Jess Explores New Horizons

This is a sequel to Jess's Babysitting Job Takes a Turn

Rachel wanted Jess to spend the night, but she was expected at home and Jess did not want to upset her parents. "Maybe you can text them to say you are sleeping here so that we can make love all night and tomorrow morning," Rachel teased.

"I wish. I'd like that," Jess flirted back. Rachel could not resist kissing Jess and running her hand over Jess's perky, small breasts. "Maybe next time."

"That would be delightful," Rachel said. "Remember that we are visiting my folks next weekend, so we won't see you," Rachel added with a faux frown. "Are we on for the following Saturday?"

"On for babysitting, or something else?" Jess shot back.

"Ooooh, you sassy little brat, you may need a spanking," Rachel said laughing. She squeezed Jess's boob and then said "Anyway, both if I get to choose."

"Both it is, then... and the spanking is up to you," Jess said, bringing a big smile to Rachel's face. Jess was surprised by her flirty comments, but she was having fun. "You can do that harder if you want," Jess said nodding toward Rachel's hand on her breast.

"Wow, where did you ever come up with that naughty idea?" Rachel asked with feigned surprise, squeezing Jess's tit harder, making her wince.

"I once knew a sexy lady who liked it, so I gave it a try," Jess said haltingly as Rachel pinched and twisted her nipple. Jess reached to grope Rachel's big breasts roughly, making Rachel moan. They lay like that, kissing, as well as pinching and twisting, for about five more minutes before Jess rolled out of bed to dress. Rachel laid in bed watching Jess put on her clothes and absent-mindedly pulled and twisted her own nipples.

"Do you like it rough when you are alone?" Jess asked, again surprising herself with the bold question.

Rachel was surprised by the question too, but she admitted: "I do. It's not as good as someone else, but it still feels good." Looking at Jess, she confided with a smile: "My ex-husband was the first person who didn't think it was a little weird. It's the only thing I miss about him."

"Maybe someone will be able to make you stop missing him," Jess said with a wink.

"I hope so. You're only the first person I've shared it with since the divorce," Rachel said wistfully. Jess smiled and made a mental note to make Rachel feel good about her secret desire.

***

On Wednesday, Rachel texted Jess to remind her that she and her daughter were out of town, and ended the text: "Can't wait to see you next Saturday." Planning another hook-up with Rachel excited Jess, and she was particularly aroused reading the text while sitting with her parents. Even though Jess was twenty-one, her parents were oblivious to the fact that she might have any sexual experience. Jess decided she would read the text again in bed, and she knew she would end up masturbating thinking about Rachel. To set the stage for her fantasy, Jess told her parents that Rachel might start working later and that she had suggested that Jess could just sleep on Rachel's couch instead of driving home at 3:00 a.m. Jess's parents blissfully decided that Rachel's concern for Jess was very thoughtful, and Jess sleeping on the couch was a splendid idea.

To Jess's surprise, on Thursday, she was asked on a date for Saturday night by Max, the cute boy in her university Literature class. He asked Jess out to dinner and to a club where Max's brother was playing in a popular local band. Jess had been excited all week thinking about seeing Rachel again, and she had to switch gears for her date. She was pleased to find out Max was as sweet and funny as he was cute, and Jess had a great time. She noticed, though, that thoughts of Rachel popped into her head a few times during the evening.

In the parking lot outside the club where the band played, Max and Jess made out even before getting in his car. Jess was sexually aroused thinking about Rachel, the text, and their upcoming time together, and Max was in the right spot at the right time. Once in the car, he drove to a dark corner of the parking lot and asked if she wanted to "sit and talk for a while." She smiled and said yes even though she knew they wouldn't be talking a lot. Instead, Max leaned to kiss Jess and his hand slid over her boobs. A few minutes later he slid his hand under Jess's top and began feeling her bare breasts. Without thinking, Jess whispered, "you can do that harder if you want," and she was immediately mortified.

Max was silent for a few seconds and then he squeezed her breast very hard. "Like that?" he asked. Jess gasped and then nodded her head.

"Yes, even harder is okay," Jess said, still a little embarrassed but very turned on.

Max pinched and twisted her nipple roughly and Jess moaned again. "That's so hot Jess," he said, much to her relief. His hand moved to her other breast and he dug his fingers in and pulled like he was trying to tear it from her body. Jess yelped in pain, but Max did not back off as he felt Jess shudder from his very rough treatment of her boobs. Jess was so aroused that she began rubbing Max's erection through his pants causing him to pinch and pull her sensitive boobs even harder. Max was over the moon and, fortunately, oblivious to the fact that Jess was imagining Rachel clawing at her tits. But Max did benefit from Jess's aroused state when, for the first time in her life, she went down on a guy on the first date.

The following week dragged on, and Jess masturbated twice thinking about Rachel. She was turned on to see that Max had left her with several scratches, red marks, and one bruise on her boobs. She could not resist sneaking a feel of her own boobs when she saw Max in class, and her breasts ached when they chatted after class. The soreness reminded her of their date, but mostly it made her fantasize about rough play with Rachel. On Thursday morning, Jess texted Rachel to ask "What time do u need me there?" She took over an hour drafting that one sentence, wanting to make it as flirtatious as possible without being too much or too forward.

Within ten minutes Rachel texted back more directly: "I need you all the time. But if you mean for Saturday sitting, 6 p.m." Jess trembled when she read the text, and she had an urge to be with Rachel right then. But she replied only with the red lipstick kiss emoji, and Rachel responded with two of the same kisses. So the anticipation brewed all day until Jess went to bed early, stripped naked under the covers, and pinched and twisted her breasts that were just recovering from the prior weekend. Just a few minutes of the erotic mix of pain and pleasure, coupled with thoughts of abusing Rachel's breasts, brought Jess to a satisfying orgasm. Before she fell asleep, Jess marveled at how much had happened and how much she learned about herself in the last two weeks.

On Saturday Jess arrived nearly thirty minutes early, which was a first. Sarah wasn't even home from a play date, so Jess and Rachel were alone, and Rachel invited Jess into her bedroom where she was getting dressed for work. As soon as they were in the room, Rachel closed the door and moved toward Jess, backing her against the closed door. "I missed you Jess," Rachel said breathlessly.

"I missed you too," Jess said sincerely, before Rachel leaned in for a deep, open-mouth kiss. Jess' hands immediately were on Rachel's large boobs, squeezing hard and twisting. Rachel groaned, stepped back, and quickly lifted her tee up over her head and off, leaving her standing in a white bra that struggled to hold her big tits. "You can do that harder if you want," Rachel said seductively.

Jess dug her nails into Rachel's fleshy breasts and tore at the luscious mounds. "Oh yes,... god damn, that hurts baby," Rachel panted. She then reached behind her back and undid the bra, which she slipped off and threw on the floor. Jess stood there, totally enthralled by the sight of her hands moving back on to Rachel's huge tits. Jess then looked up at Rachel, whose eyes were pleading, so Jess moved her hands under Rachel's breasts and lifted them while leaning down to suck a nipple. Rachel cooed, but Jess knew what she really wanted. Jess moved her head some and then bit Rachel's tit hard.

"Owww, fuck, yes, that hurts so much," Rachel said breathlessly.

"Good," Jess said sternly, before biting the other breast just as hard, making Rachel squeal again. Jess dug her nails in the tit she wasn't biting and scratched, immediately leaving red marks. "You better get going," Rachel said backing off, suddenly the adult in the room.

"Gawd, I don't want to leave," Rachel said. "But you're right. You're the babysitter for goodness sake."

"That's right, and you're a naughty mom who needs to wait for playtime," Jess said with a smile. Jess then pinched and twisted Rachel's nipple and pulled it almost an inch from the breast. Rachel gasped again, and Jess reached for the doorknob. When she stepped into the hallway and closed the door again, Jess's composure fell away. She leaned against the wall, her heart racing and legs rubbery. Her hand slid down to cup her crotch and through her shorts she could feel the heat and dampness of her pussy. Jess bit her lip thinking about what might happen later that night when Rachel returned from work.

***

At 11:30 Jess got a text from Rachel saying: "Work was awful tonight. Sometimes I hate this job. Please have wine poured when I get home. xoxoxo." Jess wondered how Rachel's mood might affect their time together, but she dutifully found the wine and managed to uncork a bottle with just a small struggle. Since young Sarah went to bed before 9:00, Jess had tidied up the house, fluffed up Rachel's bed, and arranged the couch cushions where she planned to be sitting when Rachel arrived. Now she changed her plan and decided she would meet Rachel at the door with a glass of wine. Jess nervously watched the clock and surprised herself by quickly downing a glass of wine she poured herself after Rachel's text.

The next text from Rachel read: "5 min away. Somehow managed not to strangle any customers or staff." Jess had never heard Rachel say anything negative about work, and she hoped she could make Rachel feel better. A few minutes later, Jess saw headlights pull into the driveway, and she poured a new glass of wine and went to the front door. When Rachel opened the door, Jess could sense her irritation, but Jess said cheerfully, "Your wine, madam."

Rachel did smile a bit as she reached for the wine, but Jess saw that she was aggravated. Rachel took a big gulp of wine, closed her eyes, and said, "Wow, I needed that." Jess stood there, not knowing what to say that would be comforting. Rachel took a step into the house and turned toward Jess, pinning her to the wall. Rachel took a small step and leaned in to kiss Jess aggressively and back her against the wall. Jess was surprised as Rachel's tongue pushed into Jess's mouth and her free left hand groped and squeezed Jess's braless right breast. Pulling away from the kiss, Rachel said in a husky voice, "Sorry, I really needed that too."

"My pleasure," Jess whispered. "That's what I'm here for," Jess added seductively.

"Then you are exactly what I need," Rachel declared. Jess pondered both her comment and Rachel's response as they made their way to the sofa, where Jess had even set out a small plate of cheese and crackers. When they sat, Rachel took another drink of her wine and Jess refilled her glass even though it wasn't completely empty.

"Do you want to tell me about work, or do you want to change first? Jess asked.

"I want to get out of this outfit," Rachel said. "I'll just be a sec. Don't go anywhere," Rachel added with her hand now on Jess's left breast. Rachel squeezed hard and twisting the nipple, making Jess wince.

"I'll be right here," Jess promised.

About two minutes later Rachel returned wearing only a white button-down men's dress shirt and white panties. The shirt reached the bottom of Rachel's butt cheeks and it fit snugly around Rachel's fulsome boobs. Three buttons were undone to the bottom of her bust, showing off her ample cleavage, and her nipples showed through the white cotton. "I feel so much better already," Rachel sighed as she sat next to Jess on the couch.

"Tell me about your awful night at work," Jess said empathically.

Rachel explained how both her staff and the customers behaved poorly all night, saying twice that specific interactions made her "feel like a piece of crap." Rachel lamented that disagreements with staff or customer complaints are to be expected, but they should be handled respectfully. "Even if the customer is always right, it doesn't mean they can treat me like dirt," Rachel said, getting more animated. "They don't fucking own me," Rachel said angrily, and Jess saw tears in her eyes.

Jess caressed Rachel's thigh just above her knee and said, "I'm sorry Rachel, you are right. that is just rude." Rachel was still seething and a tear spilled from one eye and trickled down her cheek. Jess hated seeing Rachel so upset, and she searched for what to say, before blurting out: "And they definitely don't fucking own you... and, if it will make you feel better, you can own me." The comment surprised both Jess and Rachel. First, Jess rarely used the "f-word," and hearing her swear like that was almost amusing; and beyond that the idea of Rachel owning Jess seemed to come out of nowhere.

But Jess's comment struck a chord, and Rachel smiled a warm smile. Having Jess suggest that Rachel could own her was a wonderful balm for the emotional bruises Rachel had endured at work. She reached up to stroke Jess's cheek. "You are adorable. Although I might need to wash your mouth out with soap," Rachel said with a grin. "Or maybe spank you," Rachel added, still smiling.

Jess felt good that she seemed to brighten Rachel's mood, and the spanking comment made her tummy flutter. "Whatever would make you feel good is what I want," Jess said demurely. Jess thought that things were unfolding much differently than she had imagined after their short time together before Rachel went to work.

They chatted, and Rachel shared that Jess's comment about Rachel owning her was very erotic and made her feel good after the miserable night she had at work. "After being disrespected so often, it felt nice for you to be so... accommodating," Rachel confessed. "And to hear you talk like that... whew!" Rachel said pretending to fan herself with her hand. "I don't think I've ever had a more exciting offer than that." Although Rachel was being playful, her body language had changed and she seemed more confident.

Jess looked at Rachel almost shyly. "To be honest, I'm not sure exactly what I meant, but it felt nice to say it," Jess explained. "I've read a few things online, but I'm not sure what being owned is about," Jess said, blushing a little. "But I trust you if you want that."

Rachel was intrigued by Jess's proposition. "So, when you read about it, were you interested?" she probed.

"I guess, yes," Jess answered. "When I read about it, I always thought about you, even before two weeks ago," Jess confided. "I've always looked up to you, and last time was very exciting when you took control," Jess added sheepishly.

Rachel looked lovingly at the younger woman and leaned in to kiss Jess, their tongues softly pressing together. She then reached behind Jess's head grabbed a fistful of hair, and whispered in her ear, "Do you want to be mine Jess?" Rachel's serious tone put a charge in the room.

Jess was excited and nervous. "Yes, please," Jess gasped. She was still unsure of what she was asking for, but she knew she wanted to please Rachel tonight.

"Yes what?" Rachel all but spat.

Jess was already trembling. "I want to be yours. I want you to own me Rachel," Jess said in a quivering voice.

Rachel's grip tightened on Jess's hair and her other hand squeezed Jess's breast roughly. Rachel slid closer and then moved on top of Jess, pushing her on to her back and laying atop Jess on the sofa. Rachel was bigger and thicker than Jess, and her body weight easily pinned Jess down. Rachel allowed her weight to press on Jess, effectively covering her. She then slid up a little so that her cleavage smothered Jess, who rubbed her face into and kissed Rachel's boobs.

The new dynamic took over, and Rachel told Jess to strip for her. Still under Rachel, who lifted her torso some, Jess obediently pulled off her tee and wiggled out of her shorts and panties. Rachel then instructed Jess to unbutton the rest of Rachel's shirt, before she again laid on top of Jess so that their bare chests and stomachs pressed together as they kissed deeply. Jess shuddered as she felt Rachel's fulsome breasts pressed against her. Rachel then pressed two fingers to Jess's lips until Jess opened her mouth and began sucking on the fingers. Rachel shoved the fingers in deeply, causing Jess to gag and choke a little and bringing tears to her eyes. With her fingers still in Jess's mouth, Rachel bent down and kissed Jess on the forehead.

"Will you do anything for me Jess?" Rachel whispered. Jess quickly nodded her head. "Anything?" Rachel asked with a gleam in her eye. Jess's body tingled as she contemplated the question, and she nodded again and sucked on Rachel's fingers.

Now Rachel's body shuddered. "I want you sweetie," Rachel breathed out. "All of you." Jess sucked harder on Rachel's two fingers and moaned, with a look of surrender on her face. She wondered what Rachel was thinking, and she was excited by thoughts of what the evening might bring.

Rachel pulled her fingers out of Jess's mouth and moved off her. Jess was completely naked, and she laid lengthwise on the sofa with her knees slightly bent. Rachel sat on the end of the couch near Jess's feet and turned her body partly toward Jess. Her hand ran along the outside of Jess's left leg, feeling her soft, clean-shaven skin. Jess moved her eyes between Rachel's face and her boobs, which Jess lusted for. Rachel pushed Jess's ankles toward her bum, bending Jess's legs more at the knees. That gave Rachel as view of Jess's labia and a thin pink line of her inside folds. "Show me how you please yourself Jess," Rachel said firmly.

Jess skipped a breath when she heard Rachel's words. Then she spread both her feet and her knees apart, displaying herself to Rachel as her hand reached between her legs. Rachel watched Jess run her fingers between her lips a few times before moving to massage her clit. Before long, Jess was breathing harder and her chest rose and fell with each breath. Rachel reached up and gently pushed Jess's knees further apart, spreading Jess's pussy open wider. Jess got into a nice rhythm, shoving two fingers inside herself, moving them to massage her clit, and then repeating the motion. Rachel could hear the squishing noise made when Jess slid in and out of her pussy.

Rachel lightly touched the inside of Jess's thigh as she watched Jess masturbate. Jess vacillated between closing her eyes and looking at Rachel's breasts, fantasizing about sucking and then biting them. Rachel moved and straightened her right leg so that she could reach and massage Jess's breast with her foot, without disturbing Jess pleasing herself. Jess watched Rachel use her foot and toes to tweak Jess's nipple, and she was amazed how electric everything felt with Rachel. Their eyes met and Jess smiled and rubbed herself more vigorously.

Maintaining eye contact, Rachel adjusted her body and straightened her leg so that her foot was against Jess's face and her toes against her lips. Without a word, Jess opened her mouth and began licking Rachel's foot and toes. Rachel moaned and wiggled her toes. With the hand that was not rubbing herself, Jess took hold of Rachel's foot and guided it into her mouth. She began sucking Rachel's toes in tandem with massaging her now-throbbing pussy.