My First Time, Truth or Dare

I was getting close when suddenly Jason pulled us apart. "He's about to blow, dear, hehe" She quickly got up and I felt the void of her moving away, the lack of pressure that my cock desired. I couldn't stop myself from reaching down and squeezing my cock as a shiver passed through me.

Tanya moved back to her spot and sat down with a giggle. "Mmm, that was nice, Andrew."

"And Andrew," she continued, "I chose dare."

"I, ah, dare you to take... no... " I had a surge of confidence. "I dare you to let me take off your panties."

"With pleasure, Andrew." Tanya moved in front of me and stood like she had earlier, with her panties at level with my eyes. I reached up and hooked my fingers under the straps and started pulling down. She spread her legs a bit, and I pulled them down. She was trimmed, but not hairless. I liked that, I was always disappointed with the completely bare pussies in porn. She had this light mesh of brown hair, and I could see her lips, glistening. I gave her panties a sniff and then offered them to her.

"Why don't you keep them, Andrew." she winked.

I wrapped them around my hand as a trophy, and Tanya turned to go back to her seat and wiggled her cute behind as she did so.

Jason did his turn, but he didn't need any help, and moved to level 9. I suddenly realized that we were all near the end of the game... I was on level 8 and Tanya was on Level 9 with Jason. "Truth or dare, Jason?" Tanya asked, and Jason responded with truth.

"Is Andrew going to fuck me before this game is over?"

"Yes, he is."

I looked between both of them, Tanya was sucking on her finger, and I knew what I wished that was, and I'm sure she knew that too. Jason gave me a wink.

I played my turn and I was also able to get to level 9 without any assistance. Jason looked at me, "Truth or Dare, Andrew?"

"Dare" I almost shouted in my excitement.

"Well this is just as much a dare for Tanya... you look so ready to blow, Andrew... I dare you..."

He gave a long pause, leaving me in suspense...

"I dare you to cum in Tanya's mouth."

"Whaa?" I looked at Tanya, she was still sucking on that finger, which she then slowly pulled out of her mouth trailing a bit of saliva, pointed it at me, and then curled it back, beckoning me.

I took another drink of courage, and stood up. My cock was leaking precum, and pointing straight forward, eager for some warmth... I stepped towards Tanya and stood in front of her. She was looking straight at it, licking her lips. She then grasped it in her hand, and started rubbing back and forth, and then she gripped tightly and pulled it towards her, pulling me with it. As I stepped in close to her, she opened her mouth, and quickly sucked the tip in. I could feel her tongue swirling around the tip, exploring the hole, and underneath, as she jerked her hand back and forth, moving my skin with it. I put a hand behind her head to stabilize myself, and my hips started thrusting forward and backward as I gently fucked her mouth. It didn't take long, and I came, hard, quick, spurting my cum at the back of her throat. It was forceful and caused her to cough a little, but she swallowed it all.

"That was a lot of cum, you've been saving it up for a while!" said Tanya. "Delicious though! Mmm."

She drew the next door card, it was a high level monster. "Oh lookie here, I need help to win..."

"I'll help!" I exclaimed in excitement, surprising myself even with my eagerness.

Tanya smiled at that, "Whats your price?"

I pointed down at my cock, which was already hard again...

"You got to say it..."

"I'd like to fuck you, Tanya. Let me fuck you and you win the game."

Tanya moved her pawn to the final level on the board. She then lay back and spread her legs, beckoning me with her finger again. "And don't worry about a condom, I'm on the pill."

I almost leapt on her, I moved so quickly, moving between her legs and looking down at her inviting face that looked back up at me. She smiled at me, and I leaned in and kissed her deeply. I started thrusting at her, but not really doing much, but I was just enjoying being close in her embrace and the feel of her lips on mine. I then felt her hand on my cock, and it guided me to her entrance. I pushed in, feeling the wet, silky embrace of her pussy on my cock. I positioned my arms above her head for support and began thrusting in earnest, feeling my cockhead rubbing against the wall of her canal, and she moaned into my mouth. Again it didn't take long, and I started squirting my cum deep into her. I carried on thrusting as long as I could until I was exhausted and rolled off her, panting deeply.

"That was amazing," I said. I looked over at her and realized she hadn't cum.

"Oh don't worry about me, cutie. I have two guys and all night to cum, you're bound to not last long the first time."

With that she moved over to Jason, who sat up onto the couch. She sat on top of him, facing him, and guided his cock into her. I could hear the squelching of his cock fucking her amongst my deposit. And I just enjoyed lying there looking up at the point of penetration from my vantage point. I felt really good at that moment, and I felt a large chunk of my shyness and lack of confidence slip away. Feeling tired, I admit I fell asleep at that point and woke up the next morning to find somebody had put a blanket over me and a pillow below my head. Nothing ever happened again with Jason and Tanya, it had been a once off thing. But I had new found confidence and that led me to more experiences.