Trudy
Copyright© 2020 by Paris Waterman
Chapter 2
Coming of Age Sex Story: Chapter 2 - Trudy is a 14 1/2 yr-old experiencing her first sexual encounters with her brother, girlfriend and others as the story moves forward. Others like students, teachers, mothers and wives are included. Much sex.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft mt/Fa Fa/Fa ft/ft Fa/ft Teenagers Consensual Drunk/Drugged Reluctant BiSexual Fiction Cheating Incest Mother Son Brother Sister Spanking Group Sex Interracial White Male Oriental Female Hispanic Male Exhibitionism Masturbation Oral Sex Sex Toys Voyeurism Size
The Bissell Party
The Bissell party had been going well until Elaine Naismith put her hand on her husband’s leg under the dinner table at the Bissell’s house. She was surprised when moments later he gently pushed her hand off. She brushed off the encounter and continued talking and laughing with their friends. There were four couples at the dinner party; a group of old friends that got together a few times a year for good food and a late night of drinks. The Bissell’s while childless were hosting a young student from Lithuania who was considered an outstanding collegiate soccer prospect, named Uther Pendragon. Uther was a senior at the local high school and had just turned eighteen, who after making an appearance to meet the guests had withdrawn to his room where he was perusing porn on the Internet.
Elaine got along well with everyone and enjoyed the adult conversation but the encounter under the table left her feeling hurt and vulnerable. To help her take the edge off she drank a little more wine than she usually would over dinner.
After dessert it was time for coffee. Miles offered bring it out and Elaine decided to follow him into the kitchen under the pretext of helping, hoping to steal quick kiss.
“Elaine, what are you doing?”
“I just want a little kiss, that’s all.”
“Our friends are out there, this is not the time.”
“It’s never the right time with you anymore Miles!”
Pouting she swung her hips around flaring out her dress.
“Don’t you think I look good tonight?”
“Elaine, I think you might have had too much to drink. Maybe I should take you home so you can sleep it off.”
“Why don’t you loosen up a little and have some fun?”
“My idea of fun isn’t making out in front of our friends Elaine.”
“You know Miles; you can be a real jerk sometimes.
Elaine couldn’t let the second rejection by her husband pass without reacting, but not wanting to embarrass her husband and their friends, she proceeded to drink instead of venting her feelings. That of course led to her quietly becoming inebriated, and as fate would have it, she got sick in front of everyone.
To the surprise of the others, her husband Miles declined to take her home just then; saying he was looking forward to chatting with Richard Bissell about a forthcoming opening on the Board of Education. It was an ill conceived move on his part, revealing his poor judgment in not caring for his spouse and refusing to drive her home, claiming the walk (while relatively short) would do her good.
Rita Bissell called Uther from his room and gave him the keys to her car and instructed him to see Mrs. Naismith home and see to it that she was safely inside before returning.
Uther was non-plussed about the entire affair, having had to drive his own father home on several occasions when he lived in Lithuania. He was also pleased to see that Mrs. Naismith was a very good-looking woman; in fact bearing a resemblance to a MILF he’d been watching on Porn Hub minutes before being summoned to drive her home.
Elaine had short blonde hair and was about 5’6” tall with long lean legs. Her hips were wider than she liked, but gave her body a perfect hourglass figure. She wore a simple beige top that suited her smallish breasts along with a burgundy skirt that clung to her behind and had a slit that showed her ample legs to advantage.
Uther could tell that she would need some assistance getting to the car and managed to provide it without making it look as if she required it. She held his arm before getting into the car and threw up again, then after wiping her mouth with a tissue, she assured the teenager she was good to go and got into the car, revealing a glimpse of her white panties to him in the process.
“I ‘preciate this,” Elaine murmured gratefully. “That bastard husband of mine wouldn’t even gimmie a kiss ... and I asked him nicely.”
“He is a fool then, your husband,” Uther said with a slight accent.
“You’re nice looking. Do the girls all chase after you?”
He looked at her as he started the car, considering his reply before answering.
“You might say that. But I was told to be careful. Many girls want my babies. I cannot afford a wife yet. I have college to go to, and possibly a professional career. Although that is remote it is possible.”
“Mrs. Naismith, you need to put seatbelt on before we go anywhere.”
“Ohhh, you are special!” Elaine gushed and hugged him, “Every girl dreams of having a strong young man rescue her.” Then she closed her eyes and pretended to be sleeping.
Uther poked her arm and got no response. “Great” he thought “she passed out.”
She felt her thirty-five-year-old body quiver when Uther’s warm breath caressed her neck as he reached across her for the seatbelt. His right hand briefly rested on her thigh and his left arm brushed against her chest as he brought the belt across her lap to buckle her in. Elaine’s heart was racing.
The intimate warmth of man, albeit a teenager’s body against her, jump-started her memory and suddenly she felt long forgotten feelings flow through her from her freshman year at Vassar when she and Tom Bombadil had rocked his beat up Dodge on a dusty, moonlight road.
On the eight blocks ride to her home Elaine peered through half open slits in her eyes and thought that she saw Uther stealing glances at her legs. She was proud of her long legs and enjoyed showing them off. Years ago she wouldn’t wear anything but short dresses or skirts that barely covered her. Now she mostly wore pants or long dresses. The skirt she’d worn this night was the shortest one she owned and even that nearly came down to her knees; it was the slit that allowed her to reveal her legs.
Sensing an opportunity for a cheap thrill, like the good old days, she let her body slide down several inches on the seat and pushed her knees further apart.
Uther now had a formidable erection and a hard time keeping his eyes on the road. He slowly approached each intersection hoping that the light would turn red and allow him the chance for a better look. When the opportunity finally arrived he put the car in park and openly Elaine. Her skirt had inched up her legs and his eyes lingered on the soft curves of her inner thigh. Thoughts of the white panties that he knew were hidden underneath her dress played through his head.
His revelry was broken by the sound of a car honking behind him. He quickly snapped out of it and put the car in gear. The vehicle lurched forward as his foot stumbled on the accelerator.
Elaine felt a rush knowing that just a glimpse of her legs could distract the young man like that. She knew she had a great body, especially for her age, she had just forgotten how to use it to turn men on.
“But like riding a bicycle,” she thought, “you never really forget.”
On reaching the house Uther walked around the car knowing that needed help getting inside.
“Mrs. Naismith, you’re home” He said as he gently nudged her arm.
Elaine slowly shook her head from side to side pretending that she was just waking up.
“Huh, are we there?”
“Yes, you’re home, Mrs.”
“Ohhh, you’re the --- uh, the...”
“Uther, I stay with the Bissell’s.”
“Oh, yeah, my bad!” She laughed and touched his right thigh. “Um, I think I’m going to need some help, do you mind?” Her voice was noticeably slurred.
She held her arm up for him and swung her right leg out as far as she could. Uther stood frozen as her red panties came into view as the slit in her skirt strained against the pressure she brought to bear on it and parted much more than the skirt was designed to do. Elaine watched his face and pretended to struggle so that she could prolong the show but eventually kicked her other leg out and let the dazzled teen pull her up out of the car. Uther had to put his arm around her waist as they made their way up to the front door. Elaine accidently dropped her purse while looking for the house keys and bent at the waist while keeping her long legs straight. She knew that his eyes would be devouring her ass, which she thought her best asset sexually.
Uther did grow hard on seeing her derrière clearly outlined against the tightened material of her skirt and recalled the night two weeks prior when he’d had the pleasure of being the first one to enjoy Deirdre Ng’s fourteen-year-old ass, and the promise that her twin sister would let him have hers on their fifteenth birthday, the following month at her birthday party.
Once inside, Elaine began to lose her balance, but regained it before she could fall, and she tried to feign her way through the mishap by prying off right shoe. In the process providing Uther with a great view of her breasts as she leaned to do it as well as the other shoe.
Then Uther’s strong hands were around her—one on her left breast, the other on her right hip. “Whoa ... I kinda lost my balance there, didn’t I?”
Uther’s hands remained in place as he whispered into her ear, “It’s okay you are in good hands—like the TV commercial says.”
He didn’t want to let go and Mrs. Naismith didn’t seem like she was in any rush to get away from his young, athletic body.
After what felt like an eternity she slowly straightened up and his hands fell away from her body. He did relieve her of her purse and place the house key in it, and then made sure the front door was properly closed.
“Are you sure you are okay, Mrs. Naismith?” His cock was rock hard and he was already thinking that he would masturbate in the car before leaving her driveway.
Elaine’s voice rang through the living room to the front entry where he stood, about to take his leave. “Uther, can you come here for a minute. I think I need a little more help.”
“Sure,” he called out, and retraced his steps to find her sitting on a coffee table, legs spread, providing him with a view of her panty clad crotch.
.
“You called, Mrs. Naismith?”
“Yes, Uther, and please, call me Elaine.”
She held the pose while he took it in. she put a finger in her mouth, and holding his eyes with hers, began sucking on it as if it were a penis.
“Can I do something for you, Mrs. Naismith?”
“Mmmm, yes you can, Uther. I need your help with this dress.”
She was holding her pearl necklace with her other hand, but renewed sucking on the finger. Her eyes followed him as he walked up to her and paused before slowly opening the buttons at the front of her pale green dress that they both knew she could have handled with ease even if inebriated.
“Uther?”
“Yes, Mrs. Naismith?”
“It’s Elaine, Uther.”
“Yes, Elaine?”
“Do you find me attractive?”
“No, Elaine,” he said and paused.
“Wwwhaa?” She stammered groggily as her hands fluttered in the air. It was not the answer she expected from the youthful Uther.
But the tender kiss he placed at the nape of her neck told her he didn’t mean what he’d just said. And when his fingers told hold of the clasp of her bra, opened it and tugged it free of her still perky breasts she relaxed knowing he would be giving her exactly what she needed that night even before he whispered, “I think you’re beautiful, Elaine.
She dropped her arms to her sides letting her bra slip off her body to the floor. Then she placed one hand on his shoulder for balance and let her dress follow it down.
Uther was stunned at the sight of this gorgeous MILF standing before him in nothing but a lacy white garter-belt, matching panties and stockings.
Elaine was thrilled to see the tent forming in his soccer shorts. “You’re more man than boy, aren’t you?”
“Are you sure about this?” He asked.
“Mmmm,” she replied, for Elaine was unable to speak, from looking so hungrily at his bulging appendage.
“I guess your eyes are answering my question,” Uther said softly.
Elaine nodded. He was already a man in so many ways, she thought. Then finding her voice, she said, “I’ve always liked it when men look at my body. It’s a big turn on for me to know that someone is thinking about my naked body. Have you ever thought about what I look like naked?”
“Silly question to ask when you know the answer ... Elaine.” His pause before saying her name brought her to the cusp of an orgasm.
She reached out and pulled on the elastic waistband of his shorts pushing it down past his hips. “I want to see what you’ve got in there for me. Um, you don’t mind do you?”
As if they were trading back and forth, Elaine reached up and rubbed her nipples, hardening them until they jutted out about ¾ of an inch from what Uther considered average sized breasts, but for a woman roughly thirty-five years old there was no visible sag at all.
“You don’t need to wear a goddamned bra, Elaine,” he said, shucking his shorts off and kicking them away. “Your tits are fine. No, they’re fantastic.” She didn’t know it, but he was mentally comparing hers with those of Deirdre Ng, whose breasts were smallish and perky, but her nipples, when contrasted with Elaine’s, were mere eraser tips; nice enough but when he’d bitten on them she’d complained that he was hurting her. He was certain he could bite on Elaine’s all night long and she wouldn’t complain at all.
While he was comparing breasts mentally, Elaine hooked her thumbs into the waistband of her panties and slid them down her legs and watched as Uther’s lips tightened. Satisfied she had his attention; she moved her hand to her hairy dirty blonde pussy and began massaging herself.
“Ohhhh” Uther moaned as her middle finger slipped inside her pussy. His cock sprang out and up, although it pointed more to the left than straight up. He was more than a gifted athlete; he was gifted in the size of his manhood as well, with a penis that was roughly eight inches in length and quite thick around.
“Ohhh, you’ve the loveliest cock, Uther!” Elaine said dropping to her knees and engulfing him in her mouth. After sucking him for five or six minutes, she removed his saliva coated cock from her mouth and said calmly, “I’d like you to bone me with this lovely cock, Uther. Would you please do that for me?”
Uther did. In fact he boned her twice in the forty-one minutes they fornicated, and left, just missing Miles Naismith’s return home by some twenty-two seconds.
Miles strode into the bedroom ready to apologize for his actions at the party, but Elaine pretended to be sleeping, and Miles showered then joined her in bed, running a hand over her body hoping she would wake up and have make-up sex.
Elaine refused to play along and continued to feign sleeping. This may have been a mistake on her part, for Miles sent his hand between her legs and fingered her briefly; briefly because he encountered a pussy that was filled to the brim with semen. There was no mistaking exactly what was on his finger and he swore, got up from the bed, and after washing his hands, grabbed a blanket and pillow from the bedroom closet and went to sleep on the couch.
Serves you right you bastard, I know you’ve been fooling around on me. Serves you right! Elaine thought and sent two of her fingers in to sample the semen still dripping from her well fucked cunt.
I need to call the Bissell’s tomorrow and thank them for having Uther drive me home. Maybe I’ll get him a little gift. And she fell asleep thinking about how easy it would be to reserve a room at the Maplewood Motel some afternoon Uther was free for more of the same.
The Naismith’s were still cool with each other following the Bissell’s party two days later. Elaine had obtained Uther’s cell number and an agreement to meet her at the Maplewood Motel on Wednesday afternoon after school.
Miles was chagrined at finding Miss Bee Haven breaking off their sexual activities because he’d as much as promised to remove his wife as a threat to their relationship by getting her involved with another party or even joining them as a willing partner.
“You think she slept with that---that kid from Lithuania. You don’t know it for a fact!”
Miles couldn’t bring himself to admit that he’d found the boy’s semen in his wife’s vagina.
Bea rejected out of hand his claim that his wife had been unfaithful to him with the exchange student, saying “Relationships with students are against the law, and dangerous if they are under eighteen.”
“Elaine’s not a teacher! It’s not illegal for her to have sex with an eighteen year old!”
But Miss Bea Haven turned and left him standing there. Neither realized that Miss Bea Haven’s breaking off their affair so abruptly would set a different set of actions in motions for both of them. She had a plan of her own with respect to a student. That student was Gary Jordan Sullivan, but just then he was unaware of her plans for him.
Miles Naismith & Rachel Ross
Fifth period English Literature – Mr. Naismith and Rachel Ross were alone after class when he said: “Rachel I can’t accept this paper as written.”
Rachel’s lips tightened. Hadn’t they had just had this conversation?
“Let me be perfectly clear. I can’t allow you to write like this in class. This is pornography. This isn’t erotica.”
Rachel blushed and squirmed in her seat, waiting for him to continue.
“Do you know the difference between pornography and erotica?”
“Pictures and words,” she answered, already hating the way her voice pitched upward like a cowardly lion in that Oz movie.
“That’s correct!”
He leaned back. He looked at her. His fuck you finger made idle circles on her manuscript lying flat on the desktop.
“You watch pornography, he continued. “You don’t know what’s going on in their heads. But maybe you can guess.”
Rachel grinned awkwardly in response.
“They’re acting. They and a director want you to think they’re having great sex. How do you know? The woman would have you believe she wants it---or him desperately. He too tries to simulate desire for her. Some actors do this better than others. That’s why some movies---R-rated ones mostly—depict this more effectively that the pornographic ones simply because the director and the actors are better prepared. They do not have sex on camera, nudity, yes, but the end result is actually more believable than watching someone actually having sex.”
Miles abruptly stopped, blushing furiously. Rachel’s heart rang in her ears. Her stomach was at the top of the roller coaster, at the very top, just before the cars let go. Both of them were on the verge of panting with excitement.
“I’m so sorry, Rachel... “I didn’t mean to be so graphic.”
“I know,” she fumbled for the right words... “Um, I didn’t take it that way. I mean, I would never...” She laughed awkwardly. “I um, I’ll bring a different story to our next class; if that’s all right with you.”
She couldn’t bring herself to meet his eyes. All she could think of was finding the nearest bathroom so she could touch herself before she exploded.
Gary and Miss Bee Haven
Earlier the same day, Miss Bea Haven was telling her class: “My favorite time of the school year is coming, class,” and proceeded to regale them with several antidotes about prior Mock Congress sessions held at the school.
Gary learned they would be paired off into groups (“committees”) and would need to push a proposed legislation. Gary thought of himself as a loner and didn’t like working with other people on projects, although he got along with most of his classmates. His group turned out to be: the wise-cracking David, overly talkative Emily, and Vicki Ostrowski.
He could have done without David and Emily – he wasn’t nearly as funny as he thought he was nor was she as interesting as she figured she was, but Vicki Ostrowski—well, she more than made up for them. She was beautiful in a movie star sort-of-way. Vicki had been the new girl last fall so not a lot was known about her, but one of his friends apparently tried to cop a feel at Homecoming and got punched in the nuts. Regardless, Gary had been working up the courage to talk to her for a while now and with this development -– plus a growing confidence from having gone down on, and then fucked Daphne Xu to her obvious satisfaction - – it was going to happen.
He tried not to stare at Vicki as Mrs. Haven announced their little group, but Vicki made that a bit difficult as she chose that day to wear a dangerously short skirt that displayed her well tanned legs. She was outwardly a shy thing, but she seemed to at least have a decent idea of how hot she was.
After class, Mrs. Haven asked those selected to stay a few minutes to talk about how they might practice putting their respective legislation formatting in place. Gary wanted to follow Daphne’s swaying ass right out of class, but quickly changed his mind on seeing Vicki cross those tanned legs and Miss Bea Haven’s rear end when she bent over to pick up a piece of chalk she’d dropped.
Daphne could wait. Just maybe he might get some time alone with Miss Bea Haven. After all, their last time together she’d pointed out his hard on, maybe this time she’d want to see it.
As fate would have it, or so he thought at any rate, Vicki had to leave for a dental appointment leaving him alone with the sexy teacher.
“Well, hopefully, we can finish here without any ... um, other distraction, Gary, Miss Bea Haven said with a wry smile.
Staring at her for a second, Gary wondered if she was just giving him some good-nature ribbing or if she was enjoying the attention. After his recent conversations with his sister he decided her comments certainly went beyond those a teacher would normally use on a student and countered with: “Well, I’m a teenager, and when I deal with distractions, they inevitably find their way back into my life.” The words just flew out of his mouth without much thought.
“Oh, I recall,” she replied with a wry grin, “It wasn’t that long ago that I was a teenager myself.”
“Now, about this essay...” she started, but he cut her off. “You should dress sexier. Really show off your assets.”
She should have slapped him or reported him. She could have reaffirmed that she was the teacher and he was the student. She could have said anything other than what she did say.
“What assets would that be, Mr. Sullivan?”
“Well,” Gary began as he tried to keep in mind that there was a limit to what he could say. “You clearly have a nice ... chest that you keep hidden. Maybe some tighter clothing would help.”
“And who might that help, Mr. Sullivan?” Had she not been smiling as she uttered those words, Gary might have run from the classroom in a panic.
“I’m just saying ... if you got it, flaunt it.”
“Like you are, Mr. Sullivan?” Miss Haven and nodded her head slightly toward the tent that was now evident in his slacks.
“I’m not a teenager, Gary. I know what you think you want and why.” She sat back in her seat and looked him directly in the eye. She brought her left hand over her right forearm causing her breasts to strain even more against the fabric containing them.
“Is this what you think I should do, Gary? Wear my clothes tightly over my...” she paused for effect before saying: “Chest as you so innocently referred to it? Think you could learn about the Supreme Court with this happening?”
Gary fumbled for an answer, but he too paused before answering, and then chose his words carefully. “Personally, I think I would do even better.”
And that forced a laugh, a genuine laugh from Miss Bea Haven.
“It’s true. See, I couldn’t possibly focus on anything else in the classroom but you.”
“I don’t think you’d do your best work with only one organ demanding so much from your blood supply,” she said drolly.
“Maybe, but I’d like a chance to try.”
She smiled up at him before looking at his package, as the female teacher’s often referred to their male counterpart’s penis’s when noting them outlined against their slacks.
Gary wanted to whip his dick out, but that would be taking things too far. Expulsion would follow that act and he knew it. What followed was for Gary, a stroke of genius.
“Answer me this, Miss Haven. Just how much of a thrill is it to know how excited you make me? Wait, excited is a poor choice of words. I mean how hard you make me while dressed conservatively?”
“I don’t follow you, Gary?”
“Does it turn you on?”
For a moment he feared he’d gone too far. Her facial expression kept changing and any hope he might have had of reading it to gauge her response faded quickly. They were at a crossroads as the accepted boundaries of any teacher/student relationship and he knew it.
“To your last question, Gary ... yes, though I can’t quantify it anymore than that,” she replied. “And with that, Gary, you should go to lunch.”
He grinned at her, his conversations with his sister though embarrassing and humiliating at times served him well at this point in time. “You’re right. I know exactly what I want to eat.”
“Then go to lunch,” she said and looked down at some papers on her desk thinking he realized he’d been dismissed.
“But what I want is right here.”
Miss Bea Haven continued looking at the paper on her desk, but a tic appeared on her right cheek that she couldn’t rid herself of. Of course Gary saw it, although he didn’t connect it to his words. But he did realize she couldn’t meet his eyes, so he brazenly stared at her breasts, but was afraid to touch her. He knew if anything was going to happen, she would have to start it.
“Gary, whatever you think is going to happen by this admittedly foolish avenue of communication I’ve let us wander down is going to have to stay in your head. Remember this: The reason why you call me Miss Haven is because I am your teacher.”
It was her attempt to push off what was now clearly obvious from their exchange. She liked this banter. She wanted to be flirted with. And maybe, she wanted more. And that’s exactly how Gary saw it. He was not about to let their relationship simply fall back into a hole. He had learned far too much from Trudy.
He could tell she was looking out of the corner of her eye at the bulge that was now on display only two feet away from her. She took a deep breath and looked down at the paper. Moments passed as she either searched for the words or battled her conflicted emotions about what to do next. Finally, she decided what to do and turned to stare right at his bulge and never wavered. “It’s pretty good--– this essay of yours. It could use some work. Sometimes, you walk around the point rather than just letting the point stand out on its own merits. Be sure to tighten up your prose before turning in the final version.”
With that, she handed him his paper. But in doing so, her hand brushed over the top side of his erection. His eyes met hers. He couldn’t tell if it was accidental or not, but the fact that her hand remained there until he picked up his paper.
“I have a question for you, Gary.”
“Yeah?”
“Is this the image you’re going to have in mind when you jerk off later?”
A surprised look flashed across his face before he could compose himself. Then he smiled and said: Kind of, but without the clothes. It heightens the orgasm you know?”
“I should think so.”
“And your hand will be on it as well as mine.”
“That’s an interesting concept, Gary.” She turned away from him, saying: “You’re dismissed.”
“Thanks for advice, Miss Bea Haven.”
Gary grabbed his paper, tucked it into his backpack and set the pack in front of him rather than strapping it on his back.
“Oh, Gary?”
“Yes, Ma’am?”
She licked at her lips. “I’d like you to know that I will give a lot of thought to what we have discussed.”
Rachel and Trudy Browsing at Barnes and Noble’s
“And then what did he say?”
“I felt so sorry for him, Trudy!”
A woman with a small child squeezed past them without apologizing.
“Rachel!”
“What?”
“He wants to do you.”
“What?”
“He wants to fuck you. He doesn’t give a fuck about your writing.” This was more in line with Trudy’s current thought processes about her brother, but she didn’t realize it just then.
“Trudy!”
“Rachel, what he said to you was total bullshit. You should report him. That was completely out of line. He knew perfectly well what he was saying.”
“Trudy, he was red as a beet!”
“Guys get red faced when their horny,” Trudy said, knowing full well it was a total fabrication on her part.
“Trudy, stop it.”
“How many other girls has he duped into fucking him?”
“Trudy, he was so embarrassed. If you had seen him you would know it was a complete mistake. He’s not like that.”
“And you---you Rachel? Weren’t you getting wet when he was telling you all that shit about actors fucking?”
“Um, well ... maybe, but so what? I mean he’s a good-looking guy and just being near him has that effect on me. You too for that matter!” she added defensively.
“So exactly what did he say?” Trudy asked again.
“He wanted to know why. Why describe the sex? Why make it erotica?”
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