“Honey? Can you help uploading my camera roll to iCloud?” My stepmom Diana called to me from upstairs. I shouted back through the bathroom door “in a minute!” I jerked faster at the thought of her walking in on me, jerking off to my Instagram feed. Photo after photo of the women in my life. It had been 4 years living with her since the split, her college administration position made her the household earner and I ended up living with an early 40’s Mexican stepmom at age 27.
Diana had long dark hair, parted and pulled back a bit usually, with almost porcelain skin that reddened instead of tanned in the sun. Her body wasn’t anything spectacular: thicker thighs in ratio to her torso, no outstanding tits or ass to focus on. However, her attitude and approach to life made her irresistible. She’d make penis jokes, sex jokes all the time and constantly discussed men in detail in front of me with her girlfriends. I was just another body there, she had no boundaries in discussing anything with me. Though I never thought of her in a sexual way, I couldn’t deny a draw to her, a deep sense of wanting that I couldn’t place.
Her townhouse was in a predominantly black gated community, upper class with everything taken care of. The property itself was stunning: floor to ceiling glass windows on both floors and an expansive back deck on the 2nd floor that overlooked the basketball court. The bedrooms were on the second floor, set up in a way that her bedhead and my bedhead were separated by a thin wall, just one of the overlooked parts of the townhouse. That and the huge glass window that was in the 2nd floor bathroom were strange design ideas, but otherwise, living with her was a dream. I had my own bathroom on the first floor that was adjacent to a study and the kitchen. The only thing was if you are in the kitchen cooking, you had a direct line of sight to my bathroom door and my study.
I finished jerking off in the bathroom, pushing and pushing every little drop of cum into the toilet to make sure I didn’t leave anything behind in my boxers and ran up to Diana’s room. She was sitting on the edge of her bed, on her phone, scrolling through her photos. “I’m trying to upload a bunch of these to iCloud but they’re not going, can you try? I already put the ones I want in an album.” Diana handed me her phone and I sat next to her. I tapped through the album, adding photos in groups to iCloud and started seeing a bunch of selfies with a guy. A black guy. “Hey mom, do you have a new boyfriend? Who’s this guy?” I asked, hoping that he was some actor or rapper who she met randomly. There wasn’t enough space in our place to have someone new.
She put her arm around me and put her hand under mine to take the phone, “ah you saw Mr. Steele, he’s the new head of sports administration at the school and he’s actually on the board for the community here. We’ve been hanging out a bit, but nothing serious, you have nothing to worry about.” She looked at me with a little unease, “I can date though, I mean it’s normal”. I took the phone back to continue uploading her pictures, slowly glossing over the pictures with Diana and Mr. Steele. I lingered over a screenshot of an instagram post of his, shirtless and wearing loose basketball shorts hanging off his hips with a gorgeous blonde woman on his right kissing his cheek. There was a red oval around the crotch of his shorts and the 🤤 emoji.
Something in me clicked, and I felt a combination of warmth and nausea and my penis twitched in my shorts. Diana grabbed the phone from me, “you didn’t need to see that, that’s his ex girlfriend, they broke up a couple weeks ago… I see you think she’s hot.” Diana’s eyes were glued to my crotch, at a tiny pointed bulge poking just slightly through the gray shorts with a tiny dark spot. I hadn’t even noticed the woman, just fixated on Mr. Steele’s enormous bulge, at least 10inches and thick as an old tv remote.
“Yeah sorry mom, she’s pretty hot” Diana looked at me; her arm still around me as we sat on the edge of her bed. “Can’t believe you, she’s my age, old enough to be your stepmom, but I guess I understand, she’s basically a bimbo.” Diana laughed and patted my back, “but I guess she’s hot.” She kept glancing at my tiny bulge as I tried to shift away. I kept scrolling and uploading and noticed from my peripheral Diana wasn’t wearing a bra, and her boobs looked bigger than usual, maybe around a D cup even. I tried to change the topic, “does Mr. Steele have a first name?” Diana kept glancing down at the dark spot on my shorts, growing darker. “Yeah, Jesse.. are you ok honey? You seem a bit tense.” I crossed my legs to hide my tiny erection unsuccessfully, instead, my penis and balls were pushed up further in my shorts and my stepmom could clearly see the outline and size. She went to grab her phone and our hands bumped, dropping it directly on my penis. I started to reach and then hesitated as Diana did the same. She looked at me and held me closer as she scooped her phone; her pinky slowly grazing my tiny penis as she picked her phone up. I hopped up and started leaving the room and I saw the surprise and shock on her face, followed by stifled curiosity. “I gotta go mom! Gotta meet a friend”. I ran downstairs and locked the bathroom door. I sat on the toilet and watched the precum dribble out in a long string before I jerked off furiously, to Diana and this newfound awe of Mr. Steele.
I need to be used and punished hard