#5 Masturbate On Webcam

I think it is about time I told this story and no it doesn’t involve me just whipping it out on Chatroulette like many guys did a few years back. This took place just under two years ago and is probably a different experience than you might imagine. It all started on my Erotica twitter page, which at the time had about 10,000 followers. I received many messages daily, but one in particular progressed further than most. It was a man from Canada who just was interested in talking shop, until the day he propositioned me.


He said he and his lover were quite kinky and were interested in being watched on webcam while a guy masturbates to them. At first I was a bit taken back, for some reason I never thought I would be one to do something like that. I just gave him the basic maybe and he said he’d have to discuss it with his wife first. I still wasn’t sure about it, so I told him to take all the time he needed.


A week had passed and I figured I wouldn’t hear from him again, but sure enough I recognized his avatar in my inbox. She was thrilled to do it and thought I was cute; the ball was now in my court. I remember discussing it with a friend of mine who basically always tells me to step outside my comfort zone, so it was no surprise he said I should do it. I took the plunge and said yes. We agreed to do this the next night and I began getting a bit nervous. I was excited to see two people having sex basically for me, but it was a bit intimidating having to sit there on camera masturbating to them.


The night came and I made my way downstairs and got comfortable in the guest bedroom waiting for them to log onto Skype. When the notification that they were online popped up, I immediately felt my heart pounding. I positioned myself the correct way and clicked the call button. I sat there waiting until it popped up a dimly lit room with bed in center frame. The guy asked if the quality was good and I said it was just fine. He walked into frame, he was maybe in his mid forties and was in only his underwear. Then his wife walked into frame, she wore just a bra and panties and it was then I realized this was really going to happen. I half expected it would just be the guy tricking me into watching him.


She was hot with shoulder length dark hair, the two of them looked at the camera and smiled. He directed her on top of her and she began pulling off his underwear and without hesitation began sucking on his flaccid cock until it grew hard. Every now and then they would look over at the camera to see what I was doing. I took this as a cue to join in. I slid my pants right off and grabbed a hold of my growing cock. They began looking over at the camera more often as I stroked myself.


He flipped her over onto her back and slid off her panties; I was becoming increasingly hard. She rested her head back on the bedding as he went down on her. This didn’t last long before he climbed on top of her and slid his cock into her. The two began fucking in the missionary position. To be honest it wasn’t the greatest of views because all I could really see was the man’s ass clutching with each thrust between her spread thighs. The two couldn’t see the webcam so I just sort of held onto my cock as they went at it.



After I’d say a good five minutes he climbed off of her and she leaned forward to suck his cock a bit more. He was on his knees on the bed looking over at the camera as her head bobbed back and forth. Then he laid down and had her climb on, she never took off her bra. The angle was terrible once again, but suddenly he realized that. “Shuffle this way, so he can see you,” he said. They positioned themselves facing away so I could see the back of her as she rode his cock. This was by far the hottest position I got to watch. The arch of her back and her ass pounding down onto his thighs.


I quickly stroked faster watching this random couple fuck for my viewing pleasure. This was something many people have to pay for. I couldn’t last much longer as I felt the climax building. They said they wanted to know when I was going to cum, so I said softly I was about to cum. She turned her head and he peaked over her to watch me ejaculate. She let out a moan and he said something like “way to go” and then went back to fucking. I wasn’t sure if I was suppose to stick around, who knows the proper etiquette when it came to a situation like this. I watched a little longer, but the novelty wore off and I just hung up the video call.


We didn’t speak again until the next day and they both said they enjoyed themselves. He said his wife asked if they could watch me with a woman and I explained I don’t really have anyone who would be willing to do that at the moment. We talked every now and then, but now we haven’t had any contact with one another in over a year. It was definitely an experience I’m glad I took part in. If nothing else, I got a story out of it.


Until next time. Happy cumming,


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