I Look Like Jail Bait-Blind Date Ch. 01

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"Oh, my God, Kim, I'd love for you to stroke my cock while sucking my cock. I'd love to cum in your beautiful, willing mouth while I stroked your long, lush, black hair. I'd love to watch you staring up at me with your big, beautiful, blue eyes while seeing my erect prick buried in your mouth. I'd love to feel and fondle your big breasts while fingering your nipples as you blew me. I'd love to hump your mouth and fuck your face. I'd love to watch you swallow my load of warm, oozy cum," he wrote.

Now that she told him her sexual fantasy, she was more than curious to know his sexual fantasy too. She couldn't wait to know what his sexual fantasy was too and if his sexual fantasy corresponded with, compliment, and connected with her sexual fantasy. Wouldn't it be wonderful if they both shared the same sexual fantasy? Just as one of the requirements in her sexual fantasy was to have sex with a much older man, it would be perfect if his sexual fantasy was to have sex with a much younger woman.

'What are the odds that their sexual fantasies would be the same,' she thought in her naiveté.

"Now that I told you my sexual fantasy, tell me your sexual fantasy? Tell me, Walter. I want to know," said Kim.

She impatiently waited for him to respond. As if taking forever, as if waiting for a microwave to heat her food, she stared at the blinking cursor. Then, finally, he wrote back.

"Not here. Not now. Not online, Kim," he said. "I don't want my sexual fantasy uploaded to the cloud," he said with a (lol) laugh sign and a smiley face.

When he paused, she responded.

"I understand," she wrote.

When she paused, he responded.

"If you decide to meet you in person, when we're alone in the safety and privacy of my house, other than to have sex with you, I'll tell you what my real sexual fantasy is in great detail. Only, I can't tell you that now. I'm from a different generation than you are. I don't trust computers in the way that you do. I can't help but think that someone is reading all that I write. For all I know, you could be much younger than 23-years-old. You really could be jail bait. For all I know, I could be writing to a policeman waiting to arrest me."

She was disappointed that she told him every personal, sexual thing about herself and that he didn't share ever, personal, sexual thing about himself. Yet, she understood his reluctance and his hesitation. Moreover, whether he knew it or not, he gave her even more reason to meet him in person.

"All that I can tell you is that I really am 23-years-old and am not jail bait," she wrote with her own (lol) and smiley face sign.

### ILookLikeJailBait ###

Their e-mails and written correspondences progressed from chatroom roleplaying to long winded telephone calls discussing their plans to meeting one another. Obviously, especially in the beginning, he wanted to meet her more than she wanted to meet him. She wished he was more her age. She wished he was forty, thirty, or even twenty-years younger than he was. Yet, not wanting to ruin a good thing, she knew she either had to invite him to her hometown or go to where he lived.

She felt pressured to take the next step in their cyber relationship. Sitting on the fence before taking a giant leap of faith, it was a bittersweet moment when she agreed to fly out to Detroit. She had never been to the automobile capital of America. She had never been anywhere. This would be her first time on a plane and she was just as nervous about meeting him as she was about flying. Meeting him would be quite the adventure and something she'd, no doubt, talk about to her friends and co-workers for years.

Only, she was afraid to take the plunge. If he lived closer, she wouldn't think twice about meeting him for coffee, for a drink, or for lunch. Yet, this entailed her packing a bag. This entailed her getting on a plane and flying to Detroit. This entailed her staying overnight or longer in his home. After sharing her outrageous sexual fantasy of roleplaying rape with him, this entailed her trusting him to keep her safe and not to take her sexual fantasy so literal by taking sexual advantage of her. What she wrote online was one thing but what she'd never do in person is something else.

What if he viewed her sexual fantasies as more than roleplaying? What if she agreed to meet him and he wanted to play out some of her sexual fantasies? What if he wanted to play out some of his sexual fantasies? What if she didn't like him as much as he liked her? What if he pressured her for sex? Fear replaced her sexual excitement.

What if he thought she really wanted to be taken, tied to a beam in his cellar, and stripped naked? What if he thought she really wanted him to rape her? What if he was insistent that she suck his cock and not stop until he ejaculated his cum in her mouth and she swallowed? What if he was intent on eating her pussy and fucking her? What if he really was a rapist and/or serial killer?

'Oh, my God. What have I done? How can I possibly meet him now? He must think me a real slut and a wicked whore. What I wrote in a chatroom, I'd never do in real life. Writing to him, a total stranger didn't seem real. Writing all that I wrote was as if I was writing in my diary. Only, he'd never understand any of that. What I wrote aren't things that I'd actually go through and do with a total stranger, especially some much older man that I met on the Internet.

"I can't meet him. With me 23-years-old and him 66-years-old, I can never meet him. Somehow, I'm going to have to break it off. Maybe I just won't answer him when he e-mails me, respond to him when he asks for a chatroom request, or calls me on my phone the next time. Maybe he'll think I moved or I died. Yet, with my luck, he'd travel here and come looking for me. I need to take the bull by the horns and end this right here and right now," she said talking to herself as if she was talking to one of her girlfriends.

### ILookLikeJailBait ###

She didn't have the courage to break it off with him. Instead, she was curious enough and sexually excited enough to meet him. She needed to meet the man behind her computer screen. 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.

Now, no longer confined to a chatroom, here she was at the Detroit airport ready to meet her cyber lover. Surprising even herself, she couldn't believe she was actually doing this. She couldn't believe she had boarded a plane and flown here. Having never met anyone she met online in person before, Kim was nervous. A big risk, a gamble, and a crap shoot, already having second thoughts about meeting him, she didn't know what to expect. A woman alone, a woman who writes erotica on a pornography site online, and with him 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 this. I should have broken it off with him.'

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, she'd never have sex with him, of course, a complete stranger. Taking her against her will, he'd have to drug her for her to give him sex. 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. She could be walking into some sort of diabolical trap.

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 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 there 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.

### ILookLikeJailBait ###

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, 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 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 30-years older than she was.

She had never dated anyone old enough to be her father, only never having known her father, she 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 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 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 with him roleplaying while he sexually and incestuously abused me.'

To be continued...

*****

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  • COMMENTS
11 Comments
Marklynda2Marklynda2over 1 year ago

Careful what you wish for. Being of the older generation I too am hesitant to put my true self out there. Good story and I'm looking forward to reading chapter 2. Thank you for sharing your vision and talents.

MstrPussyEaterMstrPussyEateralmost 2 years ago

She is the kind of woman I seek and want... As a let 50's successful Sigma Male with worldly experience and a life of many adventures having done more than most dream of and yet I still have to find the special submissive woman that can be close to being my equal outside the bedroom and yet my submissive yearning to learn and explore all the pleasures and fantasies one can have. I wish to let the "inner slut" of her out and reap the benefits and maybe even share her with others to fulfill all her desires and dark fantasies safely as i protect and watch over her and orchestrate the event allowing her to really be free and let go and express herself without reprisals, jealousy or bad and hurt feelings as long as I have her heart and love then i will give her the world as I expand her horizons and teach her all the thins she was afraid to try and never had a man who would allow her that freedom. Setting her free but knowing she was always going to be Mine and that she knew that my Loyalty was forever as long as hers was to me. The perfect epitome of a Master/Sub relationship bonded together on a much deeper level literally sharing Everything without question as she knew I had her back and I could Always trust in her and thru honest communication, respect and trust we would venture together as one. Whether she was younger or the same age as long as she wasn't so mentally scarred and damaged from abusive men or trauma as sadly there are bad people and for those of us who have strived to stick to our belief in Integrity and Honor and Commitment taking it to an even higher level with the ones we have relationships. As it means so much more to have a connection and a relationship as one night stands and fwb are nice but to have a really Deep level now relationship that is what i truly seek. Hopefully without games or bs that women tend to do when they find man they find attractive or has money. Some of them see him as a way to support and take care of herself until the point he asks for a Real Commitment and then suddenly her true colors of just being a greedy gold digger are revealed. I wish to have a Princess and to be her King as she described in the story and have a woman who can release herself to being my lovingly ravaged submissive slut that i keep forever. My last gf was so turned on by my special skills as i made her a squirter and capable of having multiple orgasms to the point she came constantly after i trained her. She became a local slut afterwards chasing the orgasmic delight and not finding it in one man so she would take on two or more to achieve the same level of orgasms but never got them as then they tossed her aside as just another slut so she ended up so disappointed and dissatisfied and hadn't realized the deeper connection i offered her until it wasn't there and she couldn't find it. so in spoiling her I spoiled her for other men and now she wants that but finds it elusive as she chose the physical way and didn't see the mental and emotional connection. So I want it ALL from a Woman.. Her Body, Her mind, Her Soul and thru that she will have an experience and Lifetime of Adventure and Fulfillment with freedoms singles have but commitment of a married couple in our Dom/Sub ideal relationship.. The absolute Ultimate for the absolute perfect woman.. Oh and I am 6 ft, got the 6 figure and working on the last 6 pk and over 6 in what they like so being in construction company owner i keep myself in top shape and is why i have all the crazy ones chasing me but i want that is Like this young Lady... As a Sigma male she has to be a top flight all around package and not just a pretty face, or smart egg as I want it ALL from her and will give it all to her too and maybe she is out there reading this, I hope..

ModdyModdyover 3 years ago

Love it!I feel the same as you. I too have daddy and pop pop issues. I also share the same fantasies. I get off flaunting myself. I love teasing.My dreams came true.I found a 61 silver fox, with a beefy,muscular body and a libido that challenges mine.It's incredible when he's aggressive and on top of me .To be to taken like that is mind blowing.He's a great teacher.

NaughtySouthernGentNaughtySouthernGentover 5 years ago
I like the versatility of where this story can go...

I love, love, LOVE buildup. Gaining insight into a woman's perspective is always captivating and makes it impossible not to follow the story!

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