Friends Finally Connect

Everyone in this story is 18 or older and any resemblance to people real or fictional is coincidental.

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I am a slightly chubby band nerd and generally just a nerd with a life-long fetish for girls in pantyhose or thigh high stockings. I don't know why but I just love the way women look in them. My love life up to this point was basically non-existent. I had plenty of crushes but by the time I built up the courage to ask the girl out I had either missed my window or she was not interested in me.

Bailey was one of my best friends. I knew her since elementary school and we were both band nerds throughout high school and shared a loved of Disney movies. She was very thin, with small breasts and a small but not bad butt, and was a bit of a tomboy. I could confide in her and we had no problem making dirty jokes and wrestling around without making it weird between us, this is how we went from that to becoming each other's first lovers and significant others.

How it Happened

It was the spring semester of our senior year in high school. A small group of me and my friends were headed to high school state band competition. This meant we were in our uniforms: the guys in tuxes and the girls in long black dresses and black pantyhose. There was four of us in the car, Addy and Brian up front, they had a very temperamental off and on romance with constant friendship, and me and Bailey in the back seat.

I kept shooting glances and the small amount of Bailey's legs in pantyhose I could see. Her dress was restricting the view to her mid-calf down, but the black sheer nylon clung to her leg shaping it and making it look amazing to touch.

Bailey asked, "Are we still meeting for steaks before prom at your house Addy?"

"No, we are going to have my favorite cold chicken and grape salad that my dad makes." Bailey and I shared a look at this reply. I slid my cell phone out of my pocket and texted her:

Does that sound like good to you?

No. I was looking forward to steaks.

Me too 

"So Luke, who are you going to prom with" asked Addy.

I jumped slightly and quickly snapped my eyes away from Bailey. "What?"

"Who are you taking to prom?"

"Uhhh, I guess I was just planning on going stag."

"WHAT?!?! You have to have a date. It is our last big event in high school and you can't be the only one without a date."

I looked down and muttered "Well I don't know who to ask..."

"Hmmm, what about Hattie?"

"I mean we were friends but I haven't talked to her since she graduated last year."

"Hope? Everyone thinks you two are dating anyway."

"She has a date already, besides when I asked her out she said that she didn't want to ruin the friendship or some bullshit like that."

The car sunk into silence as everyone considered who else I could ask. My eyes returned to Bailey's pantyhose covered leg and my horny teenage mind teamed up with my semi-erect penis and seized control of my mouth and before I could overthink it I blurted "How about you Bailey? Will you be my date to the prom?"

She blinked at me in surprise but a smile took hold of her face. "Yes, I will. Otherwise I was just going to go with my gay friend but this makes more sense."

I couldn't believe it. My stomach fluttered with butterflies and a slight amount sweat broke out on my back. "Sweet!"

I couldn't keep myself from smiling. My mind couldn't stay on a conversation, I kept staring at her revaluating our relationship and letting her legs take my mind on an adventure. My phone buzzed. I tore my eyes from her to glance at my phone.

Why do you keep looking at my legs?

My blood froze in my veins, the amount of sweat on my back felt even colder and my mouth went dry. My eyes flicked up and met Bailey's. I decided to just tell her the truth, she was my best friend and I didn't keep secrets from her.

I have this thing where I'm really into girls in pantyhose or thigh high stockings. I don't know why but I always have, even in elementary school I would sit next to girls who wore tights. I can't help but stare no matter what, I've tried.

I waited nervously for her to receive the text. She looked at her phone and then glanced down to her legs then began texting a reply.

Thigh high stockings?

Basically they add the same look as pantyhose but leave access to the good parts.

She got the reply and laughed. Brian asked "What?"

"Nothing" said Bailey. She smiled at me and crossed one leg to rest that ankle on her other knee, sliding her dress backwards revealing her pantyhose clad leg from slightly above the knee essentially doubling the amount I could see. I stared wide eyed. The cheap band uniform tux pants did nothing to hide my full-on erection and her eyes flick down and her smiled widened.

I didn't notice due to my distraction but her eyes now rested on the bulge at my crotch the same amount my eyes spent on her legs the rest of the car ride.

The Night After Prom

Prom was great. All the girls dressed up so prettily it was very fantasy fulfilling, some even wore pantyhose though I could not see if Bailey was because she had a floor length blue ball gown. After the prom, our group went back to her house and switched into pajamas, a t shirt and athletic shorts for me and her in pajama pants and a cami. I don't remember what anyone else had on.

We played some games and watched Disney movies on a fold out couch and piles of cushions and pillows until everyone fell asleep. I was next to Bailey unable to sleep so I decided to cuddle up closer to her. She moved in her sleep and I froze but she just rolled over to her side and scooted back into me so that we were spooning. I couldn't believe what I assumed to be my good luck and pressed myself up against her. My erection began to grow but I decided to roll the dice and did not back up but pressed myself against her butt. I slide my arm over her and gently rubbed her hand. That's when I got the surprise of my life.

SHE WAS AWAKE!

She took hold of my hand and squeezed it and rubbed her stomach and lower chest while grinding her butt into me. Unsure of what to do but following instincts I moved opposite of her grind so that I was thrusting harder against her. My erect penis pushing out against my shorts and pressing against her butt crack.

She released my hand and reached back and held my thigh so that I was pressed up hard against her and I slide my now free hand to cup her small breasts. They were firm yet soft and felt so nice that my cock pulsed in excitement. Fearing that was a sign of premature ejaculation I pulled back slightly but that only providing her the chance to roll over to face me.

Now face to face, both of us breathing fast but quietly, I whispered "Is this ok?"

She nodded and moved in and we began to kiss. It was my first and greatest kiss. Her lips were extremely soft yet pressed and moved with a slight urgent passion that invite me to reply in kind. I continued to explore her body with hand but staying outside of her clothing fearful of overstepping.

Apparently my kissing and touches were doing the right things to her because she put her hands in my hair and pulled me harder toward her while never stopping our kissing. I knew vaguely what French kissing was and that it was supposed to be next in our make out so I went for it and slide my tongue into her mouth and explored it. Her tongue instantly responded in kind and one of her hands slide under my shirt and ran up and down my back.

I moved my hand down to rub her thighs but still fearful to go too far. Then without breaking our kiss her hand ran down my back out of my shirt and back towards herself but moving in a way that had her hand brush against my erection until she grasped my hand moved in between her legs. I rubbed her slit through her pants terrified and excited at the same time. The flannel material was slightly rough and warm but I was not going to stop.

She moved her hand back in and took my hand and put in the waistband of her pants. Understanding somewhat what she wanted I moved hand down so that I was rubbing her vagina from only above her soft cotton panties, curly pubic hairs brushing against me where they stuck out from the panties. The fabric gave much more and I was very aware of the fact they were wet and my touching was pushing slightly inside her but she wanted more and pulled her waistband outward of both her pants and panties and I just went for it.

I slide my index and middle finger into her, first toward the front where I brushed her clit which made her squirm, then farther back where the slid in deeper. I was still focusing on this and the kissing hoping to not do anything wrong but by the renewed vigor and desperateness of her kissing and hoe she was grinding back on my hand I knew I must be doing it right so I kept going increasing the speed that my fingers slid up and down until she broke our kiss, grabbed my arm still and let out a soft moan while her vagina flexed and shuddered around my fingers.

She looked into my eyes and then down at our sleeping friends and moved away. Fearing I had done something wrong I sat up as she walked out of the room. I was confused and scared when she stepped back into the doorframe and gestured for me to follow. I instantly did and she lead me by the hand upstairs and into her bedroom. She closed the door behind us and I whispered, "I hope this is ok."

She walked to me and pushed me onto her bed with a long, powerful kiss. She pulled away, breaking the kiss which I had wanted to never end and said, "It's very ok, I can't believe it took you so long to finally make a move on me."

I laid there speechless and searched for a reply to lost any idea of that when she pulled her cami off over her head revealing her slim frame and a loose fitting pink bra. She then pushed down her flannel pajama pants to reveal rainbow panties with brown pubic hair poking out and to my utter amazement thigh high nude stockings!

I managed to choke out "You remembered..." then fading to silence as she smiled and said "Right after state, I went to the store and bought some just in the hope that they might make you act toward me. But my prom dress was so long I think you couldn't tell so I left them on afterwards just as a last hope."

"Wow" I stammered you're amazing. She laughed and said "You already knew that. You were just too scared to act until tonight" Any reply I could've attempted to form died on my lips because at that moment she leaned forward and pulled my pants and boxers down.

My erect penis leapt into view, a drip of precum glinting right at the tip. She did one thing I knew had even imagined this innocent tomboy would do and took me into her mouth. The feeling was incredible. Warm and wet with her tongue running around stimulating me would've caused to almost immediately cum if I hadn't had the break of coming upstairs to slightly calm my arousal. It probably only lasted 30 seconds at max but I would never know I was in so much bliss.

She let me go and rose and said, "Fuck me, please Luke" I whispered, "Are you sure??" "More than ever" she replied. I sat up and pulled my shirt over my head leaving myself naked as I stood, grabbed and kissed her fiercely. I finally broke the kiss and rotated us so she was now the one with her back to the bed and I gently pushed her down onto it. I stood between her legs and pulled her panties down and off making sure not to remove her stockings which I than began to rub my hands on.

The silky feel of the nylon with the soft flesh of a woman underneath was intoxicating, I continued rubbing but acting on a sudden impulse to return the favor I lowered myself and began to kiss and rub her pussy with my tongue. Her legs twitched in surprise but also pleasure and she wrapped her legs around my head keeping me there as my tongue flicked and caressed her clit.

I would've stayed there forever drinking those amazing juices and feeling the stockings against my skin but she released me and said, "Let's do it." I rose and noticed that she had removed her bra exposing her small pointed breasts, nipples hard with excitement. "Do you have a condom?" At first I panicked but realized that my wallet was in my shorts and I tore through it to find the single condom I owned and carried around like every young guy.

I struggled to open it but she sat forward and took it from me. She calmly tore open the package and unrolled it onto my still very hard penis providing one last bit of stimulation before I entered her. She lay back then and spread her legs as I stepped to the edge of the bed and with the help of a slightly shaking hand I guided myself inside her. She moaned slightly and so did I. The sensation was incredible. I thrust slowly and bent down and we resumed kissing as I rubbed her nipples between my fingers.

She looked so beautiful nude except for stockings and I was so aroused that I never broke the kissing or penetration. I moved in and out slightly accelerating but trying to remain slow so I could last long enough. No matter my level of excitement that layer of fear still existed in the back of my mind until it was washed away, by her wrapping her legs around me holding deeper inside of her and her trembling in waves of pleasure. The orgasm she was having and the stockings pressed tight against me was too much and I came as well, my penis flexing with each new blast of cum inside her and each time me thrusting a little deeper.

After I came I noticed my legs shaking from a level of tiredness I had not noticed before. I backed up sliding myself out of her but I leaned forward for another long passionate kiss. When the kiss broke, I said, "Wow that was amazing, imagine how much sooner that could've happened if I had been smart enough to know you were interested." She laughed quietly and replied with a smile "I guess we will just have to make up for lost time. Now let's sneak back downstairs and hope no one noticed." "I don't care if they do notice" I said, "I want to brag about my first girlfriend." She rolled her eyes and pushed me onto the bed but kept smiling.