Naughty Encounter With Best Friend and Asleep Mother

As Steven and I were practising our shots in the driveway, my mom drove up, interrupting us. Steven has always had a thing for my mom, and today was no different.

She stepped out of the car, and Steven immediately made his move. “Hey, let me grab those bags for you, Claire,” he said, reaching for the door.

“No thanks, Steven, I’ve just got this small bag from the pharmacy,” she replied, holding it up.

Steven has always been open about his attraction to her, but my mom seems oblivious. Or maybe she doesn’t care. I feel like I’m the only one who notices.

“Hey, let’s keep playing, I’m only one point behind!” I called out, anxious to get back to our game.

“Sure thing, Darren. I’ve got to make a comeback and beat you!” Steven said, moving away to let my mom through.

Mom has always been curvy, but ever since she hit 40, her tits have become massive. Every time she bends down, I can’t help but stare. Sometimes, I even catch Steven checking her out.

“Have fun, boys,” she said, heading into the house. After she was in the house and out of earshot, I took a shot that bounced off the rim. Steven grabbed it and dribbled over to me. I knew what he wanted to talk about, and deep down, I liked talking about her, too.

“Man, dude, your mom is fucking hot for forty years old,” he said, standing there dribbling.

“I guess, but I ain’t ever really noticed,” I said nonchalantly.

“How big are those fucking tits of hers?” He asked, eager for me to refresh his memory.

“34D, I think. Well, I overheard her talking to Aunt Sandra before,” I said with a slight smile.

“Nice, her ass looks fucking amazing in everything she wears, especially those short skirts she wears to work,” he finally said, taking a shot.

“Man, do you jerk off a hundred times a week thinking about my mom?” I asked him, retrieving the ball.

Steven grinned and said, “Oh, like you don’t notice these things.” He looked at me with curiosity. “Did you see the medicine she got?”

“No, why should I?” I replied, wondering why he was asking.

“She got those new sleeping pills that are strong. They say you sleep for eight hours straight with them,” he told me.

Then, suddenly changing his mind, he said, “Actually, I’m going to head home now. Tell me tomorrow if those pills help your mom sleep,” and with that, he left.

We were both eighteen years old, and as far as I knew, we were both virgins, neither of us getting past second base. I think we spend too much time fixating on milfs and older women rather than girls our age. So I was going to make sure when Mom got up the next morning I would find out if she got a good night’s sleep, I was unsure why he wanted to know, unless he was thinking of getting some.

Dinner was uneventful; Mom was tired and did not feel much like talking, so she offered to do the dishes for her so she could rest.

I took all of the dirty dishes out to the kitchen; she then changed for bed, took one of her pills, and went to bed.

The following day, my mom looked really refreshed.

“Morning, Mom. Did you sleep well?” I asked her as she was about to leave for work.

“Oh, I had the best sleep in a long time. Love you, see you later,” she said quickly, heading out.

At school, Steven kept asking me about how my mom slept, which I still found odd. But I told him during lunch while we watched a game in the gym.

“She said it was the best sleep she’s had in years,” I shared.

“Can you text her and see if I can stay over this weekend, starting tonight?” Steven asked eagerly.

“Okay, I’ll text her now,” I said, pulling out my phone.

After I texted her, Steven was anxious to know her response.

“She’s okay with it, but we have to be quiet when she goes to bed,” I told him.

“Cool. Since today’s Thursday, I’ll need to grab some stuff from my place for the weekend,” Steven said, planning.

“Alright, catch you at my house after,” I said as the bell for class rang.

After school, I headed home to knock out my homework before Steven showed up. He arrived a bit before my mom got back. She rang me to say she’d grabbed pizza for dinner and needed a hand with it in the driveway.

“I’ll grab it,” Steven offered, sprinting to meet her.

I peeked out and saw him take the pizza from her, following her into the house and keeping his gaze fixed on her. Mom had one piece of pizza and a small salad at dinner, sticking to her diet. On the other hand, Steven and I wolfed down the pizza while he kept up his usual charm and compliments towards my mom.

“Darren, you could learn something from Steven about giving compliments,” my mom teased, making me feel awkward.

“Yeah, Mom, but just so you know, Steven and I have had about the same luck with girlfriends this year,” I shot back, and Steven’s face turned red.

“Don’t worry, boys. The right girl will come along for each of you. I’ve got some work to finish up. I’m planning to go to bed around nine, so please keep it down after that,” she reminded us.

We gave her space for the rest of the evening and hung out in my room playing video games. Right on schedule at nine, my mom popped her head in to check on us. She was dressed in silk pyjamas, and it was apparent she did not have a bra on.

“Good night, boys. I’m off to bed,” she said.

“Night, Mom,” I replied.

“Good night, Claire,” Steven chimed in. “Have sweet dreams.”

About an hour later, Steven quietly got up and tiptoed down the hallway to the bathroom. He carefully opened the medicine cabinet, removed the prescription bottle, and started counting the pills inside. Then, smiling, he returned to my room and sat down.

“I say let’s give it another hour and see how asleep your mom is,” he said.

“Are you fucking nuts? That’s my fucking mom,” I exclaimed.

“Dude, this will be the best time to find out,” he said. She took a pill tonight, and if they are as good as advertised, this should be interesting.”

“Alright, if we do anything you better let me go in first and see if she wakes, I can come up with an excuse for being in there,” I explained to him.

“You got a deal,” He said as we went back to playing for another hour.

At eleven o’clock, we crept down the hall, slowly opened her bedroom door, and crept into her room. We could hear her breathing from across the bedroom as she slept soundly. I slowly went up to her bed and gently shook her shoulder, then again, and then a third time a little harder and said Mom in a low voice.

“See, I told you she was out,” Steven said.

“So what are you going to do?” I asked him.

“We have to see those tits of hers, what you say, you want to see your mom’s boobs.” He said, reaching down with trembling hands.

Slowly, he undid the top button, then the next one to reveal more and more of her ample cleavage. The way the silk moved against her skin made her nipples start to harden against the fabric. He then undid another, then another, the top only had five buttons left the last one together and slowly slid off to her shoulders to expose her beautiful breasts.

“Holy shit, those have to be the best tits I have ever seen in my life,” Steven exclaimed softly.

“I can’t believe I’m standing here looking at my mother’s tits,” I whispered; at the same time, my cock started to harden in my pants.

Steven then touched one of her boobs; he started to caress one of my mom’s tits. Then he lightly stroked the nipple, which was now hard from the cooler air and the stimulation. He surprised me when he gave it a gentle squeeze, then the other a gentle squeeze, and then rubbed the nipple. This made my mother moan in her sleep; she must be enjoying the stimulation as she showed no sign of waking.

“Damn, your mom has got me so hard right now. You must feel them; you won’t believe how firm they are.” He said, moving his hand away to let me feel it.

I ran my shaking hand over her left breast, enjoying her soft skin. I took her nipple and pinched it while marvelling at how hard it was; then, I gave the breast a gentle squeeze; he was right steadfast. I continued to alternate playing with her tits while Steven ran his hand down to the bottom of her pyjama.

His hand slowly crept inside, he smiled as he worked his way down over her mound, and her legs were slightly spread so he had access to her pussy. My mother let out another moan, and you could see a look of pleasure on her face as her lips were now open like the letter o.

“She is so fucking wet and very clean-shaven down there too.” He said as he was rubbing her pussy.

After a while, I quickly buttoned her back up and left her to resume her peaceful sleep, and we hurried back to my room. I couldn’t get the sight of her tits and bald pussy out of my hard. Steven went to sleep, but I couldn’t sleep with this rock-solid hard-on. I went into the bathroom and jerked off damn I cum within 60 seconds thinking about my mom, what the hell is wrong with me. I then went back to bed and fell straight asleep.

Morning arrived and Steven told me he had to nip out, when he finally came back he had a filthy grin on his face. “Look what I got” he pulled out a box of condoms.

“What the fuck Steven, do you honestly want us to have sex with my mom? it’s a bit sick isn’t it, I mean fucking my mom.” I asked him.

“You saw last night how out she was. I think we can get away with it. Let me go first. Your mom is so hot, I’m willing to take a chance,” he said.

“Your fucking stupid man, she will know the next morning that someone has fucked her, and guess what? We are the only ones here, dumbass,” I asked him.

“Well, she might think she got fucked, that is why I got the condoms, and we won’t leave any evidence behind.” He replied.

“Man, you are fucking insane and perverted,” I exclaimed.

“Well, I saw how good your mom’s sexy body was last night; I want a piece of it. I can’t wait for bedtime.” He laughed.

My mom arrived home a few hours later, visibly worn out from her day at work. Just before leaving the office, she mentioned she had been stuck in a long meeting. Heading straight to the kitchen, she tossed a salad together and asked Steven and me if we could sort out our dinner. I assured her it was no problem, and Steven and I decided to grab a pizza from the takeout place down the street.

Returning home with our pizza, we found Mom relaxing on the couch. She had just showered, her hair still damp, and was wrapped in her large, fluffy pink robe. She was deep in conversation on the phone with Aunt Sandra. I couldn’t help but overhear bits of their talk – Mom was sharing her thoughts about possibly having another baby, but the challenges of being single made it complicated. After ending the call, she seemed to relax, popping in a DVD to watch as the evening wound down.

While watching the movie, my mom commented without looking away from the screen, “I’m not sure why you young lads want to hang around with an old lady like me on a Friday night. You should be out having fun with girls your age.”

I shrugged and said, “Well, I tried asking someone out on Thursday, but it didn’t go well. Not sure about Steven, though.”

Steven grinned and said in his usual flirty tone, “I didn’t even try. When Darren told me I could spend the weekend here with him and his charming mom, I couldn’t pass up the opportunity.”

Mom laughed softly at his comment. “Oh, Steven, you’re so sweet,” she said. She stretched as the movie neared its end and added, “Once this is over, I’m heading to bed. I’m fatigued. Might even take one of those new sleeping pills to help me drift off faster.”

“Okay, Mom. Those pills should help you get a good night’s rest,” I replied, hoping she’d sleep comfortably.

An hour later she got up to go to bed, She left the two of us alone downstairs to watch television; we waited a couple of hours before we went upstairs.

Now, it was one in the morning, and I could see my parents’ bedroom door half open.

We crept inside her room. Mom was out of it, and she was wearing a short silk night shirt tonight. Steven slowly pulled the blanket down off of her to reveal her legs which he now slightly spread; Mom had some sexy pink panties on, which Steven stretched over to the side, resting on one of her pussy flaps. She was clean-shaven.

He got on the bed and moved her legs further apart. He then climbed up between her legs; I can’t believe I was watching this. My best friend slid a condom on his dick and was ready to take my mom.

He got up inches away with his cock to her pussy as he positioned his cock to the entrance of her pussy; Inch by inch, he sunk his stiff cock into my mom’s pussy; I could hear him moan gently as he slowly started to sex with my mom. Mom just lay there taking it as her body swayed slightly with every thrust he gave her.

Steven was now getting too carried away, thrusting in and out of my mom slowly, at first, trying not to wake her or cum too fast. But the temptation was hard to fight for him as he soon started thrusting faster and faster.

“Oh Claire, Claire, your pussy is so wet and tight.” He grunted as he slid in and out of her.

“Mmm, Mmm, Mmmm, Mmmm.” My mom moaned softly as she was sleeping and getting fucked by my best friend.

He picked up pace, holding her hips as he slammed into her hard. “This feels… mmmm so good, dude your mom’s pussy is tensing up on me argh fuck” he said as I heard his body slapping against hers, and his balls slapping against her ass as his cock just pounded her.

Steven was grunting hard, and he moaned aloud, “Arrgh fuck” he was now emptying his load and cumin hard into his condom. He slowly finished cumming, and then he climbed off of my mom, sweat on his body as he walked towards me.

“Holy shit, dude, your mom is awesome; you got to try her pussy.” He said.

“I guess it’s my turn to have a pop at her. This feels wrong,” I said, getting undressed.

Remembering the phone call earlier I decided to leave the condom in my pocket. I’m not sure if this was a good idea or not. But maybe something good will come out of this for her.

I climbed onto the bed, and I stroked my cock a few times before I pushed it towards her pussy. Then I gave it a push. I was mesmerized by seeing her pussy lips open as the head of my cock slid inside, she was very wet still, and she groaned when she felt my cock.

I slowly started to move my dick in and out movements as her pussy hugged my shaft. I got one of her boobs out and sucked on it as I continued to fuck her pussy slowly.

This felt so good; it was wrong, but fucking hell, my cock felt good in her pussy. I started to go a little faster as my cock pounded her pussy. Oh shit, this was amazing. I started pounding my cock into her as hard as I could; my mom was grunting with each of my thrusts.

The bed started squeaking as I went faster, lifting her legs and placing them over my shoulders. Now I can drive deeper into her as I pump and pound her pussy. Looking down turned me on, seeing my cock in a blur going in and out at a fast rate fucking her.

I couldn’t hold on any longer as I felt my balls tingle as I kept pounding into her pussy, looking down at my mom as her tits bounced around. I reached the point of no return, “Fucking hell”, I grunted and groaned as I held her hips tightly and pumped her until I finished shooting my load.

I could feel a lot of cum flowing through my dick; I stopped pounding when I finished cumin. I took a deep breath, slowly pulled out, and climbed off my mom.

Steven looked at me with shock. “Dude, what the… You didn’t put on your condom” he was right, fuck, what have I done.

“Can’t believe you emptied your load inside your mom, man. Now she defiantly will know she got fucked. Also, I can’t believe how you hammered the hell out of her.” He said as he went towards the bedroom.

Before leaving my mom’s room, I leaned in and kissed her cheek, “I am sorry Mom; I know you can’t hear me. But I didn’t wear a condom on purpose as I know how much you want another baby, the sad excuse I know” and I straightened her panties back to normal and went to bed.

“Dude, she’s your mom, damn man, you pounded the fuck out of her like she was a piece of meat, anyway. Goodnight motherfucker. I wish I could do her tomorrow, too, but I must go home.” He said.

“Goodnight motherfucker.” I replied, laughing.

The next day, Steven went home, and I felt guilty eating me away. But at the same time, I was getting addicted to fucking my own mom.

Later that day, Mom was in the kitchen cooking food. It smelt lovely, and I was so hungry.

I sauntered into the dining room, my eyes fixated on my mother’s voluptuous figure. She was dressed in a skimpy, floral sundress that barely concealed her ample cleavage and juicy ass. The sight of her was enough to make my cock twitch in anticipation.

“Has Steven gone home, sweetie?” she asked as I took a seat across from her. I carved into my sausages, savouring the salty, fatty meat on my tongue.

“Yes, he had some insignificant errands to run, but he seemed to enjoy his stay here over the weekend,” she replied, her voice dripping with disdain.

“You both seemed off this weekend or maybe it’s just my imagination,” she mused, fidgeting with her fork. “I’ve been feeling strange since I started taking those fucking sleeping pills.”

She looked up at me, her eyes glazed over with a mixture of boredom and irritation. “But I’m sure it’s nothing, just the medication playing with my mind. I’m glad that little bitch had a good time here. We should invite him over more often, don’t you think?”

I chuckled at her sarcasm. “Definitely, Mom, he’d love that,” I said, my mind filled with the memories of our debauchery the night before.

Later that night, I waited patiently in the hallway outside my mother’s bedroom. I could hear her soft snores as she slept peacefully, her breathing steady and slow. I gently pushed the door open and crept inside, my heart racing with excitement and anticipation.

The nightlight’s soft glow dimly lit the room, casting eerie shadows on the walls. My mother lay on the bed, her smooth, delicate body exposed for me to see. She was wearing a thin, lacy nightgown that barely covered her full, round breasts, and her hair was tousled, making her look even more seductive.

I approached the bed, my cock already hard and throbbing with need. I slowly lifted the sheet, revealing she had no panties on and I could see her smooth, hairless pussy. I could see her labia glistening with wetness, inviting me to plunge my cock deep inside her.

I climbed onto the bed, positioning myself between her legs. I wet the tip of my cock and gently pushed it inside her. She was warm and tight, her walls clenching around me as I slid deeper inside her.

I began to thrust in and out of her, my balls slapping against her ass with each stroke. She moaned softly in her sleep, her body writhing with pleasure. I grabbed onto her hips, pulling her closer to me as I fucked her harder and faster.

The sound of our bodies slapping against each other filled the room, along with my grunts and groans of pleasure. I could feel my orgasm building up inside me, my balls tightening as I got closer to the edge.

I couldn’t hold back any longer. I thrust deep inside her one last time, my cock twitching as I released my load. I could feel her pussy contracting around me, milking every last drop of cum from my balls.

I collapsed onto the bed, spent and exhausted. I slowly pulled out of her, my cock covered in her juices. I adjusted her nightgown and tiptoed out of the room, feeling a mixture of guilt and satisfaction. I knew what I did was wrong, but I couldn’t help myself.

Three weeks have passed since that night, and I have done it several times within the last three weeks. I finally started to control myself and talked her into stopping taking the tablets.

One morning, I woke up to the sound of my mother vomiting in the bathroom.

I quickly got dressed and went to check on her. She looked pale and weak, and I immediately regretted my actions. Was she pregnant?

After a few days of feeling sick and tired, I convinced her to go to the doctor. I went with her, feeling a sense of guilt and dread in the pit of my stomach. I couldn’t believe I had taken advantage of her while she was under the influence of sleeping pills.

The doctor confirmed my worst fears: she was pregnant. She was shocked and confused.

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