Devoted Wife to Ultimate Fucktoy Pt. 05

'Oh yes, that's what I've been craving! That's it, deeper please -- I want it deeper,' she said, turning to look at him sticking his cock into her. Orlando gave her another couple of inches and watched her eyes widen, then her face broke out into a naughty smile. 'I think getting fucked in the ass is my new favourite thing!' she said.

Gina had also come to love observing Orlando's transition from being a dutiful and friendly trainer, helping her to stretch her ass, to actually pleasuring himself by fucking her. Both of them were more relaxed this time and it didn't take Orlando long to start screwing her. Even when only half of his cock was inside her, he choose to move it in and out of her ass, giving her the time to take more and more of him. He was considerate and attentive to Gina at all times, but she got the sense from him that he had been looking forward to this too and that he was determined to enjoy himself.

'I love how tight you feel around my cock,' Orlando said as he fucked her deeper and harder with each thrust. Her immense pleasure was tinged with pain, especially as she felt the tip of his bulging cock pressed deep inside her ass, but it's what she expected and what she wanted because she knew this wasn't any normal sexual experience. It was a very special and unique experience to get fucked by a man in this way and she liked that it felt different to how Matt used to fuck her.

'And I love feeling your cock in my ass,' she said, looking over her shoulder at him and fascinated by the sight of his huge cock going in and out of her ass. The whole scene was so erotic for her: she couldn't have been more glamorous and posh looking in her stylish evening gown, with her hair done up, and wearing her expensive diamond jewellery, and yet she was bent over her bed and getting fucked in the ass like a cock-hungry whore.

Orlando didn't rush his climax this time. As the person responsible for her extensive anal training, he had a good sense of how much Gina was able for. When they had only been using dildos, there were evenings when she had spent up to half an hour with the extra-large dildo in her ass. And now Orlando was determined to push her to this limit with his cock. Towards the end, when he was finally nearing his climax, he slowed the pace of his thrusts and screwed her as tenderly as it is possible to do in her ass. He lay on her, kissed her on her shoulders and neck and called her 'an amazing fuck'. Gina was so turned on that she had to pleasure herself with her hand.

'My ass is yours, Orlando. Nobody could fuck me there like you do,' she said as she was about to climax. Orlando came a few seconds after, letting out a loud sustained moan as his orgasm overtook him. He remained on top of her, his cock almost entirely inside Gina's ass. He eventually pulled it out of her and stood up.

Gina, still lying flat on the bed with her legs spread, looked over her shoulder at him and smiled. 'You're quite naughty too deep down!' she said.

'You know how to bring it out in me!' he said and walked towards the en suite bathroom. Gina could see that he had once again shot a huge load, which made her curious about tasting it sometime or getting sprayed on her face.

She stood up when Orlando was in the bathroom and tried to adjust her dress. She walked to the mirror and saw that her hair and make-up and dress needed adjusting. She looked like she had just been fucked, which pleased her to see.

'I feel like you really opened me -- even more so than normal,' she said as she walked into the bathroom after Orlando.

'Can you feel it when you walk?'

'Oh absolutely! It's almost like I still have the butt-plug in me. I feel open, like my ass is getting ready to take more cock.'

'It's a good thing you have a date with Josh tonight so!' Orlando said.

'Well, I'm not sure I'm going to let him fuck me in the ass tonight,' Gina said as she fixed her hair in the mirror. 'Call me a conventional gal but I think it's enough to suck his cock and take it in my pussy on the first date!'

'You're right -- that's more than enough. Let him earn the opportunity to fuck you in the ass,' he said and they laughed.

Orlando hung around for another while and they chatted while she finished getting ready. Gina loved being in Orlando's company because she felt so comfortable with him. She trusted him, he was one of the sweetest guys she had ever met, and he made her laugh. And she was enjoying the excitement in the fact that this was unlike any relationship she had had. They were essentially close friends who enjoyed anal sex together. She wondered if it was sustainable to keep doing this, especially considering that she was very attracted to Orlando. She fantasized regularly about sucking his cock, even touching his cock with her hands, which she had never done, tasting his cum, letting him come on her face and tits, and of course feeling his cock inside her pussy. But all that was way beyond the scope of anal training and perhaps something to be left to her fantasies only.

Orlando offered to drive her to the wine bar to meet Josh. She had been planning to book a cab, but she accepted his offer since he had his car with him. Before they left, they stood inside the front door, and Gina turned to Orlando to thank him for another very special evening. She leaned in and kissed him on the lips. But rather than stopping at a single peck, they both lingered and started making out passionately, their tongues intermingling and enjoying each other's taste. The kiss lasted for about three minutes and made her pussy wet. She was tempted to reach a hand down and feel for his cock but she resisted.

'Wow, that's quite the goodbye kiss!' Gina said when they eventually broke off the kiss.

'I just wanted you to know how sexy you are and how much I enjoyed this evening,' Orlando said. 'And I wanted to send you off on your date with Josh horny!'

'Well, mission accomplished!' Gina said. 'I just want to be fucked now!'

She and Orlando left the house, got into his car, and drove off in the direction of the wine bar.

Gina's pussy was wet for the entire drive to the Sterling Wine Bar. Orlando was being a great friend by comforting her because he could tell how nervous she was.

'At least you know Josh is going to love how you look,' he said. 'I'm sure he'll get a hard-on the minute he sees you walking in and he'll have to calm himself down somehow! You're going to have a memorable night, I just know it, Gina.'

'Thanks, Orlando. I don't know what's more terrifying -- being on a date with another man, sitting across from him and making conversation, or knowing that I'll probably be going home with him later and fucking him!'

'That's understandable,' Orlando said, turning onto Warren Street, where the wine bar was. 'Until quite recently you were living a normal life in a conventional marriage, and now you're going on a date with another man and planning to embark on your first extra-marital affair. It's all so new, of course you'd be nervous.' He pulled in the car and parked a few feet away from the wine bar. 'My one piece of advice, though, is to enjoy Josh's big cock,' Orlando continued. 'For two decades, it's just been Matt's cock and that's a long long time! So, even if you don't hit it off with Josh tonight, at least make the most of the experience by having a great night of sex with him. Enjoy tasting a new cock in your mouth, enjoy the feel of a new hard cock deep inside your pussy... Just have some fun! You deserve it after a difficult few months.'

'You're right, Orlando. I'm just going to go for it. I'm so wet just talking about it. And listen, thank you so much for coming over this evening and...'

'...fucking you in the ass!' Orlando said and smiled.

'Well, yes... I was going to say "preparing me for my big date", but yeah -- thanks for fucking me in my ass... again!'

'My pleasure, Gina.'

'And I just want you to know that no matter what happens tonight with me and Josh, I want you to continue training me. And... I might as well say it -- I'm hoping you will fuck me in the ass many more times. I'm not ready to give it up, even if Josh and I do have an affair.'

'I see -- I suggest we play it one week at a time and see how things are progressing with Josh. I wouldn't want to get in the way of anything.'

'You won't,' Gina said. 'Could you come over to my house on Monday evening as normal for a workout? I'd like to tell you everything about my date too.'

'Absolutely, I'll see you Monday,' Orlando said. 'Just in case Craig asks me -- will I be coming over to oversee your workout or to fuck you in the ass?'

'How about both? We can do our usual workout, then move to the bedroom to fuck?'

'Sounds great to me! Now off you go -- you don't want to keep Josh waiting.'

Gina reached across and kissed Orlando once on the lips and said: 'Alright, wish me luck!'

'Good luck!' he said as she got out of the car.

Orlando watched her as she walked towards the wine bar. Before going inside, she turned and smiled at him, then walked on.

20

Inside the door of the wine bar, Gina was greeted by a man in a stylish black suit.

'Good evening, Madam, you're very welcome to the Sterling Wine Bar,' he said. 'Do you have a reservation?'

'Yes, well my date booked a table,' Gina said. She glanced to her right and saw that Josh had already arrived and was sitting at the bar. He stood up when he saw her and Gina waved to him. 'Actually, I can see him over there.'

'Very good,' the man said. 'May I take your coat?'

'Yes -- thank you,' Gina said and the man helped her out of her coat and took it from her.

Josh walked towards her and got to see the big reveal of her glamorous white dress, which showed off her fit body in exactly the way she wanted.

'Gina, hi, you look absolutely stunning!' Josh said and kissed her on the cheek. She was struck once again by how big he was in comparison to her. She was a petite five feet, one inch, while he was well over six feet tall, which meant he had to bend down to kiss her cheek.

'Thanks, Josh -- it's nice to see you again.' Gina felt awkward and nervous, not being at all accustomed to being on a date with a man she barely knew.

The man who greeted her at the door returned and showed them to their table. Gina had been concerned that she was overdressed, but when she looked around and saw the other women she was relieved to see that she had chosen well. The wine bar was busy and all the women were wearing very glamorous dresses and the men were in stylish suits. As they were led to their table near the back, Gina got a better look at Josh and was impressed by how handsome and sophisticated he looked.

They were seated in a nice private booth with soft lighting and a candle burning on the table between them.

'You chose well -- this is a nice place,' Gina said after they were given the wine menus.

'I have to say, I was thrilled when you agreed to meet me,' Josh said. 'I wanted to book somewhere special. Honestly, I wasn't sure about your situation with your marriage if you'd even be open to meeting.'

'I'm glad you took a chance and asked me,' Gina said, still finding it hard to settle and relax.

'Me too and forgive me for being so forthright, but I'd like to get clear on it at the beginning. What is the situation between you and your husband?'

Gina could see that Josh had noticed her wedding ring, which she assumed would have surprised him.

'Oh, we've been together for 23 years,' she said. 'A long time. We have a 19 year old daughter together who's now in college. But my husband and I are on a sort of trial separation since a few months ago.'

'Okay, and do you think you will end up getting back together?'

'I really don't know. It's starting to look more unlikely as time goes on, but he wants to. And our daughter is hoping we will work it out.'

'Thanks for telling me, Gina,' Josh said. 'I promise I won't pry anymore unless you want to talk about it. I just don't want to get in the way of anything.'

'Don't worry -- I'm glad to be out tonight with you.'

'Me too. And if I'm being completely honest, I'm very attracted to you. You're a very beautiful woman and so I can understand if your husband was determined to win you back!' Gina couldn't help blushing at hearing Josh's compliments. 'I'm sorry -- I should warn you that I have a tendency to speak my mind,' Josh continued. 'Often gets me into trouble! I know I should try and be more subtle.'

'No -- it's fine. I like a man who says what he's thinking.'

The waiter arrived to take their order and Josh looked at the menu again.

'I had my eye on one of these Bordeauxs,' he said to Gina. 'What do you think?'

'Sure, sounds good,' Gina said.

For the next hour, Gina and Josh got to know one another over a fine bottle of red wine. And much to Gina's relief, she was enjoying herself and finding it easy to talk to Josh. He really did have a habit of saying whatever he felt like saying, which could be disconcerting for Gina, but she also liked it because it was quite a rare quality. At one point, he started talking openly about how much he had been admiring Gina's body, both on the previous Saturday at the club and this date. He asked all about her training regime with Orlando and she explained most of the steps, leaving out the anal training side of it. However, after a couple of glasses of wine, she was feeling more adventurous and revealed that she often takes off all her clothes in her home gym so that Orlando can properly monitor her progress.

'Orlando is such a meticulous and skilled personal trainer, and he's a very close friend and I trust him,' Gina said. 'So, it seemed appropriate to let him critique my body fully.'

'That's very interesting,' Josh said. 'And the approach obviously worked. Was it difficult for you being a married woman and being naked around another man?'

'It was after my husband and I separated,' Gina said. 'But yes, it wasn't a simple thing for me. Especially since I'd only ever been with...' Gina stopped herself, a little embarrassed. 'Sorry, you don't need to know that about me.'

'No, what were you going to say? Were you saying that you'd only been with your husband?'

'Yes,' Gina said after a pause, 'which I know is strange.'

'Not at all,' Josh said. 'It makes perfect sense. You were young when you met your husband and you were faithful to him throughout your marriage. I think it's admirable actually.'

'Thank you,' Gina said, choosing to remain quiet about the fact that Orlando had since fucked her in the ass twice, breaking her long streak of being a strictly faithful wife to Matt.

'I can appreciate how huge a deal it must have been to be naked with Orlando,' Josh said.

They continued chatting for another while. They talked about Kim and how she had made out with Josh's friend Andre at the club last Saturday. Josh revealed that Andre really liked Kim and was hoping to hook up with her. Andre even said that he could be discrete and didn't mind that she was married. But Gina was adamant that she wanted to discourage Kim from cheating on her husband.

As they came close to finishing their wine, they finally got onto the subject of Josh. He had been directing the conversation up until that point, but Gina was curious to find out more about him.

'So, you mentioned in your message that you've recently come out of a relationship,' Gina said. 'When did it end?'

'About six months ago,' Josh said.

'And how long had it been going on?'

'We were coming up to three years.'

'So it was serious?'

'Yes, very,' Josh said. 'We were thinking about moving in together. But that would have been a big mistake. Ultimately, we weren't compatible.'

'Incompatible in what way?'

'Lots of ways. We had different tastes. Sexually. That was a big one where we didn't really connect.'

'Sexually?' Gina said and he nodded. For once, he seemed to be holding back. But Gina was intrigued so she asked him to elaborate.

'Yes, sexually we were on different wavelengths,' Josh paused again and smiled. 'This isn't exactly typical first date material.'

'Maybe not, but I'm interested,' Gina said.

'Okay, then, but stop me if it sounds too crude or explicit for you,' he said. After a few seconds, he continued. 'In the bedroom I enjoy being dominant. And I'm extremely turned on by women who enjoy being submissive. The more submissive the better because I like having as much control as possible. I have to emphasize, though, that this is strictly a bedroom thing. It's how I prefer to play. I work hard and I like to play hard! I wasn't asking her to be submissive outside the bedroom. She tried it and we experimented but she just wasn't comfortable with it. Which was fine, but it meant there was always that incompatibility in the bedroom.'

Gina was listening, fascinated, while wondering what this meant for her if she went back to his apartment.

'I see -- and in practice, what did you want your ex-girlfriend to do?' Gina asked. 'In what way did you want her to be submissive? Like tie her up?'

'I do enjoy using restraints, yes,' Josh said, but he was measuring his words since he was unsure about Gina's tastes and didn't want to put her off. 'Mostly, I enjoy being in control of when the actual sex happens, when she was penetrated and where she was penetrated... Sorry, I really wasn't expecting the conversation to go in this direction. I don't want to scare you away!'

'Don't worry. I'm glad you told me.'

They had come to the end of the bottle of wine and so it was decision time about what to do next.

'Do you want to order another bottle or go somewhere else?' Josh asked.

'I'm thinking I'd better go easy on the wine,' Gina said. 'This being my first ever extra-marital date, I can't help but feel nervous and I can feel the wine going to my head.'

'Okay -- let's get out of here so,' Josh said. He ordered the bill and paid quickly, eager to move on to the next part of the date.

Gina and Josh left the wine bar together and when they got onto the street, he turned to her and said: 'I don't want to be pushy on the first date, but would you like to come back to my place for a nightcap?'

'A nightcap -- sure, I'd like that,' Gina said casually, as if it wasn't a huge deal for her.

Josh flagged down a cab and they got into the back together. After telling the driver the address, he turned his attention to Gina. She looked back at him, feeling awkward again. Josh looked like he was about to say something, but then leaned closer to her and kissed her on the lips. He just did it once and watched her reaction. She kissed him back and smiled, and within seconds they were making out passionately. Gina got the sense of an enormous release from Josh, like he had been waiting for a long time to kiss her and was now savouring it. She felt her pussy getting dripping wet once again as she felt his tongue in her mouth. They made out all the way to his place and she was impressed that he managed to resist touching her body because she knew he desperately wanted to.

They had to practically pull each other apart when the cab pulled up outside his apartment building. Josh paid the fair and they got out and walked to the front entrance. Inside, they took the lift to the sixth floor and he led her down the hall to his apartment.

21

Josh turned on the lights when they got inside and Gina glanced around the apartment -- there was a large living-room area, with a kitchen to the right and a door which she guessed was to his bedroom on the left. The place was very tidy and neat and the furnishings were modern and minimalist. Gina's mind, though, was preoccupied with sex and with Josh's next move, and she felt like she had to try hard to hide her nervousness and excitement.

'Let me take your coat,' Josh said and stood behind her. 'I was looking forward to see you in this light,' he said as he held her coat and walked around her, getting a good look at her from the back, side, and front. 'Your body is stunning, a thing of beauty!'