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I Had My First Sissy Boy Sex

Personal Stories, Advice, and Support 38 People

    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 erection when I was naked or looking at pictures of naked people, and vague images in my mind of parts of people’s...
    harlanfi harlanfi 70+, M Jun 22, 2011

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    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 becoming a sissy slu*t! My name is "Yvette" or at least it is when I'm feminized ;-) I've been wearing girls things since I was five years old...
    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 city. Working with me was an older lady Joan about 45 who ran the old fashioned telephone switchboard and a young man about 25 named Fred. I...
    omegapilgrim007 omegapilgrim007 61-65, M 1 Response Feb 7, 2012

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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 slu*t! My name is "Yvette" or at least it is when I'm feminized ;-) I've been wearing girls things since I was five years old...
    quorumvette quorumvette 36-40 3 Responses Apr 24, 2012

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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, he was a blatant pervert. He was 11 and I was 13. We would parade around naked, touching each others boners and...
    deleted deleted 26-30 2 Responses Jan 11, 2013

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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 we didn’t have to form up in the Quadrangle and march there, but could walk together ahead of time to get ready to serve...
    harlanfi harlanfi 70+, M 3 Responses Jun 22, 2011

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    Related Experiences

    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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    Yeah I won't lie I'm down so where's this room at ??
    kerw94 kerw94 18-21, M 1 Response Jul 7

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    Would love too! Anyone in ontario? Feel free to add and message me!
    jack4770 jack4770 18-21, T 2 Responses Jul 9

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    This is what I would truly love to find at some point!!!!!
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 2 Responses Jul 12

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    Emotional Affair: Was she Narcissistic or Borderline Waif? I am a married man with two beautiful children and a wonderful wife. I have never “physically” cheated on my wife...
    DriveRiggins DriveRiggins 41-45, M 2 Responses Jul 9

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    I started dating a girl, we'll call her becka, well over a year ago. When we first got together it was amazing, for months at the beginning we were the perfect couple. I loved...
    mitchel71 mitchel71 26-30, M 1 Response Jun 29

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    So back when I was younger, I would always play with girls more often than boys (as any typical girl would). Every now and then I would be hanging out with a girl friend or...
    ShyBi416 ShyBi416 16-17, F Jun 30

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    So back when I was younger, I would always play with girls more often than boys (as any typical girl would). Every now and then I would be hanging out with a girl friend or...
    ShyBi416 ShyBi416 16-17, F 1 Response Jun 30

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    It's good/bad to see that I'm not the only one living in hell. This is my story... In 2009 my wife and I got married, at this time I accepted a transfer to different location. I...
    EEProj EEProj 41-45, M 1 Response Jul 6

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    I'm lonely. I'm so lonely. I used to have so many friends and used to go out and have tons of fun. I cut most oft friends off because of things that have happened. All my friends...
    akillen akillen 18-21, F 1 Response Jul 18

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    I had a stillborn boy at 31 weeks into my pregnancy. This was my third pregnancy. My first daughter passed away shortly after her birth. She was born at 24 weeks. Then pretty...
    Amberjacobs Amberjacobs 18-21, F 1 Response a week ago

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    I went back and looked at the first stories I wrote on here. I haven't been here all that long. Joined in November of last year and didn't really come back on consistently until...
    coffeeflavoredkisses coffeeflavoredkisses 46-50, F 5 Responses 1 day ago

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    I hate him but I love him too much to leave him (lol I know.) We've been together for almost 16 months and I'm already so attached. He's my first love and first proper boyfriend...
    Feliciajake Feliciajake 16-17, F 2 Responses 13 hrs ago

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    I was 15 when I first gave oral sex the boy was 18 I was very shy of course I didn't know what I was doing but I did it & he told all his friends I did & he said he wanted more I...
    cutelilshawty cutelilshawty 13-15, F Jun 29

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    Few times in my life sexually have I been outdone by a man in bed. Even at my age I've got more grip down there than most men can take. I have had to be more gentle with men than...
    Marymarthazetta Marymarthazetta 56-60, F 3 Responses Jul 5

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    It's been six years since my wife and I have had sex. The problem is, I can't do without it, or at least, I don't want to. I have always been drawn to men all the way back to 8th...
    HappyHiker719 HappyHiker719 61-65, M 10 Responses Jul 12

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    I love sex , I think about it all the time. But I don't have sex often. I've always had a steady boyfriend but for the past two years I've been dating and it seems I'm only...
    Renee175 Renee175 26-30, F 2 Responses Jul 17

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    I miss this experience I had with this boy but years have past and he's grown up now he's been through puberty and he's my big brothers' friend's little brother and I think my...
    AlisonA123 AlisonA123 22-25, F 1 Response Jun 29

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    I was four and put all my building blocks down my shirt until I looked really fat. It turned me on, and I had no idea what sex was. Turns out I have a pregnancy fettish.
    wishingIknewme wishingIknewme 36-40, M Jul 1

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    My boyfriend is 21. We have been dating for a while now. He's my first 'real' boyfriend. I moved in with him about 3 months ago.. I'm finished school and thinking about joining the...
    LovelyJay5232 LovelyJay5232 16-17, F Jul 17

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    You know that feeling when you want a boyfriend but you don't? Iv had those feelings a lot but now I'm tired of being alone and single and have been for ages, I still have feelings...
    AnotherTomboyGamer AnotherTomboyGamer 13-15, F 1 Response 1 day ago

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    I have a clotting disorder called factor V Leiden. Basically I have placental abruptions (where the placenta detaches effectively cutting off baby's life line). I lost my first...
    xlxSpiraxlx xlxSpiraxlx 26-30, F 1 Response a week ago

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    yesterday i read a report on a 8 years old boy sexually assaulted by a 36 years old women. i am just wondering how its happened. how a woman can sexually abused a child?? and also...
    kirat1990 kirat1990 22-25, M 2 days ago

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    *An update* well last time i updated we had agreed that he was moving out as his **** addiction had won over our sex life. well any way the next day we had another make or break...
    desper8 desper8 31-35, F 18 Responses Jul 2

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    I'm 14 and never had a real boyfriend .all my bf was online from different states or countries and i never new them. tbh I never held hands with a guy before. smh...and I'm going...
    lovealway14 lovealway14 13-15, F 1 Response a week ago

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    I've posted my affair story, so not going to repeat. I've finished my Affair, which is why this title says, I HAD an affair. It's been 5 months since I was together with the...
    OnAlert OnAlert 56-60, M 11 Responses 3 days ago

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    Anyone's spouse have a former relationship with someone else that included mind blowing sex??? During counseling yesterday he revealed the girlfriend before me they had non stop...
    LuckyOctober LuckyOctober 31-35, F 29 Responses Jul 2

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    it started off that i was hanging out with old high school friends. we were all talking and walking around in a house. we found ourselves in this huge room. it was like half the...
    sadisticbitch sadisticbitch 26-30, F 2 Responses Jul 3

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    I bought my girlfriend a riding crop and blindfold for her 30th birthday. Then lightly flicked it all over her body -- with a few surprise hard swats on the bottom. The suspense...
    Bircher Bircher 56-60, M 3 days ago

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    Why am I having an affair? All marriages go thru lows.. Yes.. mine hit rock bottom. He was out of work and drunk everyday... He was miserable.. He had no desire for sex...
    Differentforever Differentforever 46-50, F 8 Responses 1 day 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 41 mins 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 35 mins ago

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    My situation is so messed up. I've been seeing a married man for 7 mos who claims he no longer loves his wife whom he had a daughter with 9 mos ago. He comes to see me nearly...
    hysgirl hysgirl 31-35, F 1 Response 1 hr ago

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    I still love that person.i wrote a post last month or something.got loads of help and advice.and my craving to hear his voice or see him has reduced.but still I can't forget him...
    Naina94 Naina94 18-21, F 35 mins ago

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    Things get better all the time!! Have been so happy together lately <3 had our ups and downs but he is the one, I can feel it. I love my Boyfriend so so much. And I know he...
    PrincessDemeter PrincessDemeter 18-21, F 18 mins ago

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    There is so much controversy over abortion laws in different countries and those in the mindsets of the people around. A woman is looked down upon if she has had sex in India...
    TheNextSin TheNextSin 22-25, F 8 Responses Jul 19

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    We were twelve. I have dressed and been at peace with being a girl in a boy's body all my life. I got a huge crush on Josh, the cutest boy on earth, but he didn't know (as most...
    bookreader2000 bookreader2000 13-15, T 5 Responses 4 days ago

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    I love great sex with hot younger women and they love the way I please them!
    John0406 John0406 61-65, M 55 mins ago

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    I used to date a boy named Sam who used to be really sweet until the last two months of our relationship. Even though I broke up with him I want to date him again (which I know is...
    Teenager1421 Teenager1421 13-15, F 46 mins ago

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    Let my start off by saying that I'm a Christian and I am gay. I live with both my parents and my younger brother and I have a dog. I've been dating a guy for the past 2 months. We...
    jowaymedina jowaymedina 13-15, M 3 Responses Jul 3

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