Taing the Deep Plunge

"Are you nervous?" Julie asked.

"Um, yeah, a little bit" Scott replied.

How could he not be? He's being set up on his first date with a man, after dating women all his life. Oh sure, he's always been curious about guys, but this was a big step.

Julie knew her friend well, and knew he seemed unhappy with the women he'd been seeing lately. She always sensed her friend might be into guys, if given the chance. She had been helping him down this road, hinting that he should be open to new things and starting to point out attractive guys when they were out. She could tell it excited him, and she knew it was time for him to take the plunge.

There was an attractive gay guy at her office, Jake, a bit younger than Scott and very good looking. She knew he was single and asked him one day if she could set him up. She told him all about Scott and he was excited to meet him. She invited him over to her house for dinner Saturday night.

When she told Scott, he was caught off guard. He had had thoughts about men, but it was something he had never admitted to. At first he tried to protest, but Julie always made him feel comfortable and he ultimately confessed that he was quite turned on at the thought of actually meeting a guy.

That evening when Jake arrived, he shook hands with Scott and you could sense the electricity between them. They flirted all night, laughing through dinner as the wine loosened everyone up. Julie suggested they move to the balcony, it was such a nice night.

As she brought out another bottle of wine, she stopped when she saw the two guys embracing each other, their lips locked together. She watched for a minute or two, and couldn't help but be turned on a little as she watched them grope each other as their kissing intensified.

Finally she cleared her throat as she walked out to them, and they reluctantly pulled apart smiling sheepishly. Jake excused himself to use the restroom, and Julie took this time to talk to Scott.

"Oh my god, how was it?" Julie asked.

"I almost feel light headed, he's such a great kisser. It just happened." Scott confessed.

"I'm so happy for you!" Julie squealed, squeezing his hand.

"Yeah, it's strange in a way, but it just felt so right." Scott said.

The wine was hitting them both when Julie leaned into him and whispered in his ear.

"Why don't you go seal the deal?" she suggested.

She reached down and squeezed his cock through his pants, which was rock hard.

"Use my room, I'll hang outside here." she said.

Scott was so turned on, he hadn't expected things to move so quickly but he just smiled and gave Julie a quick kiss to thank her. He started to pull away but she grabbed him behind his head and pulled him in for a deeper kiss. Their tongues danced with each other briefly, before she pulled away.

"Sorry, I didn't want to miss out on all the fun." she said.

Scott laughed and walked inside. He caught Jake coming out of the bathroom and without another word, took his hand and led him to Julie's bedroom. They embraced again, as their hands started tugging off each other's clothes.

Scott's hands went to Jake's belt, undoing it and his pants as well. Scott instinctively dropped to his knees, pulling down Jake's underwear and coming face to face with his first cock. It was long and thick, and as he wrapped his hand around it, it felt so warm too. He stroked it a few times as he slowly moved his mouth to it.

His tongue licked the head and he could taste the precum leaking out. This taste made him want more, and he began sucking his first cock. It felt so right to be on his knees with a cock in his mouth, he knew now what he had been missing in the past. He continued his assault on Jake's cock, his mouth moving down to suck on his smooth balls occasionally.

Finally Jake's hand grabbed the back of Scott's head as he began thrusting into his mouth. Scott knew what was coming, and he sucked even harder as he heard Jake breathing harder and felt his cock swell in his mouth. With a deep grunt, Jake's cock erupted in his mouth, and like a pro, Scott swallowed every bit of his load. Jake slowly pulled out as Scott stood up, and Jake pushed him back on to the bed.

"Your turn" Jake said.

As he lowered his mouth to suck Scott's cock. Scott laid back, enjoying the moment. His mouth was incredible. But Scott knew he wanted more, he wanted to be turned out and broken in, he wanted to fully switch sides and become the gay man he always felt he might be. He reached down and pulled Jake's mouth off of his cock.

"I need you inside me, I want you to fuck my ass and make me yours." Scott said.

Jake smiled as he moved his body up on Scott's and they began kissing like lovers. Jake's fingers moved down to Scott's ass and he inserted one, then two, as they kept kissing. Finally, after a third finger was in and he was practically humping his hand, Scott spoke up.

"I can't wait any longer, make love to me." said Scott.

Jake pulled Scott's legs up on his shoulders and placed his hard cock at the entrance to Scott's ass. Just as he started to push in, Scott noticed Julie standing in the doorway, one hand down her pants, enjoying the show. His eyes met hers as Jake's cock slid in his ass. It was painful at first, but Jake just held his cock deep in his ass letting him get used to the feeling.

Scott was in heaven, the first cock up his ass, and he knew it wouldn't be the last. Jake began pulling out slowly, then back in, stretching his ass out and building up a rhythm. Scott looked to Julie again, only to see her standing much closer to them. His hand reached over and slid between her legs, rubbing her pussy through her dress.

"Join us" Scott said.

Julie quickly shed her clothes, and crawled onto the bed beside them. Jake pulled his cock out and told Scott to get on his hands and knees. He did so, as Julie slipped under him. Her mouth found his and they began to kiss as Jake pushed his cock back into Scott's ass.

With each thrust Scott's cock inched closer to Julie's pussy, which was soaking wet. Finally she scooted down a bit and she felt Scott's hard cock slide deep inside her.

The three built up a rhythm, Jake's thrusts pushing Scott's cock deep inside Julie. The room was filled with sounds of grunts and groans and flesh slapping together. Jake increased his pounding, getting close. Scott could tell and his cock felt like it was ready to burst too.

Julie's own orgasm was building and as Jake let out a large groan, he gave one last thrust in Scott as his cock erupted inside him, filling his ass with his warm cum. At the same moment, Scott came hard inside Julie, her screams matching his moans and she came along with him. They all collapsed together, a tangle of sweaty limbs.

The guys kissed, and Scott felt so complete, finally embracing his true self. He broke the kiss and turned to Julie, kissing her as well.

"Sorry" she said "I just couldn't help myself, you guys looked so hot together."

"You can join us anytime" Jake said, "but his ass belongs to me."

They laughed as they lay together, all wondering if their night was over or just beginning.