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The Escort and the Widower

"An escort is pleasantly surprised with her latest assignment"

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Amy Treadwell sighed relief as she closed her apartment door behind her. It had been a long day at the doctor’s office where she worked as a nurse. This had been one of those days with just too much trauma and drama and she was exhausted, and looking forward to a glass of wine and a soak in the tub.

She almost didn’t notice the blinking red light on her answering machine. She kept her land line strictly for business calls. Amy was a nurse by day, but an escort by night and it was much more lucrative than her daytime job.

Reluctantly she listened, relieved somewhat that there was only one message. Ellen, her “director of services” as she preferred to be called, left the message with the enthusiasm of an excited teenager.

“Amy, you’re not going to want to miss this one; he’s a widower, and says he doesn’t want much, but he wants someone tonight. He gave me a list of specifics, including some instructions. They don’t sound unreasonable, so I wrote them down and sent Kenny to drop the list into your mail slot this afternoon. He said it was strictly a sex related date and he agreed to pay DOUBLE without even asking any prices, Amy! I did the usual research and confirmed his name and address, so he should be safe. Good luck, and call me tomorrow!”

Groaning her disappointment, Amy stepped back out into the hallway and opened her mailbox with her key. Mixed in with the electric bill and a bunch of sales fliers was a folded page that Ellen had delivered. Amy made a cup of tea, slipped off her shoes and sat down in the kitchen to read the list:

She must have normal pubic hair, not shaved off or in any designs.

She must not shower or bathe before she comes over.

She must wear the same panties she has worn all day.

Amy slapped the list onto the table, groaning with slight disgust. “Jeezus!” she gasped, “Another 70 year old pervert on Viagra probably.” She sipped her tea, stretched her legs out and rested her feet up on another chair as she continued to read:

She must have long hair, any color, but wear it down.

She must wear dark or bright red lipstick with matching fingernail polish.

She must wear a white, tight blouse but no bra.

She must wear a loose skirt that does not hug her curves, and it must be as short as possible.

She must wear thigh high stockings, and heels that are comfortable.

Sipping her tea again, Amy thought, “Well, although it seems he’s some sort of voyeur, wanting a trashy looking hooker, at least he’s willing to let me be comfortable.”

The door will be unlocked; I will be waiting in the den, to the left down the hallway.

Please ask her to arrive at 7:30 p.m. and tell her to rest assured that I will not require intercourse.

Please thank her for coming and for honoring my wishes to the letter.

Amy laid the paper on the table and gazed out her kitchen window, wishing she had other options but acknowledging that the money she was accumulating and investing would allow her the comfort she wanted when she grew older and could not attract men so easily.

Later, after she had eaten and was picking clothes from her closet she began to dread the assignment, but double pay was hard to refuse from any client. She sighed and hoped that whatever he wanted would be over soon.

That evening she arrived and entered his modest home at exactly 7:30 p.m. She found the place neat and clean. As she made her way to his den, she noted several attractive pictures and paintings on the walls and the furniture blended well with the carpet. She was pleasantly surprised when she found him seated, fully dressed and waiting for her.

She guessed he was in his early fifties, dark brown hair with a little gray, soft blue eyes and quite distinguished looking. He stood and offered his hand and she shook it. Gentle grasp by smooth hands. Warm smile. He offered her a seat and sat opposite her as he spoke.

“I want to explain the reasons for my requests,” he said. “My wife died eight months ago and I’m very lonely. We had a wonderful marriage and I miss her terribly, but as you might imagine, I’m not past the age of having sex and, well….I’m in need of some special attention.”

Amy felt better about the visit already. “But you don’t want intercourse?” she asked, “After eight months, I would understand if you did, and I’m willing to….”

“Not necessary,” he said, interrupting her, “at least for right now, but maybe later, another time. The last time Marion and I had sex we were having a little role play and I just would like to repeat that and then I can move on.”

“Role play?” Amy asked.

“Yes,” he said, “Sometimes she would tease me for days or make me do things that aroused me terribly but she would withhold intercourse, but when she was ready, our sex was primal and so intense that it left us both exhausted.”

“So the clothing, not bathing, etc. is what it was like the last time with her?” Amy asked.

“Yes,” he continued, “that’s why you’re dressed as she was then. She surprised me after work; I never knew what she would do or make me to. That night she made me smell and lick her dirty sex until she climaxed. Then she made me masturbate in front of her while she watched. That’s all I want you to do tonight, just that, and you can do it however it pleases you.

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Is that all right?”

Amy leaned back in her seat and crossed her arms across her chest. “Stand up and take your clothes off except your underwear,” she said firmly as her answer. Suddenly the look on his face was one of relief as he smiled slightly and complied.

“Kneel on the floor; lean on your hands behind you,” she instructed. He obeyed silently. She stood and walked around behind his head so that he had to tilt his head up to look at her. She unbuttoned her blouse and opened it until both her breasts were exposed. As she leaned over him, lowering her breasts to within inches of his face, his mouth opened and he whispered, “Oh, my.”

“Take your cock out and stroke it slowly, very slowly,” she said. He licked his lips and with one hand fumbled with the fly of his briefs until his erection sprung free. She smiled as he fisted it, and she lowered one nipple to his lips.

“Kiss it, nothing more, just once,” she offered. He closed his eyes as her nipple touched his pursed lips and his hand quickened on his shaft. “Slow down,” she warned, and his hand complied. “That’s better,” she replied as she shifted her other nipple to his lips. “Now this one, just a kiss, now; behave.”

His lips were so warm, so inviting that she wanted to push her flesh into his mouth and let him suckle her, but she remembered her purpose. She stood and walked back around in front of him. “Sit up,” she said quietly.

When he did she turned and bent over in front of him. “Slide my panties off,” she instructed. He did so, reaching up under her skirt with his free hand and finally managing to roll them down her legs. When she stepped out of them, she said, “Lean under my skirt and kiss my ass.” She wasn’t sure if his wife might have made him do this, but she wanted him to do it. And he did, kissing each buttock several times, close to her dark crevice.

Surprisingly, the feel of his head under her skirt aroused her. She stepped away and decided it was time to satisfy his requests. “Lean back on your hand again, head up,” she said, “Keep stroking, slowly.” When he was in position she walked back around him, close to his head and swung a leg over him with her back toward his feet.

Straddling his head, she lifted her skirt and looked into his excited eyes. The height of her heels positioned his face nestled in her mound, her pubic hair curled around his nose. “You may smell me now, nothing more,” she said authoritatively.

He closed his eyes and inhaled deeply, over and over. She wondered how the smell of her day’s activities, including some arousal in the past few minutes could excite or satisfy him, but she let him enjoy his quest until she heard soft whimpers from his muffled lips.

The whole scenario was driving her insane with arousal. She was glad that the activities he requested included giving her oral sex because she wanted it and needed it now. She let her skirt fall loosely fall over his head, leaving him in the warm darkness between her thighs.

“Lick me, just as you did for her,” she said as she put her hands on her hips. His face pressed up into her and his tongue gently slipped between her labia. Just feeling his breath aroused her even more and she knew it wouldn’t take much to reach an orgasm.

He was not only talented with his tongue, licking and teasing, he was patient and he knew how to work a clit with his tongue and lips. She held back the urge to grab his head and hump his face and she let him complete his mission. Her legs trembled and she bit her lower lip as he brought her to a sweet climax, sucking gently on her clit.

When she began to relax from the surge of pleasure, he slipped his tongue inside her, lapping at her wetness. She allowed him to indulge until he pulled his face from her folds. She lifted her leg, stepping away from him and took a seat on the edge of the large leather chair where she had found him upon her arrival.

He had not given her specifics as to what to do during or after his masturbating but she decided to use her own judgment. “Stand here and masturbate so I can watch, and don’t come until I tell you,” she demanded.

He stood and stepped close to her and began stroking his erection. She took her breasts in her hands, squeezed them and played with her nipples as she looked up into his eyes. He moaned and stopped his stroking, obviously awaiting permission and avoiding ejaculation.

“Keep going, slowly,” she reminded him and he resumed his task. He stopped again in a few minutes. She was impressed with his self-discipline.

“You may come now, but stroke it slowly until you do,” she said.

He resumed, as instructed, licking his lips, staring at her breasts. Finally, as his legs began shaking he muttered, “I’m going to….I’m going to…” and then she quickly leaned forward so that his sperm splashed into her cleavage. His eyes were huge with disbelief as rope after rope of his seed hit her chest and drizzled down into her cleavage. When he was finished, she buttoned her blouse, stood and kissed him lightly on the lips.

His astonished face was silent when she whispered, “Call me anytime; my name is Amy and the next visit is free.”

He was still standing, clutching his deflating cock as she left his den but he never spoke or looked back to watch her leave. She closed the door as she left, and felt his cum soaking her blouse. She smiled and out loud told herself, “I bet he’ll call me before eight months go by.”

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Written by benawriter
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