14/08/2011
I'm going in to my second year of college, and for a summer job I took a late night bartender job at a really popular restaurant/bar on the ocean. Being a hot spot, it draws a lot of big spending businessmen, and I learned quickly that sex sells, so I'm taking advantage of that. The bartenders here (either male or female) wear white shirts and black either pants or a skirt, so I started out in a pair of heels, black pants and the white blouse, nothing special. I'm fairly tall (5'9") and slim with long legs, but big (36C) boobs, so I get noticed a lot. The first week I got lots of male attention, and decent tips, but I had this one guy that kept flirting with me, pretty cute actually, and he said I'd get some really great tips if I switched to a miniskirt and some stilettos, so I decided to try it. Next night, a nice, short black mini, bare legs and a pair of 4" black stilettos, and he was right, the tips went up. He told me the nice legs are what guys want to see, and I had them, and he commented that guys love boobs too, and I had those too, maybe ditch the bra. I thought about it, but didn't do it, but continued with the miniskirt and stilettos until he was back the next week, good tips all along. We got some spirited banter going, and he bet me $100 that I wouldn't dare go without my bra the next night, which was Friday, our busiest night. I start at 9, so back at my apartment I showered and got dressed in my miniskirt, stilettos and I'd resigned myself to paying him the $100 and wearing my bra. Just on a lark, I put on the blouse without a bra and tucked it in and put on my belt, then buttoned up just to check the look in the mirror. As I walked towards my full-length mirror, I just looked really HOT, my boobs jiggled just a little bit and my nipples poked out proudly, as the blouse had no pockets. I tought about it for a few minutes, then jusr decided to go for it, so I left the bra home so I wouldn't chicken out, and got in my car for the 20 minute drive. My guy was there when I walked in behind the bar in all my glory, and he smiled broadly when he saw I wasn't wearing a bra, and I smiled right back. I was really enjoying the attention, my co-worker behind the bar was a guy my age from another college, and he couldn't seem to keep his eyes off my tits, but I was really turned on by my businessman friend, I was showing off just for his benefit. About midnight we were chatting a bit as I polished some glasses and he asked if I had panties on under my miniskirt, and I told him of course I did. He said maybe I should've left those home too, and I just got the most sexy feeling, so when my co-worker went out to the other end, I checked and we were alone right there blocked by an open cupboard, so I quickly reached up my skirt, slipped the panties down, stepped out of them and handed them to him, and he was as surprised as I was, I'd NEVER done anything like that before. It was really turning me on working the bar the next 2 hours both braless and comando in a miniskirt, fuck me pumps and a button front thin white blouse, and when 2AM came, I was ready. We walked outside and he said he'd get a cab back to his Hotel, but I insisted on driving him in my '10 Mazda Miata, and we were pretty heated by then. It's not too easy driving a stick shift in stilettos, much less easy with a guys hands on your boobs and up the skirt, but I managed to get us to his Hotel. He asked, and I obliged in going up to his room, and we had the most incredible sex I've ever had. Since then, I've been doing the miniskirt/stilettos/no bra thing, and my tips have been great, and he's in town every week, so the sex has been great too.