He is uncertain of his wife’s virginity because there was no bleeding
Question

                I got married about five months ago and intercourse with my wife was difficult at first, but she did not bleed until now. I do not know if she was a virgin or if something happened that I do not know about – Allaah forbid – especially since she was engaged before I got to know her, to a young man who is known for his immoral ways such as drinking, taking drugs and committing zina.

 Please advise us, may Allaah reward you. I do not want to wrong or be wronged, but the Shaytaan is not leaving me alone.
Praise be to Allah.
    Firstly: 

    You should note that the shaytaan is extremely keen to cause 
    division between a man and his wife. It is narrated in a saheeh report that 
    the Prophet  (peace and blessings of Allaah be upon him) said: “Iblees 
    places his throne on the water, then he sends out his troops, and those who 
    are the closest in status to him are those who cause the most tribulation 
    (fitnah). One of them comes and says, ‘I did such and such,’ and he says, 
    ‘You have not done anything.’ Then one of them comes and says, ‘I did not 
    leave him alone until I caused division between him and his wife.’ Then he 
    brings him close to him and says, ‘How good you are.’” Narrated by Muslim, 
    5023. 

    In order for the shaytaan to reach this objective of his, 
    there are many methods he uses to reach a man, one of which is creating 
    doubt about his wife’s chastity. 

    Secondly: 

    You should also note that the fact that a woman does not 
    bleed the first time she has intercourse does not necessarily mean that the 
    woman has been unchaste, because the hymen may be elastic and there is no 
    bleeding when intercourse takes place, as has been stated by doctors.  

    It may also be broken for many reasons other than 
    intercourse, such as sports, jumping and so on. 

    Moreover, the blood that is usually expected may be only one 
    or two drops, and this blood may come out mixed with other secretions, so 
    the man does not see it because it is not visible. 

    For all of these reasons and others, it is not permissible 
    for a man to doubt his wife’s chastity because she does not bleed when he 
    first has intercourse with her. The fact that there is no bleeding does not 
    mean that she is not chaste, just as the presence of bleeding does not mean 
    that she is chaste, because some women have surgery to repair the hymen. 

    If your wife is a chaste woman and is religiously committed 
    and of good character, then you should not let the shaytaan have any way of 
    getting to you and spoiling your life. Seek refuge with Allaah from the 
    accursed shaytaan, and do not doubt your wife without any clear proof. 

    May Allaah bless you both, and join you together in goodness, 
    and divert the plot of the shaytaan away from you. 

    See also the answer to question no. 
    40278 for more 
    information. 

    And Allaah knows best.