My Sister's Nylons

Author's Note

This is a full-length story in several parts. It features a man who enjoys cross dressing, not only because he likes it, but to attract his bisexual sister. These is no male gay sex, only because that is not this story. There are several bi females, however. Scenes that appear as first to be forced sex are enjoyed by all parties from the outset and at times and are more benign that at first thought. Included in later chapters are scenes of incest, bondage, group sex, lesbian sex, FFM, FFFM.

If that's not your thing, fair warning. Probably best to look elsewhere.

This one's a slow burn, so if you're expecting hard sex in the first few pages, you'll be disappointed. But if you enjoy a good buildup to some very explicit and beautiful romantic sex, then stay right here.

I'd love some feedback.

Everybody's 18 or over.

~~~

Chapter One

Mom is 39. As a media personality, she dresses very elegantly. Her best physical feature is her legs. Long and lean, they are spectacular. At work she would wear beautifully custom-tailored business suits. They fit her tall hourglass form perfectly. A typical outfit for her would be a low heel and knee-length pencil skirt, with a fitted jacket and blouse. At home, she'd be casual. Jeans and sweats, but usually a nice skirt when she goes out.

About six months ago, something changed. Mom started shortening her skirts. Her heels got higher. Everything got a little tighter. She wore her long, honey-blonde hair down more frequently. Even at home Mom started wearing nylons and skirts, and even heels. I love looking at her fantastic legs. Before, I'd have to steal a look before she went to work. Now I can look at them all the time we're home.

Up to a few months ago, Dad was kind of remote. It was obvious he wasn't putting much effort into their relationship. Mom would do her thing and he would do his. Weekends, he'd be out golfing with his buddies, or watching a game on TV. He had passed most of the household chores to me and my older sister Diana. Even if Mom asked him to do something, he'd put it off and put it off until she had to nag him to get to it. I'd been noticing a bit of strain between them, and it was getting worse.

Lately though, he's been much more attentive. In fact, I would say he's been almost -

submissive

. She can pretty much get him to do anything now. He can kiss that afternoon baseball game on TV goodbye whenever Mom has other plans for him. Could be anything. Fixing stuff around the house. Cleaning the bathroom. Seriously.

In recent months, if anything Mom's upped her game.

Yesterday, she ordered Dad to come shopping with her. Her outfit bordered on fetish wear: tight little shorts, tall high heels, and oil-shine pantyhose. She wore a tank top that clung to her tiny waist and squeezed out her fantastic cleavage. Mom's a 34DD. I know. I looked in her closet drawer one day and checked.

Now Dad follows her around doing her bidding like a trained puppy.

Something's definitely changed about Mom and Dad. She's got a whole new attitude about showing what she's got. I like it.

I mostly inherited my Dad's features. We're both tall and slim. Very little muscle. Soft features. Low, smooth voices. If you close your eyes, you might think Dad's voice is almost feminine. We're not the types that usually attract hot girls. But the fact that my gorgeous mother married Dad gives me hope I might find someone sexy and compatible.

My sister Diana gets her looks from Mom. She's 22 - two years older than me. She's been living at home while going to college. Now that she's graduated, she's got a job in upper New York State. She's moving out in few weeks, just around the same time I'm going off to college. We'll both be in Albany. I have an apartment all set up, but I don't have anyone to split the rent with yet. Diana's not interested in living with her brother, so I'm hoping I can find someone once I get settled. I am worried, because once you start the year, pretty much everyone has their living arrangements organized. And I don't want to live with just some random reject.

Dad suggested Diana and I share the apartment. Like Diana, I'm not sure that's such a good idea. I'll need quiet to study, but my sister's a bit of a party animal. She's got lots of friends and I'm sure she'd be bringing them over.

Diana takes after her mother. Even if she is my sister, I can honestly say Diana is fucking hot. She's got this amazing long, wildly-thick platinum blonde hair. She's 5'8", slim, pretty, and she's got a pretty nice rack on her too. Almost as good as Mom's.

Diana also shares another fabulous trait of Mom's. Legs. Holy fuck, I can honestly say my sister has the most gorgeous legs I've ever seen. Like Mom's, Diana's legs are a mile long, perfectly sculpted, and lean. The weird thing is though, she doesn't flaunt them like Mom. Mom really loves to show off her legs. Diana is less 'out there'. I see her in jeans and pants quite often. Too often.

But like Mom, Diana recently started to change. Maybe Diana's starting to realize she has to dress better for work. She started wearing skirts, dresses, and heels right after she got the job. And when Diana goes out, holy fuck, the skirts she wears are so short I nearly cum right there, just looking at her legs.

Mom was the big influence there, I'm sure of it. One day, she took Diana shopping. The two of them were gone for hours. When they came home, the SUV was packed with packages. I helped bring everything in. On the final trip, when I was outside at the back of the car, I took a peak inside a couple of the bags. A few bright silver boxes caught my eye. I pulled them out to have a look.

The boxes were made of high-gloss cardboard, about the size of a hard-cover book, and about a quarter-inch thick. The pictures on the front gave me an instant hard on. They were models wearing brown, high-gloss nylon stockings. The label on one box was 'Gio, Fully Fashioned stockings, 100% nylon, Havana'.

The seal on the box had been broken. So Diana and Mom had already looked at the contents. That meant I could take a peak too, and no-one would be the wiser.

Looking around to be sure I wasn't spotted, I put the little box on the floor of the trunk. I carefully opened the box. Inside was a sheet of folded tissue paper with a stick-on seal holding it together. The seal had been broken, confirming that either my mother or my sister had already looked at it.

Carefully I pulled the tissue paper back to expose a shiny light-brown sheet of nylon. It was very fine, with no flaws or variations that I could see.

I realized I was looking at the nylon stocking. It was folded around a piece of light cardboard. I had to admit, I was getting a little excited. The quality of the stocking was incredible. It was like a piece of art.

I looked around to see if anyone was coming. In the house, I could hear Mom and Diana talking excitedly to Dad about their purchases.

So I was alone.

I picked up the cardboard with the stocking wrapped around it. The ends of the stockings, the open part at the top of the leg, hung below. They looked so filmy, so sexy, I couldn't resist. I picked up the nylon and put it to my face. The feel of the soft glossy material was intoxicating. It was so damn feminine. I began to grow a hard on.

I was so overcome that I fumbled with the nylons. Before I knew it, the cardboard had fallen away and I was holding the stockings in my hand. I was surprised how long they were. They were so light and filmy, they wafted in the slightest breeze. They had a light brown tint and were almost transparent. There was a lot of stitching in them too. There was a seam along the full length, and the ankles had a complex pattern on them. The toes were dark with reinforcement.

These were works of art. I tried to imagine how such gorgeous, fine-meshed nylons were made.

I felt a deep stirring in my cock. I wondered, for just a moment, what a girl feels like wearing these on their skin...

"What's going on here? Ted?" Diana had come up behind me.

"Nothing, nothing," I stammered. "I was picking up your things and this box kind of came apart. I was trying to..."

"Seriously? You want me to believe your bullshit story? I saw you looking at my stockings."

"Your stockings? You wear these?" I was incredulous. I'd never seen my sister wearing anything like these. Of course when I thought about it, I couldn't think of a finer pair of legs to wear them.

"Well, not yet. But yeah, they're mine. Look what you've done! They're all over the place. Don't you realize how delicate these nylons are? And what are you doing opening this anyway? What are you up to, little brother?"

"Nothing, nothing, I told you, it just came apart."

"Hmmm." Diana looked at me with a pained expression. She has an excellent bullshit detector and I was pretty sure it was on full alert right now. "Well, give it here. I don't want you touching my stuff."

For the rest of the afternoon, I couldn't think about anything except the women in my house, with their gorgeous legs and their glossy, sexy nylons.

I was definitely beginning to look at them both in a whole different way.

That afternoon, Mom announced to Dad that he was taking her out for dinner to some fancy place that she's been talking about. My sister's getting ready for a date tonight so I'm on my own. I've never had a steady girlfriend and so I had nothing much to do.

I'm not really very attractive to girls, I'm afraid. At school, jerks have said I've got a body like a girl's, only without the good parts. I've always felt I had to overcompensate by acting more manly. When I was younger, I pretended to be cynical about life; I talked tough; I was always sarcastic.

Of course that was silly and stupid. I'm not really that person.

And so I've resolved to look for a girl who is attracted to the real me. Tall, slim, soft features. I had to force myself to realize that was OK. That a lot of successful, happy men go through life like that. And they have wonderful, sexy women as wives. Look at Dad. I'm a lot like him and look at who he's married to.

I ate my dinner over the sink and thought about what movies I might like to watch.

***

My sister had disappeared into her bedroom for something like a couple of hours. I wondered what the hell she was up to.

I was halfway through The Batman when she came out. I'm telling you, I had to do a double take.

Holy fuck.

Long, thick, wild platinum blonde hair to her lower back, skin-tight blue tank top with gorgeously proportioned size C's, tiny, tiny waist, brilliant red lipstick, and - holy fuck I can hardly believe I'm saying this but - the shortest, tiniest, tightest little skirt I've ever seen. And she was wearing those stockings!

She didn't seem to care that the bottom of the dark reinforced parts of her stockings was showing.

"Sis, you're nylon tops are showing." I felt it only fair to point it out to her in case she hadn't noticed.

"You don't get out much, do you Ted? That's the style now. You've got to show a little edge when you go clubbing. This is my edge."

Fuck her legs were spectacular. The glossy nylon stockings were chocolate brown with a black seam running up from her ankle and disappearing up her skirt. The heel had a darker area that extended up the back of her calf a few inches, kind of like a triangle. Her shoes were open-toed so you could see the dark reinforced toes of her nylons. She was wearing five-inch heels and they made all the muscles in her calves and thighs stand out. Her legs were sculpted masterpieces, the embodiment of pure sex.

Fuck. I started to build a boner right there. I had to adjust myself so my sister wouldn't see it.

Diana turned and headed out the door. I thoroughly enjoyed the view of those amazing legs in stunning nylons walking away from me. And I thought, someone is a pretty lucky guy.

After that I couldn't really concentrate. Everything I put on TV was simply not interesting to me. The image of my sister's legs wouldn't leave my brain. I began to think about what I'd do if she was here, right now. Would I get up the nerve to touch them?

I ached to caress her smooth, silky legs wearing those incredible fully-fashioned nylon stockings.

The more I thought about it, the more I needed to get myself off.

But tonight, with those legs etched into my brain, I had to do it differently. I had to do it better.

I had a plan.

I went into my sister's bedroom. It was a total mess. Clothes hanging on her desk chair, strew all over her bed, piles of shoes on the floor, vials and tubes of makeup on her desk, along with brushes and pads and lots of other stuff.

Not what I was looking for.

I went to her closet. She's got a six-drawer dresser in there, full, I'm sure with all her underwear and other delicates.

I opened the top drawer. Bras, panties, stuff like that. I closed it.

The second drawer was crammed with socks and shorts and t-shirts. I did see some tank tops that gave me a brief flush. I picked one up and imagined my sister's gorgeous tits pushing out the fabric.

Pushing it

way

out.

The third had bathing suits, a coverup, some hats and sunglasses.

Then I opened the fourth drawer.

Jackpot.

There were several unopened boxes and thin envelopes. Each had stockings and pantyhose in various colors and patterns. There were a couple of lacey belts, a couple of silk corsets, and other lingerie stuff. I picked up a black stocking belt and held it in the air. Eight little straps, each with its own fastener, hung from the belt.

Even better, there were several little Ziplock baggies, each containing a pair of nylons. There had to be a couple of dozen sets. They were all labeled with black sharpie in my sister's printing.

Diana had been busy this afternoon.

My boner grew with the prospect of what I was about to do.

I pulled out a clear baggy. It was labeled "Cervin, Tentation Fully Fashioned Seamed Nylon Stockings 15DN - Color: Chocolate".

As good as any, I figured.

Now that I was in Diana's closet, I was getting a pretty heavy dose of her scent. I looked at the clothes she had hanging in two separate stacked rows, one above the other. I ran the back of my hand across the skirts and dresses hanging from the lower rack. Below them, several pairs of high-heeled shoes in various colors, sheens, and heel heights were scattered all over the floor.

I pulled out a couple of skirts. They were short and silky, light, and smooth. I shook them lightly and the fabric danced in the air. I thought about these filmy, silky skirts brushing my sister's incredible legs. The pressure in my pants was getting seriously painful. And so I thought, 'what the hell'.

I made a little space on the floor of my sister's closet and sat with my head immersed in Diana's skirts and dresses.

I wanted to get the maximum tactile feel of the stockings. So I put my thumbs into my waistband and swept my sweatpants and underwear right off and out of the closet. My cock stood right at attention, pointing straight out the door.

Excitedly, I opened the baggie and pulled out the nylon stockings. I picked them up from the fat end and held them high. They were so light and filmy; I could see through them. Dark seams outlined the stockings. The elaborate stitching was intricate and beautiful.

I decided to get a really good feel for the stockings. I pulled the top of one open and placed my hand inside. I made a little fist so my fingernails wouldn't snag the nylon, then pulled the stocking all the way up my arm. I put my hand to my face and swished it around. It made me feel sexy and really fucking horny.

I held the nylons up high and dangled them over my cock and balls. The feet of the stockings caressing my skin sent little shocks up and down my shaft and made my dick twitch.

I grabbed a couple more baggies and pulled out more nylons. I dangled them all over my legs and balls. They made my skin tingle, and my cock was so hard it seemed to be reaching out to them. I took one and wrapped it around my shaft, around and around until the entire stocking was coiled up. Then I pulled it away and let the silky nylon slide off my throbbing cock, sending shockwaves up and down my body.

I wondered if Diana got this kind of thrill wearing these.

Enough of that.

I slipped the end of the stocking over the head of my cock and pulled it down around my balls. Slowly, I gathered the nylon around the base of my cock and drew it down its length. Little nerve impulses coursed up and down my sex as the nylon foot drew closer and closer to my dick, bringing me oh so close to the edge of cumming. I had to slow the gathering of the stocking around my cock because it was twitching so fast I knew one wrong move and I'd blast into the nylon.

Sure that was the plan, but I wanted to savor it.

Soon the dark stitched heel passed over the head of my cock. Getting really excited, I pulled the beautiful silky heel of the stocking further down and fitted it around the base of my scrotum. Before long, the head of my sex was fully imprisoned in the dark toe of the gorgeous French nylon stocking. I pulled the Cervin tight around my shaft and laid a full grip on my cock and its nylon sheath.

There it was. My cock pulsed and twitched inside the foot of the sexy nylons that have encased Diana's incredible legs. And will do so again soon, I'm sure.

I decided I wanted to prolong the climax. I put my head under the hemline of one of Diana's silk skirts and imagined the legs that usually occupy this spot. I thought how wonderful it would be sliding my head under her skirt and kiss and lick and rub my face all over those silky, glossy nylon thighs. I thought about Diana sitting beside me wearing this silk skirt with these ultra-sheer nylons, crossing her legs, letting me put my hand on her thigh, gently placing my mouth on the glossy nylon.

I pressed the silk skirt around my face with one hand and gently stroked my dick through the nylon stocking with the other.

It occurred to me that this was a really great idea. I knew this would not be the only time I would whack my dick inside this closet, with my sister's nylons as my fetish and her glossy legs as the image of my fantasy. This was definitely to be the first of many.

As I stroked and fantasized, my entire core was on fire. I kept the pressure off the sensitive part of my dick to prolong the stroking because I wanted this to last and last. But I was building into something really, really powerful. I knew that when I was ready, I'd drive my fingers deep into my glans and I'd blast my load into Diana's gorgeous nylon stocking.

I hadn't really thought through how I was going to clean and dry her nylons after I was finished. I'd figure it out.

I realized there was another stocking I wasn't using. Keeping my head buried inside my sister's dresses, I picked up the other stocking and swept it all over my legs and stomach. Now I was on sensory overload.

Oh god, oh god, here it comes, here it comes.

I prepared to dig in my fingers and get my just reward.

At that instant, the dresses were yanked off my head. The overhead lights were on.

"What the fuck is going on here?" Diana was standing there, scowling.

Her gorgeous legs were at eye level, showing the dark tops of her glossy nylon stockings. But I couldn't look at them now, because my sister was screaming at me.

"You fucking little pervert. I can't fucking believe this. My stockings? Fuck, fuck, fuck. I can't believe you're using my gorgeous French stockings to whack your cock into. Have you? Have you cum all over my stockings? Well, have you, you little fucking pervert?"