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I Had My First Sissy Boy Sex

Personal Stories, Advice, and Support 39 People

    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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    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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    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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    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

    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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    Related Experiences

    Lies, Fault, Goodbye. I was in a relationship with this guy since March and he broke-up with me at the beginning of August because he said he wasn't happy the last two months we...
    Samaccino Samaccino 16-17, F 6 days ago

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    Before I start this, I want to say that I know that this shouldn’t upset me as much as it does. The problem is my boyfriends’ brothers’ girlfriend (my boyfriend and his...
    faithtrustandpixiedust faithtrustandpixiedust 22-25, F Aug 27

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    How could anyone not remember their first painful breakup? Mine was in 8th grade with my first boyfriend. We lasted for around 5 months. Since it was my first ever relationship, I...
    KenKitty KenKitty 16-17, F 2 Responses Aug 24

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    I once was in a rather intimate long distance relationship with a Spanish girl. This relationship was fueled by sexual desire for one another, but lacking the ability to act upon...
    AlbertFeynstein AlbertFeynstein 13-15, M Aug 25

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    I never had an amazing real sex. I had sex twice. The first one was just 2 mins, he was lame and came right away and I broke up with him throught text the day after. Yeah he took...
    genejanexx genejanexx 18-21, F 14 Responses Aug 24

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    OK, so I don't actually have a totally a sexless marriage but here's my input & what we have that others don't have. Communication. We've been together for 20 years, married for 13...
    Xlandria61 Xlandria61 61-65, F 5 Responses Aug 26

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    I met her a year ago today. I didn't notice her wedding ring at first but soon found that she never took it off, even when she took everything else off. She told her husband...
    pcflvly pcflvly 46-50, M 1 Response Aug 31

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    I loved Halloween because I dressed as a girl from as long as I could remember. Nothing scary, always cute and feminine. My other earliest experiences was playing "dress up" with...
    AndiSissy AndiSissy 51-55, M 1 Response a week ago

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    I want a boyfriend so much. I feel so pathetic and like no one wants to date me. I'm a senior in high school and have never had a real boyfriend. I had a brief thing freshman year...
    Justanotherperson1234 Justanotherperson1234 18-21, F 4 Responses 1 day ago

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    My wife was always just plain vanilla sex, nothing else, over the first few years, sex became less and less. These days it is virtually non existent, ie I might get hand action...
    bigmoe47 bigmoe47 46-50, M 1 Response Aug 31

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    My H and I have been together almost 15 years. In the beginning of our relationship, of course, we had sex constantly. He would even make a 2 hour drive to give me sex before I...
    beentoolongLily beentoolongLily 46-50, F 13 Responses Sep 9

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    I guess I'm a very sexual person, I've had a lot of sex partners and I've enjoyed it all. I don't dress trashy, but I will dress sexy. Sex is awesome and I always enjoy doing it...
    YellowGirl225 YellowGirl225 22-25, F 15 Responses Sep 10

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    I was warned by several people on here that having had our child, the sexless marriage thing would get a lot worse than before I was pregnant. How right you all were. Husband has...
    Pattycakey Pattycakey 36-40, F 13 Responses 6 days ago

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    So it's been a long time since I have had any talk about sex with my wife. So I want the perspective of a female refuser. How would u feel if u r husband brought up wanting to have...
    lauraCD805 lauraCD805 36-40, T 5 Responses 5 days ago

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    Anyone else never had a girlfriend/boyfriend? Share so we can all be single together :)
    jm4life jm4life 16-17, M 1 Response Sep 9

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    I read on EP a lot, about various Boys who tell how they love their Boyfriends so much, then proceed to tell the world in every detail of what they say they did to each other...
    Joshiskierons Joshiskierons 13-15, M 2 Responses 4 hrs ago

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    Hi. I think I need help but I can't talk to anyone about it. I'm 20 years old now and a month ago I woke up because I had a dream that reminded me of the nightmare that happened...
    Diana1994 Diana1994 70+, F 1 Response 7 hrs ago

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    Hello Everyone! Have been reading experiences for few days, found people across the globe in same situations share their sadness on the issue. Inspired by such experiences...
    Raaj4rp Raaj4rp 41-45, M 3 hrs ago

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    My boyfriend asks me everyday if I miss him. Before he left I had planned on being strong,on not admitting that I do miss him, on keeping focused so I won't be upset, but I can't...
    VousEtesBelleCM VousEtesBelleCM 18-21, F 7 hrs ago

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    As a child I was sexually abused by my father it went on for year I was eight when it first happened nine when I ended it first I really didn't know what was going on he would call...
    Somechick47 Somechick47 18-21, F 4 Responses 6 hrs ago

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    I'm in a very strange position. I had been in a long distance relationship for about three years on and off with the same person. We both have too many emotional problems, but my...
    ofthisgirl90 ofthisgirl90 22-25, F 7 hrs ago

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    Here is something odd. When we first got married we had our own cell phones on different carriers. I can't remember the exact time frame, but my cell phone broke and I was...
    sartur sartur 36-40, F 7 Responses 1 hr ago

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    During my early teenage years, I met someone at a summer camp and pretty early on fell in love with him. I was attracted by his accent, sense of humour and caring attitude. Being...
    chestnutpuree chestnutpuree 31-35, F 18 mins ago

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    Hello my name is Jenny and my Ex boyfriend, his name is Bobby,......has wore all my clothes, well at least all my dresses and lingerie. I know it sounds so yucky, but as he grew up...
    jennylee911 jennylee911 46-50, F 2 Responses Sep 12

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    I was chatting to this guy on Grindr a few weeks ago, he didn't have a profile pic or any kind of profile, but he was 2 streets over and wanted to suck c**k, nothing else. So I...
    crake101 crake101 31-35, M 9 hrs ago

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    You Tell Me I can understand why some of my friends think I'm girly or even gay (which I am, but they don't need to know right? ^^; ). I’ll just compare myself to most of the...
    noahman97 noahman97 16-17, M 2 Responses Aug 25

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    Yes it would be nice to have a boyfriend, who like to hugs and cuddles.
    DiscoNight1970s DiscoNight1970s 46-50, F 1 hr ago

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    I had a successful sexual experience last night. I didn't feel dirty or used after. I really talked at length with my husband about the events of my childhood. He assured me I'm...
    coffeeIover coffeeIover 26-30, F 5 Responses 4 hrs ago

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    You Tell Me I can understand why some of my friends think I'm girly or even gay (which I am, but they don't need to know right? ^^; ). I’ll just compare myself to most of the...
    noahman97 noahman97 16-17, M 2 Responses Aug 24

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    You Tell Me I can understand why some of my friends think I'm girly or even gay (which I am, but they don't need to know right? ^^; ). I’ll just compare myself to most of the...
    noahman97 noahman97 16-17, M 1 Response Aug 24

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    The few times I've actually been with men I've usually asked that they live alone and/or can host with a hotel room. The reason being that I had two different men become stalkers...
    Vboots Vboots 26-30, T 5 hrs ago

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    It was five months ago, in April. It was one of those things that aren't supposed to happen: it was my sophomore year of college and I was visiting my boyfriend of three years for...
    skinnesn skinnesn 18-21, F 5 Responses Sep 10

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    ever since ive had my abortion it has changed me for the worst. im not the same person as i use to be. my day to day life has different patterns of mood swings. ive gone from a...
    cjay89 cjay89 22-25, F 1 Response 10 hrs ago

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    I don't have anyone I could talk to, but I am dying for sex. I was sex deprived as a kid, because my parents controlled my life too much. They consider sex as a kid of sin. In the...
    pblack pblack 41-45, F 7 Responses Aug 26

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    I'm a 22 year old guy. And believe it or not, ladies, you're not a lone. The History with my girlfriend and I: We dated briefly in high school before she went off to college. She...
    daveR80 daveR80 22-25, M 1 Response 1 day ago

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    This one time my friends were skateboarding and I threw some pebbles on the road to see if they'd fall. They didn't. Then I borrowed my friend's skateboard, one of them pebbles...
    evobulgarevo evobulgarevo 26-30, M 2 hrs ago

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    Sissy white boy. All I do is crave c*ck
    raelynnCD raelynnCD 22-25, T 3 Responses Aug 25

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    Reading all these stories of women who have stayed for 10+ years makes my heart ache. I don't want to put up with this emotional turmoil for that long. How did you ladies find the...
    Galaxystar25 Galaxystar25 22-25, F 3 days ago

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    39 year old male maid is seeking a mew role. My previous Mistress has found a new boyfriend who doesn't want a sissy maid about.
    sissymaidsteph sissymaidsteph 36-40, M 2 days ago

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    I came out of two very abusive and manipulated relationships. I had bad dating experiences and now I am scared for life. I honestly, do not want to DATE ever. I do get lonely at...
    Elizabethgl7302 Elizabethgl7302 26-30, F 4 Responses 2 days ago

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    Yesterday I came back from work quite late, prepared dinner and set the table with candles and flowers, wanted a romantic dinner. He was still not there, I phoned him and he said...
    bigkiss1979 bigkiss1979 31-35, F 26 Responses 10 hrs ago

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