FirmTech rings use a peno-scrotal design, so fit depends on two loops, not one. The first sits under the testicles and the second around the base of the penis. The strap should feel snug and secure, never painful. The Performance Ring and TechRing are rated 3 of 5 for tightness, and the MaxPR, a slimmer and snugger version, is rated 5 of 5. If the Performance Ring feels loose even at its tightest setting, the MaxPR is the step up. If anything feels painful or numb, loosen it or take it off. Every ring is covered by a 30-day money-back guarantee if it simply does not fit.