Lily really wasn’t in the mood for this tonight but Gretchen thought she’d be the best girl to take the call. Gretchen had always been very fair to her girls, she only kept twenty percent of what they made and generally let them pick what nights they wanted to work. Lily had been working for Gretchen for about seven years now and was living quite the good life. She had a few regulars and Gretchen’s service catered to higher-class men.
Just like anyone else in the business, Lily remembers her first trick well.
She was seventeen and had just left home for college when a girl in one of her classes approached her with the name of a madam who was always looking for fresh faces. Lily mulled it over for a few weeks and deciding she could really use the money, she gave Gretchen a call. It really wasn’t as bad as the after-school specials make it seem. There were no tears; no getting beat up on a regular basis. As long as you could remember a few key rules, it was just sex. People do it anyway, why not get paid for it.
Lily was getting ready to turn down the job for tonight but then Gretchen told her how much he was paying. It was a lot of money and there was a new diamond bracelet that Lily had her eye on. That kind of pay would get her the earrings to match.
“But,” Gretchen continued, “he’s got a couple of requests.”
Gretchen explained that David, the client, had a thing for the June Cleaver type. He wanted someone to dress like her, come over and make dinner and maybe do a little light cleaning. Lily figured it sounded a little goofy but not too bad and she could practically see that bracelet on her wrist.
With the better part of the afternoon to prepare, Lily took her time shopping. She had a tough time finding the right dress but finally found it in a vintage thrift shop. She then went to get her hair done in a sophisticated up do. When Lily got back home she started dressing the part for her date. She put on modest undergarments, stockings and her new dress. She then topped it off with sensible heels and a string of pearls.
Giving herself a once over in the mirror, Lily realized she looked like she was straight out of a 50’s television show. Just before she left her apartment, Lily added the finishing touch of a deep red lipstick.
When Lily arrived at the address Gretchen had given her, she found a nice house and manicured lawn with the proverbial white picket fence. She walked confidently up the path to the house like she belonged there, and as instructed, let herself in. David was sitting on the couch watching a football game. He was wearing jeans, a t-shirt and ballcap.
“David. Please go get cleaned up for dinner.” she said with a gently commanding voice. Lily knew her job and got paid well to do it.
“Yes ma’am.” David replied shyly.
David looked to be in his early forties, a touch thick in the middle, maybe a bit of a nerd, but overall, not too bad looking.
As David went off to shower and dress, Lily got dinner started. A casserole, of course. After dinner was put in the oven, Lily donned her yellow rubber gloves and began to tidy up the kitchen.
When David came into the kitchen dressed in khakis and a button down shirt, he leaned against the doorway and watched Lily finish up the dishes. After they were washed and dried, Lily took off her gloves, placed them neatly by the sink and turned to survey David.
Giving a nod of approval, Lily then opened the pantry to retrieve the stepstool and feather duster. David followed her closely as she walked towards the living room. She placed the stool in front of a tall bookshelf, stepped up and began dusting. Lily lifted one leg behind her bending at the knee. As she did this, David took a long look at her legs. Lily glanced down at him, saw that he was staring, then lowered her eyes further to notice his pants growing tighter in the crotch.
Just then the oven timer beeped. Lily set down her duster and rushed back to the kitchen. After setting the casserole on top of the stove, Lily went to work setting the table. When everything was ready David pulled her chair out for her then sat down at the opposite side of the small table.
They made small talk during dinner discussing the news, the weather, books. The usual things. When Lily and David were done eating, she stood to begin clearing away the dishes. Again, knowing her job, Lily decided to get things moving.
Lily shrieked and jumped up onto her chair claiming she’d seen a mouse. David looked confused for a second but then seeing that Lily had grasped the hem of her dress and was pulling it up to expose the tops of her stockings, he caught on to what she was doing. He quickly came around the table and offered his arms out to her. She fell into him and he carried her into the living room. After David set her down, Lily threw her arms around him, buried her face in his neck and pretended to be very upset. David ran his hands up and down her back trying to soothe her but had no control over his growing cock being pushed into her stomach.
When Lily lifted her head from David’s shoulder, she found that she’d gotten some make-up smeared on his collar. She began unbuttoning his shirt telling him they’d better get it in the wash right away. Lily took her time with the buttons, letting her fingertips brush his bare skin with each one. David still had his hands on Lily’s hips, holding her close to him. After she got the last button undone and the tail pulled from inside his slacks, he pulled her close and kissed her gently. She placed her hands on his chest and leaned further into him.
David reached down and scooped Lily up in his arms. On the way to the bedroom she nuzzled into David’s neck. When they got to his room, David set her down on his bed then went around the room lighting the many candles he’d put around earlier that day. Lily could tell that even though he’d paid for his evening with her, he was still trying to seduce her.
When he was done, Lily stood and walked over to David, she then turned her back to him so he could unzip her dress. She turned to face him again and slowly pulled her conservative dress off her shoulders, down her arms and her waist to finally let it fall to the floor around her feet. His eyes drank in the sight of her standing there in a white bra and panties with silk thigh high stockings.
Lily climbed up on the bed and resting on her elbows with one knee bent, looking like an old time centerfold, she waited for David. He undressed while never taking his eyes off of her body then laid down next to her. She rolled over to him and began kissing his neck and ears while his hands roamed over her silky, cream colored skin. He unhooked her bra and helped her pull it down off her arms. David quickly pushed Lily onto her back and rolled on to her, settling his weight between her open legs. He took her full breasts in his hands and began covering them in kisses. He pinched and sucked on her dark nipples and traced around her large areolas with his tongue. David sat up on his knees and pulled Lily’s panties off, then let his hands move slowly back up her legs feeling the silk under his fingers. He lowered himself down again and let his tongue glide from the top of her stockings to the moist folds of skin between her legs. He pushed two fingers inside her while his tongue darted around them.
Lily knew in keeping with the part that she shouldn’t make much noise, but David really knew what he was doing and she was finding it hard to stay quiet. She had learned over the years to let herself go numb when she was with a client, but then none of them had ever tried so hard to please her. They were more interested in using her as arm candy at a high-society function or just for a quick fuck in some seedy hotel. In spite of herself, Lily’s breathing quickened and she gave in to David’s well-trained fingers and mouth. Lily bit her lip when she came; it wasn’t very lady like to scream and moan.
David moved up Lily’s body and reached over to open the drawer in his nightstand. He pulled out a condom, put it on and slowly pushed inside Lily. She wrapped her legs around his and ran her hands over his smooth chest. He was being very gentle, really making love to her. There were a few times Lily had to remind herself that this was a job, and while she could enjoy it, she had to fight to not get swept up in it. She closed her eyes and let her head drop to the side when David brought his lips to her neck. Lily moved her hands to his back holding him tightly feeling his body’s motion in and out of her. Between the weight of David’s body on her, his mouth on her skin, the candles and his hands running through her hair, Lily got lost in the moment. With her fingernails scraping across David’s skin and her head thrown back, Lily started to moan. She found his mouth with hers and their tongues danced slowly together.
David sat back on his knees, bringing Lily up with him, then pulled his legs out from under himself. With both hands running through his hair, Lily moved slowly. She made long, slow circles with her body feeling him over every inch inside her. She then pushed David down onto his back and tucked her legs under herself. Lily was riding David at a good pace with her hands on his chest for support. She didn’t care anymore about the role she was supposed to be playing. Lily reached up and let her hair fall down her back.
She let her hands graze over her breasts, down her stomach and back to David’s chest. She began to ride David faster and letting her hand move between her legs, she gently stroked her hard clit. David grabbed on to her hips and raised her up a little higher with each thrust.
It wasn’t long before Lily climaxed again. She had really let herself go with David. After she’d recovered a bit, David pulled her down to him then rolled them both over with his arms wrapped securely around her. He placed his hand at the back of one of her knees and pushed her leg into her body while he raised up over her. David was moving faster. Lily had her back arched, moaning in between sharp intakes of breath. She had her hands wrapped around his arms digging her nails into his flesh. After a few more hard thrusts, David pulled out of Lily, hurriedly took the condom off and with one long, loud groan he let his seed spill on her flat stomach. He ran his hand over his come, rubbing it into her skin.
After lying together for a little while, Lily told David she needed to go. He helped her get dressed and gather her things. When they got to the front door, David presented Lily with a small silver box. In it was a pair of beautiful diamond earrings. Lily hugged David tightly then placed a gentle kiss on his cheek before turning to walk away.
David became one of Lily’s regulars and as hard as he tried, he could never talk her into quitting the business and becoming his wife.