Wicked Wednesday — Underdog

I look at the calendar.  The lack of W’s seems to indicate yet another game loss for you.  And we don’t have anything planned for the day so it seems like a perfect opportunity to give you a chance.  I like you being the underdog but it might be fun to let you think I’ll make it easier this time.

You are doing the dishes as I come around the corner.  “I’m giving you the chance for a total game win if you can keep from begging to cum all day.  Of course, if you ask me to stop at any point….well, let’s just say you will be chalking up a bigger loss.  Do you want to risk it?”


“Uh…I guess?”

I laugh.  There might be a hint of my evil plan in the sound.  “You don’t think that’s going to be enough, do you?  Full in or full out.”

A longer pause and then, “What’s the loss?”  You turn and look at me realizing that no answer is coming.

I pull off my shirt and drop it on the floor, then grab my tea and start to walk out of the room.  “If you want to play, go take off the cage.  If not, no problem…”

Knowing how long it has been since one of my games went in your favor, I hear an exasperated huff.  You walk past me and I smile.  You pause again and I can see the indecision.  I stand up, pull off my shorts and sit back down to take a sip.  You head down the hall and return with the cage off.  Game on.

As you finish wiping down the counter, I stand behind you and start stroking.  You lean back against me as I stroke your chest and then harden as I move down to your cock.  Less than a minute later and I can feel you just hitting the edge.  I stop and head back to finish my tea.

Every time you walk close, I stop you to stroke some more.  Fondle your balls, play with the PA, suck a little, stroke some more and generally keep you right near the edge.  But I know how much you want to win and that makes you a formidable opponent.  Time to up the ante.

“Let’s go swimming.  Nice day for it.  Why don’t you make a pitcher of margaritas and I’ll put together chips and salsa. ”  I can feel the tension rising just a little.  I change and come back wearing your favorite and tiniest bikini.  It really wasn’t my fault how often I needed to bend over in front of you to get the bowl and chips.  And the salsa is on the top shelf of the refrigerator just next to where you were mixing.  It was just a coincidence.

*STRETCH*  “The sun feels fantastic.”  I can see you watching me as I dip my toe in the water to check the temperature.  “Could you pour me a drink?”  I sit down and put my feet in your naked lap, settling in.  Chips and salsa and margaritas and just a little bit of wiggly toes.  You are looking way too confident so…  “Stand up.”

You do and I pull you over to me.  I take you in my mouth and start sucking.  Just as you hit the edge, I stop.  I count to 5 and start stroking you.  Right back to the edge.  And stop.  You grab the edge of the table to steady yourself and just look at me.  I see your eyes darken and then you close them again.  Another edge.  And more until you are drenched in sweat.

While you are recovering from the last one, I take a drink and grab an ice cube.  You still have your eyes closed and jump when I start rubbing it on your hard cock.  Your eyes fly open and you gasp.   I can see the resolve starting to crack just a little.  Hmmm…

I stand up and off comes the bikini top.  You can’t seem to decide if you are excited or terrified because you know me.  Then I slide off the bottom and get into the pool, motioning for you to follow.  Yeah, now you know that you are entering dangerous territory.

I swim back and forth a few times to get used to the water.  I can feel your eyes on me.  I swim back and stand next to you.  I look up at you and you know.  This win is going to take every last bit of resolve that you have.  And probably some that you don’t.

I wrap my legs around your waist and kiss you.  I grab your hair and hold you in place while I nip at your lips and tongue.  I bite down and you try to pull away but there is nowhere to go.  And then… I slide you into me.

I watch your eyes roll back a little and close then.  I pull my head back.  “Open your eyes.  No closing them or the game is over.”  You struggle to open them and focus on me.  The water is splashing over the side of the pool as you thrust into me.  You reach down to rub my clit and watch me tumble over the edge.   The feeling is enough to bring you to the edge and I hear you growl to stay in control.   You start to slow down and you hear, “No!  Keep going.”

I lose track of my orgasms but I’m pretty sure that you could tell me the exact number.  And possibly the duration.  You are fighting for control with everything that you have, trying to keep your eye on the prize.   You are feeling confident and then…

“What would you do if I told you to cum?  Right now?”  Just as I ask the question, a strong orgasm rips through me and you can feel every last ripple.  And the words slip out before you can stop them…

“Oh God…fuck…yes…please…”

I’m still breathing hard and you hope that maybe I didn’t hear it.  It wasn’t that loud.  I was distracted.  I cling to you as I come down and you relax just a bit.

We get out of the pool, dry off and head back to the food and drinks.  As I sit down you hear, “You didn’t even make it until lunch.  Just wait until you hear the consequence….”  as I laugh.

36 thoughts on “Wicked Wednesday — Underdog”

  1. Oh…Face/palm moment there at the end. I knew he would fail, but I was so rooting for him. She was so confident, I just wanted him to succeed. However, they both still win, now don’t they?

  2. This was flippin’ glorious! I am now itching to get home and play a similar game myself. Very inspiring indeed 🙂 Thank you muchly x

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