Jen's Big Secret

Brian placed one hand in his pocket and rubbed his chin with the other. "I haven't ever done this before, so pardon me if I seem nervous."

Jennifer chuckled, "What's that...never been with a woman before?"

His laughter broke the tension and then he stepped towards her, putting one hand around her waist and into the small of her back, pulling her close to him. He leaned in to kiss her. His other hand was placed on the other side of her waist and slid down softly to her hip as she returned his kiss. He opened his eyes and looked into hers, then kissed her quickly again. His hand moved up her bare spine to the adornment behind her neck and she could feel him finding and then fumbling with it as he tried to uncover the secret to its removal. She was about to assist him when she heard a soft click and then felt him easily unclasping the fabric that held the garment up around her neck.

As the tie came undone, the fabric fell naturally forward, revealing the strapless bra. Brian broke his kiss and began sucking softly below her ear and neck and his hands moved over her breasts. He paused slightly as he felt the fabric of the bra and pulled away to look at her. He smiled broadly. "I didn't expect to see anything here, do I just ...pull...like this?" He slid his fingers under her breast and pinched the fabric between them and his thumbs. The cups had some natural suction, and took a little tug to come free. He threw the garment onto the dresser and then held her large bosoms in his palms, rubbing his thumbs across her aerolas and nipples.

She placed her hands slightly above his wrists as he continued to adore and attend to her breasts. As she peered between his arms, she could see the tenting in his trousers that further testified to his desire. "Can we lie down?", he asked, letting go of her so that she could move towards the bed. She sat on the bed, first removing her shoes and then laid back, resting her head just below the pillow. He removed his shoes and tie and then climbed in next to her, placing his body half on to hers, with his face at her breast. His mouth moved to her left tit and took the nipple into his lips. He sucked on it softly and she could feel his cock pressing against her outer thigh. His left hand began teasing the nipple on her right breast again. She sighed softly, expressing her pleasure.

This continued for a few moments until Jen spoke. "Let me remove this so it doesn't get ripped." Brian rolled away from her and watched her get up to remove the rest of the gown and was ecstatic to see the fishnet thigh high stockings that weren't visible until now. He rapidly unbuttoned his shirt and pulled the belt from around the loops of his slacks. Jennifer now crawled onto the bed and straddled him below his groin, resting on the tops of his thighs and began unloosening and unzipping him. His cock strained against the athletic boxers beneath them. She rolled the waistline down and he raised up slightly to allow easier undressing. "You don't need any encouragement, but this is sort of standard." She slid off of his legs, and then to the side, resting her upper body on his right leg. She took his penis into her right hand and directed it to her open mouth. Then she slid the dark red head into her mouth and closed her lips tightly around it, pushed her head up and down slightly over the first inch or so shaft, teasing him to want more. His groans signified that the teasing was effective. She paused for effect, tossing her hair back away from her face, then resumed, going more deeply than before. He responded by flexing his hips upward, trying to drive his cock into her throat.

"Oh my gosh, that is so fucking good." He said in a rasping voice as he strained his head downward to look at her.

She was use to rougher treatment and didn't object, but only pulled away as she started to gag. She smiled, a little embarrassed and then got up from the bed and began to push the panties off of her hips. Brian continued watching, enjoying the presentation. She left the hosiery on then went to her purse and retrieved a condom. She put the package to her teeth and tore it open, discarding the wrapper in a nearby waste can then returning to the bed. She adeptly placed the condom over his shaft, rolling it down to the tuft of pubic hair at the bottom. Then she climbed back across his lap and looked at him. "Is girl on top, alright?"

Brian nodded enthusiastically, "I want to do it a couple of ways, if we can."

She started to lower herself onto him. "Anything but anal is alright with me."

She eased him slowly into her and then started grinding against his cock as she rested her buttocks against his thighs. Brian gulped hard, trying not to come quickly. He massaged her breasts again, pushing them together and tugging on the nipples carefully. She lowered her body over his and they kissed again as they fucked.

"You may be the most beautiful woman I have ever been with, Jennifer." Brian said after they paused from kissing. Jen said thank you, and was sincerely flattered even though she had heard many men say this to her in the middle of passionate sex. "Can we do the reverse cow girl now? I want to get a good look at that ass."

Without comment, she lifted and spun around, gripping his dick and holding it still as she lowered onto it again. She twerked up and down and felt his hands rest lightly on the globes of her butt. He let her motions move the skin against his hands and spanked her lightly once on each cheek. In this position, she touched herself, playing with her clit as she moved Brian in and out of her body in a steady rhythm. She panted softly as she began to feel it the climax edging on her now. The sounds of her pleasure filled Brian's ears and he strained not to release yet. "Yeah, Jen, oh yeah, that's it, get it, get it," he encouraged her on, now sorry that he couldn't see her gorgeous face in ecstasy.

She sucked her top lip into her mouth and closed her eyes, tuning him out and focusing on herself. God, how she loved cock! She pushed down hard and slid backward, causing her to edge even closer, then leaned forward, putting her hands between his knees and twerking rapidly. Her neck extended upward and then fell as the orgasm finally broke through and rode through her body over and over in the delightful waves that only happened occasionally on these trips. She was grateful for it and could now hear her client reassuring her that she had done a great thing.

He was still rigid however and wanted his own release. He waited patiently for her to roll off and turn to look at him over her shoulder. He nodded, sensing she wasn't ready to ask, but was willing to finish him. He sat up and got to his knees, then started shuffling towards her. Without any words spoken she moved to her hands and knees and crawled up closer to the headboard. Brian's hands went to her hips and he got himself directly behind her, moving his cock back to her honey hole. He slid into her so easily now that she was thoroughly wet and didn't hold back as he pounded her. His groin slapped against the back of her buttocks, getting louder the faster he pumped her. A few minutes later, he was filling the condom with cum, his fingers gripping into the firmness of her ass cheeks.

Jen's new client backed himself out of her loving hole slowly, and he winced as the last few drops of seed were pulled from him. After releasing himself from her pussy, he slapped his cock against the top of her butt a few times to express his satisfaction. "If there was a way to write an online review of your services, Jen, you would be five on a five scale."

The escort laughed as she rolled over in the bed and Brian laid down beside her, tucking his legs up slightly so that the condom and its contents wouldn't fall off. "I am glad you approve. And I hope it was everything you hoped for."

"Oh man, yes! You know you are welcome to stay here with me tonight, unless you have another...obligation?"

"No, no I don't." Jennifer rose up out of the bed and stood up on the floor. "But you get what you paid for, and nothing more. That's how it goes." She smiled so brightly as she said it, Brian couldn't help but agree. He got up and went to the bathroom to remove the condom and put on a robe. Jennifer was already in her panties and was putting the bra cups back into place. Brian came out in time to assist her with the dress, zipping up the back and putting the decorative clasp back on the joining parts at the neck. He kissed her on the shoulder softly as he finished.

She turned and put her arms around his neck, giving him a long passionate kiss good bye, then broke their embrace and walked past him to the door. "I hope you enjoy the rest of your stay in Sin City, Brian. It was a pleasure to have met you. Look for me again if you ever come back." She heard him reply with an enthusiastic affirmative as she opened the door to let herself out. She looked at her watch. They had gone a little over the allotted time, but that was common and she rarely spoke about it unless it getting close to an additional hour. As she walked down to the lobby she checked her phone for more messages. There was only one call from someone looking for a date that evening. She would return the call to apologize for her unavailability once she was back in her hotel room. After claiming her car from the valet, she returned to her own hotel and after a quick shower, she went to bed. There was still her client for tomorrow and she wanted to be rested.

The next day, Jen enjoyed the morning sun down by the pool after breakfast. Her phone rang while she was there. It was another potential customer. This gentleman wanted her for a late dinner date but she had to decline because of her flight plans. She apologized and asked him if he would like her to call him again in two weeks. He complained that he would be leaving early next week as well but thanked her for taking his call. She resumed checking her cam girl accounts; looking at email and for any offline tips. Soon it would be lunch and then she would take a short nap before getting ready for her date with Derrick.

Her time with Brian was enjoyable, even sweet. She liked encounters like that because it actually did seem like dating followed with a one night stand. But this afternoon would be different. She was going to get fucked and used hard by a man who had no reservations about treating her like a whore. The very thought of it made her pussy wet and brought an embarrassed smile to her face. It was the kind of reaction a young girl might experience when met with an unexpected compliment from a suitor.

After a light room service lunch of a turkey cranberry sandwich and salad, she took a bath and then rested for an hour. It wasn't quite the nap she envisioned, but the rest was good. The alarm on her phone went off and she got up and began to get ready.

Since she didn't need to wash her hair again, getting ready for her encounter would be easy. Still in the bathrobe, she returned to the bathroom and begin brushing out her hair, trying to get it as flat as she could without actually taking a flat iron to it. She then played around with putting her hair into a ponytail and letting it hang down as the night before. She opted for the single ponytail positioned high in the back of the head and then began to apply her makeup. Normally, Jen didn't use much makeup and just paid attention to her eyes. But today, she would put it on a little darker and thicker than usual. The occasion seemed appropriate for it.

She sprayed on her perfume and then returned to her room to find the costume Derrick wanted. She had a very short pencil skirt that would easily reveal her cheeks with just the slightest bend at the waist and then a white dress shirt. Instead of buttoning the shirt entirely, she left most of the buttons open at the top so that any casual movements she would make would reveal more of her breasts than a woman would normally show. She wasn't wearing a bra and decided to now remove her panties as well. There really wasn't much point in wearing them. Derrick would probably be stripping her very soon anyway.

The slutty secretary now contemplated hosiery and placed several pairs against her leg in comparison to each other. Ultimately she decided against them too but did put on a pair of five inch heels that had an open toe. She walked back and forth across the room a few times, putting a little more sway in her hips than usual and landing each step she made in front of the trailing foot. She giggled at herself and bit her thumb nervously. Even though she wasn't new to this at all, it still amazed her that she could be doing this at times.

At that moment there was a knock on the door. Jennifer partially opened up the door and hid her body behind it in case it was a bellboy or a hotel guest at the wrong room. It was Derrick arriving a few minutes early. "Hi Jen! So happy to see you again!" She opened the door and he kissed her on the cheek as he walked past her. In his right hand was a bouquet of flowers, still in the plastic wrap from the florist. In his other hand was a business attache case. "I hope you don't mind the flowers, I was just so excited about seeing you again."

Jennifer took the flowers after locking the door and propped them up inside of a glass she had kept from an earlier dinner. "These are really pretty, Derrick, thank you so much! What's in the briefcase?"

"Ah yes..." he said with enthusiasm as he laid the case on the dresser and opened the latches. Inside was a bottle of red wine, two plastic cups and a padded paddle. "Just a little lubricant before we get started, and my own contribution to the props for today's play. I must say I approve of your costume, dear."

She took a few steps around in a circle, modeling the outfit for him and giggling. She then noticed his own attire. "I am assuming that since you are in a suite, you are the my boss?"

He was now pouring the liquor into the cups and smiling. "That's right, and you are going to be visiting me for..." he paused to think about it. "What? Dress code violations? Poor performance? Inappropriate fraternization?"

Jennifer giggled again as she toasted to Derrick. "Do you think I would be allowed to dress like this at work?"

"Definitely not." He drank his glass and then said, "So let's get down to business."

He sat in the small desk chair at the corner desk and turned to face her. "Miss Jennifer, I was told you were in dress code violation today, and can see that is the case. Your skirt is too high and that shirt...totally unacceptable."

Jen could hardly keep a straight face. She giggled and tugged at the skirt, lifting it slightly, almost nervously. "I am sorry Mr. Derrick. Do I need to go home?"

"No, this has happened too many times with you. It is so distracting to the the men in marketing. They can never go up to the presentation board to give their product demos with hard-ons in their pants." Derrick now was smiling even though his delivery was dead panned.

"Oh no, I didn't know, sir. What is going to happen to me?"

"I am afraid, Miss Jennifer, that corporal punishment is what is mandated for this kind of infraction." He reached behind him and retrieved the paddle. "Please approach me and lay across my lap."

Jennifer laid across his lap, her breasts now perched against the outside of his leg and her legs draped over the outside of the other other leg. Derrick pulled up on her skirt and saw her exposed buttocks and exclaimed, "You aren't wearing any panties!" The prostitute cackled and Derrick continued playing the part. "This is definitely out of standards!" He raised the paddle and brought it down on her golden globes, not terribly hard, but enough that it made a sound. He smacked her twice on each cheek then put the paddle down and began to rub over the red splotches left on her ass.

"I hope you have learned your lesson. But tell me...why aren't you wearing any panties? Why do you display your breasts so prominently?" His hand was now moving down the crevice of her ass and pushing her legs apart slowly so that he could touch her barren pussy.

"I don't know why, boss." Her voice was tense with desire. His hands were stroking the lips of her womanhood and slowly prying them open to touch the moistened flesh inside.

"Is it because you are a slut, Jennifer? Do you crave the attention of the men? Do you want to feel their hands on you?" He was now rubbing against the sensitive nerve endings under her clitoral hood. His voice was soft and teasing.

"Yes, sir," she responded obediently, playing the part to the fullest. She closed her eyes and enjoyed the continued massaging of Derrick's fingers. He pushed a finger inside her wanting cooch and wiggled it teasingly.

"I see. And can you feel my erection growing against your tummy, Miss Jennifer?"

Jen shuffled a little bit against his lap, she could feel it. "Yes sir."

"And that's the kind of reaction you want, isn't it?"

"Yes, sir."

"You are a slut. Slide off of my lap and kneel on the floor in front of me," Derrick commanded.

She rose up and then shifted around in front of the chair. Derrick's legs were parted and his erection was plain to see inside his slacks. "Take off that ridiculous shirt. What kind of business do you think this is where you can just show off your ass like that?" He was sounding very mean, enjoying his dominance over her in this game. She complied unbuttoning the remaining buttons that held the garment closed. She let it fall from her shoulders and it caught in the bend of her elbows. She crossed her hands into her lap and looked up at him passively. Derrick was watching intently but was undressing himself as well. He loosened his belt and unbuttoned his trousers, then slid the zipper down. The tip of his dick was now visible through the fly of his boxers. "This what a slut wants, isn't it, Jennifer?" He pushed the fabric of his underpants down to the scrotum, exposing himself fully to her.

She nodded dutifully. "Oh sir! Yes, yes!", she said melodramatically and leaned forward to meet his throbbing meat. She opened her mouth and tilted to the side allowing her manager's shaft to enter past her lips fully. She began moving her head around, grazing the tip of his penis against all sides of her mouth. Derrick sat still with his hands resting on the arm rests.

"That's a good, uh...I mean bad girl. You are a..., " he paused as he shuddered, her mouth clenching more tightly as she pulled at his cock with her lips, "such a bad girl, Jennifer. Oh my god, so bad!"

Jennifer was giving his love stick a workout like it had never had before. She tugged, stretching the flesh as far as it would go and then slapped the soft side of his meat with her tongue repeatedly before forcing him down into her throat again.

Derrick let out a big sigh at last and then said, "My dear, that's very good work, but I am afraid you still need to be punished."

She leaned back and looked up at him as he started to stand. He offered his hand to help her arise and she asked, "More spanking?"

He pushed his lips out and frowned. "No, I am going to punish that pussy this time."

He pushed the chair aside and took her firmly by the arm and pushed her towards the desk. Jen fell forward against it, bending over the edge and exposing herself to him again. Derrick was quickly behind her with his saliva coated staff in hand, positioning himself to fuck her from behind. His other hand found her neck and gripped it firmly, pressing her breasts and face hard against the table.

His entry into her would have been rough if she hadn't been so wet and excited. He slid into her honey hole quickly and pushed himself balls deep. She squealed loudly, almost with laughter as he started sliding in and out of her slowly but always pushing himself hard against her. Her ass cheeks wiggled like jelly with each thrust and she rolled forward on her juicy jugs each time.