I Look Like Jail Bait-Blind Date Ch. 02

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Kim meets a stranger, a much older man that she met online.
7.6k words
4.35
22.9k
17
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Part 2 of the 2 part series

Updated 06/08/2023
Created 10/07/2016
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Kim meets a stranger, a much older man that she met online

Revised, rewritten, and continued from chapter one:

She didn't have the courage to break it off with him. Instead, she was curious enough and sexually excited enough to meet him. As if she was curious who was the Wizard of Oz, she needed to meet the man behind her computer screen. Only, she wasn't going to Kansas, she was going to Detroit.

With her not having a manly mentor in her life, she'd love to have someone who'd take the place of the Daddy and/or the Pappy she never had, always missed having, and always wanted. Tired of listening to her friends bore her to death talking about their dads and granddads, she'd wanted and needed to know what it would be like to have someone like that of her own. She'd love to have an older man in her life to call Daddy or Pappy.

Now, no longer confined to a chatroom, here she was already at the Detroit airport ready to meet her cyber lover. Surprising even herself, she couldn't believe she was actually going through with this. She couldn't believe she had boarded a plane and flown here.

Having never met anyone in person that she met online before, Kim was nervous. A big risk, a huge gamble, and a roll of the love dice crap shoot, with her already having second thoughts about meeting him, she didn't know what to expect. A woman alone, a woman so young, so pretty, so sexy, so innocently naïve, she was a woman who writes erotica on a pornography site online and he was a man who reads all that she writes. He could be anyone.

'He could be a real whacko,' she thought. 'He could be a rapist. He could be a serial killer. God, what have I done by agreeing to meet him? He could have a bevy of girlfriends. He could be married. I never should have agreed to do this. Instead of flying here, I should have broken it off with him. This is crazy and I'm nuts.'

For all she knew he could be just another harmless, dirty, old, lonely man and another one of her perverted, cyber fans, followers, and stalkers. For all that she knew, in the way she was looking for her Daddy, he could be looking for his daughter. For all she knew, and no doubt that was the case, he could be someone who just wanted to meet her for sex.

With this becoming so real, so fast, she'd never have sex with him, of course, a complete stranger. For her to have sex with him, he'd have to take her against her will. He'd have to forced her to have sex with him. He'd have to drug her for her to give him sex.

When thinking of him forcing himself on her, she thought of her sexual fantasy. She thought of roleplaying in person instead of over the computer of him stripping her naked and raping her. Then, again with those thoughts creeping in her mind again after watching so many crime shows on television, for all she knew, he could be a manic ready to rape her, sexually abuse her, and/or murder her. With her so naive and so innocent, she could be walking into some sort of diabolical trap.

### ILookLikeJailBait ###

A smart thing to do to protect herself, instead of going to his house, which is what he suggested originally, she decided to meet him at the airport. From there, she could go for a drink or for something to eat. After making some small talk, she'd know if there was anything there to start a romance. After spending some public, face-to-face time with him, she could tell if he was as nice as he portrayed himself to be in his e-mails and in their private chats or if he was a crazy psycho killer. After getting to know him better, she'd be able to tell if he'd be her boyfriend, her lover, her Daddy, and/or her Pappy.

With the airport so hustling and bustling, she felt safe enough in a crowded, public place. She'd feel much safer meeting him here than she would meeting him alone in his house. If she didn't like the looks of him, she could just turn around and hop on the next plane home. If they hit it off, at least she'd have a ride to his house instead of having to pay for a cab.

Having a conflict of mixed emotions, she was as nervous to meet him as much as she was sexually excited to meet him. Even though he was much older than her, what if he was her knight in shining armor? What if he was the one special someone she dreamt about in her dreams and imagined in her sexual fantasies? With him always knowing the right words to write, maybe he was her Mr. Perfect. She hoped that what he portrayed himself as in his love letters was just how he was in person. Unless she met him in person, which is why she was here, she'd never know if he was the one.

She thought about all that he wrote to her and all that she wrote to him. Maybe this was her Mr. Right, albeit an older Mr. Right. Maybe this was her one chance in a lifetime to find everlasting love, that is until he died of a heart attack while they were having sex. There was no getting around the fact that he was more than 40-years older than she was. How would she really feel about a man who was so very much older than her? Could she love him as if he was her lover, her boyfriend, her Daddy, and/or her Pappy?

She had never dated anyone old enough to be her father, only never having known her father, she definitely did have Daddy issues. What the Hell, if this man wants to be her Daddy and shower her with gifts, who is she to stop him? Yet, if he wanted to be her grandfather, as well as her boyfriend, and her lover, that was fine with her.

If nothing else, instead of him being her lover, instead of him being her boyfriend, he could be her dad and the father she never had. He could be her grandfather, the grandfather she never had. Then, if she perceived him to be her father or her grandfather, how hot would that be to have pretend, roleplaying, incestuous sex with her surrogate father or grandfather.

'Oh, my God,' she thought. 'I'd love to suck my pretend father's cock. I'd love to suck my pretend grandfather's cock. We could have so much fun roleplaying while he sexually and incestuously abused me and while I gave him oral sex.'

Chapter two:

His name was Walter and he lived on the Detroit River in an old industrial complex of mostly dilapidated buildings that had been reclaimed and modernized with large studio apartments, residential lofts, and swanky penthouse apartments. From buildings that looked as if they were targets in a bombing raid to buildings that were reclaimed, rebuilt, and refurbished, Detroit was returning back to life after the auto companies abandoned them. Detroit's Riverwalk was a spectacular place where people walked, gathered, and dined at one of the fine restaurants that dotted the water view.

"Oh, my God," said Kim when she saw what the city had done. "Wow! It's beautiful."

Detroit was the home towns of Christie Brinkley, Charles Lindbergh, Henry Ford, Kristen Bell, Jerry Bruckheimer, Ellen Burstyn, Francis Ford Coppola, and Charlton Heston. Detroit is where Sugar Ray Robinson, Gordie Howe, Al Kaline, John Smoltz and Tom Selleck were born and raised. Detroit was where Alice Cooper, Madonna, The Four Tops, Aretha Franklin, Kid Rock, The Temptations, Diana Ross, Stevie Wonder, Smokey Robinson, Eminem, Sonny Bono, and Bob Seger all started life. Back in the heyday, Detroit was Motown.

Nonetheless, Detroit's revitalization and transformation, Kimberly had a negative opinion of Detroit and of the Detroit Metropolitan Airport. With the guns, murders, violence, drugs, rapes, and robberies that happens there every day, with police roaming the airport with dogs and automatic weapons, she feared for her life leaving the relative safety of the airport. As bad as leaving O'Hare Airport in Chicago, she imagined being caught in the crossfire and a hail of bullets after leaving the airport. She imagined a terrorist randomly shooting people or setting off a suicide bomb vest in the airport.

If that wasn't enough she was sexually accosted by a female TSA worker. Her first time flying, she couldn't believe how familiar the female TSA security person got with her body. How dare she? For the woman to touch and feel her where she touched and felt her, the woman was obviously a lesbian hoping to get lucky with her. Unaccustomed to a woman groping her and having her sexual way with her body, the agent touched and felt her everywhere men usually touch and feel her on a first date.

### ILookLikeJailBait ###

After e-mailing her back and forth and exchanging photos, Walter asked her for explicit, sexual photos of her wearing her panties and bra, topless, and/or naked. She couldn't remember the last time she sent anyone such revealing photos. He was an attractive man, yet something she seldom does, she didn't know why she relented in sharing her sexually inappropriate photos with him but she did.

Then, after she sent him explicit, sexual photos of her in her panties and bra, topless, and naked body, he sent her explicit, sexual photos of his naked body, mainly his cock. With every photo of his cock taken with him having an erection, he seemed very proud of his big prick. For an older man, he did have a nice cock. Just as she wouldn't mind stroking that big, hard thing, she wouldn't mind sucking and fucking that big, hard thing either.

Making her sexually aroused and horny when she saw his engorged penis, he did have a nice, hard appearing cock for an older man. His cock was the first sixty-something-year-old cock had she ever seen. If she didn't know his prick was as old, she'd never know it. Being that one of her favorite things to do was to masturbate a man and blow a man, she loved to see his big, hard prick in person. Now, with her on the way there, she couldn't wait to hold his prick, to stroke his prick, and to suck his prick before fucking his prick.

'God, on my way to being a whore, I'm such a slut,' she thought to herself while laughing.

Unlike other women who don't suck cock and who don't swallow, and/or who don't even allow men to cum in their mouths, even if they do suck cock, she not only swallowed but she enjoyed sucking men dry. She wasn't like other women who dabbled when sucking cock. One of her favorite, sexual things to do was not only to flash and tease men but also to give them blowjobs. There was something so sexually satisfying about controlling a man with her hand and/or with her mouth, as well as with her pussy.

It was one thing to fuck a mana but it felt more personal for her to suck a man. She loved staring up at men with her big, blue eyes while teasing them with her tongue and while blowing them. She loved it when they became sexually aroused to get really hard and sexually excited enough to cum in her mouth. With them putting a gentle hand to the back of her pretty, black haired head, she enjoyed it when men humped her mouth and fucked her face while fondling her big tits and fingering her erect nipples. To her there was nothing like stroking a good looking man's prick, licking his prick, and sucking his prick while fondling and cupping his testicles.

'Hump my mouth, Walter. Fuck my face,' she imagined saying. 'Cum Walter. Cum in my mouth. I want to taste you. I need to swallow you.'

### ILookLikeJailBait ###

Other than his request for explicit, sexual photos, by judging him on the value of all that the wrote her, he seemed normal enough. Actually, not such an unusual request, there wasn't a fan who read her erotic stories who didn't ask her for explicit, sexual photos of her semi-naked and naked body. In the way that most men do without even asking, he sent her photos of his erect cock. He sent her videos of him masturbating himself. He even sent her videos of him cumming big, white, gobs of cum.

For an old guy, someone who was collecting Social Security, he did have a nice looking prick. For an older man, someone who was collecting Social Security, he sexually aroused her by showing him cumming. She couldn't help herself from imagining stroking him. She couldn't help herself from imagining putting her mouth on his engorged prick. She couldn't help herself from imagining him cumming in her willing mouth and her swallowing his cum.

Unlike many of the older men she knew, he certainly didn't have erectile dysfunction issues nor was he out of shape. Unless he took a Viagra, his cock looked as hard and at the ready as any of the much younger men she dated and sucked. With his photos and videos, as well as his written words making her horny, she wished she was there to touch him, fondle him, stroke him, suck him, and fuck him. She wished she could feel her lips stretched around his big prick. Most of the older men she had seen at the mall all had potbellies but he was slimly muscular and looked to be in great shape.

Then, once she was okay with all of the pornography he sent her, he sent her romantic love letters before he sent her a one-way, first class, airplane ticket to his city, Detroit. She was as stunned by his romantic love letters as much as she was stunned by his videos of him cumming, and as much as she was stunned by receiving an open ended, first class, plane ticket in the mail. Suddenly, shit or get off the pot, this was real. He wanted to meet her as much as she wanted to meet him. Nonetheless her eagerness to meet him, suddenly, she felt pressured to either meet him or end their online correspondence.

If anything, she was curious if he was as nice as he was in his correspondences. If anything, she was curious if he was as romantic in person as he was in his love letters. If anything, she needed to know if there was a romantic connection. If anything, tired of masturbating herself over his salacious letters and over his videos of his cock cumming, she needed to see, feel, stroke, suck, and fuck his cock in person.

"I'll gladly pay your way home, if you decide to come," he wrote. "I'm just dying to meet you. I'm just dying to see you in person. I'm just dying to hold you in my arms, stare in your big, beautiful, blue eyes, and kiss you," he wrote.

'Kiss me, my ass? Yeah, I bet that's all he wants to do is just hold me in his arms, stare in my big, beautiful, blue eyes, and kiss me,' she thought to herself. 'What a crock of shit?'

She shook her head in disbelieve over the line he was trying to feed her.

'No doubt, after all of the sexy letters, chatrooms, telephone calls, sexy photos, and salacious videos of his cock cumming, he wants me to suck his cock,' she thought. 'No doubt, after I confessed my sexual fantasies to him, he can't wait to tie me to a pole and strip me naked. No doubt, he wants to finger my cunt while licking my cunt. No doubt, thinking that this is what I really want, he wants to rape me,' she thought. 'Then after he rapes me, he wants me to suck him and swallow his warm, oozy, load of cum.'

### ILookLikeJailBait ###

Going against her better judgment, she agreed to meet him. Yet, with her alone with him in a crowded airport, if he was a perverted weirdo, she could always turn around and take the next flight home. The plan was to meet him at Detroit airport. As if he was her personal, private chauffeur and as if he was her father, her Daddy, or her grandfather, her Pappy, Walter would be the one holding a 'Kim' sign.

This was it. This was finally it. After months of writing back and forth, they were finally about to meet face-to-face. She was so nervous to finally meeting him. She hoped he looked as he did in his photos. She hoped he was as nice as he was in his e-mails and letters. She hoped his cock was as big and as hard as it looked in his videos.

As if she had known him forever and as if he was her long, lost Daddy, immediately drawn to him, she saw him as soon as she left the departure gate. When seeing him for the first time and from a distance, especially with his snow, white hair, he looked older than his photo. He said he was 66-years-old and she was hoping that he'd look 56-years-old instead of 66-years-old, but he looked more like he was 76-years-old.

'Oh, fuck,' she thought while already ready to turn around and go home.

She had been with older men before, men who were ten and fifteen years older, but not this much older than she was. Even if he was 66-years-old, he'd be 43-years-older than she was. As she neared, with his white hair throwing her off, she could see that he probably was 66-years-old. Instead of looking younger or older, thank God, he looked his age.

"Oh, my God," he said giving her a big smile. "You look just like your picture only much better in person. You're so tall, much taller than you appear in your photos," he said looking at her as if she was a model and he was a photographer. "You're so shapely," he said looking down at her curves. "You're so sexy."

Suddenly feeling in the way that Christie Brinkley must have felt with Billie Joel, she beamed him a smile at his compliments.

"I was sitting down in my photos," she said with a laugh. "Moreover, I'm wearing heels and this hat that makes me look 6'2" tall," she said. "It's finally so nice to meet you, Walter," she said holding out her hand.

He frowned obviously by her calling him Walter instead of Daddy.

"Daddy," he said wrapping his arm around her slender waist and pulling her to him

He slid his horny hand down and cupped her sweet, shapely ass through her short skirt in his palm. Not done there, whether inadvertently or intentionally, he lifted the back of her short skirt enough that she knew her white, bikini panties were exposed to any man walking behind her. Only, with her an exhibitionist, she didn't care that he was exposing her panties to other men. If anything she was sexually excited that he was taking such exhibitionistic and voyeuristic views with her panties.

"Okay," she said.

At that point, she would have agreed to anything. With him flashing her panties in a crowded airport terminal, she was becoming too sexually aroused to think straight.

"As you did in all of your sexy correspondences, please call me Daddy." He gave her a sly, sexy smile. "I prefer thinking that you're my dear, sexy daughter instead of my cyber, slutty girlfriend."

She gave him her best smile and he surprised her when he gave her a peck on the lips. As if testing the waters, it was just a little kiss but then when he tried parting her lips with his tongue, too much too soon, she pulled away. While still holding her around her waist and with his hand still on her ass, he squeezed her shapely behind while trying to move his fingers under her skirt and between her thighs.

'Good God,' she thought. 'He's ready to finger-fuck me right here in the airport terminal.'

"Okay, Daddy," she said moving his hand off of her ass by taking his hand in her hand and holding it.

He took her carry-on case and escorted her out to his car, a baby blue, 2011, Lincoln Town Car, the last of the Lincoln Town Cars. She knew that because one of her foster father's had a 2011, Lincoln Town car. Actually, with them all looking so much alike and with Lincoln not making any real changes in the car other than adding side air bags in 2009, a 2007 looked exactly like a 2011.

With them immediately hitting it off, there was no reason to waste any more time at the airport having coffee, a drink, or lunch. Seemingly, as much as he was interested in learning more about her, she was curious to know more about him. Yet, surprising one another by their sudden silence, seemingly, they were already done talking. The lustful lull before the sexual storm, it was as if the only talking they both wanted to do was to have hot sex.

It didn't take long for him to drive from the airport to his penthouse apartment. Less than 20 miles from the airport to his place, he even gave her a brief tour of his city. Her favorite part of Detroit was the new Riverwalk. She imagined strolling hand and hand with him after dining in one of the many restaurants.