.

I would suggest maybe blindfolding her while you initiate foreplay; good to heighten her senses. Play with her body and get her aroused. Work your way to her clit. Then tell her that you don’t have enough hands or that you could use another mouth to suck ether other nipple while you finger her clit to orgasm. Bet her orgasm will be stronger than normal.
 
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Wifey and I started the same, very timid but now takes out the bbc dildos and vibrators in her own. I shared another story here, but over the summer she came up to my office and started sucking on one of them while starring at me and then had me go down on her while she sucked on it. It’s a slow process, but Wifey and I are frequently spit roast with toys and she’ll smile at me and talk about taking other cocks. Not sure if we’ll ever really take the plunge, but Wifey loves teasing and posting with me.
 
That's so good to hear! That's exactly where I'm hoping we can get to eventually. I'll pick up a slightly bigger dildo as soon as I can. She knows it turns me on when she uses them so I'll keep very slowly encouraging it go a little further each time.
Maybe a dildo that has more girth versus length. Make sure she enjoys the feeling of being filled.
 
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I've been getting some great ideas from these posts but thought I'd start asking for help to see if I can progress things along.

My situation may be a little different as I've accepted that a hot wife relationship with my wife will probably never happen. We've been married for 20 years so I know her well enough to be understanding of the situation. Of course I'd love to be wrong as it's been a fantasy of mine since the beginning.
What I'm hoping for however is that we can progress onto at least role-playing the scenario.

I've been treading very lightly and slowly introducing a few ideas here and there. Her confidence has always been low about her looks so I always make a point to say how sexy she is. I've brought her some dildos in the past but she has never been all that keen on them. Recently we've been using them more and I've been telling her how hot it is to see another cock in her. She's not into large ones unfortunately and keeps saying I'm a perfect size. I'm only small really and she only just takes the 6 inch long dildo. I'm hoping to buy her a black dildo next. Maybe something a little thicker than me but not too intimidating. The hope is to have her start saying that she wants dildo instead of my cock etc.

Anyway, tomorrow while I'm at work I'm going to ask her to play with herself. I know she'll use a vibrator but I might tell her to use the dildos too if she wants and then she can tell me when I get home. I'm wondering if I should give her a situation to fantasise about. I was thinking something along the lines of me organising a massage at home for her. The guy turns up and I wait in the other room. I don't want to jump straight in and say it's a sensual massage etc but maybe tell her that we'll be having some fun after he leaves? Of course I'd be open to any other scenarios people think might work better.

I'm hoping to give it a few more months of subtle hints before finding the right time to be more direct about it. I appreciate any advice.
If you don't know her fantasies then this isn't really likely to work. It may turn her off or just not be her thing at all. Honestly, the overt, sexual fantasies may all be too much for her to start. Having a complete stranger over to the house for a "massage" would be tough. Other guys touching her, alone in your house, might creep her out entirely. So might the thought of you setting her up for it. Guys look over the simpler but still adventurous activities that might turn a wife on. This may sound simple, but does she go out without a bra ever? Without panties? Does she wear something subtly revealing at all? Would she wear a symbol such as an anklet, or even an anklet with HW symbols on it? Would she consider a belly button piercing? Will she chat with you or others about a sexy television show or movie she's seen? Would she consider attending a lifestyle "meet and greet" just to talk to other lifestyle women in a safe environment? Would she go to a topless or nude optional resort if you have the means and desire?

The list is endless, but trying to jump right in to sexual infidelity is way too big of a step for most wives. It takes time and seduction. And I mean in very subtle increments in most cases. If your wife is one of those who actually fantasizes privately about having another sex partner, then she might go through with that situation if she is encouraged and you give her blanket permission and then leave her alone about it. This may not be the way you wish for it to happen, but if she can have sex with other guys on her terms and not worry about fulfilling your wishes at the same time, then that might open her up to telling you about her experiences and perhaps including you.
 
My advice… just be honest in how you feel and with what you want. My wife to struggled with her self esteem etc… now being a Hotwife she’s horny all the time and her confidence is through the roof.

It took a year of just talking about it off and on. But I was totally honest with her about what I felt and what I desired and what I wanted.
 
You might want to consider continuing longer with the roll playing and allow that to become more comfortable and exciting for her and slowly and patiently expand things little by little. Unless she brings it up herself about wanting a bigger one, or even a black one, just keep building up her excitement and confidence before putting your own wants and desires first. Remember.. It’s all about her!!