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I Am A Sissy That Likes To Be Fucked With My Legs In The Air

Personal Stories, Advice, and Support 579 People

    I've always felt that the term sissy was

    deragotory and even though I do cross dress, I don't really identify with the term sissy. But I am comfortably bi and I do like to s*** a c*** every now and then, and given the opportunity I really enjoy spreading my legs in the air and being penetrated by a nice firm c***. So...
    RayanneA RayanneA 56-60, M Nov 10

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    Afternoon Delight

    My boyfriend emailed me last Monday. He had been gone to Utah for business on the weekend and was back in town and horny for some tgirl *****. I had a lot of work for the afternoon but really enjoyed the feeling of his 10" hard **** in my **** so decided to hurry and get...
    michelleats michelleats 56-60, F 2 Responses Dec 13, 2010

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    Yes.....

    This is by far my favorite sexually position. It makes me feel so fem, I love when a guy pushes my legs over my head! And takes me like his girl!!!!!
    InTransitionM2F InTransitionM2F 41-45, T 5 Responses Nov 20, 2013

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    Yes Please!

    This is the way, this is the only way. I love it. Hole up, legs up, your man up top so he can hold you and kiss you and wring the sissy milk out of your stiff clitty. The more animal my man is, the more shameless I becum.
    SissyMia SissyMia 31-35 8 Responses Nov 3, 2010

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    I Love The Face-to-face Intimacy

    Yes, I love the intimacy of this position, gazing into my man's eyes, when we are both in the throes of passion. My black-stockinged legs wildly cleaving the air, utterly beyond control as we ride towards ******.
    Silkendreams Silkendreams 46-50, M 7 Responses Dec 2, 2010

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    I would love to try this I have fantasized

    about this a lot laying my back a strong man ******* me missionary I want to wrap my legs around him pulling him it to me with every thrust while biting his neck and digging my nails into his back. God I need this so bad. I don't dress up but for this I gladly would.
    suxintx suxintx 51-55, M 1 Response Aug 25

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    Table, couch, bed, floor.

    I love being ****** on my back like a ****. Me uncle loves me this way. He loves seeing my tiny little **** poking out while he bang **** me. I like when he hold me ankles and push me feet away. Like how he hold them back while he ram inside of me. Sometime he jerk on my little...
    deleted deleted 26-30 1 Response Dec 5, 2013

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    I have never been with a man

    but my wife likes to peg me and my favorite position is on my back with legs up.
    CdKimmi CdKimmi 66-70, M 1 Response Nov 5

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    Face Up Is Best

    The very first time a man used me was face up. He preferred it so he could kiss me. he also wanted to see my face so he could tell if I was enjoying it. At first I didn't but he was gentle and understanding and took his time to let me relax and learn about what I should be...
    amandatrane amandatrane 56-60 2 Responses Feb 8, 2012

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    I Really Did It

    Iposted an ad as a CD and a picture, I am not at all passable, but I have nice latex mask and chest, with a nice set of 42 DDD **** on it and their soft and pliable, anyway, I got allot of responses, I chose a nice guy that is fit and clean, a closet gay. I made arrangements for...
    deleted deleted 26-30 2 Responses Mar 23, 2013

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    Sissybitch

    what can i say just that i am a sissy that likes to be ****** with my legs in the air so i can feel his **** ******* me hard while my stocked legs are out wide or around his neck!!just love to be ****** in the carpark against his car with my body on his boot and just my panties...
    mandiejune mandiejune 51-55, M 4 Responses Sep 10, 2010

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    Love This Position

    Even with men that i've been with that did not know the side of me that crossdresses seem to love to **** me in this position. I do love doggystyle and almost every other way but it always seems to end like this :)
    marla1979 marla1979 31-35, T 3 Responses Sep 29, 2010

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    I especially like it

    when my leg is in a pink cast and my toes are painted all pretty
    Gaylegcaster Gaylegcaster 41-45, M 1 Response Dec 8

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    High heels, stockings,

    really short skirt and a bustier on, nothing more except my Wife's collar. She's smiling, the leash in Her hands, while She drags me to F. house, my face red in embrass. "Lay there on your back, ****!" F. command as W/we enter the room and i obey, the leash tucked not so...
    SlutAi SlutAi 31-35, M 3 Responses Dec 4, 2013

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