Jay's Life Ch. 01

AUTHOR'S NOTE: This story is planned as a long series and will contain many different topics. if you are uncomfortable with any type of story, then you may not want to start this story, or you may want to just skip those stories, though some may be mixed in. An example is that in this story there are elements of gay, hetero, and milf. Thanks for your interest after this note and feel free to make suggestions. All feedback is appreciated!

Chapter 01: Pool Dares

Jay walks out of the local college's building, freshly released from his class prison. It was Friday and classes always seemed to linger on and on on Fridays. He walked outside, his medium length blonde hair waving in the winter's wind. His shorts blowing up a little giving him a slight chill in his nether regions. Jay never wears pants. Shorts year around, no matter what. He even wore shorts to a football game once where to temperature was 12 degrees.

He pulls out his phone and slides it open, the image of Jessica Alba's ass is on the screen as his wallpaper. He scrolls through the options until his reaches his text messages. There is one unread message from his friend Ben. It says "Hey man, are we hanging out tonight or what?." Jay quickly replies with "yeah dude, on the way" as he walks up to his car. He gets in and as quickly as LMFAO 's "Sexy and I Know it" can come on the sound system he is driving off.

About 5 minutes later Jay pulls up to Ben's house and turns off his car. He's walking up the drive way as he's greeted by Ben's mom. Both Jay and Ben are 21 but are still living at home while in school to save some cash.

"Hey Jay, Ben is down stairs, as usual." She tells him with a smile. "So what do you boys what for supper tonight?" Ben's mom is on the average side as far as looks go. She is about 5'2, curly blonde hair and glasses. A little chubby, but not fat. Not bad for about 45.

"You know I love whatever you fix! Doesn't matter to me." Jay says back. He smiles at her and walks inside.

Jay walks through the living room, seeing a Baseball game on the TV from where Ben's dad had it going. He isn't in the room so he doesn't know where old Steve is. He walks through the kitchen to the basement door and heads down the stairs to find Ben watching TV. It's on World's Dumbest and Ben is watching, not noticing Jay having walked into the room.

"What's up dude?" Jay says, making sure to let Ben know he had arrived.

"Hey man, what's going on?" Ben answers as Jay walks over and plops down on the couch.

"Your mom was just totally hitting on me is what's going on!" He says with a smile.

"You know how I feel about that. If you could stomach fucking her than I don't give a shit." Ben says acting as though your mom jokes don't phase him.

"Come on man, you know your mom isn't that bad. I'd definitely want to fuck her if your dad wasn't such a cool dude. I wouldn't want to do that to him."

"Whatever. so what we doing today?" Ben asked.

"I don't know, maybe take a dip in the pool, play some pool, watch some TV. You know, the normal stuff." Jay answered, sarcastically.

"Alright, well let's get in the pool first. I was mowing grass earlier and it's hot as a bitch out there, so I know the water will feel real nice."

Jay agreed and they both began to get ready to get in the pool. Jay headed back down to his car to grab his spare set of clothes he kept in case he needed them. He went back inside and down to the bathroom downstairs to get changed while Ben went to get changed in his bathroom upstairs. Jay slipped off his shirt revealing his newly remodeled torso, which looked better than ever before be he had recently lost over 100 pounds and was now in the best shape of his young life. He then dropped his shorts and underwear to put on another pair of shorts. Jay hated swim trunks so he just wore some mesh shorts instead. Ben was not as proud of his body as he left his shirt on while only changing into a pair of swimming trunks. They both met back upstairs and headed out to the pool.

They played around, splashing and horse playing a while. Once when Jay went to slam Ben, his hand went between Ben's legs and landed on his cock. This was the first time Jay had touched a penis other than his own. Jay had had some bi-curious feelings for a while but never acted on any of them because he knew his friends wouldn't be receptive. This turned Jay on a lot but he quickly moved his hand as to not seem suspicious to his friend.

Ben felt Jay grab his cock, but figured it was an accident and thought nothing else of it. He was growing bored of this horse play and the sun was beginning to go down. They had been in the pool longer than they realized.

"Man, it's getting dark. This sucks." Ben said, hinting that he was ready to go inside.

"Yeah, too bad the sun can't stay out all night." Jay responded.

"Well, you wanna go in and do something else?" Ben asked.

"Yeah sure." Jay answered.

They both go out of the pool and made their way into the screen porch to dry off. Jay left the towel laying on his lap to cover up the erection he got from grabbing Ben's cock. He really wanted to move it and pull his shorts down and jerk off right there, but he restrained himself. They sat there talking for 10 minutes or so before they were ready to go inside. Jay headed down stair to change as Ben went to his bathroom. Jay got an idea on the way down the stairs. He decided that he would change out in the basement instead of going into the bathroom. the thought of being naked in public was a huge turn on.

As Jay began to pull down his pants, Ben's mom walked down the stairs to retrieve the cat that had gotten down the stairs. Jay hadn't noticed as he went down stairs that he didn't close to door all the way, letting the cat down. The stairs were carpeted so there was no noise as Thelma walked down. When she got to the bottom of the stairs, there was Jay, newly reformed body, totally naked. He was just standing there, looking at the TV, taking his time changing. He was listening for the door to open before he would rush to put his dry shorts on. Thelma had never thought of Jay in any sexual way before, but seeing him naked like this, she couldn't help it. She felt guilty and quietly turned to head up stairs, deciding to get the cat later. When she got to the top of the stairs she closed the door, alerting Jay to put his clothes on quickly. He was a little confused when no one came down right away but he moved past it quickly.

"Food is ready" Jay heard Ben say down the stairs as the door opened. Jay saw the cat grabbed him and ran upstairs.

"What do we have?" Jay asked.

"Steak Fajitas and baked potatoes." Thelma replied. Jay and Ben made their plates. Jay couldn't help but notice Thelma noticing him. He tried not to make it obvious but he saw her slightly lick her lips as she gazed at him. He grinned a bit and headed down stairs behind Ben. The boys ate while watching a re-run of Two and a Half Men on the TV. Once they got done Jay suggested playing some pool. Ben agreed and they headed over to the table. After two games of Jay getting his ass beat, he decided to make a wager.

"OK, well I'm pissed. You aren't better than me. How about we put some pressure on so I can perform my best?" Jay said.

"OK, I don't mind winning something from your ass! What do you have in mind." Ben responded.

"How about Truth or Dare pool. Every time you make a shot you get to give the other person a truth question or a mild dare. Then the winner gets to give a big dare." Jay suggested.

"OK, sounds like a plan. You better get ready to do some dares and answer some hard questions." Ben said, in a playful but competitive manner. Ben went to break the balls and made two solids. He turned to Jay and said "Truth or dare?"

"I'll go one of each since you made two." Jay responded.

"OK, well first the truth. Hmm, how often do you jerk-off?" Ben asked.

"Well, I guess an average would be once a day," Jay said, matter of factually.

"OK, well for your dare, I dare you to send Ced a text saying you want to suck his dick."

"What the fuck! Getting intense aren't we? OK, fine. I guess I have to do it." Jay pulled out his phone and typed the text 'I wanna suck your dick' and showed it to Ben for approval before hitting send. There was no immediate answer, so the game carried on. Jay made hit next 3 shots, leaving him with only 4 balls on the table. "OK, I've got 3 to give. What do you take for your first one? Truth or Dare?"

"I'll take truth." Ben said, nervously. Ben was a very private person. He didn't like the thought of being asked anything.

"OK. What did Sara's tits look like?" Jay asked. Sara was Ben's ex and Jay's best friend Chris's current girlfriend. Their break up and Chris and Sara's new relationship caused a riff in the group. Jay was still friends with all four but Sara and Ben and Chris weren't with each other.

"Interested in my ex?" Ben said, half surprised and half intrigued.

"I've always thought she was cute. I'm just curious as to what her boobs look like."

"Well, they were pretty nice. When she started gaining the little bit of weight they got bigger. A nice handful, not that she let me touch them much. She wasn't exactly sex craved. Her nipples where the little cute ones. Not like drop gum, but medium size I guess."

"Nice, she's a bitch but I'd still like to hit that" Jay said with a chuckle.

"Even though she's with Chris and used to be with me?" Ben asked with curiosity, not anger.

"Yeah sure. Not like I'd cheat with her, but I'd still like to fuck her. Anyway, what's next? Truth or dare?"

"Hmm, I guess I'll take dare." Ben said, with nervousness.

"OK, I'll be easy on you, not like you were on me. I dare you to take 5 shots of vodka in a row." Jay said.

"Wow, 5 shots in a row is a lot. I usually only do 3. OK fine. Let's go upstairs and do this." Ben said in a tough guy type of attitude. The boys headed up stairs and Ben got out the Vodka and set up 5 shots in front of him. "Here goes nothing." Ben said and a moment later he downed all 5 shots in succession. "I'll take truth for my next one, by the way."

"Pussy!" Jay said with a grin on his face. "OK. I got a good one. Have you ever had a gay dream?"

"What the fuck? Well, I don't guess that's any worse than me making you tell Ced you wanna suck his cock." Ben said.

"You didn't answer the question."

"OK fine. Yes, I had one, one time."

"What was it about."

"Nope, that wasn't part of the question. I answered your truth question, truthfully." Ben said with a sense of accomplishment. "Time to get back to the game."

The boys went back down stairs. Ben's parents had already went to bed so they knew they needed to be politely quiet. The game carried on and Ben made one ball before he missed.

"Truth or dare." Ben asked, feeling a little tipsy from the 5 shots of vodka.

"Dare."

"OK, well I'm starting to feel a little drunk and I don't wanna be the only one with a disadvantage so I dare you to take 5 shots of vodka too!"

"Damn, you know I''m a lightweight! That will get me totally drunk."

"Exactly." Ben said as he started walking upstairs. Jay followed and Ben was already setting up his shots. Before Jay knew it, there were 5 overflowing shots of Vodka sitting in front of him. He nutted up and choked down all 5 shots. They went back down stairs and the game resumed. Jay missed he next shot and Ben made one ball. "Truth or dare?"

"Truth" Jay said, feeling tipsy, and knowing it was gonna get worse quickly.

"If a hot girl you were about to sleep with had a dick, would you still sleep with her?"

"Wow, what a question. I think my honest answer would be 'it depends'"

"Bullshit, answer the question. Let's say she looks just like Kristen Bell"

"Oh hell yeah then." Jay said, something he never would have admitted if he were sober.

"Fag" Ben joked as Jay went to take his next shot. The alcohol was really kicking in but he did manage to sink one ball. "Truth" Ben said before even having to be asked.

"How big is your cock, fully hard?"

"That's so gay." Ben said, not wanting to answer the question. He knew he had to though so after stalling for about 30 seconds he answered "about 3 inches."

"Wow, no wonder Sara dumped your ass!" Jay laughed, jokingly.

"Asshole. You better hope I don't make any balls." Ben went and he did actually make 2 balls., leaving him with just one and the 8.

"Truth or Dare, bitch"

"Dare"

"OK, I dare you to take off your shorts and keep them off for the next 24 hours." Ben said, knowing this would be difficult because he would have to go home eventually.

"Damn, that's a good one." Jay said, feeling defeated. Jay was sporting a semi as he slid down his shorts and tossed them aside. His underwear was kinda tight so you could clearly see the outline of his cock. Ben's eyes lingered a little and Jay noticed but didn't say anything. He just grinned to himself and went on with the game. He was pretty drunk by this point but still managed to get 2 balls in. this left Jay with just 2 balls and the 8 and left Ben with 1 ball and the 8. "Truth or dare?"

"Truth."

"Man, what's with you and all these truths! You pussy!"

"I'll pick dare next. Just know the pay back is gonna be a bitch."

"OK, hmm let's see. What was that gay dream you told me about earlier about?" Jay asked, betting Ben had thought he'd forgotten.

Indeed Ben did think he'd forgotten. Fuck, he thought. He had to tell him the truth. "It was when me and Sara were together. I dreamed that Me and her asked you and Chris to join in on sex with us."

"Dude, that's a gang bang, not gay."

"Well, Sara wanted to see us three do stuff, so we did."

"What the hell is going on in your head! What did we do?"

"No, sir. That's classified."

"Whatever. Now you have a dare. I dare you to strip down to your underwear and run down to your mailbox and back. And then leave your clothes off."

"That's so gay, but whatever, dares' a dare." Ben replied to Jay's dare. He secretly loved the idea of being nude in public, but this was about as close as he would have ever been. Ben took his shirt off and tossed it aside, then started up the stairs. Jay followed to make sure he did the dare in full. Ben was beginning to get turned on as he thought about what he was about to do. His 1 inch penis began to grow about before long it was at it's full 3 inch length as hard as a rock. The problem is he was wearing some tight underwear because all his boxers were dirty. As the boys go to the front door, Ben began to lower his pants and his small cock sprung out pressing against his underwear.

"Damn, you weren't kidding about that 3 inches." Jay joked, standing in his friend's kitchen in his underwear himself. Ben was now in just his underwear.

"Shut up, dick. Crap, this door makes a lot of noise, how about you edit the dare." Ben asked, hoping for mercy.

Jay thought about it for a minute. He was in his underwear too and the loud door was sure to wake his parents. They could come out to see what was going on. "Nah" Jay finally answered, holding Ben to the dare he came up with. Ben looked angry but opened the door and stepped outside quickly. Then Jay did something totally unexpected. The door was, in fact loud and he knew it probably had woke one or both of Ben's parents. As Ben was running down the driveway, Jay shut the door and locked it. Then he quickly went back downstairs before with Thelma or Steve had a chance to come out and catch him. When Ben got back up and discovered the door locked he freaked out. He was also kinda upset, but was also still drunk so he thought it was kinda funny too. He began to walk to the sliding glass door to the basement. Just as he walked out of view his Mom looked out the window. She didn't see anything and went back to bed.

Ben knocked lightly on the sliding glass door and Jay pulled back the curtain, laughing. He opened the door and let Ben in, but not before taunting him.

"That was bullshit. Totally not part of the dare." Ben said, half mad half laughing.

"No one ever said you can't pull a prank in the middle of truth or dare." Jay replied. "Man, I think I need some more to drink."

"OK, let's run upstairs real quick and get some." Ben said, thinking about both him and Jay being in their underwear and him with no shirt. "But we gotta make it quick in case my dad gets up." The boys went upstairs into the kitchen. Ben poured 3 more shots each while Jay grabbed a pack of Smirnoff Ice drinks. These were his favorite type of drink to sustain an inebriated state. They chugged down all three shots each and made their way down the stairs with the other drinks. Then the game carried on. Ben made his last, non-8 ball but failed to make the 8 so he didn't get the big dare. "Truth or dare" he asked Jay.

"Dare"

"I dare you to run upstairs and take 2 more shots." Ben said. As Jay started toward the steps to go upstairs Ben spoke back up. "Naked."

"Shit. I guess I have to." Jay replied to the dare, the most risky one of the night. He was still pretty buzzed, but did know enough that if he got caught upstairs, naked, it would be an extremely awkward situation to explain. Ben had secretly wanted to see Jay's cock ever since Jay accidentally touched his in the pool earlier. He had never had actual gay feelings, but this incident sparked his interest. He was excited that this situation had come up. Always having such a small dick, he was curious as to what his friends size was. Jay slid down his underwear and his large cock was revealed. Ben guess it was about 6 inches or so. It was very thick, however. Not something he could say about his own. Ben could see it start to harden and it grew a little bigger before Jay turned to head up the stairs. This make his tiny little dick start to grow. He walked up the stairs behind Jay and stayed at the top as Jay went through the door to get the shots.

As Jay was pouring his second shot he heard Ben's parents room door open. It was Steve. He had gotten up to go to the bathroom but heard some noise coming from the kitchen so decided to go check it out. Jay was standing behind the island as Steve walked into the kitchen. It was just tall enough to not reveal he didn't have pants on. By this time Jay's dick was rock hard, all 9 inches of it.

"Good morning." Jay joked, still buzzed but surely aware he could not let Steve see that he was nude inside his kitchen with a hard cock,

"Yeah, sure." Steve chuckled. He began to walk over to the fridge. As he did this Jay moved his way around the other side of the island, making sure to keep his lower half of his body out of view. "Where's your shirt?"

"Downstairs. It got kinda hot with the fire place." Jay lied, using the electric fire place as an excuse to have no shirt in the middle of the night when Steve knew that he and Ben were still hanging together.

"Well tell Ben to turn it down." Steve said as he grabbed something from the fridge and turned around to walk back to bed.

Jay was relieved as he downed the two shots he was dared to do. Throughout this entire situation, Ben was peaking through the basement door, stroking his tiny little cock. He couldn't believe how much his friend being naked in his kitchen with his dad being right across the room from him was turning him on. As he saw Jay walking back toward the door, he put his cock away and moved back down the stairs.

"Damn that was close!" Jay said as he put his underwear back on.

"No shit. I wonder what he would have done if he'd seen that you were butt ass naked."

"No idea, but I'd rather not find out." It was now Jay's turn and he went and sunk both normal balls he had left on the table, giving him two and leaving only the 8ball for both boys.

"Truth or dare?"