I used to be just like the OP in so many ways. I am usually in the spa not here, as I hire masseurs and not escorts. But this topic is close to my heart and I felt compelled to weigh in. I was 130 lbs overweight. Short, bald, smaller package, not the ideal man bait. I had weight loss surgery 10 years ago. Lost 100 lbs, but put 30lbs back on. Left me down a net 70. Still 60lbs overweight when I enteted the massage scene. I picked what I thought was the hottest guy in my area. We have become regulars. He has built me up, encouraged me, and motivated me. By sharing myself with him, I have now lost another 30 lbs and my massage experiences are now incredible. Many masseurs are used to dealing with guys with confidence issues and if you find the right one, it can really help. Dont stop trying. Put yourself out there. If you connect with right guy, it can change your whole life. I credit the 2 masseurs I see regularly with my new found self acceptance. They both say, in total honesty, it's the energy the client brings that determines how they respond to you, much more than the physical attributes. Go get em tiger!