The Girl at the Sex Shop and My First Time with a Toy

I never thought I’d end up writing something like this, but there are experiences that need to get out of you or they keep turning over in your head forever. I’m twenty-one years old, I live in Medellín, and until that afternoon I’d never imagined curiosity could push me that far.

It started the way these things usually do: with a screen, an internet connection, and too much free time. I’d spent weeks watching porn late into the night, nothing unusual, and then suddenly the algorithm dragged me toward clips I had never even searched for. Men with men, men playing alone, men with toys. The strange thing was that, instead of changing tabs, I kept watching. And watching. And hard, painfully hard, with my cock printing itself against my pajama pants, not really understanding what was happening to me.

One night, after an hour of that silent game of searching and deleting the history, I typed “first time with an anal toy” into Google. Forums popped up, blogs, an erotic story site. I went into that last one and spent three hours reading stories from guys who had shoved everything up their ass and talked about orgasm as if their brains had blown apart. In the middle of the night, my balls already hurt from so much contained arousal, and I’d jerked off twice without being able to get the idea out of my head.

That night I made the decision. If so many people had tried it and all of them talked about it like some revelation, why not me? I lived alone in a studio apartment in Laureles, so no one was going to find out. The only thing missing was the toy. And for that, I had to take the step that scared me most.

At five in the afternoon the next day I showered, put on a black shirt, jeans, and a cap, and went down to the street as if I were headed anywhere else. The sex shop was on Carrera 70, in an old building with yellow walls. Fourth floor. No sign in sight, just a discreet arrow and a staircase that smelled of damp. Every step I climbed felt like a bad decision.

When I reached the door, I almost turned back. I took a deep breath and pushed.

—Hi —said a voice from the back of the shop.

The girl who helped me had her hair tied back in a long braid and thick-framed glasses that gave her the air of a librarian with a secret. Early twenties, twenty-five at most. She wore a tight white T-shirt with something written in English on it —underneath, two small breasts were outlined with no bra, her nipples pressing against the fabric— and a pair of denim shorts that really should not have been allowed. I felt my face burn before I even opened my mouth.

—Hi, uh… —I started, not knowing where to look.

—First time? —she asked, smiling faintly.

I nodded like an idiot.

—Relax, everyone comes in like that. Are you looking for something in particular, or do you want me to show you?

I forced myself to look her in the eyes. They were a strange color, like dark honey. I swallowed.

—A dildo —I said, and the word came out rough, as if I were saying it for the first time—. Something realistic.

She didn’t laugh, didn’t make a face. She just turned around, walked to a display case at the back, and started taking out boxes. I followed close behind, trying not to let my eyes stick to the curve of her lower back, to the way the shorts rode up and shaped her round ass, to the way the braid brushed her right shoulder every time she moved.

—We have several sizes —she explained, lining up three boxes on the counter—. If it’s your first time, I’d recommend this one. Medium, soft, easy to use.

I looked at the first one. A flesh-colored silicone piece, about six inches long. Nice, manageable, sensible. But something in me, I don’t know what, didn’t want sensible.

—Do you have bigger ones? —I asked, and felt stupid instantly.

She raised one eyebrow, amused. She leaned over the display case —the shorts rode up another inch— opened a sliding door, and took out another box. This one came with a printed image that did the product justice: a thick, veined cock, balls included, with an engorged, glossy head.

—Twenty-four centimeters. But seriously, if you’ve never done anything before, this is a lot.

I picked it up. I weighed it in my hand. It was heavy, cold, disturbingly realistic. I could feel everything inside me clench imagining that thing buried in me all the way to the base, and at the same time my jeans started to feel uncomfortable, my cock growing diagonally against my thigh. I looked at the girl. She looked at me. Her eyes dropped for a second to the bulge and came back up as if nothing had happened.

—I’ll take it —I said.

—Okay —she replied, and I swear I caught a slight tremor in her voice—. You’re going to need lubricant. Want me to show you?

I nodded, again without words. She took out two bottles, explained the difference between water-based and silicone-based lube, and in the end she chose for me. While she scanned the barcode she asked, as casually as anything:

—So why today?

I shrugged.

—Curiosity.

—Curiosity is good —she said, looking at me over the top of her glasses—. As long as it’s handled with respect.

I smiled without meaning to. I paid in cash. When she handed me the bag, her fingers brushed mine a second longer than necessary.

—If you have any questions —she added—, you can come back. I’m here every day except Sunday.

I left the shop with my face burning and my heart slamming against my ribs. I went down the four floors in one go, walked three blocks without knowing where I was going, flagged down a taxi, and gave him the address of my studio. For the whole ride, the paper bag sat quietly on my lap. I didn’t.

***

I got there, locked the door twice, put the bag on the bed, and stared at it for a long while, as if it were alive. Then I laughed to myself. I’d been tense for too long, and this was starting to feel like some exaggerated ritual.

I opened the box carefully. The dildo was even bigger than I remembered. I took it out, laid it on the bedspread, and looked at it like it was an archaeological artifact. I touched it. The silicone warmed quickly in my palm. I brought it close to my body without thinking much and compared it to myself. There was no comparison possible: my cock, already rock hard, barely reached halfway up the rubber dick. I let out a nervous laugh, the kind that covers something else.

Without really knowing why, I put it in my mouth. Just the tip at first. My tongue circled the silicone head, testing the shape. Then I pushed more, feeling the piece part my lips, digging into my palate, until the gag reflex stopped me. I closed my eyes. I thought about what the girl at the sex shop would look like doing the same, kneeling there, her glasses about to slide off her nose and my cock going in and out of her open mouth, a thread of saliva hanging from her chin. I felt my own erection throb against the zipper of my jeans, a warm drop already staining my briefs. I took everything off. Each garment fell in a different corner of the room.

I went back to the bed, naked, my cock hard against my belly, my chest rising sharply, my whole body asking for things I didn’t fully understand myself. I opened the lubricant. It smelled neutral, almost like nothing. I put a good amount on my fingers, warm and thick, and took a deep breath before lowering my hand between my thighs.

The first contact was strange. Not bad. Just strange. The tip of my index finger traced the seam, stopped at the closed, tight hole, and started making slow circles. My ass clenched reflexively every time I pressed more. I pushed the tip in. Just a centimeter. Like finding a button that had been installed in my own body my whole life and I’d never touched. I pushed further. The whole finger slid in and I arched on the bed, surprised by how concentrated the heat was in there. I moved it in circles, back and forth. I added more lube and pushed in the second finger. The pressure doubled. I felt the sphincter give under force, felt it settling around my knuckles. My cock was leaking on its own, without me touching it, a sticky little puddle forming on my navel. My breathing was breaking apart into short gasps. Every movement sent shocks up my back like tiny sparks.

I curled my fingers forward, searching blindly, and suddenly something answered. A warm bulge, a softer spot. I pressed and my whole body jerked from the pelvis. I let out a stupid gasp, mouth open against the pillow. I pressed again. Again. My cock was throbbing so hard I thought I might cum just from that.

When I felt ready, I pulled my fingers out and slathered the whole dildo with a generous squeeze of lube. I rubbed it with my hand as if I were jerking it off, watching it shine all over, twenty-four centimeters of silicone ready to go into me. I propped it up on the bedspread, wedged and standing upright against a folded pillow, the base pressed to the mattress. I climbed over it in a squat, knees open to either side. I thought about her again. About that last look over her glasses. About the way she had said “with respect.” About what would happen if I went back on Saturday, just before closing, and she had to teach me how to use every toy one by one.

With my left hand I spread one cheek open. With my right I guided the tip of the dildo to the hole. The thick, slippery head pushed against the ring.

I took a deep breath.

And then I went down.

***

The feeling the first time isn’t like anything else. There was a moment of resistance, a dull burn, an alarm in my brain saying, “You won’t be able to do it,” and a second later the silicone head pushed through the sphincter with a wet pop and something gave way and my whole body trembled. I felt my own ass clamp down just beneath the cap, trapping it, not letting it out. I let out a rough groan I hadn’t known was in me.

I stayed still for a few seconds, thighs shaking, adjusting to that feeling of being opened wide. I lowered another centimeter. Another. The rubber cock was slowly working its way into me, opening me, filling a space I hadn’t known could be filled. I didn’t lower it all the way at once. I wasn’t that crazy. But I went down more than halfway, and the pressure inside was so different, so complete, that I let out another groan, longer this time, almost feminine.

I closed my eyes. I imagined her there, sitting on the edge of the bed, legs crossed, glasses on the tip of her nose, watching me impale myself with that calm of hers, giving me whispered instructions. Slowly. Slower. That’s it. Bring it all the way down, to the base. Like that. Good boy.

I started moving. I came up a little, feeling the silicone slip out and leave my ass hollow, pulsing. I went down again, deeper this time, and gasped when I felt it strike something inside. The internal friction changed my breathing rhythm. I could feel my cock pounding against my stomach without having touched it yet, hard as stone, the tip red. From the slit a clear thread started leaking, stretching all the way to my navel. I didn’t stop.

Each time I went lower, lower still. On the third or fourth thrust into myself I felt it fully, the base hitting my perineum, the rubber balls squashing against my own. I was impaled to the hilt, sitting on the whole cock, mouth open, a drop of sweat falling from my chin to my chest.

After two or three minutes I found an angle. A point. I didn’t know what it was called, or whether it even had a name, but when I put a little more of my weight forward, hands planted on the mattress, the head of the dildo hit that soft area I’d found with my fingers, and my whole body jolted from the pelvis to the nape of my neck. My cock jumped against my belly on its own, spitting another thick drop. I let out a longer moan. I leaned forward. Repeated the motion. Repeated it. I started bouncing on the cock with a stupid rhythm, mouth open against the pillow, moaning broken words.

—Fuck, fuck, fuck —I muttered into the empty studio air—. How it goes in, fuck, how it goes in.

For a moment I felt like the girl at the sex shop. I felt like any girl. I felt like myself, but different. A version of me I hadn’t known existed and that had been begging for an open door for years. Suddenly I imagined her behind me, with a harness, pushing from above, grabbing me by the hair, spitting on my back and whispering filthy things in my ear. Move that ass. Fuck the cock yourself. Show me how you do it when you’re at home. I picked up the pace. Then slowed it down. Found a rhythm. The rhythm turned into something else.

My ass made a wet sound every time I came down, a sticky pop of the mixed lube. I took one hand to my nipples and pinched one hard. It was like plugging in a cable. My whole body tensed at once and my legs started shaking uncontrollably.

The first orgasm hit me without warning. Without touching my cock, without even grabbing it. I felt everything clench inside me, my stomach floor open, my ass squeeze hard around the dildo, trapping it, and suddenly a warm jet shot out with no control and landed on my chest, another on my neck, another shorter one that painted my chin. It wasn’t two short bursts. It was five, six, one after another, while I kept bouncing because stopping felt impossible. My cum slid through the hairs on my chest, warm and thick, and I kept moaning, my ass squeezing the cock as if it never wanted to let it go.

When I thought I was done, I was wrong.

I got up with my legs trembling, leaving the dildo still standing there, shiny and plugged into the pillow, coated in lube and me. I felt the emptiness all at once, my ass open, air getting in where it didn’t belong. I lay back on the mattress, grabbed my cock, still hard and slick with my own semen, and jerked off with both hands. In less than half a minute the second orgasm ripped another load out of me so heavy it scared me a little: the first spurt reached my collarbone. I laughed, panting, my chest rising and falling like I’d just run a marathon, smeared with myself from my neck to my navel.

I ended up sitting on the edge of the bed, completely emptied out, my whole body feeling brand new and my ass still throbbing, hollow, as if asking for more. It took me a long while to move. I cleaned everything carefully. I washed the toy with mild soap, dried it, and put it back in its box, under a stack of T-shirts. I got in the shower and stayed under the hot water ten minutes longer than necessary, feeling the stream run down my back and along the crease of my ass, still sensitive, still stretched.

***

That night I didn’t read any more stories. I didn’t open porn. I went to bed with a clear head, staring at the ceiling, going over everything in order. What had happened to me wasn’t like what I’d read. Mine had been something else. Something of my own.

I thought a lot about her. About the girl with the glasses. About why she’d looked at me like that when she handed me the bag, whether she’d deliberately fixed her eyes on the bulge in my jeans or whether I was making it up. I got hard again just imagining her.

The following Saturday, just before closing time, I went back up the four floors. This time my legs didn’t shake so much.

But that, if you’ll let me, is another confession.