Trudy
Copyright© 2020 by Paris Waterman
Chapter 7
Coming of Age Sex Story: Chapter 7 - 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 girls spent over an hour on the phone discussing what they would wear to the party that night, from skin tight fuck-me dresses that each owned but hadn’t dared to wear anywhere outside their respective bedrooms. It was then that Rachel dropped her bombshell.
“You’re not gonna believe me Trudy, but I had my cousin Ashley dye my hair.”
“You are shitting me. You’re a natural blonde. Everyone envies the shit out of you in that regard.”
“Nope I did it and I love it! I’m a flaming fuckin’ redhead now!” She said with such glee that Trudy believed her.
However they spent another twenty minutes talking about it before switching to which guys they wanted to be with at the party.
“I wouldn’t mind making out with Nick,” Trudy opined.
“Which one, Scipio or Urfe?” Rachel countered.
“Gotta be Urfe,” Trudy answered, “because Scipio’s probably hangin’ with Alexis.”
“Siefert?” Rachel said in disbelief.
“Well rumor has it that he copped her cherry, Rach. What’s he gonna do ignore her at the party?”
Rachel snorted, “Why not, he’s eighteen, and he flirts with most of the decent lookin’ girls in our class and a few sophomores and juniors as well. But it’s curious he hasn’t been seen dating any seniors.”
“Yeah, well maybe he’s not up to their high nosed standards.”
“If Siefert gave it up ... if the rumor’s true, she didn’t marry him. But he was obviously up for her.”
Trudy said, “She’s not bad looking.”
“Speaking of good looking, Davie Shaw’s a really good lookin’ guy,” Rachel offered.
“He is,” Trudy admitted, “but I prefer Al Steiner, he’s seventeen and has that little goatee going for him.”
“Is he hung?”
“How the fuck would I know? They don’t wear signs telling you they’ve got seven or eight inches for Christ’s sake.”
“Yeah, that’s true enough...” Rachel conceded wistfully, “But you know, girls have to show their tits, I don’t know why guys don’t have to let us see their packages.”
“Oh, you want to see every swing dick in the school as he walks by?”
Rachel laughed and said, “It’s an idea. We’d probably kill each other going after the biggest dick.”
Trudy started to snigger but couldn’t contain it and burst out laughing as she gasped out, “And-And he’d probably be a real dick as well!”
After they regained control of themselves (Rachel confessed that she’d peed in her pants laughing.) they got back to what they would wear again, this time settling on tops and skirts, with Trudy selecting her powder blue top because it was extra tight and showed her tits to great advantage and a pair of denim shorts. Rachel on the other hand went with a yellow top for the same reason Trudy did, it clung to her breasts almost as tightly as her skin did. She also chose a pair of beige cutoff pants that let her show of her navel. And after further discussion both agreed to go commando, having finished their respective periods three days earlier.
Gary calls on Miss Bea Haven
While his sister was on the phone with her girlfriend Rachel, Gary was finishing his breakfast of Cornflakes and toasted bagel with orange juice and coffee. He was also agonizing over how to explain himself to his teacher, Miss Bea Haven for missing the invitation to her home for what had to be some serious fooling around.
If she’d of given me her number I could have called. She must be plenty pissed at me for not showing up. No way is she gonna forget that I stood her up. Man oh man; I’m in some deep shit.
But by the time he finished his breakfast he was thinking more clearly and decided to face the music and throw himself into the lion’s den by calling on her at home and telling her about a family emergency. He had already seized upon his mother’s need of a ride home the previous night. It was true enough ... and changing the time frame slightly left him with a true story that her questioning wouldn’t expose any outright lies.
It could work, he told himself. It will work; he thought and smiled as he pondered how to dress for the occasion.
Thirty minutes later he sat in his car just across the street from Miss Bea Haven’s house on Grove Street. He could hear Miss Bea Haven’s voice and realized she was standing behind the hedge that ran along the sidewalk talking to someone, perhaps a neighbor or the mailman? He couldn’t make out what she was saying or who she was talking too, and decided to sit in the car and wait them out. She would return to the house eventually and then he’d approach her front door.
It was the longest five minutes of his life, or so it seemed. The other person was a female neighbor, a woman in her fifties who apparently lived next door to Miss Bea Haven. She came out to the sidewalk and strode quickly to the adjacent house and closed the door. Gary got out of his car and walked quickly to Miss Bea Haven’s front door and knocked twice.
Miss Bea Haven was quick to open the door, thinking her neighbor had forgotten something.
“Sullivan ... what... ?”
Gary quickly moved past his surprised teacher and stopped mid-way into her living room.
“I’m sorry about not coming by last night. I am so sorry, Miss Haven, I...”
“Why are you here, Mr. Sullivan?”
He paused before responding, taking in Miss Bea Haven as she stood there in a bright green night gown that showed him the start of some very interesting cleavage.
“We ... I mean ... I was ... I was supposed to come by last night, but...”
“I think you had better sit down. Would you care for a drink?”
“Yes, please,” he managed and realized he was sweating profusely.
Miss Bea Haven hurried into the kitchen and quickly returned with a glass of ice water. Gary appeared to drain the water in one giant gulp.
“Did anyone see you at my front door?”
“I don’t think...”
“Oh but you must think, Sullivan. I was just talking to my nosey neighbor, Mrs. Angleton. Did you see her, or more importantly did she see you?”
“Um, I saw her leave. I saw her go into her house. I don’t think she ever turned to look in my direction. Anyway, I stayed in my car until she was inside her house, and then I ran up to your door and knocked.”
That seemed to reassure Miss Bea Haven that she had no explaining to do over his visit. “More water, Gary?” She inquired gently, calling him by his first name for the first time.
“Yes, please,” he answered and waited until she had refilled his glass before speaking again.
“Look, about last night...”
“Yes, tell me about last night, Sullivan.” There was just a tinge of anger in her voice.
“I really wish that I had your phone number.”
“I’m in the book,” she said caustically.
“Ohhhh,” he replied sorrowfully, and put the glass down then covered his eyes with both hands.
He looked so pitiful that Miss Haven took pity on him and decided not to berate him any further.
“What happened, Sullivan?” She whispered in his ear, wanting to nibble on it in the worst way, but constraining herself from doing so.
“I—I was about to leave when we got a call from my mother’s friend Mrs. Ekies, do you happen to know her?”
“No I don’t believe we’ve met. Go on.”
“I really hate myself for having stood you up, but she asked me to come over and bring my mother home.” Gary looked up and met his teacher’s eyes. “She’d had too much to drink and they wouldn’t let her drive. It was a family emergency. I had to go and couldn’t, or didn’t think of looking your number up. My mother was out of it. I had to stop twice on the way home because she got sick. And then when I got her home, we---my sister and I---had to put her to bed, only to have her get sick again. Aw, you don’t want to hear this...”
“So by the time you and your sister got your mother under control and put to bed for good it was too late to drop by?”
“It was about eleven by then, so yeah; kinda late for me to be going out again. Then too I had no way of knowing if my mother would need us again that night. I mean ... turned out she didn’t but I couldn’t know that, so I stayed with her until around one in the morning before I went back to my bed.”
She moved closer to him and cradled his face in her hands. “I’m glad you could make it today, Gary. I understand your emergency. I’m not angry that you didn’t make it. You may not believe it, but I’ve been stood up before.”
Still quite nervous, Gary knocked over his almost empty glass and it fell to the floor but miraculously didn’t break. He crouched down to pick it up and realized it had rolled under Miss Bea Haven’s left leg. He bent at the waist and righted the glass, but didn’t sit back; instead he let his hand touch her calf, and when she failed to say anything, moved it between her legs to the point that her knees met.
She kept them together until he gently pulled on the left knee almost repeating what he’d done previously in the classroom. It was as if he’d said ‘Open Sesame,’ for her legs parted magically leaving his hand free to explore as much as it liked. Gary risked a glance at her face and saw that she was also staring down at where his fingers were disappearing under her nightgown. She made absolutely no attempt to stop him and there was no look of fear or shock on her face.
Once his knuckles touched the fabric covering her vagina she said “Wait,” and stood up.
Concern that he had gone too far to fast was written all over his young face. But vanished when he turned to face her and found his teacher raising her nightgown and tugging a pair of yellow panties down to her upper thighs. Gary’s jaw dropped on seeing the small tuft of red hair at the top of her mound. Moreover, her left breast was all but out of her nightgown. He gasped for air. Miss Bea Haven giggled school-girlishly, and with a deft move exposed both breasts for his edification and perusal.
“How about these baby’s?” she asked, cupping both breasts in her hands.
This was the woman he’d dreamed about. “Lovely,” he answered after a long moment, for he wasn’t capable of speaking just then.
Miss Bea Haven laughed raucously, then teasingly let her right hand drop to her groin and took hold of the yellow panties and stretched them out, revealing her red tufted genitals to him.
“You fingered me in the classroom Sullivan; this time you’re going to kiss it, lick it and fuck it. And you’re going to do a wonderful job too. You will, won’t you?”
“Yes—Yes I will.”
“I’ve heard you talk in class, but talk is cheap. Have you ever eaten a pussy? Don’t lie. I’ll know if you haven’t.”
“I—I have. Two different girls; they—they both told me how good it was and they were serious.”
His teacher smiled and turning away from him leaned forward so that her ass jutted out inches from his face. “Tell me Sullivan, what do you think of my ass?”
Gary took it in: the spidery web-like design of her anus seemingly beckoning to him. He sighed and stuck his middle finger out and skimmed the flesh of her anus ever so lightly.
“Oooooohh, you’ve got the loveliest touch!” She turned back around to face him again. “I think you’re going to make a wonderful lover.”
He wasn’t really listening. He was taking in her breasts now that she was facing him and comparing her with his mother, who he realized was larger; and his sister who was somewhat smaller. Daphne was only slightly bigger than Trudy, but Rachel was slightly larger than Miss Bea Haven. The realization of the number of breasts he’d seen in recent days astounded him.
She brought him out of his momentary daydream by chiding him, saying: “Do you approve or should I put my clothes back on?”
“No fucking way,” he replied quickly, drawing a wide smile from her.
“Would you prefer I call you Sullivan or Gary?
“Um, Gary, please.”
“Good, then please call me Bea from now on; at least when we’re alone.”
“Bea,” he said testing the sound of it at the same time his fingers found her pussy. The smooth flesh gave away to the far more sensitive slit between her pussy lips. Keeping his eyes on her face as Miss Bea Haven tried to remain composed; Gary slid his index finger from the top of the slit downward, and felt her pussy swallow the finger as if grabbing it. Her cunt was literally a swamp at this point.
“Fuck...” Bea whispered under her breath. Her hand fell to his wrist, but applied no pressure as if to push him away. Instead, she let her hand rest there as if to hold onto him more than anything. In the quiet of her living room, the wet and squishy sounds of her cunt grew as Gary fingered her more rapidly.
“Oh, shit!” She exclaimed, and closed her eyes. “Maybe we shouldn’t...”
Gary didn’t let her finish the sentence. He crooked the finger inside her love channel and drew a long satisfied moan from her throat. Inspired by that sound, he began to seek out her little love nubbin, watching her face for any tell tale sign that he was on or about the hard to find clitoris.
His sister’s had been relatively easy to locate, but Miss Bea Haven’s was more difficult, until his thumb rolled across a tiny bump that caused her to convulse and he knew he’d found it.
“Oh ... fuck ... ohhhh, fuckkkk!”
She turned to find his eyes. “No ... I ... oh, yes ... right there, Sweetie!”
He needed nothing else from her and renewed his fingering while rubbing at her clit even faster. Her reaction told him that he was doing exactly what she needed.
“I can’t ... I can’t believe this,” she whispered hoarsely. Her grip on his arm grew more and more urgent as if his fingers and arm were becoming more and more a part of her and they couldn’t leave. Her moans grew louder, though she made sure not to get too loud. The smells emanating from her pussy filled the room and turned him on even more.
Gary was ready to taste her, but continued to finger-fuck her tight little cunt while his thumb throttled her hard clit. He wanted to see if she would cum for him this way.
“Why ... are you ... doing this?”
The question threw him and for a moment Gary forgot himself. “What?” He rasped as he stopped fingering her.
“Um, I—I guess I’m doing this...” But he couldn’t think of an answerable response. Instead he took hold of her left breast with his free hand. Meanwhile the fingers of his right hand dropped from her cunt to his side. The nipple on the breast he held stiffened before his eyes, and he leaned in and took it between his lips and squeezed it hard enough to elicit a hard groan from Miss Bea Haven.
“Ahhh, ahhhhh, yeah ... worship those tits, Sullivan!” She croaked as she cradled his sucking mouth to her breast. Gary responded by dragging his teeth across her soft skin and squeezing her breasts in his hands.
“Mmphhh...” Bea gasped, as the teenager nursed on her nipple just the way she liked it, pinching it with his lips and tonguing it rapidly.
This action let him gather his thoughts and he pulled away from her breast and said, “Um, I—I’ve wanted you from the first time I saw you walk into the classroom. I’m sure you give every guy there a boner. I know half of them race to the bathroom to jerk off at the end of your class.” He paused and licked his lower lip. “Did you know that?”
He didn’t wait for her to answer; he had decided to continue talking dirty to her. It was what had forged their sexual connection in the first place. But it was not necessary as she gripped his arm so hard he knew there would be a bruise the next day. He resumed fingering her, this time using two fingers instead of the one. She closed her eyes and humped his fingers riding out the oncoming orgasm. Her breathing was erratic and she let loose a high-pitched squeal that was impossible for her to keep in as she hit the crescendo of her orgasm. Her mouth opened, but no sound came from it.
Gary wanted to kiss her but didn’t, somehow finding it inappropriate.
As her orgasm faded, Bea applied a different pressure to his arm. Instead of holding it to her, she pulled it away. Her eyes pleaded with Gary and he slowly withdrew his fingers from her vagina.
“Too ... too sensitive...” she breathlessly whispered, explaining why she wanted him to stop touching her.
“Sorry, Miss Bea, but you’re so hot you drive a guy crazy.
“Do me a favor, Sullivan, will you?”
“Sure anything, Miss Bea.”
“Take that shirt off. I need to see you.”
“Oh ... sure!” Gary pulled his shirt off and stood before her, half naked. “Um, should I take the rest off too?”
“Yes, please. I’ve felt your penis before, but I’ve never seen it.”
He was nude in a flash, and she looked him over with lust filled eyes then took him in hand and began stroking his shaft. “It’s bigger than I thought it would be.”
“Seven and a quarter inches,” he said proudly as the copious supply of precum on the knob of his penis made a soft, slurping sound as she fisted him a little faster.
“And the girth?” she inquired innocently thinking he knew.
“Err, I don’t...”
“Ohhh,” she said delightedly and allowed his shaft to escape her slippery fingers.
“Then let’s measure, shall we?”
She had him stand the holding his penis while she looked for her tape measure. Finding it in another room caused his erection to wilt a bit and he was somewhat embarrassed since his penis had been the major topic of their conversation.
“Ohhh,” she said, sounding disappointed at his flagging penis. “Let’s get him back up there, shall we?”
And without another word she dropped to her knees and took the head of his cock into her mouth and sucked and licked him while cradling his testicles in her right hand for about two minutes before his cock was clamoring for action again.
Miss Bea haven applied the tape to his rampant prick, and shouted four and a third in circumference! Pretty thick piece of meat you’ve got there Sullivan!”
Pleased with himself, Gary went to kiss her, but she moved her face away and said, “Stand still!”
The teacher-student relationship took hold and he did exactly as ordered.
“You’ve the loveliest body, Sullivan,” she said softly while running her right hand over his chest. On reaching his abdomen she paused and frowned. “My word, you’ve muscles here that I find unbelievable. You’re what sixteen or seventeen?”
“Sixteen, Miss Bea,” He answered. “But I do five hundred sit-ups every day.”
“What on earth for, Gary?” she asked as she continued testing his muscular stomach.
“Um, well I saw this porno film about six months ago...”
“And?”
“And the guy was different than other guys I’d seen before. I mean you could see that the girls he was ... um, you know...”
“Fucking?”
“Yeah ... fucking. Um, they really came. They weren’t faking it and the cameras didn’t stop or anything that would have told you they were faking it. Um, the reason they came was this guy fucked them relentlessly. I mean he started slow enough, um, like normal, I guess. But after a while he got going. I mean he really got going, like hammering away at the woman. Now I’ve watched other guys do this for maybe thirty seconds before dropping off to slow stuff. But this guy kept going. I timed him once and he pounded this girl for a minute and ten seconds before she came and he kept going until she rolled away from him unable to take anymore.
“So you figured his strength was in his abdominal muscles?”
“Yeah,” he said and grinned at her.
She pinched his nipple hard enough to make him cry out.
“What the fu ... what’d you do that for?” He said as he rubbed the sore nipple.
“Don’t get too confident, muscle man. I’ll let you know if you’re as good as you think you are. However, not wanting to hurt his feelings being brought to a very pleasant orgasm with his fingers, Bea decided to put the stick aside and offer him the carrot, giving him a half smile and slipping her hands behind his head.
Gary thought she was going to kiss him, but she leaned in and began sucking at his neck. Fully aware of the dangers inherent in leaving hickies, Bea did not suck hard at any one place before changing tactics. She extended her tongue and began licking her way down his chest, following his sternum only to deviate and leave a wet trail to his right nipple. After placing a light feathery kiss on it Bea began sucking. It was the first time a woman had really done it to him and Gary really enjoyed it as the blood rushed to further engorge his cock. Each lick on his nipple sent an electric jolt straight to his penis.
Bea made sure they maintained eye contact and a slight smile appeared on her face as she abandoned the nipple and continued her southern descent, pausing to lick circles around his belly button before plunging her tongue in. It was a weird but pleasant sensation and he moaned signaling his satisfaction as she took hold of his throbbing shaft again and slowly stroked him.
“I should tell you that I’ve wanted to play with this baby since you took it out.” That said, Bea’s tongue darted out and licked the head. The resulting sensations had Gary gasping for air, so she did it again and then again. She turned her green eyes up and met his, then swallowed most of his cock, deep-throating him the way she had learned from her times with Miles Naismith. Gary was awed by this and even more when she took him from her mouth only to kiss and lick her way down the length of his shaft to the point where she met his dangling balls.
“I’m sure you’re gonna like this, Mr. Smart Ass,” she crowed and took them both into her mouth, swishing her tongue over and under; thoroughly saturating them with saliva before spitting them out and then laughing in his startled face.
“Follow me, Mr. Smart Ass if you know what’s good for you,” she said sharply.
Gary followed her like an obedient puppy into the bedroom.
“Kneel on the bed, I’ll be right back.”
He quickly complied and Bea returned with a towel in one hand and a cup with some kind of oil or lotion in it. The towel went under his legs, and then she had him spread his knees apart with his chest on the bed.
“Ever read the Kama Sutra?”
“No I haven’t.”
“Ever heard of it?”
“No I haven’t.”
“It’s the Wikipedia of sex, Gary. You should go to a bookstore and buy it. The ladies will love you all the more for applying the techniques it has in it.”
Bea works a soft, fluffy pillow under his head. “Comfy, baby?”
“Yeah ... I guess ... what...”
“Quiet, I’m working here,” she whispered into his left ear while her thumb rolled over the stream of
pre-cum oozing from his penis.
Gary couldn’t have felt more comfortable.
“Remember, be quiet, I have to concentrate,” she said; and he detected a huskier vibe in her voice as she took his seven-inch cock in hand, poured some oil on it, and then rubbed the oil all over his shaft. Next she pulled the foreskin back as far as she could. And then added more oil to the precum on the cockhead itself.
He was startled when she released his appendage only to begin massaging the oil into his buttocks. He didn’t complain for it felt marvelous. She used both hands to massage and spread his cheeks further and further apart. Gary was completely relaxed, perhaps even off to another world as she stood by his side ministering to his ass with loving care and tenderness.
Then she stood up, came round and kissed him on the mouth. He responded by sending his tongue into her mouth and the kiss lasted for roughly two full minutes before she broke it off, whispering, “More to do, Sweetie.”
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