Ooh. I feel you there. I'm the same way, but I haven't lost a ton of weight. I have always been really thin. I'm tall, and am thin for MY frame, which is small (i can get my third finger past my thumb knuckle when I wrap my 3rd finger and thumb around my left wrist). I wear boxer brief and sometimes just boxers, and usually just let it hang loose. I always wear loose jeans though (i did before I even knew I was hung or showed a bulge). It will likely become more comfortable, but it may take some time.
The best of luck to you!
Me