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I Had My First Sissy Boy Sex

Personal Stories, Advice, and Support 35 People

    My Sissy Sex History. A True Story! - My Sissy Sex History. A True Story! quorumvette says: This is a true account of the trip I've taken down that slippery slope towards...
    quorumvette quorumvette 36-40 3 Responses Apr 24, 2012

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    Discovering I Was A Sissy On My First Job - My first full-time job was the summer I turned 18 and it was as a front-desk clerk at an older hotel dowtown in a medium sized midwest...
    omegapilgrim007 omegapilgrim007 61-65, M 1 Response Feb 7, 2012

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    Leslie And Me - When I entered an all-boy boarding school at 14 I was almost completely lacking in knowledge about sex. All I knew was a few stirrings of my body, getting an...
    harlanfi harlanfi 70+, M Jun 22, 2011

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    Leslie And Me Part 2 - Leslie and Me Part 2 Both Leslie and I were Waiters in the school Dining Hall. That meant for our parents a big discount in our tuition. For us that meant...
    harlanfi harlanfi 70+, M 3 Responses Jun 22, 2011

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    Johnny And Anal Sex. - Johnny was obviously a girly type. This never really bothered me but he had a dual personality. He acted so proper around other adults, but when were alone...
    deleted deleted 26-30 2 Responses Jan 11, 2013

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    My True Sissy Sex History! - My Sissy Sex History. A True Story! quorumvette says: This is a true account of the trip I've taken down that slippery slope towards becoming a sissy...
    quorumvette quorumvette 36-40 3 Responses Apr 24, 2012

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    He lived in Europe and I in the US. We fell madly in love, and were in a long distance relationship for 2.5 yrs before I finally was strong enough to break it off. He was...
    deleted deleted 26-30 2 Responses Mar 27

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    Thank you for thinking about me today! I am an effeminate little pretty boi who loves to bottom and be the wife in a relationship!
    FemGayBottom FemGayBottom 26-30, T 2 Responses 6 days ago

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    I was with a boy for a year and 5 months I was 15 he was 17, we were so happy and a got on so well and tbh we were perfect but it came to the point where he got rather clingy and...
    brokensouls brokensouls 16-17, F 2 Responses Mar 16

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    I've never had a real boyfriend. I had a two week thing with a guy who had not yet come out of the closet. No, not a sex thing. But.. there were some heavy make out sessions. He...
    WhoNeedsNormal WhoNeedsNormal 16-17, F 1 Response Mar 17

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    where I come from, most often than not you marry your high school sweetheart. I've had 2 serious boyfriends in my lifetime (that doesn't count guys I've casually dated & hung out...
    countryanon countryanon 16-17, F 2 Responses Mar 28

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    I know what's in the past should stay that way, but I have a hard time not thinking about my boyfriends sexual past. It was only a few girls, but one in particular I hate because...
    AjLeePunk AjLeePunk 22-25, F Apr 2

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    Last night: We've been spending nights on separate rooms for more than 1 1/2 yrs now, no sex. I've made it clear that I don't want to form enemity or strife as we part ways...
    lovegentle lovegentle 36-40, M 6 Responses Mar 30

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    I was 16 when i had my abortion, was very young and naive. When i found out, i was just about 3 months and was told i had to make a decision- fast. My boyfriend was petrified and...
    jodiexo jodiexo 18-21, F 3 Responses 6 days ago

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    My daughter was born March 15 2014 she was perfect . Two days before I lost her due to a blood clot in her umbilical cord I was at the doctor and she was up and moving all around...
    londynn londynn 16-17, F 6 days ago

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    When I had first discovered I was bisexual and had my first experience with a guy, it was magical. Everything - every sensation was different and just more intense. My ****** was...
    thataussieguy thataussieguy 26-30, M 1 Response 5 days ago

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    I remember one boy in 3rd grade that had a crush on me. He gave me a silver butterfly with no antennae. He moved schools after that year. If anyone else had a crush on me they've...
    Schism7 Schism7 18-21, F 1 Response Apr 5

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    One month update on my one month update. My wife continues to try to fux me out of this group. The last 4 weeks (totalling 8 now if my math is good) we have been having a lot of...
    HusbandOfOne HusbandOfOne 41-45, M 18 Responses Apr 7

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    Reading these stories lets me know I'm not alone. When I met my fiancé he was just getting out of a seven year relationship I thought it was odd that she moved out with 2 kids in...
    Walkedinblind Walkedinblind 31-35, F 1 Response 5 days ago

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    After my husband cheated on me with prostitutes (see the experience before this), I've found I want sex all the time now. I had a fairly high sex drive before, and he certainly...
    MrsElizabeth MrsElizabeth 31-35, F 6 Responses Mar 23

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    I had a abusive boyfriend, Jason. He would hit me,kick me, and touch me in ways. i feel uncomfortable. He kept on threatening to rape me if i didn't do what he said. When i was...
    GirlWhoWantsToDie GirlWhoWantsToDie 22-25, F Apr 4

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    Me and my wife have been separated for a bit now due to the military but she's coming to visit until we can get her here, anyways we've had plenty of unprotected sex but this time...
    DC0813 DC0813 22-25, M 1 Response Mar 28

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    I caved. I was feeling detached and was not really thinking about him much. It felt really really great, to think maybe I was moving forward to ending. Then I caved into seeing him...
    pencruz pencruz 46-50, F 3 Responses 3 days ago

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    In case you think that Opposite Land is perfect, it isn't. No tax refund for me this year. Instead, a $6,500 tax bill due to how things worked out for me in the divorce settlement...
    Mettamomma Mettamomma 61-65, F 11 Responses 15 hrs ago

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    i was 17. i told my step mom i wanted to be a model and enter the beauty pageant. she said we would see. the next week was my sister party. she was having a party and her and her...
    loverboy758 loverboy758 18-21, M 6 hrs ago

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    Seriously need advice :(....Soo I'm new at this... I'm 23 years old.. Got married really young, have 2 babies, one of which was born this year. I've been married for 5 years. My...
    missme90 missme90 22-25, F 6 Responses 1 hr ago

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    the reasons why i dont want to do anything sexual before marriage : reason number 1 : what if i had sex with my girl friend before marriage , and after few days i met with...
    lifetriangle lifetriangle 22-25, M 4 Responses 15 hrs ago

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    It It Quite Simple Really part 2 I combed her bangs straight down and cut them blunt just above her eyebrows. She looks at me and asks, "Are you done?" "Done? I'm just getting...
    TemplarKnight2 TemplarKnight2 56-60, M 6 hrs ago

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    I don't want to brag or anything, but I have a reason why my boyfriend and I have a great sex life. We don't worry or care about other peoples sex life and only care and focus on...
    TanTwink TanTwink 22-25, M 11 hrs ago

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    Hi, it's Dakota again. I've already told my story of being raped by my uncle and three strange men last summer, just after I turned 14. One of the men was killed in a bad drug deal...
    mouthdakota mouthdakota 18-21, M Apr 4

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    Hi, it's Dakota again. I've already told my story of being raped by my uncle and three strange men last summer, just after I turned 14. One of the men was killed in a bad drug deal...
    mouthdakota mouthdakota 18-21, M 9 Responses Apr 4

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    So my boyfriend died very unexpectedly just under two months ago, and I feel like things are just becoming more and more difficult. We would talk to each other every single day and...
    teneal teneal 16-17, F 1 Response 8 hrs ago

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    My first kiss was so much fun and with the best person. I had my first kiss when I was 22 so I was also overthinking it. I didn't know where to really put my lips. It was not his...
    jlhhlj123 jlhhlj123 22-25, F 3 hrs ago

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    For the first time in almost 3 years, I will be meeting with my Mother and 2 sisters. the last time I saw them was the day that I graduated from college and informed my family that...
    NoreenA NoreenA 22-25, T 5 Responses Mar 21

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    Recently I've gained feelings for an ex again. I was dating this guy for about 7 months and the relationship was good but he lied about little things, seemed to have trust issues...
    kayceebby kayceebby 18-21, F 1 Response 20 hrs ago

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    I have been living in this sexless marriage for several years. I haven't had sex in about 8 or 9 months. My husband refuses to admit there is an issue. Well, I finally had sex but...
    nurse594 nurse594 41-45, F 18 Responses 6 hrs ago

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    A text message I sent my girlfriend ... I think I'm going crazy watching how you are with your phone and your constant need for a connection with the online world, it's an...
    supercat01 supercat01 31-35, M 5 Responses 14 hrs ago

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    Its not the fact that i'm a 13 year old who's complaining. But the fact that i'm turning 19 this year and i've never had a boyfriend. Never even been kissed. Or more accurately...
    Lifeshouldsparkle Lifeshouldsparkle 18-21, F 3 Responses 13 hrs ago

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    Nobody deserves hurtful pain. Weather you are a mean person or your really nice. Nobody deserves pain. I am going to tell you a story that will warm your heart but will make you...
    JenniferArvayo JenniferArvayo 18-21, F Mar 16

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    So a couple days ago I went on my first vacation with a man ever, my boyfriend of over 1 year. 1 Year 3 months to be exact. The second day of vacation I received a friend request...
    awkward11 awkward11 18-21, F 2 Responses 5 days ago

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    I was in a happy long distance relationship you know Islands apart only.Last Saturday, a usual typical evening where I usually talk with my boyfriend asking how was his day and...
    katypurrry katypurrry 22-25, F 1 Response 18 hrs ago

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    Last night he bent me over the side of the tub and we had sex
    bendovergirl88 bendovergirl88 22-25, F 1 Response 17 hrs ago

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    I took shrooms only twice in my life and then, I was done with them for like forever. First time i did not take much, only about ten small shrooms, I enjoyed tripping and stuff I...
    Progenitor Progenitor 18-21, M 16 hrs ago

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    I've had 3 bear death experiences. First u was a toddler, & my dingy grandma was watching me a day. I was I'll, I had liquid medicine. I was suppose to receive 2 teaspoons during...
    taiterz taiterz 26-30, M 2 Responses 14 hrs ago

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    Affairs and marriage two completely different things!!! I want to be 60 with my husband and have my grandchildren come to the house. My husband takes care of me because he loves me...
    circlesnomore circlesnomore 31-35, F 6 Responses 7 hrs ago

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    I want a bf but the last guy I dated destroyed me. We had a really bad break up and I luckily (or maybe not) moved away straight after. I sort of let go and now I'm over weight...
    chrisisyourfriend chrisisyourfriend 16-17, M 1 Response 7 hrs ago

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    My boyfriend cheated on me last year. Long story short, he slept with her in our flat, in our bed I should say, and I found out the next day when I found him hypo-glycemic. That...
    Jenezebel Jenezebel 22-25, F 1 Response 5 hrs ago

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    am looking for a man or women to take me an dress me up as a sissyboy so i can be set free live in lakeland fl have spouse who dosenot want me in a sex less marreg to help me all...
    eaglecry eaglecry 61-65, M 4 Responses Mar 26

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    I want be a feminized sissy wife for a hot gentleman. I want to be his feminine partner and companion. I would make him dinner in sexy outfits, give him spontaneous, non...
    erintgirl erintgirl 26-30, T 1 Response Mar 30

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    Love dresses! 💜 I grew up in a family mostly of ladies. I was 6 when I was put in my first dress by my cousins. I was embarrassed then but I really liked that experience. Since...
    sissyyumi sissyyumi 22-25, M 5 Responses 4 days ago

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    It was on my birthday this year (12th April 2014). I had my best friend over and also my boyfriend. I was feeling quite tired, so I put a movie on for my boyfriend and bestie to...
    imirox1999 imirox1999 16-17, F 1 Response 23 hrs ago

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