Hallow Dear, Masturbation is a normal physiological act. Woman can masturbate in two ways - clitoral masturbation and vaginal masturbation. Clitoral masturbation is performed by simply stimulating clitoris. It does not require any article to entre the vagina and still gives a feeling of orgasm. However, clitoris should not be stimulated dry lest discomfort and pain. Use of some lubricant or even water is advised. Vaginal masturbation requires putting some article inside the vagina. Smoother and appropriate sized articles will not hurt vagina and cause pain. Use of lubricant eases the entry of the articles. The best article is dildo of appropriate size. Usually the pain is not after the insertion; it is during the insertion as you reflexly contract the muscles of vaginal outlet during insertion. This is known as vaginismus. You may try taking deep breaths with wide open mouth during insertion, which will prevent the contraction of muscles of vaginal outlet. Whether you masturbate of your own or get it done from your boyfriend makes no difference. However, while getting it done from your boyfriend, there is always a possibility of landing into sexual intercourse. You must be prepared for it. I hope this clarifies your doubts. For any more information or clarification, you may ask me a Direct question on this forum. Dr. Nishikant Shrotri