Join the best erotica focused adult social network now
Login

One Wild Summer - Chapter One

"Shy young crossdresser gets caught which leads to the summer of a lifetime."

70
13 Comments 13
7.6k Views 7.6k
2.1k words 2.1k words

Author's Notes

"Coming of age story exploring hidden desires of being a closeted cross dresser."

I turned eighteen the year I graduated high school. I was going to college in the fall and I'd be on my own for the first time in my life, and it scared the hell outta me. I'm still kinda quiet but back then I was almost painfully shy. You know the type, not all that good at sports, nose in a book most of the time, total nerd, 6' tall and barely 155 pounds, not even remotely a chick magnet unless it was to repel them. Looking back it's probably why my mom sent me to live with an old friend of hers for the summer.

Fran was in her forties, Mexican, divorced and totally hot! Jet black hair with soft curls that fell in waves to the middle of her back and an hourglass figure. She was the star of a few of my fantasies and I wasn't sure how I was going to survive the summer living with her, let alone working in her used clothing store to earn a few bucks for school. I didn't even have a car so I had to take the train with as many clothes as I could stuff into a couple of suitcases.

I was a bit nervous getting off the train because she was a hugger and she really likes to pull you close. I spotted her as I was walking into the station and she already had her arms opened wide. I set my suitcases down and gave her a tentative embrace which made her say, "You call that a hug? Come here and give me a real hug."

With that, I was enveloped in her arms and she crushed me against her body and rocked me back and forth a little.

"Oh my God, how you've grown! I hardly recognized you. What's it been - three years since I've seen you?"

"Yeah, about that," I muttered in her ear still engulfed in her crushing embrace.

She finally let me go and we walked to her car. Asking about my mom, was I excited about college, and all kinds of small talk as we walked to her car and then drove to her place. And all the while I was trying to be as sly as I could sneaking glances at her legs and chest. But mostly I was looking out the window taking in my new surroundings.

It didn't take long to drive to her house and get myself settled into her spare bedroom. She showed me around and apologized for having to share a bathroom. I said it was no big deal until I saw her hosiery hanging to dry on the shower curtain rod and that secret urge welled up in me. The urge I spent so much time trying to ignore, and here it was staring at me in sheer glorious nylonic wonder.

I was jolted from my reverie by her asking if I would be ok by myself for a while.

"Sure," I said, "I'll be fine."

She told me she had a bunch of errands to run, I asked if she needed any help but she said it was fine and I should make myself at home and we'd have dinner when she got back. With that, she was out the door and I was alone. Just me, an empty house, and a bathroom full of sheer stockings and pantyhose.

I decided to distract myself in any way I could. Looked around for things to read, turned on the TV, rummaged in the fridge, but I kept going back to thinking about how glorious that hosiery would feel on my legs. My self-control was obliterated by my desires and with a tripping heart and trembling limbs I slunk into the bathroom and started to remove my pants and socks.

I had no idea how much time I would have so I set about my explorations, quickly picking a pair of tan stockings and carefully sliding them up my legs as I sat on the toilet. The sensations of the nylon and the taboo nature of what I was doing had the obvious effect on me and before I had the first one on I was fully erect. I quickly slid the other stocking on and admired how sexy my legs looked, rubbing them together to feel the wondrous swishing of nylon on nylon. Drunk with nylon lust I started to look for a hamper, maybe there were panties!

Not finding a hamper in the bathroom I became emboldened and nervously dashed through the house to Fran's room. My heart was pounding even harder as I opened the door and nearly jumped out of my skin when I spied myself in her full-length mirror. Forgetting about the panties for the moment I took in my reflection, turning to check out my legs and ass, stroking myself, watching my hand slide along my hard cock in the mirror.

I was so totally mesmerized I didn't hear the door open and Fran return home. I must have left the TV on a little too loud because I didn't know she was home until I heard her clearing her throat behind me. Oh shit! I turned around and tried to cover myself, but it was totally in vain. There she was, standing there with her hands on her hips, but she didn't look angry, or even disgusted.

"So this is what you do when I leave you alone for a few minutes?"

All I could do was stand there, blushing and silently dumbfounded, yet amazingly still hard as a rock.

"Go take those off, finish what you were doing, and then we need to have a little talk."

With that, she turned around and walked off to somewhere else in the house. I scurried back to the bathroom, amazed that I was still hard. Locking the door I quickly finished myself off, spurting into a wad of toilet paper and flushing it down. A wave of guilt started to wash over me as I carefully took off the stockings and put my clothes back on. Leaving the bathroom I went looking for Fran feeling ashamed of myself for what I had done and dreading our upcoming 'little talk.'

I found Fran in the kitchen pouring a glass of wine. there was an open pizza box in the middle of the table.

"Finished so soon?"

That stopped me in my tracks. "I thought I was in trouble," I said feeling a little perplexed.

Mireyasquirt
Online Now!
Lush Cams
Mireyasquirt

"In trouble for what honey, masturbating or wearing my stockings?" she said as she sipped her wine. "I thought you'd like some pizza so I picked it up on my way home."

I sat down slowly opposite her. "So, you're not mad at me?" I was still feeling like a bug under a magnifier.

"I admit I was surprised to find you in my bedroom doing what you were doing, especially after you just got here, and wearing my stockings no less. By the way, what were you doing in my bedroom? I mean, why did you go in there in the first place?"

I felt no reason to lie considering I was literally just caught with my pants down. "I was looking for a pair of panties and when I saw myself in the mirror I started to admire myself and well, you know the rest," I mumbled into the table, not really able to look at her.

I heard her get up and walk around to sit next to me, turning me to face her and lifting my chin. "You're not the only boy that ever got caught masturbating, you know? You'll survive the embarrassment."

I blushed at that, but my eyes went wide with shock at her next statement.

"You're not even the only boy that ever got into his mother's lingerie."

She looked at my surprised face, my mouth hanging open.

"Yeah, your mom warned me I might see a few things misplaced here and there, I never thought you'd get into them your first day here though."

"My mom knows!" I stammered out.

"Oh honey, moms always know," she said as she patted my knee. "So let me ask you a few things, you dating anyone?"

I huffed a little, "Nah, girls aren't interested in me, they all go for the jocks."

"So you do like girls, then?"

I suppose I should have been upset by that question, but I just answered, "Yeah, but they don't seem to like me."

"Oh honey, you'll have plenty of girls after you in no time, don't feel like you have to rush into things. Besides, from what I saw you'll make some girl very happy."

With that, she winked at me and I blushed again. Then she said she had something for me and went off to bring me a small paper bag. Confused I open it to find several packages of pantyhose and a few pairs of panties.

"Don't look so surprised," she said. "After your mom warned me I figured I'd just get you your own so you wouldn't have to sneak my things. I just didn't think I'd be giving them to you so soon. But we have to have a few rules. First, you do this in private, no parading around the house, ok? And no leaving messes when you masturbate, use tissue or something. And we can talk about anything you want, ask me questions about anything, ok?"

With that, she turned with her glass of wine and said, "Aren't you going to have any pizza?"

"Not feeling very hungry right now actually, think I'll just go to bed."

"Well, tomorrow is going to be a busy day at the store for you, better get some sleep." She gave me a little smile like she knew that I was up to something as I slunk off to the privacy of my room.

After ensconcing myself in my room I sat on the bed thinking back over my day. What was I thinking! Can't I control my lust for hosiery at all? Replaying everything that happened in my mind brought up so many questions. How long had my mom known about this? Would I ever be able to look her in the face again? Would I ever get comfortable around Fran? I mean I have to live and work with her all summer! Was I just some freak that would never have a girlfriend? Then I remembered Fran asking about being finished so soon, what did she mean by that?

The soft knock at the door brought me out of my mental tailspin. "Come in."

The door opened and Fran was standing there with the stockings that she caught me in. "Hope I wasn't interrupting anything. Here, I thought you might like these for a souvenir." With that, she kissed me on the cheek and told me to have fun.

She closed the door and I just stood there with her stockings in my hand, heart racing and feeling myself growing hard. I wasted no time getting undressed and slipping them back on, grabbing a pair of panties from my goody bag I got busy humping one of my pillows. I almost couldn't roll myself over fast enough when I felt myself starting to cum, spurting all over my belly. I lay there panting in the aftermath and could have sworn I heard the door creaking a little, but I was so lost in the lust of what I'd just done to know for certain or even care.

I lay there panting and wanting to scoop some of the cum off my tummy and bring it to my lips, but as usual, that urge was dying rapidly. So I just wiped myself off with the tissues I could have sworn weren't there when I got settled in I drifted off to sleep with dreams of Fran and her stockings.

I woke from a wet dream just as I spurted into my panties, which always happened to me for some reason. I took them off and decided I had enough nylon fun for one day. I slipped off the stockings and grabbed a pair of boxers to go get some of that pizza from the fridge as I was really hungry all of a sudden. Walking past Fran's bedroom I thought I heard her call out my name and it stopped me in my tracks. I listened carefully at her door and thought I heard soft moaning and then everything went silent.

Wondering if this day had all been a dream I decided that maybe I should just go back to bed and sleep it off.

Published 
Written by luvsnylons
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments