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  1. #1
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    Default What do I tell my Girlfriend?

    So i started seeing this woman acouple months ago. She is every man's dream. Nice and cute, but she is my type, so to me she looks gorgeous, very sexy body, well educated, reserved in public, but a freak in bed. She is the first non-escort woman ever to massage my prostate while giving me oral. A keeper if there ever was one!!

    One day we are talking and the subject of porn comes up. she loves porn. She watches gay porn, shemale porn, all types. She only uses it as inspiration to masturbate though, not for general recreation

    Once during sex, she turned me on my stomach after massaging my prostate and starts to dry hump my ass while laying on my back and rubbing her clit. In fact she came that way. She admits to fantasizing about my ass all the time. I am starting to think I could let this girl do me with a strap-on.

    I know she is bi-curious, she often points out hot women to me. She even said she once thought about having sex with a shemale, but didnt even consider going through with it because she would be freaked out.

    I like her a lot, and this might be my only chance to share more of my true self with a woman I am seeing, and not have to hide so much about my sex life. I am looking for suggestions on whether or not, and if so, how to tell her that i love to receive anal sex. I am not sure I even want to tell her that I have had multiple sessions with shemale escorts...dont think that would go down well...freak or no freak.

    Any advice?

    -Söze



  2. #2
    Chased Thru The Woods... 5 Star Poster bte's Avatar
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    I would guess that telling your girlfriend that you have paid for sex at all would probably be a turn-off. I am not saying it will and I don't speak from experience, but I think that aspect of the conversation you can do without. If she thinks about your ass and was humping your ass, then maybe she wants to fuck you in the ass. She probably doesn't want to say it, because she doesn't know if you are into that or not. Just sit down and have a talk with her and just discuss it.


    Blood's thicker like a virgin's pussy on Homecoming.

  3. #3
    Eurotrash! Platinum Poster Jericho's Avatar
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    The truth will set you free (one way or the other )


    I hate being bipolar...It's fucking ace!

  4. #4
    Professional Poster timxxx's Avatar
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    I know her
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  5. #5
    Gold Poster Helvis2012's Avatar
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    Begin with a strap-on and see how she likes it. Go from from there. Over and out.


    This has been a recorded message.


    "That's what i thought you said."

  6. #6
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    Be easy super freak. If your girl is into that, then let ther come to you with it. But you dont want to tell her you paid for tranny hookers, have some common sense. But you have to resist the urge to blurt out wierd shit. If you even told all that to a TS, then 9times out of 10 you would be rejected then too. Think about it



  7. #7
    Gold Poster Helvis2012's Avatar
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    Quote Originally Posted by LBCDO
    Be easy super freak. If your girl is into that, then let ther come to you with it. But you dont want to tell her you paid for tranny hookers, have some common sense. But you have to resist the urge to blurt out wierd shit. If you even told all that to a TS, then 9times out of 10 you would be rejected then too. Think about it

    I agree.


    "That's what i thought you said."

  8. #8
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    Your mission, should you choose to accept it, ....

    Quote Originally Posted by Helvis2012
    Begin with a strap-on and see how she likes it. Go from from there. Over and out.


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  9. #9
    Silver Poster hippifried's Avatar
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    Don't be a wimp. Just tell her to break out that strap-on she carries around in her purse waiting for you to stop being such a putz. After a few times of that, unload about your other interests. If she insists on setting up a romp with a transexual girl, don't be surprized if she invites one or two of her girlfriends or boyfriend to cum play. Lighten up. Sounds like you found ms right. Being uptight & secretive might bring your a good thing to an end. Be honest.


    "You can pick your friends & you can pick your nose, but you can't wipe your friends off on your saddle."
    ~ Kinky Friedman ~

  10. #10
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    Suddenly I'm thinking about Richard Pryor in " Which Way is Up " for some reason!



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