Double or Nothing?

(All persons engaged in sexual activity are over 18 years old and any similarities to real life are purely coincidental.)

*****

"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.

Before I tell you about my escape from this predicament, let me first tell you how I ended up here.

I was working as a bartender at a very nice Italian restaurant in the Little Italy neighborhood of San Diego. I had graduated college 2 years earlier, completing my degree in world history, quickly putting it to good use making alcohol-based drinks for people to enjoy.

One Friday afternoon as I was setting up my bar for a busy evening of bar patrons, Gino, the general manager of our fine establishment, walked up and introduced me to Sharon; a new waitress.

"Bill," Gino said, "This is Sharon."

"Hi Sharon. Nice to meet you," I said.

"Nice to meet you, too," she said with a pretty smile.

Sharon looked to be in her early 40's and hot as fuck. She was about 5' 3" tall, a bit plump, but made up for that with her fabulous rack and nicely rounded ass. She was obviously an experienced waitress (you don't get assigned to work a busy Friday night your first day without years of experience) and she knew how to dress to get tips. Her black, button-up blouse was as tight as it could be and unbuttoned as far as she could have it without being considered topless. When you weren't looking at her ample cleavage, you could easily see her lacy bra through the space between buttons.

She came off a bit shy. Probably self-conscious about being the new girl and having all the cooks, male waitstaff, and even a few of the female waitstaff, take long gazes at her body. We were all used to each other, so having someone new around to peek at was a nice change of pace.

I walked her through how orders were placed on the computer system and how they were filled, with odd numbered areas to bar #1, my bar, and even numbered areas to bar #2. "Which area do they have you tonight," I asked her?

"The front area and sidewalk patio," she said.

"That's area #3. You've got me tonight," I said.

"Oh great. You seem easy to work with."

As she walked away to review the menu specials and wine list I dropped a fully intended sexual innuendo, "I'm easy in general." I got no response.

Amy, a fucking hot lesbian that was working bar #2 that night, heard my comment and said, "Strike One, Mr. Bill."

"Whatever," I replied.

"Maybe she'd respond better to me," she laughed.

"Well, she's working one of my areas tonight, so you can have her another night," I replied.

As the orders started to pile in, Sharon did very well, handling all her tables with professional ease. I piled on the flirtatious comments and glances and slowly she loosened up a little bit. As the restaurant started to clear out, Sharon came up to me and asked, "Do you know how to make a Ramos Fizz?"

"I can make anything," I replied with a wink.

"Oh really. What do you make best," she asked?

She really shouldn't make it so easy on me. "I'm best at making hot women burst."

"Excuse me," she said blushing.

"I'll explain it later," I said as she walked away smiling.

"Strike two," Amy said from behind me.

"I'll make her orgasm by morning," I said.

"Fuck off you pig," Amy said. "You're so full of yourself."

"How about a little wager?"

"Sure! $100 says you can't bring in proof that you make her orgasm by the start of our shift tomorrow."

"Deal," I said, shaking Amy's hand.

About an hour later, Sharon came up to the computer nearest bar #1 and started through the process of closing out the night. I grabbed a bottle of French champagne from the cooler and poured her a glass.

"Here you go, Sharon," I said setting the full champagne flute near her.

"What's this for," she asked?

"It's to say you did a really amazing job tonight. You're better than most of the people that have been here for years."

"Thank you. That's very sweet," Sharon said taking a sip from the glass.

As she sat at the bar sipping her drink she asked me, "So, what's the deal with getting food after a shift around here?"

"Well, you can scrape together whatever the kitchen will give you at this time of night, or you can do what I do."

"What do you do," she asked curiously?

"I head down the street to the wine bar where I know the chef and bartender and let them serve me."

"So, if I wanted to do that, would I have to go with you," she asked?

"You say that like it's a bad thing. And, the answer is yes, you do. But there's an upside."

"What's that?"

"I'll treat."

"What's the catch," she asked?

"Damn girl. You're on to my game, aren't you?"

"Well, what's the catch," she insisted?

"You have to sleep with me, get pregnant and then stay home barefoot in the kitchen."

"Sounds good. When are you off work," she asked laughing?

"Hey Amy," I said turning to the person who might soon owe me $100, "Can you close up?"

"Sure. Take off. See you tomorrow," Amy replied from bar #2.

Turning back to Sharon I said, "I'm off right now. Let's go."

A few minutes later as we were leaving, Sharon in front of me, I looked at Amy and made hand motions that indicated she'd soon be paying me off. She flipped me off.

Sharon and I covered the distance to the wine bar very quickly, mostly talking about her first night at work. We sat at a quiet end of the bar and my buddy, Jack, quickly served us some wine and put in an order for some food. We chatted comfortably with each other. Sharon told me she was recently divorced and recently moved to San Diego from Los Angeles because her daughter was in college in San Diego.

"You have a daughter in college," I asked surprised?

"Yes. She's a freshman."

"Damn. Did you have her when you were 10 years old or something?"

"That's very sweet, but you're full of shit. How old do you think I am?"

"I was thinking like 33," I said with a straight face.

"Again, I call bullshit. I'm 43," she said.

"No fucking way. You look amazing," I said.

"I'll take that as a compliment," Sharon laughed. "How old are you?"

"Um, well, 25."

"Oh shit. I need to go," she said starting to stand up.

"Age is just a number, right? I mean, you seem like you could easily keep up with a 25 year old."

"Keep up? Keep up doing what?"

"In bed, of course," I said laughing and pouring us more wine from the bottle we'd been served.

"You never stop, do you," she asked?

"I'll stop anytime you tell me too."

Our food was served and we chatted and ate while we finished off the wine. I signaled for another glass each to follow the bottle we'd had.

"Do you think if you get me drunk I'll sleep with you," she asked?

"No. I think you'll sleep with me sober."

"Fuck! You are insatiable," she said.

"I am when I'm in the presence of someone as gorgeous as you are."

"So, now you switch to being romantic?"

"No, now I switch to being honest. You're a fucking babe. If you don't know that you're crazy."

"Thanks. It's nice to hear. My ex used to tell me how fat I was."

"Some men are born dumb asses. You are sexy as hell."

We chatted more as we finished up our food and our last glass of wine. I dropped some cash on the bar and invited her to leave. As we were leaving the wine bar, I asked her how she was getting home.

"Well, now that you got me pretty buzzed, I'm going to ride share home. How about you?"

"I guess I'll ride share, also," I said.

Sharon called for a ride share via the app on her phone and then turned to me and said, "Aren't you going to call for a ride?"

"Can I share one with you?"

"Well, where are you going," she asked?

As her driver was arriving I said, "Your place?"

She shook her head no, opened the door to her ride and got in the back seat. I leaned over and looked in sheepishly and she said, "Okay, get in."

As we pulled away from the curb, we started kissing. It wasn't making out, but we were definitely enjoying our lips and tongues coming together passionately. Arriving at her house, we barely got the front door closed before we were making out and ripping at each other's clothing as we headed down the hallway to her bedroom. Arriving next to her bed, I worked on the buttons of her blouse while she fumbled with my pants. In a matter of minutes, I was down to my boxers and reaching around her back to unhook her bra. It popped open easily and fell off, revealing her mature tits with huge pink nipples that were already hard.

She laid down on the bed in her black panties while I dropped my boxers, revealing my stiff cock, and climbed on the bed after her. I climbed between her legs and started kissing and sucking her tits while my dick pressed into the crotch of her soaking wet underwear. I reached down and started to work her panties down so I could fuck her and she squirmed out from underneath me.

"Whoa. Wait just a second," she said. "Before we go too far, I need to grab a condom for you. Being pregnant at 43 is not on my bucket list."

As horny as I was, and dying to fuck this hot MILF, this was perfect timing. I grabbed my phone and quickly turned on the voice recorder and set the phone on the nightstand. I couldn't wait to have sex with Sharon, but I also wanted proof so Amy could pay me.

Amy resumed her position on her back and I dove in, head first, between her legs. I kissed and licked my way up the inside of her thighs before giving her a long, deep lick up the full length of her slit. She moaned with pleasure. I fucked her pussy with my tongue until her clit came alive and gave me a chance to start sucking on it; in and out of my lips it went.

"Yes. Yes. Suck my clit. Yes. I'm going to cum. Oh please, please make me cum," Sharon yelled.

"Yes Sharon. Cum baby," I yelled, making sure I used her name so Amy wouldn't try say it was someone else.

A minute later, Sharon tensed up, arched her back, started shaking and released her pussy juices as she achieved a monumental orgasm. While she was still having an orgasm, I climbed up on her chest and guided my cock into her cunt.

"Oh god. Oh yes," she screamed, "Fuck me. Keep my orgasm going."

"You like it hard, Sharon?"

"Yes. Pound me. Fuck me hard, Bill."

I drove my dick deep in her pussy, my balls slapping against her thighs, until I couldn't hold the pressure and blew my load into the protection of the condom. As my cock pulsed, she instinctively tightened up her pussy muscles and milked it into the rubber sleeve. Pulling out and rolling onto my back, Sharon carefully removed the condom and then took a few licks, tasting my cum. We collapsed and fell asleep spooning each other.

I would have preferred to fuck our way through the night, but we'd had quite a bit to drink and the next thing I remember my eyes were blinking away and the room was coming to life with the rising of the sun. Sharon was sleeping very heavily, so I slipped out of bed to take a leak. I put on my boxers and a t-shirt and headed out to her kitchen to find some coffee.

I found the coffee maker, filters and grounds and started the brewing process. I checked my phone, with the volume down very low, and confirmed that $100 was as good as mine. Smiling ear to ear while I listened to the recording, I was shocked to hear the front door open. I had nowhere to go as the entry foyer was between me and the hallway to the bed room. Dropping a full laundry basket on the floor and turning toward the kitchen, a young woman wearing yoga pants and a cut off, bare midriff, t-shirt, was suddenly standing right in front of me.

"Oh shit," she screamed, "Who the fuck are you?"

"Sorry. I'm Bill."

I could see her look down at my boxers. I glanced down and quickly tucked the tip of my penis back through the opening.

"You scared the shit out of me, Bill. Who are you?"

"Oh, um, I work with Sharon."

"My mom. I'm Kathy, her daughter. She obviously forgot I was coming home this morning to do laundry. Whatever," she said disgusted. She retrieved her laundry basket and headed toward the laundry room.

I poured two cups of coffee and headed down the hallway to the bedroom. Sharon heard me come back into the room and rolled over in bed. "Here's some coffee," I offered.

"Oh, that is really sweet. Thank you," Sharon said.

"Um, Sharon. I met your daughter."

"What? Oh fuck. Oh just great. I forgot she was coming home. Dammit. She'll kick my ass."

"Why? You're a grown woman."

"We have an agreement. No guys over when the other person is here."

"Ah. Got it."

"Wait. Were you in your boxers," Sharon asked?

"Yep."

"Oh shit. You better go. Sorry, but I'll see you at work later."

I totally understood and didn't want to jeopardize another round with Sharon, so I called for a ride share and got dressed while I waited. Kissing Sharon goodbye when my ride arrived, I thought I had successfully slipped past another meeting with Kathy until I got out front and she was there."

"Hey Kathy. Um, sorry about that. It was nice to meet you."

"Yeah. It's cool. At least my mom has good taste," she said smiling as she went back in the house.

As I climbed into the back seat of my ride, I thought to myself, "That sure ended well."

Kathy clearly got her good looks from her mom. She had long, dirty blonde hair, and a perfect, bubbly ass. She didn't take after her mom up top, but her tiny little tits poked through her shirt and looked fun as hell to play with.

I got into work later that day and couldn't wait for Amy to show up. Fortunately, she came in before Sharon reported to work. I greeted her with a big smile. "Well, want to hear it?"

"Fuck you. You're kidding," Amy said.

"Nope. Listen for yourself."

Amy took the phone into the bathroom for privacy. When she returned, she reached into her wad of cash and ripped off $100 and slammed it on the bar.

"I told you, Amy. Don't doubt Mister Bill."

"Fuck you. You're a tool."

Sharon came to work a little while later. While she was at one of the computers checking herself in, I came up behind her and rubbed her ass. She was wearing a black, long-sleeve, scoop neck shirt that offered an amazing view of her cleavage. Her perfume was intoxicating.

"Want to replay last night again tonight," I whispered to her?

"My daughter is having some friends over, so no."

"My place is free," I offered.

"Rain check?"

"I suppose," I said dejected as she walked away.

Amy came up behind me and said, "Looks like the little lovers will have to just gaze at each other all night from a distance."

"Why do you say that," I asked?

"She's in one of my sections. I get to stare at her sexy tits all night."

"Stare away. I can assure you, after last night, she doesn't lean your way."

"Really? I'll bet I could change that," Amy said.

"What are you saying," I asked.

"Double or nothing. I'll bet I can bring Miss MILF to orgasm before you do again."

"Are you fucking kidding me? That's easy money. It's a bet," I said shaking Amy's hand.

The night was just another night behind bar #1. I finished up my shift, pocketed my cash tips, and headed off to grab a late night snack. I listened to some music at a nearby jazz club and then caught a ride home with a buddy that lived near me.

I got into work that night and was anxiously awaiting Sharon's arrival. I guessed her daughter would be gone tonight and I wanted to get back in her sack before Amy tried a lesbian encounter with her; not that it would be successful. I saw Sharon's car come into the lot. Pretending like I was checking something outside the restaurant, I ran into her.

"Hey gorgeous," I said. "How was your night last night?"

"It was fun. Kathy's friends are a lively bunch."

"Is she home again tonight," I asked hoping for the best?

"No. But, I agreed to go out with Amy tonight."

"Amy?"

"Yes. Amy. You know, the bartender."

"That's not what I meant. Why Amy?"

"Why not? She invited me out for a girls night. We had fun chatting last night at work and decided to hang out."

"Okay," I said pouting.

"Smile, or your face will stay like that," Sharon said laughing.

When I saw Amy, I said, "So, I guess you made your initial move."

"I don't know what you mean. It's just two co-workers hanging out."

That night, I went home after work and put on a movie. I sat there on the couch wondering what was happening with Amy and Sharon. There is no way Sharon was a lesbian, but with $100 on the line again, Amy would pull out all the stops.

I was goofing around on Facebook, looking at pictures of Sharon, when I saw her daughter on the website. Kathy hadn't bothered to tighten up the privacy settings on her Facebook page and I had full access to her pictures. She was a wild little college coed, that's for sure. What she lacked in big tits, she more than made up for in outfits she picked. The teal colored bikini she had on in several photos was a few strings and three, tiny little triangles of material. Damn she's tight. I figured it couldn't hurt anything, so I sent her a friend request that was almost immediately accepted.

A few minutes after becoming friends with Kathy on Facebook, she messaged me.

Kathy: Hey John.

Me: Hey Kathy.

Kathy: Nice to meet you the other day.

Me: You too.

Kathy: So, are you and my mom like an item?

Me: No.

I kept bouncing around Facebook, looking at stupid things people were posting and political comments that got people all fired up. About 5 minutes later, Kathy messaged me again.

Kathy: You surf?

Me: Yes. Why?

Kathy: I saw your photos on Facebook.

Me: Got it.

Kathy: Can you teach me?

Me: To surf?

Kathy: Yes. What did you think I meant?

Me: I guess so. Do you have a board?

Kathy: No. Can I borrow one?

Me: Sure. I have a couple.

Kathy: When?

Me: I'm off work the day after tomorrow.

Kathy: Perfect.

Me: You don't have class?

Kathy: I'll skip it.

Me: What will your mom say?

Kathy: Don't tell her. Please!

Me: Okay.

Kathy: Here's my cell number. 555-901-4001. Tell me where to meet you.

So, I was going to teach Sharon's young, hot daughter how to surf. And yet I couldn't tell Sharon because Kathy was skipping school to do it. It all seemed like a perfect opportunity to be with a really hot, 18 year old college girl and yet there was no way I could touch her unless I wanted to lose any chance at being with her mom or run the risk of her mom castrating me. In any event, it sounded like a chance to check her out at least. I texted her a note to meet me at Pacific Beach in two days. She quickly replied that she couldn't wait.