Her New Boots

Jill waited near the corner of Main and Fifth Avenue in her new boots. These were not any boots, but the kind made for fucking and useless for walking any distance more than the living room to the bedroom. But here she was on a street corner with them on.

With her new boots, she was now five inches taller than her 5 feet, 2 inches. Jill is usually a confident, bold woman; this was well out of her element and a little exciting in that 'new experience' kind of way.

The black boots were not hard to find, she had always seen them in the window of her favorite shoe store, but the rest of her outfit she worried over for days before finally picking a short, red spandex dress that hugged all of her curves! Jill would have been too self-conscious to wear this out of the house, but with a short leather jacket and black tights she almost felt comfortable enough.

Her makeup she applied heavier than usual, focusing on her lips and picking a lipstick that matched her dress. She wore a wig for the occasion. It wasn't unusual to find her wearing one as she enjoyed changing her hair colour on a whim and the power to act a little differently because of it. It was a short bob, the front ends curled in nicely, her blue eyes accentuated by the dirty blond colour of the wig.

Jill was alone; it was an area of town she was not familiar with and the people walking by she would not have known. That was part of the thrill, being somewhere new, doing something that pushed the envelope of anything she had ever done. It was not the safest fantasy she could have chose to fulfill but this one she really wanted. Pushing aside all the anxiety and fear and negatives to get to this point, standing on a street corner looking to give someone head was her goal.

Taking one last deep breath, she walked to the curb, picking the black BMW parked there as the car she would approach, she would start.

"Hi" she said leaning over, letting the man get a good look at the deep cleavage revealed by the low cut dress.

"Hey, how much for a blow job" he said as he licked his lips while staring at her chest.

"Fifty" she demanded like she knew what she was doing.

"What? 25!" she had his attention, he looked in her eyes now!

"Fifty, take it or leave it? And, just to make it interesting, don't bother with a condom"

"Fine then, but its twenty-five unless you get all of my cock down that sweet little throat of yours."

She winked and opened the door.

Getting in, Jill was a little at ease now. She had won first the little battle, all that was left was the easy part although; she had never had any man's cock fully in her mouth.

The guy turned down the first side street and Jill had slid over to the driver, her hand massaging the hard cock through his pants. She loosened the zipper as he put the car in park and by the time he eased his seat back to give her room and to watch; her head was bobbing up and down the length of his cock.

Struggling not to gag, she worked at the bulbous head, shifting her tongue this way and that, trying to get him past the furthest point anyone had ever been. What Jill was doing must have been working; the man was having trouble holding still, he was grunting already with effort to keep from coming. He was determined to hold out until he was fully inside her.

Taking him out of her mouth, she took a breath and thought "one full movement" and as she slid him into her mouth again; Jill simply did not stop this time; did not think about her gag reflex, and did not concentrate on where he even was in her mouth. It wasn't until she felt his pubic hair tickle her nose did she realize that all of him was inside her, and luckily she did. He started to come at that moment and she was thrilled to feel him splashing come into her, feel his strong thighs buck against her mouth, feel the throb of each spurt as it went through the shaft of his cock.

Finished, she sat up, wiped her mouth with a Kleenex and smiled at her satisfied customer! " $50 please", she said with a triumphant smile!

"Your really going to make me pay?" he said with a pained look on his face.

"Damn right, how am I going to pay the babysitter Robert?" laughing as all of the tension of the game was gone, she had fulfilled her fantasy and was elated by the result.

"Lets go home, Jill. I am anxious to see you in that outfit without the jacket." With a wink to his wife, they were off.