My Bet to Fuck a Straight Guy

"After this, I am gonna sit on your hard dick and place my feet on your face" I whispered in his ear and he smiled a bit.

I doubt I ever fucked a virgin ass until that moment. I was also a bit nervous. It was possible that he would just hate it. But we had both come too far to back down. This was happening. Thank goodness my penis was an average size.

I used to try to loosen up my partner's ass by using my finger first. But later I learned that it was better just to use my dick. So, I placed the tip of my dick on his butt hole and very gently started to push. His spread legs were on my shoulders and he stopped breathing for a second. I was in.

I gently pushed my dick a bit more and stopped. He was clearly in pain and not liking this at all. But I sensed that he really wanted to give it a shot. I pulled out about an inch and after a few seconds, I pushed in again, and very slowly kept repeating the back and forth. His face seemed more relaxed and that was a sign for me to push further in. About 3 minutes after we started, he had about two thirds of my dick in his virgin ass. I decided to fully pull out and restart. As I pulled out, his ass hole opened and closed, like it was winking at me.

"How are you hon? Hope it is not too painful?"

"Oh it was at first, but the pain lessened later"

"Should we continue or stop? Your call"

"No, I want to continue" he sounded a bit too enthusiastic.

"Okay me too. Believe me, in 5 minutes, you will not want it to end" I said it and stuck my dick in his butt hole once again. He was definitely loosening up. A few more back and forth and I finally shoved my entire dick in his ass. He sighed out of pain, so I stayed there motionless for a while.

"Okay, I am good, you can continue," he said.

"Great, let the fun begin", I replied and started moving. His body was definitely a lot less hairy than any guy I had ever been before, and I liked it. He put his feet on my boobs and spread his legs open. I kissed his toes, it was kinda nice, but probably not my thing. Then I started going a bit faster and faster.

"Oh wow, this feels so good. Holy cow, unbelievable" he almost shouted.

"You like it hon? Didn't I tell you? I am loving it too"

"Heck yeah, can you go faster? fuck me faster"

His last sentence gave me a rush of excitement that I had never experienced before, it almost made me cum. He was definitely into it. I dropped his legs off my shoulders and laid down on him and started kissing him. He had my tongue in his mouth and my dick in his ass. Every inch of our bodies was aroused by our intense fuck session, which was also amplified by the high from the joint we smoked. As we were fucking, I decided to push him a bit further, and just spat into his mouth without thinking it through.

"Did you spit into my mouth? Damn that was hot, just fuck my ass and give me your spit again" he almost begged.

I gave him my spit a few more times too and I asked him for his spit. The exchange of saliva in that very moment was like gas on fire. We were both overwhelmed by the intimacy and sensation we both were feeling. I could not resist much longer and started to cum.

He seemed a bit sad that I came.

"Can you get hard again?" he asked.

"I don't think so honey. Not tonight. but it means it is your turn to fuck me and I expect you to fuck me good" I said while grabbing his head with both hands and shaking it playfully. We both laughed.

I asked him to lay down, and gave him a blow job to get him hard. I put a condom on his hard dick and applied some lotion to his dick and my ass and got over him. I like missionary when I bottom, but for me to start, the easier position to loosen me up is for me to be on top, not to mention I wanted some more foot worship as I had promised him before.

I grabbed his dick and slowly directed it inside my ass. I was not as tight as he was and within a minute or two, I was sitting on him with his entire dick inside me. I started to move up and down and back and forth. but I started to sense that he was getting soft.

"What is happening hon? Don't you like this position?" I asked.

"No, it is nice, not sure why I am getting soft"

"Maybe I can help" I replied and repositioned myself with my hands back on his thighs. I asked him to put two pillows under his head and I placed my feet on his chest with my toes near his mouth. He started kissing my toes. I slapped his face gently with my foot a few times.

"You naughty boy. You like feet, yeah? Tell me you like dirty stinky sweaty feet in your mouth"

"Yeah I do, your red pedicure is such a turn on for me baby"

"What else do you like to do to my feet? Keep talking"

"I wanna lick each of your toes, one by one"

"Hold on" I said, I grabbed my right foot and spat on it a few times and put my foot on his chest again.

"Wanna suck my toes clean? Wanna drink my spit off my toes?"

"Hell yeah" and he started doing just that. I could feel inside my ass that his dick just got harder. I let him suck my toes and I started to move myself. His dick was thick and I was filled with it nicely and the sensation was just explosive. Apparently it was for him too, because in a minute or so, he started shaking and cumming. Too bad. I still wanted to play for hours.

"That is okay honey. Looks like you enjoyed fucking my ass, but something tells me your mouth was having more fun than your dick"

"Haha, tonight was a unique night. I had sex and my mouth and my ass had more fun than my dick. Definitely a first for me" he confessed.

"You have no idea how happy that makes me to hear. Can I make a confession too?"

"Sure, what is it?"

"I made a bet for $100 with a friend a few days ago to find a straight guy and have sex with him. So, my initial goal tonight was just to win the bet"

"Really? I thought you liked me. So all of this was only for a bet?" He sounded disappointed.

"But wait. If I knew tonight would be this fun and you would turn out to be such a nice lover, I would have gladly paid $100 instead. You are not the only one who had first experiences tonight. I did too and I am glad that I got to share it with you" I said and kissed him, we made out for a while.

"What about you? Can you get it hard again tonight?" I asked him.

"Unlike you sexy, I sure can. We are not done, not even close" he replied with a smile.

I was glad to hear it, the night was about to continue and I had several more thoughts and ideas to explore with my new boy toy.