When Stephanie met Vanessa

My experiments with crossdressing and indulging my pantyhose fetish were becoming unsustainable if I was to continue raiding my mum's undergarments and dresses. I was begging to be caught that summer. On top of that, my parents had begun to badger me about my plans now that I had left high school. I graduated with a 3.0 gpa but just wasn't motivated. Beyond my circle of role playing game buddies, I had no friends. My latest girlfriend had already moved out of her parents and was getting ready to attend university. To say I was distracted was an understatement.

One morning over breakfast, my mum casually mentioned, "I was talking to your sister in law Vanessa on the phone last night. Your brother took a job on the North Slope and will be gone for 90 days. She said she has plenty of work for you keeping up that fixer upper they bought last year. I think it'd be good for you to head down there and take her up on the offer. Besides, I don't think she should be in that place all alone. What do you say?"

My brother was 12 years older than me. Most of my memories of him from growing up were of him fighting with my Dad about his music and long haired, "dead beat" friends. Truthfully, he seemed to me like a distant cousin more than an older brother. Even though we lived four hours north of them, we rarely saw each other. Vanessa, his wife was six years younger than him. They had been married for a little over a year. Aside from meeting her just prior to the wedding, I didn't know much about her. She was attractive and curvy, standing about 5'10" in heels. I knew she had worked as a blackjack dealer at a casino when my brother met her. Other than that, I didn't have a clue.

"Sure. I could use the money. Problem is, I don't have a car. How would I get there?" I was actually interested in escaping my current predicament. I was on a collision course to getting found out staying in this house with that silken temptation beckoning me from my mum's hosiery drawer and closet.

"I got you a train ticket. You head out tomorrow morning. Better get packing, hon." My Mom said breezily as she cleaned up the dishes from the kitchen table. Did it feel like I was getting the heave-ho? Sure, but any shiftless 19 year old with no ambition could see that coming with half a brain. I shuffled off to my room to shove some clothes into a backpack along with a shaving kit and toothbrush. I thought this could really be an opportunity to break away from the Stephanie persona I had discovered that summer. If I was truly going to move out and actually go to college, I just didn't see a way that could actually work. I was surprised I found myself sort of sad about the whole thing but I figured it was the best for everyone.

The four hour train ride south was uneventful and bumpy. I brought along a Walkman with a couple of albums on cassette - Bowie, The Clash, Devo. The stuff I enjoyed wasn't all that popular in the suburbs of the smallish city I was leaving. "Maybe they'll be some decent record stores and used book sellers down there," I thought to myself. It was the biggest City in the State, after all.

"STEPHEN!" The sound of my name being squealed reverberated all over the cavernous train station as I stepped off the train. Before I could see who uttered my name I heard the clack of heels on the marble floor. Out of the crowd she emerged. The first thing I noticed were her shapely legs in sheer, shimmering, tan pantyhose as she rushed toward me. My heart pole vaulted into my throat. I honestly was not expecting to be greeted like THIS. Vanessa looked like a wholly different person from cute, curvaceous hippie lady I had last seen. She had on a turquoise silk blouse tucked into a white, above the knee pencil skirt. The slit in the front revealed a lot of silken thigh as she approached.

"Vanessa?" I awkwardly asked as she wrapped me up in a perfumed hug. I didn't recognize you for a moment..."

"Van, sweetie. Call me Van," She answered sunnily as she took my hand and led me off towards the station exit and parking lot. "Did you finally get your license? You can drive my Camaro home. I'll give you directions. My God, it's been ages since I've seen you. You're all grown up now!"

We walked up to a weather beaten Camaro and Van tossed me the keys, "put your pack in the back seat and let's go. I'll navigate since we're on the edge of town." As I situated myself behind the wheel, I looked over as Van opened the passenger door and started to take off her strappy silver heels, "Ooh I've been aching to get these off!" As she did so, her skirt rode up and the slit widened. I caught a glimpse of her pantyhose gusset and a small strip of public hair underneath. I quickly turned away fully aware now I had a gold medal erection in my jeans. I sincerely thought for a moment I was dreaming.

It took a Herculean effort to not stare at her glossy pantyhose shimmering in the afternoon sun as I drove us back to the house. At one point she leaned back a bit and put her nylon feet on the dashboard, "so what don't you think, Stephen?" I nearly drove us off the road for a moment in shock.

"I uh, think they look nice, lovely even. I really like your toenail polish." Her toes underneath the sheer pantyhose were painted a deep shade of plum I have never seen before. I instantly wanted to paint my nails in the same shade so desperately.

"No silly, the Camaro!" Van laughed loudly. "You're Mom told me you bus it everywhere and rarely drive it ever." My face turned crimson at realizing my misunderstanding. I was at a loss for words. Here I am perving out on my sister in law's pantyhose and I haven't even been in town more than an hour.

"That's very lovely of you to say such sweet things about my feet and toes," she added, her tone softening. "A lady does put in the effort and you're a sweetheart for noticing."

We arrived at 50's era craftsman and after a quick tour of the place I was shown the room where I was to be staying. Modest, a bit outdated second hand decor. "We can make some improvements so it'll be more comfy," she said moving down the hall towards the kitchen. "Put your stuff anywhere and come catch up with me on the couch. Want wine? I'm going to have some! I can't believe you haven't said a single thing about my hair!"

"Oh, sorry," I stammered settling into the worn leather couch in the living room. "It looks great. I like that style - sort of a mix of Ziggy era Bowie and Markie Post." It was striking and a bit of a shock as the last time I saw her she had a Dorothy Hamill style wedge.

"I needed something different when I started working at Park Avenue Hosiery downtown. Retail. Fine tights, stockings, and pantyhose - many imported from Europe. Oh! You'll flip when I take you there. I can't wait for you to meet Jean, the owner. I know you'll both get on fine!"

I was glad she was busying herself with opening the wine and getting out glasses otherwise she would have witnessed what could only be described as me having a stroke. I could literally feel my jaw hit the coffee table hearing this information. My brother's wife whom I last remember being a cute and slightly spacey hippie chick was this leggy fashionista working in what could only be described as a pantyhose fetishist's El Dorado. I was also simultaneously looking nervously around the room in spasms of paranoia. I wondered if she knew about my fetish and experiments with dressing. Half of me wanted to bolt out the door and half of me wanted this to go on and on. I knew which half would win out.

I had only slightly regained my composure when Van padded out of the kitchen with two glasses of red wine and a lit joint in her mouth. Smoke tendrils wafted behind her as she sat down on the couch, handing me a wine glass in the process. She tucked her legs under her as she eased back into the leather upholstery. She took a long drag on the joint and offered it to me.

"Um, wow I confess I'm a bit of a lightweight when it comes to this kind of stuff but why not?" I took the joint and took a hesitant drag. "Good stuff, not like the dirt weed my gaming buddies pass around." I exhaled and took a long sip of the wine, allowing the alcohol burn to make my face blush. "So what kind of work will I be doing..."

"We can talk about that later, right now II want to catch up with you. So how long have you been wearing your Mom's pantyhose and clothes?" she coolly asked as her eyes narrowed."

At first it didn't register and it only hit me as I passed the joint back to her. I had the sensation that I was sinking into a black hole located directly under me. She knew. My mum knew. Cover blown. Maybe it was the pot or the wine but I simply looked up at the ceiling like I was watching my dignity leave Earth's orbit. "About a year ago. but I've had a thing about women's legs and pantyhose ever since I could remember. I guess... I guess it built from there."

Van stubbed out the joint in an ashtray on the coffee table, never taking her eyes on mine. She took a sip of wine, placed the glass on the coffee table and pulled me into a warm embrace. "It's okay sweetheart. She's your mom and worried about you. She's an old fashioned woman. You're an adult now and finding your own way. Here, right now you can just relax and just be who you are. I think you'll find me much more understanding. She then cupped my face in her hands and gave me a kiss on the mouth. Her creamy lipstick was ias intoxicating as the wine and reefer. Our lips lingered long enough to make my cock find its way out of the black hole of shame to erect attention.

As the kiss broke off she stood up and padded back to the kitchen saying she hoped I like spaghetti. I wiped traces of her lipstick off my lips and stared into the middle distance, struck dumb by it all. What the fuck have I gotten myself into? I puzzled. Again I was split in two with one half of me wanting to bolt out to door and into the deepest wood and the other half wanting this to go on and on. I already knew which half was going to win out.

During dinner and another bottle of wine I recounted the origin story of Stephanie in detail and in all honesty it felt good to share it at last. A couple of times during my "confession" Van reached out to grab my hand in what I took to be a gesture of support. "You're so brave opening up to me like this sweetheart. I'm so touched you feel comfortable enough to share your thoughts and feelings with me. It's been quite a long day. Why don't you take a nice long shower while I clean up here. Oh, there's fresh razors in the medicine cabinet in case Stephanie needs to shave her legs."

"Thanks Van. You're so wonderful" At this point in the evening I found myself letting my guard down enough to let my Stephanie persona out. I was buzzed and feeling good. I went to the bathroom and shaved myself smooth for the first time in months being careful not to leave any nicks or cuts. When I got out, I applied moisturizer to my legs and pubic area, now completely shaved. Returning to the guest bedroom I found four packages of Calvin Klein Daytime Sheer pantyhose in various shades with a note from Van that read, "Stephanie! I'm so glad you're here. These are for you to get you comfortable and settled in. I KNOW you'll enjoy. I'm off to bed. Get some rest. Love, Van." The signature was punctuated with a lipstick kiss print and I noticed the paper it was written on had been spritzed with perfume.

I carefully removed a pair from on of the packages marveling at the sheerness of the material. The waistband was a lot thicker than I had encountered before and there was no thick control top. "Sheer to Waist, Off Black, "I whispered to myself as I carefully slid them over my legs. The feeling on the pantyhose on the whole of my lower half was transformative. It was like I went from a black and white movie into color. I crossed and uncrossed my legs several times and climbed into bed. Things just felt right like. Within minutes, I feel into a deep sleep.

I don't know what time it was but I was awoken in the dark by the sensation of someone climbing into bed with me. I didn't startle, the night's revelry had made me groggy and slow to react. I recognized Van's perfume and presence next to me in the queen sized bed. I remained still unsure if I was dreaming or not. I felt her soft arm and leg drape over me and felt the whisper of her pantyhose on mine. As she spooned me I felt her lips give me the gentlest kiss on the nape of my neck. Her warmth and her perfume softly lulled me back into a beautiful slumber.

"Sweetheart Stephanie, wake up sleepy head. I made coffee. Come sit with me before I have to get ready for work." I opened my eyes and saw Van in the doorway of the bedroom dressed only in a black bra and off black sheer pantyhose. I instinctively looked away out of modesty only to hear her laugh as she padded away, "don't be a prude sweetheart! You've seen me in a bikini before. This is the same only my legs look prettier. I put a silk dress shirt on the bed. Put it on and come join me!"

I buttoned up the loose white silk shirt and admired myself in the mirror, glad to see the shirt tails were just long enough to cover my pantyhose clad cock. In the dinning room, Van sat at the table on her pantyhose and bra motioning for me to take a seat. I saw several pairs of Danskin tights and a black leotard hung over the dining room chairs and a couple stacks of Vogue and W magazines on the dining room table next to a steaming cup of much needed coffee.

"I picked these casuals out for you, Stephanie sweetheart," cooed Van as I took a seat. "I figured while I'm at work, you could have some real Stephanie Time - look through fashion mags for looks and tips on makeup. Now you can decide what YOU want Stephanie's style to be. When I get home from work we can have some serious Girl Time and start trying out some looks. Meantime, I thought you'd like to spend the day being girlie but comfortable," she said pointing to the tights and leotard.

"Wow, I don't know what to say Val. I love the dance tights and leotards. I can go for the Edie Segwick look." I replied in my best attempt at approximating Kathleen Turner's husky voice.

"Ooh! I LOVE your Stephanie voice and your hair looks just like Edie's already!" Van squealed. "You and I are going to have SO much fun together." She took a long sip of her coffee and sat down the cup leaving a crimson lipstick print on the edge. Noticing my eyes glued to the cup rim Van added, "I put out some makeup on my vanity for you." I can't wait to see my Stephanie sweetheart all made up!"

Van finished getting ready for work, looking just as fantastic as the previous day. She came out of her bedroom and tossed a couple of pairs of shoes on my bed, "looks like you're a woman's size 10, so you're in luck because that's my size. Here's a pair of ballet flats and some kitten heels for you. We'll get you better fitted for shoes and clothes tonight sweetie. Now I'll be home a bit after 4 pm. We're gonna have the best girlie evening! Ciao!" She blew a kiss as she walked to the car.

With Van off to work and the house to myself, I slipped on the kitten heels and walked into the master bedroom with a copy of W magazine. After a few minutes of lounging on the bed looking at the glamorous models in the photo shoots I got hard in the sheer to waist pantyhose. Linda Evangelista made me particularly horny. Her almond shaped eyes, long legs and that bright red pixie cut titillated and inspired me. I began touching my hard cock in the sheer to waist pantyhose. The sensation was electric, "where have you been all my life."

I moaned as a rocked my hips against to sheer fabric. When I came, I climaxed so hard a thick white rope of semen shot through the pantyhose and landed on my neck. The hot cum felt so good I actually cried out. "OH!" I exclaimed massaging the sticky cum into my chest. This was Stephanie running the show and Stephane was a highly sexual creature.

After my act of silken self love, I slipped out of the pantyhose and took a shower. Once I was all cleaned up and moisturized, I put on a pair of black opaque Danskjn tights and the leotard Van left out for me. To cap the Edie Segwick look, I went to my room and pulled my army surplus Breton striped shirt out and pulled it on. Now in the ballet flats Van had provided I really felt Stephanie was coming into her own. Boyishly cute in body con clothing I sat down at Van's vanity desk, I applied concealer, foundation powder, blush and mascara. I went more dramatic with the lipstick, applying cherry red shade. I put a bit of mousse in my short hair and tousled it to get a messy look. "Damn, I look cute," I whispered with newfound confidence.

I spritzed on some Revlon Charlie perfume and strode back into the kitchen. I cleaned up the cups and dishes, poured a second cup of coffee and looked out the sliding glass door to the deck overlooking the backyard. The hedges that surrounded the property were so overgrown it rendered the yard virtually invisible from the neighbors. "Perfect," I said to myself noticing a pair of red narrow vintage cat eye sunglasses on the counter next to a pack of Dunhill cigarettes and Bic lighter. I donned the sunglasses and stepped out onto the deck with my coffee, copy of Vogue, cigarettes and lighter. Stephanie was not only stepping out from the shadow of her mum's hosiery drawer and closet but literally out into the world.

I whiled away the hours in the sun, reading Vogue and smoking Dunhills now and then, fondly admiring my lipstick traces on the cigarettes. Bowie's Station to Station cassette was playing on the kitchen boom box. Girlie heaven. I was sitting on the chaise lounge with Dunhill in mouth when Van appeared at the open sliding glass door.

"You sexy bitch!" she exclaimed. The next few moments would remain hard coded into my mind for as long I will be able to think. Van took off her pumps and calmly walked over to me, gingerly took the cigarette from my lips, took a drag and exhaled as she sat down on the chaise lounge. She cupped my head in her hands and leaned in to deliver the most passionate kiss I had ever experienced. Our creamy lipstick felt amazing mingling with tobacco and coffee. Both our tongues danced as she cooed. Van tossed aside the magazine I was holding, took my hand and guided it up her skirt to her pantyhose gusset. "I couldn't wait to get home to see you. I got wet in the car thinking about you. Take me to bed right now sweet Stephane."

She got up and led me down the hall stopping at the doorway to my bedroom. She leaned in and pulled a package of Calvin Klein Daytime Sheer pantyhose off the bed handing it to me. "Strip. Put these on and come to my bedroom. I'll be waiting. My heart hammed in my chest sliding into the sheer off black pantyhose. My hard cock felt amazing in the sheer nylon. I padded down the hall in my stocking feet to find Val nude except for a pair of black sheer to waist pantyhose.

"Come to me, sweet girlie boy," she purred. "We keep the pantyhose on. I want to feel you" I crawled on to the bed and began kissing her again. "Suck my tongue like it's your first little girlie cock," she cooed. I complied, wrapping my lipstick lips around her little pink tongue. I reached down and began feeling her amazing pantyhose crotch. Van's pantyhose gusset was warm and wet. The sheer fabric conformed to her pussy lips as I began to massage her lovely cunt. I could feel her nylon leg gliding over my erection in the sheer pantyhose. That seductive hiss of nylon on nylon inspired me to bob my head slightly as I sucked her tongue.

"Ooh baby, yes." Van pulled me on top of her. Warm, soft breasts against my chest I could feel my pantyhose cock on her swollen vagina. The two layers of sheer nylon were slick with her juices and my precum. The sensation was like nothing I'd ever felt before. Lightheaded, I broke off her kiss and moaned in pleasure.

"Slow, baby. Let it build. God your cock is big. I love it, Van whispered. "I wanted you last night when I came to your bed. You didn't wake up but I masturbated in my pantyhose right next to you while you were sleeping. When your mum told me you were a pantyhose pervert I wanted you right then. Fuck my pantyhose girlie boy. I want to feel your hot cum on my nylon pussy.

There was no holding back anymore. So much blood had rushed to my gentiles my brain felt like it was on autopilot. I began to frantically edge her soaked pussy while moaning rhythmically. Van began to shriek as she wrapped her legs around me, thrusting back with animal passion. We were like a single nyloned entity spasming in ecstasy. At that moment, my cock erupted in the sheer pantyhose. My hot sperm on her cunt triggered her own orgasm. I could feel Van's fingernails dig into my back.

"OH FUCK! YOU BITCH WHORE I'M GONNA CUM! Van convulsed and screamed as she came. Waves of pleasure smashed over the both of us. Our pantyhose slick with my hot cum, I felt like I had been thrown over a waterfall. I rolled off Van and tried to catch my breath.

"God, that was hot," Van gasped while she gently massaged my cum into her pantyhose. "You're sleeping in here with me now girlie boy. I expect a repeat performance. Did you enjoy that bit of silky naughtiness?"

"I did and you are the naughtiest thing in nylon, aren't you?" I joined in with Van, massaging my cum and her pussy juice into my own pantyhose. "Stephanie appreciates a woman know knows about the power of pantyhose."

"That's why I want you to meet Jean," Val said turning on her side to face me. "Ever since I started working at Park Avenue Hosiery, Jean has been my guide into the fetish world. She's helped me to become the woman I was always meant to be just like I'm helping you. Now let's shower and get ready together for a special night with all three of us, okay?"

I nodded but as thrilled as I was to plunge headlong into fully embracing my Stephanie persona, I still felt a twinge of apprehension at sharing her with someone else besides Van. On the other hand though, admitting my pantyhose fetish and crossdressing to Van actually kicked of this girlie wild ride. "Let's do this Val, darling. Stephanie can't wait to meet this fabulous creature."