It depends on if condom is too tight, exercising b4 appt, mind somewhere else. Peens have a mind of their own. Im speaking from my own experiences in sessions
Serious question. OP, how long have you been having sex, and how long have you been using a condom when having sex?
There is not enough information to answer your question. Did you marry your high school sweetheart, and 20 years later you are just no venturing into extracurricular sex? Did you just recently lose your virginity? How old are you?
Or as stated earlier just ask the lady if she does bareback.
The condom might be too small. If you're thick, use a larger condom, such as Skyn Large. (Trojan Magnums are the same width as regular Trojans, so avoid those.)