I'm Not a Cross-Dresser 02

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This work of fiction is tagged as Incest/Taboo and describes sexual activity between siblings who are 18 or older. If that type of story is not for you, try one of my others.

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As the name implies, it ventures slightly into cross-dressing as well. That will not be the focus of the story.

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Nadine called the next day. I was halfway between the front room and the kitchen when I saw her name pop up.

Since I was curious about what she would have to say, I answered.

"Hey, Jake."

"Hey."

"You wanna come over? My folks are out."

I liked Nadine. I really had thought maybe she was the one.

She made it sound like we were gonna fuck. Yesterday, I wouldn't have even had to think about it.

I kind of wanted to see if she'd suck my cock; I kind of just wanted to be done with her; but I kind of wanted to know what was going on.

"What happened to the other guy?"

"What guy?"

"From the shady area by the library ..."

"Oh. That's just my cousin."

My brain was figuring out how to ask the next question.

"So, you see me with somebody else and you just assume I'm cheating on you?"

"I never said that."

"You know what, Jake? Fuck you. I don't need your shit. I can't believe - after all this time we've been together - you'd start shit like this."

"Well, I only asked because none of my cousins kiss me the way yours kisses you. I guess I'm just a little confused."

She ended the call.

"That Nadine?" a female voice inquired.

I just about jumped out of my skin.

"Fuck, Jessi!"

"You asked her?"

"She invited me over to her parents; said they were out."

"Ballsy. She's either playin' the field - or his cock just didn't measure up."

She groped my crotch, "I'm guessing number two. You've got a nice package, little bro. She knows she fucked up - but now you called her out - and she's gotta get all offended because you suggested she's a fucking slut."

I looked into my sister's eyes. She was still massaging my tented pants - and it was about to go from a one-person tent to a two ...

"Will you please stop that?"

"You don't like it?"

I didn't respond. An honest answer was going to get me into trouble.

"You want me to suck you off?" she offered.

She felt my cock lurch between her fingers and grinned wildly.

"Jake, you're a naughty boy! You want to put your pecker in your sister's mouth and make her suck on your dirty dick until you dump your secret-sauce!"

I felt like I was being played on both sides. I don't like being manipulated. I turned and headed for my room.

"Jake! What are you doing?"

I kept walking. I got to the stairs before she decided to change tactics.

"I'm sorry. I'll stop. I won't touch you without your permission."

It wasn't much - but it was a start. I paused mid-step and turned to look at her.

Jessica said, "She's going to call back. She'll either admit she tried the other guy - or she'll tell you it didn't get past what you saw in the pictures."

I considered how I felt about each of the directions the conversation could go, where they would lead, what my responses would be, and the likely outcomes.

She continued, "I don't have proof - but - after I took those pix - they walked off together. I don't know where they went - and I don't know if - or when - they came back."

It would have been simpler for my sister to lie to me. She could have just as easily told me that she saw them fucking. This was probably the truth.

"Scout's honor," she affirmed.

"You're not a Scout."

"I'm not lying, Jake."

I stared at her from across the room. Neither of us had moved.

My sister persisted, "The fact that she's already called back today either means she was planning to fuck you both - like the whore she is - or she already realized she fucked up. Either way, if I know you, that's not what you want."

"I'm not planning to take her back."

"She'll be persuasive."

"As you said, I'm not good with sharing - and she would have to earn back my trust - but how do I know she's not still lying. I think we're just done - whether she's figured that out yet or not."

"Good."

I turned to head up the stairs.

"Jake."

I looked at her.

"Can I take her place?"

Before I had time to even consider a response, the front door opened and mom stepped in.

"Jessica."

"Hey, mom."

I turned and headed to my room. My mind filled with pictures - images - and memories. The images were of my sister's naked body. The memories were of the way it had felt when my cock was in her hand, her mouth, and her pussy.

"What cost?" I asked myself.

I'd "lost" a year with Nadine. I didn't really want to start over again.

Jessica - my sister - my older sibling - was definitely hot - definitely a good fuck - definitely had me firing on all cylinders. The physical attraction was there - no doubt.

I just wasn't sure I could deal with where we'd ended up the last time. Somehow I knew this clothing thing - whatever it was - whatever she wanted to call it - it wasn't going to be a one-time thing.

"Would she quit? Could she? Could I make her?"

I could threaten to out her to mom - but that would be shitty.

Even if she didn't decide to tell mom that I'd fucked her - regardless of how much of it was by her design - it would mess things up - not just between me and her - but for the whole house.

That event - that whole thing - needed to remain private - forever. It was amazing - and I'd love the chance to do it again - but - if she wants to dress me up ...

"What if - next time - she wants me to wear a sundress or some shit?" I wondered.

Although the idea of my sister - sticking her head up - underneath - and deepthroating my cock was arousing - her movements billowing out the flowing fabric - outlining the back of her head - as she banged my cock against the back of her throat - sucking like a vacuum cleaner ... I wasn't wearing some flowery, yellow Easter dress.

I lay on my bed and thought about my choices until mom yelled that dinner was ready.

Dad must've been off on some trip again - because it was just the five of us. Jessica didn't (of course) say anything at dinner and - after only having to put up with my younger siblings for several minutes - I cleared my dishes, packed the leftovers away, and headed back to my room - hoping mom wouldn't call me back to the living room to help the little turds with their homework.

I was laying on my back, staring at the ceiling, when Jessica came in and sat down beside me.

Her hand reached for my crotch again - but she paused before it touched. Her open palm was hovering an inch above my now-growing bulge - fingers spread wide. She looked into my eyes for permission.

I did not grant it.

She opened & closed her fingers - clenching them - as if fondling an imaginary cock-head.

When I didn't react, she laid her hands in her lap.

"You don't want me to?" she asked.

She seemed to seriously want to know my answer - not just tempt & taunt me with rhetorical questions.

"I had fun," I admitted to her.

"Then why are you hesitating?"

I looked for signs of the succubus. I didn't see any.

"Jessi, I'm not sure it's a good idea."

"I get that. If I wasn't your sister - just another girl."

I thought about it.

"You're beautiful. If you weren't my sister, I don't think there would be any question that I would be interested in a long-term relationship."

"Okay. So. Assume we can just keep this between the two of us."

I looked into her eyes, "Jessi, that's a lot of work."

"More work than finding somebody else?"

"Touché."

"Jake."

She was looking at her hands.

"The dress-up thing."

Now we were getting somewhere.

"It's kind of a thing for me. I'm not sure what it is. I don't want a relationship with a girl - I want a guy - but I want to see and feel my clothes on them. Please don't say I'm weird."

"You're weird, Jessi."

She pulled her hands to her face.

"... but only slightly more weird than your little brother daydreaming about getting another chance to shove his cock inside of you."

I waited until the words went through her ears - to her brain - and she lowered her hands to look at me.

"You'll do it?"

"Can I ask you why?"

"I don't know. I don't. I just ... I ... regular sex - no matter how you do it - it doesn't do it for me."

She still looked like she was being honest. She sounded like this hurt to talk about.

"My last two boyfriends left as soon as I asked them to do it," she admitted. "It didn't matter that I'd sucked them - and fucked them - raw - and done everything they had asked - they were just done."

"It's a big ask, sis."

Her hands went to her face again. I couldn't hear crying - but her shoulders were moving in a way that told me she was weeping.

This whole thing was just fucked up. I'm not supposed to fuck my sister. She's not supposed to fuck her brother. And - in my perfect world - she shouldn't need her lover to wear her clothes to get excited.

"Have you tried wearing men's clothes?"

She pulled her face out of her palms and looked at me. Her eyes were red from crying.

She got up, walked to my door, locked it and walked back. She started undressing. I watched her for a couple minutes before she asked me if I was just gonna lay there.

Apparently, the answer to my question was that she had not tried it - and we were going to do an experiment.

I was down to my underwear when I looked over - to my sister - standing less than two feet away - who was gorgeously naked once more - this time in MY bedroom.

"God, you're hot," I told her.

"Finish getting undressed, jackass, or you ain't gettin' shit," she replied testily.

I peeled off my underwear and handed them to her. She pulled them on.

I had to admit she looked pretty fucking hot - standing there in my briefs. Was this what she saw when a guy was dressed in her clothes?

She pulled on the pants and the T-shirt, shoved me back - until I was sitting on the edge of my bed - and then climbed onto my lap - with her knees on either side of my waist - resting on the mattress. My naked cock rubbed against the fabric of my jeans.

She put her arms around me and attacked my lips & mouth with her own.

When we were both out of breath, I looked into her eyes - asking the question.

"Not sure yet," she admitted. "Let's up the ante."

She pulled the neck of my shirt up, sniffed it - and then grabbed the hem - and lifted it over my head - trapping my face inside - smashed up against her breathtaking breasts. I gobbled them up, I groped them, I worshipped them.

She was writhing and moaning.

"Oh, Jake. Keep doing that."

Her pelvis was rubbing into my lap - my hard-on was being buffeted by the crotch of my own jeans.

I pulled my head out from under the T-shirt - off of the taut teats belonging to my older sister - and grabbed her face - pulling her in for a long, hot kiss - which she returned with gusto.

"Maybe we're good ..." I thought.

I stood up, carrying her with me, and spun us - so that I was facing the bed. I laid her back (onto the mattress), unbuttoned & unzipped the pants, pulled them (and the briefs) halfway down her thighs - and then shoved the pants (and her legs) back towards her face - exposing her glorious slit.

I fisted my cock and nudged the head against her opening - waiting for her to approve.

She looked into my eyes and nodded.

I pushed forward slowly - squeezing my raging hard-on into her depths.

She bit her lip and continued to watch my eyes - and mouth.

When I was almost all of the way in, I got a little resistance - so I stroked out - and back in again - repeating that - until she loosened up.

I had a good rhythm going - and my balls were churning.

I was fucking my sister - on my bed! She was probably the hottest girl/woman I had ever fucked.

Her pussy felt amazing - slippery but tight - she was beautiful & sexy.

I had been fucking her for several minutes when I realized that I wasn't receiving any of the feedback that I usually got by this point of sliding my cock in & out of a girl's pussy.

I looked at Jessi's face. She was watching my eyes. I saw when she recognized that I realized something was off.

"You okay?" I asked.

"I can't cum," she said, getting a little misty-eyed. "It feels amazing. I love your cock. It's nice - we're a good fit - physically - but my orgasm just keeps alluding me - running ahead of me - and I can't catch up to it."

I looked down and saw her panties on the floor - a half-step away.

I unplugged myself, reached down, grabbed them, and put them in my mouth.

I wedged my cock back inside of her and went back to fucking her amazing cunt.

She let me go another couple minutes before she shook her head no.

I took the panties from my mouth and pulled them onto my head like a stocking-cap.

She just started laughing at me - her cunt threatening to eject my meaty-pole. She shook her head again.

I sighed, unplugged my cock once more, pulled the panties from my head, stepped into them - shoving my erection through the left leg-hole - along with my leg - and lined up to jam my aching cock back into my sister's pussy.

The cottony fabric brushed against the inside of Jessica's thigh and she moaned.

As I tried to move into position, I realized that the leg hole was too tight. There wasn't enough room there for both my leg and my cock - and to still be able to move like I needed to.

I looked up at my sister's face - waiting to have my cock inside of her once more - and back down at the panties - her panties - that I was wearing.

I really didn't want these things on - but I really WANTED my cock back inside of my sister's pussy - and - if I was going to get off - she should be able to as well.

"Rip them," she told me, impatiently.

I pulled at the leg-hole - but the reinforced material wouldn't give.

I dragged the pink undies off, once more, and brought the material up to examine it for weaknesses. The crotch was reinforced - but that's not where I needed a hole. I stuck my thumbnail into the thin cloth - at the front - and pushed in - until it finally gave. I stuck my other thumb in and pried the tear wider - to make sure I had wiggle room.

I pulled the frustrating thing back up my legs - and onto my waist - wedging my stiff cock through the jagged hole.

I grabbed a hold of the pants - and my sister's legs - and plunged back inside of her glorious gash.

Almost as soon as Jessica felt the material of her underwear rubbing against her legs & ass - as I fucked my cock into her tight slickness, the moans started.

I was tired of fighting my own pants - and the experiment had, obviously, failed - so I wanted them out of the way. I pulled my cock out again, yanked my pants off of her (but left the briefs in place}, and shoved her legs toward her face once more. Using my underwear (which was trapping her knees) as a hand-hold, I rammed my penis back inside of the luxurious velvety sheath that was my sibling's vagina.

"Fuck me, Jake!" she cooed.

I had been getting closer the whole time we had been experimenting. There wasn't much left for me.

The cloth of my sister's panties - contacting her skin - as I fucked my prick in & out of her twat - seemed to have flipped the switch for her - which meant I would be able to cum soon.

"I'm close, Jessi. How close are you?" I grunted, still fucking her.

"Close, Jake. Close. Give me a dozen more like that. Please. I'm there. Cum with me, little brother. I want to feel your hot seed exploding inside of me."

I was only able to give her ten more before my fight was over. I was tired. I pushed in as deeply as I could - as the sperm started blasting from my cock. I grunted each time it fired.

"Fuck, Jake! Oh, fuck! Rub my clit!"

I reached down, with the thumb on my right hand and stroked her nub. Her body started spasming.

The clasping of her pussy muscles was trying to suck the rest of the semen from my body. I was already over-stimulated - and it was almost painful - but I stayed put until she got all of hers.

Jessica had closed her eyes when the tremors began. Now she opened them - and opened her arms to me.

I leaned down, wrapped her in a hug, and gave her the naughty kisses she seemed to be asking for.

Kissing her - with my cock still buried in her pussy - that was still kind of vibrating - was amazing.

We made out for several minutes like that before she pulled back and just looked at me.

"Thank you, little brother. I needed that. I know this is not your thing. I'm grateful for you working so hard to help me out. I promise to be very appreciative."

I looked at her eyes, her mouth, and her face - damn, she was beautiful. I'd be stupid not to want to fuck her any chance I could get.

Her eyes got worried.

"Can we work something out, then?" she asked.

"You're going to be super-appreciative?" I asked, smirking slightly.

"Very," she said, grinning wickedly.

"I guess we'll just have to see," I said. "Does this mean I don't have to do your laundry for the rest of the month?"

She looked like she was going to object for a minute - but then changed her mind.

"You were very patient with me tonight. That's probably a fair trade."

I jumped when somebody knocked on my door.

I felt naughty - responding - when my cock was still buried inside of my older sister's cunt.

"Yes?"

Mom called out, "Can you put the dishes away before you go to bed?"

"Sure."

"Do you know where your sister is?"

I looked down - to where the root of my dick was just visible - while the rest of it was wedged inside of her warm, gooey snatch.

"I can go find her - but I'm kind of ... in the middle of something ... at the moment," I yelled.

"Okay. Her stuff's still in the dryer and I have a load waiting."

"I'll get it," I replied - glaring at my sibling - "I still owe her a couple days' worth of laundry for messing with her T-shirts."

"Okay. As long as you two have everything worked out," she said.

My sister did a Kegel or something - and the muscles of her vagina milked my penis again. She grinned, wickedly at me - and then bit her lip.

"Yeah," I hollered, "we're working things out."

"Sounds good," she said, "goodnight, Jake."

"Night, mom."

~~~

Two days later, I got a text from Nadine.

"You and your sister seem to be spending a lot of time together lately," she said.

"If that's your attempt to get me to sleep with you again, I don't think it's going to work," I replied.

"Why would I want you back?" she asked.

"If you're so bored that you need to spend your time stalking me, then your cousin must not be keeping you very busy."

She didn't reply.

When Jessica got home from class, I showed her the messages.

"She's not very bright - or she's phishing," she said.

I nodded.

"If we change anything, she'll accuse you of fucking me - just to appease her ego at getting caught cheating on you."

"Guess I need to find myself a new girlfriend," I said.

Jessica got pensive and finally said, "Let me think about it."

I headed to my room to work on my assignments.

Several minutes later, my younger siblings - who'd just arrived on the school bus - stuck their heads in my room to let me know they were home.

I sent them to the dining room and headed to get them a snack to hold them over until mom got home to make supper.

I gave them celery - with peanut butter smeared down the groove - and a parade of raisins marching across the top.

My sister accepted the snack - and the glass of milk - without complaint; Rodney (of course) felt the need to incite violence.

As soon as he started complaining, I picked up the plate & glass and took it to the kitchen - setting it in the refrigerator.