Theresa Relieves Enny

Kenny was getting dressed to go out with Anna-Marie. They had been dating for several months and he was starting to develop serious feelings for her. He'd even thought that she could one day be "the one." She was fun to be around, she was kind and considerate. He could tell by the way she treated his nieces and nephews that she would one day, probably make an excellent mother.

The problem was, after nearly twelve weeks and countless dates, Anna-Marie refused to let Kenny consummate their relationship. Sure, she loved making out and they spent many an evening parked in a secluded spot, kissing and exchanging some "heavy petting," but that would be the extent of it.

Kenny had yet to even have his hand in her shirt, much less down her pants. And the frequent make-out sessions were making it more and more difficult to resist ripping he clothes off and taking her against her will.

"For crying out loud, we are both 20-years-old!" he would think. Surely, they were old enough to advance their relationship to something more intimate.

But Anna-Marie was raised a good Catholic girl. She had promised herself and her god that she would remain a virgin until her wedding night. She loved Kenny, but she had made the rules very clear on their first date, nothing more than kissing. She had already gone too far allowing Kenny to rub her breasts through her shirt.

But for tonight's date, Kenny hopes were high. He wanted so badly to touch the flesh of Anna-Marie's tiny tits, to kiss and suck the hard nipples that he had felt through her t-shirt and bra.

But more than anything he wanted Anna-Marie to make him cum. These three and four-hour make out sessions left him a stiff, aching boner. After dropping her home, he would need to race home afterward to get to the bathroom to beat off for relief. Sometimes, he was unable to wait and had to pull off to the side of the road to masturbate.

This arrangement was just not getting it done for him. He needed his girlfriend to grab hold of his cock and jerk it, maybe even put it in her mouth and let him explode all over her.

Part of him knew that was never going to happen until they got married one day, but the more hormonally charged part of him dreamt that one day soon, he could strip her naked, climb on top of her skinny body and fuck her in a dozen different directions.

Of course, if Anna-Marie had any idea that these thoughts were running through his mind, she would put an end to their relationship. She could never be with anyone so wicked and perverted.

Kenny finished buttoning his shirt and making sure his hair was perfectly combed for his date. His beard was neatly trimmed, (just the way Anna-Marie liked it) and he splashed on a drop or two of cologne, hoping maybe the scent might somehow magically intoxicate her into giving into his desires.

He walked downstairs to the bottom floor of the split-level home where he lived with his mom, dad and his younger brother and sister. As he reached the bottom floor, which led to the door out to the driveway, he passed his sister Theresa's room.

"My goodness," his sister yelled to him, "don't you look pretty tonight? Somebody's working awfully hard to get lucky." She then cackled with a smile.

"Yeah, I wouldn't bet on that," he replied in the saddest face he could muster.

"Aw, what's the matter?" Theresa asked. "Saint Anna-Marie not blessing you with her heavenly body?" With that, she let out a louder laugh in the direction of her older brother.

Now when it came to heavenly bodies, Kenny's sister cornered that market. She was a lovely Italian-American with thick, dark brown hair, a stunning face accented with chocolate brown eyes, thick lips and high cheekbones. Her body was the exact opposite of Anna-Marie's. Her breasts were huge, at least at 38D and her waist was thin. This made her wide hips even more voluptuous and her longs legs as sexy as you could ask for.

She was tanned and toned and was never without a boyfriend. And while he never bothered to confirm any of the scuttlebutt he had heard, Kenny had it on good authority that Theresa's (many) boyfriends always seemed very satisfied after exploring all of the wonders her body could offer a man.

To Kenny, at the moment of course, she was just his 18-year-old sister and now she was giving him shit that he didn't really appreciate.

"Enough trash-talking about my girlfriend," he shot back at her sternly. "She's a good girl and we're just taking our time."

Theresa laughed back, "Yeah, but I know you. You're like all the other boys, eventually you're going to get tired of 'taking your time.' How far are you getting? Has she let you suck on those tiny titties of hers yet?"

Kenny paused for way too long with his reply.

"What the hell is she doing? Is she just sucking face with you for three hours and then cutting you off?" she asked incredulously.

"Yeah, pretty much," muttered Kenny.

"Jesus, that sucks. I don't know how you've put up with that for as long as you have," she said. "I know you're no virgin and you're not that religious. But honestly Kenny, is that scrawny little bitch really worth the wait?"

Kenny was pissed; he said nothing and turned and walked out of the room, down the hall and out the door to the driveway. As he pulled out he spun the tires of his car in a display of frustration and disgust.

Maybe Theresa was right. Maybe Anna-Marie really was just a cock-tease. What if he waited another year or two and married her, only to find out that they were sexually incompatible? What if even after marriage, she turned out to be a prude and was unwilling or unable to satisfy him? As he drove to pick up Anna-Marie at her father's house, his mind tumbled with thoughts of doubt about their future.

Tonight was going to have to be a turning point in their relationship. He could not seriously consider asking this woman to marry him if she was reasonably willing to give in to his desires. He didn't need to take her virginity, he just wanted to touch her and caress her skin. He needed her to hold his manhood in her hands and relieve him of the sexual pressure that had been building up inside of him.

When Kenny got to Anna-Marie's, he did his best to carry out the usual small-talk routine with her father. He was a nice enough guy, but very strict and quite the stiff.

Anna-Marie came down the stairs and to no one's surprise, looked every bit the innocent virgin: White blouse with a navy blue cardigan sweater and a conservative (not-too-short) flower-print skirt and a pair of black flats. Her short curly brown hair and lightly freckled face looked sweet and pure.

Suddenly, in his mind, Kenny couldn't help but picture what her pretty face would look like covered with his sperm and his dripping cock stuffed into her mouth. These were visions that would normally only come to him at the end of the night, after she had got him so worked up that he had to beat off.

They left for the restaurant and Kenny was so preoccupied that he barely uttered a word. Halfway there, Anna-Marie detected that something was wrong. Kenny was usually very talkative, but tonight something was definitely bothering him. But she decided to not push it, hoping that he would cheer up once they sat down for dinner.

But Kenny's mood didn't change during dinner. He barely said a word and kept watering the seed that his sister so casually, yet so calculatingly planted in his mind. After they had finished eating, she could no longer stand the wall of silence that he had built over the course of the evening.

"Kenny, are you okay?" she asked with genuine concern.

"Yeah, I'm fine. Just aggravated with Theresa," he said, she can be so rude sometimes."

"Well, you know I don't know her very well, but based on some of the stories I've heard, rude is just the beginning with her," said Anna-Marie, somewhat indignantly. "Did she say or do something? I've never seen you like this."

"Nah, don't worry about it," she was just being a smart ass like always. Sister-shit. I'll get over it. I always do with her. What stories have you heard about her anyway?"

"I just heard that she runs with a rough crowd and hangs around a lot of college boys that aren't known for their manners. I heard that she's pretty friendly with the boys."

"She's got plenty to be friendly with," Kenny snapped back. "She's a very attractive girl. Besides most of those rumors are just that—rumors."

"If you say so. But enough about that, what would make you feel better? Would you like to go on to the movies or would you like to go park and talk a little while?" she said with the most devious grin a good Christian girl could muster.

"I think we probably need to talk," replied Kenny. "And tonight I need the kind of 'talk' that will relax me. I'm obviously feeling a little tense."

She giggled, completely oblivious to his insinuation, "Well, go on and pay the check and let's go."

"Yeah, sure, pay the fucking check," he thought to himself. "Then we can go park so I can give you a raging hard on and then leave you alone to deal with it."

He paid the tab and as the sun set, they headed out to Saddle River Park, which was their normal make-out spot. Kenny parked the car and turned off the ignition and tilted his seat back a few degrees.

Anna-Marie reached over and put her hand to his cheek and asked, "Now what can I do to help you feel better and ease your mind?"

"You can start by kissing me," said Kenny, looking down at he sexy thin legs as her skirt began riding up.

She leaned over further and placed her lips to his. He kissed her hard, more aggressively than normal. It didn't go unnoticed. She may have been naïve, but she sensed that he was very hungry for her, much more than usual. She began to silently pray that he would relax and asked God for the strength to protect her vow to him.

They kissed for nearly ten minutes, Kenny shoving his tongue deep into her mouth and caressing her small breasts over the top of her shirt. The feel of her body tonight was more irresistible than ever. He had finally come to the realization that the only way he would ever have her was to take her.

His cock throbbed in the crotch of his tight khakis and he took her hand and moved it onto the gigantic bulge in his pants.

"Oh my, gosh," uttered Anna-Marie. "You are so hard." And with that, she began to reciprocate his aggressive, violent kissing.

Kenny decided to make his big move and quickly slid his hand up Anna-Marie's skirt and began rubbing her between her legs. It was the first time that he had ever come this close to touching her pussy and as he massaged her with his fingers he noticed that her cotton panties were soaking wet.

He saw this a sign—the turning point that he had hoped for. She continued to rub the massive bulge in his pants and he felt as if he could cum at any second. He needed to feel her hand wrapped around his cock. He needed to show her his thick, hard manhood now.

Kenny reached down and began to undo his belt. Annie-Marie was shocked and immediately pulled her hand away and leaned back from him.

"What are you doing?" she cried before he could get the top button of his khakis undone. She looked horrified.

He looked back at her, his face full of wanton desperation and desire, "I want you to touch it. I need you to touch it!"

"Well that's not going to happen, Kenny," she said sternly. "I told you that there were lines we simply could not cross. What has gotten into you today? Does this have anything to do with what your sister said? What on earth has you so angry?"

"She made a wise remark about our relationship, that's all. It just struck a nerve."

"Our relationship?" asked Anna-Marie, very surprised.

"Yeah, she was busting my chops about us not having sex yet," he replied, knowing that he had just opened the lid on Pandora's box even further.

Anna Marie was incensed. "What business is it of hers whether or not we have had sex?" she shrieked. "Your sister is a whore Kenny! She will let guys do anything to her."

"For that matter, why on earth were you discussing sex with your sister. What are you, some kind of freak? Go home and ask her to jerk you off. I'm sure she would," she screamed with angry sarcasm.

"I just want you so badly," he explained. "If find you so attractive and sexy and when we kiss like this it makes me want to go further with you."

"Well, if that's that case then the kissing needs to come to a halt," she said firmly. "And quite frankly, I'm not so sure that I want to even be with a man that discusses sex with his sister. That's sinful and disgusting. Take me home, now!"

Kenny knew that he had probably dropped Anna-Marie off at her house for the last time. He had wanted her so badly. He needed to feel her touch. But there was no way both of them could be satisfied with the current relationship. Most assuredly, she would say something to her father about this and there was no telling what kind of grief would come from that.

He drove around several hours that evening, defeated and depressed and still horribly sexually frustrated. He thought of pulling over and jacking off to get some relief. It had been over two weeks since he had cum. He was so sure that tonight would be "the night" for he and Anna-Marie that he wanted to be full of spunk and impress her with a huge explosion of his manhood.

He finally pulled into the driveway and reached the back door to the house at about 1 AM. He let himself in with his key as he walked past his sister's room he noticed that the door was cracked and the TV was on.

He put his head to the door and said softly, "Hey Tree, you still awake?" Tree had been his nickname for has sister as long as he could remember.

"Yeah, I just finished watching a movie," she replied, "You can come in."

She reached over and flicked on the bedside lamp and as she did, Kenny could see that all that she was wearing was a pair of tiny pale yellow bikini panties and very tight t-shirt with the words, "Daddy's Little Princess" stretched across her gigantic jugs. She was not wearing a bra and her nipples were clearly visible through the thin material.

"Great," thought Kenny, "After all this, I come home to a half-naked teenage girl with a gigantic rack. I can't catch a fucking break."

He struggled to keep those thoughts out of his head as he sat down in the chair across from his sister's bed. She leaned back on a pillow, on top of the covers and Kenny could not resist looking at her long, tan legs as well as the space between them. Her tiny panties did little to conceal her neatly trimmed mound. Her manicured patch of dark brown pubic hair was clearly visible through the sheer light yellow material.

Kenny wasn't sure if his sister was purposefully letting him see her like this or if she simply didn't give a shit if he saw her or not. She always walked around the house in a t-shirt and panties, but he never really paid much attention.

But tonight, considering what Anna-Maries had said about his sister's promiscuity, the evening's events and the condition he was in, he carefully studied everything that she allowed him see. The sight of her sitting there rekindled the stirring in his trousers and he could feel himself beginning to grow stiff again.

Theresa immediately took note of his bulge.

"You were gone so long, I was sure that you your sweetheart had finally got down to business," she said. "But from the looks of that mound in your pants, I'm guessing that she only took you halfway there again. Am I right?"

Kenny was embarrassed. He muttered a yeah and then let out a deep sigh.

"Aw, poor thing," said his sister, as she shifted her legs, now sitting criss-cross, giving her brother a better view of the crotch of her mostly transparent panties. Kenny could clearly see the outline of his sister's pussy lips through the material.

"From the looks of it, she took you pretty far. There's a couple of tell-tale spots on the front of your pants," Theresa said, pointing out the evidence of some pre-cum leakage from earlier in the evening. She was now paying very close attention to the swelling in her brother's crotch. She began to wonder how big he might actually be. Theresa was very much the size queen. She dated several boys in high school that were infamous for their large members. She couldn't resist a big cock—even if it belonged to her brother.

Kenny's mind was racing and he was beside himself. He began to tell her everything. He had nothing to hide. Maybe his sister could offer some advice. He was desperate for some relief. Maybe Anna-Marie was right about that too. Maybe Theresa would be willing to give him the physical relief he needed so badly.

"It was getting very hot and heavy and she was rubbing my cock through my pants," he told her.

This immediately got Theresa's attention. Nobody got turned on more by a dirty story than Kenny's sister. She leaned forward in delight, allowing the heel of her foot to rub up against her clit as she listened.

"So did you have you hands on her?" she asked eagerly.

"Yes, I had slid my hand up her skirt and was rubbing her through her panties," he told her and as he did, he felt his dick get even harder. There was really no way to hide his hard on any longer, so he sat back and spread his legs apart to give his growing cock some much needed room and to give his sister a better view of his package.

"Mmm, was she wet?" asked Theresa, now with her eyes glued to front of her brother's pants, which were beginning to show another spot of moisture.

"Yes, she was very wet," he answered and then he looked at her and asked, "Is this making you wet?"

She grinned at her brother with only a little embarrassment. "Yes, I just love to hear nasty stories. Sorry if it creeps you out, it's just so hot that my big brother was able to make the sweet little Catholic princess's pussy wet."

As she spoke, she got up from the bed and went over and closed her bedroom door. She was sure that everyone had been asleep for hours, but there was no sense taking chances. She wasn't sure what exactly was going to happen, but her desire was growing rapidly and her pussy was soaking wet. Her immediate objective was to get a good look at her brother's gigantic dick.

Instead of going back to the bed, she knelt down at Kenny's feet as he leaned back in the chair. She folded her hands and placed them on his knee and as he watched her gaze at the huge bulge in his pants, he began to sense that she was very willing to do what Anna-Marie wasn't.

"So, what happened then?" she asked as she moved her hand up her brother's thigh and began massaging his cock through his pants. "She was rubbing you like this, right?"

This sent a shiver down Kenny's spine and he did his best to answer her. He glanced down and noticed that that Theresa's free hand was down her panties, giving her wet twat a good fingering.

"Yes, that's exactly what she was doing and it was driving me crazy," he said. "So I started to undo my pants and that's when she completely freaked out!"

"Aw, Kenny honey, I can't believe she got so upset" sympathized the little sister. "Tell me why you wanted to take it out of your pants. Did you want her to see how big and hard it was?"

"Yes, that's exactly what I wanted," Kenny answered, breathlessly.

His sister then looked straight into his eyes and said, "You can take it out for me. I want to see it Kenny."

"Are you sure," He asked. Theresa nodded with great anticipation at the prospect of seeing her brother's undoubtedly enormous penis.

Kenny began undoing his pants, just as he did in the car with Anna-Marie. Only this time the woman with him was his little sister and she wanted to see it in all its glory. He unbuttoned his trousers and lowered the zipper of his fly. He then stood up and stepped out of his shoes and let his pants fall to the floor. The gigantic pole in his now very damp briefs was directly in front of his little sister's face as she knelt before him.