Making good progress!

For cuckoldresses and the men who serve them.
Charlie Kennedy
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Making good progress!

Unread post by Charlie Kennedy » Wed Apr 05, 2023 12:01 am

So, I have an interesting story for you but I may require a little guidance on what comes next.

Let's start at the beginning, I'll make it brief. A few months ago I told my partner about the life style. I did it openly and honestly and withheld some more extreme details of course to ease her in. She of course was confused and really didn't understand it. But, she was open to talk about it, however made it very clear that she isn't interested in the idea herself.

One night we started the foreplay watching a little bit of porn as we occasionally do. I stupidly jumped the gun a little here and put on some Hotwife porn... Bad idea. This actually made her a little upset and I feel that we actually took a backwards steps or two. Leaving out some more detail, the short version is that I left the life style out of our conversation for a few weeks until I could break it down a bit better to her.

When the time was right, we had another chat about it. I explained how much I like the idea and that in reality it's not something I'm really looking for, it's more to pretend ;) as I like feeling jealous and competition. Of course as we all know it's a little more complicated than that, but I thought serving the idea in bite sized chunks may go down better. She actually sprung to life a little and I could tell she was turned on, if only by how much I was talking a out it.

Over the next few weeks I actually got her to sext chat people online whilst I watch (she was very uncomfortable at first but eventually got into it.) But this is where I am right now. I bought her a couple if toys in the meantime. A wand and a dildo. Again, she was extremely tense about using them. Over a little time she has learned to love the wand and even asks for it sometimes... But the dildo is still a no for now. We have tried once or twice but she doesn't feel too comfortable with it. We only manage to ge the tip in before she backs out. Of course that's okay and she is willing to try again, it just hurts her a little due to the material and the fact she is really tight. Even lots of lube and foreplay didn't quite get us there. But the fact that she tried at all is huge progress.

So that's where I am so far. From absolutely nothing to the small begining steps. If anyone has any tips that worked for you then of course fire away and ask any questions you like. I'll be sure to keep you posted on any progress we have.

Abrandnewstart194
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Re: Making good progress!

Unread post by Abrandnewstart194 » Wed Apr 05, 2023 6:21 am

I think that one of the biggest things you can do to make her feel more comfortable, and able to process it all us just to communicate honestly, and openly with her about it. That includes listening to, and respecting her reactions, even if they aren’t what you hope they will be.

When you played the HW porn for her, you were springing something on her, which put her on the spot, and probably made her feel like you were ignoring her protests, and pushing it on her. When you approached her directly, and not in bed to discuss it with her, and explain it to her, she’s going to feel more respected, and therefore receptive - ESPECIALLY if you don’t try to sell her on anything she doesn’t want, and if you take it at HER pace, and drop it when she wants you to drop it.

Cuckoldry is about female agency. I honestly have no idea how done guys (not you) think they can convince their women that they’re all about their women’s agency by…not respecting their agency to decide what they like, or don’t like.

Charlie Kennedy
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Re: Making good progress!

Unread post by Charlie Kennedy » Thu Apr 06, 2023 1:26 am

Couldn't agree more and thank you for the advice. Taking it slow, steady and listening to what she wants and feels comfortable with is certainly key. We are pretty open about the way we feel and can talk about almost anything which is great. Give it time and plenty of casual organic chat and I'm sure progress will follow. I'll keep you posted. Any other tips on what our next steps should be would be greatly appreciated of course.

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Pufferfish
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Re: Making good progress!

Unread post by Pufferfish » Thu Apr 06, 2023 3:13 am

I mostly agree with Abrandnewstart194, especially about her feeling like you were springing this on her all of a sudden. And to be rather blunt, your tactics and communication with your partner need a lot of work here I think.

Sounds like the hotwife porn definitely set you back, and that's because women in general don't really like porn, or at least most women and most porn. It's probably mostly, something she endures for your enjoyment rather than something that particularly turns her on. Men are visual, women are more in their heads. This is why porn is popular with men... while women read erotic stories. And when a women is suddenly put on the spot, she responds in conditioned ways. Just about every woman is conditioned to at least say, even if she doesn't believe it, that she has no interest in other men, would never cheat, doesn't think about other men having sex with her, she's a good girl, etc. And she doesn't believe that you would really want anything different, that you just THINK you do, or that you'll change your mind later and send her packing. It's (most likely) poor communication on her part, telling you what she believes she's supposed to, rather than the full truth. No different than her asking you if "this dress makes me look fat?" It puts you on the spot, and you have a conditioned answer.

The next thing is your poor communication. Just like her, you're being selective with the truth. Withholding details about what you think/like from her. Being dishonest (I presume) about how this is just a fantasy and not something you'd want to actually do. "Giving her bite sized chunks" to process. To me, it sounds like she's trying very hard to do things that make her a little uncomfortable, simply to make you happy. Watching porn, using toys she doesn't enjoy, sext chatting people online... and might feel like you are pressing her to do more and more stuff she doesn't want to. When really, she might like it, but the communication isn't there yet. Also, it might not be what you're saying, but HOW you're saying it. I'm not sure on the wordage you chose, but you should think carefully. If you tell her "I don't care if you have sex with someone else", that's bad. "Not caring" is bad. Where "I'd love it and would think it's so sexy if you had sex with someone else", that's good. Again, I don't know what words you used when talking to her, and don't mean to insult, but don't overlook those details. "How" is more important than "what".

My advice would be this: Sit down and have a formal conversation with her about your sex lives (This might be more than a single conversation). Not something you do in bed before or after sex, but a serious conversation. Put her at ease doing something nice like a foot massage, or brushing her hair, neck massage, whatever while you do it. Talk about what she loves about your sex life, what she would like to improve on, any fantasies of hers she's willing to share, then talk about your fantasy. Enough with the selective honesty, and just lay your cards on the table. Make sure she knows that you don't want her to do anything that she doesn't want to do, or force her to do something, but that you want her to know exactly what you'd like to happen someday whenever she's ready, or not. The more you trust and confide in her, the more she'll be willing to open up to you. It's A LOT easier for a guy to say to his woman that he wants her to sleep with other men, than it is for a woman to say to her man that she wants to sleep with other men... for obvious reasons. She might struggle to lower her guard for a bit until she actually believes you're sincere. Once she believes you, once there are no secrets and no "bite sized pieces", then you might to actually make some progress.

Where I don't agree with Abrandnewstart194, is this isn't just about her. It's about both of you. It's something you're going to do together, even if it's something that she does when you're not there. It has to be something she actually wants and is comfortable with, yes. But it will also be something she does because you want her to. Because it's something you want and are comfortable with. In order for it to work at all, even a little, you both have to be completely on the same page. No secrets, no bullshit. So stop bullshitting her and just talk. No porn. No roleplay. No bite sized crap. Just talk. Then you start introducing all that other stuff when the defenses are down and there's nothing more to hide.
_____________________________________________________________________

Our story: viewtopic.php?f=5&t=62359#p1198704

Her pics: viewtopic.php?f=9&t=63848#p1229721

wannabecUKold
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Re: Making good progress!

Unread post by wannabecUKold » Thu Apr 06, 2023 5:21 am

Pufferfish's advice is very good, very full.

I would add that you need to address her obvious likely riposte that you too would not actually like it if she had sex with another man. You only fantasise that you would enjoy it.

The solution and response I think is to work out how you believe it could happen successfully, what do you believe would be the most successful way for her to do it and retain her piece of mind? And you yours. On a nudist beach, or with a masseur, or a swingers' club, or in the hot tub with a known friend, or on a night out with her ex by herself, 'cheating' with someone she knows, picking up a guy on holiday or sex with a hot youth off the internet?

She surely will have a type of guy in mind once she contemplates the idea. So who is he and how does she get him? It will be a trade-off - safety, health, scandal, repugnance, risk to the relationship etc. Knock this barrier down so she can give herself permission to contemplate her new future.

gilder145
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Re: Making good progress!

Unread post by gilder145 » Thu Apr 06, 2023 11:25 am

Sexting is ideal but not while you watch. Sex toys did not work for us at all moving into this, it only worked when we were close rather than toys. Give her space and time alone with her phone. It may hurt a bit but it will probably work if she is curious about the lifestyle.

Charlie Kennedy
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Re: Making good progress!

Unread post by Charlie Kennedy » Sat Jul 01, 2023 6:10 am

So a quick update with some good news. It's been a little while but we ended up chatting about it again. We ended up agreeing that this is early days and we need to take it slow with an option to back out at any time. Which is exactly what I wanted to hear myself too. We then agreed that the next step would be to go online and sext as that's what she enjoyed and was excited to do. She said it made her feel hot that other men were chasing after her and really boosted her confidence. Which again, was music to my ears. Jumping forward a little we went onto a website and she started to flirt with a few guys. She got a little excited and then got even more turned on seeing how excited I was. She started to play with herself and shortly after ushered me to help. We did this for some time, teasing her as she read message from men explaining what they would do to her. Things got hot and tense and she demanded that I fuck her... So I did. Neither of us lasted very long. She came hard and so did I. But it didn't stop there. Within minutes she was ready to go again so I made her cum a second time with my hands. She was fully satisfied and loved the experience.

I tried to cut out the fluff of our conversation because it was quite long and had many topics. For example, she mentioned downloading a chat app so she can speak to them through the day rather than having to sign in to a website... But wanted to see how this session plays out first. Also conversation about actually sleeping with someone. The answer there was a clear "definitely not ready for that and might never be" which is certainly expected.

Hope you enjoyed this update. Any comments or questions questions would be greatly received

SlimScott
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Re: Making good progress!

Unread post by SlimScott » Mon Jul 03, 2023 4:47 am

Great update. The fact that she demanded that you fuck her, and the fact that you complied with her demands is really good. It shows that she is willing to be in charge (dominating you), and you are submissive. It is progress - you are on the road to being a cuck! Good luck, and keep us up to date on your progress!

Whenwillshe
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Re: Making good progress!

Unread post by Whenwillshe » Mon Jul 03, 2023 5:02 am

Sexting with someone is much farther than many ever get.
Have fun!

subbieCuck
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Re: Making good progress!

Unread post by subbieCuck » Mon Jul 03, 2023 7:50 am

Sounds great! Well done for both of you! My advice is let her lead the way, and I believe, that soon enough you will be an official cuckold! Keep us updated! Cheers!

Charlie Kennedy
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Re: Making good progress!

Unread post by Charlie Kennedy » Tue Jul 04, 2023 2:14 am

Okay, so another quick update!

These last few days have been a little wild. The day after we had our breakthrough it was quiet. She ignored all the messages coming through on the app and we didn't really talk about it. To be honest we were both working throughout the day so that had some impact on the want to sext in the middle of the day (she works from home). I did ask for an update on our "friends" and she brushed it off, telling me she doesn't have time to do that. I understood her point of view to be honest. She is really popular on the site and is getting hammered by constant messages. After work I lightly brought up the topic after logging in myself to see over 50 different requests from men. I joked with her that she's Miss popular and it's really hot. She smiled and laughed but moved the conversation away. I thought to myself that, this could be a one and done thing and I didn't want to push it any further. But that's when the night rolled in. We both jumped into bed and I tried one last effort to test the water. "I haven't stopped think about last night all day today". She backed into me slowly "Really?" She smiled. I nodded. She grabbed my hand and guided it to her pussy... She was already wet. From there it is a bit of a blur (I'll explain why). We both talked about the experience the night before and how hot it was, all the while I was teasing her. Again, it ended with her asking me to fuck her. Which I did. Again, we both came very quickly.

Now to last night... Well. Basically just repeat the day time. Other than the fact I have set up an app for her with the one person on it she actually properly sexted. She still hasn't used it but we discussed it and still sounded a little nervous. Until the night came again. This time I made the move... Kind of. All I did was run my hand up her leg and she stopped it on her again soaking pussy. "I think you're having the same thoughts as me?" I chuckled. She nodded all shy and blushed. I started to tease her and tell her how hot it is that she's starting to enjoy it as much as I am. I asked her to tell me what it is she likes as I played with her. She said it was the amount of men that want to fuck her brains out and the amount of effort they are going through to try it. And then also the amount it turns me on and how loving i have been as a result of these past few days. An interesting and great response. To wrap this up, we had amazing sex once again.

We discussed a little afterwards about her concerns with texting. One of her big concerns is that she doesn't want to say anything that would upset me or make me cringe. I again reassured her about this. There is literally nothing she could say to make me feel those things. I have now had the thought to tell her that I wont log in for a few days so she can have some privacy with the guy. Maybe that will help? Im not sure. She also then thanked me so much for the way I'm handling this and taking her thoughts into account and how slowly I'm willing to take this. Which was really nice and reassuring that she feels comfortable where we currently are.

These always go on longer than I initially intended, so sorry again. Any comments and feedback always loved here. Thank you in advance.

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Lucky Dog
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Re: Making good progress!

Unread post by Lucky Dog » Tue Jul 04, 2023 2:44 pm

It's very exciting to read about how the two of you are going down this road together and you express yourself very well. Keep on trying with her and please keep on telling us about how it's going.
Many times, good sex is the best and quickest end to virginity.

central
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Re: Making good progress!

Unread post by central » Thu Jul 06, 2023 2:14 pm

Charlie Kennedy wrote:
Tue Jul 04, 2023 2:14 am
Okay, so another quick update!

These last few days have been a little wild. The day after we had our breakthrough it was quiet. She ignored all the messages coming through on the app and we didn't really talk about it. To be honest we were both working throughout the day so that had some impact on the want to sext in the middle of the day (she works from home). I did ask for an update on our "friends" and she brushed it off, telling me she doesn't have time to do that. I understood her point of view to be honest. She is really popular on the site and is getting hammered by constant messages. After work I lightly brought up the topic after logging in myself to see over 50 different requests from men. I joked with her that she's Miss popular and it's really hot. She smiled and laughed but moved the conversation away. I thought to myself that, this could be a one and done thing and I didn't want to push it any further. But that's when the night rolled in. We both jumped into bed and I tried one last effort to test the water. "I haven't stopped think about last night all day today". She backed into me slowly "Really?" She smiled. I nodded. She grabbed my hand and guided it to her pussy... She was already wet. From there it is a bit of a blur (I'll explain why). We both talked about the experience the night before and how hot it was, all the while I was teasing her. Again, it ended with her asking me to fuck her. Which I did. Again, we both came very quickly.

Now to last night... Well. Basically just repeat the day time. Other than the fact I have set up an app for her with the one person on it she actually properly sexted. She still hasn't used it but we discussed it and still sounded a little nervous. Until the night came again. This time I made the move... Kind of. All I did was run my hand up her leg and she stopped it on her again soaking pussy. "I think you're having the same thoughts as me?" I chuckled. She nodded all shy and blushed. I started to tease her and tell her how hot it is that she's starting to enjoy it as much as I am. I asked her to tell me what it is she likes as I played with her. She said it was the amount of men that want to fuck her brains out and the amount of effort they are going through to try it. And then also the amount it turns me on and how loving i have been as a result of these past few days. An interesting and great response. To wrap this up, we had amazing sex once again.

We discussed a little afterwards about her concerns with texting. One of her big concerns is that she doesn't want to say anything that would upset me or make me cringe. I again reassured her about this. There is literally nothing she could say to make me feel those things. I have now had the thought to tell her that I wont log in for a few days so she can have some privacy with the guy. Maybe that will help? Im not sure. She also then thanked me so much for the way I'm handling this and taking her thoughts into account and how slowly I'm willing to take this. Which was really nice and reassuring that she feels comfortable where we currently are.

These always go on longer than I initially intended, so sorry again. Any comments and feedback always loved here. Thank you in advance.



Hey Charlie, enjoying reading of the progress you two are making.

It seems as if she is into this now, and in her mind she is a lot closer to making this a reality than she thinks you are. She was soaked! Nice!

I underlined the telling part above, She is eating it up that other men are so hot for her. Probably receiving many great compliments. This is likely boosting her confidence and revving her up sexually. And, she knows you support her and are more loving to her. Seems she is mentally accepting that she could have fun and not cause damage to your marriage, which is a big hurdle.

She is likely already visualizing meeting the guy that she is sexting with, kissing and making out with him, and probably thought a lot about having sex with him. That might be what she is concerned that might upset you.

Great idea for you to back off a bit and give her some space when it comes to logging on and checking the progress, may be better to just check in every 2 - 3 days and ask her daily for updates between her and him (assuming she is sexting only one guy). It could be very exciting for You to hear her tell the details of their conversations to you. Very soon it could become more intense between them if she doesn't get cold feet. You could start asking her when and where they are planning to meet - be very supportive. In her mind, she likely has ideas about when and where.

She is getting wet and turned on talking and thinking about it, she knows men want to fuck her brains out, her husband is on board. She likes that you want to take it slow. The lights are all green! Keep us updated.

Charlie Kennedy
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Re: Making good progress!

Unread post by Charlie Kennedy » Tue Sep 12, 2023 12:18 am

It's been a little while. Life got in the way abit over the last couple of months but this week I brought it up again just to see where we stood. Some good, some not so good I guess. Let me explain and maybe you guys can help with the next step.

So, I told her I was thinking about our last experience a couple of months ago and how good it was. She brushed it off at first with a smile. But I pressed a little further. To cut to the chase, we started a long conversation about what works and what doesn't. We came to the conclusion that the texting just isn't viable at this moment. It's not gone completely out of the picture but she is just way too busy to hold that kind of responsibility. A small disappointment but a fair point nonetheless. We agreed that a small step back into it would be watching some "Hotwife" porn to my suprise. So that evening I let her choose what to watch within that category. She chose well and whilst watching it she made comments such as, I love how involved the husband is, holding her hand whilst she gets fucked. Fast forward a touch and she again asked me to fuck her and she came a lot.

The next evening rolled around and I just blatantly said, I want to do that again, and she happily obliged. This time she chose a shorter 2 minute amateur video to get us started. Then we shifted over to a another amateur video of a woman coming on a large cock over and over. Very different from the night before where we watched something a bit more sensual. This time she wanted to make me finish with her hands whilst we watch, which she did very well. After I had recovered I turned my attention to her and she was dripping. I used my hand on her clit and before I knew it she was cumming really really hard. Feet curling, back arching and she just kept going. And that's where we are at now. I enjoy doing this but I'm just addicted and don't want to over step any mark. She's obviously having fun too but how much of it is the concept and how much is it just the fact we're having fun. Neither is bad of course, but I'm not sure what the next step should be and how to go about it.

Tryn
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Re: Making good progress!

Unread post by Tryn » Tue Sep 12, 2023 7:10 am

Love the update! Have you tried the dildo when she’s super turned on and dripping? Perhaps after watching a video with a hung guy and she’s dripping, that may be the time to try it out.

What app have/were you been using?

Charlie Kennedy
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Re: Making good progress!

Unread post by Charlie Kennedy » Tue Sep 12, 2023 7:57 am

That's not a bad idea at all. She is really apprehensive about the dildo as she's really tight and she finds it a little off putting using something that's not flesh. She's used it successfully once a few months back whilst I got off to watching which really helped her. It's not her "go to" as she prefers the wand toy. I'm not sure what would encourage her to use it more but timing might be key so may try to suggest it next time.

We have used a mixture of porn sites and dating apps to weed out a couple of guys. Then we give them her Google Chat email address for more personal conversation. But that project is on hold... for now :)

curioushubby1965
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Re: Making good progress!

Unread post by curioushubby1965 » Tue Sep 12, 2023 11:41 am

Charlie Kennedy wrote:
Tue Sep 12, 2023 7:57 am
That's not a bad idea at all. She is really apprehensive about the dildo as she's really tight and she finds it a little off putting using something that's not flesh. She's used it successfully once a few months back whilst I got off to watching which really helped her. It's not her "go to" as she prefers the wand toy. I'm not sure what would encourage her to use it more but timing might be key so may try to suggest it next time.
I have enjoyed your thread, thanks soo much for sharing.

On the toy front, have you shopped for a dildo she may be more comfortable with? My wife has always been somewhat tight as well and the slimmer dildos are a better fit for her. She enjoys extra length but nothing too thick. Takes some effort to find the best one for her as they usually increase the thickness as they increase the length.
Not sure what material hers is, but some of the life like, high quality silicone ones may be more comfortable for her.
Even though she gets very wet, may be worth trying a high quality water based lube for the toys as well.
My wife also prefers the wand, that is by far her favorite, just recently upgraded to the wand XL.
We usually start her with the wand, either me or her driving, then as she gets more into it, she will take over the wand and I will use a dildo on her, making sure I go slow and easy to get her used to it.
Just some thoughts for you.
Good Luck

Charlie Kennedy
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Re: Making good progress!

Unread post by Charlie Kennedy » Wed Sep 13, 2023 12:56 am

Some solid advice once again, thanks guys! I'll keep you posted when I can.

Charlie Kennedy
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Re: Making good progress!

Unread post by Charlie Kennedy » Mon Jan 08, 2024 12:14 am

It's been a little time since I last posted but I wanted to give this time to develop, amongst just life stuff being more important too. So this is where we stand today. We have been in discussion about the lifestyle once every couple of weeks I would say. It's been a semi regular topic in our sex life now which is great progress from it not being a thing at all. She is very comfortable talking about it and using it to her advantage in the bedroom. So what progress have we made if any? Well, it's more of a small but important shift. As I said, the topic itself is no longer a strained one. Where do I stand and where does she stand?

I have made it clear that I am open to pretty much everything. I elaborated about specifics to her of course but you guys already know. And she told me what she is comfortable with at this moment in time. She wants to find someone that she has a connection with, to be able to chat to and make sure they're interested. This is mainly for confidence and an ego boost as she can be pretty shy and lacks a little self confidence. This is her biggest hurdle. So she is actively on a dating app now chatting to a handful of different guys. (To clarify, the app/site she was using in the past was basically a porn site just to mess around on. This is an official dating app where she has multiple pictures uploaded and what she's looking for in a man. Mostly PG details but a little flirty and serious).The main goal of this? Well for her, it's too sext, swap pics and have some fun online. For me? Well, I'm hoping it may grow into a little more with a bit of encouragement.

This topic is a slow burner but I think the pace in which this is moving is a healthy one. As eager as I am, I find it reassuring that she's taking the time she needs.

What are your thoughts on this? :)

CuriousHusband91941
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Re: Making good progress!

Unread post by CuriousHusband91941 » Fri Jan 12, 2024 4:05 am

Exciting.
I look forward to updates as this is how I would like to proceed with my wife too.

eater
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Re: Making good progress!

Unread post by eater » Sun Jan 14, 2024 8:49 pm

i'm enjoying your progress. thanks for sharing

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