r/SensualPeggingStories

I'm 18 years old and have never engaged in anything like to pegging. I was anxious when my 23-year-old boyfriend mentioned pegging, but after seeing films about it, I saw that I was also interested in it. He cleaned himself after we selected a strap and lubricant, and since I had no idea where to begin, I began sucking his cock and gradually moved in the direction of his asshole. I used some lubricant, massaged his hole with my thumb, and carefully inserted my thumb. My whole body burned with want at the moan/whimper he gave out; I had no idea I was so aroused. As I sucked him, I worked my tongue around his cock while my thumb pushed in and out of his asshole. After that, I moved to my pointer finger and gradually added another finger until I had three fingers working in and out of him. He had entirely vanished, weeping, groaning, and again calling my name. After putting the strap on and lubricating it, I pushed the dildo's tip into his hole and watched it pop into his asshole. I was amazed to see my strong, masculine partner crumble while wearing my strap. I increased my tempo and used long strokes as I gradually pushed all the way in. I had no idea what I was doing, but I quickly developed a good rhythm and began caressing his cock, continuing until I sensed that he was going to cum. While my hands caressed his shaft and my hips continued the lengthy strokes with the strap on, I leaned over and placed my mouth on his tip to begin sucking. He just moaned and cried out in delight as he came so loudly and forcefully. We had the finest sex ever that night once he cooled down and it was my time. It was a novel and thrilling experience for both of us, which is why I am so happy he asked.

https://preview.redd.it/6pvp2u532exg1.png?width=1376&format=png&auto=webp&s=d596c76fd8e77b712f5ca5f1d2aaf6f9c3bdf268

>(Prefer to hear me read it to you? I have an audio of this over here: www.peg-finder.com/diary/wide-open )

The trail wasn’t long but it was ours. Twenty minutes through pine and birch until the trees opened into this bowl-shaped clearing that caught the late afternoon sun like a palm catching water. Warm amber everywhere. Air thick with earth and resin. And silence - the real kind, the kind that only exists when you’re genuinely far from anyone, filled with nothing but birds and the slow pulse of wind through the canopy above.

I’d been planning this for a week. Ben knew something was up - I’d been too cheerful packing the backpack that morning, too specific about which trail we were taking. But he didn’t know everything. He didn’t know about the new toy zipped into the bottom of my pack, nestled next to the lube and the blanket. A strap-on with a feature I’d been dying to try: a reservoir built into the base that could release warm fluid on command. I’d loaded it that morning while he was in the shower, grinning like someone wrapping a gift they already know is going to land.

When we reached the center of the clearing I dropped the bag and turned to face him. His eyes did the thing they always do when he reads me and understands what’s coming - that half-second shift from relaxed to alert, pupils widening, breath catching before he can stop it.

“Strip,” I said. Quiet. The way you’d offer someone a dare they already want to take.

He didn’t hesitate. That’s one of the things that still undoes me about this man - when he trusts, he trusts. No nervous deflection, no stalling. Just his shirt over his head, shorts in the grass, and then him standing bare in golden light looking at me like I was the most dangerous and safest thing in his world at the same time.

I worked slowly. Let him watch me pull the harness up my thighs, adjust the straps, run my hand along the curve of something he hadn’t seen before. Let the waiting stretch until the air between us felt heavy and charged and almost sweet, the way it gets right before a storm breaks. The toy was thicker than our usual. Realistic. Sun-warm in my hand. The hidden reservoir was invisible unless you knew where to look, and he didn’t.

I brought him to his knees. Fingers threaded through his hair, gentle pressure, the kind of eye contact that makes language unnecessary. The grass was warm under him. A breeze moved across his shoulders and I watched gooseflesh rise in one slow wave down his arms.

I stepped out of my shorts. Let him watch me buckle the harness low on my hips in golden light. The toy sat heavier than usual against me - the reservoir full, a secret weight he didn’t know was coming. His eyes went to it and stayed there.

“Open your mouth.”

He did. I let him take the toy slowly, gripping the base, my free hand in his hair. Watched his lips stretch around it. Watched him look up at me with that particular wrecked reverence he only gets in open air, where there’s no ceiling to bounce anything back. I fucked his mouth gently for a minute, one hand on the back of his head, guiding the pace, and when I pulled the toy out his lips stayed parted and shining and his cock was flushed and hard between his thighs.

“Good. Over to the log.”

I guided him across the sun-warm log. Hands flat on bark. Knees in moss. I moved in close behind him and pressed my chest against his back before anything else, so he could feel how steady I was. Reached around and wrapped my fist around him. Slow pull, base to tip, my thumb tracing the ridge on the upstroke. He was already slick against my palm before I had even pushed into him.

“Easy. Breathe.”

I lined up. Went in slowly - head first, held, then another inch on his exhale, then another, until my hips were flush against him and his whole back had come up into a long surrendered arch. The first sound out of him left his mouth and kept going - traveled across the clearing, hit the tree line, didn’t come back.

“God, Maya -”

I found his rhythm on the second stroke. His spine had a long, deliberate curve out here that it never quite finds indoors - like he had more room to give. My fist kept pace with my hips. I pulled him root-to-tip on every deep stroke, squeezed harder on every withdrawal, and watched his whole body answer me in small helpless waves. The bark creaked under his palms. A bird I couldn’t name answered something far up the valley.

And the base of the harness was pressed firm against me on every return, warm and wide and exactly where it needed to be. My own climb started earlier than I’d planned.

I let it. Out here, with no one to hear, I let every sound out of me that wanted to come out. I felt his cock thicken in my fist and knew he was close too. I slowed. Not to deny him - to sync him to me.

“Wait.”

“Maya -”

“Wait. A minute. I want you there with me.”

I gave him back a gentler rhythm. Long slow strokes, both hands on him now - one working him, the other flat on his lower back, feeling the tremor there, feeling when it deepened. I fucked him the way I wanted to come, matched him to the pace of my own climb, let my hips drive the base of the harness against myself in a slow steady build that made my thighs shake and my vision start to go soft at the edges.

When I felt us both at the edge I reached down and found the reservoir.

I squeezed.

Warmth pulsed from the base of the toy in slow, full waves, deep inside him. I watched it cross his face in stages - confusion, then recognition, then the thing that made the whole week of planning worth it: a low, ruined sound, half laugh, half something I have no word for, as his forehead dropped to the bark and his hands curled into two tight fistfuls of grass.

“What - what is that, what -”

“Shhh. Go.”

Another pulse from the reservoir. I squeezed my fist tighter around him. Drove my hips deep, held there, ground the base hard against myself.

And then he went.

Everything in him broke open at once - cock pulsing hot across my palm in long shuddering bursts, back arching, a sound ripping out of him that the clearing took and spread and never quite gave back. I rode him through it. I had wanted to hold mine off another breath but his going over took me with it, a deep hot rush from my hips all the way up to my scalp, and I pressed my forehead between his shoulder blades and didn’t even try to be quiet.

I kept pulsing the reservoir. One warm wave after another. He kept coming - shocked, wrecked little aftershocks, his cock twitching in my fist every time another pulse of warmth hit inside him. I did not know, before that afternoon, that you could keep a man there, on the far side of his own climax, just by being in charge of the weather inside him.

When I finally let go of the reservoir he was boneless against the log. Face pressed to his forearm. Breathing like something had genuinely happened to him, out loud, in the open air, where the clearing could hear it.

I stayed inside him for a while. My palm still wrapped around him, loose and slick and careful. Let the aftershocks finish working through both of us. Kissed the back of his neck and, slowly, carefully, eased out.

Afterward we lay flat in the clearing while the light shifted from amber to rose to the first bruise of violet. Grass against bare skin. Sky the size of everything. His head heavy on my shoulder, both of us buzzing and unwound and covered in the evidence of a very good plan executed perfectly. He was quiet for a long time - the full, satisfied kind of quiet - and then he turned his face toward me and said, “We’re never hiking indoors again.”

I laughed so hard my shoulders finally dropped all the way. Then I kissed him, tasting sunlight and pine and the particular sweetness of a man who just let himself be exactly who he is. The sky went dark around us. We didn’t move.

--

I post more of our moments weekly on peg-finder.com/diary