By now most of you are aware of the instantly popular website Chatroulette. For those of you who don't know what it is, it's a site that links your webcam up randomly to someone else's webcam who's logged onto the site. It links you up randomly with people from all over the world, from different backgrounds, demographics, ages, races, and regions. It's all random. At any one time there are thousands upon thousands of people on the site, so the chances of seeing someone you know are very small... or so I thought.
One night, I decided to log in and see what came up. I was bored and I wasn't really ready to go to bed just yet. I browsed the site for awhile. As most of you know, more than half of the time, the person on the other webcam is a guy showing his penis. Luckily you can click next, and it will bring you to a different person. After about 20 minutes, I had chatted with 4 legitimate people, a guy in a Santa outfit, and I had seen 18 different dicks, one of which ironically had a little Santa hat on the end of it.
I was about ready to sign off when I clicked next for the last time. What came up were two middle aged women on the other end. It took me a moment to realize that one of them was Mrs. Wolfe, my former piano teacher. I had taken some lessons with her throughout high school. She was French (though she barely had an accent), and very attractive in her mid to late forties. She had dark hair and a stunningly beautiful face. I also had it on high suspicion that she had a great pair of breasts, but she rarely wore anything that flaunted them.
It was Mrs. Wolfe and another fairly attractive woman. Mrs. Wolfe was off to the side, and it was the other woman who was doing the typing. Here's how things progressed:
Me: Hello.
User: Hi.
Me: Mrs. Wolfe?
[I could see from her expression that they had definitely perked up. Like I was, they were probably getting bored and only paying half attention to who was on the screen until now.]
User: Who are you?
Me: This is Jackson, I used to take piano lessons with Mrs. Wolfe.
[They were both laughing and looking at each other. I could also see that there were two wine glasses in front of them, so I figured they were both a little tipsy.]
User: She says hi!
[Mrs. (Leslie) Wolfe gave a smile and wave into the webcam.]
Me: This is crazy, I've never seen anyone I know on here before.
User: Us either.
Me: What is your name?
User: My name is Janet, I'm a friend of Leslie's.
[It was pretty well known that Mrs. Wolfe was a lesbian or at the very least bisexual. I had always heard rumors about her girlfriends. I assumed that this was her partner.]
Me: Nice to meet you. Are you two enjoying yourselves?
User: Immensely. Lots of cock lol.
Me: I know lol.
User: Do you come on here a lot?
Me: Not at all, I just decided to tonight because I was bored. How about you two?
User: Same with us, this is our first time.
Me: A little overwhelming isn't it?
User: Yes, we have seen a wide variety of people and penises tonight. We noticed you don't have a shirt on. Are you one of the flashers?
[I had the webcam pointing at my face. I guess they had noticed that I wasn't wearing a shirt. The webcam only showed from my shoulders up, and since my shoulders were bare, she asked if I too was naked.]
Me: Nope, I'm wearing pants lol.
User: I don't believe you.
[I could see they were both laughing and enjoying themselves, but at the same time intently watching me. I stood up showing them that I indeed did have shorts on.]
Me: I'm sorry to disappoint.
User: Stand up and give us a little show. You have a nice looking body young man...
[I stood up showing my exposed abs and chest. I gave a little spin and sat back down. I was proud. I had been working hard at the gym to maintain my body.]
Me: Do you approve?
User: Yes. We like. Show us more.
[I could see that Janet was a bit mischievous. Again, she was the one typing, and I could tell from Mrs. Wolfe's reactions that she was a little embarrassed by Janet's questions. Everytime Janet spoke for her, I could see her shake her head.]
Me: You want me to get up and spin again?
User: Nope.
Me: What more do you want to see then?
User: You know. We want to see what you're packing. You're cock.
[I could see Mrs. Wolfe was now thoroughly embarrassed.]
Me: I don't know.. this is a little embarrassing.
User: You don't have too. We can always click "next" and find someone willing to show us their package.
[I pondered for a moment whether I should do it or not. Oh heck, she wasn't my teacher anymore, what was she going to do, discipline me?]
Me: Ok...
[I stood up and slid down my shorts and underwear to reveal my semi erect cock. I stood there looking into my computer for some kind of reaction from them. They both looked intently at my cock on the screen.]
User: Not bad.
Me: I'll take that lol.
User: I want to see it at it's hardest.
Me: It's already growing. This situation is exciting me lol.
User: What excites you?
Me: My teacher is now watching me get completely naked. Wouldn't that excite you?
User: I wouldn't know, I've never gotten completely naked on a webcam in front of one of my teachers before.
[Janet was also a smartass as it turns out.]
Me: Here you go..
[At this point I was fully erect. I moved back so they could get the full view. I turned to the side to show them my cock fully erect.]
User: Stroke it for us.
[With one hand I grabbed my cock and moved it up and down my hard shaft slowly, now baring everything I had to these two older women.]
Me: I've showed you all of me. Am I going to get to see anything of you?
User: Fair is fair.
[Janet stood up. She was wearing a dress. She turned around and lifted her dress exposing her rather large but nice ass. She was wearing a bright yellow thong which only helped to accentuate the shape of her ass.]
Me: I like.
User: Does that make you want to cum?
Me: Yes it does.
User: We want to see you cum. It's been a long time since either of us have seen a man cum.
Me: Okay, I can do that for you.
[They both stared intently at the screen watching me stroke my cock. The excitement of this situation, plus the sight of Mrs. Wolfe's beautiful face would be more than enough to get me off. Janet decided to help me out anyway.]
User: Something tells me this isn't your first time pleasuring yourself while thinking about Leslie.
Me: You are correct.
User: You've fantasized about her before?
Me: On more than one occasion, yes.
User: What about her turns you on?
Me: Her eyes, her face is just beautiful. Her body. Her fingers. Everything about her.
[Janet grabbed Mrs. Wolfe's hand and slowly began sucking on her long fingers. She sucked them slowly and lovingly. Janet took Mrs. Wolfe's index and middle fingers and sucked them from her fingertips to her knuckle. The sight was almost too much for me to take. I could now tell that Janet was the dominate one in the relationship. Janet was calling the shots. She was getting off too. Telling Janet what I adored about Mrs. Wolfe only made her more excited.]
User: Are you almost ready to orgasm?
Me: Yes.
User: What's going to put you over the edge?
Me: I want to see Mrs. Wolfe's breasts. I've always wanted to see them.
[I could see on the screen that Mrs. Wolfe was opposed to the idea. I watched as the two of them spoke. It didn't take much convincing from Janet, and before I knew it Mrs. Wolfe was standing up. She reached her arms through her dress, sliding it down to her torso. I could now see Mrs. Wolfe wearing just a light blue bra. This was again almost more than I could take as I was very near the point of no return. She reached her hand behind her back to unclasp her bra. This was it, the moment of truth. She unclasped her bra letting it fall to the floor. There they were, the most magnificent breasts I'd ever seen. As I suspected they were plentiful and ample. I can only describe them as perfect. That was the last straw. I felt my toes curl and my legs straighten. I could feel a tight clenching deep in my balls and before long I began to spew load after load of hot cum. I stared at her breasts and the look of satisfaction on Janet's face, and that was all it took to keep my cumming. It shot from my cock like a rocket. The cumshot never seemed to end, it just kept cumming, load after load. The years I spent fantasizing and imagining Mrs. Wolfe naked body erupted when I finally got to see her exposed breasts. They watched me intently as I stroked and squeezed every last drop out. To this day, I've never had an experience or orgasm quite like it.]
User: Satisfied?
Me: Very satisfied. Were you?
User: We'll be in touch.
[Session end.]
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Submitted by:
soultosqueeze
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