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 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 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. 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. He hailed her a taxi, and this time she let him pay for her, 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 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 every time 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 bearable 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.
His arm around her back stroked down from the nape of her neck to her ass, openly cupping it. He looked down at her, her up at him, as his other hand slowly adjusted the controller, and she felt the vibrations in her pussy intensify. Her legs parted again, involuntarily, and she loved the way that made her felt, that her instinct was to open her legs for him. HIs hand on her ass pulled, and her thigh slipped over his so that his thigh muscle was now pressed against her, against her pussy with the vibrator working inside her. She moved her hips a little, pushing her clit against the pressure and moaned. She thought she caught sight of someone flicking their view over to her in that moment and blushed but then Jack adjusted the vibrator again and that pulse began and she nuzzled into Jack’s chest and her breath came in pants. His hand was so firm on her ass, pulling her against him, that thigh of his feeling so huge against her young body. “I love your ass, Kristine,” he murmured to her and she squirmed a bit under his touch and that sent all new shivers through her. Someone walked past them, a guy, and she wondered if he was watching Jack’s hand grip her little ass. Probably. He’d be a fool not to. A few blankets away, she was pretty sure the girl with the sunglasses was faking a doze as she watched what was going on. Hell, if Kristine saw this, she’d totally watch it. She wished she could see, could watch this, see her trembles as the secret vibrator poured pleasure into her.
He worked it expertly, his eyes always on her face whenever she could concentrate enough to meet his gaze. He took her arousal close in a rapid climb, she thought he was just going to make her come show her how quickly he could do that, but then he drew back and spent a long time with his hand on her ass, pulling her to him, sliding her imperceptibly but astoundingly wonderfully along his thigh. She was so fucking wet and the vibrator inside her was such a constant presence she was going out of her mind with happiness. She kept wanting to moan and panting out little half-cries half-laughs. He murmured to her, “You’re so fucking hot, Kristine. You’re such a good girl,” and that warm dark voice of his poured into her and if he hadn’t dialed it back just then she would have come and finally after so much time of this she had to she asked “Jack, I want to come,” and he held her close and kissed her and took the vibrator on a soaring ascendancy of stimulation and she put her hand in her mouth and bit it as she came shaking still moaning a little around her hand. She knew people must have seen must be watching and she was so fucking happy and delirious with pleasure. It lasted and lasted and she shook in his arms and finally her orgasm was fading into just echoes of pleasure and she realized the vibrator was off. She was still shaking though and his arms went both around her, he caressed her back and said “Good girl.” again and she felt so fucking good there in his arms and her pussy felt so fucking good with the vibrator still inside it.
She drifted off a little while later, her breath finally calming and Jack held her like that as she slept, her face and hand on his chest. When she woke up an hour later she stretched and felt the pleasure of that, too, of a nap in the sunshine and she still felt like the orgasm had just happened, looked at Jack with a wonderfully stunned expression. He kissed her until she really awoke, and they got up and he asked her if she wanted to see the boxing gym where he had worked.
“Of course,” she said, “What’d you do there?”
“Boxing instructor,” he said, “I used to box,” and how could she not like that?
It was a totally cool old place, an old hand-lettered sign just saying “Gus’s Gym”. But inside it was meticulously clean and well lit. A handful of young men were working out in one way or another, hitting heavy bags, shadowboxing skipping rope– something she always found adorable and ridiculous when a guy did it. A large black guy was wandering around, stopping to offer a little advice, to adjust a pose. When he saw Jack, he smiled big and said, “Jack, my man, what’s up? You looking for work?” Jack shook his head, but said, “Just coming by to say hi. And to introduce you to Kristine.” He looked down at her, “Kristine, this is Perry. Probably my best friend who ever knocked me the fuck out.” Perry grinned and slapped a big hand onto Kristine’s and shook it forcefully, “Jack’s the dude,” he said, “Talks a lot of shit but some sense too. You liking it?”
She laughed, taken a little aback, and said, “Yeah, I am. Jack’s alright, I guess.” Perry laughed again, “Well, I know you’re smart, because that’s the only way Jack likes women, but what else you got going on? You want to learn how to box?”
Jack was grinning, leaving her on her own to deal with this, and she felt a desire to impress but mostly she actually just liked this guy and it made her like Jack even more. “Sure, actually,” she said, “I’ve got a lot of aggression to get out.”
“I bet, scary girl,” Perry said, “Well come in any time, and I’ll set you up for free with some training, see if you like it.”
“Thanks,” she said.
“‘sides, anytime we get a girl in here, the guys all work double-hard to try to impress her,” Perry said, “So you’re good for business.”
Another boxer had noticed Jack and waved him over, and Perry took the time to talk more to her. He was sizing her up, she knew, and she could feel some of the same shrewdness in him that she saw in Jack. Whatever test this was, she’d passed, or Jack had, and Perry was clearly now just enjoying her company. He explained he was the manager of most of the fighters in here, and though it made a pretty poor living, it was a lot of fun shepherding his guys along.
Jack came back over at that part, wrapping his arm around her waist. “Perry and you going into business together yet?”
“Apparently you work for me now,” she said, and got another laugh out of Perry.
“Well, I’ve got to get back to work,” Perry said.
“Can I show her around the whole place?” Jack asked, and Perry winked, “Sure.”
As well as the gym room, with its central feature of a boxing ring, there was a stairway leading up. Jack took her up it, and found an even more antiquated looking room, with ancient machines, simple iron weights, and bare benches. “We had bare knuckle boxing fights here every once in awhile,” Jack said, “Sort of a fight club, but bare knuckle boxing is a lot safer than gloved boxing. You can’t punch people in the head, basically.”
“That makes sense,” she said, “Did you do that?”
“Yeah, I did, and was pretty good at it. I liked it better than regular boxing, more about precision. Lots of fun.” She squared off then and punched him in the arm and he grinned and swatted back at her hugely slowly and she dodged it. She punched at him again and he reached into his pocket smiling and said “Pow,” and the bastard had turned on the vibrator and she stopped in mid-stride and said “Uh,” and almost sank to her knees. And then his hands were on her pushing her down and his voice was saying “Get on your knees” and she did. She could still hear the sounds from the floor below distantly Perry’s voice and the sounds of bags being hit.
She knelt there in front of him and the vibrator continued inside her and she was so wet again already so fucking wet for him. Only part of it was this vibrator inside her, much of it was the force of his hands on her, the force of his words on her. She’d known she was like this but having it in reality was something altogether different, even better, even more amazing. She felt freed somehow and smiled up at him and he shook his head admiringly and she loved that. He held the controller out and she saw as he turned it up and she tried to kneel still for him because she thought he wanted that. He reached out his hand and tangled it in her hair, and she sighed and moaned quietly for now. Someone might come up the stairs she supposed but she was going to kneel here as long as Jack wanted, with waves of pleasure spreading from her pussy through her body.
His hands were on her shoulders now and he was taking the straps of the sundress and pushing them down over her shoulders, taking the straps of her bra with it. Within a few seconds, she was stripped bare to the waist, her arms caught against her side, her young breasts exposed. She’d loved the way the fabric had felt as it pulled over her nipples and now his hands were on them lifting them pulling them up roughly and she arched her back to press them further into his palms. “”Such fucking gorgeous breasts, Kristine,” he said. “Why thank you, Jack,” she said, looking down at his hands pulling on them, “I thought you liked them.”
“Such a smart little mouth,” he said, his voice going down to that husky growl she fucking adored. His hands were on his belt buckle then, and right in front of her, so close to her he pulled out his cock, she could feel the heat of it– already hard. She looked at it happily– “I did that,” she thought to herself, as the vibrator inside her slowly ramped up the well of pleasure inside her. Her arms at her sides, she couldn’t reach out for it, but she leaned forwards to kiss it, to press her tongue on it. He smiled down at her but took it in his hand and slid it against her cheek. So fucking hard against her, she closed her eyes as the velvety skin and hard shaft pressed against her.
“You look perfect on your knees,” he said, and his cock slapped against her cheek then, surprising her, and at the same time making something jump in her sexual soul, something that had never been reached before. “I’m going to fuck your little mouth, Kristine,” he said, as he slapped his cock against her other cheek, the solid weight of it just so fucking arousing.
“That’s what it’s there for,” she managed to say with a shaky breath, and that fucking did it, his hand firmly wrapped in her hair then and she opened her mouth for him and he put his cock against her lips and pulled her head and she made a tight ring of her lips. He pushed and his hands drew her to him and her tight lips passed over the head of his cock and the shaft of it filled her mouth and he held himself there for a moment and then pulled her hair again and pumped his hips and it was too much but she wanted it she even forced herself forward a bit as she gagged on his cock and he pulled back and she gasped and he fucked it back in and again and her lips were dragged back and forth along his shaft so wet from her mouth as he just used her fucking mouth. The vibrator inside her pussy took on a new dimension, when the beat of it coincided with a thrust or pull of his cock it exploded another bomb of pleasure inside her and struggled to stay upright under the assault of the vibrator and his cock and his hand shift
She could still hear the sounds from below and that just aroused her further. Here she was on her knees with Jack’s cock ramming in and out between her tightly-held lips. She was giving him a good blowjob she knew she could hear his grunts, his gasps as her little mouth sucked that cock. Her pussy was so goddamn wet as he just kept fucking her mouth sometimes just letting it slowly slide on her tongue as he looked down on her– she loved looking back up at him them, imagining how she looked to him– and sometimes he challenged her again, gripped her hair hard and fucked that cock to the back of her throat until she gasped and he relented and let her breathe again.
She felt his touch on the controls match what he was doing even more closely and fucking hell she was going to come again she was going to come with Jack’s cock filling her mouth, while he fucked her mouth. “Fuck yes, Kristine,” he murmured as he held her hair tightly, looking down at her, “Come for me like a sweet little slut. Show me how hard you come while I facefuck you.”
She moaned at that and that turned into the start of the orgasm and he fucked her mouth throughout it holding her aloft by her hair and she tried to keep her lips wrapped tight but she was moaning so hard and her pussy felt just so good but oh god now just aching for more the bullet not enough she wanted what she always wanted she wanted Jack to pick her up and fuck her.
And he was, his hands pulled her off the floor and roughly slung her down on one of the old benches. She barely had time to grip it before he had her skirt up in back and had pulled out the vibrating egg– that moment of release was another huge gush of pleasure. Then his cock was entering her– her breasts slick from the facefucking she’d received, hanging down as his very first thrust penetrated her to the hilt, knocking her forwards and making her shout. They might have heard that on the first floor she thought and gripped the bench because he wasn’t going to stop he was grabbing her hair in one hand and pulling back hard again fucking taking her like he knew she wanted.
“Fuck that little pussy, Jack” she said, bucking back against him as he pulled out, trying to keep that whole cock up inside her. He laughed and spanked his hand down hard on her little ass and fucked his hips forward, pushing her up on the bench again. “You like it like that, slut?”
“You know I do. You know,” she said “I want to you to fuck me like a bad good girl.”
And she thought of Perry’s wink, that he must know that Jack was taking up here to fuck and she didn’t care she loved it she loved that Jack would kiss her in public and she just fucking loved this and didn’t care who knew it loved to show it her mind was melting as he just fucked her over and over, his hips slapping into her ass, him rising above her as her hips tilted and filling her impossibly far over and over again. Her breath was getting knocked out and her bruised lips made her remember panting around his cock–he had a habit of fucking her breathless one way or the other–and then his thumb was pressing up into her little ass and she rose up on her arms and pressed back against him and his hand went under to strum across her clit and his hand pulled her hair back and kept her in a perfect arch and yes “Fuck yes Jack fuck yes make me come”. He growled “I’m fucking coming Kristine I’m fucking coming inside you” and she felt it as he pumped back in one last time and was so deep in her but she could still feel it even as her pussy squeezed him she could feel the cum exploding out of him filling her pussy up joining her wetness. She came all through his orgasm, feeling her pussy sucking on him like her mouth, feeling his finger still invading her ass, reminding her of the assfucking she looked forward to again. And he said her name again and again as his cock pulsed the last of his come inside her and she must be so full of it, it felt like so much.
He lay on her for a few long minutes, and then slowly withdrew, his now-soft cock finally slipping out of her with a deliciously wet sound. She lay there face down, smiling, thinking of the picture she made, her legs still spread and looking so well-fucked. Finally she pushed herself up, and made no effort to cover herself as she hugged him and he lifted her up and kissed her bruised lips.
They made out for a while in a strange state of tenderness, and his hands deftly helped her back into her sundress. And then his fingers were holding the vibrating egg, and sliding it back inside her, and she realized today wasn’t even over.
And as they walked back down the stairs, a lot of glances went in their direction, and Perry gave her another wink and cheery wave. And inside her, the vibrator buzzed, mirroring that pleasure, and Jack led her out to who-knows-where.
Source: reddit.com/r/eroticliterature/comments/utkvbc/lions_tigers_part_3_final_chapter_a_young_woman