tagIllustratedSister's Shemale Friend

Sister's Shemale Friend

bysilkstockingslover©

Sister's Shemale Friend

Summary: Family seduced and dominated by an irresistible shemale.

Note 1: This is a Summer 2018 Contest Story so please vote.

Note 2: Thanks to DarkBreezly for creating the pictures in this story.

Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story.



I came home from work a couple hours early, as our manager had overscheduled us and since it was 90 degrees in the shade, I'd rather be in my pool than perched in the bright sunshine high above one, supervising as a lifeguard.

I saw Della's car in the driveway, meaning my sister's super-hot, best friend was over again... as she had been every day this week since my older sister Amber had returned from college. For me this had meant a week of long jerk off sessions to thoughts of Della... and sometimes to the idea of a lesbian romp between Della and my sister... yes, I was a sick pervert who fantasized about his hot sister doing the nasty.

I went upstairs to my room to change and glanced out the window, hoping to see Della and my sister sunbathing or frolicking in the pool.

I saw something far more shocking.

So shocking I literally rubbed my eyes, thinking I was seeing things.

When I opened them a second later, I was still seeing the same thing.

My sister between Della's legs.

My sister was a lesbian??? Hot damn!!!

Yet as I craned my neck to get a better look, my angle so poor that I could mostly see Della's back, it seemed to be that Amber's head was moving up and down.

Strange.

I dashed out of my room and rushed to Amber's, thinking I would be able to get a better angle.

Then I was shocked again.

Amber wasn't a lesbian.

Della... the beautiful Della... stroke-worthy Della... had a cock. A huge fucking cock... and Amber was sucking it.



I stared in complete shock.

I'm not going to lie... I watched a lot of porn. Some of it was actually shemale. I couldn't explain it, but in my opinion a beautiful girl with a cock was the hottest thing. Now for the record, I'm not remotely gay... I like women... a lot... but for some reason I find a cock on a female body intriguing. Of course, all my experience was from porn and I never imagined encountering an actual shemale.

Yet, there it was... Della was a shemale; Della had a huge cock and Amber was bobbing on it like a bitch in heat. This was even hotter than my imaginative stroke fantasies.

I could have watched forever, but I wanted both to get a better view and to hopefully hear the sounds of sex and whatever was being said, as it seemed like Della was speaking while Amber was bobbing. So I hurried downstairs, went through the garage, snuck around the side of the house and tip-toed closer as quietly as I could as I heard Della ask, "Want to get fucked?"

"Is it a hundred degrees?" Amber asked rhetorically... it was 101 by the way.

"Get in the pool," Della ordered as I found a great spot to be a peeping Tom. I peeked around the side of the building and watched my sister, unfortunately still in her bikini, jump into the water. Della followed, although she walked towards the edge and down the underwater steps with a sexy saunter, before moving behind my sister.

"Hurry up, I need your cock," Amber demanded, in her usual bossy tone.

"You always do," Della said, as she appeared to slide inside her.

"What can I say?" Amber moaned. "I love your fucking cock."

"And I love my fucking cock fucking your fucking cunt," Della responded, as she began fucking my sister.



"Oh God," Amber moaned, clearly enjoying the hard fucking.

"Your cunt is even tighter in the water," Della said.

My already hard cock flinched when Della used the word 'cunt', a word I had never heard a female say in real life... except in porn.

"Your cock is always fucking huge," Amber moaned loudly.

"You're such a size slut," Della teased, holding my sister's hips firmly as she slammed into her.

"I am since I discovered what you were packing," Amber agreed.

"Now shut up and take it, my little slut," Della ordered.

"Mmmmmmmm," Amber moaned happily, as I continued gazing in fascination at my sister getting fucked, at my sister loving being called a slut.

Suddenly realizing I should get evidence for blackmail or just for my own future jerk off sessions, I pulled out my phone and began filming.

I watched for a couple of minutes before Amber moaned, "Oh God, I'm getting close."

"Then come, you little slut," Della ordered.

"Yes, don't stop," Amber pleaded, clearly seconds away from coming.



"Oh yessssss!" Amber screamed, signaling her orgasm had hit her.

Della kept fucking her for another minute or two before she pulled out, climbed out of the pool and looked my way. I quickly backed away and hurried back into the house, not wanting to get caught. I rushed back up the stairs, back to my sister's room to see my sister was now on her knees and sucking that big cock again.

I began rubbing my cock in my pants as I watched... desperately needing to come.

I filmed and rubbed myself for a minute until Della coated my sister's face with cum, which triggered my own cannon blast into my underwear.

I zoomed in as best I could to get an image of my sister with a load all over her face.



I kept filming as Amber stroked Della's cock and sucked out the last drops of cum.

They then both grabbed their bikini bottoms and I finally got to see my sister's pussy and wasn't surprised to learn it was completely shaved.

Seeing Amber heading inside, I decided to have some fun. I rushed downstairs and to the front door. I then walked towards the kitchen, timing it so I startled her when she walked in.

"Oh, God!" Amber gasped at seeing me. "What are you doing home?"



"What's on your face?" I asked in return.

She stammered, "I-I-I got suntan lotion all over me. I was just coming inside to wash it off."

"How did you...." I began but was cut off.

"It was an accident," she said tersely and rushed to the washroom.

I smirked at her lame lie, grabbed the milk from the fridge and poured myself a glass. I downed it quickly and heard the door open.

Della walked in and greeted, smiling warmly, "Oh, hi, Harry. When did you get here?"

"Just now," I lied.

"Oh," she said. Then added, as I tried not to look down at her crotch, "I thought I saw you outside."

"N-n-nope," I stammered, realizing she likely did see me when she looked my way.

"Weird, I was sure I saw you," she said, smiling that knowing smile.

"Must have been you fantasizing about me," I countered suavely, as I could no longer resist gazing down at her bikini bottom, wondering how she could possibly hide her massive cock in it.



"I'm usually the one making fantasies come true," she countered wickedly.

"Oh," I said awkwardly, unsure what to reply to that even as I continued staring at her crotch.

"My eyes are up here," she pointed out.

I looked back up and laughed, "Sorry."

"So what have you been doing this summer?" she asked.

"Work mostly," I said.

"I've been getting a lot of workouts myself," she said slyly, her innuendo clear to me.

I played along, acting oblivious, "Yes, a good workout a day is key."

"I often have two or three," she continued.

"That is impressive," I said, as I wondered what it would be like to suck her cock, maybe even to be fucked by her.

"So I've been told," she said, sauntering past me and down the hall to my sister's room.

Fuck, I thought to myself staring at her ass as she left.

That night I read shemale stories and watched shemale porn. Although I had already been obsessed with sucking their cocks... after watching Della pound my sister I was suddenly equally obsessed with taking it in the ass.

I wasn't sure I could actually take it in the ass, but my curiosity had been sparked.

.....

The next day I walked in on a second stimulating fuck session... this time in the living room... this time it seemed it was orchestrated for me... since they were fucking in plain sight when they knew I would be returning home.

This time I even got to see my sister completely naked... her big tits bouncing around as Della slammed into her hard.

"Hey, big boy," Della greeted, still slamming.

"H-h-hi," I stammered, as I stared at my sister's beautiful body and the big cock powering in and out of her.

"Take a picture pervert, it lasts longer," my sister said snottily even as she didn't try to hide her nudity.



After a moment, when I kept staring, Amber snapped, obviously I'd missed her earlier sarcasm, "Get the fuck out of here."

I turned and left and headed to my room... to jerk off.

I opened my laptop and it was warming up when there was a knock at the door. I opened it and Della, now dressed, pulled me into the hallway.

She greeted coyly, "Hi, Harry."

"Hi," I replied, my eyes unable to not be drawn to her breasts, and the nipples that were poking through her skimpy top like two excited headlights.

"Did you like what you saw?" she asked.

"It was something," I vaguely answered.

"That wasn't the question," she smiled coyly.

"It was hot," I admitted.

"Do you like my t-shirt?" she asked, posing for me in a way that somehow made her tits even bigger... was that even physically possible?

"It's awesome," I said.

"I wore it for you," she surprised me.

"You did?" I asked.

"Yeah," she said, glancing down at my crotch. "You had me curious about what you were packing down there."

Before I could respond, although I'm not sure what I would have said, I was utterly beyond myself, she pushed me against the wall, moving right into me as her hand went directly to my hard cock. "Mmmmmm, it's as big as I hoped it would be."



I don't know why I said it, like I really cared, I stammered as she tugged my shorts open, "W-w-what about Amber?"

"She doesn't have a cock," she pointed out, as she lowered herself down and pulled my shorts and underwear down in one quick move. "Lift your feet up," she ordered.

I mindlessly did as I was told as this beautiful girl undressed me, my hard cock saluting her.

She tossed them aside and asked, "Have you fantasized about me sucking your cock?"

"God, yes," I moaned, as she grabbed my cock and slowly stroked it.

"Do you want me to suck this big cock for you?" she asked, slowly stroking it.

I repeated the only words I seemed capable of, "God, yes."

"What will you do for it?" she asked, as she slid her tongue down my shaft.

"Anything," I moaned, knowing I would indeed do anything for her. If she wanted me to suck her cock, I would; if she wanted to bend me over and fuck my ass while my sister watched, I would. I was completely at her whim.

"Remember those words," she purred, as she moved her tongue back up my shaft.

"I mean it," I reiterated, wanting to let her know I would be her cock sucker if she wanted me to, "I'll do anything to please you."

"I know you will," she said, so confidently that I wondered if she understood what I was really offering.

"No coming until I say so," she ordered, before asking, "Is that clear?"

"Yes," I agreed, as she licked my cock head.

"Good boy," she said, before she took my cock in her mouth.

"Oh, God," I moaned, as her warm, wet mouth enveloped my raging hard-on, dissolving me into a puddle.

She bobbed slowly, and I wasn't sure where to put my hands. In my fantasies I would put them on her head, but it was clear she was in charge and I wasn't to take any liberties uninvited. And there's nothing that says you're taking charge like grabbing someone's head when they're sucking your cock. So I awkwardly crossed my arms, indicating my willingness to be grateful for whatever she decided to give me, as I watched her from my perfect view.



She slowly bobbed for only a minute, although that was enough for my balls to begin to boil, when she suddenly stopped, stood up and said, "Are you ready to prove you'll do anything?"

"Yes," I nodded, knowing what she was about to order me to do.

"You know I have a cock, right?" she asked, looking into my eyes.

I nodded, excited. I was right!

"And you know your sister has already sucked it," she continued. "Don't deny you saw us yesterday."

"Yes I did, it was hot."

"And now it's your turn," she said, putting her hands on my shoulders and pressing gently downwards.

I didn't need any further instructions as I lowered myself to the floor.

"You want to suck my cock, don't you Harry?" she asked, as she looked down at me... the power position changing in seconds.

"Yes," I repeated, as I looked at her crotch area... seeing the bulge.

"Go ahead, fish it out," she ordered softly.

"Okay," I said, as I unbuttoned her shorts. As soon as I pulled down the zipper and opened her fly, her hard cock popped out like a jack-in-the-box.



My cock was raging as I tugged down her shorts.

"It's already nice and hard for you," she pointed out.

"And so big," I said, in awe of what was in front of me.

"And so ready for your mouth," she said, as she stared possessively down at me.

"I've never done this before," I admitted, somehow wanting her to know this.

"Sucked cock?" she asked.

"Anything sexual at all with anyone," I admitted.

"You're a virgin?" she asked, sounding surprised.

"Totally," I admitted.

"Interesting," she smiled, as she moved her cock around against my lips.

"Can I suck it?" I asked, desperately wanting her manhood in my mouth, if that makes any sense.

"Suck what?" she asked, tapping my lips with her cock.

"Your big cock," I answered, not at all ashamed I was about to become a cock sucker... although I was happy to realize she had sucked my cock briefly first, so I got a blow job before giving one.

"How badly?" she asked.

"I've never wanted anything more in my life," I replied, which was the truth. I had to have her cock.

"You want to become my cock sucker?" she pushed, continuing to tease me and draw me deeper into her web of submission.

"Yes," I admitted without hesitation.

"Like your sister already is," she added.

"Yes," I again agreed, willing to admit and do anything to please this cock.

"Go ahead Harry, become my cock sucker," she said.

Being named a 'cock sucker' somehow only added to the excitement, as my own hard cock flinched in midair. Permission granted, an order given, I closed my eyes, opened my mouth and took her cock in my mouth, even as I felt her hands move to the back of my head, reasserting her control over me. I felt something melt inside me as I surrendered.



As I did, I moved my hand to my cock.



"No touching your cock, cock sucker," she scolded. "From now on I control your orgasms, is that clear?"

I was surprised by her order and expectations, but the term 'anything' meant just that, anything, and I agreed, as I moved my hand from my cock, "Yes, it is."

"Good, cock sucker," she approved.

I had long wondered what it would be like to suck a cock... a shemale cock that is. Now as I did it, I couldn't believe how natural it felt.

As my mouth took in her cock head, I felt at home.

As I leaned forward and took more in, I couldn't believe how hard her cock felt. I mean I shouldn't be surprised, my cock was always this hard... although the hardness felt a lot different in my mouth than in my hand.

"Can you taste your sister on me?" she asked.

I hadn't even thought about it, but obviously I was sucking her pussy juice off Della's cock. "I guess so," I admitted.

"She has a tasty cunt," Della said.

"Yes she does," I replied, realizing the first pussy I ever tasted was my sister's, even if it was second hand.

"It's kind of hot, your sucking my cock just after it was inside your sister's wet cunt," she said.

"I'll suck your cock right after whatever hole you plug first," I awkwardly, weirdly pledged.

"Good to know," she laughed.

After a few bobs, she moaned, "Good, cock sucker," as I began bobbing harder... feeling the ridge between her shaft and cock head with each bob.

I loved the approval. I loved knowing I was doing a good job.

I was soon taking over half of her cock in my mouth when she said, "A good cock sucker worships the balls too."

I allowed her delicious cock to slip out of my mouth as I did what pornstars do and slid my tongue down her long, hard shaft until I reached her balls. Although I had watched girls suck on balls in porn, it wasn't something I had ever put a lot of thought into. Yet, as I reached her big ball sac, I knew what to do. I sucked the bag into my mouth and searched for a testicle... finding it easily.

"Good, ball sucker," she moaned, as until now I had no idea having one's balls sucked could be pleasurable... I just assumed it was a porn thing. I had also never heard the term 'ball sucker' until I was being called one.

I sucked on one ball, then I found the other and replicated my new skill of ball sucking, before she instructed, "Good boy, now show me how much you like my cock."

"Yes, ma'am," I awkwardly responded, not sure what to call her, but wanting to make it clear I understood the hierachy between the two of us.

"You really are a natural little cock slut," she smirked as I took her cock back in my mouth. Being a virgin, being called a slut was rather humourous, yet the fact that here I was half naked, sucking my sister's shemale friend's cock, in the middle of a hallway where we could get caught at any moment, was a pretty slutty thing to do... especialy since I couldn't care less if I got caught. Okay, that isnt exactly true, I didn't want to get caught, but that fear was superceded by the wonderful reality of the task at hand.

So I responded like so many porn stars do when called such a name: as I moved my left hand to her ass, I moaned and bobbed faster.

She again moved her hands to the back of my head, a silent guesture that made it clear once again she was in charge, as she added, "Oh yes, you're a natural cock sucker, just like your sister."

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