Tuesday, September 02, 2014

Hounded by Exes

I thought queer dating was incestuous, but queer-plus-kinky dating takes it to a whole new level. I like to be friends with my exes, or to at least end things as cordially as possible, but if someone mistreats me or if things felt really bad, my normal course of action is to walk away and cut ties.

I've had a string of relationships this past year or so, in which I came to discover things that I couldn't accept and things ended poorly. I want very much to never hear from them again, but instead, I'm faced with these women constantly due to mutual friends, clubs, interests, and events.

Do you know what it's like to be constantly bombarded by exes that you don't particularly want to see ever again? Ones that you're not on speaking terms with, for very good reason? Maddening, that's what.

There's one that just started being active at club functions, so I feel social pressure to be nice, even though I don't want anything to do with her. One is a prominent bootblack, which means I encounter her constantly through mutual friends and events. Another has gradually become friends with a bunch of my friends, independent of me; two of her best friends are in my club, one of whom has obviously been told a bunch of stuff because her attitude toward me is different than toward other people. I actually extended an olive branch to this ex when we stumbled into each other at Dore and wound up feeling pretty dissed.

I feel like there's some sort of lesson from the universe here, like having to learn to deal with people instead of just cutting them off. I hate it. I like it much better when they go away and I can sort of mentally erase the person's existence.

Thursday, July 10, 2014

Onward

When my service ended recently, I was a little afraid that I'd have too much time on my hands. Two days per week were Ma'am-related alone, plus all her bootblacking events and the unscheduled times that she would request my service. My schedule felt pretty full, so I dreaded the sudden idleness. I hated that feeling when service to ex-Mistress ended; I put in so much time there per week that its absence was uncomfortable. Too much time on my hands is never a good thing, especially when I'm going through the ending of a relationship.

Happily, though, the holes in my schedule have been filled in by other things, without effort, and I haven't really felt like I miss the service. There are certain things I'm sad about and that I'll miss, especially the lost opportunity to be her bootblack apprentice, but there are a bunch of things I am quite honestly glad to not have to deal with anymore.

I never voiced it or let on, but her Sir was really beginning to annoy the fuck out of me. It started with the limitation that I couldn't go down on her or fuck her ass ("his", he said), but then continued to add further limitations like she had to ask permission to have me spend the night (which, considering that it never happened, seemed something he was not freely permitting). Then there came a work night curfew for social media and TV, which then turned into an additional visitor curfew of 9 pm. She got home at 7:30, so if I came over because she wanted something, I would only have an hour and a half to spend with her.

THEN, there were the times that he totally cockblocked me. Annoyingly, they were in constant contact via text. I was second fiddle to that phone of hers and the stupid 'ding!' that signaled a text from him. So, there were evenings when she and I were saucy with one other all night, knowing that we were totally going to go home and leap on each other. I don't know if she expressed this in their texting throughout the night or if he picked up on it, but "Sir" would proclaim near the end of the night that he wanted a Skype date when she got home, meaning instead of getting to fall into bed with her, I got sent home at the curb. That or he would declare, while I was with her, that he wanted her to come for him later on Skype, effectively cockblocking me once more. Not to mention the times that I got kicked out because she had to Skype with him.

I won't lie, I totally resented his presence in our relationship. I worked to accept it because it was a non-negotiable part of things, but I discovered it increasingly irksome to constantly have someone else's hands in my relationship. I mean, poly is challenging enough as it is, without the meddling, but this was just a recipe for resentment on my end. It's one thing if the person is my Domme and issuing orders; I might not like them, but I accept them because the person is my Domme. "Sir" was not my Dom and his infringement on my liberties was a thorn in my side.  I thought some of the rules were just plain arbitrary... like, I could fist and fuck her pussy, but not go down on her. The day things went to shit, she told me she wanted to work toward ass worship, so licking her ass is apparently okay, but fucking it isn't? I could fuck one, but not lick it and lick the other, but not fuck it. What?

He was going to come and visit for a couple of weeks in September and she stated she was taking that time off work while he was here. I was very unsure about what this meant for me and her, possibly my not really seeing her for a couple of weeks, other than a Folsom-related event I was supposed to help her with. I was a little sad at not seeing her, but mostly relieved because I didn't want to hang out with him. She and I had discussed her upcoming move and she offered a place for me in her new life with him, but it was little comfort. I just had no desire to have anything to do with him in real life. His cyber presence at a distance was already intrusive and irritating. I also had a feeling that I would be expected to defer to him as she does and I was not interested in having any part of that. Not my dominant, don't even like him, no thanks.

There are other things I won't miss; lugging that heavy bootblack stand in and out of places, being unpleasantly cold/hot and bored at bars while she blacked, being an unknowing accomplice in not tipping bartenders that served us all night, and that disgustingly dirty house and her super lazy, filthy roommates. I spent two hours cleaning her personal bathroom and four hours cleaning the kitchen -- and didn't even finish all that really should have been done. Four hours in a small kitchen is ridiculous. That place is so gross and depressing.

It's obvious, as I hash it out now, that it wouldn't have worked. It's fortunate that it happened now, only a month and a half in, rather than later, when both of us would be more attached. Not to mention, she was planning to move home, a few states away, next May. I was seriously dreading a repeat of all the feelings brought up by helping ex-Mistress pack up and seeing her off. Even if things went a million times better, it would still feel shitty; it's her going on to a shiny new life and me left behind, once again.

Instead, I'm back to what I was doing before: trying to expand my kinky social circle. I'm cultivating new friendships and focusing my service toward the community. I love my leather club and it feels really good to be around them, so I'm working on participating more and have taken on some volunteer opportunities, including being our volunteer coordinator for Folsom Street Fair. Things are pretty good.

Wednesday, July 02, 2014

Finale

I spent the days following my last post thinking and talking over the situation with a variety of people, many of which are experienced in poly dating. I was able to get a lot of validation about my position.  Once I felt more clear-headed, I wrote her a very calm and reasonable letter to state that I felt that I wasn't being heard or understood, and went on to explain where I was coming from.

A couple of days later, I got a long wall-of-text letter in reply, telling me she was shocked to have read mine and then choosing to focus on semantics and the language I chose, instead of any real issue. In fact, the only real issue here is that we each have a boundary that is in direct opposition to the other. I couldn't manage to get her to discuss this point, instead she kept trying to bring misinformed and irrelevant elements into the argument, such as wildly misinterpreted words and phrases. She seems hell-bent on being pissed-off at me, grasping at anything she can as further reason to hate me. She accused me of manipulating and guilt-tripping her. She signed off by telling me that if I felt the need to discuss it further, to bring it up with her Owner, as her patience on the matter has been exhausted.

I sat there, floored at the animosity and because so much in her letter was flat-out wrong and full of misunderstanding. It was so wrong that it felt like a punch in the gut. I couldn't let it rest like that. I wrote her back to clarify; she'd taken huge issue with my use of 'D/s' and 'poly', so I tried to explain what I'd meant. I told her I'd always had realistic expectations of our relationship and that we were on the same page there. We had only discussed that there would be other people, and we were each free to do whatever we wanted on our own time. I pointed out that we had never had a discussion about how to handle other partners, just that there would be others. I ended by saying that I understood if she felt she had to walk away, but that she'd be missed. Thanks, it was fun while it lasted.

She wrote back right away, and instead of addressing anything, took immediate offense then to my use of the word 'partners', saying we weren't partners and my using the word lets her know I'm a fucktard or whatever (paraphrased) and 'yes, it's a loaded word for me'. She then told me she was pissed off and annoyed that I couldn't or wouldn't see that not talking about dating violated our agreement. And ended with, "And that's all I got... seriously."

At this point, I realized there really was no further arguing with her and that she was hell-bent on being pissed off at me, grasping at whatever she could to justify that stance. Most of the stuff she said had nothing to do with the actual issue, they were just ways to paint me as a clueless, inexperienced poly failure to avoid having to get to the heart of the matter. Her last email made it clear that there was no rational discussion to be had and that she would derail my attempts with irrelevant details and fallacious arguments.

So...... I gave up. I didn't bother responding. I felt like anything I could possibly say would just piss her off, it wouldn't matter what it was. What's the point? Going down that road, I would be driven mad by trying to argue with someone who is being incredibly irrational and self-centered. I threw up my hands and moved on.

She, however, has not -- far from it. She is incredibly angry at me right now and it feels profoundly unwarranted because I didn't do anything! All I did was speak some very reasonable feelings, which was met with outrage and then she immediately turned on me. If anyone should be pissed here, I think it would be me, no?

Last week, I went to a mixer for my leather girl club and had the fortune to run into one of my good friends, who knows everyone in the scene. She saw that I was a little out-of-sorts and asked what was going on, so I started to tell her. All I had to say was, "Well, I was in Ma'am's service for a month and a half... we had a disagreement, I tried to talk to her about it, she freaked out, and is now super pissed and not talking to me."

My friend calmly replied, "Oh.. yeah... She does that."

"What! Seriously?"

"Yep. She's been here since, what, November? Already she's got a string of people she's done this to and everyone knows it. If she's not careful, soon everyone will avoid her."

Immediately, a weight lifted and I felt a thousand times better. Later at the mixer, I talked with another friend, who, completely independently of the first, said, "Oh, yeah. She does that."

Here I was, worried that she would be trashing me and ruining my reputation, when she is the one with a reputation! It made me feel worlds better to know that it had nothing at all to do with me. I felt like I'd received a gift, the 'why', which would have driven me crazy otherwise. It was super validating to hear two different people tell me the dirt. I now know to ask my girls about people in the future!

Pride was upcoming and my friend asked if I was going to attend a particular girl party. I told her that I'd been planning to, but that Ma'am would be there, so I wasn't going to go. "What? No! Fuck her, you're going," she proclaimed. "I'll be there. You're going."

And that is how I wound up having one of the best days ever! I asked some friends if they wanted to go, and I was able to roll up with a posse of two hot femmes and a handsome butch, all of whom are genuine, fun, and wonderful people, so I had the best company all day. Once they heard that Ma'am would be there, they all got protective and said, 'Oh, girl, we got you. Don't worry.'

We got there, I scoped the place out, located Ma'am for avoidance purposes, and got some drinks. Eventually, we made our way outside onto the sunny deck, me following them to what happened to be a rather conspicuous spot. When we first arrived, I saw her outside and she was smiling and having a good time, so I'm pretty sure she saw me because after that, she looked pissed and no longer seemed to be enjoying herself.

I was genuinely having a great time and completely forgot about her, so I lost track of her whereabouts. We headed inside to get more drinks and ran smack dab into Ma'am in the hall by the bathrooms. It took me entirely by surprise and I quietly said, "Oh, shit. There she is."

There was no avoiding walking past her and once she noticed me, she was visibly taken aback. I was nervous and in the brief moment of eye contact, I tried to smile. She frowned and pointedly looked away. I just continued the smile, shrugged a bit, and kept walking to catch up to my friends at the bar. "Well, that was awkward..."

It's cool, though. I'm glad I was challenged to face my fear in this area because I can't avoid her forever. We have friends and interests in common, which means we are going to see each other around. I would have avoided her all day, but I was gifted a face-to-face meeting, something of which I was most afraid because I wasn't sure how it would go down. I suspected it would be like this, her being pissed off and acting like she didn't know me, but I dreaded any sort of angry confrontation. So, now that I know what it's actually like, I feel much better.

I'm good, actually, and pretty much have moved on. I never had the romantic feelings or whatever she thinks, so I've been able to calmly and reasonably accept the end. Mostly, I feel like I dodged a bullet here in a bunch of ways.

Wednesday, June 18, 2014

Abrupt Ending

I've been practicing poly relationships for a few years now, with mixed results. Part of my displeasure is that I keep finding only secondary-type relationships and it's starting to wear on me a bit. What I've come to realize is that I need something a lot more safe and stable, like a primary relationship, to be able to date as I have been.

As I mentioned in a previous post, I recently started a service relationship and things have been super good. The thing is, my Ma'am has a Sir, and he takes precedence over everything and frustratingly places limits on our relationship and on her behavior in general. My Ma'am and I had clear communication about what our relationship was; non-romantic D/s with sex, play, and friendship.

A few days ago, I was over at her house to both hang out and to do a few things for her. Gave her a massage, had sexytimes, and then I got to folding her laundry. While I was doing that and putting clothes away, she was playing on her phone and made it quite clear that she was on OKCupid. Started telling me about this one hot person who messaged her, but she hadn't gotten back to them... and then it was another really hot person that she wanted to fuck.. and so on.

It bothered me a lot and felt disrespectful, so we began to talk about it, but she basically told me to check myself and to "remember what we are". Seeing that the response was 'suck it up, buttercup' only made it worse for me and I told her I didn't want to talk about it anymore.

I should mention again that I have alexithymia, which I explain to all new people in my life, and this makes it nearly impossible for me to discuss how I feel in difficult moments like this. It takes me some time to process and think about it, before I know what's going on.

I tried to hide how bad I felt until I left, because I needed time to sort it out. By the time I got home, I was angry and really hurt. I wrote about it in my journal, which helped me find words for what I was feeling: disrespected, angry, hurt. Not only that, but the feelings were really strong and it felt like a big deal... I knew we'd have to have a conversation.

I'd wanted to do it in person, but she called me because she said it was unfair to tell her that I was upset and then not talk about it. Anyway, I kept trying to tell her that it felt really disrespectful of my time. Like, I don't see her every day and the time that we spend together is precious to me. When we're together, she has my undivided attention, and I would never be browsing OKC while I was with her because it feels disrespectful and wrong.

She kept turning everything into me being jealous. 'Okay, you feel disrespected because you feel jealousy,' kind of thing. I tried to explain that I have certain limits when it comes to my partners dating other people, such as I don't really want to know the details and I have an expectation that they won't be trolling for new fucks while with me. I don't think that's all that much to ask, but it turns out she is totally unwilling to change her behavior.

She said that doing so would cross over into girlfriend territory, that she refuses to censor herself that way for anyone in any non-girlfriend relationship, and if I can't deal with it, then this isn't going to work. I personally feel like this is a hard limit for me; I don't want to know the details and I certainly don't want to discuss all the 'hot' people my partner is sleeping with or whatever. Do what you're gonna do, but I don't need a play-by-play, you know?

I feel strongly about this as a limit and I think this is going to be a dealbreaker for both of us. I am pretty sure that I can't live how she wants me to, and she is unwilling to change to increase my happiness or comfort. And let me tell you, it really fucking sucks, because she is SO awesome and wonderful and hot, and everything else is amazing.

I slept on it and then sent her a text the next day, to remind her to make a doctor appointment as she requested of me, but also to say that we needed to talk. I said that it didn't have to be immediately, but I didn't want to ambush her on our next day together, and that I thought that we should put things on hold until that happened. Usually, she's piercingly good at reading my feelings, but this time, she said that I blindsided her. "Whoa. What's going on?"

I told her that I was upset and unhappy with what had happened. She took a break and called me. Our phone conversation went much like the previous evening's; it felt like she was having an odd knee-jerk defensive reaction and wasn't really hearing me. As I kept trying to explain my position, she kept cutting me off or interrupting me, both unusual behaviors for her, but leaving me with the feeling that she wasn't really hearing me.

I told her that I want a form of a 'don't ask, don't tell' policy and that I have the expectation of my partners not trolling for new fucks with me right there. Since our time together is somewhat limited, I feel that her focus should be on me, plus with my obsessive brain, knowing less information about things is simply much better to prevent my brain from going nuts.

I've since discussed this with other people, including experienced poly folk, and I now feel certain that what I'm asking is not ridiculous, inappropriate, or whatever. Even though she told me that censoring herself that way, or not browsing OKC in my presence, 'crosses the boundary into a romantic relationship', I and other people don't share this feeling. If one partner is uncomfortable with something, the other partner should be reasonably accommodating. Not sharing details is not just something reserved for primary relationships, it's a respect and consideration thing for all relationships. I didn't think of it until after, but my friends don't unapologetically trample all over my feelings.

I realized later that she didn't even think about it before answering. Didn't stop to consider everything that she'd be tossing away to maintain her hard-line stance. I've become a big part of her life and she has started to lean on me and to need me... like, does she really have any idea what it'll mean going forward if we split? I can't help but feel that she hasn't considered just how much she'll miss me and my service, and just how much she has come to rely on it.

Right after this conversation, she defriended me on Facebook. Really? Are we in high school? She told me it was for 'privacy' and that completely set me off. Privacy for and from what? What the fuck do you have to say that I can't see? It's all the more ironic and hurtful because she and I had had a conversation about us being very private people and strongly disliking being discussed by others. So, now I get to think about her saying who-knows-what about me/us to a bunch of people who know me. Super fucking mature and awesome, thanks.

Saturday, June 07, 2014

Play Date

I've been very good lately and put in several hours of deep cleaning at Ma'am's house, so she has been simmering with desire all week in anticipation of yesterday's play date. She gets turned on by my service and obedience, which pleases me to no end, especially as she is rather expressive about it. It's a lovely change, to know what she is thinking and feeling, and so hot to me that the things I do are intensely aphrodisiacal to her. I haven't felt this desired in a long time and it feels amazing.

She has been very pleased with me lately, which for her translates directly into a desire to rip me apart. It feels a lot sexier than it sounds! So, she's been playfully threatening me with both a heavy beating and her ginormous cock, Moose. Last time, I thought she had fucked me with "the big cock", so I sputtered a bit when she told me I was in for an even bigger one. I admit, I was a bit nervous, especially after I told her so and she cheerfully pulled it out of a drawer and placed in my hands for a closer look. I definitely like 'em on the big side, but this was eye-poppingly big. It was very much like this guy. She told me to think about her fucking me with it while I cleaned for her. Hot!

Our play date rolled around and I was both excited and nervous, knowing I was in for an intensely painful and pleasurable session. She had me undress and sit at the foot of the bed, then handed me the task of putting huge Moose in her harness. It was challenging, as it barely fit in the ring, and she seemed surprised that I managed it so quickly. "Well, look at you..." she said.

She set the harness aside and sat behind me on the bed, pulling me against her and enveloping me with her arms and legs. She began to bite my neck, the most sensitive part of my body, which always makes me utterly melt. She took a handful of my hair, pulled my head to the side, and held it there, exposing my neck and preventing me from the involuntary scrunching-up that usually happens. At times, the hand in my hair would find its way to my nipple, ratcheting up the pleasure as I turned into a puddle by her soft lips and wet mouth biting, licking, and sucking my neck.

I groaned lazily when she stopped and she instructed me to brace myself against the waist-high cabinet. She started out by lightly punching my shoulders and back, then moved on to a stiff leather flogger. Starting off easy, she began to punctuate her throws with much harder force, reddening my ass, back, and legs. She put me through my paces, spanking me with leather gloves, paddling with both leather and wooden paddles, flogging, and then I heard the rattle of my cane bag being emptied.

I whimpered a little, knowing the sadistic glee she feels with a cane in her hand. She doesn't play nice and she makes sure to give me plenty of extra hard whacks that leave marks for days. I have a love-hate relationship with canes: love the marks later, but hate the actual being hit-with-them part.

When it came time for the giant cock, I asked in a tiny voice if she'd please go slow at first. Last time, she'd rammed it in there and the cock wasn't lubed enough, so it kinda dragged on my bits in a painful and uncomfortable manner. She was nice and started out very easy, and it didn't take long for me to get used to the size and be blissed out in pleasure.

I seriously love a girl who has a drive to strap-on and fuck me. Part of why my sex life with JC was so hot was that she loved packing and she really enjoyed fucking me. She had a sort of boy persona when she was wearing the cock and I found it super hot how she totally owned it. I found it even hotter that her boy persona was on the dominant side, especially because I tend to feel extremely submissive while being fucked.

Ma'am definitely has that drive and she is super hot with a cock on. She had me use the Hitachi on myself as she fucked me, me on my back and legs over her shoulders. I sometimes have a hard time getting off in positions other than on my stomach, so I was really close and dying to come, but I couldn't quite get there. She must have figured this out over our sexytimes, because she instructed me to flip over and told me I had three minutes to come. Luckily, I was almost there with even the first touch of the wand, and then she slid some fingers in and began to pound me from behind. I came in like 30 seconds, max. I should not have worried. Haha.

Today, I have bite marks, plus sore nipples and bits as souvenirs. :)

Monday, May 26, 2014

In Service Again

I spent the beginning part of this year being completely single and 100% happy with that fact. Something in me changed and for the first time ever, I found myself wholly uninterested in anything relationship-related, including FWBs. Usually, when I get to the point of 3 months with no sex, I'm driven mad by all the pent-up energy and start seeking out sex partners, but oddly, 3 months went by and I didn't even notice.

I rejected the bitchy Domme, Miss S. I found her very self-centered, so I just could never get attracted to her enough to want to do things. Something has shifted in me and I'm no longer interested in wasting time on things that are 'okay for now' -- things that aren't ideal and that don't feel 'just right'. I know my value and I'm tired of wasting energy on people who don't see it. Furthermore, I would much rather be happy single than miserable in a relationship.

Even after four months, I really felt no desire whatsoever to be involved with someone. Every time an opportunity came up, I quickly dismissed it due to strong feelings of not wanting any part of it. In light of that, it's kind of interesting and ironic that I recently sort of fell into a service relationship.

As I said, I genuinely had no interest and have instead been seeking to make friends and build my social group, which is going really well, especially since I've started learning to bootblack. My friend Boots, who is my bootblack quasi-mentor, texted me to let me know that she knew a femme redhead who was looking for a service person. Intrigued, I requested more details and it turns out that we'd actually talked a little on OKCupid back in November. I had a lot on my plate at the time and frankly, I dropped the ball, but the fact that she was presented to me again as a possibility made me think there might be a reason.

So, we met for breakfast and hit it off immediately. She thoroughly enjoyed me blushing my face off, and persisted in making me talking about my kink likes in the middle of the restaurant (blush, blush, blush...). I found her captivatingly sexy. She has this really delicious, primal undercurrent of sexiness that I find magnetic, to say the least. Things felt good, comfortable, and the sexual chemistry was practically tangible. I thought, I didn't want a relationship..., but weirdly, I didn't mind for the first time in forever. Things were easy and felt right, so I kind of shrugged and went with it.

It's nice to once again be with someone who is a service aficionado and who knows what to do with me! That is such a good feeling. She identifies as a slave and is actually owned by someone else, but she certainly has no problem dominating me or directing me to do things. She told me she's not my dominant, which I find a little confusing because her role in this whole thing is to dominate me, but semantics? Instead, she says she's my Ma'am and I'm her service girl.

She's a very experienced bootblack and seems to know everyone, which is pretty awesome! I get to learn more skills, plus I'm called on to attend to her at various events, including being her keeper when she bootblacks. Not only that, but because she is so respected and well-liked, being in her service boosts my cred as a service sub within the community. Already, a couple of doors have opened for more prestigious service opportunities and I'm absolutely certain that being her service girl has helped my case immensely.

Finally, things are looking up! It's been a long time since I was in service, like really in service to someone with a deep appreciation, who knows what to do with me. It's been a really long time since I've had truly kinky play... J just wanted to talk about it, but she never would make time to actually do it. Doubly exciting for me is that this is the first time that the power exchange with a woman has also included sexual service and I love it! I have wanted that for a long time and it's been really fucking hot so far. :)

Monday, April 28, 2014

Bootblacking 101

I've recently gotten into bootblacking and I find it really enjoyable! Getting to do the boots while the person is wearing them generally leads to a surprising and pleasurable energy exchange.

Your basic kit doesn't have to be very fancy:

* a couple of horsehair daubers (round)
* a couple of horsehair brushes (rectangular)
* toothbrush
* saddle soap or glycerin soap
* leather conditioner (4-Way, Cadillac, Huberd's, Obenauf's)
* cream polish or wax polish
* shine cloth or old cotton t-shirt
* nylons/pantyhose
* spray bottle with water
* low-lint towels (t-shirt cloths, sold in packs in the paint dept. at Home Depot, are commonly used)

My favorite polish is Kelly's, but that has little to do with performance and mostly because I love the flowery/jasmine smell. Meltonian, Angelus, Lincoln, Kiwi, and others are also popular. Really, main thing is that you want cream or wax polish and should avoid those liquid polishes with the sponge applicator bottles. Also, you'll want one rectangular horsehair brush per color of polish in your kit. You want to avoid using a brush with dark polish on lighter leather.

Notes on cream vs. wax: Cream polish will give only a light shine and is best for garments and any other items on which you desire a more matte polish. Wax polish is what you want if you're trying for a nice, bright shine on boots and shoes.

If you start to do research, you'll see that everyone has their own way, so it can get a bit confusing. The first thing is determining whether you have a polishable ('high shine') boot or whether it's oil tan leather. This is probably the hardest thing in bootblacking, because it takes a little experience with feel and the appearance of the leather to determine quickly. I read somewhere that if you put a drop of water on the boot, let it sit for 30 seconds, and wipe it off, if the leather is darker where the water was, you're dealing with oil tan. Some types of boots, like harness boots and cowboy boots, are generally oil tan, but not always.

Most high shine boots will have a smooth finish and appear glossy, although sometimes, there is too much dirt to tell. However, finished leathers aren't always hard like on high shine boots; with a softer coating, the leather will feel softer and supple. Because the leather is coated, usually with resin, it will feel cool to the touch when under your hand.

Oil tanned boots generally have a pitted look to them, a bit of a nap when you feel the leather, and are either dull or medium shiny (low luster). This type of leather will warm easily under your hand and is often described as 'buttery soft'.

I know this is very confusing when you start out, so rest easy in the knowledge that every working bootblack has accidentally polished oil tan boots at least once. The good news is that it's not harmful to the leather and is simply a sort of embarrassing novice fuck-up, so if you do polish oil tans, don't fret! Just apologize, clean the polish off, and condition.

Step 1, remove laces and set aside. If doing on someone's feet, roll up their pant legs and try to remember how they like their boots laced because you'll have to do them up again at the end.

For oil tan boots:

Get a dauber wet and mist all over the boot with the spray bottle, as well as the surface of the saddle soap. Rub the brush in the soap, then apply it to the misted surface in small circles. You're going for a nice, satisfying lather... not too much water, but not so little that it's not soaping up. You don't want the saddle soap to dry on the boot, so if you're quick, you can do the whole boot at once, but if the leather is really dry, you'll have to work in sections because the soap will dry super fast. Spritz a clean t-shirt cloth until damp and wipe soap off thoroughly. Get all up in the crevices, the tongue, straps, etc. If a boot is really dirty, I'll repeat this process. Having a small bowl of water is helpful to rinse your brush once it gets dirty, as is a cheap toothbrush to clean the catwalks and other details. When you finish one boot, set it aside to dry a little and start on the other.

Starting on the first boot, work in your conditioner, gently massage it in if you can. If you like the person, make it a foot and ankle massage through the leather. Pay extra attention to the creases because it'll help maintain flexibility where the leather gets stressed. You don't really want to use tons, necessarily. Sometimes, leather is thirsty and may take a lot of conditioner, but overall, you're aiming to leave no excess on the surface. Huberd's can take a bit to fully soak in, depending on how dry the leather was. I would condition the first boot, set aside to soak in a bit, do the second boot, and then use my grease brush (used only for conditioner) to buff off the excess. You could likely use a lint-free cloth like a t-shirt to buff off the conditioner. Too much conditioner can actually weaken fibers. Also, keep in mind, if you have non-black leather, some conditioning products might darken the leather leather a bit.

For polishable boots:

Same beginning steps as oil tan boots, but I've been cautioned against using Huberd's before applying polish. Some experienced bootblacks do it, but the idea is that Huberd's is oilier than the other products and polish won't adhere as well. I'm a baby bootblack still, so I haven't much personal experience in this matter, but a very experienced bootblack busted out some science to explain it and I'm convinced. So, basically, you can use anything but Huberd's if you're planning on applying polish. Obenauf's is maybe a bit pricey, but it's natural, soaks in quickly, and can be polished over.

Once you've cleaned and conditioned the leather (don't forget to buff), apply polish to the boot in an even coat. You can use a dauber for this, a smooth damp cloth, or your bare fingers. Get it in all the cracks, creases, etc., and be careful about getting dark polish on non-black stitching. If you do get polish on light stitching, a cosmetic (pointed) q-tip dipped in rubbing alcohol generally helps a lot. Or you can sort of cheat and get yourself white and yellow China markers, which is what the veteran bootblacks all stock in their kits to brighten up stitching. Depending on the design of the boots and the color of the laces, you may or may not want to polish the tongue, as polish will wear off against the laces. Do this on the first boot, set it aside for the polish to dry a little, repeat on #2.

Lightly mist your polish brush -- barely damp, not wet -- and starting with the first boot, lightly brush the boot in quick, repetitive strokes over one area, then change angle and do the same vigorous brushing motion while going across the same area (like an X). I find I need to do this longer than I think I do, but I suspect that I might be using more polish than necessary.

What this does is knock off extra polish, but it also is building up heat via friction to melt the polish a little and make it smooth. Keep the brush barely damp and repeat until you're satisfied. Set the boot aside and do #2.

With the first boot, take out your buffing cloth. I have a shine cloth with a soft side and a hard side, but some people use t-shirt cloths, which I've heard works just fine as long as it is laid flat with no creases. I buff lightly with the soft side, then I flip the cloth over and buff lightly with the rougher side.

To get a better shine on high-shine boots, people tend to use nylons. A little pressure is required in this step. If someone is wearing the boots I'm doing, I'll flatten the nylons like a cloth (no creases) and do the classic shoeshine back-and-forth thing on the toes and heels. You can put your hand into a leg of the nylons and it makes it much easier to rub the sides, or if you're trying to polish empty boots. You're aiming for friction and you know it's good and polished when it starts to squeak.

You can repeat the polish step as many times as you like, or even just do extra on the heel and toe.. additional layers will increase shine to make the toes and heels stand out against the rest of the shine. I personally don't do the nylon step with every pair of boots because I've found that it's best on high shine boots, and can actually reduce shine on other finishes.