Since you didn't indicate what type of herpes tests he had, I am going to assume that he had the blood test. And it is true that the herpes blood tests have higher false positive/negative results than do the swab tests, the probability of having 3 false negative results is highly unlikely. So I would say chances are that your bf is negative for herpes. My first thought, after reading your post, was that your boyfriend contracted a yeast infection from this one night stand. Yeast infections can be transferred back and forth between partners, that is why it is suggested that both be treated when, most typically, the female is diagnosed with a yeast infection. Itching and redness, and even a rash are common symptoms of yeast in men.
Hope this helps!
Hugs!
Kimi