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I Had My First Sissy Boy Sex

Personal Stories, Advice, and Support 39 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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    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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    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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    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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    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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    Related Experiences

    Hi amy here just got back from work, found my sissy boyfriend still dressed as I left him. Hes great sissy name katie. Love him for doing as I tell him all the time.
    naughtyamykevin naughtyamykevin 41-45, M 7 Responses Oct 20

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    I am in need of a strict Mistress to serve. Please be real and sincere. If asking for money or to fill out a profile on Alt.com I will ignore it as those are scams. I am 100...
    sissyboy4Mistress sissyboy4Mistress 31-35, M Oct 22

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    I am in need of a strict Mistress to serve. Please be real and sincere. If asking for money or to fill out a profile on Alt.com I will ignore it as those are scams. I am 100...
    sissyboy4Mistress sissyboy4Mistress 31-35, M Oct 22

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    I am in need of a strict Mistress to serve. Please be real and sincere. If asking for money or to fill out a profile on Alt.com I will ignore it as those are scams. I am 100...
    sissyboy4Mistress sissyboy4Mistress 31-35, M Oct 22

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    I am in need of a strict Mistress to serve. Please be real and sincere. If asking for money or to fill out a profile on Alt.com I will ignore it as those are scams. I am 100...
    sissyboy4Mistress sissyboy4Mistress 31-35, M Oct 22

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    I am in need of a strict Mistress to serve. Please be real and sincere. If asking for money or to fill out a profile on Alt.com I will ignore it as those are scams. I am 100...
    sissyboy4Mistress sissyboy4Mistress 31-35, M 1 Response Oct 22

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    Well, I don't have a boyfriend, but I would love to have a sissy guy. Ehe! 😁
    iamcarlolita iamcarlolita 26-30, F 3 Responses 4 days ago

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    hi im a 18 year old sissy after a strict skype mistress im very obedient and need owned skype id live:aka_jamie123
    jamieleeaka jamieleeaka 18-21, M 1 Response Oct 23

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    Rediscovering Sex in a Sexless Marriage: Rediscovering sex - This is where things are at now. For those who are reading my story for the first time let me point out my marriage...
    Fireflyz26 Fireflyz26 31-35, F 13 Responses Oct 2

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    Rewiring Needed! I was wondering today how many people have gone from one poor relationship partner to the next? It seems to me that a lot of us in this group have been with an...
    Artvg Artvg 41-45, F 12 Responses Oct 18

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    I'm a gay man (30) and I'm looking for my first real boyfriend. I was married for three years, divorced now and I knew I was gay the entire time but fought it (stupidly). I've...
    CW3185 CW3185 26-30, M 2 Responses Oct 18

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    It was about 16 days after I moved from Ireland to England and I was in my mum's friends house (she had only 3 boys, 1 older than me, 1 the same age as me, and 1 about 5 years...
    ChocolateCoveredKFC ChocolateCoveredKFC 13-15, F Oct 18

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    My situation is getting more real by the day. I'm in love with my best friend and I'm pretty sure she has a good idea how I feel. I think it's just freaking her out. The other day...
    CollegeStudent22 CollegeStudent22 22-25, F 2 Responses Oct 7

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    I Escaped nearly two years ago. During this time i went through a range of emotions and ups and downs. I met a new girlfriend, who adores me and i am still with. It is bliss...
    punchbag2012 punchbag2012 41-45, M 10 Responses 4 days ago

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    I am feeling lost, or losing a part of myself. I love my husband, and he loves me. But we have not had sex for 4 years. We actually are a very good team, we work together, we...
    LostSophya LostSophya 26-30, F 18 Responses Oct 24

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    The freedom I feel just to be able to walk around knowing I no longer have a penis is just so totally awesome. Being born a girl with a penis made my early life very difficult. I...
    Iamsasha Iamsasha 18-21, F 1 Response Oct 23

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    Best ever with my 47 year old boyfriend!!! Sex with older men is amazing <3
    mdkp mdkp 22-25, F 11 Responses Oct 15

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    Im almost 18 and i have never had an actual boyfriend. The last time i kissed someone was when i was thirteen and our "love story" lasted for like three months, and i say it wasn't...
    whateverqqq whateverqqq 18-21, F 1 Response 4 days ago

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    I Remember it like it was yesterday I was 15 with my first real boyfriend and now im not 19 and havent kissed anyone since I really miss it a lot :( it makes me sad to think about...
    TheSameOne TheSameOne 18-21, M 1 Response 2 days ago

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    I'm single. I have had only one boyfriend in my life. It didn't last. I'm 21. After that experience I understood that the most important thing you can find in couple is honesty...
    Johnmza Johnmza 18-21, M 4 Responses Oct 5

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    Soooo, It's been a while sine I've been on EP. I thought I'd give an update. We DID go for his appointment. I decided to stay in the waiting room so that he could be more open with...
    beentoolongLily beentoolongLily 46-50, F 10 Responses 1 day ago

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    I'm the youngest of 5, before I was born my father left my mum and sisters, mum has had a few boyfriends since but nothing ever came of it. My sister have always treated me well...
    YngLee YngLee 13-15, M 4 Responses Oct 12

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    I am a fairly introverted, creative, intelligent, independent, and empathetic young woman. I take pride on being all of those things. I love art and music, and express myself...
    zsigginz zsigginz 18-21, F 2 days ago

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    I think this is a wonderul idea! I once was chatting with a friend, "Emma". while she was waiting for her 2 kids at a balet class until the kids came out. Whe nclass was over, she...
    nothingnobodynowhere nothingnobodynowhere 26-30, F Oct 18

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    To my fellow suffers I have a question. Let me first say that I know I'm an idiot. I married my first wife when I was 26 y.o.a. and I had some red flags but I thought I could fix...
    Nick5211 Nick5211 51-55, M 5 Responses Oct 11

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    A dare that sort of backfired! It was in early April, 1971. I was 16, and was in grade 11 (third year of high school). There were a bunch of girls in my class that got angry...
    kink54 kink54 56-60, M 1 Response Oct 18

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    Once your wife decides to have you become her personal sissy maid, being a sissy becomes second nature to you after awhile. Like yesterday. My wife had to leave early for a...
    deeken deeken 36-40 3 Responses Oct 21

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    My wife and I got married in our 40's. Neither of us had been married before. We were best friends for a few years before things got serious. She had come from a family with an...
    notsureofanythinganymore notsureofanythinganymore 56-60, M 9 Responses Oct 12

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    I have learned so much fro my past two experiences. I always stayed away from younger men because of the misconception that they were less mature and more prone to cheat. I have...
    Morenita79 Morenita79 31-35, F 2 Responses Oct 18

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    It is what it is. By the end of my first marriage, I wasnt having sex with my wife. Not because I didnt want to, I just couldnt. I was not attracted to her anymore. I dont mean...
    RobertCarlos RobertCarlos 46-50, M 8 Responses Oct 18

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    at first I thought I was in the wrong until I read so many other people on here with similar things happen to them. thigh I'm not sure when to begin really it all started when I...
    babygirl102514 babygirl102514 18-21, F 2 Responses 5 days ago

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    Mistress and her happiness is all that this sissy slave lives for and there is no other way that life could be any better. For some this would be a hell, a prison that would crush...
    SissySonja SissySonja 41-45, T 1 Response Oct 6

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    I need some advice and would like to hear from people who have some experience with this topic.Its quite a long story so bear with me. I have been with my boyfriend for 2 years. He...
    PeppermintLove21 PeppermintLove21 18-21, F 1 Response 3 days ago

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    I was weathering the effects of massive amounts of steroids. My heart raced, and then it began to skip. Feeling the familiar sensation of terror acutely, I realized my entire body...
    tenar108 tenar108 26-30, F Oct 14

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    So last night, my boyfriend and I had a little fun before bed and it was truly magical. I'm not like most girls tho and that's why it was so magical to me because I'm a girl with a...
    GrangerDanger21 GrangerDanger21 18-21, T 5 Responses 1 day ago

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    I have gotten into it a lot the more sexual I get and activity love being taped to watch later
    alexiswcd alexiswcd 56-60, T 1 Response 1 hr ago

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    A little unintentional bombshell last night. Wife had a concert, out until late (11pm). Told her I was going to upgrade her MacBook Air to OS X Yosemite after boys were in bed...
    HopefulDude HopefulDude 36-40, M 17 Responses Oct 18

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    Staying Married for the Sake of the Kids - The following article published in Teen Vogue this month was written by someone who's parents divorced when she was a teenager - we...
    CherishMe2 CherishMe2 51-55, F 16 Responses Oct 22

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    When I was younger i hade 2 girls from work dress me i wore panties to work one girl saw as I was bending down so she told her friend who worked there and it was at a video store...
    girlyboy09 girlyboy09 26-30, T 5 days ago

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    This is the first time I'm telling this story. I don't want sympathy and I'm sure a lot of you will think I'm stupid. I have a boyfriend. His name is, let's call him, Stephen. I've...
    thatgirl0926 thatgirl0926 18-21, F Oct 11

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    I met my boyfriend in art class in eleventh grade.I always saw him around school, but that was the first day we actually talked.He sat next to me.I was making something unique with...
    ChelseaMonroe ChelseaMonroe 22-25, F 2 Responses Oct 15

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