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MILKING SISSY

12 December 2025 by Lady Alexa 15 Comments

As regular readers of my blog know, I don’t allow my sissy husband to orgasm. I have many reasons for this, amongst them, the problem that once sissies orgasm, they lose a lot of submission for a day or so and that’s unacceptable.

Another reason is that I don’t like the mess or smell they make when they cum. But there are even more good reasons not to allow a sissy to orgasm. A dominant woman in an FLR should have the focus on her pleasure, not the sissy’s. So it’s best to remove any chance of the sissy getting pleasure so they can concentrate on their Mistress without any distration. And of course, it’s so much fun to tease them mercilessly. I don’t know why every Mistress doesn’t set this rule.

But I am conscious there may be health reasons connected with not allowing a sissy release. I don’t know and I’d prefer not to allow a release whatsoever, but to be sure, I milk my sissy husband once a month.

You may now be thinking that if I milk Girl, my sissy husband , I have to put up with her smelly mess, she gets to masturbate herself and she gets to orgasm. Well, no.

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The monthly milking

I make Girl’s milking a regular monthly event and I strip it of any sexual context. It’s organised and planned. And since I don’t allow her to touch herself sexually and because I don’t like male discharge, I will wear latex gloves, a plastic full length apron and one of those surgical masks we had to use during COVID.

GIrl is usually a little frustrated by the end of the month. As I mentioned above, one of the reasons I don’t allow her to orgasm is because I love to tease her. Some evenings we’ll sit on the sofa watching TV, me dressed, her naked. I lightly rub her little clitty all evening with my fingers to keep it hard, but never allowing her to cum.

chastity devices

I’ve trained her to hold for ages. She’s not orgasmed for so long you’d think she’d have a feather trigger. But no. It’s amazing what training can do. Even if she is close, I’ve trained her to let me know. I just love to hear her tell me knowing how she’d really like to orgasm but knows it’s against my rules.

You cannot imagine the power I feel, and the fun I have, taking her to the brink and then stopping, letting her calm, and then starting all over again. This is one of my favourite games.

lockdown feminization book set
Locked down and helpless in an a dominant women’s household and they don’t want any males – click on the book covers for more info.

I read that male discharge is dispersed in the body and is good for them as it’s full of minerals. I’ve also read some reports that say that males need to cum for prostate health. So as not to take any chances, I therefore milk her monthly.

She will stand in front of me naked. I will have the plastic medical apron, latex gloves and face mask. I don’t want any accidents and it all ends up on my clothes or hands.

femboy love book cover
Charlotte loves her boyfriend, but wants to improve him. She thinks a touch of femininity might help – click on the book cover for more info.

I make Girl stand sideways on and I rub her little thing with my gloved hand. I don’t allow her to talk unless she needs to tells me she’s about to cum. Generally, the moment is obvious. I can talk of course and I like to chat about the weather or a film I’d like to see. I want this to be non-sexual; I want it viewed as a necessary and tedious process, which is exactly what it is.

Here’s my AI image of us in the milking process. I can get frustrated at times because it’s a nuisance.

naked sissy and a dominant woman

When Girl is on the brink, I stop rubbing and her orgasm is ruined but the cum still drizzles out. She turns away and catches the mess in a tissue. We go together to the bathroom where I watch her clean herself up, making sure she doesn’t play with herself while doing it.

Here’s another AI image of us during milking.

Milking upgrade sessions

I’d like to remove myself entirely from doing the manual milking as there is obviously still some sexual connection, despite my efforts to turn it into a mechanical process.

One idea is to play a porn video of two sissies having sex while I’m rubbing her with my gloved fingers. Whilst this is clearly sexual, it’s the right type of sexual — sissy sex. I still won’t permit her to have an orgasm, but it’s good training for her to associate some kind of release with sissy sex. Sissy or T-Girl porn is the only porn I will let her see anyway. In fact, I regularly make her watch sissy on sissy porn or sissy on man.

My next step is for Girl to collect her mess in mug and to make her drink it. More good training for when she swallows other sissies cum.

This of course leads me to the logical conclusion that the milking be done by another sissy. I’m not sure we can always line up the regular monthly session that way, but maybe I need to be a little more flexible. Of course, I won’t allow Girl to orgasm since the problem with loss of submissiveness would still apply. I would order Girl to bring the other sissy to orgasm after she’s cleaned Girl up. A thank you blowjob and swallow (hee-hee).

I like the idea of the other sissy being allowed to orgasm but not Girl. It’s another fantastic, controlling tease.

feminized 2 book cover

Milking sissy

As in all our FLR activities, Girl’s no-orgasm rule and the milking has been discussed and agreed. In fact, Girl tells me that it’s highly erotic and exciting that I control things this way. She says she loves the feeling of constant arousal that never goes away and she loves how she’s always left as my horny, obedient girl.

Let me know if your Mistress milks you and why.

If you’re a Mistress, do you milk your sissy? Some Mistress like to milk their submissives to keep them drained, which is the opposite to me. Do tell in the comments.

And please let me know if you like my AI images of my sissy milking. Squeeze your eyes together, and the cartoon images look a little like me and Girl.

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Filed Under: Female led relationships, Femdom, FLR, wife led marriage Tagged With: humiliated husband, humiliation, married sissy, Sissy, sissy husband

Comments

  1. Vangie says

    17 April 2026 at 16:03

    My wife reliefes me more often via peggin, she uses and strap-on.
    After she has made me cum, I have to pretend her strap on is a genuine penis and I suck it until it is clean.
    (I wash it later anyway)

    Reply
    • Lady Alexa says

      26 April 2026 at 18:57

      She lets you cum?

      Reply
      • Vangie says

        29 April 2026 at 13:34

        Yes she does, time ago I felt somehow embarrassed due to the whole scenario, but I eventually fully embraced the FLR time ago. I event went through some suegeries to improve my figure, now I yave sexier boobs, hips and derriere for the joy of my wife.
        My cumming are no longer dense or large, probably due to my diet (I am vegan)

        Reply
  2. Naddy says

    2 February 2026 at 03:15

    I have fallen in love with you mistress, your thoughts are my fantasies. I can give you my life

    Reply
  3. Leighanne says

    26 December 2025 at 18:20

    My wife prefers to milk me with her Hitachi Wand onto a large spoon. I do not waste a drop. Once I fill the spoon I squeeze out the very last drops and wipe the tip with a finger that I immediately lick clean. The she simply puts the spoon into my mouth and I swallow the entire warm load of semen. She like to repeat the milking several times a day. At least three or more. I have learned to enjoy the taste.

    Reply
  4. Bill says

    13 December 2025 at 16:54

    I know that you intend to make Girl give one of your sissy friends a blow job, and that Girl is very uncomfortable with the whole idea. It could be that she is totally put off with the idea of having semen deposited in her mouth. Have you considered having Girl ingest her own semen immediately after milking? Once, she is used to swallowing her own semen, it may make the thought of giving a full blow job less intimidating for her.

    Reply
    • Lady Alexa says

      15 December 2025 at 20:31

      Yes I intend to make her swallow her own cum as training

      Reply
  5. Steve says

    13 December 2025 at 16:13

    When I was an owned sissy bitch, I too received regular milkings. My sissy clitty was always locked/caged, so receiving a milking was the only time my cage was removed. The milkings were irregular. Sometimes my clitty got relief a couple times a week and sometimes it was 2 or 3 months in between milkings. However the routine was pretty much always the same. My owner would tell me to “go and put something slutty on to wear bitch”. That generally meant stockings and garters for access to my clitty and my 6 inch locking heels. Then, once dressed, she would say something like “now go retrieve your restraints whore”. The restraints consisted of handcuffs and a spreader bar, and although not a restraint, a large penis gag was locked into my mouth. She would then have me in a standing position and the spreader bar was secured. My hands were cuffed behind my back so I had no chance of touching my clitty. and the milking process began. I would always cum into a wine or champagne glass and it was fed to me slowly as she wanted to coat my lips with cum. Sometimes she would have me cum into an ice cube tray so that I could have cumsicles with my “ice water”. I am grateful that she had me get used to consuming my cum before I was required to swallow a different sissy’s cum or one of her bulls. I believe that all milkings of a sissy should be consumed as this training in invaluable for a sissy to become the whore her mistress wants her to be. When the milking was over, I was still in my restraints while she locked my cage back on. Often times after being unrestrained I was allowed to bring her to orgasm orally and then receive a good pounding in my sissy pussy from the largest strapon she owned. Ms Alexa, does your sissy girl put up a fuss when required to eat and swallow her seed?

    Reply
    • Lady Alexa says

      15 December 2025 at 20:30

      I love the idea of cumsicles

      Reply
  6. Audra says

    13 December 2025 at 13:42

    It’s good to read that sissy has still strict rule about no cumming as real men do. Also nice porn choice. I believe it will confirm her place.
    I never had real FLR but my ex was quite dominant and she often kept me in chastity and only way to release was if I played with a dildo she gave me. After sissy orgasm I was still very horny and frustrated, more than before. She also made sure I consumed my sissy juices.
    Waiting for next update.

    Reply
    • Lady Alexa says

      15 December 2025 at 20:29

      I think it’s a good practice to make a sissy consume her own juices

      Reply
      • Colleen says

        17 July 2026 at 04:09

        Oh in the past I have milked Todd periodically and frozen his semen each time until we have a good 6 ounces.

        Then when I have teased Todd and denied him to the sexual breaking point……I thaw out the cum, warm it to body temperature, squirt it inside me with a syringe and all over my belly and hips dripping to my back door….. then invite Todd to give me oral pleasure

        I tell him the most outlandish story about me taking on 8 of his best friends, and his job is be a good little cum eating cuckhold and lick me clean. Every drop Todd, lick me clean or I’ll tickle torture you to comply and make you suck the boys off yourself

        Reply
  7. Sissy Andrea says

    13 December 2025 at 04:24

    I am milked here but not fortunate enough to be free when I am as i am locked due to previous “misbehaviors”. Since there is no traditional orgasm let down is minimal at best and leaves me with no real sexual pleasure. Any emissions are captured in a condom and disposed of by consuming them.

    Reply
    • Lady Alexa says

      15 December 2025 at 20:28

      Sounds about right to me

      Reply
  8. Donald says

    12 December 2025 at 23:27

    When I met Joyce she made it clear that if I got out of line I would regret it! I liked her strong take no prisoners approach.
    We dated for 4 months with no affection except teasing. I fell more & more in love with her as she became more dominant. I fell into an FLR quickly.
    I asked her to marry me & she said maybe! If I agreed that she handle all of our finances, I did not expect sex & would only get it if & when she agreed & I was to do the laundry, house cleaning, dishes & all car care
    Of course I agreed!
    She told me that my tiny dick would be of no use for her! I figured I could satisfy her in other ways
    We got married ‘ I signed her agreement! What I essentially agreed to was to slavery & cuckold ism.
    Trust me, I had no idea what I was agreeing to!
    Joyce is a sadistic narcessist who humiliated me & sexually tortured me but never let me cum!
    I had to submit to submissive sec from her lovers. She gave me opportunities to leave but I chose to stay! She kicked me out & I begged to be allowed back.
    This is the abusive life I accept!

    Reply

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