Being a senior in high school was very hard on Jane. She didn’t have many friends and many of the girls in her school were just bitches. Considering the fact that she’d never really known her dad, she had a general mistrust for men in general and that was a big reason for her introverted behavior. She was incredibly smart and she dreamed of the day that she’d return to her high school rich beyond everyone’s wildest imaginations and then laugh at all the people that had been so horrible to her. For most of her years, she tried everything she could to not be noticed. So even though she had blossomed into an attractive young woman, she hid it. She wore baggy clothes, very little makeup and even though she had contacts, she usually hid her dazzling green eyes behind big glasses. There was only place that she felt good and that was when she was with her mentor, Mr. James. Every freshman was assigned a mentor and she had been lucky enough to get him. Over the years, they had enjoyed many a laugh and she’d shed many a tear on his shoulder from the harsh treatment of other students. During her junior year, she’d actually been cornered by some jocks and what started out as teasing became physical and she thought she was going to be groped or worse, but Mr. James showed up and saved her. From that moment on, her thoughts of him turned erotic. She wondered if he had any idea that she fell asleep every night dreaming about his cock. Her life was almost like two as away from school, she lived a very different life. She worked in an upscale department store where she dressed in some of the finest clothes while catering to rich women. She actually went by a different name, wore makeup and was almost completely unrecognizable from how she looked at school. One time a couple of girls from her own class came by and didn’t even recognize her. She took great pleasure in calling security on them and having them escorted out of the store as she told security that they looked like shoplifters.
While at work, she’d been hit on by so many affluent men and their sons that she’d lost count, but she had zero interest in any of them. Simply put, she wanted Mr. James to be her first and that was the only thing she would even consider. Unknown to any friend or even her own family, underneath her normally nondescript clothes, she wore the most incredible lingerie. Many times it was items rejected from the department store that she bought for a fraction of the normal cost, but usually it was vintage items. She loved the look and feel of the more glamorous styled lingerie and the silky nylon garments made her feel so sensuous and alive. Many days as she sat in class trying to ignore the teasing that she’d received earlier, she would rub her hand down her skirt feeling her silky half slip rubbing against the stockings and garter strap that no one else knew existed under her baggy long skirts. She’d lost count of how many nights one hand had teased her nipples through the silky bodice of a vintage slip as the other rubbed the silky fabric against her equally silky nylon panties. The teasing feeling on her pussy would slow grow as she rubbed the silky nylon garments together until she couldn’t stand it any longer and then she’d bury one and then two fingers in her tight pussy and silently hump her fingers until she came. The only face that ever graced her fantasies was Mr. James. He did so many lovely things to her in fantasies that some days she couldn’t look him in the face because of the things she’d imagined. As she readied herself for work, she thought of their last mentoring session. He’d scheduled it for her birthday and so she suspected he was going to surprise her. Sure enough he gave her a cupcake that was ridiculous looking with 18 candles jammed into it. She thought he was going to set off the fire sprinklers when he had them all lit. They giggled and shared a light hearted moment and then he handed her a card. He told her that she couldn’t open it until she got home or he’d be very angry.
She found that odd, but she tucked it in her book bag and then tucked her leg up underneath her as she peeled the wrapper off the cupcake. She offered him a bite and then at the last minute, she snatched it away and took a big bite. A big glob of chocolate frosting remained at the corner of her mouth and she tried to get it with her tongue. She noticed him watching her intently and then she finally reached up and gently wiped it up and then offered her finger to him. Their interactions had always been very casual yet friendly, so when he playfully took her finger in his mouth, she didn’t really think about it. However, as his mouth closed around her finger and slowly sucked the frosting off her firmer, she squirmed in silent pleasure. His soft lips made her heart race and she imagined his lips on her lips and then elsewhere. He seemed to sense the change in her mood and so he loosened his grip on her finger, so she could pull her hand away. As she slowly pulled her hand away still buzzing from the sensational feeling of him sucking on her finger, he gently grabbed her hand and said, “Oops, missed some.” He then slowly licked the length of her finger and she felt her pussy throb as she wished his tongue was licking her hot pussy. He smiled and seemed to have an extra twinkle in his eyes as he asked how she was spending her birthday. She rolled her eyes and said something usual, “You know, a date with Brad (the star quarterback) and then probably a night of dancing.” They both giggled, but her eyes turned sad at the realization as it was just going to be another night at home with her mom and little sisters.
He reached his hand out and patted her leg. Just the light touch thrilled her. She was wearing one of her traditional long baggy skirts and it was bunched above her knees from her tucking the one foot under herself. However, underneath was something else. She was wearing a dazzling emerald full slip that she had found made her green eyes literally dance when she’d looked in the mirror, but underneath the full slip, she was actually wearing a silky black half slip as well. She loved to pass the time in class by rubbing the layers together. He was saying something sweet about how he knew things would change for the better for her and sooner than later. She was gazing into his adorable hazel colored eyes and felt mesmerized. The hair on the back of her neck started to rise when she realized that his hand that had been resting on her thigh was actually ever so lightly caressing her thigh. His hand was casual in its light movements, but he was rubbing the two slips together and as they rubbed against her nylon stockings, it felt like little tiny static electricity shocks were going straight to her pussy. She closed her eyes and lightly said, “I know it will be better once I’m away from my miserable classmates, but I’ll miss you and graduation seems so far away.” They were seated on his small couch in his cramped office and she turned towards him and leaned back and sighed. What she didn’t realize was that when she’d turned her legs toward him, her skirt had been pulled higher and the emerald slip was on display.
She felt his hand moving and without opening her eyes she softly said, “That feels nice, please don’t stop.” Little did she know that he hadn’t intended to stop, he’d actually been moving his hand so he could rub directly on her slip. He’d always found Jane to be such a wonderful and beautiful girl. His moral standards had always made him resist any temptations, but ever since her 18th birthday, he couldn’t stop thinking about her. He’d caught glimpses of her glamorous lingerie before, but he’d always pushed it out of his mind, but now that she was sitting so close and with several inches of her slip showing, it seemed to be calling out to him, ‘touch me, touch me’. Since she’d essentially said the same thing, his cock was throbbing in his pants as his hand reached out and slid along the silky fabric. She sighed again and let one leg fall off the small couch. Her legs were now spread in a decidedly unladylike fashion, but her long skirt was still protecting her modesty. Having quite a fetish for silky lingerie, he was in heaven. As his hand moved higher, he immediately realized she had another slip on underneath and he found that to be sexy as hell. Her breathing was deep and a bit ragged and he softly pushed the emerald slip up until the lacy black one came into view. He rubbed the two slips against each other and slowly pushed them higher.
He had continued talking through all of this and wasn’t even sure what he’d said, but as she shifted on the couch to free up her skirt so he could move it higher on her legs, he whispered, “I don’t think that you’ll have to wait until after high school for things to get better; you’re certainly due for some good things to happen to you.” It was a fairly innocent comment, but the good thing he wanted to have happen to her was his cock buried in what he knew as a sweet little innocent pussy. In her mind, she was imagining that very same thing. Having her eyes closed made his light caresses feel even more magnified and her pussy was throbbing from need. She could feel that her skirt and slips were pushed nearly to mid-thigh and if he went much higher, he’d see her stocking tops and maybe even her matching emerald panties. They were soaked from her arousal and she wanted to pull his face down to her pussy and feel those soft lips against her. They had shared hugs in the past, but this time his touch was so deliciously erotic that she was giddy with anticipation. She didn’t want to speak as she thought it would break the spell, so as his hand dug a little more firmly into her inner thigh, she simply moaned slightly. He made some comment about her thighs feeling very tight like maybe she’d overdone it while running which he knew she enjoyed doing. In his best clinical sounding voice he commented that he’d rub both her thighs to see if that would loosen them up.
She nodded slightly to signal that sounded just fine with her and then he was shifting on the couch and he draped her closest leg over his thigh. He pulled her leg that had fallen open and off the couch up as well. She silently thought that wasn’t good as it would hinder his view, but then she felt him slowly push her skirt all the way to her waist. She stifled a gasp as she found this exhilarating and he prattled on about getting her pretty skirt out of the way. She could tell that one or both slips were still covering her stocking tops, and she groaned loudly when both his hands firmly massaged her thighs. His thumbs were on the inside of her mid-thighs and she mentally willed them to move higher. His massages through her slips felt sensuous, but she desperately wanted him to see her matching emerald panties. They had detailed lace running across the front and a tiny bow with a fake pearl right in the middle of the waistband. She could feel that the double nylon gusset was pulled tight against her pussy and she was sure he would be able to see the outlines of her pussy lips. She shifted again and moved the leg that he had had placed over his own thigh. As she did so, she let her plain flat shoe fall from her foot and without intending, she placed her foot between his thighs only inches from his bulging erection. He immediately moved his hands from her thighs and started massaging her foot that was in his lap. She realized suddenly that the hard thing under the sole of her foot was not his thigh bone, but it was his erection. As he massaged her toes through the silky stocking, she raised her other knee and felt her slips slowly fall towards her lap. She was wondering what he could see, but then she realized the slips got stuck at mid thigh. She figured they must have gotten hung up on the garter straps, so she stealthily used her hands to pull them past the straps until the silky slips were pooled in her lap.
She wasn’t sure if he could see her panties, but her garter straps were clearly on display and she waited for some reaction. Little did she know that although he was seductively massaging her foot, his gaze was riveted to the sexy sight at her waist. He was absolutely amazed at the sight of her shapely legs clad in the stockings and the garter straps added an extra degree of sexy. As he watched, she wriggled as he tickled the one foot and her slips finally moved out of the way and he was treated to the sight of her panties. He immediately noticed that she was wearing them over the garter belt which he knew was functional for her, but also seductive as he could simply peel them down her legs to get at her pussy. As she had suspected, the panties were pulled tight over her mound and he could clearly see every detail of her pussy. He also noticed with satisfaction that the panties were very wet and he wanted to desperately press his face against her and drink in her womanly scent. He gently placed her completely massaged foot right on his throbbing cock and started lightly rubbing one hamstring. He whispered something about it looking tight and then added that he hadn’t known she had developed into such a glamorous young woman. His compliment thrilled her and she wanted to show him exactly how much of a woman she was. One hand was kneading her hamstring while the other one held her inner thigh. She knew his fingers were mere inches from her pussy and she squirmed as her arousal spiked.
He quietly asked if he was hurting her and she quickly gasped, “Oh no, it feels terrific.” She knew from his erection that he was feeling quite aroused from this and wondered if he would take it further. He pressed hard into her hamstring again as he slid his other hand the necessary two inches so it grazed against her panties. The combination of the dig into her hamstring and the feathery touch against her pussy caused her to throw her hips up as if she was meeting the thrust of his cock and she delighted in the result of her pussy being pushed up more firmly against his hand. She really moaned this time and held her hips up for several seconds against his hand. He dug his hand even harder into her hamstring and turned his other hand to press his knuckles into her pussy as he pushed her hips down to the couch cushion. One of his knuckles knowingly found her hard clit and she bit her lower lip as it was the most exquisite sensation she’d ever experienced. She’d played with her clit hundreds of times, but he was doing something different and oh so much better. He softly said that he should probably stop and she grabbed his arm as her eyes pleaded with him not to stop. She softly said, “Please, don’t stop……not yet.” He looked unsure, but then she smiled softly and said, “It is my birthday; you sort of have to do what I say, right?” Not waiting for an answer, she laid back down and closed her eyes and waited.
She didn’t have to wait long and his hands were back; this time on her other leg. Now it was his right hand that was near her panties. Just as before, he kneaded her hamstring and this time he brazenly cupped her pussy as his thumb slowly caressed her clit through her silky panties. The last twenty minutes of his teasing touch had built up her to this point and she covered her mouth with her hands as she tried to stifle the resulting screams of pleasure. She humped his hand as his thumb lovingly caressed her clit. She wasn’t sure how many times she came, but she apparently passed out. When she opened her eyes a few minutes later, he was standing over her and smiling at her. She sat up and immediately noticed that her clothes were completely corrected. She looked at him quizzically and he softly said, “You fell asleep while I was massaging your foot, but you have class in five minutes so you better get going.” She thought that it couldn’t have been a dream as it had been so real, but he was acting like nothing had happened. She giggled and grabbed her book bag and thanked him again for the card. They had a brief hug and then she was rushing to class. As she sat in class later, her hands moved along her skirt to rub her slips together like usual. Something didn’t feel right and then she sat up so abruptly that her teacher gave her a look to see if she was alright. She realized that her black half slip was gone and she smiled as she imagined Mr. James sliding it down her legs and maybe even kissing her pussy through her panties. Little did she know that Mr. James had done exactly that after she had passed out from her multiple orgasms. As she thought about him, he was intoxicated by the sweet scent of her pussy that was imbedded in his nose as he slowly stroked his cock with her silky slip.