I do travel quite a bit and I try to keep in touch with my wife by phone and by email, both. My laptop had a built-n camera and I often would take a picture of the body part of mine she says she misses the most and send it to her to keep her company.
So, after three days away, I got myself up to maximum and took a good pic and sent it to her.
The second I hit 'Send" I knew I fucked-up. Off it went to Janine, my sister-in-law instead of Janis, my wife. Shit, shit, shit. I wasn't really paying attention and the autofill on my computer just filled in "Janine" as soon as I typed, "Jan..." and I pressed the button and off it went.
Now, they were both in their mid-thirties, my wife is thirty-five, her sister, a year younger. So, here I was sending a salacious picture of my cock to my wife's sister.
There was nothing to be done but send a follow-up email to Janine which I did trying to explain what happened and hoping that the picture file was closed when she got it.
Now, my sister-in-law looks a lot like my wife. They're both tall, willowy blondes with very nice figures. You would immediately know they were sisters when you saw them together. And, thankfully, the both have a terrific sense of humor. I just might need that, I thought.
A few minutes went by then an email popped into my inbox. There it was ... from Janine.
I opened it and read: "hehehe, no problem, Holt, my sis is a lucky girl if she gets to have fun with that all the time. Thanks for the nice look. Janine"
Whew! I was right to count on her sense of humor, lucky, I guess, so I fired off a reply thanking her for her understanding and that now she knew just how perverted her sister and I are when I'm off traveling and that I'm glad that I didn't send her the video I made that I sent her on my last business trip. And I hit, 'Send.'
Now I knew that last bit about the video was, well, maybe, meant to tease a bit, after all, I was in a hotel room, all alone with a fierce hard-on, and she was my wife's sexy little sister. I sat there at the desk, naked, rubbing myself with one hand, searching the files on my laptop with the other. There it was the video of me jacking-off, about five minutes worth, ending is a great cum scene with long ropes of sticky semen spurting like a fountain.
Yes, I sent it. Maybe I shouldn't have had those two brandies after dinner.
I sat there watching a video of a threesome I have on my laptop just for times like this when I'm traveling and bored in a hotel room somewhere. Slowly stroking myself as the video played, I saw an email come in and it was from Janine. "Well. All I can say is, WOW! It made me more than just a little wet watching you having fun by yourself. How did you know that it's something I just love to watch. ;-) Janine"
So, I emailed her back and told her that she could watch me do it any time she wanted.
We sent little emails back and forth like this for the two more days I was out of town, just kidding around having a little sexy fun. I had ended with a more or less kidding offer to do it for her in person the next time were together.
Her last email to me was that we would be getting together at the end of the month at her parent's lake cabin for a full week near the end of summer, so maybe then.
Well, it was kind of fun, just fooling around, anyway, life went on and I had pretty much forgotten about it until Janis reminded me of our upcoming visit to her parent's lake cottage. Then, the memory of it popped in my mind and gave me a bit of a hard-on as I thought back to it.
Well, a little joking, it was fun.
When we finally did see each other at the cabin, it was a large one, five bedrooms, we hugged and pecked each other's cheeks as we always did but there was something else there, a definite sexual charge between us. It was strong enough not to be missed and I just hoped that no one else picked up on it.
Time went by, there were so many of us there, that Janine and I were almost never together but on the second night, we did find ourselves alone in the kitchen making some drinks to take outside to the bonfire. I took the opportunity.
"Gee, Janine, I'm a bit embarrassed seeing you again after you've seen so much of me."
"Don't be embarrassed, Holt, I've thought of that a few times when I've been alone."
It could mean only one thing. She was masturbating thinking of the pic and video I'd sent her. Oh, my.
"Well, Janine, that's kind of a turn-on for me. I may need to seek a little relief pretty soon, myself."
She looked over at me, smiled and said, "Oh, really?"
Wondering just where this might lead, I posed, "Yeah, in thirty minutes, I'm going to head back to the bathroom at the back of the house for a little 'quick relief.' You just might catch me cumming again," and she flashed me a cute grin and took a tray of drinks outside.
I knew I had raised the ante between us but now the ball was clearly in her court. I would have a nice little jack-off session whether she came to watch it or not.
We were all sitting around the fire, drinking and talking and having a good time then the half-hour rolled around, so I told Janis I needed to use the bathroom, got up and walked into the cabin and down the hall to the bathroom at the back.
I got in the bathroom and decided to waste no time, so I unzipped my jeans and wrangled out my, now hard, cock and began getting it even harder. I wasn't sure what would happen but I was a combination of excited and nervous as I stroked back and forth.
My cock was starting to feel pretty good when there was a soft rap on the door. I pulled it ajar and it opened and Janine was standing there.
"I'll just watch from here, Holt, so I can see if someone's coming. Well, I mean other than you," she added with a snicker. "Go ahead, I want to see."
I turned more toward her and resumed jacking-off. Her eyes were staring at my cock as I pleasured myself.
"Hurry, I want to see you cum," and I turned a bit toward the sink as my cum began spurting out, most of it landing in the sink. I stood there, a string of cum dangling down from the tip, my hand covered in my cum.
I let go of my cock which stood straight our and she said, "Oh, that was great. Thanks, Holt," and wrapped her fingers around it and gave me a few strokes, then wiped her finger across the tip, slid it into her mouth and walked away.
I went back out a few minutes later and busied myself getting people refills and did catch my sister-in-law smiling at me once as I shuffled back and forth, our secret sealed between us.
The next few days, we flirted a bit back and forth when the opportunity arose which, of course, meant my cock arose, as well.
.... There is more of this story ...