I heard her sigh.
“Yes Mike, it’s me. Kevin is fading, he may not last the day. Will you come?”
“I’ll call back just as soon as I can confirm my flight. Hold on.”
Kathryn was his old personal assistant, but was more than that. She was more like the mother he never got to have. While most walked around him fearfully, she chided him for scaring the employees.
When he was having a bad day, she shored him up, maintaining his balance. He loved her probably more than anyone in the world next to Martin Coombs, his oldest friend.
Though he never asked for guidance or an opinion, she provided both when she felt it was needed. Most times she was right, although he almost never admitted it to her.
Shrewd, intelligent, she was much more than a personal assistant. Many times a deal was turned on a suggestion by her, with an insight many underestimated.
Childless, he became more of a son than either would admit. He was devastated when she had to quit and move to the arid Southwest due to the failing health of her husband.
She was in a quandary, hers was the income they depended on, and their health insurance was through her company. Mike, a multimillionaire, stepped in, paying her full salary out of pocket, and keeping her insurance premiums paid. She tried to thank him once by he silenced her.
“I owe you more than I could ever repay with money. Please, let me do this and never speak of it.”
Kathryn was a lean, striking woman in her middle fifties, wearing her gray hair proudly. It framed her face, giving her an air of wisdom and timeless beauty. Despite her age, men, many younger, sought her attention.
Mike was huge, six and a half feet tall, platinum blond hair and piercing grey eyes. He looked like the tv actor he used to be. He was the only man besides her husband she ever had a lustful thought about.
They teased each other sometimes with innuendos, and he sometimes joked she was his fantasy Mrs. Robinson. She called him her blond boy toy in the privacy of their office.
He made a point of calling her once a week. Sometimes the talks would last for hours. He had his heart broken by his fiancee, after almost eighteen months of living together she had gotten cold feet over making the final commitment, and they had parted.
It hurt her, the thought that he had someone after spending his life alone gave her comfort when she moved away. Though you couldn’t tell it by looking at her, she was a transsexual. Still, she had great physical beauty, a petite person, half Indian by way of London. She had an exotic beauty, and up until they broke up seemed to love him madly.
Kathryn found it amusing that she landed what amounted to the Great White of San Francisco bachelors after so many regular women had failed.
He went through several temps before he settled on his new assistant, a tall striking blond in her mid forties. Kathryn met her once, and they lunched together. Edie Montrose had been with him six months by then.
“You’re sleeping with him. Don’t try to deny it, I’ve known him too long, and it’s written all over your face. Please don’t fall in love with him. He seems fond of you, but there is no future there.”
She told her a little about his background. Left on a church landing when he was less than a year old, growing up in orphanages and foster homes, he even spent months in juvenile hall.
“He doesn’t really have a moral conscience because of his upbringing. Some of the things you consider unspeakably cruel he would do without hesitation or remorse. If you’re loyal to him you have nothing to fear. Hurt him or someone he holds close and it would be very unpleasant for you. I don’t think forgiveness is in his dictionary.”
Mike arrived just in time. He held her as her husband passed. While not close to her husband, he had liked him. They had been married for thirty one years.
She was shattered but stoic. A two pack a day smoker since he was fourteen, he had never been able to kick the habit. He ended up with lung cancer, and the damp sea air of San Francisco aggravated his condition. They had lived there all their lives, and the decision to leave was hard.
The arrangements for his funeral had been made well in advance. There was a memorial in Tuscon for the circle of friends they had developed over the year they had been there. Per instructions, he was cremated.
An avid deep sea fisherman and sailor, his last wish was to have his ashes scattered over the ocean where so many of their fond memories were made.
They made the journey back, and Mike rented a helicopter. They hovered over the water, and Mike watched as she bowed her head in a silent prayer. Her eyes shone with unshed tears as she opened the urn and shook out the ashes, the helicopter rotors scattering them across the ocean.
She put the lid back on the urn, saving a bit of the ashes, wanting to keep some small vestige with her, and then collapsed into his arms, finally allowing the grief to come out. He held tightly, stroking her hair. She cried until the copter landed. Then she pushed him away and made an attempt to fix her face.
She stayed with him a week in his luxury apartment, visiting old friends and places that had been dear to her.
At the end of the week, she walked into the living room and sat beside him on the sofa, taking his hand.
“I can’t thank you enough for standing by me. I had no one.”
He held her hand and made her look into his eyes.
“You’ll always have me. I still intend to have our weekly chats. I really wish you would reconsider and come back to work for me. Mrs. Montrose is very capable. I’ve been thinking about promoting her, and having her run our office on the east coast.”
“No, I won’t change my mind. There’s just too much here to remind me of him. We really loved Tuscon and made some good friends. My life is there now. I’ve got a flight at noon to catch tomorrow. Time to move on.”
She was holding both his hands now, looking intently into his eyes.
They had been drinking wine. She had already had three glasses.
“If you want to do something for me, I have a request. Hear me out before you say yes or no. This is something I don’t think you’d expect.”
He lifted an eyebrow but didn’t say anything.
“I remember all the times we flirted. You always said I was the hottest MILF you ever saw. It’s more like GILF now, but I’ve tried to maintain my shape. I even saw you naked twice, when I came into your suite without thinking. I have to tell you, it doesn’t look real.”
He was leaning forward, looking hard into her eyes, wondering where she was going.
“I’m just going to come right out and say it. I’ve always fantasized about you, wondering what it would be like. I’m unattached now, like you, so there’s no one to cheat on, I would never even be talking about it if Kevin was still with me.”
“I haven’t been with a man sexually in four years. I want to spend the night in your bed, and do everything we can think of. I want you to show me your legendary skills I’ve heard so much about.”
“Just for tonight, Mike, never again. As Shanna would say, it would just be a ‘one off’, never to be repeated. Please?”
He sat there for a second before leaning forward and kissing her, tenderly at first, then becoming more demanding. She gave in, opening her mouth, feeling his tongue push hers back, establishing dominance. She marveled at the ease he pulled her to his lap. Soon his hands were traveling, brushing over her breasts, sliding up her thigh. She could feel his enormous erection on her butt. She jumped off and stood in front of him.
“Patience, dear. I want the full experience, remember?”
She reached behind her and pulled the zipper of her dress slowly to the bottom, shrugging out of it, standing before him in a red corset and hose, clipped to it. The panties were miniscule and bore the trademark weave of Rose’s shop.
She slid her hands languidly up her thighs, across her stomach up to her breasts. She took the cups off, massaging herself until her nipples were standing straight out.
“Help me out of these, would you?”
Mike was more than familiar with the panties. He sought out the end, and pulled, slowly, watching the weave unravel until the remnants dropped to the floor. She turned, and he could see the moisture below her bare mound, her clit hardened with arousal.
He stood, moved behind her. She leaned back into him as he stroked his way down her body, teasing her nipples and cupping her breasts before traveling downward. He dipped a finger inside her drenched pussy, pulling it out and stroking her clit. Slowly at first, then vigorously, sliding two more fingers inside her until sje was dripping down her thigh. She experienced her first orgasm of the night, only remaining upright because of the arm wrapped round her waist.
She pushed him away.
“You have way too many clothes on” she said, as she tugged at his belt. He started to help her but she gripped his hand.
“Let me do it, please?”
He dropped his hands to his side as she unbuttoned his dress shirt, admiring his broad shoulders as she slipped it off. She covered most of his chest with small kisses, biting down lightly on his nipples. He shivered in appreciation.
She removed his belt, unbuttoned his pants and slid the down to his ankles. With a slight look of fear in her eyes, she pulled the silk boxers out so they wouldn’t get caught on his erection, and slid them down. She knelt before him and removed his shoes and socks, pulling the pants and underwear off and setting them to the side.
Not being able to stop a little gasp that came out when she was eye level with his cock, she reached out with both hands and stroked, gently.
She leaned forward, sliding her tongue across the head and down the shaft, marveling again at the size. Sliding back up she took as much as she could handle into her mouth, bobbing slowly. He gave a small groan of happiness, and played with her hair, gripping it lightly time to time. Increasing her speed, trying to get it deeper, she had him teetering on the edge. He pulled her head back and warned her.
Kathryn looked up, still stroking him.
“I can’t say if I can swallow it all, but I need to try. Just warn me a few seconds beforehand.”
He tried to control it, but five minutes later he had her head clutched in both hands, trying not to ram it down the throat. When he came, she couldn’t believe the volume. She stopped trying to swallow and just let it flow out of her mouth and down her chin, dripping off onto her breasts.
She sat back on her heels, trying to get her breath back. Mike had brought her a warm moist towel, and she cleaned up a bit before taking it back into her mouth.
“I’m not the only thing that needs cleaning” she quipped. After about a minute he declared her done, picked her up like a feather, and carried her to the bed, tossed her on, and grabbed her legs.
“You wanted the full treatment.”
He started on her ears, nibbling all the way down her body, spending time on her breasts but avoiding the nipples, even as she arched her back, offering them to him. He kissed and licked on down to her ankles, passing over her pussy with just one swipe across her clit. Then he flipped her over, kissing all the way back up to her neck, spending a lot of time making sure he didn’t miss a millimeter of her ass. He ended up nibbling just below her hairline while she pounded into the pillow in frustration.
Suddenly flipping her over, he locked his mouth around her clit, sucking furiously, running his tongue over it rapidly, while his hands snaked up her body to grasp both breasts, pinching her nipples. She came instantly, then writhed through two more before he stopped. Thinking she would get to rest, she grunted as the air left her lungs.
He slid into her slowly, steadily, marveling at her tightness. Once all the way in, he started rocking back and forth, lengthening his stroke until he was pounding into her steadily. She tossed her head back and forth and her hands waved randomly, grunting and moaning.
As he neared his climax he pounded furiously, and as he finished she gave a final lunge upward and screamed. She lay semiconscious as he gathered him to her and covered them. She was asleep instantly.
She was awakened two hours later, spooned to him, his erect cock already sliding into her. He rocked her through one climax before he pulled her to her knees. Sliding off the bed he lined up and entered her again, firmly. He stroked faster until she was slamming back into him of her own accord. He held her, not letting up, as she came almost continuously. In the end he was pounding savagely as she collapsed, her tight ass held up by his grip. When he erupted he put his weight on her back, pushing her down until he covered her body. He lay there for a second before rolling her over and covering her mouth in a deep kiss. She was so overcome she was crying, clinging tightly. He kissed and soothed her until she was asleep.
She woke up, spooned again to him, once again feeling his massive cock pressed against her. She eased out of his arms slowly, sliding down the bed until she was inches away, staring in fascination for a moment. Then she slid her tongue across he crown, pausing as he stirred.
By the time he was fully awake she had half his length in her mouth, moving rapidly. When she felt his hand on her head she stopped.
“Goody, you’re awake. I didn’t get to try this last night, do you mind?”
She had risen up to straddle him, sinking down onto him inch by inch, stopping to slide up and down occasionally. When she rested fully against him she sighed. Then she began moving, rocking her pelvis in little circles before rising up and slamming down. His hands found her nipples, rolling them.
“Yes!” she cried.
“Rough them up, honey. I’ve never had it that way. Show me what a dirty girl I am.”
He began pulling her nipples until her small breasts stood straight out and left her gasping, before letting go and slapping them. Her juices started flowing.
“More! Harder!” He began mauling them, sure he would be leaving bruises.
He literally lifted her and turned her round, slamming her back down, hard.
“Now ride me, bitch. And if I don’t think you’re putting enough effort in it, I’ll spank that hot ass.”
He slapped both cheeks hard enough to leave a red spot. She orgasmed again.
“Oh! That’s it. Spank your dirty old girl, make her ride that cock. Own it!”
It was the magic word. By the time they were through she was bruised and her cheeks were glowing. She collapsed.
Continuing the fantasy, he grabbed her hair and dragged her down to his cock.
“Clean it! Do a good job, or you’ll be punished.”
She deliberately did a lackluster job until he rolled her nipple and she shrieked. After that, she licked and sucked him eagerly, until he started getting erect again.
She raised up, and looked him in the eye.
“I’ve got one more fantasy. No one has ever had my ass. I hinted around to Kevin but he thought it was to dirty. I experimented with a couple of vibrators and found it intense. Would you, Mike? Fuck my ass, I mean.”
His erection returned to full mast.
“I’d love to. But let’s take a shower first, relax a bit.”
He led her into the shower, marveling at her body something a thirty year old would be proud of.
They splashed, they played. He used the soap to lube his fingers, and worked two fingers into her ass while he played with her clit with the other hand. She came so hard she squirted.
“Rest a bit, and call the airline. You won’t make that noon flight.”
She got one for nine.
Mike rummaged around in a dresser drawer. She came over to look.
It was a bottom drawer. deep and wide. And it was full of sex toys. Dildos, vibrators, ball gags, whips, handcuffs, collars, some thing she didn’t recognize and wasn’t sure she wanted a description of.
Mike grinned at her.
“What can I sat. Shanna and I played a lot.”
At the mention of her name his forehead wrinkled in pain. Kathryn knew better than to talk about her. She put her hand on his arm, changing the subject.
“That’s another fantasy, being collared and cuffed. Will you?”
He smiled again, and soon she had her hands secured behind her, a wide black collar round her neck. He surprised her by holding up a ball gag.
“Last chance to change your mind. Once this goes on there’s no going back.”
She opened her mouth.
Gagged, bound, and collared, she lay face down on the bed. He worked on her, spreading lube generously and going slowly. Soon she felt him against her and experienced her first moment of fear.
He surprised her by sliding an eight inch vibrator int her pussy, set on the highest speed. He worked it in and out for a minute until she was squirming, then slid the first inch into her ass. It didn’t hurt at first, but as he got deeper the pain got worse. It took ten minutes before he was fully inside, and tears flowed freely down her cheeks.
But then he started moving. Short, slow strokes, gradually increasing. Soon he was sliding almost completely out before plunging back in.
The pain had stopped, superseded by a numbness, that eventually gave way to a most pleasant sensation. She started climaxing, especially when he would reach around and saw the vibrator in and out to match his stroke. She was crying and gurgling into the gag in passion, lost in the sensation. At the end, she actually lost consciousness.
She came to her senses as he unlocked the cuffs and removed the gag. He reached for the collar but she stopped him.
“I want to be owned by you, at least for awhile. I wish there was some permanent way to show you.”
He regarded he with a strange glint in her eye.
They showered again without playing.
He took her out to his favorite Mexican restaurant.
Over a post meal beer for him, wine for her, he asked her.
“That remark about a permanent symbol? Did you mean it?”
“Yes I did.”
They left the restaurant and he drove to a rather seedy section of town. They stopped in front of a tattoo parlor.
The owner greeted Mike like an old friend. He was French, and actually kissed her hand when they were introduced.
In a matter of minutes she was face down on a table, while he shaved just a bit of hair off her neck, assuring her no one would notice.
It hurt very little and was done in just a few minutes. He put a bandaid over it and told her to keep it moistened with the gel he gave her for a few days.
“Wear your hair up for a week, if you can. It should be healed by then.”
They went back to his apartment so she could pack. He took his high end digital camera, put it on zoom and took a picture for her.
It was a word, so tiny it almost couldn’t be read by the naked eye.
She looked at him, wondering how many others wore that brand. She decided not to ask.
“What are your plans now?” he asked, as he drove her to the airport.
“I don’t know. Thanks to the insurance policies, I don’t have to work. I may volunteer, or I may take a part time job, something to keep me busy.”
“This sounds awful so soon after Kevin passing, but there’s a man there. A man I’m interested in. We met through our social circle. He’s actually a few years younger.”
“His wife passed away two years ago, auto accident. We’ve danced at several of our mixers.”
She giggled suddenly, like a young girl.
“I’ve felt him, when we danced. He’s not in your league, hell bells, most humans aren’t, but it feels like a very nice package. He’s never been improper, he was a friend to Kevin too, but I could see his interest.”
“Best of all he has a large family, five kids and a dozen grandchildren. I miss not having kids, I’m hoping he will share his.”
“So, after a month or two, if he doesn’t call me, I’m going to call him. Does that make me a bad person?”
He squeezed her hand.
“No, it makes you a good woman with a lot to offer. If it’s not him, it’ll be someone else. After all, your the hottest GILF I know. Be careful, if you show him the energy you showed me last night, you’ll be a widow again.”
She giggled again and swatted his arm. Then she became serious.
“Mike, I want you to do something for me. Hear me out, please.”
“I need you to talk to Shanna. I had dinner with her and her friend Suzy. She doesn’t look good. She’s thin, and the spark has gone out of her eyes. She’s talking about going back to England. You’ll never find anyone who loves you more.”
“She broke your heart, but she was influenced by someone with a motive to break you up. She hasn’t dated anyone, doesn’t go out. Suzy says she’s waiting for you to take her back. Please Mike, If you love me just a little, promise me.”
He held his silence until she sighed.
“Well, at least promise me you’ll think about it.”
He smiled. “I promise.”
It was a tearful farewell at the airport. He sat with her through a delay until she boarded.
They hugged and kissed as the friends they were.
“Don’t forget me, Mike.”
“Are you kidding? Expect my call on Thursdays, same as always. After all, you’re the hottest GILF I know.”
She laughed, then gave him a smouldering kiss. A man beside them watched in amazement.
She walked through the gate and he looked over.
“Hottest MILF in the world, without a doubt.”
Laughing at the man’s expression, he went back to his car.
Driving home, he thought about what Kathryn had said. Deep down, he had to admit, he wasn’t over Shanna. That’s why he didn’t date. He was getting all the sex he wanted from Chantal and Edie, but that’s all it was. He was fond of them, but that was all.
He got home and pulled out a framed picture of them. It was at a party they had attended about six months into their relationship. He was sitting on a bench, and she was on his lap, looking up with love and adoration. He was looking down at her, bending to give her a kiss. It was his favorite picture of her. He sighed and put it on the night stand.