tagTransgender & CrossdressersMy Big Sister Ch. 02

My Big Sister Ch. 02


So here's the second installment, enjoy.


My head gently landed on my desk as the last bell rang, signaling the end of school. Usually I'd be the first one out of the door, but right now I'm having....certain difficulties with the lower part of my body preventing me from doing anything too suddenly.

"Yo, Pete!" Paul's voice caused me to suddenly jerk up in my seat, and that particular motion caused my ass to start burning once more. Paul noticed me hissing in pain, and arched a confused eyebrow at me.

"Dude, you alright?" he asked as the students continued leaving the classroom.

"Yeah....I'm fine," I groaned. "You just startled me a bit."

"Huh......man you've been banged up lately. Have you been getting in fights?" Paul snickered. "Tsk, tsk. And here I thought you were the "Golden Boy" Pete, you're the last person I'd think would be in a fight."

"You're overthinking things again," I sighed at him. "I'm just feeling a bit....sore I guess."

Paul suddenly laughed. "What you've been getting rammed in the ass or something?"

I felt as if a red flag had suddenly appeared as I shot up and slammed my hands on the desk, shooting an alarmed look at him. "W-What the hell are you talking about?!"

Paul immediately shot his hands up in mock surrender, still laughing "I'm joking man, you know me."

I fell silent and hung my head at my foolishness, it's a wonder how my secret hasn't been outed yet. I began gathering my things as Paul's hand touched my shoulder. "Seriously, I know you're not like that. We've been friends since Pre-K remember? Besides," his eyes darted toward the other side of the classroom. "I know a certain cutie you've been eyeing."

I turned to look in his direction and rolled my eyes. "Paul, you know I don't like Brittany that way....not anymore."

"Now what could have changed so quickly?" Paul grinned. "Just a few weeks ago you were ready to bend her over, now you're not interested? Maybe you are gay."

I glared at him but said nothing. What could I say? That I'm more into my sister who has a giant dick she's always willing to drill me with? Come on now, this is high school. Reputations mean everything here, and Paul tends to have a big mouth, even when he tries to keep a secret. I suddenly felt a hard object smack the back of my head snapping me out of my thoughts.

"Now what do we have here?" my other best friend, May, glared at me through her bright blue eyes. "A couple of perverts scouting for their next prey?"

"Damn it May, didn't I tell you to stop being so violent?" I glowered.

"I'm not being violent, just necessarily rough," May grinned at me. "You deserve it, you know it's rude to drool over some girl. In some cases that could be sexual harassment."

"Spare us May, we don't have time for one of your feminist rants again," Paul said earning a hard sock to the shoulder.

"Someone has to keep you pervs in line!" she growled.

I shook my head at the two of them, they got into arguments daily, so much that one would suspect that they were secretly into each other. However, I know that's not the case, those two would kill each other if they spent time with one another without me around to act as a buffer.

"So," May said as we began departing the classroom. "It's Friday...."

"Good," I sighed. "I could use a two day vacation."

"You said it bro," Paul agreed putting his hands behind his head.

"Any plans?" May asked.

"Well I was thinkin' about-"

"I wasn't talking to you, numb nuts," May spat at Paul. "We already know you're gonna spend the entire weekend watching that 'high-class' porn, or whatever it is you call it."

"Hey, those women are high-class," Paul grinned. "They use their pinkies."

May simply made a face at him and turned to me. "Please tell me you won't be joining this weirdo."

"Of course not," I shook my head. "For once, I don't have any plans this weekend."

What I was telling was the truth, Kimmy had to go on some sort of charity event in New York for a few days, so I'll be left with a lot of free time to myself. At the very least, this gives my ass a chance to heal up without her wrecking it every half an hour. I suddenly felt my pocket begin to vibrate, reaching into it to pull out my cellphone.

"Hmm, it's Kymberly." I said.

"Your older sister?" Paul asked.

"Yeah, she wants me to....see her off before she goes. Talk to you later guys!"

"Wait I wanted to ask you-"

"Yes to whatever you want me to do, May! I gotta go!"

I sprinted out of the school and toward my house, luckily I live close enough that it normally took me five minutes, three when I'm running this fast. I entered the large home and found Mom in her usual spot; sprawled out on the couch asleep with potato chip bags, beer cans and cigarette buds all over the floor with the television volume at the max.

"Ugh, you're such a worthless slob," I sighed, as my sister entered the room carrying two suitcases.

"Oh, hello Peter," she greeted before taking a look at Mom and rolling her eyes. "Mommy, I just cleaned this place. Why do you have to be so messy?" Mom uttered some incoherent words in her sleep making Kimmy let out a similar sigh that I had.

"Don't worry about it, I've cleaned up after her before," I told her, sitting on the couch. "You know it sucks you'll be gone for the weekend."

Kimmy smiled and sat next to me while gently pinching my cheeks. "You're so sweet, are you going to miss me, little brother?"

"Yup," I said leaning in close. "And there's something else I'll miss as well."

"Oh?" Kimmy's asked cocking her head to the side. "And what would that be?" I smirk deviously as my hands ran along her creamy thighs before I reached under her pink skirt and cupped a soft bulge in between her legs. "Oh, Peter!" Kimmy gave me a warning look. "Y-You know I can't get.....once it goes up it won't go....." She closed her eyes and bit her lip as my hand continued rubbing her bulge before moving her underwear aside, letting her flaccid male organ breath. She let out a small moan as I gripped the cock and rubbed it against her inner thigh. "Peter....Mommy's right there."

"She's asleep," I shrugged, cupping her chin and pulling her into a passionate kiss.

Our tongues began wrapping around each other as I continued playing with Kimmy's slowly stiffening rod. When we broke our kiss, Kimmy was now at half mast, giving me a hard look. "You want me to bend you over this couch right now, bitch?" she growled softly, gripping my shoulders. My smirk grew wider at her sudden switch to nympho-mode, as I merely gave her a nod and tried to dive back in, only to be interrupted by a loud honking sound outside.

"Oh!" like a light switch, Kimmy suddenly went back to normal. "That's the bus." She jumped up and grabbed her suitcases, ready to bolt out of the door when I yelled "Kimmy, wait!"

"Peter I have to go n-"

"You might want to look down." I pointed to her crotch, where part of her cock was dangling from her skirt.

"Oh my," her face flushed as she quickly stuffed the monstrous object back into her underwear and adjusted the skirt. "Thank you Peter.....um, we can continue our 'session' when I return, if you want."

"Lookin' forward to it," I winked as the flush on her cheeks darkened. Without another word, she gave me a quick wave, turned on a heel and was out the door. Right as it slammed shut, I groaned and fell back onto the couch, looking down at the obvious tent in my pants. "Oh well, I'd better go masturbate."

I started toward my room then stopped suddenly, turning to look at my sleeping mother. The woman could sleep through a brick to the face, something that's happened before, so I knew my sister's moans couldn't have woken her up. Looking down at her, it's obvious to see where Kimmy gets her looks from, my mother was a stunningly beautiful women, even when passed out on the couch in her underwear.

Her long normally curly blonde hair was messy, her face looked more naturally beautiful when not covered in make-up as it usually was, and of course who could take their eyes off those beautiful, luscious breasts she owned that sat on her chest proudly, heaving up and down from her loud, unfeminine snoring. She looked extremely mature, as one would suspect, however, she had the mind of a ten year old sometimes. This whole thing between me and her started because she was jealous of Kimmy's 'special treatment' that I gave her, she even threw a small tantrum about it until I finally gave in and began giving the both of them 'special treatment'.

I will say, it's tough dealing with two women with dicks bigger than your own. It's even worse when the both of those women are obvious tops.

My eyes trailed down from my mother's smooth exposed stomach to her creamy thick thighs until finally locking onto her crotch. Though she was quite soft, I could easily still see the outline of my mother's proud cock through her tight boxers. I couldn't take my eyes off it, and I felt myself begin to lick my lips hungrily.

"Well, she would want it, even if she's asleep," I told myself, moving toward her. "Besides, this is revenge for the last time when she caught me off guard." I grinned evilly and got on my knees before mom's sleeping form. I started rubbing her smooth cheeks getting a bit startled when she let out an loud snort in her sleep, I then traced her lips with my index finger before dipping it into her wet mouth.

"Mmm," she moaned softly onto my finger. "Tastey.....hotdog....."

I grinned at her sleep talk and removed my finger, finding my other hand already caressing one of her large breasts, I listened as her breathing began to quicken and her body started to squirm slightly at my contact. Deciding to up the ante, I pinched one of her nipples through her shirt, earning a small approving moan. My eyes quickly turned back to her crotch, watching as her cock steadily began to grow as if it were being awaken from a long slumber.

"Mmm, Mom's dick needs attention?" I licked my lips once more. "Well, who am I to deny it?"

Once more a licked my lips and squeezed her cock through the material of her underwear, the beast was not even at half mast and it was already so thick that I could barely fit my hand around it. I slowly pulled Mom's panties down, allowing her cock to spring free and fall flat against her stomach. Already, it began to harden as my hands stroked along the shaft. When she was fully hard, she was actually bigger than Kimmy, which completely terrified me the first time she jumped me. However, after a few sessions both me and my ass managed to get used to her size.

I quickly position myself in between her legs and wrap my lips around the pre-cum soaked head, slurping all the clear liquid that oozed from it. Her moans increased in volume as I licked around the head and pumped the shaft before finally taking the monster into my eager mouth. Unfortunately, I could never get anymore than four inches down, as it proved far too thick for anything further than that. As I slowly began bobbing my head along her length, I noticed that Mom's breathing had slowed down and she was no longer moaning, instead I heard chuckling above me.

Oh crap.

"Come on now, sweetie," her smooth voice spoke to me. My eyes shot up as I stared at the beautiful, smug expression looking down at me. "Surely you can do better than that, right?"

"Mom, you're so damn thick I can hardly manage what I already was," I explained once I released myself from her cock. "Damn, what vitamins did you take when you were a kid?"

"Oh stop it, you're making me blush." Mom smiled, sitting up and wagging her cock in my face. "So you were gonna mouth-rape me in my sleep?"

"I would hardly call it 'rape', I just wanted a snack and Kimmy had to leave."

"Well I'm wide awake now and very hard, thanks to you. So you'd better be prepared to do something about it," Mom stuck one of her fingers in her mouth. "Should I just fuck your mouth today? I know you must be still sore from that pounding you took from Kimmy last night, I could hear you screaming like a wittle baby, she's really rough on you isn't she?"

I rolled my eyes and gripped her cock hard, earning a surprise gasp from her. "Come on Mom, I'm a big boy now, I can handle it."

"If you say so," she smirked. "But I'll be a lot more gentle than Kimmy was, I can't hurt my baby."

She pulled me into a kiss and began unbuttoning my shirt, sliding it over my shoulders. Once she was done with that she started kissing along my chest and softly biting my nipples while working on getting my pants off.

"Mommy's gonna take good care of her little boy," she whispered sliding off my pants and boxers. "Then she'll have her fun afterward."

She got on her knees and took my stiff rod in her hands, slowly giving my shaft a long tentative lick. She then finally took me into her warm, wet mouth, engulfing my entire dick in a matter of seconds. I ran my hands through her curly blonde hair as she bobbed her head back and forth.

"Oh shit...." I groaned, pushing her head farther down my cock. "Mom, I'm gonna...."

"Go ahead," she told me, pushing up her breasts. "Shoot it all over me, baby."

I nodded and started to furiously stroke myself, feeling all the cum from this week building up. It didn't take long for my release, as I shot blast after blast of my hot cum all over my mother's face and tits. "Oh my, you came so much this time," she giggled. "Kimmy must not be letting you cum lately, that girl needs to learn some better manners."

Mom then stood up showing me her now steel-hard dick that twitched in excitement and anticipation, more pre-cum was now drooling from the tip as she gently stroked her angry beast.

"Geez, look how hard you are," I said reaching out and running my thumb along the large mushroom head.

"Now, lean back on the couch and open wide," she instructed.

I did as I was told, shooting my mouth open as wide as I could as she slowly guided her cock toward it. As per usual, hardly any of it could fit, but Mom was tenacious enough as she continued pressing forward. I coughed as she somehow managed seven inches of that thick piece of meat into my mouth before stopping suddenly, realizing that any more than that and my jaw would certainly pop from it's socket.

"I always said you had a big mouth," Mom giggled as she began to retract her cock only to thrust it back it. "You okay? Mommy's not killing you is she?"

Of course I couldn't answer her, so I just shook my head and allowed her to go back to her rhythm, she started off slow and careful to allow my jaw to adjust, but it didn't take long until she'd had enough of that and began to fuck my face seriously. I even managed another inch as the head began slamming the back of my throat, Mom then stood on the couch and pressed her hands against the wall allowing her to go at a much faster pace.

"Mmm, yes baby," Mom moaned picking up even more speed. "Mommy's gonna cum soon!" I took that time to use my free hands, my right one finding its way to her massive balls.

"Ohhh!" her thrusts became spasm-like, I knew that her balls were overly sensitive even to the touch of her underwear, that's why she wears loose boxers rather than panties. Well that and she's got an enormous cock attached to her. "Oh my God, I'm gonna...." Right as I heard those words I immediately removed my hands from her balls, slamming them onto her hips and effectively stopping her from thrusting anymore.

"Wait, what the hell are you doing?! No fair!" she whined trying to thrust back into my mouth, but luckily I'm much stronger than she is. "I was so close! Don't you do this to me!"

"Sorry Mom," I grinned once I removed my mouth from her dripping cock. "But you have a large quantity of cum, there's no way I can survive if you shot it in my mouth with your cock in there as well, I'd suffocate to death."

Mom gave me a blank look before her face scrunched up and her eyes began to water. "No!" she cried falling back onto the floor. "It's not fair! You let Kimmy cum in your mouth all the time! Not fair! Not fair! Not fair! Not fair! Not faaaaaair!!"

I rolled my eyes at her crocodile tears, something Kimmy also inherited from her, before turning around and pressed my hands against the wall while making sure to stick my bare ass out at her.

"I'll let you cum here," I sighed. "Kimmy's never done that before."

Mom, who had stopped her immature tantrum for a second, sat cross legged on the floor and folded her arms, sticking her nose up in the air. Even in that position I could still see her cock proudly standing up against her stomach. "Why should I?" she pouted. "You wouldn't give me what I wanted."

I chuckled and wagged my ass her way, knowing full well she couldn't get her eyes off it. "Are ya sure?" I teased. "You know you want to."


I shook my head and decided to go another route, giving her my best puppy dog expression. "Please Mommy?" I asked her in the smallest, quietest voice I could muster. Almost like a switch, Mom's eyes lit up and her face turned red as she quickly grabbed my waist and forcibly bent me over the couch, shoving my face into the pillows.

"You're lucky you're so goddamned adorable," she growled not even bothering to give me any time to prepare as her cock began pushing against my hole. "Oh wow, you're as tight as ever."

"No," I growled in pain clenching the couch cushions as I could feel her enter me. "You're just so big."

"Semantics," was the only answer I got as she worked more of her cock into my hole until she'd finally gotten the entire thing in. Despite having gotten used to the pain, I still didn't very much like the first entry. It wasn't until she'd started getting a good rhythm that I could feel most of the pain starting to go away. She gripped both my ass cheeks hard, a signal that she was about to pick up the pace.

"Oh fuck....." I groaned as her thrusts became harder and faster. "Damn it Mom, you said you'd be gentle...."

"I am," she hissed, grabbing me roughly by the hair. "This is the most gentle I can be, sweetie."

"God damn it," my growl was mostly muffled by my face being pushed back into the couch cushions.

"You really are a bad boy," she panted, keeping up her turbo thrusts. "Using that bad language right in front of your Mommy, you deserve a good spanking."

I felt her hand slap right across my ass hard, causing me to let out another muffled moan and clamp my ass down on her rod. Almost immediately, I felt her cock swell, as her nails dug into my flesh. "Damn it," she moaned loudly, shoving herself all the way inside me. "I'm cumming! Too soon!"

The unmistakeable hot liquid shot load after load into my ass while Mom let out a very loud scream, keeping me locked in her iron grip. As her release slowly started to subside, she suddenly collapsed, falling backwards and allowing her halfway hard cock to slip right out of me.

"That should teach you a lesson about depriving me of what I want."

"Whatever," I panted not bothering to move from my spot. I suddenly heard loud snoring sounds and turned around, finding that Mom was now out cold on the floor. As always, whenever she came she would go right to sleep as if she were completely exhausted.

"You really are a worthless slob," I snickered.


"Tch, where the hell is she?" I groaned to myself, looking at my cellphone once more. "She's fifteen minutes late."

May had called me a few minutes after Mom and I were done, saying that she wanted to meet me here at the mall for something important. But that damn girl was so slow when it came to getting ready sometimes, now she's left me sitting here looking rather suspicious outside of a womens' underwear store with my insanely perverted friend. Speaking of which.....

Report Story

byDaBlackMamba© 25 comments/ 171090 views/ 251 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: