I Turned My Husband into A Cum Loving Sissy

sisst in pink socks and panties

You may have read about my husband giving my bull a blowjob and then becoming a bi cuckold and if you haven’t I encourage you to do so because things have moved on dramatically since then and now my ‘husband’ is a fully-fledged cuckold sissy. When I look back I wonder how we even lived our lives without this fun and pleasure, having that conversation was the best thing we ever did.

My Husband Wasn’t Always A Sissy

man and woman in selfie

He enjoyed being a cuckold, watching me sleep with other men, he enjoyed watching from afar and getting off on me having fun without him and enjoying the person I was with. He loved nothing more than fucking me after the person I was with was done and feel how wet and even stretched I was from then and not him. He got off to the humiliation, it’s what fuelled him. I always had bigger fantasies than just cuckolding and when I opened up to him, I was in for a big treat.

I Always Had A Fantasy Of Him Fucking One Of His Male Friends

woman revealing mans penis underneath pants

I started planting little seeds after we talked about my fantasies. I used to get him to fuck me in the ass and then I would tell him to think of me as a man and he would cum right away. He cleaned up my bull’s cum and he even gave him a blowjob.

I then brought a pegging dildo and we tried pegging, it took a while, but once I got the hang of it I mentioned while fucking him, imaging I’m your best guy friend with my big cock fucking you in your tight ass. He didn’t want to enjoy it, but he started cumming all over the bed. After that my bull fucked him in the ass for the first time too and that’s where everything began to unfold.

Training Started When I Put Him Under Lock And Key

He loved cock cages before but this was different. After my bull fucked him and we both agreed on him loving being a sissy and being degraded I got him a cute pink cage for his tiny cock. It was much smaller than his other one, it was pretty and pink and his cock was tightly squeezed in there. It was a much harder test for him but the humiliation of it was a bigger reward for him and it fuelled us and turned us both on even more that it had done before. It felt as if we were stepping into a new world of fantasies and pleasures.

It Was Not Long Before I Named Him Cindy

In the bedroom when my bull was there and even when he wasn’t my husband was now known to me as ‘Cindy’, he responded to the name and he knew his place. Having this name gave him an alias, it allowed him to be her inside of the bedroom and really let loose and be who he wanted to be.

I have also mentioned before that he gets off on the humiliation aspect of cuckolding astronomically and so when we figured out that he loved humiliation in many forms replacing his name with that of a typically female name was very humiliating to him, which got him off even more.

Meet My Sissy Husband

man wearing panties

Here my sissy husband is, her dick is now her tiny clit and her ass is now her pussy.

We’ve been using plugs to help stretch her out a bit more for the real thing again. She loves wearing slutty thongs and sheer lingerie sets. Her favorite is to dress in her slutty French maid outfit, that I picked out for her. She wears it around the bedroom when I am being fucked by my bull and then she cleans us both up, she also gets teased and humiliated by us in her little outfit too.

Cindy wears her wig, she shaves everything so that she is nice and smooth, I want to wax her soon. She practices all the time, sucking my fake dick, she wants to be amazing for one she sees my bull and it gets her off when I watch her take my fake cock down her throat.

I taught her to eat my ass correctly, so she could do it to my bull when he asked. This took some time, she just kept on trying to pleasure herself through the cage but we eventually got there.

Training Her Ass (She was Too Tight)

husband on bed in red panties

My bull had fucked her ass before, only once and he didn’t get all of the ways in. Cindy my sissy was also very aroused at the time. We knew that we couldn’t just do it again, it would take time and preparation and so in the lead up to meeting my bull again I used different pegging dildos on her, I taught her the best cock sucking techniques, pretending I was my bull and later getting her ready to be double penetrated. I trained her ass to take an array of different sizes and when I knew she was ready it was time to get my bull inside of my sissy.

The First Time My Sissy’s New Pussy Got Stretched

sissy on all fours showing off butt

I have a bull I’ve been seeing for a while now and I got my sissy started by letting her clean up his cum off me and later his cock.

My bull would use her as a cum rag, just for cleanup and have her clean his big fat cock, just after he’d finished in me, my sissy would sit starry-eyed with her mouth open and he’d just slip his cum covered cock in Cindy’s mouth for her to clean it up and then he would leave.

The first time it happened properly was a momentous occasion, it all happened so naturally. After my bull had slipped his cock into my sissy husband’s throat he ordered him onto all fours, parted his legs, pulled his panties to one side, and gently slid himself inside of his stretched pussy, his clit was straining at his cage.

When my bull is done with me now, I watch him take my sissy husband and insert every inch of his massive cock into Cindy’s tight pussy while I watch and usually masturbate. Seeing Cindy have her thong pulled to the side and then later covered in my bull’s cum is bliss. Knowing that I planted the seed and got them to this place is even sweeter.

Seeing my husband a man who would never go near another man, bent over and being fucked by another man and shaking and moaning from enjoyment is powerful.

Cindy Is Now A Little Whore

censored images of man having sex with a sissy male

She gets as much dick as me, my bull taught her to suck his cock just how he likes it and her throat skills are better than mine, she swallows his cum but she prefers it in her ass or dripped over her clit.

Seeing her jealous when I’m getting fucked by the bull is an empowering feeling and knowing she has to have my sloppy seconds if she’s lucky is enough to make me quiver with delight.

Cindy, my sissy husband is now such a little whore in the bedroom that I sometimes don’t know what to do with her. My bull loves taking control of her and humiliating her in front of me and her tiny clit just strains at the constraints of her cage, if she is really, really good she might be let out for a tiny orgasm but even then that’s only if she’s very lucky.

She Can Take A Bigger Dick Than Me :’)

It’s true! I struggle way more with my bigger bulls than she does, she takes them like a champ and they always remark about how tight she is. I am so impressed by her. My sissy husband also told me how much she enjoys a bigger dick, she told me it can feel like more of a challenge.

Would You Let Me Turn You Into A Sissy?

man dressed as woman laying on bed

I loved turning my husband into a sissy, testing boundaries, and ultimately fulfilling his desires and I want to do it again. I want a few sissy men in my life who follow my orders and fuck when I say, clean up cum when I say and do as I say. Would you let me do it for you?

You can read this, and see if you like the idea of cleaning up after my bull and me.

I have more stories I can share from my sissy husband, let me know if you want to post them for Jack and Sarah to share!

I love submitting our tales here, it has been eye-opening for us and I am forever grateful to Jack and Sarah for allowing us to share our lessons and stories.


  1. I have a Mistress and she calls me her sissy slut. I’m hopping some day her boyfriend cums in her before our session so I can lick her pussy clean. I would also like to clean her bulls cock and have him fuck me in the ass if he wants. I’d love it.

    sissy slut joe

    • My wife and mistress loves to peg my boi pussy and she loves to be dominant. Maybe we can find us a big beautiful black bull to serve. I love to be submissive to my bbc . My mistress has permanently locked my little clit in chastity cage it’s just been a month and I hope that we can find us a dominant black bull

      • I love sucking BBC!

        • It’s been a fantasy of mine for long time, I would obey your commands. Never saying no.

      • I would love to be shaved, caged n feminized for you n your bulls pleasure.

    • Im new at researching cuckolding. Put a few years back
      when I didn’t even know
      what cuckhold meant.
      I basically was a cucked closet submissive wanta be cocksucker. Fantasizing of my hot petite nympho spinner fiance catching me slobbering on her lover’s,
      A hot, handsome Mexican stud, big brown Verga .
      I would so love to talk with others,. Finish this story with someone who can appreciate it.

      • Yes I would do as you say mistress make me a sissy slut for all cock

    • I have always wanted to be a cum slut for a couple. I love sucking cum out of men and women and would like to take piss from both.

  2. You did amazing with Cindy, well done. I am a bull and very impressed by what you did.

  3. I want my wife to make me her sissy. How do I make her think of it (it has to be her idea). She knows I’m a crossdresser and she has a boyfriend. All she needs is a sissy and that’s me. Do I just tell her to have him move in and I’ll take the spare room. That I’ll be their live in sissy maid and I’ll pleasure her boyfriend anytime he wants. I dream about sucking her boyfriend’s cock. I need to be a sissy so bad I ache. I would be a real soft sissy girl.

  4. When my wife found out about desire to become her sissy maid she loved the idea and i have been that way for five years. She has a man that takes care of her need for cock and she has me to make sure she is clean when he leaves. The mix of her juices and his is extremely tasty. I am bent over writing this comment and his cock is buried deep inside me . My wife took time making sure i looked really feminine before he arrived. I couldn’t be any happier. My wife has changed a lot and has made her choice to divorce me and marry that guy. I am now hunting for that well hung bull of a man to take me for his own.

  5. Im a sissy cuckold husband and my wife has a bull when he calls he wants sex now. If my wife is not in the mood then i must stand in even though his cock is hugh and rips me apart ever time i still do it. I love my wife and ill do anything to make her happy.

  6. I enjoyed the stories
    Wanting to be a cuck

  7. Love being a sissy cuckold

  8. my wife pegged me for about 5 years in roleplay and started slowly making me a sissy finally she made me fuck and suck 3 of her male friends and from then on sold my sissy ass to to men she knew with money

  9. When my wife left my neighbor Steve turned me into his personal cocksucker. I can’t get enough of his beautiful juicy cock down my sissy throat. Now I crave his huge cock loads all the time. He says my mouth belongs to his Superior huge juicy cock. I feel my boi pussy is twitching just thinking about it being the next thing to be taken by master Stephen. I definitely love being his cum dump faggot.

  10. Very HOTT!! My clit is oozing and my ass is open and ready!! Love to eat my tasty load and my ass stretched to the max, I can easily handle a 10″ very Thick COCK, love the feeling of being full!! I can get off hands free! Pierced nipples I have are so sensitive!! Into BDSM!! Thanks for the stories, your SubSlut Sis, Angie

  11. I would do what ever you want sounds like fun

  12. I like that Cindy keeps her feminine little rear end so nicely shaven clean for the men who fuck her. Is she getting good at doing her makeup?

  13. If I become your sissy you can bring more then one bull home

  14. I wish my wife would do this to me, she knows I want to be a sissy but not how far I want her to go, can you help us please.

  15. Would You Let Me Turn You Into A Sissy?
    I’d say yes! I would ask for a slow gradual process but it would also have the proximity factor.
    So I’m open to it if you are!

    • Yes I would. Have Skype?

      • Yes still a closet sissy full dress smooth just need a stern woman to guide me in my fantasy

  16. I’m a crossdresser & my wife likes to play with me even taught me makeup I love being a sluty girl & want to be her sissy I’d even let her rent me. I love to suck cock & swallow & please fuck me once I had been popped I’ve craved it I love watching her get pleasured and then cleaning her out mmmm

  17. My ex girlfriend and I started with bi threesomes. I was open about my bisexuality in the beginning of our relationship. She would give me the opportunity to let out my need for male male sex whenever I asked. I was never caged or controlled but was definitely the beta in the room. She would joke the next morning about my needing a pregnancy test or telling me my boobs were swelling “that time of the month hun?” She and I ended up splittling over other things but I enjoyed our odd relationship. I even dated one of her ex boyfriends for several months.

  18. Soon after we started dating I told my now wife I had been with a Guy that made me wear girl cloths and suck his dick daily.marreied ten years now I’m her personal assistant secretary maid shopping helper,driver .I fluff dick hard to fuck her ,clean up pussy and cock after he fucks her.i wear girl cloths 24 7 hormones have made me soft with tits . To earn my keep she rents me to friends as a maid part of my maid dutys is sucking dicks and eating creapue pussys. I love being my wifes pussy ass dick sucking property

  19. I am a sissy,sub,slut.,I really love Domme type transgender MtF gurl D,doing what they want with me,also love servicing k9s, orally n anally,I can swallow 9+ incheand anally take 9 inches.i love to be broken sexually.please break me.exavier

  20. i need a lady like you to help release the inner female in me…

  21. I am a total sissy slave for my ex-wife and her husband I love the way he has me suck his cock and he has a friend come over and I get to suck him will his friend fucks me then my ex-wife will take pictures of me and I must do what they want and beg for more cock they take me to all the adult bookstore where I am put in the bouth and told that I will do everything they say I love being a little sissy sexslave more than anything in the world I have been with 35 men in one night and I was in heven

  22. I would love to be a sissy cuckold for any woman

  23. Cindy is a very lucky girl. My wife and I have the same relationship. I love nothing more than dressing totally sissy and being Leanne then watch her being fucked good and hard. I always clean them both up and if I’m lucky he will stretch my pussy too.

  24. I would love somebody to make me a sissy slut. Use hypnosis to train me to a trigger word which makes me instantly horny and put sissy clothes on wherever I am.

  25. I love the stories on here, would love to be like some of you but I’m married and my wife would never consider anything like this.
    She’s as strait as they come.
    It would be divorce court for sure.
    I love her but would like to play with someone maybe in the Houston area!!

  26. I wish her bull would cum all over her stinky socks and make her sissy husband lick all the cum off her stinky socks

  27. oh yes I want you to turn me into a total sub sissy-fem cd bimale cuckold. Robbie in Norman, Oklahoma.

  28. I am a sissy cuckold and love it, big cocks covered in my wifes cum juices , she likes black cock but anythung over 7 inches will do,

  29. I want this so much

  30. Mmm I would love to be a good boy for ,and let you train me properly

  31. that was awesome account of turning your hubby into a sissy. id really like to be owned by a sexy mistress who does same sort of thing to me, and i cant resist being degraded an humilated too

  32. I am 59 recently divorced male, my sex life has always been so so. This year I decided that I wanted to try everything at least once. I’ve never been with a man and only with five women throughout my life. Where does someone like me start?

Leave a Comment