8/26/2012 9:31:25 PM: A guide to playing with me for those born with a penis  This guide is primarily for men. If you are in possession of a uterus, it is much easier to arrange a date with me (as either a man or girl). Just ask! If we click, I'm be willing to try anything twice (maybe three times, just to be sure). This guide isn't really for you, but feel free to read and enjoy. If you're a domly-Dom sort of guy, fair warning: I might come across a bit bitchy, demanding and controlling in this article. It's really only out of necessity. I'm not nearly this assertive in real life. Especially when I dress up as a girl. I am usually quiet, soft spoken, shy and obedient. I'm not a doormat, though. Coming on too strong or being an asshole will not get you very far with me. I am not gay and I don't even really consider myself bisexual. I am sexually attracted to women. I have played with several different men over the last few years and I can enjoy it. I just need to be feeling especially femme to do so. I enjoy the attention I get from men. I find it very flattering as long as they're respectful and don't come on too strongly. Anyway, I frequently field requests from men to meet and play and I'm not always sure what to tell them. It can be very difficult for me to be comfortable enough with a man to play with him, but I wasn't exactly sure why. Lately, I've done some thinking and I think I have figured out that that there are three key things that need to be communicated or figured out if you want to play with me: What are your intentions? Compatibility Logistics What are your intentions? Be honest. What do you want to do with me? What are your short term and long term goals? Think about it for a moment and then read through some of the following answers to see what my response would be:  I just want to be friends Great! I can never have enough friends. I tend to be quite shy and introverted, though. If I'm not super talkative and outgoing, don't take offense. That is just how I am sometimes. Of course, there is still the issue of compatibility. And for friends, I need to connect on an even deeper level than I do for a play partner. If we don't share a lot of common interests (outside of kink, BDSM, sex, etc.), similar sense of humor or some cultural touchstone, then it will probably be difficult for us to bond as friends. However, I invite you to say 'hi' and see what happens. I just want to be friends (but really, I just want to hang with you because I find you attractive)I understand. We all want to spend time with people we find attractive. It's only natural. However, if not interested in connecting on some other level, it's not likely to work out. I just want to be friends (but really, I just want to get you to let your guard down so we can have sex)I get it... I have a penis, too. I'd be lying if I said I've never thought about trying this one. Unfortunately, it's dishonest, creepy and doomed to fail. You'll have better luck just being honest. I just want to bend you over and fuck youI just want you on your knees sucking my dickWow... Well, I appreciate your honesty. No, really. I'm not being sarcastic. Of course, if you ever meet me in real life, I would suggest being less crass. Seriously, though, when I'm feeling particularly feminine and attractive, the idea of being used as a sexual plaything/fucktoy or having anonymous encounters is quite thrilling. I have very little experience with casual sex and I prefer to be cautious. If we can develop a high level of trust, a regular fuck-buddy thing isn't totally out of the question. But if you're really only interested in a random hookup, it's not likely to happen. I just want you to bend me over and fuck my assI just want to get on my knees and suck your clit/dickAh... I appreciate your honesty. Most guys who contact me are looking for this sort of hook-up. Unfortunately, I am not comfortable being sexually on top with men. This sort of relationship just won't work out. Anal is right out. Receiving oral or manual sex from men doesn't really do anything for me. I just want to make out with youI just want to cuddle with youI have to admit that this is something I've never been comfortable with with men. Being intimate or romantic in this sort of way is too much for me. Kissing, cuddling and that sort of thing are hard limits for now... Maybe someday I won't have this hangup, but don't hold your breath. I just want to tie you up/down and beat youExcellent!! I'm sure we can work something out! If you don't require sexual interaction with me, then you can skip right to the sections on compatibility and logistics below. If sex is a requirement or a long-term goal, it's something that requires a high degree of trust. We can discuss the possibility. I want to make you my live-in sissy submissiveI want to turn you into my transexual TPE slaveI want you to be my wife/girlfriend/life-partnerThese scenarios make wonderful fantasies, but reality makes them infeasible. I'm married, I have a career, and I'm content with being a man most of the time. These are things that I am not willing to give up. A long-term, romantic relationship is out of the question. I'm not going to fall in love with you or commit to an exclusive relationship (exclusive with respect to other men may be possible, but I will still make love to my wife and play with women as a man). I want to be your Dom/MasterI want to tie you up/down, beat you and then fuck youYes, Sir! Well... as long as you understand that this is a temporary arrangement (but possibly, recurring). As mentioned above, I am married, I have a career and I have no interest in becoming a woman full time. A D/s relationship like this would need to work around these things. Having a framework for the relationship would probably work best. For example: 'i am your slave while i wear your collar or while i am with you in private or in a kinky setting'. If I can trust you to look out for my health and safety and to respect my limits and boundaries, the possibilities in this scenario are just about endless. Oh, and with regard to sex, it's something that requires a high degree of trust and isn't something that will happen on a first 'date'. It may take a few sessions for you to train me to be your perfect sub/fuck-toy/whatever. I like to think that am capable of more than adequately rewarding your patience. I want to be your slave/submissiveI just want you to tie me up/down and beat meI'm sorry, but when I'm dressed en-femme, I don't have a dominant bone in my body. I want to have a three-way with you and your wifeHrmm... This is complicated. I'd be lying if I said it was absolutely impossible, but perhaps you should pick a different answer that just involves me and work your way up to this down the road. I want to have a three-way with you and my wife/girlfriendI'm listening... A third person does complicate things considerably. However, if the chemistry between us is right it certainly improves your chances with any of the other answers in this section. I'm a crossdresser, too. I want to dress up with youI'm a crossdresser, too. I want you to show me how to dress upI'm a crossdresser, too. I want you to top you/bottom to you while dressed upI always find this request awkward. I'm not always comfortable around other CDs and I certainly don't consider myself qualified to teach. Perhaps it's superficial of me to feel this way, but being around other CDs while I'm dressed up spoils the illusion of femininity for me. It's less of a problem in a large social group. But 1-on-1 situations, like those involving BDSM or sex make me too uncomfortable. If you're transexual, I might be more openminded.   Compatibility This is a tricky issue. It mostly depends on the ingredients of the relationship you're seeking with me: SexIf either of us going to be interacting with the other's genitals in some fashion, then we must agree on safe sex practices. Condoms are a must for all sexual activities! Also, there needs to be some modicum physical or superficial attraction. You already have an idea of what I look like or you wouldn't be reading this. The good news is that you don't need to be some kind of physically perfect adonis or anything. I do ask that you be near my own age (+-10 years), in reasonably good shape and healthy and know how to dress nice. Bonus points if you're tall, well endowed and/or a few years older than me. The one thing I am quite picky about is hygiene. Brush your teeth and take a shower before you see me.Also, keep in mind that I am not gay. I prefer women. I am very shy and will certainly not not initiate sexual activities with men. Bondage, Flogging, Beatings, Power Exchange, Roleplay and other kinky activitiesIf our relationship involves any of these sorts of kinky activities, then the most important thing is trust. This one is a bit nebulous sometimes. Some people can do and say all right right things and meet all my other criteria and yet some voice in the back of my head will say I can't trust this person. What I can say for sure is that you must respect my limits and safe words. If bondage or rough body play is involved, then you should either be skilled with the play of choice or at least be willing to learn by practicing (preferably on someone/something not me). I'm willing to do a bit of teaching in some areas, but it would be nice if I didn't have to.Also, it helps to have some common kinky interests. I'm willing to try some new things, but it would be best if we have something in common. Of course, it never hurts to ask. I try to keep an open mind. I respond best to men that are assertive, know what they want and aren't afraid to ask for it (or demand it, if we're roleplaying a D/s scene). I enjoy it when a top pushes my limits, but respects them if things go too far (that's what safe words are for). I also am more compliant and willing to try things when I'm with someone who makes me feel feminine and desirable. Yes, my femme side is quite vain and insecure. The best way to keep me in the mood, it to remind me how hot and attractive I am. Of course, just because you I'm ok with you telling me how much you want to fuck me, doesn't necessarily mean it will happen.In terms of humiliation or degradation, I can be pretty sensitive. Insulting my femininity or intelligence is going to turn me off pretty quick. I can be ok with emasculation or calling me a slut or similar things... I think. I don't have much experience with that kind of play, so caution is advised. Social/FriendshipWe need to be able to connect on a more intellectual level here. It helps if we have similar ages, education levels, cultural backgrounds. I can socialize and be friendly with anyone, really. But if you want us to be best buds, we'll need a lot of common ground. My interests are varied, but tend heavily toward the nerd/geek realm.   Logistics I've found that the biggest obstacle to meeting and playing with me has been simply been one of logistics. Most men that contact me don't live in the Chicago area or can only meet at odd hours of the day (probably because they're cheating on a spouse or girlfriend - no thanks). I live in the city of Chicago, proper. I have a full-time job that's roughly 9-5, M-F. I'm married and have numerous hobbies and responsibilities outside of kink. LocationLiving in the Chicago area is a must. Even if you travel to Chicago frequently on business, the chances that we could coordinate our schedules to meet with any regularity is almost impossible (one night stands in some hotel rooms is just too sketchy for me, sorry). The closer you are to the near-north side of Chicago the better. If you live out in the distant suburbs, you will need to be willing to driving into the city to meet me at GD for most of our sessions. Public playMost of my dressing up and exploring of kink is done at Galleria Domain. It's a members-only BDSM club that is open Fridays, Saturdays and Sundays. I try to make it out there two or three times a month and I am able to bring guests with me when I go. All this is to say that if you're willing to meet me at GD, your chances of getting to play with me are pretty good. This is considered 'public' play, but it is possible to have some privacy there when you play. Private playIf you're not comfortable playing in a 'public' space like Galleria Domain, it is still the best place to meet me for the first time to see if we 'click'. If we've met at GD already, and we've developed a high level of trust, I would be willing to play at your place, in private. Bear in mind that this level of trust does not come easy for me. Playing at your place isn't going to happen on the first date. Or the second. And probably not even the third. I also attend the Lakeview Munch regularly. But I go there in 'boy mode' and am usually busy chatting with a dozen different people. Developing that trust here will be challenging to say the least. ScheduleAs mentioned before, I usually only play at Galleria Domain. It's only open on Friday, Saturday and Sunday nights from 8:00PM to 3:00AM. Saturday nights at the club are easiest for me. Meeting other nights of the week may eventually be possible, but my schedule tends to be really tight. EquipmentI have a small but versatile collection of toys to play with. Enough for an interesting evening. Any equipment you can supply would be welcome as long as it's clean and safe.   SummaryI hate to reject potential play partners, but I have to be realistic. Trying to force a situation that won't work out will end up just being frustrating and disappointing for both of us. If you've read this and honestly feel that we can both have fun together, by all means, send me a PM and let me know! There's no guarantee that things will actually work out, but it never hurts to try. If anything in this article is confusing or ambiguous, please ask me to clarify. If there you have a scenario that I didn't cover, let me know. Good Luck!