Act 2: The Show Must Go On

After a brief rest, Alex rolled over onto one elbow and looked into Evan’s eyes. That predatory grin was there again. He had the feeling that Alex was going to take things further now that Evan had crossed the line and was now technically part of the group.

“So, Evan...” Alex began.

“Now that you’ve tasted cock, did you like it?” His fingers lightly danced over the skin of Evan’s thighs.

“I ... I did, surprisingly enough,” Evan admitted, feeling this was going somewhere.

“Except for the gagging at the end,” he finished with a nervous laugh.

“Oh, no worries ... It happens to everyone their first time,” Alex assured him.

“But what I want to know is how far you’re willing to go from here?” His hand was getting close to Evan’s cock. Alex pushed his fingers between Evan’s thighs and motioned to have him spread them.

Evan obliged but snapped his thighs together quickly around Alex’s hand as Alex’s finger pressed against Evan’s perineum. It was clear now what Alex had in mind.

“I don’t know ... I mean, I’ve never.” Evan stammered, but Jake whispered to him on his other side.

“If it isn’t for you, then that’s okay, but why not let Alex test the waters?” For his size and build, Jake had a surprisingly gentle voice that made Evan feel at ease.

“One finger, if you don’t like it, we’re done.”

Evan nodded and relaxed his legs and spread them again. Alex began rubbing Evan’s perineum, which gave him an odd sensation that ran up his spine. Then Alex pressed his index finger against Evan’s sphincter and began to rub gently. Evan involuntarily sighed a sigh of contentment.

“Ahh!” Evan gasped as Alex’s finger pushed into his anus. Alex didn’t move.

“I’m okay,” Evan whispered, and Alex began moving his finger in and out of Evan’s anus.

“Should I try adding one finger” Alex whispered into Evan’s other ear. His breath was hot and his lips just barely brushed Evan’s ear.

“Umm Hmm...” was all Evan muttered as his eyes drifted closed from the feel of Alex’s finger gently fingering his anus. Evan gasped and his back arched as a second finger was inserted, but quickly he became used to it and relaxed.

The slow in-and-out motion of Alex’s fingers had once again lulled Evan into a state of near euphoria when Jake’s voice broke through the haze.

“So, do you think you want to try going, further?”

Evan wasn’t sure why, but the thought of Jake taking him was less daunting than having Alex do it. Jake was more muscular and bigger, in every way than Jake. But there was something about his quiet demeanor that was not just disarming, but quite charming.

“Will it be you?” Evan asked, only half aware of what was happening. Alex was still massaging his anus with his fingers and his cock was beginning to stiffen.

“If it’s you, Jake, then I think I can do it.”

“Oh goodness...” Alex gasped.

“It seems our new guy has a crush on you Jake,” Even heard a slap and Alex shouted.

“Ow! That was uncalled for...” Then he went on.

“I might be jealous if it weren’t for the fact that I’ll be able to get his sweet lips around my cock again.”

Alex’s fingers came out of Evan’s ass and Evan felt himself being maneuvered around on the bed. Jake spread Evan’s legs apart and began rubbing something cold between Evan’s buttocks. Evan was sure it was lubricant. Then he felt Jake’s weight atop him.

It was kind of comforting, not oppressive. Evan thought that the big man’s soft smooth skin felt wonderful. Jake lowered his face to Evan’s “I’ll go slow ... just tell me if it’s too much.”

“Okay,” was all Evan could manage at the moment. He felt the tip of Jake’s cock poke against his sphincter and tried to brace himself for the intrusion. But it was too fast and too sudden. Ahh ... Fuck!” Evan hissed.

“Wait ... Don’t go any deeper,” Evan placed his palms against the big man’s chest to hold him in place.

A few moments later, Jake whispered to Evan.

“Hold me around the neck if you need to...” Once Evan did, Jake relaxed his hips and let them fall a few inches pushing his shaft into Evan’s tight ass.

“Holy Fuck! You’re thick...” Evan observed as Jake stopped again. Now only three of his seven inches inside of Evan.

“It hurts, but it feels good at the same time,” Evan admitted, and Jake took that as permission to go further.

“I’m going to give it all to you now, Evan,” Jake said softly.

“Just hold on I’ll go slow,” Jake proceeded to feed his shaft deep into Evan’s rectum. It was one single stroke pushed in slowly as if injecting his cock into Evan.

Oooh!” Evan whined as the thick shaft drove into him. He began panting, trying to mitigate the pain. It surprised Evan that the pain was easing as Jake pushed deeper. Once he felt Jake’s pelvis against his own, he took in a deep breath.

“You’re doing great pal,” said Jake in his calming tone. He grabbed Evan’s thighs and lifted them. His cock slipped in a little further and Evan gasped.

“Just close your eyes and breathe. I’m going to fuck you now.”