Webinar hosted by Cherish Amber of CHERISHAMBERCOACHING

Join us for an engaging and inclusive webinar on Strap-On Sex, where well take you through a comprehensive how-to guide on using straps for any gender and experience level. Whether you're a beginner or looking to refine your skills, this session will provide practical tips, techniques, and insights to enhance your sexual experiences and confidence.

Choosing a Dildo: Shape, Size, and Material

Shape, size, and material all matter, and the options are far broader than most newbies assume. Glass, silicone, and stainless steel are all on the table, and the aesthetics range from realistic skin tones to octopus tentacles to something that simply looks like you have grown a dick in the middle of the day. Amber's point was less about any single recommendation and more about broadening the mind rather than assuming a dildo must look a certain way.

Pegging dildos and vaginal or vulva-penetrative dildos are different shapes, and Amber held up examples on camera to illustrate the difference. She also flagged where in the world shoppers get the best experience. Berlin, she said, has the best strap and dildo shops, with walls offering something like two hundred options to choose from. Toronto and various cities across the US and Europe also have shops offering full trying-on sessions. The United Kingdom doesn't have this yet, and she is working on creating a bespoke try-on experience to change that.

The recurring frame here was beginner's mind. The right strap for one person is not the right strap for everyone. Comfort, fit, the experience both partners want, and past experience all factor into the decision.

Start Small, and Talk First

Amber's most emphatic safety insight was simple: start small, and do not run before you can walk. Because the person wearing the strap cannot feel anything, they receive no feedback about pressure or depth. A fantasy of being penetrated by an enormous penis is therefore not a sensible starting point, and this applies to both vaginal and anal play. Taking a large dildo vaginally is very different from taking a partner's penis, precisely because it is not attached to a body.

Communication belongs before the purchase, not after it. Amber urged couples to talk before they shop, try on, or attempt strapping anything at all. Simple openers do the job: how would you feel about trying this, and what are your expectations? She pointed attendees toward her Whet Your Appetite video for open communication tools, framing the goal as mutual pleasure and satisfaction, with both partners on the same page before anything begins.

Fit, Feel, and the Harness Itself

Practical fitting advice was straightforward: try the harness on before any sex happens. Amber gave the example of a suede strap from Skin Two where the piece sitting between the legs can feel uncomfortable, exactly the kind of discovery best made in advance rather than mid-moment.

Demonstrating live over yoga pants, she walked through a laced suede and fabric strap-on designed with a female body in mind. It came with three interchangeable O-rings, and she explained that larger dildos need a bigger ring so the base pulls tight for thrusting. The dildo can be threaded so its base sits against the skin or in front of the material, and the harness includes D-rings at the back for all her kinksters.

Her fitting tips were specific. Adjust and fasten everything before play, because poppers and buckles are fiddly and unsexy in the heat of the moment. Find your buckle number in advance. Wear it high, and get it really tight for maximum front control and sensation. On materials, she strongly advised avoiding nylon-strap starter kits, because the webbing feels like rucksack straps against the skin and she wants everyone's first experience to be a good one.

The Ring, the Leverage, and the Biggest Myth

The ring in a strap gives the dildo something to push against, which is essential for firm grip and leverage. On some designs the dildo mounts behind the ring so that the ring presses against the wearer's body, which matters if the wearer is also receiving vaginal sex and means the harness will get lubed up and exposed to body fluids.

Positioning changes everything. Worn high, the thrust comes from higher up. Worn low, it comes from a completely different place. For people with a tummy, tightening the straps can leave the tummy sitting over or under the harness, shifting the dildo's angle. This is why Amber recommends treating first sessions as an open-hearted, open-minded experiment rather than a performance.

Then there is the myth she debunked again and again: putting on a strap-on does not give you a penis. There is no sensation in a strap-on. The only sensation comes from watching what a partner is doing and receiving. Wearers cannot feel depth, tension, or resistance the way a penis owner can, which makes communication the direct substitute for sensation. Start with explicit verbal cues such as just the tip in, and learn the nonverbal cues over time. Amber pushed back firmly on the idea that asking lots of questions breaks the mood. It doesn't, though wearers will need to ask far more than usual.

Laughter, Nerves, and the Window of Tolerance

For a first session, Amber's advice was to laugh. Laugh and joke about the awkward mechanics, the doing up of buckles, the sudden growing of a dick, the appearance of a dildo or a tentacle. Also, playful dirty talk can help set a fun tone.

Through a coaching lens, this matters more than it might seem. Amber wants people to stay inside their window of tolerance rather than grin and bear it, a habit she attributes to porn and would like to completely eradicate. Laughing signals to the nervous system that what is happening is okay.

She also offered reassurance that the awkwardness is temporary. Once someone learns to use a harness, the buckling up becomes sexy anticipation, because you know you're about to get fucked. And here is the counterintuitive part: the giver is often more nervous than the receiver. The receiver is anticipating pleasure, while the giver is wondering how they're going to do it, and what they need to do.

Lube and Cleaning, Done Properly

Use a lot of lube. Amber recommended an industrial size bottle kept bedside rather than a teeny travel bottle. Water-based lube is preferred because it doesn't degrade silicone toys. Plant and oil-based options that are hormone-free, glycerin-free, and organic offer more slipperiness for anal play and suit stainless steel, but they degrade condoms, so choices need to be made with that in mind.

For cleaning, a detergent-free toy cleaner spray is essential. Harness bases are hard to rinse, get dirtier than other toys, and leather or suede harnesses are ruined by water and repeated soap. Silicone, stainless steel, and reinforced glass dildos can go in the dishwasher on a sanitize cycle, top shelf, with no dish soap.

Anal Play: Hygiene, Shame, and Safety

On hygiene, Amber advised avoiding shower-hose douching, because the water pressure is too strong for internal organs, and going easy on soaps, which can irritate the anal lining and cause pain. Practical alternatives include keeping baby wipes nearby, showering together, and using toy cleaner or the dishwasher for gear.

Her shame-reduction message was central. Encountering poo during anal play is natural and no different from someone starting their period or spit landing somewhere unexpected. As she put it, we create space for nobody to feel shame.

One safety rule was repeated emphatically: never use an anal toy without a flared stopper or base. They go in and they won't come back out, and nobody wants a trip to the ER or A&E to explain it. For preparation, butt plugs make a good on-ramp to pegging, with slightly longer plugs preferable to short ones when building up to penetration. Start very small and work up.

Positions and Audience Questions

The possibilities are endless, but for anal and pegging beginners Amber recommended positions that open the pelvic area, such as knees bent and drawn toward the chest, or lying on the back. Once the receiver is comfortable, they can take it from on top, which is where, in her words, the strap can really come into its own.

During the Q&A, anal orgasms were confirmed as a definite thing. Amber also flagged audience questions she promised to return to, including how to find harnesses that fit women's bodies and suggestions for beginner couples.

Original webinar was live-streamed on SDC.com on Friday August 23, 2024