First Time
AN: This story is based on the following lyrics:
"Like a virgin
Touched for the very first time
Like a virgin
When your heart beats [after first time, "With your heartbeat"]
Next to mine
Gonna give you all my love, boy
My fear is fading fast
Been saving it all for you
'Cause only love can last" (Lyrics from Madonna's Like a Virgin)
Shane tossed and turned as he tried to get Jack off his mind. He was having a hard time falling asleep and he couldn't stop thinking about kissing Jack. He knew it was wrong, after all the pain that Jack had caused him, but when they kissed it felt so right. Hell...he was even getting an erection now just thinking about Jack's lips on his.
He stuck his hand down his boxer shorts and grabbed his hardened penis. He pumped it up and down as he imagined that Jack was here with him.
He heard a light tapping on his window, so he turned around and saw Jack sitting on his roof looking in his window. Was he imagining things or was Jack really here? "Jack?" he asked as he opened the window.
"Can I come in Shane? It's really cold out here?" Jack asked.
Shane moved out of the way so that Jack could climb into his room. "What are you doing here?" Shane asked.
"I couldn't stop thinking about kissing you and I just really wanted to see you and feel your tongue inside of my mouth again," Jack whispered as he moved closer and closer to Shane until their mouths were touching. Shane slightly opened his mouth as they kissed. Shane let Jack's tongue enter as he could feel his erection getting bigger and bigger as it rubbed against Jack's erection.
"I want to make love to you Shane," Jack stated as he reached down and grabbed Shane's erection through the hole in his boxer shorts.
"My...um...parents are down stairs," Shane stated.
"I can be quiet if you can," Jack whispered.
"I don't know...I'm a virgin...I've never been with anybody before...what if I disappoint you?"
"You won't. I've never been with anybody before either. I don't know what I'm doing, the only thing that I know is I want my first time to be with you."
"I want that too," Shane stated as he grabbed Jack's hand and led him towards his bed. Shane laid down under the covers while Jack removed his pants and underwear. Shane couldn't help but look down at Jack's erection as he shivered at the thought of feeling it inside of him.
When Jack was undressed he laid down next to Shane. They tangled their naked bodies as they continued to kiss one another. Jack could feel Shane's hard erection between his legs and he wanted to know how it would feel inside his mouth.
"What are you doing?" Shane asked as Jack knelt over him.
"I'm going to give you the most pleasure that you've ever experienced," Jack stated as he placed his mouth around his penis and began to suck as Shane let out guttural grunts of pleasure.
He continued to suck as Shane's body tensed and he could taste his cum flowing into his mouth until Shane's orgasm was complete. "Do you have any lotion?" Jack asked as soon as he was done swallowing.
"Yeah, why?"
"I want to experiment with anal, but I don't want to hurt you."
Shane grabbed the lotion and helped Jack spread it on his bulging cock and then he laid over the bed exposing his ass to Jack. He could fill the tip of Jack's penis slowly begin to enter him. It hurt, but it filled him with a tingling sensation as well, and the pleasure was worth the pain.
"Are you okay?" Jack whispered once he was completely inside of Shane.
"Yeah...don't stop...I want you to cum inside of me," Shane whispered.
Jack began to thrust harder and harder as he entered Shane over and over again with increased speed. The tightening of Shane's ass around his cock felt so pleasurable that he never wanted it to end, but he also knew that the pleasure was so intense that he couldn't hold onto it for much longer. "Oh...god..." Jack moaned as he reached the brink of his orgasm and released his cum inside of Shane.
"Oh my god Shane...that was fucking amazing," Jack stated as he kissed him. "I wish that I could spend the night, but I don't want my mom to realize that I snuck out," Jack stated as he put on his clothes.
"I understand...what happens now?" Shane asked as he tried to understand what his relationship with Jack was.
"I'm still grounded, so I don't think that I'll be able to see you tomorrow day, but leave your window open and I'll come see you tomorrow night."
"So, are you my boyfriend now?"
"I honestly don't know what we are...the only thing that I know is that I love you and I don't want what we just shared to ever be over."
"Me either. I love you too Jack, I'll see you tomorrow night," Shane stated as he kissed Jack and climbed back into bed.
"I'll see you tomorrow," Jack stated as he climbed out the window and left him.