my first time pegging my best friend
I’m 22 and he’s 24. Sean has been my best friend for almost three years. We’ve always been close. Movie nights, late talks, teasing each other mercilessly, but nothing more. Until last weekend.
We were at my apartment after a couple of drinks. The conversation turned flirty, then suddenly honest. He admitted he’d been curious about pegging for a long time but had never trusted anyone enough to ask. My heart was racing. I was nervous as hell, but the idea lit something inside me I didn’t expect. I told him I’d been watching videos lately and was curious too. One thing led to another, and we decided to try it that night.
He went to clean up while I pulled out the strap-on I’d secretly bought two weeks earlier and a big bottle of lube. When he came back, we started slow. We made out on my bed like we’d both been waiting years for it. I kissed down his chest, took his cock into my mouth, and felt him throb against my tongue. Then I moved lower.
I poured lube on my fingers and gently circled his hole with my thumb, just like I’d seen. He let out this shaky breath that turned into a soft whimper when I pressed inside. That sound did something to me. Heat flooded between my legs instantly. I sucked him deeper while my thumb worked in and out, loving how he trembled under me.
“Fuck… that feels so good,” he moaned, his hand gently gripping my hair.
I switched to my pointer finger, then added a second. By the time I had three fingers slowly fucking him, stretching him open, Sean was gone. He was whimpering my name, hips pushing back against my hand, completely lost in it. I had never seen him like this. My strong, funny, confident best friend was reduced to needy moans and trembling legs. I was soaked.
I pulled my fingers out, wiped them, and buckled on the strap. The medium-sized dildo looked intimidating, but the way Sean looked at me, eager, trusting, a little nervous, made me feel powerful. I lubed it generously and pressed the tip against his hole.
“Ready?” I whispered.
He nodded. I pushed forward slowly and watched the head pop inside him. His eyes fluttered shut and he let out the deepest groan. Inch by inch I sank into him until my hips were flush against his ass. The sight of my strap buried inside him made my clit throb.
I started moving. Gentle, long strokes at first, finding my rhythm. Sean‘s moans got louder, more desperate. I leaned over him in missionary so I could see his face. Every thrust made his cock twitch between us. I wrapped my hand around him and stroked in time with my hips.
“Oh my god… keep going,” he begged, voice breaking.
I fucked him a little harder, stroking him faster, kissing his neck. His whole body tensed. He cried out my name as he came harder than I’d ever seen anyone cum. Thick ropes across his stomach and chest while I kept thrusting through it. The sounds he made were unreal.
When he finally came down, breathing hard and looking dazed, I pulled out carefully. We cleaned up a little, then he flipped me onto my back. He ate me out like a man starving, two fingers curling inside me while his tongue worked my clit. I came so hard I saw stars, shaking against his mouth.
We lay there afterward, sweaty and tangled, laughing softly in disbelief.
“I can’t believe we waited this long,” he murmured against my neck.
“Me neither,” I whispered, tracing circles on his chest. “But we’re definitely doing that again.”
That night changed everything between us. What started as curiosity became the most intense, intimate sex I’ve ever had. I had no idea pegging my best friend would feel this good, both the power and the connection. I’m still smiling just thinking about it.