Try on the Pantyhose

By S M

Published on Apr 21, 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

Apologies for the last story being somewhat brief, I was rushed, and would probably rewrite it if it was possible....caught in the heat of the moment!

Part 4

Jeff had slipped out my window. Being in a bungalow, nobody really thought of someone sneaking in or out of my window but the fact that my neighbors garage was so close, someone literally just had to climb up there and walk to the edge. Being young, it was easy to climb and we all were pretty fearless, jumping up to my window wasn't that big a deal at all. That night after Jeff left my room, I didn't fall asleep for hours. My mind was like a snapshot playing the same movie over and over in my head of what we did. Part of me was worried I'd wake up and tell it was a dream.

The next morning I awoke and was still in my hose. That worry that it was a dream hit me but as I peeled off the hose, the dried cum sticking to my thigh reminded me that it was very true. Jeff and I had played around and it was no dream whatsoever.

Going downstairs my mom greeted me with her usual sunshine smile and was chippy as ever.

"Good morning sweetie" she said as she did her best June Cleaver routine.

"Hey mom" I replied as I stretched out and sat to have some cereal.

As she poured me some cheerios, she asked what she probably thought was an innocent question: "I hope you didn't have bad dreams, I could have sworn I heard some moans coming from your room. Everything okie sweetheart?"

Thankfully she wasn't looking at me, my eyes must have bugged out of my head at that comment. All I could muster was "I'm ok, I don't remember any bad dreams".

Shit, that was close! She had heard me and Jeff and wasn't really aware of what happened. Fuck, I couldn't do that again! This was way too dangerous and now I had been seen by someone with Leah and now my mom heard me and Jeff. Oh shit. Jeff. Are we gay? Is that what gay boys do? My mind was filled with all these thoughts as my young sexuality was being unleashed. Of course, with anything like this, my dick got hard so I'm sitting there trying to eat and play it cool but my dick has a mind of it's own of course. Thankfully, mom left before I slowly finished so I could get back upstairs and out of sight from her with my raging, youthful hardon.

The day was kind of typical for a summer vacation day. It really didn't matter what day of the week it was for me except weekends because my newspaper route. Weekends just meant getting up early and delivering papers. Weekdays meant papers went out in the afternoon. I ended up going with a few friends on our bikes to check out the train tracks and just be dumb setting up rocks and pennies for the trains to run over while we laughed from the bushes. We always thought we'd be shot by the guy in the caboose with a 'salt gun' which always seemed to be an urban legend.

The afternoon meant I'd be on my bike and by Leah's house for sure. I didn't mind it, but now I had things piling up. What would Leah want to do? What would Jeff want to do?? This was getting really crazy complicated and I didn't know exactly what was going to happen next.

Getting the papers going wasn't a big deal at all. I made it through the route and sure enough I saw Leah. Fortunately, no Jeff in sight.

Leah was with her sister in the front yard and I stopped and said my hello's. It was very very discreet. No big hug or scene for anyone to suspect we were anything other than friends. Dang, Leah was cool, she didn't become some sappy and clingy girl right away. As I went to leave, Leah got up and came over to me and flashed her smile. She told me that tomorrow her parents were going to take her sister to a summer camp for special needs kids and that she was going to stay behind and probably play at her friend Trisha's house. As she got quiet she said that maybe we could meet back at her house before lunch so she'd leave Trisha's and we could 'go to her room'?

I smiled and said that I could do that for sure.

The rest of the day was uneventful. Normal paper route duties and and such. Me and my friend Mike got together after dinner and played basketball until it started to turn dark. That night, I did wear some pantyhose in bed and thought about how much I liked Leah dressing me and getting me off. But also there was the very hot feeling of being sucked off in my very bed by Jeff, that was impossible to forget. I stroked to another young orgasm before bed and changed into my underwear and was asleep in no time.

The next morning was filled with some chores like yardwork and the time flew by quickly. It was almost 10:30 when I realized I'd probably be late to Leah's, I took a quick shower which mom thought was weird, I never took showers in the day. Then hustled over to Leah's. Being cautious, I took a different way, not wanting Jeff to see me, I came in the far side and hopped the fence. Knocking at the back door, I had to wait an extra minute as Leah came and looked at me like I was crazy.

"Why the back door?"

"I just didn't want people seeing me going into your house by myself, you know, keep it kind of quiet"

Leah smiled like I was crazy and said "Ok secret agent" and motioned me in.

We stood there for a moment as we both had silly smiles, my dick was so ready it already was getting hard. She leaned in and gave me a little kiss on the cheek. I was blushing and she said 'I have a new surprise, something I wanted to share'. Taking my hand we went upstairs to her room. When we went in, there was the outfit I had on before, pink skirt, black pantyhose laid out on the bed. I took a look, the window Jeff must have seen me through was at a bad angle to the bed, no way he could see it. As long as I stayed away from her desk and the very head of her bed, no way could he see us. From where I was, the best I could see was the edge of the house next door, just bricks.

"You want to?" she asked with her warm smile.

"Mmmhmmm" I replied and she stepped out of the room for me to change. That was funny, the privacy of it even though she had held my dick and sucked it, she was letting me change alone. In only a few moments, I was in the hose and skirt. Now that I knew how to zip it properly, it fit well and I could feel my heart pounding with anticipation. Leah entered and had a surprise, a pair of shiny black high heels. Now, mind you, we're not talking 5" stilettos, but they were high for that era - maybe 3". She looked nervous as she asked "maybe you'd try these on, you know they make legs look so attractive and I'd love to see if they look good on, well, you."

At this point, I didn't want to blow anything that would ruin my chances of more oral sex with Leah. I was hooked! A part of me inside screamed "High heels? Hell no!" but an ever louder voice said "Do it so she will suck your cock!!"

Guess which voice won?

She had me sit as she knelt and slid on each shoe. She called them pumps and I slipped each one on. They were her moms, she figured her mom had feet bigger than hers and mine seemed bigger too. It was lucky, they were almost a perfect fit. They felt weird tho, tighter on my feet than any shoe I'd had and Leah said I should stand and see how they are. Fuck I nearly killed myself standing up. The weight balance is totally off and I stood up almost as fast as I flopped back to the bed!

"Whoa!" I shouted and Leah giggled.

"Not so easy is it Steve?" she said smugly.

"Look, no fair, first time and it's not like you gave me much help Leah!" I propped back up and slowly stood, holding her hand as I steadied myself. At first I tried to stand all on my front foot but it hurt fast so I relaxed and settled back on the heel. Those things are dangerous! It's hard to find the balance, and I was a bit wobbly. Leah looked and asked me to turn which I did as if I was standing on eggs. She was smiling and said my legs look so sexy! This was really weird for me but oddly exciting being so foreign to me. She caressed my thigh and said I had 'killer legs' and giggled more.

Kindly, Leah told me I didn't have to stand unless I wanted to. I did try to take a step or two but wasn't bold enough to actually walk, I felt like I was on stilts!

I sat back on the edge of her bed and she leaned down and gave me a kiss, on the lips. Our lips touching and causing us both to breath hard. She slowly knelt between my legs, her fingers finding their way up and down my legs in hose once more. It was electric fire once more as my cock stood rigid in the skirt, which had semi-hiked up as I had sat down. Lewdly displaying myself as she nestled in.

She was so relaxed with my body and it was so good to feel her between my legs. She touched me from the heels all the way up my thighs, slowly exploring me and we both felt our bodies getting so hot together. My cock was aching as she finally touched me with her delicate fingers. Leah was growing bold and she leaned in and kissed my shaft through the hose and licked causing me to moan.

Her fingers slid up and pulled the waistband of the hose down. Her moms hose were larger than hers so the were not nearly as tight to my body but still held it well and gave me room to 'tent' them with my dick. Leah freed my cock from the hose, so firm it sprang out and her fingers slipped around it and I watched as her mouth opened to cover my cockhead and that hot feeling of her mouth covering me was back again. This was the first time she actually had me in her mouth without hose. I groaned softly, watching this vision of her sweet face, blonde hair and blue eyes going down on my firm young cock so well. She sucked on me, taking about half of my length in her mouth and slowly bobbing up and down on me as my whole body wanted to tense in pleasure from each special move she made. It was pure heaven.

After only what felt like just starting Leah stopped and said to me in a whisper "I have a surprise" and she said "close your eyes, cover them too, I'll be right back." There wasn't any conversation, she got up and left me. Sitting there with my cock standing up straight, a little glistening from her saliva. I closed my eyes and covered them.

In a moment I heard her feet shuffle in and could tell from the movement that she was close. Her body just between my legs and moving down to kneel. I did my best to keep from looking though I wanted to. Her fingers wrapped around my dick and I felt her lips kiss the head, a little slowly and then the sensation of her tongue taking some long licks came next. Oh it was good. I hadn't felt her lick up and around my dickhead like that before and it was so good I felt my legs tense uncontrollably. My moans started with these movements and I wanted to watch her, but the sense of only feeling her was sensual and maddening, totally addictive.

Next, I felt a different sensation, her lips kind of kissed my dickhead and slowly parted to let me in. Hot and wet and so good but this time I felt her teeth scrape my cock. Not just gently but a bit roughly which caused me to wince and my body contracted. I groaned the word "teeth" and she paused and pulled off...no words, she just started over and this time, no teeth until I reached her limit and she was about to gag a little. At that point I felt her teeth again and groaned again, the sensation of teeth there was so different and scary!

I looked, my eyes opened and could see through my fingers over my eyes. It wasn't Leah, a girl with chestnut hair....it was her friend Trisha! I moved my hands down and she was looking at my body and sucking me in and out of her mouth. Her eyes met mine and she froze, the most amazing word came from her mouth as she pulled off my cock: "sorry".

Sorry? Holy hell, she was sucking my dick, and apologizing! I looked at her and then at the doorway, where Leah was watching us. Her face surprised and pleased at the same time. She froze as I looked at her and then back at Trisha. To be fair, if Leah was cute, Trisha was pretty. She had curves like a woman but was still developing. I know she had breasts and her hips started to have curves. Her hair was longer and thicker than Leah's and I thought she was very pretty. Trisha was much more of my 'type' I suppose.

I watched as she held my hard cock next to her mouth and she had this smile that was incredible. Leah whispered to us both - 'don't stop' and that's all it took for Trisha to continue. Her mouth went back to my cock and she sucked me back in. I couldn't help it, my body was on fire for this girl and I sat up and took what I felt was a chance, I reached down and squeezed her tits, one in each hand. They felt soft but with a firmness. Her teeth scraped me as I did it and we both gasped. I could feel her breathing on my privates as she kept composure. I released one tit and put my hand on her head, just very gently, while the other felt her and could now touch a firm nipple inside the fabric.

We both groaned and I wasn't going to last long as she looked me in the eye, almost pleading for some kind of approval from me and I nearly fainted in pleasure. My eyes rolled back as my body became stiff, the visuals and feeling were too much, I had to cum and my cock began pulsing as the orgasm hit my body once more. I squeezed her between my legs and she seemed to freeze and I found my hips started to buck into her mouth, wanting to make sure she still continued to take me in and out. Cumming so hard I felt the spasms and gasped with each one until they stopped after the 5th or 6th 'blast'.

Slumping back on the bed, I released her from my leglock. I could feel her so tentative as she let me go from her mouth and she held my still hard dick as it began to soften. Moaning I felt her grip the base and touch my balls one last time. Then it was just me, in my pantyhose/skirt/heels heap on Leah's bed. Fresh from orgasm and spent.

I looked and watched her get up with a smile that was like she had stolen something. Her and Leah met at the doorway of her room and I could hear giggles and am sure I heard Trisha say something like "It got so big and then it started to just have this feeling over and over but nothing came out, wow".

As I caught my breath, I wondered what the hell happened and Leah came back in after a minute.

"Don't be mad, I told her about what happened and she was curious Steve. Girls don't know what boys can do and when I told her you don't have anything come out, she wanted to try, you know, without a mess"

Mad? I just had this really pretty girl in my class suck me off. I don't know how mad could come into that equation.

Next: Chapter 5


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