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If you could go back in time, what would you change?

Posted: Sat Sep 20, 2025 2:28 am
by surry
We have been married 50 years. My wife and I had an exciting sex life. We have been dating since age 14. Looking back, there are some things I would love to change. When we first started dating, I wish I had groomed her to flirt and accept other boys touching her. My Girl is shy, and I would love to
Tell her that boys flirt and touch her because they find you very sexy and want to fuck you. She should feel good if a boy touched her ass. Instead of being upset, she should feel flattered and allow him to rub your ass. She could push back on his hand slightly just to let the boy know it is OK. If his hand slips towards her pussy. she should open her legs for him. He is hand is on the outside of your clothes, so no harm is done. You both feel good about this. You are excited because you excited him, and he feels good because he felt up a girl he finds sexy.
My older brother had a car and we double-dated. We went to the drive-in to make out with our girls. My brother and I would go get snacks. What I wish is that we had switched seats.
My GF had a crush on my 19-year-old brother. I would have loved to see him fuck her virgin pussy. I would love to see her belong to both of us. She would have loved to be the only girl on a date with two boys.
In the Army, when I was in the field, my best friend, Dave, and his wife would stop by to check on my wife. I wish I had encouraged Dave to fuck my wife so she would not get lonely.
Another one is my friend Doug fucked my wife with a condom because she was not on birth control. I wished now he had bred her with my blessing. I would have loved to get my wife so turned on that she removes Doug's condom and takes his sperm. I wish Doug and I had talked her into having his baby, not mine. I would promise Doug in front of my wife, I would not fuck her until he put a baby in her. This would have excited my wife, and went along with it.

Re: If you could go back in time, what would you change?

Posted: Sat Sep 20, 2025 2:45 am
by luvwives999
We will also be married 50 years this Dec. There are so many missed opportunities I look back on and wish we could do differently. I'll just mention one for now. Wife and I had a 3-some with a friend. The next weekend he and I played basketball as we did every sunday morning. Came back to my apartment and my wife was in the shower. I mentioned to him, we could both use a shower, maybe we should join her, but alas neither of us had the balls to just do it. My wife loves sex in the shower, even after all these years, and I told her what we wanted to do later in the day, and she told me that she wishes we just walked in. I still regret my hesitation, and fantasize about the two of us sliding on her soaped up body.

Re: If you could go back in time, what would you change?

Posted: Sun Sep 21, 2025 7:15 am
by ucaneffher
I have a few things I would have changed.

1. Knowing that this is what I truly want and go after it with more focus and dedication.

2. Be up front from the start and Not waste time if both parties values don't align. If she's not into it, move on to another one who might be instead of waiting 5 years to discover she thinks you're disgusting.

If all else fails, here's a crazy idea that might work

3.Instead of dating normally... Consider looking for escorts my age or a few years younger and coordinate a cuckold experience with her. Explain that I am a cuckold and want her to fulfill my fantasy. Pay her for one full day of her pretending to be my wife as well as pay her to have sex except it will not be with me.

We will go on a date where we dress up, she wears a provocative sexy little dress so that after dinner we end up in a nice lounge or dance club. While she is a paid girl, I make a genuine effort during dinner to impress her and maybe win her over a little. After dinner the plans are for us to go to a venue where she, my wife will find the man of her choice to flirt with and take back to our hotel room. She will of course tell the man her husband likes to watch and that he must be cool with it.

At the end of the night she makes her money, goes on a nice date, has a nice dinner, and gets to have sex with a man of her choice for once instead of anyone who pays her. I get to live the cuckold experience and enjoy it. If chemistry is good and her and I clicked during the "date" and I like her hot wife performance that she puts up from night club to hotel room, then I continue scheduling such outings with the full 9 yards and dates.

During the dinners or "hangouts" before going out is my chance to get to know her. I become her regular and she trusts me. We do this quite frequently to the point where she knows exactly what to do and plans everything herself. We become friends outside of this weekend activity of ours and maybe within due time she might like me for me and she likes that I approve her line of work.

One thing leads to another and I end up in a relationship with the gorgeous escort who fulfilled my cuckold fantasy for the first time ever and who has since been cuckolding me for pay twice a month for the last 2 years and has been my friend after 6 months of cuckolding me.

Can you imagine landing yourself an escort this way and who will make the perfect hot wife? As a numbers guy, I'd love a girlfriend or wife who would have sex for a living and is in bed with 7 or 8 different men every work day. She would benefit from your support and you from her activities.

Re: If you could go back in time, what would you change?

Posted: Sun Sep 21, 2025 7:47 am
by ucaneffher
I have a few things I would have changed.

1. Knowing that this is what I truly want and go after it with more focus and dedication.

2. Be up front from the start and Not waste time if both parties values don't align. If she's not into it, move on to another one who might be instead of waiting 5 years to discover she thinks you're disgusting.

If all else fails, here's a crazy idea that might work

3.Instead of dating normally... Consider looking for escorts my age or a few years younger and coordinate a cuckold experience with her. Explain that I am a cuckold and want her to fulfill my fantasy. Pay her for one full day of her pretending to be my wife as well as pay her to have sex except it will not be with me.

We will go on a date where we dress up, she wears a provocative sexy little dress so that after dinner we end up in a nice lounge or dance club. While she is a paid girl, I make a genuine effort during dinner to impress her and maybe win her over a little. After dinner the plans are for us to go to a venue where she, my wife will find the man of her choice to flirt with and take back to our hotel room. She will of course tell the man her husband likes to watch and that he must be cool with it.

At the end of the night she makes her money, goes on a nice date, has a nice dinner, and gets to have sex with a man of her choice for once instead of anyone who pays her. I get to live the cuckold experience and enjoy it. If chemistry is good and her and I clicked during the "date" and I like her hot wife performance that she puts up from night club to hotel room, then I continue scheduling such outings with the full 9 yards and dates.

During the dinners or "hangouts" before going out is my chance to get to know her. I become her regular and she trusts me. We do this quite frequently to the point where she knows exactly what to do and plans everything herself. We become friends outside of this weekend activity of ours and maybe within due time she might like me for me and she likes that I approve her line of work.

One thing leads to another and I end up in a relationship with the gorgeous escort who fulfilled my cuckold fantasy for the first time ever and who has since been cuckolding me for pay twice a month for the last 2 years and has been my friend after 6 months of cuckolding me.

Can you imagine landing yourself an escort this way and who will make the perfect hot wife? As a numbers guy, I'd love a girlfriend or wife who would have sex for a living and is in bed with 7 or 8 different men every work day. She would benefit from your support and you from her activities.

Re: If you could go back in time, what would you change?

Posted: Sun Sep 21, 2025 12:20 pm
by cucking88
I would’ve become a cuck a little earlier, I resisted for ten years

Re: If you could go back in time, what would you change?

Posted: Sun Sep 21, 2025 2:21 pm
by D+D
We didn’t actually get into the lifestyle until she was 60 years old although I tried years before to get her to try it. She now says if only she had become a hotwife years ago. She was not able to get pregnant due to having had a hysterectomy but had this happened years earlier perhaps I would have raised another man’s child.

Re: If you could go back in time, what would you change?

Posted: Sun Sep 21, 2025 6:59 pm
by knight4princess
Ya know, I wouldn't have changed one thing -- despite how painful some of it was. That's because I'm convinced that any other ka-plink along the way might have dramatically changed where I am now -- which is good. I'm 68 years old now, amazingly, and my wife is right behind me by a few years.

Just yesterday we had an encounter with a guy my wife and I have been seeing for a year or so. We have a vibe with this guy that we've never had with, let's say the many men ... she's been with extra-curricularly over the years. Could we have gotten in to this earlier? Maybe we could have but when we got the internet in 1995 we were sort of pioneers into the naughty stuff on line. There's no way we could have gotten in to this any earlier also because of family child-raising and other real life stuff. So we got into it just about as early as we both were ready for it. And we still embrace it to this day. We're celebrating our 40th anniversary this year.

Re: If you could go back in time, what would you change?

Posted: Mon Sep 22, 2025 8:07 am
by Thebestdays1
I wish I didn't used to get so turned on when I knew she was with another man.

I wasn't allowed to ask her anything when she went with another woman so I was able to keep my emotions under control, despite getting turned on as I imagined what they were doing at the time. She could come home and I'd just say hi or, after a number of years and lovers, ask if she'd had a good time.

When she'd been with another man however, I used to ask her any amount of questions, especially how many times they'd cum, what positions, where he came and if there was anything left for me to eat. She'd masturbate me as she told me everything and over time she grew tired of having to give me so much information, especially if she'd developed feelings for him. This eventually ended up with her cheating on me for a few one off's but also with two long term lovers, one of which was her nephew which I only found out about over 20 years later.

Eventually I ruined our relationship by asking so many questions. She'd started to develop strong feelings towards her nephew and also for the other man, a married colleague of hers. She knew nothing could happen with either of them but her feelings for them were enough to drive a wedge between us. When I suggested a trial separation she admitted seeing her colleague and said she'd kept it secret because she was tired of answering my questions. I'd watched her suck her nephew off 4 years earlier but didn't know she used to fuck him during foursomes with her sister and her partner. Some of the reasons she gave for not telling me were because she was ashamed she was fucking her nephew and because I'd have bombarded her with questions, like I always did. There were a couple of other reasons but they were the main ones.

The wife of her colleague actually found the phone he used to talk to my wife and she kicked him out and he moved in with my wife that same day so the separation ended up with us getting divorced.

If I'd been able to contain my emotions better we may never have split up.