My Sister My Mentor...
Taboo/incest Story

My Sister My Mentor...

by Originsunnown 19 min read 4.7 (23,000 views)
sister mother anal straight sex
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This one contains a scene of anal, I know it's not something everyone likes so here's your warning. Likely to write more on this later, need to finish off a few I have going first! Enjoy! O.

I got to enjoy the quiet for a while at home. My older sister, Jenna, had been living with her boyfriend for a year but he cheated on her and after an explosive break up, she moved back home. Since she'd moved out, I had inherited her larger room. She was too upset to care when she got mine on her return and put her rage into redecorating and making it her space. Mom fully expected a fight about it but I guess she'd matured a little on her own and simply said 'I am just grateful for a place to live' and carried on.

I had kept some of the things from her old setup. She had a great accent wall with built in shelves that I kept. I got a new, larger bed and did my best to show that after turning 20, I too could be seen as more mature. Mom was more understanding. Dad teased a little but he was away a lot being a long-distance trucker so it was all fine.

Once Jenna got over her breakup, she vowed to stay single for a while to 'find herself' which involved a lot of remembering how much she loved to tease me. I'd messed around with a few girls, lost my virginity to a pretty girl at a party but I was very inexperienced when it came to sex. Being a little shy didn't help me so you can imagine how Jenna liked to tease about my lack of girlfriends and assumed I was still a virgin.

One Saturday evening, I was sitting in my room watching porn on my laptop. I had my lights out and was watching one of my videos with the sound down really low. It was one of my favorites, cliche I know but it was a mean stepsister that eventually (5 minutes into the video, porn timelines) seduced and fucked her nerdy stepbrother. My own sister was hot, I will fully admit to enjoying views of her in a bikini or low-cut top but didn't think I'd get to cross that 'forbidden line' in a thousand years. As I got close to climax, I noticed light coming from my accent wall. I had loaned a couple of my books to my friend so it would usually have been covered but I got up and investigated. It was about chest height and when I looked closer, I could see it was a tiny peep hole. I looked through and it gave a clear view to where my bed used to be. It was now Jenna's bed and I had to stifle a gasp at my view. She was laying completely naked on her bed, legs wide open and was fucking herself with a dildo as she held a small vibrator on her clit. My cock had softened a little but the view had me rock hard again. I couldn't help it, I stroked my cock at the same speed she was fucking herself and when she covered her mouth to stifle her moans, I came too and sprayed cum all over my wall and floor. I looked through again and she still had the toy half inside herself, her vibrator was off and beside her on her bed as she caught her breath. I quietly cleaned myself and my wall up then went back to bed.

Usually after cleanup I'd roll over and go to sleep but I couldn't get the hole out of my mind. I jerked off a lot, even when Jenna still lived at home. Had she been watching me? I'd never seen any holes in my wall but I never really had a reason to look. I eventually got to sleep and had forgotten about it until later that Sunday. Mom was out running errands and after I'd cut the grass, I went to my room with the intention of jerking off again to the mental images I got the night before of Jenna. I didn't need to imagine though, I moved the replacement book I'd put over the hole and looked through again. Jenna was on all fours this time, she had a plug in her ass and was fucking herself with the same dildo from Saturday night. I was hard in seconds.

I covered the hole back up and was on my bed with my pants and boxers round my ankles in no time. I didn't last, five or six strokes and I was covering my t-shirt in cum. I cleaned myself up and grinned at the amazing show.

The next few days went the same. The hole was like my obsession and I would cum so hard watching Jenna fuck herself with various toys. It was almost like she was putting on a show for me each time too, she'd look right at me when she climaxed and I swear I almost blacked out I was cumming so hard.

Her attitude towards me outside her room didn't change. She'd still tease and pick on me and I just accepted it as a price for getting the shows. After one pretty intense session though I decided to take things further. I wondered how many times she'd watched me jerk off looking through that very same hole. She would have seen so much. Confronting Jenna about it when she got home that day, didn't go how I planned in my head.

"So, how long did you watch me for?" I said to her. She was sitting reading something on her phone.

"What the fuck are you talking about, weirdo," she replied.

"I found your hole."

"Again, what are you jabbering on about?"

"I watched you, no doubt where you would have watched me."

"Marcus, if you don't start making sense, I'm going to punch you in the balls."

"I watch you play with yourself through your hole in my wall!"

She stared at me for what felt like forever.

"You watched me masturbate?" she said quietly.

"Yes," I replied.

She didn't say anything else, I heard her go upstairs and into my room. A few thumps and a couple of minutes later she came back and handed me a roll of painters tape.

"If I find you've taken pictures or told anyone you spied on me, I'll cut your fucking dick off. Do you understand me?" she said, getting right in my face.

"Y.... Yes," I stammered.

She stormed out of the kitchen and went to watch tv. I went back to my room and found the books I had covering the hole on the floor. She'd covered up the hole on her side too and had covered up the keyholes in her bathroom door. I thought it best to let it go and went to wishing I'd kept my mouth shut. Her wrath was pretty relentless. She'd wear low cut tops then would glare at me if I dared to look at her cleavage. Any time she'd leave the room after Mom she'd mutter 'fucking perv' if I dared look in her direction.

After a week or so, things settled down again. She seemed to forget about being mad at me and life went back to our usual back and forth. Life soon handed me something amazing though and I couldn't believe my luck.

"Jenna, let's go, any longer and we'll be stuck in traffic all fucking morning!" yelled Mom. They were going to the store.

"I can't find my shoes," she yelled back.

"They're down here where you left them."

Jenna was moving pretty quickly just wearing her socks on her feet. She slipped on the top stair and landed pretty hard on her ass but just swore and sprinted down the stairs. I went out to the hallway to make sure they had left; I had plans to just jerk off while they were gone since it was pouring rain and spotted a tiny remote sitting at the top of the stairs. It must have fallen out of Jenna's pocket when she fell, I picked it up and couldn't believe what I had. "Lovejoy, Couples Remote" it said on the label. It had 3 different vibrate patterns and an up/down button for intensity. The light at the top was blue at first but then went red, the icon looked like a connection symbol. I thought about what to do then just put it in my pocket until she got back with Mom.

They were unloading the groceries from the car when I saw the connection light go blue again. I walked downstairs and before I got into the driveway to help unload the car, I pressed first button and set it to level 1 on the screen. Jenna immediately froze and looked right at me with her mouth open a little.

"What's wrong with you?" asked Mom impatiently.

"Just remembered I forgot something. It's fine," she said and gave me a look.

I grinned as they both walked by me then pressed the button to make it level 2. I grabbed as many bags as I could then took them into the kitchen.

"Is there many more, honey? Madam is feeling lightheaded and had to sit down," said Mom.

"No, one more trip should do it, I'll get it if Jenna can close the trunk behind me," I replied.

My hands were full when she passed me in the garage. She stopped beside me and said 'no higher' through her teeth then went to close the trunk. She managed to help put the groceries away with Mom and I then sat down again.

"Why don't you go lay down, Jenna, you look a little peaked," Mom said to her.

"I think I will, not sure what's come over me," she replied.

She gave me a look as she left the room, Mom was putting stuff into the fridge so couldn't see her face.

"You need any more help, Mom?" I asked.

"No, I'm good. Thank you for your help," she said and kissed me on the cheek.

I got to my room and noticed the book covering the hole had been laid on it's side and to my delight, the hole was uncovered on her side. I got a text from her too. "Don't tell anyone, don't be a dick about it," it said.

She was naked on her bed, her beautiful body on full display to me. She was kneeling up with her legs open and she was pinching her nipple as she rubbed her clit. She was soaking wet too, she'd occasionally lick the cream from her fingers. She let go of her pale nipple and sent me a text that just said 'L3', I almost dropped the remote but managed to set it to level 3 and continued watching. I was hard as steel, I watched intently as she furiously rubbed her clit then almost convulsed as she climaxed. I watched her pull the small egg-shaped vibrators from her pussy and she texted me 'off'. I looked down to find the power button and after I pressed it, I looked back through the hole and she was gone. I jumped when she was suddenly standing beside me in my room.

"What do you want," she said, still catching her breath.

"W... What do you mean?" I stammered.

"You're standing there with your dick in your hand, you just made me cum."

"I uh, I don't know."

She looked at me for a second then led me to my bed and had me sit down. Without saying anything, she got on her knees between my legs and started sucking my cock. I gasped in pleasure, she was more talented than I'd ever experienced before and before too long I was ready to cum. I managed to warn her, she let my first spurt spray into her mouth then she aimed my cock at her chest and stroked me as I came over her breasts. She looked up at me as the last few globs of cum oozed over her hand then wiped that on her chest too.

"Keep the remote charged. I'll text you when I'm wearing. Do not tell anyone about this, do you understand?" she said quietly.

"I won't tell a soul," I replied.

"Good. Figure out what you want."

"I want to watch you in the shower." I blurted out.

She paused before she left.

"The door won't be locked," she said then went to the bathroom.

I heard the water running a minute or so later. My heart was pounding in my chest. I was still naked from the waist down but I walked in slowly, half expecting to be screamed at despite my obvious green light. Jenna had her eyes closed and was letting the water run over her face. She really was beautiful to me, her blonde hair was wet and stuck to her head, her large breasts with pale nipples glistening in the water. She looked at me then slowly rubbed her shower gel over her body. It didn't take long, I felt myself getting hard again and I slowly fondled my balls as I watched her. She smiled and shook her head then actually opened the shower door and stepped out, still half covered in soap.

"I can see I have a lot to teach you. Lose the shirt and get in here," she said.

I was shaking when I stepped into the shower with her. She poured shower gel into my hands and leaned back against my chest.

"I don't think I did a good job washing your cum off my chest, maybe you should wash them again for me," she said.

She was just a little shorter than I am but I was able to wash every inch of her breasts. My cock was throbbing by the time I was done, she could feel it pressing into her back. She took control again and leaned forward, reached between us and fed my cock into her pussy. She took my hands and put them on her waist and looked over her shoulder at me.

"Hopefully since you've cum you'll last long enough to get me off. Fuck me nice and hard," she said.

I did as she asked and held on to her waist as I slammed into her. I'm not sure how long I lasted but I felt her pussy tighten a few times as she gasped in pleasure. I felt myself getting close again.

"I... I'm gonna cum," I said to her.

"I'm on the pill, push it in nice and deep," she gasped.

I did as she asked and pushed my cock deep inside her and sprayed what seed I had left into her. Before I started to soften, we felt the water getting cold.

"Shit, we used up the hot water," laughed Jenna.

She turned the shower off and grabbed her towel as she got out.

"Go dry off and get dressed, we'll talk in a bit, okay?" she said then went to her room.

I was sitting in my lounging sweatpants when she came to see me that night before dinner. My mind was all over the place, I felt guilty for some reason. I think I started shaking again when Jenna jumped on my bed and cuddled with me.

"I'll be wearing them at dinner so if you wanted to be naughty and get me all excited during dinner, you totally could," she said to me.

"Okay," I replied, quietly.

"Marcus, I'm giving you control of my pussy. Why are you so afraid?"

"I don't know, you were so mad at me before when I was watching you."

"Well I'm not mad now. You have a nice cock and we can have fun while I'm single. You haven't been with many women have you? I'm not teasing, just asking."

"I lost my virginity to Heather at a party, have had a couple of blow jobs and had this other girl at the lake but nothing serious."

"So let me teach you, I'll help with your confidence and I'll get to cum with something other than a toy in me."

"Okay."

"Or if you're not sure, I could go back to being a bitch to you and lock my bathroom door, is your choice," she said, grinning.

I responded by grabbing her ass and kissed her firmly on the mouth.

"Well, now you're getting it. Do me a favor and don't get cocky though okay? Enjoy this, we like, really shouldn't be doing this but we're both adults so why not."

The following few weeks turned into months and were amazing. I'd use the remote all day when we were with Mom then she'd pounce on me when we were left alone. She would sit on my face and taught me how to eat pussy. In between our frenzied fucking she'd teach me how to find her spots and not just slam into her. We'd kiss for hours too, she told me I was a natural at that. One evening, while Mom was out to dinner with Dad (he was just home for a couple of days) we had just finished making love on her bed and were cuddled together. I looked at the wall with the hole and laughed.

"What's so funny," she said, poking me in the ribs.

"All the time I thought you were putting on a show for me and you were really just watching yourself in your mirror," I replied.

"Well, yea. I still don't know why that hole is there, I swear it didn't make it."

"Maybe a happy coincidence."

"I'll take it, led me to a great fuck toy that I don't have to pretend to like," she said, laughing.

"Hey!"

"It's because I already love you, doofus."

My heart jumped a little. I'd held back on any kind of attachment to Jenna.

"I... I love you too, Jenna."

"Marcus, as your Sister, I love you as your Sister. When you get yourself a girlfriend, you'll use what I taught you and she'll keep you, trust me. I think I'm ready to start dating again and I just don't want you getting hurt, okay?"

"Sorry, I misunderstood."

"It's fine, it's why we talk. Are you spent? I think we have time for a quickie before they get back."

"Might take you that long to get me hard again, I think I'm done for the night."

A few weeks later it was all over. Jenna came to me and gave me a soft kiss then took the remote away. She'd met a guy, he was pretty nice but she didn't want to cheat on him with me. I was a little sad at first but she saw my face and gave me a hug.

"Marcus, you gave me 3 months of the best sex I'll ever have with anyone. No hangups, no stress, just really fucking good sex. Use what I taught you. You're a good guy, make her laugh and make her cum as hard as you made me and I promise she won't walk away."

When she moved out a few weeks later I was a little down but Mom was pretty supportive for some reason. I was jerking off one night when she came to my room, I quickly covered up and acted like I wasn't doing anything.

"Pretty hard going back to the hand after a hot blonde, huh?" she said with a grin as she sat on my bed.

"Wh... What?" I replied. I could feel my face going red.

"If you don't want this, I will cope. I've been watching you for a while, you really do have a beautiful cock and I was almost jealous that Jenna got to enjoy it," she said, smiling.

"I'm just shocked is all. I didn't know that you knew what we were doing," I replied.

"Neither of you hid it very well but it doesn't matter, you were having fun and making her happy again."

"Does she know that you knew?"

"No. Same as we'd not tell her if you want this."

To say I wasn't in awe would have been a lie. Mom had a few more curves that Jenna's slimmer frame but when she dropped her gown and negligee to the floor, my cock answered for me and I was soon tenting the sheet I was trying to hide under.

"You can stop this if you don't want it my love," she said softly then slowly pulled my sheet back.

I felt like I was in a dream. She took my cock in her mouth and sucked me long enough to get me fully hard then mounted me, taking my cock all the way inside her. She gasped then slowly began to ride me, looking into my eyes with a look of lust on her face. I reached up and began to fondle her breasts, feeling her nipples harden at my touch as she increased her pace. Jenna had taught me how to last ages when she rode me, I did it to Mom and she was soaked in sweat by the time she'd cum the first time. When she'd cum, I was still rock hard inside her, she looked down at me as she caught her breath.

"Not sure if I should be mad at her for teaching you or thanking her. How about you get on top, cum in me my love," she said.

I didn't last, five or six deep thrusts and I was spraying my seed into the very same pussy I was born from. The taboo nature of our coupling, deeper than I had with Jenna, blew my mind and I didn't go soft.

"I felt you cum, that was a nice load but you're still hard," she said to me.

"Well, I've never looked at you in any kind of sexual way, Mom but you're sexy as hell," I replied.

"Thank you. My thighs ache a little, do you want to finish him off from behind?"

"I'd like that."

"Let me catch my breath a little first."

I'm not sure what drove me to the decision. It may have been the crude image of my cum, mixed with hers, leaking over her asshole. When she got up onto all fours, she had rubbed it over herself and it looked so inviting. Her pussy was beautiful too, her labia was more pronounced than Jenna's but I knew I'd enjoy eating her. I figured she'd stop me if she didn't want it but I held my cock and slowly pressed it into her ass.

"Ohhhhhh, fuck yes. Does my dirty boy want to cum in Mommy's ass?" she said to me.

"I think I would, yes," I replied.

"Take it slow to start but I love it. I may get more vocal than you've had before but yea."

Mom wasn't kidding about being more vocal. By the time I was thrusting, groaning at the hot, tightness of her ass, she was pretty loud.

"That's it, fuck my ass you dirty cunt, fill me with cum, fuck me harder," she screamed.

When she started cumming, she was rubbing her clit with her fingers and I couldn't hold back, I pushed deep into her and came so hard I almost blacked out. We collapsed together on the bed and she rolled over to face me as we caught our breaths.

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