I didn't catch what MOS you are going in for, but let me offer some insight from what I know. I spent a little over 4 years as an enlisted Infantryman, went to OCS and became a Signal Corps officer. I didn't buy my first skirt until I was in OCS, but I did have a lot of TS/TG pictures on my computer. One day my roomate let someone else use my computer and my stash was found. Other than a whole lot of teasing - seemed that the entire company knew about it, nothing was said - and I was selected for OCS by the commanding general of the division at the recommendation of all my commanders from the brigade on down. Infantrymen are known for having odd fetishes anyway, so I just blended in. Depending on where you go, your chances of being able to dress in your home are slim - most likely you'll live in the barracks. That said, the new barracks tend to have separate private bedrooms with a shared bathroom/kitchen area. You're biggest problem will be the unannounced room inspection or health and welfare inspection. You might be better off storing your clothes in your vehicle. Rarely will there be a vehicle inspection - something really bad has to happen like a lost sensitive item (think rifle, night vision device) or someone has a gun or drugs in their room. I never had a vehicle search when I was enlisted and had 2 as an officer. When you go through the gate, they generally don't open bags - never have had them ask to see inside one of mine. As far as the computer network, most of what people have posted is wrong. CID doesn't monitor any network. The Army is behind a firewall and web filters. If you try to go to a site it doesn't like while at work, it won't let you. Sometimes they haven't found all the sites; took them 3 months to lock out BME. Your best bet is to keep it professional at work. Your barracks internet is paid for by you through a commercial provider. There are no filters and no one is sniffing it, other than maybe the ISP. You can do anything that is legal on that network. The same basic rules apply while deployed. The work network is more heavily filtered, depending on who runs it, but this is mostly for bandwidth reasons. I know of a guy who was googling all sorts of porn sites - he had an open line, which should tell you how high up he was. When found out, all that happened to him was getting fired and sent to a new job. Not the greatest thing for a career - officers getting fired generally means that your not getting promoted anytime soon. The commercial network that you pay for is yours to do with what you will, subject to the rules of the ISP and General Order 1A, which prohibits porn anyway. I have been involved in investigations of soldiers for extremist activity and child porn on their personal laptops. No one has ever come to me and asked me to look for evidence of crossdressing, or anything else because there's nothing they can do about it. Trust me, the 1SG is really who you want to be most concerned about, and they generally have more than enough to keep them busy with real problem soldiers. That said, don't give them a reason to examine you from a bad perspective - good advice for CDers and everyone else. As long as you have thick skin, you'll be fine.

As far as a security clearance, I have a Top Secret/Secure Compartmentalized Information (TS/SCI). The only questions the investigator asks are very general - have you any knowledge of dishonest acts - theft, etc; do you know of any reason why this person shouldn't have a clearance; does this person drink a lot? They are looking for issues that would cause concern for your level of responsibility. Being enlisted, your chances of requiring a TS/SCI are low unless you go into intelligence. Later, if you go into special forces, civil affairs, or psychological operations, then you'll need one. To get a Secret clearance, they simply do a records check. If you haven't been arrested and don't have a lot of speeding tickets, you'll have no issues.

The Army can be a great life. It's what you make of it. Do your job to the best of your ability, don't create headaches for your superiors, know your place (very important), and finally, don't act high and mighty because of a college degree. Very few people will be impressed - remember, 2LTs have them as well. I walked into my company as a SPC and was chipping tile from under the urinal on my second day. Seize the opportunities that get presented. Once I finish vet school, my plan is to go back in. One day you may walk into a clinic and meet a veterinarian who has pierced ears, likes to wear skirts and Mary Janes, and has a Y chromosome.