Tuesday Advice! Yes, it’s Wednesday. But, sugar daddies!

It’s been a while since I’ve been answering questions here, but I got one recently and have been stewing on it a bit. Here’s my stab at it.

Dear Delilah:

I hope you had a delightfully kinky May Day! Maybe the change in season will inspire a fever of questions ;). I know I have one for you!

In my kinky relationships, I am primarily Mistress. Sometimes that aspect of the dynamic extends to financial and practical matters, in which I pay for the majority of meals, evenings on the town, and even household bills. I didn’t ask for anything sexual or otherwise in return, but it always felt nice and different on the rare occasions when the roles were reversed, and I was treated. When that happened, I found myself even hornier than usual.

Still, I never thought that the concept of actually having an “official” Sugar Daddy or Sugar Mama would seriously intrigue me and turn me on, but as I continue to explore the wide world of fetishes, it’s the one I keep coming back to. I am turned on by the idea of having someone, preferably someone older, provide support in exchange for companionship. I’m not interested in receiving things like jewelry or cars, but I want to make sure I know how to get my value.

I have joined related communities on Fet Life and conducted Internet research, but you are the guru when it comes to exploration. How do you suggest I pursue my interest and be taken seriously? Have you encountered any reliable resources for those searching for a Sugar Daddy or Sugar Mama?

Thanks in advance, and have a great day!

M.

Oh, my dear, I do appreciate your confidence in me, but having the word “guru” bandied about makes me just a tad uncomfortable. Still – let’s look at this, shall we?

Let me start with a disclaimer. Having been a sex worker for some time, I have a particular bias when it comes to kinks around money. I quit in part because I wasn’t comfortable monetizing my sexuality, and that discomfort gives me a little bit of a blind spot when it comes to people who kink on it. However, I also recognize that money is just another way to exchange energy, and a powerful one at that. Our society is almost as sick about money as it is about sex, and it’s not all that surprising that they frequently get snarled up together. I know a dominatrix who used to make her clients kneel at her feet and count the money out to her, because she wanted to highlight the humiliation of having to pay her to make her pay attention to them. I, conversely, used to have them leave it in an envelope on a desk on the way in, as I wanted to de-emphasize the monetary part of the exchange. Call it differences in style, call it differences in kink, or call it me perpetuating the denial about what was really going on. I was never comfortable doing blackmail or financial domination, either.

Part of my discomfort, though, also stems from the simple fact of how easy a monetary relationship is to abuse – from both directions. A person being given money for sexual favors can leverage his or her attentions, demanding more money for increased time, special activities, or even being nice. A person giving money is in an even greater position for abuse: just look at traditional patriarchal marriage. To many people’s minds (particularly men, unfortunately), the fact that they’re paying for something gives them carte blanche to treat it however they wish: it’s their car, they can crash it if they want.

I’m saying all of this by way of highlighting the peculiar dangers in what you’re looking for: tread carefully.

Before you go ahead and look into finding a sugar daddy or mommy, I’ll ask another question: do you need the money? It sounds like you don’t, as you have had some fun being something of a sugar mommy or “mistress” yourself. If you did need the money, I might caution you against engaging in this type of play, as you may find yourself being a sex worker when you don’t want to be.

Not that there’s anything wrong with being a sex worker. But if you’re not interested in being one, this is a slippery slope: you might wind up spending a lot of time with someone you don’t really care for because he or she is providing support that you need. If you’re not realistic about that, you can start feeling pretty icky, pretty fast. And you can start allowing someone to have power over you in ways that are uncomfortable and difficult to dislodge.

If you still feel comfortable going ahead, here’s what I’d recommend.

Start off just playing with this fetish. As with most things in kink, it’s a good idea to dip a toe in and do some role play first rather than diving in collar-first to a 24/7 arrangement. You might even try this with someone you’re already kinky with, who is willing and able to pamper you a bit financially. Go on a weekend with them, where they pay for everything, and in return, make yourself available to them in whatever ways they like (within reason).

Here’s where another caveat comes in. We all know how fun it is to play with power dynamics – that’s why we’re here. Sometimes it’s really fun and challenging to push yourself to do things you might not ordinarily do in order to please your dominant. Keep in mind that when money enters into these kinds of dynamics, it can get really blurry: women especially are burdened in this society with a lot of guilt telling them that they have to do or put up with certain things because after all, the guy is paying for everything. This goes back to my original caution: be sure you don’t need the money too much.

If you can’t find someone to experiment with, and/or if the experiment is successful and you want to dive in, you’ll need some resources – which is what you asked for to begin with. (Gods, Delilah, yap much?)

The hottest site for this right now is called Seeking Arrangement, and it puts together rich older folks with “ambitious” younger folks. It’s free to join if you’re the “sugar baby” (which term gives me the heebs, for some reason). Also, the guy in the picture on the front page of the site is smokin’. Unfortunately, the site is a bit creepy in terms of condoning extra-marital affairs and citing “human nature” and historical references about concubines. It seems much more focussed on the monetary aspect than it is on any potential fetish, and it sounds like you are more interested in playing with how “dirty” the whole sugar daddy thing is than you are with doing it seriously. Also, are you 19?

If you search for “sugar daddy” on Google, you’ll get a bunch of sites like this. A search on “sugar daddy fetish” turned up Alt Sugar Daddy, which focuses on people who are kinky but “also appreciate the finer things in life.” This might be closer to what you’re looking for, but I definitely wouldn’t discount the potential creep factor here, either. You’ll probably be a hot commodity there, though, if you’re already someone who has her freak on; this site is more likely populated with sugar daddies who have odd tastes than with kinky people with a sugar fetish, if that makes sense. My bet is that here you’ll find guys who want women who will let them piss on them or suck their toes, or who will want you to wear particular clothes, or whatever.

Something you have to decide is whether you’re wanting to play with the sugar daddy/mommy idea in a kinky context, with the self-awareness and slight irony that that implies, or whether you want to enter into a real arrangement like this with someone who may or may not be kinky in other ways, or be able to see the potentially problematic nature of such an arrangement. If it’s the former, you may want to stay within the circle of people you already know; if it’s the latter, go to town, keeping all the caveats I’ve put out there in mind.

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Got a question? Email me!

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Monday Advice, One Day Late

I am not actively involved with anybody at this particular juncture in time and I am very shy when in comes to being involved with new partners. My last partner turned out to have been a very skilled and loving Dom. This was not something that I really knew about him prior to being involved with him. However, with that experience in my past, I am pretty sure that I would be unhappy in relationship that was completely devoid of that dynamic. I find that telling people of that particular long term goal appears to suggest that I wish to escalate things sexually. I definitely wish to wait a good while before sex and an even longer while for kinky pleasure. How do I seek fellow kinksters out in the initial phases of meeting a person, before introducing sexuality? How shall I broach the subject? And, is being kinky a more fixed personality trait, as orientation is for some folks? For instance, if a person is uninterested in kink, will they always be uninterested?

-Challenged At Clever Acronym Creation

It sounds like you’re running into a similar issue to another questioner who wants to meet kinky people, but doesn’t want to talk about sex right away. The trouble here is that if you meet someone through an explicitly kinky venue, then the subject is already out there on the table, and one is almost expected to talk about it. But if you meet someone in another way, and you start to fall for them without talking about it, then when happens if you bring it up later and they freak out? Right?

Here’s my advice, CACAC. If you feel like you need kink in your life in order to feel fulfilled, I would start working on meeting people through explicitly kinky venues. I don’t mean you have to go to play parties or even a fetish night at a dance club. If you live in a major metro area, there should be a kink organization or two out there. Such organizations tend to hold munches: meetings of kinksters in non-kinky public places to meet each other and talk. Now sometimes, kink organizations are broken and creepy, and so, therefore, are the people involved in them. And even if you find a good one, you might not meet anyone at a munch that you want to pursue a relationship with. But if the vibe is good, you’re opening the door to meeting more people who have kinky interests. Attend classes and workshops. Spend some time at your local woman-owned sex shop. Or even look around on Fetlife for folks – it’s a fast-growing online community that works well for networking.

By going this route, you’re guaranteeing that your dating pool is going to consist mainly of people who already know about and want to do this stuff. The next step is finding one you like, and who’s willing to go at your pace.

Should you meet someone outside of this purview, I recommend the following: fly your freak flag a little. If you get to the point where you have him over to your place for dinner, make sure you have a flogger hanging on the wall, or whatever the equivalent is for what you’re into. Wear a pretty cuff bracelet with a D-ring on it. Keep a kink-positive button on your backpack. Be open to questions. Flirt with information. Let him know in subtle ways what you’re into, without having an explicit conversation until you’re ready.

And here’s another thing: if you’re into dominant men, it’s likely that you’re going to be attracted to dominant men. Whether that manifests itself as whips and chains and rubber or whether it just means he’s the kind of guy who’ll grab you by the hair and toss you against the wall for a good stand-up shag, you’re likely to get what you’re looking for simply by virtue of your tastes. If you get involved with someone who is inexperienced but open, you can always introduce him to the joys of kink when the time comes.

As far as your other question – is kink an orientation – I really can’t answer that with any authority, because Science Just Doesn’t Know. But I do know that people “get kinky” sometimes after years of not being drawn to it. And it seems pretty clear to me that once someone gets kinked, they don’t really get un-kinked. So you have that going for you.

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Monday Advice Time! – The Beginner’s Corner

Hello, all! Today I have two questions from people just starting out; let’s hope that I can give them some good insight and not send them running screaming from all things kink. 🙂

If you’d like to ask me a question, write me at delilah@dommedelilah.com, or if you’re really brave, comment here!

Now: on with your questions!

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Dear Delilah,

Let’s say you’re taking your first baby steps into kinky stuff. Let’s say you’re not the kind of person who just throws hirself into new things with outrageous abandon. How would you recommend finding out what it is that you like safely, both physically and emotionally?

-Aroused in Arlington

Dear Aroused,

I’m so glad you asked. There are many ways to go about this task; your job is to figure out which one works best for you.

One of the better ways of getting a sense of what you might like in the kinky world is to take a look at your fantasies. What do you think about when you jack off? What kind of porn turns you on? What things have you wished your partner would do to you – or wished you could do to your partner – when you’re having sex? This information can be invaluable when you’re trying to navigate the waters of BDSM and its offshoots. Start noticing it. Write it down in your journal. Observe trends.

The next step is trying things out. Now, a warning: one of the more interesting phenomena I’ve encountered is that sometimes the fantasy and the reality don’t match. Maybe your fantasy is something that’s simply not possible in our consensual reality: I have a client who has a giantess fetish, and while I am six feet tall, there’s no way I can be sixty. Or sometimes you might try out a fantasy and discover that in reality, it’s actually scary or uninteresting or even repugnant: maybe it’s nice to fantasize about being vomited on, but the smell, ach!

But you never know until you try, and if you’re a cautious person, the thing to do is pick one of your tamer fantasies first. What constitutes “tame,” you might ask? Depends on you. To you, tickling may be extreme edge play (it is for me; I detest being tickled). Having someone run a knife along your body without cutting may be perfectly tame. (For me, it’s extreme: I have a terror of knives.) When you think about making your fantasy into reality, how does it make you feel? Scared? Aroused? Intrigued? If it’s something closer to the latter two, give it a try. If it frightens you, try some tamer things first.

Finally, you need to share the fantasy with a partner and see if they will indulge you. If the person you’re involving is someone close to you and also new to kink, remember to be gentle and ask that they be gentle with you: you’re revealing something vulnerable about yourself, and you’re asking them to participate in something that may be intimidating. Make sure you make it clear that this is something you want to experience together: if it’s something you wind up enjoying, it’s more likely to be repeated if you both enjoy it. If you’re asking them to bottom, don’t forget to talk about safewords: they should have a word they can say that will stop all activity and give you a chance to check in. (Safewords are important for tops, too, in case you feel you need to stop.) If you’re asking them to top, reassure them that you won’t be critical during the experience; having the first experience be less intense but safe and pleasant is a good gateway to having more intense experiences later.

If both of you are new, it’s also important that at least one of you know what you’re doing. This is why it’s probably better to pick something less complicated: perhaps your partner could tie you to the bed with scarves, but you probably don’t want to be suspended from hooks just yet. There are plenty of books, classes and trainings in the Boston area and country-wide on various types of kink; I myself offer trainings for singles and couples if you are interested.

Another way to go about it, particularly if you attend kinky parties, is to approach someone experienced whom you’d like to play with, and ask them if they’d be willing to do “x” activity with you, a novice. Many experienced players are happy to “break in” newbies, and can (but may not always) provide you with valuable feedback. They also will likely already have good skills and boundaries around BDSM play, and will be able to more easily provide you with a safe environment to experience your early scenes.

Happy playing!

Dear Delilah,

As someone who has little practical experience with kink but who has recently started dating a man who is into BDSM, and is a “dominant,” I am unsure about many things: a) how to explain a willingness but a nervousness about participating in such sexual behavior b) what to expect c) where on earth this desire to be dominated came from.

-Unsure Me

Dear Um,

This is a marvelous tangle, isn’t it? It sounds like you’re on the cusp of something big for you. The question is, how do you make the experience exciting and safe and not let your trepidation keep you from going forward?

You ask how to explain a willingness yet a nervousness to engage in kinky-type sex. If this person you’re dating is a good guy (which I hope he is), then it shouldn’t be too difficult, or at least it shouldn’t come as a big surprise to him. You’re new to this, and that he knows, correct? Let him know that the idea of it turns you on, but you have some fears and he’ll need to take it slow. Make sure that you work out safewords: a word that either of you can say that will stop the kinky activity and give you a chance to talk about what happened. If he is dismissive of your nervousness, that’s a big red flag: BDSM is tricky territory, not to be entered into lightly. Make sure you can trust him before engaging in what could be risky behavior.

As far as what to expect: that depends. When I first got into kink, it was a whirlwind of emotions and sensations I never had encountered before. I started as a pure submissive, and among other things, I had some internal bridling about what it meant to be a feminist who wanted to be sexually overpowered by a man. I had some fear about giving over my power to another. But I also had (and continue to have) some of the most fulfilling and exciting sex of my life. As I grew into my kinky identity as a switch, I experienced the rush of power exchange in both directions, the sacredness of trust given and trust received, and the incredible closeness it can engender. But the experience is very individual.

One thing to be careful of is not to think that you have to be forced to endure anything that you don’t like, either to “prove” how kinky you are, or to satisfy your dominant boyfriend. While in some relationships submissives sometimes endure things for love of their dominants, this is not a necessary component of kink, and if something he does causes you suffering without pleasure (as distinguished from the pleasure one may derive from suffering “for” someone), then don’t agree to it.

And where did this desire come from? Boy, did I ask myself the same question years ago. For you, it may be coming from this person in particular, and how his desires affect yours. Or, he could be pushing buttons that you’ve just never had pushed before, that were just there waiting to be pushed. I wouldn’t worry about that part too much: not everybody’s kink comes from some childhood trauma or repressed memory. Some of us just desire a more intense experience than plain vanilla sex can usually provide, and kink is how we go about getting it.

Above all, be safe, trust yourself, remember your safewords – and check in with yourself frequently about your own power in the rest of your life. Giving someone else power over you temporarily can be incredibly erotic, trust-building, and intimate. Giving someone else control over your life, however, rarely works out well.

***

That’s it for this week. Remember to send me your questions: delilah@dommedelilah.com.

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It’s Monday, time for your letters – or, The Advice Part!

Last week was a slow one on the business front. I wasn’t feeling especially well, I had a lot of flaky callers who steadfastly refused to leave messages, and I think that the Monday snow-dump that took a crap on our fair city early in the week squelched any spring stirrings that might have been beginning.

Then this weekend came with its springing-forward and 60-degree temperatures and all of that wonderfulness.

But today it’s in the 30s again, with sleety slushy shit again, and everyone’s back in their hidey-holes until the weather warms up and the girls start wearing their sandals again.

So while you’re all huddled in front of your fires with your computers on your laps, here’s some answers to your questions!

Dear Delilah,

I’ve been exploring kink lately, and I’m a little worried that once I jump full-on into the kinky, I’ll start to find non-kinky sexual relationships less fulfilling. What has been your experience with this, and should I be concerned?

Curious And Really Excited, Fearing Uninspired Lovemaking

In my experience, CAREFUL, the answer to this question depends on a lot of factors. Do you have more than one partner? Do you have a steady partner, with whom you’re accustomed to having vanilla sex? Is that partner open to kinky sex, and if not, do you have another acceptable outlet for it? Do you actually enjoy the vanilla sex you’re having now? And what is vanilla, anyway?

I have a number of lovers. One of them hardly ever uses toys with me, and yet the sex we have – which is mostly “standard” heterosexual sex acts – is almost always kinky. Why? Because our mental relationship to each other has that content: it’s all about the type of dirty talk we choose, the ways we hold each other, the power dynamic that emerges when we fuck.

Another lover and I share an intense energetic connection. Our sex is incredibly hot, but I’d call it vanilla in the sense that we don’t engage in power dynamics, nor do we do a lot of sex acts that might be considered kinky.

Sometimes I play with people using rope and whips and clamps and all kinds of things, and we don’t have actual sex at all.

I like all kinds of things. After all, so-called “plain vanilla,” done well, is one of the most exquisite and complex ice cream flavors there is. If you already have a fulfilling vanilla sex life, I wouldn’t be too concerned about losing interest in it.

On the other hand, if you have been feeling for a long time that your vanilla sex life has been missing something, and your drive toward kinky activities is really strong, you might find that once you start adding such activities into your sex, you might not be too interested in going back. If you and your partner are both into the kinky stuff, this might not be such a bad thing – it’s not like you have to do a full rope suspension every night. Remember, kink isn’t an all-or-nothing proposition: what was vanilla sex one minute becomes kinky the next when one of you suddenly holds the other’s wrists down to the bed.

And if you have more than one partner – I’m guessing from the plural in the “non-kinky sexual relationships” part of your question that you do – the important thing is to let each relationship find its own groove. Try things out together. Find out what you like together. Sex is a kind of alchemy, and doesn’t just involve a certain set of acts or only one person’s desires. The best partner sex happens when the two of you are exploring (or in time, repeating!) the kinds of things that turn both of your cranks. For some, that might be vanilla: when my vanilla lover and I try plugging into D/s, it just feels silly and we go back to what works. For others, that might be hanging upside down from the ceiling and poking their privates with a rubber chicken.

The short version (too late) is that I wouldn’t worry about losing interest in non-kinky relationships unless you have already lost interest in those relationships. And if that’s the case, then it’s time to re-evaluate those relationships anyway.

Dear Delilah,

Strap-ons. Have you found a particular harness style that actually holds the damn thing on securely enough that you can have decent thrust control and have both hands free?

-Damn, It’s Loose! Do-Over?

I’m so glad you asked, DILDO. I have a favorite harness that I heartily recommend, and at this point (it was given to me as a gift nearly six years ago, now), there are probably others that emulate its perfect style. The original and my favorite, though, is the Venus Envy, available at Toys of Eros in Provincetown, MA, and through their online store. It’s made of buttery leather, is in a jock-strap style so you’re not dealing with butt-floss while you’re trying to fuck, has plastic climbing-type closures for easy in and out (heh), and is incredibly adjustable. They actually carry a number of great styles, including ones made especially for larger women.

I think that there are some general qualities in a harness, though, that can contribute to a nice solid fit so you can really get your hips behind your action without worrying that your cock is going to go flying across the room:

1. Material. Leather is my favorite, because it molds to the body over time, has a gentle stretch without too much give, gets more beautiful with age, and doesn’t cut into the skin like neoprene or other synthetics. Those who are against leather or who want something a bit cheaper will have to compromise on this, but I really do think it’s the best choice.

2. Adjustability. The harness I have adjusts on all of its axes; that is, each strap adjusts individually to accommodate differences in body proportions as well as size. If you’re going to pound someone vigorously, it’s important that your harness be well-secured to your body.

The other major factor is vanity. When you see the pictures of the harnesses on the models, they look all nice and sleek and smooth against their bodies. But most of us have some body fat, unlike most models. In order to make the harness secure, you may have to tighten it enough so that your fat bulges around the straps a little, which may not look especially flattering. Don’t sweat it: I guarantee you that whomever you’re fucking will be much too happy and busy getting the relentless pounding that you’ll be able to give with a harness that fits well to notice that you have a little pooching going on.

Well, that’s it for this week. Remember to email me at delilah@dommedelilah.com with your questions, or comment here on the blog. Look for the next Advice Edition on Monday the 16th!

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