Trapped and Trained Ch. 16

"Remind me," she continued, "in the limo, did you accomplish wrapping those sexy lips around my man's throbbing cock?"

I was sure she remembered and was just fucking with me, but seeing little other choices but to play her game, I informed her that no, I had not succeeded in getting my lips on Mitch's dick in the limo.

"Ohhhh, that's right - you took quite a load though, huh?! I told you he shoots like nothing you'd ever seen before. Just wait until it's leaking out of your pussy, you'll feel like someone stuck a fire hose up there as it continues to pour out of there. But anyways - so you didn't get your lips on him, meaning that you have to be punished. I mean, if I didn't punish you, how could I expect you to take future games seriously, right? So... let's see...".

She began to scan the pool for a few minutes, he mind going into overdrive as she wracked her brain to come up with a suitable punishment. Finally her vision locked in on a group in the middle of the pool. There were three men and two women - one of the women was topless with perky B-cup breasts while the other was wearing a white wicked weasel bikini, just like the ones I tanned in back at my apartment. They were so skimpy and revealing she may as well have been topless. The men they were with were your typical preppy jocks with their long, baggy swimming trunks, tanned shirtless bodies and intentionally messed up hairstyles. They were most likely on a vacation from college, being in their early 20's or so and making the most of their time here in Vegas... most likely on their parents' dime, also. They all had some type of mixed drink in their hands, the women dancing on one another and teasing the men mercilessly as they would periodically grind up against them, their cocks undoubtedly stiff as a board underneath the deep blue water. Vivian seemed intrigued by them, staring at them for a couple minutes before snapping back to the moment, turning her attention back towards me.

"Okay, Candi - this may be more of a reward for you rather than a punishment, but given our surroundings and environment, I can't exactly bend you over that table in the middle of the pool and spank you, now can I... tempting as it may be seeing that ass of yours swaying back and forth as you walked over to be a little cocktease to Mark. You've really learned how to walk like a whore. Anyways - you see that young group having the time of their lives there in the middle of the pool? I think it'd be splendid if you made their trip here to sin city a bit more memorable - give them something to talk about when they get back to school with their friends. So, this game is simple... there are 2 women and 3 men, meaning your mouth will have to come in contact with 2 pussies and 3 cocks before you come back to this canopy. The water is clear enough that, if I move my chair to the edge of the pool, I'll be able to get a front row seat."

She really expected me to be able to just wade into the pool and convince 5 people to let me go down on them? It'd be one thing if this was some kind of a sex party like the other night, but this was just at a pool on top of a casino. What if they just said no and sent me back to Vivian as a failure? I shivered as I stopped myself short of thinking what a 2nd degree of her punishment could be as I stood to my feet and tried to gain my composure to come up with a plan of how to make this happen.

I went to the stairway of the pool and waded in, the water coming up just past my navel as my silver chain jewelry floated up hanging from my belly button. The water was extremely comfortable - not too hot, not too cold, heated up perfectly by the sun and the obvious temperature control they had from the hotel. I decided that my ticket in to the group would be to win the women over first - if they didn't approve of me then there was no way I'd be able to get into their panties. The men would be easy enough - I figured that once they saw me playing with the girls they'd be easily manipulated and seduced.. their swim trunks would practically pull themselves off.

But how to win over the women - the girls I'd come in contact with so far seemed intimidated by me and almost angry at me without me even saying a word to them. I was going to need to lay it on thick to make sure they knew I wasn't there for long term competition, just a bit of fun and then be on my way. I decided to focus on the brunette girl in the white wicked weasel bikini first, figuring that if I got in with one then she could help me out with the topless blond next to her. I wandered over close to them and then put on my biggest fake smile before initiating contact.

"Oh my GOD! I LOVE that swimsuit! Is that a wicked weasel? I've heard about those but never seen one in person - and you wear it SO SO well! I'm sorry to be so upfront and to interrupt your group but I just had to come in for a better look - I mean, wow, you are just SO sexy in that, right?!"

The brunette turned to me, at first a bit confused by obviously flattered by the continuous compliments, especially coming from what she would normally view as competition for attention. The men were nodding approvingly with every word I said, more fuel in my favor and the topless blond seemed a bit taken aback, but also loved her friend getting such positive attention. The brunette thanked me and introduced herself as Jasmine, complimenting me back on my bikini and placing her hand on my arm as she talked to me.

"Aww, that's so sweet of you, thank you so much! And you - well, I mean, just look at you - these guys here have been eying you ever since you walked in with your friend over there. Yea, Mandy and I have seen you guys stealing looks over there, you aren't that slick!"

I couldn't believe it but I actually found myself blushing. She and I continued to chat, mostly consisting of me complimenting her and her modestly thanking me. As we talked, I started to see that all five of them were considerably wasted, being out here in the sun for a few hours, drinking who knows how many mixed drinks. They obviously had few inhibitions given that Mandy was topless and Jasmine was practically on full display. I continued to make contact with Jasmine and some of the boys as much as possible, touching the boys chests or having Jasmine show me her tattoos and tell me about her piercings. At that time Mandy chimed in that she had her clit pierced, obviously becoming a bit desperate for attention and trying to nudge her way into the conversation Jasmine and I were having. This was working beautifully.

Mandy was becoming so desperate for attention that she was beginning to rub up against me, pushing her tits up against mine and hinting repeatedly that she'd love to see the bows on my bra come undone and perhaps even the one on my bottoms covering my crotch. I gave a nervous laugh and told her that it could happen if she played her cards right, sending the boys into a frenzy and causing them to continue to reference how hot it would be to see the 3 of us playing together, complete with howls and high fives as the drinks kept coming.

Mandy was pressing her breasts up against my back this time, feeling her hands wandering around my hips as Jasmine backed into my crotch, her perfectly round ass fitting deliciously into my midsection. Mandy was losing control and was wasted as her hands traveled up my torso and found their way on my breasts. She was licking and sucking on my ears as I let my hands begin to massage and caress Jasmine's ass. If this were six months ago I'd be waiting to wake up from this wet dream disappointed - yet here I was and all I could think about was accomplishing a goal rather than thinking about two drop dead gorgeous women bumping and grinding against me. Mandy's hands moved over my bra and I felt the bows release their tension, the material separating and putting my breasts in full view for the three men eagerly watching us, their jaws stuck halfway open while the three women in front of them fulfilled their wildest fantasy.

I started walking forward, causing Jasmine to move forward towards the center island of the pool and Mandy to keep up with us. I whispered in Jasmine's ear for her to sit on the edge and, as she lifted herself out of the pool I hooked my fingers into the strings of her thong, letting her upward momentum pull the bottoms down over her ankles and off. I playfully tossed them to one of the men, causing more cheers and more high fives. Jasmine laughed and turned to face me, now sitting on the edge of the island with her legs spread, inviting me in between them. Mandy continued to follow me as I kissed my way in from Jasmine's knees all the way up to her pussy. Her legs were tanned beautifully all over, obviously meaning that she periodically tanned in the buff, with a small landing strip of pubic hair just above her vagina. I breathed patiently on her mound as Mandy's hands were massaging my ass and periodically rubbing up against my fake pussy while I faked pleasureful moans in response. I had Jasmine just on the edge and finally dove in with my tongue attacking her pussy while she leaned back and just enjoyed my masterful tongue. It only took a few minutes before I felt the warm gush of cum leave her pussy and enter my awaiting mouth.

I quickly turned to face Mandy and locked lips with her, transferring the cum back and forth from my mouth to hers as women had done with me at various parties. Mandy was taken aback at first but in no time was shoving her tongue deep into my mouth in return. Jasmine laid back and took in the show Mandy and I were now putting on as I put my fingers to work on Mandy now, sliding her pink thong bikini to the side and teasing the outside of her pussy while the men looked on with shell shocked expressions, probably thinking that this stuff didn't really happen anywhere but in pornos.

Mandy was bucking and grinding against my hand now, extremely close to orgasm as she was just moaning in my ear. I disappeared under the water, feeling her hands on the back of my head as I gave her underwater head. Her body shook in an eruption of an orgasm as I allowed myself to float back up above the water. She too was spent as I thought about how I was done with the hard part. Mandy made her way over to Jasmine, picking herself up out of the pool and delicately kissing her friend, talking about how hot all of this was and dropping the "what happens in Vegas" line with one another. Lucky for them, I thought.

I turned my attention now to the men, all sporting significant bulges in their trunks under the water now. I walked over and picked myself up out of the water, walking to the pool chair in the middle of the canopy on the island. They didn't move, just watching me walk, mesmerized by my ass and tits bouncing, jiggling and glistening as the water ran down them. I motioned for them to come over to me and they practically got in a fist fight trying to be the first out of the pool and over to me. Typical men, I thought, before remembering that I was a man underneath all of these prosthetic lies.

The men lined up shoulder to shoulder in front of me as I motioned for them to all pull their shorts down. They looked a bit tentative, obviously not wanting to appear homosexual to their other two friends, but Mandy and Jasmine cheered them on from the side, still recovering from their own pleasure rides on my tongue. That was all they needed as their shorts hit the deck. I faked a seductive smile and began to stroke the man on the right and the left while I stuck my tongue out and teased the head of the cock of the man in the middle. Up and down I stroked, having to multitask as I now started to bob up and down on the cock in my mouth. The show I had put on with the two women had obviously had an effect on the men as, in no time, all three cocks felt engorged and throbbing, each man groaning periodically. The man in the middle was getting the best of it, obviously, and immediately shot his load in the back of my throat as he pulled my wet hair forward to take him all the way into my mouth.

With him finished I took my left hand off of one of the cocks and continued to stroke with my right, now taking another cock in my mouth. This one was larger and thicker than the first man and he was uncircumcised, causing a new difficulty for me, but I expertly swirled my tongue around his shaft, letting my tongue piercing do all of the work and send him over the edge, quickly feeling a long stream of cum shoot out as he pulled my head off of his cock, shooting his entire load all over my face, covering my nose and eyes.

I had to keep my eyes closed as I knew that the last man was nearing completion as well and didn't want him to get off without getting my mouth on his cock as Vivian would surely consider that a failure. It only took a few deepthroat maneuvers before he too pulled my head off of his cock and stroked out a load of semen. I was surprised when I didn't feel any cum landing on my face, instead he had shot it across my chest, giving me the infamous "pearl necklace" from the feel of it. All three men collapsed on the various pool chairs in the area as I laid back on the one I was currently on. In no time I felt a tongue lapping up the cum all over me, from the pearl necklace all the way up to my eyelids, opening them to see that it was Mandy collecting it all in her mouth before returning my cum filled kiss with her earlier with one of her own, only she didn't allow me to transfer the cum back into her mouth, thrusting her tongue into mine and leaving it there until I swallowed it all down.

Mandy peeled off of me and went back to laying next to Jasmine, all five of them talking about how fucking hot that was and thanking me for being so giving. Across the pool I heard a clapping noise, opening my eyes to see Vivian sitting in her chair with a small video camera, obviously catching the whole thing on tape, cementing the memory for forever and no doubt intending to share it with Miss Vicki once we returned back home, whenever that would be. She collected her things and stood, calling out to me.

"Wonderful job, Candi - be sure to get a contact number for this lovely group and let them know that we're staying in the penthouse suite here in case they'd like to get together another time before we head out. Now let's head back to the room and get cleaned up for a busy night out - plus I'm sure Mitch will be up soon and wonder what we've been up to."

With that she subtly tapped her video camera, signifying that she intended to show her footage to Mitch, which would certainly put him in the mood to actually get my lips on his cock this time around, among other things. I rolled off of the chair and got the room number that Mandy and Jasmine were staying in before giving each of them a quick kiss goodbye, then blowing one to each of the three men and making my way back across the pool to the awaiting and very pleased Vivian.

"Fuck, Candi" she said so only I could hear. "I got myself off twice just watching that! Now tie your tits back up and lets get back to the room, we have a big night ahead of us and many, many more games to play!"