Tom

“Tom,” you said eventually, a little disappointed. You were hoping to get Miranda, or at least Nicole or Matt to hook them up. A nagging voice in the back of your head said that Nicole would’ve been a pretty good draw too..”

“Well? C’mon, don’t keep me waiting. Whatcha got?” Tom blurted out, almost too excited. If it wasn’t for the fact that he was naked and sporting quite the boner, he could’ve just as easily been a child expecting a birthday gift.

“I dare you to… let the girls service you until you have an orgasm, but they do what they want, you can’t tell them what to do,” you said after a moment’s thought. Truthfully you didn’t want to risk Tom getting upset over being left out of all the good dares (or at least when Sarah wasn’t the one giving them), but you also didn’t want to be responsible for putting your best friend’s crush on that dick… also, there was no way in hell you were putting your other best friend or your crush on that dick. This way, you at least had plausible deniability… whatever happened from here was out of your hands.

Matt seemed to realize pretty quickly what you were doing, judging by the mixture of apprehension and relief in his eyes. Tom didn’t show any signs of disappointment in his dare, leaning back onto the nearest piece of furniture he could find and crossing his arms behind his head.

“Well, I’m open for business, ladies. Do whatever.”

“Ooh, too bad I just got off,” Sarah said, winking at Tom. Matt winced a little at the memory of her riding you to completion, but otherwise showed little reaction.

“I, uh – what if we don’t want to do anything?” Nicole asked, eyeing you warily. “I mean… I’m… with all three of us…”

“You have to at least touch him,” you said quickly, eyeing Tom. He just shrugged, and you saw a look of confusion cross Matt’s face that probably mirrored your own. Despite being so left out, Tom seemed very calm about someone trying to avoid doing anything.

“If you don’t want to do anything don’t. He didn’t dare you, he dared me, and it’s not like we’re trying to **** anyone here,” Tom said with a casual shrug. “I’d be more concerned if you stopped talking to these two dorks just because of something we made you do that you really didn’t want to.”

“I… thank you,” Nicole said. It seemed everyone except Tom and Sarah was a little taken aback by the sudden compassion. It was a little out of character for Tom, who had by some rumors once beat one of his teammates bloody for telling him he’d called a play wrong. Forgiveness and humility were not strengths he was well known for. But apparently Nicole’s attitude wasn’t offending him, for whatever reason.

Perhaps emboldened by his calm nature, all three girls moved ahead, rubbing their hands over him. You were pretty sure that Sarah and Tom had gotten together at one point, so it made sense that she was the most aggressive of the group, going straight for his erection and pumping it with her hand. Matt looked away, obviously uncomfortable, but he made no sound or attempt to stop the ongoing dare.

The girls crowded around, working over Tom on different levels. Before long Sarah was bent over, gently sucking on the head of his cock, while Nicole and Miranda were gently rubbing along his body, providing backup stimulation. Tom wasn’t actually getting all that much attention for having three girls attending to him, but he kept surprisingly quiet and didn’t complain. The more the night went on, the more you were starting to doubt all those stories about his attitude problems.

It didn’t seem like long at all before Tom was groaning in pleasure, and a few moments later he was gently thrusting into Sarah’s mouth as – obviously – he came. Matt looked upset, but was doing his best to hide it. He didn’t seem angry, just uncomfortable, perhaps knowing that the options were limited. Either your crush or his, or the woman both of you thought of as a sister, were going to have to do it. No doubt he wished it hadn’t been Sarah all the same, though…

“Holy shit,” Tom said, leaning back into his seat and obviously enjoying the afterglow, “you girls are insane.”

While not putting too much effort into doing so, Tom reached forward and began to search for a name in the hat.