Strip Pirate Penguins with Sheri, Tobi, Keenly, and Sassy (HD)

The game: Team Pirate Penguins, Sassy and Tobi vs. Sheri and Zahara. The eager spectators: Johnny and Dante. The players take turns placing pirate penguins on a wobbly boat. If a girl places a penguin that doesn’t stay upright, or if a penguin is knocked off the boat, her team loses the round and both members must strip. (Actually, both members must strip each other.) The forfeit: Johnny and Dante get to use the two losers however they see fit. The remainder of this clip description will contain spoilers for the outcome, so if you want to be surprised, stop reading here and just buy it. It’s a good one.

Longtime fans will recall that Sassy was brought to LostBets back in 2010 by her then-boyfriend Dante, and she had an annoying habit of winning, like, all the time. We didn’t get to see very much of her. When she returned last year, her luck had turned a bit and she didn’t win quite so often. We got to see her masturbate (and her incredibly quick orgasms) but though she risked hardcore, she's never had to do it. After this shoot, she was moving to a new home in a faraway city, so this was likely to be her last for awhile, possibly forever. This might have been the last chance we'd ever have to see Sassy lose and get fucked. And if I’d let her escape unfucked, I don’t know if the fans would have ever forgiven me.

Which brings us to the subject of rigging games. I hate to do it, and hardly ever do. Not only does it offend my innate sense of fairness, but I think it makes the games worse when the players already know the outcome and are faking their reactions. I couldn’t do anything to soothe my sense of fairness, but I thought of a way to keep the players’ reactions genuine: don’t tell them that the game is rigged. Let them think they’re playing a fair game, and they’ll strive as hard as they can and be just as disappointed when they lose, or excited when they win.

I still hate rigging the games and still will do it almost never. But this was a special case. So I approached Tobi privately before the game.

”You know, Tobi,” I said. “This might be Sassy’s last shoot. And a lot of the fans would really, really like to see her get seriously fucked by her ex-boyfriend.” Tobi thought about it, laughed, and told me she’d take one for the team.

So Tobi was playing to lose, and to drag her hapless teammate down with her. Sassy wasn’t aware, and as far as I know still isn’t aware, and will only find out when she reads this clip description. When she does, I hope she doesn’t me, or Tobi for that matter. (Sassy, it was for a good cause.) Tobi did a fantastic job of playing the part. She caused her team’s first three losses, but did it subtly and non-obviously. And the thought of her impending nudity (and railing) made Sassy so nervous that she was responsible for their last two losses and their ultimate punishment. It’s over in 15 minutes, and poor Sassy actually apologized to Tobi for making her lose. I have a feeling that apology is going to be angrily retracted now.

There was a brief break between game and forfeit, during which the losers put their bras and panties back on, giving the gents something to strip off of them. As Dante goes to work on Sassy and Johnny goes to work on Tobi, there’s a real contrast in their fucking styles. Frankly, if I were a girl, I’d rather get fucked by Dante, who seems much more interested in his partner’s pleasure. It starts off with oral: Johnny makes Tobi suck his dick, while Dante goes down on Sassy and makes her shiver. The winners grab cameras to immortalize the event, with one of them whipping out her cellphone cam. Then Sassy goes down on Dante for a bit, and both losers are on their knees sucking dick. Then Dante rolls Sassy onto her back. Remember how Sassy is extremely quick to reach orgasm? Yeah, that comes into play. She’s also multiorgasmic.

Side note: it’s important that everyone knows (and I assume everyone does know) that No means No. Usually. This, however, was one of the rare cases where No meant Yes. These are two old lovers who know each other’s bodies very well and know what each other likes. It was kind of touching to watch. Anyway, during the ride, Sassy called out “no no no no no” repeatedly, so much so that I interrupted to make sure she was okay. She was. She was saying “no no no” when she was close to orgasm and she didn’t want Dante to make her cum so fast. He didn’t listen, and Sassy is pounded by orgasm after orgasm as she covers her own mouth in an effort to stifle her cries of ecstasy.

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