My Little Silver Ring Thing [F] [Masturbation] [Anal] [Confession]
I used to wear one of those little silver rings. All my friends did. We got them at this "celebration" they called it, with a band and banana bread and our pastor standing up on stage talking about purity and waiting and all this stuff I barely had any idea about. And then there was this promise we had to make, and we got these rings to wear as a "symbol of my pledge."
Whatever... I wasn't even thinking about dating, never mind having sex but apparently my pastor thought I was supposed to be.
And it got even weirder when I heard what girls would do with their boyfriends to "stay pure."
"Gross!" I would say.
~~~
I'd been staring at the dildo for ten minutes.
I was in my college dorm and my roommate was home for the weekend.
It was small. The smallest realistic one I could find online. I'd just picked it up from the delivery locker students could use to get orders.
I was 19 and had my first boyfriend, Jacob, and was still wearing my ring.
I was thinking I should probably practice before, you know...
I was committed! This was love, after all.
I had a mirror propped against my dresser across from the bed. Just big enough to see everything... including just how embarrassed I was.
I'd followed the article's advice. Every embarrassing step of it. The fiber supplement two days ago. The careful diet yesterday. The enema at 4:00 this morning when I thought the bathroom would be empty. That had made me want to die from mortification even though I was alone. I'd prepped. I was clean. I knew I was clean. I had to be... right?
But my brain kept whispering: what if you're not?
Anyway, I was sitting on top of the covers with a towel over the pillow wedged under my bum to tilt my hips up. Just wearing a t-shirt, legs spread, leaning back on my hands. The bottle of lube sat next to me, cap already off.
Just in case of what? I didn't want to think about it.
In the mirror I could see everything. My thighs spread wide. The hair between my legs. My pussy already glistening. And below that, barely visible, the tight pink pucker I was about to test.
I looked clean. I was clean. The article promised I'd be clean.
"Just stop thinking, Nat," I muttered. "Just try..."
I picked up the dildo. It didn't feel as small as it looked. The rubber had this slight give when I squeezed it, but it was firm. Realistic, i guess. The head was smooth and rounded. The shaft got a little thicker toward the base.
I squeezed lube onto my fingers. Too much. It dripped onto the sheets. I didn't care.
I reached down. Found myself. The tight ring felt surprisingly soft, but clenched the second my fingertip touched it.
"Relax," I breathed.
My finger circled just a little. The lube was cold and the rim kind of tickled? Every tiny movement sent sparks through me. This was new... a little electric almost.
I started to press and felt myself tighten up.
In the mirror I could see my hand between my cheeks. Could see how small the opening looked. Could see my finger testing it.
I bit my lip and pressed a little harder.
My fingertip slipped in. Just to the first knuckle.
"Oh fuck!" I heard myself say... I don't ever swear!
The rim screamed at the intrusion. That ring of nerves firing all at once, tingling. A burn that was almost too much. But as my finger sank deeper, past that tight entrance the sensation changed. Became more of a pressure than a sharp sensation. A fullness I'd never felt in that way.
My reflex to push it out. Every muscle clenched. I could feel my finger being moved around.
"No. Relax." I whimpered out loud, "I got this."
I waited and let myself adjust. As things relaxed the burning heat around my rim turned into more of a warmth... a humming, buzzing warmth.
I pushed deeper.
It was my whole finger now. The stretch at the entrance was still there where my finger angled away, still tingling, but inside was different. Inside was all pressure and more of that warmth. I could feel my heartbeat in the walls around my finger.
I pulled out slowly. The drag back through that sensitive rim made me gasp. I squirted more lube. On two fingers.
The stretch was immediate but I pushed through it, felt it give way, felt my fingers sink into that deeper pressure.
Two fingers pumping slowly. In and out. Every stroke dragging sensation through that tight ring of nerves. And deeper, something else was happening. The fullness was pressing against... something. From inside. Creating an ache that spread forward into my pelvis.
My other hand found my clit without thinking. The moment I touched it, everything connected. The pressure inside. The tingling at my rim. The direct pleasure at my clit. Like they were all the same circuit suddenly lit up.
In the mirror I watched myself. Watched my fingers disappear. Watched my face flush. Watched my tiny boobs rise and fall under my shirt with each breath.
I was ready. Or as ready as I'd be.
I lubed the dildo. Coating it. Making it shine. Then more lube on myself. Better too much than not enough.
I adjusted the pillow, leaned back further so I could see everything in the mirror. My legs were spread as far as I could. The tiny dildo looked huge in my hand. Too big. But I'd committed.
I pressed the head against my asshole.
The pressure was immediate. More than my fingers. Way more. My body resisted. The ring of muscle clenching automatically, trying to keep me out.
Or keep something in.
That's what it felt like. Like I needed to push. Like my body was confused about which direction things were supposed to go.
"It's okay... normal," I was panting. The article said that. Said it would feel like you need to go. Said to push out gently, not clench up.
I pushed. Not the dildo. Pushed out, like I was trying to... god, this was humiliating even alone. But I did it.
The pressure changed. My body opened a little. I pressed the dildo forward at the same moment.
The head started to sink in.
"Oh fuck. Oh fuck."
It felt wrong. Not painful yet, but wrong. Like everything was going the opposite direction. My brain screaming that things come OUT of there, not IN.
But I kept pushing, watching in the mirror as that tight pink ring stretched wider. As my body slowly accepted it.
"Breathe. You're clean. You're fine. Just breathe."
The head was almost in. Right at that point where it felt impossible. Where the stretch was burning and my body was trying to push it back out and I was terrified to look at the dildo when I pulled it away.
I pushed harder.
The head popped through.
"FUCK!"
I froze. Every muscle locked up. My whole body shaking.
In the mirror I could see it. The dildo lodged in my bum. Just the head. My hole stretched pale around it, gripping it. And everything was clean. The rubber was still just shiny with lube. Nothing else.
Thank god. Thank god!
I wanted to pull it out. Wanted to stop. But I also wanted to see if I could do it. Wanted to know what it felt like all the way in.
I held still, panting. Let my body adjust. Slowly that sharp rim burn faded to a throb. The ring of muscle still stretched tight around the shaft, still sending signals, but they were changing. Less alarm, more humming.
Another inch. I felt it slide past that sensitive entrance and into the deeper channel. The rim stopped screaming and started singing. A constant hum of sensation. And inside, the pressure built.
"Good girl. Good bummy." Bummy?
My voice surprised me, but felt so natural.
Another inch. I could see it disappearing into me. Could see my rim stretched pale around it, gripping it. Could see my pussy getting all wet.
My fingers found my clit again. The moment I touched it, everything shifted. The deep pressure inside my ass suddenly felt like it was pressing against something from the other side. Creating an ache that spread through my whole pelvis. My clit wasn't separate anymore. It was all connected. All the same network of nerves lighting up at once.
I pushed deeper.
Halfway now. Maybe more. The thickness was constant. Unrelenting. And that internal pressure was building. Pressing against places I didn't even know could feel sensation. Like the dildo was reaching something through the wall, touching my clit from the inside.
"Good girl! Good girl!"
I started moving it in and out. Tiny little strokes. Every time it moved, I felt it in layers. The rim responding to the drag, that electric tingle. The deeper pressure shifting, releasing, throbbing. The sensation was still weird, still felt like the wrong direction, but that was ok... it was more than ok.
I pulled it almost out, just the head still inside, then pushed back in. Faster this time. I was getting it.
I glanced at the dildo. Still clean. Just lube. I was good.
The relief mixed with the pleasure and suddenly I wasn't afraid anymore. I could do this. I was doing this!
And I began to fuck myself with it. Watching in the mirror. My small boobs bouncing slightly under my shirt with each thrust. My thighs trembling. My pussy glistening and wet. And that rubber cock disappearing into my ass over and over. The rim stretched around it, the internal pressure building, that ache spreading deeper into my pelvis with every stroke.
My fingers worked my clitoris frantically now. The two sensations weren't separate. They were feeding each other. The fullness in my ass made my clit even more sensitive and my clit made the my bum feel like... like something that was building toward a peak.
"Oh fuck. Oh fuck! I'm gonna..."
I pushed it as deep as it would go. All the way. As far as I could take it. Held it there. The rim stretched tight. The pressure inside me massive. And something responding. An ache that had spread through my whole pelvis.
Boy did I cum hard!
The first contraction was way different. My pussy was clenching on nothing but my ass clenched around rubber and suddenly I could feel the orgasm in a way I never had before. Feel the pelvic floor muscles gripping, releasing, gripping. Feel them working around something solid. Each contraction squeezing the dildo, creating more pressure, which triggered another contraction.
It built on itself. My whole body convulsing. The dildo still buried in my ass. Every clench making the rim sing. Every release making me aware of the fullness. The intensity was blinding. It wasn't just my clit, it was everything! My whole pelvis spasming way deeper than ever,coming from places I didn't even know could feel like this.
When it passed I fell back with the dildo still inside me. I could feel my ass clenching around it rhythmically still, pulsing. Then slowly, I pulled it out.
The sensation of it sliding free was almost as intense as it going in. That reverse pressure. That empty feeling left behind. I watched in the mirror as it popped free, as my hole gaped for a second, pink and puffy, before slowly closing.
I looked at the dildo in my hand. Clean. Just lube and my own wetness coating it. I brought it closer to my face.
~~~
But Jacob never asked... and when I mentioned it later (a little hopefully) he was like no! That's cheating. We need to wait.
He's such a good guy.