Hopefully Lee's journey to cuckolding me
Hopefully Lee's journey to cuckolding me
I have been lurking in the shadows for a while. Now it is time to come out and finally post.
Lee and I met in school and have always been a couple. We got married right after school so we could live together as I went to college. When I graduated we moved across the country to start a new life.
Now we live in a two bedroom apartment and have made a nice way of life for ourselves here.
So why am I here. Well, after much thought and consideration I want to share my wife with another man or multiples. I want her to have sex with them and a relationship if she wants it. I would be fine with her dating since we don't know a lot of people here and I travel a lot for work.
My desire for her to see others started when I was in college. We would go to parties and I would see guys hitting on her if I was not right there with her. She is beautiful to me and others say the same. She is 5'7 with light blonde hair with white streaks in it. She has bluish green eyes, 34C breast that I think are her beast feature outside of her glowing smile. A lot of guys like her ass since it is pretty big for her frame. She weighted around 165 when I was in college, but has gotten us both on health kick now and she weights 135.
I am 5'4 with brown hair down to my mid shoulders. I have blue eyes, with a very boyish look. I am undersized due to hormone issues and heart/blood flow complications. I am not going to die from it, but it caused me to be undersized. If was always picked on in school and picked last in gym.
Lee and I were both virgins till we got married. On our honeymoon it was really fun. She later admitted she didn't cum that night but she enjoyed it. Then my senior year of college I started noticing that I would get hard, but it would start to go down quickly. Then I noticed it wasn't as hard as I usually was. Lee said I should go to the doctor and I did. The doctor found the issues and said it would only get worse the older I got. He suggested exercising and that never really helped. We tried pumps and some other things. Finally we just went to toys.
First it was a small dildo about five inches and thin. Similar to what I was. Then she found me watching porn one day. She was a mad and I explained I was trying to see if I could get hard watching it. When I didn't she wasn't as mad weirdly. She later admitted to watching it from time to time. That just made me want to do it together. We did and I would let her pick what we watched. Then she started asking me to pick. I always found the ones where the girls looked like her. It was one of those nights that I first saw a cuckold video. It was so hot. I started researching it and found this site.
I began encouraging her to dress more risque. I like to point out guys looking at her. She is very shy and doesn't think she is pretty. I also got her to go out with her friends more. They go dancing and shopping. Jill is her best friend here and she is definitely wilder. She goes through boyfriends pretty quick. We have a really close relationship after I helped her with somethings at her job that got her a promotion.
We have talked in the bedroom about how I would love to see her with someone else. She said she would never do it. I do think there is some hope there now. She finally will dance with other guys and has been more open to flirting. I have gone just a couple times when they go dancing. They flirt and dance to get free drinks.
So that is a little start about us. I am looking to share my story and get input from others who have been or are cuckolding someone.
Lee and I met in school and have always been a couple. We got married right after school so we could live together as I went to college. When I graduated we moved across the country to start a new life.
Now we live in a two bedroom apartment and have made a nice way of life for ourselves here.
So why am I here. Well, after much thought and consideration I want to share my wife with another man or multiples. I want her to have sex with them and a relationship if she wants it. I would be fine with her dating since we don't know a lot of people here and I travel a lot for work.
My desire for her to see others started when I was in college. We would go to parties and I would see guys hitting on her if I was not right there with her. She is beautiful to me and others say the same. She is 5'7 with light blonde hair with white streaks in it. She has bluish green eyes, 34C breast that I think are her beast feature outside of her glowing smile. A lot of guys like her ass since it is pretty big for her frame. She weighted around 165 when I was in college, but has gotten us both on health kick now and she weights 135.
I am 5'4 with brown hair down to my mid shoulders. I have blue eyes, with a very boyish look. I am undersized due to hormone issues and heart/blood flow complications. I am not going to die from it, but it caused me to be undersized. If was always picked on in school and picked last in gym.
Lee and I were both virgins till we got married. On our honeymoon it was really fun. She later admitted she didn't cum that night but she enjoyed it. Then my senior year of college I started noticing that I would get hard, but it would start to go down quickly. Then I noticed it wasn't as hard as I usually was. Lee said I should go to the doctor and I did. The doctor found the issues and said it would only get worse the older I got. He suggested exercising and that never really helped. We tried pumps and some other things. Finally we just went to toys.
First it was a small dildo about five inches and thin. Similar to what I was. Then she found me watching porn one day. She was a mad and I explained I was trying to see if I could get hard watching it. When I didn't she wasn't as mad weirdly. She later admitted to watching it from time to time. That just made me want to do it together. We did and I would let her pick what we watched. Then she started asking me to pick. I always found the ones where the girls looked like her. It was one of those nights that I first saw a cuckold video. It was so hot. I started researching it and found this site.
I began encouraging her to dress more risque. I like to point out guys looking at her. She is very shy and doesn't think she is pretty. I also got her to go out with her friends more. They go dancing and shopping. Jill is her best friend here and she is definitely wilder. She goes through boyfriends pretty quick. We have a really close relationship after I helped her with somethings at her job that got her a promotion.
We have talked in the bedroom about how I would love to see her with someone else. She said she would never do it. I do think there is some hope there now. She finally will dance with other guys and has been more open to flirting. I have gone just a couple times when they go dancing. They flirt and dance to get free drinks.
So that is a little start about us. I am looking to share my story and get input from others who have been or are cuckolding someone.
- armyguyot1
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Re: Hopefully Lee's journey to cuckolding me
Welcome to the forum leeshubby.
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venus-can99
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Re: Hopefully Lee's journey to cuckolding me
Interesting start LH. Has she expressed any curiosity to explore interactions with other men/women ? Hope things progress and both of you get what you are looking for.
Something new viewtopic.php?f=13&t=75158
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Dream Weaver
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Re: Hopefully Lee's journey to cuckolding me
You told her you were really interested in seeing if you could get hard watching it? And she believed it?
I have a feeling things will progress really quickly. Good luck!
I have a feeling things will progress really quickly. Good luck!
Re: Hopefully Lee's journey to cuckolding me
venus-can99 wrote: ↑Wed Dec 03, 2025 10:46 amInteresting start LH. Has she expressed any curiosity to explore interactions with other men/women ? Hope things progress and both of you get what you are looking for.
No not at all. She does flirt with other guy friends and with guys at bars or clubs that she goes to with friends. I have gone with them and can go anytime i want with them. I just don't like to dance. She knows i like her doing it. She knows when we are in bed I will talk about it some, but not that often. I don't want to freak her out. I know if she ever does this that it might take some time. Not sure what the next steps need to be to get her to try it.
Re: Hopefully Lee's journey to cuckolding me
That was a longer story than what I told there. I had been to the doctor already and she knew I was struggling with not being able to stay hard.Dream Weaver wrote: ↑Wed Dec 03, 2025 2:19 pmYou told her you were really interested in seeing if you could get hard watching it? And she believed it?
I have a feeling things will progress really quickly. Good luck!
Re: Hopefully Lee's journey to cuckolding me
Little update that I don't know if it will lead to anything, but maybe I can get some suggestions on how I could use it. Two nights ago we played around and after watched tv . The episode showed a married couple that went to hotel and then wife went to bar. Husband came down later and acted like a sales man. He then pretended to pick her up. It was a comedy so there wasn't really much to it.
I said lets do it. She said really. I said ya. She said sure if I get to pick your character. I said sure as long as I got to pick hers and what she wore. She agreed. I told her when we travel to see our family for the holidays we will try it then.
I have been searching for pickup bars and hotels close to them. I found one that has a bar with a place to dance as well. It is about an hour from our family, but close to the airport. The reviews all point to a lot of travelers and it being a hookup bar.
Last night she brought it up and said she wants my character to be a propane and propane accessories sales man named Hank. We both laughed. It is from a cartoon series we watch. She asked me and I said visiting your family and recently separated. She joked saying oh I will be extra horny when hank walks in then. I said I wanted to buy her a couple new outfits and she said ok but I had to get Jill to help me. I said I would. We are going out tonight or tomorrow during the day. Depends on when she is free.
I said lets do it. She said really. I said ya. She said sure if I get to pick your character. I said sure as long as I got to pick hers and what she wore. She agreed. I told her when we travel to see our family for the holidays we will try it then.
I have been searching for pickup bars and hotels close to them. I found one that has a bar with a place to dance as well. It is about an hour from our family, but close to the airport. The reviews all point to a lot of travelers and it being a hookup bar.
Last night she brought it up and said she wants my character to be a propane and propane accessories sales man named Hank. We both laughed. It is from a cartoon series we watch. She asked me and I said visiting your family and recently separated. She joked saying oh I will be extra horny when hank walks in then. I said I wanted to buy her a couple new outfits and she said ok but I had to get Jill to help me. I said I would. We are going out tonight or tomorrow during the day. Depends on when she is free.
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johntigger1469
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Re: Hopefully Lee's journey to cuckolding me
Good luck...hope things progress in a way that you both enjoy!
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Wantsomefunto
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Re: Hopefully Lee's journey to cuckolding me
Maybe say you want to watch her have another try to pick her up at the bar and see how she responds
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Wantsomefunto
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Re: Hopefully Lee's journey to cuckolding me
Maybe say you want to watch her have another try to pick her up at the bar and see how she responds
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Dream Weaver
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Re: Hopefully Lee's journey to cuckolding me
Oh! Hey, that's a huge context changer. Glad you said something and I wish you the best!leeshubby wrote: ↑Fri Dec 05, 2025 6:54 amThat was a longer story than what I told there. I had been to the doctor already and she knew I was struggling with not being able to stay hard.Dream Weaver wrote: ↑Wed Dec 03, 2025 2:19 pmYou told her you were really interested in seeing if you could get hard watching it? And she believed it?
I have a feeling things will progress really quickly. Good luck!
Re: Hopefully Lee's journey to cuckolding me
Thank you!johntigger1469 wrote: ↑Sat Dec 06, 2025 6:22 amGood luck...hope things progress in a way that you both enjoy!
Re: Hopefully Lee's journey to cuckolding me
Thank you!johntigger1469 wrote: ↑Sat Dec 06, 2025 6:22 amGood luck...hope things progress in a way that you both enjoy!
Re: Hopefully Lee's journey to cuckolding me
That is a great idea. I had not thought of going that route, but maybe she would like that.Wantsomefunto wrote: ↑Sat Dec 06, 2025 7:10 amMaybe say you want to watch her have another try to pick her up at the bar and see how she responds
Re: Hopefully Lee's journey to cuckolding me
Weren’t there one or two threads similar to this a couple of years back?
I recall a girl named Lee. And the guy was not that big of a guy as well. I wonder if this is the same poster with a different scenario but the same physical makeup of those involved.
Does any else recall anything like this?
I hope I am wrong. Just sayin’.
I recall a girl named Lee. And the guy was not that big of a guy as well. I wonder if this is the same poster with a different scenario but the same physical makeup of those involved.
Does any else recall anything like this?
I hope I am wrong. Just sayin’.
Re: Hopefully Lee's journey to cuckolding me
This is my first time posting. Sorry if you were hoping I was someone else.joel68 wrote: ↑Mon Dec 08, 2025 6:05 amWeren’t there one or two threads similar to this a couple of years back?
I recall a girl named Lee. And the guy was not that big of a guy as well. I wonder if this is the same poster with a different scenario but the same physical makeup of those involved.
Does any else recall anything like this?
I hope I am wrong. Just sayin’.
Re: Hopefully Lee's journey to cuckolding me
Jill and I went and looked at some clothes. We hit three spots and got five dresses. My two favorite are like two long sheets of fabric connected at the neck. Then the two go down each side. It is held together with a belt in the middle. You can make it look slutty by opening it up. Or you pull it out to just show an opening down the sides. She said this is what a separated women on the hunt would wear. Jill loved the idea.
We also got two short skirts. One was very small. The other was more on the average. Two tops that showed off her chest too. One only covered the front and it was my favorite. The last was a little black dress. I picked the shortest one of the bunch. It also showed off her top with a slit in the front. It was Lee's favorite, but she liked the dresses that could be changed as well. I had to go ahead and show them to her to make sure they fit. She was really excited and showed me that before bed.
We also got two short skirts. One was very small. The other was more on the average. Two tops that showed off her chest too. One only covered the front and it was my favorite. The last was a little black dress. I picked the shortest one of the bunch. It also showed off her top with a slit in the front. It was Lee's favorite, but she liked the dresses that could be changed as well. I had to go ahead and show them to her to make sure they fit. She was really excited and showed me that before bed.
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realcucklife
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Re: Hopefully Lee's journey to cuckolding me
Sounds like your journey is well underway!
Re: Hopefully Lee's journey to cuckolding me
Atleast we can pretend at the hotel and that should be fun. Maybe take it further if she will.
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Scud Farcus
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Re: Hopefully Lee's journey to cuckolding me
Let her sit at the bar a bit longer than agreed upon and text her that she looks so hot. Ask her if any guys have shown interest and encourage her to hold eye contact.
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Dream Weaver
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Re: Hopefully Lee's journey to cuckolding me
One of the best Modern Family episodes ever. Definitely a great way to take off the defenses in your situation!leeshubby wrote: ↑Fri Dec 05, 2025 1:02 pmLittle update that I don't know if it will lead to anything, but maybe I can get some suggestions on how I could use it. Two nights ago we played around and after watched tv . The episode showed a married couple that went to hotel and then wife went to bar. Husband came down later and acted like a sales man. He then pretended to pick her up. It was a comedy so there wasn't really much to it.
Re: Hopefully Lee's journey to cuckolding me
LH, no. I was NOT hoping you were a previous poster.I am actually relieved that you are not he as I thought it was mostly bullshit.
Yours is interesting and I will be following your story. Sorry for the confusion.
Yours is interesting and I will be following your story. Sorry for the confusion.
Re: Hopefully Lee's journey to cuckolding me
I love that idea. Right now she is focused on two different ideas that she has. One I mentioned and the other she said is a surprise.Scud Farcus wrote: ↑Mon Dec 08, 2025 11:50 amLet her sit at the bar a bit longer than agreed upon and text her that she looks so hot. Ask her if any guys have shown interest and encourage her to hold eye contact.
Re: Hopefully Lee's journey to cuckolding me
Thanks and I look forward to suggestions and ideas.
Re: Hopefully Lee's journey to cuckolding me
Just a quick update. Lee has been really excited about the idea she had that I mentioned. She has another but hasn't told me what it is. She said I could have the rest of the nights so I like that she wants to go there more than those two times. I am looking at maybe adding a day or two, but won't know for a bit on that.