Anal Play Progression & Toys

Fisting toys, figging, and fulfilling French maid fantasies—Lilith shares her journey of shedding shame, embracing trans identity, and diving headfirst into kink and self-pleasure.

🔗 LILITH LINKS |  @lilithmkieffer

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📈 STATS | 44 white trans woman, in a relationship of 15-years that is monogamous, with some kinky hall passes.

⏰ TIME CODE

00:00 From Roman Catholic shame to self-pleasure queen with bad dragons, plugs, and tails

06:15 Dressing up, public confidence, and the joy of shocking strangers

10:44 Tent sex, homemade mead, and the kinky beginnings of her current marriage

17:00 Exploring BDSM: fire cupping, caning, and fantasies of being tied, pegged, and used

24:48 Parenting while hiding creative self-expression, and finally coming out to adult kids

30:55 Deep-throating toys, oral fantasies, and wanting to be spit roasted

38:13 Building kinky community, shopping for poofy dresses, and dressing up for GenCon

45:22 Anal play progression: bad dragons, vibration, and prostate pleasure

50:12 Fetishization, sexual confidence, and what she’s still hoping to experience

54:35 Castle sex, pegging dreams, and divine timing with her supportive wife

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🤩 TOPICS | Anal beads, anal play, anal sex, art class, bad dragon, bdsm clubs, beekeeping, being pegged, being spit roasted, blowjobs, board games, body image, boots, braided hair, breast forms, burlesque, caning, catholic guilt, chest plate, cleaning in a maid outfit, clove-infused lube, community band, confidence, consent, conservative upbringing, corsets, costuming, cotton thongs, creative self-expression, deepthroat, delivery driver, dressing up, drag shows, face app, face sitting, fantasy play, fire cupping, fireplay, fingernails on cock, French horn, French maid fantasy, gender fluid, gender identity, gencon, ginger figging, graphic designer, hair pulling, hall passes, handmade lingerie, heels, hot wax, Indiana, Instagram attention, intimacy, kink curiosity, lace panties, latex, learning to sew, long hair, lingerie, married sex, medieval reenactment, monogamy with exceptions, naked cooking, nipple play, nudist lifestyle, online fetishization, oral sex, pegging fantasy, playing dress up, playing with wax, polyamorous partner, ponytail pulling, prostate play, public sex, queer identity, reenactment groups, remote-controlled butt plug, rimjob, roleplaying games, romantic connection, Roman Catholicism, satin thongs, seasonal cosplay, self-pleasure, sensation play, sewing bras, sexual shame, shibari, shoe paddle, shoes, silicone toys, size progression, solo anal play, spanking, spit roast fantasy, strap-on oral, strip clubs, subspace, submissive identity, synthetic breasts, tight clothing, toy collection, trans community, trans visibility, trans woman, Victoria’s Secret thongs, visual pleasure, warm lube, wax dripping, wedding dress dreams, winter fashion.

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