i was always really worried about it and i was in fact fingered for the first time on monday (completely unexpected) all i can say is go with the flow (we made out on and off but it doesn't mean u have to) and make sure u tell him if he hurts you, the guy i was with had also been with girls before. relaxing and enjoying yourself def helps, i was a bit tense at first and it made it slightly painful but once i relaxed i really enjoyed it