"So how did Brian do?" Nancy asked.
"He was fine. Went to bed about an hour ago, no problems," Jay responded.
"That's good. Lately he has had problems falling asleep and doesn't want to go bed. Sometimes I have to sit with him until he falls asleep."
Jay had lived next door to Nancy for 12 years. Brian came along about five years later when she was in her late twenties. Once married but now Nancy's ex-husband was out of the picture. In middle and high school, Jay had often watched Brian if Nancy was busy in the evening. Jay hadn't watched him since last fall when he left for college, and Nancy was glad he was home for the summer now.
"Why don't you come back to the bedroom," Nancy suggested, "I left my wallet in my other purse"
Jay followed her to the bedroom. Nancy flipped on a switch for the lamps on either side of her bed. She grabbed a purse off her dresser and sat down on the bed.
"It's great that you are home for the summer. Glad to have the first year behind you?"
"Definitely," Jay responded "it was a long, hard year."
"I bet," Nancy smirked to herself as she rummaged through the wallet.
"How's $20?" Nancy asked as she handed him the bill.
"Sure, that's fine."
"You know, I saw you through the window last Wednesday night as I was waiting for Brian to go to sleep."
"Oh, yeah, sometimes I can see into Brian's room," Jay didn't think to much of the comment. His room was directly across from Brian's and if he looked out his window, he could see into Brian's room himself.
"I was impressed, I didn't get to see the end though."
Jay had a confused look on his face, "When was it again?"
"Wednesday."
"Oh fuck," Jay thought. He had taken a shower and returned to his room in just a towel. He was hard as hell and in need of some relief. After he dropped his towel, he stroked his cock for a few minutes before turning off the light and laying down to finish. He didn't realize anyone had seen him.
Jay looked at Nancy with a panicked face and then turned away.
"It's OK," Nancy said with a reassuring chuckle, "I like to see guys jerk off."
Jay's face was turning red. He turned back to her but didn't know what to say.
"Why don't you do it again, but this time let me see the ending."
"Uh...," Jay responded, trying to form some words.
"Right here. It's OK."
Nothing was said for several moments. Jay looked down at the floor and around the room, trying to avoid eye contact with Nancy while she sat on the edge of the bed. She had an anticipating smile on her face as she leaned back with her hands behind her.
The only thing Jay really knew at this point was that his cock was getting hard and he was afraid she would see it through his jeans.
"Really it's OK," Nancy tried to reassure, "I've already seen it." She emphasized the "already."
Jay wasn't sure what to do, walk out the door, laugh it off, or pull it out and start stroking.
"I don't... It seems kind of weird to do it in front of you," Jay finally stammered.
"Because I am older? Because you have known me a long time?"
"Yes."
"So you have never watched me out in the yard in my bikini?"
"Uh, well...." An image of her flashed in his mind. The bikini had been lying on the floor of the bathroom that night. He couldn't resist to pick up the bottoms and feel the crotch. He had seen her several times in the backyard wearing that brown bikini.
"Does your dick get hard when you see me in it? Like it is right now."
Jay looked down at his pants, embarrassed. It was obvious the state he was in, and he could feel it starting to throb.
"It's OK, pull your jeans down," Nancy encouraged again.
With that Jay got the courage to take the plunge. He undid the top button, then pulled loose the rest. He stood there for a moment with his fly unbuttoned, the jeans still on his hips. Nancy watched with anticipation.
As Jay pushed down his jeans, the boxers hung up on his hard dick. He freed it, then continued to push both down to the middle of his thighs.
"See, that wasn't so difficult, now was it?" Nancy laughed. Probably close to seven inches, but most impressively, he was thick. Secretly she was impressed, but kept it to herself so as to not further embarrass him.
Jay shook his head, trying not to look her in the eyes.
"Don't be embarrassed, it's sexy. Let me see you stroke it."
Jay closed his eyes, took his cock in his hand and began short slow strokes. He didn't really know what to expect. Did she want more? Was she going to help him?
Nancy took in the view as she leaned back and relaxed on the bed. She could feel herself getting wet, but for now she had more control then a young college boy.
After a couple of minutes Jay began to relax and lengthen his strokes. He wondered how long he would be able to last and tried not to rush it. Where did she want him to cum, did she really want a mess on her floor? He looked down to see he was standing on a rug covering hardwood. "At least it will clean up easy," he thought.
"Need a little help?" she asked.
Jay looked up to see Nancy unbuttoning her shirt. He watched her closely as she slowly worked her way down. When she got to the bottom, she pulled the tail of the shirt out of her jeans and finished the last two.
Nancy pulled the shirt off her shoulders and laid it on the bed. Her breasts weren't huge, but they were definitely above average. And for her age, they were still firm.
Jay was mesmerized, he could see her nipples poking at the white bra and wondered if she would take that off too. Nancy cupped her breasts and played with her nipples through the bra. She was getting worked up too, they were like bullets and she could feel the dampness in her jeans.