I’m still at the very beginning of this whole lifestyle…it’s been more in my fantasies than anything else. My very vanilla wife is also very well endowed and over the years has demonstrated occasional glimpses into a highly sexual nature. Being so pitifully endowed as I am I have naturally been drawn toward the cuckold lifestyle and nothing would be more fulfilling than giving her the gift of the kind of attention she deserves. Well after a long time of discussing it here and there (she’s very embarrassed to talk about sex) I finally asked her last night to tell me I have a small penis while she was giving me a hand job. I’ve asked her once before and she didn’t want to because she didn’t want to make me feel bad. But last night I urged her that it would be a tremendous turn on for me and I really needed it. So she reluctantly said “I love your small penis” while she was stroking me…it was like an electric shock went from my brain right down to my cock! I asked her to say it again. “I love your small penis” she said quietly. Again, it was like a jolt of sexual electricity throughout my body! After a few more moments I said “Say ‘You have a small penis.’” And she did. “You have a small penis.” She was very quiet about it, I knew she felt bad about it, but I couldn’t believe the effect it was having on me! This was the first real world step toward cuckolding I’d been able to make happen, and it surpassed my wildest dreams!!! I asked her to say it several more times, and I came harder than I have in a long time, not just my little dick but my whole body and mind!
First major (for me) cuck step achieved!
- Thread starter jared7577768
- Start date
Has she had larger penises before? If yes ask her how better it felt a larger penis than yours inside her.
She’s only really had sex with mine, and the other three were over 30 years ago when she was in college, and then only briefly. The only thing she remembers about them is that they were “really long” which the more I thought about it makes sense she’d remember them like that, because she’s only been used to three inches since 1989.
The only thing she remembers or the only thing she's willing to share with you so she doesn't make you deal bad? Maybe now she can see you get off on the humiliation she'll have more to share - probably best not to push it though.
Agreed. I haven’t mentioned it since it happened…I’m giving her room to process it, as I’m pretty sure she doesn’t quite understand what it was all about. I would love for her to ask me questions, but she rarely does when it comes to sex. So I’ll continue to take baby steps and bide my time for the right moments.
Have you ever thought about surprising her with a penis sleeve extension that adds length and girth?
I’ve used them in the past, but unfortunately I am too small for them to work properly. The interior of most of them assumes a minimum length of around 4-5 inches. I’m only 3, plus the fat pad around my cock makes it so that in certain positions my cock retracts an inch or two even when hard. So I end up having an empty space between the end of my cock and the firm part of the extension, so it just flops over, and eventually I slip out of it. Even the ones that anchor to your balls don’t work because of the flopping, lol! The problems of the truly tiny…
Some of them you can trim back for a better fit.
I’ve tried that too. I think they need a minimum amount of surface area to grip onto in order to prevent slippage. I’m definitely below that. I once ordered a blowjob machine; they came in Large and Small size. I got the small, and the internal mechanism that simulated the thrusting of the mouth barely reached my head, let alone the rest of me. That was a major reality check.
what about the next time she did you by hand? did she just ignore it or talk about the previous time?
So the next time I didn’t push her and she didn’t say anything. I was bummed. Then the time after that I asked for it again and she did, and it was awesome. Then the most recent time I didn’t ask and she didn’t say anything. So I guess I need to keep asking. I’ve been creating an environment wherein we’ve been able to openly talk about my size in realistic, but non-negative ways and she seems to be getting more comfortable with that. So one goal is to hopefully get for the point where she talks about my size during play without my prompting. The last time she did I told her it was like “verbal viagra” and she thought that was hilarious!
JetDriver
Male
UPDATE:
Since my last post we have had two more times when she has been willing to tell me how small I am…I needed to prompt her but that’s fine.
The first of these most recent was about a month ago and she was getting more comfortable telling me I have a “small penis” while stroking me, and even being a little amused and chuckling.
Last night was awesome…I took a chance and asked her if she would call it a “little dick” (not language she usually uses) and she had no trouble with that and actually got into it! And I asked her questions while she was stroking me: Me: “How small is it?”
Her: “Really small.”
Me: “Have you always thought it was small?”
Her: “Yeah.”
This is a whole new level of intimacy for us and I can’t express how intensely erotic and exciting it is for me! I came so hard it actually shot past my head! I’m so happy that she is getting more and more comfortable with this, and I’m pretty sure it won’t be long before she does it without my asking!
Since my last post we have had two more times when she has been willing to tell me how small I am…I needed to prompt her but that’s fine.
The first of these most recent was about a month ago and she was getting more comfortable telling me I have a “small penis” while stroking me, and even being a little amused and chuckling.
Last night was awesome…I took a chance and asked her if she would call it a “little dick” (not language she usually uses) and she had no trouble with that and actually got into it! And I asked her questions while she was stroking me: Me: “How small is it?”
Her: “Really small.”
Me: “Have you always thought it was small?”
Her: “Yeah.”
This is a whole new level of intimacy for us and I can’t express how intensely erotic and exciting it is for me! I came so hard it actually shot past my head! I’m so happy that she is getting more and more comfortable with this, and I’m pretty sure it won’t be long before she does it without my asking!
JetDriver
Male
it is ok for the male to wear a strapon cock and fuck her with a larger cock.
Not really…at least no positive updates. Took a few steps back and then everything stopped. And now daughter is home for the summer so nothings gonna happen for a while. 🙁
Woodstock14
Male
Good luck….have been following your posts and wishing you luck!
Thank you so much! I’m hoping to have some serious conversations with her soon.
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