Reluctant Escort Ch. 02

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Tom & Sandy get the next assignment.
3.5k words
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72.1k
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Part 2 of the 2 part series

Updated 10/29/2022
Created 05/31/2005
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For the past three weeks, since the encounter at the club, and later at the hotel, Sandy and Tom had led a fairly normal life. They didn't discuss the events of that evening, preferring to concentrate on outside activities such as church services and choir practice. Time at work was tense, not knowing when they would run into Mr. Stern. Whenever they met, he was always courteous but remote. Their sex life was nonexistent. A week after the events they tried, which resulted in both of them breaking down and crying in each others arms. They tried on one other occasion, after a choir practice, but it satisfied neither of them. In the back of their minds they knew it was just a matter of time before Mr. Stern called.

Thursday afternoon about an hour before quitting time Sandy got a call from Mr. Stern telling her to come to his office immediately. Nervously she walked up to his secretary, Marsha Keller, who told her to go on in. Mr. Stern was sitting at his desk doing paper work as she walked in, and he motioned for her to close the door. For what seemed like an eternity she stood at his desk trembling. Finally he looked up and said "take your clothes off." She stood there in a panic as he watched her, then in a commanding voice..."now." She slowly unbuttoned her blouse, and after another glare from him she removed it. "Now the bra" he commanded! The process of glares and commands continued until she stood before him totally nude, with tears running down her cheeks.

Mr. Stern motioned for her to come around the desk as he stood up. As she approached he reached out and cupped her breast. She stopped in her tracks, trembling. He stepped forward cupping the other breast "Spread your legs" he commanded. With one hand still on her breast he reached down and ran a finger over her slit. He slowly worked one, and then two fingers into her tight hole. "Unbuckle my belt." Tears started flowing as she slowly reached for the buckle. She didn't wait for further commands as she slowly unzipped his pants. He stepped out of the pants, as they dropped to the floor. "Take it out!" She slowly reached for the waistband of his underwear and pushed it down. "Put your hand on it," as he slowly moved Sandy back to the edge of the desk. As her butt hit the desk he pushed her up onto it, moving between her legs.

"Sandy, you and your husband stole $10,000.00 from me. Both of you agreed to pay it back with services performed. This is one of those services." He reached down and moved his cock into position. Her arms were behind her with her hands on the desk to keep from falling backwards. "Put your legs around my waist," he commanded. As she complied he slowly worked his cock into her until he was buried.

Sandy was expecting him to continue, but as he stood there completely inside her, with her legs around his waist, he reached over and picked up the phone. After dialing she heard him say "Tom! Mark Stern here! You and Sandy have an assignment tomorrow night. There will be four men, all from the same company. They're in town for a convention which wraps up tomorrow. Being one of our better customers, they called me to see if I could line up some entertainment for their last day here. Sandy will be that entertainment!"

"Here's the scoop. You take Sandy to their hotel tomorrow night at 8:00. I don't know exactly what they have in mind, but whatever it is; Sandy will accommodate them with no exceptions, and with no interference from you. Take Sandy shopping and buy something extremely sexy. Don't worry about telling Sandy about the assignment, she already knows. One more thing, tell her to completely shave her pussy tonight."

Mr. Stern didn't wait for a response. He abruptly hung up the phone. After instructing Sandy to lie back on the desk he placed her feet on the edge, next to her ass. He was now standing at the desk with her laying on it, with her legs spread. He could see every movement as her labia disappeared when he moved into her, and grasp his cock as he withdrew.

On the ride home both Sandy and Tom sat in silence. She mentioned that Mr. Stern had called her to the office, but didn't mention the details of their meeting. Just before going to bed, she cried as she shaved her pubic hair.

Friday was a wasted day at work for both. Their thoughts were on the unknown events coming up Saturday night. On Saturday Tom took Sandy shopping, as instructed, and purchased a full length dress, cut very low on top and slit on each side almost to her hip. They also bought matching bra and panties.

They arrived at room 1232 at 8:00PM. They both just stood there, neither wanting to know what the other side of that door had in store for them. Finally Sandy knocked gently on the door. After a moment the door opened and a man with a big smile and a drink in his hand looked Sandy over. "Welcome gorgeous, old Mark certainly didn't let us down. Come in!" As she entered three more men stood up from a table, all with big smiles. The first man did the introductions. "My name is Frank, the big guy there is Stan, this is Josh, and last but not least is Mike." As the door closed on Tom, he slowly turned toward the elevator to wait in the lobby for Sandy to call.

Sandy tried to smile as she surveyed the group. Frank was about 5'10" average build, and appeared to be in his mid thirties, as did the other three. Stan was quite a bit taller, and quite muscular. Josh was a light colored black man of average height and build. Mike was the largest, about 6'2" and 260 pounds. Josh took Sandy's arm and escorted her into the room.

Josh escorted Sandy to the table that all four men had been seated at, as they resumed their seats. "Sandy, although we didn't know anyone as pretty as you were coming, we've been talking about the evening. The plan is to continue our card game, with you as the stakes. Is that OK with you?" Sandy had no choice but to smile, which to them meant acceptance.

"Here Sandy." as Josh gave her a deck of cards. "You can move around the table dealing cards. Each player ends up with five cards, all face up. Best hand wins." Sandy picked up the deck and turned a card up for Josh and laid it on the table. "Hold it," Mike interrupted, "what stakes are we playing for?" Stan had a quick answer. "The winner gets to peal her dress down to the waist and gets first taste of those gorgeous tits." They all laughed and agreed that was a good first bet. Sandy moved around Josh to her left, this time between Josh and Mike. As she dealt Mike a card she could feel both Josh and Mike run their hands up the inside of her legs. She wanted to move on, but was held in place briefly, as they explored her thighs up to but not touching her crotch. They didn't go any further, knowing that her pussy was not the bet.....yet.

Sandy eventually moved on to her left, dealing a card to Stan as she stood between him and Mike. Mike now ran his left hand up her thigh. Stan moved his hand over her butt. Moving on she stood between Stan and Josh, as two hands again moved into the side slits on her skirt and played with her legs. This continued for four rounds until all players had four cards. On her last trip around the table for the fifth card she wasn't slowed much as they concentrated on each others hands. Stan was leading with a pair of jacks. Each of the other men showed disappointment as Sandy dealt them loosing hands. Finally, as Frank received the last card, and also couldn't beat the jacks, Stan jumped up, pumped his fist, and let out a big "yeeeeow!"

"Come around her sweetheart," yelled Stan, as Sandy slowly made her way to him. He slowly, as if he was going to break something, moved her shoulder straps down her arms, and reached around unzipping her dress to the waist. He then very slowly and gently pulled the top of her dress down, revealing the new bra. All eyes were on Sandy's tits as he reached around her and unclasped the bra. Sandy's arms were at her sides as she just stood there. She felt herself trembling, but hoped that it wasn't noticeable to the men. Stan held the bra in place and looked over the table. "Ready guys." He received unanimous approval, and pulled the bra away. There was applause from the other three, as Stan ran his hands over her tits. As he bent down to suck on one nipple, and then the other, the three losers decided to cut for high card, to see in what order they got a turn at her tits. Mike got high card and moved to Stan, jokingly pushing him aside, and then started his own exploration of Sandy's breasts. This was repeated two more times, as each man took his turn. Sandy felt like a piece of meat, as each pawed at her.

Finally Mike yelled "OK, let's get back to business," and all four sat back down. "Next winner gets to undress her." Sandy was given the freshly shuffled deck and started laying the cards in front of the players. This time her tits got as much action as her thighs as she moved around the table. Frank, with an ace, had high hand, and laughingly offered to sell it for $500.00. They all laughed as he got up and approached Sandy. As she stood there with her hands to her sides and her top down to her waist, he reached behind her and unzipped the dress. With a slight tug it dropped to the floor, leaving her standing in front of four strangers in only her panties. Frank walked around her, admiring his handiwork as the other three urged him to take the panties off. He put his thumbs in the waistband and teasingly pulled them down slowly to just above her slit. Stan picked up a packaged deck of cards and jokingly threw it in the general direction of Frank, as he commanded "take it off." Their joking stopped abruptly and each felt a twinge in their groin as Frank lowered the panties, exposing the shaved pussy.

"God, let's get on with this," said Mike. "I'll have a heart attack just standing here looking, without touching her."

Frank escorted the now nude girl back to the table, and handed her the cards. "This time we play for a blow job. That OK with you Sandy?" She just smiled, but wished she were anywhere but here.

Sandy started around the table, dealing one card to each player. Stan got an ace, and let out a loud "OK." On the second time around Frank had two eights. The third pass had Josh ahead with twin jacks. Sandy's body was getting rubbed all over as she moved around the players. The only thing that wasn't touched was her pussy. That still wasn't the bet. On the last pass Josh was still ahead with his jacks until Mike got a third three. That was the winner. He reached up and grabbed Sandy and in his excitement brought her to her knees. After apologizing for being so rough, he whispered in her ear that he would like his prize to be under the table, if that was OK with her. Sandy just smiled as she moved under the table. He didn't see the tears in her eyes as she unzipped him. As she pulled his cock from his pants, she knew why he wanted privacy. His rigid cock was rather small. She swallowed hard and reluctantly started licking the tender underside. After a short time she took him completely into her mouth. The other players were watching Mike as his eyes rolled up. He knew that he wouldn't be able to cum with three co-workers watching, but it sure felt good.

Suddenly Stan spoke up, "who has seconds." He retrieved the cards, shuffled, and cut a card. The other two took their turn, with Josh winning. Laughingly he unzipped his pants and pulled out his now erect cock. Sandy saw this and assumed it was time to move on. She moved under the table to Josh. Although she was turned off by what she was doing, she was grateful that her nude body was at least under the table, rather than standing nude in front of four strangers. Josh was getting excited as Sandy held the tip of his cock in her mouth and slowly licked the underside. Sandy felt both of his hands on her head, and then he was pulling her head down on his cock. She tried to hold back but he was too strong, as his cock moved into her throat. He started fucking her throat. She couldn't breathe each time he pushed in. Finally he started to spasm. She swallowed as much as she could, having no other choice. Looking to her left she saw Frank motion to her. As she crawled to him, he took his erect cock from his pants, and held it as if presenting it to her. She slowly licks him, and then ran her mouth down as far as she could, and immediately felt his cum hit the back of her mouth. Sandy started swallowing. There was one more to go! As she moved to him, Stan hadn't taken his cock out so she unzipped his pants. As her hand grasped his cock she was amazed by the size. He was much bigger that the other three. It was all she could do to get her mouth around the head. She held her hand around his cock, hoping that he couldn't force it down her throat. After about two minutes she heard Mike, "OK, lets get to the main event. Enough of this five card stuff, let's cut for high card to see who gets to fuck her first! Anyone want to lick that nice pussy to warm her up." Josh raised his hand.... "hell yes."

Sandy felt herself gently moved backwards until her butt hit the table. Frank and Stan lowered onto him back onto the table, as Josh moved between her legs. She closed her eyes as Josh licked first one nipple, then the other. He then slowly ran his tongue down her stomach, stopping at her navel. He licked around the navel, then his tongue moved on down. He continued along one side of her slit, and down her thigh. He then moved to the other thigh, moving closer to her pussy. He licked completely around the slit, and then down the middle, opening her as he went.

Sandy's mind was racing. She didn't want to feel anything, but the whole process started her body tingling. When his tongue touched her clit she climaxed. As much as she tried not to, her whole body trembled, and her hips rose to meet Josh's tongue.

The sensation was short lived as she heard Mike... "lets cut high card to see who fucks her, I've got a jack," as he pulled his card from the deck. Stan was next, and got a five. Josh reached in and got an eight. Frank slowly reached for the deck, cut into the middle and yelled "Yeoow!" and he held a king high for all to see.

Frank took Sandy by the arm and led her to the bed. "Get on your hands and knees, I love doggy style." Sandy climbed onto the bed and positioned herself as instructed. As Frank mounted her from the back she glanced at the other three, seeing complete lust as each held his rigid cock.

Frank reached down and ran his hand over Sandy's pussy, then gently massaged her clit with two fingers. She could feel herself getting wet from the stimulation. He removed his hand and slowly worked his stiff cock into her, as he reached around and took a breast into each hand. Sandy closed her eyes and tried to get into rhythm with his thrusts. He continued the process of almost pulling out of her, to being completely buried. She then heard low moans as he quickened his pace, and then felt his sperm as he pushed into her one final time. He collapsed on her back for a few seconds, her arms and legs supporting both of them.

Sandy glanced at the spectators. Not one of them had moved, as they watched the sex act unfold in front of them. As she dropped her eyes to the bed she heard, "let's each take a card to see in what order we fuck her." Frank left the bed totally exhausted, as Sandy stayed on her hands and knees awaiting further instructions.

Josh was up next. As he quickly took his clothes off, it crossed Sandy's mind that this would be her first black man. As he approached the bed, he motioned for her to turn over onto her back. He moved between her legs and had no trouble penetrating her now wet hole. She put both arms around his neck as he started to quicken his pace. Sandy moved with him, meeting each thrust. Two thoughts crossed her mind. The more she moved as he fucked her the quicker he would cum, and secondly, the sensations she felt increased as she moved with him. Suddenly she felt him push as hard as she could into her, and at the same time felt his cock spasm, as she was once more filled with cum. As he collapsed on top of her she felt all of her strength leave as she went limp.

Josh was not even off of the bed before she felt Mike penetrate her. She could feel him moving into her, as she remembered that his cock was very small. He may have been small but she felt every thrust as it crossed her clit. He had definitely worked on his movements to compensate for his lack of size. As she started to feel the first twinges of a climax he pushed into her hard, and she felt the third load of cum fill her pussy. Once again all of her strength left as she collapsed, laying there on her back with legs spread and cum dripping down her butt crack.

Stan waited for Mike to come back to the group, then walked to the bed and lay next to Sandy; He gently put his arm under her neck, rolled onto his side and whispered into her ear. "I know that this not nearly as enjoyable for you as it is for us, and you are only here for the money, but you are a very sweet girl, and have been more cooperative than we could expect. Thank you! One more to go and your evening is finished." As he rolled onto his back he brought Sandy with him, as she rolled on top of him.

Stan positioned her so her knees were drawn up and she was sitting upright. Without his asking, as he rubber her nipples, she raised herself and reached down to grab his cock. As she touched him she remembered his size, and the trouble she had getting her mouth around the head of it. Now she was frightened! She knew that this thing was going into her pussy, and feared the pain and damage that it might do. Stan saw the fear in her eyes. He smiled and whispered, "Take your time, I think you'll like it."

Sandy worked her hips in a circular motion as she gradually lowered herself, feeling the large cock going into her now very wet pussy. The size of it was pushing her internal walls in a way that she had never felt. There was pain, but since she was being allowed to go at her own pace, she could tolerate it. There was also a feeling of fullness that mixed with the sexual stimulation, causing all thoughts except the sex act to leave her mind.

After a few minutes of working at it, she was finally fully impaled, and started moving his cock in and out at a slow pace. She could tell by Stan's face that he wouldn't last long. She was also getting close to climaxing. Suddenly he reached for her shoulders, pulling her down on top of him, as he pushed into her as hard as he could. She could feel his spasms as she was again filled with cum.

After a couple of minutes she slowly got off of the bed, walked to the table and started getting dressed. There wasn't a lot of conversation. Everyone in the room was spent. She got either a thank you or a smile from each of the men as she walked out the door.

Her husband would be waiting for her in the lobby.

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