All characters are over the age of 18.
My mother is very proper. She would never do anything to jeopardize her reputation in the community. So it was very difficult to muster up the courage to ask her to jack me off. I don't know why I did it, but something about how professional she was about every aspect of her life made me want to upend that whole faΓ§ade and have her pump a fat load out of me.
My legs almost gave out as I walked into the living room. "Mom, will you jack me off?"
Shock. Pure shock.
"I'm sorry," I said, finally going all in. "I'm just really horny right now."
My mother visibly tensed, and I could see she was trying to figure out how to get herself out of the situation without embarrassing us both.
"What if I watch," she finally said, her voice a little too quiet.
"What?" I said, almost falling over, bracing myself on the sofa.
"I said what if I watch." She tried to raise her voice, but it was still too quiet for me to comfortably listen. "Men have asked me for much worse in the past. So I guess I'm not that taken aback. I do have to say it's sickening how our society is so broken that it leads a son to ask his own mother to pleasure him! But I am not entirely shocked." She paused for a moment. I almost died from the anticipation. She finally continued, "I won't do it, but I am willing to sit here and bear witness as you indulge in your fantasy." Her voice was dripping with what at first seemed like disgust, but there was a slight feeling of doubt in my mind about her total disdain for the situation.
I gulped, not sure how to proceed. "Okay," I squeaked out after a few moments of apprehension.
"Good." Her voice was back to its usual authoritative self as she briskly told me what to do next. "Take off your pants and if you really have the nerve, start stroking your cock right now."
I removed my pants immediately. I also took my shirt off to be a little more comfortable. I was about to pull down my underwear when she interrupted.
"Stop," she said softly. "Come here."
I walked over to her, standing next to the sofa. She leaned in towards me and encircled my legs with her hands, forcing me to lean back in order to keep my balance.
Her face was slightly below my bulging dick. She looked up and met my gaze before whispering, "I'm going to free this cock."
She moved her hands up to where the elastic band of my underwear met my hips and started to slowly pull them down, all the while never breaking our gaze into each other's eyes. Her nails grazed my skin as she slid them beneath the waistband and peeled the fabric over my hips. As they moved further down, my cock bounced straight out from my body and rose until it pointed out and slightly up, hardly an inch from her face.