Try on the Pantyhose

By S M

Published on Apr 7, 2012

Transgender

The following story contains graphic sexual scenes between a young man and young woman. If material of this nature offends you then you should not read this story.

Additionally, if you are under 18 years of age in most states you are not allowed to read this story by law. This story is purely a work of fiction. Any resemblance to person's living or dead, or to events that may have occurred, is purely coincidental.

Additionally, the actions of the characters in this story are in no way intended to show approval of, or give sanction to, their actions. The author claims all copyrights to this story and no duplication or publication of this story is allowed, except by the web sites to which it has been posted, without the consent of the author. Comments are always welcome and you may e-mail them to lacieman@yahoo.com

Try on the pantyhose

When looking back on growing up, there are some amazing moments and amazing people that come into our lives. We really don't understand or appreciate it until sometime much later. But these people shared something with us or introduced us to new experiences that help shape who we are.

This story is of a young woman who was my friend at that age when girls and boys cross that threshold from 'us versus them' to awkward youth and curiosity about new feelings, sensations and urges. Unspoken things like why our bodies felt a certain way or what is and isn't allowed.

Suddenly, breaking rules and, more importantly, keeping secrets seemed to be a bit easier to pull off.

For me, as a 7th grader, I was in my second year of middle school. At 13, girls were becoming attractive. Many of the girls who I had known for years Transformed from being friends to something more. Sure, seeing sexy adult women in a stolen Penthouse mag with my friends was exciting. But the girls my age didn't look like that at all, and my mind couldn't transform them in my fantasies just yet. Girls my age were still cute, but none were 'hot' if that makes sense.

With hormones beginning to brew inside me, my mind raced as my curiosity of sexual things started to grow. Talking with my friends, we would talk about the hot girls in the magazines and what it would be like if we could have sex. However, none of us had a clue what to do. We were all in pure bullshit mode.

A girl I had known growing up, Leah, was 12 and lived a few blocks from me. She had been a friend and we both seemed to get along well. Leah was a fair skinned blonde with blue eyes. At that age, girls and boys were still roughly the same height and size. I was a bit of a late bloomer, so she and i were very close in dimension. Looking back, she was my first girlfriend of sorts. But really she was the first girl I confided real secrets to. I just didn't realize how important it would be.

In the summer, i stayed home, like most of my friends. At that time, only one parent worked so mom would be around and every summer day was spent basically being gone with others until dinner. Seriously, in this day and age, kids wouldn't have any freedom like that. I used to see Leah while doing my paper route, she was about half way through my route. I'd see her and she'd get her bike and ride with me and we'd talk until I was done. Usually I finished at about 2 so there were several hours before dinner.

If I went to her house, her mom would greet me warmly and treat me like family. Being in her house was never a bad thing. At that time, I don't know if parents worried about kids fooling around, mine and hers sure didn't. Mostly I'd spend time at her house or block, but she did come to my house several times, it was just more common for me to be at hers mainly because she lived closer to my other friends in the neighborhood.

Anyway, a few incredible weeks happened that summer.

One day, as summer started, I was putting away my laundry and found a pair of my moms pantyhose in the leg of my jeans. At first, I didn't think anything of it. But as I held the sheer hose, I thought about those sexy women in the Penthouse mag my friend had. They all wore stockings and my curiosity was so strong. What would a woman's leg in those sheer stockings feel like?

As I thought about it, I quickly hatched a plan. Simply put them on, touch my own legs and get a sense of it on my own, no embarrassing first time with a girl, I would already know. Nobody was home, and I was in the upstairs in the only room in my family's bungalow. In a flash, I had stripped myself naked and pulled in this pair of pantyhose. Good lord it felt amazing! Like nothing I had ever felt before. It hugged my legs, my butt and my private areas so well, I was instantly turned on.

So, here I was discovering this new sensation and feeling an intense pleasure from it. My dick became rock hard instantly and it was impossible resisting touching myself. Rubbing my legs together, feeling them with my hands, rolling around on my bed, it was sexual dynamite. It was jaw dropping.

Needless to say, these hose became mine, I didn't want to give them back after what I had felt.

But this was a taboo. Normal boys didn't wear hose! Only girlie-boys would. Prissy or sissy boys. I kind of freaked out for a moment, I wasn't a sissy, not a prissy boy. We called girlie acting boys 'fags' but we didn't really understand what it fully meant, or what being gay really meant. I officially had a secret, one to be buried in the closet so to speak. Nobody could ever know, I would have to be closed lip about it.

So when it was night and about time for bed, I had my secret but kept it totally hidden. There must have been something in the air because about a week later, it grew.

I was with Leah on a Saturday morning. My paper route meant afternoons on the weekdays but mornings on Saturday and Sunday. She met up with me and when I finished we went to McDonalds for breakfast. It was a bit of a ride but we did it. Afterwards, we went to her house, her parents were there but they had to take her little sister to an appointment. Her sister has Down syndrome, which made it tough for them, maybe they trusted Leah because she had so much responsibility, she was more mature by circumstance.

It was mid morning and we were talking about what we'd be doing this summer, it was June so the whole summer was before us. We usually were in her family room when I was over but when her parents left, she asked me to see her room. Being naive, I went up to check her room out. Inside, it was the typical girl room, dolls, pink, flowery things and all that. She showed me her books and I was surprised to see so many books that I also had at home from growing up.

Leah was really a great guide, giving me a tour of her room. It was all very normal, like I had seen at my cousins house, reminded me of her room. On her dresser, she had her Sunday church clothes set out. A dress, shoes and pantyhose with panties. Leah got embarrassed when I saw her outfit and she scooped up her clothes and put them in her closet quickly. She explained that her mom always said that boys should never see a girls underwear and things. I told her it was ok, not like she was wearing them when I saw them.

She blushed deeply. When she blushed, it was impossible for her fair skin to hide it. She told me how she hated what her mom pulled out for her. Wearing pantyhose was a hassle, felt uncomfortable and made her feel warm and sweaty. The whole time, I'm thinking to myself how much I enjoyed the sensations, never thinking that someone would dislike it.

I tried to counter what she complained about. I told her guys thought legs in pantyhose were good. We didn't know why, we just thought women's legs looked good in them. She said if guys tried them, they'd hate them too. I laughed and tried to pretend that idea was insane, even though I already knew I loved it.

She stood next to me silent for a moment, wheels turning in her head.

"Wear them"

I frooze.

"W-what?"

"You heard me, you wear them and see what I mean"

She was stone serious. I was being dared to wear pantyhose by Leah!

"Come on, be serious, I can't do that."

She was determined, a kind of attitude I had never seen before.

"Prove me wrong Steve, put them on for five minutes and tell me you don't see what I am saying."

I was kind of caught. She went to her drawer and pulled out a pair of nude hose and said that since we are about the same height, I shouldn't ruin them, but I should fit. She stepped to the door of her room and said she would leave me alone to put them on, said I should put on the hose and then put my shorts on.

Before I could answer, she walked our saying: "get going"

Click. Door closed.

My heart was pounding. In my hand was a pair of Leah's nude hose. The perfume scent in her room enveloped me. I felt like I was in a dream, this was surreal. Was she serious? I had to choose, do it or not. Something inside me wanted to do this and convinced the butterflies that I could. Leah was right outside the door and told me how to put on the hose. How to gather them up and slide them on. Totally unaware I had done it a few times and had a good idea what to do. She wasn't going to get anyone and embarrass me, and this was before any kind of digital camera where I'd be on Facebook within seconds, thank god for the no tech 70's!

The flash of courage came and I did it. Took off my underwear and shorts and put on the hose. Carefully I put each foot in, pulled things up snug, then Made sure the waistband was pulled up. My cock, with a mind of its own, strained against the fabric as hard as it could. I was nervous she would open the door before I had my shorts back on!

As fast as possible, my shorts slid back on and Leah asked if I was done. With my heart beating out of my chest I responded and she entered the room with a huge smile on her face.

"Wow! You put them on! I thought you wouldn't!"

Feeling a bit played I responded "Oh thanks, you didn't want me to really do it!"

"Oh no, no! I am glad you did Steve, maybe now you'll know how much of a pain these are"

The entire time she is staring at my legs in hose, almost inspecting me. Without much hair on my legs at all, it wasn't easy to see, but being barefoot, she knew I was dressed in them right away.

"No snags or runs, nice job."

I smiled and said she would be dead meat if she told anyone I did this. Leah was actually very warm and honest, reassuring me she wouldn't tell a soul. After giving me the once over, the questions started, what did I think/how bad do they feel/did they feel too tight/could I imagine being in them all day? On and on. But what slowed her was my hardon, as it was contained in my shorts. However, every move I made let it reposition and become more and more obvious.

She was staring right at it. I began to realize what she was fixated on. My answers got slow,as my face turned beet red. Fuck, she was realizing my secret.

She stood next to me and had a stunned look on her lips. Finally, she said in a whisper "you ok?"

Nodding, I told her I couldn't help it and apologized. She had a focused look on her face, totally intense. "You are hard?"

"Y-yeah, I am, it just kind of happened Leah, don't be mad."

She wasn't mad, she was studying my tenting shorts. In her room, me 13, her 12. My dick so hard and excited and she is almost drooling with interest.

She sat on her bed, and invited me to do the same. I stepped over and sat with her, my heart pounding so hard I swear I could hear each thump. Sitting on the frilly pink and whit comforter, my legs felt tingles as it touched me. I breathed deep as I settled on the bed. Leah was gazing at me and recording this in her mind.

"Steve, how does this feel?".

I told Leah that the hose were so different from anything I had worn. For a brief instant I wanted to tell her this wasn't my first time wearing hose but held that back. I didn't need to freak her out at this point. What I did say was that it felt surprisingly good and that I didn't expect it to have this effect on me.

Now, Leah comes from a pretty religious family. I was really worried she would freak out and tell me to leave and let everyone know I was a pervert, but she was very understanding, a true friend.

Within a few minutes we were discussing me wearing hose as if it was totally normal. Almost like everything was natural. My hardon didn't care though, it was as rock hard as ever.

Then, she reached and caressed my leg gently. Causing me to jump and gasp in surprise and pleasure. It didnt stop her, only made her giggle. The feeling was pure erotic electricity. Her soft fingers started at my thigh and went to my knee. Gently she did this and smiled as our eyes met. I froze to a degree wanting her to continue doing that. My mind felt like any words may make her stop and that would be a disaster. She read my thoughts and continued to gently caress my leg in hose for what felt like an hour but was probably 30 seconds. A gasp escaped as she went up my thigh, no one had ever touched me like that ever.

Here is my friend Leah, caressing my leg in pantyhose in her room. If anyone knew, we would both be dead meat. My eyes closed as she did this and my breathing got deep with the touches. I opened my eyes and turned my head to her to see her face, still so focused on my legs, she was almost acting like I wasn't there, just my legs and hardon.

She whispered, not really asking, more like she was verbalizing her intent.

"I want to feel it"

Her hand moved up and the shorts of the day were short and a bit snug but she slid her hand right up, instantly cupping over my shaft and gripping it. Simultaneously, I gasped in pleasure and she gasped in shocking delight. My eyes opened to see her mouth wide open with a smile of amazement. Her fingers held me firmly without being rough. I groaned and my eyes winced in the intense shock of pleasure.

Leah looked like someone who had just won the lottery. Her hand gripping me and feeling me throb. She probably didn't know at all what to do. Hell, neither did I but I didn't complain. She whispered "does that feel good?"

I was nodding wildly and gritting my teeth, my teen hormones were ready to explode. Her hand was trapped in my shorts, holding my dick in the hose, giving me enough pressure for me to enjoy sexual pleasure. I couldn't see straight as she tried to massage me with her fingers and I exploded at her touch. It was a dry orgasm, but an orgasm for sure as my dick grew hard and then spasmed, wanting to shoot hot semen, I simply didn't have the actual ammo yet from mother nature.

Leah held tight, unsure what I had done. She was rubbing me and leaned in close as my cock spasmed several times. She asked if she was doing it right and when I could actually form a sentence, I gave her a shaking response of "oh yes".

My first handjob. Quite the experience. In Leah's room wearing her pantyhose.

I felt like it wasn't real even as she pulled her hand out of my shorts.

"You ok? Nothing came out and you are still hard Steve."

I groaned, having to explain my body felt so strange. I told her I didn't have anything come out yet and that I had been told by my friends older brother it would start to happen soon. He actually was making fun of us and said we were dry shooters and still children, ah youth.

Leah was so damn curious and asked so many questions until I had to ask if her parents were coming back soon or not. We both decided to straighten up and get downstairs, we didn't know when they would be back and being caught in this way was not an option.

Things between us seemed very different at that moment as I finally felt my dick soften. She was my friend but now she was something more I supposed. She leaned in and gave me a brief peck of a kiss. This was so different to me, was she my girlfriend? I went home to have lunch and try to figure this out, my secret about wearing pantyhose was known, in the best way possible.

Next: Chapter 2


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