The first couple of weeks last year were driving me crazy. As a freshman in college, I had never shared a room, and lamented the inability to jerk off whenever I needed to. I worked around Josh's schedule, but it was still a pain in the ass. One night Josh sheepishly asked me if he could have a half hour alone. I said no problem, but pressed him as to why. He finally told me he was going to have video sex chat with his girlfriend who was at another school. I went to the common room, and was all boned up, thinking about Josh and his girlfriend getting off over the net. While I was in the common room, called my girlfriend (still in high school) and told her how jealous I was of Josh. To my delight, she said she would like to do it too, so we set up a time the next day for us to do our first ever sex video chat.
Josh texted me the all free message, and I came back to the room. He was on his bed, shirtless in gym shirts with a huge shit eating grin on his face, arms behind his head. I let him know that Maggie had agreed to do it too, and that if it was ok, could I have the room at 3:00 the next day, when Maggie would be home alone. He said sure, and I prodded him how it went. He was really open talking about how hot it was to watch her undress, then play with herself as he directed her what to do. He said seeing her pussy from the camera angle was really hot, and that when she came, the sight of her lips covered in sheen sent him over as well. I was hard again thinking about the next day, but made it through the night without doing it.
The next day I was excited as we started. First we stripped for each other, then positioned the cameras between our respective legs. I urged Maggie on with some fairly filthy talk, telling her how I missed her beautiful wet pussy, and how much I wanted to fuck her. I told her when to play with her tits, when to rub her clit, and when to fuck her fingers. When she groaned my name, and thrust her hips, gasping she was going to cum, I lost it and sprayed a load onto my chest. We both laid there naked, catching our breath and talking about our afterglows. I cleaned up, and we said goodbye, and I sent Josh an all clear text.
When he came into the room, I was in the same shirtless, hands behind the neck pose he was, with an equally broad grin. He pointed out to me that my chest and face were a bright pink flush, something that always happens to me when I orgasm, which apparently with Josh's Italian background doesn't happen to him. I gave him a recap of the session, and saw he was tenting in his shorts.
Over the next few weeks, this went on three to five times a week, each of us getting off with our girlfriends on the net.
We both had external cameras, because the quality was better, and it was much easier to position the cameras where we wanted to, and still see the screen. One night, Josh was on his bed, texting with his girlfriend, but no camera. He told me to come over, and when I did, I saw his girlfriend was masturbating for him. She had trimmed her pubic hair very short, and was rubbing her fingernail lightly over a very large dark clit, and tracing her labia, which were the biggest I had ever seen. I was mesmerized. She was pulling on her nipples, alternating left then right, and swirling her hips. He looked up at me with a devilish grin. He typed her some raunchy instructions, and she complied. He looked over his shoulder at me, and his face was inches from my tented shorts, and pulled his head back instinctively, and laughed. Then he lifted his laptop off his crotch, revealing his tent, then to my surprise he said fuck it, this is too hot, and pulled his shorts down. He put the laptop between his thighs and started to stroke.
Watching the two of them masturbating, I pulled my shorts down and started to jerk as well. When she started to cum, he started breathing hard, and when she rolled her head and her hips lifted up, he shot onto his belly, and I hit the floor. I quickly pulled my shorts up, grabbed a towel and cleaned up the tile, Josh mopping his stomach with his t shirt, then pulled his shorts up. He typed some more, then logged off. Josh told me I owed him a look at Maggie, and I said okay. I reciprocated the next night, convincing Maggie that my camera wasn't working, and Josh stood behind me and jerked off to Maggies much pinker twat.
After that, we decided to jerk off whenever we wanted to, and that it was ok to stay in the room for the others video sex, and the girls were never the wiser.