I am a straight guy, but I want my girlfriend to wear a strap-on and have sex with me. I don't have ANY idea if she would be turned on, offended, or indifferent about this request. She has told me she's not interested in anal sex, but I'm pretty sure she meant being on the receiving end; I don't even think she knows I have this fantasy. I don't want her to think I'm gay, or a cross dresser, or something. I love this girl and don't want to ruin our awesome relationship if she gets weirded out and turns me down. This is a really big fantasy of mine and I want to her so much to do it, but I also don't want her to do anything she's uncomfortable with. I don't know if I can talk to her about it without scaring her off, is there anyway to slowly coax our normal sex life into this without freaking her out with the full-fledge, hard-core images I have in my head? How do I handle this dilemma?
Desperately Seeking Strap-On
I will tell you what I tell everyone with any relationship issue; be honest and direct about it. Trying to manipulate your normal sexual activity without talking about it first is some pretty shaky ground; you may cause more damage in the long run than if you had just asked her flat-out. If you can't be open and honest with her about what you want, then how can you expect to keep the relationship healthy? Chances are she loves you a lot and wants to give you pleasure as well as make you happy (as I can tell you care about her the same way). But you still must exercise restraint and tact; you can't just hit her with your hot, sweaty, deep back-door action fantasies right from the get go. You must approach the subject gently and respectfully.
Tell her you have a fantasy and you want to know if she is interested in making it a reality. Let her know you will respect whatever decision she makes and you want to hear about her fantasies as well. Then tell her that you are interested in having her play with your ass and maybe perform anal sex on you; you might want to leave the word "strap-on" out of it until you feel out her reaction, it may be too much at once. Assure her you are not gay, nor want to be a woman; when you look back behind you during anal sex, you want a woman to be there, and not just any woman, the woman you love. You merely want to experience your sexual relationship in a different way. Be honest about your feelings for her: she is emotionally inside you all the time, but you want to feel what it would be like to have her be physically inside you, the way she has trusted you to be inside her. Explain you are willing to work with her and do whatever she needs to feel comfortable with your ass. If she says no, then move on and don't try to talk her into it.
If she seems cautious but still willing to give it a try, then start with stimulation to the perineum (the area between your balls and your anus), that will provide a way to get near the ass but not dive head-first into the forbidden black hole. Whether she is licking this area, or massaging it with her hand or a toy, clean your asshole like you would if she were going all the way that night (even though she most likely won't). She needs to feel completely comfortable with your ass if she's going to approach your back door, so be a good host and clean house before she gets there. Don't rush her let her go at her own speed, if you only get as far as the perineum in one night, be happy about it and don't nudge her.
Try reading a book on anal sex together; maybe take turns reading it to each other. I recommend Tristan Taormino's book The Ultimate Guide to Anal Sex for Women: 2nd Edition, her style of writing is casual, yet compelling. The book gives plenty of information about men as well; Ms. Taormino does not assume a woman is only interested in being on the receiving end of anal pleasure. If you two don't have reading time together, try watching the DVD "Bend Over Boyfriend" for instructional yet completely pulse raising entertainment.
Never underestimate a woman in love, she maybe fantasizing about the very same thing; you can only find out if you ask her. Bon voyage, on your anal adventure and don't forget the lube!