Also my new boyfriend has psoriasis and dry skin on his hands.
Welcome to the Forum. You do not have the option of choosing who answers your questions. As you know, Dr. Handsfield and I share the forum. Today you happened to get me. FYI, the reason we share the forum is because we have worked together for over 30 years and while our verbiage styles vary, we have never disagreed on management strategies or advice to clients.
It appears that you have had sex with at least two partners over the past few months, participating in a number of different sexual activities. Most exposures with your prior partner, who sounds to be rather low risk from what you say, were unprotected while with your current partner genital exposures are condom protected but oral sex is not. I would not count your receipt of masturbation (fingering) as a risky activity at all for any STD.
STDs can be present in both men and women as asymptomatic infections and for that reason regular screening (testing in the absence of symptoms) is recommended for persons who have new or multiple partners on an annual basis- it sounds as though you do this (good job!). In your own circumstance, it sounds as though your prior partner was not particularly high risk (most people do tell the truth and you seem to believe him) and indeed, most people do not have STDs of any sort- thus your risk for infection from that relationship is probably low. In your current relationship, oral sex is a rather "inefficient" means of transmitting STDs and even if your partner did have infection, oral infection would be uncommon and his performance of oral sex on you would be unlikely to result in transmission from his mouth to you even if her were infected. Condoms make your genital sex safe.
Unless you have a particularly strong reason to distrust either your prior or your current partner, or you develop symptoms, you will probably be fine not seeking testing until your next routine GYN check in a few months. Both you and your partners sounds to be rather low risk as long as you remain monogamous going forward.
I hope this is helpful. There are no absolutes as to when the best time for asymptomatic screening is. While there is no urgency to seeking testing at this time, it is ultimately, of course, up to you. EWH