My 23yo self pegging my shy roommate for the first time while he begged
I’m 23 and I’ve been teasing my roommate for months about how cute he looks when he gets flustered. Last night I finally decided to do something about it. I came home from my shift wearing a short black skirt and thigh-high socks, and I caught him staring again. I just smiled and told him to come to my room if he wanted to stop pretending. He followed me in without a word. I pulled my harness out of the drawer and watched his eyes go wide. “You’ve been wanting this, haven’t you?” I asked while I stepped into the straps and tightened them around my hips. He nodded, cheeks burning. I made him strip and get on all fours on my bed. I took my time lubing him up, sliding two fingers inside while he whimpered into the pillow. When he was shaking I lined up the strap-on and pushed in slow. He gasped so loud I had to cover his mouth. “Shh, you’re okay,” I whispered, rocking my hips until I was buried all the way in. I started thrusting, nice and deep, enjoying every little sound he made. Every time he tried to reach for his cock I slapped his hand away. “Not yet. Good boys wait.” I kept a steady rhythm, grinding against him until his legs were trembling. When he started begging I finally reached under and stroked him while I fucked him harder. He came so fast it surprised both of us, spilling over my hand while I stayed inside him. I pulled out gently and kissed the back of his neck. “Next time I’m not going easy on you,” I told him. He just nodded, still catching his breath. I think my roommate is officially mine now.