Her Dirty Secrets Pt. 02 Ch. 03

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Widowed Single Mom Provides
3.9k words
4.65
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Part 2 of the 4 part series

Updated 06/08/2023
Created 07/23/2013
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She advertised as an escort in multiple classified ads online and her phone rang before the alarm was due to go off. Instantly it was as if she was never asleep. She sprang out of bed with cell in hand, answered and the caller was addressed in what seemed one single motion from being dead asleep. Naked she walked into the master closet with this regular client on the other end.

She didn't like him much but he had what seemed to be an endless supply of $100 reasons to answer the phone. It wasn't that he was offensive to look at he was actually not bad looking. It was his constant drug habit that disgusted her. He was forever gritting his teeth and offering her the stuff and pleading with her to join him and she was not interested. She didn't mind having a drink with him as long as she was in control of the libations and he couldn't take advantage of her. She had to laugh to herself. Who was taking advantage of whom? That was a good question she thought.

He drank like a fish when he was high and she spent a good amount of money on alcohol entertaining him but the spending meter tilted largely towards him. He called on a weekly basis at all times of the day or night from a different hotel room, wasted on his currently favorite drug and always when he was out of alcohol. She would stop and pick up whatever he wanted from the liquor store on the way. If she didn't know better she would think he was sober because he acted so completely normal except for the excessive drinking which seemed to have no effect on him.

She wondered what he would want from her today. He was wildly unpredictable which scared her and more than a little excited her at times. More than any other client she let him have his way with her by playing his little games and being the complete slut her soccer mom friends didn't know existed. She carried in her car trunk a medium sized bag full of what she referred to as her "props". It was filled with the things she used to entertain regular clients like this.

Regulars were more demanding than the occasional client because their ongoing visits required a slow but steady escalation of kink to maintain their interest. Let's face it, who is willing to pay over and over for the same old thing, right? She pulled into the hotel parking lot and called him from the car.

He answered and asked her what she was wearing. She indicated tan short-shorts, a semi-sheer grey tank top and sandals. He snorted "Not hot enough, you need to change and meet me in the bar downstairs".

Great, she thought he is in one of his demanding moods which meant she would have to try and calm him down. She grabbed her bag, slipped into the hotel and then the restroom on the first floor. She knew better than to look towards the registration desk when she passed.

She had been here many times before. She also knew who was working this shift and that she would be taking care of him financially afterwards. It was a small price to pay but she regularly tipped hotel staff including the cleaning ladies. They weren't stupid and it was just smart business to make sure they looked the other way. She would occasionally see one of these hotel employees or one of her clients in public at the grocery store, one of her kid's ballgames or a school function. They would smile at one another and keep moving. That was the unwritten rule. You watch out for my back and I will watch out for yours. No need to create a scene in front of others and promote unnecessary questions right?

In the restroom, she unzipped the bag and extracted a pair of grey heels with a miniskirt to replace the shorts. The semi-sheer grey tank top worked perfectly with the too-short jean skirt and heels. She left her push-up bra in place but removed her matching panties. Once they were secured with the shorts and sandals in the bag she exited and headed directly to the front desk. She told the desk-clerk she knew all too well, "My husband's flight has been delayed and he will be checking in later, would you mind checking this bag for me while I wait for him in the bar?" He grinned and said, "Of course, please hang onto this ticket and I will see you later".

She strutted to the bar and swept the room with her eyes. He wasn't there and she was not surprised. This would somehow be part of his game today. There were three men sitting at the bar and it was as if someone famous had entered. Their conversation sputtered to a sudden and complete halt and they tried to act like they didn't notice her. She smiled at them which only made it worse. They were at one end of the bar so she sat in the middle by herself. This would be interesting to see what Cokehead would do next. All of her regulars (unbeknownst to them) had nicknames and his was more than appropriate.

The bartender brought her a gin and tonic with a slice of lime at her request and she thanked him. Then her client entered and walked right past without a glance and sat himself one seat away from the group of men. They exchanged pleasantries and he commented something about watching the game currently on the flat screen over the bar in his room prior to coming in. She wondered what he was up to because he surely had something in mind.

She was almost to the bottom of her drink and just beginning to get annoyed while the four men chatted amiably about sports. Suddenly they stopped talking and out of the corner of her eye she saw all four heads swing her direction in unison. "Here we go", she thought. "What is he up to?" Two of the men excused themselves and left the bar leaving one of them with him. Cokehead got up and walking towards her sat down in the seat next to her. Still annoyed she asked him what he had in mind for this afternoon. He laughed and said "that nice young man down there is hot for you but he thinks you are out of our league. I bet him $ 100 I could get you to buy me a drink" and he laughed. She had to admit she was amused at his little game, ordered another gin and tonic and a double scotch neat for him. The poor bastard at the end of the bar was watching and shook his head.

Cokehead waved him over and asked him to join them. He pulled out the barstool on the other side of her and introduced himself as Dave. He was about six feet tall, slender and well-built but had freckles all over his face. He made her think of Opie from that old television show and she knew instantly the nickname would stick. There she sat between Opie and Cokehead, wondering where this was going but she already knew. That rat bastard had planned it all along. Within 30 minutes they were all three headed to the room upstairs.

Upon entering the room Opie was instructed to have a seat on the overstuffed armchair in the corner of the suite. She excused herself to the restroom to freshen up. When she returned she was surprised to see Opie was completely naked and tied to the chair with duct tape on his wrists, mouth and legs sporting a massive circumcised erection. It was so large she was shocked. Damn if it didn't look to be the same size as her black suction cup member from this afternoon, but as pale and pink as a baby's bottom.

Cokehead laughed at her reaction, "who would have thought he was packing that?" he grinned. "I told him if he was a good boy I would let him give you that $100 bill instead of paying me for the bet. It's only fair since I cheated him..." followed by another grin. He continued, "So - here is what I want to see..." She knew she was going to be in for a long afternoon and was thankful she had called her sister on the way. The kids were going to spend the weekend with her and she had agreed to pick them up at school.

Opie was nodding his head vigorously once the questions started. Cokehead was running the show. "She's a hot piece of ass isn't she? Would you like to see her cleavage a little better?" He said. "Go on sunshine -- take that top off... Wait a minute, I need another drink first." After the drink was made he instructed her again to take her top off. Playing his little game she turned around with her back to the boy facing him. She grabbed the bottom on each side and reached up with both hands and slowly lifted her top. When she was done she tossed it on the bed and walked slowly around the room. She softly touched Opie's knee when she walked by and his cock jumped. His eyes followed her every move looking her up and down. He was enjoying every minute.

Cokehead was gritting his teeth and grinning at the same time. He was enjoying himself very much. "Take your panties off and leave the skirt on for me." He said. "No" was the reply. He almost dropped his drink, "WHAT?' he said. "I said no, because I'm not wearing any, see?" She slowly lifted her tight little jean skirt. It didn't have to move far to reveal a little red landing strip above the slightly swollen lips below. "I don't have any on. If you boys were smart enough I would have showed you in the bar but you didn't think of it." She laughed.

"Sit on the bed and spread your legs right here" he said, indicating the corner of the bed right in front of Opie. She thought "he is going to give this kid a heart attack by the time this is over but ok..." Once she was seated and instructed to remove her bra she reached behind to unsnap the clasp. Now she had her hands crossed holding the cups of her bra in place and she grinned. She felt her pussy swell. It always did when she was being a tease. Poor Opie didn't stand a chance. His cock was twitching and jumping at only being a foot away from her. Helpless he pleaded with his eyes to see her tits.

She laughed and showed him a stiff nipple and covered it up. Cokehead roared at the poor boy's reaction. Opie had thrown his head back and tried to thrust his hips forward to touch her. Of course it didn't work but now there was the slightest hint at pre-cum on his cock. She leaned forward with the bra still in place and gave it one little lick to clean it off.

She didn't wait for the next instruction and dropped her bra. She cupped her breasts lifting each one to her mouth and flicked the nipple with the curl of her tongue. Then she leaned forward and placed a hand on each of his spread knees and slowly dragged her hanging breasts back and forth across his cock. Opie was almost out of control and she backed away quickly. She was enjoying this too much now and wanted it to last.

Cokehead was in the other corner and had whisked himself out of his pants and into view pulling rapidly on it. "Damn" he said, "You are so fucking sexy. I want some of that". She winked at Opie and walked across the room. She spread her legs and bent forward at the waist giving Opie a new vista to admire. She lowered her hair softly into his lap and curled her tongue around him. Then she held the tip with two fingers and dropped to the base of his cock and licked slowly up the full length of it. She took the head in her mouth and swirled her tongue around to coat it with saliva, then slowly worked her hand up and down in a twisting motion. She could hear him sucking air through his gritted teeth and the ice cubes rattle in his glass.

She stood up quickly with a grin on her face for a change. "I'm sorry did you want a drink instead?" She laughed. She knew he didn't want her to stop but she was in control, at least temporarily and wanted to take advantage of it. She didn't have it for long.

"We are out of ice smart-ass! -- Go get us some. Wait -- I'll take you. Put your top on." He said. She reached for her bra and he said "no -- just the top". "But you can see through it" she replied. "That's right, you can see through it. Put it on." She dropped the bra and pulled the sheer grey top over her head. There was no mistaking she was practically naked. Her full breasts were in clear view and her nipples jutted out like they wanted through the soft cloth. She felt naked, no, she felt worse than naked, like she was going to be put on public display. In the room it was fine but she was terrified to go out in the hall like this. She also knew he would not take "no" for an answer, and that he would compensate her well for pushing her own boundaries for him. Then he produced his own prop and she gasped.

He had pulled it out of a bag next to his chair. She hadn't noticed it before and wished she had. It was a butt plug like the one she had at home. This one was a shiny metal that looked almost like chrome. It was about the same size as hers but the ball was a little larger. Instead of a T-shaped stand or handle it had a purple gemstone about the size of a golf ball on the other end. He motioned her to come closer and when she did he put the bulb end in her mouth. "Turn around and bend over" He said. She turned towards Opie and looked at him with this giant thing in her mouth. He had his tongue out of his mouth reaching towards her with sheer lust.

He pulled her apart with both hands and licked her ass and pussy until she was soaked. Then he asked for the plug and she gave it to him. She rubbed her clit furiously while he pushed it in place. It was so much bigger than what she was used to but it finally found its way. She had never felt so full there before and it was uncomfortable. She made herself focus on relaxing and it helped a little.

She turned around and he had a leash in one hand and a collar in the other. After they were both in place he made her walk around the room to display this new look to them. He held one end of the leash and walked her like a puppy. She was now a puppy with 4 inch grey heels and a sheer top, her nipples jutting out over the very short little mini-skirt with long smooth creamy bare legs and her auburn hair hanging in her face. She was trembling at what might happen next.

"Hey Dave, I am going to take our little bitch here for a walk would you like to come along?" He said... "Oh you can't because you're all tied up. No worries I will leave the door wide open so you can listen to her heels all the way down the hall and back." He was really enjoying himself now, she thought. He said, "Come on sunshine lets go see if we can find that ice machine" and out in the hallway he pulled her by her leash.

"Now listen to me", he said softly. "You are not to address anyone we meet. You are not to talk at all. You are my possession right now. I expect my possessions to stand up straight, walk pretty and look straight ahead." She nodded OK not knowing what else to do. She was still trembling and tried again to calm herself.

He left the door wide open and Opie was clearly appalled at his plight. He was in direct view of anyone that walked by, duct-taped naked to an armchair with a very large cock sticking straight up in the air. It bobbed wildly every time he moved drawing even more attention to his member. She winked at him again to try and help him calm down and he got it... He had no choice but to wait for their return.

Her handler walked patiently by her side as she walked slowly down the hall looking straight ahead. She prayed silently to make it there and back with no interruptions. She strutted just a little because he had told her to and it helped her regain some confidence. Then she panicked. The elevator was between them and the ice machine. "He wouldn't!" She thought to herself. To her dismay he paused at the door and looked at her. She looked straight ahead as she had been taught. He laughed and said "good girl - If you broke character I was going to make it a lot more difficult for you but you are a good girl".

They reached the ice machine and he filled the bucket and then handed it to her. "Hold this against your chest" he said. She did as she was told and gasped when it touched her. The sheer top was no protection at all and her nipples landed directly on each side of the cold glass. He turned her around and they headed back to the room. Then the elevator chimed its arrival. She panicked again and felt like she was going to collapse but somehow she held it together.

Out of the elevator first came the maid's cart and then the maid herself. "Oh, I am so glad I know her" she thought. She had tipped this girl many times in the past. The young Hispanic was clearly startled at this sight but recovered quickly when she recognized the woman on the leash. She said "hello", turned and practically ran down the hallway towards the other end. As she passed the open door she glanced inside, tripped and almost went down. Finally reaching her destination she looked back towards the couple for another look and let herself in the room.

They returned with no further incident and the leash, collar and top were removed. She made him another drink and sat down quietly on the bed. He was clearly amused and enjoyed his new drink while he thought of his next moves. Cokehead turned to Dave and asked him 'Are you ok?". He nodded vigorously in response. He asked him "have you ever watched a man and a woman have sex in person?" Opie shook his head and his cock strained upwards again.

"Take off your skirt and leave the heels on" he said "and lay down on your stomach with your legs spread". After she had complied he grabbed one of the pillows off the bed. She raised her hips and ass while he stuffed it beneath her and between her legs. The gemstone at her anus sparkled in the fading afternoon light streaming through the sheers from behind Opie.

The pillow hit just right on her most private spot and she started moving instinctively. With the plug in her ass and the pillow between her legs, her ass and hips made slow wide circles and their speed began to increase. She didn't want this - "not now" she thought. She could feel the black man's presence and she willed him away. She would not let him come here, not like this, not in front of these men.

Cokehead removed his clothes, and stood beside her head next to the bed. She moved towards him and engulfed him. She had to shift a bit from the pillow but that was fine with her because she did not want to lose control. While she serviced him she was acutely aware of Opie watching the show from behind her. He was starting to become more vocal and she knew he wanted released from his binds and more. He was forced to watch as this man forced her over onto her back and mounted her. He was clearly very turned on and didn't last long. It was only then she remembered the condoms in her purse. "DAMN" she thought. "DAMNIT why did I forget - I never do that!"

His cum was now leaking out onto her thighs. Cokehead sprang off the bed and grabbed the other man's slacks and pulled $100 bill from the wallet, rolled it tightly and walked over to Opie. He removed the duct tape from his mouth with one swift pull. "Dave, open your mouth, here's the money you owe me." He said. Opie didn't get it but he did what he was told. Then Cokehead whispered his directions in her ear and she grinned.

She rolled off the bed and approached Opie, dropped to her knees and took him into her mouth. Just like her toy at home she could barely get it in but she managed, using two hands to work him while she sucked and licked the head. Then she turned around.

She backed onto him with great anticipation of being filled completely. His cock barely fit but she worked it in her slick pussy and leaned back on him like he was her chair. He was clearly very excited and tried to move with her but was unable. She did it for him and began to grind and work herself on top of him. Then she hopped off and faced him, stepping up onto the chair, with one foot on each side of his hips and dropped back down on him again. She whispered in his ear as she bounced up and down "I would have fucked you if you asked me in the bar". With that he could not hang on any longer and lost his load in her already soaked pussy. She stood up on the chair, turned around and planted her messy crotch right on his face. "Put the 100 in my pussy baby". Once it had been inserted she removed herself along with the money and turned to him with a grin. He was now completely spent and lay relaxed still taped to the chair, with a big grin on his messy face. "That was fantastic -- Can I see you again?" He said.

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