Shemale Step-Sister

Story Info
Teen boy spies on his shemale step-sister and gets a treat.
3.6k words
4.53
711.6k
1k

Part 1 of the 2 part series

Updated 06/08/2023
Created 01/22/2017
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

Someone was watching me. It was my 18 year old step-brother Ethan. He was standing right outside my door, peeking in though the almost imperceptible gap where the door handle was too small for the hole it was in. It was a defect born of my dad's determination to fix the old handle and buying too small a replacement.

I noticed the sudden lack of light through the hole as Ethan stealthily positioned himself outside my door. I smiled to myself. So predictable.

When our parents left for their weekly "date night", I hung out with Ethan for a little before announcing that I was going to take a shower. Ethan barely looked up from his video game, but I could tell from the way his eyes travelled over my body that he would continue his habit of spying on me naked. And why wouldn't he?

It was only natural that a horned up high school senior would want to peek at his new, hot, 21 year old step sister. When the four of us first moved in together at the beginning of the summer I figured it would happen once and that would be it. Because while I kept myself in shape, took care of my long blonde hair, and wore clothes that accentuated my D-cup tits and showed off my perfectly formed ass, I knew that I had one thing that boys usually don't like on girls.

I had a dick. And not just any dick, I had a dick bigger than most men, complete with a set of golf ball sized balls. It was 10 inches long and as thick as a soda can when fully erect. It was the reason I had never had a real boyfriend and why the pussy underneath was still untouched by anyone other than me.

Then one day a couple weeks after I got back from college, he walked in on me while I was in the shower. He got an eyeful of everything I had to offer. He stood and gaped at me, his jaw twitching open. Finally he stuttered an apology and slammed the door.

He had acted differently towards me after that. He was distant and we never seemed to be in the same room together for very long. But eventually things started to get back to the way they were before our parents got married. That's when I noticed his peeping tendencies.

To be honest, his attention flattered me. I was shunned by a lot of the boys at school because I had a reputation for not putting out, so eventually they all stopped trying. So for a boy to look at me with desire when they knew everything I had to hide excited me. I began looking at Ethan in a different way too, I noticed how much he'd grown up in the 4 years I'd known him. He ran track all four years in high school and so had a nice lean runner's body. He also had his moms raven black hair and fair complexion. He was exactly my type now that I thought about it.

I started exaggerating my movements to give him better views of my body, leaning over to dry my legs, shaking my upper body as I dried my hair, and a couple of times I even stroked myself naked while he watched. It gave me such a thrill that I came almost instantly. But I was still horny, I shifted my ball sack aside and slipped a few fingers into my pussy. I moaned loudly enough for him to hear, reaching up with my other hand to play with my tits.

Stifling a laugh, I moaned out "OHHH, EEEETHAN" one time. I heard a bump from my door and discovered a small wet spot on the floor when I left my room a few minutes later.

This time I had a plan though. I knew he was jacking off to shemale porn. A few days ago I found his web history filled with all sorts of videos and pictures of shemales dominating men.

I needed him nice and horned up, but didn't want him to cum. So I put on a careful show, shaking my ass and tits just enough to get him hard and thinking about me. Then I played with my cock for a minute before I put my robe on and went to leave my room.

Unsurprisingly I found ethane exactly how I left him down stairs. I chatted with him and sat on the chair next to the couch he was sitting on. I put my leg up on the coffee table and let my robe slowly slide down my thigh. I shifted positions and felt my shaft flop out into the open.

I have to give Ethan credit, he didn't react in the slightest to my wardrobe malfunction. He did pause his game to look at me more often when I was talking though.

Finally I declared that I was going to bed, and that our parents would be home soon. Ethan agreed and together we walked up the stairs. We said goodnight as I slipped into my bedroom and shut the door.

I grabbed my phone and opened the app that let me control my action camera. You know, those small cameras people attach to their helmets when they go bungee jumping or skiing or something? Well I had strategically placed mine in Ethan's room this afternoon. The cool thing about the app was that it showed me a preview of what the camera was seeing, essentially giving me a spy cam.

I watched Ethan get ready for bed before pulling out his laptop and popping in headphones. Luckily I could see the screen from where the camera was and I saw him pull up a porn website. Now I knew I had him. He browsed around a little before picking a video and taking out his stiffening prick. This was the first time I have seen his cock and I was impressed. It wasn't as long or as thick as mine, but it was still probably bigger than average.

I quietly opened my door and tiptoed down the hallway to his door. I hit send on the email to him that contained the video I made for him earlier in the day. I saw his head tilt in puzzlement as I watched him open the email on my camera. Then I put my hand on his door handle and waited for my cue.

------------------

"Alright Ethan, I think I'm going to take a shower now! Be back in a bit." Morgan said as she started towards the stairs. I took a long sidelong glance at her legs and ass in those short spandex shorts she was wearing as she passed. I mumbled an "alright" as she passed, hoping I wasn't showing the rapid excitement I was feeling.

I waited a few minutes until I heard the bathroom door open, presumably to let the dripping wet body of my step sister out of the steamy bathroom.

I paused my game and slipped as quietly as I could up the stairs. I knelt down in front of her door and pressed my face against my favorite spot in the whole house. The hole was barely big enough for one eye to see through, but it was a clear and unobstructed view into Morgan's room.

My breathing quickened as she dried off her legs, bending over to show me that nice ass of hers. Then she seemed to shake her tits just right as she toweled her hair off.

I slipped my hand down my pants and grasped my cock as Morgan laid on her bed and began stroking herself, lightly moaning at her touch.

Then my heart dropped in disappointment as she began to stand up. She reached for her robe and I knew that was my cue to leave. I tiptoed back downstairs and picked up right where I left off in my game. 20 seconds later Morgan came striding down stairs in her tiny robe that showed way to much skin.

She sat in the chair to my left and I had to watch out of my peripherals as the robe slid down her leg, exposing more and more thigh to my hungry eyes. Then she shifted position and I had to use all my willpower not to react as her beautiful cock flopped out into the open.

Morgan managed not to notice it for almost 15 minutes, before she readjusted and it was concealed back under her robe.

"Okay Ethan, I don't know about you, but I'm tired as hell and want to go to bed!" Morgan chimed.

"Yeah I'm pretty beat too." I responded, saving my game and turning off my console.

"The geezers should be home in an hour or so, but we should lock up and turn the lights out just in case right?" She yawned. I nodded and we got to it, meeting back up at the base of the stairs.

We climbed the stairs together and said goodnight at her door. My balls was aching for release. Morgan was the biggest tease ever. Sometimes I wondered if she knew what effect she was having on me and teased me on purpose. I stumbled through the pitch black hallway until my fumbling hand found my door handle.

I changed into my pajama bottoms, sat at my desk, and pulled out my laptop. I put in my headphones and pulled up my favorite porn site. I typed in a few of my favorite search terms to check if any new shemale videos had been added. I saw one new one with a girl with a big cock standing over a bent over guy in the picture.

I clicked on it and the opening moans filled my headphones. I reached down and released my hard manhood from its prison.

Suddenly my computer dinged to let me know I had an email. Who would be emailing me at this time of night? Without thinking about it, I clicked on the icon and saw that it was from Morgan? That was odd. It had a video attachment. She never sent me emails. I didn't even know she had my email address.

Something inside me told me to open the video, so I did. It was 2 minutes long, so I played it.

Morgan's head and shoulders popped up on my screen. Behind her was the door to her bedroom, meaning this was probably recorded on Morgan's laptop sitting on her desk.

"Hey Ethan." She began in a sultry voice. "Soooo, I know you've been peeking on my last couple of weeks." She said sluttily, smiling at the camera.

Woah, what the fuck. She knew??? And she never said anything before now? What the fuck? The video continued.

"I know you enjoy seeing my body" Morgan said, making dirty faces at the camera. She ever so slowly stood up, more and more of her body appearing on screen. It soon became apparent that she wasn't wearing a shirt.

"I know you like looking at these tits" Morgan said, her boobs filling the screen, she reached up and began fondling them, lightly squeezing them and giving her nipples a little pinch. "Oh yeah, I bet wish these were your hands running all over my nice big tits huh? They're so nice and firm baby!" She continued, then turned around and angled the camera down, showing off her huge ass.

"And how about my butt? You like that too don't ya? Yeah you do you dirty little boy..." a smacking sound drowned her out as she spanked herself several times. Was this real? Did my step sister actually send me a video showing off her tits and ass?

"But I know what you really want." She breathed. "You want something special don't you?" Ethan's heart pounded in his chest in anticipation of what he hoped would come next. Morgan turned around painfully slow. But finally the image of her huge cock filled his screen. He released a deep pent up breath as the object of his desires the past month and a half was paraded in front of him, so close, but so far away!

"You want my cock don't you?" Morgan squeaked cutely. "You want my nice big girly cock don't you?" I subconsciously nodded yes to video Morgan.

"You want to feel my throbbing cock in your hands don't you?" I nodded again. Morgan ran her hands up and down her shaft, teasing me.

"You want to feel it in your mouth? You want to taste it? Want to suck all the cum out of my balls and swallow it for me?" I nodded even harder to this. That is exactly what I wanted to do. I cannot even begin to tell you how many times I've fantasizes about giving that beautiful piece of cock meat the most wonderful blowjob every given by anyone! And finally the icing on the cake:

"And I bet you reallly, reeeaaallly want to bend over and let me fuck your ass as hard as I want, for as long as I want, don't you?" I nodded so hard I thought my head would fall off. I couldn't stop staring at Morgan jacking off on my laptop.

And then the video concluded. "Then all you have to do is one little thing for me! Can you do one little thing for me dear Ethan?" Morgan's voice asked sweetly.

"Oh GOD yes, I'd do anything for that." I muttered to myself.

Morgan giggled. "Then all you have to for me is turn around and suck my cock my little cock sucking brother!" Then the video ended.

I hesitated, not sure what it meant. But I spun around in my desk chair and my heart stopped. Standing behind me, fully naked, one hand on hip and one hand slowly stroking her massive erection, was my beautiful step-sister Morgan.

"Well?" She asked. "You said you'd do ANYTHING for me didn't you? Get sucking sweetie!" Real life Morgan moaned sexually.

Moving automatically, I practically leapt halfway across my room to fall to my knees in front of her. I finally grasped the object of my sexual desires and it felt just as soft and firm as I had hoped it would be. A broad grin stretched across both our faces and we both gave into what we'd wanted to do for a long time now.

I leaned my head forward and stretched my mouth open as far as it could go to fit the head of Morgan's cock into my mouth. I bobbed up and down on it, emulating what I'd watched in porn. It was really warm, and a bit salty. I loved it. It felt right.

Morgan's hands rested on my head, helping me establish a rhythm of sucking. I tried deep throating her massive length, but couldn't get more than 3 or 4 inches down before choking and had to pull off.

"Oh my god. You have no idea how good this feels Ethan! You were born to suck my cock!" Morgan hissed.

I pulled off and grinned up at her, using both hands to jack her off.

"I can't tell you the amount of times I've fantasizes about you being down there, your smiling face looking back up at me." She breathed.

"I can't tell you how many times I've fantasizes about being down here!" I told her. I got back to sucking, focusing mainly on the head but occasionally running my tongue up and down the shaft. I fully knew where this was going and I didn't know if we had any lube.

"Oh. Baby. Yes. Just like that." Morgan moaned in pleasure. "Oh that feels so good! I might cum soon!" She groaned.

Encouraged, I sucked harder and faster. I reached both my hands up and stroked the shaft I could fit in my mouth with one hand and fondled her giant balls with the other. Her moaning increased, as her hands pulled my head down further and further on her shaft.

Finally she reached her peak and her cock twitched in my mouth as she shot 4 huge spurts of cum down my throat. I choked, not able to swallow it all at once. I had to pull off to keep from suffocating. Morgan was still cumming however, and a further couple of large jets of cum rocketed out of the top of her cock and splattered all over my face.

"Holy fuck that was good!

"But you know this isn't all I want right?" She asked. I nodded eagerly and stood up. I went to clear off space on my bed for us but Morgan couldn't wait. She grabbed my and bent me over the side of the bed. She yanked down my pajamas and fondled my ass.

"Oh I've wanted this ass for so long! It's so nice and plump and fuckable!" Morgan exclaimed. I heard a tube pop and glanced back to see Morgan dip her finger into a tub of Vaseline. She slathered it on her fingers and slowly inserted her pointer finger into my butthole.

"Ooooh" I groaned at the new sensation. After a few slow thrusts, Morgan gently pushed her middle finger in beside her first. The stretching was a little uncomfortable but it didn't hurt. A few more thrusts and she added a third finger.

"Oh yeah, your ass is gonna be nice and ready for my thick cock baby!" Morgan squealed excitedly.

"Oh god, that thing is gonna split me in half!" I said in mock protest.

"Don't worry" Morgan said soothingly "I'll use plenty of lube!" She grinned.

She dipped three fingers deep into the Vaseline and lathered a large amount of it all over her cock, focusing mostly on the head and immediate shaft area. Finally she nodded and stepped up behind me. I felt her head positioned at my sphincter and a sudden stab of worry shot through me. What if it hurt too much? I didn't have much time to dwell on it though, and probably had no choice in the matter anyways. Morgan has this sexually crazed look in her eye and was getting steadily more forceful with me.

There was no warning when it happened. One moment she was outside of me, the next she was splitting my ass open. I screamed a little louder than I meant to and Morgan giggled.

"Sorry baby, I'll go slower!" She said, patting my ass cheeks and she slowly thrust into me. She stopped moving to allow me to adjust to her size, which I was grateful for. After a minute or two she slowly picked it back up again, working herself in and out, slowly feeding more of her monster inside me. It hurt a little bit, but that pain was slowly fading.

It started to feel good actually. As she picked up speed the pleasure elevated, her dick hitting something inside me that sent waves of pleasure radiating through my body.

Once she had built up a good rhythm she stopped and she laid me down on my back on the bed. She pulled my legs up to her shoulders and pushed her way back inside me again, picking up her earlier rhythm.

Quite a few unmanly sounds came out of my mouth as she steadily fucked me for a solid 15 minutes.

"Oh shit, I wish I could record you moaning like a girl as I assfuck you!" Morgan laughed. Finally her moans quickened and her movements became more frantic, all the tell-tale signs of an impending orgasm.

"Shit! I'M GONNA CUMMMMM" Morgan screamed, not caring if the neighbors hear her. And boy did she cum. It felt like gallons of cum flowed out into my asshole.

When she finished we collapsed onto my bed together, where we lay for the next 15 minutes.

Finally I managed to get up and waddle down the hall to the bathroom. I cleaned myself up as best I could, noticing I couldn't stop smiling. I leaned against the counter, stretching my sore legs and glutes. I wouldn't be walking straight for a while. I thought to myself.

Suddenly I felt hands on my hips and a familiar cock slipping back inside my stretched asshole. I gasped in surprise and a little pain. I was sore from the earlier fucking and this time it kinda hurt.

"Aww does that hurt?" She asked maniacally. "Too bad hun, I'm fucking your ass whether you like it or not!"

I apparently had awoken the sadistic domme in my sister as she fucked me with wild abandon. I couldn't believe how hard she was fucking me, I thought I might go through the counter.

I grunted and groaned as my ass was continuously assaulted by a large foreign object. Morgan grabbed me and brought me out into the carpeted hallway where she threw me face down before slipping back inside me and attempting to pound me through the floor.

Finally she came again, this time for the last time. She helped me up to my feet.

"I'm so sorry Ethan! I have no idea what came over me just now, your ass was just so delectable I had to have it again." She said, real concern showing on her face.

"It's okay Morg, just a little unexpected. It actually kinda turned me on to be dominated like that." I grinned at her. She smiled back and gave me a huge hug.

I cleaned myself up again and slipped under the covers right as the front door opened and I heard my parents walk in. I was already sound asleep before they made it to the top of the stairs.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
56 Comments
1manthinks1manthinks26 days ago

What a great story So turned on! Hot!

AnonymousAnonymous2 months ago

OHHHHH, I'm NEXT, please???

AnonymousAnonymous4 months ago

The story would be sexier with realistic size genitals. The Barnum and Bailey 10 inch cock, as thick as a soda can, sounds like it came from the mind of an adolescent.

AnonymousAnonymous10 months ago

I would love to get fucked by a she male like that and I am 68 years old. I know it will never happen but I can dream

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
More Stories