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I Want To Be A Sissy Cuckold

Personal Stories, Advice, and Support 183 People

    In The Beginning (part One)

    Emma, my wife, was straddling me, pinning my arms down and slowly moving up and down on me, the head of my **** just inside her vagina. She was teasing me and it was exquisite! Her voice sounded almost honey-like as she continued to **** me like this, nice and slowly, keeping me...
    jessicasissymaid jessicasissymaid 41-45, M 1 Response Nov 6, 2011

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    My Story

    1 After reading some Penthouse letters about guys watching their wives with other men, I started telling my wife about some of the fantasies I was having about her with other men and me watching. Libby is about five feet tall, with curly brown hair and dark brown eyes and a...
    downfall1964 downfall1964 41-45, T Sep 7, 2012

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    So Many Exciting Possibilities...

    Not long ago the thought of this would have completely shocked me. Not in a million years would I have imagined that I would want my wife to be ****** by another man. Now, after reading too many stories on this subject, I seem to have been converted. Now, not only would I be...
    jessicasissymaid jessicasissymaid 41-45, M 2 Responses May 18, 2011

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    My Story Continued

    1 After reading some Penthouse letters about guys watching their wives with other men, I started telling my wife about some of the fantasies I was having about her with other men and me watching. Libby is about five feet tall, with curly brown hair and dark brown eyes and a...
    downfall1964 downfall1964 41-45, T May 21, 2013

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    Related Experiences

    Please anyone come on me ill be ur sissy maid :)
    sissyslave18 sissyslave18 18-21, M 8 hrs ago

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    Well... as it stood, I am nineteen and in college. Well, colleges and teens equal to many challenges especially when you are away from home. Okay, at first, I cannot make any...
    thelonercollegestudent thelonercollegestudent 18-21, F Jul 19

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    I love being a sissy, even more than that I love playing with others. There's nothing better than licking down someone and ripping a hole in some nylon stockings thirsty for her...
    raelynnCD raelynnCD 18-21, T Jul 19

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    I got 100% Sissy on The Sissy Test, Found it on Google, now I am going to take the Inner Gender Exam or something, will goggle it and let you know my results and the name of the...
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 2 Responses a week ago

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    I believe you are who you see you're self as and if that's a women even tho you're a man who the **** saids ? Religion ? Pfffft **** that be who ya want even if it does mean you...
    kerw94 kerw94 18-21, M 4 Responses Jul 7

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    Would love to meet a cool guy who was Dom and into a Sub Sissy Boi!
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T Jul 15

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    I'm a proud sissy, and I want to play. Message me. Please. You won't regret it :p
    raelynnCD raelynnCD 18-21, T 2 Responses 4 days ago

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    Part 3 In the world, but not of the world. Malachi was once again staring out the window at a blizzard. Death was exactly like life except that the apartment and its occupants...
    Eitan Eitan 22-25, M Jul 15

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    Hey! Sissy gay bottom submissive here! Anyone in ontario? Add me ;)
    jack4770 jack4770 18-21, T Jul 9

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    I want a master or mistress to train me so bad!! I'm not sure if I'm good enough though
    thepenguinbosss thepenguinbosss 13-15, M Jul 13

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    I just passed my sissy test with a hundred%
    abbyseaney abbyseaney 16-17, T 1 Response 1 day ago

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    The world is getting cold and it's only getting colder but I don't think it will ever get as ice cold as the hearts of many of our own.Greed,Fear,Money,Religion,etc. these are some...
    PeaceAtSoul PeaceAtSoul 16-17, T 2 Responses 22 hrs ago

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    I haven't been on here for a while, but I feel the need to really write out my feelings. Two weeks ago I came back home to the Bahamas for a year. I was pretty excited on coming...
    rainee12 rainee12 13-15, F 14 hrs ago

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    I have wanted to ask my stylist for a women's hair style now for years, but I never seem to work up the nerve. I feel that I need to develop a relationship with her first before...
    tpoh tpoh 46-50, M 1 Response 12 hrs ago

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    I wrote 50 random facts about myself last night. and i'm bored so i'm going to write another 50. so um yea... here we go. 51- I have met a lot of bands. 52- 90% of my wardrobe...
    sugarcakes143 sugarcakes143 18-21, F 5 hrs ago

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    I've always wanted to fly with my own angel wings! :) I would be able to get away from everything and fly peacefully through the clouds anytime I wanted to... If I didn't want to...
    Redhy11 Redhy11 16-17, F 2 Responses 6 hrs ago

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    I do not want a donor!!! I will shamelessly come out and say that I want to be a mommy and get pregnant! You guys can hate on me all you want, but like I said: SHAMELESS! If I...
    BrittannyLynn BrittannyLynn 16-17, F 2 Responses 3 hrs ago

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    About 5 months ago, me and my boyfriend broke up. I am over him for the most part but lately, I think about our old times. Not necessarily the relationship part but the friendship...
    uhtobehonest uhtobehonest 16-17, F 23 hrs ago

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    A young couple were dancing the night away on a hot evening in a London nightclub. So sweltering, many of the men were shirtless. Not this guy though. The gf unbuttoned her bf's...
    jasblyth jasblyth 31-35, M 1 Response 19 hrs ago

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    Yes I do I want to because when I'm alone I feel like there's no one to hurt me and I can't hurt anyone. I can't trust people because I've always had people in my life that hurt me...
    Coolman1222 Coolman1222 13-15, M 18 hrs ago

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    I constantly try and reach to be better. More understanding, more patient, more giving, more thoughtful, in every aspect of life I try and be a better person in general always work...
    Atromitos Atromitos 31-35 13 hrs ago

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    I am very fond of art and painting and i love to paint. 3 of my aunts are amazing painters. I set a goal for myself that this summer i will paint extensively. I am also hard on...
    Dana93y Dana93y 18-21, F 2 Responses 9 hrs ago

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    Today... Me and my bf were having sex and I kinda felt like I had to pee so JUST IN CASE I went to the potty and went potty and I went back to his room and sat there and said hang...
    FandJ15 FandJ15 16-17, F 7 Responses 3 hrs ago

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    I want to kill myself because I have no one anymore. I just lost the only person in my life that meant something to me but they didn't die they just left. Again. And they didn't...
    slater666 slater666 13-15, F 13 Responses 3 hrs ago

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    I haven't been dating for a while due to a really bad break up at the end of a long term relationship. I'm pretty scared..I don't want to get hurt the way I did before. I just want...
    faithisadino faithisadino 16-17, F 1 Response 41 mins ago

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    I want to lose weight too, but I get concerned for so many young people who post on here. Wanting to try this extreme fasting or diet. The goal should be to be healthier and not...
    MegMichelle29 MegMichelle29 26-30, F 7 Responses 1 day ago

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    I've wanted to die forever. My life used to be much worse than it is now no friends, no freedom, drug problems, nobody to care about. I just sat alone with pure nothingness for...
    LizardKing420 LizardKing420 16-17, M 2 Responses 23 hrs ago

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    Well I want to take a **** but I'm clogged up. Moral of the story: We don't always get what we want.
    CrazyHippieChick CrazyHippieChick 18-21, F 2 Responses 23 hrs ago

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    I hate how money can change a person. It's crazy but some how it happens. My ex boyfriend was one of a kind. Our freshman year, he was quirky, a band geek, down to earth...
    uhtobehonest uhtobehonest 16-17, F 22 hrs ago

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    how can you say you torture me? you're already thinking about someone else. when he comes home, you'll be in his arms and I'll be gone but I know my day will come I know...
    mierdamundo mierdamundo 31-35 21 hrs ago

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    I wish people understood me better. No one knows what I want except me. When I tell people what I want, they look disappointed or shocked. Everybody expects me to be their...
    dourpenguin dourpenguin 18-21, M 1 Response 21 hrs ago

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    1. I am gay & 14. (Nearly 15)yay 2. I live in the north west of England 3. I have no gay friends at all 4. I have not come out yet 5. I live with my nan and grandad 6. I love old...
    Lolbeansarefun Lolbeansarefun 13-15, M 1 Response 20 hrs ago

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    I'd be glad to do whatever a master wants. I only want a female master though. Please, I'll do anything that u need
    itsbigT itsbigT 16-17, M 16 hrs ago

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    It doesn't matter what people think of you, it more about how you think of yourself. If you think you are amazing and great but in a none-full of yourself way, then one day you...
    EvelynElf EvelynElf 16-17, F 1 Response 15 hrs ago

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    Dear lord I have spoken to you for many years, and I have no doubt about your blessings. But I'm confuse, I no longer understand why you still holding me on earth. I'm loosing it...
    esscape esscape 36-40, F 3 Responses 14 hrs ago

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    I was introduced to this guy at a town street fair the other night. We chatted and had fun. I don't know many people in the area, but the ones I do know are twice my age and this...
    WiredCritter WiredCritter 22-25 1 Response 13 hrs ago

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    Well I'm 32 years old and probably started drinking when I was 14-15. I grew up with my father being an alcoholic but a loving fully functioning one. I have associated most all Do...
    Blackgold32 Blackgold32 31-35, M 2 Responses 12 hrs ago

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    I just want to tone up. I want to be fit. This is my dream body
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    I want to read good books.Once I wanted to take up acting but I think I am too shy for that.I once acted in a school play and the lead character forgot his dialogue and I prompted...
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    I speak Spanish, English, and German but I want to learn so many more languages. Languages are fascinating and so intricate because you can take one phrase and in a different...
    Steffi627 Steffi627 18-21, F 2 Responses 8 hrs ago

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    Well I'm not sure I really want to. I've honestly never really been attracted to guys up until now. I like the cute type, maybe 13 or 14 years old, I'm 15 so it's ok. Message me if...
    joefromlondon joefromlondon 16-17, M 7 hrs ago

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    I want to find someone and fall in love. I want that rush, the butterflies in the stomach, the anticipation and the wonderful sensation of being someone's special.
    Skywalker1979 Skywalker1979 31-35, M 7 hrs ago

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    I've been stuck in this Southern Californian town for 28 years of my life. I've always hated it here; I hate how everyone knows everyone's business, I hate the heat, I hate the...
    mrcoolbeansguy mrcoolbeansguy 26-30, M 1 Response 6 hrs ago