Catching My Stepbrother (Twice)

Mom remarried when I was in high school, and my sister and I gained two stepbrothers. The older, cooler one graduated and moved out the next year, so I got stuck living with the younger brother. Bradley was my age and had been in school with me all through middle and high school during our parents' courtship, and he was a jerk. He was kind of dorky and a little overweight and socially awkward like me, but he took it out on me by being kind of a bully both at school and at home. 

By the time we were seniors in high school, I'd stopped caring about Bradley's crap. I had a newfound boyfriend and sex life and knowledge of how to give and receive pleasure expertly. My whole personality changed at that point as I became more confident and embraced the sexy curves of my body and dressed in more form-fitting clothes. I know Bradley noticed. He was still obnoxious as ever, but now I caught him staring at the cleavage that peeked from my shirts, at my ass as I bent to pick something up. I especially enjoyed early mornings before school as we all got ready at the same time. It would thrill me to stay in my PJs, my braless tank tops and low-slung sleep pants, as we moved around the kitchen together. I loved to take a big luxurious yawn and stretch in his presence, arching my back and rolling my shoulders so my breasts gently bounced under my shirt, the hard nipples pushing against the fabric, my shirt riding up to show a strip of skin at my hips just above my pubic area. When I would finish my stretch and open my eyes again, he'd always look hastily away. It felt so empowering to know he thought I was sexy, and these little teases felt like payback from all his years of being a jerk.

Bradley's bedroom was downstairs off the family room, where the video games and computer were. I didn't spend much time down there, so he was used to having the rooms all to himself. I'm sure that made him careless. One evening I was sent downstairs to tell him dinner was ready. I walked quietly down the stairs to find the family room completely dark. I could hear a faint, rhythmic thumping sound in his room of a headboard against a wall. He was in his room masturbating. A weird combination of feelings rushed into me -- disgust, annoyance, a mean excitement at the thought of catching him and scaring him, and an unexpected arousal. I knew I should just yell his name from the safety of the family room, but instead, I crept down the hallway.

As I neared his bedroom, the thumps never slowed. I dropped down to my hands and knees and crawled the rest of the way. When I made it to his open door and peered inside, there he was.

He was lying on his stomach on the bed, head away from me, face pressed into the mattress. His pillow and blankets were bunched up under his hips along with both his hands shoved beneath him. He'd taken off his shirt, and he'd pulled his pants and briefs down to his ankles. With short thrusts he humped hard against the bed. 

I couldn't stop watching. His chubby ass dimpled as he pressed himself into the bed, jiggling a little with every movement. He was really going at it. I wanted to laugh at him, but at the same time I started feeling unbelievably turned on. It just seemed so raw, so purely sexual, the way his needy movements jerked against the bed, rubbing his cock toward ecstasy. Other than my boyfriend, I'd never seen anyone masturbate before. Catching him unawares took away the performative nature of it all and showed me a window into what everyone must look like when they're getting themselves off alone, the reckless abandon, the carelessness about how they look, nothing mattering in the world except the mounting climax. I was disgusted, and feeling ashamed of sneaking around and watching what I shouldn't be seeing, but I was also incredibly turned on.

My hand moved between my legs almost unconsciously, pressing against my clit that throbbed for attention. I didn't want to move more than I had to, so I just held still, pressing hard where I ached to rub, and watched.

Bradley's movements sped up and became less regular. His heavy breathing turned to grunts with every thrust as he kept fucking against the bed, his ass rocking faster, his hips wiggling a little from side to side as his cock grew closer to exploding beneath him. Finally he let out a long, high whine and held still with his ass flexed hard into the mattress.

I wanted to cum so bad, but I was scared to even breathe. I held perfectly still with my fingers still pressed against my clit, my panties growing damper by the second beneath my hand. For what seemed like a long time, Bradley didn't move. But then he relaxed his body and slowly rolled onto his back, still breathing heavy. He'd made such a mess. Slimy cum was all over the blanket and pillow under him, and smeared all over his skin. His dick looked so different from my boyfriend's, skinnier with an upward curve. Bradley lay there, his hand idly smearing the cum on his belly, eyes closed.

I took my opportunity to crawl backward away from the door, and I made my way silently down the hall. Safely in the family room, I called to him, "Hey Bradley, dinner's ready!" There was a scrambling inside his room. "Okay, okay!" he yelled back to me before slamming his door. I went up to my room and rubbed out the fastest orgasm of my life before dinner.

In the weeks that followed, I wanted to catch him again, but I felt increasingly guilty about spying on him and so I stayed away. That all changed one Sunday after church, when our parents dropped us kids at home before leaving for some errands. My sister had a paper due at school the next day and locked herself in her room to work, and Bradley went downstairs, leaving me alone. After a stretch of boredom and starting to feel hungry, I went downstairs to ask if he wanted to order pizza.

All the downstairs lights were on and his bedroom door was open, so I just trotted inside. "Hey, Bradley, we should order--," I stopped and stumbled at his doorway at the sight of him.

For a frozen moment we just stared at each other. He'd been humping the pillow again, and he stared over his naked shoulder at me with eyes wide in horror. At last he scrambled up to a sitting position, dragging the sheets and pillows into his lap, and curled up against the wall. "Jesus, can't you knock?" he yelled.

"Don't blame ME, your door was wide open!" I snapped back.

Bradley looked like he was about to cry. "Please don't tell on me. Please."

I should have felt triumphant that I'd achieved some revenge for all his meanness, but instead I just felt awful guilt mixed with pity. He was in the same situation I was in, growing up in this strictly anti-masturbation Catholic household where anything related to sexuality was strictly taboo. At least I'd been lucky enough to find a boyfriend and explore sharing pleasure. My poor stepbrother was just doomed to hide in his bedroom all alone, humping his bed in secret.

With him naked and vulnerable, I found myself in a position of power I'd never had over him before. I felt uncharacteristically brave. I walked further into the room and sat down in his desk chair adjacent to the head of the bed. "It's really okay," I assured him. "You know, I do it too."

His face was partly shocked and partly skeptical. "Shut up." He was still angry and horrified, with that near-tears look still in his eyes.

"All the time. Every day. Honest." I rested my hand on my leg above my knee, on the hem of the church skirt I still wore. The feelings of guilt and pity melted away and arousal flooded in. "You don't have to stop. I know it sucks when you have to stop right when you're starting to get the good feeling."

His eyes flicked from my face down to my leg where I was slowly lifting my skirt, then back again. 

I wanted so bad to spread my legs for him, to pull up my skirt and pull down my panties and finger my wet pussy to an orgasm right before his eyes. If all those times he'd been sneaking looks at my body were any indication, I knew he wanted it too. But something stopped me. I couldn't do it. But I couldn't just walk out of there.

I stood up. "I promise to knock next time. I'll leave you alone."

"Wait--"

He stopped talking abruptly as I reached up my skirt. I slid my panties off and let them drop to the floor. We both could see the wet spot in the crotch where my swollen pussy had been. "Have fun. Here." I picked up the panties and placed them gently on the edge of the bed. 

The look on his face was delicious. I'd never seen such a gaping look of dumbfounded shock on anyone before or since. He stared at my underwear sitting on his bed, the pink satin looking so out of place against the rumpled navy blue plaid of his sheets, and he didn't meet my eye as I turned and left the room, closing the door with a click.

I went directly to my room, locked the door, and lifted my skirt and furiously rubbed myself to a crashing orgasm. I buried my face in my pillow to keep quiet, knowing my sister was directly next door. After I came, I lay there and pictured Bradley downstairs with my panties pressed to his face, inhaling my scent as he humped and spurted all over his sheets. The image revved me up again, and I massaged my clit with one hand, shoving two fingers of the other hand inside my cunt as the contractions started again, gripping my pussy walls around my fingers as waves of pleasure flooded over me.

By the time our parents returned, I was changed out of my church clothes (and now wearing underwear again), acting like everything was totally normal. When Bradley emerged upstairs for dinner, he could barely look at me. I gave him a nonchalant smile, and the evening went on as if nothing had ever happened.

We never acknowledged it, and it never happened again. Our relationship improved a lot after that though, and he eased up on the bullying and treated me a lot nicer. Sometimes I would notice I hadn't seen a particular pair of panties as I put away my laundry, and when they'd reappear after the next wash, I always wondered if he'd gone through my hamper and taken another souvenir to enjoy. The thought turned me on a lot, and I spent many nights in that house rubbing myself off and imagining him in his room below me doing the same and smelling my stolen panties' sweet pussy scent. Now he lives hours away with his wife and kids, and we only ever see each other once a year during the holidays. When we get together, there's an extra fondness between us -- we seem to have a slightly closer bond with each other out of all the stepsiblings. I know that even though he's a grown, successful man, a part of me will always see the obnoxious chubby teenage boy he used to be, fucking his pillow, thinking of teenage me.