I've been sneaking out of my house to go off on wild sexy adventures with my two best girlfriends ever since I entered high school, in 9th grade. One of our favorite activities was to go sneak into clubs downtown. We've always looked older than our age and to slip by the bouncers, we'd find two single guys (they were always willing) and pretend to be their dates just to get inside. I turned 18 over the summer between 11th and 12th grade, and we celebrated my birthday at one of my favorite clubs. We didn't have fake IDs or anything, but we could always count on coaxing some guys to buy us our drinks for us. Anyway, we had been there for about twenty minutes, long enough for us to have downed a few drinks and we hit the dance floor together, all three of us, kind of half-drunkenly grinding against each other in an effort to garner some male attention.
Not too long after, we were approached by an attractive guy in his early 20s and his slightly less attractive, though still perfectly handsome friend. They came carrying several bottles of corona and told us they were for us. We thanked them and agreed to dance with them and so the three of us girls started dancing with the two guys and it was pretty hot and we got pretty into it. After a while we took a break and all sat down and they bought us more drinks and we chatted amongst ourselves about all sorts of stuff. They introduced themselves as Mike and Bret, Mike being the hotter of the two. As we talked, the conversation drifted from mundane, everyday topics to our personal lives. We ended up disclosing all sorts of stuff like that we were all single, around 18, and none of us were virgins, and it was obvious they were interested in us. Not wanting to get in too deep, and realizing it was getting kind of late, we professed that we really should be going. They both readily offered us all rides home if we wanted, and my friends politely declined, saying they were just going to take the subway back, but I agreed to let Mike drive me home because I didn't feel like walking all the way to the station and he was pretty cute anyway.
So I said goodbye to my friends as we departed and I followed Mike out of the club and to his car. On the way to the car he kept telling me how hot I looked and how nice my outfit was. I was wearing this cute gold sparkly dress. It was pretty short at the bottom, falling about 6 inches below my waist, and the top, although a snug fit, showed considerable cleavage amongst its seemingly loose folds of fabric. During the ride, while he drove he kept glancing over to me and smiling and talking to me about all sorts of things. I was a somewhat drunk, I guess, but I laughed and answered all his questions. I loved all the attention I was getting, especially when he started commenting on how my dress "accentuated my lovely chest," saying my boobs were the perfect size. He asked me what my bra size was and I laughingly told him that I don't always wear a bra, but that when I do, I wear a 34b, adding that my boobs look bigger since I'm only 5'1" and 110 lbs. He said that he likes smaller sized boobs like mine better than big ones, especially since they're real. At the next red light he turned to me and stared at my chest for a few seconds before asking, "I can't tell. Are you wearing a bra under that dress?"
"No," I replied sheepishly grinning.
"I'm impressed," he confided, "Most girls your age don't do that. At the club it's mostly the single ladies in their thirties that can't admit their past their prime who go braless." I just grinned, unsure of what to say.
I'm not sure I believe you that you're braless," he continued, "You might have to prove it to me." I told him he could feel my boobs through my dress and feel that there was no bra. With his right hand, he reached out and groped at me for almost a minute before finally concluding that my dress was too thick and he still couldn't tell. "Yeah, right," I joked, laughing, "Sure you can't tell."
"Maybe if I could feel a little more?" he asked, "I would be able to tell." I laughed and let him go back to fondling me through my shirt. I noticed his hands creeping towards the seam of my shirt and trying to slip under but I didn't stop him. Soon I felt his hands caressing my bare breasts under my top and fondling my nipples and I was enjoying every moment of it. I felt him start to pull down my top and a moment later my bare boobs were on display. He grinned, and said I was right about being braless. I jokingly told him that "I told you so."
After several moments with my boobs on display, I started to pull my dress back up but stopped me and said not to bother, because he was still enjoying the view, and in my drunken state I thought that was such a cute thing to say and so I just left my boobs on display for the rest of the car ride. The thrill of being exposed topless and felt up by a stranger in his car was making me really horny and wet and I guess he noticed a little wet spot on the hem of my dress where I had tucked it between my legs to cover up while I was sitting that I wasn't wearing panties either (haha).