1 comments/ 6016 views/ 1 favorites Jen's Big Secret By: MrYowman Jennifer had been a cam model for a few years now and had been very successful at it. She had a large fan base, a few regular tippers and members who spent time with her in private. And recently she had started earning some money through her phone with an application called "ringhop." But unlike some of the other women in her profession, she really hadn't branched out in social media or 'at home' video productions and candid professional photography. Jen wasn't really gifted at these new kinds of technologies and didn't enjoy the hassle of expanding her presence, but there was a more intimate reason that she didn't move into these areas. Jen had worked very hard for a long time to sculpt herself into the body she now so proudly displayed. But those kinds of ventures, while they may be profitable for some, weren't satisfying for her personally. The real joy of camming was that she actually got to enjoy her body with others. It amazed her sometimes to think that she could actually get paid for the admiration of others and pleasuring herself with them. And why not? She was nearly sixty and she could still pass for a woman in her thirties, but the truth was that nothing ever lasted forever. It was time for her to enjoy what God and with hard effort had rewarded her. So, after a few years of camming and becoming comfortable with exhibiting herself, she was beginning to think about what came logically to her as the next step. The idea of working hard and being paid and pleasured for it had led her into the world of cam girls, why not venture into escorting? Jen was ready and excited for this experience, but she wasn't as willing to share the idea with her friends and family as she was when she told them that she was going to be a online model. The biggest concern of her friends at that time wasn't her reputation, but just that she wasn't very well versed in dealing with computers and the internet. But she wasn't as sure that this new enterprise would be as warmly received. And she obviously couldn't share her new business with her My Free Cams community. There were international rules at work here and although she had never experienced a problem before, this willingness to actually meet people could draw a little more attention than she desired. No, it was better to venture into this work as an unknown novice rather than try to integrate that her current business clientele into a new one. Of course the decision wasn't that easy of one to make, but making the decision making was much easier than the next steps necessary to get the business started. California had very restrictive laws about what she was considering, and she wasn't interested in that kind of risk. But neighboring Nevada was a much friendlier to that kind of enterprise. So after making a few road trips to visit a few brothels and calling a few 'back page' girls for advice, she decided that being 'on call' would be more to her liking. This would allow her to work when she wanted to and not interfere with her Monday through Friday routines of yoga, camming, and real estate studies. Then after purchasing a new simplistic cell phone and signing up for an affordable monthly plan, she set to work. When she traveled to Nevada to look into this new career, she had acquired a few tabloids and periodicals that catered to the escort business. The few she picked were based on the recommendations of the other women who had used them and Jen set up an ad to run for a weekend rate. The ad, carefully worded to suggest companionship only, would appear on Friday and Saturday of the weekend she had designated, and she would be available for Saturday and Sunday. The advertisement contained either her new cell number or the number of the place she was staying with the extension number. She would leave for Nevada on the Friday before or Saturday morning, staying at a moderately priced, higher rated hotel or motel close to shopping and entertainment in case she didn't have a successful weekend. By far, the best part of this arrangement had been the shopping that preceded the travel. She picked a variety of clothes since she was unsure of what the environment would be like on her dates. And although she felt a little awkward, she anticipated that someone might request a costume or two. It didn't take long to decide on one in particular. One of her MyFreeCam fans had once suggested to her that she should get a school girl costume when she had placed her hair into some loosely fashioned pigtails. It was easy costume to create and a favorite fantasy for a lot of men, so she always carried the short plaid skirt and a tight button down shirt with her on the trips. The other costumes were fashioned from clothes she already had; a secretary or boss (for those who liked to be dominated), and a teacher. She had purchased a long dress in case someone decided that there would be a social outing, and several styles of lingerie. But most of the attire was comprised of what she had and could best be described as business casual. It wasn't necessary to draw attention to herself and she believed that most men would prefer not to have too much attention drawn to them either. On this particular outing, Jen arrived on Friday at a hotel where she had worked before. The bell hop and doorman knew her by now and were very friendly and happy to see her return. The recognition made her nervous at first, but after a few visits, she actually began to speak to them and get to know them a little better. This was Nevada after all, and she had little to be concerned about. She proceeded up to her room after a brief conversation with the two employees. After settling into her room and unpacking, Jen opened a small bottle of wine and poured herself a drink into the glass tumbler provided next to the ice bucket. She then dialed the message service of the hotel and listened for her messages. There were a few hang-ups (there always were), and two messages. One was a man who wanted to discuss her availability, and the other wanted her to return his call so that arrangements could be made. She jotted down the two numbers and finished her wine before dialing the first second number. Since this gentleman sounded like a sure thing, it would be best to contact him first and try to schedule in the first caller later if possible. The phone rang a few times and then the familiar voice answered. "Hello, this is Brian." "Hello, this is Jennifer. I am returning your call." It was always best to let the man confirm his intentions, just in case he was not in a position to discuss the proposition at the time. "Jennifer! Yes, thank you for calling me back. I have been looking forward to meeting you." His voice sounded warm and excited. "I am anxious to meet you too. Have you given any thought about our day or evening together? Or do you have any questions that I can answer?" "I was think about the two hours you advertised. We could get dinner and get to know each other a bit before returning to my hotel, if that's alright?" "That's sounds nice. Should I meet you at the restaurant? Your time starts when we meet." Not only did this arrangement settle any disagreements about time management, it also allowed Jen to maintain access to her rental car if things didn't work out between her and the gentleman caller. This was less of a concern for men who paid for overnight or weekend sessions. "There is a very nice restaurant at the Treasure Island hotel where I am staying, called Phil's Italian Steak House. I thought that would be most convenient. Are you free tomorrow evening?" "I am, I could probably be there by 6:30 or 7:00." "Seven is good for me too," Brian replied. "I think I will recognize you from your pictures, but how will you be dressed?" "I am not sure yet. If you would send me a picture of yourself to this number, I will send you a picture of me in the dress before I leave." She recited the digits to her cell phone number. "How will you be paying?" "I will be paying with cash, if that's all right?" Although cash sometimes made her nervous, it had advantages. She didn't have to report it for taxes and it meant that she didn't have to mess around with the credit card swipe attachment on her iPhone. That device could sometimes be unpredictable in performance. "Yes, please place it in an envelope under my plate before I arrive to the table." That was one of the downsides of cash, it was a little less discrete than other methods. But this arrangement would not likely catch the attention of any of the diners. "I understand, is there anything else I should know?" "Not unless you have any questions you want to ask now before we meet." "No, I suppose not. I will save all the rest of my casual talk for dinner tonight. I will send my picture soon and look forward to seeing you shortly." They hung up the phone together and then Jen returned the other caller's message. to the other voicemail. She dialed the digits and waited for him to answer. "Jen? How long have you been in town?" It was Derrick, a man with whom she had been with a few other times. She liked Derrick because their relationship was now a comfortable one and he was versatile. He enjoyed role play and was also varied in his approaches to lovemaking. Sometimes it was soft and romantic, and other times, when agreed upon, it simulated rape. "Hi Derrick, I just arrived at the hotel an hour ago. How have you been?" "I have been scanning the BackPage ads for weeks, looking for you to return. I would like to schedule another appointment with you if you aren't booked up already. Can you squeeze me in somewhere?" Sunday was completely open for now. Jen was looking at a profitable weekend. "Yes, we can work out something for Sunday before my flight leaves at 10:15 that night. What did you have in mind? "Did you bring your secretary outfit this weekend? I really want to spank a naughty girl. I figure we can get an hour in sometime in the afternoon. If you are at your usual place, maybe I can be there around three, what do you think?" Jen was beaming, nearly blushing as she pictured herself with him, placed over his knee with his hand sliding her skirt onto her back and revealing...what? A thong or maybe nothing. "That would be fine. I am in room 304." "That's great, Jen. I am dying to see you again." "Me too, Derrick. I will see you on Sunday, don't be late!" She hung up her phone and paused for a moment, collecting her thoughts and plans for the evening. She decided to go out for a small dinner before returning back to the hotel for bed. In the morning, she would get up and work out in the hotel gym, have room service bring her breakfast while she showered and then plan on shopping or sightseeing until her dinner date with Brian. A few minutes later, she received a text message from Brian that included his picture. He appeared to be in his thirties to forties, had all of his hair and wasn't overweight. She didn't always accept her clients if they were too unsightly, but most were at least normal in looks and fitness. She would reply to him tomorrow after she was dressed. Saturday afternoon, Jen left the hotel for a light lunch and then went to a salon for a manicure and pedicure. It was a good way to relax in preparation for the evening. She paid and tipped the ladies of the shop and then went back to the hotel to get ready for the evening. Jennifer had two options in mind for this evening's dinner. There was a long, black gown that had straps that went behind her neck with a decorative clasp. It didn't reveal much of her breasts, but was very open from the back of her neck all the way down to just above her buttocks. The bottom of the dress flowed out just slightly at the hips and had a mesh overlay. It was the kind of dress a couple might wear to an anniversary dinner. The other dress is more along the lines of a cocktail dress. It was bright blue, short at the hem and didn't have a collar or sleeves. Her shoulders and neckline would be bare. She would put both on and send Brian a picture in each and let him choose what she would wear. After sending the pictures, she began putting on her makeup and styling her hair again. About thirty minutes later, her phone chimed indicating that she had a message. It was Brian's response. "Wow! Tough choice. Let's go with the black one. See you soon." After finishing with her hair and makeup, Jen undressed from the stylish sweatpants and top she was wearing and removed her undergarments. She sorted through the lingerie still in her suitcase and picked out a nude, seamless, front closing, strapless, demi bra and red, no show cheeky panties. After getting dressed again and buckling the straps on her shoes, she checked herself thoroughly in the mirror, applied her perfume and then left the room to go down to the valet desk to pick up her rental car. It was a short drive to the Treasure Island hotel. It was considerable larger than where she was staying and it made her feel more excited about the date. The hotel was actually an entertainment complex hosting restaurants, entertainment facilities and betting lounge for sports and racing. The valet took her keys and directed her through the door to the front desk. Once there, she asked the young woman for directions to Phil's Steakhouse. The friendly blonde pushed a small diagram across the counter and began to draw on the map. "Go back down towards the entrance and turn left at the Lobby Store, then proceed down to the Coffee Bar and turn left. Phil's Italian Steakhouse is here at this bend on the left. If you reach the elevators, you have passed it." Jennifer took the map and thanked the girl then proceeded down the corridors to the hotel. Upon arriving she was greeted by another pretty blonde who asked how many were in her party. "I am joining Brian tonight, I believe he may be here already." Jen was deliberately late so that her date could be seated prior to her arrival. She hoped that a last name wouldn't be necessary. The woman peered over her seating chart and guest list. "Yes, he is here. Maurice will seat you." Maurice was now standing behind the woman and extended his arm in the direction they would walk. "How are you this evening? Is this your first time here?" By the small talk was finished they were standing at the table and Brian stood up respectfully as Maurice pulled her chair out for her to sit. "Enjoy your dinner." Brian offered his hand as she began to sit down and she took it lightly, smiling and saying, "Nice to finally meet you." He was wearing a dark business suite and yellow and blue striped tie with a lightly tinted blue shirt. The suite jacket and trousers fit him well, although she doubted it was custom tailored. He appeared very pleased to meet her as well. "You look absolutely stunning, Jennifer. Thank you for agreeing to meet me this evening." He indicated with his open hand to the envelope under the dinner plate and she slid it out and placed it into her small black sequined clutch. She would investigate the contents in the bathroom later to verify that the five hundred dollars was there. "Absolutely. This is a very nice place. Did you say you were staying here too?" She knew the answer of course, but also knew the art of conversation. "Yes, I have to come to Vegas every few years for training with our licensing partner and we get a pretty good rate here." "So you have been here before?" "Yes, but...this is my first time with a date." Jennifer smirked at his delicate wording. "Well, I hope we have an enjoyable evening then. I would hate for your first experience to be a disappointment." Brian scoffed in a friendly manner, "It certainly is starting off well enough. How long have you lived here?" In very general terms, she described her infrequent trips to Las Vegas and indicated where she was from. Brian was gracious enough to respect her privacy and didn't push for more specific details. The waiter appeared and introduced himself and the evening's specials and house favorites. Jen opted for the crispy roast citrus chicken and Brian inquired about the Australian lobster tail, but seemed surprised at the price, so chose the smoked duck bucatin with pasta noodles instead. After the waiter promised to bring them their water, Jen excused herself to the bathroom to verify that the contents of the envelope were intact and complete. A few minutes later she returned and Brian again rose to her presence. "Everything come out alright?" He joked softly, unsure if she would appreciate the bathroom humor. She chuckled and nodded, giving a polite thank you. They resumed their casual conversation, getting to know each other better, until the meal came in a timely manner. For the most part, they ate in quiet, remarking sometimes about the taste of the food and restaurant itself. Brian then stated, "Unfortunately, they don't have a dessert menu here, but the Coffee Shop has great cakes and pies, if you are interested." Jen declined but suggested that they have a dessert wine instead. He agreed as long as it was white, and when the waiter returned, the three of them conversed about the selection and then settled on a Riesling. As they enjoyed the chilled liquor, Brian poured his eyes over Jennifer as he drank in the wine and her beauty. Jen was very accustomed to being the dessert of the evening on nights like this and looked away slightly so that he could enjoy her charms unhindered. She did however look at her watch, and nearly an hour had passed. "Thank you very much for dinner, Brian." "It was a real pleasure for me too, Jennifer." The waiter brought the bill and he signed for it, then closed the copy into the presentation book and stood up, moving to her chair and assisting her out of it. He offered her his arm, but she clasped his hand instead, choosing to appear less formal. They were after all, about to end any formalities in this relationship. "My room is on the fifth floor." He tried to sound casual, but she could sense a little uncertainty in his voice. It wasn't unusual, but she preferred men who were confident and commanding. For sure, this was his first time with an prostitute. She replied reassuringly, patting his arm and staring directly into his eyes, "I can't wait to see it." They boarded the elevator with another couple and were taken quickly up to the fifth floor. When they exited the elevator, they turned left and went down a long hallway and around a corner. His room was just a few doors down from there. He squeezed her hand before letting go to reach into his jacket pocket for the room key. The magnetic lock on the door released and he held the door open for her after flipping on the wall switch located on the wall. The room was called a petite suite. It was set up as small studio apartment with a king size bed. It had a very large bathroom with a full size Jacuzzi tub and separate shower. The TV was 42 inches wide mounted to the wall across from the bed and there was a small lounge with a couch and chair that faced the full wall window with a view to the mountain horizon in the distance. "This is really nice! It's maybe the nicest hotel I have been in here in Vegas or anywhere for that matter." Jen was genuinely impressed. Brian smiled proudly as he watched her take in the view of the mountain range, now barely visible as the sun set behind it. He was removing his jacket and hanging it up in the closet. She noticed that his luggage wasn't visible which meant he was probably using the furnishings to store his clothing. "I have to say the same thing. You can spend a lot of money in this town, but hotels seem very inexpensive for the quality that you get." He stood looking at her until she turned around and set her purse down on the business desk near the lounge area. She took a deep breath and smiled, looking back at him. 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. Jen's Big Secret "I am not mad at you Miss Jennifer, but for now on, when you feel this way, you just need to come down to my office, understood?" "Ooof! Yes, sir!" It felt like he was trying to push his whole body into her. He suddenly picked up speed and pumped her some more, then extracted himself out, feverishly jerking on himself and spraying her backside, skirt and butt with his cream. He roared loudly as he did. Derrick was one of the few men allowed to go bareback with her under the condition that he pull out. Jennifer stayed in position until she heard him step back, then rose up slowly. The more liquid semen rolled off of her back and around her sides as she moved. Derrick now was crashed into the chair again. His cock was bright red and going flaccid as he set there and his chest heaved up and down. He was still oozing juice. His face was nearly as red as his member was and Jen wondered if he was on the verge of having a heart attack. "Is everything alright?," She asked softly. He glanced up at her and nodded, a smile forming on his face. "Perfect, just like always, Jennifer." He reached up and put his hand on her waist, pulling her a little closer. He looked at the clock on the night stand. Time was up. "When will you be back, hon?" Jen smiled. "I don't know for sure. I am trying to come back at least once a month. I will be right back, I need to clean up." Trotting towards the bathroom, she grabbed a discarded towel and began to clean up the cum from her legs and back. She would shower soon after Derrick left. He was soon standing in the doorway, pants on and buttoning his shirt. "I really am glad to have met you, Jen. Listen, just count on me as a customer each time you are in town, okay? Just shoot me a text when you know you are coming so I can be sure I can clear my schedule." She held the towel up over her body. Even though they were very intimate with each other, it still felt a little awkward having him watch her clean up. "Sure, Derrick. I can do that. And thank you. It goes both ways, you know. I am glad to have met you too." He stepped into the bathroom, now completely dressed and leaned his body toward her with his lips puckered. She returned a soft kiss and then he held out his credit card. "Oh shit! I almost forgot!" She laughed at herself, but was glad that he had remembered. A few tries on the swiper and the transaction was complete. Derrick had even included a one hundred dollar tip! "You are the best Jen." Derrick said as he let himself out the door. "See you soon." The tawdry secretary locked the door behind him and returned to the bathroom to start the shower. She would be leaving to go home soon. She was nine hundred dollars richer. It wasn't a great weekend financially, but she had her sexual desires filled, and that was profit enough. The end.