“I’ll try but I don’t know if I’ll be able to get it in…”
“Suck on it first slut.”
So Sarah took the heal end of her shoe and sucked it to lubricate it enough to fit into her ass, tasting the dirt she had walked through to get there.
She slowly worked it into her tiny asshole, letting out little screams of pain while pushing it in and out until she was able to make the entire heal disappear inside her, to the applause of everyone in the room.
“Good job slut, now the other one.”
Sarah’s ass was already stretched further than it ever had been with one heal in it, there was no way she could fit another one.
“Craig I don’t think that’s possible.” she pleaded.
“Then go the fuck home.”
“No no I’m sorry! I’ll try, i just don’t know how to do it…”
“Help her.” Craig said to Shawn, who had been sitting in silence and disbelief as his girlfriend defiled her ass with a shoe in front of everyone.
“Um yeah, sure ok.” Shawn snapped out of it.
He awkwardly stumbled over to her with an obvious erection covered by his pants and examined the situation.
“Umm maybe if you hold the first one in I can try to squeeze this one next to it.”
“Ok if you think so babe.”
Shawn held the second shoe to her mouth so she could lubricate it while Sarah held the first shoe in place up her ass. He spread her ass as much as he could to make room for the second shoe but her tight asshole clung to the first one without leaving room for anything else.
“I’m just going to have to force it in, is that ok?”
“Just do what you have to do!”
Sarah screamed in agony as Shawn lightly tried to wiggle the second heel into place.
“I can’t do it, it isn’t going to fit”
“Babe just shove it in! please!”
The second heel was only a quarter inch in, but Sarah’s screams were too much for Shawn to handle.
“I don’t want to hurt you”
“Get out of the way” Craig shoved Shawn to the side, grabbed the second heel and immediately shoved it all the way up Sarah’s ass next to the first heel.
Sarah’s screams were deafening, even over the music from the stereo. Tears ran down her face and she felt the most intense mix of pain and pleasure she had ever experienced. Craig grabbed her hands and put one on each shoe, “Hold them in slut.”
“Yes baby.” she whimpered.
Shawn wondered if she must have thought she was talking to him and not Craig, and was just calling him baby out of confusion in the moment of intense pain.
Before he could think too much into it he was interrupted by one of the guys in the crowd. “Holy shit Craig!”
Craig had unbuttoned his pants and out flopped the biggest cock Shawn had ever seen, easily three times the size of his own.
Before Shawn could process what was happening, Craig shoved his massive cock inside Sarah’s already soaking wet pussy, all the way down to the base.
“Oh FUUUUUCK Craig!” Sarah screamed out. Every cell in her body was on fire. She could feel all ten inches of Craig’s cock deep inside her, filling her up more than she ever dreamed possible.
Craig slowly pulled it out, then slammed it back in.
“Oh my GOD!! Again! Again! Please Craig! your cock feels INCREDIBLE!!” Sarah begged for more.