Girlfriend Pegged Me Until I Came Hands-Free

It's funny how the things you swear you'll never try have a way of finding you when the right person walks into your life. I used to think of myself as open-minded about sex—threesomes, public risk, the occasional toy—but the idea of something sliding into my own ass always sat firmly in the category of "not for me." Then I met Megan.

Meg was a teaching assistant in the department where I lectured. Thirty-two, five-foot-six, long dark hair that she usually wore loose, green eyes that never quite stopped assessing whatever was in front of them. Athletic enough that her body looked strong under clothes, but soft in the places that mattered—full C-cup tits that strained against her blouses, hips that filled out a pair of jeans in a way that made me lose my train of thought mid-sentence. We started with coffee after a faculty meeting, moved to drinks, and within two weeks we were fucking like people who had been waiting years for the right match.

The sex was already excellent. She came hard and often, liked it deep, liked it a little rough, and had no problem telling me exactly what she wanted. One night after I'd spent the better part of an hour with my tongue buried in her cunt and then fucked her until she shook, she rolled onto her side, traced a fingertip down my chest, and started asking questions.

What had I tried. What had I loved. What still made me nervous. What I was curious about but had never admitted out loud.

I told her the truth. Public bathrooms, a one-night threesome that had gone better than expected, the time a girlfriend had worn a small plug while I fucked her. When I finished the list she smiled that slow, knowing smile that always made my cock twitch.

"Would you let me show you something new?"

"Depends what it is."

She reached into the drawer beside the bed and pulled out a flesh-colored dildo—six inches, thick enough that my mouth went dry just looking at it. She tapped it lightly against my thigh.

"This. In you."

I laughed, more out of reflex than anything. "That's a little ambitious, isn't it?"

"A girl takes that much every time she gets fucked," she said, voice calm. "We're smaller. And I've taken your whole hand. Remember?"

I did. The memory of my fingers disappearing one by one into her stretched cunt still lived rent-free in my head. She had been so wet, so open, so fucking proud of herself when my knuckles finally slipped inside.

"I want to work you up to it," she continued. "Slow. Careful. I want to watch your face while you learn how good it feels to be filled."

Something in the way she said it—confident, almost tender—cut through the automatic refusal. I nodded. "Okay. But slow."

"I promise nothing," she whispered, leaning in to bite my lower lip. "You'll get what you deserve."

We didn't talk about it again for almost three weeks. Life got busy. Then a text arrived on a Thursday afternoon: film festival this weekend, my place after. Wear something easy to take off.

We had dinner, two artsy movies that neither of us really watched, and enough wine that the walk back to her apartment felt like floating. The second the door closed she pushed me against it and kissed me hard, tongue sliding deep, one hand already cupping my cock through my jeans.

"I have a present for you," she murmured against my mouth. "Been waiting to open it all week."

In the bedroom she lit candles, stripped me down to nothing, and made me lie on my back while she changed into a short satin robe that barely covered the tops of her thighs. No bra. No panties. Just the robe and the knowledge that she was already wet.

She spent a long time with her mouth on my cock—slow, wet, deliberate—until I was leaking and twitching. Only then did she pull the black velvet bag from under the bed. Out came a purple silicone cock, eight inches long, thick, with a flared base and a remote. The head was slightly bulbous. A second smaller toy—smooth, tapered, maybe four inches—followed, along with a large bottle of thick lube.

"You're going to learn to love this," she said, voice soft but absolute. "I'm going to teach you."

I started to protest. She silenced me with two fingers against my lips.

"Trust me. Legs up."

I bent my knees. She slid a pillow under my hips, draped a towel over it, and settled between my thighs. The first touch was just a fingertip, circling my hole while her other hand stroked my cock with long, lazy pulls. The sensation was strange—intimate in a way nothing else had ever been. When she added lube the finger slid easier, pressing gently until the tip slipped inside.

I clenched. She waited. Kissed the inside of my thigh. Whispered that I was doing so well. The second finger took longer. She worked them in and out, scissoring carefully, curling until she found the spot that made my vision blur and a low sound escape my throat.

"That's your prostate," she said, almost conversational. "I'm going to make you come from this alone before the night is over."

She took her time. Fingers became the smaller toy. The stretch burned at first, a deep, insistent pressure that made me grip the sheets. She kept my cock in her mouth the whole time, sucking slow and wet while she eased the toy deeper, twisting it, pulling it almost free and then pushing it back in until my hips started lifting on their own.

By the time she switched to the purple cock I was already leaking steadily, balls tight, breath ragged. She strapped it on over her hips, the harness framing her cunt perfectly, and knelt between my legs again. The head pressed against my hole. She locked eyes with me.

"Breathe out. Push back against it. That's it. Good boy."

The first inch made me gasp. Two inches and my thighs trembled. She paused, leaned down, and took the head of my cock into her mouth again, sucking hard while she rocked her hips forward another inch. The stretch was enormous. I felt every ridge of the silicone as it opened me, filled me, claimed space that had never been claimed before. When the thickest part finally slid past my sphincter I made a sound I didn't recognize—half moan, half sob.

"Look at you," she whispered, voice thick with lust. "Taking it so well. Your pretty little hole stretched around my cock. Fuck, that's beautiful."

She fucked me slowly at first. Long, deep strokes that dragged over my prostate on every pass. The vibration started low, a steady buzz that turned the pressure into pure, liquid pleasure. My cock jumped untouched. Clear fluid ran down the shaft and pooled on my stomach. She wrapped one hand around it and stroked in time with her thrusts, watching my face the entire time.

"Tell me how it feels."

"Full," I managed. "So fucking full. God, Meg—"

"Does it feel good to be fucked?"

"Yes."

"Say it properly."

"It feels good to be fucked. It feels good to take your cock in my ass."

She smiled like I'd just handed her the world and started moving harder. The wet slap of her hips against my ass filled the room. Every thrust punched a fresh wave of sensation through my gut. I could feel the shape of her cock inside me, the way it forced my body to open and accept. My own cock was rock-hard, bouncing against my stomach with every impact, leaking steadily.

She switched angles, lifted my legs higher, and drove deeper. The head of the toy pressed hard against my prostate and stayed there, grinding in small circles while the vibration intensified. Something inside me coiled tighter and tighter until it snapped. A thick, milky stream pulsed out of my cock without a single contraction of my balls—just a continuous, helpless flow that coated her hand and my stomach. The pleasure was different from any orgasm I'd ever had. Deeper. Longer. It left me shaking and half-delirious.