It had been a month since Lydia had slept with her boyfriend for the first time ever. At 19, she knew how late a bloomer she was – her friends at worked teased her all the time, and she was certainly one of the last girls among them to lose her virginity – but her boyfriend Max appeared to have been patient.
As a matter of fact, he hadn't been. Max had been desperate for sex, knowing full well that he was "falling behind" his friends who bragged constantly about their triumphs over girls – a fact that only got tougher as they entered their first year at the state college, where all it took was a little liquor to get lucky. One night, a few months before, while Lydia was busy working at the seafood restaurant in town, Max went alone to a party near the school. Frustrated with Lydia's seeming disinterest in anything sex-related, he took home a high-school girl and lost his virginity to her in his dorm. When Lydia finally gave up her own virginity to Max a little later on, she was confused as to why he seemed so bored, being completely oblivious that Max and the girl from the party had been hooking up for months.
What Max never understood was that Lydia was no prude – she seemed rather plain but was in fact obsessed with the idea of sex. The reason she waited so long to lose her virginity was not because she was scared of sex itself; in fact, she explored it so deeply, and on such a regular basis alone that she often feared she would lose control when the time came.
Unlike her boyfriend, she did not go to school and spent all of her time working in order to pay for her small apartment, where she and her cat lived alone. She was often alone there most of the day, browsing porn sites, reading erotic stories and comics, and chatting online with strangers to satisfy her increasingly unique taste for sex. She collected toys, took photos and videos of herself using them, and roleplayed fantastic scenarios on instant messager. Meanwhile, she had only actually had sex with Max twice – he was getting more and more juvenile, and she found it unattractive. At the same time, it was getting harder for her to control her urges.
After a particularly explosive session with one of her chat partners, she went to work and found herself unable to focus, and unsuccessfully tried to masturbate in the bathroom. Finding herself unable to orgasm, she went to her manager and begged them to let her go home sick – she said she had thrown up. Once she got out, she raced home and immediately went to work exploring her kinks: cumplay (she had never tasted it), breast expansion (she always wished she was bigger), sizeplay (Max was not exactly impressive in that department), bondage. For hours she flipped through videos and pictures with her vibrator glued to her pussy. She was getting obsessed. Still not satisfied, she fired up her instant messenger and began chatting with someone who had previously described themselves as an "older, married man," named James.
She secretly relished their conversations. He was so self-assured, so experienced – and unapologetic about his taboo desires. That night she vented about Max, about her frustrations and her sex obsession, and he seemed to listen carefully. He told her he wished he could be there to comfort her, and that he'd never be uncomfortable with her wishes.
"Thanks," she said cheerfully, optimistically imagining what he must look like.
As if he read her mind, he quickly typed, "You're probably too cute for him, anyways."
"As if," she laughed. "I'm nothing special."
"I'll be the judge of that. Send me a pic."
She froze. She had always kept most of her play private, and had definitely never sent a stranger a picture.
"I don't want you to know what I look like," she typed.
"Please? I bet you're beautiful."
Lydia was nervous, but he seemed like he really just wanted to see her face. Even for all her deviance, she was still too naive to imagine a stranger in some faraway place, horny and desperate to jerk off to her picture. She reluctantly sent him a clothed picture of herself that featured her face. "Now you," she wrote, her heart pounding. Some part of her knew where this was going.
Almost immediately he sent a return photo. She couldn't help but gasp.
In the photo she saw an older man – not unattractive, and while not very built certainly out of shape – standing entirely naked before a mirror, holding a ten-inch erect cock in his hand.
"Wow," she wrote.
"Too much? This is more what I was getting at."
Lydia's heart was beating even harder, but her pussy was also betraying her. "One sec," she wrote, and stood up and walked towards the mirror. She dropped her panties – the only piece of clothing she wore – and wrote "HI, JAMES" in lipstick across her small breasts. Then she took the photo.
Looking back at herself, only five feet tall with a single blonde braid and small breasts, wearing only glasses and a strangers name across her chest in red, Lydia suddenly felt amazing. After hovering for a moment over the button, she smiled and clicked "send."
This is my first story in awhile, feel free to message me with questions or suggestions!
Source: reddit.com/r/sexystories/comments/3jf4hc/becoming_lydia_pt_1_f_mast_internet_chat