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.

Self Adventure: I Heart My New Toy!!

On Saturday when I went to drop off the ropes, our meeting place happened to be right by my favorite sex toy shop. I’d just gotten my job back and my birthday’s coming, so I decided it was the perfect day to buy my first butt plug.

I get a gold star because I did such a good job of asking the salesgirl questions about which materials and lubes were the best. She steered me towards silicone and of course I chose the lavender one. I looked at the little size, I looked at the big size, and with hope (and honesty) in my heart I chose the big one. It sure doesn’t fit in there but I imagine I’ll grow into it.

Once I had what I needed, I couldn’t wait to get home. My bus took forever to show up and I was tingly and smushy for the whole ride.

Sometimes I like to get fancy for myself so when I got home I put on a purple lace top and lay down on the bed. I lubed my new toy and placed it under my ass, eased it in and felt a rush of urgency and joy. I pushed down on it as hard as I could, rocking back and forth onto it and rubbing my nipples through the lace. I did that for a long time, happy moans and wiggly butt.

When I got around to touching my pussy, it was wetter and more swollen than I’d ever made it on my own before. The harder ass-thrusts brought about eensy little squirty feelings up front—I definitely am capable. I told myself not to be embarrassed to just go ahead and let it happen when it’s time. I may have actually said it aloud.

I was so excited that I was giving all of this amazingness to myself—it was an enthusiasm that felt a lot like new love.  I got out the original Big Purple Thing, turned it on, ran in over my nipples and showed it inside, the two toys ratcheting up the sensation exponentially. At that moment I had a realization that I’m embarrassed it took me so long to get to—I turned off the Big Purple Thing and put it in my mouth. I licked it, sucked it, shoved it down my throat. I turned it back on and ran it over the part of my cheek that always wants to get slapped. I ran in over my pussy and then sucked it some more.

My entire body was thrumming and thrilled. I sat up and pushed harder into the too-big butt plug, fucking it hard and feeling my pussy open further and further, wetter and wetter. I alternated sucking off the Big Purple Thing with  putting my hand over my mouth until I was in a frenzy, then I pushed the Big Purple Thing up my hoo-ha and fucked myself hard until I came. (Not in the fancy new way yet, but still.) I couldn’t believe I’d done all that for myself! I was so proud.

Whenever my ass comes into play, though, I get a little fear-hangover from it, a little triggering. It usually lasts for about half a day. I sometimes wonder if maybe when the bad thing happened in high school they might’ve done things to my ass while I was passed out, but I think it’s more likely that it’s just garden-variety shame. There are so many layers of it that still need peeling away.

I took the rest of the night to myself, wrapped up in a pretty sheet and watched sitcoms. I am so excited for my next self-date, and the next. And the next!

Welcome to the Summer of My Ass

It’s funny to have a whole body part that I’m really just getting to know. Toward the beginning of this project, around last spring or so, I started pushing the boundaries of what I did with myself and discovered (among other things) that I have an asshole that would really like some attention.

Aside from encouraging Sweetie to put knots there when she’s harnessing me up, I’ve never really shared that part of my body with anyone but myself. There have been times when I’ve used the above Little Pink Thing during sex with Sweetie, but I was always really shy about it, putting it in myself and not really inviting her to participate, asswise. (Except to smack it, of course.)

Even with partners I felt less shy around (I feel like I can be dirtier with guys for some reason) I’ve always reflexively steered errant fingers and other things away from there, and now I am resolving to steer things toward it.

Last Saturday, Sweetie and I only had a few hours before we had to get up and clean for the in-laws’ impending visit. (That we were thinking of having sex at all shows that I’ve come a long way when it comes to compartmentalizing and getting on with things—it used to be that a family visit would shut me down for WEEKS) I put on a little nightgown and some lacy undies and Sweetie stripped down to nothing. I got the Little Pink Thing ready with a condom (Just to be safe since I don’t know what kind of plastic it is), got on all fours and put it in. I’m not usually one for buzzy things, but this one feels like a massage from the inside and a sense of calm descended over me. I put my arms around Sweetie and kissed the heck out of her.

The earth-shattering thing happened midsex when I asked her to push on the Pink Thing for me.

“Like this?” She reached around and moved it in and out gently.

“Ohmygodyes. Yesyesyes. Ohmygoodness.”

I could NOT get over it. Just the way that little bit of pressure from her fingertips on the toy turned a mild little ass-massage into fireworks and turned me into a very happy animal. I felt so inspired and grateful and close to her. I feel silly for waiting so long to invite her to be part of my ass-love, but I just thought she was too…pristine or something. Dumb. Should stop putting artificial limits where there are none.

So with that auspicious beginning, I decided I’d like to spend this summer having many things done to my asshole by others. Three out of four partners seem willing to lend a hand. Wish me luck! Hooray!

Oh, Big Purple Thing

I’ve never had my own big vibrator, and I’ve been wanting one for a while—something really insistent to shut my brain off and make me stop thinking about lesson plans for a few minutes.

So the other day when I was out window-shopping with my friend Angel Face, he helped me pick one out. It was big enough, had the right not-real look (I like the real thing a lot, but for whatever reason I don’t want a sex toy that looks real.) without too many bells and whistles or complicated punch-button controls. I was shy to ask the clerks if it was the bad plastic, so I just bought a box of condoms to go along with it.

It was the first box of condoms I purchased for myself. Sometimes I feel pretty worldly, what with the edge-play and all, but on this matter I am strikingly naïve and brand-new. Angel Face pointed out that condoms are available for free in, like, every queer space around town, and I made a mental note to start taking advantage of that.

When it came time to play with the Big Purple Thing with Sweetie, I felt ashamed. I guess I still feel penis-liking-shame around her (she has made her share of nasty comments over the years, though not recently) and this was almost like having a penis in the room, especially with putting a condom on it. (First time I put a condom on anything myself, actually—can that be right?) I felt like I was being disloyal to her, even as I was wrapped up in her arms.

It felt good, thought, of course it did, and I didn’t know how I’d gone without the sensation for so long. It vibrated my whole body and made me forget the pretty feather thing I was tickling Sweetie with. And then the memories came, and the regrets, somehow not being able to keep Bill in there, MKT and his perfect (but ultimately monogamous) penis, Mr. Popular who never called again afterwards. I miss them, I need them, not those men, but men.

My first time with a nice big dildo didn’t make me feel all sassy Sex-in-the-City-independent; it reminded me of just how needy I am on the inside. Instead of feeling empowered like a good sex-nerd should, I feel pathetic for needing a piece of plastic for something I should be able to get a human being to do. That’s not the right feeling, to be sure, but it’s the one I had.

Throughout my adventures, especially my self-adventures, I’ve noticed that new experiences can sometimes be triggering—the first time I put something up my ass, I had space-issues for days, but it didn’t stop me from trying again. The Big Purple Thing is upsetting to me specifically because I missed that sensation so much—needing something inside me that way has always made me feel too vulnerable, too out of control, and that’s exactly the reason I need to practice it. I’m resolving to try it again until it doesn’t scare me, and to go back to finding ways to let actual men into my life, even if it means answering even yet still more OK Cupid questions.