Ruined Orgasm

What is a ruined orgasm?
How do I ruin my orgasm?
Why should I ruin my orgasm?
Why not just deny myself instead?
How is a ruined orgasm different from a milking?
Can I ruin my orgasm multiple times?

What is a ruined orgasm?

It is an orgasm that does not feel fully satisfying, it is still an orgasm and there is some ejaculation but it does not give that stronger orgasmic spasm and often gives a sense of leaving you wanting for more. A ruined orgasm also tends to not reduce your sexual appetite that much and therefore can be very frustrating if that is ALL you get

How do I ruin my orgasm?

When you get to the “point of no return” you ejaculate and you get a normal orgasm. However just before that if you stop and do not hold your cock, then it just slowly leaks out a bit. So just when you feel it is coming… just let go and do nothing. Stop all stroking and just let it leak out. Most can do this without any training, and it is quite easy to do on someone tied up that you play with. Since they do not really have a choice in the matter.

Why should I ruin my orgasm?

You get horny in no time, it does not ruin your sexual mood, it is a good way to show you truly submit to someone, and you can ruin quite a few times a day but it is often hard to cum hard that much! It means more sex and keeping yourself sexually ready for longer, and having your brain crave release even more!

Why not just deny myself instead?

Because if you keep denying yourself for too long, especially if you are not even touching, then your cum production and sexual appetite “Your libido” goes down. We do NOT want this, do we?

How is a ruined orgasm different from a milking

A ruined orgasm comes from stimulation on the head, which is taken away “to early”. However, milking is when you keep pushing the prostate over and over causing an involuntary orgasm. I mean involuntary in the way that there is nothing the person can do about it. If you are not the mood I doubt you can really milk someone or have them cum that successfully. Sissies in their earlier stages are a bit different than girls here. Girls can definitely have forced orgasms, and to an extent, sissies can too but it is by stimulating these erotic points at least. Milking a sissy or man stimulates a point that does not need to give them pleasure. However, done in certain ways they can get some pleasure anally. A good dominant at milking should be able to milk without any pleasure. When milking results in ejaculation there is not real orgasm other than the spasm and it comes with no release from frustration at all, even if the milking felt good it is as if cum comes leaking out and the person is still just as horny. This is really an evil thing to do. One can also milk someone with an electric device, that triggers a forces ejaculation spasm. This, however, is painful, does not feel good in the slightest and is way more hardcore. Of course, that just makes it that much more fun to do. Any sissy that things a chastity device plus forced electric milkings sounds like a hot idea tend to soon be very willing to do anything for you. Even the most rebellious ones. This is truly evil and yet sooo much fun!

Can I ruin my orgasm multiple times?

As long as you can stimulate yourself to the point of orgasm then you can any number of ruined orgasms. However even though a ruined orgasm leave you hanging, it still seems to lower the sissy’s libido a little bit each time and also increases the sensitivity of their little clit. Sissies are different in what they can handle, and how fast they are back up to maximum horniness. I am also quite sure that the training and experience of having ruined orgasm makes it easier to do it more often, and it also seems that there are differences in how it is ruined or who is doing it. A sissy being ruined in the setting of a mistress tends to be able to tolerate many more ruins than they could with their girlfriend at home for example. This can be confusing when teaching the girlfriend or boyfriend of a sissy. The mental part clearly seems to be important for all forms of sex xD

68 thoughts on “Ruined Orgasm

    • sissy courtney says:

      I agree totally with the a author’s statement
      “One can also milk someone with an electric device, that triggers a forces ejaculation spasm. This, however, is painful, does not feel good in the slightest and is way more hardcore. Of course, that just makes it that much more fun to do. Any sissy that things a chastity device plus forced electric milkings sounds like a hot idea tend to soon be very willing to do anything for you. Even the most rebellious ones. This is truly evil and yet sooo much fun!”
      When that probe is inside my sissy pussy, sometimes combined with electrodes on my swollem full ovaries form chastity or even worse a probe inserted in my pee hole as the current begins to flow, especially when the pulses are random and so intense as the electrical force is increase my pussy, ovaries, shaft, and whole body will shake with what feels like intense plain, but the forced contractions continue to build and milk me painfully and helplessly I have been made to ejaculate, being milked of my sperm but getting no pleasure, having my sperm extracted but not getting a real orgasm all while begging Mistress to make it stop confessing to or becoming willing to do anything for her as the current was flowing.

      • Tiffany says:

        Oh my fucking god, I think your narrative just proved i am one of those sissies who finds forced electrical induced milkings to be hot!! I can cum without touching anything, with just my imagination, porn and or poppers. It also doesnt require all three, and i dont orgasm, lose libido or even feel left wanting, Im extremely pleased with what has happened, but my libido definitely stays, and being such a bottom slut who lives to be fucked, keeps me going strong.

        • sissy courtney says:

          I completely understand your feelings . When Mistress forced milks me, especially with the probe. After the screaming begging and spasms stop. And of course after I clean up my mess. By that I mean eat my cum as she watches and laughs, my balls feel relieved if the pressure of stored cum but I am left feeling frustrated, unsatisfied and still horny as I go back into chastity. It is a frustrating and very emasculating experience being milked that way but she loves it. But saves it as a punishment if I have been a bad girl. Thank God it doesn’t happen too often as the current flows it is so intense.

    • Michael says:

      I’m totally addicted to watching beautiful dick and ready to put one in my mouth. I know I can please and obey. I love the taste of cum along with the small feel and texture

        • Diane H says:

          There is nothing quite like an anally penetrative milking, I am entirely left on the precipice of orgasmic fulfillment, in a constant low level condition of feminine horniness, It’s what makes a sissy sexually compliant….

      • Stephanie says:

        Do you swallow your own cum?

        I love lick it from the source…. As the first drop dripping from my clitty to my mouth….
        I fuck myself while my clitty is locked up… And then it enters my mouth….
        Warm, tasty…. Sometimes I am not able to stop fuck my pussy…
        And I do a few times a day… Like today.
        I fucked myself already 3 times today….

        I am visiting a friend right now… But I am still plugged and caged….
        How it should be….

  1. Jasmineslut says:

    I use to do this all the time when I was in my twenties. I forgot all about it. I’m going to start doing this again! I’m staying in a hotel next week and this technique will keep me in the game longer so I can please more men!

    • Pam says:

      Anally probed as prostate is rubbed brings on the deepest longest orgasms for me especially when I am in chastity for a long while.

  2. Marcia says:

    Hi, This sounds a lot like “Edging” Stroking to the “Edge” of orgasm… I have been doing this for more than a decade, I love to taste the pre-cum… I can reach with my tongue. I have gone over 12 hours many times, I use a variety of things to stay horny for long periods, like responding to this posting and browsing the web store for sissies. I also use a small assortment of toys and lingerie. I am extremely restricted of privacy here, but it is what it is. I had offers from a few people I liked but without privacy I would be punished a LOT… Lol Enjoy your ruined O’s, i know I do… Try sounding if you dare, just read up and be CLEAN and SAFE… It’s a tiny painful for me cuz I am tight as a MoFo, my ass is too…lol
    Luv your site(s) M

    • Moxie says:

      I relate to this. Self care is so important these days. Doing what you need to do to feel good is something we should all strive for. Like, the right person/people will come along eventually, but in the meantime we get ourselves ready.

  3. Michelle says:

    I love this. I had a session with a bbc shemale friend. She kept me locked in chastity while she repeatedly deep throated me and drained herself in my ass. I was dripping cum from my clit and dripping hr cum from my ass. During the entire time her friend worked my helpless caged cock over with a hitachi vibrator. I think I had 20+ ruined Os. As our 2 day olympic session came to an end, she took me out of chastity and fucked me one last time as her friend licked, sucked and played me to orgasm. Only then did she allow me to clean all the dried on cum off my face, thighs, stomach and chest and fix my makeup. She locked me back up, plugged me and sent me home until.the following weeker end. She told me to expect more of the same next weekend, but with three more of her bbc shemale friends. Im dripping already.

    • Kinkybrenda says:

      That is a very hot story. I would love to hear more about it or about that next weekend with her friends and you. My two most flavorite things are dressing up for a BBC shemales. I have no one to share my feelings with much less to french a BBCwith. I hope to find a friend I can exchange common interests with. Please tell me more, love hearing it.

    • Kandi says:

      I love all the stories but mine is a little different. I go to the doctor for male hormone but someone has replaced male hormone with estrogen. So unbenounced to me the shots im given for over a year by a reputable doctor make me feel so light headed soft spoken and so feminine acting and feeling. Men are suddenly so handsome to me n I can’t stop looking at there chest there bulge and there butts. I meet a man about six foot two very strong muscles tan and a big bulge. We start to hit it off and one day he hurts his shoulder in tennis and asks me if I can rub it out nn i gush and get the butterf lies just thinking bout it. He tells me to come by his house that he is showering when I get there he’s in a towel and lays down on the bed tells me there’s some hot oil there to rub his shoulder I massage his shoulders and he asks me to do it in front as he turns around I start to massage his chest and start blushing and am a little embarrassed he tells me that he knows I’m blushing then puts his had to my chheek parts my hair leans in and starts kissing me passionately I am feeling so horney and as he kisses me he takes my hand and movrs it to his bulge I unzzip his jeans and there’s about 12 inches of cock I ❤️ wat i see he pulls my head onto his very large cock and I start sucking its my first time and it is so delicios and as i suck and kiss him down there he strokes my ass and it feels so good he pulls my sweats down and keeps stroking my bottom but im in cuts panties and fake vagina he then take my top off and im wearing fake breasts bra and halter top his cock is fully errect all 12 1urn me into a feminine girl. I can’t sto

      • Kandi says:

        I want to finish this story so he is fully erect 12.5 inches and pulls me onto his cock I want him so bad by now he starts kissing me again passionately and I feel his large member part my wet lips he puts it in a little and I moan like a girl and then while I have my legs wrapped around his waste arms around his shoulders I give into him fully trusting him now and I relax then I feel all of him slide deep inside me oh God I tell him you feel amaxing as I’m sitting on his lap withvhim deep inside me he pulls me so close I feel his throbbing cock with its almost 2 inch girth he then moves In n out of my tight pussy strong hard and firmly in in out slow hardvand deep I screem in jou just like a girl god this is eat I want so bad all the time i want him to desire me so after sex i call a plastic sergen and get butt implants he loved them and then i secretly get my breast done for him a large c-cup i am so inlove then he puts a ring on my finger n we get married the end

  4. Jane rose says:

    My new favorite way to orgasm is the ruined orgasm ! Insight on this is great 🙂 I think it keeps my energy level more enthusiastic especially for those who enjoy penetration

  5. SissyAmmie says:

    I’ve had a long standing humiliating fantasy about one of submissive girls that loves recording herself being used as a sex toy for my pleasure while she watches the previous movie of her kinky sexual fantasies being fulfilled. Accidentally finding my sissy and forced feminization porn videos I have stored on my phone, ” she would love to see me used and humiliated for her pleasure for once ” then convinces me to let her see me in some of my hidden panties tied to the bed and immediately tells me she’s going to shave, shrink with ice packs, and use the smallest homemade chastity device she can all on video. Telling me that I must choose between her posting and showing everyone that I am a sissy, or I must beg her to make me into her sissy sex slave the whole time she records my chastity humiliation. Once my now useless tiny sissy clit is trapped with me begging her to do this to me she makes me ask her to take me to a sex shop dressed like a sissy schoolgirl and lock the smallest cage possible on me in front of everyone and thank her as she destroys the lock willingly becoming her sissy for life. Or she will castrate me and start training me to be her forced feminized sissy prostitute living permanently restrained, publicly humiliated online/in front of groups of her friends and strangers, and filming porn videos to sell of me getting trained to do anything a real man or woman wants of me. She tells me that she knows a few black gang members who would love to train me as their little white sissy with their huge black cocks and leave me bound at drug houses to be used by all their customers until they get a permanent location to start being pimped out. I have imagined my life in both scenarios, and she has almost found out my secret fantasies a few times when watching her videos or showed up unexpectedly and I had sissy porn playing wearing only panties… hope you enjoyed my fantasy as much as I do!

  6. friskysissy says:

    Since i was accepted at Sissification Academy (only two days ago! seems like a week) i have been so aroused…..watching sissy trainers and getting close, but not letting myself cum. cage on order.
    Oh my!
    What a glorious day to be a sissy

    • Christian says:

      I want to see you get aroused and denied the chance to cum, to build up your girlyBOY cum store’s then I will take you to the edge of ecstasy and let you cum cum cum everywhere and all over us to be treated like a cum dumpster…

  7. sissyCindy says:

    i am so excited and will start to work on ruined orgasms as a daily sissy task. as a young ‘man’ i experienced a ruined orgasm once and remember how incredibly horny i was immediately after.
    dreaming of cruel feminization and chastity, ending up as a siss gloryhole slut

  8. SissyKim says:

    I’ve been doing this for years. I love how I’m still horny afterwards and able to go again right away. I was wondering, if I do this multiple times a day, will my clitty shrink from the loss of testosterone? I certainly hope that it will. I’d love my clitty to shrink. It’s only 5 inches when hard now, but I’d love it to shrink to a third of its size, both hard and soft.

    • Polly says:

      Awww sister mee too, I wear a cock ring 24/7 amongst other things in the hope to shrink my dink, I dream of a micro clit, anyone who reads this may like to focus their attention on my quest for a shinky dink, I believe your well wishes in this regard will certainly help me become truly smaller than the average fun size weekend warrior,
      thanks in advance well wishers

  9. Krista Bograeus says:

    A perfect way to control your sexuality. You will never have a true orgasm and the feeling of deep humiliation is breaking your masculinity dowm. Thank you soo much for your goog advices.

  10. Salvatore says:


    I have been into being a sissy and sissification for about 20 years. First, I was brought up only by women, and im very into fashion.

    Second, I am what is now being called Mostly Straight.

    Third, I very much enjoy Domme/sub being the sub.

    My true desire and starting to wear women’s clothes started when I was married. It was very secret. Even my ex wife didn’t know. Yes I wore womens shoes and clothes that just fit better and were more stylish. But wearing women’s underwear, dresses, heels, bras, lingerie, etc. started for a different reason.

    My marriage was not going well. My ex wife just didn’t love me, and it was very obvious. She started having less and less sex with me, to the point it was once a month, or less frequently.

    So…i turned to self love and self sex. I didn’t get out of my marriage because we had 4 children. When my wife was away with our kids, I started to wear her clothes and shoes. She never wore the sexy clothes I bought her at say Victoria’s Secret, so I did. I never cheated on her with a woman or a man.

    After my divorce (she initiated the divorce) I was single living alone. So I was finally free to dress at home however I wanted to. This went on for 10 years. And after my divorce I simply told the truth to women I dated.

    SURPRISINGLY, virtually All thr women were totally ok with it, and even embraced it, and loved that i was so honest. I also told them I had sex with a few men over a 30 year period. Again, they were cool with it, and were actually very turned on by it.

    The best part was we started dressing together as “sisters” and “girlfriends”. It was amazing and so liberating.

    I now have an extensive wardrobe of womens clothes, sometimes wear womens underwear and bras under my clothes, dress as a woman at home often.

    I finally started telling more people, and they were cool with it too. Finally I went out dressed totally as a woman in an openly LGBTQ area in Sacramento, California. I felt SO FREE !!!! It was like my sexuality and who I really am was not only ok, but completely liberating.

    All my girlfriends the past few years are also into Domme/sub and light BDSM. We incorporated Sissy talk, sissification, etc. Into our relationship. It was wonderful for BOTH of us. The woman got to be powerful, express their lesbian desires, and overall it IMPROVED our relationship greatly, and the Power Exchange really turned the women on.

    Its now so much FUN, being a girl and even just talking about “girl things.” And now we sometimes go out together either dressed totally as women, or my girlfriend knows im wearing women’s clothing under my regular clothes which are also often metrosexual clothing.

    Finally, unfortunately I have beem sexually DISCRIMINATED against, called names in public, etc. What they quickly find out is that I am also a “tough guy/girl ” when I need to be.

    I strongly encourage other men to act out their sissy desires. It’s overall WONDERFUL !!!

    • Lexy Jolie says:

      OMG, your text really stroke me. My wife recently (around 2 months) left me also (apparently she lost interest in me), and now I´m fully embracing my sissy side. We have kids too, and they spent most time with me, but when they´re out with her, I can have a few hours of sissy time.
      The fact you found girls that are into sissies gave me some hope one day can find someone I can share my lifestyle and have some fun with it.

  11. Sissy Malvika says:

    I have a question, how often is ruined orgasm recommended? Like daily, weekly etc.
    Any specific guidelines to follow to cum more or less?

    • Sissy Jamie says:

      Good sissies should always ruin their orgasms to maintain a high level of arousal. This will make it easier for them to focus on pleasuring others and to always swallow their ejaculate like a good little cum slut.

      • Chloe says:

        It’s really true, isn’t it? I’ve been edging and watching sissy interracial hypno for days now and I just stay obsessed with sex and my little pp stays swollen. I feel like this method just makes me want to submit to someone completely for the express purpose of being lewd. It’s becoming so overwhelming to me!

      • Tamarabj4 says:

        I couldn’t agree more, while I yearn for anal penetration, seems the only real way for this sissy to orgasm.

  12. Jennifer says:

    My exwife simply would stroke my small hard clit, with me full of Viagra, and edge me, then finally as I was about to cum hard, she would laugh, let go and walk away. Often she was squatting over my face, and I was ordered to lick her ass, instead of cumming, so as soon I as began to orgasm, I was instead lap her ass. It hurt a bit as the cum flow stopped suddenly and dribbled out. Her boyfriends got to cum deep inside her, and i was usually locked in chastity, living as a woman. So a ruined orgasm was better than nothing.

    • tailfreak says:

      The best sexual relationship I’ve had so far was with my ex fiance and it was basically exactly this. I always had distant sissy fantasies in private but it was my desire to worship ass and her willingness to humiliate me that made me crave being a sissy/cuckold almost as much as I crave a dominant ass to serve.

  13. roundhand says:

    The great thing about ruined orgasms is the appetite to eat cum does not diminish. Collect the sperm as it oozes out and pour it into mouth, getting more accustomed to the taste and texture. Hungry for more!
    Thank you for the opportunity to learn in the sissy academy!

  14. Weinny says:

    it’s fun and delicious to ruin the orgasm. to be able to taste your semen and be very hot in the attempt how much I would like to have a man who gives me his milk all the time

  15. jasmine jules says:

    Hello all,
    Ruined orgasms are not only a part of my daily life now, but they also serve to please and amuse my Dom-Wife. With just a few minutes of her teasing of my sissy titties, i spill my jism into my panties. This not only humiliates me, but it also demonstrates her mastery over my body – her property. Even though i am restrained in my chastity cage daily, i still “bloop,” as we call it – on demand; HER Demand.

  16. Isabel says:

    I tried many times the ruined orgasms the way indicated here. It works a bit, but unfortunately I still have some pleasure when the sperm flow, and after that, nearly all my desire stops. In other words, orgasm is nearly not ruined and I cannot go on a second time. Do you have any trick to overcome this problem ?

  17. Stephanie says:

    I am Sissy and live as a girl all day long…. I also work as woman since tis month (1 February 2021)

    I have to be honest…. I love my chastity cage and it will get smaller and samller. Since a few months I wear this one

    I have my problems with cumming in it…. I can not control myself…. I watch my favourite Sissy Porns and on sometime I start playing with my cage… I can not get hard and I also do not want that. But there is a point where I am not able to controle myself and cum in the cage….
    I know….I should not be allowed to but I have no friend or mistress. Nobody which can control it for me. Which can train me and make with me only ruined orgasmn.
    I would love to achieve this level.

    Also I am not sure how long I should where my cage. The whole week is not possible because of work.
    I wear onces a month the whole weekend and as long I am in my chastity, I also plugged.
    If I start leaking….. of course I eat it but it is not that much I want.
    I want to swallow a whole load…. and playing with it while he is watching me.

    Have anybody have a suggestions how I can go the next step? Can anybody help me be a better Bitch? Be a better slut?

    • Ashley says:

      Try to wear fake breasts , if possible . the female satin panties or bras will make you more feminine and trust you will feel amzing . For anything else you can contact me at [email protected] . I be more than happy to solve any issue you got.

  18. jessica says:

    i try to ruin all my orgaisam to keep me in the sissy mind set and be a good girl but did not know why it was becoming so sensitive and not going to lie rubbing ruin and cumming in panties is the best felling

  19. Trish says:

    I just started ruining my orgasms and I love it. I produce a lot more cum and more for me to eat. I can’t wait until I can eat a real man’s cum and getting fucked like a true sissy.

  20. Bobbi says:

    Great article. I just started to ruin my orgasms about 2 weeks ago. I did it so I would taste my precum and ruined ejaculate. I started to enjoy it. I stay so horny and can do it 3 times in a day. Its driving me crazy but fun. I think I am ready for chasity now. I’m feeling very feminine and my nipples are getting sensitive. Thank you!

  21. Roxy says:

    Good day. I am a newbie and I have a question. and if you can just milk whether you still need to get a ruined orgasm. Or if milking, you can completely abandon the usual method and strive only for sissygasm?

  22. stephaniecurl says:

    Thusfar i have only read a few of the wonderful sissygasm excerpts but they are sooo erotic and wonderful i am breathless reading only a few!!! thank You so much for such a wonderful venue. kisses stephaniecurl

  23. Chrissy says:

    I have actually been doing the ruined orgasm for awhile. I’ve actually been stopping sooner and pushing like I’m peeing and I get I really nice puddle out for me to eat:) so yummy ? I’d love to try being milked though. It sounds really hot:)

  24. Gabbi says:

    I experienced my first ruined rgasm today after reading this article. It has changed my life!! Still horny and no shame. Thank you so much from a grateful little sissy xoxo

  25. Daisy says:

    OMG … I have just started to ruin my orgasms. What have I been missing.
    I’ve done it on two occasions and both times ruined my O four times.
    Each time a shot of cum fell into my hand, I eagerly licked it up. Not that I need encouragement as I luv cum, but a great way to learn to eat cum for sure.
    When I finally did orgasm, there was no cum … a sissigasm ???

  26. Lili says:

    Thank you. All of your stories are so very delicious! I hope to be sissy and slave for women. I am waiting for get training.

  27. Desire says:

    I have multiple sissygasms when I have anal sex or deep throating bigger cocks. Would that be considered ruined orgasms? Don’t cum a lot, but with each O I get hornier. Have been training myself to have my small clit act and respond like a true clit and experience Os like a woman. My clit doesn’t get hard anymore and I can have multiple sissygasms that grow in intensity and make me hornier with each O. Would that be considered a ruined orgasm?

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