Caught! Pt. 08

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Jon gives Vanessa permission to have sex with Angelica.
3.2k words
4.45
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Part 8 of the 19 part series

Updated 06/11/2023
Created 03/22/2022
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JQueen9
JQueen9
653 Followers

28 Days

3200 words

Jon hadn't felt so good in a long time. Vanessa had completed her 28 day test. She'd messed up once, when she smoked without permission, but her behavior had been flawless otherwise. She'd even begun to think she felt better since she'd surrendered her freedom of choice to Jon.

It was still true that the only reason Vanessa was submitting to Jon was fear of prison. She knew he'd send her away if she didn't do everything he demanded. But he'd never told her to do anything that wasn't in her best interest, and she had to admit his judgment was better than hers.

His insistence on daily workouts had her in the best shape of her life. Four weeks of forced sobriety meant she didn't crave alcohol every day. She still had urges to smoke, but the urges weren't so powerful, and she could tell it was good for her health. Mandatory meetings with a therapist was a good idea.

Mainly, she was glad to know that she was acting like a woman who deserved to be Jon's lover. She'd felt like an imposter for so long that she hadn't realized how good it would feel to give up her life of lies. Being a sex slave wasn't as bad as being an inmate.

As always, she was dressed in sexy lingerie when he walked in the door. "I hope you had a good day, lover," she said. "I am going to make sure you have a good night."

Jon smiled at her. He'd begun to believe she might not be manipulating him anymore. "I have some surprises for you," he said.

He pulled out a brown envelope and removed a sheaf of papers. "This is the eviction notice that says you have to move out today," he said. Jon ripped the notice in half. "You can forget about being evicted."

Vanessa was so touched she began to cry. "Thank you," she said. "That is such a relief."

"Come with me. I want to show you something."

Jon had driven a dark blue pickup and parked in the garage. "Here are the keys," he said. "You have wheels again."

There was nothing fancy about the truck. Vanessa could tell it was getting old. There was a dent in the left rear fender. It was smaller than most of the trucks on the road. Still, she'd gone four weeks without transportation. She'd never driven a truck, but she realized this was a blessing.

"I'm sure you'd rather drive one of my sports cars," Jon said. "But you know I was concerned that you were driving recklessly when you had the Porsche. You'll be safer in this truck. I want you to practice driving cautiously. If you can learn to do that, we can talk about giving you something sportier."

"I will, baby," Vanessa said. "It will be nice being able to drive again."

"I hope so. I should warn you that the stereo doesn't work. But this truck is reliable. It won't break down on you."

Vanessa had expected that Jon would want to have sex as soon as they went back inside. She was mistaken. He had another surprise.

"Would you like a cocktail?" he asked.

Oh God. Did she ever! "Yes, please," she said.

Jon removed a small bottle of expensive vodka from his jacket pocket and used soda from the refrigerator as a mixer. By adding a couple of ice cubes, he produced a very nice beverage they could use to toast the end of her four weeks of bowing to his will. She was still a virtual slave, but at least she wasn't in imminent danger of being evicted and arrested.

"Taste good?" he asked.

"Very," she said.

"I would like it understood that you are never to drink before 5 p.m., and you are never to drink alone. Can you agree to that?" Jon said.

"Of course, Jon. I'll be more careful in the future."

They sat next to each other on the sofa. Both of them were glad that the 28 days had passed with only one major incident. Vanessa remembered how much it hurt when Jon used his belt to whip her ass; she'd do her best to avoid a repeat of that.

She felt the effect of the drink before she'd finished half of it. Cutting out alcohol seemed to make it work better.

"How are things going with your therapist?" Jon asked.

"Slow. He wants to talk about everything that has ever happened to me, including all kinds of things that I don't think are important. But I'm doing it. He's the professional. I'll talk about whatever he wants."

"Has he offered any judgments at all?" Jon asked.

"He has said that it's obvious that I'm pretty smart, but that my intelligence doesn't seem to stop me from doing stupid, risky things. That does not seem to be a very startling insight, frankly. I've known that for my whole life."

Talking about her therapist made Vanessa look defeated. "Don't worry about it, babe," Jon said. "Just keep putting one foot in front of the other. There's no hurry. You'll get there."

"I hope so," she said.

Jon wanted to change the subject. "How are your workouts doing? Notice any improvements?"

Vanessa brightened. "Yes! Big improvements! I have actual muscle tone now. Feel this!" She flexed a bicep and placed his hand there.

"My aerobic fitness is much better. It's all very, very noticeable. I'm surprised to see so much progress in such a short time, but my trainer isn't surprised at all. I work with her five days a week, and she knows exactly what it takes to whip me into shape. I've never exercised much before. I had no idea I could get fit so fast."

Jon wasn't surprised. Vanessa was a strong, athletic woman who'd never tried to cultivate her athleticism. A month of smoke-free sobriety combined with daily workouts was just what she'd needed. He was happy to see that she had something to feel proud about.

"How are you getting along with your trainer? Is she still flirty with you?"

Vanessa grinned. "More than ever. Trying to get a rise out of me has become a game for her. She knows I have a boyfriend, and I think she sees me as being some kind of challenge. I think she wants to recruit me to play for the other team."

Jon chuckled. "I can sympathize. It must be nice for her to train someone as sexy as you. She gets to hang out with a beautiful woman, and she gets paid for it. What a great deal for her."

"We both know it's not going anywhere, but it's nice. Harmless flirting can be a lot of fun."

Jon knew Vanessa had been with women before. She considered herself to be heterosexual, but fluid. She'd always prefer men, but she thought women's bodies were beautiful and tempting. Vanessa liked touching women and being touched by them. Her erotic needs could only be fully satisfied with men, but women held a lasting, sensuous fascination for her. She wished her experience with women wasn't so limited.

"Baby, I think it might be a good idea if you let this go beyond flirting," Jon said.

Vanessa wasn't sure she'd heard Jon correctly. "Did you just say I should seduce my trainer?" she asked.

"Well, yeah, I guess that's what I'm saying," Jon said. Vanessa found it hard to believe.

"You know I'm worried about you," Jon said. "I have no intention of ending our current arrangement anytime soon. I'm more convinced than ever that it's in your best interest to have me make your decisions for you.

"Look at how well you're doing. This needs to continue. I don't know how long. Maybe forever. But you can't live forever in a cage, waiting for me to tell you what to do next. That's not reasonable. It's not something I expect.

"Listen, our relationship is pretty complicated. The thing is, we are not in an exclusive relationship. We may have been heading in that direction, but it didn't happen. It's unfair to expect you to be absolutely faithful to me if I'm not faithful to you.

"But I don't trust you to be able to be with other men and not be tempted to resume your risky behavior. And I'd be jealous if you were with other men. I know it's hypocritical, but it wouldn't bother me if you were romantically involved with a woman. Especially if it's your trainer. She's a health nut herself, and she knows you're struggling to quit smoking and drinking. She'd be a positive influence.

"I want you to have friends. I want you to have a life that goes beyond the boundaries of our relationship. If you'd like to pursue a relationship with your trainer, it's fine with me."

Vanessa cringed a bit when Jon mentioned that they weren't in a monogamous relationship. She knew that Jon wasn't willing to be faithful to her - not after she'd humiliated him so thoroughly. Plus, he may have known that she'd cheated on him once. He'd probably figured that out, and just hadn't mentioned it because there were so many other things wrong with their relationship.

"Jon, that's a very generous way to look at things," she said.

"I think it's just practical. For the last 28 days, you've lived in a way that isn't sustainable over the long term. That's one reason I'm giving you that truck. You need more freedom, and I think I can trust you to be more responsible with it. You have my permission to get reacquainted with your friends, as long as you don't let them convince you to do something risky or self destructive. I think you understand what I expect.

"Long term, your emotional life needs to include more than just me," Jon said. "I'm talking too much. Is this even something that appeals to you?"

Vanessa thought about it. "The idea is pretty new. I'm not sure. I mean, I'm sure that I'm very attracted to Angelica. Until this second, I never imagined acting on it."

They sat silently for a moment. "It's up to you. Let me know what you decide."

Vanessa wrapped her arms around Jon's neck and gave him a long, warm kiss. This was the first time in her life that she was romantically involved with a man as kind and generous as Jon. Thinking about the shabby way she'd treated him made her feel ashamed. If she hadn't been such a horrible person, they'd probably be living together and enjoying an exclusive relationship. She doubted that would ever happen now. How could he ever fully trust her again?

Jon pulled her to him and kissed her in a way that made her feel protected and loved. He led her to the bedroom and gently removed her nightgown. They got on the bed and slowly began to make love. Jon and Vanessa both enjoyed wild, rough, uninhibited sex, but that's not what either one of them wanted right then. Vanessa wanted Jon to treat her like a woman he loved.

It was easiest to concentrate on those good feelings when they were in bed, with Jon moving slowly on top of her and Vanessa welcoming his every move. She began to moan softly as he made her cum, and he let himself cum soon afterward. They held each other for a long time. Their relationship might have a future after all.

XXXXXXXXXXXXX

Vanessa arrived at the gym early, hoping she'd have a chance to speak to her trainer privately. Angelica was in her office when Vanessa walked in and closed the door behind her.

"Vanessa! Are you early?" she asked.

"A little. I want to talk to you about something," Vanessa said.

"Anything for you, doll," Angelica said, turning on the flirtatious manner she'd shown to Vanessa since their first workout. "What's up?"

"I feel a little awkward, so I'm just going to be completely honest," Vanessa said. "I'm sure you know that I'm attracted to you. You're either a very good actress, or you're attracted to me, too. I have no idea if you're open to a relationship with me, but I'd really like it if you are. I can't stop thinking about you. It's been fun flirting with you, but I'd love it if we could move on to something more."

That was abrupt. Yes, there was a mutual attraction. Yes, they'd engaged in some pleasant flirtation. But Vanessa had a boyfriend. Was he willing to let her have a relationship with a woman, or was Vanessa thinking Angelica would be willing to sneak around and keep everything secret? Angelica had been involved in some pretty unpleasant romantic entanglements over the years, and she wasn't anxious to start another one.

But Vanessa was so beautiful, so sexy, that Angelica felt her heart pounding. She couldn't possibly ask any questions or resist. She walked around her desk, took Vanessa in her arms, and kissed her.

Vanessa thought Angelica had the softest lips she'd ever tasted. Angelica was taller and stronger than Vanessa, and her powerful arms felt a bit like being hugged by a man. But her feminine body felt completely different. They were both so aroused that it was hard for them to stop kissing.

"Why don't we cancel your session and go talk about this?" Angelica said. Vanessa nodded agreement. They both knew this "talk" was the kind of wordless communication that happened when two people were naked and in bed.

Angelica's apartment looked like a place where an artist lived. Nothing matched, but everything fit beautifully with everything else. It looked young and hip - the kind of place that Vanessa had always wanted for herself, but had never been able to arrange.

They were in each other's arms as soon as they closed the door. Angelica had a strong dominant streak, and she wanted to make Vanessa do all the erotic things that women did together. Vanessa felt Angelica taking control, and that was fine with her. She liked being told what to do. She longed to do everything Angelica wanted.

Vanessa was soon naked and on her back in bed, with Angelica's soft hand moving insistently into her warm, wet pussy. There wasn't actually much difference between the ways Jon and Angelica touched her, but their bodies felt completely different. Angelica's soft lips and tongue explored Vanessa's open mouth, and she gently eased Vanessa's legs apart. It was happening very fast, and that was fine with both of them.

When Vanessa felt Angelica's tongue licking up and down her wet slit, she got so excited she came almost immediately. Angelica was very assertive, using both hands to spread Vanessa's pussy open and pressing her entire face into it. She'd thought a lot about how sexy Vanessa was, but she'd never seriously expected to get her into bed. Angelica didn't want it to happen just once, so she was determined to make her cum so many times she'd want to do this again and again.

It was working. She made Vanessa cum, and cum, and cum again. She finally lifted her face from between Vanessa's legs. Angelica moved swiftly to press her own pussy into Vanessa's, scissoring together vigorously. Vanessa had never experienced that particular position, and she was surprised that it felt so good. She caressed Angelica's long, muscular leg and felt glad that they were finally making love.

Sometime after her next orgasm, Vanessa began to think she wasn't doing enough to give pleasure to Angelica. She wanted to eat her pussy. But Angelica was so firmly in control that Vanessa felt helpless to do anything but surrender to the intense pleasure of her touch. She felt Angelica press one a hand directly on her clit, then resume scissoring, and very soon Vanessa was crying out as she shook in her strongest orgasm yet.

Angelica was getting tired by this time. She was an extremely fit, strong woman, but she'd thrown her whole body into the conquest of Vanessa. The way she always made love was hard, energetic work. Even if they never had sex again, Vanessa would know that Angelica was an extraordinary lover.

They lay wrapped in each other's arms for a long time. Angelica hadn't cum herself, but she'd enjoyed the feeling of grinding their pussies together, and she'd absolutely loved the feeling of power she got from driving Vanessa wild with pleasure. It was exactly what she'd wanted.

At length, Angelica went to the kitchen and returned with two soft drinks. They were healthy choices, of course. "Here you go, baby," she said to Vanessa.

"That was quick," she said.

"Are you complaining?" Angelica said.

"Not a bit. That was wonderful. It was everything I'd imagined it would be."

"I'm glad. I'm also glad you recognized how much I like you. How attracted I am to you. I never expected this would happen because I know you have a boyfriend."

"He knows. I told him how gorgeous you are. I started talking about you after the first time you trained me. He understands how important you are to me."

"And he's not threatened?"

"Well, he says he'd be jealous if I did anything with another man. Being with a woman doesn't bother him so much."

"Sounds like a typical man," Angelica said. "He'll want a threesome soon."

"I don't think so. He's a very nice man. He knows I'm attracted to women, but I haven't had much experience. What he said is that he wants me to feel free to have friendships and relationships that don't necessarily include him. He knows I'm crazy about him."

It all sounded depressingly familiar to Angelica. This wasn't the first time she'd been intimate with a woman whose main commitment would always be to some man. Angelica had been with men in the past, and she'd enjoyed it, but she'd always preferred women, and she wished she could find a girlfriend who wanted to be in a committed relationship with her and her alone. She knew she wasn't the only woman who had problems finding the kind of romance she wanted. She wasn't the only woman who had to settle for what she could find.

But looking at Vanessa's beautiful naked body beside her made that seem alright. For now.

"I love how assertive you are," Vanessa said. "I felt like I was swept up in passion from the moment we started."

"Good. Get used to it," Angelica said.

"That's my plan," Vanessa said.

They finished their drinks. "There's something I didn't get a chance to do," Vanessa said.

"What's that?" Angelica said.

Instead of answering, Vanessa crawled down and put her face between Angelica's legs. She moved slowly, tentatively, but it made Angelica feel wonderful. Vanessa might not have had a lot of experience with women, but she knew how to eat pussy.

Angelica was so happy that this was happening. When she went to work, she had no way of knowing that such a wonderful surprise would begin when Vanessa showed up at the gym.

Vanessa spent the night, and it felt like they'd been lovers for a long time when they finally parted the next morning.

JQueen9
JQueen9
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Caught! Pt. 07 Previous Part
Caught Series Info

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