Re: Performance anxiety and vacation...advice?
I am not a quick to suggest the pill. He is fairly young to be needing medication for any truly physiological reason. As you state, he is most likely psychologically concerned that he will cum too quickly and leave his partner with a very bad impression of his abilities as a lover.
Here is the best solution I know.... Make it clear that the play will continue past his first orgasm. Have the other woman make clear her desire to have him "let go" the first time they have intercourse and get his orgasm over as quickly as he'd like. The less pressure he feels with that first interaction, the more likely he will be able and willing to recover for a second, grander performance. Build in an intended break of between 10 and 20 minutes before you continue with the sexual interaction (get a drink, have some light conversation, do whatever). Once he has been given permission not to perform well, he will likely be able to perform better the first time and be able to come back for a second and third performance later into the evening.
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