How to Woo – Details, episodes & analysis

A total power exchange with his wife, partner-focused pleasure, and exploring piss play—Steve shares how his 20-year vanilla relationship transitioned into a consciously designed, mutually nurturing connection.

00:00 Scalding hot baths, outdoorsy adventures, and grounding in himself

06:16 A magnetic spiritual connection with his partner and how they balance their disparate relationship needs

12:17 How a 24/7 dynamic with contracts and monthly meetings helped him connect more fully with his partner

19:59 Protecting mental well-being + preparing safety measures following sub drop and top drop

24:56 CUM PLAY!!!

26:59 Growing up feeling like an outsider with Protestant, Catholic, and Jewish influences

32:43 Condom lessons from his classmate’s nurse mom, detailed anatomical drawings, and watching a graphic sex ed video with his family

37:38 How a book from his grandfather led to his first masturbation session

42:57 Why pleasing his partner is always his focus

44:16 Early masturbation exploration, bedsheet burns and baby powder on private parts

47:49 AOL phone sex adventures with “hot babes” to practice flirting

54:43 Rediscovering his innate confidence through Dominance and plans for writing smut

58:01 Early softcore and R-rated film influences on his sexuality

1:02:53 Making classic movie moves on a first date and his first sexually exciting touch

1:08:33 His first time fingering and revisiting sexy shared memories during sex

1:11:41 An absolute love of blowjobs and navigating his “unreasonable” shameless desire with partners

1:16:41 How a mismatch of communication and sexual needs led to consciously designing a D/s dynamic

1:23:32 Breaking out of the relationship rut of a rare sexual “rewards” system to embrace explorations like watersports and cum play

1:29:19 Daddy Dom bedtime rituals and his ongoing Domination development

1:34:46 Piss play and watching his partner pee

1:38:14 How a college class helped him talk openly about sex and why he thinks everyone is sexy

1:42:52 Looking forward to progressing as a Dominant, building community, and working through mutual jealousy to ultimately add more play partners

1:48:15 Shared desire for accessible sex ed + teaching that it’s okay to explore and break out of expected “norms”

📈 STATS | 40 heteroflexible Dominant white dude, he/him pronouns, monogamous, 24/7 power dynamic, married with kids, works in education, US east coast, into: spanking, cum play, watersports, and his submissive

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

Mermaid roleplay, creating sexy safe spaces, and de-stigmatizing sex work—Kaylani shares how working at a legal brothel has led her down a path of self-discovery, independence, and deeper human connection.

00:00 Why sex work is “intimacy therapy”

03:20 Community, conquering shame, and feeling empowered as a legal courtesan

09:15 Creating safe judgement-free sexy spaces that allows lovers to express their vulnerability

12:51 Mermaid role play and fulfilling partners’ fantasies

17:19 Client success stories and the magic of changing mindsets

19:21 Why do people go to the legal brothel?

23:45 Noticing relationship patterns and what she’s learned from toxic partnerships

27:26 Growing up boy crazy with mixed sex ed messaging

30:13 A long-time lesbian porn fantasy come true

33:28 All-girl orgy configurations

34:43 How she goes deep with clients

36:47 Virgin parties, foreplay tips, and teaching partners how to make her cum

39:05 Why she likes to connect with words before connecting physically

42:51 Feeling supported by her partners and debunking the “transactional” nature of sex work

45:38 Consistent self-care routines and staying curious

48:45 A future of intimacy coaching and helping women leverage sexual energy into financial freedom

51:44 How she’s spreading happiness, acceptance, and compassion

📈STATS | 32 heteroflexible multicultural female, she/her pronouns, single, elite companion, Las Vegas-based legal courtesan, into: meeting new people, deep conversations, spending time with partners, initiating the inexperienced, playing with lady friends, role play, and creating safe spaces for partners

🔗 KAYLANI LINKS | @xoxokaylani

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

Nude car shows, sex toys, and swinging—BJ returns to share his recent explorations and his discovery of a new kink.

00:00 The importance of always having a towel at a nudist car show

05:37 Heightened sensuality in nudity and the different types of nudism

12:19 Expanding his sexual tool shed with FirmTech’s data-collecting TechRing and Performance Ring

17:44 Reclaiming his sexuality post-injury through prostate play and his new favorite cock ring

23:53 Reflections on perfectionism and pursuing excellent ongoing connections

28:45 Exploring a clothing compersion kink and appreciating mutual nurturance

34:01 Post-divorce swinging experiences and getting back into the swinger lifestyle

38:27 Cultivating open-mindedness to live a better, happier life

41:58 Excited for meditative knitting and serving the kink community through leather work

BJ’s episode from October 2024 | Sexagenarian Sexologist

📈 STATS | 60s non-monogamous cis male divorcé, retired protestant pastor, American Midwest, into: nudism, new sex toys, swinging lifestyle

🔗 BJ LINKS | vvrc / sexuality resources

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

30s heterosexual white female, she/her pronouns, monogamous, divorcée, founder and CEO of Afterglow, ethical porn and guided masturbations.

Topics mentioned:

Accounting background, adult film production, aftercare, Afterglow, average penis size, avoiding complacency, awkward sex talk, bisexual curiosity, body movement, boyfriend of 15 years, boy crazy, boundaries in sex work, butt stuff, casual sex, clitoral stimulation, communication, conservative upbringing, cunnilingus, dating apps, deepthroating, divorce, douchebag porn, ethical porn, experimenting with toys, exploration, face fucking debate, female pleasure, first orgasm at 24, friends with benefits, guided masturbation, guided sex audio, health and safety conversations, high school sweetheart, Jewish summer camp, kink openness, kissing, lassoing creative chaos, Lelo vibrator, libido changes, Liberator sex couch, lingerie, lube use, making porn for women, male performance pressure, masturbation, mental health vs sexual health, monogamy, morning sex, natural food startup, non-clinical definition of sex, not orgasming, one partner for 15 years, oral sex, orgasm discovery, partners' reactions to porn, pillow talk, porn consumption, porn creation, porn for women, Pornhub, production logistics, professional sex performers, reading erotic romance, romance novels, same vibrator for years, sensual dance, sex and cannabis overlap, sex as acceptance, sex couch configurations, sex education gaps, sex industry boundaries, sex-positive conversations, shame and vulnerability, startup mindset, STD testing, stress and libido, toy integration, use more lube, vanilla sex, vibrator shopping anxiety, vulnerability, website and tech management, women-focused porn company.

🔗 LILLY LINKS | xoafterglow.com / @xoaftergloww / x / linkedin / facebook

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

34 queer pansexual cis woman, she/her pronouns, polyamorous, co-producer of Failed Films Fest, Los Angeles-based.

Topics mentioned:

Alicia Silverstone fantasy, art films, artful porn, artist residency, ass in the air, BDSM, blood play, blowjob, bratting, butthole, camming, collage art, coming out, communal living, consensual kink, consensual ravishment, cunt worship, daisy chain, daddy kink, desert motorcycle dildo, double penetration, dom/sub dynamics, eating pussy, emotional connection, erotic art, erotic dreams, erotic film, erotic fantasy, erotic house party, exhibitionism, failed films, female orgasm, fingering, flogger, gangbang fantasy, glass butt plug, glory hole, good girl programming, group masturbation, group sex, hairy bodies, health and safety, Hitachi, HSV1, HSV2, impact play, kink discovery, kink.com, kinky collaging, lesbian crush, masturbation routine, masturbation with Hitachi, motorcycle dildo, mutual masturbation, naked beach whipping, nipple clamps, non-monogamy, oral sex, orgasm denial, outdoor sex, pansexuality, pegging, play party, play space etiquette, pleasuring women, poetry events, polyamory, porn festivals, power bottom, pussy, queer sex, ravishment fantasy, rope play, rough sex, safe sex conversations, San Francisco queer scene, sex club, sex education gaps, sex positive community, sex worker art, shame smashing, shared fantasies, shower masturbation, sleepover fantasies, spanking, spitting, strap-on sex, submissive identity, taboo fantasy, tarot-inspired sex art, threesomes, throat herpes, toy sharing, trauma-informed kink, UTI from toys, voyeurism, watching partners masturbate, wax play, whipped on the beach, witchy porn, women-led porn, writing sex scenes.

🔗 LAUREN LINKS | Failed Films / @failedfilmsfest / x

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

A compilation episode!

Topics mentioned:

Acrylic chair, adult theater, anal sex, asses, BDSM, bisexual cum factory, blowjob, brainwashing, brunch play party, chastity, chest writing, cisgender, collie sub, community kink, consensual nonmonogamy, crossdressing, cum eating, daddy dom, daytime play party, dildo, dominant top, domme advice, electric stimulation, erotic photography, experienced players, femme domme, fetish for vacuum cleaners, fisting, flogging, full-time sex work, gender affirmation, gentleman dom, giggling sadist, hand expression, hood play, hypnosis fetish, impact play, indoctrination, introvert kinkster, lactation kink, latex fetish, leather ass, long-term power exchange, makeout, marking up, masked play, mind fuck, mommy kink, muse pedestalization, mutual obsession, nipple feeding, nonbinary dom, objectification, OnlyFans, pansexual, parenting and sex work, partial breath play, pee play, pheromones, play party, podcast guest, polyamory, positive kink stories, professional bully, psychological domination, punching kink, puppy play, queer sex, Razor Cake magazine, responsive desire, rope bondage, sadism, safety and negotiation, scatological themes, scent fetish, sex stories, sex toys, sex work, sexual self-discovery, shared fetishes, spanking, spanking skirt, submission, submissive husband, switch dynamics, synched vacuuming fantasy, tits, top and bottom dynamics, transmasc identity, trans women, vacuum blowjob, vacuum boob play, vacuum fetish, voyeurism, wet brush spanking, wristband signals, writing on body.

🔗 LORDE DESTROYER LINKS | @lordedestroyer / linktr.ee/lordedestroyer

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

A board certified pediatrician with extensive training in Women’s Health, Maternal-Fetal Medicine and Newborn Intensive Care who in 2022 founded Artemis Luxury Wellness to facilitate discussion and exploration of human sexuality through a feminine lens.

Topics mentioned:

Abstinence culture, adolescent patients, adult toy stores, AIDS, anal play, anatomy, artists in residence, Artemis Luxury Wellness, BDSM, bisexuality, boudoir photography, breathwork, chastity, childbirth, Cirque performers, clitoral stimulation, clitoris-vaginal distance, clinical sexology, condoms on bananas, concierge pediatrics, consent education, continuing medical education, cultural norms, deep throating, desert retreat center, direct primary care, doctors and sexuality, ethical non-monogamy, event planning, fire play, food and sexuality, gender identity, genital anatomy, group sex, gynecological care, healing through pleasure, herpes, high-risk pregnancy, holistic wellness, HPV vaccine, HSV-1, HSV-2, immunocompromised concerns, in vitro fertilization, infant care, kink community, lingerie fashion show, luxury experiences, masturbation, medical training, meditation, mindfulness, monogamy, motherhood and sexuality, newborn care, obstetrics, orgasm, orgy play, ouchie boundaries, outercourse, over-the-top events, pap smears, parents and sex ed, pediatrician sex educator, pelvic floor dysfunction, perineum exams, personal boundaries, playfulness, porn, porn literacy, postpartum recovery, postpartum sex, pregnancy hormones, professional boundaries, public shame, recovery and sexuality, rectal swabs, relationship dynamics, resident artist housing, retreat center design, safer sex practices, same-sex education, scolding monogamous culture, sensory play, sexually transmitted infections, shame and culture, shawls of shame, single motherhood, sleep deprivation, slow sex, solo polyamory, spanking, sparkle, spiritual sex, STI testing, swinger culture, talking to teenagers, temperature play, threesomes, toy play, trauma and healing, trust building, vaginal dryness, vaginal orgasm myths, Vegas retreats, vulnerable conversation, wellness events, women’s pleasure, and youth sex education.

Dr Amber’s update from August 2024 | Under the White Coat

🔗 DR AMBER LINKS | artemisluxurywellness.com / @ArtemisLuxuryWellnessLV

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

42 Black straight cis male, married, Colorado-based creator

Topics mentioned:

Anal play, ass worship, athletic partners, baby care scheduling, bareback sex, BBQ bull, bisexual curiosity, black community and sex, body confidence, body image, cock comparison, cock play, cock sucking, communication in threesomes, condom use, consent education, cuckold feelings, deep connection, doggy style, dominant energy, ethical non-monogamy, fantasies, fuck licking, gangbangs, group sex, handoffs, hot wife, hotel meetups, intimacy, interracial dynamics, kink exploration, kinky redhead, lifestyle parties, male bisexuality, male submission, marital communication, masturbation, military marriage, mutual pleasure, nipple play, OnlyFans, open relationships, pansexual moments, peer pressure, play party vetting, porn preferences, postpartum sex life, privacy, reclaiming, redheads, relationship honesty, roleplay, same-room sex, secret sex life, sex education, sex shame, sexual awakening, sexual confidence, sexual trauma, shared partners, size comparison, soft dominance, stag, swinger websites, threesomes, trust building, video production, voyeurism, watching wife, weekly testing, young sexual experiences.

🔗 JAY LINKS | OF / @hotwifesheila

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

Topics mentioned:

Adventure, Airbnb, artisan floggers, ass cheeks, ass cutout, attraction, BDSM, blowjobs, bucket list, camgirl, camming, cock worship, communication, companions, consensual porn, content creation, cuck fantasy, degradation kink, ethical porn, fantasy roleplay, feet, female pleasure, flogging, floggers, Florentine flogging, foot fetish, fuck sandwich, fucking machine, goddess worship, group sex, hot tub, independent sex work, kink, Layla, masturbation, masturbation vacation, masturbation reset, Masan Clothes, masturbation techniques, mutual desire, non-monogamy, OnlyFans, orgasm, o-shot, oxytocin dump, panty selling, pegging, play parties, porn, porn recommendations, Pornhub, producer brain, pussy worship, reclaiming, relationships, roleplay, safe container, Sex Panther, sex stories in the park, Shakespeare and sex, shared fantasies, Simian, spanking, spanking skirt, spit play, stage and cock queen dynamics, stags and cuckolds, submission, submissive dynamics, swinger dynamics, trampolining fantasy, trust, voice memos, wetness, worship, writing porn fantasies.

🔗 KATHY LINKS | strictlyanonymouspodcast.com / @strictanonymous / x

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

40s bisexual female, she/her pronouns, erotic romance author, host of the erotica fiction and sexuality podcast: Oh F*ck Yeah with Ruan Willow, a voiceover artist, audiobook narrator, and blogger, into: power play, exhibitionism, and outdoor play.

Topics mentioned:

Audiobook narration, author identity, bad sex education, being judged for kinks, bespoke erotica, blowjob scene research, body pleasure education, clit mapping, clit sucker, clit junkie, communication about sex, consent education, content creation, cunt vs pussy, dirty talk, editing audio, educational erotica, erotic fiction, erotic romance, erotic writing process, erotica podcast, exhibitionism, fantasy exploration, foreplay as daily care, food play, fucking, giantess fetish, gratification, grinding, hot audio stories, human dildo, kink judgment, kink shame, kink variety, Licking Sip Coffee Shop, Linktree, masturbation, master/slave kink, microphilia, morning writing, naughty narration, non-linear storytelling, NSFW podcast, orgasm, outdoor sex, penis owner identity, personal fantasies, pillow humping, pleasure discovery, power play, pussy saddle, reading erotic fiction, reframing romance, restraint play, romance vs erotica, Ruby Glow, Ruby Blush, rules of romance novels, same-sex giantess sex, sex acts and identity, sex audio content, sex blogging, sex furniture, sex norms, sex outside, sex shame, sex toys, sexy audiobook acting, sexy writing, shame-free living, size fetish, smut, social media sexiness, spanking bench, spicy romance, squirting, taboo fantasies, Twitter polls, vagina terminology, voiceover artist, voyeurism, writer identity, writing inspiration, Zoomio.

🔗 RUAN LINKS | linktr.ee/ruanwillow

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo