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My Son’s Sleepover

"Sharing my room with one of my son’s friends"

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My son had turned eighteen at the beginning of the week, but had decided to delay any celebration until Friday when we could host a sleepover. The plan was for him to hang out with friends in the afternoon and finish off the day with a sleepover at our house.

Friday night, the boys were playing video games and listening to music in my son’s room while I figured out where they would be sleeping. More boys than expected had shown up, which meant that not all of them would fit in my son’s room and the living room, and at least one of them was going to have to sleep on my bedroom floor.

Jordan, who I already knew from previous visits, was the boy who volunteered, and it didn’t surprise me one bit. What he and the other boys didn’t know was that besides noticing their wandering eyes, I had overheard them talking about me sexually in the past. They had described me as a MILF and PAWG, among other things, seemingly to tease my son. In fact, if it hadn't been for the loud music, I was sure I would’ve been able to hear some comments about me.

The reality was that I couldn’t blame any hormone-driven teenager for seeing me as a walking masturbatory aide. I took care of myself by working out four times a week, which sculpted my physique to resemble that of a porn star’s – a body built for sex.

I placed a couple of blankets and a pillow on the floor, forming a makeshift bed for Jordan to the right side of my bed.

Shortly after the music stopped and the boys were ready to sleep, Jordan knocked on my door.

“Come in,” I said, from underneath the covers.

He walked in, closing the door behind him, “Sorry to bother you.”

“As long as you don’t keep me up all night,” I joked, which wasn’t uncommon for me to do with the boys.

“I won’t, I promise,” he smiled and settled on the floor before I turned off the nightstand lamp.

In the middle of the night, I awoke to movement down to my right. I didn’t make much of it until I saw a bright flash through my closed eyelids. I opened my eyes and saw Jordan holding his phone, looking at was an indistinguishable picture from my position. I figured he had pressed the wrong button and closed my eyes.

A few seconds later, the room lit up with his phone flashlight, and this time I could clearly see what he was doing. He was taking pictures of his penis, presumably sexting, or creating content for a future sexting session.

From my view, I could only see the head of his penis, a mushroom-shaped tip. I didn’t want to say anything and make it an uncomfortable and embarrassing moment for the two of us, so I decided to keep observing quietly.

I moved slightly to the right so that the bed wasn’t blocking my view and that’s when I laid my eyes upon his monstrosity. The length of it dwarfed his phone, which he had to hold closer to his face in order to get his penis entirely in the frame. The picture flashes illuminated his veiny shaft and left no doubt that it was longer and thicker than any penis I’d ever seen in person.

He’s fucking hung, I marveled.

After he was done with his phone, he put it down, leaving me unable to see what he was doing.

This was a matter of conflicting moralities for me. One side of me was appalled by his audacity to do such a thing with his friend’s mom mere feet away while the other side was turned on by the wickedness of it all.

I couldn’t just go back to sleep. I had many thoughts swirling in my head, but they were all betrayed by how quickly my body had become aroused. It was hypocritical to try playing the responsible mother when there was a wanton mess between my legs.

You’re lusting after your son’s friend, I reprimanded myself, feeling my soaked thong clinging to my lady bits.

A couple of minutes passed by and in the darkness of the room, I couldn’t quite make out where he was until I felt his weight creeping under the covers.

What the fuck is he doing? I asked myself.

The last thing I wanted was to confront him and wake up the rest of the boys, so I let him proceed while I pretended to be asleep. I was curious to see what his plan was, and I was too aroused to cut it short. He positioned himself behind me, close enough that I could feel his breath on the back of my neck.

He carefully removed the covers and pulled up my silk robe, pressing his throbbing cock against my ass. He grabbed a handful of my left ass cheek and spread it, wedging his hard shaft between my soft, warm cheeks. Encouraged by the hotness emanating from my forbidden entrance, he pulled my thong aside, exposing my wickedness. He didn’t know that I often masturbated to fantasies of fucking my son’s friends, but he had confirmation that my body was accepting of his intrusion.

I figured he would just fondle me and masturbate, but he had other ideas when he whispered into my ear, “I know you’re awake.”

My marriage had severely lacked sexual satisfaction and post-divorce I’d only had uneventful one-night stands through dating apps. My weak flesh couldn’t reject his advances, but it wasn’t like I was brazen enough to do or say anything. My body yearned for this. I was my own worst enemy.

He turned me on my stomach, putting me in a prone position then mounted me with his left arm around my abdomen and his right arm around my neck.

“But since you’re pretending to be asleep, I’ll tell you a little secret,” he continued.

He pressed his hips downward, spreading my labia with his tip but not penetrating me.

“I was sexting your son’s crush,” he revealed.

Hearing that caused my dwelling depravity to awaken. I knew it was immoral, but it ignited my lust into an inextinguishable fire.

“You’re such a naughty boy,” I said, breaking my silence.

“She loves my big dick but she’s afraid to take it,” he added.

While I found his revelation incredibly hot, it was equally immoral. I couldn't be a hypocrite, not when I had wicked fantasies of my own.

“I can take it with one condition,” I said, feeling his tip stretching my opening.

“What’s that?” he asked.

Even though I was committing a taboo act, I still had a semblance of being a good mother. I loved my son and would never allow anyone to hurt him in any way.

“That you leave my son and his crush out of this,” I pleaded.

His response was to hold my flesh tighter, lightly choking me with his right arm, and pushing himself inside. Inch by inch my pussy accommodated his thickness, stretching like I was a virgin and not a woman who had given birth.

He began pummeling me, with the ass cheeks he had salivated over many times providing a cushion for his thrusting. It was a position I had seen in porn videos, but one I’d never experienced before because my ex-husband and former partners would’ve had trouble penetrating me from such an angle.

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The position made my pussy narrower and if it wasn't for the two full portions of my cheeks, every thrust would have been accompanied by a bumping of my cervix. Nevertheless, the position showcased the versatility of his length to reach those deep erogenous zones.

He was the first to discover these unexplored depths in my body that contorted my face and enhanced my natural lubrication. I wanted to unleash my cries of pleasure, but all I could do was whimper while I gripped the sheets, knowing that my son’s room was only several feet away from mine.

I'm sorry for being a bad mother, baby, I thought, thinking of how I was betraying my son.

He moved his right hand over my mouth to keep me quiet, leaving only the squelching of my pussy to be heard. My mind had gone blank, all it could process was the feeling of my guts getting smashed. Although I was his friend’s mom, I had gone from his masturbatory fantasy to his sex doll.

Overtaken by my lust, I pushed my ass back into him, getting into the position that all the guys, including my son’s friends, who lusted after me, wanted me in – the doggy style position. I could no longer play the role of the innocent mother who was getting taken advantage of. I wanted my cheeks clapped.

My back was arched, with my face resting on the bed while my ass presented a special invitation for him. I took pride in knowing that none of his high school girlfriends or fuck buddies had an ass like mine.

After adjusting my thong further to the side, he ran his hands over the soft flesh of my ass cheeks, spreading them and aiming his cock at my entrance. He let a glob of saliva fall directly over my asshole, splashing on it then dribbling down to his cock. He slid himself in with the added makeshift lubrication, pushing his hips forward until my cheeks pressed against his thighs. He took a moment to enjoy the different sensation before pulling three-fourths of his length out and jamming it back inside me.

He placed his hands firmly around my hips and began violently thrusting into my squelching wetness, stinging my cervix with his tip, and making my cheeks ripple every time they crashed against his thighs. He was a madman reveling in his lust, determined to satiate it by any means necessary.

This angle allowed for a more profound penetration. I knew it well from all the times I had placed my suction cup dildo on the wall and thrown my ass back on it. The difference was that he was an improved version of my toy, one that was made of real flesh and came with the risk of pregnancy.

Every thrust, deep and long, stimulated my anterior fornix, making my pussy smear his shaft with my creamy, ovulating lubricant. The repeated bruising of my cervix brought me closer to, what was for me, an elusive penetrative orgasm.

I didn’t know how experienced he was having sex, how many high school girls his age he had fucked, but he surprised me with his endurance. He easily outperformed any of my previous partners.

His breathing got heavier but his assault was unrelenting. It made my juices drool on his cock and onto the bedsheets. I clenched my teeth, keeping my ass firmly in position, enjoying the vigorous pounding of my flesh.

The intense beating forced my body into submission. I muffled my moans by biting down on a pillow while waves of orgasmic ecstasy shot through my convulsing body. He groaned, burying his cock deeply, feeling my juices streaming out of my pussy. Rope after rope of his virile seed splashed against my cervix, knocking on my fertile womb – the womb where his friend had been conceived.

Exhausted, he dropped beside me, remaining motionless for several seconds as we enjoyed the post-orgasm aftershocks. He pulled up the covers and embraced me in the spooning position. Even if it was just for the night, we were going to numb ourselves and pretend everything was okay. As we drifted off to sleep, the moment reminded me of my early marriage days, full of love and affection, except for the fact that he was my son’s friend and we had just satisfied each other's carnal desires.

When I awoke in the morning, Jordan was gone, but not without having left me an insurmountable sense of guilt. To make matters worse, when I turned to look at the alarm clock on the nightstand, I spotted a note from Jordan.

I won’t tell anyone, but I want more, the note read.

Our taboo fantasy had been realized but now it was time to face the consequences of our actions. There was no telling how far things would go, but my immediate objective was to ensure that things didn't get out of hand. I couldn't run the risk of Jordan spilling our secret. I had to protect my son.

What have I gotten myself into? I asked myself.

I shook my head, realizing the magnitude of the problem I was in, but I didn’t have much time to think about it. I had to go see if Jordan and the rest of the boys had left or if they were hanging out in the living room.

I took a deep breath and exited my room with a mixture of regret and satisfaction. I didn't know if I'd ever be the same woman again and the worst part was that I didn't know if I wanted to be.

I walked into the living room, finding no trace of the boys, then I went into the kitchen to find my son serving himself a glass of orange juice.

“Good morning, sweetie,” I said, feeling a wave of shame crashing over me that made my face flush with guilt.

“Morning,” he said, before chugging his orange juice like he normally did.

It was a moment of normalcy until I sat down at the kitchen table and realized my creampied pussy was sore from the beating Jordan had given it.

Drowning in my guilt and shame, I found the courage to ask, "Did you have fun yesterday?"

“Yeah, it was great,” he said, joining me at the table.

I gave him a faint smile and said, “Well, er, just let me know when you want another sleepover and we can do it."

“Sounds good, but you don’t mind someone sleeping in your room?” he asked.

“Uh, no, I don’t mind. I mean, you could sleep with me next time,” I nervously replied.

“That’d be embarrassing,” he said.

With a sudden lurch in the pit of my stomach, I countered, “Oh, I don’t know, maybe you and Jordan then. It could be fun."

I was beyond the point of no return. In fact, I had already arrived at the destination of depravity and there was no way back. The whirlwind in my head was long from settling but one thing was clear, if I had become a taboo-breaking mother then I was going to be the best mother I could possibly be. Looking at my son sitting in front of me, I couldn’t help but wonder what would happen if I shared my bedroom with him and Jordan.

Published 
Written by Issabela
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