Well, it finally happened, she fucked me in the ass

Discussion in 'Chastity and orgasm denial' started by AnonJohn97, Jul 20, 2022.

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  1. AnonJohn97
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    AnonJohn97 Member

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    For those who dont know: I'm new to male chastity and have been locked up continuously since two weeks, longer than I ever have and my girlfriend is only willing to unlock me for piv sex-thing is, she hasn't been feeling like it since july 6th and she just recently told me she's been so satisfied with her sexual life in this new direction we've been taking things that she doesn't think she'll feel like piv for at least another couple weeks, which was utterly devastating for me to hear.

    Thing is, she is still really sexual, I dont think she sees the irony of the situation, just the other day she mentioned if she goes a few days without an orgasm she starts to go insane. We have sex almost every night, her favourite is me fingering her while kissing and caressing but she also likes oral and nipple play.

    Needless to say touching her privates every night only increases my frustration a hundred fold, since the beginning it's been her strict rule that I am not allowed to ask to be unlocked under any circumstances, the decision only lies with her, and I've followed that despite the difficulty. However last night I was in such discomfort I started to whimper a bit during sex, I know that sounds pathetic but I am hyper sexual and before chastity would masturbate all the time, I'm going positively insane. She noticed and commented on how it's been a really long time since I've been unlocked and she knows that must be hard for me, and that she really truly appreciated what I was doing for her, that it makes the relationship work and feel satisfying for her. She even said she's never been as attracted to me as since I've been locked up this long.

    All of this made me hopeful she'd release me and allow me to cum, but instead she told me that it "really sucks I just dont really feel like piv lately" and "I'm sorry but honestly the sex is so much better lately, I really don't expect to crave piv in a while, like a long while so maybe don't get your hopes up for a long time". She then revealed that she thought of a compromise, she apparently has a strap on from a relationship with a previous much smaller boyfriend and offered to fuck me with it mentioning prostate orgasms and that I wouldn't have to be unlocked.

    Well, normally I'd be 100% opposed to it, I've never put anything in my ass and honestly it felt/feels way too submissive to a girl/gay for me to enjoy. It also sounded painful. But I have heard of prostate orgasms before and I was absolutely desperate, so in a moment of pure need for release I agreed and she got the strap on out.

    All I can say is holy fuck that was an experience. I finally got to orgasm after such a long time, at least. It definitely messed with me a bit psychologically, as an otherwise normal straight guy taking a 5 or 6 inch dildo up the ass by your girlfriend as she slaps your ass is really confusing, especially when you climax from it.

    She's mentioned wanting to try it again and that it might make a good substitute for me cumming from piv sex. I'm not really sure how I feel about that. I do really miss piv though
     
  2. archie
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    archie Active member

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    great, great stuff. i love getting pegged, and she likes doing it, but it’s not nearly often enough. it sounds like your lady is farther along in the journey than mine. either way, i’m just happy we’re on the journey. sounds like you are too
     
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  3. Kepoke
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    Kepoke Long term member

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    So incredibly hot and so incredibly jealous lol. I've been trying to convince my Mistress to peg me for years and she keeps dangling it over me, but we still haven't done it. The thought of that role reversal and her taking charge to fuck you like that is just so exciting. I'm hoping eventually one day she'll surprise me and do it. I'm super happy for you!
     
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  4. NsToy
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    NsToy Long term member

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    you got a anal orgasm on your first try?
     
  5. King Hippo
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    King Hippo Long term member

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    It sounds like she is more attached to the chastity then she is into you. She hasn’t been honest about the whole relationship from the start… you do your thing but it sounds pretty toxic.
     
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  6. Drews
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    Drews Long term member

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    Hopefully you are having fun but it sounds like there is no communication. She seems to only get what she wants. You might like that but how far are you willing to go? Enjoy and hopefully you are enjoying the experience
     
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  7. starflyer
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    starflyer Junior Member

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    I'm sure you'll love it ....I do !
     
  8. IB-Chaste
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    IB-Chaste Long term member

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    I’m confused. The title is about it ‘finally happening’… but the story is about how you didn’t expect that to happen and you’ve never experienced etc…
    I don’t really know if this is true or whether it’s click bait??
     
  9. NowIveDoneIt
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    NowIveDoneIt Long term member

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    I am feeling more and more that this is a story. 100mph into MC, her saying and doing everything 'to a T' out of a how-to guide but instead of over a year its a month and then out of the blue pegging and you orgasming the first time?
     
  10. IB-Chaste
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    IB-Chaste Long term member

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    here you are again. Questioning the integrity of this poor man. He’s been punished with chastity with no means of escape. His supposed dreams of being locked up are turned into a nightmare… console the guy. Look after a fellow chastity bound gimp. Help him find his way. Do not ridicule his obviously real unrewarding life journey into enforced cuckholding (that’s his next chapter. Spoiler alert)
     
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  11. NowIveDoneIt
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    NowIveDoneIt Long term member

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    To quote Andy from American President- "That's sass, you're sassing me aren't you"...
     
  12. IB-Chaste
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    IB-Chaste Long term member

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    oh know. I’m concerned you’re not taking this guy seriously. He’s finally found the mythical unicorn of our dreams. A supportive community like us should be supportive and reassure it will be ok. He’ll cum again one day. Not kick him when he’s down. Struggling with the integral cogs that make a man’s mind tick. Dying inside from his need for release.
    This guy. He’s the guy. He’s the chosen on. he’s the reason they made the saying “careful what you wish for”. Living our dream. Craving some support through it.
    Help him. Help him before it’s too late
     
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  13. NsToy
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    NsToy Long term member

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    We’ve seen this on the site before so he is No chosen one. I personally agree it is dubious.
     
  14. NowIveDoneIt
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    I believe IB's statements are in jest...
     
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  15. NsToy
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    NsToy Long term member

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    Woosh
     
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  16. JaySaysYes
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    JaySaysYes Level-4 Sarcasm Master, PhD in Google, Ace Pedant.

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    After this epic adventure did you smell any shit, more specifically bullshit?

    I ask because it sure smells like bullshit to me.
     
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  17. Andy88
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    Andy88 Long term member

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    (Readjusting my specs)… holy george..ok, she fucked your ass.. did she make you suck it clean for its next use?
     
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  18. borbulls1961
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    borbulls1961 Madame Vanilla's property

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    Nah she hooked up a hose from his arse to his throat...to stop him vomiting all this bullshit.
     
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  19. King Hippo
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    King Hippo Long term member

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    And just like that…. The online fantasy was over quicker then the time it took to write it down…
     
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  20. NowIveDoneIt
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    NowIveDoneIt Long term member

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    Those types of buys tend to cum quickly....
     
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  21. SubSnuggler
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    SubSnuggler Owned by Mistress2and4you

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    It was a cool story. I liked it.
     
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  22. IB-Chaste
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    IB-Chaste Long term member

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    It was much sexier than real life stories of 60 days locked, not sure if my KH remembers me…
     
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  23. IB-Chaste
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    IB-Chaste Long term member

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    Ok so I made it more true to real life.


    Well it finally happened… she hates me


    For those who dont know: I'm new to male chastity and have been locked up continuously since two weeks, longer than I ever have and my girlfriend is only willing to unlock me for piv sex-thing is, she hasn't been feeling like it since july 6th and she just recently told me she hasnt been satisfied with her sexual life in this general for a while now and she doesnt think she'll feel like piv again.

    Thing is, she is still really sexual, I dont think she sees the irony of the situation, just the other day she mentioned if she goes a few days without an orgasm she starts to go insane. We have sex almost every night, her favourite is me fingering her while kissing and caressing but she also likes oral and nipple play. At least that’s how I thought she was feeling… what she’d later tell me was devastating.

    Needless to say trying to touch her privates every night only increases my frustration a hundred fold, since the beginning it's been her strict rule that I am not allowed to ask to be unlocked under any circumstances, the decision only lies with her, and I've followed that despite the difficulty. However last night I was in such discomfort I started to cry over the situation, I know that sounds pathetic but I am hyper sexual and before chastity would masturbate all the time, I'm going positively insane. She noticed and commented on how it's been a really long time since I've been unlocked and she knows that must be hard for me but it’s exactly what she wants. I’d locked myself and when I showed her she’d laughed… with relief i now come to realise. She even said she's never been as attracted to me.

    In some warped version in my own head all of this made me hopeful she'd release me and allow me to cum, but instead she told me that it "really sucks I just dont really feel like piv lately but the menopause has changed my body" and "I'm sorry but honestly not having sex is so much better lately, I really don't expect to crave piv in a while, like a long while so maybe don't get your hopes up for a long time, honestly I’m so dry down there now that when you’re inside it feels like your penis is coated with acid dipped razor blades". She then revealed that she thought of a compromise. “If you stop saying pee-eye-vee, honestly you sound like a loser, you’ve said it so much even I’m saying it now, you can use this” she apparently has a strap on from a relationship with a previous much satisfying lover and offered the dildo to me mentioning prostate orgasms and that I wouldn't have to be unlocked.

    Well, normally I'd be 100% opposed to it, I've never put anything in my ass and honestly it felt/feels way too submissive to a girl/gay for me to enjoy. It also sounded painful. But I have heard of prostate orgasms before and I was absolutely desperate, so in a moment of pure need for release I laughed this off as a complete joke.

    Later when she was asleep… All I can say is holy fuck that was an experience. I finally got to try and orgasm after such a long time, at least. It definitely messed with me a bit psychologically, as an otherwise normal straight guy taking a 5 or 6 inch dildo up the ass by your own hand would as she sleeps. The lack of anal training, proper lubricant or any sort of understanding of what to do. Fuck that hurt.

    She's might not want to try it again and that it might make a good substitute for me cumming from piv sex. But as she slept, I placed the end of the dildo in her hand and fantasised that she was thrusting it inside me. I whimpered for the first time through sex. My tiny ass hole was in agony.

    And that’s how it’s happened. She finally fucked me in the ass…
     
  24. Mimi
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    Mimi Long term member

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    Click bait fantasy
     
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