What are my odds, honestly? Help, please!

[Possiblyso2025]

I’ve been enjoying this site and reading all the different perspectives. I’d like to proceed with dropping some hints to my wife that I’d like her to experience another man. We’ve been together for almost twenty years and I believe we have a great relationship. We’re both extremely busy so our sex life is about once a week. When we do get to enjoy each other, we both orgasm but I believe we both could use something extra. My stamina isn’t what it once was, with the exception for oral. She’s lovely, so I could give her oral for hours, seriously! I’m average size and I know she’d enjoy someone larger, girth specifiy, than I am, especially him having more stamina and being able to literally pound her.
Some details about her. She’s very pretty but I know she’d like to lose weight. In my opinion, she’s beautiful exactly the way she is. After children, she hasn’t been as comfortable with her body. She is an all around good person, doesn’t drink, doesn’t watch porn, doesn’t cuss. If you knew her, she’d be the last person you’d think would go for something like this. She’s only been with one other man besides me, she was married previously. But, she has surprised me with a few things. She enjoys riding my face to receive oral. In this position, she either ride my face until she has an orgasm, yes she’s a squirter, or she’ll slide down and mount me. She enjoys her ass played with while she rides me and it always helps her orgasm. A few times after riding me and both of us having an orgasm, she slide up over face to receive another oral stimulated orgasm.
My struggle is, how to present the idea of her being with another man. She doesn’t like dildos because she says they don’t feel real and she would be turned off watching porn.
Honestly, what are my odds of being successful with her being sexually pleased by another man?

[armyguyot1]

Welcome to the forum Possiblyso2025.

[Possiblyso2025]

Thank you!

[hornedhubby]

As a forever wannabe, now 67 and having encouraged my wife for 40 years to give this a try, I'll try to help.

But we really need to know a lot more about you and your wife. Kids still at home? Does she work? Travel by herself or with girlfriends? Do you share fantasies of any type? Is she playful? Sense of humor? Assertive or dominant sexually? Does she enjoy flirting, texting, engaging with others on social media? Does she masturbate? Pre or post menopausal?

Are you willing to play the long game of planting the seed and nurturing it? Or do you want to just find out, yes or no, if she'd like to try this? (So that, if no, you can try to get it out of your head).

It helps that she is multi orgasmic and enjoys oral and being on top and, sometimes, feeding you your own creampie.

The more she truly loves sex and the closer she is to her sexual prime, the higher your odds.

It probably doesn't help that she doesn't drink at all, disdains porn and toys. Also, you're telling us she'd be the last person to go for this.

If you decide to bring the subject up with her, tease it a little at a time, don't dump your kinks on her like a truckload. And never push.

Odds? Depends on your answers. But those who have hung out on OHW for years have read about many pleasant surprises.

[Possiblyso2025]

Thanks a bunch for responding!!!! I thought I provided a lot of details, but these are great questions. I’ll answer them one by one.

Kids still at home? Yes, two teenagers
Does she work? Yes, full time.
Travel by herself or with girlfriends? No, but I do encourage it.
Do you share fantasies of any type? Not often, she’s typically quiet about it.
Is she playful? Sense of humor? She can be once she’s comfortable and has a good sarcastic sense of humor.
Assertive or dominant sexually? No, she’d rather me take charge. But, she isn’t shy about accepting oral, even to the point of stripping down and climbing on my face.
Does she enjoy flirting, texting, engaging with others on social media? No, she’s too shy.
Does she masturbate? She has but I haven’t been aware of it in recent years.
Pre or post menopausal? I guess post because she had a full hysterectomy a few years ago. She does take hormone medication.
Are you willing to play the long game of planting the seed and nurturing it? Or do you want to just find out, yes or no, if she'd like to try this? (So that, if no, you can try to get it out of your head). I don’t mind playing the long game. The way I see it, I’ve got nothing to lose.

40 years. Have you been successful?

Thanks again for the help!!!

[Colliercuck]

If you have never broight it up before, why not tell her you had a dream, where she was with another guy
You could start to tell her, then tell her you’re unsure of sharing your dream, as it even took you by surprise.
Once you share it and gauge her reaction or questions she asks.
You can tell her how surprised you were, that you emotions were up and down, but woke up with an intense hard on, which shocked you.
This will allow you to build on the conversation later.

I am 63 my wife is 59………i had been a wannabe for 30 years and brought it up to her between 30 and 25 years ago.
I had told her numerous times and even wrote to her about it in cards and letters.
It helped that she had told me how small i was and that her ex-fiance was much bigger.
It did not go over well the very first time………how could i have these thoughts?? Did i still love her?? Was i looking for an excuse to cheat???
The first several times i brought it uo, she shut it down.
Then one night while at a hotel overnight for a romantic night, i told her another man had his huge cock inside her and was going to fill her with his cum, i was fingering her, amd as she said no, her pussy was soaking wet, dripping!!! i had never felt her pussy so wet, i entered her as she was saying your all i want, and i told her he has his huge cock in you!!! He is going to fill you with his cum!!! She started moaning and breathing heavy, pulling my ass into her (she had never really been into sex before, very very conservative) she had her first orgasm with me (a good 20 years into our marriage) she was begging for more.
Then after she came, she attacked my dick with her mouth, and swallowed my cum for only the second time, the first while married, we fucked 3 more timed that night, she could not ger enough, then woke me uo to her mouth around my dick again and not stopping until she swallowed me.
This went on for a week, as I told her he was fucking her and filling her, she just wanted more, as i fucked her in the shower each day, i kept telling her that he was filling her pussy.
I absolutely was in heaven , and pleased with myself, I thought i found a magical key!!! (We only had sex once or twice a year prior to that, maybe 3 or 4 times on a really good year, and sometimes not at all (my wife is bipolar and there have been clues that she might have experienced some trauma, sexual abuse, but every time it seemed that a door was going to open and she was sbout ti get very vulnarble, she would shut down)
Anyway, after a week or 10 days, dhe said she never wanted to hear it again, and that i deeply wounded her heart.


So, i wasnt going to bring it up again, but she would tell me she thinks she needs a boyfriend, or she would tell me guys she thought were goodlooking and very sexy, she would tell me cuckold jokes her friends told her, and then teasing me about my size and sexual inadequacies………i loved it all but was hesitant to act on it.
I did bring it uo again, but she would shut me down
I found a huge huge stain in the crotch of her panties .
I asked her and she said it was normal discharge for a woman.
Then she found me wearing her panties and outed me very publicly and humilating, which she knows i love.
Then i approached her again, she told me, if you really really want to be a cuckold, and you really desire me to be with another man, then I want you to tell your father and sister (which I did, and she told her girlfriends)
Then one day, I find her texts on her phone, she is having an affair and it’s going on for 8 months.
I wasn’t mad, I was so hard looking at the texts and pics….it would be a couple months before she found out that I knew.

[parklife]

At first glance… I’d say your odds aren’t good.

That being said, you have a long and lasting marriage that, on the face of it, seems stable and built on a foundation of love. You’re at least in the position of being able to own up about your thoughts and desires. Doesn’t mean you jump to the end and exclaim you want her sleeping around and bringing home creampies.

I doubt she jumps in with two feet but a way to at least tiptoe is to start by talking about things that turn you on. Or the periphery of things that turn you on. The chances are most likely that she’ll never go down the road, but you that shouldn’t even be the goal. The goal should be having a relationship you can share your fantasy with and have some engagement on her end. If not in reality, in fantasy. And cut her some slack if she’s not keen on it…. She works a full time job, with two teenagers and is on hormones after a hysterectomy… know that her fantasy probably revolves around having a loving faithful marriage with a husband that supports her in running a household filled with crazy life obstacles. Not saying your fantasy isn’t valid, but she doesn’t sound like the kind of woman that is open to going in this direction.

I say all this coming from a marriage with a wife that was insistent it would never happen but eventually (after 8 years) had a run of 9 years that she engaged in being a hot wife who is now taking a break. It’s possible for people to open up to exploring… but that only came after fantasy talk for 7 years.

[Possiblyso2025]

Thank you both parklife and colliercuck. I do like the dream idea and I appreciate the honest feedback from both of you. I agree, it’s a long shot. But to quote Lloyd Christmas: “So you’re telling me there’s a chance. Yeah!”. Why not ever so carefully gradually tip toe into this and see what happens. The suspense is an adrenaline dump, which is a lot of enjoyment!
I’d love to hear any other recommendations, especially ones out of the box.

[hornedhubby]

The dream is not a bad way to broach the subject. If she gives you a fun and favorable response over breakfast, or asks interesting questions, then perhaps you could bring it up in the bedroom during playtime. What if we pretend...etc.

But the long game is your best option. See if you can plant the seed, find ways to have sexy fun with it, etc. But wait until your wife has an empty nest before you encourage her to fuck another guy. Focus on growing and sharing the fantasy. Kiss her ass and maintain her desire for sex. It sounds like your sex life is far better than average for your age and situation (teens at home).

Keep that alive. Make it all about her and you will keep it all moving in the right direction.

[tiedyeHotwife]

Ask her out for a date.
Encourage her to dress a bit sexy (you are remembering some of the hot outfits she wore back in the day).
Give her the best sex of the year when you get home.
The day after needs to be totally normal

Rinse - repeat.

There will be an opportunity for her to go out with friends. Maybe office party?, girls Birthday .....
Ask her to be the "sexy her". Tell her its ok if men look and that it turns you on more than it makes you jealous.
Fuck her senseless when she gets home.
The day after needs to be totally normal.

Rinse - repeat.

You are creating and reinforcing a pattern of her being sexy, feeling sexy, getting fucked sexy - and then the next day, her life is totally normal. Zero negative consequences for letting her sexuality out and enjoying her sexual side.

This takes time.

Along the way, encourage her buying sexy clothes, shoes, etc. Hair, waxing, all of it.

Next - tell her that her sexy adventures have been making you super hot for her. Lots of hot dreams.
One in particular keeps occurring.
"you were out, dressed super sexy (office party, bar, etc), you got a bit drunk and got fucked by (co-worker, hot guy etc).
you came home and instead of me being upset - I was super turned on because you were sooo sexy, and we had the hottest sex ever.
The next morning - it was just us, being our perfect together love".

more in a bit

[Jelz]

You could try the mojoupgrade questionnaire with here. Tell her you 'heard' about it. Both fill it out separately and then compare the results.

That led to some interesting progression for us.

[Possiblyso2025]

Thank you hornedhubby, tiedyeHotwife, and Jelz for commenting. I really appreciate your input.
I agree the dream idea is good, but I don’t think we’re there quite yet. At this point, if she honestly was interested in listening to the details of a scene where she slept with another man, I don’t believe she’d admit it. During some casual chat, after numerous times of me saying it’s ok, I understand, it only bothers me because I know it could be more enjoyable for her, etc., she almost kinda sorta admitted she would it enjoy it if I was larger and lasted longer. This doesn’t seem like much, but I believe it’s a huge step. We had some fantastic sex, that was a little kinder than normal, after that conversation. I’d prefer to keep the details to myself. I’ll probably won’t mention it again for a few days, then see how she responds.

Jelz, I couldn’t locate the quiz. Do you have a link?

tiedyeHotwife, I like where you’re going with your suggestion! Maybe I can tailor it to fit our life and what keeps us busy.

hornedhubby, I believe you’re all over it! If, and it’s a huge IF, this was to work out, it’ll have to be on her time. So the long term game it is. To be honest, I’m surprised how our conversation went last night. Even with that, it’ll take much much more of it. I’m not sure what the average sex life is like for a couple that both work long hours and have two teenagers at home. My goal will be just as you said, make it about her.

Thanks again!

[hornedhubby]

Any progress or updates?

[Possiblyso2025]

Any progress or updates?

I wish. Life has been crazy busy. I’ve had some small talk, nothing really worth noting, but it didn’t go really far. I did receive the “you make me happy…” response. But, I figured that was coming.

[BrunetteLover]

My wife has a thing for perceived danger. Not roller coasters, not slippery roads, not mean or hurtful people, more of an urban milieu or dark scary forest type of thing.

She loves to go to urban areas and take subway trains to the last stop and see if it is possible to walk back to center city/downtown or the hotel we are staying at, or wherever we started from, etc. You get the idea.

We have done that in Boston, Washington DC, and to a lesser extent NYC (when it was cleaner in the 1990s) - when we are in the woods, she also likes to follow coyote or bear tracks to where they may lead.

But when she is with me doing those things, she feels (and is, mostly) completely safe.

Why am I telling you this?

Because for a woman to explore her sexuality fully, in my opinion, she must feel danger and complete safety at the exact same time. You CANNOT create the danger yourself, that would be cruel and possibly illegal.

But you can let her take chances, if she - SHE - really wants to.

BUT only if you are completely able to catch her if she stumbles. You have to be good at this to make it happen.