Simon and Samantha

Here they are, I thought to myself as I grabbed a pack of Falke Shelina tan tights for women, I smiled to myself as I read the description, it should say tights for women and crossdressers. The supermarket was quiet as I popped the nylons into my basket and headed for the checkout. I couldn't wait to get home and enjoy every second of sliding the sexy material over my feet, up my legs, over my bum and gaze at my reflection in the full length mirror. The thought of it made my cock twitch in my trousers.

I'm Simon, I'm nineteen years old and love wearing tights and stockings and although I've had a few girlfriends, I'm a virgin.

I headed to the self service tills and had a quick look around to see if I would be recognised, nope, all quiet. The best thing about the automated tills is that no one took much notice of me as I purchased tights and stockings. Whereas in the staff-operated checkouts I would always think they knew my secret and my face would turn red as I paid for and bagged my new nylons. Nope, all good these days I thought as I scanned the barcode. BEEP! "Item not recognised, an assistant is on the way," sounded the till. Fuck and bollocks. My heart pounded as I waited, I flipped my debit card with my fingers, shuffled my feet and had another glance around to see if anyone was looking at me.

"Sorry for the wait," said the shop assistant, a nice looking girl in her early twenties as she tapped in her code number and re-scanned the tights. "Shelina," she commented as she looked at the pack, "expensive, but worth every penny, are they for you?"

"No," my voice was raised slightly as I felt my face turning bright red. I swept my card feverishly over the payment machine and it bleeped as the payment was accepted, "they're for, for my mum."

"Of course they are," she gave me a little wink as she put the tights on the packing area, "Falke are my favourite tights, I love how they make my legs look and feel, I'm wearing a pair now."

I gulped, "I, umm." I couldn't speak. "I, they're no mine, I mean not, not for me." In utter embarrassment I left the tights on the till and almost ran to the exit. This was too much, I'd been caught, it'd be all over social media, I'd be a laughing stock. My heart pounded as I whizzed through the shopping centre in total confusion, shops blurred into one another as if I had just robbed a bank and was being chased by the police.

Eventually, my heart slowed down allowing me to focus and I noticed a coffee shop, I let out a loud sigh, I needed a caffeine fix and slumped into a chair outside the shop.

"Can I take your order?" asked a guy wearing a barista's apron. He offered me a menu.

"Just a cappuccino please," I replied, "large." The guy nodded and walked off. I closed my eyes and thought how stupidly I behaved when I got embarrassed, worse I'd left my tights behind at the store. That girl must be having a real laugh at me right now telling all her work colleagues about me and...

"You left these behind." The girl from the supermarket placed my tights on the table and smiled, "Are you going to thank me?"

I felt my face going red again, "Um."

"I'll take that as a thanks and an invite to sit down and join you shall I?" She pulled out a chair, adjusted her skirt as she sat down and crossed her legs exposing a nylon covered thigh. She caught me looking at her legs, "Falke Shelina, beige," the girl said with the merest hint of a smirk. I was about to make another sharp exit when the waiter plonked my cappuccino on the table, "Can I have the same as him please?" asked the girl. The waiter nodded and headed to the counter.

"Still not going to say thank you?"

"Yeah, uh thanks," I managed to blurt out. "Thank you, uh, miss."

"My name is Samantha. And you are?"

"I'm Simon and I'm really embarrassed right now and I know I'm red and I know what you think and I'm sorry for, sorry for running out of the," my heart was racing and the tempo of my speech was joining it for the ride. The waiter placed Samantha's cappuccino on the table, Samantha thanked him and reached over to take my hand.

"It's me who should be apologising, I shouldn't have teased you like that. I'm sorry," said Samantha with a most apologetic look in her eyes, "are they really for your mum?"

I felt a lump in my throat. Samantha had short blonde hair, a pretty face, a slim figure and was holding my hand, her eyes were looking into mine searching for the truth. My heart started to race again and my face was getting more ruddy by the second. "Won't you get into trouble for leaving work?" I tried to change the subject.

"I just finished my shift. I thought I'd grab your, sorry, your mum's tights and return them to you." She sipped her coffee and I did the same. 

I looked around, looked back at Samantha and sighed, "They are for mine, I mean me. Please don't tell anyone."

Samantha's eyes lit up as she squeezed my hand, "I won't tell a soul Simon," she looked as if she meant it, "they feel wonderful, don't they? Pull your jeans up a little bit." I did as I was told and pulled a trouser leg up. I heard a shoe hit the tiles as Samantha kicked off one of her flats and felt her nylon covered toes stroking my calf. "Nice?"

All I could manage was a muffled "Mmmm," as I enjoyed that incomparable feeling of sheer nylon on skin. I looked at Samantha, who was smiling and seemed to be unaffected that the tights, the ladies' tights, on the table were mine.

She slid her toes up my calf and used them to tickle the back of my knee, I gasped and Samantha giggled. She moved her foot to my thigh, "I'd love a foot massage."

In my haste to feel Samantha's foot, I spilled my coffee as I clumsily lowered my cup down to the table. We both burst into laughter as I used a napkin to mop it up, I suddenly felt at ease with the situation. My heart's pounding had reduced to a tolerable fluttering and I could feel the colour of my face returning back to normal.

After a quick glance around, I slid my hand under the table and cradled Samantha's silky soft, nylon encased foot. Samantha's eyes closed, her head dropped back and she sighed as I gently circled my fingers in the arch of her foot. "That is just lovely Simon," she breathed as I moved my other hand under the table to tickle her toes.

Samantha played with her hair, giggling softly as I caressed her foot. I wondered if her toenails were painted and if so, what colour. I had to have a look. I leaned back from the table for a moment and stole a glance at her foot, her nails were painted bright pink and her little toes looked good enough to suck. As I gazed at Samantha's small, beautiful foot I heard her voice again. "Like what you see?"

I nodded, "it's perfect."

"Would you like to see some more?"

"I'd love to."

"Then we should head somewhere quieter," Samantha said, "I have one request though."

I was ready for it, she could ask me to do anything right now, "What is it?"

Samantha held the Falke Shelinas in her hand, "I'd love it if you'd put these on before we go."

I froze. "What now? I uh, I'm not sure if, I don't think I could," I felt my face turning red again.

"Nothing would turn me on more than the thought of walking out of here holding your hand knowing you were wearing tights," Samantha whispered, wiggling her toes against my fingers.

"Uh, Ok. But where do I go to put them on?"

"In the restroom of course," said Samantha, I nodded and let her foot go. "Simon," her voice sounded urgent.

"Yeah," I replied.

"No socks or boxer shorts, just your legs in nylon," said Samantha with a smile as she teased a few strands of hair with her fingertips.

I nodded, took the tights from her and headed to the restroom. I felt like everyone was eyeing me and had a look around expecting stares and people sniggering at me, but no one was even looking, they were all wrapped in their world of smartphone-fuelled social media and I walked calmly through the cafe. The restroom was empty and I entered the cubicle, locked the door, opened the pack of tights and took out the flimsy 12 denier nylons. They glistened in the light and I felt my cock twitch, it knew what was coming and was heading out to enjoy the feeling of nylon encasement.

Aware that Samantha was waiting for me, I quickly took off my shoes, socks, jeans and boxer shorts. With my breath held, I rolled the nylons over my toes, up my legs and netted my semi-hard cock in the sheer panty, letting the waistband snap into place. I stopped for a few seconds enjoying the look of my legs, all the little blemishes were hidden, my knees looked smooth and the entire lower half of my body shimmered in its sexy nylon case. Would Samantha like me I wondered, or was she doing this for fun, would she take a pic and post it on social media. My heart suddenly sank, maybe this was all a prank, I felt my hard on subside and considered taking the tights off and sneaking home.

A knock on the door startled me, "Hey, are you going to be long?" An impatient voice accompanied the knocking. "Well?"

"Just, uuh, just finishing," I stammered and cursed inwardly as I realised my escape plan had been foiled. I quickly pulled on my jeans, slid my feet into my trainers, stuffed my socks and boxers into a trouser pocket and flushed the toilet. I kept my head down to avoid eye contact as I headed to the sink, where I quickly washed my hands. Once the new occupant of the cubicle had locked the door, I made my way back into the cafe.

As I headed outside, Samantha smiled and her eyes danced as I approached, "I've paid for the coffees, are you suitably dressed for some fun?"

I placed the empty Falke wrapper on the table and pulled my pocket open a little showing my boxers. Samantha's eyes widened and she grabbed my hand, "Let's go." Her excitement was obvious as she led us away from the cafe and to the exit, "We need to go somewhere quiet, you can choose."

"We can go to my place, my mum will be home but we'll have my bedroom to ourselves," I said feeling a bit inadequate at not being able to take Samantha back to a place of my own and wondered what she thought of me living with my mum.

"Ideal," Samantha said, "lead the way."

Still holding hands we left the shopping centre, made our way to the bus terminal and jumped on a coach for the ten minute ride to where I lived. I had no idea what to say or do sitting next to Samantha, although I'd had a few girlfriends, had done nothing more than kiss along with a few clumsy attempts at fondling breasts.

"Simon, give me your hand." I held out my right hand, Samantha grabbed it and slid it under her skirt. Her upper thigh was warm and silky smooth. "Mmmmm, nice," mumbled Samantha as she opened her legs a little, allowing me to explore her inner thighs. Lost in the depths of warm, nylon-covered flesh I hardly noticed that Samantha had grabbed my trouser zip and was pulling it down.

"Not here, people will see. Samantha, no." But I was too late, the nylon covered tip of my helmet was just visible through the zip opening and Samantha gasped as she saw it.

"That is just beautiful," she whispered as we both looked at it, my bright purple helmet was covered by a silky veil of nylon which was giving it a satin sheen, a tiny bead of clear pre cum oozed from my pee hole. After a quick glance to make sure no one was looking, Samantha used the tip of her middle finger to scoop it up and without hesitating put her finger into her mouth. Her eyes closed as she took in the flavour of my wetness. "Mmmmm, sweet and salty," she remarked as she rolled my juice around her mouth using her tongue, "I'm just as wet myself."

"Really?" I'd hardly finished the word when Samantha grabbed my arm.

"You are now going to feel how much I'm turned on by us both wearing tights," she whispered as she guided my fingers to her pussy.

"Oh, fuck," I mumbled as I detected a warm, wet patch of nylon. I could feel the outline of Samantha's pussy lips with my fingers through the moist material and more with luck than judgement found the bump of her clit. Samantha moaned, leaned forward and kissed me. I caught a taste of her cherry lip balm as she gently bit my bottom lip before sliding her tongue into my mouth. As we kissed I traced little circles on Samantha's warm labia, my fingertips now damp from Samantha's abundant pussy juice, her sexy aroma wafting into the air.

Samantha slid a hand inside my trouser opening and took hold of my cock, making me gasp out loud. She slowly wanked it through my tights, causing the thin nylon to stretch over my twitching helmet. Samantha dropped her head to kiss it, but was interrupted by the sudden hiss of pneumatic brakes indicating we were at our stop. I tutted out loud as Samantha sat upright and winked at me as she carefully packed my cock inside my jeans and did my zip back up.

"C'mon, let's go," Samantha said urgently. She grabbed my hand and led me off the coach.

"This way, it's only two minutes to mine," I said as we almost ran along the pavement. I could feel my hard cock straining against its nylon case as it acted like the point of a compass, guiding me in the direction of my house. "This one," I said as I led Samantha up the path and through the front door. I looked at Samantha and pressed a finger to my lips, she squeezed my hand and nodded. "Hi mum, I'm back," I said loudly, hoping my mum was watching TV in the lounge and would stay put. As I looked down the hallway, mum gave me a wave and turned back to the TV. "This way," I said, guiding Samantha up the stairs and into my bedroom where I closed the door. At last, privacy.

As I turned around, Samantha unbuttoned her skirt, lowered the zip and let her skirt fall to the floor. I felt my jaw drop as I stared at her, but before I could say or do anything she grabbed her T-shirt and pulled it up and over her head before tossing that on the floor too. Samantha was wearing a pink cotton bra and I reckoned her breasts were 34A, the outline of her tiny nipples were visible through the soft fabric. I looked down to see her sheer to waist tights encasing the lower half of her very petite body. I felt like I was in a trance.

"Your turn," Samantha giggled.

"Uh," I muttered, suddenly unable to string a sentence together.

"Your turn to take your clothes off Simon, I want to see your cock again, but your jeans are kind of in the way," said Samantha and I felt my face going red once more as I unbuttoned my jeans, lowered my zip and with a gulp, let them fall down to my knees. My cock, my ridiculously hard nylon covered cock, was now on full view to Samantha whose eyes were on stalks. Her obvious delight seeing me like this eased my self consciousness and I kicked my jeans off my feet. With my new found confidence I wrenched my T-shirt off my torso and threw it on the floor. I stood as good as naked in front of the prettiest girl I'd ever met.

Samantha slowly walked up to me, grabbed my hands and guided them around her back, pushing them down onto her small, soft buttocks. I let my palms cup each cheek and pulled her towards me, my cock squashed into her pubis mound causing her to sigh with pleasure.

Samantha wrapped her arms around me, grabbed the waistband of my tights and pulled me towards her. As we hugged, I felt Samantha lift her foot onto mine, her arch gliding over my toes and up my calf a little, I could feel my cock twitch and knew Samantha could feel it too.

"Can you unfasten my bra please?"

"Ok," I answered and fumbled with the clip for a few awkward seconds until it sprang apart. I returned my hands to her warm little butt.

"Thank you," said Samantha, hooking her thumbs under the bra's shoulder straps allowing it to slip down her chest. It fell to my cock with one of the cups landing on my helmet, Samantha giggled again, a soft, infectious giggle that I was finding a real turn on. The bra cup felt warm on my bell end and the straps were sandwiched between our thighs.

I looked down and stared at her breasts, they were small and pert with little pink nipples.

"You are beautiful," I whispered. Samantha smiled, put her hands back onto my bum cheeks and pulled me towards her. I felt those hard, hot nipples drilling into my ribcage, causing my cock to twitch again.

"Thank you," replied Samantha, "I think you look gorgeous too, sexy as fuck in your tights." and with that, Samantha's mouth found one of my nipples and started sucking it. My head fell back as I moaned loudly and I raised a hand to hold her head to my chest. I found a handful of her glossy hair and I gently teased it through my fingers, tugging at it softly.

After a few minutes of Samantha kissing and gently biting my nipples, I whispered, "Your turn now," as I placed my hands under her thighs and lifted her up. Her breasts were level with my face and I could feel her damp gusset on my bare stomach. She instinctively wrapped her legs around my waist and I lowered her a little so my helmet was poking into her ass crack. We smiled at each other before Samantha grabbed my head and pulled my mouth towards her breasts.

I latched onto a nipple and sucked, making Samantha squeal. She grabbed the hair on the back of my head and pulled me into her, while digging her heels into my buttocks and grinding her wet crotch onto my stomach. I swapped to her other nipple, sucking its firmness while feeling Samantha's nylon-encased thighs gripping my waist.

"Let's get onto the bed," Samantha said urgently. I reluctantly lowered her to the floor, I was enjoying holding her against me, her small frame was easy to carry and I was loving the feeling of my cock pressing into her slinky ass crack. I slowly lowered Samantha down, enjoying the sensation of our tights sliding together as her feet reached the floor.

"Sit down just here," she said, gesturing to the edge of the bed. I did as I was told and allowed her to pry my legs apart with her hands before kneeling in between them. With her head level with my cock she smiled at me before leaning forward and kissing my throbbing helmet. My cock was rigid, as solid as it ever had been in my life, twitching in time with my pounding heart which was trying to hammer its way out of my chest.

With her hands around my hips Samantha flicked my helmet with her tongue, another drop of precum leaked from my slit, soaking into the taut nylon shrouding my bell end and creating a large damp stain. Samantha looked at me, licked her lips and dropped her mouth onto my helmet, swirling her tongue wildly over the soiled nylon, savouring my tangy juice, the whole experience was something I'd only dreamed about. Samantha sucked my helmet noisily while dragging her fingers up and down my thighs, her nails snagging on my tights as she took more and more of my cock into her mouth.

I felt my balls tense up and knew what was about to happen, "Samantha, I'm, uh, I'm going to cum."

Samantha stopped, "Not yet you're not," she said, giving my cock one last flick with her tongue. She stood up, pushed me down on my back and crawled onto the bed. As she turned around she flipped a leg over me to face my feet and lowered herself onto my abdomen, letting her pussy smother my cock. 

Her warm, wet gusset chaffed my shaft and I felt her little tits sliding up and down my legs. Samantha moaned as her nipples slid along the nylon and said, "Tickle my feet Simon." Only then did I notice her feet were either side of my waist, I wrapped my hands around them and used my thumbs to massage the soles of her feet. Samantha moaned again and wiggled her toes, "That is just lovely. Are you enjoying the view?" I looked up from her feet and stared at Samantha's little butt cheeks. They quivered slightly as she moved her gusset back and forth on my cock, the nylon sheen glistening in the light. The faintest swish of our tights was just audible as she glided over my body, her butt hole and pussy obscured by nylon.