A few months ago, I moved into an older neighborhood with homes close together. One side of my house faces the courtyard and side wall of the neighbor, and there's only about ten feet between our houses. The neighbor on that side is a widow who is in her late 60s. Debbie is not in great shape but still healthy and works in her garden. She's cute, and I can tell that she used to be a looker.
We became casual friends, and we often wave and share small talk when we're both out in the side of our houses. My desk is near a window on that side of the house, and Debbie waves when she sees me through the glass.
After a stressful week, I decided to get a massage to relax. I'd used a service before that I liked, and called them for an appointment. This time, I decided to have them come to my home for the service. I asked if a woman I'd had before was available, and sure enough she was. Her name was Jewel, and she was not much younger than Debbie. She had done a great job before, including a super happy ending when she handled my eleven inches to perfection and teased it before pumping a gusher out of me.
I cleared a space in the room facing Debbie's house with three large windows facing her garden and the side windows of her house. I knew she could see into my house and might observe the massage, but I figured I was in my private space and she could choose to look or not. It was just a hunch, but I thought she might like the option of enjoying the scene from the privacy of her property.
The masseuse arrived for the appointment and brought a folding massage table into my study. I helped her set it up near the windows but with room for her to work. I undressed, wrapped a towel around myself, and laid face down on her table. She began to work on my shoulders and back, and it felt wonderful.
Every so often, I peeked out the windows to see if Debbie was watching. All of a sudden, she opened her back door and stepped out onto her patio to water plants. She looked up and saw me. I smiled and waved, and she gave a quick wave but soon disappeared into her house. Moments later, I think I saw her peeking through the blinds.
I was still in modest condition, with a towel covering my buttocks. Jewel didn't seem to notice that we were being watched. Soon, Debbie came out again, pretending to putter over something, but I'm sure she wanted to let me know that she could see me. She looked at me and made a funny face, like she knew I was doing something naughty.
I pretended to have my eyes closed, but I was watching her. The scene was making me very aroused. Jewel's excellent massage, Debbie's peeping, and anticipating what was to come made my heart race.
Soon, Jewel removed the towel and massaged my buttocks and legs. I parted them slightly so she could see the effect of her touch on my cock as it lengthened down the table between my legs. After working on my feet, Jewel's hands traced up my inner leg and her fingers dragged along the length of my cock. That was my cue to turn over.
As I did, I saw Debbie's eyes peering at us through the blinds covering her widow. What was they thinking as my cock flopped into view? Once on my back, Jewel rubbed my chest and arms for a while, then my legs, but all the while the effect of her touch was making my cock thicken and harden. Soon, my dick was arched upward in a semi-erection.
Jewel matter-of-factly dribbled a line of oil on my prick, then she used just one hand to smooth the oil down my shaft and up over its plumb shaped head. She kept her hand open and only touched my dick with the palm of her hand, applying no pressure. She just pushed my cock with her slippery hands as it gradually rose higher and higher. At this, she was an expert.
Then she only used a finger, a single finger, to move my dick this way and that, playing with it and teasing me when she knew I craved a firm grip. Debbie was clearly watching us the entire time.
Only when my cock was fully erect and standing tall on its own did Jewel first grip it with her fingers not quite being able to surround the entire shaft. She pulled up and released, pulled up and released, over and over. The she started at the top and encased my bulb with a hand, squeezed tight, the slowly descended to the base of my shaft. Over and over, slowly, she kept this up while my neighbor watched.
Finally, Jewel wrapped both her hands around my dick, leaving about three inches clear at the top, and gave me a fierce pumping until I was close to an ejaculation. Then she would stop and repeat her gentle teasing touches. When the hour was coming to a close, she renewed her baseball bat grip and gave me one of the best finale's a man could have.
When I climaxed, spurts of cum rocketed out of my dick on each stroke. She knew how milk a man, that's for sure. Even after the first few blasts of cum that launched high into the air, she still nursed out another five or six spurts. I was exhausted. But oh so relaxed!
And my neighbor was entertained, I was sure.
I arose and paid dear Jewel and promised to have her back as I saw her to the door. Then I hit the showers.
The next day, Debbie was sitting on her patio with a lady friend about her age. Her friend looked quite attractive. I don't think she saw me, so I watched as Debbie talked and occasionally pointed to my windows. I decided to take a risk.
I walked out into the side yard, just a few feet from where they sat, and greeted Debbie. I walked over to introduce myself to her friend, Rose. They were old friends and had been active together in the Junior League and Women's Club when they were wives, but both now were widows. Debbie said they were planning a get together of some of their friends.
Did Debbie tell Rose about watching my display the day before? I could only use my imagination.
When Rose left, I came back out and chatted with Debbie. I decided to be bold, "Last week was very stressful, and I scheduled a massage at my house. I hope you didn't mind that you saw me through the windows."
Debbie looked surprised but answered, "Oh, no, you deserve to relax after a busy week."
"I forgot to close the shades," I added, not wanting to say more until she volunteered her thoughts about what she saw.
"That's OK, I went inside."
I pushed a button by asking, "Did you watch through your windows?" I asked her.
Debbie was silent and was obviously trying to decide what to say. Finally she laughed and told me, "Well, a bit."
"And what did you think?" I asked.
She seemed to blush but managed to say, "Well, someone's got a whopper."
"A whopper what?" I asked. I was enjoying putting her on the spot.
"Well," Debbie said, "let's just say that you have more than twice what my husband had."
I was extremely pleased to hear her say that, and you can imagine the effect this talk was having on my pecker.
I smiled at her and said, "Well, we're good neighbors, so there's no reason to have secrets." "By the way, I've scheduled another massage for next week. Would you like me to close my shades?"
Debbie looked flustered as she tried to give me an answer that wouldn't make her look like a cockhound, so I laughed and said, "My curtains are always open for you."
I left it at that and walked back to my house. I wanted to let her perk for a while before pushing anything farther. But I had a plan.
The next Friday evening after work, I saw Debbie in her yard and stepped over to visit. We shared small talk about this and that, and then said, "The masseuse will be over tomorrow at 3:00, and you're more than welcome to come over, too."
I didn't wait for a reply since I knew she would take a while to figure out what I meant by such an invitation. I wanted her to think about it and decide if she wanted to get closer to things or remain at a safe distance. After all, it should be the lady's option.
On Saturday, my masseuse Jewel arrived right on time, but no Debbie. As Jewel was setting up the table and as I was getting undressed, there was a knock at my front door.
It was Debbie. She said she didn't know if she had heard me right about "an invitation."
"Sure, please come in," I said to her. I bare chested and wrapped in a towel when I introduced her to Jewel. I had alerted Jewel to the possibility that my neighbor may come over, and promised to give Jewel an extra large tip if we had company.
I showed Debbie to a comfy chair and then I hopped up on to the massage table. As she rubbed me, Jewel explained what she was doing as if she was training Debbie how to do it. Every so often, Debbie stood to see better.
When I turned over and exposed my dick and balls, Debbie muttered, "Just incredible."
I asked her, "Sorry, what did you say?" I had heard it, but I wanted to draw her into the action.
"I said it's just so big."
Of course, that made my dong leap up and gain strength for the stroking to come. After her foreplay, Jewel got ready for the big tease and the finale. She asked Debbie if she could give her some help. Debbie stood and looked puzzled.
Jewel said, "Put this oil on his penis, would you?" Debbie took a bottle of oil and squeezed out a river of oil the entire length of my dick.
Jewel pretended to be busy and asked, "Dear, would you rub the oil into his skin?" Jewel knew she was breaking in a new hand, and Debbie was lucky to be taught by the best.
Within a few minutes, the two of them, one on each side of the table, were inventing new ways to torment me with gentle touches, tickles, ball games, and devious grips and strokes.
When the hour was up, Jewel said, "Well, I'm only hired for one hour and I've got another appointment next." "Gotta run, but maybe Debbie can finish the job."
I arose, Jewel folded up her table and left, with an extra large tip, I might add!
And there we stood, Debbie dressed in her casual clothes and me totally naked, erect, and dripping.
"Debbie, you were a good sport, thanks for coming over," I told her. I waited for her to take the initiative, if any.
"I think I'll sit out on my back deck and finish what you and Jewel started," I said. I walked through my house and Debbie followed after me.
Once outside in the open air, I reclined on a lounge chair and started to touch myself. Debbie sat next to me and took over. She seemed to adore the extra large serving of cock in her hands and gave me her full loving attention.
I tried to hold back and let her take her time, but it was too much. Soon I was beginning to rumble and feel cum boiling up. I told her, "Be careful, move your head back, you're making me cum." And just then the first blast leapt up a few feet into the air, followed by about eight more of decreasing volume and force.
When I was spent, Debbie just sat there next to me nursing my limp member in a pool of sticky spilled cum.
"Wow," she said.
"Did you like that?" I asked.
"What do you think?" she replied.
It's been a week since this happened. I've asked her about Rose and about the coming party for her friends. She hasn't said anything to me yet, but each time I see her, I've teased about how much her friends might like to enjoy a cock show. We'll have to give it a little time for my witches brew to bring results.