That time I got naked in downtown SF

For those of you that watch the League, I'm sure you're familiar with the episode from Season One with the Usual Bet. If not, here's a little background, there is a scene in the first season where one of the girls loses the Usual Bet, which means she had to strip down naked in a dark alleyway for two minutes. If you haven't seen it I would youtube that scene or something. I know my boyfriend really liked it and had always talked to me about doing it.

Well that opportunity came up one night a couple of years ago. We were watching that episode with a bunch of friends so it was fresh in our minds. We went out with another couple that night to bar hop, and play some pool. Pool always happens to be a game where I end up losing and having to do something crazy btw. It really is just an excuse to have me get naked somewhere public usually…lol! And my bf also uses it as a tool to get girls naked!

But anyway, we went out and played pool, and we kept joking that the losing couple had to do the usual bet, but no one took it that seriously…or so I thought. My boyfriend and I lost, and I think he secretly wanted me to follow through with it, so he brought it up again, and the other couple also chimed in, saying that I should have to do it, since I was the worst one. The other girl said that if she had lost, she knows that we would have made her do it, so it was fair that I had to do it. My bf didn't really protest, and I know he had wanted to see it. He normally doesn't like me to show my slutty side in front of his male friends, but since he kind of went along with it I decided to do it and see if he would stop me.

So we were about a block and a half away from where our car was parked, and we came across an alleyway. They said I should do it here and they would block the entrance from people walking by. It was freezing cold that night too! So I stopped, checked with my bf one last time to see if he would protest, and when he just smiled, I took off my coat, and pulled my shirt over my head, and handed them to him. The moment of truth came, and as it turns out, the other girl was the most vocal one. She was shouting, and cheering me on to do it, so I reached behind me, unclasped my bra, and after a moment of hesitation, slipped my bra off and handed it to my bf. The girl cheered loudly, and my bf and his friend just laughed and clapped. I asked how long I had to do this, and they said I had to do it until we got back to the car. I yelled that that was over a block away and they just said that they would protect me until we got there. Chivalrous men right? Lol!

I glanced out of the alley and saw that there was still a decent amount of foot traffic, for that late at night in downtown SF. It was probably the crowd leaving the bars at that point. I asked him again if he was sure he wanted me to do this, and when he said yeah, I said "ok, fuck it." If he wanted me to have my boobs out in front of complete strangers, he was going to get what he asked for. So we started walking out of the alley, with my hands over my boobs. Partially out of modesty, partially because it was cold. Right when we exited I saw a couple of guys on the other side of the street, walking in the opposite direction, so I surprised everyone when I dropped my arms from my boobs, and waved and said hi to the guys, who both did a double take and stopped in their tracks. They waved back until we passed them, then kept going. We continued on our walk, which even included stopping at a crosswalk where at least two cars drove by. The last block was the worst actually, and no less than six guys saw me, including four that were on our side of the street. There were two guys chatting on the sidewalk who didn't even hide their shock when a completely topless girl walked by them. Oddly enough, I found the girls there to be more loud and boisterous than the guys! The men we passed just chuckled and stared, but the girl I was with was loud, trying to purposely draw as much attention to me as possible. And another girl we passed on the other side of the straight raised both arms and yelled "YEAHHHH" when she saw me.

It was quite a chilly night, so I was happy to finally get to the car and put my clothes back on, but inside, I was burning up. It was such a thrill and turn on.

Source: reddit.com/r/gonewildstories/comments/3cbwmv/that_time_i_got_naked_in_downtown_sf

18 comments

  1. Ehhhh sounds like you weren’t even naked, just topless. Hardly that out of the ordinary in SF.

  2. The hardest part is taking off your bra! After that it’s all freeeedom!

  3. Naked or just topless, still hot. Love to read about girls who get off showing their boobs! After some initial convincing my GF eventually loved going topless at the beach, and her DD’s certainly got plenty of attention! We always had great sex after coming home from the beach. She also flashed the pizza guy a few times. Do you think you’ll do this sort of thing again? I second the call for /r/gonewild – would be a huge turn on to see a picture to go along with your story, and I can absolutely promise you that I’d jack off to it [/r/NSFW_Tributes](https://www.reddit.com/r/NSFW_Tributes/) perhaps?

  4. I totally agree! There’s no feeling like the cool air hitting your nipples.

  5. Lol, we’ve done the pizza guy flashing thing once, although I don’t have nearly the boobs your bf does. Hope you guys got a good discount! And that was just one of my many adventures, I’ve done much more and much worse over the years.

  6. Hot! Yeah the pizza guy got a lot more than a boob flash in the ensuing weeks. I’ve posted about it previously somewhere in here. Looking forward to reading more from you, and now I need to troll your history! ;)

  7. Well from what I’ve read, you’re a pretty interesting gal! And just FTR, I’ve never had sex with an Asian girl, but would definitely love to. Sadly, I suspect I never will. My advice to you is to seize every opportunity you can (though it sounds like you don’t need to be told that!) ;)

  8. How about just a PM for me then? I don’t really care about the community, I just want to see those (now famous) boobs

  9. Just saw some of your pics. You should get your gf to try this dare…

  10. Sounds like I need to head to SF soon if you are going to have more nights like this! When’s the next bet happening? ;)

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