Work on friends, starting with Jenn

Mark thought he would be best suited to ask the girls he knew best. Although it would be more than a little awkward if they were weirded out by it, they were overall probably a better chance to say yes than other girls he asked.

Letting the conversation flow a little more, Mark waited for the right time to ask Jenn, not wanting to creep her out. That moment came as they started speaking about the fact that he was now on the football team.

“I’m proud of you though, never thought you’d be one for the sport but that’s great Mark,” Jenn complimented him.

“Thanks Jenn, that means a lot,” Mark replied.

“You getting along with all the guys on the team?”

“Ahh yeah sort of, really trying to earn the respect of them but yeah I guess so,” Mark said, now preparing how he could turn this into what he wanted from her. “They’re actually doing this contest thing tonight, it’s a bit silly but it’s who can get the most girls out of their underwear sort of thing, like actually give us their own pair.”

Mark thought it would be best to gauge her reaction first before actually asking her. If she looked appalled, he would bail and not push her for her own pair of panties.

However, her reaction was one of laughter, “Really? You guys are wild,” she said, still giggling, “So have you had anyone actually give you their panties?”

“Uhh no I haven’t. I haven’t actually asked anyone yet, why? Are you offering?” Mark asked, happy with where this was going.

Jenn laughed again, still surprised this was a real contest, “Well if I was going to give anyone from the team mine, it would be you.”

Bingo. Mark began to smile too, he almost had her panties in his hands and it was as easy as that. “Not going to lie, that would be awesome if you could, just so I’m not going back there with zero points.”

Jenn smirked, she looked around the hall. It was way too packed of people in here and she wasn’t the kind of girl to start undressing in front of a big crowd, even if it was just slipping her underwear off under the skirt. “We’ll have to do this outside or something.

“You’re actually a legend, come with me,” Mark said, leading them both outside.

They made their way away from the crowd of people, trying to find just a little bit more privacy outside in the dark. Once they were definitley alone, Jenn slid her hands up from the bottom of her leopard print skirt to retrieve her panties. She quickly hooked her fingers inside before sliding them all the way down her legs.

“Well there you go, simple black pair,” she said, passing him the nice simple cotton pair of panties she wore.

“Oh my god, thanks so much Jenn, I owe you one. But before I forget, we have to take a photo with the girl and the panties just to prove it’s legit, is that alright?” he asked her.

She laughed again, “Sure thing Mark.”

Just like that, Mark and Jenn took a selfie together. Flash light on, the photo captured the two together with Jenn holding up her black panties in her right hand. Mark was on the board with his first point of the night.

“So I’m guessing I won’t see those again?” she asked him.

“Well I don’t think we have to keep them after tonight or anything so I can give them back to you after if you want?” he responded.

She shrugged, tilting her head a little, “Don’t think I really need those ones but may be a good excuse for you to come and see me one time...”

“Oh I don’t need a reason for that, I’d be happy seeing you any time,” Mark said, winking.

“Swing by my dorm some time in the next couple of weeks then mister,” she said, poking him in the chest before saying goodbye.

Well that couldn’t have worked out much better. But one wasn’t enough to stop there, he needed to keep working at it. Who could he ask next that would definitley say yes?