John tried to remember what he was thinking when he accepted this deal, Jenna had asked him to wait on her and her friends as she held a "girls night in" party, John had refused the request in a heartbeat, and remained adamant when Jenna had offered him a good sum of money to do so.
Jenna then sighed and said that she wished she "didn't have to do this", and proceeded to detail her plan in full.
She basically wanted me there to play a strip game with her girlfriends, where they, in their finest slumber wear, got together and played a strip game with their waiter, who was dressed in the finest clothes a butler could wear.
The numbers would still be in his disadvantage, however it would be quite easy to strip one or two of them.
To make the game even more fair, John would be allowed which piece of clothing he wanted to take off, either from him, or any of the other girls themselves, and included girls who didn't ask the question answered.
that meant that if John wished, he could go through the girls one at a time, stripping them slowly but surely.
As for the game itself, it was a simple game of trivia; as John continued to serve the ladies, they would indulge him with questions throughout the night, while he couldn't prompt them to ask himself, he was assured that he would get at least one question every twenty minutes, or receive a single item of clothing (or its equivalent) in return as compensation.
The girls had a deck of cards to assist them, they didn't have to use it, but if they did, they had to read that question, so difficulty of the questions was quite random, meaning that a guaranteed hard question must come from memory, but that was as much control as the girls had, provided they didn't cheat, of course.
of course, being the only one among many girls, his chances were still slim, despite the elaborate outfit he would don, he would still be at a disadvantage in numbers even against girls in their scantily clad state.
Of course, this wasn't planned for his own pleasure, that much was obvious, it was simply Jenna's way of acquiring help for the night, and, if things turned out badly for him (as it would most likely do), she would also have some entertainment.
Regardless, John couldn't help himself, he kept imagining any of Jenna's friends, even in the worst case scenario, where he cannot even get one of them naked, they'd probably be dressed in something revealing, knowing the kind of company Jenna tended to keep.
On the day of the party, John came early to help Jenna prepare everything before the arrival of her guests, essentially making sure they had their food, their drinks and their other means of entertainment ready, other entertainment ranging from the mundane, such as movies, cards, and party games, to the more... erotic variety, a wide arrangement of sexy toys that John had to organise prior to the arrival of the first guests, which included several butt plugs, vibrators and dildos, whips, leashes and handcuffs, at the very least, this assortment told John that the guests were indeed willing to play fairly, as much as that was possible in this situation, otherwise, there would be no need to prepare more than one butt plug, for instance.
Just before the first guests were scheduled to arrive, Jenna gave John his uniform for the night, it consisted of a white dress shirt, black tuxedo pants, a bowtie, a vest, a belt, socks and shoes and finally a pair of black speedos that hugged his crotch quite tightly.
eight items in total, he would have to lose nine rounds to even get to his first forfeit, meanwhile, he could have two girls naked and doing forfeits in the same time, or have one naked and very embarrassed "target".
John was finished changing (in the privacy of a bathroom, thankfully) when Jenna herself emerged in her outfit for the evening, a rather sheer, pink nightie and a pair of panties, comically enough, the third item of clothing she had was a pair of pink, fuzzy slippers.
The first arrival was Jenna's friend Lindsey, a curvy girl with glasses long and curly, black hair, it was certainly a showcase of different models of beauty when she stood next to Jenna's more traditional look, thin and athletic, but still retaining all her feminine charms, the two were essentially opposites in physical characteristics, yet somehow they were both gorgeous.
"Hey John, guess Jenna
did
end up convincing you, eh?" Lindsey's attitude was her usual, dry and humorous, almost as if she knew something everyone else didn't at any given time "Then again, how could you refuse?"
John could only muster a sour smile, as if his participation in this wasn't even questioned, and what made it worse was that John himself wasn't sure if he would have that much faith in himself.
Lindsey had decided to go with a typical t-shirt and boxers ensemble, John could only guess that the third item was a pair of panties, as she wasn't wearing anything else, it wasn't anything special, but Lindsey made it work, the material of her shirt and shorts stretched snugly across her body, accentuating it in all the right places.
The next arrivals were Lauren and Stacey, two brunettes who were the best of friends, known to often share their clothes since they were the same size and thus were usually referred to by the affectionate nickname "the twins"; petite and slim, they weren't sexy so much as they were cute, with a bubbly attitude that matched their innocent appearance, Stacey sported a shorter haircut, while Lauren's hair was done up in a ponytail that stretched to the her lower back.
As Lauren and Stacey went to change, the final guest showed up, a girl by the name of Mackenzie, a busty redhead a freckled face, if anyone could rival Jenna in the sexiness department, it was Mackenzie, and to top it off, Mackenzie was a show off, she had an exhibitionist side of her that would put streakers to shame, it wasn't unusual for people to catch glimpses of Mackenzie's nude form if you hang around her long enough, and Mackenzie was well known for practicing a policy of free love, provided you were nice enough.
Just then the twins emerged from their changing areas, once again, their outfits were coordinated, both wore panties and a pair of baggy t-shirts, the colours were similar but reversed, one girl's t-shirt matching the colour of the other girl's underwear, the colours, in this case, were yellow and pink.
Finally, it was Mackenzie's turn to emerge from her changing room, and John's heart skipped a beat; she wore a black, low cut bra that pushed her ample bosom together, creating a delicious cleavage, and a matching pair of see through panties, and he could see that Mackenzie was completely shaved.
But no matter how hard he looked (and he looked long and hard) John could not figure out the third piece of clothing, but he guessed he'd find out if he was lucky anyways.
Finally the party was on its way, John prepared his tray with the drinks and snacks in the kitchen as the girls took hold of the living room to enjoy themselves, serving his duties just as requested, John kept the refreshments coming as the girls began by putting on a romantic yet steamy European movie, sitting on the floor right at the floor of a perfectly serviceable couch.
The first question came from Lauren, who held up a card as she read out her question: "I'll keep this one real easy Johnny, what is stored inside fort Knox?"
Lauren was right, This question didn't even give him pause: "That would be gold, right?"
"Correct!" Lauren's enthusiasm was infectious, she clapped her hands together and smiled "So what'll it be, lucky boy?"
John thought about this for a second, he finally spotted Jenna in her nightie, he'd been tricked, goaded abused and humiliated by Jenna more times than he could count, his desire to even the score and also catch an early glimpse of her topless form won out for him.
As Jenna heard his choice, she pouted but proceeded to remove her nightie all the same, and so there she sat, topless with her perfect breasts on display, in fact, she sat there in nothing but her panties and pink fuzzy slippers, John could feel the blood rushing to his shaft, the night was quite young and already he was glad he agreed to this.
The next question came from Stacey as she help up her card: "This one's from my favorite book series, what year did the last Harry Potter book come out in?"
This one had John thinking a bit, he'd read the books, but remembering the year they came out in was a challenge, he tried to think back, it was certainly before 2010, but not by much, he took a stab in the dark.
"2007?" John asked, half looking for confirmation.
"Wow, I did not expect you to get that, actually, who's the lucky girl?"
Feeling he's on a roll, John picked Jenna again, requesting her panties, this time Jenna Glared at him as she peeled the panties off, her trimmed blonde bush coming into view, though he couldn't see much below that from his point of view.
The next question came from Lindsey "I'm not going to go easy on you, John, I wanna see some skin as much as you do."
"Which gulf gave its name to the 1991 Gulf War?" Lindsey recited the question in her card, and John's streak stopped dead in its track, he was not familiar with the geography of that region, so he ventured his best guess:
"The... Iraqi Gulf?" John guessed.
"Nope, wrong! Sorry John." Lindsey smirked, betraying her true feelings behind the apology "now off with those shoes."
John kicked his dress shoes off his feet, they were a bit uncomfortable anyways, he thought, and went back to his work, it had been an hour already, and he was enjoying watching Jenna's embarrassment at being the only naked person in the room.
He knew his enjoyment would be dampened pretty soon, as Jenna was asking the next question, he knew she was holding a grudge, so I knew she was going to give me something impossible.
"So John, how many years did the Great Plague of Milan last?" Jenna asked with a large grin on her face, probably guessing that John was struggling with the question, which he was.
"Ten years?" John's guess was a shot in the dark, he'd never even heard of the great Milan plague, he doubted his answer was correct.
"two years, actually, you lose again." John removed his socks upon hearing this and started back to the kitchen, but Jenna stopped him "would you like another question?"
John turned back, Jenna seemed a bit too eager to play, as she was giving John more questions that she probably should, but he wouldn't pass up such an opportunity.
"Alright, go ahead." John was more than willing to continue.
"What year did the Three Mile Island accident occur?" Jenna asked, once again smiling, she probably prepared many difficult questions thinking she could stump John that way, but John was no slouch at, he knew about the nuclear accident, and he knew that it took place in the late 1970's, but he wasn't quite sure which year it was in.
"nineteen seventy... nine." John hesitated for a second, but he was glad to see that Jenna's face turned into a frown yet again, John wondered if he should incur Jenna's wrath any further, after all, she would probably be more likely to stop if he started targeting someone else, he decided that this would be a good idea and picked Stacey, asking her to remove her shirt.
