Famous Age-Gap Relationship: Oliva Nuzzi (18) and Keith Olbermann (52)

Keith Olbermann and Oliva Nuzzi

Ryan Lizza, the CNN analyst and former fiancé of Vanity Fair’s former West Coast editor Olivia Nuzzi, posted “Part 1: How I Found Out” on his Telos News Substack. In the post, Lizza shared that when Nuzzi was a teen, from her “unhappy home in suburban New Jersey”, she randomly “messaged” 52-year-old Keith Olbermann, the former MSNBC host. Consequently, Nuzzi moved into Olbermann’s Manhattan apartment, where they began an age-gap affair. Lizza wrote:

Not that long ago, I had helped her untangle herself from an unusual relationship with Keith Olbermann, the former MSNBC host. She had messaged him out of the blue. They started talking, and soon after, she fled her unhappy home in suburban New Jersey and started living with Keith in Manhattan. 

Rhetorical question: Did Nuzzi initiate the affair with Olbermann because she was looking for a loving (age-gap) relationship, or was she looking for a Sugar Daddy, or both? I ask because Lizza posted that Olbermann paid for Nuzzi to attend Fordham University. (The Lincoln Center campus, I presume.). He dressed her in designer dresses. He draped her in Cartier. And he paid for her luxury West Village apartment. Lizza wrote:

He paid for her to attend college, outfitted her in Tom Ford and Hervé Léger dresses and some $15,000 worth of Cartier jewelry. Later, he covered her rent and furnished her apartment in a doorman building in the West Village. 

There are a number of conflicting reports about exactly when Nuzzi and Olbermann’s age-gap affair began; however, the correct report is that it began when Nuzzi was an 18-year-old high school student at Middletown High. 

Olbermann shared with the New York Times that 18-year-old Nuzzi moved into his apartment in a “Trump building on the Upper East Side”, where they had two Maltese puppies and an “marriage-y” age-gap relationship.

Ginia Bellafante related in the New York Times piece “In This Scandal, the Journalists Are the Story” (Nov. 21, 2025):

Mr. Olbermann had lived with her for a while in a Trump building on the Upper East Side, “if you can believe the irony,” he told me. He said he had discovered her writing on Twitter, where she provided witty political analysis as a student, and he wondered if she might be a good fit for the TV show he had hosted in those days.

They met for dinner. She was 18. He was 52. Instead of working together, they began dating, he said. They got two Maltese puppies and James Thurber-inspired tattoos. “It was marriage-y,” Mr. Olbermann said. “It was very much an at-home-with-the-dogs sort of thing.”

However, a day after their conversation, Olbermann shared with Bellafante that he and Nuzzi didn’t have sex until after Nuzzi turned 19, which is extremely hard to believe. 

It’s worth noting that prior to his relationship with Nuzzi, Olbermann was 47 when he had an age-gap affair with 23-year-old journalist Katy Tur. Nuzzi was 25 when she began dating 44-year-old Lizza. Nuzzi was 30 when she began a “digital affair” with 60-year-old Robert F. Kennedy Jr.. And when Nuzzi was 16, she recorded “Jailbait”, which included the salacious lyrics like: “Bad things happen when you hear my name / Deny your attraction, but I’ve got no shame / Sixteen will get you 20 — I’ve got you locked for life” 

THE CUT’s Sex Diaries: The NY Party Girl (23), Ricky in Finance (43) and Sex Tape Fetishes

New York Magazine’s THE CUT posted: “This Week’s Sex Diary: The Party Girl Whose Date Sends Her Money and Gift Cards” (September 5, 2025)

The Party Girl is a 24-year-old New Yorker - “born and raised in the city” who has: “no money and no rich parents,” because her parents are “struggling artists”. Consequently, she’s “on a strict budget”, she tries “not to spend any money during the day,” and at night, she tries: “to get as much paid for as possible”. The Party Girl “barely” has food at home, and she can’t afford to order GrubHub, because it “will cost too much money.” Therefore, if she can’t get a free meal, she eats, like, peanut butter with “a few sticks of celery”.

The Party Girl is the co-owner, with her sister, of a beauty line. The Party Girl focuses on “relations and marketing”; thus, she keeps samples from the beauty line in her bag. She shared that being a party girl is: “conducive to getting our product in the right hands, since I go out every night.”

However, when the Party Girl goes out, unsurprisingly, she’s not strictly business. For example, at a rooftop party with an actress friend, the Party Girl met a vacationing Frenchman. After some “dancing and getting steamy”, she “pulled[ed] him into the bathroom”, where they “fuck[ed] against the door” before she had a “powerful orgasm”. However, the Party Girl, an apparent feminist: “Never got his name. Ha!”

Most relevantly for our purposes, the Party Girl is in a “situationship” with 44-year-old Ricky, whom she described as “very wealthy, actually fun, funny, [and] cool”. “He’s in finance, obviously.” They met at Soho House in Dumbo when she was 23. Of the age-gap situationship, the Party Girl shared: “Sometimes we fuck, sometimes we don’t.”

On cue, after sexual activity, Ricky sends the Party Girl gifts (e.g., $300 via Venmo, Amazon or Seamless gift cards). The Party Girl opined that Ricky sends her gifts after sex, because “he’s a nice guy.” However, she admitted that their age-gap situationship “sounds suspicious”. The Party Girl shared:

And just because he’s a nice guy, he’ll do things during the week like Venmo me a few hundred bucks or send me Amazon gift cards or Seamless gift cards. It sounds suspicious, but it’s really not. He’s rich and nice, I’m young and broke, and he’s generous to me.

The Party Girl wrote that she would like Ricky: “[...] even if he was a poor schmuck. You don’t have to believe me, but it’s true.” We believe her! Think about all the coed crushes on proletariat professors.

One afternoon, Ricky took the Party Girl “to some art-gallery-drinks thing”. “After the boring art thing,” they went to a restaurant for dirty martinis, where she kissed Ricky’s neck. Later, back at her tiny studio in Nolita, the age-gap couple had a “fun night”. They kissed, and Ricky fingered the Party Girl to orgasm. The Party Girl related:

After the boring art thing, we go to a restaurant and have dirty martinis. I’m kissing Ricky’s neck while he tells me about his ex-wife and work drama. He’s in finance, obviously. I don’t know or care who Ricky dates or fucks when we’re not hanging out. We never ask each other such questions.

Ricky drives me home, and I invite him into my tiny studio, but we’re both pretty tired. We kiss. He fingers me until I come. Then he drives away. A fun night!

On cue, the next morning, the Party Girl recieved a “massage gift certificate from Ricky” - “such a nice place, too!” To thank him, she “text[ed] him a million heart emojis.” After the massage at the “fancy spa”, where she spent “90 minutes of heaven [on earth]”, she “text[ed] Ricky a million thank-yous, which he hearts.”

------

On Amazon Prime’s Cruel Intentions (2024), Caroline and Lucien, step-siblings and Manchester College students, attempted to seduce Annie - the 18-year-old freshman and daughter of the Vice President of the United States. Interestingly, Lucien had a “camera thing”. In other words, he couldn’t have sex unless he was making a sex tape; thus, every time he had sex on campus, it was recorded. (Note: Lucien shared his sex tapes with Caroline, whom masturbated in her sorority house bed while she watched her step-brother’s sex tape on her MacBook.) The Manchester College coeds whom Lucien made sex tapes with were willing sex tape participants, and, with the exception of the Vice President’s daughter, they had a disregard for whom saw the sex tapes.

This is relevant to the Party Girl, because after a “friend in PR” sent the Party Girl a “vibe” (i.e., a vibrator), “a tiny little guy”, from a company that the friend in PR represents, the Party Girl “double-lock[ed]” her doors and tried it out. Her verdict: “The vibe is a gem. I text my PR friend that I fully support her client.” Subsequently, the Party Girl filmed herself “using the new vibe”, and she sexted her Gen Z amateur porn to Dylan - a business school student whom lives in an apartment, “which is owned by his parents.”

Fascinatingly, like the Manchester College coeds, the Party Girl didn’t care if someone other than Dylan saw her sext. The Party Girl wrote:

I film myself using the new vibe and send it to Dylan. I am not worried about what Dylan will do with the vid. He can jerk off to it. Or show his friends. Who cares!

(Note: Dylan never responded to the Party Girl’s sext. Is that because receiving sexts is so common (for Dylan) that they don’t warrant a reply?)

And this is not an uncommon sentiment among Gen Z, which is a shift away from Gen X and even some Gen Y, whom are, in general, more protective over the distribution of their sexts.

For instance, on the “Spilling all of my FIRSTS” episode of the Extra Dirty podcast (June 5, 2025), a questioner wanted some advice from Hallie Batchelder, a NYC influencer with 645.6K TikTok followers and the podcast’s host, for some “extra dirty advice” about making sex tapes with three (!) of her “sneaky links” (i.e., casual sex partners). Understandably, the questioner was hesitant about making the three (!) separate sex tapes, because she had only made sex tapes in high school with her “long-term high school boyfriend”. The questioner asked Hallie: “Have you ever made a sex tape with a casual hookup?”

Hallie, who, à la the Party Girl, had a Venmo Sugar Daddy too, responded by sharing that, like Lucien, she has a sex tape problem and kink too, because she makes a sex tape with every casual hookup. Hallie opined that making a sex tape is similar to making a YouTube podcast; thus, she feels obligated to perform for the camera during casual hookups, because, to Hallie, having casual sex is almost like being on stage. Hallie said,

“Oh my god, I've made sex tapes with everyone. It's actually a problem and a kink of mine. Like, every casual hookup I've ever had, I'm, like, whip out the camera. I do have a podcast, so, like, whenever a camera is out, I feel, like, I perform. I kind of look at sex tapes the same way. It's, like, almost, like, I'm on a stage.”

Hallie said that she loves the idea that her sextapes enter the “spank bank” (i.e., saved content for masturbation), because she gets gratification from knowing that a guy is masturbating to, say, a sex tape of her oral sex performance. Hallie said,

“And I just, like, love the idea cuz, like, these are going to the spank bank. Like, these videos are going straight to the spank bank. And there's just something - a thought of a guy, like, you know, like, jerking off or whatever to, like, a sex tape of you, like, sucking them off or whatever that just makes - brings me gratification.”

In addition, Hallie shared that it’s hot to watch her performances in sextapes, because it’s similar to an athlete analyzing game film. While watching her sextapes, Hallie has fun analyzing the angles, the lighting, and assessing how she looks from the camera’s perspective. Hallie said,

“I think it's hot. Like, I think it's so hot to make a sex tape and then watch it back. Like, you know how like sports players they have like film and then like film meetings after. That's how I treat sex tapes with my casual hookups. We'll have a sex tape. We'll get all the angles, you know, maybe get a light in there. [...] I want to be filmed. I also, like, want to see what I look like from, like, a camera perspective. I think it's, like, fun. Maybe I'm just like a narcissist [...]”

However, Hallie advised that making a sex tape should happen organically.

“I wouldn't plan it. [...] No, I think it should be on a whim. Like, this is how I do it. I'll be, like, fooling around with a guy in my bed and then I'll just, like, "Oh my God, film me. This is so fun. That's so hot. And they'll always be, like, ‘Yep.’”

And Hallie warned the questioner about the possibility of sextape leaks, but Hallie said that, sometimes, like the Party Girl, she wants her casual hookups to leak her “amazing” sex tapes. Hallie said,

“But, like, sometimes I'm, like, I wish they would show their friends the amazing work that I've put into them.”

In the end, Hallie advised the questioner to have fun and make the three (!) sex tapes with her “sneaky links”, because making casual hookup sex tapes is fun and hot. Hallie advised,

“And yeah, I would just say have fun with it.”

“I would say do it. It's fun. It's hot. But at the end of the day, just like be careful [...]”

Further reading: “Influencer Hallie Batchelder: (Teen) Anal Sex and Venmo Sugar Daddies”

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 3) | Elementary and High School

The summer before Julia began elementary school, she went to Italy. Chiara, Julia’s 15-year-old cousin, “smokes like a chimney, drinks like a sailor, and curses like a truck driver.” But, unlike 14-year-old Julia, Chiara doesn’t wear makeup, thongs, and padded bras. (p. 60) [Later, Chiara informed Julia that their classmates were keeping track of the color of Jullia’s thongs in their notebooks. (p. 70)]

At the local bar down the mountain, Julia and Chiara downed “shots of vodka back-to-back” where Julia flirted with “hot older guys who ride motorcycles and drive muscle cars.” The boys in town didn’t “excite” Julia. Plus, Julia got a “rush” when she “succeed[ed] at the art of seduction.” Julia wrote that most of the men didn’t care that she was 14, which is not surprising since the age of consent in Italy is 14. (p. 60) 

Julia described 23-year-old Giovanni as the most beautiful man she had ever seen with an “Irresistible”, “Venetian drawl” and long eyelashes. (p. 61) And it didn’t hurt that Giovanni drove a purple Porsche Cayenne. 

After some Anima Nera and red wine, Giovanni kissed Julia with his “soft and succulent” lips. Giovanni unhooked her bra, lifted her skirt and kissed her breasts. Julia pulled down Giovanni’s pants, admired his penis, and she “suck[ed] it for a few seconds” before she squatted over Giovanni and sat on his uncircumcised yet “pretty” penis - “in the middle of the cobblestone road.” Thus, Julia lost her virginity at 14 in the middle of the street in Italy. (p. 62) 

Unsurprisingly, Julia and Giovanni were seen by a voyeur. However, days later, Julia and Giovanni had age-gap sex again - behind a “desolate church” “under the stars”. (p. 64)

Julia returned to New York, but, days later, she asked to go back to Italy whItaere she texted Giovanni: “Hi G. It’s Julia. I live in Italy now. If you're ever in Como, we should meet up.” G never replied. (p. 68)

In a basement café, while they all “chain-smoked cigarettes”, Julia showed some schoolmates her nipple ring. Consequently, they lost their minds! However, Julia's Italian classmates were “experienced too”. For example: “They wear heels every day to class. They wear layers of bronzer and their highlighted hair is always perfectly coiffed.” And Tatiana shared that she “has a thing for fucking married men”. For instance: “She’s been dating the butcher in secret for the past two years.” (i.e., Tatiana started dating the (married) butcher when she was 13.) (p. 74)

Julia returned to New York during Christmas break where she accompanied Trish to Trish’s “dealer’s apartment”, which is where Julia met Ace. Not one for pleasantries, Ace, with his “milky” skin and “jet-black hair”, simply dropped a white pill, which Julia popped. (p. 83-84)

Minutes later, in front of everyone in the dealer’s apartment, 16-year-old Julia climbed on top of Ace and rode him until she felt “fireworks” in her vagina. She wrote that she was “overwhelmed by the euphoric bomb that exploded” between them. Interestingly, Julia shared that that was her first penetrative orgasm, but she did not share when she had her first non-penetrative orgasm. (p. 85) 

Subsequently, Julia ran to the bathroom, in the nude, followed by Ace where she asked for more ecstasy. Moments after showering, dressing and popping another white pill, Julia rode Ace “hard and fast and soft and slow” in the back seat of a Honda while Dougies drove through midtown. (p. 85)

Days later, after Julia inhaled cocaine off Ace’s fist, she felt a “lightning bolt” strike that went from her spine to her panties and caused a “tingling sensation” in her vagina.  Consequently, in the bathroom, Julia ripped off her top, got on her knees, devoured Ace’s penis, and slurped on his “salty sweat juice.”  (p. 92)

Before her flight back to Italy, Ace gave Julia a Xanax, so she could, “[...] sleep on the flight.” However, after arriving in Italy, Julia told her grandfather that she needed money for an abortion. She lied. Julia used the money to buy a plane ticket back to New York. (p. 94-95)

Julia was back in New York, but she hadn’t been home in weeks. Consequently, Julia’s family posted a “missings persons poster on 59th Street”.  (p. 108)

Ace was abusive. For example, once, after he “chucked” a porcelain lamp at Julia, he dangled her “upper body out an open window.” (p. 112) It appears that Julia didn’t share Ace’s age, but he was at least 21, because the police threatened to arrest him for “kidnapping and statutory rap.” (p. 117) 

Unsurprisingly, Julia wasn’t the only elementary school girl whom had sex with Ace. Julia found “an entire collection of X-rated photographs” on Ace’s computer. For example, among the “endless photographs”, Julia found a photograph of “a petite girl with long chestnut hair, a spray tan, and the biggest boobs”. (p. 120-121)

A judge sent Ace “back to Rikers. No bail” (p. 122) where he threatened to murder Julia and her entire family. (p. 126) Consequently, while on the phone with Ace from Rikers, Julia attempted suicide and was admitted to the “psych ward” at New York-Presbyterian where she stayed for weeks. (p. 127-135)

After Julia was discharged from the “psych ward”, her father enrolled her “in a public high school downtown” where she “smoked so much weed and pop[ped] so many pills”, and where she was called the “weird white girl with a fat ass.” (p. 139) 

(Interestingly, Veronica, Julia’s wealthy “beautiful blond Italian” friend, visited New York. Consequently, to Julia’s shock, Veronica began an age-gap affair with Julia’s father. (p. 146-147) 

During high school, Julia became a teen it-girl after she “pose[d] semi-nude for a prominent street artist.” At night, Julia would “bounce around nightclubs all over the Meatpacking District” and she would wake up the next day with her “pockets and bra stuffed with crumpled-up dollar bills and” her “purse overflowing with cash”. However, Julia didn’t share how she got the cash. (p. 140) Subsequently, Julia applied for the (teen) dominatrix job and prayed for a Sugar Daddy.

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 1) 

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 2) | Middle School

[In addition to Down the Drain being a New York Times Bestseller, per Simon & Shuster, New York magazine opined that Julia Fox is “one of the all-time pop-culture greats”. Per Amazon, Elle named Down the Drain one of the "Best Books of 2023". And Elle’s Juliana Ukiomogbe opined that Down the Drain is a “masterpiece”.]

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 2) | Middle School

We related in part 1, that Julia Fox shared in Down the Drain (Simon & Shuster, 2023) that she was a teen sex worker and, after literally praying for a Sugar Daddy, she became a teen Sugar Baby. In addition, in the memoir, a New York Times Bestseller, Julia related some salacious from middle school. 

Julia wrote that when she was 11, she started 6th grade in the fall of 2001 at East Side Middle School in Manhattan where she smoked “the occasional cigarette here and there”, and she started “wearing dark lipstick to class”. (p. 28-29)

Ella, Julia’s straight-A student classmate, introduced Julia to marijuana. Julia wrote that before her first hit in Ella’s bedroom, her heart pounded through her Playboy tank top. Ella taught Julia how to “roll joints with a filter, ‘like the French’”. And Julia and Ella kissed each other “like the French too.” Ella, who had “beautiful thick auburn hair and big green eyes”, insisted that their pre-teen girl-on-girl kissing was “practice for the real deal”, but Julia sensed that Ella liked kissing girls. (p. 33)

Julia wrote:

“We play[ed] games like spin the bottle and seven minutes in heaven [i.e., in the closet kissing], and then we pretend[ed] like it didn’t happen.” (p. 33)

[In a bit of foreshadowing, Julia wrote that Kat, Ella’s 17-year-old sister, was a teen dominatrix whom “beat guys up for money.” Interestingly, Julia found a “vibrating crotch toy” in Kat’s bedroom. (p. 34)]

Julia and Ella got their belly buttons pierced on Saint Mark’s - in the 6th grade! (In addition, Julia got her tongue pierced in the 7th grade!)  (p. 34) Julia wrote:

“We decide to get our belly buttons pierced on Saint Mark’s, taking turns on the phone outside pretending to be each other’s moms, tricking the piercer into doing it. It becomes our little secret as we proudly show off our matching belly rings to our envious classmates in school.” (p. 34)

11-year-old Julia met 26-year-old Mickey at one of Kat’s house parties. After Julia took a hit from Mickey’s joint and chased it with a “swig of Jack Daniel’s”, Mickey said, “I know it might be wrong but I don’t give a fuck. I’ve wanted to kiss you all night.” Julia dared, “Well, then do it.” (p. 35-36)

Mickey did it, and Julia pulled Mickey down on top of her. Julia wrote that Mickey’s tongue tasted like “smoke and spearmint”. They didn’t have sex, but Julia wrote that it was an “exhilarating encounter”. 

Consequently, Julia became hooked on the power she had “over someone by simply just existing.” In addition, she shed her baggy clothes and embraced her figure. The hot-pink padded bra she stole from Victoria’s Secret made her B-cups “look like double D’s”. And Julia shared that she had “the biggest butt”, “which the boys at [middle] school always comment[ed] on,” but that made the girls jealous. However, Julia admitted: “I love[d] the attention.” (p. 36-37) 

After Ella moved to Catalina Island, Julia befriended “beautiful” Trisha whom was known for “blow jobs with older guys in the park.” But Trisha only gave one blow job in the park. It happened when she was in the fifth grade (≈10-years-old) and the boy was 17. Trisha shared with Julia that the blowjob in the park, which happened at night in the bushes near the entrance, was her idea, because she “really wanted to try it.” (p. 38-39) Apparently, Trisha was not afraid of NYC’s rats!

To accompany their piercings, Julia and Ella flirted with the “old tattoo artist guy” on Saint Mark’s whom gave them free tattoos. In addition, 12-year-old Julia and Ella got their nipples pierced. (p. 45-46) Julia wrote:

“We get our nipples pierced. We are twelve years old but my dad says we are worse than the girls in the movie Thirteen. He laughs and thinks it's funny.” (p. 46)

After Trisha moved to Oklahoma, Julia befriended Rose - a rich classmate. “Penthouse on Fifth Avenue rich.” Julia loved sneaking into Rose’s penthouse after hours where the schoolgirls would, “[...] sit cross-legged, facing each other on her floor, and pass each other love poems.” Sometimes Julia and Rose would: “[...] massage each other with oils”, “dribble hot wax over each other’s bodies’ or take “baths together” where Julia couldn't stop staring at Rose's “enormous double-D breasts, covered in thick purple stretch marks.” (p. 48)

When Rose was grounded, Julian hung out with Alice whom “lost a bunch of weight using diet pills [...] [and] started tanning and wearing makeup.” (p. 55) Julia and Alice had a crush on Tommy whom invited them to his house via AIM: “My mom is out of town, you guys should come over!” (p. 54-55) 

After a “few beers”, Tommy handed Julia and Alice a pair of boxers and they squeezed into Tommy’s “tiny twin bed” where, after Julia put Tommy’s penis into her mouth, he immediately ejaculated all over her hair. Consequently, Julia was “half thrilled, [and] half horrified.” Julia wrote:

I quietly slide under the blanket until I’m face-to-face with IT. Wow, it’s beautiful. I put my hands around it and grip it tightly with my sweaty palms. I move my hands up and down, his body twitching at my every move. I stick my tongue out and taste the tip, as if sampling an ice cream cone. It doesn’t taste bad! I put my mouth over it and before I can even start sucking, he ejaculates all over my hair. I shoot up from under the covers and run to the bathroom. I begin scrubbing the gelatinous goop out of my hair, half thrilled, half horrified. (p. 56)

Days later, Julia graduated from middle school; however, before she started elementary school, she lost her virginity to 23-year-old Giovanni - in the middle of the street in Italy. We recapped Julia and Giovanni’s age-gap affair in part 3 along with other salacious details that Julia shared about elementary and high school. 

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 1)

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 3) | Elementary & High School

[In addition to Down the Drain being a New York Times Bestseller, per Simon & Shuster, New York magazine opined that Julia Fox is “one of the all-time pop-culture greats”. Per Amazon, Elle named Down the Drain one of the "Best Books of 2023". And Elle’s Juliana Ukiomogbe opined that Down the Drain is a “masterpiece”.]

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 1)

Down the Drain (Simon & Shuster, 2023) is Julia Fox’s memoir. Julia shared in the New York Times Bestseller that when she was an 18-year-old student at City-as-School High School in Manhattan, she applied for a job as a (teen) dominatrix where she “could make up to a thousand dollars a day.” 

To get the job, Julia submitted a “full-body picture”, her bio, and she had to: “Describe in detail [her] most sadistic sexual fantasy”. Julia’s “sadistic sexual fantasy” was trampling a man’s cock and squatting on his face to suffocate him to muffle his cries before he masturbated and had an orgasm “in under ten seconds”. (p. 163-164)

Unsurprisingly, Julia got the job. (p. 166) Her first client was Stewart, an old man, whom she found “simultaneously repulsive and fascinating”. (p. 170) Stewart was fond of golden showers; therefore, Mistress Valentina (i.e., Julia) obliged. Julia wrote: 

I stand up, towering over him, and crouch down, releasing my bladder [...] He gargles and gags as the golden substance trickles down his face. “Mmmm,” he “begins to moan, and I notice that he’s finally getting an erection. (p. 171)

Source: Blue Supreme\Tumblr

Eventually, for “great money”, Julia became a sub. During one submissive session, an “older British businessman” with an “opulent watch and an impeccably tailored suit”, paid 18-year-old Julia $100 per article of her clothing, $100 to hook her arms to a suspension bar, $200 to whip her, “and another hundred to do it hard.” (p. 174) Of the submissive session, Julia wrote:

The room we’re in is lined with mirrors, and as I stand there, completely naked with my legs apart and wrists tied up and hooked to the ceiling, I can’t escape my reflection. I can see myself from every angle [...] flinching with every strike from the leather flogger. [...] And then the most forbidden thought of all crosses my mind: What would my parents think if they saw me like this? Cringe.

It’s impressive considering I’m only eighteen and the youngest girl to ever work there.

Julia became “addicted” to making “thousands of dollars a week, most of it cash.” However, Julia learned from the other dommes that “pretty dommes” didn’t “typically last more than six months at the dungeon.” Why? They got “plucked by sugar daddies who don’t wanna share them!” Consequently, Julia, literally, prayed for a Sugar Daddy. (p. 179) Julia wrote:

Every night before bed, I spend an hour scrolling through Backpage searching for my long-lost sugar daddy. I shut my eyes and pray: “Please, God. Please send me a sugar daddy. I promise I’ll be so good. I’ll never do anything bad again.” (p. 179)

Source: Blue Supreme\Tumblr

“After six long months at the dungeon," Julia, then-19-years-old and still in high school, met Rohan at The Union Club. Julia described Rohan as a “gentleman in his late forties with tan skin, jet-black hair, big brown eyes, and a warm smile stretching from ear to ear.” (p. 189-190) And “in good shape for his age.” (p. 197)

After their first lunch date, Rohan handed Julia “a check for seven thousand dollars.” Consequently, Julia gave Rohan “a long passionate kiss with lots of tongue.” At their second lunch date “at a restaurant in the Financial District,” with Jerry Springer “sitting less than five feet away,” Rohan dropped a “thick wad of cash” (i.e., “ten thousand dollars”) into Julia’s purse under the table. (p. 193) 

With the newfound money, Julia “went out every night until dawn” where she chased “Xanax bars with unlimited shots of tequila”. She and a friend did “lines of coke off each other’s feet for the viewing pleasure of older graff heads.” And Julia got nude on the stage at The Box. (p. 194)

Rohan rented Julia “a new apartment in the East Village”. Consequently, she felt “guilty for hiding” her “addiction from him.” When she was with him, she would “hide the tracks” on her “arms with long sleeve shirts”, but when she got home, she would “have a spoon” on her “nightstand waiting”. (p. 196)

After Julia “pop[ped] a Xanax” and “chug[ged] two glasses of champagne”, she “doze[d] off” while they were having sex for the first time. (p. 197)

On her 20th birthday, Julia and Rohan had lunch before Julia returned to her East Village apartment “while clutching the bundle of heroin” she had been saving. (p. 198) But for her 21st birthday, Rohan purchased Jullia a “cherry-red Mercedes Benz” and upgraded her to a $10,000/month “spacious loft in Soho”. (p. 200)

Subsequently, Rohan invited Julia and her friends to: “the opera, the ballet, and front-row seats for shows like The Book of Mormon”, “courtside [seats] at Knicks games”, “shopping sprees at Bergdorf’s and Saks” and “Thanksgiving and Christmas Day together at Cipriani.” P. 200

Eventually, Rohan became “needy and possessive”. Consequently, the “weight of his affection” became “too heavy” for Julia, but she “live[d] in constant fear” that Rohan would “take everything away”. (p. 201)

Subsequently, Julia began an affair with Shane – a skateboarder whom gave Julia “pussy tingles”. After the “messiest, sweatiest, [and] raunchiest unprotected sex” of her life, Shane said, “May I ask what the deal is with your sugar daddy?” And he asked, “Isn’t he married” However, Shane opined that Julia being a Sugar Baby was “pretty cool” and “fuckin’ badass”, and Shane promised, “I won’t fuck it up for you.” (p. 203)

During the summer, Rohan rented Julia a house in the Hamptons where Rohan caught Julia and Shane in the pool. After Julia “wrestle[d] a towel” around her naked body, she introduced Rohan to Shane. (p. 205)

Julia, “This is Marcello, my gay hairdresser!” 

Rohan, “He doesn’t look very gay to me.” [LOL]

Rohan, seemingly, fell for it. (p. 206) However, weeks later, a private investigator in Miami delivered Rohan a photo of Julia “straddling Shane in the pool, topless.” (p. 207)

In the end, before both relationships soured, Julia learned that Rohan had another Sugar Baby named Sabrina whom looked more Italian than Julia. (p. 217) Rohan got Sabrina a Porsche and the keys to the house in the Hamptons (on the weekends). (p. 221) And after Julia informed Shane that she was [temporarily] pregnant, she learned that Shane was “dating a Norwegian model” and that “he had a cocaine orgy in the bathroom […] with, like, ten people.” (p. 221)

Prior to sharing her life as a teen sex worker and teen Sugar Baby, Julia related some salacious details about her childhood, which you can read about in part 2. For example, during middle school, after Julia put her mouth over Tommy’s “IT”, he ejaculated “all over” her hair.

[In addition to Down the Drain being a New York Times Bestseller, per Simon & Shuster, New York magazine opined that Julia Fox is “one of the all-time pop-culture greats”. Per Amazon, Elle named Down the Drain one of the "Best Books of 2023". And Elle’s Juliana Ukiomogbe opined that Down the Drain is a “masterpiece”.]

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 2) | Middle School

Julia Fox: A Teen Sex Worker Praying for Sugar Daddy (Part 3) | Elementary & High School 

Influencer Hallie Batchelder: (Teen) Anal Sex and Venmo Sugar Daddies

Hallie Batchelder is a New York City-based influencer slash content creator who was recently signed to Alex Cooper’s The Unwell Network. Batchelder was on Cooper’s Call Her Daddy “The Hamptons Confessional” podcast (Aug 28, 2024) Hallie she shared, after having “about seven drinks”, that she recently had anal sex - on the first and apparently last date, that she dabbled with sugar daddies, and she was caught having (teen) anal sex in Aruba - when she was 15. 

“Hi, my name is Hallie Batchelder. I'm about seven drinks in right now, and guys, I'm feeling fucking fuzzy. I'm feeling warm and I'm feeling curious. I'm not gonna lie. Okay, I'm from Boston, Massachusetts, but I live in New York right now. My current relationship status is single. So single. Kind of sad. Honestly, the fall is gonna be really lonely, whatever.” 

“Okay, my confession is, last week, I went on a first date, and honestly, we had oysters as the appetizer. So I'm gonna, like, blame the oysters, because it's like an aphrodisiac. He fucked me in the ass, I'm not gonna lie, and I liked it. I hope they put this in.” 

Next Hallie, who is reportedly now in her late twenties, shared that when she was a college girl, she had sex on the same day with two different neighbors. Why? Because, per Hallie, she can’t turn down an offer for sex.

“Well, have I ever fucked multiple people in one night. There's so many answers to this question. Yes is the immediate answer. I mean, like, are we talking about threesome? Production? Wait, in college, there was one night, so I was on like, the basement floor of my building. That's where I lived. I used to, like, fuck this guy that lives in the basement, but I also fucked this guy lived on the third floor. It's like they were friends in the same frat. They found out about each other. I'm just a girl guys, I don't know, like, I don't know what to do. Like, like, they were both hot. Like, what like, am I gonna say? No, I don't know how to say, No, I'm working on it.”

In almost every age-gap memoir there are contradictions. And Hallie’s (verbal) memoir is no different. For example, Hallie began by stating that she was in a relationship with a man whom was “probably 13 years older”, and whom “used to spend, like, a daddy”. But then she said that since she came from money, she didn’t need money from a sugar daddy.

“Have I ever dabbled with the sugar daddy? I don't know if he was daddy's status. He was like, I mean, he was like, probably 13 years older than me, but he used to spend, like, a daddy.”

“Honestly, I don't need men for their money. Like, I come from money, so like, it like, doesn't bother me. So, like, when guys, like, think I need them for their fucking bag. I'm like, get be fucking frail for a second. I don't need your fucking pockets.”

Hallie went on to elaborate on the man, by relating that he was 36 and that she was turned on by his one-thousand-dollar tips. 

“He was probably 36. I was 23, which to me, was a daddy, but he used to go out to a restaurant. We'd get drinks. Say I was, like, two margaritas. He would always be like, “Should I tip a thou? Should I tip a thou?” And I be like, ‘Yes, tip a thou, and fuck me sideways.’”

Despite the fact that Hallie comes from money, she called her sugar daddy for three weeks to ask him to pay for her breast implants. 

“Okay, I have a funny story, actually, about the sugar daddy. So he was in London one night, and he FaceTimed me and he ghosted me for like, three weeks. So he finally picked up the phone. And I was like, “Okay, hi. I'm thinking about getting my boobs done. And he was like, ‘I'll pay for them, whatever. I'll Venmo you.’”

Apparently, Hallie’s sugar daddy’s best friend was Hallie’s sugar daddy as well. And both of them felt like they owned Hallie's tits. (I wonder what could have given them that impression?)

So him and his best friend, Venmoed for my tits. They, like, both think they own my tits. 

Interestingly, in the end, Hallie’s (wealthy) parents paid for her breast implants, and she “pocketed the money” from her sugar daddies.

“Little did they know my dad and my mom, if you pass your real estate licensing exam, like, I had no job at this point. So, like, if you pass your real estate license [...] we'll pay for that surgery. [I] [p]assed in two weeks, and then I pocketed the money that that guy gave me, and then had [an] amazing rack after that.”

And speaking of Hallie’s parents, Hallie shared that when she was a nymphet, and having anal sex on a pull out bed in Aruba, her mother stepped into the room. 

“Wait, when I was 15, my mom walked in. I mean, getting fucked in the ass on a pull out bed in Aruba.” 

Hallie’s Call Her Daddy episode has raised a (rhetorical) question: Why do influencers slash content creators like Hallie, Talia Lichstein, and Brianna Chickenfry share their (teen) sex stories? Is it for likes? For followers? For clout?  For money? All of the above?

Famous Age-Gap Couple: Aoki Lee Simmons (21) and Serafina co-founder Vittorio Assaf (65)

Tamantha Ryan posted on "Page Six": "Aoki Lee Simmons, 21, kisses Serafina co-founder Vittorio Assaf, 65, on romantic trip to St. Barts" (April 5, 2024) Ryan wrote that 21-year-old Aoki didn't let her 43-year age-gap with 65-year-old Assaf stop her from having a "romantic vacation" on St. Barts with the grey headed restaurateur. 

A 43-year age difference didn’t stop these two from having some fun in the sun.

Aoki Lee Simmons, 21, was spotted kissing restaurateur Vittorio Assaf, 65, during a romantic vacation to St. Barts on Tuesday.

In photos obtained by Page Six exclusively, the youngest daughter of Kimora Lee Simmons and Russell Simmons packed on the PDA with the much-older Serafina co-founder while enjoying time at a beach.

However, the pictures of the vacationing age-gap couple were obtained exclusively by Page Six, because neither Aoki or Assaf posted vacation pictures of them together on their respective social media accounts. Ryan wrote:

On Friday, Aoki posted some snaps from her trip to the Caribbean island on Instagram — but she notably did not include her beau in any of them.

And on March 27, she shared a video of herself on a beach wearing the same bikini as she did in the photos we obtained of her and Assaf together.

The Milan-born businessman also posted pictures from his trip, featuring one of his friends whom he said he has known for “25 years.”

However, Aoki, an apparently unabashed teleiophile, posted an Instagram Live video with Assaf (off-screen). In the video, Aoki referred to Assaf as her "boyfriend", and she said that she was "happier" and "more chilled out". And the age-gap couple referred to each as "baby".

Vittorio Assaf and Nya Gatbel (Getty Images)

In addition, Ryan shared that prior to Aoki, Assaf was "linked to 24-year-old model Nya Gatbel." However, Francesca Bacardi reported in the "Page Six" piece: "Serafina restaurateur Vittorio Assaf makes full recovery after week-long hospitalization" (June 28, 2023) that Nya was 22 when she was Assaf's girlfriend.

Russell Simmons and Kimora Lee (Getty Images)

Connectedly, per Barnaby Lane's Business Insider piece "A complete timeline of Russell Simmons and Kimora Lee Simmons' marriage and divorce", Aoki's parents, Russell Simmons and Kimora Lee Simmons, met when Russell was 35 and Kimora was 17. Lane wrote:

Simmons, the cofounder of Def Jam Records, first met Lee while she was modeling at New York Fashion Week in 1992, according to People.

Despite Simmons being 35, and Lee being just 17 and still a sophomore in high school when they met, they soon began dating.

In 2020, Simmons said that they didn't begin dating until Lee turned 18 and that Lee's mother approved of their relationship.

"She was legal at 17 but she turned 18 that may her mother and her manager Bethann Hardison approved supported and rushed us (we really didn't need a push)," he wrote on Instagram.

Per Lane, Russell and Kimora Lee were in their age-gap relationship for approximately 14 years. 

In the end, it appears that Aoki and Vittorio won't be having an age-gap wedding, because, per the Atlanta Black Star, shortly after their affair went public, they went their separate ways - at least publicly. But interestingly, in 2023, Aoki warned her father that if he didn't raise her budget, she would, like a number of NYU students, get a Sugar Daddy. 

The Hidden Price of Sugar: A Sugar Baby Desires True Intimacy from Sugar Daddy

Frankie Beach posted the piece "The Hidden Price Of Sugaring: Does being a sugar baby bolster capitalism?" on Killer and a Sweet Thang (NOVEMBER 13 2019). In the piece, 22-year-old Beach shared that she's a sugar baby, because she "needed money". [Emphasis added]

However, Beach was disturbed by the cold and transactional nature of sugaring. After an older sugar daddy informed Beach, "in a business-like manner", that he would pay her after they were "intimate", Beach was: "[...] lost for words, attempting to conceptualize an intimacy that exists isolated from a relationship: an intimacy that is performed." She wrote: "If intimacy is a service provided, is it intimacy at all?"

Despite their non-verbal debate over semantics, Beach and her sugar daddy met at a hotel room where for an hour, she gave him her young mind and younger body, and he gave her $500. 

At a hotel room, close to work, we met for an hour. I gave him my mind and my body and he gave me five hundred dollars in cash; to him it was a traditional relationship stripped to its bare bones, without any superfluous time spent or energy expended. Only the minimal requirements, an experience that offered a cathartic mental and physical release, then abruptly ended.

Interestingly, Beach wrote that most sugar babies don't consider sugaring to be sex work! Why? Because sugar daddies don't only pay for sex. In addition, they pay for "the illusion of intimacy". In other words, a sugar daddy pays for how much time he spends with his sugar baby, when and where they're intimate, and the nature of their intimacy.

By most who engage in it, it is not considered sex work. I don’t know if it is or not, and I don’t think it makes a difference either way. There’s nothing wrong with sex work for people who are fulfilled by doing it. But the fact remains that he was not only paying for sex, because he could do that a lot more cheaply and easily. What he paid me for is the creation and maintenance of a specific illusion, namely, the illusion of intimacy. He pays to be able to control how much time we spend together, when and where we spend our time, and the nature of the time spent. He pays to curate the experience of intimacy he wants.  

Despite, Beach's claims, there still appears to be very little difference between a john and a sugar daddy and a sugar baby and prostitute. #semantics For example, subsequently, Beach wrote: 

"[...] I was selling my body for sex." 

"And After he pressed the cash into my hand at the hotel room, I felt a rush. I felt a rush because having money made me feel powerful."

Unfortunately, Beach is convinced that her "personal value" is determined by how much money she makes, "[...] because money is the dominant societal indicator of value." And unfortunately, Beach has an inferiority complex and feels "worth less as a person", because she makes less money than most of her friends and family. 

We grow up convinced that our personal value is determined by how much money we make, because money is the dominant societal indicator of value. I know this is true because of the inferiority I feel at making less money than most of my friends and family, like I am somehow worth less as a person. 

Without fail, every piece of age-gap non-fiction we've recapped is littered with contradictions. For example, Beach shared that she's "in a place of privilege" and that her sugaring is simply done to make her life "a lot more comfortable". And she confessed: "I am not in a desperate situation." But then Beach blamed sugar daddies for the woes of sugaring. She wrote that she "cannot ethically support" sugaring, because it: "[...] encourages a practice of “intimacy” that ultimately benefits men."

I acknowledge that I am in a place of privilege. Although sleeping with men for money would make my life a lot more comfortable at this point in my life, I am not in a desperate situation. Not yet, at least. But sugaring is not empowering for me anymore because it requires me to avoid the truth that I am engaging in a system I cannot ethically support. Sugaring, in encouraging the creation of transactional relationships, also encourages a practice of “intimacy” that ultimately benefits men. Other forms of sex work don’t necessarily aim to construct such a controlled illusion of intimacy; they are straightforward about the service and the reward. 

In the end, it appears that Bleach would rather be a traditional prostitute, because she "cannot ethically support" "the illusion of intimacy" that comes with sugaring - despite the additional comforts that comes with the extra money.