They spent that day bumming around Chicago, just looking at things. She'd never felt this immediately comfortable with a guy before, which was weird, but a good weird--considering what she'd let him do to her, what she'd wanted him to do to her. He showed her his places, his view of the city; the top floor of the public library, where she'd never been before. A glass-walled, glass-roofed strangely empty space, they saw no one else while they were on that floor. While she looked out over the city Jack stood behind her, his hands casually lifting up her shirt to caress her bra-cradled breasts, and she was half-afraid and half-wanted him to just fuck her right here, up against the glass. Instead, he kissed her and took her to a nice little lawn where old Italian men played bocce ball. They sat and watched the rhythmic clacking for awhile, and then got sandwiches at a nice little deli nearby. The girl behind the counter obviously knew--and liked--Jack, and Kristine felt a surge of jealousy at that interaction, found herself pugnaciously sticking her chest out. The sandwiches were excellent, though.
After that, Jack took her along the rattling Red Line, barreling down through the city from the area she'd know, the safe and sane semi-suburbs of the north and the Loop, down into the ghetto, with crumbling fine old buildings that were beautiful and sad. Along the trip, Jack pointed out the amazing artwork of the taggers on the side of the building, glorious scenescapes of whatever the hell was in the artist's mind, some pure abstraction and some very plaintive. And Jack's hands rarely left her, as they sat together his hand was on her thigh, or around her. She knew she must be so young next to him and they drew a few disapproving glances and some overly appreciative glances but he was focused on her, telling her about the places he'd been, the fun he'd had, the great people he'd known.
She gathered courage as he talked and told him about her escapades too, about being too bright and bored in class but a good girl so learning subversion, sneaking around, becoming sly. He liked that, smiled at her, kissed her hungrily. Even after the fucking he'd given her last night--she still hurt, in a delicious way--just a kiss from him was enough to start to make her wet. And he really didn't care who saw them; he just wanted to kiss her. And that was fine by her.
They got off in a totally bombed-out area of town, enough to make her nervous even with Jack along, but they got on a bus immediately and passed by lots of hollow-eyed wrecks of houses, haunting and as full of promise as they were despair, until eventually the neighborhood picked up and they were near the university where Jack had gone. He took her around there, to the couple of places he'd worked at as a waiter, to the theater, where some people knew him and he introduced her and wrapped his arm around her. They were fun, interesting, and obviously liked Jack and didn't bat an eye at his new teenage girlfriend.
He showed her the prop shop where he'd worked in the off-season from firefighting, making the flats and scenes for the plays, and told her about a late night there with another girl where he'd bent her over the woodworking table and fucked her. Jack said this casually, not taunting her, and it caused a roil of emotion; of jealousy, of desire, of pleasure that he trusted her with stories like that. She kissed him, then, after that story, wrapped her arm around his neck and dragging his head down to her lips and he responded in kind, his hands going to her ass and squeezing and pulling her up against him, his hard body against hers almost lifting her off her feet until they were interrupted by one of his friends walking in. They broke the kiss, both half laughing, and Jack's friend laughed too and said, "Sorry, guys, I have actual work to do."
Jack took her for a cup of coffee at one of the places he'd worked. The cooks in the kitchen came out to say hi to him and he joked around with them for awhile; they were oddly decorous to her, respectfully shaking her hand. She liked this world he moved in; far removed from her sister's slick music production world, her parent's globe-trotting. It was amazing that somehow she could have this connection with Jack when they came from two such different paths.
At the end of the coffee, he told her he was going to have to work that night, probably until four in the morning--a commitment made awhile ago. She felt a pang at that, a sudden weird fear that she'd just made him up and if she lost sight of him he'd vanish and she'd never get him again, never feel him fucking her so hard she trembled again. He put his hand over hers and said "I still have that thing to buy you. I'll have it for you tomorrow--if you're free?"
She nodded, and managed to keep the panic-pang under control as he gave her a long, searching kiss goodbye, this time really lifting her off her feet. Passersby smiled or frowned and he finally put her down and god damn it she was wet again how could he do this, summon this from her, but as she leaned against him she felt him hard inside his jeans and knew that it was mutual. That reassured her, somehow. She called an uber and he kissed her again and sent her on her way and she spent the whole trip back up to her house thinking of all of this.
She thought of Jack working at whatever party or bar he was that night, and she wished she could join the crowd. She decided to get Jack to get her a fake ID, wrestled briefly with herself over whether that was too stalkerish, and went back to the memory of sucking his cock there at the party, letting him come down her throat, the amazing feeling of that thick cock pumping into her and then she had to retire to her bedroom and masturbate, using just her fingers, delicately on her well-fucked body, still aching a little from what Jack had done to her.
She slept in rosy dreams and awoke excited already, coming to consciousness far more quickly than usual. She checked her phone, and found a text from Jack telling her to meet him at noon a downtown coffee shop, and to wear a skirt or a dress. She responded simply with "okay". She showered that morning and her hands on herself felt wonderful, like she had a new body, like the things she'd been doing with Jack had really changed her. She felt like she was walking different, standing different, wondered if others could tell, if people looked at her and thought "She's getting fucked the way she deserves."
She put on semi-daring lingerie, a thong which she rarely wore. She chose a gingham sun dress that was almost too demure, but cut low and showed the tops of her breasts excellently. It fell only to mid-thigh, and she felt wonderfully naked in it. She took the train downtown, daydreaming and almost falling asleep and having to leap out the door at the last minute when it finally was the right stop. She went to the coffee shop and saw Jack already sitting there, observing the room, looking calm and at ease. A smile lifted him up as he saw her, he just grinned from ear to ear and she walked towards him happily feeling awkward and yet wonderful and he wrapped her up in his arms and again pulled her in for a deep kiss, just forcing her mouth open and pushing his tongue into her mouth. She tightened her arms around him and sucked his lower lip between hers as he disengaged the kiss, and he smiled at that, too.
"Hi, Kristine," he said, not letting go of her, "You look fucking hot as hell." He was looking down admiringly at her exposed cleavage, at her face, his hands on her hips, holding her in place. The feeling of her eyes on her was like a caress, and she shivered again; goddamn, she couldn't ever hide from this guy what he was making her feel. But she didn't want to. She liked this display, almost too much.
He bought her a coffee, and she noticed the bag he had with him. They drank coffee together, and he told her how he'd found this place--a really cool Armenian joint with classic brass and wood and the steam from the espresso engines floating like fog everytime one was made. And then he gave her the bag, and told her to go to the bathroom with it. She nodded, and walked there with the bag, every step mounting her excitement. She locked the door behind her, and looked in the bag, took out the box that was in there.
It was a small, discreet egg-shaped thing. A card was included. She read it--a remote controlled vibrating egg. There was a small pouch of lube in the bag as well. She held it in her hand, surprisingly heavy for a small thing. Then, looking in the mirror, she pulled her dress up with one hand, and reached under with the egg, pulling her thong to the side. She pressed it against herself--fucking hell she was already wet, just from the idea of Jack getting this for her, and after a moment's force it slipped inside, held securely in her tight pussy. It felt good just like that, and as she straightened up she could feel it shift slightly, a faint pleasure in that alone.
She looked at herself in the mirror for a few moments, marveling at how well she was combining demureness and hotness today, and loving that she had this inside her, that Jack had given it to her. She opened the door and walked slowly back to the table, sitting down. "Thank you, Jack," she started to say, and his smile widened and she gasped loudly because he'd started it, his hand holding the controller right there on the table. The feeling was incredible, and she had trouble catching her breath for a moment. She spread her legs unconsciously and flushed and wondered if anyone had caught sight of this. Jack took her hand in his giving her cover and she gripped it tightly and oh god he turned it up changed it from a small buzz to a pulsing force inside her. She hadn't thought such a small thing could be doing this to her.
She bit her lip and caught sight of a guy staring at her and she almost laughed because whatever fantasy he was having what she was doing was even hotter. She squeezed Jack's hand harder and he squeezed back and leaned in to kiss her again and she met his mouth eagerly. His hand was up in her hair then and she loved that, the feeling of that control he had, his forearm muscles against her cheek. She moaned into his mouth as he kissed her and she felt him smile. He dialed down the vibrator, and she regained some self control as he broke the kiss. She laughed, just a happy, purely pleased laugh, and resettled herself on the seat, the buzzing sensation still causing her pussy to fill with pleasure but dealable now.
"How do you like your present, Kristine?"
"I love it, Jack," she said. Nobody was immediately next to them, so she had the courage to say, "It feels so fucking good in my pussy." She was rewarded by his eyes widening and excitement flaring across his face; why the fuck did it feel so good to please him?
"You're going to wear it all day, Kristine," he said, and she nodded happily, "Yes I am, Jack." He grinned, and dialed it almost all the way down, and finally off--but she could still feel it in there, even as her arousal subsided to a quite hot ember. She wanted more, she wanted to beg him to turn it back on but she loved the sight of the control in his hands, his strong fingers, giving this up to him. She got up when he did, and walked only a little unsteady out the door with him, his hand holding hers.
He led her to a park, where he stretched out a blanket for them. The park was well-populated, freaks throwing frisbees and students studying, mostly the young and the hip in this part of town. As she lay down on the grass, he slipped his arm under her and she put her face down on his chest, looking up at him. A classic, 1950s boyfriend girlfriend thing, this out in the park on a sunny afternoon, except she had let him fuck her in the ass, except that she had a vibrator in her young pussy that she'd been ordered to use by her much older lover. But even so, Kristine thought as his hand stroked the nape of her neck and yes, the buzzing started to rise in intensity again, this was sweet, in a weird way. Weird good.
