Waking up in my stepmother’s luxurious king-sized bed after a wild night of sex had my head spinning. Only hours before she had asked me to fuck her ass, a task I willingly obeyed. With that act, my wildest fantasies had been fulfilled. Or so I thought. There was nothing I could imagine that could top the sight of my cock stretching her tight little anus. Despite cumming in both her ass and her pussy during the night, I was still semi-erect just thinking about it. I threw the sheets back and admired my large eighteen-year-old cock, proud and engorged as I stroked it to full measure. Debbie’s constant praise and the vision of her sweet ass stoked my ego.
But now as I looked up, my smile turned to angst when I saw her standing in the bedroom doorway, naked except for a large strap-on dildo that projected menacingly from her groin. Her smile did little to comfort me.
“So what do you think of MY cock? It rivals yours although I prefer the real thing. This was a present from your father. Turns out, he had a kinky side to him.”
“It looks like the real deal, but I’m unsure what you intend to do with it.”
“Well, you know how I enjoyed your cock in my ass last night. I thought I might return the favor.”
I didn’t know what to say. Debbie had placed a finger in my ass once or twice during sex, and it had made me shoot like a Saturn V rocket into her waiting pussy, but this was different. The fake penis adorning her voluptuous form was much larger than her tiny finger. I couldn’t imagine how it would feel in my ass if indeed that was what she was thinking. Why else would she be wearing it that way?
“Scary looking isn’t it? I have to say when I used it on your father, I got tremendously excited. I can see why men like to fuck doggie style. It was exhilarating to watch this big cock sliding in and out of your dad’s ass. And even more so because he liked it. What do you say? Are you willing to give it a try? I’ll be gentle. I think you’ll like it.”
She gripped it in her small hand and slowly stroked it as if it needed encouragement. She crawled up on the bed and lay next to me and kissed me as she reached over and grabbed my cock. She held it next to the fake one for comparison.
“It’s about the same size as yours. Are you game for some kinky fun? I promise I’ll be careful. And later I’ll let you do whatever you’d like to me if you let me do this. God, I’m practically squirting just thinking about it. Let me start by giving you a blowjob while you think about it.”
Debbie kissed me passionately, her tongue exploring my mouth and my ear as she whispered dirty thoughts there. I was now wide awake and somewhat intimidated by the image of a thick dildo invading my ass. At the same time it was exciting to imagine my stepmother doing this to me.
Soon Debbie’s lips were wrapped around my cock and I watched as she fellated me while keeping her eyes glued to mine.
After several minutes, she kissed me and put her lips to my ear as she whispered hoarsely, her warm breath sending waves of pleasure to my brain.
“Roll over, Sweetie. Let me give you a little early morning massage. You seem tight and I know all the right places to make you relax.”
Normally I would never have considered a request like this, but it was coming from my stepmother–my gorgeous busty stepmother who was promising things I never dreamed of. Obediently, I rolled onto my stomach and heard her grab the Vaseline from the nightstand where I had returned it previously. Suddenly I felt something cold and slippery being rubbed over my butt cheeks and between my thighs.
“Get on your knees for a sec so I can put this pillow under your stomach. There, that’s better. Perfect. Spread your knees a little, like that. You’ve got the cutest little butthole, Jimmy. I’m going to make it nice and slick and go very slowly. I love your muscular ass. Mmm, it’s so inviting!”
I felt her hands spread my cheeks and then the cool ointment being spread over and around my anus. Suddenly a fingertip slipped inside me and briefly wormed slowly in and out of my ass.
“See, doesn’t that feel wonderful? Just wait.”
And it did feel good, once I was over the initial shock of having my ass penetrated. I felt Debbie’s lips kissing my butt and my lower back. She raked her breasts over me, dragging her rubbery nipples over my back and then she fumbled for a second before I felt something larger at the opening to my ass.
“Nice and slow. Fuck, it is so exciting watching this ivory cock head trying to get in your tiny asshole. I’ve used lots of lubrication. “
I felt more pressure as Debbie gripped the shaft and pushed a bit harder.
“You’re going to love this, I promise. And there it goes. I’m in your ass. My god, this is so cool.”
My eyes opened wide at the invasion, and then I relaxed as a couple of inches of plastic cock entered me. The feeling was indescribable. It was scary and exciting at the same time. It felt like a sexy bowel movement if that’s not too weird, and knowing that my stepmother was doing it made it all the more incredible.
“I bet you won’t be telling THIS to your buddies, will you? That your mother fucked your ass. God, this is so exciting. I wish you could watch it. I’ll have to get my phone next time and take a movie so you can see.”
Next time? Was she planning on making this a regular event? I panicked at the thought, but then I began to get into it as Debbie slowly pumped the slippery shaft in and out of my ass. Suddenly I felt a hand reach around me and grab my cock, now fully erect and rigid again after overcoming my anxiety.
“You are going to cum like a firehose in a while, Honey. I promise. Just relax and enjoy this. Your momma loves fucking her teenage son’s ass. Isn’t this fun?”
And it was. Well, maybe fun isn’t the right word, but it was erotic. I imagined her big tits flattened against my back and her hips working the dildo in and out of my little channel. We continued this way for several minutes as she described how she loved being in control and fucking me.
“When you come I want you to tell me how it feels. Describe it for me. God, this is so exciting, Honey. Thanks for going along with me. Later you can do whatever you want with me. Mmmm, your cock is so hard in my hand. Not as hard as the one in your ass but close. Are you almost there? Just let it go. It doesn’t take long this way, especially the first time.”
Her banter along with her hand jerking me in sequence with her hips put me over the edge.
“Oh, fuck, Debbie. I’m going to cum. Jesus! This is so fucking wild. I can’t stop it.”
“That’s a good boy. Cum for your momma. Shoot all your hot cum while I fuck your sweet ass. That’s it. I can feel your cock throbbing. It’s going to be a big one, isn’t it? Go ahead, Sweetie. Cum for me.”
Suddenly an explosion went off in my brain, and I felt Debbie press her hips to my ass and hold them there. A wave of pleasure surged in my bowels as my cock erupted with a stream of sperm onto the bed sheets and the pillow under me. Debbie stroked me rapidly until my cock slowly softened in her hand and she rubbed the remnants over the crown and my piss hole.
I felt her hips release me and the dildo slowly retreated from my ass.
“Did you like that? Isn’t that the wildest feeling? I wanted you to see what I felt. Like I said, it’s not for every day. Just special occasions and this is one of them. Let’s just relax for a while. Looks like I’ll need to do some laundry. That pillow took a soaking from you.”
“Jesus, Debbie. That was wild. You took me by surprise with that thing, but fuck–talk about intense.”
We lay there cuddling and dozing. When I awoke later, Debbie was gone. I closed my eyes and tried to picture what had just taken place. I realized that I was lying on a huge wet spot on the sheets. I rolled over and saw the tool that had just invaded my ass.
The strap-on was lying on a chair across the bedroom. I swear…it was grinning at me.
