Try Me Too Pt. 01

A standard blue T-shirt went together with a pair of white shorts and brown leather flip flops. His coworkers may have recognized his face, but they would be spread out during the day working. Anthony left his cellphone behind in his room, that way he wouldn't be bothered by it constantly ringing and vibrating from within his pocket. His next stop would be to dial up room service and play up a made up tale to get someone working room service to sell him a bottle of wine. He still had doubts in the back of his mind, wondering if Kate was playing him but Anthony had to do something to take the risks. Upon calling up room service and hearing a woman answer the phone, Anthony suddenly got a better idea in mind. He insisted on a fake story that he was Kate's husband and needed a bottle of wine sent over to her room. The request went over smoothly and then it was time to make the journey back to the seventh floor and travel to her room.

With a bit of luck, Anthony felt he could intercept room service before they knocked on the door. He knew the pain they went through having to travel back and forth with the service elevator. Along the way, he caught sight of his old friend Scott. He was down on the floor in a hallway leading among the fifth floor suites. He seemed to be on clean up duty today for janitorial work. Someone had spilled drunks all down on the floor and made a mess on one of the walls. Anthony didn't envy what his friend was stuck doing for the day. He was thankful that he didn't have to worry about Scott poking his head out and learning of the games he was currently playing with another gorgeous buxom model. There were no ill feelings he had towards his friend, but Kate was someone he absolutely did not want to share with Scott whatsoever.

Stepping back into the elevator, Anthony brushed past a few people that were wearing summer type outfits. That was common for guests checking in and spending time at the hotel. So far, he blended in with them and was happy his outfit had served that purpose. The elevator came to a halt at the seventh floor and then he made his exit all along. Across the hall, Anthony witnessed someone else stepping out with a tray cart pushed. It had to be room service delivering the bottle of wine directly to Kate, coming from the service elevator on the opposite side. Smiling to himself, he felt lucky to get off that elevator in time and catch the butler journeying to her door. Anthony stepped closer, making his way there and noticing the bottle of wine, two glasses and large tray of ice. The butler was in fact a maid. A black woman, someone new at the hotel who clearly didn't recognize him. He offered a smile and played it up pretending to be her husband.

"Hi there, mind if I take this to my wife?"

"Oh, sure."

The woman offered a smile and stood there as Anthony carefully grabbed the metal tray. She then walked towards the door.

"I'll knock for you, sweetie."

"Thanks, appreciate the extra hand."

A laugh was shared between them before the woman knocked with her right hand. Anthony had to think for a moment, hoping Kate would be back hours later, assuming she did go to the pool.

"Who is it!?"

Her voice came yelling from inside the room. Anthony called out to her.

"It's me! I've got a surprise for ya, honey!"

The maid began pushing her cart back down the hall for the service elevator while Anthony stood there carefully holding the tray in both hands. Within seconds, the door came swinging open and once again, Kate greeted Anthony. This time she wore a white two piece lingerie outfit. Her flat stomach was visible along with her huge breasts that once again looked barely contained in a tight bra. Down below, Kate was barefoot, no need to put on any shoes of sorts without a destination to go. She raised her hands up, positioning them at the edges of the doorway while gazing back at his curious face. Kate had pinned her hair up in a high pony tail, gazing back at him with a soft smile.

"Oh, it's you. I haven't ordered any wine yet."

"You told me to impress you, so I took a shot and figured you might want some served early. Are you disappointed, Kate?"

"No, I'm not. Some good timing on your part. It's not dark yet, but I like to relax most afternoons."

"Well, I'm happy to hear that. So are you gonna let me come in?"

Giving her a goofy grin, Anthony held back from laughing.

Kate stepped back from the doorway, allowing Anthony to enter with the tray. He stepped slowly and carefully, reaching the kitchen and placing the tray down on the wooden table. Kate had shut the door behind him, eventually walking in front to give him the view of her buttocks. The white lingerie panties she was tucked down the crack, revealing those thick cheeks. He took a glance and then waited until she turned around to look at him, then he finally spoke up.

"How was your swim? Did anyone recognize you out by the pool?"

"I didn't go out. Changed my mind after you left and started thinking about playing dress up. I wanted to get warmed up and ready before I go to my photo shoot tomorrow. It's been a while since I dressed up all sexy to stand in front of cameras."

His eyes watched her grab the while bottle and examine it. Kate then moved her hand towards the metal handle of the ice bucket, pulling it off and setting it down. She grabbed a handful of ice cubes, dropping two in one glass, then the last cube down in the other. Kate grabbed the glass with two cubes and then spoke up.

"I'm sorry, I should've asked if you wanted ice first."

"No, this is fine."

She wasted no time unscrewing the top off the bottle to open it. Anthony had noticed Kate didn't bother checking the date like some wine buffs preferred to do. That was something he had picked up on after having to deal with cork sniffers in the past. She poured her glass first and then filled his. Together, they raised their drinking glasses as she smiled back at him.

"Cheers, guess you're getting lucky today."

Her words hit him point blank, causing his heart beat to accelerate while Kate swallowed down her entire glass of wine. She had admitted her own plan and now Anthony knew they would soon be fucking. He sipped on the wine glass, tasting the strong flavor and swallowing it down. Kate was already on her second glass, drinking down half of it by the time he could respond.

"So you've taken it up yourself to try me, huh?"

"Mmmmmhhhhhmmmmm..."

Kate muffled her reply between finishing off the glass of wine. She let out an audible 'ahhh' after having swallowed it down. Smirking back at Anthony, she gave him a nod before replying.

"Yeah, I don't know what it is about you. Something about you gives me a good vibe, you know? You remind me of a man I used to fuck before I got married. He was good looking, but I liked him more for who he was. You've got balls and know how to speak your mind. I like that in a man."

"I'm flattered."

Placing her hands on her hips, Kate smirked back at him.

"Tell me something, Anthony. What's your ultimate fantasy for me? Are you the type of man who likes to take it slow in the bedroom.. or are you a little rougher around the edges?"

"My ultimate fantasy?"

"Yeah, go on and tell me. I'm listening."

Biting down on his lower lip, his eyes glanced down at her heavy cleavage before blurting out his words.

"It's easy. You know what you're built for Kate? To have a nice cock shoved between those big, beautiful titties. I know where I want it."

"Oh really? I used to get that a lot."

She giggled.

"It's been a while since I've had a guy tell me to my face that he wants to fuck my tits."

Anthony smirked, flashing his teeth.

"To answer your question though, I'm somewhere in between. You get me in the bedroom, I'm gonna make sure that I explore all your curves and give it to you where you want it. All three holes, between your tits and in the end? A face full of cum if you want it."

"Mmmmmm, been quite some time since I've had my face all sticky."

Kate had replied in a soft, low and seductive tone of voice. Anthony had nothing more to say as he set the wine glass down and leaned closer to her. Her heavy tits were still contained in that bra, but soon they were brushing up against his chest. Kate reacted by throwing her arms around his neck and at long last, their lips met for a passionate kiss. She moaned into his mouth, taking a few steps back and pulling him in as they continued to trade tender kisses. When their lips pulled apart, Kate went back in for another series of kissing while roaming her hands at the front of his shirt and balling her fists for grips in the fabric. This only made Anthony want to move his hands at her breasts and squeeze them from within the bra. Kate moaned in his mouth and finally broke the kiss.

"Ohhhhh, let me help you with that."

Loosening her hands from his shirt, Kate stepped back and then smiled at him as she moved her hands behind her back. She wanted to see his eyes fall, glancing down into her heavenly cleavage as she loosened the bra straps from her shoulders and then tossed it off. Anthony's eyes became enlarged as he was now face to face with Kate Upton's famous breasts. She threw the bra at him, laughing when it landed on his face to distract his view. He pulled the bra off as Kate began to step backwards and grin at him. She then turned her back and ran to the bedroom, knowing he would chase right behind her while she giggled the whole time.

"You want these titties? Come and get 'em!"

When she turned around, Anthony nearly tackled her as he knocked Kate down to the bed and shoved his face between her amazing breasts. She giggled before letting out a moan and moving her hands to her breasts to smother his face with them. He began to shake his head around and slobbered, properly motorboating them before getting up. As Kate had a moment to lean up with her elbows pushed into the white blankets of the bed, she then began to shake her breasts. They smacked and pounded his face back and forth. Anthony eventually moved his hands to grab at her breasts and then squeezed them, listening to Kate moan. His eyes shifted up to her face when he fed her right nipple to his lips, sucking on it. She let out a moan and patted his head, just before he alternated to her left nipple, shoving it between his lips and sucking it lovingly.

"Mmmmmmm, I can tell you love those tits. Ohhhhh, I bet you used to dream of getting your hands on them. Your dream came true today, Anthony!"

She lay back on the bed, moaning at his touch. Anthony then moved off Kate. Setting his feet down over the carpet floor, he kicked off his flip flops and smiled down at her as he began to pull his shirt over his head. Kate crossed her leg and propped her head up with her left arm against the bed. She lay on her side, watching him strip. When Anthony pulled his shirt off, she giggled.

"You're nice and slim. I think you've got the body of a man who can handle me."

Anthony blushed but smirked back at her when he unbuttoned his shorts and then dropped them to reveal his white pair of underwear. Kate glanced down to see the outline of his hardening cock poking up with an apparent bulge. She licked her lips upon witnessing his thumbs push down beyond the elastic band and then drop his underwear. Kate then bit down on her lower lip, flashing the front row of her pearly white teeth at the sight of his hardening cock. That was before she leered those big blue hues back to Anthony's face and then patted her right hand in the middle of the bed.

"Come on, get up here."

She moved her hand, pointing her index finger directly at his cock.

"I want that."

He thought of telling her to come and get it, but Anthony was going to play along instead. He leaned down, sinking the palms of his hands into the white sheets of the bed and then crawled forward. Kate was to his left hand side before he turned around and laid his back down, resting his head onto one of the pillows stacked at the front of the bed. She leaned over him, lowering her right hand to wrap those slender fingers around his cock while pressing her lips to his. As Anthony kissed her, he gently cupped Kate's face, caressing her skin as he felt her hand pumping up and down to make his hard dick rise into full size. Trading kisses with Kate, he slipped his right hand down to her breasts, fondling one of them and giving it a squeeze. All that did was make Kate pump her hand up and down at a faster pace.

When their kiss ended, Anthony gazed back at her big blue eyes as she pulled away. Kate tightened the grip of her hand around his shaft and then began to move on the bed. She pushed her legs together, bending her knees to lean over and play with his cock. When Kate let go of it, Anthony decided to tease her with a trick in mind. He waited until Kate had parted her lips, opening wide. Since her hand was no longer holding his cock, he could twitch and pull the muscles, moving it away as she tried to slip her lips around it. Kate giggled when her mouth missed his cock and instead the head pushed against the right side of her upper lip, rubbing against her beauty mark. With her tongue she licked the head, circling it around and making another attempt to place her lips over it.

Again, Anthony twitched his cock and it missed Kate's mouth a second time. This time she reached back for it with her right hand, gripping it at the base with authority to hold it straight. Kate lapped her tongue across the head, shifting her eyes up at Anthony's face to look at him as she pushed the head of his pole between her lips. He let out a soft moan as she began to suck his cock, slow and sensually. 'Mmmmmm', she let out a muffled moan, shoving more into her mouth as she began to pull her lips back to the head. A popping noise was heard as Kate pulled her lips off his cock and began to tease him by wiggling her tongue across the slit of his head. Anthony sat there, moaning as he moved his left hand to stroke through Kate's golden hair.

She broke eye contact upon shoving his cock back into her mouth. For now, Anthony was getting a real showing of how slow and sensual Kate Upton liked to begin a session like this. She took her time, bobbing her head up and down to suck his cock at a slow pace. All he did was lay there, relaxing as he then used his right hand to caress down her back. He playfully grabbed at her buttocks, causing her moan a muffled sound with his cock still in her mouth. Kate responded to his touch by shoving her lips all the way down, forcing the head of his cock to meet the back of her throat as her lips buried at the base. She removed her hand, allowing her more room to suck. Her strong gag reflexes caught Anthony by complete surprised as he grunted at moaned. All Kate did was pull her lips back to the head and release his cock with a popping sound.

"God, that was amazing."

Ignoring his words for now, Kate began to lick up and down the side of his shaft, then pushing her lips against. Anthony listened to the slobbering noises her lips produced as she went up and down and then came to a stop. She grabbed his cock again, stroking it back and forth with her right hand while smirking up at him.

"Mmmmmmmmm, nice cock you've got there. You like how I suck it, huh?"

Smiling Anthony nodded his head to her.

"Yeah, you know how to handle it well."

Still smirking at him, Kate let go of his shaft and began to move around the bed. She crawled in front of him and then pushed her legs together. With her knees bent, she held her large famous breasts up and then winked at Anthony.

"I know this is what you really want."

She began to wobble her tits, shaking them in her hands to make sure that Anthony's entire attention was devoted to her busty chest. Kate smirked, licking her lips when she noticed him reach down and grab his cock. Anthony held it directly up for her and then Kate pulled her breasts apart. This position was a first for him when it came to the act of titty-fucking, but Anthony rested back on the bed, watching as Kate squeezed her tits around his cock and then he removed his hand entirely. She remained resting on her knees as she began to pump her boobs up and down, fucking his cock with them.

"Ohhhhhh, man..."

Swallowing his breath, Anthony moaned as he was now experiencing one of his greatest fantasies. The feeling of his cock pumping back and forth between Kate Upton's famous breasts was almost too good for him. Once again, he had memories of his three day long affair with Kelly Brook, wishing that was enough to prepare him for something like this. Kate went slow, pumping his cock back and forth from his position as she was bent over. She studied the expression of pleasure on his face, smirking as if to tease him with her angelic eyes anytime he glanced away from the action down below. Her breasts were so big, they easily swallowed his cock up with the poking up from each full thrust.

"Mmmmmm, feels good, don't it? Ohhhhh, it's been so long since I've had a cock right between my tits."

Kate giggled, flashing her teeth as she continued to work her breasts up and down. She broke eye contact to glance down, but from this position, there was no way she could dart her tongue out and lick the head. She concentrated on pumping her breasts up and down, all while Anthony lay there moaning and developing new ideas in his head. This fun with Kate wasn't enough. He knew that he was a greedy man and would want more, just as he did with Kelly Brook last month. Swallowing his breath, he thought up a game, inspired by what he did with Kelly.

"Kate..."

"Yes, darling?"

"I... I wanna play a game with you."

Still working her tits over his cock, she moaned upon replying.

"Mmmmmm, what kinda game?"

Biting down on his lower lip, Anthony smirked back at her.

"See who can cum first when we do the next round. If you force me to cum first, I'll pay the bill on your entire week stay. But if I manage to make you reach your orgasm first... then how about we do this again during your whole stay? I'll be your dirty little secret. No strings attached after you leave."

She laughed at him for a moment. Kate continued to work her boobs up and down over his cock but slowed down now.

"Oh my god, you really have put some thought into that."

"Yeah, I guess you can say I have!"

Laughing again, Kate made one last thrust of her breasts sliding down his thick rod. She then let go of them all together, freeing his cock as it fell from her tits. Leaning up, she looked back at Anthony while biting down on her lower lip and shoving her fingers down at her lingerie panties. Kate had to lift herself up a bit as she shoved them down, revealing her wet pussy without a single hair in sight. Anthony licked his lips as he studied her beautiful vulva lips. Eventually she was able to tug those panties beyond her knees, lean from behind and grab them to pull them entirely off her legs and toss them to the floor. Kate then smiled at Anthony as she crawled over him. Pressing her hands into his chest, her mighty tits shook and wobble above him. Anthony took this moment to caress her breasts with his hands, then squeezing them hard. The feeling of her erect nipples poking his palms had made him moan.

Kate had moaned for him too and when he raised his head, that was the moment she needed to pull her breasts apart and smother him with them for a second time. When Anthony moved her hands, she proceeded to rub her boobs up against his cheeks, flapping them up and down as he made a desperate attempt to suck and slobber on them. Anthony failed, causing Kate to shake her tits again, slapping up against his face and shaking all around. When he placed his hands back around them and gave a hard squeeze, she removed her hands entirely. Guiding her right boob to his mouth, Anthony licked at her nipple and then moaned at the touch of her hand. He could feel both of Kate's hands gripping his shaft down below. She squeezed her fingers tightly as she held it up and then leaned back up. When he pulled his face from her breasts, he leaned back over the pillows and watched. Kate carefully lined herself up, hovering his cock above her juicy pussy.