Strip Game Addict - Part 2

John Benson, Age 18, is a normal and healthy teenage boy, for the most part at least, since he also had an unhealthy habit, he is completely obsessed with strip games, to the point where he has never refused a challenge, something that was quickly exploited by his friends, some family, enemies, and even some teachers.

John is a 6’0 tall blond haired boy, somewhat skinny, and what is frequently described as fine ass, frequently described as such since it has been so frequently seen.

his friends found his obsession both hilarious and exciting, they certainly didn’t spare any opportunity to get John into a game, neither did his enemies and rivals, while John did enjoy the thrill of the game, losing was still quite embarrassing to him, he never balked on a forfeit, but that didn’t mean he was always excited to do it.

unfortunately for John, that was often the case, his clumsy nature often meant that he was, more often than not, the loser of the games he played.

Today was such a day, John was tutoring Jenna today in maths, Jenna was a hot, brown haired bombshell, with an hourglass like figure to die for and big green eyes that you could get lost in, she seemed more than capable of actually understanding the material, but lacked any sort of motivation to do the work.

“I don’t get why I even have to do this,” Jenna complained, sick with boredom, she flinged her pencil down on the coffee table “I’m never going to use it anyways.”

“Look, you have to learn this stuff, you can do it, just try.” John, at the end of his rope, begged her to try and solve the questions.

Jenna got a glint in her eyes, she knew what John’s weakness was, and she figured this was a good way to alleviate her boredom.

“Tell you what John, how about we take the next five questions, if I get even one wrong, you get to do whatever. You want. With me.” Jenna kept closing in on John, invading his personal space more and more, John couldn’t help but look down Jenna’s shirt at her ample cleavage.

“Of course, if I get them all right…” Jenna continued, but her voice soon trailed off as she traced a finger down John’s stomach and rested on his thigh, who was finding it very hard to swallow all of a sudden “I get to do whatever I want… With you.”

John was getting excited, not just at the prospect of seeing and doing whatever he desired with Jenna’s naked body, but especially at the aspect of playing a strip game with her.

A slow strip and reveal by the gradual loss of clothing was good and all, but John was also a big fan of sudden death games, ones where the loser was completely naked in front of a completely clothed winner.

He couldn’t say no to that.

“Okay then, you’ve got a deal.”

And so John prepared for her five questions, and she began to solve them, his heart was pounding, and sunk once he saw that she somehow managed to solve all five problems correctly.

“Yes! That means, you are mine.” Jenna happily proclaimed, and shot John a knowing look “You know what to do, strip!”

John got off the couch, and began to strip with shaky, nervous hands. First he began with his shirt, pulling it off to reveal his bare chest, it wasn’t that impressive, as he was not very athletic.

Next he began unbuckling his belt, dropping his jeans to reveal a pair of boxers underneath, with a noticeable bulge at the front, something that elicited a catcall from Jenna, and made John all that much more conscious of his impending nudity.

Finally, John slid his boxers down to reveal his already rock hard cock, standing straight at a respectable 7 inches long, though John felt anything but respectable.

“Very nice!” Jenna commented appreciatively, it was only then that John noticed the phone in her hand, his hands immediately shot down to cover his erection “Ah ah! You do what I say, and I say no covering, in fact, hands on your head.”

John had no choice but to obey, he rested his hands, fingers intertwined behind his head, he felt as if his throbbing cock was on the edge of bursting, and now Jenna was taking pictures, the loud and artificial shutter sound made it even more real to him.

“Everyone’s going to love this, though I hear you’ve already got quite a collection floating around already.” Jenna laughed, she approached John and pushed down on the tip of his cock with a single finger, then let it bounce back energetically, producing more giggles from Jenna.

“Wow John, you look pretty uncomfortable, what’s wrong?” Jenna knew exactly what was bothering John, but he knew that she wanted him to say it.

“Uh…” The words didn’t seem to want to come out though, he just stood there, looking at Jenna with begging eyes.

“You look like you need some relief, John, why don’t you go ahead and jerk off.” Jenna gave John permission, and he didn’t waste time obeying her command.

John’s hand grabbed his meat and began beating it fervently, groans immediately emanating from him as Jenna couldn’t help but giggle loudly, John was already thrusting his hips, he looked over to Jenna, who was wearing a wide grin on her face as she seemed to be video taping his masturbation now.

John quickly reached a climax as he shot his load right there on the floor of the living room, he could hear Jenna’s giggles and catcalls beyond the hazy veil of his intoxication, which was slowly fading away.

“That was fun, John, but how about something more...” Jenna said in a cheerful tone as she began rummaging in her purse, and eventually produced a dildo and some lube from within “... Hardcore?”

“W-wait, you don’t mean…” John stammered, but he knew where this was going.

“I heard from Emily that you enjoy the occasional anal, is that true?” Jenna asked, waving the pink, 6 inch dildo about.

“Yeah…” John Cursed Emily’s name under his breath, Emily was his sister, his junior by two years, and very much into humiliating her older brother, she’d gotten him stripped, humiliated and, of course, penetrated, countless times already, though he’d gotten her back on occasion.

“Alright then, get on your hands and knees and get ready.” Jenna ordered, and John did as told, he saw Jenna go behind him, heard the sound of the lube cap popping open, and soon after, he felt the dildo push up against his anus.

gritting his teeth, John felt the dildo sliding inside him, he also found himself producing grunts against his will, soon the dildo began sliding in and out of him.

“Well, looks like someone is back to life.” Jenna quipped, John’s cock was hard once again getting hard, signaling its readiness to be used.

Jenna wasted no time flipping John over and holding him in such a way that his cock was pointing directly at his face, she continued fucking him with the dildo with one hand, while using the other to now stroke his cock, John was too lost in ecstacy to resist now, and soon came once again, this time on his own face.

“That was fun John, invite me over to play again some time.” Jenna called out as she began picking up her things and left John on the floor, too exhausted by the experience to stop her, after all, they still haven’t finished the tutor session.