Disclaimer: This story and all characters are fiction. All characters are 18.
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Phillip watched Donna through his living room window, as she talked to his mom and dad in the fading light. After his parents got in the car with his sister and drove away, he continued watching Donna in her yard, smoking a cigarette. The pretty brunette neighbor must have just arrived home from work, looking dressed up in her black skirt and white blouse. Philip was told that Donna was over fifty, but it was hard to believe. She was so slender and trim. Just look at those legs! And she has grandchildren! Everything about her, her walk, her movements, her hairstyle, exuded sex appeal. Alone in his house in the dark, peeking through the window, Phillip started rubbing his teen-aged dick through his slacks. When Donna entered her house, he kept watching. He had never come close to seeing Donna naked through the window, but he kept trying. He had seen her in a short nightgown a couple of times, and once in a bathing suit, but that was about it.
Phillip watched Donna in her kitchen, pouring herself a drink from a liquor bottle. She seemed to absent-mindedly stare out the window, but when she looked over towards Phillip's window, he ducked back. He watched for another five minutes, but Donna wasn't in a hurry to change, so he left the window. Not three minutes later, the phone rang.
"Hello?"
"Hello, is this Phillip?"
"Yes."
"Hi, this is Donna, from next door." Phillip's heartbeat picked up. He had only talked to Donna a few times in the presence of his parents and her husband. He had never talked to her on the phone."
"Hi."
"Is your mother there?"
"Uh, no."
"Will she be back soon?"
"No. They won't be back until after eleven." Phillip thought it strange that Donna would see his mom drive away, then immediately call looking for her.
"Oh. So you're all alone tonight?"
"Yea."
"So am I. My husband won't be back until real late. So how are you Phillip, I never get to talk to you." Donna's voice was low and a little sultry.
"I'm fine."
"Got any plans tonight?"
"No. Just watching TV." And watching you, he thought.
"Me neither. I stopped off for a drink after work, and just got home. You don't have a date tonight?"
"No."
"Do you have a girlfriend?"
"No."
"You're a good-looking young man, I was watching you out in your yard the other day."
Phillip's cock jumped. He couldn't believe a woman approximately three times his age was checking him out. "Thank you." He didn't know what else to say.
"You're pretty quiet, aren't you?"
"I guess."
"I'll bet you'd get lots of girls if you tried. Sometimes if you just ask a girl a direct question, you'll get what you want."
Phillip sat in the dark with a hard-on, but could only shyly grunt an affirmative to the married neighbor that he had jacked off so many times while thinking about.
"Have you ever watched me through your window?"
"Uh, I've seen you outside."
"It's OK to tell me. I won't tell anyone. I thought maybe I saw you in the window once or twice. Don't you look at me?"
"Well, yea, a couple of times."
"Well, I'm flattered that an attractive young man like yourself would show me any interest at all. Do you think I'm attractive?"
"Oh, sure, yea." Phillip restrained himself from divulging how hot he really thought she was.
"Well, thank you. I'm looking at your house, and I don't see you. What room are you in?"
"I'm in the living room,"
"I'm upstairs. Why don't you come upstairs? Are you on a cordless phone?"
"Yea. I'll go upstairs." Phillip sprinted up the stairs two at a time. Looking out the upstairs window, he could see Donna clearly in her upstairs bedroom, with the lights on, standing in the middle of the room. She had her cordless phone to her ear, and a drink in her hand, still in her blouse and skirt.
"Turn on the light." Donna requested. Phillip turned on the light and stood in the middle of the room. He and Donna were watching each other through their windows, each with a phone up to their ear. Donna waved at Phillip and said, "Hi" in the phone. Phillip waved back. "You're getting big. How tall are you now, Phillip?"
"I'm about five-foot-six."
"That's pretty tall for your age. That's how tall I am." From fifteen yards away, Phillip watched the slender, mature woman watching him. "I really need to get out of these work clothes. You know, from here, you're the only person that can see me. Would it bother you if I changed?"
"Uh, no." Phillip tried to keep his voice at an even tone. She couldn't have meant it the way it sounded. He watched Donna put her drink down, but she kept the phone held to her ear with her shoulder.
"I have to get these shoes off." The window only revealed her from her knees up, but he watched her lean over, lift her knee, and remove her right shoe. She did the same with her right shoe. Philip didn't know what to say. He stood watching silently.
"I had a busy day at work." Donna continued making small talk, but as she did, she reached up and unbuttoned the top button of her blouse. Her conversation only half- registered as he watched her slowly unbutton all of the buttons down her blouse. He could see just part of her white bra inside of her blouse. He heard her breathing as she pulled the blouse out of her waistband. She unbuttoned the cuffs, then held the phone in one hand while pulling off her blouse with the other, letting it fall onto the floor.