Double or Nothing?

The next afternoon when I showed up at work, Amy was already waiting for me in the parking lot. I was looking forward to picking up another $100.

"Hey Amy, where's my money," I asked?

"Hardly. You owe me," she replied!

"You're full of shit," I said.

"I have proof," Amy said.

"What proof?"

Just as I said that, Sharon's car pulled into the parking lot. Amy and I ducked into the back door of the restaurant just in time so Sharon didn't see us talking.

"I'll show you after work. Don't leave early," Amy said.

"What if I have a chance to go home with her?"

"You won't. I turned her."

"You're full of shit. I can't wait to hear."

The night went by painfully slow. The entire time Amy would drop little hints and I was dying with anticipation. Reservations were light at the restaurant so Sharon, the newest waitress, was sent home early. As Amy and I wrapped up the night at the bar, we walked down the street to the wine bar together. We sat down at a high top in a quiet corner of the bar, got some wine and snacks, and then I jumped in.

"So, spill it. What happened?"

"So, we went out for drinks and food and were just talking. Girl talk."

"Sounds boring," I interrupted.

"Shut up and listen. I let her talk all about her failed marriage and essentially gave her a shoulder to cry on. She got pretty emotional."

"Nice move," I said laughing.

"Right? I tell you. I'm good at this shit. As we finished up the wine and food, I invited her over to the place I'm house sitting at. It's up in The Heights and has a hot tub."

"You haven't invited me up there," I said.

"You, my friend, have a dick. I don't do dicks. I didn't say anything to her about the hot tub, but when we got there I opened more wine and was showing her around this sweet house and we came upon the hot tub. She was in seventh heaven and really wanted to go in, but she didn't have a suit. I told her since it was just us girls, we could skinny dip. She thought that was funny, but gladly got undressed right there with me."

"She has a fucking hot body for a 43 year old."

"She's 43? Fuck. I was wondering, but didn't want to ask."

"Yep. She's a fucking MILF."

Amy continued, "So, as we're in the tub, I told her to sit in front of me and I started rubbing her neck and back. After massaging her for a while, she leans back into me, so I ran my hands under her tits and just started fondling them. Her nipples got hard instantly, so I pinched them. She moaned happily, so I kept it up. She kept one hand under water and when the jets shut off a few minutes later, it was easy to see why; she was touching herself while I flicked her nipples."

"You realize you're making me horny as fuck, right?"

"I can't help you there. I got up out of the tub, grabbed her hand, and led her into the master bedroom. We never even talked about whether she was into women, we just climbed into bed and I led the way by spreading her knees and diving into her muff with my tongue. She came almost immediately and then it was her turn to eat me out. She was a pro. I haven't had an orgasm like that in a long time. She ended up spending the night and we did it all night. First thing in the morning, I even got a strap on out. She loved it."

"Fuck. That's crazy. But, what's your proof of all this."

"Look at this," Amy said. With that she brought up a video on her phone. Obviously, Sharon didn't know she was taking it, but there was Sharon, on her knees, face buried in a pillow, while Amy rode her from behind with a strap on.

"But, that doesn't show her having an orgasm," I argued.

"Don't be a fuck head. Pay me."

I whipped out my roll of cash and peeled off $100. As I handed it to her I said, "I don't suppose you want to give me a blow job or something. I need to relieve myself."

"Get the fuck out of here. No."

"Are you going to see her again?"

"I hope so," Amy said with a wink.

It was at that point in the night that we could have gone our separate ways with each of us in the same financial position as we were when we started. And then, as a consummate gambler, I opened my mouth with what, even to me, sounded like an outrageous bet.

"So, the night I spent at her house I met her 18 year old daughter. She's a college student."

"Yeah. So what?"

"She contacted me on Facebook and I am meeting her tomorrow on my day off to teach her how to surf."

"Okay. Does her mom know?"

"No."

"Go on," Amy said.

"I'll bet you $100 I fuck her daughter before you do her mom again."

"You're fucking insane, but I like it. There's no way this girl will fuck you and I'm hoping to see her mom in the next couple of nights."

"Bet?"

"Sure." Amy said shaking my hand.

I got home, logged on to Porn hub, and found a video to jerk off with. Amy's story had me going and there was no way I could fall asleep without relieving the pressure.

The next morning, I threw my board, and an old one I had, into the back of my truck and headed to the beach to meet Kathy. I knew we'd be sticking close to the shore in the smaller, body surfing waves, so I just wore a swimsuit, some deck shoes, and a t-shirt. When I arrived, she was already sitting on a yoga mat near the lifeguard stand that was out meeting spot.

"Hey Kathy," I yelled from a little ways off.

"Hey Bill," she said bouncing up to her feet.

She was wearing a sundress as a cover up and had her hair pulled back in a ponytail. She followed me to my truck so she could help with the boards. We made small talk and she made sure I wouldn't tell her mom we were together. We got back to our spot on the beach and I talked to her a little bit about how we'd float around on the boards for a little bit, get used to paddling on them, and then try a few smaller waves on her knees.

"You ready to go out," I asked?

"Yes. I'm excited," she said.

With that, she pulled her sundress up from the bottom and I damn near popped a boner right then. She was wearing the tiny teal bikini I had seen on Facebook. It was about the worst suit for trying to learn to surf, but I wasn't about to complain. While she had small tits, they were perky and sexy as hell. Her stomach was flat and tight and her cute little ass just screamed it wanted to be fucked.

For a few hours, we paddled around and I helped her catch a few baby waves on her knees. It gave me a great opportunity to sneak peeks at her perky nipples whenever she'd adjust her top. Fortunately, the water was cool enough it kept my dick from getting too excited.

When we finished, we warmed up in the sun and dried off. We decided to grab some food nearby and so we hit up a little Mexican place where I know the bartender. He didn't even bat an eye when she ordered a couple margaritas and he kept giving me the "thumbs up" when she wasn't looking. I ignored his gestures.

As we walked back to my truck, she said, "So, can I hitch a ride?"

"Sure. Where?"

"My moms. I need to run by there."

"Um, you think that's a good idea?"

"She's at work tonight. She won't see us."

We hopped in my truck and headed to Sharon's about 7 o'clock. Kathy was definitely feeling buzzed. As we talked about the day and laughed about her progress on the board, or lack thereof, she kept reaching over and touching my leg. I think she could tell I was getting a hard on.

As we pulled up to their housing complex, Kathy said, "Park in the visitor parking around the corner over there."

"Why am I parking?"

"Don't you want to come inside," she invited me?

"For what?"

"Follow me in and find out."

The entire time there was a battle raging in my head between the good voice and the evil voice. The good voice didn't stand a chance. I parked around the corner and followed her in the house.

As we got inside, she stood right at the entrance to the kitchen and said, "This is where I first saw you."

"Yes. This is where we met."

"And where I saw your dick poking out of your boxers."

"You saw that," I asked embarrassed?

"Yes. And that's why I think it's only fair that I show you." With that she slipped her sundress off her shoulders along with her bikini top. "They're small, but they're sensitive as hell."

"Kathy, this is not a good idea."

"Really," she said walking toward me? She reached out and grabbed my cock through my swimsuit. It was 90% hard. "Your cock seems to think it's a good idea."

Kathy pulled my shorts hard and they came down around my knees. She dropped to her knees, grabbed my stiff shaft, and started kissing and licking it. She was very good. I pulled her up to a standing position, pulled my shorts up so I could walk, picked her up by the ass, grabbed the clothing she had stripped off, and carried her down the hallway to her room.

Once inside her cute, girly room, she climbed on her bed and slipped out of her bikini bottoms. She hiked her knees up, spread her legs, and said, "Fuck me. Fuck me like you fucked my mom."

Her pussy was totally bald and I could tell she'd be tight. All her features, not just her mosquito bite tits, were dainty. I was afraid I'd crush her, but she seemed to know what she wanted.

I started by going down on her, licking her and fucking her pussy with my tongue in hopes she would cum and it would help lubricate her tight cunt. I was right. Within a few minutes she let out a cute little yelp and started convulsing with an orgasm. Her pussy was now soaked, so I climbed on, eased the tip of my hard dick past the entrance to her vagina, and then slammed it in. She screamed with pleasure. Immediately I started working my cock in and out of her pussy.

As a young, strong stud, I knew I could make this last for awhile, but there was still a tingle of fear in the back of my mind about fucking Sharon's 18-year old daughter just across the hallway from where I had fucked her brains out.

"Fuck me harder. Fuck my pussy," she screamed.

"You like this, baby. You want me to cum in you?"

"Wait. Oh shit. My mom's home," Kathy said.

"Are you fucking kidding me? How do you know," I replied while I pulled out of her tight pussy?

"I just heard the garage door open. Holy fuck. Here. Hurry. Hide in my closet," Kathy said as she scrambled under her covers.

Without saying a word, I pulled my shorts on, grabbed my shoes, and took up my hiding place in the closet. I sat on the floor, motionless, with my knees pulled up to my chest and hanging clothes partially hiding me. I tried to slow down my breathing and heart rate, but it had already been racing due to the sex we were having, add in the terror I'd just experienced of almost being caught, and there was no use. I felt like I was about to have a heart attack.

"Hey Kathy. Are you in there," I heard Sharon say as she tapped lightly on her daughter's door?

"Yeah mom. I came home from school. I feel sick," Kathy replied.

The next sound made me stop my breathing completely. The door to her bedroom opened and Sharon walked in to check on her daughter. She was literally only a few steps away from my hiding place.

"Let's see. Well, you don't have a fever. What's bothering you, honey," she asked Kathy?

"Just my stomach. I'll be okay. I just want to rest," Kathy played it off perfectly.

"Okay. Why didn't you text me?"

"I didn't want to bug you at work. I figured I'd just come here where I could rest. The dorms are noisy."

"Well, I'm glad work was slow then. They let me go early."

"Oh okay," Kathy said.

"If you need anything, let me know," her mom said as she left the room.

I heard Kathy get up and click the door lock on her bedroom door. The next thing I knew, she opened the door to the closet and whispered, "Holy fucking shit. That was close."

"You're telling me. Fuck. I thought I was literally going to have a heart attack. What the fuck do we do now?"

"I don't know. I'll think of something. Just be quiet."

"What if I have to pee?"

"Hold it," Kathy laughed as she shut the closet door and sealed me back in my dark little jail cell.

I heard Kathy open the door of her room and call out to her mom, "Mom. Do we have any ginger ale and crackers or something?"

"No, but I would be happy to go get you some."

"Would you really? That would be awesome."

"Sure. I didn't eat at work, so I'll stop and grab myself some take out."

"Thanks mom, I love you."

"Love you too," Sharon said.

"Thank god," I thought to myself. "I would soon be free."

About 5 minutes later, Kathy opened the closet door and let me out. I headed immediately for her door and she grabbed my arm, "Wait a minute."

"What," I said?

"We have at least 30 minutes. Don't you want to fuck me until you finish," she asked as she tugged at the waistband of my shorts?

She took off the robe she had put on when her mom came home, bent over and laid her chest on the bed with her little ass up in the air and said, "Fuck my pussy from behind. You'll cum faster."

As proof I was still in a right mind, I stood behind her, eased my cock back into her pussy and started fucking her. With her face buried in her bed, I was able to grab my phone, slide it open to the camera without her knowing, and started taking a video of my cock ramming in and out of her pussy doggy style.

"Do you like me fucking you in your mom's house where I fucked her, you naughty babe?"

"Yes. Yes. Fuck me. Fill me with your cum."

I dropped the phone gently, grabbed her hips with both hands, drove my cock deep into her, held it tight, and started shooting hot, sticky loads of cum deep into her pussy. I held my sperm shooting dick in place for about a minute while she willingly took it all.

As I finally slipped back out I was careful to catch the dripping cum with some tissues she had nearby. She rolled over on the bed, spread her legs, and smiled at the cream pie I had given her. I handed her a tissue and she cleaned up a little that had oozed out.

"I wasn't sure you'd do that," she said.

"Do what," I asked?

"Cum inside me. I'm not protected you know."

"What the fuck? Are you crazy?"

"No. I just know my mom would make you wear a condom and I wanted sex with me to be better."

"What if you get pregnant? Oh my god."

"Relax. The clinic at school will get me a morning after pill,silly."

"I need to go."

"Yeah, you better. After all, I'm home sick," Kathy said laughing.

I gave her a quick kiss goodbye and just about ran out of the house. I jumped in my truck and took the long way out of their neighborhood so there was no chance I could run into her mom.

Once I cleared their neighborhood, I pulled over and texted Amy while she was at work.

Me: You owe me $100!

Amy: What the fuck?

Me: Meet me after work and I'll show you the video.

Amy: Video?

Me: Yep.

I already had a few drinks down when Amy walked into the bar I was waiting at.

"Okay. I need to hurry, so show me you fucking pervert."

"Me? Pervert?"

I grabbed my phone, made sure the volume was down very low, and pressed it to her ear so she could hear it. Amy's mouth dropped open, stunned with astonishment. When she pulled her head away, I held out my open palm and asked for my $100.

"I don't have it right now. I have a deal for you though."

"What? No. I want my money."

"How about double or nothing again?"

"On what bet," I asked?

"I'm heading over to Sharon's right now. Is Kathy still there?"

"Yes."

"Double or nothing I have a threesome with them tonight?"

"It's a bet," I said as we shook hands.