I would like to ask you a question.......I don't want to make a big deal about it but it's important to me so I'm going to ask....I want my first time to be special. I'm a virgin and I don't want to just give it up to the first woman that wants my ass. I want to find someone who is way cool, smart, sexy, likes to laugh, is willing to be equals in public and dominant in the bedroom. A lady who might spank me if she thinks I'm not trying hard enough. A lady who would really enjoy helping me be the best I can be. A lady who would take advantage of my desire to be orally submissive to her anytime, anywhere. I want my first strap-on experience to be very special. Do you think I'm making too big a deal out of wanting my first time to be special?? I am on a website, and most of the women that have responded seem to be mean and want little sissy bitches that they can humiliate and hurt. That's not what I'm looking for. I'd like to hear what you think I should do because I already respect your opinion.
First of all, I love the incongruous juxtaposition of a man who wants his first time to be special! Important and serious question, however. Thanks, dear reader, for sending it in. Here is what I think....
Anal play necessarily requires a significant degree of vulnerability. I find it important to trust the person you are going to allow yourself to be that vulnerable with. Perhaps consider being intimate with them a time or two without the whole anal deflowering thing so that you can build some trust and get a sense of how they play. I wouldn't hold your anal virginity up as something really special that only the right woman "deserves" to get...more that you want to choose the right woman so it is a good experience for you, her, and your ass.
Asses require warm-up before thrusting a dildo or a cock in there, especially inexperienced asses. Choose a partner who is either experienced in this or willing to gently explore with you - since it sounds like you do not want the experience to be painful. Know that asses have personalities and sometimes it just isn't an ass night. Make sure your partner will respect that, too; not force you as your dominant if you are truly uncomfortable. I suggest reading "The Adventurous Couple's Guide to Strap-on Sex" by Violet Blue...full of excellent information about warm-up, technique, equipment, lubes, etc., interspersed with some hot pegging (strap-on) stories.
Domination. There are different kinds of dominant women. If you do not enjoy humiliation or feminization, then don't choose a woman to be with who enjoys that. In other words, make sure your kinks are enough of a match. Just as there are Dommes who prefer sissy-boy slaves and feminization, there are indeed women who enjoy it when they can sexually dominate a masculine, assertive man. There is no right or wrong list of Domme/sub rules (other than consensuality) - which makes it even more important to communicate about what your desires are. Which brings us to...
Communication. Imperative. Talk about everything; What experience you have had with your ass, what experience she has had with asses and strap-ons, your interest in spanking, her experience with spanking, whether you like to be tied up, her experience with restraints, what turns your crank, what turns hers, what your hard limits are, what hers are. The importance of this cannot be overemphasized. If what she really likes is CBT (cock and ball torture) and you let her tie you up without discovering that...well, I think you know where I'm going with this.
A more unusual example of kinks that match: I met a woman who regularly fucks her husband in a rather rough fashion (after sufficient warm-up play). Although this does not hurt him, he does not enjoy it, yet submits to it because what gets him off is pleasing his dominant wife. She does enjoy pegging him, but what gets her off just as much is the fact that he does not enjoy it, yet lets her do it to him anyway. Their kinks match.
Enjoy your first experience. I hope you are left with a happy ass!