Making slow progress but she is admitting things

[drakebelg]

Before I admitted to her I want to be a cuckold (September 2023)

• She told me several years ago that she was very disappointed the first time we had sex. I came after a few minutes before she did.
• At the beginning of our relationship she joked saying I was only her second best lover. After a while she let it go and said now I was the best. I didn't believe her. This became true.
• Even though I am 7x5.5 she said she would prefer it if I was a good bit thicker and a bit longer.
• For about 8 years we have been using large cocksleeves regularly. Her orgasms are totally different, crazy intense and multiple.
• She laughs when she feels my dick falling out of her big pussy.
• She loves the idea I am not big enough to fill her big pussy.
• She enjoyed telling me about her intense sexlife with a huge cock ex who was recently a colleague.
• Sex is almost always in a position with her back to me.
• She loves to ride a big dildo with me watching.
• She manages our finances.
• She defines when we have sex.
• She agreed that I should try jelqing or penis pumping to make me bigger.
• She admitted she is a size queen.
  

After admitting I would love to be a cuck in September 2023

• She admitted recently after 21 years together that she had 2 better lovers than me. One definitely had a bigger dick than me and probably the other also. They both were assertive dominant lovers. I am guessing there are even more lovers who are better than me. She laughed when I said this.
• She admitted if she would be a hotwife she would like a dominant guy.
• She fantasizes at least once a month about fucking a strong athletic guy.
• She said she doesn't want me watching while she is with someone else. I must wait somewhere.
• If I cum too quickly she is annoyed, orgasms with a vibe. If we have a second session she will orgasm quickly with a vibe and not let me cum.

New developments November/December 2023

• She has listened to a podcast about cuckolding (Cuckoldress) and said afterwards that the main thing is I must not push her, to be patient, and it will be her decision.
• Her Bukkake fantasy (wow): Gets crazy turned on thinking about the video of cap dagde woman giving 2 guys a BJ. She cums super fast when she thinks about this. She doesn't want me there and wants them to cum on her tits.
• Asking me once a week for Max (her favourite sleeve) to fuck her.
• While I fuck her in spoons she imagines she is in reverse cowgirl with another guy and I am licking her pussy.
• Her favourite story that I have ever written, was me caged and her fucking her self upstairs with a huge dildo pretending it's another guy. She totally dominates me and I cleaned her up in the story.
• I told her she won't let me lick her anymore and asked if it's because I am not any good....no answer. I asked if she had guys much better than me, she said no. I said I know that's a lie and she laughed out loud.
• She might be interested in going to a swingers club and or an erotic expo.

 

[Cuckindeep]

Very interesting to see your progress! Keep updating.

 

[toolman2c]

Before I admitted to her I want to be a cuckold (September 2023)

• She told me several years ago that she was very disappointed the first time we had sex. I came after a few minutes before she did.
• At the beginning of our relationship she joked saying I was only her second best lover. After a while she let it go and said now I was the best. I didn't believe her. This became true.
• Even though I am 7x5.5 she said she would prefer it if I was a good bit thicker and a bit longer.
• For about 8 years we have been using large cocksleeves regularly. Her orgasms are totally different, crazy intense and multiple.
• She laughs when she feels my dick falling out of her big pussy.
• She loves the idea I am not big enough to fill her big pussy.
• She enjoyed telling me about her intense sexlife with a huge cock ex who was recently a colleague.
• Sex is almost always in a position with her back to me.
• She loves to ride a big dildo with me watching.
• She manages our finances.
• She defines when we have sex.
• She agreed that I should try jelqing or penis pumping to make me bigger.
• She admitted she is a size queen.

After admitting I would love to be a cuck in September 2023

• She admitted recently after 21 years together that she had 2 better lovers than me. One definitely had a bigger dick than me and probably the other also. They both were assertive dominant lovers. I am guessing there are even more lovers who are better than me. She laughed when I said this.
• She admitted if she would be a hotwife she would like a dominant guy.
• She fantasizes at least once a month about fucking a strong athletic guy.
• She said she doesn't want me watching while she is with someone else. I must wait somewhere.
• If I cum too quickly she is annoyed, orgasms with a vibe. If we have a second session she will orgasm quickly with a vibe and not let me cum.

New developments November/December 2023

• She has listened to a podcast about cuckolding (Cuckoldress) and said afterwards that the main thing is I must not push her, to be patient, and it will be her decision.
• Her Bukkake fantasy (wow): Gets crazy turned on thinking about the video of cap dagde woman giving 2 guys a BJ. She cums super fast when she thinks about this. She doesn't want me there and wants them to cum on her tits.
• Asking me once a week for Max (her favourite sleeve) to fuck her.
• While I fuck her in spoons she imagines she is in reverse cowgirl with another guy and I am licking her pussy.
• Her favourite story that I have ever written, was me caged and her fucking her self upstairs with a huge dildo pretending it's another guy. She totally dominates me and I cleaned her up in the story.
• I told her she won't let me lick her anymore and asked if it's because I am not any good....no answer. I asked if she had guys much better than me, she said no. I said I know that's a lie and she laughed out loud.
• She might be interested in going to a swingers club and or an erotic expo.

this is long but very interesting, TY for bravely posting it here, do any of your friends or family know?, do u think she's told anyone?

 

[drakebelg]

I have told no one, excpet for online. My guess she has not discussed it with anyone. There is one fairly sexually wilder girlfriend that she might talk about it to.

 

[CONST65]

Before I admitted to her I want to be a cuckold (September 2023)

• She told me several years ago that she was very disappointed the first time we had sex. I came after a few minutes before she did.
• At the beginning of our relationship she joked saying I was only her second best lover. After a while she let it go and said now I was the best. I didn't believe her. This became true.
• Even though I am 7x5.5 she said she would prefer it if I was a good bit thicker and a bit longer.
• For about 8 years we have been using large cocksleeves regularly. Her orgasms are totally different, crazy intense and multiple.
• She laughs when she feels my dick falling out of her big pussy.
• She loves the idea I am not big enough to fill her big pussy.
• She enjoyed telling me about her intense sexlife with a huge cock ex who was recently a colleague.
• Sex is almost always in a position with her back to me.
• She loves to ride a big dildo with me watching.
• She manages our finances.
• She defines when we have sex.
• She agreed that I should try jelqing or penis pumping to make me bigger.
• She admitted she is a size queen.

After admitting I would love to be a cuck in September 2023

• She admitted recently after 21 years together that she had 2 better lovers than me. One definitely had a bigger dick than me and probably the other also. They both were assertive dominant lovers. I am guessing there are even more lovers who are better than me. She laughed when I said this.
• She admitted if she would be a hotwife she would like a dominant guy.
• She fantasizes at least once a month about fucking a strong athletic guy.
• She said she doesn't want me watching while she is with someone else. I must wait somewhere.
• If I cum too quickly she is annoyed, orgasms with a vibe. If we have a second session she will orgasm quickly with a vibe and not let me cum.

New developments November/December 2023

• She has listened to a podcast about cuckolding (Cuckoldress) and said afterwards that the main thing is I must not push her, to be patient, and it will be her decision.
• Her Bukkake fantasy (wow): Gets crazy turned on thinking about the video of cap dagde woman giving 2 guys a BJ. She cums super fast when she thinks about this. She doesn't want me there and wants them to cum on her tits.
• Asking me once a week for Max (her favourite sleeve) to fuck her.
• While I fuck her in spoons she imagines she is in reverse cowgirl with another guy and I am licking her pussy.
• Her favourite story that I have ever written, was me caged and her fucking her self upstairs with a huge dildo pretending it's another guy. She totally dominates me and I cleaned her up in the story.
• I told her she won't let me lick her anymore and asked if it's because I am not any good....no answer. I asked if she had guys much better than me, she said no. I said I know that's a lie and she laughed out loud.
• She might be interested in going to a swingers club and or an erotic expo.

Something tells us thst she us hoing to.be a great hotwife and cuckold you havi g her buy her outfits to fuck.in as weel.as nakimg dinnner reservations hotels etc maybe even help.her getvrrsdy to.go.out tonfuck with total.open communication it can be great

 

[fmwanon]

Before I admitted to her I want to be a cuckold (September 2023)

• She told me several years ago that she was very disappointed the first time we had sex. I came after a few minutes before she did.
• At the beginning of our relationship she joked saying I was only her second best lover. After a while she let it go and said now I was the best. I didn't believe her. This became true.
• Even though I am 7x5.5 she said she would prefer it if I was a good bit thicker and a bit longer.
• For about 8 years we have been using large cocksleeves regularly. Her orgasms are totally different, crazy intense and multiple.
• She laughs when she feels my dick falling out of her big pussy.
• She loves the idea I am not big enough to fill her big pussy.
• She enjoyed telling me about her intense sexlife with a huge cock ex who was recently a colleague.
• Sex is almost always in a position with her back to me.
• She loves to ride a big dildo with me watching.
• She manages our finances.
• She defines when we have sex.
• She agreed that I should try jelqing or penis pumping to make me bigger.
• She admitted she is a size queen.

After admitting I would love to be a cuck in September 2023

• She admitted recently after 21 years together that she had 2 better lovers than me. One definitely had a bigger dick than me and probably the other also. They both were assertive dominant lovers. I am guessing there are even more lovers who are better than me. She laughed when I said this.
• She admitted if she would be a hotwife she would like a dominant guy.
• She fantasizes at least once a month about fucking a strong athletic guy.
• She said she doesn't want me watching while she is with someone else. I must wait somewhere.
• If I cum too quickly she is annoyed, orgasms with a vibe. If we have a second session she will orgasm quickly with a vibe and not let me cum.

New developments November/December 2023

• She has listened to a podcast about cuckolding (Cuckoldress) and said afterwards that the main thing is I must not push her, to be patient, and it will be her decision.
• Her Bukkake fantasy (wow): Gets crazy turned on thinking about the video of cap dagde woman giving 2 guys a BJ. She cums super fast when she thinks about this. She doesn't want me there and wants them to cum on her tits.
• Asking me once a week for Max (her favourite sleeve) to fuck her.
• While I fuck her in spoons she imagines she is in reverse cowgirl with another guy and I am licking her pussy.
• Her favourite story that I have ever written, was me caged and her fucking her self upstairs with a huge dildo pretending it's another guy. She totally dominates me and I cleaned her up in the story.
• I told her she won't let me lick her anymore and asked if it's because I am not any good....no answer. I asked if she had guys much better than me, she said no. I said I know that's a lie and she laughed out loud.
• She might be interested in going to a swingers club and or an erotic expo.

Is her pussy big from the sleeve or large dildo or is it naturally big? If it's from the toys, how big are they?

 

[C102987]

Slow and steady wins the race. Gives you more time to plan and really dial in what both of you want to experience together.

 

[SexualOptions]

I love how you wrote this. I want to be able to do this as well. If we ever progress...

 

[drakebelg]

Is her pussy big from the sleeve or large dildo or is it naturally big? If it's from the toys, how big are they?

She was always roomy but we started stretching her with my hands in 2015. 9" girth is very easy for her. Largest was 11" girth.

 

[drakebelg]

Very happy here: Back to 24/7 chastity, FLR and premature ejaculation (PE) training.

An update and a questio (at the bottom). From mid Feb I was in 24/7 chastity, signed FLR contract and my wife was training me to go from severe PE (45seconds) to under 10s. We were at a solid 15s. I was spoiling her, massages, house chores, sex how she wanted etc.. We were both really happy.

Then for the easter holidays we were heading away with our kids, so she said to take a break and go vanilla for a while. Due to habits it was still her calling the shots while away and me doing whatever she wanted. When we returned, due to me having a very difficult time at (unemployed and re-education) and just not feeling good we didn’t get back into it and I didn’t ask.

Things have settled and I am feeling good, so yesterday I sent her this list of questions (and her answers) about restarting.

She answered yes to these: FLR including the full contract, 24/7 chastity, PE training, big cock sleeve sex, strap-on sex (me to her), long two handed pussy stretching sessions, her fisting herself and riding big dildos while I watch.

These she left blank which usually means a no or not yet for her: my orgasm denial+ruined orgasms, sitting on my face for oral, me wearing her thongs.

We are both very happy with this restart. She didn’t want to push me, so she was waiting until I was ready. So here I am locked up, just after giving her a massage, stretching her and giving her a very big orgasm from a huge sleeve. I wasn’t allowed in her, and I have to wait for two days do my first ejaculation time trial to set the new base line. I am working while she is upstairs resting and masturbating with her new vibrator. Life couldn’t be better.

A question. I was surprised that she chose PE training above orgasm denial. I am wondering what her motivation is here. Enjoying the power of humiliation? She knows I am 100% open to cuckolding so could it be a way of opening the door for her if I cum on insertion? Other ideas?

 

[drakebelg]

Small progress, but still progress.
We had sex this morning on her demand. She told me to unlock, last time was 4 days ago. First we took care of her with my hands, then she told me to set the countdown timer with 90 seconds as the target (last time I reached 105s). While giving her a back massage she told me to start. I entered her amazing loose pussy and started looking for some friction. I kept up a normal thrusting, nice and gentle, not too fast, no moaning from her. After about 20 seconds i knew it would be fast and at 50seconds i came, cool.

Then during breakfast we had a talk about sexuality, her satsifaction etc... and once i mentioned her "free pass" it was clear she wanted to talk about it. I haven't brought it up in months.

Main points from our talk:

• She's has been thinking about cuckolding, she is not ready yet but is think about it.
• She loves that i am locked and submissive and could never imagine me being dominant in sex, eventhough that's what she fantasizes about.
• She knows i don't need another woman and the my PE is even making this even more certain.
• She again said that due to my PE, normal PIV isn't really satisfying so it's better it's it's done fast. Ohh lala, as a sub I love that.
• She is 54 and if she is going to have other lovers she needs it to happen pretty soon.
• Her fear is still if it starts that she doesn't know where it will go, feelings wise.
  • I said that it's okay to develop new relationship feelings but that we need to be open about it. It can happen she has a regular bull, that she tells me that she is starting to have "feelings". She asked what would i think, and she was happy when I said if the feelings are just normal new relationship ones then that's fine by me (She like that). But, if it felt like it was getting more serious then it's better to find someone else (she also liked that idea).
• She was interested in that fact that there are young bulls wanting to fuck women her age and many are avialble lcoally via SDC.
• She likes the idea that there are young bulls not at all looking for a serious relationship with a woman in her 50's.

Now I will continue my chastity, respecting our FLR rules and becoming a severe permanent prejac. I love how she is now totally secure that I have no interest in other women.
I won't bring up the cuckolding again until she does. So hoepfully slow and easy......

Opinions or suggestions are appreciated.

 

[lonlonepona]

Are you truly sure you want to do this ? She hesitates for a good reason. It’s never too late to stop now. I’m sure she will actually be relieved if you say to her, “you know what, I let me horniness get the better of me. I just want to be us, and spend time together doing other things. I love you.”.

The reasons wives hesitate is because they know sex cannot just be easily turned off as a means of connection with that person. Not when they have been with someone for so long especially.

 

[drakebelg]

Thanks, I fully understand what you are saying. I believe I am sure but I am not naieve about the risks. I will think about your suggestion though or even openly talk about it with her. Maybe we might just play around with her openly flirting with guys and stop there..... We'll see. The openess is strengthening our relationship and she is much more satisfied now in our FLR.
It's no where near a must for me. We'll be very carefull not pushy and see where things go.

 

[lonlonepona]

Thanks, I fully understand what you are saying. I believe I am sure but I am not naieve about the risks. I will think about your suggestion though or even openly talk about it with her. Maybe we might just play around with her openly flirting with guys and stop there..... We'll see. The openess is strengthening our relationship and she is much more satisfied now in our FLR.
It's no where near a must for me. We'll be very carefull not pushy and see where things go.

How would you view a bull in an FLR ? Is he also there to please her and ultimately submit to her, but in a different way ?