The Agent- Daisy Edgar Jones
You and Alex hung out for a few days and nights in NYC, just drinking and hanging out and talking shop but you could tell he was ready to get back and see his kiddo which you knew all too well. You hugged him and made plans for another visit soon to see Savannah and departed with that melancholy of joy and sorrow for your friend but you knew you'd see him sooner rather than later which made his parting a little easier.
You had one more night left in NYC but knew you were gonna be summoned at any moment and you finally were a little after 5pm with a text from an encrypted number with the Madames masquerade mask in a picture, followed by an address as the text. You got dressed and made your way over to the nice hotel Lowell Hotel, one of the nicest hotels in all of the country let alone just NYC.
You stated your business and the room number and the front desk let you up as you felt a bit nervous about this all but knew that whatever it was the Madame was wanting taken care of, she'd at least been more straight forward with you then anyone else. You reached the floor and two guards checked your ID and then verified with someone on the phone before letting you through the double doors as the Madame was sitting on the couch as she asked you to come sit while pouring a glass of wine.
You did as she asked and she nodded to the bedroom to say the issue was in the room, but that she wanted to talk to you first about what was going on behind the curtain. She didn't know much, only that Tiger, or who you knew as the Tiger Masked Man, had decided he didn't want simply one agency having too much power and all the push and gains they did behind the scenes for you had effectively been stopped. Everything over the course of the last few months was either a result of your own hard work, or their working to benefit the other agencies in some way. When you asked why she didn't have an answer, but wanted you to know that most of the group were still helping you in their ways, you just wouldn't see it yet.
When asked why even help you to begin with, she smiled and said it was partly to bring Damien down who had gotten too far on his over reliance of his own ego, and that some people had dealt with your parents before, and while your father always turned down the opportunities, they respected him all the more for it which made you feel like more of a sellout then you had ever felt before. She must've noticed your reaction and said that it was no shame for you to accept help, most of your growth had slowly been happening anyways, but the last year was just the push into expansion and giving you enough high dollar clients to warrant such. Everything now was under your control, win or lose.
You asked if Tiger was gonna nuke the Bollywood deal and she said she wouldn't know, but Bear would. The Bear Masked man you had met once before but never had many dealings with. The Madame proclaimed that if you help get her problem under control, she would facilitate a meeting with Bear, which wasn't normal and could potentially get her in trouble as there was a hierarchy to their doings. You didn't press for answers there but asked what she needed handled and she explains that she had helped facilitate a push in the career expansion of a few up and comers, but the one she was having trouble with was Daisy Edgar Jones, the lovely British actress whose star was in the rise but you had failed to grab her up prior to her big break two years ago and with the success of Twisters.
The Madame explains she needs Daisy to participate in a particular fashion event overseas but that Daisy has been unwilling to sign for the event. So the Madame made her a deal. If someone of her choosing could make her cum twice, she'd have to do the event, and if not, she'd have to which Daisy apparently eagerly agreed too. When you asked why, the Madame says that Daisy is a notoriously hard to please young woman and that many conquests, at least according to Daisy herself and those closest to her, have often failed to even get her off once let alone twice.
You didn't think this would be difficult, though you didn't voice such things as you knew that hubris would often befall those who thought otherwise. You made no promises but said you'd try which the Madame just smiled and said she believes in you. You drank from the wine glass and headed towards the room as the Madame just lit up one of her filtered cigarettes and turned on the TV, turning the volume up high.
You closed the door and saw Daisy already naked, rubbing her legs together as she smiled and asked if you were the guy supposedly that would rock her world as you shrugged and said you'd try as she eye rolled and said she'd heard it all before as she leaned up a bit and said she sorta recognizes you as you tell her you had a lunch meeting with her three years ago when you tried to sign her. She shrugged and said it didn't ring a bell which was a more common thing then you'd like to tell as you began to take your clothes off as she watched you carefully as she bit her thumb when she saw your manhood as she smiled and said it looked nice but that she's had bigger which did surprise you a bit.
You said you knew how to use it and she laid back and spread her legs as she told you to get on with it but you didn't take the bait as you grabbed her thighs and yanked her further to the edge of the bed as you leaned down and began to tongue at her slit, Daisy moaning as she said this was nice but she doesn't cum from oral which only made you lick and suck faster and more pointedly. She was clearly enjoying it as her hands rubbed her tits and she was moaning at your actions but she didn't seem to get wetter then she already was and as you stuck two fingers in, she yipped a bit and moaned in approval but still nothing.
You pumped your fingers while curling them again the top of her cervix as your tongue lashed at her clit, and this had Daisy moaning and screaming but still, no spasming no extra wetness, she let you go on for a few minutes before saying it was a nice attempt but she doesn't orgasm from oral and as you pulled out your fingers she leaned up on her elbows with a smirk and a condescending good job but that you wasted time as she tells you that you only 24 minutes left as the deal was you had to get her off twice in half an hour, something the Madame did fail to remind you.
You quickly pulled her legs up and draped them to your shoulder as she moaned and grabbed your arms as you lined your cock up and pushed inside as Daisy nods that she likes being stretched as you felt some resistance as her pussy was tight, so the idea of her having bigger than you while also being this damn tight is a marvel.
Your hips began to move quickly, Daisy locking eyes with you as her cock smirk meant you were in trouble but they didn't stop your hips from moving quickly, each stroking build up more speed as your palmed the bed while she kept a hold of your arms, her feet rubbing against your head as she felt your pushing deep as you went harder, Daisy starting to moan more as if she was enjoying it and not as a bodily reaction, and this made you smirk as you found the right rhythm and stuck to it for a few minutes as you knew she wouldn't cum yet but that you had the right speed and power to get her there.
You eventually pulled out and checked to see you had 19 minutes as you turned her around and got her ass up as you smacked her cheeks and got her to moan as she seemed to like this as you pushed into pussy from behind as she felt your hands rubbing and smacking her ass hard as your cock went in and out of her cunt at the same pace as you were doing before while reaching deeper, and this was triggering her as she was moaning more consistently and loudly then she was before, her hips slowly moving back to add more as perhaps she wanted an orgasm.
You lifted a leg up onto the bed to allow more room for your cock to crash into her as she worked herself back and the harder you went, and the angrier you smacked at her reddening ass cheeks, the closer it felt like something was gonna happen as she grabbed the sheets tightly and was screaming into the bed at this point as she finally curses loudly and threw herself back as hard as she could as you didn't relent at all feeling your body getting tired from how rapid and wild this was but you never slowed down and this seemed to be what did the trick as Daisy bucked back and then gyrated her hips like crazy as she orgasmed, wettening your cock with so much orgasmic liquid that you were sure she was squirting and as you pulled out from the pressure you watched as she quickly rubbed clit while soaking the edge of the bed and your lap with a large amount of orgasms fluid.
Having made her squirt you felt fairly confident you would get this second orgasm out but she turned to her side and held a hand out to give her a minute as she exclaims she has had one that intense for a year or so, as you just shrugged and said 16 minutes which made her smile as she said it would be harder to get her off this next time as you pushed into her while she had her legs together and to the side like she did, telling her you still had to try.
The next ten minutes passed and nothing you did seemed to be working. Between the sideways missionary, more doggy style, a very wild cowgirl ride that made you cum inside of her deeply which didn't even trigger anything close to her having another orgasm you were really as she was sucking you off now tasting your cum and her wetness off of you cock as you hadn't expected to be left with so little options.
You asked if she was okay with anal and she shrugged and said it didn't really do anything for her but you quickly got her into reverse cowgirl as she lined herself up and let your sensitivity but still achingly hard cock slowly sink into her ass as she leaned back and braced herself by palming the bed as you held her hips and slowly worked yourself into her colon as she was moaning but wincing a bit as well as you worked her down till you got a little more than half of your length into her.
Daisy asks you to slow but you knew you didn't have time and you just worked her down as you pumped up, immediately jamming your cock into her rectum as Daisy began to scream and moan out and your cock began assaulting her asshole with sharp quick strokes as your body was a sweaty mess from the exertion of how hard and fast you were going to get anything out of this woman. You needed and wanted more answers to what was happening and if this was the only way you had to succeed. You had too.
Daisy pushed up onto her heels and began to work herself down as she pumped her hips straight up and down as you jammed your hips up and then positive torque of these flashing actions made your cock throb as you knew you were gonna cum again but the way Daisy was moving, the speed and pace made you think she really didn't expect to cum again and this made you furious as you moved a hand from her hip to her cunt and stuck two fingers in as she screamed out in surprise as you began to pump and curl your fingers as you fucked her ass and as you did you felt both holes react almost immediately as her pussy began to spasm a bit and her anal walls clenched up more, which with her hips thrusts and your own pumping hips and moving fingers, Daisy was losing it as she was screaming angrily and shaking her head as you felt her fighting it but you were determined and you went as hard as you could for as long as you could.
Daisy screamed loudly as she held her body down with a screaming cry of helplessness as you felt her pussy spasming as she was a whimpering mess as she felt your body continuing to slam up before holding her down as you kept your fingers inside of her while your cock was pumping thick globs of cum deep into her asshole as Daisy was still a screaming, groaning mess as she felt you letting rip before you pulled your fingers out and let her slip off to the left of you as you looked at the time to see you had only two minutes to spare as you were groaning and moaning and breathing hard as Daisy was just lamenting she couldn't believe it as you smirked and just was happy you made it happen.
Daisy covered herself as she asks why you were helping the Madame and as you explained you could see her starting realize your own plight as she explains she just didn't want to be stuck to the whims of the Madame anymore then she had and you said you'd see what you could do for her as she asked why you would help her, as you shrugged and gathered your clothes and said it was the right thing to do. Daisy genuinely seemed stunned by this and she blushed as she thanked you and you nodded and headed out of the room.
The Madame looked at you and smirked as she thanked you for your help but seemed surprised by you sitting back down where you were before. She said she would get you a meeting with the Bear and that your help was appreciated but you shook your head and asked that she didn't let Daisy do the event, or at least let her go after she honored the event.
She took a drag and thought about this before asking to pick one. The meeting or getting Daisy out of her desk. You rubbed your face and knew she had you and you chose Daisy and stood up and began to storm off as the Madame asked why you would do that for someone you didn't know.
You said the same thing you said to Daisy and then left as you didn't see the Madame nod with a smirk on her face as you rode the elevator down and grabbed an Uber to take you home so you could be ready to leave to hear back to LA. A failed signing and now further away from getting any more answers, what a bad trip ultimately.
End of chapter.