Devoted Wife to Ultimate Fucktoy Pt. 05

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Gina goes on her first extra-marital date with Josh.
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Part 5 of the 12 part series

Updated 04/17/2024
Created 12/04/2022
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(Chapters 17 -- 21 of 'Devoted Wife to Ultimate Fucktoy'. Recap of where we are in the story: Gina had been married to Matt for over two decades when he confessed that he had been having an affair with another woman. To deal with the devastation of her husband's infidelity, Gina turned to her best friend Kim for support, as well as to her personal trainer Orlando. Orlando is gay and is in a serious relationship, but he cares deeply for Gina and helps train her in many additional ways beyond mere gym training. He helps prepare her for her first affair with another man, including preparing her for anal sex, which she has never experienced. Gina and Orlando have become comfortable enough together for her to be naked around him during her home gym workouts. He is also keen to introduce her to the right guy that would help her to move on from her husband's infidelity.

Orlando suggests a friend of his named Josh, and he arranges a night out with a group of friends including Josh. On the night out, at a club, she meets Josh for the first time and they get along well. But she leaves early because her best-friend Kim, who is married, makes out with Josh's friend Andre. Gina felt obliged to take Kim out of the situation before she went further with Andre. Later that night, though, Josh sends Gina a message asking her out. She accepts and they arrange to meet the following Friday night in what would be her first ever extra-marital date.

Meanwhile, Gina has made great progress in her anal training with Orlando at her home by taking the largest dildo in her ass for the first time with his help. However, as the training progressed, they continued crossing more and more lines, which eventually led to Orlando fucking her in the ass and taking her anal virginity. Afterwards, Orlando jokingly said that he would be glad to do it again before her date with Josh on Friday.)

17

When Orlando finally left Gina's house, it was close to midnight. At the front door, they hugged and she thanked him again for being such a considerate lover and for taking the huge step with her of fucking her in the ass. He said it was a privilege for him and one of the best sexual experiences he ever had. He also reiterated that if she wanted to do it again before her date on Friday with Josh, he would be delighted to make himself available for her. After he left, Gina was still feeling elated and found it hard to come down and relax. She wanted to tell Kim, to talk to her about how she had finally done it -- she had fucked another man and not only that, she had taken an enormous cock in her ass. But she felt it would be unwise to tell Kim yet, so she had to keep it to herself. She drank another glass of wine, went to bed and climaxed a few times, before finally going to sleep soon after 2am.

The next day at work was surreal. She felt like a new woman with a new life stretching out before her and it was thrilling. She chatted with her colleagues at the office, attending the usual boring meetings, but all she could think about was that she was no longer an anal virgin. Josh had been in touch to say he had booked a table for them at the Sterling Wine Bar this coming Friday, which she was aware of as one of the classiest and most exclusive wine bars in the city. She was very pleased with the choice because she would need to wear a glamorous evening gown and Josh would have to wear his best suit. Gina was already imagining how the evening would go. She would have fun watching Josh doing everything he could at the wine bar to seduce her, despite the fact that she knew it was unnecessary because she had already made up her mind to fuck him on their first date. While in a board meeting in the afternoon, attended by over 20 people, Gina's mind was wandering and she was imagining wearing a glamorous dress, complete with high heels and expensive jewellery and her hair done up, but being back at Josh's apartment on her knees sucking his cock, tasting it for the first time. Gina got so turned on thinking about it that she had to go to the ladies room afterwards and make herself come in one of the private stalls. She had never done anything like this at work before, but the trend continued through the rest of the week. The next day she came prepared and packed the largest dildo she had and lube in her handbag. During the afternoon slump, she went into the ladies room again and entertained herself by taking the dildo deep in her ass. Her thoughts moved between Orlando and Josh -- from reflecting on how Orlando had fucked her on Monday evening to thinking about how Josh was going to fuck her on Friday.

Gina felt like a woman possessed and went around all week thinking about little besides big juicy cocks and taking them in her mouth, pussy, and ass. She also couldn't stop herself from thinking about cum. In her filthiest moments, when lying in bed, her ass filled with the extra-large dildo, she wondered if it would be out of line to ask Orlando to cum on her face some time. She wouldn't be able to pretend it was part of her anal training, but maybe he could do it as a once-off gift, like on her birthday. She wouldn't even have to suck his cock. She could just kneel down in her bedroom, naked, and let Orlando stand in front of her, jerking off until he sprayed his load all over her face. Realistically, though, she knew it would be more appropriate to rely on Josh for such 'gifts'. She was looking forward to Josh cumming on her face, as well as in her pussy and ass. There was so much she wanted to do with him. But Orlando had a special place in her fantasies too because he was the one who opened up this new sexual world to her. It felt right to her that he would also get the opportunity to make her feel like a cum-hungry slut by spraying his load on her face. But perhaps that was asking for too much, being greedy when she should be focusing on Josh alone. And she didn't want to go too far, to betray the trust that both Orlando and Craig had shown in her.

On Wednesday evening, Gina had a long videocall with her daughter Lily. Lily updated her on how she was getting on at university and she revealed that she had started dating a guy.

'That's fantastic,' Gina said. 'How long has it been going on?'

'About three months,' Lily said. 'His name is Pierre.'

'Pierre? Is he French?'

'Yes. And he's a really sweet guy. Clever too. He works as a university lecturer.' Before Gina could react to express her concern, Lily quickly added: 'So, yes he's a few years older than me, but he's a really good guy. You don't have to worry Mum.'

'I'm not worried -- I just want to know that you've thought this through,' Gina said. 'What age is Pierre?'

'He's not that much older. He's 32.'

In Gina's mind that was a big age gap considering that Lily was only 19, but she also knew that she couldn't risk alienating Lily by disapproving too forcefully. She could predict how it would go: if Gina objected, Lily would carry on with Pierre regardless and shut her out. Gina didn't want that. If Lily was going to be dating an older man, Gina at least wanted Lily to feel like she could talk to her about it in case she ran into relationship difficulties. However, there was one other major concern that Gina felt she had to address.

'Surely it isn't ethical for a professor to date a student? Won't you both get in trouble over it?' Gina asked.

'Pierre doesn't work at my university, Mum -- he's at a different one. Honestly, I don't want you to worry about it. He's a really nice guy and we get on so well. I'd like you and Dad to meet him soon. Trust me, you'd rather I was dating Pierre than any of the guys my age here, who are interested in only one thing.'

Gina accepted that Lily had a point and she decided to say nothing more about it for now. Lily also wanted to talk about her father and how Gina and him were getting along. Gina didn't want to say anything to distress her, so she just said that they were working on it. She chose to say nothing about her date with Josh on Friday, or her feeling that the marriage was in greater trouble now that she was going to fully embrace having sex with other men.

18

After work on Thursday, Kim called around to Gina's house. They opened a bottle of wine and sat and drank together in the sitting-room. Gina admitted that she had been feeling insatiably horny all week and that she could hardly wait until Friday to see Josh.

'I don't know if I'm going to be able to hide it during our date,' Gina said. 'He'll probably see it my face, that I'm dying to fuck him! I'm almost tempted to suggest we skip the wine bar and meet up at his place.'

'I have to say, it's incredible to see this side to you, Gina,' Kim said. 'You used to always be so reluctant to talk about sex, but I guess you've always had this sexual side. Being married, you probably just didn't get a chance to express it.'

'You're right, but Matt and I did have a pretty great sex life over the years. I have to give Matt credit: he was an excellent lover, he really knew how to satisfy me sexually. And he liked that I had a strong sexual appetite and that I love to get dirty and be submissive and be used. Deep down, I know what drove him to have an affair with Amber. For one reason or another, with both of us being busy with work, we hadn't been making enough time for sex. And he needed it, so he went looking for it elsewhere.'

'Still, there's no excuse for him cheating the way he did.'

'Of course not. I could never excuse it, but I do understand it. But I also know why he's so against me having an affair. It's not just that I'm his wife. It's that he knows me and knows that when I do eventually have sex with another man, I'm going to be so aroused that I'll become a total submissive slut for him. And of course, he's right. I've been preparing myself to be fucked in every conceivable way by Josh.'

'You have to admit, though, your attitude to having an affair has changed a lot since you first found out about Matt cheating on you. You were reluctant to even consider having sex with another guy back then and that's only a few months ago.'

'That's because in my mind I was still the dutiful and faithful wife to Matt. I couldn't just switch out of that. But really, it's because of Orlando that I've been willing to expand my horizons sexually. He's given me so much confidence.'

'I can see that and it's very inspiring!' Kim said.

'Which reminds me -- how did your first personal training session with Orlando go yesterday?'

'It was fantastic. He kept talking about you, as a matter of fact. He said he wants to do for me what he's done for you.'

'Really? And did you and Orlando discuss how far your training will go?' Gina asked.

'You mean, is it going to progress into training me for anal sex?' Kim said and smiled. 'We didn't discuss that yet but I'm really hoping that he'll do that with me too eventually. I think Ben would love to fuck me in my ass. It might add some extra spice to our marriage after all these years.'

'And are you sure it's Ben he would be preparing you for?'

'What are you suggesting?' Kim said playfully. 'That I would cheat on my husband!'

'Well, things were progressing very quickly with Andre last Saturday at the club. I saw where his hand was under the table! You were letting him finger your pussy!'

'Alright, Gina. I suppose it's hard to believe me now after that,' Kim said. She paused and took a drink from her wineglass and continued, hesitantly at first, as though unsure of how much to reveal to Gina. 'You're my best friend, Gina, and I trust you.... So I feel I can say this to you without being judged...'

'Okay...'

'Well, I did have a fantasy involving Andre...'

'Go on, I'm curious!'

'Okay, but it's very dirty, very slutty,' Kim said.

'If it's a fantasy, that's fine -- the sluttier the better as far as I'm concerned!'

'Yes, well I was fantasizing about having an anal-only affair with Andre. I would ask Orlando to get me ready for anal sex the same way as he did for you. And when the time came, I would arrange to meet Andre and go home with him, but on the strict understanding that he could only fuck me in the ass. I want to keep my pussy and my mouth for my husband, but I would let Andre fuck me in the ass as much as he wanted.'

'That's very sexy, very erotic, Kim,' Gina said. 'But it seems closely grounded in your real life. You're not seriously considering doing it for real are you?'

Kim was silent for a moment and couldn't resist smiling mischievously.

'Kim, you wouldn't!' Gina exclaimed.

'But would it really be so bad? Ben doesn't use my ass anyway! I was thinking it would be sexy to have another man have exclusive rights to my ass.'

'Kim, I know you're trying to rationalize this because you're tempted by Andre. And I get it -- he's a really hot guy who's also clearly very attracted to you. But think about it for a second. You would have to be completely naked with Andre back at his place and you would be letting him stick his cock inside you. There's no way of looking at that that makes it alright. You would be cheating on Ben and I think you'd end up regretting it, no matter how much fun you have taking Andre's cock in your ass.'

Kim looked disappointed but said, 'You're right, of course. I'm just getting swept up by the fantasy. And I guess I'm feeling jealous of you. It's hard to be envious of the fact that tomorrow night you're going to be in Josh's apartment have sensational extra-marital sex.'

'I know and I'm sorry. It isn't fair that I'm telling you all the things I'm planning to do with Josh. I should be more considerate.'

'No, I want you to talk to me about it. And I'm hoping you'll tell me about how you got on the next day too.'

'Of course, if you're okay with it,' Gina said. 'If it makes any difference, I'd rather have my stable and loving marriage back than be in this position of being separated and going on dates with other men. But, to be honest, being free to fuck other guys is certainly a nice consolation!'

19

Orlando came over to Gina's house on Friday evening and fucked her in the ass for the second time. And it was somehow even more spectacular than the first time on the previous Monday. Gina answered the front door at 7pm wearing the glamorous white evening gown that she had chosen for her date with Josh. It was a very stylish dress that she had bought two years earlier when attending a lavish ball with Matt. The ball was attended by hundreds of people connected with Matt's company and she remembered getting a lot of attention from men at it and being hit on throughout the night. The dress had a plunging V-neck that left part of her cleavage exposed but without being slutty. And the dress covered most of her legs, but there was a long slit that went all the way up to her left thigh and revealed her leg as she walked. Gina also vividly remembered how Matt had fucked her up against the wall in their bedroom when they got home. He was so turned on by her and how sexy she looked in the dress that he insisted on fucking her while she was still wearing it, and she was more than happy to do it.

She was hoping for a similar reaction from Josh tonight. She wore her long blonde hair up in a sexy ponytail and completed the look with long dangling ear-rings and a diamond necklace. Her choice of jewellery was provocative, at least secretly for her, because each item had been a gift from Matt. Matt tended to buy her jewellery on their wedding anniversaries and he had pretty good and expensive taste. The ear-rings and the necklace were two of her favourite pieces from her collection. She was feeling extremely naughty and it was turning her on so much to go with it rather than resist it. But her most daring choice was to also wear her wedding and diamond engagement rings. This was a momentous evening for her, to be going on a date with another man. But she didn't want to pretend to herself that she wasn't married. She wanted to embrace the fact that she was a married woman going on an extra-marital date. And it excited her to wear the jewellery that showed that.

'Look at you -- you look like a fucking movie star!' Orlando said when Gina opened the door and revealed the outfit to him.

'A movie star who is going to get fucked in the ass!' Gina joked.

Orlando laughed as he stepped into the house and took off his coat.

'And you're sure you want to do this?' he said. 'This is your big night with Josh. I don't want to get in the way of that.'

'You won't be -- I'd really love for you to open me up before I meet him. Actually, I sort of got started without you. I've been playing around with the dildos and I have the largest butt-plug in my ass right now.'

'I never cease to be amazed by you, Gina! I'd never have thought there was this bad girl underneath this sweet, polite exterior! I mean look at you: you look so beautiful and glamorous and yet underneath that dress you have a butt-plug in your ass!'

'I know -- I guess I'm a real bad girl deep down!' Gina said smiling. 'But I'm just putting into practice what you taught me about keeping my ass open and receptive to a big cock!' Gina had poured a glass of white wine for Orlando and left it next to hers on the coffee table in the sitting-room. She walked over and got it for him. 'By the way, how did Craig react when you told him that you had fucked me?'

'He was genuinely thrilled for you,' Orlando said and took a drink. 'He said he'd like to take you out and celebrate with you.'

'So, he's really okay with it?'

'Absolutely. Craig and I have a very solid relationship. And he's so happy for you that you had such a positive experience having anal sex for the first time.'

'It was so incredible and special and I have you to thank for it. You and Craig. I've been thinking about it all week.'

'Me too,' Orlando said.

They were both standing in front of the sofa. Gina stepped closer to Orlando and said: 'And honestly, I can't wait to feel your cock deep inside my ass again. I was hoping you would fuck me this evening while wearing this. Would you do that?'

'I'd love to,' Orlando said and put down his wine glass on the coffee table. Gina did the same, smiled, turned around and walked towards the stairs.

'What time is your date with Josh?' Orlando asked as he walked behind her up the stairs.

'I'm meeting him at 9 at the wine bar. I'll leave around 8:30, which gives us more than enough time to have some fun here first.' Gina went straight into the bedroom when she reached the top of the stairs.

'So, tonight is another first for you,' Orlando said as he walked into the bedroom and closed the door. 'Your first time to have sex with two different guys in the same night!'

'I know -- and neither of them are my husband!' she said and walked over to the bed.

'I'm sure you never imagined when you got married that there'd be a night like this in your life?'

'Absolutely not!' Gina bent over the bed, keeping her feet on the floor, and her upper body spread on the bed.

She remained in that position and watched as Orlando started taking off his clothes on the other side of the room. He didn't stop until he was completely naked, his cock already bulging and fully erect in anticipation of what they were going to do. He put on a condom and walked over to the bed, standing behind Gina.

'I'm very curious to see how easily you take my cock this time,' Orlando said as he raised the thin white fabric of her dress all the way up her legs. He saw that she wasn't wearing any underwear and that she did indeed have the large butt-plug inside her ass. He could see only the round shiny handle end of the butt-plug, which he wrapped his fingers around and gently pulled out of her to reveal the large gaping hole of her ass. Gina remained silent as Orlando put the butt-plug aside and guided the tip of his cock to the entrance. As he expected, the thick bulbous head of his cock passed into her ass with very little resistance, though Gina couldn't help moaning when she first felt the sensation of his cock in her ass again.