This was weird for me to admit to her, but yes…I do like it when her boyfriend teases me about my small cock. Goes hand in hand with her pussy belonging to him too
I would yes !
You were surprised when you boss asked your wife out on a date, and even more surprised when she accepted the invitation without telling you about it or asking your permission -- and now you're surprised that she is asking your opinion on whether she looks sexy enough in this dress to make sure that he will want to have sex with her tonight. What has become obvious is that, in her mind she has already started cuckolding you, and you can sense that nothing is ever going to be quite the same after her date tonight.