(Chapters 10 -- 12 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, where Gina can be introduced to him. Kim encourages Gina to just fuck Josh, and Gina prepares herself to go through with it. 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, Gina and Orlando crossed another line in the process: at her request he stripped naked too while stretching her ass. She was so turned on seeing Orlando naked for the first time and getting to see his enormous hard cock that she could take the huge dildo in her ass. Although there is an implicit acceptance that they are not going to have sex, being naked on her bed and watching Orlando with his huge erect cock sticking an enormous dildo into her ass over and over again has been one of Gina's most thrilling sexual experiences. In a few short months, Orlando has managed to turn Gina into the ultimate fucktoy. But is she ready to take that big step and have sex with another man?)
10
The rest of the week, leading up to the night out when Gina would meet her potential lover Josh for the first time, was quite eventful. Orlando came over to her house on Tuesday and Thursday evening. And although the official reason was for him to oversee her home gym training, as he had been doing for a few months by now, there was only one thing on his and Gina's mind: to discover how much of the biggest of the three dildos Gina could take in her ass. They were both committed to achieving the best result possible, so they repeated the same procedure from before -- which was for both of them to strip completely naked in Gina's bedroom, get onto her bed, and slowly build up to her taking the dildo while she lay on her front with her legs spread wide open. On each occasion, Orlando's cock was rock hard and Gina wasn't shy about gazing at it for long periods and secretly fantasizing about it being inside her. It had the desired effect at least of getting her extremely aroused, which helped Orlando penetrate her ass deeper and deeper with the extra large dildo.
On Tuesday evening, Gina remarked when they were both naked on her bed: 'You know, being around a hot naked guy with a huge cock has made me realise just how much I've missed sex. I haven't had sex once since I found out that Matt cheated on me.'
'That is such a shame, Gina,' Orlando said while spreading lube over the huge dildo. 'You deserve to be satisfied sexually by a worthy man.'
'Well, if I do have an affair, the guy will have you to thank for doing such an amazing job of preparing me for him!' Gina said as she tried to relax in anticipation of taking the dildo. Orlando was going about his usual routine of sensually massaging her back, moving to her thighs, and finally to her ass. His transition from massaging her to fingering her ass was skillful and seamless, though it never ceased to shock and excite her to reflect on how she was allowing a man other than her husband have complete access to her body.
On this evening, they made great progress. Gina took well over half of the enormous dildo in her ass and this time, Orlando kept it in her for much longer.
'I know I've told you that Josh's cock is enormous,' Orlando said, trying to motivate her further, 'but if you keep taking this dildo like this, you'll have no difficulty letting him fuck you hard in your ass.'
'That's what I'm hoping!' Gina said, between moans.
'I doubt he'd ever believe you're an anal virgin!' Orlando said, moving the dildo in and out of her ass.
'I don't feel like one anymore thanks to you!' Gina said and they laughed.
On the Thursday evening, they made even more progress. Gina expressed concern during the workout that they were going too far and crossing a line they shouldn't be crossing, especially considering that Orlando was in a serious long term relationship. But, to Gina's surprise, Orlando assured her that he had already told Craig about what they were doing, including about Orlando being naked during their most recent 'workouts', and Craig was very supportive of it and wanted her to meet her target.
This spurred Gina on to relax even more about what she was doing with Orlando. She even stroked his body when they were both naked on the bed. She ran her hands over his muscular torso under the pretense of admiring how great shape he was in -- which was true, but her real reason was that she just wanted to touch him. Her hands wandered down towards his waist but she had to use all her will power to not touch his erect cock. She would have loved nothing more than to wrap her hands around the shaft and stroke it hard. Or even better, to wrap her lips around the head of his bulging juicy cock and suck it deep until her mouth started filling with his cum. But she knew she couldn't do it because it would be like a betrayal of trust. Yes, this was one of the greatest sexual experiences of her life, having Orlando prepare her for her first extra-marital affair. And even though it had become customary for them to be naked around each other, they each had an implicit awareness that there was a line they were not going to cross. They were not going to fuck, as much as Gina might have wanted to.
On this Thursday evening, Gina felt so insatiable and aroused that she shocked both herself and Orlando at how much of the dildo she managed to take.
'Experienced pornstars would struggle to take it this deep and for this long,' Orlando remarked when he saw how most of the dildo repeatedly disappeared into her ass and out again. 'You have an exceptional talent you didn't know you had until now!'
'Perhaps I should update my resume!' Gina joked and continued lying down with her legs spread while Orlando opened her more and more.
11
Gina woke up on Saturday morning and instantly started masturbating, thinking about the night out later and the prospect of meeting Josh and possibly even going home with him afterwards and fucking him. She had finished work early the previous day and had stopped into the beauty salon to get her bikini line waxed. However, on a whim, she decided to ask them to tidy up the rather thick bush over her pussy. But 'tidying up' turned into removing it completely as she got up the courage to ask the woman to leave the area completely bare. Gina associated having a completely shaved pussy with pornstars because most of the women in porn she had seen had gone for that look. Gina had never done it but she was feeling adventurous and it felt right to do something extra, something different for potentially having sex with a new man. When she got home she felt incredibly aroused when she saw how she looked in the mirror, wearing nothing except a pair of classy high heels. She had spent a large portion of that evening pleasuring herself, including sticking the largest of the three dildos in her ass.
And on this Saturday morning, she was merely taking up where she had left off. In her fantasy at least, the course of events for the night ahead was crystal clear: she would be introduced to Josh at the club, she would flirt with him and get to know him, dance with him, then eventually leave the club alone with him, make out with him in the back of the cab back to his place, politely accept a drink when they got there but take the first opportunity to continue kissing him, encouraging him to explore her body with his hands and undress her, until they were finally in his bed, both naked, with him on top and his cock buried deep inside her pussy. She figured Kim was right -- she should stop overthinking it and just fuck Josh. It had been too long since she had had sex, her longest drought in decades, and it was affecting her everyday life.
Gina also had bought the perfect outfit for her night out: a tight-fitting black dress with a halter-neck. It was tasteful in covering her breasts and not showing off her cleavage, and at the bottom it came up just above her knees. But the dress was still very sexy because it left most of her shoulders, back and arms exposed, and its tight-fit showed off the curves all over her body, especially her ass. And because it was backless, she couldn't wear a bra with it, which anyone looking at her would surely notice. Depending on how she moved, her nipples could be slightly detected through the thin fabric covering her bust. When Gina bought it and tried it on again at home, she took a picture of herself in it and sent it to Kim for her approval. Kim responded by remarking that the outfit screamed: 'Married but ready to fuck another man!'
Later that morning, Gina got a call from Matt.