Now I don’t want to pressure you in any way and I’m sure you never would have considered doing anything like that, but quite frankly I’d much rather pay you than some hooker I’ve never met. You’re so incredibly lovely that I’ve wanted you since you opened your mouth at the front desk.
If you’d consider it, you’d have a safe place to spend the night and leave tomorrow with $500 extra in your purse. If you don’t want to I’ll certainly understand, but then I’ll definitely have to call that service now because just thinking about bedding you has got me horny beyond words.”
Jennifer stared across the table at Ben’s eyes. He looked more frightened and embarrassed than horny. “Would the form of your solution be any different if I admitted to being a virgin?”
It looked to Jennifer that he was actually giving her comment some serious thought. “It’s certainly surprising and I know that would ring the bell for a lot of guys, but quite frankly I don’t think my dick could get any harder than it was already from just looking at you.”
Jennifer took a deep breath and exhaled. “Mr. Roberts, you’ve got yourself a roommate!”
Ben signed the check and the two of them were riding up in the elevator when Jenn said, “I said you’d gotten yourself a roommate. As I think about it though I guess that’s not really true. I guess you just hired a whore, didn’t you?”
“I wouldn’t exactly put it that way.”
“Why ever not? I didn’t want to admit a mistake to my dad, so instead I’m fucking someone I’ve just met for money. That makes me a whore! It’s an interesting feeling. I’m not sure yet, but it might almost be exciting!
I take it you’ve hired professionals before?”
“A few times.”
She took his arm and squeezed it. “Well then you’ll have to teach me what to do. If I’m going to do this I want to be the very best whore you’ve ever bought!”
Ben took her in his arms in the elevator. He had his tongue in her mouth and his hand under her bra before they got to his room.
As soon as they got to the room Jennifer took off her jacket and started unbuttoning her shirt.
“Okay, if I’m supposed to be your teacher, a pro never does anything until she’d collected her money.” He took out his wallet and counted they cash into Jenn’s hand.
She whistled. “I guess this makes it official.” She continued removing her clothes as Ben sat on the end of the bed. When she pushed down her jeans he stood and put his arms around her, unclasping her bra as he kissed her. Jennifer’s hands began to unbutton Ben’s shirt. When they were both naked Ben sat back on the bed and with his hands on her shoulders pushed Jennifer to her knees. She didn’t need any instruction at this point, having sucked off a few boys in her high school. She grabbed his penis around its base and began licking her way along the shaft and around the head. When she was sure it was properly lubricated she lowered her head consuming more and more of the shaft until it slid down her throat. She smiled inwardly at his gasp. She thought, ‘Jennifer Reynolds is the name, deep throating’s my game!’ She knew she was good at that. Her head started bobbing up and down like a girl on a mission. Ben laced his fingers into her hair but made no attempt to run the show, as he’d never had a blowjob like this before. Five minutes later he could feel himself getting ready to shoot his load and he clenched his fists in the sheets rather than pulling her hair out.
Jennifer felt wave after wave of sperm shooting down her throat and for the first time in her life found herself completely turned on. She’d always thought of blowjobs as being just for the boy’s benefit but she was as wet as she’d ever been and was just a few strokes short of her own orgasm. She felt a moment’s sadness as his cock slipped out of her mouth but Ben grabbed her by the armpits and threw her on her back on the bed. He kissed his way from her lips to her erect nipples and on to her stomach. He positioned himself between her legs and slid his hands under her, tightly grasping her butt cheeks as he rubbed her wetness along the bridge of his nose. As soon as his tongue started rubbing her clit she exploded. Jenn unashamedly tried her level best to scalp Ben as her fists twisted as they were filled with clumps of his hair. Her scream was mixed with a prolonged groan as she squirted her juices over Ben’s face.
Ben pulled himself up level with Jenn and kissed her. “Do you want to shower?”
She kissed him back. “I will if you need the time to recuperate, but I’d just as soon give you the fuck you paid for. I’ve never felt like this before. It feels like my pussy’s on fire!”
Ben continued kissing her. “Sounds like a plan to me!” With his arms locked around her Ben rolled onto his back pulling Jennifer onto his chest. His fingers dug into her ass cheeks as he thrust into the previously unexplored territory of her vagina.
Jennifer quickly overcame the moment of pain and started performing a reasonable imitation of a bronco rider on Ben’s cock. He reached up and grabbed her very erect and very prominent nipples as she rotated her hips and continued to grind against him.
Ben moved her off him and pulled up on her hips so he could enter her doggie-style. As soon as he entered her the room’s phone began to ring but he ignored it. His balls slapping her clit was driving Jenn rapidly toward another orgasm as he began to cum. Jenn screamed again as they both charged across the finish line.
They lay in each other’s arms trying to catch their breaths. Ben just snorted out one word. “Wow!”
Jennifer smiled up at him, “So I did good?”
Ben kissed her forehead. “Best I’ve ever had!” He noticed the message light blinking on the hotel phone so he got out of the bed, dialed the access number and then redialed.
“Charlie? Ben Roberts, you left me a message to call you.” He listened to the response and replied, “I’m pretty well tied up for the rest of the evening but why don’t I find out and call you back?” He hung up the phone and dropped back on the bed next to Jennifer.
“Remember the guy who stopped by the table at dinner last night?”
Jenn kissed his shoulder. “Sure. You called him Charlie. I take it that was him you just called?”
Ben nodded. “Returned his call, actually. He wanted your number.”
“My number? I never saw him before.”
“He saw you at the dinner table and put two and two together since only an hour before that I turned him down when he invited me to dinner.” Jennifer had a puzzled look on her face as Ben continued, “I had told him I couldn’t make dinner because I was going to hire a sweet young thing and spend my evening fucking. He wants to hire you for tomorrow.
When does your friend get back in town?”
“Tuesday.”
Ben buried his face between her breasts. “So I provide shelter for you tonight, Charlie’ll take care of Saturday so you only will need to find two other clients to cover Sunday and Monday nights!”
“This guy Charlie, it’s okay for me to feel safe around him?”
“I don’t know anything about his sexual habits, but Ido think of him as being pretty much a stand-up guy.” He was nursing and tugging on her right nipple. “Do you want to book him?”
Ben’s assault on her breasts was producing the desired result. Jenn reached for Ben’s cock and as she lowered her head she smiled and said, “Sure, why not? After all, a whore’s got to make a living, doesn’t she?”
Ben’s laugh quickly turned into a groan. He reached for the phone and dialed. “Hey Charlie, you’re booked with Jennifer for tomorrow night. One thousand dollars and she’ll fuck you blind. I’d let you talk to her but her mouth is otherwise occupied right now…I don’t know, I’ll ask her.
Hey Jenn, one of Charlie’s buddies wants a wake up call from you at around nine a.m., interested?”
Jennifer never broke rhythm. “Tellm tobmook id.”
Ben groaned. “What’s the room number?” He hung up. “832 for your morning client and 716 that evening. I’ll write it down.” After writing down Jennifer’s schedule he began going down on her, thrusting his tongue into her while his thumb started massaging her clit. She began to moan as she thrust her hips at his face.
—-
Jennifer woke at around 7 AM, crawled under the covers and started sucking Ben’s cock to life.
“S’was goin’ on? It’s like dawn out!”
“I couldn’t decide whether I should let you sleep in or if you wanted one more quickie before I get cleaned up and head out for Room 832.”
Ben tousled her hair and kissed her lips. “I can’t believe how lucky I got last night. I have no idea if you’re going to keep this new career up, but talk about my being at the right place at the right time! You are, hands down, the best whore I’ve ever been with.
Let’s fuck!”
Jenn smiled, “My kinda man!”
—-
Jennifer rang the buzzer on the suite that was room 832. She had showered, washed and blown dried her hair, and thought she looked pretty good considering the busy night she had just gone through. Her bag was totally filled with jeans and casual wear, so she was wearing the same dress she had worn to dinner with fresh panties and no bra. While she was waiting at the door she vowed to spend some of her earnings on a new outfit for that evening. If she was going to live the part of a high-class whore, she’d better dress the part!
The door opened and Mr. 9 a.m. turned out to be in his mid twenties, and if Jenn’s judgment was at all accurate, was totally in love with himself. Jennifer had only had sex with one person in her life, but she immediately suspected that this guy would be a step down from the previous evening. Weird. Two days ago she would have suspected that when it came to sex, 20-something would always trump 50-something, but now she wasn’t so sure.
“Well, come in. Charlie said you were hot and I’m glad the old bastard’s problems don’t extend to his eyes.” He turned around and headed for the bed. “You’re supposed to be my wake-up treat so hurry up and get naked before I wake up.”
Jennifer just stood by the door. “I think we need to get the money thing ironed out first, don’t you?”
“Get in bed, baby. I’m sure not going anywhere!”
“I know, baby, it’s just that I don’t want any distractions while we’re having a really good time.”
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