Author's Note:

Kripe is a genious. Jared and Jenson aren't too bad either ; )

Here's the deal: I was feeling a little depressed and needed a pick me up. So I invited a few friends over. We started drinking and doing the whole "Remember the Time..." thing.

I'm going to capitalize on our stories (Don't worry - Names will be changed )

The guys involved will always be Sam or Dean or both, there are a few really naughty stories - yikes - did I just write that!

Anyway. This will only work if I get enough people reading. If you want me to keep going. Let me know.

Enjoy

GEM1588

Sam Winchester had just transferred to yet another high school. He met Bridgett simply because their lockers were next to each other. She was pretty. And rumor had it she was pretty easy too.

Her parents were divorced. She and her older sister lived with their mother who traveled extensively for work. Sam and Bridgett hit it off immediately.

It didn't take much to get invited to her house. Dean was proud of him.

Sam brought his gym bag with him. She already told him he was spending the night. He'd only been with two other girls and hoped his inexperience wouldn't show too much.

They hung out in her bedroom drinking her mother's liquor mixed with Hawaiian Punch. Her sister came home with her boyfriend. When she saw Sam in the room, she warned them to keep it down. She didn't want to hear them fucking all night. She was taking her SAT's in the morning. Her sister was a bitch.

Around 10 pm they finished the small bottle of Vodka and began a game of truth or dare. Well, there was no truth just dares which were all very sexual in nature. Sam got his first blow job that night. Bridgett didn't swallow, but he could live with that.

The dares got more and more intimate. Bridgett was asking him to do things he'd only seen in porn. He couldn't wait to brag to Dean.

It was her turn.

"Sam, truth or dare?"

"Dare." (of course!)

"Do you think a girl can have an orgasm from anal sex?"

"What?"

She repeated the question.

"I have no idea." How would he know something like that?

"Do you want to find out?"

"YES!" Anal with a girl! This was going to be fucking awesome.

"Have you ever had anal sex before?"

"No." His excitement dimmed a bit as he admitted that.

"I think you'll like it," she replied. "The bathroom is the second door, why don't you grab the tube of Vaseline out of the medicine cabinet. And don't let my sister hear you, ok."

"Sure."

It was close to midnight and the hallway was dark. Sam fumbled his way to the second door. He reached for the light switch flipping it to the 'on' position. Nothing happened. He flipped it down and back up again. But the light wasn't working. In the dark he opened the medicine cabinet and a shower of medical supplies fell out crashing into the sink. SHIT. He hoped the bitch hadn't heard that. He quickly grabbed the tube and headed back to Bridgett's room.

Her room was just as dark as the hallway now.

"What was that noise?" she asked.

"Some stuff fell."

"We have to be quiet, okay."

"Okay."

She kissed him. Her lips were soft and wet. When he put his arms around her he touched bare skin. She was completely naked. Just like that he was hard.

He put the tube on her nightstand and quickly stripped off his clothes. She took his dick in her hand stroking him.

Thank God for high school sluts.

"You ready?"

"Yeah."

She told him what to do with the Vaseline. She laid on her stomach on the bed and spread her legs. Sam grabbed the tube from the nightstand. He popped the cap off and squeezed half the tube's contents into his hand, rubbing it inside her. She moaned as his fingers went inside her ass.

He was just about to rub the Vaseline on himself when she hopped off the bed.

"OWWW!" she cried out. "My ass is fucking burning!"

She grabbed the tube out of his hand. "What the hell Sam!" she screamed. "Can't you FUCKING read? This is ICY HOT not Vaseline!"

Bridgett screamed as she tried to wipe it off herself. But it was already inside her and the warning label clearly states "NOT FOR INTERNAL USE."

Hearing Bridgett screaming her sister came stomping into the room. She flipped the light on giving them both instant eye-shock. She looked at Sam first he was still at full attention. Then she looked at her naked sister who was in tears as she tried wipe her butt. Her last glance was to the tube of Icy Hot sitting on the bed.

"I don't even want to know," she muttered as she walked out of the room. "Just keep the volume down, please." Then she shut the door behind her.

Sam walked home at 1 am.

Bridgett never spoke to him again.

This is a true story. Cross my heart.

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