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Friend In Need

Posted by: Age: 38 Posted on: 1 comments
5 likes 988 views Category: Masturbation Male-Female Tags: facebook chat, cam, masturbation, old friends, Oral, big boobs, Snooping, Mom catches me

Seeing an old friend from high school online one night leads to new perspectives...


It was well past midnight and I couldn't help but keep looking to skype and kik on my phone. Nope. Nothing. Not a single message from anyone. No one online that I'd be able to chat with. And then there's the "chat" that I was longing for. The kind to help relieve the tension that built in me all night. But no. Nothing. I switched to facebook for a bit and saw the list of people online in the messenger. One of the names that popped up was a girl I went to high school with, Judy. We shared the same homeroom because our last names started with the same letter. She usually ended up sitting next to me in most of our classes. A bubbly, friendly and outgoing girl who was always quick with a laugh. Judy was a very hefty woman back in school and nothing changed since then. Still having glasses and her hair pulled back in a pony tail. The only difference was now I noticed she had a lip piercing. Well, that and the fact that a year before she posted a story on facebook about ways a man should eat a girl's pussy so she can truly enjoy a good oral session. That post stuck in my mind for quite a while. I never looked at Judy as a sexual person before that moment but her putting it out there so easily really grabbed my attention. I admired her as well as saw her in a new light. Without realizing it, my thumb tapped her name and the message window came up. Shrugging, I started to say hello and tease her a little about being up so late at night. Pushing SEND, I put my phone down not expecting her to bother writing back. Moments later the messenger app showed I had a new message. Sure enough, there was Judy writing back, just as bubbly as ever. We went back and forth a bit, joking and catching up. Then I decided to broach the topic of that post she shared about oral sex. After that the conversation seemed heated quite a lot, with us circling around the idea of intimacy and what we both would love to have right now if we could. I took a moment to admit that I didn't want to push the subject on her if she didn't feel comfortable. She only wrote back one word: Push. So we probed a bit deeper, with me admitting I was climbing the walls a bit that night to find release. She was flattered I'd turn to her in a moment like that but fully admitted that she wasn't home that night, instead she was spending the weekend at her brother's house a few states south and didn't feel comfortable doing things like this without being in her own home. That led to me shrugging, admitting defeat and not pushing the issue any further. We said goodnight to each other and planned to talk again soon. The next night I saw her on messenger again and sent a "hello" her way. Quick to respond yet again, we picked up where we left off, chatting and whatnot, though the subject of our talk from the night before easily made it's way into the conversation again. "I'm flattered you thought of me to do this, but I know you're married and that's just hard for me to ignore," she messaged me. "I understand. I'm not expecting or pushing anything on you. I did like how the conversation was going last night but if you aren't comfortable, then we can talk about other things." "I actually liked talking about the "other" things. I just don't feel right talking to you about that considering your situation," she admitted. "Yes, I am married. But no we don't have sex very often. I'm not looking for someone to cheat with or get involved in any way physically. My hope with this is to just find someone who wants to enjoy themselves with me. If you'd like that, I'd like it too. If not, that's not a problem as well. I won't push if you don't feel comfortable, Judy." There was a moment or two of silence. "So basically you're saying we'd be like two good friends helping each other?" she asked. "That's the way I see it. I'm not asking you to come over and do anything with me. But if you don't mind me doing things and showing it to you on cam, that would be a very fun way to find release over just watching a video. Again, not trying to push, but the idea is very sexy to me." She responded back with a word that now I've looked at in such a sexy way it's difficult not to be aroused... "Push." "So you'd let me video chat with you?" I asked. Thankfully my typing didn't sound like my voice would in that moment, probably as excited as a kid at Christmas. "Well, normally I'd rather you just video so I can see you but if you really want to see me, I guess I can turn a light on." "Yes, please. I want to see you too, otherwise the screen just shows me and my hand jerking it and that's just not a very fun sight for me." "Fine, I'll turn the lights on then. Call when you're ready." I hit the video chat button quickly and after a few quick rings there was Judy smiling at me on the other side of the chat. The overhead light in her room was on, her hair was pulled back in a ponytail just like the old days. Glasses on, smile constantly playing on her lips as she saw me and how I've become over the years: bald with glasses and a salt and pepper scruffy beard. A few extra pounds of my own, too. I noticed, though, that Julie didn't have anything on like a shirt as she sat on her bed. "Oh my God, it's you! I like the beard," she said with a laugh. "Yeah, it's showing off all the crazy I've dealt with since high school. I feel too young to have a salt and pepper beard." "It looks good on you," she beamed. "Are you sure you want to do this?" I asked, slowly stepping into the world I never entered with her before. Judy used to be my lab partner in chemistry class. She was just the happy girl that I had fun laughing with and trading homework with in homeroom. And now here was the moment where we would see each other in an entirely different way. "Yeah, I'm here aren't I?" Judy grinned, a twinkle in her eye. "Do you want to see me?" "Please," she said. I aimed the camera down to my hard cock that was sticking straight up, almost touching my belly button, even with my dad bod belly. "Oh wow," she sighed. I wrapped my hand around the shaft and held it up to her so she could see me for real. Admittedly, it swelled a bit more at the thought that Judy was watching and enjoying it. "That is such a beautiful cock," she moaned. Her hands traveled to her huge breasts and began playing with her nipples. Her breasts were a thing of beauty, so large with nice, large nipples with bumps all over her dark pink areola. Judy's fingers pulled on the hard tips, massaging her breasts against her chest as her breathing got more shallow. I kept hearing a noise in the background from her connection. She smiled as she admitted, "That's my vibrator. I have it inside of me and I'm riding it." "Can I see?" "No," she laughed, "I don't want to show you everything! But you can focus on these at least." With that she brought her breasts back up into camera and stared intently as my hand worked my cock. She seemed almost like a woman possessed as we continued, riding her vibrator harder as her look grew more and more dreamy. But what I was very amazed by is how her tongue loosened and suddenly she had words coming from her mouth that I never thought I'd hear from her. "Oh fuck, that is such a beautiful cock. I want to taste it. Put it in my mouth. Suck the head. Fill my mouth with it and rub my tongue over it to make you fill my mouth full of your cum. So beautiful!" My hand kept stroking. The fact that I didn't get relief the night before and it was pent up all day only added to how sensitive and sexy this moment was for me. I grabbed my cock hard and began to truly work it. The feeling of my cum surging up from my ball sack to the point where I knew she was going to watching me spill my seed on my stomach was nothing short of intense. "Judy, I can't last much longer," I admitted, my hips moving as I kept thinking how lucky that vibrator was in her warm, wet, chubby pussy. "Don't try to. You want to give me that cum, don't you?" "I do, I really do. I wish we could sneak away right now and you could let me finger you while you sucked on me." "I know," she moaned. "So tempting but just keep things here. Let me see how much you need to cum." I stroked faster and kept looking at her. I was never into overweight girls but over the years I understood that sometimes those were the girls who enjoyed sex more than others. They put themselves heart and soul into enjoying the attention and making sure the man they were with would give in to their pleasure. Did I want to fuck her? In that moment, yes. I would have loved to push her back on her bed, legs spread open wide, take a long look at the pink, soaked slit between her chubby legs and whether or not she shaved down there. Then plunge myself inside her and take her to make her breasts bounce everywhere while her tummy and thighs jiggled with every movement. That was all I needed to do. Before I knew it, I rubbed the swollen, red mushroom head of my cock just a few more times before it swelled and shot the first and second long rope of white cream all over my hairy stomach. Judy watched with her eyes fixated on my cock and the mess it was making on me. She smiled devilishly as she rode her vibrator harder and pushed herself to enjoy a nice climax with me. Shivering from the rush, Judy moaned and sighed. And, yes, the thought of being inside of her while she did that was still very, very close in my mind. I laid on my couch completely spent, my balls emptied on my stomach. Judy looked at the mess and giggled a bit, pointing out that I should get going so I can clean myself up. I smiled, agreed and with that we simply said "good night" and ended our talk.

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