I'm Not a Cross-Dresser 02

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

"Why'd you do that?" he asked, angrily.

"Mom has the menu on the refrigerator. You already knew what you were getting for a snack today - and, yet, despite the fact that 99% of the murders in the Bible happen between family members, you decide you want to try my patience."

"Fine. I'm sorry. Can I have it back?"

"No. You can take it up with mom."

"Jake!"

I stared at him like he was the world's biggest idiot.

The fuck-tard did the smartest thing I've ever seen him do - he shut his mouth and went back to working on his homework.

I sighed - loudly - went back to the refrigerator, retrieved his stuff, and set it down next to him.

"Thanks, Jake," he said - actually sounding like he (maybe) had learned his lesson. I wasn't holding my breath.

"If I have trouble with my Math, can you help me later? I'm not sure I understood what she told us."

I tried not to sigh again.

"If you have made an honest attempt to do the problems yourself - before you ask for my help - I will look at what you're doing wrong and help you get it right."

"Thanks, Jake."

I headed back to my room. Realizing that I had never checked my Xbox - to see if he'd returned my headset - I took the time to confirm that it was where it was supposed to be - before I went back to working on my own homework.

Dad had returned from his trip and - since I was keeping myself occupied - and had already given the brats their snack - I was exempted from helping prepare dinner.

I came out of my room to Jessica coming down the hall. She leaned in, grabbed my butt, kissed my lips, and whispered, "I need to give you a little ... appreciation ... later."

I watched the ass of her Daisy Dukes - as she prowled down the hall to head to dinner.

I quickly had to set a picture of Margaret Thatcher in my head - to get my hard-on to dissipate.

~~~

I was in the middle of an intense fire-fight when soft arms went around my neck and soft breasts smashed against the top of my head - before soft lips pressed against my right temple.

I died.

I respawned as Jessica moved around to stand to the left of the TV.

My headphones were loud enough that I wouldn't have heard her response but - when I asked if she had locked the door - she nodded - and smiled - and started unbuttoning her blouse.

I wasn't doing too badly as she removed the top, tossed it to the floor, cupped her breasts through the bra, and then reached back to unclasp it.

But - when she released the over-the-shoulder boulder-holder - and the lacey garment slowly slid down - revealing her mouth-watering breasts, I took a shot to the head.

My teammates were not happy with me - and I was respawning again.

Realizing this was not going to end well, I hit the power button on the controller and told the system to shut down.

Just before the game screen faded, I heard my buddies screaming at me to get my ass back to their positions to support them.

I laid my headset and controller on the Xbox and leaned back in my gaming chair, admiring the view.

My sexy older sister was peeling her shorts off - to reveal that the only thing she had on her body underneath was the heart tattoo.

Finally, fully naked, Jessica dropped to her knees in front of my crotch.

She stared into my eyes as she unbuttoned my jeans, unzipped them, and - with a little shift of my hips - pulled them (and my underwear) down - and tossed them onto the pile of her clothing nearby.

My balls were just hanging off of the front of the chair.

She caressed my fun-bag and slowly jacked my cock - her eyes still watching my every reaction.

She leaned forward and sucked one of my nuts into her mouth - teasing, hugging, and caressing it with her tongue.

Her right hand continued to stroke my stiff rod.

She switched to the other nut and showed it the same affection.

I had to tell myself to remember to swallow all of the saliva that was pooling in my mouth.

She leaned forward and pressed my cock between her taut titties.

She wasn't really built for a titty-fuck - but I didn't complain as she held me against her breastbone with her right palm and slowly fucked my penis with her gorgeous chest.

She took my member in her hand, sucked the knob, and then smeared her saliva - using the head of my dick - around her areolas and nipples - flicking the stiff nubs across the mouth of my urethra - teasing it - encouraging it to add a little spit of its own. A little precum oozed out and she used my dick to lather it around each of her breasts.

Her hot mouth - enveloping half of my rod - took my breath away.

She sucked hard - as she slid my cock in & out of her mouth - rubbing it between her lips - licking along the bottom with her tongue - on entry & exit.

The need in my balls was building.

She stood, leaned over me, kissed my lips - and then pushed my knees back - forcing me to sit a little straighter. She sat on my lap - fully embedding my sex-organ inside of her gripping vagina.

She kissed my lips - and all the rest of my face - as she proceeded to drive my penis in & out of her fabulous pussy.

"I thought you needed ..." I began to ask.

"This isn't for me; this is for you," she said.

She never stopped - and never slowed - and several minutes later - I roughly clenched my fists down on her breasts as my cock spewed inside of my sibling's sex.

Jessica took my face in her palms and kissed the life out of me as the last of the jizz geyser'd inside of her.

We were still kissing - and cuddling - a half-hour later when mom knocked on the door and - once more - needed my sister to move her laundry.

I grinned at her - still mounted on my cock.

"I want to watch you cum," I whispered.

"Some other time," she replied, "this was for you."

"We can use one of the dildos ...," I suggested.

"It doesn't work," she complained. "I thought I just needed to try a different one. I gave up after three."

"Shit," I said.

She grinned and kissed me, again, on the lips.

~~~

Jessica texted me - in the middle of Calculus - the following morning, "Meet me at the food court at noon."

After my next class ended, I headed that direction.

My sister was sitting with a hot blonde with big glasses - nice breasts - and pretty eyes. Her pixie cut - which I thought normally made girls look cute - made her look like a woman who knew how to take charge.

"Jake, this is Kitten."

I looked over at the girl/woman - to see if it was a joke.

"She's not kidding," she said. "Dad named me - and wouldn't let mom change it. As soon as I move out, it's getting changed. Your sister is one of the few that knows it's not just Kit. Please call me that in public."

I nodded and sat down.

My sister waved at someone - and I turned to see Nadine - sitting nearby - watching us.

"Competition?" Kitten asked.

"Ex," I replied.

Kit looked over at her - studying her for a minute - and then looked back at me.

She turned to my sister and asked, "She already try calling to get him back?"

Jessica nodded, glancing - once more - back to my cheating ex-lover.

"'Bout fuckin' time, bitch," my spiteful sibling called out.

I glanced over to see Nadine leaving.

I turned back to see both women looking at me.

"Going after her?" Kitten asked.

I laughed, and said, "She tried to tell me he was her cousin."

Jessica showed Kitten her phone - which, I assume, had the photos.

"Kissin' cousins," Kitten giggled.

"Jake," Jessica whispered, drawing my attention in.

"Without going into detail, Kitten is in the market for a boyfriend who can handle her ... uh ... specific needs."

Resisting the urge to look at our guest, I said, "Okay ..."

"You know my challenges with keeping boyfriends; hers are the same."

"Understood."

"Is that a problem?" Kitten asked.

I looked into her face. Her lips were very kissable. Her eyes were intelligent. She was hot. She was sitting down - so her hips, butt, and legs were hidden - but - from what I could see - she was a knock-out.

"My foremost concern, obviously, is to find a person I can be with who will not be looking for ... uh ... entertainment on the side."

Both women stayed quiet, waiting on my answer.

"While I'm not super-excited by the idea, if I found the right person - and it doesn't require much more than my sister needs - I believe we could come to an amicable arrangement."

"So, to be completely honest," Kitten replied, "I don't know the answer to your question because nobody has ever stuck around long enough for me to be able to find out."

"I see ..."

"Your sister has proposed a test."

I looked at her, curling an eyebrow, and said, "A test?"

"If you are willing," Kitten said, worrying her lower lip with her teeth.

"Where do you suggest we ...?"

Jessica jumped in, "We'll skip class and go to the house."

"We?"

"You don't need to be going through my room when I'm not there. I was going to grab the ... item ... and let Kitten use it."

"You're not watching, right?" Then I looked to the blonde, "Unless you need her to?"

Kitten looked to Jessica - and then me. "I don't think so. I mean she'll be next door, right?"

"Yes," Jessica confirmed.

"I mean," the woman said, "you've been super-honest with me so far - so it's not like I shouldn't trust your brother - I just ..."

"It's fine," I assured her. "If you needed her there, we could work something out."

"Really?" she said, incredulously. "You are very ... uh ... accommodating.

"How many brothers know their sisters as well as I know Jessi?" I asked.

"True," she replied.

"Shall we?" Jessica said.

"In a hurry for me to fuck your friend?" I asked, smirking.

Jessica looked at our guest and back to me, "Actually, I am a little curious to see if you two can work this out. I know how frustrating it's been for me."

Kitten looked back and forth between us - then rose to her feet.

Her blue plaid skirt made her white blouse turn the whole outfit into a "Catholic schoolgirl" look - and I was already getting hard.

"Fuck, you're hot," I moaned.

"Easy, boy," my sister giggled, "you need to get her home first."

Kitten hid a smile behind her hand - she was adorably cute when she did that. I was already hoping this would work out. She seemed nice - and she was definitely hot.

I got to my feet and headed for the car.

"Let's take mine," Jessica said. "I'll drive and you two can climb in the back and ... chat."

Kitten and I made out all the way to our house. She was a fabulous kisser - fucking took my breath away - I was a little worried about how desperate I was to stick my cock inside of her.

"What would I be willing to put up with?" I asked myself.

When we got to the house, I got out first, held the door open for her, and extended my hand to help her out.

She raised her eyebrows at me and took my hand, standing up into my personal space, and giving me a peck on the lips.

She didn't release my hand - and twined her fingers into mine. I led her to the house, trailing behind my sister.

I looked back and she was eyeballing my ass.

I laughed.

She said, "Just checking out the merchandise."

Jessica left the door open for us and was already headed up the stairs. I think she was more excited about this than her friend was.

When we got upstairs, Jessica called out, "Just bring her in here. If you guys take too long, I'll need to intercept the littles. Your room is too close to the stairs."

By the time Kitten and I got into the room, she handed me the special panties and was headed out the door.

Kitten laid her glasses on the nightstand and turned to see me holding the panties.

"Can I?" Kitten said.

I handed them over; she laid them on the bed.

She put her hands on my neck, leaned in for a kiss, and said, "I should probably go first - since it's my hang-up - but can I undress you - and put them on you? I think I'll know by then - and save you wasting your time."

"I'm not sure how you think I'd be wasting my time, trying to squeeze my cock into your pussy to see if we can work something out - but that's fine."

She gave me a scorching kiss and - without much delay - started undressing me. Once I was naked, she stepped back and then collected another hug - and kiss - saying, "Thank you."

I started to reply but she dropped into a crouch and sucked my semi-rigid cock into her hot mouth.

My response turned into a gush of air - rushing out of my body fast enough to collapse a lung.

The heat disappeared. Seconds later, without thought, I raised my feet - as she touched the sides of my knees - one at a time - and then she was sliding the panties up my legs.

She gripped my cock, stroked it once, and then directed it through the rip in the undies, whispering, "Nice," as she snugged the crotch of the feminine garment up against my taint & balls.

She groped the bulge of my ball-sac - rubbing her palm all the way to the head of my cock - and back again - taking my jewels in-hand - and standing up for another kiss.

I watched as she wasted almost no time getting out of her clothes. Apparently, she was satisfied that this was going to work.

She was down to her pink panties - almost a match to the pair I was wearing - when she asked, "Can I keep these on?"

"Can I see it?" I asked. It sounded a little like begging when I heard the words.

She bit her lip and dropped them to the floor.

It was bare - but there was a little blonde peach-fuzz coming back - a natural blonde.

I couldn't remember what color her eyes were - and looked into them - brown. Not the blue-eyed blonde of renown - but I'd take intelligence over cliché every day of the week.

She smiled at me, took my hand, and led me to the bed.

When I glanced over, at the discarded panties, she said, "Let's try this first. You are being very accommodating - and you seem to like how I look. We'll go without to start."

"You look fabulous," I sighed.

She giggled and half-turned to pull the covers out of the way.

She lay - with her head on the pillow.

I stepped across her leg and knelt between her knees.

I lowered my head to her sexy slit and slid my tongue up & down her trench - avoiding her clit - but teasing across the top of the clitoral hood - before dropping back to the bottom to tongue around her entrance.

Her fingers twined into my hair, "Oh, fuck, yes! A little more, please. You're bigger than I expected. This will make things go faster - and you're doing an amazing job!"

I licked, lapped, and teased - and tried to pay attention when her body responded. Once her vagina was getting good and wet, I decided we were ready to proceed.

I started to wipe my face but she told me to let her taste herself on me. I rubbed my cock around her tight entrance as she kissed & licked her juices from my face, mouth, and tongue.

I got my prick about a quarter of the way inside before she put her hand on my chest and took a gulping breath. When she nodded, I pushed in a little more - getting about half-way.

"Out & back in, please," she asked, almost gritting her teeth.

I took one stroke, paused, and took another. I felt her relax a little but did two more short-strokes before I paused.

She nodded again.

Her fingertips clenched into my skin a little as I slid farther in - but she didn't object. When I was all the way in, I stopped until she relaxed a little more.

Her eyes were closed but she nodded again.

I slowly stroked in & out of her until her eyes opened and she watched my face as I fucked her - without changing anything.

"That's nice," she said, smiling. "Go a little faster and let's see if you can get this orgasm to pop."

I sped up until she nodded, once more, and then tried to keep the pace steady.

She bit her lip and closed her eyes again - focusing.

She reached a hand down and tried to grab the waistband of the panties - and reach her fingers underneath to stroke along my taint & balls again.

I stopped to let her rub a little and she said, "Keep fucking me, please."

I went back to what I'd been doing - but she was still trying to touch the garment.

"Jessica!" I hollered.

My sister opened the door.

"Come here," I grunted, as I fucked her friend.

She closed the door and locked it, stepping over beside us.

"Give her a pair of your panties to touch," I ordered.

She complied but - almost as soon as the garment was in Kitten's fingers - she threw it aside - still focusing on trying to grasp her elusive climax.

"Take off your pants," I told Jessica.

Without hesitation, she complied. Seeing what I intended, she took Kitten's hand and rubbed the fingers across her panty-covered mons.

Somebody moaned - I wasn't sure which one it was - and Kitten's pussy muscles started grasping at my fuck-meat.

I watched - still rhythmically fucking the blonde hottie - as her fingers wandered across my sister's groin & thighs.

I felt my dick stiffen a little - as the lusty images made my heart race faster.

"Fuck, fuck, fuck!" Kitten rasped. "Oh! Oh! Oh! Oh! Fuck! Yes! Fuck! Yes! Oh - fuck - yes! Ughhhh!"

As the woman's vagina seized around my stiff cock, I grabbed her breasts - so similar to my sister's - in my merciless fists - and pounded my aching cock into her - my climax so close - watching her face - and feeling her body finally reach what she'd been working to grasp.

I felt my sister's lips on mine and growled - shoving my cock as deeply into my lover as it would reach - an explosion of my seed erupting into her - hoping to reach her womb.

I briefly wondered if we should have been using protection - but we were a little past that.

When Kitten felt the heat of my spunk splash inside of her, her body jolted a little - and she cried out as another orgasm blasted through her.

My sister's hands held my face - kissing the life out of me - as I went back to slowly fucking my cock in & out of her friend's trembling tightness.

Kitten laughed. Jessica & I separated to look at her. She looked from the two of us - and then down her right arm. Her fingers were buried in my sister's pussy.

Jessica's panties were pushed to the side - with three of her friend's fingers jammed into her vagina. My sister's sexy juices were running down Kitten's wrist.

Kitten wiggled her fingers and Jessica said, "Easy, sister, you've got things feeling a little sensitive in there right now."

"Am I to assume," the freshly-fucked blonde asked, "that we can work something out - between the three of us?"

She looked back and forth between my sister and me.

I raised my eyebrows and deferred to my older sibling.

"Did he cum inside you?" she asked her friend.

"He fucking exploded - and I came a second time!"

Jessica giggled and said - looking at me and then her friend, "So, you're okay with this?"

"Jessi," Kitten said, "I came so fucking hard, you could ask me to give you my liver right now and I'd probably do it. Before today, I'm not sure I'd ever really had an orgasm - and I just had two that nearly killed me."

Jessica gave me another kiss.

"I had wondered," her friend said, "but you two can do whatever you want - or need to - as long as I can get more of this."

I laughed and said, "I'd rather not have to wear this thing to have sex - but - if it means the two hottest women I know make those amazing orgasmic faces as I fuck their tight pussies, I think we're in agreement."

"Did he just call us needy bitches?" Kitten asked my sister.

"Kind of. I'm sorry. He knows how desperate I've been. I told him I'd be super appreciative if he'd help me get off on a regular basis."

"Hmm," Kitten said, "I suppose we could spoil the little man-bitch a bit - as long as he keeps our pussies happy."

"Is yours a pussy - or a kitty?" I asked, smirking.