[Tommytomjj]

“Well done, you’ve earned yourself a question babe” joked Meg, teasing her boyfriend as he stood there, exposed to her and her friends.

Jay was a logical boy, studying maths at university. You never would have guessed by looking at his athletic body, that his brain was his most impressive feature. He was also incredibly competitive. Ever since he was a boy, he hated losing. Whether it was playing football at the weekend or playing a board game with his family as a child. He even sometimes cried when he lost when he was younger. Because of these characteristics, Jay thought he’d be able to guess who the mystery girls were quite quickly, and thought of a question to try and rule out as many people as possible. He was playing the most sexual game of Guess Who anyone had ever played.

“Okay, do I know any of the mystery girls, so not including you Meg, from university?” He asked confidently.

He knew that this was unlikely as people from university lived all over the country and it would’ve been much more difficult to organise. He hoped Meg responded with a “no” and then that ruled out a lot of people.

“Yes. You met at least one of the three girls at university.” Answered Megan.

Jay was shocked. He wondered how Meg could have possibly done this. His brain starting to think who the girls could be. Was it one? Was it two? Was it all three? He wanted answers but he had used up his question and now it was time for his next dare.

“Okay babe, your next dare is easy. All you have to do is stand there in the middle of the room with your hands on your head for 20 seconds. I’ll count them for you.” Meg described his dare in detail. “We’ve moved all the furniture so we’ve got a big open space in the middle of the lounge. Just walk forward and put your hands on your head.”

Hesitantly, Jay did as he was told, creeping forward slowly. A pair of hands grabbed him by his sides and positioned him in the centre.

“Okay, hands on your head babe” instructed Megan.

Jay raised his hands and put them on his head and Megan began counting behind him. Immediately, Jay felt lips touching his own. One of the girls was kissing him, or trying to anyway. He didn’t kiss her back.

“Babe, you have to go along with everything. Today is your only free pass that you can do anything with another girl, and I’ll forget about it by tomorrow. Trust me it’s fine, I want you to do it.” Meg explained in a caring manner.

Jay correctly believed her. He began to kiss this mysterious girl back passionately. She was a fantastic kisser and he was really enjoying himself. Suddenly, he felt a sharp pain on each nipple. It was like a pinch but not from hands. Then, they began to twist, causing even more pain.

“10...” Meg continued the countdown.

Jay’s sense of touch was at maximum capacity. The touch from the girls lips adding more and more arousal; the pain from each clamp on his nipples also began to feel good. Meg knew he liked a bit of pain in the bedroom. Next, his briefs were yanked up into the air, giving him a painful and humiliating wedgie. The girl pulling the underwear did not stop though. She pulled each leg hole as hard as she could, forcing the boy to let out a small squeal. He had never been wedgied before. His bum crack was in so much pain, and so were his balls. Everything felt like it was getting crushed together and he didn’t know if he liked it or not.

“5...”

Jay was convinced she was counting slowly. How can so much humiliation happen in such a short amount of time? With only 5 seconds remaining, the lips moved away and the clamps were ripped off his nipples leaving them feeling tortured. Then the spanking began. He didn’t count how many. There were two different girls spanking each cheek as hard and as fast as they could for the remaining seconds. Each hit caused Jay to flinch. They hurt so much.

“Times up” Meg called out and the spanking stopped, “well done babe, did you enjoy that?” Meg laughed loudly.

“No!” Jay lied.

Although it was painful and humiliating, he loved every second of it. His cock still rock hard confirmed that he had enjoyed himself. His bum cheeks had started to redden, and he could feel them still stinging, along with his bum crack that was still in the wedgie.

“You can move your hands now, but don’t you dare unpick the wedgie.” Meg warned, “you’ll be punished if you do.”

Jay lowered his hands and crossed his arms over his nipples, subconsciously protecting them whilst he could. The girls giggled at his misfortune and he could hear them. They were loving every second of this, and they would never get this opportunity again so they were going to make the most of it. Jay could hear the laughter, but he couldn’t make out who the girls were.

“Okay babe, next question. The last one must’ve really help narrow it down!” Meg said sarcastically.

Jays logic had gone. He had been utterly humiliated and his brain was all over the place. He knew that at least one of the girls was from university, but he didn’t suspect that all of them were, so he didn’t bother asking if he knew some from before university too.

“Regarding the girl that I know from uni, did I meet her on my course?” Jay asked.

He knew some girls from his course, some from societies, some from sports teams and some of his neighbours. He also asked this in a way to hope that it confirms that only one of the mystery girls are from university.

“Yes, she’s from your course.” Meg answered, “now it’s time for your next dare....”