I read thru all these posts just before Halloween of this past year. I was invited to a Halloween party and I wanted to really go for the shock factor. I'm relatively conservative, so I figured dressing up as a female would really freak out my friends.....and it did!
First of all a big thanks to all the contributors to this thread. There is tons of good info in here. Some of you are a bit out there in left field, but I've got no issues with any of that. If that's what rocks your world, go for it! After my crossdressing experience, I kinda like playing shortstop.
Anyway, to help return the favor, I thought I'd post my experiences so other dudes might be successful trying to do the same thing. I suppose if I was brave enough, I'd even post some pictures, but I'm thinking maybe that's not the best idea. I don't know. You be the judge. If there's enough interest, maybe I can be coerced to include some pics. In the meantime, here's how I did it:
1) First thing, if you're the least bit turned on by doing this, your penis is not gonna behave like you want it to. Go "take care of business" if you have to, otherwise you're gonna have problems. Even a semi erect penis will be a problem. You also want your scrotum to be as close to your body as you can get it. A coolish shower might help or a quick application of some ice....whatever you can deal with.
2) Find yourself some privacy. Bedroom, bathroom, whatever.
3) Ok. You need to be naked at least from the waist down, but you might as well just be fully nude. Being shaved helps some, too, but it's not a requirement.
4) Stand like you're taking a leak at a urinal: feet spread apart a little and both thumbs providing "alignment", i.e. at the top of your penis near the base.
5) Place the index and middle finger of your left hand under your left testicle and the index and middle finger of your right hand under the right testicle. Using your thumbs as leverage, push up and in on the testicles with each hand. If your scrotum is cold, they should go right up into your abdomen.
6) Once they're up there, use one your hands to reach from behind your legs and grab your penis and pull it down towards your anus. As long as you hold it there, you testicles should stay right where they are, in your abdomen. If you let go of your penis, everything will return to the way it was and you get to start over.
7) To keep everything in place, there's a couple things you can do. I had really good luck using a pair of women's boyshorts. They generally come in S, M, L sizes. Make a guesstimate and get one size smaller than you'll need. They are usually very stretchy. Once you get your tucking figured out, pull a pair up to your thighs. When you get your penis pulled all the way back, pull the boyshorts the rest of the way up and everything should stay right where it's supposed to.
8) For extended "hold", use the technique that was posted here earlier. Buy a box of panty shields and some surgical tape. When you have everything in place, tape the panty shield against your body and it will keep every thing looking "smooth". I did this for my costume. Yeah, it'll be a hassle using the bathroom, but as long as you haven't covered the end of your penis, you can sit down and take a leak, no problem. One thing I discovered in MY particular situation is if you do happen to get "excited" AFTER you get everything secured, nothing happens. For me, it's pretty much impossible to get an erection with my penis taped back. Even if I just use the boyshorts to hold things in place, an erection is almost impossible.
As I mentioned earlier, the costume turned out great! I'd do it again in a heartbeat. I still catch flack from my friends, but I can deal with it. I worked hard to get the look I was shooting for and I think I was very successful. Some of my friends didn't even dress up, but the best part was some of my friends didn't even know who I was. That was worth it right there!
Best of luck to all of you! Comments and suggestions are always welcome.