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Teeny Weenie My Journey 5-02-2026

by ricklittle

I sincerely apologise to any followers for not completing my last journal satisfactorily and for not updating my followers on our journey. This may be a long post - my apologies.
 
F reviewed my last update and correctly observed that I skipped the detail on the conversation that occurred around the dinner table once I had informed my brother and my business partner on the lifestyle that F and I now lead. F updated their respective Wives at around the same time, although separately,  and when F and I returned to join them outside it was clear that everyone was on the same page and the dynamic around the table was somewhat different.
 
If I am totally honest with F, you and myself, it was probably for that reason that I did not discuss it in any detail here as it was very difficult and to a large extent humiliating for me. But that is neither F's or Your problem. I must own it. I've been trying to think of the best way to document everything as I remember it and I have decided to split the events up between my brother and business partner and how they reacted into separate sections. I will also add a section on how their respective Wives reacted.
 
My brother is a mans man. He is loud and boisterous and has very little filter between his brain and his mouth. He says what needs to be said whenever he feels the need to voice his opinion. As I briefly mentioned before his first reaction was of disbelief and disgust that I would willingly give my manhood up and my Wife for another man's pleasure. He told me in no uncertain terms that I don't deserve F and that She should have left me and found a real man who would respect Her and provide everything for Her. He also aired his opinion on F saying that he could not understand how She would let me get away with doing what I did and that she should have stayed with Andrew. But he also said some nasty things about F which I don't want to get into because it is very disrespectful to Her and any other Woman who chooses this lifestyle, no matter the reason. My brother did not understand because he is well endowed and he can keep his erections for prolonged periods. Quite the oversite to me. He also does not have the cuckold tendencies that I have, so he would never understand the craving to know that your Wife gets Her rocks off with another man. He told me that I needed to see a psychiatrist that it was not normal for a man to want his Wife to have sex with another man. Specifically, and bigger and better man. He then got into me about our FLR. He said that we should be equals in our relationship if nothing else. He said that Women are not superior to men and that a Wife is not superior to Her husband and perhaps he is right. But that is not the case in our relationship. I needed F back in my life and I suppose F needed me. But it had to be on Her terms because I had broken everything. I broke it due to my selfishness. He was not impressed that F now essentially owns everything that we had together. I have discussed this before. He did not understand that I have to ask permission to do anything in our house. This includes what I wear, when and where I can go out to basic toileting. Yes, I have to ask F if I may use the bathroom. This blew his mind; He called me a wimp. He had very little knowledge on chastity and could not understand how I would let my Wife lock my tiny penis in a cage and that I would have to ask her for permission to remove it. Both for hygiene and any sexual release. He then found out that I have not had penetrative sex with F since I started the Teenie Weenie hypnosis and asked about whether or not I at least masturbate, I told him that I do, but only with F's permission and mostly supervised. And when he found out that I had and do go down on Her (if She instructs me too) after She comes home from a date pushed him over the edge. So much so that he wanted to leave. His wife calmed him down.
 
My business partner is a playboy. He is a total womaniser and a total flirt. More so when his Wife is not around. He is well built, goes to the gym a lot, so he is in shape. He is good looking and is always well groomed. He found most of what I had to say quite funny. He agreed that if a Woman cannot get what She needs at home that She should be able to get it from wherever she can.  He then said that he is lucky that he is good in bed or his Wife might have left him years ago....bit of a giggle all around the table. There was a lot of discussion between all 4 of them about sexual toys for Women. He joked that you don't see many small dildos around and that the reason for that was obvious. He said that if I knew that my penis was small, I should have discussed that with F and encouraged Her to find a lover, rather than breaking what I had. He did say that it was selfish of me. He wanted to know if I had been wearing panties and bra to work specifically when we were in meetings with clients and questioned me on whether or not I had worn the chastity cage to work. I told him I had done all of those. He found that particularly amusing. He commented on who's idea it was that I was showing off that I was wearing that night. I told him that F had instructed me to wear it and the matching panties, and that She had also requested that I unbutton my shirt so that it was more visible to all at the table. He wanted to know if I was going to get those fake boobs ( I guessed he was talking about breast forms) and I told him that it would be F's decision. I got the feeling he was quite into the feminisation of his business partner.
 
The Wives were a lot more understanding and to some extent companionate. They did not understand how hypnosis had actually worked, They joked that if they knew about that working, they may have used it on some men that they knew. I got the feeling my partners Wife was indirectly referring to him. They wanted to know if I bought my underwear of if F did my shopping. I told them that F does most of it, but at times I do buy my own panties and bras. They showed particular interest in how F feels about sleeping with other men and how that has affected our relationship, They also questioned her on the emotional side of this. F was very open about the fact that She fell for Andrew, and it hurt Her to leave me and hurt Her to leave him. But She now feels that She has the best of both worlds because She now has both of us and others if She chooses. The Wives questioned F on whether She had any guilt especially if She had just spent time with a man and then came home to me. They also questioned Her on the guilt when flirting and setting up potential dates. I think that these two questions hit home the hardest. F said that She did at first, but Andrew had  "F'd" the guilt out of Her. She also said that the first time I went down on Her after she came home from a date with Andrew, She realised then that I would be ok with it. That it was not something that I had an issue with and at that moment She new I was her cuckold.
 


Comments

Response - grover27

I can see why that would have been hard to write and share. I appreciate that you did share it and I think it\'s important when sharing these types of stories to share also the humiliating and psychological parts of it, otherwise it may all just feel like perfect fantasy to some. This part of the story makes it feel more real. I hope you share more stories about not only what things are like with you and F but also how things are like for you in relation to the people who know about your dynamic. I find this all both titillating and generally interesting to read about. You can know that you have at least one active and interested reader - although I am sure you have others. \r\n\r\nI can understand the reaction of both your brother and your business partner. Obviously, your business partner is much more open minded sexually and probably has been exposed (and maybe even turned on) by some of this more fetishy stuff like chastity, femdom, cuckold, etc. I\'m curious what you think F\'s motivations were in terms of having you share this much detail with them. Do you think this was embarrassing to her in any way or was it simply empowering for her? I know F can answer for herself on that question, but I am also curious to hear what you think the answer is to that.

Response - grover27

I can see why that would have been hard to write and share. I appreciate that you did share it and I think it\'s important when sharing these types of stories to share also the humiliating and psychological parts of it, otherwise it may all just feel like perfect fantasy to some. This part of the story makes it feel more real. I hope you share more stories about not only what things are like with you and F but also how things are like for you in relation to the people who know about your dynamic. I find this all both titillating and generally interesting to read about. You can know that you have at least one active and interested reader - although I am sure you have others. \r\n\r\nI can understand the reaction of both your brother and your business partner. Obviously, your business partner is much more open minded sexually and probably has been exposed (and maybe even turned on) by some of this more fetishy stuff like chastity, femdom, cuckold, etc. I\'m curious what you think F\'s motivations were in terms of having you share this much detail with them. Do you think this was embarrassing to her in any way or was it simply empowering for her? I know F can answer for herself on that question, but I am also curious to hear what you think the answer is to that.

Response required - ricklittle

g, grover27 is waiting for a response\r\n\r\nfF

grover27 - Reply to your PM - ricklittle

Hi grover27,\r\n\r\nI have replied to your PM. Please let me know if you don\'t receive it as it seems to be sitting in the outbox.\r\n\r\nF

questions about the past - grover27

I decided to start to re-read the entire journal and I have questions for you both at where I have left off in 12/2020:\r\n\r\n1) F - In December 2020, you started feminizing g by having him wear your panties. What made you come around to that? Were you just rolling with a bad situation and trying to make the most of it? Where was your mind with all of this? Were you disappointed and devastated and resentful at that point or were you loving and just having fun?\r\n\r\n2) G - you said in Dec 2020 that for the first time you might be regretting your decision. I\'m sure you regret how you went about it but the reality is that the way you went about it was likely the only way to be where you are today. Are you happy with where you are today?

Answers about my past - ricklittle

Hi grover27\r\nI will let F answer the few first questions if She decides too.\r\n\r\nIt is true that I regretted my decision at the time. I regretted breaking my penis and how I went about it. In hindsight and after long reconciliation discussions with F, we could or would have eventually come to the same place we are now anyway if I had just been open with Her. Obviously, F would have needed to be open and honest with me too. I know that this is a generalisation, but girls don’t typically admit that their partners are inadequate in bed. They may offer tips on how they like things done and what makes them feel good, but size is very rarely discussed as a problem. Unless they have a very special relationship which is where F and I are now at. After all we have been through, F has admitted that I never really satisfied Her in Bed. As She mentioned to you, She felt that I was ok, not good, not great. Before I started my journey with the Teenie Weenie files, I was below the average size anyway, so I didn’t see any harm until it stopped getting hard. I had never been able to make F, or any of my previous girlfriends before I met F, orgasm through PIV sex alone. I perfected the art of oral and made sure that I brought them to an orgasm at least once before I entered them. And even them, I didn’t last. I have always had a hair trigger and would orgasm within minutes if not seconds. Not something that I am proud of, but now, I don’t mind being F’s little prejac as She sometimes refers to me as.\r\n\r\nSo yes, I am extremely happy with where we are now. At times I do wish that my penis still worked because I miss being able to masturbate properly, however, rubbing it like a clitoris works for me, for us, but it takes time and we are working on anal orgasms which is different for both of us.\r\n\r\ng\r\n

Feminising g – answer to grover27 - ricklittle

Hi grover,\r\n\r\nI cant remember exactly were or when that happened. It just came to me one day. I think the first time was after a night out and I wanted him to fuck me, but he couldn’t. his little penis just didn’t preform and given what I know now, I understand why. At that time, I hoped that him feeling my warmth and dampness on his penis would help. Once he put them on, he looked quite cute, quite natural and almost normal as there was nothing to show.\r\n\r\nI think I just thought that if it is that small and that useless, then it might as well be in panties, because jocks are for real men – right? \r\n\r\nYes maybe I was being vindictive, maybe I was angry. I don’t think resentment came into it, but I did feel confused. I didn’t know if it was because I didn’t turn him on anymore and why so suddenly? And why was he talking about me finding a lover? Did g want me to drive a wedge between us by cheating so that he had an excuse to leave me? All those thoughts went through my mind, and all those issues had to be worked through before we could reconcile our marriage\r\nI am sure I was upset at the time, but I didn’t know the cause. I asked him to see a doctor about his ED but he refused at first and when we did, g refused to take the medication. I know now why he did it but at that stage I didn’t and I didn’t under stand. I thought he was just being a male and didn’t want to have to take meds to get his penis to work. I thought maybe it was a male thing….\r\n\r\nThe feminising really didn’t come into play until later, but I did make him wear panties. Mine at first, then we got him his own. If his penis didn’t work…….\r\n\r\nRegards\r\nF\r\n

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