A gay sex story: 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.”
[zilla_likes]