OMG I Almost Forgot This Awesome Ass Update!

Waaaaaay back during the Steampunks in 2013, I remember being jealous of Steampunk Girl’s story about her first anal sex. Her guy at the time had been so gentle, so careful, she said. He listened to her and let her go at her own pace, making it about intimacy, not conquest or transaction.

Marooned as I was with Steampunk Guy and my main partner, Divorce Grief, I couldn’t imagine a man ever being that kind, that tender towards me.

I’m kinda glad (Though still irritated!) that my Ass Project with Steampunk Guy got vetoed on account of feelings, because my ass journey with The Shy One was beautiful. I don’t remember exactly when my asshole came into the mix, but I love the memory of him playing there sweetly and lightheartedly, mischievous and amused. Standing over me, next to me, or behind me while I was on my knees.

Whereas Steampunk Guy would have ripped off the Band-aid (Probably a little traumatizingly) with gusto and wrecklessness, the Shy One was in it with me. He tried a few times, after lots and LOTS of other things, to enter my ass, but, though I relaxed my jaw (Like I learned in that one anal sex class I took!) and took deep breaths, I couldn’t convince my inner sphincter to relax. He tried, ring of pain, he stopped, repeat. Deliberate, responsive. A dream come true as he almost always was.

The closest The Shy One and I got to anal sex was during his after-the-big-trip visit. He’d missed me and he wanted all of me—even fucked me even though I was (I almost always was!) on my period. I wanted him to have all of me, and I pushed through the pain as much as I could. He was too big, or I was too deep-down tense, but it was close. He was inside me in a way that was totally new, in a way my body and my curious mind had wanted for SO LONG. Painful as it was, I was woozy with gratitude and wildly, helplessly in love, even more than I’d already been.

So part of the dream came true, hooray! Cue choir of slutty angels! But then, jetlagged and getting sick and also just him, he withdrew afterwards, both went home and became a little less reachable, and I felt abandoned. Abandoned is a big scary dramatic word for a grownup to be using, but there we are. In those needy, vulnerable, most love-dizzy moments, he went away from me. Even if he only withdrew a little, I felt foolish, lost, stupid. I felt like the world was being taken away just as quick as it had been given. Like the sun had stopped shining.

(I do wonder how much of that emotion I owe to my own trauma. I kinda wish he and I had been able to sit down and sort out our traumas like laundry. I wish I could know more about what he was feeling, whether those shifts to not-liking-me after sex were as real as they felt. But in the end, it’s as simple as “this feels bad” I think.)

I think, someday when I restart this part of the project, I’d like to be kinder to myself about it. I’d like to hold out for someone who wants to be with me after. A guy who feels the afterglow with me and wants to bask in it. Somebody patient who can pat my head and soothe the vulnerable feelings. He’ll bring me fizzy water and tell me what the experience was like for him. We’ll talk all night.

Oh Wait, It Wasn’t My Drama

I’m sorry to revisit the same stupid playdate-that-wasn’t over and over again, but it’s still weighing on me and it’s still taking away my fun. This seems to be the month of unpleasant conversations that give me lots of insight—this morning, when I touched base with Steampunk Girl to apologize for not saying hello and tell her that I miss them, I found out the truth about those cancelled plans: It wasn’t my expectations and drama that he was aggravated with, it was drama and expectations that she invented and projected onto me.

It turns out that she was upset that I hadn’t cancelled after she explained that I would need a more loving situation for my first ass-time. In fact, I had cancelled, but then I uncancelled when I realized that we weren’t the same person and didn’t need the same things. I felt perfectly capable of doing the gentle breaking-it-in parts myself (I think we’ve established that I’m awesome at that!) and taking care of the emotional parts on my own too. There are many other valid reasons besides love to play with somebody, and in this case I chose him for competence, chemistry, and release. And also because (I thought) he was my pal. I think I’d have rocked at that playdate, if the planning process hadn’t turned crazymaking.

She was then bothered when I declined to have my first anal time with Cute Master, which she’d deemed a more loving situation. Actually, it probably was, and CM may still get the honor, though it would only be in the most casual and matter-of-fact of ways. But even if CM WAS the better choice, who in the world was SHE to decide that? Whose asshole are we talking about here?

It was also her issues causing the schedule mess—she thought I’d have all this “aftermath” that he would have to deal with, even though I’d already taken responsibility for that part and asked him to just tell me when he was expected home. All that I’d really asked for (besides wanting to make him cupcakes) was a time-margin away from the school week so I’d be more relaxed, a high sex-to-snuggle ratio, and to be treated gently about the scheduling part.

I did romanticize the friendship, but that doesn’t mean I expected more than friendship. Regardless of my feelings, I never asked him for anything that went beyond the bounds of an FWB or play partner. And even if I did, all he had to say was no, there was never any reason to put me down and e-yell at me about it.

All this time I’ve been feeling like I failed to be friends with them, especially with her, but they were the ones who dropped me over one mismatched set of expectations, most of which they’d invented. They were callous, mean, and defensive all along. It if weren’t for something she decided I needed and shouldn’t have, the plans would probably have come and gone, a nice story and a happy step along the way, and I could have kept my muse and friend. But I guess if he let all that happen to me, then it was never really a friendship to lose.

I wish this had been a conversation with him and not a way-after-the-fact whisper-down-the-lane with her and more stupid paragraphs. I wish he would have acknowledged that I deserved better, that I had the right to prefer whichever partner I preferred, that just because her first time meant “loving” and “aftermath” didn’t mean that mine had to. It’s helped to realize that for all of my mess, I’m actually much more self-contained than she is, and certainly less insecure.

Of course any good poly reader could say that all of this would have been avoided through direct communication and a more transparent approach by all parties, but I knew those things weren’t there for them from like the second date and I proceeded anyway. I hope that I can treat myself more humanely in future partnerships—how many times have I said that?

As for the dungeon, TPG was so sweet and posted pictures of her bruises just as if I were a real Dom. Hopefully Old-Timey Guy will forgive me for running out, I’m sure he had a million other fun things to do. I may not go back for a while but when I do, I hope that I can find the brave person I used to be there, or at least find myself able to cry soulful tears.

A Strange and Lovely Day Part Two: Some Literal Fireworks

Steampunk Guy texted that I should wear a butt plug to the class, but I confessed that I still didn’t have a wearable one. I forgot to mention that it wasn’t a hands-on class, but I don’t think he would’ve cared. The class was at a toy shop, I did start to think that if I found the right one, it might be fun to wear it to the party.

I learned a lot in ass-class. My favorite fun fact was that it’s easier to relax your ass if you relax your jaw. That’s a handy one since I know I need more day-today relaxation if this project is going to turn out as well as I want it to.

I think I’m proud that, when the teacher asked if she could skip one section of her lesson, I was the lady who piped up and said “I would like to hear about enemas.”

Take that, shame! I want to make everything nice.

All in all, I was really glad I’d signed up—it helped me to feel much more oriented and also gave me an excuse to buy some more pillows.

Lots of people stayed after to ask more questions, but I went downstairs to shop. “Do you have a butt plug I can walk around with?” is another thing I’m proud to have said, especially when I consider that two years ago when I started this project, I had a pretty strong fear of sex toys.

I ended up going with a little metal one because I’d heard women recommend them so often and because it looked just like a piece of jewelry. A text came through from SG suggesting that I get a glass one and warning me that the ones in the case are superexpensive, and I gleefully texted back:

“My ass deserves the ones in the case! :D”

It was a little expensive, but the very least I could do for a body part that I spent nearly four decades ignoring—it deserves everything. SG is kind of the-ones-in-the-case himself, come to think of it.

Since my life is odd, I got picked up from this happy errand by my ex-wife, who’d brought me supper. She listened as I chattered excitedly on about the class and the toy. Getting to spend that quality time with her made a fantastic day even better, even if I did feel guilty for not having driven myself. I guess I’ll have to soon enough.

I stopped home to change and texted Pretty Slave to ask if there was any reason not to wear my new toy to the party. She said she didn’t think so, so in it went, chilly for a second but not in a bad way.

As has been documented here, my driving is not necessarily awesome enough to support an altered state, but I did just fine. The hum of the car and the gentle pressure of the Little Metal Thing gave me warm spots all over my body—my knees, my shoulder blades, my blushing face. It was an all-over mood lifter, kinda like one little hit of really good pot.

In front of me on the highway, there was a fireworks display going on in a nearby town. Each burst made me feel lucky and loved by the universe. Just as I got to their exit, the grand finale came, bright and insistent. (I’m still talking about literal fireworks.) I wondered if the folks at the party were gathered outside watching (probably not) but it kinda felt like the fireworks were just for me.

Next: I go ahead and tell them to find a sex loophole.

A Strange and Lovely Day, Part One: State of My Ass

In the month or so since I chose Steampunk Guy to be my first ass-guy, I’ve been gradually getting myself ready. He doesn’t have very much time, so I’m doing the gentle parts on my own. This appeals to my sense of independence but also makes me feel (like the Steampunks almost always make me feel) like he’s rooting for me and there are many treats to look forward to.

So, every Saturday afternoon, Sweetie makes herself scarce and I climb into bed naked with a library book until the stress of the week leaves my body enough and I settle all the way back into my own skin. Once my mind starts to wander, I put the book away, feel the warms sheets on me and let myself daydream—about whatever I’m hoping will happen at the night’s party, about past adventures, about the end goal of being covered and filled up by him, crying grateful tears.

Then I’ll start to feel myself up for a while, pulling the blankets down for the feeling of showing off my breasts, loving them wholeheartedly just as I’ve done since they first began to grow. If only all the parts had been so consistently and emphatically celebrated.

Then I’ll let my fingers wander to my ass. For a while I was shy and only touched it with toys, but I’m getting less so. There’s still the psychological barrier of the ick factor—probably more handwashing than the average self-adventure. Should get around to ordering some pretty pink gloves. Also there are some other steps I need to learn, but mostly I just want to teach myself away from the shame.

Anyway, I don’t appreciate that the stress of my Friday is directly expressed inside my asshole. The harder my week has been, the trickier it is to enter, and the more pain there is once inside. I try to massage it away, but still. I must be getting my life slightly more in order though, because on this particular Saturday, everything was open and easy.

Once I’m all soft and ready, it’s time for toys. As you may know, the only butt plug I had up until then is far too big for its intended purpose (I learned that this is a common mistake. And, I think, an optimistic one.) but excellent for wiggling around on. By now, my hoo-ha was opened up and emphatically wet, like a library book that’s been left out in a rainstorm. Every fold was swollen, alert, and perfectly slick.

I usually have the Big Purple Thing out, for sucking or for using in front, but this time, I tried an experiment: I lubed it up and crouched down onto it. Whereas the butt plug, which is about the same width, kept refusing to go all the way in, the BPT went all the way in on the second try, easy and natural as if I’d been doing it my whole life. (I’m realizing it’s not the best tool for this purpose, since it doesn’t have a base, so I guess it’s back to the toy store I go.)

Nonetheless, vibrating and filled up with the BPT, I felt washed with a sense of perspective and realized that absolutely NONE of this, really, is a very big deal. I can do it just like anybody.

I went as long as I could without touching my clit—I didn’t want all of the sensations to culminate just yet. I lay back and thrust against the BPT, squeezing my nipples and moaning my head off.

As soon as I got off and washed up, I texted Steampunk Guy (still on the other side of the country) a high five and told him I’d be ready for him when he gets home. He asked some follow up questions and told me I probably wasn’t ready just yet, gave me some more tasks which I happily agreed to. It was one of my favorite conversations with him. I chose him partly for his roughness, for the catharsis, but these texts felt gentle, insightful and humane, like we really are in this particular project together. Some of my pals make fun of me for waiting for him, but it turns out I knew what I was doing. We may not have known each other long, but we’ve been through a lot of paragraphs:

“It helps not to push yourself too hard or try to prove something.”

Who, me? It surprised me that my I-have-to-catch-up-to-the-other-girls urgency was gone and had been replaced, at least in that afterglow moment, with something like faith.

I had a snack and read some more, daydreamed and texted, almost forgot that it was time to get ready to go to Intro to Anal class and then to Cute Master and Pretty Slave’s clothing optional party. I was running so late that I’d missed the window for taking the bus and parking is from the devil, so I had to ask Sweetie for a ride. My life is just a little strange right now.

Next: A pretty new toy and some literal fireworks.