Wager - Part 1

[sassnclass]

I cannot believe Joel pulled this crap again. I’m so sick of him flaking on things at the last minute!  Well, to hell with him! I’m going anyway.  I don’t care if I’ll be the odd person out of the couples.  I took the week off work and I’m not throwing away the free stay at the cabin.  I take a deep breath to try and calm myself and focus on the drive.  This last winding part is my least favorite.  There are so many hair-pin turns, it gives me a headache.

I slow down and veer right on the narrow dirt road that will lead to the cabin.  I try to push the nerves in my stomach away.  Hopefully Caleb is okay with me showing up without Joel.  Maybe I should have tried calling ahead.  Oh well, too late now.  I pull up next to the cabin and I’m surprised that I only see Caleb’s truck.  I was certain I would be the last one here.  I waited for Joel for an hour before he told me he was not going to be able to get away after all as he didn’t finish a project that was due at work.  Maybe if he had not stayed up all night playing Call of Duty three nights this week, he would have finished his work project and had been able to take this vacation.

Grabbing my bag and totes of groceries, I step out of my car into the crisp air.  I feel my stress immediately melt away.  I love this place.  Caleb has owned it for several years and is very generous about hosting group getaways.  I walk up to the door and knock. 

Caleb appears in the doorway, “Hey, let me get that for you,” he grabs the groceries and looks to the car, “where’s Joel?”

Following him into the cabin, I close the door behind me.  When we get into the kitchen, he sets the bags on the island.

“Joel had a work issue and decided at the last minute he couldn’t come.  I was all packed.  I hope it’s okay that I came on my own,” I nibble on my lower lip as I hope he will not send me back down the mountain.

“Dude is such a fucking flake,” he responds, “of course it’s okay you came without him.  I swear he gets more flakey each year that I know the guy.”

He puts away the groceries and as he talks.  I look around as I realize how quiet it is.

I ask, “Where’s Cassidy?”

Caleb pauses as he finishes putting items in the refrigerator.  He slowly folds the tote bags.  Then he says, “We broke up on Tuesday.”

“Oh, no.  I’m sorry.”

He lifts his head, “Yeah, thanks.  It was heading that way for a long time.”

There’s an awkward silence, then I say, “Well if you need to talk.  I’m here.  Are Chris and Jenna running late too?”

Caleb pulls out his phone, “I haven’t heard from them.  I thought they would be here by now.”

I realize that I’m still holding my suitcase, “I’m going to go put my stuff upstairs.  It is okay if I take any room since I’m here first?”

He looks up and smiles, “Go for it.”

I place my bag down in my favorite of the three guest rooms and go into the adjoining bathroom, my bladder is reminding me that it was a long drive.  When I go back into the bedroom, I move to the window and take in the stellar view.  I say out loud., “Fuck you, Joel! I’m going to have fun without you.”

I jump as Caleb barks out a laugh.

He says, “Sorry, didn’t mean to scare you.”

I feel my face heat, “I didn’t hear you come up.”

He lets out a sigh and lifts his phone, “I just got a text from Chris.  They’re not coming either.  Jenna’s sister went into labor a few hours ago, so they’re flying to Florida tonight.”

“Oh wow,” I say as it dawns on me, “so it’s just the two of us for the week?”

Caleb leans against the doorframe, “It looks that way. Are you okay with that?”

I reply, “I am if you are.  It sounds like a nice quiet week to me.  But, if you don’t want to stay all week, I understand.”

“I don’t have anywhere else to be.  Make yourself at home as usual.”

A smile spreads across my face, “Thanks.  How about I make dinner tonight?”

He replies, “Sounds good.  After dinner, we can skip game night and watch a movie if you want.”

“That’ll work,” I try to hide my smirk, “I know my board and card game skills are intimidating.”

He raises an eyebrow, “You think I’m intimated?”

I shrug my shoulder in response.

He straightens and takes a step toward me, forcing me to crane my neck up to look up at him, “I thought our choices would be limited with only two players.  But now it looks like you have challenged me to a game tournament this week.”

I smile, “It’s your funeral.”

He throws his head back and laughs, “Oh, I think I smell some wagers happening.”

A giddy thrill runs through me, I have not had this much fun talking shit in some time, “Sure, I’ll take your money. Or we can make it interesting.  Whoever loses tonight will have to make breakfast in the morning.”

He replies, “Good idea.  Each round of games will have specific stakes.  We’ll work out the details after dinner.”

After we eat, we clean up the dishes together.  It strikes me that Joel does everything humanly possible to get out of helping to clean up while Caleb insisted on helping.  I had forgotten how nice it is to share the task.  Even the conversation during dinner was relaxed.  No arguments, just easy flowing conversation.  Joel is always itching to get to his after-dinner gaming. 

Caleb receives a text and steps into the other room to make a call.  I pull out my phone as I hear a message notification.  I have signal, but it’s only two bars.  I move closer to a window, and I get one more bar.  I pull up social media and I notice that I have a direct message from an unfamiliar name, Brittany. 

     Brittany: I’m Joel’s girlfriend. He’s been seeing me for 3 months.  He said he was single.  But I found out about you.  I’ve forgiven him for lying.  But he’s breaking up with you. Joel is mine.  He should have taken me to the cabin.  Enjoy your last week there bitch.

My stomach drops.  I call Joel.  It goes to voicemail.  I message him asking about the message I received.  His responds.

     Joel: Yeah, sorry.  But I’m with Brittany now.  When I get back we can work out getting anything you left at my house and mine at yours.  Brittany’s just gets me.  Good luck.

 

I don’t respond.  I walk to the backdoor and go outside.  I stand looking out into the woods as I play through all the crap I have tolerated with him.  After about ten minutes, I hear Caleb calling me.  I call out to him.  When he finds me he pulls me to him and hugs me closely.  I lean into his embrace.  After a couple minutes it hits me.

“You knew?”

He shakes his head, “Not until a few minutes ago.  It was Joel on the phone.  He told me about the chick and that she was messaging you.  The fucker has no class, I told him that.  Having his side piece message you instead of being a man and telling you himself. What an ass.”

He pauses and rubs my bare arms, “It’s getting cold out here, let’s head inside.”

He leads me back into the cabin.  We sit in silence in the living room.

Finally, I say, “I’m not going to let Joel ruin this trip.  I think we had some games to play and stakes to decide on.”

Caleb smiles and we work out the three games that we will play tonight.  The best out of three will win tonight’s round.  The loser must make breakfast tomorrow.  We will then have another round of games.  Loser will need to make lunch.  The details for the rest of the day will be worked out after lunch when we decide if it is fun or a dumb idea.

Caleb wins blackjack.  I win the dice game, Farkle.  Then we play the card game, Nerts and I win.  I get up and dance around.  He sits back and smiles as he watched me.

He says, “I never realized how competitive you are.  How have I missed that?”

“I do like to win.  I mean, who enjoys losing?”

He laughs.  We watch a movie and then head to bed.  At the door to my room, I turn to him.

“Caleb,” he looks to me, “thanks. I mean it.  For letting me stay here and for making me laugh after…well, just thanks.”

He nods, “Don’t mention it.  I’m glad you’re here.  And I will have my redemption in the next round of games.”  He smiles as I laugh, “Goodnight.”

I struggle to fall asleep as I think about Joel and all the signs that I must have missed in the last few months.  It is late when I finally drift off.  In the morning, Caleb makes sausage, eggs, and toast.  I help him clean up. 

“Thanks for breakfast, I think I like this tournament. Maybe we should add a shoulder massage to the next stakes.

He leans back in his chair and says, “Winner of next round gets lunch and a shoulder massage?”

I nod with a smirk on my face.  He agrees.  We play another round of Farkle and he wins.  Then we play a game that is new to me, The Fox in the Forest.  He wins.  There is no need to play a third game, but we decide to play The Fox in the Forest again and again he is the victor. 

Caleb looks very smug as we clean up the game, “I think I’ll take my massage before lunch, thanks.”

I reply, “Fine.”

I move behind his chair and grab his shoulders.  He stops me.

“No, not here, let’s go sit on the porch.  The view will help me relax.”

I roll my eyes but follow him outside.  It is a beautiful day, the air is so clean and crisp. When we are on the porch, he straddles a bench and I stand behind him.  I massage his shoulders, arms, and upper back.  He lets out a sigh of pleasure and I am shocked by my instant response.  Arousal stirs in my core.  I ignore the feeling and continue to rub him.  After about ten minutes, I stop.

“I think I have fulfilled the bet.”

He says, “Alright, we’ll need to be more specific for the next set of stakes.”

We take a walk in the woods and discuss the next round.  After lunch, we will play again.  This time, the loser will have to not only make dinner, but also share a deep secret.  The winner will decide if the secret shared is acceptable and qualifies as a deep secret or not.  If after three attempts, no secret is deemed “deep” enough, then the winner can pick an alternate prize of their choice.  The loser will not have veto power.

The walk in the woods is just what I needed.  I feel relaxed and comfortable with Caleb.  When we get back to the cabin, we go our separate ways.  I make lunch and Caleb heads down to the basement.  I have never been in the basement of the cabin.  Caleb and Cassidy would head down there sometimes when the couples split off for alone time.  I figure there is a bedroom down there and they could be as loud as they want without the rest of us hearing.  Cassidy always emerged from the basement with messy hair and swollen lips.  Jenna would tease her about it and Cassidy would just blush.

After lunch, we start the next round of games.  I win at a brutal game of Nerts.  Caleb breaks out the classic Battleship game.  I am having such a good time playing that I do not pay attention to strategy, and I lose.  I beg for another round and Caleb agrees.  I lose again, much to my frustration.  When I was nine, I always won at Battleship.

We clean up the games and go into the family room to watch another movie.  Caleb says that I can have time to think about my deep secret that I’m going to share.  The movie is not a great one.  The lead guy sleeps around and there are several scenes where he is supposedly going down on his date and he makes her scream in orgasm.  He brags about his oral skills.  He meets the lead woman and when they get to the bedroom scene, he cannot make her cum with his famous oral abilities.

I blurt out, “Finally it’s more realistic!”

Caleb pauses the film, “What do you mean?”

I feel my face turning red, “Sorry.  I didn’t mean to say that out loud.”

“What did you mean?”

“It’s just this guy.  I mean, come on.  He makes every other girl cum from going down on her?  Not likely.”

Caleb studies my face, “You don’t cum from oral?”

I shift and look away.  He stays silent waiting for my response.  I look back at him and I can tell he is not going to let this go.

I respond, “No, I’ve never cum from a guy going down on me.”

“How many guys have done it to you?”

I hesitate, “Nosey, much?” When he just stares at me, I respond, “Um…four or five.”

He looks surprised, “And none of them have made you cum?”

I shake my head.

“Have you told them what feels good?”

I start to tell him to mind his own business, but something in the tone of his voice makes me want to answer, “I tried with a few of them, but they didn’t take it well.  Joel doesn’t like to be given any direction or feedback. He gets angry and will just stop.”

He watches my face as asks, “Do you cum from being fingered?”

“These are really personal questions, ya know,” but I continue, “Yes, I’ve cum from being fingered.  But not with Joel.”

Caleb shifts so that he’s facing me, “I tell you what, we can count this conversation as you sharing your deep secret.  But you can decide not to answer anything. Okay?”

I think it through and decide this could be interesting, “Okay, but what is shared at the cabin, stays at the cabin.  Deal?”

Caleb extends his hand, and we shake on it, “Deal.”

He continues, “Did you cum with Joel at all?”

“Yes,” I reply, “but not all the time.  In a specific position I would cum.”

“Did he ever ask why you didn’t or talk to you about what he could do to help you get there?”

I laugh, “No!  Joel never worried about that.  He liked to have me give him head and then we would have sex and it would be over in a few minutes.  He would tell me how good it was and then get back to playing his game or head out to hang out with friends.”

Caleb shakes his head, “Why did you stay with him so long?”

I pause, “You know, I really don’t know.  He made me laugh a lot at first.  He was sweet and we would do a lot together.  But slowly it became all about gaming.  Although, I guess some of that time may have actually been spent with Brittany.  Who knows what he was really up to?”

Caleb pauses, then he says, “I have a thought for our next round, if you’re up for it.  I don’t want to make you uncomfortable, and I won’t be upset if you say no.  But I’m competitive, and you have me very curious now.”

My eyes open wide, “Do I even want to know what you’re thinking?”

He smiles, “I bet I can make you cum with my mouth.”

My jaw drops, “Are you serious?”

“I am.  We can make that one of the games.  Whether I can make you cum using my mouth.”

“But…I mean…even if I lose, wouldn’t I be winning?”

He barks out a laugh, “That’s true.  But I know it puts you out of your comfort zone.  I won’t try to take it any further.  Just me going down on you.  Unless you ask for more.”

“I…um…I mean,” I blow out a breath, “What would the winner get?”

He appears to be thinking, then says, “If you win, I’ll make dinner instead of you having to from your last loss.  When I win, you let me bend you over my knee and spank you.”

My jaw drops again, “Spank me?  You want to spank me?’

Caleb says firmly, “I do.”

“As in you spank my ass with your hand?”

He nods, “Exactly.  Your bare ass and my bare hand.  The palm of my hand striking your ass ten times.”

Moisture pools at my core as I picture his hand striking my bare ass.

I take a shaky breath, then I ask, “Just spanking, nothing else after that?”

Caleb gaze narrows, “Not unless you ask nicely.”

My stomach flips at the intensity of his words.  I’m seeing him in a completely different light.  I’m not sure how to respond to him.  He lets the silence sit.

I ask, “You want to…um go down on me?”

His response is firm, “Of course, I do.”  Then he asks, “Do we have a deal?”

A big part of me wants to take this challenge, but I need to be sure I understand what the stakes are.

I ask, “What are the perimeters?  I mean, you can only use your mouth…you know lips and tongue?  No fingers or anything else?  Also, there needs to be a time limit.”

He smiles, “Yes, only my mouth.  I will need my fingers to spread your pussy open.  But I will not use them on your clit or insert any fingers inside you.  Let’s set a limit of fifteen minutes as I would like to take my time and I assume you will be nervous.”

I get wetter just hearing him say the word pussy.  Suddenly the idea of his mouth on me is so arousing that I crave it.

I say, “Okay, deal.”

I excuse myself to freshen up.  He tells me to remove my clothes, at least my pants and panties, and lie on my bed.  I can cover myself with a blanket if I am more comfortable that way.  I am lying in bed half naked with a throw blanket over my bottom half when he knocks on my bedroom door.  He enters the room and sits on the bed.

He says, “Relax, just let me do the work.  Normally, we would kiss and make out a bit.  But since that was not part of it, we will get right to it.  If you tell me to stop at any time, I will stop.  Understand?”

“Yes,” I say in a quiet voice.

He lifts the blanket from near my feet and pulls it up above my knees. He moves my legs so that my knees are bent, then lies on his stomach between my legs.  I close my eyes and focus on breathing. I jump when I feel his hand on my inner thigh.

He sooths, “Shh, just relax.”

He gently pushes my bent knees further apart.  He slowly moves his hands up my thighs.

Caleb says softly, “I’m going to touch you now.”

His fingers gently touch my mound and spread my pussy lips apart.  I feel his breath against my wet heat.  I bit my lip to keep from making a sound. 

He whispered as if to himself, “Beautiful.”

His tongue makes a slow and long stroke from the bottom to the top of my slit.  I gasp when his tongue strokes my clit lightly.  One hand continues to hold me open for him, the other holds me firmly in place.  He strokes me with his tongue again.  I suck in a breath of air and slowly release it.  He shifts so that my legs are over his shoulders.  Then he runs his tongue in circles around my clit, not quite touching the little nub.  When he slides his tongue inside me I let out a soft moan.

He hums in pleasure and says” Fuck, you taste good.”

His words have an immediate effect, and my pussy grows even wetter.  He slides his tongue back inside me and thrusts as deep as he can.  He fucks my pussy with his tongue in sensuous strokes.  My body craves more, I bite my lip to keep from begging him to fill me with a finger or his cock.

He pulls his tongue out and teases my clit again.  He circles it and I find my hips lifting to get closer to him.  He holds me still and then sucks my clit into his mouth.  I release a deep moan of pleasure.  As he sucks my clit, his tongue flicks against it inside his mouth.  It feels so good. 

I moan, “Oh, fuck.”

He hums again, and I feel it vibrate against my clit.  He sucks harder and continues to flick his tongue.  I bite my lip again as I want to beg him to slide a finger inside me.

He pulls his mouth away and goes back to thrusting his tongue inside my core.  Then he licks all around my clit again.  I want his mouth on my clit so badly.  I cover my mouth to keep from begging.  He teases me for another minute and then aggressively sucks my clit into his mouth.  My orgasm hits me hard and I cry out in pleasure and shock.

He keeps sucking until I push against his head.

I gasp out, “Please no more.  I can’t.”

He lifts his head.

Caleb asks, “Did I hurt you?”

I manage, “No, but I was about to beg you…um I mean…um never mind.”

He leans forward and licks my sensitive clit again, “You were about to beg for what?”

“Oh fuck, please…I can’t.”

Caleb continues to lick, “I think you can.  What were you about to beg for?”

I arch my back and say, “For you to fill me.”

“Fill you how?”

Lust is consuming my logical brain, “I…um…oh fuck that feels good.  I was going to beg you to fill me with you finger, you cock, with something.  I ache.”

He hums again, “Ask me to finger you and I will. And I promise you will cum again.  Even harder this time. But you will ask for it.”

He licks my clit again and I whimper.  I can’t believe that I actually whimpered.

“Please, Caleb,” I say softly, “please finger me.”

He makes a sexy growl, “I like the sound of you begging.”

He raises himself up on his knees, my juices are still on his lips and chin.  He looks down and presses his middle finger inside me.  I gasp and his eyes meet mine.  He watches my face as he slides in deeper.  He turned his hand and curls his finger.  My breath catches as he finds my g-spot. 

“Oh fuck,” I whisper.

He smiles as he slips another finger inside me.  The pleasure is intense.  I am so wet.  His fingers continue to rub, increasing the pressure. My head thrashes from side to side as the sensations overwhelm me.

My orgasm approaches, I try to form words, but nothing makes sense.  I’m just making sounds that are a cross between a whimper and a moan.  He rubs my clit with his thumb and I cum hard. My pussy milks at his fingers and I see spots in front of my eyes. He keeps stroking me, drawing out the pleasure.

Finally, the spasms subside.  He slides his fingers out of me slowly, then pushes them back in.  He fucks me with his fingers.   I watch him through half-closed eyes as pulls out his fingers and licks them.  It is one of the sexiest things I have ever seen.  I never knew an orgasm that powerful existed.

Caleb pulls the blanket back over me and lies down beside me.  I catch my breath.  I suddenly feel awkward as the fog of lust clears.  I’m not sure what to say or what to do.  I feel like I should offer to reciprocate, but then I remember that this was one of our games.

“Um, Caleb?”

He makes a humming noise again, “Yes?”

I reply, “Looks like you won.”

He laughs softly, “I certainly did.”

“I’m not sure what to do or say.  I mean, will this make things weird?”

He rolls to his side and looks down at me.

Caleb smiles, “It doesn’t have to be awkward.  I liked tasting you.  I enjoyed making you cum.  I’m going to enjoy spanking your ass as well.”

I say, “Do you want me to…um…should I uh…do you need me to…um…you know.”

He laughs, “Are you asking if I want you to give me head?”

I nod as my face flushes.

“Fuck,” he says, “you’re adorable. I’d love to have your mouth on me.  But not out of obligation.  For right now, we’ll take care of the wager.”

He sits up on the edge of the bed and tells me to lay across his thighs.  I move into position, and he easily adjusts my body to where he wants me.  He places a palm on my ass.  I can feel the length of his cock against my side.  A thrill runs through me at the confirmation that he is aroused.

He says, “You’ll receive ten strikes of my palm against your ass as was our agreement.  If you need a break, tell me.  I will pause.  Do you understand?”

I say soft, “Yes, I understand.”

He rubs my ass cheeks slowly.  Then he lifts his hand, and the first spank hits my ass.  It stings but does not hurt.  The second also stings.  The third is firmer and I let out a little gasp.  The fourth lands and I realize my pussy is growing wet again.  The fifth strike stings more than the others and I let out a little whimper.  The sixth follows quickly.  The heat and stinging are triggering more moisture in my core.  The seventh spank causes me to grunt.  The stinging intensifies.  The eighth quickly follows.  He pauses and rubs my ass cheeks.  I realize that evidence of my arousal is dripping down my leg.  His cock is a like a steel rod against my side.  He lifts his palm, and the ninth spank causes me to cry out.  The stinging and burning steals my breath.  The tenth strike lands and I feel tears start to form in my eyes.

His hand gentle rubs my ass cheeks again as he says, “You did very well.  Your ass is a lovely shade of pink.  Your pussy is drenched.  Do you need to cum again?”

The thought of his fingers entering me is this position is incredibly erotic.

I whisper, “Yes, please.”

His hand on my ass moves lower.  He slowly slides two fingers inside my soaked pussy.  He immediately finds the perfect spot.  He rubs against it as he slides his fingers in and out of me.  I am pushing back against his fingers, trying to take him deeper.  The wet sounds of his fingers moving in and out of my pussy should be embarrassing, but I find it so erotic.  I don’t remember ever being this aroused.  My orgasm is slithering closer and closer.  He speeds up his motions and it hits.  I cum hard, I feel my muscles clenching his fingers. 

He says, “Fuck, you are so sexy when you cum.”

[Lonely and divorced]

Another great story Sass. Thank you.!! I can’t wait for part two!☀️

[sassnclass]

 

On 11/23/2022 at 12:10 AM, Starving said:

Sassnclass this was great! I can hardly wait for part 2! Has me dripping wet after reading! Thank you for writing again!

 

 

Thanks! Glad you enjoyed!

 

 

 

[sassnclass]

Thanks @Lonely and divorced

[Mamasugas]

On 11/22/2022 at 10:09 PM, sassnclass said:

I cannot believe Joel pulled this crap again. I’m so sick of him flaking on things at the last minute!  Well, to hell with him! I’m going anyway.  I don’t care if I’ll be the odd person out of the couples.  I took the week off work and I’m not throwing away the free stay at the cabin.  I take a deep breath to try and calm myself and focus on the drive.  This last winding part is my least favorite.  There are so many hair-pin turns, it gives me a headache.

I slow down and veer right on the narrow dirt road that will lead to the cabin.  I try to push the nerves in my stomach away.  Hopefully Caleb is okay with me showing up without Joel.  Maybe I should have tried calling ahead.  Oh well, too late now.  I pull up next to the cabin and I’m surprised that I only see Caleb’s truck.  I was certain I would be the last one here.  I waited for Joel for an hour before he told me he was not going to be able to get away after all as he didn’t finish a project that was due at work.  Maybe if he had not stayed up all night playing Call of Duty three nights this week, he would have finished his work project and had been able to take this vacation.

Grabbing my bag and totes of groceries, I step out of my car into the crisp air.  I feel my stress immediately melt away.  I love this place.  Caleb has owned it for several years and is very generous about hosting group getaways.  I walk up to the door and knock. 

Caleb appears in the doorway, “Hey, let me get that for you,” he grabs the groceries and looks to the car, “where’s Joel?”

Following him into the cabin, I close the door behind me.  When we get into the kitchen, he sets the bags on the island.

“Joel had a work issue and decided at the last minute he couldn’t come.  I was all packed.  I hope it’s okay that I came on my own,” I nibble on my lower lip as I hope he will not send me back down the mountain.

“Dude is such a fucking flake,” he responds, “of course it’s okay you came without him.  I swear he gets more flakey each year that I know the guy.”

He puts away the groceries and as he talks.  I look around as I realize how quiet it is.

I ask, “Where’s Cassidy?”

Caleb pauses as he finishes putting items in the refrigerator.  He slowly folds the tote bags.  Then he says, “We broke up on Tuesday.”

“Oh, no.  I’m sorry.”

He lifts his head, “Yeah, thanks.  It was heading that way for a long time.”

There’s an awkward silence, then I say, “Well if you need to talk.  I’m here.  Are Chris and Jenna running late too?”

Caleb pulls out his phone, “I haven’t heard from them.  I thought they would be here by now.”

I realize that I’m still holding my suitcase, “I’m going to go put my stuff upstairs.  It is okay if I take any room since I’m here first?”

He looks up and smiles, “Go for it.”

I place my bag down in my favorite of the three guest rooms and go into the adjoining bathroom, my bladder is reminding me that it was a long drive.  When I go back into the bedroom, I move to the window and take in the stellar view.  I say out loud., “Fuck you, Joel! I’m going to have fun without you.”

I jump as Caleb barks out a laugh.

He says, “Sorry, didn’t mean to scare you.”

I feel my face heat, “I didn’t hear you come up.”

He lets out a sigh and lifts his phone, “I just got a text from Chris.  They’re not coming either.  Jenna’s sister went into labor a few hours ago, so they’re flying to Florida tonight.”

“Oh wow,” I say as it dawns on me, “so it’s just the two of us for the week?”

Caleb leans against the doorframe, “It looks that way. Are you okay with that?”

I reply, “I am if you are.  It sounds like a nice quiet week to me.  But, if you don’t want to stay all week, I understand.”

“I don’t have anywhere else to be.  Make yourself at home as usual.”

A smile spreads across my face, “Thanks.  How about I make dinner tonight?”

He replies, “Sounds good.  After dinner, we can skip game night and watch a movie if you want.”

“That’ll work,” I try to hide my smirk, “I know my board and card game skills are intimidating.”

He raises an eyebrow, “You think I’m intimated?”

I shrug my shoulder in response.

He straightens and takes a step toward me, forcing me to crane my neck up to look up at him, “I thought our choices would be limited with only two players.  But now it looks like you have challenged me to a game tournament this week.”

I smile, “It’s your funeral.”

He throws his head back and laughs, “Oh, I think I smell some wagers happening.”

A giddy thrill runs through me, I have not had this much fun talking shit in some time, “Sure, I’ll take your money. Or we can make it interesting.  Whoever loses tonight will have to make breakfast in the morning.”

He replies, “Good idea.  Each round of games will have specific stakes.  We’ll work out the details after dinner.”

After we eat, we clean up the dishes together.  It strikes me that Joel does everything humanly possible to get out of helping to clean up while Caleb insisted on helping.  I had forgotten how nice it is to share the task.  Even the conversation during dinner was relaxed.  No arguments, just easy flowing conversation.  Joel is always itching to get to his after-dinner gaming. 

Caleb receives a text and steps into the other room to make a call.  I pull out my phone as I hear a message notification.  I have signal, but it’s only two bars.  I move closer to a window, and I get one more bar.  I pull up social media and I notice that I have a direct message from an unfamiliar name, Brittany. 

     Brittany: I’m Joel’s girlfriend. He’s been seeing me for 3 months.  He said he was single.  But I found out about you.  I’ve forgiven him for lying.  But he’s breaking up with you. Joel is mine.  He should have taken me to the cabin.  Enjoy your last week there bitch.

My stomach drops.  I call Joel.  It goes to voicemail.  I message him asking about the message I received.  His responds.

     Joel: Yeah, sorry.  But I’m with Brittany now.  When I get back we can work out getting anything you left at my house and mine at yours.  Brittany’s just gets me.  Good luck.

 

I don’t respond.  I walk to the backdoor and go outside.  I stand looking out into the woods as I play through all the crap I have tolerated with him.  After about ten minutes, I hear Caleb calling me.  I call out to him.  When he finds me he pulls me to him and hugs me closely.  I lean into his embrace.  After a couple minutes it hits me.

“You knew?”

He shakes his head, “Not until a few minutes ago.  It was Joel on the phone.  He told me about the chick and that she was messaging you.  The fucker has no class, I told him that.  Having his side piece message you instead of being a man and telling you himself. What an ass.”

He pauses and rubs my bare arms, “It’s getting cold out here, let’s head inside.”

He leads me back into the cabin.  We sit in silence in the living room.

Finally, I say, “I’m not going to let Joel ruin this trip.  I think we had some games to play and stakes to decide on.”

Caleb smiles and we work out the three games that we will play tonight.  The best out of three will win tonight’s round.  The loser must make breakfast tomorrow.  We will then have another round of games.  Loser will need to make lunch.  The details for the rest of the day will be worked out after lunch when we decide if it is fun or a dumb idea.

Caleb wins blackjack.  I win the dice game, Farkle.  Then we play the card game, Nerts and I win.  I get up and dance around.  He sits back and smiles as he watched me.

He says, “I never realized how competitive you are.  How have I missed that?”

“I do like to win.  I mean, who enjoys losing?”

He laughs.  We watch a movie and then head to bed.  At the door to my room, I turn to him.

“Caleb,” he looks to me, “thanks. I mean it.  For letting me stay here and for making me laugh after…well, just thanks.”

He nods, “Don’t mention it.  I’m glad you’re here.  And I will have my redemption in the next round of games.”  He smiles as I laugh, “Goodnight.”

I struggle to fall asleep as I think about Joel and all the signs that I must have missed in the last few months.  It is late when I finally drift off.  In the morning, Caleb makes sausage, eggs, and toast.  I help him clean up. 

“Thanks for breakfast, I think I like this tournament. Maybe we should add a shoulder massage to the next stakes.

He leans back in his chair and says, “Winner of next round gets lunch and a shoulder massage?”

I nod with a smirk on my face.  He agrees.  We play another round of Farkle and he wins.  Then we play a game that is new to me, The Fox in the Forest.  He wins.  There is no need to play a third game, but we decide to play The Fox in the Forest again and again he is the victor. 

Caleb looks very smug as we clean up the game, “I think I’ll take my massage before lunch, thanks.”

I reply, “Fine.”

I move behind his chair and grab his shoulders.  He stops me.

“No, not here, let’s go sit on the porch.  The view will help me relax.”

I roll my eyes but follow him outside.  It is a beautiful day, the air is so clean and crisp. When we are on the porch, he straddles a bench and I stand behind him.  I massage his shoulders, arms, and upper back.  He lets out a sigh of pleasure and I am shocked by my instant response.  Arousal stirs in my core.  I ignore the feeling and continue to rub him.  After about ten minutes, I stop.

“I think I have fulfilled the bet.”

He says, “Alright, we’ll need to be more specific for the next set of stakes.”

We take a walk in the woods and discuss the next round.  After lunch, we will play again.  This time, the loser will have to not only make dinner, but also share a deep secret.  The winner will decide if the secret shared is acceptable and qualifies as a deep secret or not.  If after three attempts, no secret is deemed “deep” enough, then the winner can pick an alternate prize of their choice.  The loser will not have veto power.

The walk in the woods is just what I needed.  I feel relaxed and comfortable with Caleb.  When we get back to the cabin, we go our separate ways.  I make lunch and Caleb heads down to the basement.  I have never been in the basement of the cabin.  Caleb and Cassidy would head down there sometimes when the couples split off for alone time.  I figure there is a bedroom down there and they could be as loud as they want without the rest of us hearing.  Cassidy always emerged from the basement with messy hair and swollen lips.  Jenna would tease her about it and Cassidy would just blush.

After lunch, we start the next round of games.  I win at a brutal game of Nerts.  Caleb breaks out the classic Battleship game.  I am having such a good time playing that I do not pay attention to strategy, and I lose.  I beg for another round and Caleb agrees.  I lose again, much to my frustration.  When I was nine, I always won at Battleship.

We clean up the games and go into the family room to watch another movie.  Caleb says that I can have time to think about my deep secret that I’m going to share.  The movie is not a great one.  The lead guy sleeps around and there are several scenes where he is supposedly going down on his date and he makes her scream in orgasm.  He brags about his oral skills.  He meets the lead woman and when they get to the bedroom scene, he cannot make her cum with his famous oral abilities.

I blurt out, “Finally it’s more realistic!”

Caleb pauses the film, “What do you mean?”

I feel my face turning red, “Sorry.  I didn’t mean to say that out loud.”

“What did you mean?”

“It’s just this guy.  I mean, come on.  He makes every other girl cum from going down on her?  Not likely.”

Caleb studies my face, “You don’t cum from oral?”

I shift and look away.  He stays silent waiting for my response.  I look back at him and I can tell he is not going to let this go.

I respond, “No, I’ve never cum from a guy going down on me.”

“How many guys have done it to you?”

I hesitate, “Nosey, much?” When he just stares at me, I respond, “Um…four or five.”

He looks surprised, “And none of them have made you cum?”

I shake my head.

“Have you told them what feels good?”

I start to tell him to mind his own business, but something in the tone of his voice makes me want to answer, “I tried with a few of them, but they didn’t take it well.  Joel doesn’t like to be given any direction or feedback. He gets angry and will just stop.”

He watches my face as asks, “Do you cum from being fingered?”

“These are really personal questions, ya know,” but I continue, “Yes, I’ve cum from being fingered.  But not with Joel.”

Caleb shifts so that he’s facing me, “I tell you what, we can count this conversation as you sharing your deep secret.  But you can decide not to answer anything. Okay?”

I think it through and decide this could be interesting, “Okay, but what is shared at the cabin, stays at the cabin.  Deal?”

Caleb extends his hand, and we shake on it, “Deal.”

He continues, “Did you cum with Joel at all?”

“Yes,” I reply, “but not all the time.  In a specific position I would cum.”

“Did he ever ask why you didn’t or talk to you about what he could do to help you get there?”

I laugh, “No!  Joel never worried about that.  He liked to have me give him head and then we would have sex and it would be over in a few minutes.  He would tell me how good it was and then get back to playing his game or head out to hang out with friends.”

Caleb shakes his head, “Why did you stay with him so long?”

I pause, “You know, I really don’t know.  He made me laugh a lot at first.  He was sweet and we would do a lot together.  But slowly it became all about gaming.  Although, I guess some of that time may have actually been spent with Brittany.  Who knows what he was really up to?”

Caleb pauses, then he says, “I have a thought for our next round, if you’re up for it.  I don’t want to make you uncomfortable, and I won’t be upset if you say no.  But I’m competitive, and you have me very curious now.”

My eyes open wide, “Do I even want to know what you’re thinking?”

He smiles, “I bet I can make you cum with my mouth.”

My jaw drops, “Are you serious?”

“I am.  We can make that one of the games.  Whether I can make you cum using my mouth.”

“But…I mean…even if I lose, wouldn’t I be winning?”

He barks out a laugh, “That’s true.  But I know it puts you out of your comfort zone.  I won’t try to take it any further.  Just me going down on you.  Unless you ask for more.”

“I…um…I mean,” I blow out a breath, “What would the winner get?”

He appears to be thinking, then says, “If you win, I’ll make dinner instead of you having to from your last loss.  When I win, you let me bend you over my knee and spank you.”

My jaw drops again, “Spank me?  You want to spank me?’

Caleb says firmly, “I do.”

“As in you spank my ass with your hand?”

He nods, “Exactly.  Your bare ass and my bare hand.  The palm of my hand striking your ass ten times.”

Moisture pools at my core as I picture his hand striking my bare ass.

I take a shaky breath, then I ask, “Just spanking, nothing else after that?”

Caleb gaze narrows, “Not unless you ask nicely.”

My stomach flips at the intensity of his words.  I’m seeing him in a completely different light.  I’m not sure how to respond to him.  He lets the silence sit.

I ask, “You want to…um go down on me?”

His response is firm, “Of course, I do.”  Then he asks, “Do we have a deal?”

A big part of me wants to take this challenge, but I need to be sure I understand what the stakes are.

I ask, “What are the perimeters?  I mean, you can only use your mouth…you know lips and tongue?  No fingers or anything else?  Also, there needs to be a time limit.”

He smiles, “Yes, only my mouth.  I will need my fingers to spread your pussy open.  But I will not use them on your clit or insert any fingers inside you.  Let’s set a limit of fifteen minutes as I would like to take my time and I assume you will be nervous.”

I get wetter just hearing him say the word pussy.  Suddenly the idea of his mouth on me is so arousing that I crave it.

I say, “Okay, deal.”

I excuse myself to freshen up.  He tells me to remove my clothes, at least my pants and panties, and lie on my bed.  I can cover myself with a blanket if I am more comfortable that way.  I am lying in bed half naked with a throw blanket over my bottom half when he knocks on my bedroom door.  He enters the room and sits on the bed.

He says, “Relax, just let me do the work.  Normally, we would kiss and make out a bit.  But since that was not part of it, we will get right to it.  If you tell me to stop at any time, I will stop.  Understand?”

“Yes,” I say in a quiet voice.

He lifts the blanket from near my feet and pulls it up above my knees. He moves my legs so that my knees are bent, then lies on his stomach between my legs.  I close my eyes and focus on breathing. I jump when I feel his hand on my inner thigh.

He sooths, “Shh, just relax.”

He gently pushes my bent knees further apart.  He slowly moves his hands up my thighs.

Caleb says softly, “I’m going to touch you now.”

His fingers gently touch my mound and spread my pussy lips apart.  I feel his breath against my wet heat.  I bit my lip to keep from making a sound. 

He whispered as if to himself, “Beautiful.”

His tongue makes a slow and long stroke from the bottom to the top of my slit.  I gasp when his tongue strokes my clit lightly.  One hand continues to hold me open for him, the other holds me firmly in place.  He strokes me with his tongue again.  I suck in a breath of air and slowly release it.  He shifts so that my legs are over his shoulders.  Then he runs his tongue in circles around my clit, not quite touching the little nub.  When he slides his tongue inside me I let out a soft moan.

He hums in pleasure and says” Fuck, you taste good.”

His words have an immediate effect, and my pussy grows even wetter.  He slides his tongue back inside me and thrusts as deep as he can.  He fucks my pussy with his tongue in sensuous strokes.  My body craves more, I bite my lip to keep from begging him to fill me with a finger or his cock.

He pulls his tongue out and teases my clit again.  He circles it and I find my hips lifting to get closer to him.  He holds me still and then sucks my clit into his mouth.  I release a deep moan of pleasure.  As he sucks my clit, his tongue flicks against it inside his mouth.  It feels so good. 

I moan, “Oh, fuck.”

He hums again, and I feel it vibrate against my clit.  He sucks harder and continues to flick his tongue.  I bite my lip again as I want to beg him to slide a finger inside me.

He pulls his mouth away and goes back to thrusting his tongue inside my core.  Then he licks all around my clit again.  I want his mouth on my clit so badly.  I cover my mouth to keep from begging.  He teases me for another minute and then aggressively sucks my clit into his mouth.  My orgasm hits me hard and I cry out in pleasure and shock.

He keeps sucking until I push against his head.

I gasp out, “Please no more.  I can’t.”

He lifts his head.

Caleb asks, “Did I hurt you?”

I manage, “No, but I was about to beg you…um I mean…um never mind.”

He leans forward and licks my sensitive clit again, “You were about to beg for what?”

“Oh fuck, please…I can’t.”

Caleb continues to lick, “I think you can.  What were you about to beg for?”

I arch my back and say, “For you to fill me.”

“Fill you how?”

Lust is consuming my logical brain, “I…um…oh fuck that feels good.  I was going to beg you to fill me with you finger, you cock, with something.  I ache.”

He hums again, “Ask me to finger you and I will. And I promise you will cum again.  Even harder this time. But you will ask for it.”

He licks my clit again and I whimper.  I can’t believe that I actually whimpered.

“Please, Caleb,” I say softly, “please finger me.”

He makes a sexy growl, “I like the sound of you begging.”

He raises himself up on his knees, my juices are still on his lips and chin.  He looks down and presses his middle finger inside me.  I gasp and his eyes meet mine.  He watches my face as he slides in deeper.  He turned his hand and curls his finger.  My breath catches as he finds my g-spot. 

“Oh fuck,” I whisper.

He smiles as he slips another finger inside me.  The pleasure is intense.  I am so wet.  His fingers continue to rub, increasing the pressure. My head thrashes from side to side as the sensations overwhelm me.

My orgasm approaches, I try to form words, but nothing makes sense.  I’m just making sounds that are a cross between a whimper and a moan.  He rubs my clit with his thumb and I cum hard. My pussy milks at his fingers and I see spots in front of my eyes. He keeps stroking me, drawing out the pleasure.

Finally, the spasms subside.  He slides his fingers out of me slowly, then pushes them back in.  He fucks me with his fingers.   I watch him through half-closed eyes as pulls out his fingers and licks them.  It is one of the sexiest things I have ever seen.  I never knew an orgasm that powerful existed.

Caleb pulls the blanket back over me and lies down beside me.  I catch my breath.  I suddenly feel awkward as the fog of lust clears.  I’m not sure what to say or what to do.  I feel like I should offer to reciprocate, but then I remember that this was one of our games.

“Um, Caleb?”

He makes a humming noise again, “Yes?”

I reply, “Looks like you won.”

He laughs softly, “I certainly did.”

“I’m not sure what to do or say.  I mean, will this make things weird?”

He rolls to his side and looks down at me.

Caleb smiles, “It doesn’t have to be awkward.  I liked tasting you.  I enjoyed making you cum.  I’m going to enjoy spanking your ass as well.”

I say, “Do you want me to…um…should I uh…do you need me to…um…you know.”

He laughs, “Are you asking if I want you to give me head?”

I nod as my face flushes.

“Fuck,” he says, “you’re adorable. I’d love to have your mouth on me.  But not out of obligation.  For right now, we’ll take care of the wager.”

He sits up on the edge of the bed and tells me to lay across his thighs.  I move into position, and he easily adjusts my body to where he wants me.  He places a palm on my ass.  I can feel the length of his cock against my side.  A thrill runs through me at the confirmation that he is aroused.

He says, “You’ll receive ten strikes of my palm against your ass as was our agreement.  If you need a break, tell me.  I will pause.  Do you understand?”

I say soft, “Yes, I understand.”

He rubs my ass cheeks slowly.  Then he lifts his hand, and the first spank hits my ass.  It stings but does not hurt.  The second also stings.  The third is firmer and I let out a little gasp.  The fourth lands and I realize my pussy is growing wet again.  The fifth strike stings more than the others and I let out a little whimper.  The sixth follows quickly.  The heat and stinging are triggering more moisture in my core.  The seventh spank causes me to grunt.  The stinging intensifies.  The eighth quickly follows.  He pauses and rubs my ass cheeks.  I realize that evidence of my arousal is dripping down my leg.  His cock is a like a steel rod against my side.  He lifts his palm, and the ninth spank causes me to cry out.  The stinging and burning steals my breath.  The tenth strike lands and I feel tears start to form in my eyes.

His hand gentle rubs my ass cheeks again as he says, “You did very well.  Your ass is a lovely shade of pink.  Your pussy is drenched.  Do you need to cum again?”

The thought of his fingers entering me is this position is incredibly erotic.

I whisper, “Yes, please.”

His hand on my ass moves lower.  He slowly slides two fingers inside my soaked pussy.  He immediately finds the perfect spot.  He rubs against it as he slides his fingers in and out of me.  I am pushing back against his fingers, trying to take him deeper.  The wet sounds of his fingers moving in and out of my pussy should be embarrassing, but I find it so erotic.  I don’t remember ever being this aroused.  My orgasm is slithering closer and closer.  He speeds up his motions and it hits.  I cum hard, I feel my muscles clenching his fingers. 

He says, “Fuck, you are so sexy when you cum.”

Stunning story.. I want what they have..

[BamaFanNana]

On 11/23/2022 at 12:09 AM, sassnclass said:

I cannot believe Joel pulled this crap again. I’m so sick of him flaking on things at the last minute!  Well, to hell with him! I’m going anyway.  I don’t care if I’ll be the odd person out of the couples.  I took the week off work and I’m not throwing away the free stay at the cabin.  I take a deep breath to try and calm myself and focus on the drive.  This last winding part is my least favorite.  There are so many hair-pin turns, it gives me a headache.

I slow down and veer right on the narrow dirt road that will lead to the cabin.  I try to push the nerves in my stomach away.  Hopefully Caleb is okay with me showing up without Joel.  Maybe I should have tried calling ahead.  Oh well, too late now.  I pull up next to the cabin and I’m surprised that I only see Caleb’s truck.  I was certain I would be the last one here.  I waited for Joel for an hour before he told me he was not going to be able to get away after all as he didn’t finish a project that was due at work.  Maybe if he had not stayed up all night playing Call of Duty three nights this week, he would have finished his work project and had been able to take this vacation.

Grabbing my bag and totes of groceries, I step out of my car into the crisp air.  I feel my stress immediately melt away.  I love this place.  Caleb has owned it for several years and is very generous about hosting group getaways.  I walk up to the door and knock. 

Caleb appears in the doorway, “Hey, let me get that for you,” he grabs the groceries and looks to the car, “where’s Joel?”

Following him into the cabin, I close the door behind me.  When we get into the kitchen, he sets the bags on the island.

“Joel had a work issue and decided at the last minute he couldn’t come.  I was all packed.  I hope it’s okay that I came on my own,” I nibble on my lower lip as I hope he will not send me back down the mountain.

“Dude is such a fucking flake,” he responds, “of course it’s okay you came without him.  I swear he gets more flakey each year that I know the guy.”

He puts away the groceries and as he talks.  I look around as I realize how quiet it is.

I ask, “Where’s Cassidy?”

Caleb pauses as he finishes putting items in the refrigerator.  He slowly folds the tote bags.  Then he says, “We broke up on Tuesday.”

“Oh, no.  I’m sorry.”

He lifts his head, “Yeah, thanks.  It was heading that way for a long time.”

There’s an awkward silence, then I say, “Well if you need to talk.  I’m here.  Are Chris and Jenna running late too?”

Caleb pulls out his phone, “I haven’t heard from them.  I thought they would be here by now.”

I realize that I’m still holding my suitcase, “I’m going to go put my stuff upstairs.  It is okay if I take any room since I’m here first?”

He looks up and smiles, “Go for it.”

I place my bag down in my favorite of the three guest rooms and go into the adjoining bathroom, my bladder is reminding me that it was a long drive.  When I go back into the bedroom, I move to the window and take in the stellar view.  I say out loud., “Fuck you, Joel! I’m going to have fun without you.”

I jump as Caleb barks out a laugh.

He says, “Sorry, didn’t mean to scare you.”

I feel my face heat, “I didn’t hear you come up.”

He lets out a sigh and lifts his phone, “I just got a text from Chris.  They’re not coming either.  Jenna’s sister went into labor a few hours ago, so they’re flying to Florida tonight.”

“Oh wow,” I say as it dawns on me, “so it’s just the two of us for the week?”

Caleb leans against the doorframe, “It looks that way. Are you okay with that?”

I reply, “I am if you are.  It sounds like a nice quiet week to me.  But, if you don’t want to stay all week, I understand.”

“I don’t have anywhere else to be.  Make yourself at home as usual.”

A smile spreads across my face, “Thanks.  How about I make dinner tonight?”

He replies, “Sounds good.  After dinner, we can skip game night and watch a movie if you want.”

“That’ll work,” I try to hide my smirk, “I know my board and card game skills are intimidating.”

He raises an eyebrow, “You think I’m intimated?”

I shrug my shoulder in response.

He straightens and takes a step toward me, forcing me to crane my neck up to look up at him, “I thought our choices would be limited with only two players.  But now it looks like you have challenged me to a game tournament this week.”

I smile, “It’s your funeral.”

He throws his head back and laughs, “Oh, I think I smell some wagers happening.”

A giddy thrill runs through me, I have not had this much fun talking shit in some time, “Sure, I’ll take your money. Or we can make it interesting.  Whoever loses tonight will have to make breakfast in the morning.”

He replies, “Good idea.  Each round of games will have specific stakes.  We’ll work out the details after dinner.”

After we eat, we clean up the dishes together.  It strikes me that Joel does everything humanly possible to get out of helping to clean up while Caleb insisted on helping.  I had forgotten how nice it is to share the task.  Even the conversation during dinner was relaxed.  No arguments, just easy flowing conversation.  Joel is always itching to get to his after-dinner gaming. 

Caleb receives a text and steps into the other room to make a call.  I pull out my phone as I hear a message notification.  I have signal, but it’s only two bars.  I move closer to a window, and I get one more bar.  I pull up social media and I notice that I have a direct message from an unfamiliar name, Brittany. 

     Brittany: I’m Joel’s girlfriend. He’s been seeing me for 3 months.  He said he was single.  But I found out about you.  I’ve forgiven him for lying.  But he’s breaking up with you. Joel is mine.  He should have taken me to the cabin.  Enjoy your last week there bitch.

My stomach drops.  I call Joel.  It goes to voicemail.  I message him asking about the message I received.  His responds.

     Joel: Yeah, sorry.  But I’m with Brittany now.  When I get back we can work out getting anything you left at my house and mine at yours.  Brittany’s just gets me.  Good luck.

 

I don’t respond.  I walk to the backdoor and go outside.  I stand looking out into the woods as I play through all the crap I have tolerated with him.  After about ten minutes, I hear Caleb calling me.  I call out to him.  When he finds me he pulls me to him and hugs me closely.  I lean into his embrace.  After a couple minutes it hits me.

“You knew?”

He shakes his head, “Not until a few minutes ago.  It was Joel on the phone.  He told me about the chick and that she was messaging you.  The fucker has no class, I told him that.  Having his side piece message you instead of being a man and telling you himself. What an ass.”

He pauses and rubs my bare arms, “It’s getting cold out here, let’s head inside.”

He leads me back into the cabin.  We sit in silence in the living room.

Finally, I say, “I’m not going to let Joel ruin this trip.  I think we had some games to play and stakes to decide on.”

Caleb smiles and we work out the three games that we will play tonight.  The best out of three will win tonight’s round.  The loser must make breakfast tomorrow.  We will then have another round of games.  Loser will need to make lunch.  The details for the rest of the day will be worked out after lunch when we decide if it is fun or a dumb idea.

Caleb wins blackjack.  I win the dice game, Farkle.  Then we play the card game, Nerts and I win.  I get up and dance around.  He sits back and smiles as he watched me.

He says, “I never realized how competitive you are.  How have I missed that?”

“I do like to win.  I mean, who enjoys losing?”

He laughs.  We watch a movie and then head to bed.  At the door to my room, I turn to him.

“Caleb,” he looks to me, “thanks. I mean it.  For letting me stay here and for making me laugh after…well, just thanks.”

He nods, “Don’t mention it.  I’m glad you’re here.  And I will have my redemption in the next round of games.”  He smiles as I laugh, “Goodnight.”

I struggle to fall asleep as I think about Joel and all the signs that I must have missed in the last few months.  It is late when I finally drift off.  In the morning, Caleb makes sausage, eggs, and toast.  I help him clean up. 

“Thanks for breakfast, I think I like this tournament. Maybe we should add a shoulder massage to the next stakes.

He leans back in his chair and says, “Winner of next round gets lunch and a shoulder massage?”

I nod with a smirk on my face.  He agrees.  We play another round of Farkle and he wins.  Then we play a game that is new to me, The Fox in the Forest.  He wins.  There is no need to play a third game, but we decide to play The Fox in the Forest again and again he is the victor. 

Caleb looks very smug as we clean up the game, “I think I’ll take my massage before lunch, thanks.”

I reply, “Fine.”

I move behind his chair and grab his shoulders.  He stops me.

“No, not here, let’s go sit on the porch.  The view will help me relax.”

I roll my eyes but follow him outside.  It is a beautiful day, the air is so clean and crisp. When we are on the porch, he straddles a bench and I stand behind him.  I massage his shoulders, arms, and upper back.  He lets out a sigh of pleasure and I am shocked by my instant response.  Arousal stirs in my core.  I ignore the feeling and continue to rub him.  After about ten minutes, I stop.

“I think I have fulfilled the bet.”

He says, “Alright, we’ll need to be more specific for the next set of stakes.”

We take a walk in the woods and discuss the next round.  After lunch, we will play again.  This time, the loser will have to not only make dinner, but also share a deep secret.  The winner will decide if the secret shared is acceptable and qualifies as a deep secret or not.  If after three attempts, no secret is deemed “deep” enough, then the winner can pick an alternate prize of their choice.  The loser will not have veto power.

The walk in the woods is just what I needed.  I feel relaxed and comfortable with Caleb.  When we get back to the cabin, we go our separate ways.  I make lunch and Caleb heads down to the basement.  I have never been in the basement of the cabin.  Caleb and Cassidy would head down there sometimes when the couples split off for alone time.  I figure there is a bedroom down there and they could be as loud as they want without the rest of us hearing.  Cassidy always emerged from the basement with messy hair and swollen lips.  Jenna would tease her about it and Cassidy would just blush.

After lunch, we start the next round of games.  I win at a brutal game of Nerts.  Caleb breaks out the classic Battleship game.  I am having such a good time playing that I do not pay attention to strategy, and I lose.  I beg for another round and Caleb agrees.  I lose again, much to my frustration.  When I was nine, I always won at Battleship.

We clean up the games and go into the family room to watch another movie.  Caleb says that I can have time to think about my deep secret that I’m going to share.  The movie is not a great one.  The lead guy sleeps around and there are several scenes where he is supposedly going down on his date and he makes her scream in orgasm.  He brags about his oral skills.  He meets the lead woman and when they get to the bedroom scene, he cannot make her cum with his famous oral abilities.

I blurt out, “Finally it’s more realistic!”

Caleb pauses the film, “What do you mean?”

I feel my face turning red, “Sorry.  I didn’t mean to say that out loud.”

“What did you mean?”

“It’s just this guy.  I mean, come on.  He makes every other girl cum from going down on her?  Not likely.”

Caleb studies my face, “You don’t cum from oral?”

I shift and look away.  He stays silent waiting for my response.  I look back at him and I can tell he is not going to let this go.

I respond, “No, I’ve never cum from a guy going down on me.”

“How many guys have done it to you?”

I hesitate, “Nosey, much?” When he just stares at me, I respond, “Um…four or five.”

He looks surprised, “And none of them have made you cum?”

I shake my head.

“Have you told them what feels good?”

I start to tell him to mind his own business, but something in the tone of his voice makes me want to answer, “I tried with a few of them, but they didn’t take it well.  Joel doesn’t like to be given any direction or feedback. He gets angry and will just stop.”

He watches my face as asks, “Do you cum from being fingered?”

“These are really personal questions, ya know,” but I continue, “Yes, I’ve cum from being fingered.  But not with Joel.”

Caleb shifts so that he’s facing me, “I tell you what, we can count this conversation as you sharing your deep secret.  But you can decide not to answer anything. Okay?”

I think it through and decide this could be interesting, “Okay, but what is shared at the cabin, stays at the cabin.  Deal?”

Caleb extends his hand, and we shake on it, “Deal.”

He continues, “Did you cum with Joel at all?”

“Yes,” I reply, “but not all the time.  In a specific position I would cum.”

“Did he ever ask why you didn’t or talk to you about what he could do to help you get there?”

I laugh, “No!  Joel never worried about that.  He liked to have me give him head and then we would have sex and it would be over in a few minutes.  He would tell me how good it was and then get back to playing his game or head out to hang out with friends.”

Caleb shakes his head, “Why did you stay with him so long?”

I pause, “You know, I really don’t know.  He made me laugh a lot at first.  He was sweet and we would do a lot together.  But slowly it became all about gaming.  Although, I guess some of that time may have actually been spent with Brittany.  Who knows what he was really up to?”

Caleb pauses, then he says, “I have a thought for our next round, if you’re up for it.  I don’t want to make you uncomfortable, and I won’t be upset if you say no.  But I’m competitive, and you have me very curious now.”

My eyes open wide, “Do I even want to know what you’re thinking?”

He smiles, “I bet I can make you cum with my mouth.”

My jaw drops, “Are you serious?”

“I am.  We can make that one of the games.  Whether I can make you cum using my mouth.”

“But…I mean…even if I lose, wouldn’t I be winning?”

He barks out a laugh, “That’s true.  But I know it puts you out of your comfort zone.  I won’t try to take it any further.  Just me going down on you.  Unless you ask for more.”

“I…um…I mean,” I blow out a breath, “What would the winner get?”

He appears to be thinking, then says, “If you win, I’ll make dinner instead of you having to from your last loss.  When I win, you let me bend you over my knee and spank you.”

My jaw drops again, “Spank me?  You want to spank me?’

Caleb says firmly, “I do.”

“As in you spank my ass with your hand?”

He nods, “Exactly.  Your bare ass and my bare hand.  The palm of my hand striking your ass ten times.”

Moisture pools at my core as I picture his hand striking my bare ass.

I take a shaky breath, then I ask, “Just spanking, nothing else after that?”

Caleb gaze narrows, “Not unless you ask nicely.”

My stomach flips at the intensity of his words.  I’m seeing him in a completely different light.  I’m not sure how to respond to him.  He lets the silence sit.

I ask, “You want to…um go down on me?”

His response is firm, “Of course, I do.”  Then he asks, “Do we have a deal?”

A big part of me wants to take this challenge, but I need to be sure I understand what the stakes are.

I ask, “What are the perimeters?  I mean, you can only use your mouth…you know lips and tongue?  No fingers or anything else?  Also, there needs to be a time limit.”

He smiles, “Yes, only my mouth.  I will need my fingers to spread your pussy open.  But I will not use them on your clit or insert any fingers inside you.  Let’s set a limit of fifteen minutes as I would like to take my time and I assume you will be nervous.”

I get wetter just hearing him say the word pussy.  Suddenly the idea of his mouth on me is so arousing that I crave it.

I say, “Okay, deal.”

I excuse myself to freshen up.  He tells me to remove my clothes, at least my pants and panties, and lie on my bed.  I can cover myself with a blanket if I am more comfortable that way.  I am lying in bed half naked with a throw blanket over my bottom half when he knocks on my bedroom door.  He enters the room and sits on the bed.

He says, “Relax, just let me do the work.  Normally, we would kiss and make out a bit.  But since that was not part of it, we will get right to it.  If you tell me to stop at any time, I will stop.  Understand?”

“Yes,” I say in a quiet voice.

He lifts the blanket from near my feet and pulls it up above my knees. He moves my legs so that my knees are bent, then lies on his stomach between my legs.  I close my eyes and focus on breathing. I jump when I feel his hand on my inner thigh.

He sooths, “Shh, just relax.”

He gently pushes my bent knees further apart.  He slowly moves his hands up my thighs.

Caleb says softly, “I’m going to touch you now.”

His fingers gently touch my mound and spread my pussy lips apart.  I feel his breath against my wet heat.  I bit my lip to keep from making a sound. 

He whispered as if to himself, “Beautiful.”

His tongue makes a slow and long stroke from the bottom to the top of my slit.  I gasp when his tongue strokes my clit lightly.  One hand continues to hold me open for him, the other holds me firmly in place.  He strokes me with his tongue again.  I suck in a breath of air and slowly release it.  He shifts so that my legs are over his shoulders.  Then he runs his tongue in circles around my clit, not quite touching the little nub.  When he slides his tongue inside me I let out a soft moan.

He hums in pleasure and says” Fuck, you taste good.”

His words have an immediate effect, and my pussy grows even wetter.  He slides his tongue back inside me and thrusts as deep as he can.  He fucks my pussy with his tongue in sensuous strokes.  My body craves more, I bite my lip to keep from begging him to fill me with a finger or his cock.

He pulls his tongue out and teases my clit again.  He circles it and I find my hips lifting to get closer to him.  He holds me still and then sucks my clit into his mouth.  I release a deep moan of pleasure.  As he sucks my clit, his tongue flicks against it inside his mouth.  It feels so good. 

I moan, “Oh, fuck.”

He hums again, and I feel it vibrate against my clit.  He sucks harder and continues to flick his tongue.  I bite my lip again as I want to beg him to slide a finger inside me.

He pulls his mouth away and goes back to thrusting his tongue inside my core.  Then he licks all around my clit again.  I want his mouth on my clit so badly.  I cover my mouth to keep from begging.  He teases me for another minute and then aggressively sucks my clit into his mouth.  My orgasm hits me hard and I cry out in pleasure and shock.

He keeps sucking until I push against his head.

I gasp out, “Please no more.  I can’t.”

He lifts his head.

Caleb asks, “Did I hurt you?”

I manage, “No, but I was about to beg you…um I mean…um never mind.”

He leans forward and licks my sensitive clit again, “You were about to beg for what?”

“Oh fuck, please…I can’t.”

Caleb continues to lick, “I think you can.  What were you about to beg for?”

I arch my back and say, “For you to fill me.”

“Fill you how?”

Lust is consuming my logical brain, “I…um…oh fuck that feels good.  I was going to beg you to fill me with you finger, you cock, with something.  I ache.”

He hums again, “Ask me to finger you and I will. And I promise you will cum again.  Even harder this time. But you will ask for it.”

He licks my clit again and I whimper.  I can’t believe that I actually whimpered.

“Please, Caleb,” I say softly, “please finger me.”

He makes a sexy growl, “I like the sound of you begging.”

He raises himself up on his knees, my juices are still on his lips and chin.  He looks down and presses his middle finger inside me.  I gasp and his eyes meet mine.  He watches my face as he slides in deeper.  He turned his hand and curls his finger.  My breath catches as he finds my g-spot. 

“Oh fuck,” I whisper.

He smiles as he slips another finger inside me.  The pleasure is intense.  I am so wet.  His fingers continue to rub, increasing the pressure. My head thrashes from side to side as the sensations overwhelm me.

My orgasm approaches, I try to form words, but nothing makes sense.  I’m just making sounds that are a cross between a whimper and a moan.  He rubs my clit with his thumb and I cum hard. My pussy milks at his fingers and I see spots in front of my eyes. He keeps stroking me, drawing out the pleasure.

Finally, the spasms subside.  He slides his fingers out of me slowly, then pushes them back in.  He fucks me with his fingers.   I watch him through half-closed eyes as pulls out his fingers and licks them.  It is one of the sexiest things I have ever seen.  I never knew an orgasm that powerful existed.

Caleb pulls the blanket back over me and lies down beside me.  I catch my breath.  I suddenly feel awkward as the fog of lust clears.  I’m not sure what to say or what to do.  I feel like I should offer to reciprocate, but then I remember that this was one of our games.

“Um, Caleb?”

He makes a humming noise again, “Yes?”

I reply, “Looks like you won.”

He laughs softly, “I certainly did.”

“I’m not sure what to do or say.  I mean, will this make things weird?”

He rolls to his side and looks down at me.

Caleb smiles, “It doesn’t have to be awkward.  I liked tasting you.  I enjoyed making you cum.  I’m going to enjoy spanking your ass as well.”

I say, “Do you want me to…um…should I uh…do you need me to…um…you know.”

He laughs, “Are you asking if I want you to give me head?”

I nod as my face flushes.

“Fuck,” he says, “you’re adorable. I’d love to have your mouth on me.  But not out of obligation.  For right now, we’ll take care of the wager.”

He sits up on the edge of the bed and tells me to lay across his thighs.  I move into position, and he easily adjusts my body to where he wants me.  He places a palm on my ass.  I can feel the length of his cock against my side.  A thrill runs through me at the confirmation that he is aroused.

He says, “You’ll receive ten strikes of my palm against your ass as was our agreement.  If you need a break, tell me.  I will pause.  Do you understand?”

I say soft, “Yes, I understand.”

He rubs my ass cheeks slowly.  Then he lifts his hand, and the first spank hits my ass.  It stings but does not hurt.  The second also stings.  The third is firmer and I let out a little gasp.  The fourth lands and I realize my pussy is growing wet again.  The fifth strike stings more than the others and I let out a little whimper.  The sixth follows quickly.  The heat and stinging are triggering more moisture in my core.  The seventh spank causes me to grunt.  The stinging intensifies.  The eighth quickly follows.  He pauses and rubs my ass cheeks.  I realize that evidence of my arousal is dripping down my leg.  His cock is a like a steel rod against my side.  He lifts his palm, and the ninth spank causes me to cry out.  The stinging and burning steals my breath.  The tenth strike lands and I feel tears start to form in my eyes.

His hand gentle rubs my ass cheeks again as he says, “You did very well.  Your ass is a lovely shade of pink.  Your pussy is drenched.  Do you need to cum again?”

The thought of his fingers entering me is this position is incredibly erotic.

I whisper, “Yes, please.”

His hand on my ass moves lower.  He slowly slides two fingers inside my soaked pussy.  He immediately finds the perfect spot.  He rubs against it as he slides his fingers in and out of me.  I am pushing back against his fingers, trying to take him deeper.  The wet sounds of his fingers moving in and out of my pussy should be embarrassing, but I find it so erotic.  I don’t remember ever being this aroused.  My orgasm is slithering closer and closer.  He speeds up his motions and it hits.  I cum hard, I feel my muscles clenching his fingers. 

He says, “Fuck, you are so sexy when you cum.”

MMM made me so wet and throbbing for that man to do me ,,,,, 

[Katie Did It]

How did I ever miss this story? Steamy! I want to go to Caleb’s cabin and make bets. 

[sassnclass]

On 2/6/2023 at 11:38 PM, Mamasugas said:

Stunning story.. I want what they have..

Thanks!

[sassnclass]

On 2/7/2023 at 10:55 AM, BamaFanNana said:

MMM made me so wet and throbbing for that man to do me ,,,,, 

Glad you liked it.