Tails - Charlie goes first

Alexa catches the coin mid-air, slaps it onto her other wrist, and reveals what may be your best hope for not having to spend all your free time for the next week impaled on Charlie's strap-on: Tails.

"Well, Charlie, looks like you're up first" says Alexa as she strips off her clothes and sets a timer on her phone for 10 minutes. Alexa opens her arms, legs, and invites Charlie to get started as she makes a show of pressing 'start' on the timer.

Charlie starts with a page out of your own playbook, going down on Alexa with a "let me show you how its done, cucksleave". Charlie throws her arms under and around Alexa's thighs, and with a surprised yelp from Alexa, hoists Alexa's hips up to her mouth. In turn, Alexa throws her ankles behind Charlie's back - clearly enjoying the suddenness of Charlie's attack.

Charlie seems to be making short work of Alexa, and she is less than a minute into her time. You start to worry about how your turn is going to go, but not enough to feel your cage tighten as you watch the display in front of you. With 8 minutes and a lot of change still on the clock, you watch as Alexa's thighs tighten around Charlie's head and Alexa lets out a breathy "ooonnne".

Right on cue, Charlie unwraps Alexa's thighs from her head, lowers her hips to the floor, and puts her left hand behind Alex'a head and uses her right hand to guide her strap-on into Alexa's mouth, telling her "time to lube up".

Charlie only spends a few seconds forcing Alexa's head all the way down to the base of her lady-cock, ignoring her gags and half-hearted attempts to un-impale her face.

Satisfied that her strap-on is now sufficiently covered, Charlie pulls Alexa's head off her cock, and spins Alexa to face you, looks you dead in the eyes, and forces Alexa's head down into your lap. Charlie moves into position behind Alexa, bends down over Alexa, and whispers something in her ear. With a smile, and slight laugh, Alexa reaches for the fly of your pants and begins to undo them, 'freeing' your caged cock and placing it inside of her mouth.

"HEY! That's cheating" you protest.

"No, its not" replies Charlie with a slightly sultry, matter-of-fact tone. "The rules were; one: 'fucking contest, who is the real man'; two: 'Alexa is the judge'; three: 'a coin flip determined who went first'. Nothing else. There was nothing said about involving you while I convince Alexa here that I can fuck her like a man - better than you can. And the prize is the loser being the winers's cock sleeve for the next week"

All the while, Charlie is positioning her strap-on at the entrance to Alexa's pussy, and Alexa is sucking on your caged cock while she starts to play with your balls. Slowly, Charlie pushes her strap-on into Charlie, and you feel her moan into your cock. You wonder if it is at all possible for an erection to break a metal cage, but if it is at all possible, you suspect this might be the only way it could happen.

With a little over 7 minutes left on the time, Charlie begins slowly fucking Alexa. With every thrust, Alexa's head is **** down onto your cock as she moans and grunts into it. As Charlie quickens her pace, you can feel Alexa's moans grow more ****. You can feel her begin to approach her second orgasm, and there is still a healthy six minutes on the clock. Hell, you're not too far off yourself.

You attempt to slide backwards from your seat on the bed, only to feel Alexa wrap her arms around you to halt your retreat.

"Ahh. Ahh. Ah. Not so fast." quipped Charlie. "I told her to 'help you out', and that is exactly what she is going to do".

Held fixed in place, and fixed in Alexa's mouth, there is not much you can do but try to hold on. You don't want to give Charlie the satisfaction of making multiple come from the same fucking. Trying to focus on something, anything else besides the lips around your cock, making your cage feel ever smaller and more painful. Your eyes settle upon the key around Charlie's neck. You focus on it bouncing with her every thrust in Alexa.

As you watch the literal key to your manhood bounce around Charlie's neck, you feel Alexa begin to shudder. She lifts her head just long enough to moan out "twooo" before returning her attention back to tormenting you.

You take a glance at the timer on the phone, and see a little less than five minutes. Perhaps you're not totally screwed?

As if she can read your mind, Charlie forces Alexa into a prone position, and begins to fuck her even faster. You feel Alexa's mouth go slack and her voice change - it sounds like she is already approaching her third orgasm. the change in position has also brought Charlie, and the key around her neck, to within inches of your face.

"Don't think I don't I see you staring at this key. Remember, there was no end date on this chastity you agreed to. Whomever holds your key at the end of this little game gets to decide when - if - you get let out. With the way things are going for you tonight, I would say that it doesn't look good for you"

As she finishes, Alexa raises her head and stutters out "th-threeeee". Charlie pushes her head back down int o your lap, then grabs the back of your head and pulls you in for a kiss where she is practically shoving her tongue down your throat.

"Now, enough fooling around" says Charlie as she lays down ontop of Alexa, wrapping one arm above Alexa's shoulders and bracing herself with her other, before somehow quickening her pace even further.

With one minute left on the clock, has gotten Alexa to count up to seven, and at this point, in the final seconds of the timer, it seems like Alexa might be having one long continuous orgasm. Charlie's back is covered in sweat from her exertion, Alexa's face is covered in her own spit and the precum leaking from your cage, you feel like your dick is in a vice, and the whole room smells and rings of sex.

Suddenly, the timer goes off, and with one final thrust, Charlie stops he relentless fucking of Alexa. You all just lay there for a minute, catching your breath, before Charlie pipes up "so, what's the damage Alexa?"

"Well, in those last couple of minutes, I kind of lost count. It was kind of difficult to tell one orgasm apart from another. It was definitely more than seven, but probably less than ten... so lets just call it nine orgasms." Alexa recounts, still basking in the after glow.

Nine. Fucking. Orgasms. You need to beat that, because you don't think Charlie will honor a tie. That is one orgasm a minute you need to give Alexa, and you're not even sure that is possible for you. You're going to need to be smart about this.

You can either lay down flat on the bed, and have Alexa straddle your face, or you can have her sit on the edge of the bed while you kneel on the floor.

Laying down will probably be easier on your neck and help you endure the next ten minutes, but it will undoubtedly leave you exposed to any mischief the girls cook up - and they have already shown that they are not above playing dirty.

Kneeling will protect your cock more, but will **** you to crane your neck, which may make it difficult to achieve your goal.