A Sex Party Love Story
Romy Holland’s story begins at a sex party in Berkeley, where she had sex with over 40 men—many of them strangers—on the night her future husband, a man she’d only seen online, became her 35th partner. What started as a wild, experimental birthday celebration for her friend Ayla turned into a love story that defied expectations. Romy, a self-described sensation-seeker raised in a Catholic household, describes the event not as a fantasy of sexual conquest, but as an exhausting, emotionally complex experience—filled with flaccid penises, Viagra shortages, and unexpected tenderness, including coaching a virgin through his first time. The real revelation comes not from the gangbang itself, but from what followed: a pregnancy in the early days of her relationship, which led to a traumatic, multi-attempt abortion that left her psychologically shattered. She describes the aftermath as a kind of grief—feeling like a mother without a child, haunted by a maternal drive that had no outlet. Yet despite her extreme openness to sex and novelty, she now finds herself postpartum, repulsed by porn, and grieving the loss of her former hypersexual self. Her story challenges the myth that sexual freedom equals emotional detachment, revealing instead how deeply sex, reproduction, and identity are entangled.
Abortion failed three times with pills for Romy, leading to a traumatic medical and psychological experience that felt like 'borderline psychosis'.
Romy experienced profound grief after her abortion, feeling like a mother without a child, even though the pregnancy was very early.
The gangbang party was not sexually arousing—many men were flaccid, and the environment felt like an exhausting assembly line.
Romy had sex with 42 men, but only 35 were penetrative; the average duration per partner was about 30 seconds.
She met her future husband at the party, asked him out mid-sex, and they soon began a serious relationship leading to marriage and a child.
…and 3 more takeaways available in PodZeus
The Show That Doesn't Talk About Sex—Until Now
Anna Sale introduces the episode by acknowledging that Death, Sex & Money rarely discusses the physical act of sex, but this week is different. The story centers on Romy Holland, who had sex with over 40 men at a birthday party, including the man who would become her husband and father of her child.
The Gangbang That Wasn't a Fantasy
Romy describes the logistics of planning a gangbang for her friend Ayla, who wanted an intense, overwhelming experience. The event was structured around consent, with a focus on men who didn’t need emotional validation from women during sex.
The Reality of the gangbang: Exhaustion, Not Excitement
Romy recounts how the environment was not arousing—many men were flaccid, and she spent much of the night helping them stay hard. The experience felt more like hosting an event than a sexual fantasy.
The Virgin, the Confetti, and the Coaching
“I was like, do you want to try doggy? And, you know, I was like, let's give this guy a new experience. And then he can, the next time he's with a woman, he can be like, I've done doggy, no problem.”
The Man Who Became Her Husband
“Hi, Tony Hawk. I know who you are. I've seen your website and I have a huge crush on you. And I think we should go on a date.”
“He entered me and I immediately blurted out Hi, Tony Hawk. I know who you are. I've seen your website and I have a huge crush on you. And I think we should go on a date.”
“Like I was just scrolling the homepage trying to find something I could look at. And I was like, oh my God, this is disgusting. It looks so medical. Why are there so many... genitals on the screen and they're so like wet looking.”
“I think they're not this bad for everyone, but for me, I got like a fever. I was like body aches, very, very sick. And I just have having to do it over and over and over again. stuck trying to terminate this pregnancy and it wouldn't work.”
Host
Guest
Romy Holland
person
Anna Sale
person
Ayla
person
Tony Hawk
person
Slate
organization
CNC orgy
other
Planned Parenthood
organization
San Francisco Standard
organization
Zoe Aguilé
person
Luke Winky
person
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