PoliteCouple

Was this a small step or a big leap?

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Ok, so I had kind of given up all hopes of ever being cuckolded by my lovely and beautiful wife. She is a blonde, cute and shy girl for first impressions I guess, but she is first and foremost intelligent, funny and basicly my queen. She has known about my fantasies for about 10 years now (we are both 36). She was never appalled by my fantasies, but always laughed about it, and in more serious conversations she said she was not build for it (explaining to me that she was a romantic, and more traditional when it comes to sex, also that if she would fuck someone else, that would mean that she had feelings for him). I never pushed her about this, and respected her feelings. Pushing your girlfriend into cuckolding is for me the opposite of what I want from the cuckolding. I want her to be the boss of me sexually, not the other way around. So, how have I spent the last 10 years? I kept jerking off to cuckold porn, always looking for amateur videos where I could imagine my wife being the girl. We have sex only about once a month, probably due to me not being man enough to seduce her, and instead I jerk off to porn. We have had periods where she plays along with my fantasies and doesnt allow me to cum. In those weeks (3 months is the record), she gets a lot of orgasms by me eating her pussy. But not much talk about cuckolding.

But last night, I felt some progress! Not sure how much, and I would love your view on this. I had saved myself from cumming for some days (making me feel more submissive), and started caressing her while we were watching Love Island. She looked at me, and told me sternly (she going into the role of my superior) that she was not in the mood for getting her pussy eaten, since she had 3 glasses of wine and it would take to much time to get her to orgasm. She told me I could penetrate her. We hit silence for a moment, before I asked her if we could use the cock sleeve (hollow dildo) on my penis. She always rejected this suggestion every time I tried, but this time she said yes. I fucked her carefull with it (its 21 cm, and VERY thick, picture attatched), and the view wwas amazing. Her innocent pussy wrapped so much tighter around it than around my fairly thin penis, and I told her it looked fantastic. She laughed, and for the first time she had an orgasm from penetrative sex with me (...ok from the cock sleeve then.). Her face looked fantastic, and her legs wrangled to boh sides like never before. I was careful, but after a while she took it all, and pretty hard to. She told me afterwards that she was surprised that she could take it all, and that it was very good. She also laughed when whe saw that I had cum inside the very thick sleeve. (I was dissapointed with myself, as I promised her not to cum). Dont know how I managed that, since its no way you can feel pussy from inside one of those things.

Afterwards, we talked a bit about cuckolding, since she had "just fucked a much bigger man" (my words, but she gladly agreed). She wasnt that reluctant, but I didnt want to persue her with direct questions about her cuckolding me soon. She sighed about "all the drama" with inviting another man, but I reassured her I would not be all weird, and it would be a "normal threesome". She didnt reject it! But I chose to not ask more direct questions. I really felt as if she was more on board than ever, and I am not sure how to go from here.

Anyway, sorry for the long story, but for me this felt like BIG steps, even though it might not seem like it was. What is your opinon? What should I do now?

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It was a good first step!  Not huge but not small either.  See if the wine was the trick or your cock sleeve & ask if she is now more open to a "bigger" dick.  I would continually remind her of the fantastic orgasm she felt & that you can't seem to do that for her by fucking with your penis, but you really want her to experience bigger orgasms.  Maybe see if she'd try a huge dildo while you masturbate next to her.

Meanwhile, start scouting for a friend who you think would be attractive to her & start that conversation with him.

Keep trying buddy...you'll get there.

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My honest opinion is it was a HUGE first step but must be followed with baby steps.  I think you may have opened up the possibility to her never realizing the pleasures of a larger guy and to agree to a threesome when it was never an option before is majorly huge.   Just be careful and don’t just make it about sex or you could lose her, keep it intimate between you two, by not just sex but by talking honestly and openly.  let it progress slowly and it will be much more rewarding 

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I can suggest you could see now together a cuckolding video, better if while you are drinking some good glasses of wine to loosen her inhibitions

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First, it is a bid leap. She is beginning to take over her own pleasure. You on the other hand are begging to become a tool for her pleasure. Don’t be surprise I’d she starts testing the limits of your own fantasies to see if you can take it. You also need to share more pictures of that future MILF/HOT WIFE

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