I Loo Lie Jail Bait-Blind Date

While pretending he was her Daddy or the long-lost grandfather she never had, Kimberly roleplayed with a stranger, a much older man that she met online.

Something she'd normally wouldn't do, would never do, she'd never meet a stranger she met on the Internet in person. That's just crazy and a good way to put herself in harm's way. Yet, with them seemingly hitting it off in their many online correspondences, e-mails, and long chatroom sessions, Kim was thinking about taking the chance that their sexy talk could lead to romance. She knew it sounded crazy with him so very much older than her but what if he's the one?

What if she discounted him because of their differences in age and made a horrible mistake? With her only 23-years-old and with Walter, 66-years-old, he was not only old enough to be the father she never had, he was old enough to be the grandfather she never had either. Yet, already deciding her fate, in the back of her mind, she had already decided to meet this much older man who she had been corresponding with online for several weeks.

It was a big risk to leave her home and leave her state to meet a man she didn't know and had never met, but he seemed so nice. In all of the funny, sexy, and sincere things he wrote to her, he seemed so perfect. Perhaps he'd be the Daddy she never had. Perhaps, he'd be the grandfather she never had. Perhaps, he'd be her Daddy and Pappy both rolled into one. Perhaps, he'd be her boyfriend, her lover, her Daddy, and her Pappy all rolled into one.

'Wow,' she thought excited about finally having an older man in her life.

Then again, with him more than forty-years older than her, she could be making a big mistake by agreeing to meet him. Then again, if she decided not to meet him in person, perhaps, she'd forever regret her decision for the rest of her life. Instead of looking fit and trim in the way that most men her age did, he could be fat, bald, and wrinkled. He could look old, wicked old. He could have no teeth. He could have a limp dick. What would she do with him then, if he looked like that and couldn't even get an erection?

"Eww," she said for no one to hear while imagining his flaccid prick.

Having told her so very much about himself, he had already voluntarily confessed more than any man her age or older had ever freely admitted. Feeling as if she could trust him, she liked the fact that he seemed so openly honest. Different from any man she had ever met, most men aren't that forthcoming with personal information, especially when it comes to past romantic relationships. Always hiding something, a girlfriend or a wedding ring, most men don't reveal private things about themselves that this man had already expressed early on and right from the start.

With them obviously feeling perversely perverted and self-conscious about their sexual peccadilloes, most men don't confess their deepest, darkest sexual fantasies in the way he already had. Most men are only looking for sex and nothing more. Along with the personal tidbits about him, he included hints about his sexual fantasies, something that no other man had done with her so early in their relationship. He included some of the sexy, sexual things that he'd love to do to her naked body, should he ever have the lucky chance to meet her. She reciprocated by telling him some of the sexy, sexual things that she'd like to do with him and his naked, erect prick, should she ever have the lucky chance to meet him.

She had never met a man who was so openly honest in his sexuality. He literally blew her mind with all that he shared. Not apologizing for lusting over her, he wrote things in such a way that made her feel sexy instead of dirty. In the way that younger men may her feel when not calling her after she had sex with them, he made her feel like a wanted and desired woman instead of an unwanted and undesired whore. As if he was her king and she was his princess, he made her feel special instead of average. He made her feel as if he was the father and/or the grandfather she never had.

'Wow,' she thought when she read some of the kind, sensitive, sincere, and even the sexually outrageous things he wrote to her. Words to a woman he never even met from a man she probably would never meet, there was something about him that made her want to continue writing him. She knew he was a pervert but she was no virgin either. Not yet a whore, she was definitely a slut.

### ILookLikeJailBait ###

After corresponding back and forth for months in a chatroom, she was comfortable enough corresponding with him that when he suggested that they do some roleplaying, she was agreeable to having some sexy fun. It took some arm twisting but once he explained what roleplaying was, she was willing to try it. In her short, young life, with the men she dated not very bright, creative, and/or imaginative, she had never roleplayed with anyone. Yet, unbeknownst to her, as if she was a natural born actress, she was actually quite good at roleplaying. As if she was playing a sexy game, she grew to love playing this sexy game of roleplaying.

"Roleplaying? What the Hell is that? I don't know what that is," she wrote. "What is roleplaying?"

She waited for him to respond.

"As if we're actors on a stage, it's a game of pretend but spiced with sex. Instead of a normal game of make believe, it's an X-rated game of you tell me your sexual fantasies and I'll tell you my sexual fantasies. It's show and tell but on an adult level. It's truth or dare but uncensored. I write something and then you elaborate on what I've written. Then, it's your turn. You write something and I'll elaborate on what you've written," he wrote.

With the cursor blinking in anticipation of what she was going to write in response to what he just wrote, he was obviously waiting for her to respond before he wrote back to her.

'Blink, blink, blink,' as if she was stopped at a green light with her turn signal still on, the cursor continued blinking at her as if there was someone behind her beeping their horn. Suddenly, she felt pressured to perform. Suddenly, she felt pressured to write something that she knew he'd like to read. Suddenly, instead of taking it easy on the old man, as if wanting to test him, she wanted to shock him.

"Okay, Walter," she said stalling for time while she thought of what to write. "Shall I go first or would you like to go first?"

She hoped he'd want to go first. She waited impatiently for him to respond while running all of her sexual fantasies and sexy scenarios through her mind. A big step, she'd be telling him, personal, private, sexual things that she never told anyone. After this roleplaying session was over, he'd know more about her than anyone.

A lingering question, could she trust him with her secret, sexual fantasies? Taking a chance on ruining their relationship before it even blossomed, as well as ruining her reputation, maybe if she told him everything that she sexually imagined, he'd think her a whore. He may think there was even something mentally wrong with her. Truth be told, just as she could be anyone on the other side of her computer screen, he could be anyone too. He could be someone she knew, an old boyfriend perhaps.

"With this your first time roleplaying, you go first. I don't want to offend you so I'll just follow your lead," he wrote. "And don't hold back. Tell me everything. Trust me. Just as there are no right and wrong answers, there are no judgments here. I won't be shocked by whatever you write. Tell me all of your sexual fantasies. I want to know all of your secret, sexual desires no matter how shocking they may seem."

Showing her the way, she would rather he go first. With all of this new to her, she never roleplayed with anyone before. As she would soon quickly discover, just as he wanted her to confess of her sexual fantasies to him, he enjoyed confessing all of his sexual fantasies to her.

Just as he encouraged her to tell him more, she encouraged him to tell her more too. She even expanded on some of his sexual fantasies by not only confessing her sexual fantasies but also elaborating on her sexual fantasies. Then, once both of their sexual fantasies were out there in the open, they each took turns further elaborating on each of them.

### ILookLikeJailBait ###

Here goes. She was ready to tell him what she had never told anyone, not even her friends. If her friends knew what she was about to tell Walter, they'd think her a whore. They'd think there was something wrong with her for wanting to confess her sexual fantasies and confide in a man she had never met and who was old enough to be her grandfather.

Maybe there was something wrong with her after growing up in foster care and never knowing her real mother, father, sister, and brothers. She never had a stable family environment to help her filter the things that came out of her mouth. She routinely said things she was thinking without giving them a thought.

"I'd love to be taken by a man. I'd love for a man to strip me naked," she wrote. "As long as it's just roleplaying and as long as I'm safe, I'd love for a man to make me feel that he was about to force me to have sex with him," she wrote.

She couldn't believe she wrote what she just did. As if he was her psychological therapist, she had never told this to anyone. She paused while waiting to see if he'd type his reaction to what she just wrote. When he didn't, brazen enough to do so, she continued writing even more about her sexual fantasy.

"As long as it was prearranged from the start and I knew that I wouldn't be hurt, I'd like for a man to rape me," she wrote.

Something so shocking for a woman to admit that she wanted to be raped, the only thing worse than that would be a woman admitting that she wanted to be gangbanged by a motorcycle club. She was already becoming sexually aroused just from confessing her sexual fantasy to him. She was already wet by the violent thoughts of a man forcing himself inside of her. Being that her sexual fantasy was about rape, perhaps her sexual fantasy had nothing to do with sex but with a violent act. Maybe there was a subconscious reason why she felt as if she needed to be so violently assaulted.

With her mind racing with all of the thoughts she hid and never confessed, she continued play acting. She imagined a burglar breaking in her apartment and holding her at gunpoint. She imagined him stripping her naked and forcing her to do every dirty and nasty sexual thing she could imagine, including anal sex. Holding her hostage, she imagined him tying her to a pole or to a beam and forcing her to be her sexy bitch.

'Oh, my God,' she thought now wondering what he'd think of her. 'I can't believe I wrote that to a total stranger. I never told anyone that I wanted to be taken. I never told anyone that my sexual fantasy was to be stripped naked. As long as I'm safe from harm, no one knows that I yearn to be raped,' she thought.

Yet, as if she was confiding in her therapist, with nothing ever to come of all that she told him, she felt relieved telling him her private and forbidden, sexual thoughts. Immediately getting into the roleplaying mode again, she couldn't believe that she actually typed her deepest and darkest sexual fantasies. She couldn't believe she told him what she had never told anyone. Suddenly she felt like such a wicked whore. Suddenly she felt so vulnerable. Suddenly, she already felt stripped naked and ripped bare.

With him an older man from an entirely different generation, perhaps he didn't share her sexual fantasy of being raped. Perhaps he had more morals than she did. Perhaps, he was the type of guy who would never force a woman to have sex with him, even if it was only roleplaying.

With him much older than she was, she hoped she didn't scare him off or cause him to have a heart attack. A young woman admitting her sexual fantasy was to be taken, stripped naked, and raped while roleplaying was such a big deal for her to confess. As much as she felt sexually excited, she felt embarrassed and even a little foolish too. Would he understand that all that she had just confessed and divulged while confiding in him was nothing more than just her sexual fantasy?

Now she was curious for his reaction to all that she had written. Now she wondered about his sexual fantasy. Yet, more than that, suddenly she felt like such a slut. As if she was in a chatroom with s Dell customer service representative emanating out of Bangladesh, India, she waited for what seemed like forever for him to respond to the blinking cursor.

'Blink, blink, blink,' the cursor as if a flashing red light, the cursor was her warning sign to write no more. She had already written enough. As if she was dreaming all of this, she had confessed all of her forbidden, sexual thoughts.

"Wow," he wrote. "I never thought that being taken, stripped naked, and raped would be your sexual fantasy. After you told me that you're an exhibitionist, I figured your sexually fantasy would be flashing your tits, your ass, and your pussy to unsuspecting men. After you told me that you're sexually attracted to older men, I figured your sexual fantasy would be having sex with an older man. Now that you shared your sexual fantasy with me, I'd love to force you to have sex with me, Kim. I'd love to strip you naked. I'd love to rape you while roleplaying. Please tell me more about your sexual fantasy."

Even though he encouraged her to tell him more, she felt embarrassed. She felt as if there was seriously something wrong with her for wanting to be raped. Now getting the sense that she was doing more than roleplaying, she was actually becoming very sexually aroused in confessing to a stranger what she had never confessed to anyone before. She wondered if he had masturbated himself over all that she had written him in the same way that she couldn't wait to masturbate herself over all of the things he had written her. She imagined him stroking his prick and cumming in a tissue from all of the dirty, naughty, and sexy things she had written him.

Not having even met the man, how could she confess something so totally outrageous as wanting to be stripped naked and raped to a total stranger. She felt so wicked. At the same time, after confessing her sexual secrets, feeling free of them, she felt so relieved. Sharing all of the sexually intimate details, she expounded even more on her roleplaying, sexual fantasy.

### ILookLikeJailBait ###

"Feeling so very helpless, with my arms suspended over my head, I'd love for a man to tie my wrists to a beam and strip me naked. Then, once naked, I'd love for him to touch me, feel me, and fondle me everywhere that's so forbidden between a strange man and a woman he just met," wrote Kim.

Again, she impatiently waited for him to respond. Expecting him to elaborate on what she had just written, instead, he gave her a one-word response.

"Wow," wrote Walter.

With him so articulately verbose, it was unlike him to be so succinct. Normally, adding to it while asking her questions, he'd write a whole paragraph on whatever she had written. She figured he was masturbating himself and was too busy to write any more than he had written. She waited and when he didn't write any more, she continued.

"I have goosebumps just from writing all of that," wrote Kim. "I'd love for a strange man, someone I didn't know, had never met, had just met, and/or barely knew to finger my pussy while licking my pussy. I'd love for him to give me an orgasm with his fingers, his tongue, and his mouth," she wrote.

She waited for him to answer her before she continued revealing the rest of her sexual fantasy to him. While waiting for him to respond, she fingered her nipples through her blouse and bra before reaching down to finger her pussy though her panties. Lifting her short skirt higher, she pushed her panty aside with her finger and rubbed her clit with her index finger while penetrating her hole with her middle finger. She couldn't wait to masturbate herself with her vibrator and her dildo. She needed to have an orgasm. After he made her so very sexually excited, and with her already so very wet, she couldn't wait to cum over this roleplaying session.

"Oh, my God, Kim, that would be so hot to tie you to a beam in my cellar. That would be so hot to strip you naked. I'd love to do that. I'd love to slowly undress you. I'd love to remove your blouse, your skirt, your bra, and your panties. I'd love to touch you, feel you, and fondle your naked body everywhere," wrote Walter. "I'd love nothing more than to eat your pussy. I'd love to give you an orgasm with my fingers, my tongue, and my mouth."

Going for broke, as if she was the man and he was the woman, she confessed all that she'd like to see happen once she was taken, tied to a beam, stripped naked, and raped. She left nothing out for him to misconstrue her sexual lusts and deep rooted desires. She told him everything she imagined him doing to her oh, so young, naked, beautiful and sexy body. Further, going where no young woman should ever go with a much older man, she confessed that she'd love to suck his cock. Not stopping there, she told him that she wanted him to fuck her, really fuck her hard and fast.

### ILookLikeJailBait ###

She reinforced her desire not only to be taken and stripped naked but also to be eaten. She couldn't count how many men she blew in the front seat or in the backseat of a car and them not returning the favor by using the excuse that there just wasn't enough room for them to eat her. Bullshit. Just their selfish excuse not to eat her, if they needed more leg room and really wanted to eat her pussy, they'd open their car door and stick their legs out or they'd out their car window and stick out their feet.

"While helplessly tied to a beam, I'd love for a man to finger my pussy while licking my pussy before reaching up to feel and fondle my big breasts and fingering my erect nipples. I'd love for him to sexually satisfy me with his mouth, his tongue, and his fingers before he sexually satisfied me, forced me actually, and fucked me with his cock," she wrote.

She paused to see if he'd respond.

"I can do that," he wrote with a smiley face.

Satisfied that they were on the same page, she continued.

"I'd love for a man to put a gentle hand to the back of my head while humping my mouth and fucking my face. I'd love for a man to hold my head in place until he ejaculated his cum in my mouth and not let me go until I swallowed."

Again, she waited until he wrote back to her in their private chatroom.

"I'd love to satisfy your every sexual fantasy, Kim. I'd love to tie you to a beam in my cellar. I'd love to take my time stripping you naked. I'd love to touch you, feel you, and fondle you everywhere," he wrote obviously getting just as sexually excited as she was getting. "I'd love nothing more than to eat your pussy and lick and finger your cunt," he wrote.

Not writing any more than what he had already written, having taken a chance that he may have offended her by using the word cunt, he waited until she responded back in kind.

"God, Walter, you're making me so horny." As if telling him the word cunt was okay for him to use, she used the same word too. "I'd love nothing more than for you to finger and lick my cunt. If you were here right now, I'd stroke your prick while kissing and licking your prick. If you were here right now, I'd suck your cock. I'd blow you. I swear to God that I'd blow you. I'd give you the best, damn blowjob you ever had in your life," wrote Kim. "I'd continue sucking your cock until you ejaculated your cum in my mouth and I swallowed your cum."

Hoping she was making him as hot and bothered as he was making her, she waited for her beloved Walter to respond to all that she had written.