Where was the pleasure when Anthony lost his 'ass virginity' in 'And Just Like That'?

Sex in real life is messy. You end up with lube or bodily fluids on your sheets, one of your partner’s pubes in your mouth, or cramp in your leg from the new position you’re trying. However, most media depictions of sex skip over the less-than-perfect parts. Take And Just Like That's Season 2 finale: The scene where Anthony Marentino (Mario Cantone) lost his "ass virginity" is an exception because he’s visibly uncomfortable.

It feels like the phrase "ass virginity" told viewers that they should laugh at what can legitimately be an anxiety-inducing experience. Yet in the episode, Anthony seems genuinely anxious about being the receptive partner for anal sex — known as bottoming — for the first time. It's just that the show doesn’t take those concerns seriously. While there’s a case to be made for TV shows needing to show viewers more realistic sex scenes in general, choosing to start with making light of gay man’s nervousness about first time bottoming for anal does queer and straight audiences alike a massive disservice.

The Sex And The City spin-off has seen Anthony move beyond a ‘gay best friend’ accessory and into a more fully developed character in his own right. This growth is obvious in looking at his struggles to open up to his new boyfriend, Guiseppe (Sebastiano Pigazzi). In the season’s penultimate episode, Anthony gets defensive when Giuseppe tells him that he wants to ‘top’ Anthony because he’s in love and wants to make Anthony feel "something wonderful." In the final episode, Giuseppe reveals to a group of Anthony’s friends that he’s heading back to Rome soon because he’s finding publishing in New York "impenetrable." When they’re alone, he clarifies that it’s not just about sex, but because Anthony won’t open up to him emotionally either.

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Anthony has a genuine moment of vulnerability and growth, acknowledging that he struggles when he feels like he’s not in control, and ends up admitting that he loves Giuseppe – not realising that he hasn’t said that before. This is, obviously, followed by them making out. Yet in certain contexts (such as Giuseppe repeatedly calling him ‘Tony’ when he’s asked him not to), it might look like bottoming for anal was never something Anthony wanted to do, but something he felt like he had to do to keep his new partner.

If it was supposed to be a joke, it wasn’t funny; if it was supposed to be a realistic depiction of first time anal penetration, the show needed to do a lot more than just show Anthony’s discomfort.

Especially because when they do have sex at the end of the episode, Anthony doesn’t look like he’s having fun. Amid the montage of other characters sharing moments of intimacy and pleasure, Anthony’s pained expression as he lost his "ass virginity" stuck out. If it was supposed to be a joke, it wasn’t funny; if it was supposed to be a realistic depiction of first time anal penetration, the show needed to do a lot more than just show Anthony’s discomfort.

Credit: Craig Blankenhorn/Max

It’s true that experiencing anal penetration for the first time can be uncomfortable. Sex educator Topher Taylor explains that as the anus is used to "one way traffic," your first time having anal sex as the receptive partner can feel strange. The nerve endings in your anus are being stimulated in a way they haven’t before, and you may experience a burning sensation. Taylor says that it’s important to go slowly – and a crucial part of that is communicating, "Because then you can go, ‘look, you need to stop because I want to figure out what this feeling is.'"

When the topic of Anthony bottoming first comes up, Anthony responds that "I've never been fucked [...] because I'm not the woman!" While Anthony explains that this is how gay men of his generation think about sex, it’s a framework that is significantly more common from straight, cisgender people who don’t understand how sex between queer people works. The idea is that being penetrated makes you "the woman" and being woman-like is the worst thing you can be because women are weak. Taylor says this perception of anal is: "saturated in homophobia, queerphobia and misogyny. [...] It's seen as less than, like people almost reducing themselves by doing it."

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However, there are other reasons why Anthony might be anxious about bottoming – ones that don’t necessitate enjoying anal being a punchline. Although Anthony’s exact age in the show is never revealed, Cantone himself is 63. If Anthony’s age is similar, it would mean he was in his twenties during the height of the AIDS epidemics in the 80s. In 1990, AIDS was responsible for 35 percent of all deaths of men aged 25 to 44 in New York. Jokes about queer people dying of AIDS – deserving to die of AIDS – were everywhere. It probably isn’t in character for Anthony to have been at the first ACT UP (AIDS Coalition to Unleash Power) protest in March 1987, but he undoubtedly would have known people who died. It’s hardly surprising that living through a time when it felt like anal sex came with a death sentence would impact how you might feel about it.

Credit: Sarah Shatz/Max

The show uses Anthony’s unwillingness to bottom to symbolise his need for control. At Carrie’s Last Supper, he vows to let go of control, but the problem with using sex as a metaphor is that the next step is Anthony bottoming to show his commitment to letting Giuseppe in. But Giuseppe doesn’t tell Anthony that he wants more emotional vulnerability until after he’s announced that he’s planning to leave. While Giuseppe’s frustration with Anthony pushing him away is valid, that should be a separate conversation to his desire for Anthony to bottom for him. By weaving the two together, the show creates a dynamic where it could feel like Anthony "owes" Giuseppe sex to prove that he’s willing to change, so he’s no longer allowed any limits about the kind of sex he wants.

However, it’s also clear that Anthony was thinking about having anal sex before Giuseppe dropped his Rome bombshell. Earlier in the episode, Anthony tries to get hold of Charlotte (Kristin Davis) to discuss it with her, but she’s hungover from her own journey of self-discovery. Why couldn’t we have seen Anthony admit to his closest friend that he wants to try bottoming with Giuseppe, he’s just scared that his tough-guy mask will slip and he won’t be able to stay strong if his new boyfriend leaves? It would have confirmed that he did want to try something new with Giuseppe – both emotionally and physically.

SEE ALSO: How to prepare yourself for anal sex

Anthony’s concerns about anal penetration are never addressed. The position they have sex in at the end of the episode is one that Taylor recommends for beginners, as it lets you feel the intimacy of your partner behind you and makes it harder for them to go "balls deep" inside you straight away. However, it means that they aren’t facing each other, and we don’t see Giuseppe checking in with Anthony, making sure he’s ok, and asking him if it feels good. We also don’t see any of the warm up that is necessary for any kind of anal play — such as having a warm shower to relax the muscles of your anus, your partner rimming you, or your partner fingering your arse before moving on to a slightly bigger butt plug – let alone when your partner’s penis is reportedly nine-inches.

Taylor recommends that you don’t jump from taking nothing to taking nine-inches in an evening, but do it more gradually, using fingers and butt plugs or an anal training kit to get used to the sensations and the stretch of something in your anus. Skipping the warm up and preparation can result in tears, rips and fissures; going slowly and building up to penetration is essential, especially if you want it to be pleasurable for the person bottoming as well as the person topping.

Lube is another must. Although there’s a tub of Boy Butter on their bedside table, it’s the colour of the brand’s oil-based lube – which Topher points out shouldn’t be used with latex condoms as it can break down latex and make condoms ineffective. (He recommends water-based or silicone-based lube instead.) Perhaps both characters are on Pre-Exposure Prophylaxis (PrEP), a medication that prevents HIV infection, but there’s no mention of that either. Of course, it’s possible that both characters have recently been tested for STIs and are negative – and why would the show tell us that? After all, And Just Like That is supposed to be a comedy-drama, not a safer sex lesson.

Anthony’s expression reinforced the idea that bottoming for anal sex is something you do for your partner, not for your own pleasure.

With the absence of comprehensive, LGBTQ-inclusive sex education, many of us turn to media to glean what information we can. Unfortunately, mainstream media often promotes incorrect ideas about sex, like the idea that anal sex is always painful for the person being penetrated. And Anthony’s expression reinforced the idea that bottoming for anal sex is something you do for your partner, not for your own pleasure.

Taylor says that it’s important not to go into your first time putting pressure on yourself to love everything about the experience or expecting that there won’t be any discomfort. But the idea of enjoying yourself isn’t unrealistic – so in a show that certainly plays fast and loose with reality, why was it too much of a stretch (pun intended) to show Anthony enjoying Giuseppe fucking him? Anthony needed to step outside of his comfort zone and be vulnerable with Giuseppe, but that shouldn’t be at the expense of pleasurable sex or his own limits. How radical would it have been to see Anthony opening up emotionally to Giuseppe but sticking to his boundary about not wanting to bottom for anal sex? Just like Charlotte, back in the first series of Sex And The City, Anthony should get to say no to anal sex if he doesn’t want it.

If Anthony bottoming was essential for his character arc, the show should have shown the preparation that goes into making anal pleasurable for everyone involved. Taylor recommends anilingus as a great first step into anal play. It relaxes your body, which makes penetration easier and more comfortable. A shot of Giuseppe rimming Anthony followed by one of him reminding Anthony to breathe as he slowly pushed inside him for the first time would have been an equally realistic depiction of anal sex.

Anthony deserved to enjoy his first time bottoming for anal – but even more than that, the queer and straight viewers deserved to see that anal sex can be pleasurable, playful, and romantic. That’s a message we still desperately need.