It was really pretty stupid on my part, when you think about it. I was wearing nothing but a pair of panties, and I decided to raise the bet by saying ‘If you win, you get to choose. Anything, anything you want’. I knew the moment that those words left my mouth what Jake wanted to put in my mouth.
Trevor and Liv had both folded and were just watching the hand play out. I think they knew what was going to happen but I was just too stubborn to fold and gracefully give up my panties. Instead, I being ‘Little Miss Confident’ with a full house hand of Jacks over nines, offered up my ‘Anything you want’ bid.
When Jake called my bid and laid down four threes, I cried foul. Not at anyone in particular, but I was just in disbelief that I could have lost so many hands that when I finally had a nice hand I was beaten.
So when Jake said ‘a blowjob,’ it wasn’t really a surprise. In the five months that Jake and I had been dating I had successfully avoided, dodged, evaded and, in general, hid every time he wanted a blowjob. We had been fucking pretty much from the first date. We hit it off right away and well he “hit it right away”. Within three hours of our meeting his hands were on my tits and his cock was buried deep between my legs. By three hours and three minutes of our first date his cum was seeping out of my pussy and down his cock. Ever since then it’s been non-stop sexual gymnastics with the one exception, blowjobs.
Until today, I have given a grand total of zero blowjobs. Yeah, I’m something of a blowjob virgin. I’ve seen the videos and heck, I’ve even seen girls at college intentionally letting some guy impale their throat with a hard cock. But I just haven’t been able to bring myself to let a guy put his dick in my mouth.
I’ve been close. Billy Flynn was two inches away from the sexual promised land of every high school boy when I puked in his lap. Numerous guys have tried the ‘let me straddle your chest technique’ or let me ‘tittie fuck you’ with no intention of stopping there.
Billy had so generously bestowed upon me my ‘cock crazy’ moniker the night I almost gave him head. You see Billy had convinced me that he was going to show me all the things I had been missing as a virgin and led me behind a wood pile when everyone was coupling up at a party. Once we were concealed from everyone's view he proceeded to teach me the finer points of French Kissing. Five seconds later Billy awkwardly shove his hand up my blouse. He pushed my bra up just far enough so the underwire was pressing into the middle of my boob causing me to wince in pain.
Not satisfied with my boob, he navigated his hand under my miniskirt. He started pawing at my pussy and finally grabbed my panties and pulled them down do my knees. With all the tact of a gorilla trying to drink tea, Billy then attempted to shove his finger in my pussy but did nothing more than spear the inside of my upper thigh. Bill was not going to be discouraged by how ‘tight’ I was and unzipped his pants and pulled his erect cock out.
You might ask what I was doing during all of this. Well, obviously I was there and was a willing participant, but from the moment Billy Flynn tried to shove his tongue down throat, my alcohol hazed brain was telling my stomach to churn all the contents. So, when Billy placed my hand around his cock and was showing me the correct way to stroke a penis I was swallowing back stomach bile. I think Billy must have felt that our relationship was moving along quite nicely and with a gentle nudge of his hand on my head he guided my head into his lap. With a deeply passionate whisper, Billy urged me to ‘suck him.’
It was one of those truly romantic first time sexual encounters that a virgin dreams of, but I never got to that point because the churned contents that were in my stomach surged into my mouth. I had this moment of complete clarity and my alcohol haze disappeared. My moment of clarity lasted only long enough for my brain to send another request to my stomach telling it to release all of the contents. I couldn’t hold it in any longer and the vomit spilled from my mouth onto poor Billy Flynn’s hard cock. Billy let out a deep passionate moan as if I had just taken him in my mouth but when the second surge of vomit spilled out he pushed me to the side and took off running to his car with his cock sticking out in front of him and vomit coating his crotch.
By the end of the next week, the story had completely transformed. Instead, of me throwing up on Billy I had become so ‘cock crazy’ that we fucked three, five, ten times. I couldn’t keep my hands, pussy, and mouth off him and insisted on finishing him with a blowjob. I had to have his cum and pleaded for him to cum in my mouth but it was so big that I couldn’t handle it and it spilled all over his lap. In those short minutes behind the wood pile, I had become ‘cock crazy’ and developed a reputation around school.
===
Sorry, let’s get back to my current unpaid gambling wager.
Jake took my hand and led me down the hallway, presumably to the bedroom. We never reached a room because Trevor called out, “Where are you going?”
“To the bedroom,” Jake answered.
“Nah. Right there. In front of us. Just like when you lose a regular hand you have to take your clothes off in front of everyone. Why do you think you wouldn’t have to pay up in front of everyone now?” Trevor asked.
Everyone froze. He was right. I hated him, but he was right. I was about to be those college girls I laughed at. I was about to become some sort of a sacrificial lamb at the Alter of Penis.
How the hell was I supposed to do this? And with an audience! Were they going to applaud? “Wooo, wooo, deeper, deeper. Suck that cock!” What the fuck!
I had images of the stupid cheerleaders from school shaking their pompoms encouraging me to score that touchdown.
We walked back into the room, and in the most awkward way ever, I asked, “How do you want to do this? Do you want me to, like, lay on the floor or kneel down?”
Trevor laughed, “Oh my God. Just kneel down already. Jake will figure out what to do next. It’s not that big of a deal. Liv does it all the time.”
My days as an oral virgin were about to end. I could see the March of the Penises parading around and jumping for joy knowing that another mouth would be initiated into the ranks of the 'Cocksuckers.'
I knelt. Completely naked, I knelt in the center of the room and waited. Penises around the globe were popping up at this very moment because some sort of magical signal was transmitted telling them that one of their brethren was about to be sucked. Squirts of cum were flying into the air in unison as a celebratory salute to the conquering of another ‘cock crazy’ woman.
When Jake walked up in front of me, I laughed. I had all these images of cartoon penises dancing in my head. They were all singing in these really high squeaky voices and the balls were marching along as if they were the legs.
I unzipped Jake’s pants and promptly all the humor of dancing penises was gone. Jake was about to do the one thing he has been begging me to do for five months. He was going to put his cock in my mouth.
“Come on already! Just give him a blowjob,” Trevor said.
Jake’s cock was soft when I freed it from the confines of his jeans and boxer briefs. It easily fit into my hand as I started to stroke him to life.
Jake cupped my chin and tilted my head up, “You don’t have to do this.”
“Oh, fuck yeah she does,” Trevor countered while standing behind Liv with his hands cupping her breasts.
“No, she doesn’t! Whoa …” Jake countered and stopped as I took his cock into my mouth.
I really had no idea how this was going to go. Yeah, yeah I know, I know. His dick goes in my mouth and I suck, stroke, and repeatedly slide my mouth up and down. I get that part but was it supposed to be like the videos Jake and I watched of Caprice and Anjelica and Gina having amazing sex? Was I supposed to smile and look lovingly into his eyes?
In the videos, they always ended the same way with the girls sucking off the guy and these massive cumshots spreading across their faces and into their mouths.