He grazed his fingers along the length of his shaft and smiled, imagining the nasty things Brooke liked to do to it, along with the vulgar look on her face as she did them. Jake had never felt so proud of his cock before. He knew he was larger than average, he had played varsity all through high school after all, but he had never cared until Brooke yelled, “I’m glad God decided to supersize your fuckstick, because THAT’S how you nail a girl!” Jake ran the sentence through his head six times before he was able to untangle it from the thick depths of Brooke’s shuddering moan.
He had imagined her moaning the sentence several times since, each time bringing the blood to his cock. Already hard, this time it just added a thickening to the existing throb. Jake shook his head and pulled onto the highway.
This isn’t supposed to happen.
Though it sounded like an excuse, Jake really had hired an escort to improve his relationship with Sasha. That was the endgame from the beginning. Jake wanted to learn to live with, not live without Sasha. He was a lifelong learner. Maybe it was that he’d always had the means to learn whatever he wanted, or maybe it was how he was wired, but when Jake chose to learn something he made sure he got damned good at it.
He had private coaches for tennis, guitar and Italian, which was why he won most of his matches, could play anything by Clapton, and spent a month in Venice without ever saying, “Scusi?” He also had a personal trainer who kept him looking like an underwear model. So of course Jake wanted a professional when learning how to fuck. His feelings for Sasha had nothing, or everything, to do with it. What Jake didn’t expect, was for the professional to fuck him into a new breed of feeling.
Brooke was a drug, and while Jake wouldn’t touch coke, or heroin or anything else that wasn’t liquid or green, he would snort Brooke every fucking day of the week if he could. Jake had never been more addicted to anything in his life, not even close.
After his first afternoon with Brooke, Jake went home and fucked Sasha inside out and upside down. He didn’t even know she was a screamer, but Sasha split their usual lovemaking silence with her nearly violent cries. At one point, Jack had two fingers inside her, another rubbing her vulva and his thumb stroking her asshole with a circular grasping motion, just the way Brooke liked it. Sasha liked it too, at least judging by the way she nearly shattered his eardrums.
It was the best fuck-fest he and Sasha had ever shared, and yet … he couldn't stop thinking about Brooke.
As good as it had been, Sasha wasn’t the gorgeous blue-eyed nymph who charged for her pussy by the hour, which was something Jake found impossibly sexy, though he didn’t understand why and was completely surprised that he did.
He booked the following Tuesday, and the appointment confirmed what Jake already knew. Brooke was worth every bit of the risk. The situation was temporary, and as long as he kept it from Ted the doorman, he would use his rendezvous with Brooke to bulletproof his relationship with Sasha. He figured he could fuck her six to seven times for each memory he made with Brooke. But the lies got harder and harder to tell himself since he was imagining Brooke’s eyes, hair, and sultry little laugh every bit as much as he was thinking about the glistening sheen of her bald and sopping cunt.
Long ago, Jake thought there might be something wrong with his libido. While other guys his age were pounding all the grade A pussy they could get, being a wolf had never appealed to Jake. He and Sasha had sex a few times a week and that felt like enough. He rarely even jerked off beyond that.
But Jake had been adding mayo to his knuckle sandwich twice a day and three times last Thursday, in addition to fucking Sasha every time she let him. Between the change in style and the increase in frequency, he had to wonder if she was catching on. There was no denying it, Brooke had woken something up inside him that couldn't be calmed. He was always hard, and couldn't get Brooke out of his mind.
Jake was less than 10 minutes from Con Brio, playing back his last encounter with Brooke inside his mind.
She had told him to take his time so he did, sliding his large hands beneath her shirt and rubbing her tits beneath beneath her bra. He touched her careful and deliberate, his fingertips grazing her skin. He pulled off her shirt and started suckling her perfect pink eraser tip nipples for several minutes before undressing her to her panties.
He stared at her waiting body, then slid his hand down inside her panties, lightly teasing her, then pressing his finger deeper between her lips and rubbing her button in circles. He started slow, fucking her with his fingers, but then sped until it was sloppy and loud. “I need your cock,” Brooke whispered. He ignored her, shoving every finger inside and pushing his palm against her mound.
“Beg,” he said.
And she did.
Jake made her beg for a good five minutes, even though it might have been more painful for him, the way his package was purple and pulsing, head thick and veins throbbing. But the second he was satisfied that her cries were coming from her gut rather than his pocketbook, he was ramming her cabbage patch as hard as he could.
She was soaked, and the squishing was the loudest he’d ever heard, though barely audible above Brooke’s deafening moans. He was slamming her pelvis while stroking her lips with his fingers when Brooke came hard. Her screams sent Jake into a cock shot. He stayed inside her until his final blast, then pulled himself from her pussy and kissed her from her tits to bellybutton, before sliding his tongue up and along her slit, lapping the wet messes they made together.
Jake wasn’t stupid enough to think he would, or could, ever end up with an escort, but that didn’t mean he was supposed to end up with Sasha. He had no seeds to sew or points to prove. He wanted to get married and be happy ahead of schedule, just like his grandparents had. He had always figured that meant Sasha. Yet, as unbelievable as it was, after a lifetime of conditioning, an escort might have been the person to change his mind.
Sasha was a good girl, and she could probably play nasty just fine, especially if she set her mind to it. She was a lot like Jake in that way. But Brooke was unlike anyone he had ever met before, and he didn’t just mean in bed. Yes, she was sexy as fuck, and worth every cent he never had to earn, but it wasn’t just that. Brooke had an undeniable crackle of intelligence, humor and, above all, passion. Even more, she was amazingly unapologetic. She may have been an escort, but she clearly loved her job, and was proud to do it. That was something to be envied. Jake knew plenty of people with bottomless wallets, whose true satisfaction was spiderweb thin.
Jake got the impression Brooke never allowed the sun to set on a day that didn’t see her satisfied and smiling, though he was a paying customer and it was her job to show him what he wanted to see, so who was to say where the reality started.
That question was the reason he’d chosen this evening’s activities.
Jake pulled into Con Brio, relieved to see the parking lot so empty. It should have been on a Monday night, which was why he picked it. Jake had thought about meeting Brooke somewhere trashy, or somewhere outside his normal circle where he wouldn't be seen, but that would have soiled the point. So he opted for distance. The odds of him being spotted with Brooke at Con Brio, 40 minutes away on a Monday night were so small, Jake figured it was meant to be if he got caught.
Jake stepped from the car and smiled at the valet, then approached a door being held open by the tallest doorman Jake had ever seen. He glanced around the restaurant, spotting Brooke almost immediately. It looked like he got more than he paid for.
She was stunning. A red dress, strapless. Scooped low but tasteful, with her hair piled high and small earrings matching the silver and pink necklace she wore when they fucked.
Jake wanted to whisper in her ear, “Meet me in the bathroom, you filthy fucking whore so I can fill your mouth with the cum I paid you to swallow,” but that wasn’t what this evening was for. He didn’t feel bad for thinking that, even though he might have just one week earlier, but that’s because he had spent several hours with Brooke, who had invested ampl
e time into helping him understand that he didn’t need to apologize for those fierce and sudden thoughts which chased arousal. Quite the opposite, she said. Jake should acknowledge them so he could use those feelings to fuck her, or whoever else he was filling, right into a better orgasm.
Jake took Brooke’s hand and said, “You look beautiful.”
Brooke smiled and Jake sat.
Something fluttered across her face, sending a jolt of panic to his system, since Jake was the type of guy to genuinely care about the feelings he was paying an escort not to have. But he couldn't ignore it, Brooke seemed almost... unsure.
Jake asked Brooke what she wanted to drink, then ordered a cosmo for her and a mojito for himself. “Have you been thinking about me all day?” Brooke said in a purr when the waitress left.
“Nothing but,” Jake smiled, wondering if Brooke knew he wasn’t lying. Hard to tell since she looked a million miles away. “Anything wrong?”
“Of course not!” Brooke shook her head. “I’ve been thinking about you all day!”
Jake wondered if that was a lie. Brooke reached beneath the table and found his cock. It was hard the entire drive, and while Jake had managed to calm it from the car to the restaurant, his blood had rolled to a boil and settled in his dick the second he sat. “You’re already hard for me,” she said.
Jake smiled, then took Brooke’s hand from his lap and set it on the table. “Of course I am,” he said. “I woke up hard for you, and the only reason I didn’t fall to sleep hard for you was because I shot myself into your panties, just like you asked me to.”
“Are they here?” she whispered.
“They’re in the trunk.”
Brooke pouted. “Why aren’t they in your pocket.” She slipped her hand inside Jake’s pocket to see if he was lying. He wasn’t. She started stroking his cock anyway. Jake shifted in his seat, then brought her hand to the top of the table again.
“Someone wants to fuck me,” she giggled and cooed.
It went on like that for another 15 minutes. The blood in Jake’s dick continued to pound, but the clouds in his mind were starting to part. Sure, Brooke was the sexiest thing he’d ever seen, but she couldn't go more than a few minutes without leading the conversation to sex, and seemed downright uncomfortable with the prospect of sitting in a restaurant and holding her end of a conversation. That was fine. If all there was to her was sex, then at least the confusion was gone. They’d finish their dinner, he’d take her somewhere and fuck her into outer space, then return to earth where he belonged, and where he should have stayed from the beginning.
“What’s wrong?” Brooke’s eyes were suddenly large and probing.
“What do you mean?”
“Something’s wrong.” They were already on their second round of drinks and waiting on their third. Their grilled shrimp with Nam Prik sauce was already finished, and the bruschetta mostly gone. “I can tell,” she said.
“Nothing.” Jake shook his head, “I swear.”
Brooke wasn’t buying it. Her eyes fixed on his, expectant. Jake found himself unable to break from her gaze, so he spilled the truth. “I just wanted to have a conversation without it leading to the bedroom. I wanted to talk to YOU.”
Brooke looked like she’d been slapped.
She said nothing for half a minute, and for a moment, he thought she might cry. Finally, she said, “Why would you pay me hundreds of dollars for conversation?” It was an accusation, brittle behind its confusion.
Jake swallowed, then said, “Because I can afford it, and because you’re worth it.”
This made Brooke more uncomfortable. She looked away and shifted in her seat, just as the waitress appeared with their drinks and a promise that their meal was a moment away. Jake hated to see something on her face break, so he said, “You just need some more social lubricant,” then brought his mojito to his lips and set the example. Brooke followed.
Their glasses were empty two minutes later, and conversation was flying in five.
Jake learned that Brooke loved to scuba dive and had once even gone cage diving with sharks. He was most surprised to learn that she wanted to be a teacher and that she served as a docent once a week at the local art museum. Brooke’s stories of the art museum went well with his stories of being a counselor at the local rec center, just like his sailing stories matched her scuba diving ones perfectly.
Conversation grew hot, but not because it was paid to. Jake went first, telling the story of how he lost his virginity, then Brooke told hers. His was cliche, hers was unbelievable. Brooke was clearly drunk, but Jake believed her when she said, “I’m so fucking wet right now you could ring my panties in a bucket.” She laughed hysterically, then dropped her voice and added, “except I’m not wearing any. Wanna feel?”
Of course he did, and that alone almost made him cum in his pants, but the conversation was going so well he didn’t want to ruin it. Brooke leaned across the table and pulled herself to his ear, flicked her tongue along the bottom, then blew her hot breath inside his canal as she whispered. “You’re the one making me so wet, Jake. It has nothing to do with your money or this restaurant or anything else. I would happily fuck you for free, then beg you to give me more.”
“I would pay for every fucking second and consider it money well spent,” he said.
Jake already felt like he was about to cum when he suddenly felt her hand on his cock and heard her whisper, “I can’t wait, Jake. I need you to take me to the bathroom and do things to me that you can never tell anyone about.” Her hand was jerking his cock under the table. She suddenly stopped, then whispered again. “I’ll be in the ladies room if you need me as much as I need you.”
There was an attendant in the restroom. Jake gave her $100 to leave and another $100 to stand outside and make sure no one else came in. The attendant closed the door and Jake turned back to Brooke, who was already at a 90 degree angle bent over the sink, her dress lifted up to her waist. She hadn’t been lying. She wasn’t wearing any panties, and if she had been, she could’ve rung them into a bucket. Her toned legs glistened beneath the warm light of the bathroom.
Jake took her from behind, hands on her hips holding her dress up as he slid his cock inside her lubed pussy without any resistance.
She grinded against him rhythmically and he watched as her perfectly rounded ass bumped and pressed against him as her cunt swallowed his cock time and time again. He clutched her hips tighter and pulled her closer, so he could thrust harder and harder into her.
Brooke’s moans turned to screams as she bucked against him.
He slapped a hand across her mouth.
She sank her teeth into his fingers and he fucked her harder than he’d ever fucked anyone in his life. He looked in the mirror, met her wild eyes as he gripped her so tight, he was certain he’d leave bruises on her, and thrust harder still.
Her eyes locked on his and her mouth opened wide, her hands sliding up the sink as she convulsed on his cock, and he shot his load into her.
He thrust until every drop spilled from his cock, and then pulled out, watching as his cock left her pussy and cum drizzled from her.
“This can’t last,” she said, reaching between her legs and bringing her cum-laced fingers to her mouth. She sucked the cum from her fingers. “It’s just too fucking good.”
“But can’t it?” he looked her in the eyes, sweat still beading his forehead and cum still dripping from his dick. “What would you say if I offered you $2,000 to stay the night in my apartment?”
She whimpered, then nodded and said, “Can we go there now?”
“Of course.”
They were at his place 37 minutes later. Jake handed his keys to Brooke and told her to go up first, and to not look the doorman in the eye on her way to the elevator. A nod of acknowledgment would be enough.
Jake waited for 10 minutes that felt like an hour, then entered King’s Point and waved to Ted.
Jake was probably still traveling between floors when the do
orman picked up the phone and hit the number for Sasha.
“You were right,” he said. “He’s up there with her right now.”
XXX
Mark Pruit: Sex, Money & Teasing
Mark opened the bottle of 2006 Bienvenue-Bâtard-Montrachet, set it on the counter with two glasses beside it, then lit the candles on the bar before lighting the ones on the coffee table. He dropped the lighter in the drawer with a plop, then picked up the remote, turned on the music and hit pause a second into the song.
Now all he had to do was wait.
Mark’s friend, Ed, thought his rituals were ridiculous, and told him so when Mark explained how he would spend time setting the mood. Ed figured that since an escort was paid to open her legs and take everything you could give her, and smile like a bitch in heat the entire time, setting the mood was a waste of time you could spend thinking up new and creative things to do with the same old hole.
But Mark’s friend Ed was an idiot, at least when it came to women.
Ed may have been amazing at selling overpriced ad blocks to drunk execs, and using high-priced pussy to pave the way, but that was just part of what made him so goddamn clueless. The other was Ed’s fundamental misunderstanding of what Mark was expecting from each one of his encounters in the first place.
Hiring an escort wasn’t about sex.
Mark was a good looking guy in his early fifties, who made more than an excellent living as one of the partners at Miller and Hodge. If Mark wanted to have sex, he would have dialed any number of two dozen women, and had their panties past their ankles, and ass in the air by the hour’s end.
Mark had never once paid for sex because he couldn't get it otherwise. He paid for fantasy without baggage. Even killer sex with someone you knew came with history or an aftermath. Not so with an escort.
Whatever Mark was in the mood for, casual and meaningless, hard and pounding, elegant and sensual, or streetwalker back-alley nasty, he could pay to get exactly what he wanted, when he wanted, and never worry about the consequences.
Fifty Shades of Lexi Maxxwell Page 19