Preface: Just over 9 years ago, I had joined the Air Force. Basic was meh, got through it with no big deal. I don't have any stories about those 2+ months as I was so focused on just getting through it. But tech school? Right after Basic I was bussed over to Biloxi, MS (Keesler AFB) which would be my home for 9 months while I completed my job training. I got a bunch of stories of this time, most were discreet and hidden because DADT was still in effect as this was 2009. If you enjoy this one, I'll gladly share more.
I had been on base about 4 weeks, which meant I was given full privileges on the base and was immune to curfew. I had been lucky that I didn't have a roommate in my dorm room, but that had just changed. Another airman transferred to my room after changing units because he failed his course at another base. He was from the area though, so on weekends, he would be gone and staying with family. Worked for me, as I would now have privacy to jerk off whenever I wanted on the weekend. Even better, our days were longer so that every other weekend we got a Friday off. While it was nice to have some privacy, jerking off was becoming not enough. I needed to fuck or be fucked by another man.
Now biloxi is a decent sized city where the base was at, but it's still the deep south. Luckily I was able to google 1 gay bar in the city. There are/were supposedly others, but this one I tried. On the next friday night off, my roommate had already gone home for the weekend. I cleaned out (just in case I needed to bottom, since I normally top), showered, put on a nice pair of jeans and a polo shirt, and head to the bar. I was worried that my hair cut would give me away as military, but since I'm going to a gay bar, any one that would enact DADT wouldn't be in there or would want the same privacy from the military.
I taxi over and go inside. It was a little small with a tiny dance floor, but it was mostly a bar and lounge. At 6'2 and 190 pounds (mostly lean with decent abs), I was getting more looks than I thought. There were a lot of bears and large men there. Most of the fit or skinny ones were clearly also military but there were also some college kids. I decided to play it coy and go sit at the bar and get an amaretto sour. I got carded again at the bar, but being recently 21 that was expected. I sat alone for probably 20 minutes and just chatted with the bartender for a bit who was pretty nice.
All of a sudden a tall, and slightly beefy man pulled out the bar stool and sat next to me, asking if I needed another. I said yes, and we got to talking. He was just a bit taller than me, probably 6'3 and he clearly had some muscle but also a tad bit of a gut, probably 230-240. Looked to be late 30s or early 40s with a tad of grey hair, all short like he could be military too. After chatting about life, he mentioned his name was Dan and he got forward.
* Dan: "Listen, I'm guessing your military and this is your first time out of base. Now you don't have to answer that, but it's obvious."
* Me: *stares down at my drink with a casual nod*
* Dan: "That's fine by me. You're safe in here, we haven't had a problem since the mid 90s. I was military too. I got out over a decade ago. However, I live in a condo near the IP casino if you want to get out of here. I'd like you to come back. I can drop you off by the base gate whenever you'd like."
I agreed to come with him. I was getting nervous, but horny as hell at the same time. My dick was raging in my jeans, I kept it to the side to hide it but it probably wasn't helping. We left and got in his very nice Mercedes, and drove off. While driving we did more small talk, before he put his hand on my lap, rubbing my dick through my jeans.
* Dan: "I'm glad you're excited too." *nodding to his crotch at his own boner*
* Me: "I am. But to be honest, it's been a few months now since I've done anything with anyone. I'm probably gonna suck at this."
