An Online Friendship Begins

Their friendship started out simply and innocently enough. A mutual friend introduced them online. She thought they would be good for each other. She thought they'd get along really well, that they'd enjoy each other's conversation, and that they'd bring out some good in each other. She mostly thought that he would help her come out of her shell and open up conversationally, especially online. Little did she know how much she'd be right. Jim and Katherine are nowhere near the same age. In fact, she could easily be his daughter.  No matter, they seemed to have a natural connection. Conversation came easy and they never had any trouble finding subjects to discuss. When they first started chatting, every topic was innocent. They'd chat about music, baseball, exercise, and how they cope with family members. The topics were always kept platonic. Jim wanted to be careful. Katherine was young and not only did he not want to scare her away, he also didn't want to cross some line he couldn't pull back, especially with a woman more than half his age. Katherine soon began to develop a fairly strong liking for Jim. She couldn’t describe it nor explain how it began. She had never met someone that she had so much in common with. So, this is how they went along, for many months, just getting to know one another, and becoming friends, even though they only ever connected through text. Then one night, they both agreed they could take their discussions a little further, into the realm of their desires, and what they do when they needed to satisfy those desires. Again, the chat started out innocently enough, talking about what they had done that day, just at school, home, or at work. What the weather was like, since they lived so far apart from one another. Then Katherine built up the nerve to ask Jim what he was doing at that moment.  “I don't know how I should reply,” wrote Jim. “Just tell me what you're doing. We’ve been talking long enough that we can be honest with each other. I'm not going to freak out,” replied Katherine. “OK. I'm rubbing myself right now,” wrote Jim.  It took him a minute or so just to type that simple sentence. He was so afraid of scaring off a woman for whom he was beginning to grow fond of. Katherine was incredibly nervous about admitting what she was doing. She had chatted in this manner with a few others, but not with anyone she really liked. She really wanted him to know so she decided to tell him a little at first. “I’m rubbing myself, too.” Jim hesitated, hand on his throbbing cock. “Did she just say what I thought she said,” he thought to himself.  “Is this beautiful, young woman turned on by knowing what I'm doing?” The thought of Katherine naked and pleasuring herself nearly made him cum right then.  But he resisted the urge and continued with slow strokes. “Katherine, what are you wearing right now?” he texted to her. “And what are you thinking about?” Even though he had never seen Katherine naked, the images he was conjuring in his head made his cock hard as a rock.  He gently rubbed his thumb along the ridge and groaned, wishing it was her who was caressing his member. It scared Katherine a little opening up like this to someone she had never met in person. Sheepishly, she typed, “Only a light blue thong.” Surprisingly it turned her on even more telling him that. The wet spot on her thong grew a little as her arousal grew. She really liked Jim and felt safe chatting with him. She was getting a little confused also. She had never felt like this with anyone but her boyfriend. She knew he trusted her when she chatted like this so she continued. It was her turn to ask him. “What are you wearing?” After a minute or so she saw a reply on her screen. The reply said “Nothing.” She replied, “Would you like me to take off my thong?” “Yes, please.” At this point, Jim was so excited he was surprised he didn't cum right then and prematurely end his portion of this wonderful exchange.  The images in his head of her slowly sliding her thong down her thighs and being completely exposed had him harder than he had ever been. Jim continued stroking, slowly, and described to Katherine what he was doing.  “Oh, fuck. This feels so good. My cock is so hard right now. It's throbbing.” Precum began to leak out so he took it on the end of his finger and licked it off.  He didn't dare tell Katherine he did that. He didn't want to scare her off with any of his kinks, no matter how tame they were. At this point, he really couldn't believe his luck.  He had masturbated to online porn so many times. He had even chatted with people while masturbating.  But he had never done it with a woman half his age. A woman he had started to grow very fond of and who he seemed to have some unexpected connection with.  His head was swimming in a fog of erotic, horny feelings. It was as if the whole world fell away and the only things in existence were Katherine and him, and their connection over chat.  Both of them naked and pleasuring themselves, sharing what they felt comfortable with. Jim enjoyed every second of this moment, stroking his cock, imagining Katherine's naked body with her hands caressing her soft skin, teasing her nipples, and running her fingers up and down her slippery, wet slit.  He had to keep slowing down, and even stopping now and then, to make certain he didn't cum before she did. He wanted to savor every bit of her describing what she was doing to get herself off. “Katherine, how close are you?  I'd love to masturbate with you all night, but my cock is just aching to burst any minute.” “I’m getting a little close. My thumb is pushing on my clit as I fuck myself with two fingers.” Seeing that reply made Jim’s cock twitch. Picturing Katherine, a woman he thought was amazingly beautiful, was getting him almost to the point of no return. Jim thought he would try to get more from her description. “What are you thinking about as you play?” “I’m imagining that we’re sitting together, wanting to see each other cum,” she replied. Jim told Katherine, really hoping he wasn’t going to scare her off, “Let’s cum together now, as we chat. I’m so close!” They both sped up, trying to cum at the same time. Timidly, Katherine made the next response, “Almost there. My fingers are going so fast.” Seeing that triggered Jim’s orgasm. Cum erupted from his cock with a force he hadn’t felt in years. As he came, he kept stroking. Having trouble typing, he told Katherine, “OH FUCK!” Seconds after reading it, Katherine’s orgasm began. Wave after wave of incredible pleasure coursed through her, causing her hips to buck. As much as she tried to hold in a scream, she couldn’t. A scream, almost loud enough to be heard outside, escaped from her lips. She tried to type that she was cumming but only gibberish went through in her response. Jim and Katherine both sat motionless as they let themselves come down from their orgasmic highs. They were both surprised with what just happened, but for different reasons. Jim never imagined he could get such a response from a woman so young. Katherine never knew she could have the courage to cum for someone who, just a few months ago, was a complete stranger. After they rested for a few minutes, they said good night to each other and that they hoped to chat again the next day. Neither one of them realized at that moment just how special their friendship would become.