Chatting With His Dad - Sex Stories

Chatting With His Dad

As the soft glow of the computer screen lit up her face, Emily's fingers danced across the keyboard. It was late, well past her bedtime, but she couldn't help herself; she so missed her nighttime chats with her boyfriend, Jason. He was away at football camp, and she missed him terribly. Little did she know that her late-night conversation would take a turn she never could have anticipated.

Unbeknownst to Jason, his father, David, had put monitoring software on his son's laptop and had been reading their late-night conversations for months. He had been lurking in the chat room tonight, pretending to be a twenty-eight-year-old single guy named D1-4U. He'd seen Emily's cute messages in the chatroom and found himself perversely drawn to her.

Hiding behind his fake avatar and profile, he started to strike up a conversation, starting with some innocent questions about her favorite music or movies. As they chatted, he began to flirt more overtly, complimenting her on how smart and funny she was. Emily was both flattered and slightly uncomfortable, but the attention made her heart race. She wasn't sure whether to admit she had a boyfriend or not. And once D1-4U had said he was twenty-eight, she wanted to seem older than she was. Prepared to lie about her age, the guy never asked.Emily hesitates for a moment, unsure how much she should reveal to this stranger. But then, she decides to play along, telling him about her love for art and her dreams of becoming a painter one day. ...

... He responds with encouragement, telling her he can see her successful in that field. The conversation continues to flow effortlessly, with him asking her more questions about herself and her life.

As they talk, Emily can't help but notice that D1 seems to be looking for specific information about her body. He asks her about her height and weight, and even about her chest size. It makes her feel uncomfortable, yet at the same time, she finds herself growing more aroused. She assumes older people are more comfortable talking like that. She's never experienced anything like this before, and it's both confusing and exciting. And she didn't want to give herself away. She knew older guys looked at her bust, and reluctantly told him she wore a 34DD bra.

D1's response is immediate. "Oh wow, that's huge! I've always had a thing for big breasts. You must feel so sexy with them." Emily thought about that. Most of the time, she DID feel sexy with them. She'd never thought of herself in that way before, but the idea of an older, hot guy desiring her this way was intoxicating.

He then asks if she has any pictures of herself, just so he can see what she looks like, clothed, of course. Emily hesitates, knowing that it's not a good idea to send pictures to strangers, but the desire to please him and the thrill of the attention is too strong to resist. She rummages through her phone and finds a picture of herself wearing a tight-fitting top, her chest spilling out over the fabric. She ...