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Woolsey would have felt more guilty, but Radek and Rodney had some kind of 'open relationship' which Rodney brought up incessantly, and seemed to think made them incredibly modern. Woolsey was there when someone had conversationally mentioned that she couldn't imagine having an open relationship, and Rodney had berated her like she was suggesting people ought to go back to hanging bridal sheets in the window or something.
Woolsey was of the mind that non-monogamy functionally negated the whole 'marriage' thing, and rendered it little more than a fraud to bilk taxpayers. But his high-mindedness couldn't be sustained in the face of Radek's offer; he'd been terribly attracted to Radek from the moment they met, and even though he would have liked to believe otherwise, Woolsey knew he would have slept with him in almost any circumstance.
It started as flirting in the History of the Future Museum, escalated to hand-holding during the Borg Invasion 4-D, and became groping in the dark during the Klingon Experience. Woolsey had never been comfortable with public displays of affection, but they'd both been light-headed with fanboy excitement. They were going to stop for a drink at Quark's Bar, but they'd ended up going straight back in Woolsey's hotel room.
Radek looked great with his long hair a bit sweat-slick and the murmuring in Czech was a huge turn-on. The sex was good, more frantic than Woolsey was used to, but then again, he'd never been the 'other man' before. Woolsey already knew this wasn't about him, but you didn't need to know a bit of Czech to make out the word 'Spock' in Radek's murmuring at least a couple times, especially when he was in the throes of orgasm.
Woolsey knew most people would have been offended, or at least embarrassed, but Woolsey was actually kind of flattered. He'd had many of his own masturbatory fantasies about Kirk's first officer. And while he'd been told he looked like EMH, he always thought that spiritually, he was more kin to the Vulcan--that most cool-headed, logical of races.