Be careful what you wish for - how I turned my conservative wife to an hotwife - in progress

[Voyapuppyfork]

Excellent update. Congratulations!

Thank you!

[Voyapuppyfork]

I love this story ! I am also a conservative woman but curious about hotwifing…

Thank you for commenting! I'm glad you love our story and found it helpful. Let me know if you have any questions for me or Jenny. Although this is sort of my own journal, she knew I'm documenting our journey anonymously somewhere online. I can forward your questions to her.

Also, if you have any ideas or advice on how to help my conservative wife adapt to this lifestyle, including things we can try or ways for me to support her in overcoming her nature, I would greatly appreciate it.

[Voyapuppyfork]

Sorry for the delay. I've been procrastinating, and it's been really hard to find time to write. I feel like I need more time to process what's going on in real time before I can convert it into words. So, I've decided to post what happened a couple of weeks after it happens, instead of trying to keep up with what's happening in real time.

Jenny was originally planned to have lunch on the Wednesday of the Mother’s Day week. However, we made a last-minute decision to take that entire week off and embark on a road trip with my in-laws. As a result, they lunch “date” had to be postponed for another week. Little did I know, Jenny and David continued their communication throughout the entire road trip, right under the watchful eyes of my in-laws. It was only after we returned that Jenny shared all the messages with me. Most of their conversations are vanilla, with the occasional exchange of picturesque scenery photos. Yet, despite the seemingly innocent nature of their interactions, I definitely feel there was something more than just connection between colleagues, and a subtle undercurrent of sexual tension seemed to linger beneath the surface, surely enough to make me excited.

On the following Wednesday Jenny had her lunch date with David. David messaged her the night before to confirm their plans. he wanted to check if Jenny would be busy the next afternoon, because the restaurant he had in mind was a bit of far from their office. Unfortunately Jenny already meetings lined up and wouldn't be able to spend too much time for lunch. So they had something quick instead. As David's message came through, a wave of anticipation washed over me. Although it turned out to be another lost opportunity, but my instinct couldn't help but sense that there was something more to David's intentions, which gave me a titillating feeling, a mix of excitement and curiosity. However, Jenny dismissed my thoughts and insisted that David was just being nice. She does not feel David is interested in something more than a professional partnership at this moment. To be honest, Jenny has never been the best at picking up on subtle hints. It took her quite a while to realize that I’m into her rather than her best friend, Naomi (admittedly, to be fair everyone is into Naomi back in the day). I guess we will see who is right .

Even through things have been relative quiet between her and David. Jenny and I have grown even closer than ever. To keep the momentum going, I decided to surprise Jenny with a special gift - a pair of sexy panties that read “Cuckoldress in training”. I intended it as a playful reminder of what we signed up for together. The reaction of Jenny’s face was priceless. She blushed deeply and vehemently sweared that she would never wear it. We had a good laugh and I could sense a hint of intrigue in her eyes. Now the challenge lies in persuading her to wear it for me. It's all in good fun, and I believe it could add a thrilling element to our intimate moments. Building trust and open communication has been the foundation of our journey thus far, and I'm confident that we can navigate this new adventure together.

Through regular check-ins with Jenny over the past couple of weeks, I've gained confidence that she is truly enjoying our current arrangement. One aspect she particularly appreciates is the level of attentiveness I show towards her in every part of our daily lives. I've become more focused on her satisfaction during our intimate moments, ensuring that she feels fulfilled and pleasured. In our conversations, Jenny has playfully joked that if only our arrangement didn't involve her having sex with other men, it would be perfect for her. Another element that Jenny finds exciting is the sense of having a shared dirty little secret between us. The knowledge that she has a hall pass and the freedom to explore her desires, should she choose to, adds a naughty and empowering aspect to our relationship. If she suddenly decide to fuck the neighbor the next day, she know I would not say anything, if any I would probably wear a big smile on my face. Lastly, Jenny enjoys the game we're playing with David. It makes her feel like she's in her early 20s and experiencing the thrill of dating again.

During one of our recent check-ins, Jenny and I had an incredibly meaningful and open discussion that set the perfect atmosphere to discuss things down the road. I took the opportunity and proposed that we should probably reconsider and reestablish our intimacy. The truth is, sooner or later she would take a new lover, whether it is David or someone else, and he would replace me as her primary sexual partner. It's important for us to acknowledge that, and plan ahead. We are barely having PIV sex now, we need to redefine our intimacy and strengthen our bond as a couple.

I expressed to Jenny that I genuinely enjoy pleasuring her through oral sex, giving her massages, and worshiping her feet, among other things. I also offered my assistance in helping her prepare for her encounters, and while I'm not entirely certain at this moment, I expressed my willingness to potentially clean her up afterwards. As for my own desires, I shared with Jenny that I am particularly interested in being edged and experiencing ruined orgasms. Moreover, I expressed my desire for her to eventually take on a dominant role, exploring elements of BDSM within our relationship. Jenny agreed those are good ideas to start with, and she expressed her willingness to fulfill these desires for me. We also discussed the possibility of engaging in activities such as pegging and chastity play, although Jenny mentioned that, at least for now, she doesn't have an interest in those specific aspects. It's clear that Jenny is fully embracing her role as a cuckoldress in training, and we are excited about the possibilities that lie ahead.

[scarlettscuck]

This is all playing out so nicely for you both. Communication and openness win the day…Congrats! Can’t wait to see your post one day soon that you’ve officially joined the “cuckold club.” It’s an amazing experience.

[Rogueuser1]

thanks for sharing - enjoying the story so far and looking forward to the next steps!

[SoCalOHWFan]

This is certainly an intriguing story. Looking forward to further updates. Thank you for sharing.

[elina]

Your Future Cuckoldress is making wonderful progress.
Can't wait till She lets Herself go and takes charge of Her cuck and both of yours sex lives.

Please keep supporting Her and updating.

[Voyapuppyfork]

Last week Jenny had a girls’ night out with her girl gang. Instead of my usual habit of checking on her as the night got late, I decided to give her some space and resist the urge to ask for details of her evening. For one, I knew she was always the responsible one in their group. One of her friend, Kate even occasionally teased her for being “boring”, cause she was always the one wanting to head home early, and often hesitated to go dancing and clubbing with them. Also, I wanted to encourage her to take the lead and make decisions without always considering me.

To my surprise, Jenny came home around 1 am for the first time in a long while. She seemed a bit tipsy and playful. She kept smiling and she was more affectionate than usual. I can tell she had more than 1 or 2 cocktails and it had fueled her desire. Our passion was reignited as we indulged in passionate kisses and quickly made our way to the bedroom. As I reached down, I could feel her wetness, and her soft moans indicated her readiness for oral pleasure. Eager to please her, I went down on her and started using my tongue. Jenny closed her eyes an threw her head back. It was long before her breath quickened and she bit her lip. I knew those were clear signs of her climax building and I was determined to bring her to it. After a while, she reached to grab my dick. However, unfortunately, I was not prepared, and despite how turned on I was, it remained flaccid, which was quite embarrassing and emasculating right in that heated moment. I could not perform right in front of my gorgeous sexy wife, and gave what she was craving. I could sense her disappointment, but she gave me a reassuring smile and told me it is alright, we continue to chat and cuddle until we eventually drifted off to sleep.

As it turned out, during their night out, they ventured to a bar and later a club. at the club, a group of young guys were hitting on them, brought them drinks and engaged in dances. Obviously, most of her girlfriends are happily married and they were just just enjoying some harmless flirting. But Jenny seemed embracing her newfound freedom and the new lifestyle just fine.

[mastiff]

Sounds like things are moving in a positive direction

[excitedPotential7]

I'm glad you get to experience this, my wife is so religious and conservative she won't even entertain any discussions on the matter

[slayveone]

Very well written stories. I can't believe the massage therapist didn't try to do more with her. I'm hoping to something similar as you and focus my efforts on oral and very little to no PIV and her have her main intercourse with other males.

[Voyapuppyfork]

Apologies that this post has been abandoned for so long. Many things have happened in the past couple of months. It is much harder than I thought to experience everything in real-time, riding a mixed-emotion rollercoaster while simultaneously trying to document in a dairy with an online audience in mind. In addition to our lifestyle changes, Jenny and I are also going through a lot in our daily lives. We finally pulled the trigger and bought a little home, so we have been busy with many issues as first time homeowners, and let’s just say it is a lot of work. Now I think I have finally completed the processing and ready to share our progress. I want to come back give a quick update. I will try to post here more often. I cannot promise anything, but luckily we do not have a lot of audience anyway, so I guess that should be fine. I will continue with where we left.

Since my last update, Jenny has become increasingly engrossed in her phone everyday. It’s quite evident that she is chatting and flirting with David. There are times when she seems preoccupied and is short with me. I must admit, I'm not entirely sure how I feel about it. There are moments when I sense a feeling of being left out, but simultaneously, I remind myself that we are progressing according to our plan. It's crucial to give her the time and space she needs. I keep reminding myself we are making progress as we planned. In reality, this lifestyle isn't always filled with excitement.

The positive aspect is that Jenny often keeps me informed about their conversations afterward. And The good thing is Jenny often fill me in on their conversation. The topic of cuckolding/hotwifing has become a regular part of our daily discussions, almost as if it's a completely normal thing. For instance, one of our favorite activities while watching TV is speculating whether the characters or the actors in real life are part of this lifestyle or not. It's become a playful and amusing part of our routine. It seems Jenny is getting use to the changes. She is transforming into what I’ve dreamed of.

The changes happened suddenly. One day, Jenny had a dinner party with her team. I knew David would be there too, but I did not expect too much from the event as it was professional setting with other coworkers. Around 8 PM, I received a message from Jenny saying, “Party is over, gonna grab a drink with colleagues”. I didn't think too much of it initially, but two hours later, I got another message that sent my heart racing, “Honey, David is driving me home, could you turn off all the lights and pretend not to be home, please?” I followed her instructions, went to the second floor, adjusted the blinds, and sat in the dark, wondering how things had suddenly developed so fast. Questions raced through my mind – were they going to come in, what did she tell him, where should I hide, and would they have sex at our home? A while later, a car pulled on the side, the engine running, For what felt like an eternity, it was quiet. Eventually, Jenny got out of the car, waved goodbye to the driver, and the car drove away.

I observed the car carefully as it drove away, then hurried down the stairs to greet Jenny, with a lists of questions swirling in my mind. Jenny met my gaze with the grin of a guilty little girl. I could tell from her face that she had indulged in a couple of drinks. “What has happened?” I cannot wait to ask. Jenny's response was quick, “Nothing! Can I have some water first?” She was smiling while biting her lips, and there was a hint of evasion in her glance. I fetched her a glass of water and sit her down, and slowly figured out the events of that night.

As it turned out, after the party, Jenny and David managed to slip away from everyone else went to a wine bar. Under the guise of alcohol, they flirted with each other. As the night progressed, the feelings were pretty intense. To alleviate David’s concerns, Jenny told a white lie to David that our marriage is on the edge. I’m having an affair, and we were in the process of separating. Jenny got pretty tipsy, David offered to drive her home. In the car she extended an invitation for him to come inside, but he declined. Buoyed by the courage fueled by wine, Jenny kissed David on the cheek, which igniting a passionate makeout session within the confines of the car.

[avid fan]

Wow, I've reread your thread and enjoyed every step of your journey...sounds like things could be moving up a gear so hope you return to the fold and keep things updated as they develop!

[snoogaloo82]

Apologies that this post has been abandoned for so long. Many things have happened in the past couple of months. It is much harder than I thought to experience everything in real-time, riding a mixed-emotion rollercoaster while simultaneously trying to document in a dairy with an online audience in mind. In addition to our lifestyle changes, Jenny and I are also going through a lot in our daily lives. We finally pulled the trigger and bought a little home, so we have been busy with many issues as first time homeowners, and let’s just say it is a lot of work. Now I think I have finally completed the processing and ready to share our progress. I want to come back give a quick update. I will try to post here more often. I cannot promise anything, but luckily we do not have a lot of audience anyway, so I guess that should be fine. I will continue with where we left.

Since my last update, Jenny has become increasingly engrossed in her phone everyday. It’s quite evident that she is chatting and flirting with David. There are times when she seems preoccupied and is short with me. I must admit, I'm not entirely sure how I feel about it. There are moments when I sense a feeling of being left out, but simultaneously, I remind myself that we are progressing according to our plan. It's crucial to give her the time and space she needs. I keep reminding myself we are making progress as we planned. In reality, this lifestyle isn't always filled with excitement.

The positive aspect is that Jenny often keeps me informed about their conversations afterward. And The good thing is Jenny often fill me in on their conversation. The topic of cuckolding/hotwifing has become a regular part of our daily discussions, almost as if it's a completely normal thing. For instance, one of our favorite activities while watching TV is speculating whether the characters or the actors in real life are part of this lifestyle or not. It's become a playful and amusing part of our routine. It seems Jenny is getting use to the changes. She is transforming into what I’ve dreamed of.

The changes happened suddenly. One day, Jenny had a dinner party with her team. I knew David would be there too, but I did not expect too much from the event as it was professional setting with other coworkers. Around 8 PM, I received a message from Jenny saying, “Party is over, gonna grab a drink with colleagues”. I didn't think too much of it initially, but two hours later, I got another message that sent my heart racing, “Honey, David is driving me home, could you turn off all the lights and pretend not to be home, please?” I followed her instructions, went to the second floor, adjusted the blinds, and sat in the dark, wondering how things had suddenly developed so fast. Questions raced through my mind – were they going to come in, what did she tell him, where should I hide, and would they have sex at our home? A while later, a car pulled on the side, the engine running, For what felt like an eternity, it was quiet. Eventually, Jenny got out of the car, waved goodbye to the driver, and the car drove away.

I observed the car carefully as it drove away, then hurried down the stairs to greet Jenny, with a lists of questions swirling in my mind. Jenny met my gaze with the grin of a guilty little girl. I could tell from her face that she had indulged in a couple of drinks. “What has happened?” I cannot wait to ask. Jenny's response was quick, “Nothing! Can I have some water first?” She was smiling while biting her lips, and there was a hint of evasion in her glance. I fetched her a glass of water and sit her down, and slowly figured out the events of that night.

As it turned out, after the party, Jenny and David managed to slip away from everyone else went to a wine bar. Under the guise of alcohol, they flirted with each other. As the night progressed, the feelings were pretty intense. To alleviate David’s concerns, Jenny told a white lie to David that our marriage is on the edge. I’m having an affair, and we were in the process of separating. Jenny got pretty tipsy, David offered to drive her home. In the car she extended an invitation for him to come inside, but he declined. Buoyed by the courage fueled by wine, Jenny kissed David on the cheek, which igniting a passionate makeout session within the confines of the car.

Wonderful to hear that things happened in the car. I'm sure there will be much more on the horizon. Definitely keep us in the know as to what happens further!

[trecital]

Yeah, keep us in the know.

[elina]

Looks like you are in for an interesting set of developments.
Looking forward to follow your story.

Sincerely
elina

[Voyapuppyfork]

After she told me about what happened that night, Jenny sat nervously with an innocent look, quietly checking on me. My heart raced with mixed feelings, but my erection betrayed any semblance of restraint. The excitement of knowing that just moments ago, she had been making out with another guy outside our door, her lips possibly still carrying traces of his saliva, fueled my eagerness to reclaim her. I kissed her forcefully, a mixture of passion and possessiveness. She seemed somewhat relieved to witness my reaction, despite our numerous discussions about it and the fact that she had my blessings. I suppose seeing my reaction for the first time was reassuring.

I could not keep my hands off her for the rest of the event. She was undoubtedly dripping wet too. To my surprise, she declined to have sex with me. I know where her heart was. Understanding that she wanted to savor the excitement, I couldn't contain my own enthusiasm. I ended up dry humping her from behind. Jenny kindly lended her hand for me. In a moment of submission, I cum shortly in her hand. As a reward of my obedience She patted me on my head and called me a good boy. After the cleanup, we cuddled and chatted. While I caressing her body, Jenny asked if I’m genuinely ready to let her have the freedom to be a real hotwife without regrets, I answered without hesitation. She responded “Good, cause I think I’m ready too.”

In the next couple of days, Jenny and David were constantly flirting over text. Witnessing the way she communicated with him left a tingling sensation in my stomach, a curious blend of discomfort and arousal. They planned their first date for the following Friday night. Throughout the week, Jenny invested in a new lingerie, scheduled appointments for waxing and a pedicure. I must confess, participating in and observing her preparations for her date proved to be the most erotic experience for me thus far. Assisting my woman, my wife, the love of my life getting transformed into a baby doll, and willingly sent her to another man like a gift was such a turn on.

Paradoxically, this impending event brought us closer. Jenny treated me like her best friend, seeking my opinions on the color of her nails, her dress choices, and brainstorming on every aspect of what she should do, contemplating different scenarios. In a sense, it is a secret adventure for us together.

[elina]

Sounds like Jenny was really good at involving you in the cuckolding-to-come.

Can't wait to hear about the next steps.

Sincerely
elina

[lockedhappyhubby]

You are one very lucky man! Jenny never ceases to make my cage tight, what a sweetheart. She's keeping the communication open with obvious concern for you, you're doing and feeling all the normal cuckold emotions that can become an addiction. (Trust me on that one)
Being involved in the preparation to her date... Priceless!
I too can't wait for Saturday to possibly hear how it all went.
Cheers!

[David52]

I’m not sure lying about your relationship status was such a good idea for Jenny to tell David. Beside the trust issue, he is young and has a daughter. He may be looking for a life partner and Jenny may have hinted to him that she is available

[aztd]

Hopeful for you

[Twikenhamfan]

I have to agree with David52 . Jenny should confess to David that she was a "Bad Girl" . Maybe David would need to spank her, his call. I love posts, please keep going.

[Bartleby]

This story is superbly written.

I think Jenny should tell David after the inevitable sex that she had told him a lie of desperation. I am sure he is able to forgive in an instant.

[realcucklife]

She was saving herself for him, or had she remembered and started your denial/replacement?

[Wannabee]

I'm loving this journey you and Jenny are on. As with most things, it's not just about the destination. Thank you so much for sharing with us.