Background info(sorry for length)-
So I'm 21 and have had at least 8 failed experiences(all different girls) at trying to have sex. I've gotten bj's and hj's but I've never actually had intercourse. I finally figured out the problem in January(heavy porn use and masturbation for almost 10 years, in latter years its been mainly tranny even tho I'm not gay), and the past 6 months have been more or less a roller coaster of rebooting.
My first try I went 3-4 weeks no PMO, and that ended after the girl I had been seeing gave me a handjob. Around this time I honestly thought I could've had sex(after dry humping in bed a few times I was very close to ejaculating), but the girl was a virgin and did not want to. After this one handjob, I started getting the cravings back. I stayed off porn for a couple of weeks, but something odd happened laying in bed one night. I wanted to give in but restrained from touching myself. The fantasies were flowing in my head, I was rock solid, and I ended up "mentally masturbating", as in I reached orgasm without actually masturbating. The fantasies alone got my aroused enough to ejaculate. I thought that this was ok, but after one or two more times over the next week, I started looking at pictures of attractive girls and trying it out. I started needing slight manual stimulation, and slowly but surely I went back to regular porn and needing more manual stimulation.
I didn't do this as often as I used to(prior to 2011 I would masturbate at least twice a day every day), and never did it more than once or twice a week. I still never got the chance to have sex with the girl I was seeing, and we stopped seeing each other about a month ago. I ended up having a somewhat one night stand with a girl I knew from class towards the end of May, everything was going well and I could keep an erection until I began to finger her and my erection went away completely. I told her I couldnt have sex bc I didnt have a condom, and ended up just going to sleep. That made me realize that I had to start the reboot process again.
A week or so after that I began to see a different girl. I had been without PMO since then, and knew I was going to get a chance to sleep with her one night bc she invited me to spend the night. I masturbated(no porn) that day because I thought I'd be able to perform that night and I didn't want to cum too quickly. Again, I was hard all night until we both got completely naked, and it went limp. I said I didn't have a condom and we had a mutual masturbation session and that was it. I again gave up PMO and it's been about two weeks. Unfortunately, last night I was viewing facebook photos again and ended up "mentally" masturbating to orgasm.
Sorry for the long post, but here are the concerns I've been having
1.If I'm to the point where I can reach orgasm without actually touching myself(I even googled this and couldnt find anything), how far along in the rebooting process have I come? It seems like that would mean I was back where I should be.
2.How much will that one relapse set me back? I'm getting to the point of desperation. Im not bad with women(I used to have confidence issues but a lot of that has subsided since I first decided to reboot. I'm good looking and have no problem attracting other girls, but it's SO DIFFICULT having girls like you and not being able to have sex). I would like to say that I have seen some improvements(during most of my failed experiences during 2009-2010, foreplay sometimes didnt get me hard, now I can almost always stay hard except for when intercourse is actually about to happen.)
Should I stop seeing any females altogether until I can actually go without PMO for 30-60 days?