine compared to their peers. For a few, this led to cross-gender identification or crossdressing, which they sometimes connected to their prenatal exposure.

While direct causation is impossible to prove, many find comfort and meaning in the idea that their traits have a biological, estrogen-linked origin rather than being merely “psychological” or “cultural.”

4. The Broader Symbolism

Culturally, DES has become a kind of metaphor for:

Unintended feminization through modern science

The fragility of traditional masculinity under biological or social change

The ethics of hormonal interference — a theme echoed in current debates about endocrine disruptors and gender identity.

In feminist and speculative circles, DES exposure is sometimes seen as an early real-world instance of “male feminization by medicine” — not as a fantasy, but as a historical example of how fragile sexual dimorphism can be when hormones are altered.

5. Today’s Understanding

Modern research frames DES as a potent endocrine disruptor, and its history is a cautionary tale about medical hubris. It also intersects with studies of gender diversity, since it highlights how early hormonal environments can shape traits far beyond the visible anatomy.

I don't know if my mother was prescribed DES, but I do know that she had a miscarriage before she had me, so she was definitely a DES candidate. 

And so it goes.

Wearing Ramy Brook dress and Gucci bag.

Șerban Copoț and Cezar Ouatu femulating Alice & Ellen Kessler on Romanian television’s Te Cunosc De Undeva.
Click here to view this femulation on YouTube.