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    Debman's profile

    Debman Profile
    Debman
    Profile views: 57398
    Fanbase: 1571

    About Me
    Hi
    I live in Worthing, West Sussex and I like to crossdress and would love to meet others that like to do the same. I have not been dres that long but it just feels so right and so good.

    Interests
    Bi , Chastity , Crossdressing , MMF , Sissy , TV

    Signed up: 7 years and 8 months ago
    Images viewed: 14702
    Images ed: 2982

    Gender: TS/TV
    Birth: 26/05/1962

    Location: United Kingdom

    Last Online: 1 hour ago

    Connect with Debman
    Status updates
    Debman's profile
    Jan 15, 2019
    Got dressed up and went for a walk outdoors with my wife, it was dark but we did walk along the shops and bus stop with people around, Loved it and want to do it again soon.
    Trying4More's profile
    Trying4More 4 Aug, 2026
    back from countryside car park visit freshly smooth wearing stockings panties bra under joggers and t shirt. two friendly older men who liked me a lot x

    Paulaclit's profile
    Paulaclit 27 Jul, 2026
    Does she make you wear a chastity cage ?

    Daddies_Boy's profile
    Daddies_Boy 28 Apr, 2026
    Is SO Fun to risk exposure, love to have other people see me,

    biloser's profile
    biloser 7 Apr, 2026
    sounds sexy

    JamesVI's profile
    JamesVI 22 Jan, 2026
    Thrilling!

    littlesissytimmy's profile
    littlesissytimmy 2 Jan, 2026
    Love to see you out dressed

    littlesissytimmy's profile
    littlesissytimmy 18 Aug, 2025
    Hi I am also in Worthing. I would love to know when you next go for a walk

    niftychunk's profile
    niftychunk 24 Jul, 2025
    Which one of you got more attention?

    Solo_Man's profile
    Solo_Man 7 Apr, 2025
    Love to wear a short dress and no
    panties and walk around holding
    your hand and kissing you in
    public... wait till my erection pulls
    my dress up...

    Kisses

    johanna-Mary-Clayton's profile
    johanna-Mary-Clayton 7 Jan, 2025
    Oh you added gallery to favourites.

     
    Debman's profile
    Jan 3, 2019
    I would love to dress up and meet with another sissy and make out with them while my wife watched me suck on their cock.
    JamesVI's profile
    JamesVI 22 Jan, 2026
    Nylon

    Silksissy's profile
    Silksissy 2 Jun, 2025
    I am definitely up for that!

    Solo_Man's profile
    Solo_Man 7 Apr, 2025
    *Hand Raised! Pick Me, Pick Me!!

    Except your wife has to watch me
    suck your sissy dick too...

    Love to put on a show...

    erosbi60's profile
    erosbi60 29 Nov, 2024
    love to have your wife fuck my ass with a starpon as you suck my cock

    Lananew's profile
    Lananew 5 Mar, 2023
    That's a beautiful desire, I'm so with you on that one!

    welshlad4u's profile
    welshlad4u 18 Feb, 2022
    Its a lovely feeling

    electronus's profile
    electronus 10 Mar, 2020
    Write a comment...

    electronus's profile
    electronus 10 Mar, 2020
    Sounds delicious

    manofewords's profile
    manofewords 27 Jan, 2020
    I'd love to be that guy!

     


    Comments (19) (See All Comments)
    Chastity_Pia
    Chastity_Pia's profile
    Comments: 249
    Commented on Aug 30, 2026
    "Ohh mommy.. yes ..YEEES.. oh my..I wish it was me"
    Debman | Aug 30, 2026
    This isn't mummy, this is a nasty old lady that lives down the road, she likes to dress young men up as sissies and tease them and tease them and tease then and keep edging and edging them and then weeks and weeks later when they can't take any more she makes them ejaculate like they never have before, blowing there load high up into the air and then she laughs and asks them if they enjoyed it. If they say yes she starts all over again. If they say no, she locks their penis in chastity until they are begging her to do it all over again.

    Chastity_Pia | Aug 30, 2026
    oh no my panties are getting wet from the thought of being allowed to squirt like that. even though Pia is wearing sissy clothes.. ohh how Pia would like to squirt the sissy cream out

     
    Chastity_Pia
    Chastity_Pia's profile
    Comments: 249
    Commented on Aug 30, 2026
    "OMG..hear clitty is so much bigger than mine.. and it, is not i a clitty cage"
    Debman | Aug 30, 2026
    No her mummy has unlocked her cage for some well earned release, but her mummy will be locking her clit back up again now she has ejaculated.

    Chastity_Pia | Aug 30, 2026
    At least she ejaculatet milk from her big..ehm.. pee-pee

     
    thepolack90
    thepolack90's profile
    Comments: 1,129
    Commented on Aug 29, 2026
    "She's looking over at him with delight and success. She fucked him so good he is out cold from the exertion."
     
    thepolack90
    thepolack90's profile
    Comments: 1,129
    Commented on Aug 28, 2026
    "Hope she edged her sissy good then locked it back up."
    Debman | Aug 29, 2026
    Yes this is just edging he's had his orgasm for this month and can't be trusted not to play with himself behind his wife's back, just like most men. So she will be locking his penis back in it's chastity cage.

    thepolack90 | Aug 29, 2026
    Indeed. Without the cage he would be cumming far too much and not focused on what she wants. Do you think she'll try other means to bring him to orgasm?

    Debman | Aug 30, 2026
    No she does not try to make him orgasm, he's only allowed to ejaculate 12 times a year and this is not one of them, but yes when it is time for him to ejaculate she like to make him cum a quickly as she can and that includes touching his bottom and inserting a finger and then two and stroking his prostrate to make him cum, he never last long when she does that.

     
    thepolack90
    thepolack90's profile
    Comments: 1,129
    Commented on Aug 28, 2026
    "She's been training him to have prostate stimulated orgasms. He thought it was for the intensity. Really it's because she's going to start stimulating it by different means and her hand will not be helping his cock."
    Debman | Aug 29, 2026
    His wife started anally fingering him after she came home and caught him dressed in women's underwear looking at sissy porn and fingering himself. She stood and watched and when she saw how hard he cum while fingering his ass and probing his prostate, she knew she wanted to make him cum like that.

    thepolack90 | Aug 29, 2026
    Once she saw that he was cumming consistently with anal stimulation and with minimal cock stimulation, she locked his cock up. And set down the first strapon on his caged cock so show how deep it was going to go. He instantly swelled into the cage like it was going to break.

    Debman | Aug 30, 2026
    That's when after a short fingering she took her fingers out placed her strap-on against his hole and looked in in the face and asked him if he was ready, he nodded and she slowly started to push her strap-on into his ass hole, it was tight and she stopped pushing for a moment and told him to relax. As he relaxed and without her pushing any more, the could both feel the strap-on sliding into his ass, then she pushed and she was inside him. She asked if he was ok, he said he was, she said she would give him a moment to get use to it, then she slowly started fucking him. His caged cock moving with each thrust into him, he had his eyes closed and was softly moaning and his caged cock was leaking per cum that was running out and landing on her strap-on and lubricating it as she was fucking him.

     
    thepolack90
    thepolack90's profile
    Comments: 1,129
    Commented on Aug 27, 2026
    "She's showing it to you sideways to demonstrate how far it's going to be down your poor throat."
    Debman | Aug 27, 2026
    I would be more than happy to get on my knees and allow a woman like her stick her cock in my mouth and down my throat, it would be my pleasure.

    thepolack90 | Aug 27, 2026
    Same here. Even if it's my first time, she could have me up against the wall for more pressure.

    Debman | Aug 28, 2026
    I think it wouldn't be long before she would be wanting me to bend over for her and if I had to lose my anal virginity I would like to lose it to a women like her.

    thepolack90 | Aug 29, 2026
    Absolutely it would a woman like her. That's the kind of cock and body that breaks men in and keeps them addicted to her.

    Debman | Aug 30, 2026
    I would have loved for her to have been my Mother-in-law someone I could pop round and visit anytime I wanted and if I did an odd job for her here and there she could pay me with her beautiful cock.

     
    thepolack90
    thepolack90's profile
    Comments: 1,129
    Commented on Aug 27, 2026
    "Just because you watched her cum on her stomach doesn't mean she's done. Now it's time for you to lick it up and keep her hard with your mouth. As you are bent over doing so, she pulls your ass towards her and you feel her lubing your hole. Looks like her cumming was also to build up her stamina."
    Debman | Aug 27, 2026
    She loves to fuck a man with her penis.

    thepolack90 | Aug 27, 2026
    She looks like she'd like more than one man submitting to her at the same time.

    Debman | Aug 28, 2026
    She looks like she into younger men, not older men in their 60s like me.

    thepolack90 | Aug 29, 2026
    What about just to clean her up after each session?

    Debman | Aug 30, 2026
    I would love to suck her cock and have her cum in my mouth, but not after it's been up some blokes ass.

     
    Debman
    Debman's profile
    Comments: 12,279
    Commented on Aug 27, 2026
    "Mothers-in-laws, they just seam to be able to see what a younger man wants, and your seams to want to give it to you, your a very lucky man."
    thepolack90 | Aug 27, 2026
    Yes how do they know? Very lucky indeed. Just wonder if she'll ever tell my wife.

    Debman | Aug 28, 2026
    I think she would have already of told your wife, and your wife is planning to lock your penis in chastity.

    thepolack90 | Aug 29, 2026
    Looks like my sex life is going to change radically. But how will I cum from now on?

    Debman | Aug 30, 2026
    Well once locked your wife might want to start fucking other men and cuckolding you. She might ask if you would like to be there and help. You could suck them hard, guide their hard penis into her, then kneel by the side of the bed and watch as he fucks her to orgasm after orgasm, something you have never been able to do. Then wait for him to cum inside her and for your wife to ask you to clean them both up, first taking his cock into your mouth and sucking it clean and thinking how good it tastes, better than when you sucked him hard and them moving on to your wife's cheating pussy and savouring the taste of her cum filled pussy for the very first time as you would never lick her clean once you had cum inside her, but this is different, you haven't cum, your penis is locked in chastity, your feeling really turned on and you really want to please her, lick her to orgasm and hope she will unlock your chastity cage and allow you a supervised masturbation session. Or maybe she will send you to her mothers still locked in your chastity cage who will fuck you with her strap-on while calling you a Cuckold and asking you if you enjoyed it until you cum.

     
    thepolack90
    thepolack90's profile
    Comments: 1,129
    Commented on Aug 26, 2026
    "When I met these two at the cougars bar we clicked pretty quickly. They invited me to their cabin for a weekend. Said there would be lots of cock sucking and lots of anal. I had no idea what they actually meant."
    Debman | Aug 27, 2026
    I bet it was your best weekend ever, all that cock sucking and anal?

    thepolack90 | Aug 27, 2026
    It was. They were so kind in how they instructed me on how to suck and take them anally. Never once was my cock touched or did I get to fuck them. But they did let me masturbate during the times when they were using me which was generous of them. I can't wait to come back. We're finding a time soon. They also overheard them talking about something like "lock that cock" but I don't know what they meant. Probably nothing.

    Debman | Aug 28, 2026
    I think you will find out soon enough if it was nothing or not. Enjoy.

    Solo_Man | Aug 29, 2026
    Mmmm... Mr Polack I would love to see that! Knowing the weekend is coming you abstain from hand to penis punishment... you pull up to the cabin, heart is already racing with anticipation, semi-flaccid penis in your pants... the ladies hear you pull up and step-out on the porch wearing only an naughty grin... the dark hair is holding a cage on her index finger, while the other is banishing a shiny butt plug... you know the drill sweetie, no clothes in the cabin... you drop your clothes in front of the cabin and step on the porch... in seconds you are caged and plugged as they take you by the hand and lead you into the cabin... lamb to slaughter, oh sweetie you are about to be dominated!

    thepolack90 | Aug 29, 2026
    Oof. Good stuff. I'm blind sided by the cage they put on me and the plug that's in me. I abstained because I though they would let me masturbate as they used my holes but what is going to happen? And the plug. I can feel it already opening me up more. I thought they were just going to put their large cocks in me. What is happening?

    Debman | Aug 30, 2026
    Once in the cabin you see another 3 men in there all naked, all locked in chastity and all plugged. They then tell you they are ready for a wonderful weekend of sex, they ask each of you in turn if you have any fantasy's you would like to live out. The first man a young skinny bloke, says he would like to be spit roasted by them both and have them both cum inside him. Your mind runs wild as to what you would like them to do to you and can't wait your turn to tell them.

     
    thepolack90
    thepolack90's profile
    Comments: 1,129
    Commented on Aug 26, 2026
    "When I met my best friends aunt at his wedding, we both got a little drunk and talked about fantasies. I divulged a bit too much because not long after she had my cock in a cage and was training my ass. At the wedding she had whispered that she would love to be able to fuck the cum out of me and I laughed as we kept talking. She wasn't joking. She kept me denied and became clear she was adamant about making it happen. After several months of being locked with progressively larger strap-ons. She told me tonight's the night. This was the longest and thickest she's ever put on and just the thought of it displacing my insides seems like it would certainly squeeze months of cum out of me. If it didn't, I was another day without cumming with a destroyed ass. She could tell I was nervous and trembling. The precum leaking was the only sign that she knew I was eager."
    Debman | Aug 27, 2026
    I hope she used plenty of lube with that bad boy and it was your best fuck ever and didn't hold back and blew your load all over the place, while still locked in your chastity cage. This is what dreams are made of.

    thepolack90 | Aug 27, 2026
    Definitely. After gasping at the sheer amount I was filled and violated, she was able to get me to take it all the way to the hilt. It wasn't long before I was shooting ruined, thick ropes of cum out from my cage. She squeezed my balls and told me there's still some in there we need to get out. It was relentless but after another 10 minutes I was cumming again. Ruined and incomplete but cumming nonetheless. She took a picture of my horribly gaped hole, cage, and cum. Just in case I decide I want to leave her, this is what she can say she would show my friend and possibly more.

    Debman | Aug 28, 2026
    I think if she did show your friends the photos, they would be jealous and would be calling round to see her hoping she would do the same to them. As for you, she'll never need to unlock your chastity cage ever again, now she is able to fuck the cum out of you.

    thepolack90 | Aug 29, 2026
    You are probably right about that. Yes. Now that she knows she can force the cum out of me anally, what use is there taking it out. I'll likely crave eating her out more and desperately begging for anal so I can have relief.

     
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