Justin was on his way home for summer vacation on an Amtrak commuter train from Philadelphia to Erie. He had just finished his sophomore year at his all-boy boarding school, and had decided that this summer, he would finally lose his virginity. Most of the other students had lost theirs already, many of them with students from the all-girl boarding school that shared grounds with the boys' school, and many with local girls that would sneak into the dormitories.

Justin was much too nervous about getting caught to ever attempt any kind of rendezvous, since it could jeopardize his good standing at the school and distract him from his studies. Besides, Justin didn't even know what kind of girl he liked. He was always staring at girls he saw in the city, but he just couldn't remember what kinds of girls he found himself staring at the most excitedly.

What he could remember was their clothes. The way the tops of their stockings would peek out from a skirt when they sat down and crossed their legs. The way their blouses would swish about as the walked briskly across the street. The sound of high heels knocking against a hard surface. Sometimes Justin would wander through the women's intimates department at Macy's, pretending to be lost or searching for a restroom, and would brush past the mannequins wearing silk and lace underthings. When the material touched his bare skin he shivered.

Occasionally he would get the nerve up to reach out and actually touch the fabric more deliberately, but only when he was sure no one could see him. The last time he did, he gave a satin teddy a gentle tug with two fingers just see it move against the mannequin the way it would on a person walking about a boudoir.

Justin was about five and a half feet tall and not growing very quickly. He had fair skin with freckles across his nose and on his shoulders. Obviously Irish to anyone who had to guess, Justin had light orange-blonde hair and pale, shimmering green eyes. His face held delicate features: a small button nose, a soft chin, and smooth cheeks that gave no sign of cheekbones. He had a long thin neck that ended at his ever-so-slightly oversized ears which also had freckles. Justin hated those freckles on his ears and had grown his hair out as long as he could get away with to cover them.

The result was a mane that would remind someone of the teen heartthrobs of the 1970's, nearly reaching the nape of his neck in the back. Justin was skinny, but not bony, and he had yet to grow any hair on his face or elsewhere. Yet another point of embarrassment at school. Justin didn't exercise more than the occasional walk around campus or through the city on the weekends, resulting in rounder, slightly more muscular hips and thighs, but the lack of any sort of regimen left his upper body lithe and soft. Not much fat, but certainly no muscle definition to speak of.

On the train, alone in a compartment meant to sit six people facing each other three on each side, Justin was stretched out on the bench reading a newspaper that the previous rider had left there. When he got to a full page advertisement for women's lingerie he began to examine the different styles of straps and various degrees of coverage. Lost in thought, Justin didn't hear the compartment door slide open. When it clicked shut, his attention shifted. A tall, beautiful woman stood over him. He peered over the top of the paper and drank her in.

She had short brunette hair, a slim figure, and shoulders slightly more broad than the average woman's. But it was what she was wearing that really caught Justin's attention. Bright red stiletto heels anchored her to the floor. Growing from their openings were a pair of perfectly sculpted legs coated in smoky black stockings that seemed to go on forever, or at least until the hem of her short pencil skirt.

The skirt had a black and white checker pattern that was slightly askew. It looked like a staircase that spiraled around her hips and ended somewhere beneath the overflow of the purple silk tucked-in blouse. The blouse was unbuttoned about half way down revealing the top edge of her black lace bra. The little black bow it held between her small breasts seemed to be teasing Justin. His gaze continued upward to her deep red lips flanked by large gold hoop earrings.

Justin quickly turned the paper to the comics section. "Uh, hi," he said cautiously.

"Hello" replied the woman in a voice that Justin thought was refined, but sincere. "You don't mind if we share do you?"

"Of course not, please, have a seat! I'm sorry, let me just move my things." Justin's duffel bag and a few bags of chips were laid out on the opposite bench. He hurriedly shuffled them to the floor and brushed off any dust that he imagined was there. She sat down, nearly pinning his hand to the seat. Justin's heart skipped when the back of his hand brushed the black nylon stocking covering her knee as he pulled it back. He could feel the familiar warm sensation that he had felt before in the department stores. It began in his chest and moved to his groin.

Justin's underwear grew tighter as his member slowly plumped up in his dark blue uniform slacks. He crossed his legs to hide the growing bulge.

"Sorry about that sweetie," said the woman, "you almost got stuck there, didn't you? My name's Elisabeth. What's yours?"

"Um, it's Justin. I'm Justin. Nice to meet you ma'am."

"Oh you don't have to call me ma'am. Elisabeth is fine. Besides, we have a long ride ahead of us. Plenty of time to get to know each other better."

The next few hours passed by uneventfully, except for when Elisabeth would shift her position or adjust her skirt. She had Justin's full attention the entire time of course and his erection hadn't diminished. In fact it had gotten bigger and harder than his cock had ever been. He caught himself staring at the light reflecting off of her blouse as its folds rippled and rolled with her every move. Justin kept his hands in his lap, carefully stroking the head of his dick with his thumb through his pants. He wondered if she caught him looking, and a part of him was hoping she would. Another hour went by and Justin fell asleep in his seat.
When he awoke, the first thing he saw was the sizable tent he was pitching in his pants. He had changed positions in his sleep and was now lying down on the bench with his head propped up on the arm rest, and his cock at full attention. Groggily, he looked to his right to see if Elisabeth was still there and was relieved to see she was not.

The relief was fleeting however when the armrest he was resting on moved. Justin turned and began to jump up in shock, but Elisabeth, now sharing his seat and serving as his pillow, placed one hand on his chest and the other on his cheek. "Shh, shh, shh, it's alright darlin', nothing to be scared of." Justin couldn't speak. He quickly covered his erection with his hands. "Oh don't worry about that, it's completely natural to wake up a little excited. You must have been having a pretty good dream."

"I-I-…I'm sorry" Justin stammered.

"Shush now child, just lie still, and let me take care of it for you." Elisabeth reached her hands down to Justin's belt and undid it. As she did, he remembered where he was, and as if she could read his mind, the woman reassured him. "Don't worry yourself, the curtain is drawn and the door is locked. It's just us in here." Her hand was around his cock, already stroking it up and down. His hand seemed to move by itself to her stockinged leg, caressing her calf and massaging the nylon. As he became aware of what his hand was doing, he gave into Elisabeth's advance and made up his mind in that instant to seize this opportunity and let go of his inhibitions.

Immediately, Justin wondered what kind of panties Elisabeth was wearing. Were the lace or silk, maybe cotton-no not cotton. Perhaps a thong, definitely not some full-coverage brief. He sat up and came to his knees to face the temptress. Kneeling on the bench, he stared at her legs while he slid his hand up the stocking and beneath the dress, wondering when he would find the top. Finally, he found the flesh of her hips. He reached further to her ass to find the answer to his question and was pleased to feel the lace trim of panties that were as delicate as tissue.

They felt as though they covered a little less than half of her supple derriere and the waistband was much lower than he expected. Justin could feel a wedge of lattice in the back that was tied into a bow. His heart began to race again. When he looked up at Elisabeth she was smiling wryly and reaching behind her to unzip the skirt. Her long slender legs scissored together as she kicked it to the other bench.

When she opened them again her half engorged penis pressed neatly over her smooth, hairless testicles and sat plainly in front of Justin, albeit through the sheer black cloth of her panties. He was visibly shocked, and his heart pounded faster. His bewilderment with this woman quickly changed to admiration and then, worship. Instantly he knew why he had so much trouble with women. He didn't want them, he wanted to be them. He wanted to wear the beautiful clothes and the sexy shoes. He wanted to be adorned in makeup and jewelry. This Elisabeth had shown him that it was possible, and he worshipped her for it.

He looked up to meet her gaze, and as if she gave a spoken command he knew exactly what she wanted him to do. Everything in his body was telling him to give in to it. His heart and his mind were in perfect unison. He reached down and caressed the crest of the bulging underwear with his palm. Then he turned his hand over to carefully palm the balls, squeezing gently to feel the material move between her skin and his.

He leaned in close then, and retraced his palm's path with his tongue, savoring the taste and the scent of the fabric. Elisabeth's cock was getting harder and the panties were beginning to pull away from her crotch. Justin reached in and with very little effort it came loose from the panties, the fleshy purse still nestled below. It felt like it belonged there in his hands as it arched between his thumb and index finger, and the end rested on his wrist. He moved his thumb back to the groove on the bottom of the cockhead and felt the precum. It slid up to the tip and over the curved top.

The lubrication looked delicious to Justin, and he once again extended his tongue. The cock slid easily upward, hitting the roof of his mouth, and he dropped his lips like curtains around the shaft. He bobbed his head, sucking and savoring every drop of the precum that looked so tasty, and replacing it with the moisture from his mouth as he went. His hand grabbed the root of Elisabeth's cock and jerked it up and down, bunching the skin up against his lips and then stretching it back out as his tongue swirled around the plump purple knob in his maw.

When her cock was hard enough, that is, harder than Justin ever could have imagined a cock could be, Elisabeth picked up his face in her hands and kissed him. She rolled her tongue into his mouth and he reciprocated. Both of their cocks ached, begging for stimulation.

She pushed him back and took off his pants completely, taking the boxer-briefs along with them. Her finger found its way into her mouth, and then into Justin. Then two fingers, and three. Still covered in slick saliva, Elisabeth's dick was easily inserted into his stretched hole. She pushed into him slowly though. Not because it was the boy's first time, but because she wanted him to feel every contour of her perfect cock as it speared his perfect asshole.

She fucked him on his back until she was tired of the position, then moved him to the floor where she instructed him to kneel and pressed his chest up against the glass window to fuck him some more. She pulled him back then and pushed his shoulders to the floor so that his little bubble butt was sticking almost straight up. His stiff cock swung back and forth, slapping against his stomach as her hips slapped against his ass. She pulled out of him and asked rhetorically, "Ready for your reward boy?"

"Yes ma'am," he replied. Justin flipped to his back and she brought her rod to his lips. He welcomed it back into his mouth, furiously sucking and stroking it.

"Here it comes," she warned him with a heavy exhalation and a gasp. His eyebrows shot up and he saw the satisfied look on her face. She pulled her pelvis back and withdrew from Justin's mouth as ropes of her cream launched into his throat. A long bolt of it lanced across his face in a spiral as she shook from the orgasm. He leaned back and was overcome with pleasure as he grabbed his own dick like it was a loose cobra and he was fighting it for his life. It spit its venom across the compartment, away from the coupling duo and against the wall.

Elisabeth looked back at the meager load as it slowly began to slide towards the floor. She looked back at Justin with disappointment on her face. She climbed off the freshly spackled lad and collected his jizz with her finger. Returning to the floor she lay down on top of him, cock rubbing against cock, and wiped the cum onto his lips. Elisabeth collected the remains of her own load from his face with her tongue. She kissed him again then, mixing their pearly sauce. Justin swallowed what he could and his partner took the rest down her throat.

Elisabeth stood up, deftly dressed herself, and walked to the compartment door leaving Justin in a stupor. She stopped, considering the boy on the floor whose life she had just changed, and took her panties off once more. Only then did she look back at her conquest as she tossed the underwear. They landed on his chest. "Keep them" she said, "I can tell you like them." With that, she departed.

Justin never saw Elisabeth again, but he always treasured the keepsake she left him. In fact he wore them all the way home.