Ashley: Everyone deserves to be happy. Maybe you feel like you deserve to be punished for hurting other people around you. If that is true, then this: In society, we punish minor crimes with community service. So go sign up to serve Christmas dinner at the local homeless shelter, offer to mow the lawns there, sweep the floors or clean the toilets. Or if you don't want to get your hands dirty, then make a donation or two. It doesn't have to be a lot of money. And then let it go. If you want to know one of the better shelters to make a donation to, then PM me. In my job I work with a lot of shelters and rehabs.
The women you dated and hurt, they have moved on. If you feel you have to apologize to them, then find them on Facebook and send an apology. If that feels weird, then do the community service or make the donations, and let it stand as your contribution to humanity.
Now about the shame and guilt. Learn to ask "why?" Why do I feel shame and guilt? Well, as small children, we have no shame or guilt. When I was five years old and wanted to wear girls' bikinis, I felt no shame or guilt about it. No, someone put the shame and guilt there in the back of my head, and that would be my mom and dad.
After Dad had his stroke in 2009, I spent five years having shouting matches with him inside my head. Five years! Then finally I broke down, admitted to myself I was transgender, and started dressing at home. When I realized the source of the shame and guilt, and learned to put it aside, and tell myself that I deserved to live my own life, not the life someone else wanted me to live, then my blood pressure came down, and I started liking myself a lot better.
But maybe you cannot do this on your own, and this is why you have to trust your therapist.
But know this: We care about you. We honestly want you to be happy. We know that you have value. So don't be so hard on yourself.