Friends Share Everything

"You certainly did. So, does that mean that every time you two say I'm hot, or pretty, or beautiful, that you're flirting with me?

"Yes."

"Wow, boys. I have to admit, you're very smooth. It's hard to believe that you two are eighteen and have never had girlfriends."

"We didn't really have time to date. We were always gaming and studying."

"Well, it's nice to have some attention. It's been a while since I have had some attention from some handsome young men. Maybe too long." Judy smiled.

"You know mom, you're still young, you can start dating again." Ryan said.

"That's sweet, Ryan. But it's a little hard to date with two young men living in my house."

"Well, we won't be living here forever. You'll have all the time in the world after we leave."

"I know, I guess I need to enjoy you two while I can." Judy laughed. "Well, I'm stuffed, thank you for the meal. Now, you boys have had a very productive day. I don't have any more chores for you. Don't worry about the dishes."

"Well, um mom, we kind of wanted to ask you a question."

"Go on."

"Chris and I wanted to see if you wanted to play a game with us."

"A game?"

"Yeah, it's a game I read about online. A drinking game people play at college."

"I don't know Ryan; you know I have never approved of underage drinking. You boys are just eighteen."

"Come on, mom, we're adults now. It'll be fun."

"Well, what game did you have in mind, honey?"

"It's called flip or sip. You flip a coin, if you guess right, you don't do anything. If you guess wrong, you drink, then it goes to the next player."

"Hmm, I don't know."

"Come on, mom. You never do anything fun."

"Yeah Ms. H, it will be fun!"

"Oh, alright, boys. You convinced me. I'm going to shower and change into something a little more comfortable. I'll be back in 20 minutes." She walked upstairs shaking her head that this is how she was spending her Thursday night.

"Sweet! I'll go grab some beers." Ryan ran into the kitchen.

"I'm glad we got her on board." Said Chris.

"Same, here I come with the beer!" Ryan returned with three bottles of beer.

"Awesome, now we just need some shot glasses." Chris looked through the cabinets until he found them.

The boys excitedly talked to each other about girls and stuff until Judy came down the stairs. She was wearing a purple tank top that clung to her large breasts with a grey sweater over it. She had on some short shorts which were very tight on her behind. She also wore sandals; her toenails painted a light blue.

"Mom, you look amazing!"

"You can really fill out a pair of shorts."

"Ha, save it you two. Your about to lose to the flip or sip queen."

"Ok let's play!" Ryan flipped the coin and covered it with his hands. "Ladies first." Ryan winked at his mom.

"Tails."

Ryan lifted his hand. It was tails.

"Wow, I guess I'm off to a good start."

"My turn." Ryan flipped the coin. "Tails." He lifted his hand.

"Heads. Ha! Drink up."

Ryan sighed and opened his bottle. "Here goes nothing." He poured a shot of beer and drank.

"That's not so bad, right Ryan?" Judy smiled.

"Nope, not at all." Ryan flipped again and lost.

"Dang it!" He took another shot of beer.

"You're lucky you're a good-looking boy. I wouldn't put up with you if you weren't." Judy laughed.

They continued to play until they all finished their first beer. Chris got up and got three more. The trio finished those, and then started on another three.

"Ok mom, call it." Said Ryan.

"Tails." Judy answered, slurring the word a little.

Ryan flipped the coin. It was heads.

"Honey, I don't think I can drink anymore; I'm feeling kind of tipsy."

"Come on mom, we're having fun, how about from now on, you can take off an article of clothing instead of drinking."

"What!? Now I see what you two were up to this whole time."

"We just wanted to have some fun and pretend like we are at a college party." Chris said.

"Fine, I'll play your stupid game." Judy hiccuped. "But I'm not taking my shirt off, you two." She kicked off her shoes.

Ryan and Chris flipped and both lost. Ryan took his shirt off and Chris took his shorts off.

"My turn." Judy said. She flipped and won. "Ha! Nothing for me."

Chris and Ryan lost. Ryan took his pants off, and Chris took his shirt off. They were both sitting in their underwear.

"You boys wanted to play a stripping game and you only brought three pieces of clothes?"

"We didn't really plan this out well, Ms. H." They all laughed.

Judy won again and didn't have to take anything off.

"Mom, you're killing us! We are way behind." Ryan complained.

"What's the matter honey, not having a good time?" Judy winked.

Chris lost again and looked embarrassed.

"Don't be shy, Christopher. It's not like I've never saw a naked man before."

"Yeah Chris, were family here. Don't wuss out now."

"Ok." He nervously took his underwear off. His cock was half hard.

"Well, look at that. I had no idea you were so big!" Judy said, a little drunk.

"You're making me embarrassed Ms. H."

"No need to be. It's beautiful."

"Well, it's my turn. Here we go." Ryan flipped and lost. "Ah, come on!"

"Sorry, son." Judy laughed. "It is what it is."

It was now Ryan's turn to look embarrassed. He slowly slipped off his underwear. His cock was half hard as well.

"Hmm, well, look at that. You boys are very well hung." Judy giggled to herself.

"You're enjoying this aren't you?" Asked Ryan.

"Maybe. My boys are just so handsome, how could I not. How about this, since you boys no longer have any clothes, if you lose you both have to do a dare?"

The boys looked at each other.

"Sure, why not?" Said Chris.

"Fine, we accept."

Ryan flipped the coin and Judy guessed heads.

"Tails! Your winning streak has ended!"

Judy took off her sweater.

"Your turn."

Ryan flipped and lost.

"Dang it! Ok, what's the dare, mom?"

"Hmm, I want to see how big you boys are. How about you measure each other."

"Seriously?" Ryan and Chris looked at each other.

"What? You can't blame a girl for being curious. Besides, I'm your mother, I deserve to know."

"Fine." Ryan got up and grabbed a measuring tape. Chris stroked himself, trying to get as big as possible, and put his penis on the coffee table."

"Wow, six and a half inches. That's pretty impressive." Said Judy.

Chris smiled to himself. He then grabbed the tape and measured his friend. "Seven inches."

"That's my boy!" Judy said proudly. "You both have such nice bodies. You're going to make your girlfriends so happy."

"Thanks, Ms. H. We'll do our best." Chris said.

"Ok, mom, call it." Ryan said.

"Heads." Said Judy.

Ryan flipped and it was tails. She lost. Judy removed her shorts. She was now sitting in her t-shirt, a bra, and panties.

"Wow, your legs are really toned. How did you get them like that, mom?"

"Thank you, dear. It's all those morning jogs. It helps a lot, and I have a lot of fun."

"Your legs are perfect." Chris said.

"Thanks, boys. Well, looks like I've lost my touch at this game though."

Chris called his next toss and got it right. It was Judy's turn again. She lost.

"Are you cheating? Thats like five losses in a row."

"I promise mom, just a coincidence."

"Ok." Judy removed her t-shirt. She was wearing a purple bra. Her boobs looked like big round globes.

"Wow, Ms. H. You have a great body."

"Yeah, mom, I don't think we have seen you wear that type of bra before."

"Well, some people that I know have been taking peeks at my underwear, so I thought I would wear something a little more fun."

"Ok, call it Ryan."

"Heads." Ryan flipped the coin, and he guessed wrong.

"Dare time. Ok, this time, I dare you boys to tie your shirts around your eyes and sit on the couch next to each other with one cushion in between."

The boys did as they were told.

"What are you planning, mom?"

"You'll see dear. I'm just going to have a little fun with you two." The boys heard some rummaging around.

"Can you see anything, Rye?"

"No, mom."

"Chris?"

"Nothing, Ms. H."

There was no sound for a minute.

"What do you think happening?" Said Ryan.

"I have no idea!"

Suddenly, Judy sat between them. "Mmm, you boys have such nice bodies, I want to make sure I get the full boy experience." There was the sound of lotion being rubbed between two hands. Judy wrapped a hand around each of the boy's cocks and began stroking them.

"Oh, fuck!" Ryan moaned.

"Ms. H, that feels amazing."

"You boys have such nice cocks." Judy sped up her strokes. "Don't be shy now. I thought you wanted to get some practice?" The boys felt Judy spread her legs apart, so they were both touching her legs against theirs. She felt, naked.

Chris was the first to make a move. He reached his right hand over and started to run it up and down Judy's thigh. Judy moved her legs apart a little wider, giving him easier access.

"Ooh, you boys are making me feel so naughty." Judy said, speeding up her strokes.

Ryan meanwhile reached his right arm across and started manipulating his mother's breasts and nipples.

"Oh, honey." Judy moaned.

Judy began to moan and pant a little louder.

"That's it, baby. I love the way you touch me. Mmm."

Ryan started kissing her neck and shoulders, while squeezing her boobs. Judy was still stroking their dicks. She could feel that they were almost ready to pop.

"Yes, honey. That feels amazing. Are you close, Chris?"

"Yes, Ms. H. I'm really close."

"I'm right there with you." Ryan said.

Judy picked up the pace of her strokes, causing both boys to moan.

"Mmmm, that's it. Cum for me boys. I want to see how much you make."

Chris was the first to cum. He moaned and shot a huge load onto his stomach and covering Judy's hand.

"Wow, that's a lot of cum. Good job, Chris. Ok, Rye, let's see it. Show me what's in those balls."

Judy picked up the pace again and gave Chris some more kisses on the neck. Ryan couldn't take it. He moaned loudly and shot his cum onto his mom's arm and hand.

"Oh my, I guess you had a lot in there too. Good boys." Judy kept stroking until they were done cumming. She reached down and grabbed a towel she had hidden under the table and wiped the boys and herself off.

"Ok, boys, I think our game is over. That was a lot of fun, but I'm getting tired, and I have work tomorrow. I'm going to bed. Don't take the blindfolds off until you hear my bedroom door close.

Judy put her clothes on, kissed each of them on the cheek and went upstairs. The boys sat there for a few minutes until they heard her bedroom door close. They removed their blindfolds.

"Holy shit, dude."

"I know, man. What the hell just happened?"

"I think my mom just gave us hand jobs."

"That was the most amazing thing I have ever experienced." Said Chris.

"Same."

That sat in silence for a minute.

"Hey, I'm sorry I am fooling around with your mom. You're not going to be mad, are you?"

"Dude, you're my best friend. I don't think I would have had the balls to do this without you."

"Me neither, man."

"Hey, you're not going to tell anyone that my mom gave me a hand job, right?"

"Of course not, bro. Like you said, it's just practice."

The boys cleaned up the beers and straightened up the living room. They went upstairs and both passed out immediately.

Chapter 3

The next morning, the boys woke up late. Judy had already left for work. They both got dressed went down to the kitchen and made coffee and some cereal.

"Man, last night was awesome." Said Ryan. "I can't stop thinking about it."

"Yeah, I had no idea that your mom was so horny."

"Dude, she's been divorced for five years. I'm not sure if she's gotten laid since then."

"Maybe she has a boyfriend or something."

"Maybe, but I'm not sure, I never saw anyone come and go. I think my dad really messed her up with guys."

"Dang, I feel bad for her."

"Yeah, same."

"Well first things first. Women aren't going to like us if we're out of shape. Let's go to the track and get some work done."

"Yeah, sounds good."

They spent the next two hours at the track running and working out. They showered and headed back home. When they got inside, they sat at the kitchen table.

"What do we do now? Video games seem kind of fucking boring." Said Chris.

"True, I mean, what the hell is the point. All we are doing is sitting on our asses. We have no girlfriends, no money, no jobs."

"Hey, wait a minute." Said Chris. "Why don't we get jobs. We can surprise your mom with something special at the end of the summer. Like, I don't know, a trip or something."

"Hmm, I like that. That's a great idea, dude. We have the whole summer until we go to college. I say, we both get a job, save some money, and take mom somewhere awesome."

"Exactly, and while we are working, we can try and practice hitting on ladies."

The boys spent the rest of the day looking for jobs online and riding their bikes around the city doing applications.

When Ryan and Chris returned, Judy was already home and out of her work clothes.

"Where have you two been all day?"

"We got bored sitting around, so we decided to look for jobs."

"Really!? That's great! I'm very proud of you two. Do you have anything lined up yet?"

"Not yet, but we applied at a lot of places. Hopefully something will come through soon."

"Good. Well, you both should be hungry, right? Come on, how about I order a Pizza?"

"Sounds good to me." Chris said.

"Yeah, sounds great, mom."

Judy ordered the pizza, and they sat around the table.

"So, Ryan, Chris, I wanted to talk to you about last night. I think we got a little carried away."

Ryan and Chris looked at each other, anxious their fun was coming to an end.

"Ryan, I'm your mother. Do you really think it's appropriate that I would be touching you like that?"

"Um, well, I..."

"Don't interrupt, Ryan. I'm not done. You, Christopher, are not my son, but you are twenty-two years younger than me. Now, I don't want to come off as a prude, but I'm not sure we should be practicing anymore."

Ryan and Chris looked disappointed.

"Did you not have a nice time with us?" Chris asked.

"Now, that's not fair, Chris. You know, I enjoyed it. In fact, I enjoyed it so much, I thought about it all day at work. It's all I could think about."

"Then why can't we do it again?" Asked Ryan.

"Well, for one, you are my son, and that's not right. Two, you're only eighteen and I'm forty. How would that look, people would think I'm some kind of freak or something."

"Mom, you are freaking hot! Doing that with you was the coolest thing I have done in my entire life."

"It's true Ms. H. You are gorgeous. I can't stop thinking about last night."

"I had a great time too, but I can't. It's not right. I have no interest in ruining your reputation, Ryan. You will meet a great girl in college. If people find out you are messing around with your mom, that will ruin any chance you have with someone new."

"But, what about you?" Asked Ryan. "When was the last time you fooled around with someone?"

"That's not the point, honey."

"Yes, it is. It's not fair if you can't have any fun. I know it's a little weird because I'm your son, but that's kind of hot too, in a weird way."

"Yeah, Ms. H. If you are having fun and enjoying yourself, what's the problem?"

Judy started to blush.

"Look, guys, this is a sweet offer, but it's just not right. It wouldn't feel right to have sex with my own son or his best friend."

"Sex?!" The boys looked at each other. "We were talking about practice. You know, just touching and stuff. Nothing serious."

"Oh, um, well, yeah, I just assumed..." Judy trailed off.

"So, can we practice a little more? We won't ask for anything else. Promise."

"I don't know." Judy rolled her eyes and shook her head. "I'll think about it, but I don't want to hear any more about this tonight."

Just then, the doorbell rang.

"That's probably the pizza." Said Judy.

After dinner Ryan and Chris went to their room.

"What do you think, dude?" Said Chris.

"She definitely liked it. I could tell." Ryan lay back in bed. He put his hands behind his head and sighed.

"We need to come up with another plan. That drinking game worked. How else can we get her out of those panties?" Chris wondered.

"We need to take this slow. We need to take her somewhere fun. Where she'll forget that she's my mom, you know?"

"Oh, like a date?"

"Yeah, kind of. A practice date. The game we played was exciting you know. It got our heartrate up when someone won or lost. We need something like that."

"Dude, I got it. Let's go to the waterpark at Playa Vista!" Said Chris.

"The waterpark?"

"Yes! We will be half naked, hanging out at the pool, in the jacuzzi, and we can go on the water slides, it will be exciting!"

"Wow, that's genius!" Ryan got out of bed and went in his closet. He fished around until he found $300 that he made the summer before mowing lawns. "I think I have enough money to cover the day passes."

Chris went through his duffel bag and pulled out his emergency cash. "I have another $300 too, so I will keep the drinks flowing as long as I can."

"Awesome, now all we have to do is get my mom to agree."

The next morning, Judy got up to make coffee. The boys were already at the table eating cereal and watching the news. There was a fresh pot of coffee waiting for her.

"Morning, boys."

"Morning, Ms. H."

"Morning, mom. How are you?"

"Fine, sweetie. I slept great, how about you two?"

"Same. We have been up for a while packing. We're going to head out soon."

"Packing? Where are you going?"

"To the waterpark at Playa Vista." Said Chris.

"Wow, sounds like fun, when are you leaving?"

"We're leaving in about an hour. I bought the tickets for us online last night." Said Ryan.

"For us?"

"Yeah, me, you and Chris. We figured we could use a day out; we've been cooped up in the house all week."

"Well, I'm flattered, but I'm not sure I can go. I have laundry to do and..."

"Please, Ms. H." Chris cut in. "It will be fun. We'll pay for the tickets and everything."

"Yeah, mom, you work so hard. You deserve a fun day out with your son and his friend."

"Well, alright, I suppose a day at a resort sounds fun. I haven't been there in years."

"Great! Just grab your bathing suit and stuff. We will have everything else."

Judy got dressed, she wore a loose-fitting white t-shirt over a yellow bikini and some khaki shorts and flip flops. Ryan and Chris wore blue swim trunks and white T-shirts.

Judy drove to the waterpark, and they arrived within the hour. They entered the park and went to the locker room.

"We'll meet you out front, mom."

Judy walked to the woman's locker room and the boys met her a few minutes later. Judy had her hair pulled back and was wearing a big floppy sun hat.

The resort had a few bars, a water slide area, a lazy river, a jacuzzi, and an area for swimming. They had a buffet and a couple of gift shops. It was fairly crowded as it was the beginning of summer, and the weather was hot.

"Wow, this place is huge." Said Chris.

"Yeah, apparently, it's one of the biggest resorts in the state." Said Judy.

Ryan walked up to one of the staff. "Hello Sir, I rented a cabana online, is it ready for us?"

"Name please."

"Ryan Hills."

"Oh, yes, sir. It's ready for you. Follow me please."

The employee led them past the pool area and to a row of cabanas near the jacuzzi. The cabanas looked like luxury tents. They had two couches, a TV, a mini fridge and a coffee table. There were drapes that could be used for privacy, but at the moment they were all open.

"Here we are, number five."

"Thanks, man."

Ryan tipped the guy and they stepped inside.