Jay's Life Ch. 01

"I'll take one of each, I guess." Ben responded, dreading his turn after what happened to Jay upstairs.

"OK, first your truth. What happened in your dream that you wouldn't tell me earlier?" Jay asked, really curious, especially since he had been secretly bi-curious for a while.

"Well..." Ben was trying to stall.

"Just spit it out man."

"OK fine. We all took turns sucking each others dicks while the others fucked Sara. That's all. Nothing more than oral."

"Wow." Jay responded. That was perfect because that's all he ever had desire to do with a man. Sucking and getting sucked. The thought of anal sex with a man was not appealing to him at all.

"I dare you to drive up to McDonald's and get me something to eat." (I DO NOT ADVOCATE DRINKING AND DRIVING. IN FACT I STAND STERNLY AGAINST IT. THIS IS FICTION.)

"Man, that's a weak dare. I was expecting a lot worse." Ben said as he started putting his pants on to go get the food.

"Naked." Jay said, doing the same thing to Ben as he had done earlier. "And that's not all. Your cock must be hard as you pull up to the window to grab the food. I'll ride in the back seat to make sure this happens."

"Shit." was all Ben could muster.

"And I'm not done. You have to ask the person handing you the food if they wanna 'take care of this huge cock' for you." Jay said, barely controlling his laughter.

"Dude, this is going too far."

"Fuck that, I've done all your shit. Now it's your turn."

"Goddamn it! I could kill you right now! Let's go get this over with."

The boys walk down to the car. Ben walking rather quickly hoping no one comes outside. By this point it is about 2:30am so it would be unlikely. Jay, still in his underwear walked more slowly. They got in and headed toward the McDonald's. The boys pulled up to McDonald's, Jay in the backseat and Ben driving. Jay leaned over to make sure Ben was hard before going through the drive through.

"Hey man, you gotta get that thing hard."

"How am I supposed to do that?"

"I don't know, jack off or something."

"Now you want me to jack-off for you?"

"Not like I'm asking for a show, jackass. You just have to finish the dare."

Ben closed his eyes, imagining a hot girl sucking his cock. As he stroked his tiny cock his brain kept shooting from one thing to another. At one point Jay's big, erect cock from earlier popped into his head. This is when the blood actually started flowing to his member. Then Ben's mind went to his ex and the sexy times they shared together, limited as they were. Finally his dick was hard as a rock. All the while, Jay had been watching Ben and had gotten hard himself. He knew he was curious about other guys but never really expected it to be one of his friends he wanted to try it with. Ben said he was ready and pulled up to the drive through.

"Please order when ready." Ben was relieved when heard it was a woman's voice. He didn't want to be doing this but at least he wouldn't be asking some random guy to 'take care of his huge cock for him.' He ordered and took a deep breath as he pulled forward. Luckily it was late so only one window was open. "That's $7.77." The girl said, without looking, just holding her hand out. As Ben handed her the card she turned her head and saw that he was naked. "Whoa, dude! What the fuck!" She didn't seem upset of offended, just surprised.

"Would you like to take care of this huge cock for me?" Ben said, trying to sound confident, but obviously petrified by the situation.

"Let me see." The girl said. She leaned over and looked closer at Ben's tiny dick. When she saw his dick she began to laugh. But then she noticed Jay in the back. She saw the huge bulge in his underwear and perked up a bit. "No thanks, but hold on a minute." A few moments later she returned with his card, the food and a piece of paper. "I don't know what the hell you guys are doing, but here, give this to your friend." She said this and close the window and walked off. Ben drove off as he threw the bag of food and the piece of paper the girl had handed him in the back at Jay.

"Nice dude. she gave me her number. Her name is Jessica." Jay said, gloating that the girl wanted him and not Ben.

"Whatever. You got your food, you've had your fun, now it's my turn to have fun." Ben said, indicating that it was now his shot and only the 8 ball was left, meaning he would get the big dare. "what indicates a big dare anyway? I actually feel like this was a big dare."

"A big dare is a dare where it can be absolutely anything at all, no matter what and the person has to do it if it's humanly possible. Also, if that person doesn't do it, then they become the others personal slave for a year!" Jay answered.

"Fuck! well I am definitely going to sink that 8 ball then!" Ben said. The boys rode back to the house. Jay ate his food and stroked his cock in the back seat while Ben focused on the road and just prayed that they didn't get pulled over. The boys got back to the house and got inside safely. Jay tucked the number from Jessica into his shoe and returned to the pool table for the game. Ben missed his shot the the 8 ball placing it in the corner for an easy shot.

"Oh it's over now man!" Jay gloated prematurely. He lined up his shot, but being still a little tipsy, he ended up missing the shot, knocking the ball back out into the middle of the table. The boys went back and forth until finally Ben sank the 8 ball.

"This is my game, BITCH!" he yelled, then catching himself, remembering his parents were asleep. It was now 4am (19 hours left for Jay's shorts).

"Fuck!" Jay exclaimed his displeasure. He was pissed at himself for missing the easy shot early on and was now scared of what his dare would be.

"OK, here we go. I dare you to go upstairs, go in my parents room and blow a load on my mom's face while she is asleep and just leave it there."

"That is really fucked up bro! She could wake up, or your dad could wake up and beat my ass. I really like your parent. I don't want them to hate me."

Ben thought for a minute. He realized the risk Jay spoke of and took it into consideration.

"Nah, dare stays as is." Ben returned the favor from earlier. This shocked Jay as he now realized what he had to do. He was going to have to sneak into Ben's parents' bed room and jack-off until he came on Thelma's face, and then just leave it there for her to wake up to.

Jay crept upstairs. He walked to the bedroom door of Thelma and Steve and slowly turned the door knob, trying to be quite. He opened the door as carefully as he could but a small squeak did come from the hinge. this caused a stir in Thelma and stunned Jay. Jay stood there waiting for Thelma to calm in her movement. He started towards the bed again. He went to Thelma's side of the door and as he pulled his soft cock out of his underwear and began stroking it he saw Ben standing at the door. He waved for Ben to go away and in this waving he made the floor creek slightly. This woke Thelma, but instead of letting Jay know she was awake she just lay there pretending to be asleep. Here was her son's hot friend standing above her stroking his hardening cock. It wasn't long before it was at full stance. Jay stroked slowly then fast, alternating back and forth. It seemed he was enjoying this more than being afraid. Jay was stroking fiercely, about ready to come and then he swore he saw Thelma lick her lips in the moonlight. That made Jay lose it. He began to spout his thick ropes of cum on the face of Ben's mom. One shot landed on her lips. Another on her forehead. Another on her neck and blanket. The final shot landed on her cheek. Jay was spent and slowly crept from the room. This left Thelma reeling at what just happened. this turned her on so much that she began to play with herself while cleaning the cum from her face with her finger, moving it to her mouth. She hated the taste of cum normally, but this was too hot and she was loving it.

Jay walked from the room back to the basement door with a sense of pride that he had accomplished the 'big dare' Ben came up with, without a hitch. He wondered what more this interesting night might bring into his life in the future. He would find out sooner than he though as he walked down the stairs.