I told Pearl I wanted to go back to Fondler’s, which she seemed sarcastically enthusiastic about. She gave me this look when I caught up with her outside. “I just don’t want to go alone, or be alone with my thoughts right now,” I tell her.

“I can respect that,” she says. “Anything, in particular, you had in mind?”

I know she’s asking about buying something. I smirk, “well I saw this neat saddle bag the last time we were there…” I trail off, and she rolls her eyes, getting the joke that I’m obviously not going to a store called “Fondler’s” to pick up souvenirs. “To be honest, I haven’t put much thought into going back. I just think it’ll be fun. We get a lot of trouble out of us while we’re out together.”

“I love that about our relationship,” she comments. “We can just be so, open with each other. While still sharing a good bit of laughs.”

I nod in agreement, also chuckling at her poor grammar. “Maybe I’ll try on some more lingerie.” I say the last word slowly, seductively. It’s as if the word itself mustn’t be used unless flirtatiously or sarcastically.

“I wouldn’t mind,” she jokingly flirts back. “Have you even worn either of your other pairs of panties since the first time you tried them on?”

The reminder surprises me. “Come to think of it, no I haven’t. It never really occurred to me to just wear them for fun. I mostly want somepony else to see me in them.”

She laughs. “Well I’d be happy to see you in them, but they’re not totally acceptable in public.”

“It’s a step up from my regular outfit,” I joke.

“I thought you didn’t like that joke?” She reminds me. Which makes me laugh more. “It’s more the idea," she continues, "I think. You wear something like that, to draw attention to that area. Without ‘em, ponies will just see you the way you are.”

“I get that,” I confirm. “Maybe I need some more lubricant?”

“There’s no way you used that whole bottle for one time.”

“How was I supposed to know how much to use?” I jest. Her jaw drops open, without words. She doesn’t know how to respond. Obviously, I hadn’t used all the lube in the bottle for a single session. “I’m kidding, I still have plenty.” She sighs heavily.

After a few steps, she brings it back up, “How was it, by the way?”

I take a second to respond. First confirming, “Using the toy?” She nods. I feel a little blush in my cheeks. It felt awkward to just start talking about it so casually, though in truth I had wanted to talk about it to someone since I’d done it. “I thought I already told you…”

She rolls her eyes. “You told me how your anus felt afterward. I want to know more what you learned from the experience.”

I take a second to ponder the inquiry. “Well,” I begin, “it probably wasn’t a great idea to take it all the way to the base the first time.”

Her eyes go wide so quickly that I jump back slightly at the surprise she gave me. “You took that whole thing? On your first try?”

“Well, I had already been going at it on the thing for a couple minutes, and I used plenty of lube…” Thinking back, “maybe a third or so of the bottle… It felt, like, really good I won’t lie. The ring kinda hurt, which makes me think I should’ve, like…
I dunno stretched myself first?”

“Well, yeah,” Pearl cuts in. “It’s a good idea to prep the opening before really going at it.”

“Sure, now you tell me,” I tease.

She chuckles a bit. Then, “Yeah, just… Stretch, your… hole before-hoof. With a hoof, or a smaller toy.”

I nod like those are pretty good suggestions. I accidentally meet the gaze of a stallion walking past. He looks away quickly and pretends he didn’t see me, so I did too. It was basically city etiquette to pretend nopony else was around, unless it put you at a direct inconvenience. In which case, it was always the other pony’s fault. It didn’t always go like that, especially for somepony like me, apologizing profusely whenever someone ran into me for not watching where they were going.

After a year living here, it became second nature to not care at all if anyone could hear or see me, because they were probably in such a hurry, or having their own conversation, that they didn’t have time to listen in on anything I said or heard. I know I barely bothered to hear what anypony else said, let alone remember what it was beyond a second of their passing.

“Or a tongue,” Pearl mumbles.

I freeze in my tracks. Luckily no one runs into me from behind, but I still start right back up at my previous pace, just in case, then laugh silently, embarrassed.

She grins innocently. “I’m just saying, it’s a viable strategy.”

I laugh some more. Honestly, it never occurred to me, but she wasn’t wrong.

She makes some more dirty jokes at my expense while we trot the last few blocks to the store. I wasn’t sure if it would be open at this time of day, thinking it was more of something you’d want to do at night, but they were open and had a steady amount of traffic coming and going. I suddenly had a second thought about going in. The first time wasn’t so bad; I was less involved in myself, and there were fewer ponies around.

Pearl holds the door open for me so I figure there’s no turning that down, better just go inside.

“Where to first?” She asks.

I look around, seeing only five or six ponies total; two pairs I assume are couples and a few lonely ponies here and there. I look toward the back corner hiding the toys and tools and such, interested in browsing what else they had to offer. Then again, if I became too infatuated with something fake, how would I feel about the real thing? What if I got so used to so many toys that my future boyfriend just didn’t measure up? That’d be depressing…

Pearl grabs my hoof and starts leading me to the back. “You were talking about how you wished you’d prepped, right?”

I begin blushing, suddenly thinking every other patron can hear every word either of us says. The store is noticeably quieter than outside, but the same rules applied: just because it was possible for them to listen, didn’t mean they were. Most of the time they weren’t because that’d be rude. Plus, they have their own business to attend to.

At one point on our way to the back, I see a stallion I apparently recognize as the lonely fellow we scared out the last time we were here. This time he was with a spry young mare… looking at blindfolds and gags.

I look away, not wanting to be rude by investigating their otherwise private lifestyles.

Pearl drags me right back to the shelves we visited before. There are no other ponies there at the time, but I saw a middle-aged looking mare walk away as she noticed our approach.

Pearl picks up a small black object from a shelf beside the assortment of dildos. It looked like a rounded arrowhead, and much softer to be sure, with very gentle curves and a flat base separated from the rest of the rubber by a short little handle. Within the first glance, I can guess where it’s meant to go. I give Pearl a look as if to say, “Are you serious.”

She groans, “Seriously. It’s called a plug.” Then quieter, “a butt-plug. Basically, you use it to keep your tail-hole comfortably wide for whatever you’re about to put in it.”

“That’s hard to believe.” I take the object from where she suspends it in the air and inspect it more closely. “It looks like once I get past this wide part, my… I dunno, my ring would just close right around the skinny part here.” I gesture to each part as I explain my confusion. “I mean, sure it’ll spread me nice and even, but once it’s in—”

“I don’t know how it works, okay? Just, put it in carefully, leave it in there a while and it makes the next dick you take that much easier.”

I have to laugh at her excellent maneuvering of the conversation. In the end, she finds anal sex just as awkward a topic as I do. I wonder what inspired me to go into such depth in the first place. Maybe I’m finally getting out of my shell…

With a thought, “What size should I get?”

I look over the shelves at different sizes, colors and, oddly enough, designs. I just find it strange, is all, that if the plug really only has one purpose–to go in and stay in–why would it need a spiral design? Or need to look like anything but a plug?

“I suppose you might want to start small, unless you think you can get a bigger one in you…”

“I don’t know. I’ll probably want one bigger than my toy, right?”

“Not necessarily. If that toy’s the only thing you’ll be taking for a while then you only need to keep yourself prepped for its specific dimensions.”

“That makes sense,” I agree. “But what if it’s not the only thing I take? How big are most stallions?”

She lifts an eyebrow, still glancing over the rows of plugs, “How big are you?”

I flush a little, “That’s not really something I—”

“I’m just saying,” she cuts in, looking at me for a second. “You’re probably average size, right? So if you think you can take your size, or need to practice…” She trailed off to let it sink in, which it did. “If you want, get one that’s almost as wide as you, or just a little bit wider.” I snicker suddenly and she catches it and asks, “What?”

“I don’t know, just,” I’m grinning foolishly at the thought. “Talking about me… well my penis, as ‘me,’ it’s just a little silly I think.”

She laughs a bit too, “I guess so. I don’t even know where that started…” It was a curious subject, to say the least. “Why do we refer to those, as ‘them?’”

“I really don’t know, but now I’ll never take it seriously again.”

“Ha, yeah thanks a lot for that.” We laugh a few seconds more. Then, “So whatever you want, I guess. Oh, but not the corkscrew one. As easy as it might be to put in, it might also come out just as easy.”

“That makes sense.”

In the end, I went with a dark purple plug that I thought was approximately similar to “my” width, which Pearl assured me was likely within the average width of any given stallion’s penis.