Down The Road

I want to give thanks to MaryJon for editing and helping me with the development of this story. Plus thanks to MarriedinMaine2 for the final review.

*

Tim and I were over at Dave's house hoping to catch a glimpse of his hot mom. I was watching them play X-box.

The door opened and Dave looked up. "Hey Mom, are you two done with your run, or just getting ready to head out?"

His mom, May, took a huge gulp from her water bottle. "We just finished. We did a three mile run today," she said, pressing a hand towel to her dripping forehead. Looking at me, she said "Hi Jack, are you enjoying your summer?"

Karen, Tim's mom (also very hot), then jumped in with: "By the way, why did you guys stop hanging around with the two guys down the road? They seem very nice. What are their names again?"

"Not sure who you're talking about," answered Dave.

"Well, they were very nice to us just now. Look and see if you know them. They're down the road playing basketball," added May.

I glanced out. "It's those jerks Bob and Jake."

"Mom, we're not going anywhere near those dudes. They're trouble with a capital 'T'." Tim said.

Karen raised her eyebrow. "Are you sure, honey? They seem very nice."

"No, they are not nice!" Tim said, pounding his fist on his leg. "Trust me; they're just two assholes."

"What do you mean by that?" May replied, with a surprised look on her face.

"If you really want to know, sit down so we can explain it to you," Dave said.

May and Karen rolled their eyes as they sat down. Dave then started to inform them about Bob and Jake's reputation: "Yeah, we hung around with them when we were younger, but as we got older those two learned that they could intimidate people just from their large size. They started to boss everyone around, then when someone did stand up to them, they would just overpower them. You know, like smack them a few times until they finally agreed to do whatever they told them. One thing I can say, they never did mess with us, guess because we used to hang with them. I just don't like being around guys like that."

Tim jumped in: "They have no respect for others, especially women. I know that a few of their girlfriends tell everyone that they treat them badly, by spanking them when they didn't do what they wanted. Instead of leaving them they would just go back to them, I just don't understand why they would. Unless they really enjoy being treated that way. I've even heard that they hooked up with a few of the married women here in the neighborhood and some of the female teachers."

Then I added, "Of course since I'm newer in this neighborhood I never knew them when they were younger, and I've never hung around with them. But from the rumors that I have heard, even after they break-up with their girlfriends, they still have some kind of control over them. Some people call all the women their 'little harem,' but nobody knows if this really is true or not. I've also heard that the reason they have such control is they blackmail these women by taking videos and pictures of them. I know you two will not get involved with them. We're just telling you this because you asked why we didn't hang around with them and we don't want you to get caught up in their bullshit."

May nodded and gave a weak shrug. "Yes, I've heard those same rumors from the neighborhood rumor mill. Every time Karen and I run past them, they are always giving us some kind of complement." She laughed. "I'll admit, I kind of like the attention. But remember, those rumors don't mean they're bullies anymore than you three. I've heard rumors about you three also, doesn't mean they're true either."

Karen shook her head in agreement, adding, "People love to tell stories about others, whether they're true or not."

Tim added, "I know you heard about Mrs. Smith then, our English teacher. She got fired over a sex video that turned up. No one can prove it, but they say Bob and Jake had something to do with it."

With a look of concern, May said, "Again, that is just a rumor and no one really knows why she got fired. So give it a break guys." May seemed aggravated that we'd repeat these rumors, even though, from my point of view, we were trying to warn them about something serious.

Dave replied, laughing, "All righty then. Just remember what we said. If you do end up talking with them, just don't let them talk you into their garage. You have been warned!"

Karen, laughing, answered: "Why would we ever go into their garage?"

"Well just don't!!" was all Tim said.

As the moms left the room, we went back playing X-box. Of course, I kept an eye on them. As they walked out of sight, I overheard May say to Karen "It sickens me how easily rumors spread in this neighborhood, those kids they're talking about sure do seem like good boys to me."

Then she added, in a flirty type of voice, "I sure would like to find out if the rumors are true about their size, though," and she emphasized "size" in a way that made me pretty sure she wasn't talking about how big and muscular Bob and Jake clearly are.

Chuckling, Karen replied, "Well, that's never going to happen. But I agree with you, there's no reason to treat those boys differently because of some mean rumors. Some girl probably started those rumors when Bob and Jake wouldn't date them or something." Then they were too far away for me to hear any more.

That was all that was said about the subject and Tim and Dave departed for school the week after. They were such nerds that they were starting college early. Even though I'm their friend, I'm not as into school as them. Without them, though, I had a summer in front of me without much to do. Guess I could have gotten a job, but I wanted to take the summer off before I joined the real world.

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One day, bored out of my mind, I was walking and saw Bob and Jake out shooting baskets. I remembered what May had said about them being nice and went over to them and asked, "Hey, mind if I shoot some hoops with you guys?"

Bob looked at Jake and then at me and tossed me the ball. "No probs, man."

This friendly surprise shocked me, and I missed the shot. Everyone had a good laugh and this seemed to break the ice between us. I spent the rest of the day with them. They sure didn't seem to be the bullies I had heard about through the rumors. We ended up becoming friends and I was back every day to shoot hoops and hang with them.

One sunny day we were playing a small game of horse and someone yelled "Well hello, Jack!" I knew that voice, and after turning around, my suspicions were confirmed: it was May, running alongside of Karen.

She waved. "I was wondering who the other guy was playing baskets out here. Glad to see you three are getting along!" she said, panting.

I just smiled and waved at the two as I watched them run on by.

Then I heard a whisper. "You know those two MILFs?" I peered down to see Jake crouching beside me.

"I sure do, the one with red hair is Tim's mom and the other one is Dave's mom. They like to run together every day." I laughed, thinking to myself, May and Karen are so hot, MILF is exactly how to describe them.

"I see them down the street all the time. I didn't know they were Dave's and Tim's mothers!" Bob said, cutting through my thoughts.

"Now we have something else to talk about today," added Jake.

"They're the main reason I'm friends with their sons. They are some hot mature ladies." I added, smiling because Jake was right, I now had something else to talk about with these guys.

"So what else do you know about them?" asked Jake.

Wide eyed because these two were suddenly so interested in what I had to say, I continued, "I believe they are both around 40 years old and have been friends since their days playing on the women's college basketball team. They are always bragging about how good they are at the game."

Jake gave Bob a suggestive nudge. "Looks like we're going to have to get them to teach us some moves."

Smiling at that statement, I continued. "As you can tell, Karen has a slim figure, with a cute face. Men can't resist her, I've seen them try to cop a feel during her backyard parties. Who wouldn't, those breasts look so firm and large. I know I would love to play with them."

Bob chuckled. "Maybe she will let us feel her up."

"Dream all you want; she's out of your league," I said, now laughing.

With a smirk on his face, Jake said, "We'll see."

Smiling, I just continued, "May has a pretty nice rack too, though. I dream about finding out what they look like and playing with them. She is a nice person and easy to talk with. I like her cute blonde ponytail. Most of Dave's friends call her a hot dish, and hell, she is."

"Fuck yeah," Jake said in a voice that sounded more like a moan. I noticed he was grabbing his crotch and laughing.

---------------

As usual, the ladies showed up on their run the next day.

"Heads up!" May caught the ball Jake threw and took a shot; it went right in.

Then she came over with Karen. I think they started a conversation about what they've been doing lately. I didn't pay much attention to what the four of them were talking about as I picked up the ball and started working on perfecting my shot.

I heard Bob ask, "Would you two like to shoot hoops with us?"

Karen ran over to me and grabbed the ball. "Sure, why not, it's been awhile since I played."

From then on, the five of us would just shoot hoops for a few hours every day. We ended up becoming good friends, which seemed weird to me at first because I was also friends with their sons.

As the days went by, it became as if we all were friends forever, we would even flirt with each other. The women teased us by wearing tight shorts with low cut tops and bending over, making sure we could see down their tops.

Bob and Jake would whisper to them all the time, making sure I didn't hear what they were saying.

One day, I heard a surprised shout. "Have you forgotten we're married?" I dropped the ball and turned to see May sticking her ring finger into their faces. "Plus, I'm old enough to be your Mom! I'm sure it isn't that big. Now stop it."

It isn't that big? Was she talking about a penis? I tensed up thinking of that.

Karen smiled. "Look guys, enough. By now you should know we're not going to flash." She walked off for a moment until she suddenly turned around. "But if you really are that big, I wouldn't mind taking a look." The sentence was followed with a wink that made Jake take a step back. May gasped.

Bob put his hands on his hips and said in an authoritative voice: "Listen, you're both hot women and not our moms. With all the teasing you two have been doing the last few weeks, we think it's time for you two to let us see those goods." His hands made a curving motion around his chest on the word "goods."

The two MILFs shook their heads in unison and headed off. My eyes followed them until they were out of sight. "What the hell was that all about? They looked pissed off to me. You think they will be back?"

Bob chuckled. "Been trying to get them to show us their tits for a while now. We also told them how big our cocks were, but they don't believe us. I even offered to show them our cocks if they would show us their tits. They keep reminding us they're married and won't budge."

He bounced the ball. "But of course they'll be back. Haven't you noticed? They keep looking at the bulge in our shorts. They totally want our cocks."

I grabbed the basketball. "You think they'd be up for a bet?"

-------

Bob was right; they were back the next day and we shot hoops like nothing had happened.

Jake strolled over with a grin. "Listen, ladies. I know you don't want to upset your husbands, but do they know you're out here shooting hoops with us every day?"

Karen rolled her eyes. "Of course, silly. My hubby knows, and he doesn't mind."

"I tell my old man everything and he doesn't mind either. We know what you're trying to do here, and it isn't working," May chimed in. At this point, I actually doubted that May and Karen really did understand what Bob and Jake were hoping for. They seemed to think that we were too young to take seriously or something.

Jake nodded. "Well, did you tell them that we wanted you to flash us?"

May looked horrified. "Why would I need to? It's not going to happen anyway!"

All three of us guys were now laughing.

Bob patted May on the shoulder. "Hey, why don't we play a little two on two, guys versus girls?"

"Sounds nice. It's about time we stop just shooting hoops and start playing a game. We're going to show you guys how it's done!" May answered.

"Except there's three guys. Who's going to sit out?" Karen stated.

Jake looked over at me and I replied, "Guess I'll be the one watching. I need a break, anyway."

"We're going to show you guys how it is done!!" yelled May.

Bob laughed, "We'll see about that."

Jake pointed toward May and Karen and said in a commanding voice: "But here's the deal, ladies. If we win, you put on a strip show for us. No arguments about it. If you get lucky and win we'll give you a strip show. You know, to make it fair."

I just looked at Jake, thinking, I'm not even playing but this could get interesting. My cock stirred in my pants as I imagined the ladies slipping out of their clothes. Damn, I thought. The guys had better win.

May smiled, "I hope you're just kidding. What makes you think we would give you a show?"

Karen gave May a calculating look. "Well, if we win, and you know we will because these two will be too busy watching us that they won't play well, I wouldn't mind watching these three take off their clothes. Then we would know if what they've been telling us is true or not."

"Well, yes, I know we will win, and you're right, we would find out if they are as big as they advertise. Then again, we could lose and I don't think it would be a good idea to give these guys a show," replied May.

"No guts no glory!" I shouted, trying to get them to take the bet.

"I didn't think you would do it, just wanted to see if all the bragging you two have done the last few weeks about how good ball players you are was true. Guess now you two can either put up or shut up about how great you are," Jake said, in a daring voice this time.

May looked a little pissed off. "We're not bragging about how good we are, it's all fact."

She looked at Karen. "If you're game, I am. I know we can beat these two assholes."

"You'd better be as big as you advertise. Three out of five?" said Karen.

"Deal." Bob then leaned down to me with a dirty grin and whispered, "Once we get these two in the garage, we're going to make them our toys. You sure you want to be a part of this?"

I turned back to the women, gluing my eyes to their full racks. "Hell yeah, I'm in."

"The game is on! Ok, ladies have the ball first," Jake said, throwing the ball over to Karen. The first game went by fast with Bob and Jake winning it. The next game seemed to take a lot longer, with the ladies winning. After the fourth game, it was all tied up. Both my mind and cock were racing, praying that the guys would win. The last game seemed to take the longest.

Then, when I thought the suspense would make me explode, I heard a swoosh and a cheering female voice. "We win!" I looked up and rubbed my eyes to see May and Karen dancing around, exchanging high-fives.

May beamed. "Well, looks like we win!" She glanced at her watch. "Wow, I need to get home. Tomorrow, Karen and I will be back to collect on our little bet." They both pranced off.

"Meet us in Bob's garage around ten A.M. tomorrow, babes." Jake chuckled and gave a flirty wave.

As the women walked home, Bob looked at me. "You're still in?"

"No shit I'm in. I bet they're expecting all three of us to take off our clothes. Since I'm over at May's a lot when her son is home, I guess I don't have a choice at this point," I replied.

Bob smiled, "Don't worry, after tomorrow they both are going to be our sluts and do what we want."

"Just shorts and t - shirt tomorrow, nothing else." added Jake.

With that, Jake and Bob walked off laughing.

-----------

I showed up at Bob's around 9:30 the next day. The garage side door was open, so I walked up and took a look inside. It had two old couches inside and a few other chairs. I noticed a pool table and an area that looked like a dance floor; they even had a refrigerator. I continued to look around, wondering what else they had, and there stood Bob, adjusting the buttons on his stereo system.

"Hey," I said, smiling.

Bob looked at me. "Glad you're here, Jack. Could you help me set some stuff up? Cool, you're dressed the way we told you, hope you're commando."

"So what you need help with? And yes, I am."

"I got the stereo set up with some good dancing music. I figure some fast songs and then some good slow dancing songs. What I need you to do is sit over there by the couch so I can make sure the cameras are set."

"Cameras?" Looking around I continued, "I don't see any cameras." Why would he have cameras anyway? Then I realized what he was doing and smiled in lustful delight.

"Yeah, Jake and I like to film whatever happens in here. You never know what will happen, sometimes it is very interesting. We bought some shady spy cameras off the internet. We have enough cameras that the whole garage is covered," replied Bob.

I sat on first one couch and then the other while Bob made his adjustments to his equipment. Then Jake strolled in, saying, "Sorry I'm late. Glad to see Jack got here early to help you out, Bob. Looks like we're all in the same outfit. I saw the ladies walking down the street, they should be here soon." Looking at me, he said, "Jack, just follow our lead. Trust us, we've done this before, we know what we're doing."

With that, Bob turned on the stereo and sat down. Jake walked over and got himself a coke out of the refrigerator and sat down on the other couch from where I was sitting. Just then the ladies walked into the garage. They were each wearing a sleeveless blouse, jean shorts and running shoes. Each had their hair pulled back into a pony tail.

"Wow, this is a nice set up in your garage! And I like the music," Karen said, slightly swaying her hips to the beat.

May looked at me and said, "I see all three of you are here. We probably shouldn't be doing this! But I've been thinking about this all night long, so let's get the show going."

Karen gave May a reassuring hug around the shoulders, and they both laughed.

Jake shyly spoke up. "So, you two really are going to make us strip?" To me, I was pretty sure Jake's shyness was a show. But May and Karen seemed to buy it.

"Well the way I see it, you guys would've made us go through with it. So damn right we're going to make you go through with it," Karen said, chuckling.

"Then ladies, you need to go sit down over there on the couch." Bob pressed some buttons on the stereo system until he landed on a sexy song and we started to move with the music.

"Don't be shy! Let's see what you've got, boys," said May.

All three of us at the same time removed our t-shirts. The women started whistling and making comments about our muscles. Man, was I getting into this.

Then someone yelled out, "Now with the shorts, let's see what's underneath them. Come on, let's get a good look."

Bob dropped his shorts with a grand gesture. Both ladies' eyes and jaws widened. "Wow! That's the longest prick I've ever seen. Wow! Look at that, is it real?" Bob gave a modest chuckle and moved his hips like a stripper, bouncing his dick around for them.

Jake then followed suit, dropping his shorts and moving like a stripper. The ladies' eyes were moving from Bob to him. May yelled in disbelief, "It's thicker then Bob's and just as long!"