My Step-Sissy - Sex Stories

My Step-Sissy

... going deeper. I realized this was starting to feel really fucking good and started getting loud with my moans. &#034Shhh, baby we gotta go, you're gonna cum now okay?&#034 &#034Awhh,mmm, okay sir.&#034 He pumped my shaft harder and faster, my cock was completely on edge when suddenly he said, &#034Shoot in my hole, put it in boy&#034 I stood up without saying anything, I never, ever, did this before. He was bent over his desk now, his athletic thighs spread like he was getting searched. His tan skin contasted his paler, finer smooth butt. I rubbed my leaking boycock on his asscheek, guiding it toward his brown manhole. I spit on my cock like I learned in the pornos, he fingered with three fingers, spreading his entrance. It went in easy. He grunted as I put one inch and another up his tight sexy butt. Then I pulled and pushed his warm hole loose. I was closer than ever and didn't want to stop but before I could ease up, I shot hard. Pushing even deeper, with my coach who I saw everyday, grunting and moaning like an a****l. His asshole tightening as I went deeper, almost seeing how far I get my load up his sexy ass. He turned backward and grabbed my neck. Kissing me hard and wet, our tongues practically dancing. My cock flopped out of his butt, my cum followed. He was limp on his desk, still bent over. He pulled his cheeks apart, presenting. Now every stud I fucked had to take my load up his ass. It was late at night, the door was cracked...Which I found to be very ...

... strange. When I looked in, his eyes were closed, legs spread in my very direction, his right hand working his stiffy while he rubbed his asshole with the left. I thought back to my method of discipline I had relied on for so long... I remember when I caught him smoking in my bathroom, door open, not even trying to mask the smell. First fuck up in months. Pulled his pants down to find a rounder, shapely butt underneath. I hesitated and had flashbacks to the twinks and the sissy boys who I watched in my pornos. His ass was pretty sexy like theirs. Then I shook myself out of my daze and laid the hammer down. He stuck his face in the pillow, didn't scream or flinch as the blows landed on his cheeks. They were a brighter red than they have ever been and yet I could feel his ass push up against my hand, I could recall a slight moan beneath the pillows as I rubbed his baby-soft bottom to relieve some of the pain. I decided to figure out for myself at last. He left the door open, again. This time I knew exactly what my son had transformed into. It was 1:00am. On a school night and I hear some creaking upstairs in the guest room. I could see that the light was on. I crawled on my hands and knees so that he wouldn't see me. Got right up to the door and peeked ever-so-slightly. There he was. He had a shiny ebony big black dong, attached to the bed via a suction cup. He was on all fours, wearing a blue bra and panties. His mother's I know. And a blonde wig...I continued watching to my own ...