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I Want to Try a Strap On

Personal Stories, Advice, and Support 308 People

    Mistress Is Training Me!

    My Mistress has been training me with a large foot long ***** and a butt plug. I have not had Her ******* yet, but I'm training my man ***** in the hope that I'll soon be ready for Her! She told me to purchase these things and to practice, practice, practice till I am ready fir...
    sissypriscilla sissypriscilla
    41-45, M
    Apr 16, 2011

    If You Can Get Her to Try a Strap-on, By All Means Enjoy

    Although men can wear a strap-on, not sure I've had a fantasy about wearing one.  Now, getting "her" to wear one, thats a totally different subject, and one that I fully support.  I think one of the most important processes in this, is in selection of a...
    in2pegging in2pegging
    36-40, M
    Feb 24, 2009

    Strap On Wife

    Recently, my wife and I went to an adult store and bought a strap-on. We went to the hotel we were staying at, showered, and cleaned the toy. I got on my stomach and she lay down behind me. I was doing the things I usually do to her, just teasing things. After that, I performed...
    pantiescouple pantiescouple
    26-30
    2 Responses Aug 16, 2010

    Lonely Wednesday

    Ever since 8th grade when I was in the lunch line & the boy behind me got a little close to my virging area. OMG I felt I was about to burst right there. The Line kept moving closer & close together & his Sweat C*ck kept ramming me. The line died down & about 10...
    menores18 menores18
    26-30
    Oct 6, 2009

    Want Some

    I want to find or make something that will fulfill the role of a strap on for me. I wish that my wife would take me anally.  
    deleted deleted
    26-30
    1 Response Sep 6, 2009

    I Drive The Tool, You Fool

    I don't want to "try" a strap on.  I drive a strap on.I would love to find an White man in his 40s or 50s who would enjoy strap on play.I am a beautiful Black woman in my 40s. I will start off small using a slender/smaller ***** in my strap on harness.Then, after we are sure...
    ladygodiva110 ladygodiva110
    41-45, F
    3 Responses Jun 29, 2011

    I Want To Try A Strap On

    Oh yes please! I'd love to have a dominant woman **** my in my virgin *** with her strap-on! I'd love to be dressed in my sissy clothes and be told that if I like to dress like a sissy girl I should be ****** like a sissy girl. I'd then like to be ordered to take my panties down...
    jessicasissymaid jessicasissymaid
    41-45, M
    4 Responses Jul 1, 2010

    Finally!

    It has been over 10 years that I have known my wife, and we've been married for more than 4 years now. She has known of my cd habits for a very long time, since before we got married. She has also known of my desires to try a ******* for a long time as well. She has been very...
    Girlyboy1986 Girlyboy1986
    22-25
    1 Response Jul 21, 2012

    I Was Bent Over The Table............

    I was bent over the table, arms extended and clasping my hips, pulling apart so that she could get all of me. She laid on top of me, her torso firmly against mine, I could feel her nipples poking into my upper back. She was thrusting at an angle, keeping her torso against mine...
    joemcglaughlin joemcglaughlin
    41-45, M
    Dec 6, 2010

    It Would Be Fun

    It would be fun to have my wife harness on a strap on and have her take my virgin hole!  I WOULD BE IN ECSTASY!  If you have seen my other entries you know my situation.  We are going to SF this weekend and she promised she would say "yes" more on this...
    prettydar prettydar
    56-60
    1 Response Jul 1, 2009

    Pure Fantasy

    This is a work of pure fantasy and fiction. Any similarity to real persons, places or events is strictly coincidental. When my wife isn't around I like to slip into her clothes and pretend that I'm a hot woman looking for fun. I know I can't pass as a woman in public, but I like...
    sammi11 sammi11
    41-45, T
    19 Responses Sep 4, 2010

    My Third Time With A ******* Woman............

    At one point or another almost all of us get caught ************. And it is usually pretty embarrassing for all involved. I have been lucky enough only to be caught once by my wife. It was a little embarrassing, however it turned into quite a hot love making session later that...
    joemcglaughlin joemcglaughlin
    41-45, M
    3 Responses Dec 6, 2010

    Afternoon With Two Strap Ons

    One afternoon Mistress summoned me to her place. On entering i dropped to my knees and kissed Her feet in the usual greeting. She had instructed me to bring a six pack of beers. "Put the beers in the refridgerator and go and get ready." She ordered. i put the beers away and...
    jolisub jolisub
    46-50, M
    Oct 4, 2012
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