She nodded vigorously. “Yes, that’s it exactly. Why should I compromise? Why settle? Any guy who thinks he’s ‘too manly’ to wear my stockings is no man for me.”
“Just your nylons?”
Diana smiled. “It’s a start.”
Everyone she knew had shied away from her fantasy. But now, I realized I felt a strong pull to Diana’s fetish.
“OK Sis. I’ll do it, on one condition.”
Diana sighed. “What?”
“I want you to model your sexiest lingerie for me. Including stockings. And I get to help you fasten them. And I get to shave your legs.”
That surprised her. I could tell she was expecting something sinister. She grinned and clapped her hands together. “Deal.”
Diana jumped up and pulled a dozen pairs of shoes out of her closet. She sat on the edge of her bed and looked at me expectantly. I reached for one of the shoes she had bought for me and slipped it onto my foot. Surprisingly, it fit perfectly. Diana had researched well.
“Go on,” she said excitedly. “The other one. Put the other one on.”
When I did so, she beckoned me to stand. Awkwardly, I did so. Wobbling on two feet, I was afraid my ankles might break sideways. But Diana had chosen a big, chunky heel and I was able to hold my ground.
“Take a walk. Go on, just to the closet and back. Do it, Teddy. You promised.”
Fuck I felt awkward. But I powered through it, modeling my new shoes and stockings for the private viewing of my sexy sister.
“OK look.” She approached me and stood at my side. “Watch me walk. Step out and land on the heel. Don’t put hardly any weight on the heel but roll your foot to the toe. Don’t try to land on the toe, you’ll fall over. See, heel to toe, heel to toe.”
I enjoyed watching my sister’s gorgeous legs as she taught me to walk in heels. After several minutes, I managed to walk across the room without stumbling.
“Oooo, you look so, so, so – shit I can’t say it.” Diana looked genuinely conflicted.
I was fairly sure she was hung up on the word ‘sexy’. At the thought of that, my boner only grew. She noticed, of course.
“I see you like them too, Teddy. Mmmm, yes, you like them very much. Ok, come here. Put some nylons on me. No, not like that. Get on your knees mister. On your knees.”
There was something about her voice, the way she looked at me. She had instantly taken on a much more authoritarian attitude with me. I had to comply. Her voice left no doubt. I fell to my knees at her feet.
Diana gestured towards one of the Ziplock baggies strewn about her chair. “That one, Teddy. Open it and take out the stockings.”
I pulled out a pair of incredibly sheer, light, airy silk. It was the color of my arm. The stockings were long and filmy, with a brown seam and lacey welts. They were nearly transparent. My cock tingled at the thought of these encasing my sister’s gorgeous legs.
“Now you’re going to put them on me. Carefully.”
I began to bunch them up like she’d taught me.
“No, you’re going to snag them like that. Put them down.”
I looked at Diana. I was puzzled. She’d taken on a new tone with me. Imperious?
“Go to my dresser, fourth drawer, and get a pair of mesh gloves. Hurry up.”
I did so. But I guess I wasn’t moving fast enough.
“Back on your knees, Teddy. Those are hosiery gloves. Put them on. They’ll protect my stockings from your nails. I’m going to have to do something about those nails on your hands.”
I lowered myself to within eye level of her knees once again. I was glad to do it, because her thighs were so close to me.
“Take off my stay up stockings. Carefully.”
I reached past her knees and put my fingers inside her lacey welts. Slowly, carefully, I began to pull them down her thigh.
I was living one of my wet-dream fantasies. I took my time, because I wanted to savor the moment. She liked that.
“Prepare the nylons for me.”
I gathered it up in my hands.
“Good. Now dress me. Put my stockings on my legs. That’s a good boy.”
Clearly Diana believed I would do anything to touch her legs. She was about right.
She extended her toes to let me place the stocking over them. I pulled it around her ankle. Wordlessly, she put that foot down and raised her other one. I took that to mean she wanted me to put the second stocking on the other foot. I did so.
Then she stood. I was still kneeling at her feet when she issued her next command. “Come on. Ease them up my legs. Make sure the seams are good and straight. That’s it.”
Carefully, I drew the nylon up her left leg. I did it mostly from behind her so I could guide the seam properly. But it was my first time and it was a little awkward. I didn’t quite get it right.
“No, no, no. You can’t expect me to go out like this can you? Do it over. This time, do it right.”
It did take a few tries, but eventually I got her stockings up to within an inch of her pussy and nicely lined up.
“Good. Now fasten my garters. Careful now.”
It was much easier to do it for her than on my own legs. All I had to do was reposition myself around Diana and carefully push the little rubber nodules into their metal tracks and secure them nice and tight.
There was the added bonus that my face was two inches from her tight, round bum.
“Good boy. You did well. Now you may put my shoes on my feet. Those ones, the red heels.”
I picked up one of her beautiful stilettos. The heel was at least five inches long. The shoe sparkled like red metalflake. The toe was long and wickedly pointed. Sexy as hell.
I put my hand around Diana’s ankle and picked up her foot. Angling the shoe a bit, I carefully placed her nylon toes into the shoe and pulled it over her heel. I repeated the process for her other foot.
“Now my skirt. Go to the closet and pick one. Go on.”
I got up off my knees and went over to her closet. I surveyed all the skirts and dresses hanging there. Only a few days ago I was sitting in that closet fantasizing about my sister’s legs inside them.
I found the perfect one. Pure silk, it was only about 14 inches long, so it would be really short on her long legs. The hem flared a bit and the silk was light and feathery.
Diana was standing in her stockings and heels, waiting for me. I kneeled at her side and held her skirt open for her. She stepped into it. Still on my knees, I pulled it up to her waist, zipped it up, and clipped the hidden fastener.
When I had finished, I leaned back on my heels and stared at her legs. Her skirt was ultra short, displaying about 30 inches of leg. Her thighs were at eye level and so close I could kiss them. Adoringly, I gazed up and down the length of her legs, from the tops of her stocking welts and along the prominent muscles in her thighs and calves, beautifully accentuated by the sky-high heels. The delicate arch in her foot was so pronounced, I could actually see a bit of the bottom of her nylon sole in the shoe.
Still on my knees, I took a chance and slid my hand along the full length of her leg, from her hemline to her ankle.
My boner was in full erection mode. My mouth was dry. My heart was pounding. This was the sexiest moment of my life.
I put my hands on the sides of her knees and drew my face to her nylon legs.
“Stop! You’re not ready for that.”
“Diana, please. I can’t stand it. Your legs are the sexiest things in the world. Please.”
She sat in the chair and crossed her legs. She pushed the pointed toe of the upper shoe into the underside of my chin.
“You want to worship my legs? Then earn it by kissing my foot. Come on, get that shoe off and show me how much you adore my feet.”
I’d never thought about feet as a sex object, but I was willing to try it. I pulled off the shoe and carefully set it aside. I began to kiss the top of her foot. The nylon was glassy smooth and fine. Diana flexed her toes a couple of times so I decided to kiss them gently. I didn’t really know what she wanted.
“Come on, kiss them. Make love to my feet Teddy. Here.”
She put the ends of her toes on my mouth and wiggled them up and down. I opened my mouth and she slipped her toes right inside. I put my tongue on the underside of her toes and she began to flex them. I closed my mouth and began to suck and lick all her little digits. Diana responded by spreading them apart and so I pushed my tongue against the nylon, trying to push it between her toes.
“Love my feet Teddy. Love them. Here, here’s the other one.”
Diana slipped off her other shoe and put those toes on my face. Then she began to wiggle and flex them inside my mouth and around my cheeks and eyes.
She sat back and cooed.
“Ohhh, that’s so nice. My feet and toes are soooo sensitive. That’s it, just like that. Mmmmm, yes, lick them, lick them all over. Nice and wet. Oh. Oh yes.”
She started to squirm a bit.
“Lie down, Teddy. Come on, put your head on the floor between my feet.”
I did so. Diana shifted the chair so she could put the full weight of her legs on my face. I grabbed her feet and rubbed them all over my cheeks and eyes and mouth. I licked her toes; I lavished the undersides of her beautiful feet with my tongue. She responded with satisfied little oooo’s and ahhhh’s while she slid her feet all around my face.
She wanted more. She invaded my mouth with all of her toes and wiggled them deeper and deeper. I sucked and licked and kissed them. She pulled one out and wiggled her toes into one of my eyes, while I sucked on the other one. I was her slave, to lavish her feet with everything she wanted.
Oh yeah that was sexy. I never knew. Her toes had gone straight to my cock.
I was ready to explode there and then.
“Massage them Teddy. My calves too. They’re sore me being on my feet all day. Rub them, nice and firm. Careful not to ruin my lovely French stockings, or there will be consequences.”
This was getting good. I sat on the floor in front of her and caressed and rubbed her legs all around while she did her best to get all ten toes back into my eager mouth. I was in absolute heaven.
“Oooo Teddy, that’s so nice. You’re really getting it. Come on, are you up for it? Want to have some real fun. Let’s try everything. I haven’t worn every pair of stockings yet, and you’ve still got four brands you haven’t tried.”
For the next hour, Diana and I modeled our stockings, pantyhose, and stay ups for each other. She arranged the order, and they got progressively finer and silkier as we went.
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