Win a Date?

wormwood

Male
Gold
Here's the deal; My wife and I play all kinds of fantasy games about and around the cuckolding fetish. We've set up scenarios where she leaves the house alone, dressed sexy while going to places where she can be hit on by men. She's left the house while doing her shopping without a bra and has enjoyed it when men stare and ogle her blatantly. Even though she enjoys this aspect of our play, especially the reaction she gets form me when she returns home, she has always maintained that she would never do it for real and is happy to keep it a fantasy.

Recently, while sitting on the patio, enjoying the late summer weather, I broached the subject of having a contest where a man might "win" a date with her. Something along the lines of posting her picture and having men enter themselves in a drawing where they might get an opportunity to take her out for an evening.

She actually got into it, asking questions about how it would be run and how they would win. My original thought was that the "date" would be in mid May, (my birthday) but off the top of my head I told her it would be a good idea if it was for a New Years Eve date. This, I reasoned to myself, would at the very least involve a fair bit of drinking, (a guaranteed situation that would rev up her libido) and the promise of a midnight kiss at the end of the countdown.

Judging by her reaction, she seemed very interested in this scenario and never raised any objections. In fact she still questioned me about it and seemed excited by it. The fact that she was wearing a white tube top and her nipples visibly became hard and remained hard throughout the conversation indicated to me her excitement. When she said " I would like to go out on New Years Eve", something we hadn't done in years, it told me that she might entertain the idea.

I told her that I would be the sole judge and would pick out the guy from whomever replied, but that she could pick the guy if I got to pick out what she wore for the date.

So my question is; How would I go about this? I'm sure there are a lot of things I haven't considered. What site would let me do this? How much of this would I have to pay for? Dinner? Drinks? It would have to be someone local or someone willing to fly in without the promise of sex or even relief. Although I'm sure that a date where she had a lot of fun, drank a good amount of alcohol and ended in an obligatory kiss would result in her feeling obligated to give some type of satisfaction? Actually I'm counting on it.

This is the first time she's ever displayed any willingness to go along with one of my hornier schemes and I'm very eager to follow through on her willingness. I must say that I realize she could shoot this down at any time.

Ideas? Thoughts? Objections?
 
Here's the deal; My wife and I play all kinds of fantasy games about and around the cuckolding fetish. We've set up scenarios where she leaves the house alone, dressed sexy while going to places where she can be hit on by men. She's left the house while doing her shopping without a bra and has enjoyed it when men stare and ogle her blatantly. Even though she enjoys this aspect of our play, especially the reaction she gets form me when she returns home, she has always maintained that she would never do it for real and is happy to keep it a fantasy.

Recently, while sitting on the patio, enjoying the late summer weather, I broached the subject of having a contest where a man might "win" a date with her. Something along the lines of posting her picture and having men enter themselves in a drawing where they might get an opportunity to take her out for an evening.

She actually got into it, asking questions about how it would be run and how they would win. My original thought was that the "date" would be in mid May, (my birthday) but off the top of my head I told her it would be a good idea if it was for a New Years Eve date. This, I reasoned to myself, would at the very least involve a fair bit of drinking, (a guaranteed situation that would rev up her libido) and the promise of a midnight kiss at the end of the countdown.

Judging by her reaction, she seemed very interested in this scenario and never raised any objections. In fact she still questioned me about it and seemed excited by it. The fact that she was wearing a white tube top and her nipples visibly became hard and remained hard throughout the conversation indicated to me her excitement. When she said " I would like to go out on New Years Eve", something we hadn't done in years, it told me that she might entertain the idea.

I told her that I would be the sole judge and would pick out the guy from whomever replied, but that she could pick the guy if I got to pick out what she wore for the date.

So my question is; How would I go about this? I'm sure there are a lot of things I haven't considered. What site would let me do this? How much of this would I have to pay for? Dinner? Drinks? It would have to be someone local or someone willing to fly in without the promise of sex or even relief. Although I'm sure that a date where she had a lot of fun, drank a good amount of alcohol and ended in an obligatory kiss would result in her feeling obligated to give some type of satisfaction? Actually I'm counting on it.

This is the first time she's ever displayed any willingness to go along with one of my hornier schemes and I'm very eager to follow through on her willingness. I must say that I realize she could shoot this down at any time.

Ideas? Thoughts? Objections?
I’ll pay for the date, drinks, hotel… Your wife is already giving up plenty.
What area are you in?
 
  • Like
Reactions: wormwood
Here's the deal; My wife and I play all kinds of fantasy games about and around the cuckolding fetish. We've set up scenarios where she leaves the house alone, dressed sexy while going to places where she can be hit on by men. She's left the house while doing her shopping without a bra and has enjoyed it when men stare and ogle her blatantly. Even though she enjoys this aspect of our play, especially the reaction she gets form me when she returns home, she has always maintained that she would never do it for real and is happy to keep it a fantasy.

Recently, while sitting on the patio, enjoying the late summer weather, I broached the subject of having a contest where a man might "win" a date with her. Something along the lines of posting her picture and having men enter themselves in a drawing where they might get an opportunity to take her out for an evening.

She actually got into it, asking questions about how it would be run and how they would win. My original thought was that the "date" would be in mid May, (my birthday) but off the top of my head I told her it would be a good idea if it was for a New Years Eve date. This, I reasoned to myself, would at the very least involve a fair bit of drinking, (a guaranteed situation that would rev up her libido) and the promise of a midnight kiss at the end of the countdown.

Judging by her reaction, she seemed very interested in this scenario and never raised any objections. In fact she still questioned me about it and seemed excited by it. The fact that she was wearing a white tube top and her nipples visibly became hard and remained hard throughout the conversation indicated to me her excitement. When she said " I would like to go out on New Years Eve", something we hadn't done in years, it told me that she might entertain the idea.

I told her that I would be the sole judge and would pick out the guy from whomever replied, but that she could pick the guy if I got to pick out what she wore for the date.

So my question is; How would I go about this? I'm sure there are a lot of things I haven't considered. What site would let me do this? How much of this would I have to pay for? Dinner? Drinks? It would have to be someone local or someone willing to fly in without the promise of sex or even relief. Although I'm sure that a date where she had a lot of fun, drank a good amount of alcohol and ended in an obligatory kiss would result in her feeling obligated to give some type of satisfaction? Actually I'm counting on it.

This is the first time she's ever displayed any willingness to go along with one of my hornier schemes and I'm very eager to follow through on her willingness. I must say that I realize she could shoot this down at any time.

Ideas? Thoughts? Objections?
This sounds like fun to me! It looks like you already have a plan. Just do it! You won't regret it. Kisses, Tara
 
I thank you all for the well meant responses and am pleased with your interest but can anyone answer the questions I posed? The logistics of doing something like this poses a lot of potential problems as well as concerns. I imagine that there are legal issues that I haven't considered as well as the probability that I might get shut down by this or any other website.
 
I thank you all for the well meant responses and am pleased with your interest but can anyone answer the questions I posed? The logistics of doing something like this poses a lot of potential problems as well as concerns. I imagine that there are legal issues that I haven't considered as well as the probability that I might get shut down by this or any other website.
PM me with any questions
 
My first step with my wife is to find out which pics I can share so that guys can see what their getting into. So far she's put me off on even looking at the pics I think she might approve of. I guess it's her way of being non-commital about this thing. I can tell the idea intrigues her but she's dragging her feet,
So anyway, I'll try to pin her down this weekend, but no promises. I hate to pressure her about this because I know applying pressure on her usually backfires. So I'll try to be as gentle and persuasive as I can. Wish me luck. (Her too)
 
I will answer this way, and you know me if you've been on the sit for a while. This kind of post with your profile would hardly get you even a chat session with a real person or lifestlyer. No pics, really no description, not even a verification on this site. This isn't even a lifestyle "dating" site. So, as long as it's fantasy then you'll probably find guys who will "fantasy" chat you and "fantasy" make all kinds of plans. None of it makes any sense from an actual possibility though in real life.

Mrs Hotwife
 
My first step with my wife is to find out which pics I can share so that guys can see what their getting into. So far she's put me off on even looking at the pics I think she might approve of. I guess it's her way of being non-commital about this thing. I can tell the idea intrigues her but she's dragging her feet,
So anyway, I'll try to pin her down this weekend, but no promises. I hate to pressure her about this because I know applying pressure on her usually backfires. So I'll try to be as gentle and persuasive as I can. Wish me luck. (Her too)
be sure to ask her important questions about what she is not interested in so when you pick someone they will be more compatible. after all if she isn't comfortable then it will be a nightmare for her.
 
  • Like
Reactions: wormwood
I will answer this way, and you know me if you've been on the sit for a while. This kind of post with your profile would hardly get you even a chat session with a real person or lifestlyer. No pics, really no description, not even a verification on this site. This isn't even a lifestyle "dating" site. So, as long as it's fantasy then you'll probably find guys who will "fantasy" chat you and "fantasy" make all kinds of plans. None of it makes any sense from an actual possibility though in real life.

Mrs Hotwife
Thanks for your response. Constructive and well reasoned. Believe me when I say I'm sincere about this, but I don't know if she's going to shut it down and back off. I'll see how it progresses.
I've already had my share of guys responding to this who show a real lack of tact and reason. From dick pics to questions that could have been answered if they just read the original post.
While I think it could make sense, I have no reason to doubt your credibility on this site. You've given out a lot of free and cogent advice here that I've benefitted from as well as other users. Thank you for your input.