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I Had My First Sissy Boy Sex

Personal Stories, Advice, and Support 35 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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    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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    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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