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I Had My First Sissy Boy Sex

Personal Stories, Advice, and Support 38 People

    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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    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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    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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    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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    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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    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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    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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    I was 15 and he dumped me for a cheerleader. Then the rest of my four years of high school he would try his hardest to break me and my boyfriend( now husband )up. Then he found me...
    carebear1019 carebear1019 31-35, F 2 Responses Jun 23

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    So I'm dating this guy right now, and I really love him, but my ex just won't leave me alone. I dated my ex for 2 1/2 years, and now he's constantly texting me and telling me that...
    dyingalittleinside97 dyingalittleinside97 16-17, F Jun 23

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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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    My boyfriend works from 5am to 5pm. He usually gets 5-6 hours of sleep a night. I often wonder if this is the reason why he barely initiates intimacy with me. Our sexual...
    elephant70 elephant70 18-21, F 2 Responses Jun 23

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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 4 days ago

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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 2 days 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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    I'm a girl and have only really had sexual interactions with girls (really seriously with one). I have had guy friends/ boyfriends, but always felt awkward kissing them... But when...
    BecomingPerfect88 BecomingPerfect88 18-21, F 3 Responses Jun 23

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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 2 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 1 Response 5 days ago

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    I think the hardest thing for me, looking back on how I got into a sexless marriage, was that it was a long slow process (a death by a thousand cuts). In some ways it would have...
    runninginthedark70 runninginthedark70 41-45, M 10 Responses Jun 25

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    When I was twelve I had my first "real" boyfriend. After seeing each other for about a month or so, he asked me if I wanted to go see a movie. During a quiet scene he put his left...
    Becky555 Becky555 18-21, F 1 Response Jun 23

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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 5 days 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 2 days ago

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    Love having sex without protection. It is the way it's intended to be and how all of us got here in the first place. The sex is always hotter when trying to get pregnant.
    RyanB79 RyanB79 31-35, M Jun 27

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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 2 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 30 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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    He broke up with me 2 times. In two weeks. After telling me he doesn't care about my disabillity ... But then his friend decided to tell him that if we had sex it would be bad...
    annirawrmuffin annirawrmuffin 22-25, F 1 hr ago

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    I feel really good tonight. My gf and I had sex with was special and she told me she loves to call me daddy. She told me she recognizes me as her sexual dominant and a "supreme...
    cj911 cj911 26-30 1 hr ago

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    Okay. This is my first post, so it might be kinda... Whatever. I am not like gay. I'm just kinda bisexual. So it started when I was 10. I went to my cousin's house. I was kinda...
    AwesomeGuy1000 AwesomeGuy1000 16-17, M 22 mins ago

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    There's a weird one! It never occurd to me! I ran into somebody from my old schooldays recently. Back then. She was smart. Funny. Attractive. Part of the 'rich kids' club. Totally...
    picklebobble picklebobble 46-50, M 49 mins ago

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    So guys and girls I am needing some help.I am wanting to pic has my first pair of thongs.Any suggestions on brand,fabric,any bigger size,etc.I love wearing panties and I think...
    Bigboylovinpanties Bigboylovinpanties 18-21, M 2 hrs ago

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    It's so easy to let your mind wonder away from you when your upset,you know like making up sexual scenarios in your head,that's the best time for me ;) so c'mon guys tell me sexy...
    greatinbedchick greatinbedchick 16-17, F 1 Response 2 hrs 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 7 Responses 3 days ago

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    After reading some posts here about renowned marriage/relationship researcher John Gottman (the one who says the "Four Horsemen -- contempt, defensiveness, stonewalling and...
    Mettamomma Mettamomma 61-65, F 8 Responses Jun 23

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    I have had 5 miscarriages over the past 2 years but my boyfriend does not want to ttc. We are not using any prevantive measures such as condoms or hormonal birth control as we have...
    amore1993 amore1993 18-21, F 2 Responses Jun 25

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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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