[MF] I masturbated while (m)y best (f)riend watched. [cheating]

I met Kris through work. Kris is a 33 year old professional woman and at the time we met, she was married. I’m a 48 year old married professional in a slightly different line of work, but due to the natures of each of our professions, we had chances to cross paths on occasions and we kind of clicked. We got each other. Now, I am a happily married man and my wife is one of the greatest, sexiest women anyone could ever meet and I am lucky to have her. Didn’t mean I didn’t find other women attractive and sometimes my little head thinks before my bigger one does. Kris is one of those women I find incredibly attractive. She is tall, probably close to matching my 5’ 10” frame when she wears her spiked heels, as she tends to do when she works. She has a young child, but childbirth doesn’t seem to have had much of an impact on her amazing figure – Kris has a perfect body. In her little business suit, she is the best combination of nice large B/small C breasts, long shapely legs and perfect ass. I used to find ways to walk behind her just to get a glance at her beautiful butt. Soon after meeting Kris, she added me on Google Hangouts for business reasons initially, but pretty soon we would find other reasons to chat every few weeks. Those weeks in between chats soon became days and the days soon just became constant. We talked all the time when we weren’t working. I looked forward to getting home and chatting with her as I watched videos or TV or played a game on my computer. Kris’s marriage was dissolving quickly and I was a friend to her at a time when she seemed to need one. I started to consider her one of my best friends and she thought the same.

This went on for several months. We literally chatted about everything, from sex, to music to philosophy and anything in between. We even acknowledged that we both found each other attractive, but Kris made it clear from the first time talking about it that she wouldn’t sleep with me and I was okay with that – I’d rather have her as a friend than for anything to come between us. Things would occasionally get a little flirty, but it was mostly innocent and never really went anywhere. We both have an incredibly dirty mind and I think we would just generally chalk our flirtatiousness up to that and move on.

Kris’s job and recent break-up took her across town to another location, so we didn’t have any more opportunities to meet face-to-face in the course of work, so our relationship became online only. Being a busy, married guy, I don’t have a lot of chances to hang out with attractive female friends, so I just accepted that this was how things would be and rolled with it. We would send each other random photos of our lives as we went about our days, but it was never anything sexual, other than a single shot I took of my hard-on in my jeans that I sent her after a particularly arousing chat about a sexual experience Kris had with a guy she had been seeing for a few weeks. I told her that hearing her talk about getting her ass fingered by a guy was really hot. Kris said, “Tell me about it.” I replied back with, “I’d rather show you instead,” and sent her the shot of my bulge. She replied back with, “well, it does seem like you enjoyed that!” and that was the end of the conversation.

It was not long before I began to miss being able to see Kris in person. One afternoon while sitting at my PC, I remembered my webcam that I never use. I set the camera up as a full-time streaming device, so that she could log on at anytime and see what I’m up to. We had both talked about having really strong voyeuristic streaks before, so I had an idea that she’d appreciate the idea.

I was right. I sent Kris the IP address to my camera and she logged on almost immediately and started saying how much she enjoyed watching my face as we chatted. I told her that she was welcome to log on at anytime and she thanked me. She asked if I knew whether she was logged on. And I lied. I lied because in the back of my mind, I wanted her to feel completely free to log on at anytime and I had a feeling if she thought I knew when she logs on, then it wouldn’t be quite as “naughty” for her and she wouldn’t want to do it. See, when a viewer connects to the camera there’s two things that happen. First, a little beep plays and secondly, if I have the software up on my desktop, it shows the IP information for anyone connected in a little window along with the amount of time they have been connected. I told Kris that the only way I could see she was connected is if I had the software up on my desktop I would get a little beep, but I was sure to add “I almost never have the software up.” This seemed to make her comfortable, because I noticed she began to log on to the webcam more often over the next several weeks. I would always act a little surprised when she would say things like “You look nice today” or something similar. I also got really good at ignoring the little beep that plays when she connected. This tactic paid off big time after a few weeks of Kris getting accustomed to watching my face and me pretending I didn’t know she was there.

Kris and I became quite familiar with one another’s schedules. I knew she would go to bed between 10 and 10:30 most nights, even on weekends. She knew I stayed up until 12 or 1. One Saturday evening, Kris had done her usual disappearing act around 10 pm and I decided I’d play a game for a bit. My wife had also gone to bed early that night, so it was just me and my computer games for a couple hours. Just the way I like it. I played a few rounds of PUBG and got my ass handed to me several times, which is pretty typical, and closed the game out of frustration. I was still a little keyed up from losing and decided that there was only one remedy for my tension: a good jerk off session. I opened my browser up to one of my favorite picture websites, sat back in my chair and took in the sights. I landed on this awesome set of photos taken of naked girls at outdoor concerts and pretty soon, after having stared intently on several pics of ladies in various stages of undress, my hand went unconsciously to grasping my growing member through the fabric of my thin sweatpants. I was massaging myself pretty blatantly when I heard a familiar sound at a rather unfamiliar time of night.

BEEP, BOOP. It was the unmistakable sound of Kris logging onto my webcam. I had a critical decision to make and only a moment to make it. As she logged on, I was leaning back in my chair and my hand was pulling and tugging my pecker through my pants like I was trying to soften up a new jar of Play-Doh. There was no mistaking what was happening here. I could just let go of myself and return my chair to its normal upright position and pretend like I hadn’t just been caught. Or I could play this out as far as possible.

I chose the latter.

I became acutely aware of my heart beating insanely fast in my chest. It felt like it was going to burst through from the sheer excitement of what I knew was happening. I imagine my face was bright red in the camera as well. I continued to knead my ever-hardening cock through my pants while occasionally glancing at the little window for my webcam software to make sure Kris was still there and watching. By this point, I was paying no attention at all to the pictures that had initially gotten me aroused. Now I was going on pure adrenaline.

Once I had decided that this was going to end up with me putting on the show of my life, I figured it was time to commit to it. But I LOVE teasing women, so I was going to take things about as slowly as a masturbation show can go. I stood up from my seat and pulled down my sweats to the floor and dropped them to the ground, but I elected to leave my dark blue boxer briefs on and sat back down. I lifted my shirt in order to allow for a better view of my slim physique and spread my legs wide. My hands continued to massage and play, carefully lifting my cock underneath my underwear in order to allow Kris to see the general size and shape of it. I could still see Kris’ IP address in the window on my desktop and I began to get even more excited, thinking about what she was doing at the other end of the camera. Every once in a while, I’d allow the tip of my head to peek out from a leg of my underwear, but I was careful to only give little glimpses of it. I stared at the pictures of the naked women on my screen, but the only thing I could think of was Kris and her beautiful eyes glued to her own device’s screen. Watching me pleasure myself. I continued doing this for several minutes until I figured it was time for the next phase. Putting my hand into my shorts, I adjusted myself until I could get into a good jerking rhythm under my boxers. I was stroking myself and slowly allowing each successive stroke to bring the waistband of my shorts a little lower. Finally, I reached under the waistband and pulled it down underneath my balls to reveal my hard, 8 inch cock to Kris. I pointed the head toward the ceiling and kept on stroking slowly while playing with my balls and gently touching myself all over. I couldn’t believe I was jerking myself off and my hottest female friend was watching me do it. I instinctively stood up and pulled my underwear all the way off.

Returning to my desk chair, I placed my feet on the edge of my desk and leaned as far back as I possibly could. I wasn’t even looking at the screen any longer. I had my head back and was imagining my hand was Kris’. My anxiety had given way to sheer excitement, and I was loving it. My once gentle strokes were now full-on frantic meat-beatings. I was pounding myself while tugging at my balls. I knew I was getting close, so I put my head back, moaned a loud grunt, pointed my throbbing dick straight up and spasmed. Ropes of cum covered the front of my shirt and one small drop even hit me in the chin. After a long moment of shooting load after load of sticky mess all over myself, I sat still taking in what had just happened. I half-way expected to look at the monitor and see no sign of Kris, but no, she was still there. Watching. My best friend had watched me jerk off from start to amazing finish.

As I cleaned myself up, I noticed that she disconnected.

The following day started pretty much like any other. Kris and I chatted for a bit about the day ahead and things seemed pretty normal. Then, out of the blue, Kris hit me with this question:

[https://imgur.com/a/NFiF8]

She definitely watched the whole thing. I never confronted her on that, mostly because it would mean I’d have to tell her that I can always tell when she’s logged on, and keeping that close to the vest has come in handy a few times since. But that’s a story for another day.

Source: reddit.com/r/gonewildstories/comments/7czbam/mf_i_masturbated_while_my_best_friend_watched