I'm Not a Cross-Dresser

Story Info
Bro needs GF gift/lingerie advice; Sis wants something first.
4.7k words
4.65
41.5k
67

Part 1 of the 3 part series

Updated 12/23/2023
Created 08/13/2023
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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.

~~~~~

As the name implies, it ventures slightly into cross-dressing as well. That idea is a little uncomfortable for me - so this will, likely, be the only chapter in this tale.

~~~~~

I'm a happily-heterosexual male. I have a hot girlfriend (Nadine) who attends the same community college I do. We've been dating for most of a year now.

Valentine's Day is coming up and I am hoping that a well-placed lingerie purchase might result in a night for both of us to remember.

My sister is at class - and I know I've seen an outfit in the laundry that looks exactly like what I think I want to buy my girl.

In my mind, she and my older sibling are roughly the same size. All I need to do is find it, snap a picture of the tag, and I should be set.

I head down the hallway and stop in front of Jessi's room. I try the knob and the door is unlocked. I look back & forth, quickly, to make sure that neither of our younger siblings see me sneaking inside.

I reclose the door and head to her dresser. My underwear is in the top drawer - so that's where I begin.

It's a little more chaotic than I had expected. She's always cool and collected. I guess I thought she would stack the bra & panty sets together like they were outfits - but they're all just kind of thrown in. The bras are mostly to the left and the panties to the right but, other than that, there's no order to it.

I guess I should not have been surprised to find a dildo - but not three. One is the ivory-colored, glossy, pencil-shaped thing that is probably in every old woman's stash.

I shuddered for a second as I thought about what I would find if I went through Grandma Nan's dresser drawer. She was between husbands. She'd already killed off three - and had a new boyfriend.

The other two dildos in my sister's underwear drawer were... a little more exotic.

Focus.

Pink, cottony - with mesh on the side - and cute, little bows on the front.

How much underwear do girls need?

I finally found the bra - and reached to the right to set it on Jessi's bed. The bed, at least, was made - and looked like what I would have expected to find in my older sister's room. The panties were buried - but I finally found them.

They were more like bikinis than briefs - smaller than I had remembered. They would look hot on Nadine - and even better lying on the floor beside the bed - or hanging on the lampshade - as I buried my stiff cock in her tight little pussy.

I laid the panties below the bra, took out my phone, and snapped a picture - then I leaned down to get a close-up of the tag on the bra - planning to do the panties next.

I heard the doorknob turn and panicked. This was not going to look good at all - regardless of who was coming in the door!

There was no time to fabricate some elaborate tale about helping with the laundry; I was going with the truth.

Thankfully, it was Jessica.

She jumped a little when she realized somebody was in the room. Her eyes narrowed - moving from me - leaning over the bed - to the lingerie - and then my phone - glancing over at the dresser drawer that was still hanging open. I probably should have at least closed that.

"What are you doing?"

"I wanted to get a Valentine's Day present for Nadine. I remembered seeing this and thought it would look good on her - since you're about the same size. I was just taking pictures so I buy the right thing. I'm sorry, Jess!"

"You could've asked."

I realized - at that moment - that that's what I should have done. It would have been a little awkward, asking to see her underwear - but less awkward than I was feeling at this moment.

"Nadine's not the same size as me," she said, dropping her backpack at the foot of the bed - and looking at my face - trying to read my expression.

It felt like it would be a bad idea to argue with her.

She didn't look down but, somehow, I got the impression that she was looking at the slight bulge in my pants - that I'd gotten thinking about the panties hanging off of her lampshade.

She turned, stepped back over to the door, and locked it, losing her sandals next to the exit, and walking back to the side of the bed. She was reaching for the buttons on her blouse.

"What are you doing?" I asked.

"You want to see what it looks like before you buy it first, right?"

That made sense, I guess. I mumbled, "Sure..."

"I'll show you."

I felt like the appropriate thing to do - as my sister took her clothes off - would be to turn around. She was, however, staring straight into my eyes.

The implication was that she wanted to see my reaction.

She was going to have to be naked in order to put on the two scant pieces of clothing lying on the bed next to me.

I think I tried to focus on my sister's face - but I'm sure I failed.

I failed because she was doing an outstanding job of forcing my eyes to look, individually, at every single piece of clothing - as she slowly drug it across her soft skin - baring her body to me - one inch at a time.

Her blouse came off and I stared at her lacey black bra. She reached behind and released the clasps. The garment slackened - her beautiful breasts - somewhere between a B and C cup - slowly being revealed as the straps slid down her arms - the fullness of her alluring cleavage causing the breath in my chest to catch. I forgot to breathe again as the dark circles of her areolas finally peeked out over the rim of the bra cups. I swallowed, hard, as the show stop - with her nipples just out of view.

If I had looked at her face, I would have noticed a feral grin at the torture she was causing me - but I didn't - my gaze was exactly where I expected her Milk Duds to make their appearance.

The bra was moving again - sliding down once more - as gravity reclaimed its grip on the lacey lingerie.

Jessi's nipples were nearly a centimeter wide. They only stood out about half that far - but my mouth watered as I took them in. Catching myself, I had to suck the drool back into my mouth. If Jessica noticed, she didn't react.

It was all I could do not to step over to her and see how they felt. My sister had been right, of course, she was not the same size as Nadine. My girlfriend was maybe a B-cup. Her areolas and nipples were pink and puffy - not crimson and rock-hard.

After savoring the sight of my sister's mammaries for far longer than I should have, I looked up at her face and realized she was still watching me.

She needlessly crossed her arms in front of her - causing her tits to stretch and bulge - before grabbing the waistband of her jeans and struggling with the button.

Once again, my eyes were fixed on what was coming next - oblivious to the succubus-grin on my sibling's face.

She finally got the clasp undone, felt around for a bit until she got 'hold of the zipper, and eased it down - just barely revealing the top of her panties - except that all I saw was bare skin.

She pulled the fly open and shimmied her hips - struggling to get the garment to release its grip on her amazing body.

The pants finally started descending. More and more skin came into view - but still no panties.

I realized I was seeing her bare mons. Her slit had to be showing up soon. Was her entire pussy bare? Was she not wearing panties?!

The tiniest brick-red heart appeared - but it wasn't a landing-strip - it was a tattoo.

The top of her slit started a couple millimeters below the tiny piece of skin-art.

It turned out that she did have panties on - if that's what you'd call the smallest pair of short-shorts I have ever seen in my life.

The top of the hot pink pussy-wrap didn't even cover half of her tight slit - and the deep camel-toe between her legs showed that she'd pulled them up about as high as they would go.

Her pants pooled around her ankles and I watched her gap stretch - testing the elasticity of her coochie-cover - as she stepped out of her clothes - and kicked them to the side.

For no reason whatsoever, she ran a fingertip down the front of the panties - along her gap - to her perineum - and then back to the top again. Her other hand grasped the opposing side - and she slowly peeled the thing from her body like it was painted on.

Her hairless quim was lightly pinked - as if she was slightly aroused - but not like she had touched herself.

At the very top of her slit, there appeared the tiniest divot - like her clit was trying to peek out - to get a look at me - without being noticed.

My sister - two years older than me - stood buck-ass naked in front of my eyes - and it was all I could do to keep from passing out from the loss of blood flowing to my brain. All of it had been redirected lower.

"Same size?" she asked, managing to ask her question without voicing the name of my girlfriend - whoever she was - lost in the ether of space - abandoned - forgotten.

I tried to answer but had to clear my throat first. I finally gave up and just shook my head - my eyes never leaving her tight gash. I knew she saw the motion.

She waited until I looked at her face and then nodded to the lingerie, lying on her bed.

"Put them on and I'll rub your dick," she said.

A small seizure ran through my face and - for a couple seconds - my lip drooped like I'd been struck with Bell's palsy.

I looked back at my sister - closely - to determine whether or not she had been switched out for some alien or cyborg.

"Take your clothes off, put on the lingerie, and I'll choke your chicken," she promised.

She realized my brain was calculating some intense math formula and offered, "I've got a towel. You can cum in it."

"Why?"

"I'm not a lesbian or anything - I just want to know what it feels like to run your hands over somebody's body when they're wearing that stuff."

I just stared at her.

"I just want to know what a guy feels when he's touching me."

The logic part of my brain objected.

"It won't fit."

"It'll be close enough."

"No, it..."

"It will serve my purpose - and I won't have to ask somebody else."

I looked at her face.

"You want me to get naked, wear the bra & panties, and you're going to feel around on my body - and then jerk me off?"

"Yes."

For the first time, it looked like she was actually starting to think about what she was asking.

Don't get me wrong, having the bodacious beauty in front of me rub her hands on my body - regardless of the fact that we were brother and sister - was a serious turn-on - but...

"I'm good," I said. "You're gorgeous - which you surely already know - and I appreciate you helping me with this but - I'm not a cross-dresser."

"And I'm not a pervert for my brother's cock - but I'm standing here, naked as fuck, while you lust over my body."

"I was staring.. I wasn't lusting."

"You didn't think about fucking me?"

"No."

"Touching my tits?"

"A little."

"Licking my pussy..."

"Not until you just said that," I replied, looking down at her slit - before looking back up to her eyes.

"I'll put it in my mouth."

"What?!"

"Put on the clothes and I'll put your dick in my mouth. I'm not sucking you off - and you can't move - but I'll hold it in my mouth for 10 seconds."

"I don't..."

"Your cock is hard as a nail and you're going to tell me you're not seriously thinking about your penis being between my lips - even for a second?"

I needed to get out of here. My balls hurt and my dick was leaking pre-cum - just from thinking about her offer. It didn't matter that nobody could know about it happening - it was just that there was a smoking hot girl... woman... standing here, offering to suck my dick...

I jumped out of my skin when somebody knocked on the door.

My hard-on shriveled to nothing and my pulse was pounding.

In seconds, Jessi had her blouse on - having kicked the rest of her clothing behind the door - where she was now standing.

She grabbed the knob and pulled it open.

Our younger brother was there - he could easily see me standing by our sister's bed.

When I'd seen that Jessica planned to open the door, I had grabbed the bra & panty set. They were in my fist, behind my back.

"What, Rodney?" my older sister asked grumpily.

"Have you seen Jake?" he asked, focusing on the only part of her body he could see - which was the only part that had clothing - the rest was naked - and hidden behind the door.

Looking over, he spotted me.

"Oh! What are you guys doing?"

"Girlfriend advice," Jessi replied.

"What for?"

"Valentine's Day is coming," she said, like he was the world's biggest idiot.

"You gonna give me girlfriend advice?"

"Do you even LIKE girls?" she asked the elementary student.

"No," he admitted.

"Go away!"

He turned his attention to me.

"Jake, can I borrow your Xbox headset? Mine died."

"Replace your batteries."

"They're all dead."

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

"Put your batteries in the charger - all of them - and you can use mine for today."

"Thanks, Jake!" he yelled, starting to leave.

"Put it back exactly where it was - when you're done," I warned him.

"I will!"

"You break it and you're cleaning out your savings account to replace it."

"I know! I know! Thanks!" he yelled, running down the hall.

Jessi relocked the door, turned to me, walked over until she was nearly touching me - and removed her blouse once more - taking her time to pull it all the way off as she watched my eyes devour her breasts for the second time today.

My cock was hard again.

I jumped like I'd been zapped when her hand brushed the tent in my pants and she said, "Put them on and I'll suck it. Tell me when you're going to cum and I'll catch it in the towel. You only need to wear them for a minute. Once I see what it feels like, you can take them off and I'll keep my promise."

I didn't move to obey - but I also didn't move as she started removing my clothing - piece - by - piece.

My cock ached from the mental stimulation. I could tell my briefs were sticky with pre-cum.

She started with my pants - unbuckling them - unfastening them - unzipping them - and then pushing them (and my underwear) down my legs until my stiff cock sprang into view - nearly bumping her nose.

I stared at her face as she stared at my cock. Her hand closed around the shaft - near the middle - and she stroked it a couple times - studying it.

She ran a fingertip under the front, caught a droplet of pre-cum, and tasted it - still staring at my penis like it was a diamond.

She got me all the way out of my pants - removing my socks at the same time - and reached for the panties.

This was my last chance to say no. My fingers gripped the panty-set like it was a life-line.

Jessi pried my fingers open, removed the pieces, laid the bra on the bed, and tapped my knee until I raised my foot so that she could put the bottoms on me.

She drug them up my legs like she had removed her own - slowly - with her face hovering in front of my meat-monster the whole time.

She left the front hanging under my ball-sac and reached both hands behind me to tug them onto my ass. They only came about halfway up.

She pressed her closed lips against my cockhead as she finished the reach-around.

She never looked at my eyes. That was probably a good choice. I could feel myself frowning. I wanted her to touch me. I wanted to touch her. But I didn't want to be wearing this. I felt vulgar. Dirty.

She tried, unsuccessfully, to wrap the front of the panties up over my cock. She, finally, had to grab a hold of it, shove it sideways, into the crotch, and then adjust everything after the waistband was above my stiff rod.

She stood - her naked breasts nearly touching me - and looked at my face.

She palmed my hard-on and said, "It's just for a minute. You are being very helpful."

She peeled my T-shirt off and grabbed the bra - pulling my hands and arms to where they needed to go - not depending on me to help at all - because I wasn't helping.

She grabbed my hips and moved me to stand with my back to the bed. She eased me down - onto the mattress - with my knees up against the side of the bed.

She climbed on top of me - her knees to the side - her sex bumping against the front of the panties - and my hard cock beneath - but she was focused on the lingerie top.

The fabric wasn't that course - but her caresses - through the material - were much rougher than I had expected.

There was a lot of stimulation - and my nipples were stiff - but I didn't find it to be erotic.

However, when she pulled the top of the bra down, exposing my tiny teat, and sucked on it - teasing it with her tongue - I jumped. I also, very nearly, grabbed her hips and fucked her - panties or no.

Her mouth finished teasing my other nipple and she crawled up to look into my eyes.

Her lips were millimeters from my own. Her heavy, hot breath was lighting my skin on fire.

She looked at my mouth - my lips - and then back into my eyes again.

Her right hand reached down and gripped my panty-covered cock.

My scrotum fired - and my splooge oozed out of the panties around my cockhead - painting the garment, my cock - and her hand in semen.

"Hair trigger, are we?" she laughed, rubbing my spend around on my bulge and beginning to stroke the panties - and my cock - within.

Her phone rang, she reached over, picked it up, looked at the name, and answered it.

"Hi, mom."

She continued rubbing my dick.

"In my room - talking to Jake."

My heart raced.

"I caught him stealing my clothes."

She looked at me, evilly.

"Oh... uh... concert T-shirts."

She nodded at the phone and glared at me.

"Yeah, Jake!" she accused. "Mom says you should ask before you cum in my room..."

She smirked at the pregnant pause in her statement, staring at the sticky mess in her hand.

"... and get your boy cooties all over my clothes," she finished.

She collected a glob of semen from her panties, lifted her jizz-covered fingers to her mouth, and scooped the errant spend inside, rolling her tongue around to taste it - before wrapping those fingers around my cock, once again, to continue my torment.

She laid the phone back on the nightstand without hanging up. I prayed to God Almighty that mom had ended the call.

My big sister slid her soft, naked body down my lingerie-covered one - until her face was next to my crotch.

Now that my cock was half-deflated from my premature ejaculation, Jessi was able to peel the top of the panties down - releasing my phallus from its panty-prison.

I wanted the bra off - if she was done abusing my chest - but I wasn't quite ready to complain.

She took my semi-rigid cock into her hand and slowly slid it up & down a couple times.

She pulled the skin back, tight, looked into my eyes, pressed her lips against the mouth of my sperm-spigot, and sucked the front of the tip.

I groaned.

"I said I'd suck it. I'm done," she announced.

I growled, "That's not..."

She popped the head into her mouth, tongued all around the knob, and sucked on it.

"Better?"

I groaned like I was in pain.

She stared at my dick until I was taking a breath to complain - then slid it over her tongue - to the back of her throat - and pulled it out again - tracing the tip of her tongue along the bottom of my rod as she removed it.

"How was that?"

I was still deciding how to respond when she did it again. I decided the correct reply was to moan her name.

She grinned like I had lost a bet.

"You like that?"

I stared into her eyes, as she took the head between her lips once more, and nodded.

She did it three times in a row - this time - the head of my cock banging against the entrance to her throat with a "gak, gak, gak".

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