High School Days Ch. 05

Story Info
Son and friend dp mom then plan to dp friend's mom.
4.4k words
4.54
127.5k
54
7

Part 5 of the 5 part series

Updated 10/25/2022
Created 12/26/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
nikkis
nikkis
245 Followers

I was barely awake but had not opened my eyes yet. I just let my mind go over the events of the last few days. This was Sunday morning and all of this started Friday afternoon when I came home earlier than expected and caught mom fucking her ex, my dad. Dad never saw me but mom sure did. Then that night mom had me tell her about a sexy adventure with me and my friends as payback for watching her get fucked and not leaving when she signaled me to leave. I purposely told her a very nasty one in hopes that she would reply in like kind when it was her turn. The next day, Saturday, we both ran road races and did well. That night I suddenly got severe leg clamps. Mom massaged them away while I lay on the couch on my back naked but I got a hard-on. Somehow mom ended up with a face full of cum. I'm still in disbelief about that my first sexual encounter ever with my mother.

That was follow by me talking mom into telling me a sexy adventure from her high school days. And that end with me fucking someone in the ass for the first time in my life, my mom. We were caught in the act by Karen and mom shrewdly pulled her in and taught her how to take a big cock up her ass, mine.

Saturday night didn't stop there. My best friend Brad came over with his sexy ass girl friend, Sasha. Sasha seemed to "fall in love" with mom and sexually pursued mom to do several sex acts I never thought I'd see mom do. The evening ended with me fucking mom in front of my three friends. What a fucking night that was.

I was still in bed with my eyes closed but now I had a big smile on my face. I rolled over to get more sleep, after all I did cum four times last night once on mom's face, then in mom's ass, then in Karen's ass and lastly in mom's pussy. I was almost asleep again when I heard the door bell ring. Mom must have been in the kitchen because she was at the door pretty quick. I could hear Brad talking with mom. I listened closely to get a clued as to how they would talk to each other after mom was directed by Sasha to suck his dick last night and then he witnesses me fucking mom.

The conversation sound up-beat as if nothing ever happened but then mom and Brad always had an easy way about them. It seemed like they always got each other's jokes and built off of them. I couldn't hear everything clearly but I did catch that Brad was there for me. He mentioned we had a city league basketball game to play. I wasn't eager to play when he first told me about it 2 weeks ago. I told him if he couldn't find someone else, I'd do it.

I just stayed in bed hoping he'd go away but he didn't. I heard mom and Brad talking as they were approaching my room. I figured I'd make believe I was asleep.

I heard a light knock on the door followed by, "Jack are you awake?"

It was mom. I stayed silent. I could hear mom walk in with Brad. She sat on my bed and whispered, "Jack it's time to wake up."

I just groaned but kept my eyes shut. I rolled to my back and since I was naked I could feel my cock was hard and slid under the sheets. I still didn't open my eyes.

Mom said, "Baby wake up."

I said, with my eyes still closed, "Not until I get a kiss from you like last night."

I heard mom giggle then I felt her face on mine as her gave me a soft loving kiss on my lips.

I said smiling, "Yummy but I need more."

Mom let out a soft laugh but leaned over and kissed me a little longer. I reached behind her head and held her there while I opened my mouth and worked my tongue inside of her mouth. She didn't resist. So, I took my other hand and placed it on the inside of her knee and gradually slipped it up her leg while I kept kissing her deeply. I could feel the hem on a dress sliding along my arm as my hand continued up her dress. My eyes were still closed so I didn't see Brad there although, I knew he was there. I made it seem like I was just having an intimate moment with my mom after a night of fucking her.

Mom was trying to break the kiss probably to tell me that we were not alone but I didn't let her. My hand was now rubbing on mom pussy through her panties under her sun dress (I found this out later).

Mom finally broke our kiss and announced, "Brad is here to take you to a basketball game."

I opened my eyes and greeted Brad. Brad's face was a little red from what he was seeing. He talked fast explaining why he was there and how he couldn't find someone else and how I promise if that happened that I'd play. I listened to him but continued to play with mom's pussy. Brad couldn't see what I was doing under mom's dress. I had a thumb on her clit and slid two fingers past her panties and they were now inside her damp pussy as I moved them around. Mom was sitting up now watching Brad talk. I think she was just checking his facial expressions to see if he had noticed what was happening.

When Brad stopped I asked him some details about the event like I needed more information before I could make a decision but that wasn't the reason for my questions. I just wanted to keep him talking while I got my mom hot enough to get her to relieve my hard-on.

I glanced at mom from time to time and she gave me a little smile. She was getting off on the scene as well. I thought, "What a nasty little bitch mom is becoming." Letting me play with her pussy while Brad is right there unaware of the event.

I felt mom slow tilt her hips and open her legs so she could give me better access. I looked at her and gave her a smile of approval as I pushed another finger into her. Mom's pretty light green eyes were almost closed in ecstasy. I had her where I wanted her.

While Brad was still talking I whispered to mom, "Mom can you stroke my cock?"

Brad stopped in mid-sentence. The room was completely silent. I pressed my thumb hard onto mom's clit and she let out a soft moan. Mom looked at Brad then at me. I continued to rub her clit, poor mom was a slave to her own need. I could feel the juices flowing in her pussy. Since she didn't stop me I knew it was a matter of time before she would comply. I was right.

Mom looked right at me like Brad wasn't there and I could see, out of the corner of my eye, mom's hand move under my sheet and directly to my cock. "Yes." I thought. This was going to happen right there in front of Brad. This was such a turn on for me.

Mom wasted no time, she must have been close herself. I felt her hand grip my cock and immediately start to stroke it. I closed my eyes for a moment to take in the feeling. I stopped rubbing her clit so hard and started to slow down on mom's pussy. Now that I had her stroking my cock in front of Brad while I played with her pussy what else might she do?

I let the scene play out a little then I said, "Play with Brad's cock through his pants."

Mom gave me no reaction. She looked confused like she was thinking about it and what that meant. I put more pressure on her clit. She opened her mouth and let out another soft moan. I knew she was close. I stopped. Mom looked at me with this 'what the fuck' expression.

I smiled and whispered, "Pull Brad's cock out and play with it."

Mom looked at Brad put her hand flat on his crotch then looked at me and started to unzip his pants. In a moment Brad's hard cock was free and mom was stroking it. Actually, she was stroking us both at the same time. I started working her pussy again. She was now openly pumping her hips into my hand with her mouth slightly open and her eyes half closed, her breathing was laboring.

I said directly, "Lift up a little so I can pull down your panties."

She did. I quickly pulled off her panties and she sat back down. I rubbed my fingers up and down her clit and pussy.

When I thought she was hot again I whispered, "Suck Brad's cock."

Mom looked at me. I could tell she wasn't sure she could do this.

I looked right into her eyes and firmly said, "Do it."

She looked at me as she leaned toward Brad's cock while she slowly opening her mouth in anticipation. Brad put a gentle hand on the back of mom head as if to insure it would happen and it did.

Mom was now sucking Brad's cock with Brad's hand on the back of her head urging her on. She was still sitting on my bed with her sun dress hiked up as I played with her pussy in inventive ways. She still had a hold of my cock and was stroking it. She was really hot again working the shit out of Brad's cock with her experienced mouth.

I whispered to her, "Sit on me. Sit on my cock."

Mom didn't even look at me. It was like this was the most natural thing for her to do. She stepped over me with a leg positioned on either side as she pulled Brad by his cock to get close enough to do both. I was actually very surprised at her acceptance of my last command. I was prepared for more resistance but it never came. Mom was becoming my little whore.

Mom was now kneeling over my cock with a leg on either side of my body, my cockhead was touching the pink folds of her pussy. She came off of Brad's cock to concentrate on my cock. She used her hand to direct my cock just in the right position for entry then she just paused. My cockhead was partly nestled in her pussy folds but really wasn't in mom's pussy yet. Mom closed her eyes and let her weight slowly down onto my cock. Her pussy was soaking wet and my cock steadily push itself past the entrance to her pussy. Mom threw her head back and let out a long sexy moan as she let my monster cock slid deeper and deeper into her tight pussy.

Yes, her pussy was tight, I was her only child and that was a Caesarian birth. Mom's pussy was the tightest pussy I had ever fucked. She later told me that my cock was the biggest cock she'd ever fucked. It was a highly sensuous experience for both of us.

Mom finally had me in her. She just sat there for the longest time with her eyes close and head slightly back taking in the sensation. She then started an easy rocking motion as she reached up and openly played with her nipples. The combo of the sexy scene and sensation was absolutely awesome. This has long since been a fond memory for me.

Mom gradually picked up the pace. She started driving her hips into my erect cock with more conviction. As I noticed her intensity built I smiled inside. I haven't forgotten about Brad, I was just waiting for the right moment to re-introduce him.

Mom was lost in sexual lust, shamelessly fucking her own son right in front of his best friend.

I said to mom, "Pull off your dress."

She grabbed the hem and pulled the entire thing up her body and over her head then she simply threw it away. She was now completely naked. That beautiful fit body was now in full view, privately for me and Brad while she rode her son's thick cock.

As I looked at her I could see my dear loving friend and mother yet looking at her in another way she was sexy, very naughty and out of control. My curiosity wanted to know how out of control she might get.

"Mom" I softly said.

It took her a moment to come back from where she was in her mind. She slowly opened her eyes and looked at me.

I then said, "Suck Brad. Get him nice and wet. Get him wet enough to be able to fuck your ass."

Mom continued to drive her hips into my cock and looked at me for a moment then a small smile began to blossom on her face. I thought, "What a little whore she is becoming". I loved it.

Mom continued her motion while she reached for Brad's cock and pulled him close enough. She then looked up at Brad and took his cock deep into her throat again and again. I could tell Brad was excited. Mom pulled back off Brad's cock and looked at it, assessing if it was wet enough. Brad was too pumped to wait for a formal decree. He immediately pulled away and moved in behind mom's ass while positioning himself.

Mom stopped moving her hips and leaned forward to accommodate Brad and just stared blankly waiting for Brad's attempt. Brad had a lot of ass fucking experience with Sasha since she was technically a virgin Sasha's ass was the only fucking he got. I watched Brad's movement as he prepared himself then suddenly mom let out a sound that was a cross between a moan and a groan. Mom tightly closed her eyes as if in pain and continued to moan/groan as Brad worked in more cock up her firm ass. Brad never apologized and mom never complained, she just took the punishment arising from Brad's eagerness.

Brad announced to us, "I'm in. Man is this tight."

I said, "OK big guy just stay still for a while and let mom get used to it."

A little time went by but mom was the first to move. She started to slowly rock back and forth on the two young cocks buried deep in her pussy and ass. Brad and I held still and let mom fuck us both at the same time. It was heaven. Mom picked up the pace. Brad took notice and gripped mom's hips and started to fuck mom's ass. I could hear Brad's hips slapping into mom's firm ass cheeks. I could also feel each jolt of mom's body from Brad's pounding.

I started to drive my hips into mom's soaking wet, tight pussy. I searched for a rhythm to coordinate the fucking assault on my mother. It wasn't long before the three of us were completely engaged in a hot lustful fuck. We were all breathing hard and fucking for all we were worth.

Mom's body started to shutter, her breath came short and quick. She was starting to cum. Brad was getting louder and delivering more forceful thrusts. I was sure it wouldn't be long for him either and I wasn't far behind.

Suddenly, mom let out a loud sexy groan then a scream as her body shook uncontrollably. Brad and I both got off on the whole scene and exploded at the same time into mom's pussy and ass. It was so loud at that moment I could tell what sound was coming from who. A moment later all three of us were laying down trying to catch our breath.

Mom spoke first saying while softly laughing, "Holy shit, that was fucking awesome."

I was a little shocked to hear mom's language.

Brad followed by saying, "Mrs. Anderson, I know I'll never forget this moment."

He paused then added, "I want to marry you."

We all burst out in a roaring laugh.

Then mom looked at my clock and said, "What time is your game?"

Brad jumped up and said, "Crap, we are going to miss warm-ups."

I quickly said, "I think we just did that."

We laughed again. Then mom got up grabbed her sundress and while heading out said, "Let me make you some food to take with you. Jack, you should hit the shower and Brad you might want to clean up a little as well."

Mom was out the door on her way to the kitchen. I was up headed for the shower and Brad was right behind me. While I was in the shower Brad was washing his balls and cock in the sink. When I got out of the shower while toweling off, I could hear Brad and mom talking and laughing in the kitchen. I quickly got my basketball clothes on and headed that way.

Mom saw me then turned and grabbed a paper bag loaded with a couple of fried egg sandwiches and handed it to me. She picked up two sport drinks and handed them to Brad then pushed us out the door.

While in the car driving to the gym Brad and I ate up the sandwiches and drank the sports drinks. We were quiet for a moment then Brad said, "Man that was awesome."

I nodded then said, "You owe me two of your women."

Brad looked over at me and with a frown said, "What?"

I shot back at him saying, "Last weekend you filled my girl friend's mouth with a load of cum at the drive-in and this weekend you fucked my mom in the ass. You owe me two women."

Brad said, "Ok man, I get it. If it makes you feel better the night we fucked Karen, Sasha mentioned how she'd like to know what that big dick of your would feel like up her ass. Last night she said, she really wants to have your cock up her ass."

I replied, "Good to hear, we are making progress in the planning department, Bud. However, my dick hasn't touched Sasha's ass and even if it did you are short one."

Brad shockingly answered, "Shit man, you want to fuck my mom? Fuck, I haven't even fucked her. I don't have the same kind of relationship with my mother as you have with your mom."

I quickly replied, "I didn't have this kind of "relationship" two days ago. Things can happen fast if you look for the opportunities. Isn't your dad away on business trips a lot?"

Brad said, "Yeah, he supplies equipment to oil riggers and sometimes he's out of the country."

I replied, "Well that sounds like an opportunity. I guess your mom gets pretty horny between pit stops."

Brad thought about it then said, "I'll bet you're right. I really hadn't thought about it. I know dad come back off those trips horny. He's all over mom when he comes home. He fucks the shit out of her. If it wasn't for mom he'd probably fuck her in front of me."

Brad laughed then continued, "Last time he was home he caught me fucking Sasha in my room. I had her bent over my desk and fucking the shit out of her muscular ass, when I noticed a little moment coming from my door. I looked over and it was dad with a big smile giving me the thumbs up. It was a little strange and it threw me off until Sasha demanded I start to "really" fuck her. I forgot about dad and plowed her ass good."

Brad laughed again then continued, "Later, after Sasha left, dad talked to me and said, 'he owed me one'. Then he asked me if, 'I was going to be around tonight'. I told him, I was and he just gave me a wink."

I asked, "So, what happened?"

Brad smiled saying, "Well after dinner dad got a little frisky with mom he grabbed her ass and tits right in front of me. Of course, mom battled him back but she was laughing at his behavior. She finally whispered in his hear and they headed for the bed room. Dad walked behind her grabbed her ass a few time as she laughed and started to walk sexy for him. Dad moved to the side so I could see then turned, looked at me and waved me to follow them but then put he's finger to his lip signaling to me to be quiet."

Brad let out a little laugh as he drove the car and was remembering the event. He continued, "Once they were in the bed room, dad closed the door hard enough to hear it close but then opened it ever so slightly. I figured he closed it loud enough so mom thought it was close but then opened it so I could spy on them. Talk about the door of opportunity..."

We both laughed.

Brad continued, "I played it cool and waited a few minutes then I shut off the hall light and I moved to the door. There was some light coming from a lamp. I saw dad was naked and facing me while mom was naked on her knees in front of him sucking his cock. Dad saw me right away and smiled.

He then looked at mom and said, "That's it honey get it nice and wet because I want to fuck your ass tonight."

Mom never missed a beat. I gather from that exchange that she was used to ass fucking or something.

Dad took mom by the hand and guided her onto the bed. While she was getting up on it dad looked at me and gave me a quick thumbs up. He positioned mom in a sexy pose with her nice thin body looking super hot by the lamp light. You know mom isn't as muscular as you mom. She's more like a model actually, almost skinny with big tits."

I chimed in saying, "Oh yeah, I know she is definitely hot looking. I bet that sexy walk to their room gave you a hard on."

Brad replied, "Your fucking right it did."

"So what happened next?"

Brad continued, "Once mom was in position she said in a dreamy voice, "Start slow babe, my ass hasn't been fucked for a while, I'll need to get used to it again."

Dad let his hand come down a little hard on mom's ass and she jumped a little then softly laughed. He rubbed her ass then put his thumb on mom's asshole and just rubbed it, mom turned forward and moaned like she was really loving it. Dad then pushed his thumb inside of mom's ass in one motion. Mom arched her back and threw her head back and let out a very sexy moan."

nikkis
nikkis
245 Followers
12