Do you have any advice for an FTM (female-to-male) transguy for using a strap-on? Any advice for first-time strap-on users?
In a previous column, which you can read here, I answered a reader question about getting started with strap-ons. The "How-To" section of the Tool Shed website has sections on choosing a harness and choosing a dildo that also could be helpful. Your question seems to encompass using the strap-on as well as choosing it, so I'll discuss that aspect here.
When using a strap-on, most people's biggest concern is going to be the stability of and level of control over the dildo. For some transmen, feeling as if the dildo is a natural extension of the body may be particularly important. The best way to achieve this stability is to get a good-fitting harness and to practice using the harness in different positions before having sex with a partner.
It's worth it to invest in a harness with sturdy, adjustable straps that can hold the dildo close to the body and allow for adjustments on the fly. Depending on the position you and your partner are in, you may find that adjusting the placement of the dildo in relation to your pubic bone allows for greater control or deeper thrusting. Tightening or loosening the leg straps of the harness when you switch positions can also help. When choosing a harness, consider how easy it is to shorten or lengthen the leg straps quickly while you're wearing it. Buckles on the side or front of the harness help with this. Some people find that a one-strap, g-string style harness needs less fiddling than a two-strap, but this is a matter of personal preference.
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This may sound silly, but taking the harness for a test run by yourself is good practice and will allow you to make strap adjustments that keep the harness secure before you're in the heat of the moment. Set up some pillows and hump those things furiously in a variety of positions. Note the times that you don't feel connected to the dildo, make adjustments, and try again.
Sometimes a dildo will wiggle or pop out not because of the harness fit, but because the ring holding the dildo is too large. If you have a harness with a removable o-ring, you can purchase different ring sizes and/or inflexible metal rings that will hold the dildo more securely. Otherwise, you can get a neoprene or foam "doughnut" that slips over the dildo and creates a larger, more secure base in any size ring.