Hallow Dear,
Let me answer your queries in two stages as I gather you are having two concerns.
1. Regarding the difference in level of orgasms by dildo and live sex: Women have capacity to have two orgasms - one is clitoral orgasm and second is vaginal orgasm. Clitoral orgasm is achieved by stimulation of
clitoris or
labia minora also. The first to achieve is clitoral orgasm. After clitoral orgasm, there is a phase of sort of resolution or relaxation. However, if the intercourse is continued further, woman gets vaginal orgasm. Vaginal orgasm is attained by stimulation of 'G' point which is situated somewhere midway on the front wall of vagina. If during natural sex, after your clitoral orgasm, the man withdraws his penis, you will never get the vaginal orgasm. In fact about 90% of women have not experienced their vaginal orgasm in their life; moreover they are unaware of such orgasm. However, if you are masturbating with dildo, it is up to you to continue even after the clitoral orgasm; hence you have one more and higher orgasm than natural sex. If you provoke your boyfriend to continue with the sex even after the clitoral orgasm, you may reach the same orgasm that you experience with dildo.
2. You are not getting sensitive feeling that you were getting with dildo previously. It is likely that due to regular
masturbation, your erratic feelings or imaginations might have gone down. Masturbation is a state of fantasy of thoughts. If you are loosing fantasy your arousal may be delayed and so is the orgasm. If arousal is delayed or insufficient, the vaginal secretions will be less. Dry handling of the genital organs is always uncomfortable which lowers the orgasm. Therefore I will advise you :
a. To wait till you are 'wet' before you insert the dildo.
b. The other option is to use lubricants. Oil based lubricants are harmful to the woman's genital organs; please use water based lubricants like vaginal jellies.
c. I case your erotic fantasy is insufficient, make use of erotic literature or videos.
d. You may change the size of the dildo.
I hope this helps you.
Dr. Nishikant Shrotri