Wrath of the Pegging Milf

"I am not..." I began but was unable to finish. The shock yet to pass.

"Either you let me do this, or I tell your step-dad, and you also pay for the damages."

She began to unbuckle it and slip it on. I swallowed, glancing behind me, almost feeling lightheaded.

I had known this woman for years and she had always been nothing but kind to me, her house had been a second home. Especially during the years when Dan and I had butted heads the most, and she had always had sympathy for me.

I turned back to her as she secured it to her groind and took it in one of her hands.

"So. What's it going to be?"

I glanced down at the strapon then back up to her as she plucked a a tube of lubricant from the bag and began to slather it over the long shaft, until the tip began to glisten.

Not a more perfect moment for a car to come could there ever be, yet the road remained empty. My chest tightened, a swarm of butterflies had exploded into my stomach, and I felt like throwing up, and needed to support myself by leaning against the nearby birch tree.

"Take off your pants." She instructed.

"Madeline, please."

"Do it, or I make a call to Dan, tonight."

I found no sympathy in her eyes today. She ran a finger up and down the shaft then gave the tip a flick.

I felt my hand move to my belt and began to undo it, as though I was no longer in control, and some unseen force had taken over, all the while unable to move my eyes from her crystalline blues.

My pants dropped to my calves, my gaze dropping to the forest floor. Madeline took a step towards me, she took me by my shoulder and turned me round and pulled my boxers down, then positioned herself behind me.

I placed both hands on the hood, closing my eyes and wishing for all the world that the earth would open beneath me and swallow me into a bottomless pit, or that maybe I would wake up again and I would be back at rehab, and I would be making the trip home again later.

Madeline gripped me by the back of my shirt and bent me over with some force, I was taken aback by her strength. With her other hand she pressed the tip between my cheeks, I felt my sphincter twitch as it the slick tip brushed against, the butterflies rushing up into my chest.

She slowly began to push. My teeth pushed against each other until the point where my jaw begun to lock, a deep rasping grunt escaped my lips as the tip began to widen my sphinter.

"Madeline please I can't." I tried to plead further, but my words trailed off into a guttural wince of pain as I felt the tip press itself in.

She gripped my shoulder tighter and pushed harder, the shaft beginning to slide in. My insides started to feel as though a thousand angry wasps had suddenly been disturbed and were searching for their aggressor. I placed my forehead against the boot of the car as the shaft continued to move in, my bowels shifting and something deep within me clenched tight and a feeling somewhere between pain and pleasure shot through my body and caused my head to spin with a dull tingling sensation.

I let out a louder grunt as she came to a stop, all eleven inches inside. It had taken a fair few minutes, but now her belly was pressed to my backside

"Good boy." She said, rapping her fingers on the small of my back, then gave me a thrust. I let out a exclamation of pain, tears welling in my eyes.

She gave me another then began to slide it out then back in slowly, the movement more fluid now, but no less painful, the clenching feeling dissipating just as quickly as it had come.

She placed her hand further up my back as she slid it in and out for a few moments, her fingers walking back down to my backside, which she gave a firm smack. I let out a yelp.

"Don't pretend you've not done the same to girls before." She said, her voice almost high with delight as she smacked me again then thrust. "Just showing you what you consider a good time."

This time I let out a short whimper, the pitch high and quickly cutting out half way down my throat, and evidently gave her some pleasure.

I could only grit my teeth harder and dug my fingers into the metal of the car boot as she started to thrust faster, the strapon sliding in and out with relative ease now, perhaps mercifully so.

She placed both hands on my hips and began to thrust quicker now, her breathing heavy and in time with her thrusts. She came to a stop, but only for a moment to readjust herself, before she continued, the initial one causing me to wince louder, the sound that escaped my lips pitiful and weak.

She gave me another slap, then again prompting another whimper, which had been her goal, she readjusted herself again and continued, letting out a soft breath as she craned her head back, eyes closed with a deep sense of euphoria, her fingernails digging into the tender flesh of my backside and hips.

All the while my anger and hate grew from the pit of pain and humiliation.

I could have killed her, right then and there, pulled this thing out of me picked up the nearest stick or rock and beat her with it. Watch as the woman's vile smile was wiped from her face as I brought it down again and again, breaking her skull open.

I was wretched from my fantasies as she pulled out sharply, I let out a cry, hand flying to my backside and she stepped back. I couldn't move, for fear that the sharp pain would return, I could only stand there teeth clenched and bent over.

"We're not done yet." She snapped, her hand gripping my balls, I let out a yelp of pain as she squeezed. "Come."

She pulled me from the boot and towards the passenger side door which still hung open. "Bend over." She commanded.

I glared at her, eyes wet with tears and stained red. Her lips were pressed into a thin line and her eyes flashed as she squeezed again. I winced and turned, bending over so that my head and shoulders were inside the car and I propped myself up on the passenger side chair.

She repositioned herself, and now I was a little lower it was easier for her to thrust.

I let out a cry of pain as she forced the tip back inside, sliding in a little easier but no less painful. She pushed my head down before placing her hands back on my hips and began to slide in and out again, her breathing heavier and more excitable now, every movement fluid but hard, and breaking against the wall of my insides. I could feel my bowels begin to twitch and shudder.

I let out another cry of pain as she stopped to give my backside another smack louder this time and causing a few nearby birds to take flight.

The clenching feeling had returned but and had formed a tight ball somewhere within my passageway that tingled with a strange sensation that was not overly uncomfortable, and almost close to agreeable, but what pleasure there could have been was easily overpowered by the humiliation and pain that my stretched sphincter was going through.

Her breathing was higher and louder than ever.

She finally came to a climax and thrust three more times, heavier than before and causing me to let out three cries of pain, which were swiftly muted by her hand clamping down over my mouth. She pushed it all the way in and leant over me panting for a moment before stepping back and pulling it out, the sharp feeling of it sliding out casing me to wince, and my legs to buckle. I fell to my knees panting and sweating onto the passenger side door.

Madeline leant against the hood, hair sticking to her forehead as she caught her breath and regulated her breathing. I could not even bring myself to look at her, she took several more deep breaths before beginning to unbuckle the strapon.

"Goes without saying." She said through her panting. "We don't tell anyone."

I glared up at her as she slipped it off and pulled out some wipes to clean it, my insides feeling as though they had been reshuffled and smashed against each other.

She placed the strapon back in the bag.

"I'll call a tow truck and sort it out, it'll all be taken care of it."

She pulled her phone out and began to dial.

I couldn't stand, my backside still in tremendous pain and a throbbing that seemed to only intensify began to smother my senses. I knelt there for a while as she made her call then pocketed her phone.

I stood, slowly, my movements delicate as to not cause me any more pain, although now it had been reduced to a numb throbbing sensation.

"Oh, and you are invited for dinner tomorrow night. Just you." She said, her lips curled back into her wicked smile. "Bring some flowers as a thank you and we'll say no more about the car." She said, but not before snapping a few photos of it.