Black Boots Goes Downtown

Black Boots and her lover, Michael Gallagher, got into the taxi. The smell of body odor and curry was strong. Black Boots gagged. Michael said "Take us to 1st and 10th.Please." in his slick voice. Black Boots leaned against the seat as they lurched downtown. She mused...'It has been over two years since we reconnected'. The two first caught up on Linked In, where she worked at her first job as a corporate paralegal at one of the world's largest law firm, Glott, Marks, Gilman & Moore, twenty four years ago.

When Boots put her info into the profile, all of the LinkedIn members who had worked in that company during that time period popped up. She thought 'I hardly know any of these people. I barely recognize any of the names except one: Michael Gallagher, now he's a partner. Business must be slow if he has time to play with LinkedIn. What fun! I had had a little crush of him. I never got to work with him but he always had a smile and a good sense of humor.' Boots mused further ' He just never got the message that I was interested. He was so awkward and 'old man looking' before his time...and yet it was his sense of humor that had attracted me then...His humor and the fact that I knew I had power to make him hard. I loved to see him squirm back then...he was so inexperienced. Now I have him. When I knew him back then, I wanted to own him and now I do.'

Boots looked over at Michael. He looked straight ahead. He was always so nervous around her. He was tapping his stubby little fingers on the back of the driver's seat. 'He is like a little abused dog' she thought and touched the top of his balding head. He didn't even look over at her. Boots leaned over and blew in his ear and still no reaction. She bit the lobe and he reacted with just a slight movement an almost undetectable flinch. He was like a wall she thought. A wall that she could do anything she wanted with...

The cab stopped in front of his apartment. He paid the driver. It was a walk up thought Boots disgustedly. Michael made so much money but he was the cheapest man that Boots had ever met. He didn't even own his apartment. He had had it as a sublet for years since he had first come to NYC out of law school. He paid $1,500 a month for the bug infested one bedroom apartment. He was phobic about going broke. Boots was not mercenary. It was Boots who had provided all of the presents for her lover. She loved to shop for him. It gave her power to make him beholden to her. She would never have wanted his money, if she took his money, he would have power over her. He never said thank you for the gifts she had sent. He didn't feel worthy. She had taken him to task, in her way, and now he thanked her.

When they got to his apartment, Michael opened the door. He had cleaned up for her. She had stipulated that he hire an exterminator before she would set foot into his apartment. He looked so nervous. It was dark. He did not want the light on. She turned to him and opened her black bag "I brought a present for you. Let's go to your bedroom and look at it." She pulled out a ball of black material.

Michael led her to the bedroom where books, papers and old take out pizza boxes were piled in stacks all around the room. They could barely walk, there was so much clutter. "Take off you clothes" Boots commanded. Michael hesitated but did as he was told. Boots handed him a black bra "put this on now." Boots had suspected that Michael had worried about his excess weight and man boobs. She did not care...she had wanted to suck on them for months. She helped Michael into the bra. Boots handed him black bikini underwear." Don't worry they are plus sized. Take off those boxers" Boots turned away. When Michael was dressed in the underwear that Boots had provided, she looked appraising at him. "Get on the bed." He did as he was told.

Boots took off her coat and dress. She stood in her underwire black bra and leaned over the cowering Michael. He was so frightened he was having trouble getting an erection. Boots started to rub his hard belly. Michael was a drinker and his belly was like a round exercise ball from all of his fancy client dinners chased down with good wine. He had lived the stressful life of a workaholic who drank too much. Boots caressed his belly and put her tongue in his belly button. Boots knew that even if she could get him hard she would have to get on top and she wasn't ready for so much exertion...yet. She pulled his pubic hairs from the bottom of the bikini panties. She chewed on the small hairs. It smelled musty of old sweat. She parted his legs and pulled her bag closer to her side. Michael was motionless.

Boots pulled off the panties with her teeth and started rubbing his anus with spit from her fingers. She stuck one finger in. He writhed in pleasure. Boots rotated her finger slowly in his butt hole and put her mouth over his penis softly. She was very gentle because she knew that anything more than a light touch with the tongue on the penis would be too much when combined with the anal stimulation. She stopped and pulled something out of her bag. She opened up a tube of lubricant and smeared it over the device. She started the vibrator on the butt plug and inserted it gently and slowly into his anus. Within minutes he had ejaculated.