Chapter 6

Trudy ponders Rachel and Miles

During her free study period, Trudy pondered Rachel’s stunning announcement of losing her virginity to Miles Naismith. She had no reason to doubt her best friend, but still had trouble believing it actually happened. She rationalized that Rachel had a vivid imagination and wondered if his asking her to join the debate team had caused her daily daydreams about Mr. Naismith to blossom into some weird channeling of a sexual dream into actually believing he had seduced her. But Trudy knew Rachel better than almost anyone, and quickly dismissed that line of reasoning.

No, he had fucked her. Rachel had lost her virginity before she had; and to a man not just a teenager at that. Well, more power to her, Trudy thought shedding any possibility of jealousy toward her friend.

I almost lost mine too, fooling around with Gary; and maybe I will at Saturday’s party. I’m horny and I’m willing, so it might just happen. Then again I might let Gary do me. I know he’s more experienced than a lot of guys in my class. She smiled and started humming, until the teacher watching over the study class called it to her attention and she stopped.

Gary at Home

As Gary entered his home he encountered his mother in the living room reading a book. She looked up at him, but just as quickly down to her book. The last time he had seen her was the previous night when he caught of glimpse of her magnificent tits as he and his sister put her to bed. Of course that had occurred after he had taken advantage of her inebriated state in the car when she’d blown him thinking he was her lover Shon, the landscaper.

It was the way she quickly averted her eyes made him think that she knew something was amiss. Maybe she remembered the blow job. Maybe she remembered the only male she was near last night. Maybe she knew. Fuck, he uttered silently to himself. If she knew, what would she do?

He decided to not say “hello” and instead walked straight to his room and closed the door behind him. Judging by the lack of movement in the kitchen or smell of food, it seemed that dinner was a foregone conclusion. He decided to take a nap for an hour then shave and shower for his ‘date’ with Miss Bea Haven.

It didn’t last long. No more than twenty minutes later, he woke to the sound of a door closing. Gary thought it was his mother returning her own room and had he been deeper in sleep, he wouldn’t have even noticed. He groggily looked at the clock and noticed that it was just 5:40.

He leaped out of bed knowing he had to get a move on only to have his sister Trudy barge in on him looking like she was going out.

“Wanna go to McDonalds with me?”

“What?”

She smiled that knowing smile he was starting to get used to. “Seems Mom’s not in the eating mood and I’m not in the making food mood, I figured I’d get some fast food; you in?”

“Thanks for the offer, but...”

“Stop right there, Bro, I’m not really asking, you’re driving me.”

Gary cursed himself, I can’t tell her anything ... she’s got her nose up my ass and there’s nothing I can do about it ... at least for the moment. I have to get some shit on her, something Mom will be really pissed about. But for now she owns me. A moment later he relented, thinking: Fuck it; I can drive her to get something to eat that’s not a major thing.

So Gary wasn’t all that reluctant as he got up from the bed dressed and in three minutes they were on their way to McDonalds.

“So, I hear you’re seeing someone other than Daphne. Who’s the lucky girl?”

Unable to contain himself, Gary lost his temper and spat out: “What business is it of yours? Do I want to know who you’re fucking?”

Trudy couldn’t hide the shock that his uncalled for remark caused her. She hadn’t fucked anyone. Rachel didn’t count, they’d gone down on each other, but hadn’t fucked... “Let me tell you something shit for brains, I’m a virgin, and would be a pristine one at that if you hadn’t raped my pussy with that big fuckin’ mouth.”

“Fuck you, Trudy,” he shot back, “I saw the two of you going at it last night before I left to pick Mom up.”

“We were hugging, that’s all!” his sister said, raising her voice an octave.

Gary pulled into the McDonalds parking lot and parked instead of going through the drive through.

“It’s faster if you drive through,” Trudy said sullenly.

“Let me say something about last night you little smarmy bitch.”

That got Trudy’s attention and she decided to shut up and listen. Big Brother was obviously pissed.

“As I was leaving I saw, and make no mistake about it, I clearly saw Rachel pulling her panties off. You tried to shield her from me seeing, but I saw enough to know where that was going to lead when I left. You tried to distract me saying ‘Maybe you’d tell me about the bet sometime,’ and then you went over the fuckin’ line saying: ‘I really want to feel your cock in my pussy as much as she does. I get like that when I’m high and super horny.”

“No I didn’t!” Trudy lied, hoping that would help.

“But then I offered to stick around with the two of you. I knew that Rachel was hot to trot, having played with my dick after measuring it. Only you said, and I quote, sister dear—’No, its best if you leave and I fuck Rachel with the strap-on she bought over.’”

“That---that was a moment of weakness,” Trudy said hoping to find a way of changing the subject and kicking herself for bullying him into driving her to McDonalds.

“Admit it, Trudy; you’ve been a fucking bitch for the last week. You’ve got something on me and you act like you own me. You don’t fuckin’ own me. I’ve given things some thought and I’m willing to bet that if you showed Mom those pictures she’d scold me and then forget about it. Of course I could counter your charges by saying you and Rachel are practicing lesbians and maybe worse because you invited me into your room to watch the two of you go at it.”

“What about the blow job in the car, huh?” Trudy spat out vehemently.

“What blow job?” Gary countered. “You have enough nerve to suggest that I took advantage of our mother? You think for one goddamned minute she’d accept that story? Even if she knew it was true, she wouldn’t admit to it, for she’d be partially to blame herself, and she couldn’t accept that it would destroy the family.”

Trudy took a deep breath then decided to shut up about accusations and let the conversation die down for a minute before speaking up once more. “You like her?”

“Who, Rachel?”

“No, the girl I heard you gave a ride to today after school.”

“Yeah ... well, that was Katrina; she’s in this class project in Civics. Miss Bea Haven conned me into the group when some other girl transferred. She volunteered to bring me up to date on what’s what, and needed a ride home. It worked out for both of us.”

“You think she’s hot, do you?”

That question forced Gary to look at his sister. “Yeah, I guess. Why?”

“Just wondering,” Trudy answered.

Turning his head, Gary stared vacantly at the hood ornament of his car. “Actually, she’s very nice. Yes, she’s hot and I kind of like her.”

“You want to fuck her?”

“Gee, what an odd question coming from my sister,” he said sarcastically. “Of course I want to fuck her! I’m a guy. I want to fuck most girls. Then he smiled and added, but not all.”

With that, once again the conversation came to halt. Gary had no idea where his sister was going with her questions, and truth be told perhaps Trudy didn’t either. But she knew her questions would ultimately provide answers to several unasked questions eventually.

But Trudy changed course, saying: “So, I was thinking about earlier,” she said as if having him jerk off for her amusement was a normal thing to do. “You’re right. I lead you on too much and I shouldn’t be surprised that it was sending you the wrong message.”

He was speechless. His sister wasn’t in the practice of admitting to what she did wrong.

“And I am sorry.”

He hadn’t heard her apologize to him in years. And then it was only because their mother had caught her doing something she shouldn’t. It was so long ago that he couldn’t recall what it was; only that she had been told to apologize to him and had.

“You want to fuck Rachel?”

“That would be very nice. You plan on putting us together?”

“I already have shithead. You forget she took your dick into her mouth?”

“She didn’t come close to blowing me, Trudy,” he said feeling stupid in uttering the words. “The fucking phone call ruined things. But she was about too.”

“I guess,” He conceded.

“The bet Rachel and I had was because she told me her brother, Willie had at least a nine inch dick. She’d seen it several times when he walked out of the shower in the nude. He doesn’t seem to give a shit one way or the other. Anyway, she likes you, always has and wanted to know how well hung you were. I told her I didn’t know.”

“You must have seen me, Trudy. If you wanted to know you’d have found a way and I wouldn’t be the wiser about it.”

“That’s true enough, but I hadn’t any inclination along those lines. So I couldn’t tell her and she pestered me to find out.”

“Wait a fuckin’ minute! You’ve seen me. You had me jerk off in front of you!”

“Yeah, well ... that was after I’d told her I hadn’t. Then we made the stupid bet and I couldn’t tell her I’d forced you to whip it out and all.”

“Why not? You did just that.”

“I don’t know; ego?”

He had no reply to that, and put the car into gear and drove around to the drive-in-window and placed their order. When he had paid and received their nuggets and fries and drinks he parked in the McDonalds lot and they started eating and eventually resumed their conversation. “So was it Rachel or me that got you hard enough to measure?”

“Both of you. I mean one of you would have done the trick, but two...”

His sister found that funny and laughed then almost choked on some of the chicken in her mouth. When she recovered she said, “Look at me, Gary,” she began to toy with her bra-covered breasts. “I’ll make that cock of yours hard for me right here and now.”

Gary’s jaw dropped. He was stunned by his sister’s actions as she teased him, pretending to take her right tit out of its cup. His eyes followed her every movement hoping he would see more of her forbidden flesh. Only months away from her fifteenth birthday, Trudy already knew how to entice a male, and found she was comfortable in doing so, using her older brother as a sounding board by moaning softly and seeing the knee-jerk reaction it produced.

Gary had just the one clear thought before submerging into zombie like lust---Why?

“Like them, Bro?” His sister snickered as she pushed the cups of her bra down and popped her breasts free. Then quickly glanced around to make sure no one was near the car.

There was plenty of daylight left for him to take them in. “I’m a cup larger today than I was the day you ate me out. Maybe my babies will be as big as Mom’s.”

“I don’t know about that, but they look great to me. Can I suck those nipples a little?”

Trudy giggled and turning to face him, held her right breast up to his yearning lips.

She squirmed excitedly as he started sucking. “Ohhh, fuck Gary that sure feels good!”

With her breasts fully exposed to him, Gary had time to examine them as he nursed away at them. Her milky white skin showed no signs of tan lines, and he realized that she hadn’t taken full advantage of the few sunny days of early spring. Pool parties were at least a month and a half away. He made a mental note to recheck their size at their next pool party.

Breathing heavily, Trudy gasped, “Gary, could you kiss me?”

He smiled up at her. “Sure thing,” he said, and releasing her breast he leaned up to kiss her lips softly.

It was a more sensual a kiss than any they had shared before. It also lasted quite a while and when it ended the cars windows had started to fog up. Trudy wrapped her arms around his head and pulled him into breasts and he resumed nursing on them.

“You’ve made me soooo hot, Gary. Let’s go home and ... did I mention that I got you a present?”

“You’re kidding me! I wish I had something to give to you, sis.”

“Oh, you did Gary, I’m sitting on it.”

“But it will be your first time ... it should be...”

“No---Noooo! I want you to be the first, Gary. I mean it!”

She put both hands to his face and French kissed him, and then fixed her breasts back into her bra, and straightened her top while he started the car and drove them home.

6:45

Gary was more than surprised at this turn of events. He couldn’t think of anything to say. How could he turn down such an amazing gift from his little sister?

“Mom’s not home, she’s over at Mrs. Ekies again,” Trudy said taking his hand and leading him up the stairs to her room. Gary couldn’t help but notice how the bottoms of her ass cheeks peeked out from beneath her mini skirt and imagined peeling off the thong she was wearing under it.

Still leery of his sister’s trickery, he asked again, seeking reassurance. “You’re sure about that?”

“Yeah, I heard her on the phone before leaving for school. She’s having some kind of party to cheer Mom up.”

When they got to her room, she turned and faced him. “Now, you have to promise not to get mad.”
He nodded. When she tilted her head and pursed her lips at him, he said aloud, “I promise, I won’t get mad. I’m sure I’ll love it, whatever it is.”

“Good,” she said, and she pushed her bedroom door closed and led him over to her bed. I’m dying to know what happened with you and Daphne.”

“Now? You’re asking about her now?”

“No time like the present, Bro.”

“But Trudy...”

Trudy sat on the edge of the bed and pulled him over until he stood right in front of her. She lay back, lifted her mini-skirt up and out of the way and divaricated her legs. “How’s the view from there?” she inquired drolly.

“You look ... incredible,” her brother gasped.

“Thank you,” Trudy whispered sexily, “I practiced poses and liked this one. Oh, it’s just for you. Now tell me about you and Daphne, it’ll make me soooo hot.”

Gary decided to oblige her, and told her the whole story of his time with the Asian minx. “She told me to get better at going down on her the first time we did it. That---that’s why I did what I did to you. I’m sorry about that, Sis.”

“Go on,” she said, feeling herself growing hotter by the second as she recalled how good his mouth had felt on her pussy that morning.

“Well doing you certainly helped me the next time we were together. She praised my new found skills. I never thanked you for that; I guess I was too embarrassed. Anyway, the third time we were together--- Daphne’s cousin, at least that’s what she said he was---barged in on us as we were going at it. I think I was set up. I participated,” he said glumly. But there was a point that I realized I was being used. I haven’t figured out why, but I’m done with her.”

“Yeah,” Trudy said agreeably. “I spoke to her after she’d given up on your cell and called the house.”

“What’d you say?”

“Only that I had no idea what was going on between the two of you. And that you’d tell her eventually. She didn’t like it but, hey, fuck her, she had no choice. Anyway I hung up on her.”

The siblings were silent for a moment. Their noses were millimeters apart. Gary took in her lightly perfumed fragrance, a scent of blossoms from a distant memory. He couldn’t remember, but in fact it was one of their mother’s favorites that Trudy had ‘borrowed’ some time ago and failed to return.

Gary licked his lips involuntarily. “You smell so nice,” he murmured as he fumbled with the clasp of her brassiere. Trudy’s lower lip trembled slightly as she reached back to help open the bra and freed her alabaster breasts, highlighted by a pair of pink nipples that were standing proud. She pushed herself closer, pressing her breasts hard against his chest. A small, kitten-like sound escaped her throat as she kissed him, and Gary quickly returned it. Trudy’s hands moved down to hold his jaw as she mashed her lips and tongue against his while he mauled her perky tits with both hands.

Gary had completely forgotten Miss Bea Haven’s 7:00 invitation when his sister broke the kiss and laughed lewdly, “You need to shave.”

Gary scrubbed a palm across his chin, felt the stubble and chuckled. A moment later it hit him.

Miss Bea Haven! Oh shit! Oh shit!

7:10

Miss Bea Haven paced back and forth in her living room. Where the hell is he? Was he in an accident?

Was he hurrying to meet me and crashed his damned car? He’s what, sixteen?” Oh, shit, what have I done? Getting involved with a student wasn’t a good idea. No not at all. I can’t call him. I don’t dare.

She stopped her pacing and stared at the door. I need a drink. He’s not coming. Oh shit, oh shit!

Two minutes later having spilled the rum intended for her drink, she succeeded in making herself a rum and coke and finished half of it with a wild gulp. Maybe he’s just late. I should try to relax, after all he has no idea what I had planned for him; he’s only a kid. Oh, shit ... what if he tells them he was coming to my place... She sat down on the carpeted floor and began to cry.

But Gary wasn’t about to arrive at her door that night and left his teacher bereft with misplaced passion and concern over his well being. She finished off an almost full bottle of Merlot and went to bed.

7:42

Trudy inadvertently saved the day by getting to her knees and cradling her breasts with both hands, cooed, “Do my girls again, Gary. I liked the way you sucked on them before.”

“Jesus,” Gary wheezed, finding himself short of breath; then torn between his sisters looming tits and thoughts of what his teacher would say about him missing their appointment, he opted for the bird in hand and brought the closest nipple to his mouth and sucked voraciously.

Glancing upward, Gary saw that his sister’s face was flushed and still drawing hard on her right nipple, reached down and began tugging at the elastic waist of her thong.

“Mmmm, let me, you’ll only tear the damn thing,” she moaned. He sucked harder. She tossed the thong to the floor.

“Ohhh, baby ... that’s soooo nice!” Trudy crowed, and sent two fingers her steaming cunt.

While switching from one pointed nipple to the other, Gary looked at her lithe body and noticed that her throat kept bobbing, as if she couldn’t stop swallowing. He ran his hand over her belly and felt the resulting tremor it caused.

“Trudy, open those beautiful legs so I can see,” her brother croaked hoarsely. She complied and he was suddenly overwhelmed by the aroma rising out of her vagina. Obligingly, Trudy started to part her legs, but her brother’s face was so close that she hit it with her knee.

“Ow! Fuck that hurt!” He exclaimed.

Giggling, his sister slowly raised her knee, providing Gary with a close up view of her cunt. Rubbing his jaw he took a close look at his sister’s pussy and saw it was recently trimmed.

“You trimmed it for me?”

Trudy laughed delightedly and shook her head, saying, “No, it was for Rachel, you goof-ball. I had no idea we’d be doing this. So what do you think?”

Gary reached out and using his thumbs spread her outer lips apart and peered into the coral colored depths inside.

Trudy gasped as he opened her pussy; she had been fantasizing about this moment for so long, only it had been imaginary men; movie stars and rock stars, not ordinary people, and certainly not her brother; although she had wondered about him after he’d taken advantage of her that morning in the bathroom.

“Mouth watering,” he said, more to himself than Trudy then bestowed a quick kiss to her labia.

“Mmmmm, you’re a sweet talker, Gary. I hadn’t realized that about you.”

“Run your hands over your breasts for me.”

Trudy didn’t understand why he wanted her to do it, but was happy to oblige and cupped her breasts then rubbed them in a circling manner. Suddenly the effect it wrought on them caused her to gasp with pleasure, surprising both brother and sister.

Trudy’s beautiful tits are even more sensitive than I thought. Gary told himself as she rubbed over her nipples and moaned happily.

“It isn’t this way when I...” She stopped, not wanting him to know all her secrets, but still wanted to please him more than anything else.

Her brother tried to look relaxed on the outside but didn’t succeed. Every nerve in his body was jangling and he realized he was stiff as a board at what was happening between them. Trudy didn’t seem to notice. Instead she rubbed at a birthmark on her left breast before turning and looking closely at him. Gary started to wither under her stare.

“What?” he asked, fearing she was about to call things off.

She shook her head, a frown on her face. “You know you don’t seem like other guys. Have you ever sucked a guy’s cock?”

“WHAT! NO! What the fuck’s the matter with you?”

His sister nodded, still rubbing the birthmark, then without any warning she dove at him, wrapping her arms around him as she kissed him, hard, pinning him against the headboard. Once Gary recovered from the initial shock he returned the kiss but it seemed he was always a step behind his younger sister.

Her tongue was electric as it slithered into his mouth. His hands went to her back; her hand went to his crotch as she drove him down onto the bed. Tentatively his hand slid down to her ass and she boldly shoved her hand down the front of his pants and after fumbling a moment, carefully extracted his fully engorged penis.

“It’s fuckin’ beautiful,” Trudy gushed, and before he could say anything she had him in her mouth. All Gary could hear, aside from the thudding of his heart, were the soft wet sounds of her mouth sliding over his cock. The feel of her tongue was too much and his whole body tensed. With a long, satisfied groan he came, eliciting a muted whimper from Trudy. She continued sucking for another minute, and the sensations intensified with each bob of her head, eliciting loud groans from the deepest recesses of his throat.

Eventually his sister stopped sucking and allowed him to slide from between her lips. She sat back against the headboard and dabbed at the semen clinging to the corner of her mouth and chin before sucking it from her finger.

Gary lay there, stunned, pleased, vulnerable and invincible all rolled into one. The feeling of invincibility faded, though, and he gradually became aware of his now flaccid penis on display in front of his sister.

Trudy laughed delightedly. “I loved it! I had thought it might be disgusting, with your sperm and all.

But I swallowed every bit of it, see?” She stuck her tongue out at him and he noted a little cum on the furthest reaches of her tongue, but knew she told the truth.

She wanted to explore his body then, and he let her, turning this way then that way to oblige her whims, and they both enjoyed it, and soon enough his penis began to rise again.

“Now you do me, Gary. I want you too.”
{br}

“You have any condoms?” He inquired.

“No!” she groaned back. “I’m on the pill. I really want you to fuck me hard and I want to feel it when you come inside me.”

“It’s my first time!” she went on, obviously pleased with herself. “Everything we do will be a first. Isn’t that something?”

“Are you and Rachel keeping score?” He asked.

“What’s wrong with you, asking me that?” His sister said angrily.

“I’m confused, Trudy. I don’t want to piss you off. But after you and Rachel pulled that stunt about the size of my dick, I wondered...”

“Oh,” she said. “I understand now. You didn’t mean to insult me; it was like when I asked if you’d ever sucked a dick, right?”

“I guess, yeah,” he replied and suddenly all was fine between them again.

“Sooo, how do I stack up against Daphne?”

“Err, you shouldn’t ask questions like that, Trudy.”

“How else will I know if I’m good at it?”

“Did I seem put off about your blowjob, or did you get the impression I loved it?”

“Oh you liked it; you really liked it, Bro.”

“There’s your answer. No need to ask. Now if a guy pulls his dick out of your mouth with a look of disgust...”

“You’ve made your point, Gary,” she said somewhat contritely. “Mmmm, so I want you to um, kneel in front of me.”

“Okay,” and having said that he did as asked, only to have her pull his face into her crotch and say huskily, “Your turn. Eat me.”

Needing no further instruction, her brother pressed his mouth to her outer labia and kissed her, making good use of his tongue as he did.

Trudy moaned and from the start began comparing her brother’s oral skills with those of Mrs. Ann Arbor Bronwen.

Gary’s nostrils filled with the musky odor of her excitement and became light-headed. Her hips rose up to meet his mouth as his tongue delved into her opening.

She shuddered. He abandoned her cunt and softly kissed her inner thigh. In as much as Trudy hadn’t showered that day, what Gary tasted was akin to the sweetness of decaying leaves, not repulsive, but not refreshing either. He paused and once again stared into her sex, marveling at its shape, which to be candid was somewhat different than Daphne’s. His sister’s bulging clit was almost double the size of Daphne’s. The heat rising up from her opening lured his mouth back like the Sirens did Odysseus and his crew.

His guttural moan filled Trudy’s ears and his surging tongue parted her and sent wave after wave of thrilling sensations through her body.

“Ohhh—Oooohhhhh! Fuck yeah!” she crowed, and held his head in place with both hands.

Gary repaid his sister tenfold for using her to prepare for his cunnilingual session with Daphne by using slow, tender licks and kisses as he explored every nook and cranny of her, liberating her juices and coating his mouth and chin.

Low, primal sounds filled his ears only to be muted by the sudden pressure of her thighs against his head. Notwithstanding, Gary kept at his sister, his tongue darting and flicking as she trembled and shook beneath him. But there was a cost to his pleasuring, for Trudy’s thighs hugged his face, and as the ecstatic pleasure soared through her, caused her to squeeze those powerful thighs tighter around him, eventually cutting off the blood to his brain until the world dimmed around him and he passed out.

When he came to his senses less than a minute later, Trudy had him by the hair and was twisting his head painfully from side to side calling out his name in a panic ridden voice.

The moment Gary opened his eyes, his sister shrieked, “Thank god, I thought I’d smothered you!”

Trudy’s face was flushed and sweat beaded on her forehead. With a crooked smile she playfully pushed her brother away in an odd display of affection. Gary wiped his face with the ruffled sheet and realized he was hard again.

“You’re sure about the condoms? He asked again.

“Yes I’m sure, Gary. Now do me, fuck me hard!”

He doubted she was really ready for him to fuck her hard. It would leave her sore if he just pounded her tight and inexperienced little pussy. He didn’t want to hurt her, nor did he want to rush this delectable first time.

But now the reality seemed so much better to Trudy than those fantasies, and it was only getting started.

He did nod and smile at her as he began to slowly work his big dick in and out of her generous ‘present.’ He sent chills through her body as he kissed her neck and nibbled her earlobe as he felt her tight sheath giving way to his probing pole.

He whispered hotly into her ear, describing just how tight and wet her little pussy was around his cock.

Trudy moaned out loud at his words then shook as an intense orgasm swept over her as the thick ridge of his strident cock head caromed over her g-spot.
{br}

He realized what had just occurred was probably from eating her out and paused to search out her right nipple. Trudy moaned appreciatively, wanting to tell him how good it felt, but her mouth was too dry to form any words. She licked her lips and moaned again when he bit down on the nipple.

She shuddered as his cock swelled inside her and wondered why she had waited so long before getting laid. All that wasted time ... all those opportunities lost and for what? Keeping my fucking cherry?

{br}

Her brother was fucking her, and she loved every unbelievable second of it. Then his erection slipped out of her cunt and he stopped and reached down to reinsert it only to meet her hand, just as anxious as his to place it back in her hole.{br}

Trudy gasped, “OH!” as Gary’s hand dropped away leaving her to put his cock back inside her.

She deftly fed him back into her silken sheath and they shuddered simultaneously.