Awkward Sex And The City with Natalie...

New York City's finest storytellers relive their most embarrassing sexual experiences just for your pleasure. Based on the popular touring storytelling show, Awkward Sex And The City is hosted by comedian and storyteller, Natalie Wall, and features guests discussing real stories about their sexual exploits, adventures, discoveries, and revelations. For every hilarious sexual tale, there are gross moments to match and love of everything awkward.

Comedy Interviews
Commincating in Quaratine w/ Angel Yau
70 min
College Is Scary w/ Cooper Raiff
60 min
What Do You Want From Me? w/ Clark Moore
This week on Awkward Sex and the City, Natalie interviews Clark Moore (Crazy Ex-Girlfriend, Love Simon, Soul Balm Podcast) about identity, considering yourself and what you want in a relationship, and understanding what you want.
61 min
If They're Inside of Me, We’re Gonna Make Out w...
57 min
Honesty Is Our Only Vaccine w/ Calvin Cato
31 min
Even The Sex Parties Are Cancelled w/ Calvin Cato
With returning guest Calvin Cato, this episode covers whats going on with the sex parties in NYC! And that leaving NYC is for cowards, or at least you should consider your priveledge before being upset about moving.
47 min
Secret List of Shitty Boyfriends w/ Sam Reece
This week guest Sam Reece reveals that dating in NYC right now is pointless! JK, sometimes being an HBIC is more important. Natalie and Sam talk about their experiences coming out as bi, and shitty manipulative boyfriends that you're not supposed to talk about.
53 min
What's Going On In NY Lately? [Solo ep wwith Na...
This week Natalie talk about Chadwick Boseman, colon cancer, how it feels in NY, kids going back to school, and sex during Covid. Wash your hands! Get tested!
45 min
Dating In The Time Of Corona w/ Kenice Mobley
54 min
Breaking Up In Quaratine [Solo Ep w/ Natalie!]
44 min
Live Laugh Love Libido [Solo ep with Natalie!]
70 min
I Need My Cottonelle Reparations w/ Jess Hender...
It's part 2 of the itnerview with Jess Henderson, host of the soon to be released podcast, PMS : Plants, Medicine, Spirit. Natalie and Jess discuss more accountability in being anti racist and life in the NYC and the comedy community.
97 min
UM! HELLO! HELLO? with Jess Henderson
This week is the first of a 2 parter with the incredible Jess Henderson! Natalie and Jess discuss being in a long term relationship in quarantine, getting therapy, and racism in comedy through fake allyship. LEARN SOMETHING, HELLO!
74 min
Getting Out Of Fuck Boi Rehab with Khalid Rahmaan
61 min
To All The Boys I Didn't Fuck
Natalie this week is bringing a solo episode about the men in her past that maybe missed the chance to get it. She talks about the people in her life who may have caused her confidence to shrink a bit when in reality, she is a bad bitch who can get it.
48 min
Can't Not Talk About Covid and Masturbate
34 min
Two Years of Awkward Sex!
It's been 2 years and 71 episodes of Awkward Sex and The City, and this is a very special episode with Natalie Wall, your host getting personal as always and thanking you, the listeners, for supporting the show for 2 years!
43 min
Calvin Cato, Hilarious Man and Receiver of Peni...
51 min
Black Trans Lives Matter
It needs to be said. It needs to be yelled. While it seems like there's support and movement, there is still more work to be done.
16 min
From Your Polite (for now) Black Friend, Mary Dorn
This week Natalie interviews returning guest, Mary Dorn, about her experience in New York Quaratine and activism on the internet.
54 min
Eight minutes and forty-six seconds
11 min
Falling In Love With My Gay Roommate [Solo Epis...
This episode of Awkward Sex And The City is with your sweet host, Natalie Wall. She gives a shout out to Matt, her former roommate and friend, and tells stories about their life together in NYC.
54 min
Meeting Aaron and Bad Rom Coms [Solo Episode wi...
This week's Awkward Sex and the City is another update from Natalie on living in New York City during Covid-19. She tells the story of how she met her fiance and fantasizes what a recovered, sexier, kinker NY might look like in the future.
51 min
I Miss New York [Solo Ep with Natalie]
This week's very personal, special solo episode is all about New York City and Natalie's love affair with living in it. With everything going on, NYC just isn't itself, but there's hope that soon it may move back towards how we rememeber it. Natalie remineses about old times in NYC being young and implusive as one should be.
57 min
Libido in Quarantine w/ Brittany Velotta
This week Natalie's bringing back one of her first guests and one of her first friends in NYC to talk about sex in quarantine, keeping up wiht mental health, and what the olds are fraeking out about.
63 min
My Type Is Near Sighted Meerkats w/ Sam Corbin
46 min
Emotional Convos And Wanking Off To Chat Roulet...
It's an another solo episode with your host Natalie telling stories of awkward sex from her past, updating you on the status of NYC and dealing with mental health in the pandemic.
41 min
Ballad of Chewie, The Cruddy Vibe [Solo with Na...
56 min
Hypothetically Doing Artisanal Poppers with Bob...
This week is actually a break from the solo episode to feature Natalie’s good friend, Bobby Hankinson. They chat boast sex in quarantine, managing anxiety and reading the news, and whether or not Natalie should do poppers.
43 min
A Very Gross Episode [Solo with Natalie Wall]
43 min
No Sex On The Floor [Some Solo Time with Natali...
36 min
Introducing All D!ck Is Trash Podcast with Mill...
Check out a new More Banana Podcast All D!ck Is Trash with Milly Tamarez! We're taking the week to figure out production and do our best to stay safe and responsible. But enjoy this new podcast with another hilarious lady and reach out to us at
69 min
Blame It On The 'Gulg' with Hope Morawa
This week on Awkward Sex and The City, Natalie interviews friend and thrifter, Hope! They talk foot fetishes, consent, and the state of dating in Brooklyn.
34 min
Natalie Freaks Out About Time with Sharron Paul
This week Natalie has a small freak out, but don't worry it's just about time and we can't change it so whatever, party. Sharron Paul (@sharronica) is the incredible guest this week who talks with Natalie about her current relationship, watching porn on the family computer, and Natalie's engagement surprise! Follow Awkward Sex (@awkwardsexcity)
57 min
Everything Is Pretty In The Thumbnail with Gabe...
This week Natalie Wall invites on Gabe Gonzalez (@gaybones) to deep dive into his experience with working in porn (not as a star) and the industry itself.
46 min
Live, Laugh, Do Coke With Your Mom with Katie H...
51 min
It Does Get Sexy with Lorena Russi
This week's episode of Awkward Sex And The City is with comedian, soccer player, and owner of incredible hair, Lorena Russi! Natalie Wall asks Lorena about anxieties around sex, how people look when people eat you out, and not watching porn.
45 min
Kissed Me Like A Shy Vampire with Sharon Spell
This episode of Awkward Sex And The City, Sharon Spell is the hilarious guest! Natalie Wall and Sharon talk about bad bad bad relationships in the past that included mixed signals, fuck boi nonsense, neck kissing, and singing conventions!
43 min
It Was A Graveyard Of Condoms with Julie Feltman
Get ready for a rowdy Awkward Sex and the City this week with Julie Feltman! Julie and Natalie discuss sex parties, finding the right partner even while you normally might look for the worst, and riding around the city on a Vespa. It's a great and hilarious episode!
41 min
Don't Touch Spices and Then your Genitals with ...
This week is a repeat guest and favorite, Calvin Cato. He revisits some of the relationship drama form the last episode he was on. Calvin and Natalie talk about communication in relationships, sex with foreigners in hotel rooms, and cooking before touching yourself (which you should NOT do fyi).
47 min
I Have Heard You Having Sex with Karolena There...
48 min
Your First Period Is Like JFK w/ Mary Dorn
Hello Awk Sexers! This episode is for the new year and new ears. Natalie Wall, the hostess with the mostess, sits down with photography and hilarious woman Mary Dorn to talk about sex in college, New York Apartments, and Amsterdam! And everything that comes up in between.
60 min
Don't Yuck Anyone's Yums w/ Kelli Dunham Live @...
46 min
Holiday Treat Re-Release! - "My First Time Was ...
Happy Holidays! Enjoy one of our most popular episodes from this year. See you in 2020!
40 min
I'm Gonna Have Sex With This Guy And He's Gonna...
52 min
Ruin Their D*ck And They'll Be In Love With Me ...
Natalie Wall is with pun-queen and the hilarious Sam Corbin for this week's Awkward Sex And The City! Sam brings a story about seducing a man in Tel Aviv and being the person who wants to placate in relationships. They both dig into boundaries and living a healthy life for yourself while dating.
47 min
Covered in Kid Snacks For My Tinder Date with J...
57 min
The Threesome That Led Me To Community Service ...
41 min
Honey, She Peed On Your Head with Sarah Hartshorne
Natalie Wall sits down with model, stand up, and activist Sarah Hartshorne in this week's episode. Sarah talks about her work with Lady Parts Justice, being on America's Next Top Model, and the time her friend peed on her boyfriend's head.
52 min
Some Spite Can Be Healthy with Kyra Sims
46 min
Don't Use Sun-In and Nothing Matters with Rebec...
46 min
He Said He Was a Gotti with Anna Suzuki
This week host Natalie Wall talks with guest Anna Suzuki (High Maintenance, Orange is the New Black, UCB, AZN Pop) about hooking up with a Gotti? Or was it a cousin of a Gotti? Not sure. This episode covers a little about porn preferences and finding a partner for real life nice sex. Get ready for giggles and truth! Also write a review, guys!
51 min
Spaghetti Dick with Domina Franco
50 min
It Makes A Bloop When It Comes Out - Gastor Alm...
Natalie sits down with the hilarious Gastor Almonte (who has a new album out btw!) to discuss having kids and how that affects your sex life, or how to even explain to them what sex is. Listen for advice on keeping a relationship fresh (yes we know everyone says that, but Gastor legit has some great advice) and laughs about the mistakes we make as children trying to figure out how genitals work.
58 min
I Just Want To Make Out With Everyone - Odd Aci...
Odd Acidity is a Roller Derby player, podcast host, and make out fanatic. Natalie Wall talks with Odd about their experience with awkward sex from the beginning, from heavy petting to dating in Turkey. Odd shares their experience with realizing their bisexuality and gender identity, and they even ask Natalie about her own experiences with awkward sexuality. This episode will make out with you.
41 min
The Crazy Bitch in Me Recognizes The Crazy Bitc...
39 min
I Call One of My Sex Toys The Dementor - Remy K...
Natalie is back with Remy Kassimir, host of How Cum podcast! Remy shares her path to making herself orgasm for the first time with the aid of her podcast and how prude shaming is just as bad as slut shaming. Both Remy and Natalie agree that you should have sex when you're ready, because it is a big deal!
46 min
TBT Replay - Let's Get Civical and Sexual with ...
This week your glorious host and feminista, Natalie Wall is taking a hiatus! But we have a really juicy replay for you from January of this year with two other women in the More Banana family, Lizzie Stewart and Arden Walentowski, the hosts of Let's Get Civical podcast (@letsgetcivical)
38 min
I Do Dabble with the Booty - Glo Butler
48 min
Your Dad is a Little Bit Gay - Nate Hankinson
51 min
I'm Too Open to Be Awkward - Savannah DesOrmeaux
This week guest Savannah DesOrmeaux tells no awkward sex stories, because they just don't seem to happen to her. Or maybe it's that they happen all the time, but sex is always awkward for everyone?! You decide!
45 min
As a Receiver of Penises - Calvin Cato
Calvin Cato, host of Playable Characters Podcast and Awkward Sex And The City Live regular, sits down with Natalie to discuss crazy hook ups, trying out flavored condoms, the best kinds of porn and so much more.
46 min
There's A War On Instagram With Hot Gay Men - D...
On this episode, David Goldberg brings his tale of a sexual tryst with an unnamed but influential man on instagram. There's intrigue, mystery, rumination on nerd culture and mainstream hotness. This episode will have you at the edge of your seat!
50 min
When You're Significantly Hornier, The Stakes A...
On this episode, Natalie talks with coworker and friend Stevie Edwards. Stevie studies Higher Education and works in the NYU LGBT Student center. Natalie and Stevie talk about being from the south, coming out to your family as queer, and gender euphoria.
43 min
He Ate Two Grilled Cheeses In Front Of Me And I...
On this episode of Awkward Sex and The City, Natalie Wall sits down with guest, queen, mom, and comedian, Carolyn Castiglia! Carolyn tells a story about a tinder date gone wrong with a grilled cheese guy, then the ladies dip into convos about dating now in swipe culture, what it's like for teenagers now, and talking to your kids about the bird and the bees (spoiler: they know all of it already. Thanks, internet!)
41 min
I'm Very Dancey - Emmy Harrington
Guest Emmy Harrington (actor, comedian, director) tells a story about an awkward sexual encounter with a friend's brother, how she met her current partner, and never being late to the party in life. Find Emmy and her work here. Follow Awkward Sex And The City @awkwardsexandthecity Follow Natalie Wall on Instagram and Twitter
36 min
My First Time Was Gonna Be With Ricki Lake - Al...
Comedian Ali Clayton tells a story about awkward sex in New York, specially her first sexual experience with a woman! Then Natalie Wall and Ali discuss Ali's background from North Carolina, being sober, and her relationship.
41 min
Lucid Dream Jizzing - Jeena Bloom
Jeena Bloom (@jeenabloom) comes on the podcast this week to tell a story about her first sexual experience and the fate of a low ceiling in Florida.  Check out Jeena’s podcast here on the More Banana Network.  Shweet!
31 min
ICYMI Extra Awkward Sex Stories
Get ready for the little extras that are left out of the final Awkward Sex And The City episodes. With stories from Jessy Caron, Bobby Hankinson, Arti Gollapudi, Lizzie Stewart, Cait Molden, & Caitlin Brodnick! It’s a powerhouse episode about poop,
29 min
I Have a PHD in Top 40 - Jen Keefe
Just so you know, there are some thoughts on Taylor Swift in this one! Jen Keefe (@jen_keefe) sits down with Natalie to talk about an awkward crush, loving the pop top 40, and dealing with emails from exs.  Follow the podcast on Instagram at @awkwardse...
41 min
Let's Get Civical & Sexual - Lizzie Stewart and...
The slaydies from More Banana’s newest podcast, Let’s Get Civical, sit down with Natalie Wall and figure out what sex and civics have in common. Arden Walentowski and Lizzie Stewart share stories of pooping in public,
43 min
Guess What?! Babies Come From Sex - Caitlin Bro...
Author of Dangerous Boobies, and co-host of ScamWow podcast, Caitlin Brodnick guests this week to talk about having a baby and being a sexy mom. Natalie Wall hosts Awkward Sex and The City podcast every other Wednesday,
43 min
Everyone Should Just Try Reddit Once - Cait Mol...
This week on Awkward Sex And The City Podcast with Natalie Wall, More Banana founder and producer, Cait Moldenhauer comes on to discuss Reddit, pegging, and life revelations. Check out Cait's Podcasts, There Will Be Porn and World Stealers on the Mor...
41 min
A Jelly Belly Sampler Pack Of Whatever Flavor Y...
On this episode of Awkward Sex And The City, Natalie brings on her great friend and fellow tour performer, Bobby Hankinson. They cover Chat Roulette, coming out, using LiveJournal and Myspace to date, and how to freak out your parents.
41 min
All Dick Is Trash - Milly Tamarez
Milly Tamarez from the "All Dick Is Trash - Ted Talk" sits down with Natalie Wall to discuss fuckbois, UTIs, and accepting what you want.
44 min
Why Did I Get Abandoned In Vietnam? - Jessy Car...
Host Natalie Wall (@gnatalieeee) and Jessy Caron (@welcometomyvagina) talk about hate fucking, the importance of travel, tilted uteruses, and getting dumped in a foreign country.Listen to Jessy Caron's podcast, Welcome To My Vagina,
35 min
Yea, I Literally Worship Women - Veronica Garza
This week on Awkward Sex And The City Podcast with Natalie Wall, guest Guest Veronica Garza (@veronicagotjokes) sits down with Natalie to discuss religion, loving women, and Texas.Follow the podcast on Instagram at @awkwardsexandthecity on Twitter @awk...
36 min
Unofficial Experts on Hooking Up For A Printer ...
This episode of Awkward Sex was recorded live as the She Makes Me Laugh Fest in NYC with Sydnee Washington & Marie Faustin form the Unofficial Expert podcast! They talk about hooking up for a printer, NY vs LA, Insecure, and psychics.
49 min
Our Favorite Awkward Sex & Live Show Announcement
This week on Awkward Sex And The City Podcast with Natalie Wall, we’re showing off our favorite Awkward Sex moments from the season so far… AND!!!!! Awkward Sex And The City will be recording live at the She Makes Me Laugh Fest in New York on October 1...
35 min
I Was Never In Trouble, Just Trouble Adjacent -...
This week on Awkward Sex And The City Podcast with Natalie Wall, guest Sarah Kennedy discusses being proposed to, coming out to her family, the comedy scene in Albuquerque, NM. Follow Sarah on instagram @sarahkomedy and at Follow th
41 min
Learn How To Eat It Without Getting A Bloody No...
This week on Awkward Sex And The City Podcast with Natalie Wall, guest Arti Gullapudi @artiparty tells a story about burping cum and Fanta, her sensitive ex-boyfriend getting a nose bleed, and taking back sexual empowerment while being awkward,
53 min
I Need You To Look Into My Vagina - Ayanna Dookie
This week on Awkward Sex And The City Podcast with Natalie Wall, guest Ayanna Dookie shares stories about traveling to maybe get dick, her first yeast infection, how there's not enough education about pain in women's bodies,
36 min
I Hate Pussies – Carly Ann Filbin
On this episode of Awkward Sex And The City the podcast, Natalie Wall shares with Carly Ann Filbin (@caralyannhasfun) about talking sex on stage and always looking hot.  Follow the podcast on Instagram at @awkwardsexandthecity on Twitter @awkwardsex
33 min
There’s More Than Just Doggy Style – Brittany V...
On this episode of Awkward Sex And The City, Natalie Wall sits down with an old friend, Brittany Velotta, to talk about bisexuality, the not-so-kink of Fifty Shades of Grey, and humping pillows.
45 min
First Girl To See A Penis Wins - Dani Faith Leo...
Natalie talks Awkward Sex with Dani Faith Leonard, founder of Big Vision Empty Wallet. Dani tells a story about the first time she ever saw a dick, and Natalie can’t help but ask questions. Plus, the downsides of trying to bang with a new spray tan.
28 min
Periods, Poops, And Being In A Relationship – A...
For the first podcast episode of Awkward Sex And The City, Natalie sits down with Anita Flores, stand-up and fellow More Banana podcaster, to discuss getting their first period, pooping in front of their partners, sex toy hygiene,
37 min
Awkward Sex And The City with Natalie Wall Trailer
New York City's finest storytellers relive their most embarrassing sexual experiences just for your pleasure. Based on the popular touring storytelling show, Awkward Sex And The City is hosted by comedian and storyteller, Natalie Wall,
1 min