The Bet

"I'm so excited!!"



"Now listen to me carefully. Whether we do this or not depends on you. You have to consent. I'm only going to do this if you want to. You can speak now but you can only say 'yes' or 'no'. No hemming or hawing. No negotiating. Just a 'yes' or 'no'."

I hesitated. The answer was no -- but where would that lead?

"Yes," came out of my mouth weakly and I looked down at the sheets.

"That didn't sound too convincing baby. I'm sure you are a little scared. I've read many men find it emasculating to be pegged -- that's the term the saleslady in the store used -- and it is a big cock after all," she lifted my chin up to make me look at her again and began to slap my face a little harder with the cock, "but you have to make me sure you want this. You can speak freely now."

"Yes." I said more strongly.

"Yes, what?"

"Yes, you can fuck me."

My voice was petering out again.

"Fuck you?"



"Yes, yes, you can fuck me."



"Where can I fuck you?"



This was humiliating but I knew the game she was playing. I had made her beg before...

I swallowed hard and felt the shame rush into my cheeks as I uttered the words, "Yes, you can fuck me in my ass with your big cock. Please... please... do it..."



She beamed as the words came out of my mouth. It was a look of love mixed with satisfaction, power and lust.

"Say it again, louder."



"Please fuck me in the ass with your big cock! Fuck me hard until you cum!"



"Awesome!! I'm so excited.

She began fumbling with the restraints and soon I was freed. Part of me wanted to get up and run or at least try to reason with her but I knew this was a test. I had to go all in or leave. And as scared and embarrassed as I was, the powerful erection that was pulsating into the bed below me made it clear to me which way my destiny was fated.

Once she freed me, she stood over me for a moment. I think to see what I would do. As I lay there submissively she kneeled down at my side and reached underneath to grab the base of my cock. I gasped with her touch and I heard her let out a low moan of approval -- full of lust and desire -- as she felt my erection.

She jumped over me in a second. I hadn't ever seen her move that fast. Man, she was really into this. 

She ripped the plug out roughly and I felt more lube on my ass. She settled in behind me and I could feel her knees pry my legs apart. Soon the tip was at my entrance and she applied gentle pressure.

"Fuck, careful baby." I whispered.

I could feel her weight begin to shift onto my back and then all of a sudden she shoved the whole thing in all the way.

"AAHHHH!!!"



She stopped moving until I caught my breath.

"I'm in you!!" she cooed excitedly.


She started making in and out motions but it was awkward. It hurt like hell but I just moaned between gritted teeth. She popped out a couple of times and had to push all the way back in.



"Careful baby," I pleaded.

She slowed down and began to get a bit of a rhythm but she was having a hard time staying consistent. After a few minutes she was getting the hang of it. She pulled out again and I started to think it might be over but then I felt more jelly on my backside.

She came back in roughly and I swear she let out a perverse squeal of pleasure after hearing my moan of pain.

"I think I got it now."

She started going in and out. Slowly building up the pace and the lengths of her strokes. I thought she was beginning to get tired. I could feel sweat coming off her breasts onto my back. But then suddenly the switch turned.

She had it down now and began to really ram into me. I couldn't help letting out low groans of pain with each stroke in spite of my efforts to remain silent. Each groan fed her lust. She began to taunt me gently "I'm fucking you baby.... I'm fucking you hard.... I'm going to fuck you for longer and harder than you fucked me..."

I didn't say anything.

She kept it up for a few more minutes and then grabbed the back of my head with her hand and turned my head to look towards the right.
She whispered in my ear as she slowly picked up the pace, "talk baby. Tell me what I'm doing to you."



"C'mon baby, don't be shy."

She started plowing into me harder, "remember I'm fucking you until I cum. You want me to cum don't you?"

"Yes baby." I couldn't get out more than a whisper.

"Louder, baby. Tell me what I'm doing to you."

I could feel the shame rushing back into my cheeks as I forced the words out forcefully, "You're fucking my ass!"

"You're fucking my ass so hard!"



"Tell me how big I feel."



"Your cock feels so big in me!"



"Tell me you love it."



"I love you fucking me!"



Her breathing was getting heavier. The talk was getting to her. She stopped going in and out and was simply forcing herself all the way into me with her pubis gyrating in small circles creating more pressure on her clit and my backside.

It hurt like hell but I realized if I bucked back into her I would create more pressure on her pubis. I tried a few times... it was hard to get the right leverage and it increased my pain but I could feel and hear her physical response so I kept at it.

"Oh Sara," I knew she'd like it if I said her name, "Sara, you are fucking me so hard. Fuck me until you cum. Cum in my ass baby. Please fuck my ass hard until you cum!!"

I could tell it was about to set her over the top. I bucked back hard into her and began to hear the quick, little moans that typically foretold her orgasms. She bit into my right shoulder as she pressed her pelvis as deeply into my backside as she could. 

 "Fuck!!" we yelled in unison. My scream in pain; hers in pleasure.

She pressed into me a few more times in rapid succession and then relaxed. She collapsed completely, all her weight on top of me. Her breathing was ragged but slowly normalized.

"Oh my God!" Sara stammered. "That was incredible! I fucked the hell out of you didn't I?"



"Yes." I admitted weakly.



"Are you OK?"



"Yes."



"You're going to be sore tomorrow." She said with more pride than concern.


She got up off of me in a way that left the phallus in me. She nearly fell as she jumped off the bed and twirled around quickly, laughing as she fell back onto the bed near me.

"Wow, I'm totally lightheaded! I need some water. Do you want anything?"



She kicked off her left stiletto. The right had fallen off already apparently.



She ran into the bathroom for a few minutes and then went into the kitchen. She took her time but came back with two glasses of water.

Here you go. Get yourself cleaned up and come out to the living room. We need to talk." She put her robe back on and walked out.

"Oh yeah, clean up my cock and bring it out to me when you are done." She said with smugness.

I was so sore I just lay there on the bed for 10 minutes. My mind was racing 100 miles per hour. What had just happened? Did she know about the bet? Was she going to dump me? I couldn't decide if I was mad at her or more in love. I reached back and pulled out her cock (did I just think of it as her cock in my mind?) with a plop and then stumbled to the shower.



In the shower, I tried to ignore my raging hard-on. It didn't last long. I rubbed one out in seconds as I thought back to the pain of her bucking into me as she whispered in my ear. My erection wouldn't abate. I never masturbated twice in a row but I couldn't help it now. I re-lived the whole night. Getting tied up, licking her pussy, licking her ass, getting fucked... I was numb from the prior orgasm so it was hard to cum this time. I kept getting close but couldn't quite get there. I stroked myself harder and faster. My legs felt weak and I leaned against the shower wall. Somehow reliving her telling me how sore I was going to be had me on the edge.

"Fuck..." I came again with a low guttural groan.



Once I regained my senses I heard her chuckle, "are you done? I told you we need to talk."

Fuck, how long had she been in there? She clearly saw and heard that last orgasm through the opaque shower screen. I thought I couldn't be more embarrassed but then...



"Don't forget to clean up my cock and bring it out to me."



"OK." I responded hoping to disappear.

I did as she said though. 10 minutes later I was dressed and walking into the living room with her dildo in my hand. I felt scared.

She was sitting on the couch on her phone. Her robe was barely covering her. One of her perfect breasts peaked out bravely. She was talking to one of her friends in a joking manner, "I told you I'd do it. It was awesome. I fucked him harder than he fucked me," she bragged, "my cock is even bigger than his..." that was interrupted by laughter, "not by much though. I have to admit I love his cock but still... I think I might like fucking him more than having him fuck me." She knew I was there but was ignoring me. She kept on laughing as the other person said something on the other line.

I was horrified and ashamed. This was such a violation of my trust but if I complained... she knew I'd done the same at my poker game.

"Oh, there he is, he's walking a little bow-legged." She laughed and then put the phone down but kept it close enough that the listener could still hear.

"Did you clean the dildo well?"



I nodded. She looked at me sternly.

"Yes" I said loud enough for the listener to hear and then presented it to her so she could inspect. She took a quick look at it and smiled.

"Sit down."



I did as I was told.

She got back on the phone, "I'm going to have to call you back... What? Did he what? Oh no, I don't think so... but wait..." she started laughing, "did I tell you? I caught him beating off in the bathroom afterwards so I know he liked it," she looked me in the eyes as she laughed into the phone. She turned on the sofa towards me and looked down into my lap. She brought up her right leg and traced the obvious outline of my erection with her toe.

"OK let me get off. Well you know what. Just hold on a sec..."

She put the phone down once more in a way so that the listener could hear. "It looks like you like being submissive. I had a feeling that was the case. We'll talk in a bit. Go pour me a glass of wine, bring it here, then do last night's dishes. After that, I want you naked in bed. You're going to lick my ass until I fall asleep."

She got back on the phone before I could say anything, her foot still rubbing my cock. I slowly got up. As I did I heard Sara say, "Maybe... I hadn't thought about it. Yes, you're right. He'll have to provide face to face confirmation to all of you by the weekend..."

I could hear her clearly as I walked into the kitchen. I felt weak; there was no way I could do that.

"He will... Believe me, I own him now..."

I grabbed the counter for balance as her words sunk in. She was right...