Teen Anal Sex in Prime Time

I wrote in The Allure of Nymphets that the first mainstream teen film that I saw that made a reference to anal sex was Cruel Intentions (1999). In the film, Kathryn (Sarah Michelle Gellar) made a wager with her step-brother Sebastian (Ryan Phillippe) that he couldn't seduce a nymphet (Selma Blair); however, if Sebastian could corrupt the maiden, Kathryn agreed to, “[...] fuck his brains out,” and allow him to, “[...] put it anywhere.”

Let's leap over a decade to MTV's Awkward. Here's MTV's brief "about the show": 

This series takes an irreverent look at the conflict, chaos and humor that defines teenage life through the eyes of 15-year-old Jenna Hamilton [...]

In addition to other references to anal sex, on the third episode of season one, Lissa, a Palos Verdes, California high school student, offered her behymen (i.e., her anal virginity) to her boyfriend for respecting her wishes to maintain her vaginal virginity. 

In Pretty Persuasion (2005), fifteen-year-old Kimberly Joyce (Evan Rachel Wood) shared that when she was fourteen she had anal sex with Warren Prescott, which occurred after he said shyly, "I was wondering if you might let me pack your fudge chute."

We were floored when James, a teen, in Vacation (2015), asked the nymphet he recently met during the family road trip if he could give her a "rim job" (i.e., analingus).

Here's some the dialogue that took place between Katherine and Jake in front of the lockers of John Hughes High School in Not Another Teen Movie (2001) :

“Can I ask you a question? Why is it every time I tell a guy they can put it wherever they want, they always stick it in my ass?” Katherine asked Jake, the school jock, before she invitingly, and as some would opine, blasphemously simulated fellatio on the crucifix by slowly sliding the ancient symbol in and out of her wet mouth.

“That’s just way too much information for me Katherine.” Jake replied.

“Oh no Jake. Way too much information would be telling you that after they’re done, I always take a huge dump on their chest.”

And in MTV's The Hard Times of RJ Berger, RJ's high school classmate offered him: "Any time. Any place. Any orifice.:

Of course, this topic isn't limited to the United States. In the Argentinian film La Niña Santa (2004) [The Holy Girl]", there's not only teen anal sex, but a teen lipstick lesbian kiss, teen masturbation, and an age-gap affair. 

In the ABC News article "Study Reports Anal Sex on Rise Among Teens", it was reported that the Bradley Hasbro Children's Research Center confirmed my suspicions that anal sex is on the rise among teens and young adults. The rise was attributed to the ease of social mores, which sexuality educator, Cory Silverberg, attributes to the proliferation of pornography.

Consequently, Teen Vogue published "A Guide to Anal Sex [for Nymphets]", which: "is anal 101, for teens, beginners, and all inquisitive folk."

TEEN VOGUE: A Guide to Anal Sex [for Nymphets]

Update | 12/26/19 [8:27 PM]: On the day after Christmas, Teen Vogue decided to tweet a link to "A Guide to Anal Sex [for Nymphets]". Unsurprisingly, the tweet is trending. 

In the vein of Tavi Gevinson's Rookie, Teen Vogue has posted "A Guide to Anal Sex [for Teens]", which: "is anal 101, for teens, beginners, and all inquisitive folk."

Gigi Engle, the post's author, wrote that the post has: "[...] everything you need to know about butt stuff, no matter who you are, whom you’re having sex with, or who you want to have sex with." 

We know that that is an hyperbole, because as the age-gap widens, so does the displeasure. However, orthodox Jews and Muslims would say that anal sex should be avoided between all age groups.

We're a bit surprised by the backlash that Teen Vogue and Gigi Engle has receive, because nymphet anal sex has been portrayed in films and television shows for years.

And the Bradley Hasbro Children's Research Center found that anal sex is on the rise among teens. The rise was attributed to the ease of social mores, which Cory Silverberg, a sexuality educator, attributed to the proliferation of pornography.

Hulu's TINY BEAUTIFUL THINGS (2023): Teen Threesome and Schoolgirl Lipstick Lesbians

Here’s IMDb’s (lax) synopsis of Hulu’s Tiny Beautiful Things (2023):

[Tiny Beautiful Things] [f]ollows a woman who reluctantly becomes Dear Sugar; an anonymous and revered advice columnist, even when her own life is falling apart.

The synopsis is lax, because it left out the teen threesome subplot, which was, very interestingly, not only shown in the trailer, it was shown in the preview of episode 01 as well, but the teen threesome didn’t happen until episode 02. 

And it was implied in the trailer and in the introduction to episode 01 that Clare (Kathryn Hahn) and her husband Danny had a threesome with Rae - their 16-year-old daughter, but the actual (unedited) conversation didn’t take place until episode 03. 

Clare, "A threesome is a big leap. Maybe you were subconsciously worried about our little threesome."

Rae, "What?"

Clare, "Me and you and dad."

Rae, "Ew!"

And in the trailer and introduction to episode 01, Rae shared with her mother that Bethany, the other private schoolgirl in the threesome, had public anal sex on a greyhound bus.

Rae, “Bethany had anal sex on a greyhound going to Reno!”

Clare, “What?

Rae, “Yeah.”

Clare, “Why would she wanna take a bus to Reno?”

However, the (unedited) conversation didn’t take place until episode 04. (Talk about using the allure of nymphets to market a streaming series.)

In episode 02, after Clare came home from work early and discovered her 16-year-old daughter having a threesome, Clare asked Bethany, “Do your parents know? Should I just give ‘em a quick call?” Bethany replied, with her white bra showing under her schoolgirl uniform, that her parents, “[...] support sexual exploration.”

Now here’s the unedited dialogue about the teen threesome that took place in episode 03. 

Clare, “I know that you probably have had some twosomes before.”

Rae, “Mom!”

Clare, “I think a threesome is a big leap; so, I was wondering if maybe you were subconsciously worried about our little threesome.”

Rae, “What?”

Clare, “Me and you and dad.”

As you see, Clare assumed that Rae had had teen sex a number of times before the threesome; so, it’s surprising that Clare assumed that the threesome was organized by Bethany - whose parents were described as “rich and cosmopolitan”, but Bethany, whom goes by Montana, shared that the teen orgy was Rae’s idea.

Clare, “What made you think it was a good idea to orchestrate an orgy in me and my husband’s bedroom?”

Bethany\Montana, “That was Rae’s idea.”

And Bethany\Montana shared with Clare that Rae was “completely obsessed” and in love with Bethany\Montana. That’s correct. Tiny Beautiful Things has a teen lipstick lesbian slash schoolgirl subplot, which didn’t take place until episode 06, but surprisingly it wasn’t previewed in the trailer or in the introduction of episode 01. 

Interestingly, Clare said that she knew how to have a proper threesome and opined that her daughter’s teen threesome was “pathetic” and referred to it as “little pussy-ass shit”.  

Bethany, “Maybe you weren’t aware that she’s completely obsessed with me […] I can’t help that she’s in love with me.”

Clare, “And I know how to have a threesome. Not that pathetic little pussy-ass shit. […] thinking everyone wants to fuck you because you have great hair?”

In episode 04, Rae posted a video on social media of her seductively ingesting a large cucumber, which caused Clare to exclaim, “What the fuck!” In episode 04, the director took the opportunity to show Rea in her striped panties. And in episode 04, the conversation about Bethany having anal sex on greyhound bus took place, which I’ll share again to emphasize that Clare was unfazed by public teen anal sex.

Rae, “Bethany had anal sex on a greyhound going to Reno!”

Clare, “What?

Rae, “Yeah.”

Clare, “Why would she wanna take a bus to Reno?”

In episode 06, shortly after Bethany\Montana complained to Rae that she was fourth on her private school’s “Most Fuckable Girls’ List” (“Fucking fourth!”), Rae shared with Bethany\Montana that she was not a virgin, because she had sex with Stef Johnson and Sofia Serrano - respectively. And Rae related that she masturbates. (“I have a body, and I know what feels good, so”)

Consequently, upon learning that Rae’s parents were on a date night, Bethany\Montana suggested that they go back to Rae’s house, but Rae said suggestively that Bethany\Montana would have to remove her nail extensions before they had teen lipstick lesbian sex, which they proceeded to have until they were interrupted by the door bell. 

Tiny Beautiful Things (2023) received a 90% AVERAGE TOMATOMETER and a 85% AVERAGE AUDIENCE SCORE. Angie Han of the Hollywood Reporter opined:

True to its name, Tiny Beautiful Things is sensitive to the details. The series has a knack for zeroing in on moments too strange or specific to feel like anything but lived experience.

Interestingly, Tiny Beautiful Things is loosely based on Cheryl Strayed’s book, but there doesn’t appear to be a Rae or Bethany\Montana in the book. Grace Wehniainen wrote in her Bustle piece “Is Tiny Beautiful Things Based On A True Story? (April 7, 2023)

As is the case with most adaptations, not every detail is the same on page and screen. Names are changed, and Clare’s life isn’t exactly like Strayed’s. In the show, for example, she’s the mom to a teenager, while Strayed’s actual kids were still pretty young [...]

The last time we wrote about Kathryn Hahn was when she starred in Amazon’s I Love Dick (2016) where she played Chris whom, in the spirit of Nancy Friday's My Secret Garden: Women’s Sexual Fantasies and Tavi Gevinson's Rookie, (over) shared: 

"Dear Dick, I've been horny since I was six. I used to press my crotch into the belly of my stuffed Rhino [...] I'd love to hump him in front of our sitter Karen Harris. I used to say that Rhino was hungry and that I needed to feed him [...] In high school, I wanted to fuck anybody - male or female." 

Lastly, Tiny Beautiful Things shared executive producers with Big Little Lies (2017) where 16-year-old Abigail, to raise money for Amnesty International, auctioned off her virginity - online. 

THE TO DO LIST (2013): Teen Sex To Do List

The To Do List (2013) is about Brandy (Aubrey Plaza), a Boise, Idaho high school senior, who made a To Do List of sexual acts to experience before she matriculated at Georgetown University. 

Brandy made the to do list after being ridiculed for being a virgin by her classmates and her sister.  Interestingly, Brandy's sister lost her virginity when she was 14-years-old.

Among other sex acts, the list included: 

• necking
• teabagging 
• rim jobs
• finger bang
• masturbate
• dry hump
• blow job
• intercourse
• orgasm

The to do list did not include anal sex; however, despite her father's warning, Brandy had anal sex in her Georgetown freshman dorm room. And inexplicably, via anal sex, she was able to check off orgasm.

In another scene, Wendy, Brandy's high school friend, said that a young boy, horsing around in the swimming pool, put his finger up her "ass."

I shared in The Allure of Nymphets that Cruel Intentions (1999) was the first film that I reviewed that mentioned teen anal sex between high school students. And that the Bradley Hasbro Children's Research Center confirmed that anal sex is on the rise among teens. Thereby, once again, showing that art is (often) a reflection of (teen) society. 

Interestingly, the original title for the movie was The Hand Job and the Motion Picture Rating organization rated the film a R for "[...] pervasive strong crude and sexual content including graphic dialogue, drug and alcohol use, and language - all involving teens." 

PLAN BRI UNCUT Ep 10: “A Full-Ass Hour on [Teen] Sex [...] Losing Your V-Card, Anal, Porn & Masturbating”!

Episode 10 of the Plan Bri podcast is tantalizingly titled: “A Full-Ass Hour on Sex with Alyssa Sines: Losing Your V-Card, Anal, Porn & Masturbating” (September 22, 2020)

The episode was hosted by Brianna Chickenfry. Per The Sun, Brianna, originally from Boston, was 21 when the podcast was recorded. The episode’s guest was Alyssa Sines. Per Famous Birthdays, Alyssa was 21 when the podcast was recorded as well. 

Brianna described Alyssa as super hot, Ms. Sex Queen, and a sex icon with 1.1 million followers on TikTok to whom Alyssa talked about masturbating and rough sex.

“She’s just, like, a sex icon. She’s super hot. She has 1.1 million followers. She talks about masturbating. She talks about getting her back blown out.” 

Just as the title implies, Brianna and Alyssa began by describing how and when they had sex for the first time. Brianna, “We’re gonna start off by telling our Losing Virginity Stories, because that’s where it must begin.”

Brianna shared that when she was 16, she had a party while her parents were away. Coincidentally, she desperately wanted to lose her virginity, because being a virgin made her feel like a “fucking loser”. And it didn’t help that all of her friends were not virgins. And Brianna didn’t care with whom she had sex with (for the first time).

“I was, like, at that point where I was just, like, I wanna lose my virginity. Like, I don’t even care who it is. Like, just, it needs to happen. All my friends did. And I was like, I feel like a fucking loser.”

Consequently, Brianna got “hammered” and chose a younger “random kid”. However, Brianna was disappointed with her “first time”, because the younger random kid had a thin penis. 

“His dick was like a pencil. It didn’t even hurt. That’s how bad it was. My first time didn’t even hurt. It was literally like a tampon.”

But one can infer that the younger random kid enjoyed Brianna’s first time, because he commemorated the event with a Snapchat that he titled “Just fucked!” And unbeknownst to Brianna, the younger random kid put his used condom in Brianna’s younger cousin’s bag, which she unknowingly took to school and pulled out in English class the next day. 

Shockingly, Brianna shared that that was the first and only time she has used a condom, and per Brianna, she has had a lot of sex since she was 16 - including anal. 

“That’s actually the only time I used a condom. I think, is that one time - losing my virginity.”

“I went through an anal phase. Like, it was, like, anal every time I had sex for, like, a very long time. And I’m glad that’s over with because, I couldn’t shit for so long [...]”

I won’t go into how Alyssa, whom shared, “I watch a lot of porn,” lost her virginity, but I will relate that she shared that she had sex behind her high school - “so much” “a lot”.

“When I was in high school, it [i.e., sex] was more fun, because you snuck around - in cars. I had sex behind my school - so much [...] Hey, teachers, I had sex behind the school a lot. Y’all probably already knew.”

Alyssa’s high school sexcapades reminded me of Andrew Trees’ novel Academy X (Bloomsbury, 2006) where Mr. John Spencer, an English teacher at the elite Academy X:  “[...] tried to avoid using any out-of-the-way stairwells in the afternoon.” Why? He didn’t want to come upon any prep school students having sex.

And straight out of a confession in Nancy Friday’s My Secret Garden, which Ariel Levy, in Female Chauvinist Pigs: Women and the Rise of Raunch Culture, referred to as a “groundbreaking collection of women’s sexual fantasies”, Brianna and Alyssa shared that they started masturbating in middle school. 

Alyssa, “I, literally, bought my first vibrator when I was, like, 17 [...] but I feel, like, I was masturbating when I was, like, 10 or like 8.” 

Brianna, “I feel, like, I was too.”

Here’s the part of the Plan Bri episode that was most relevant to this blog. It’s not in the title, but Brianna and Alyssa discussed age-gap relationships. Brianna related that when she "18", she had “the best sex ever” with a 28-year-old whom had a penis shaped like a banana. 

Brianna, “Have you ever had, umm, sex with, like, a significant older man when you were, like, younger?” 

Alyssa, “I haven’t, like, fucked an older man. I’m, like, disappointed in myself.”

Brianna, “So when I was, for legal reasons I’m gonna say 18. I had sex with a 28-year-old. And, oh my God, it was like, the best sex ever. I feel, like, older guys. I feel, like, they know more. Because they know more.”

Brianna, “This guy, the 28-year-old guy that I fucked. His dick was like a banana. It was, like, curved [...] yeah, I still think, like, that was, like, one of the greatest sex [sic] I’ve ever had.”

Although, Alyssa related that she was “disappointed” that she had never had sex with “a significant older man”, she did share that she wanted to have sex with a 50-year-old. Why? Just because. 

“I feel like, one time, I wanna, like, fuck, a 50-year-old and just see how it is.”

Lastly, the episode was sponsored by Barstool Sports, Honey (a browser extension), and Pirate Water, but other than using the allure of nymphets to make money by getting even more advertisers, why did Brianna decide to (over) share the details of her (teen) sex life. The answer is quite simple. She was asked. 

“You guys always ask me to talk about my sex. Like my sex life, hookups - all that shit.  And I didn’t want to do it alone. And Alyssa is Ms. Sex Queen on TikTok; so, I figured let’s bring her on [...]”

[Note: Although, Brianna said, “Hey, Plan Bri listeners, you can find every episode on Apple Podcasts, Spotify or YouTube,” the YouTube video for the episode is not posted, and it appears that Alyssa has made all of her social media accounts  private.]

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?