My first word of advice would be that it is a bad idea.
You are trying to fill a void in your life with sex. And sex is not there to fill a void, but rather to add extra pleasure.
You need to get to the bottom of your feelings and emotions and understand this void you are experiencing. A good T will help you; and to combat depression, I'd really recommend you take charge of your own life and get back onto meds. I'm sorry your mom is not in agreement with the idea, but it is your life, you deserve to be happy and have a quality life, and you need to make decision.
Obviously your age would be a factor in knowing if you are indeed able to make these decisions for yourself.

Every person you sleep with takes a part of your soul. In a way, you are bound for life. The relationship you have with these guys will be very different after you've had sex with them. Hence sex was initially intended as part of an intimate relationship.
If you can, please stop this behaviour and rather get to the root of the issue and start healing yourself in a healthy way.

I've been through both the depression, as well as the thoughtless sexual encounters. The depression is painful.
THe sexual encounters may make you feel better at the time, you may consider it an achievement, but a while down the line you will look back and feel bad about those decisions or even regret them.

Feel free to PM me any time - we're here to offer you support.