Penalty match! Maddy vs Andy special event

Andy was sleeping again, gently floating in a land of strange and sensuous dreams.
Lost in the green depths of a thick, mysterious forest, the young adventurer had unfortunately falled into the cunning trap of a lustfully lethal Lamia, a mythological female creature whose upper half of the body looked like a beautiful girl, while the lower part consisted into the tail of a giant snake.
Lured into her embrace by her hypnotic hissing voice lulling and enchanting him with falsely reassuring cooings, the poor lad had been soon rolled within her coils, and she was now proceeding to rock and squeeze... rock and squeeze... her cute male victim, softening him in foresee of some next deliciously kinky play. In fact, Lamias were known to play alot with the finest male catches, before they would decide whether to swallow them or making them their husbands.... aka sex slaves. Thus, the naive adventurer's quest would miserably end into being devoured... in one way or another.

"Mnnn... w-what happens.... is the Lamia kissing me now...? I can feel that snakely tongue of hers swirling aroun..... uh...!! M-Maddy...???".
Deeply, and sweetly kissed by Maddy, Andy had started to slowly come back to the land were Lamias only exist in the perverted fantasies of some young men, being quite confused at first, but soon realizing that he was being kissed by this crazy.... intriguing... absolutely sexy opponent of hers.
"THREEE....!!! DING DING DING...!!!", went the noisy surroundings, but Andy's mind was dulled and lost in that beautiful makeout. Maddy could be a snakegirl maybe, but still a beautiful snakegirl, he thought, meekly bringing his arms up to embrace her with the long , mind-blanketing kiss.

Very slowly.... his mind started to computate the embarassing reality around them: the crowd was roaring like wild... the bell was ringing again... and he had just been shamefully pinned into defeat by a girl's kiss!!!
"Oh well.... being angry about it would be so pointless now", he thought , still moaning faintly, and meekly indulging in the pleasures of Maddy's plush lips. "mmnff...... <3"

“Sorry Andy, I really didn't want to knock you out like that, but I got..... a little carried away I think”, Maddy said to Andy close to his ear so that it was just between them.   “You seemed to be having a nice dream, was it about me”, she said with a giggle.   Maddy was glad that he was ok, she really thought that she might have hurt him there for a minute, but when he started to kiss her back, she knew that he was going to be all right.

“Well Andy, looks like this round belongs to me” smirked Maddy, “so I get to pick your penalty for round three, and believe me it will be a good one, I can picture it now”, she laughed.

“Back to the match now, time to get serious,” thought Maddy with some reluctance.  She thought that she had a good chance to win this best three of five match with Andy.  She knew that she had evened things up a little by working on his arms, so it should at least take this round for him to get them back to normal.  She would be sure to take full advantage of any small weaknesses that he decided to show her.

Maddy’s Victory in Round 2, via 3 count pin

Andy's Dream:

Alternate View:

Andy would blush at the memories of the strange sexy dream.... and how similar it was to reality after all....
"W-Well... let's put it this way... there was a snakegirl with strong sexy coils and... wasn't it for the long snake tail, I would swear that she was your twin sister... h-hehe..", Andy would admit, making a slightly flushed smile at the beautiful, and surprisingly stronger than expected, Maddy-chan.

"The penalty....!! Oh...right, almost forgotten that part. Oh well, I'm sure that you have already made your plans about that possibility... h-heh.. that's the winner privilege after all, so I guess it can't be helpled"., Andy sighed in not-so-worried surrender.
It looked like he still had not got himself to understand the... potentials of this penalty special rule. But Maddy was probably more than eager to teach him a couple of things on the matter.

Luckily for Maddy, she was not a gentleman like Andy. So she would not feel bad about the penalty that she had chosen for him, if he made it through this round with the penalty, she knew that she would pay for it later, but she just had to do it.

“Andy, I am going to be nice and give you two choices, and you can pick whichever one you want. How does that sound?” , she said with a huge grin. Maddy was pretty sure which one he would go with, at least she thought that she was. It would be very interesting either way, that's for sure.

Andy would blink with a priceless lost face at Maddy's playful offer.
"So great... ain't it nice and generous of you Maddy doll...?", he would grumble in an amusingly half-disappointed tone.

Not that he was being a sore loser there. Quite the opposite, the young lad was usually a good sport and this was no exception, so he was prepared to play along with whatever the rules of the game would bring.
But, he had to admit to himself that having been squeezed to sleep, twice, by the luscious legs of a sexy energetic girl, and finally pinned down for the count by a kiss was not exactely the best feeling for his wannabe-playboy pride.

"Alright then, let's hear what options will you gracefully offer to the loser", he would finally say with a smiling sigh of surrender.

Maddy walked over to the tables slowly, while making sure that Andy got an excellent view of her swiveling her hips from side to side as she made her way there. She peeked back over her shoulder to see if he was staring or not, she really hoped that he was, this match had started to take on a new level, as she was becoming more and more interested in a post match wrap up meeting.

She picked up one small item from the first table and one small packaged item from the other table. Maddy held them behind her back as she walked back over to Andy, admiring his chiseled form the entire time. “Andy, here are your two options”, Maddy said finally. “The first option is to wear this pair of stainless steel handcuffs on your wrists, with the wrists cuffed behind your back........or........, or you may take option two which will give you much more freedom of movement than those darned cuffs would have” she said with a giggle. “Option two is to wear this awesome costume, that I think will just look perfect on you” Maddy continued with a sly grin. “It says, guaranteed to open eyes all around and I will get to see what you are hiding under those jeans. Let's see, this says........, be the object of desire for your husband or boyfriend in this Sexy Maid Outfit, complete with stockings and high heels”.

“Those are you two choices Andy, I tried to be fair and give you options, which would you like to chose?” Maddy said with a touch of humor in her voice.

Andy had kept making light movements to loosen the tension and lessen the numbening at his arms during the small conversation with Maddy, since the girl had proved once for all that, once his arms would be weakened an/or temporarily incapacitated, Andy was going to be in big troubles against her skills, flexibility, strong legs... and crazy lust for squeezing a handsome male.

Give that, he could not certainly be happy at the idea of fighting the whole next round with his best wrestling weapons sealed and cuffed behind his back.
"Ummhh, sounds like a lot of troubles... let's hear the second option, he said scratching the back of his head as if pondering.

But... the so-called second option caused a red flush of deep embarassement to color his face. "W-What....???!!! You must be kidding, a maid uniform?!? And a skimpy one at it !!!"

Now, maybe... just maybe, the absurd idea of wearing that shameful attire for the next round could at least save him from having his arms restrainted. But then he would be forced to wear high heels... Well, Andy had always wondered how the girls could walk and move so graciously on those highly instable footing... but he had no intentions to try it in first person!

So, the next number of Tension Magazine was going to have Andy in a sexy maid outfit on its cover....?
"Not if I have any alternative choice....! You should rather prepare to wear it... or something of the likes as soon as I win the next round with my hands cuffed", the ever blushing Andy would reply with a wannabe-resolute, but actually very amusingly embarassed voice.

Like that, Maddy's kinky offer had been refused as an even considerable option, leading the young wrestler into choosing the worst alternative in terms of handicap for the incoming third round.
It was highly possible that this was part of Maddy's plans: Andy was going to be in a hard penality, probably placing himself in the condition of being Maddy's boytoy for the next round, and he could only blame himself, since she had so "graciously" offered him an "alternative" after all.

“Wha.. what did you say Andy?” Maddy stammered. She must have heard him wrong, he wasn't supposed to do the handcuffs, that would be insane. Now she was starting to feel bad for putting him in this position. “He must realllly, reallly not like maids.. ”, she thought sheepishly.

Now she was in a real dilemma, she could not backpeddle and change her choices, but how could she let Andy wrestle with handcuffs on, that would be kinda unfair. “Are you sure that you won't change your mind Andy, I really would feel bad about putting you in handcuffs, (well here at least I would feel bad about it), I don't think that I can do that to you” Maddy implored. “Anyway you would look really cute in the maid outfit, you don't even have to wear the high heels” she offered with a hopeful smile.

Andy's expression shifted from shocked, to angered... to just slightly disappointed... but with a hint of a smile appearing on his lips during Maddy's cute "persuasive speech".

All the while, the crowd had been split into 2 factions: one was booing at Andy's choice... the other was just chanting: "maid out-fit...! maid out-fit!"

But the deadly hit to Andy's resolve was vibrated by Maddy's sulking face at his words... Those damn, cute puppy eyes of hers!
Hands on his hips, head tilted slightly, he would finally decide to yeld with a surrendering sigh, spreading his arms into a "what can I do" gesture.
"Umpfff.... Okay oookay. You win, maid outfit is then.... Just don't be sad ok? I know I'm going to regret this a lot too", he concluded with a self ironic smirk.

To that unexpected change of mind from Andy's part, the crowd reacted by roaring as one man! Apparently, all the fans in the arena seemed to know very well what they wanted to see in the next round... and it was a handsome, totally embarassed guy wearing a skimpy skirt.
"O well... give the crowd what they want", he said mostly to himself, partly amused.. but still very uneased by the whole idea.

“Wow, listen to that crowd cheer for Andy”, Maddy said under her breath, “they are clearly on his side now, maybe I made a mistake with my penalty choice”. Andy was so red in the face that he looked like a stop sign, Maddy was really glad that he had not gone with the handcuffs, she would had to have put them behind his back so that he could not use them to choke her, and she was afraid of how badly she would have taken advantage of him while he was that helpless.

“Andy, you just look divine, I don't even think that I could look that good in the outfit, it is totally you!” Maddy said while holding back laughter. “Sorry that the panties did not fit, I guess you will have to be careful where you swing that thing for this round”, she said with a wink of her eye. He certainly looked like a very buff maid, that's for sure. Maddy did actually have a strategy when she chose the maid outfit, she was hoping that he would be so self conscious about it the entire round that he would not really be paying her much attention.

“Make sure that your stockings are up all the way”, she laughed. “And just a piece of friendly advice, I wouldn't do any splits in that outfit if you know what I mean”

Andy's Penalty:

Alternate View: