The late September chill had come on so gradually that the young honey blond woman did not notice it until she stepped into the house. As the warmth enveloped her, she looked down at her slender tanned arms and saw the goosebumps. She would have to put an end to these little shows, she thought, at least until Spring. Then again, if what she had seen in her brother's window was any indication maybe the shows would be unnecessary from now on.
Entering the living room from the kitchen, she was confronted by an unusual sight. Framed in the wide open front door was the skinny figure of her brother, Jerry. Unusual because he was standing there naked, except for a ridiculous looking pair of black dress socks.
"Jeez Jerry! What's gotten into you?" She exclaimed. The question snapped him out of his reverie and he turned towards her, closing the door behind him. Though clearly embarrassed he didn't try and hide his erection. Her eyes were drawn to her brother's stiff cock as they were to any cock that happened to come her way. It was definitely smaller than most of those she'd seen.
Though not a math genius like her brother, Diane could add one plus one and get two. Jerry's smile and nakedness added up to a story of success for their little scheme. The terribly shy young man had evidently experienced a break through up in his room. She suspected as much when she had seen the broad naked shoulders and chest of her spectator. The sight of the tall man's body, naked for all she could see, was what had driven her sexy show from stripper fake to a truly smashing orgasm. She was warmed by the memory of the man's rhythmic upper arm movements. The arm betrayed what was happening out of sight.
"So it went well, did it?" she asked with the same smile.
Jerry nodded and replied, "Thanks to you Sis."
"It's what I do!" she replied, striking a sexy pose. Even though she was still naked after sunbathing, she knew the pose wouldn't have any effect on her brother. Not because she wasn't damn sexy, or even that she was his sister. It was because she knew her kid brother was gay. She'd known for years, well before he discovered it for himself. If he'd discovered it even yet.
"Well, run up to your room and you can tell me about it as soon as I throw on some clothes." She took her time following her brother up the stairs. Her legs were still a bit weak from the mind-blowing orgasm she'd experienced.
After she got to her room, part of her wanted nothing more than to collapse on her clothes strewn bed and recover. While sunning herself she'd received a call from one of her coworkers at the club asking for a favor. Since she owed the girl one, she'd agreed to cover for her tonight. She should rest up for a long night of performing. Thankfully it was Amateur Night, so the work load would be lighter than on a normal night.
Another part of her wanted to hear what had happened with her brother. It was this part which won out and made her look away from the bed. She picked through the clothes which were draped, piled and scattered on every surface of her room. Finally slipping into a pair of baggy sweat pants and an equally loose fitting T-shirt, she looked into the full length mirror by habit. "My brother is right. I'm a slob," she thought, surveying the reflection of the terrible mess behind her.
She was about to head for Jerry's room when she thought of something. She went to the night stand next to her bed and opened the top drawer. She stood contemplating the choices for a few moments. Which one would be best, all things considered? When she had decided she picked it up and slid it into the large pocket of her sweat pants. "Not too big and not too small," she thought.
"Wow! You must be proud of yourself, little bro!" Diane exclaimed when she saw Jerry on his bed, laying back with his red head on a pillow with a smile on his face. He was still as naked as he'd been downstairs. She had definitely not expected to see this. Normally painfully shy he had never started out one of their talks naked, let alone sporting an erection. His dick was small, but respectable on his slender frame and its bright pink color looked very nice with the rest of his pale body.
"I'm sorry Sis!" he replied apparently thinking he might have shocked her. His hand went to his groin covering the offending member. "I was just thinking about Tom," he explained.
"Your friend must be pretty special," she said, when she saw her brother's expression going all dreamy. She walked up to the bed and stood beside it looking down at the naked boy. He was eighteen, but was so slender he could easily pass for a Sophomore instead of the Senior he was. Not for the first time, Diane thought that with a different haircut and a bit of makeup her young brother could pass as her sister. For some reason the thought intrigued her.
"Oh, he is! He is!" he exclaimed. "He is a player on our football team, a linebacker, or lineman, or something. I don't know about those things, but he is tall, strong and handsome." He gushed as many of Diane's schoolgirl friends had gushed about their latest schoolboy crushes. As she herself had done before her introduction into the world of sex changed her expectations.
"Well, scoot over some and turn over, please," she ordered. "The last thing I need to see is your stiff wiener!" After her brother shifted to the opposite side of the bed and rolled over on his stomach, she laid down beside him. At first on her back, then rolling onto her left side, propping up her head so she could look at the naked figure next to her. His face was turned towards hers so she said, "Hi."
"Hi," he replied with a sheepish smile. "I guess you are wondering why I'm naked?"
The handful of previous occasions when she put on a show for one or more of Jerry's friends had been failures. After waiting for them to leave, she had found Jerry frustrated and horny. His hopes of her masturbation displays provoking a jerk-off party in his bedroom had gone unrealized.
Diane wasn't surprised by this. His friends were just too shy, and her brother even more so, to break through their sexual inhibitions. Perhaps his nerdy friends didn't even know how to jerk-off, though it seemed unlikely. She always thought it was just an internet inspired fantasy of Jerry's, not something likely to really happen. She played along with her brother because she sunned herself in the afternoons anyway. Besides, she was a stripper.
"I assume it is because the two of you were jerking off while you stared me," she replied.
"That's not true, Sis! You know I never watch you doing that." he said in horror. For a minute she thought the boy might cry, he seemed so upset. To comfort him Diane gently ran the fingers of her right hand through his beautiful red hair.
"I know, I know you don't sweetheart, but I truly wouldn't mind if you did," she soothed him with her soft voice and gentle touch. She traced her fingertips down his neck to his boney shoulders. She marveled at her brother's fair skin and the sparseness of his golden-red body hair. How lucky he was, she thought. Imagine not needing to shave. At least not every damn day.
"Tom was!" the naked boy said, suddenly recovered from his funk. For a moment Diane didn't catch his meaning. "He was jerking off, big time," he added with a grin.
Her suspicions confirmed by his news, she felt stirrings in her pussy. "Did you get to see his cock, dear?" she asked, her interest aroused.
"Boy! Did I?!" he exclaimed, his eyes bright. "He stripped naked, before he even saw you!"
"He is a horny bastard, isn't he?" she said.
"That's because he ..." he began. His eyes shifted away from her as if he had something to conceal. Diane brought her hand down to his rib cage, giving it a little tickle.
"Come on, tell me, or you know what's coming next," she threatened. It was a tried and true method for getting what she wanted from her little brother.
"That's because he had been sniffing your panties!" he said. "Don't tickle me, please!"
She laughed aloud at the news. "Did he like the aroma?" she asked, realizing the panties in question had most likely been the pair she had worn home from the club very early in the morning. The very damp panties she had tossed in the bathroom hamper.
"I guess so. He ...," again he stopped evasively. Another slight movement of her fingertips on his naked rib cage brought out the rest. "Don't be mad at him, but he put them in his pocket."
"I can't be mad at one of my fans can I?" She had lost count of the number of times one of the men in the audience absconded with the flimsy panties she tossed to them. Usually she got them back, but it was one of the costs of being a dancer. The thought of her brother's friend taking her soiled panties to enjoy later turned her on.
"Was he already hard just from the smell?
"No, he didn't get hard until he saw you." the boy answered. Then getting that dreamy look in his eyes again he added, "I got to see it grow. He didn't even mind that I was watching."
"Mmmm, sounds nice. Describe it to me," she purred rubbing her thighs together.
"It was big before it was hard, but it was huge when it was erect. It was beautiful." He said this with his eyes shut as if replaying the scene in his head. This didn't do Diane any good though. She needed more detail to be able to picture the man's cock. She knew they came in many shapes and sizes, each beautiful in its own way.
"No, describe it to me," she insisted. "Like, was it cut or uncut? Smooth or hairy? Small or big head?"
Her brother took a gulp and answered, "Well, it was circumcised, shaved, and it had a big flared head."
With that Diane was able to draw on her limited, but growing, experience to form a picture of the cock. She knew it was probably very different than than the cock of her brother's friend. The cock that came to her mind was a cock seared in her memory. Her first cock had been all those things. The thought made her want to reach down and rub her moist pussy.
"And it felt very hot and it tasted delicious."
Diane was taken aback at these words. No wonder the little guy was feeling so happy. It had gone much better than either of them could have hoped for. The cock which filled her thoughts had been both of those things as well. "Mmm," she purred remembering its heat and flavor. To keep herself from toying with her throbbing cunt, she began caressing her brother's smooth back. From his shoulders down to the small of the back, her touch brought a sigh of pleasure from his lips.
His eyes which had been shut while he spoke of his friend's penis, fluttered open. "Sis ... could you do that thing. You know ... that you did last time?" he asked shyly.
She looked at him with an expression of mock surprise, "Well, that depends on if you get up and bring me the lube."
Her brother smiled as he brought out a small container of Vaseline from under his pillow. She had given it to him after their last talk. "In case you want to practice," she'd told him.
On that occasion she had come upstairs and found him crying in frustration. Her show had again failed to provoke the hoped for sexual release for him. His friends had rushed off to their homes, no doubt to beat off in private. Diane had managed to calm him down and somehow talked him into taking off his jeans and underwear.
The most he had done up to then was to undo his belt and jeans. He'd slid them down his slender hips along with his underwear and lain face down on the bed. He always kept his shirt on. On those occasions she had encouraged her brother as he rubbed his erection against the comforter. The most she had done was whisper nasty words into his ear, though once she caressed one of his naked round ass cheeks as he came.
She had taken it up a notch during the latest episode. After she had talked him out of his jeans and underwear, her brother had began masturbating against the bed. She'd taken the container of Vaseline out of her pocket. Then scooped some it up with a finger. Whispering nastiness in an ear, she had slowly brought the lube coated tip of her middle finger to the boy's tiny asshole. He had tensed at the first teasing touch, let out a moan of pleasure and shot his load of cum. It was over in a flash.
"Wow!" he had cried out. "That was fantastic, Sis. Thank you! I love you so much." It had made Diane warm all over to be able to give her kid brother so much pleasure. It'd been very pleasant indeed if the volume of semen produced was anything to go by. Meager in comparison to other cum-shots she'd a hand in producing, it was the largest her brother ever shot. He said so himself as he scooped up as much as he could with a finger and brought the cream to his lips. It was something she'd never seen a man do before and it turned her on tremendously.
This time he was already naked. "Like a boy scout, always prepared, aren't you?" she teased. She took the container from his hand, removed the lid and inspected its contents. "You haven't been practicing," she accused when she discovered the jar remained as full as the last time she'd held it.
"Well, I tried to once, but ... it wasn't the same," her brother replied shyly.
He made a good point. She had to admit it didn't feel nearly as nice, or naughty, to finger her own asshole as it did when someone else did it. "You really need to practice if you're going to be ready. I can't do it all," she admonished.
She figured her brother wouldn't be able to take the dildo she'd chosen for him. A week after their last session she expected he would've explored his ass to at least the first knuckle. "Well what's done is done. Or rather, what's not done is not done,"' she thought.
"Ready for what?" Jerry asked.
She set the container atop one of his naked ass cheeks and reached into the pocket of her sweat pants. "For this, among other things," Diane replied pulling out a pink plastic dildo from the pocket. She held it in front of his face and smiled as his eyes almost bugged out in surprise.
"It's too big, Di!" he exclaimed in fear. His smooth cheeks clenched together as he preemptively protected his anus.
"Don't be silly! It's not even ..." she stopped herself before finishing the ego deflating comment. It wasn't even as big as his cock. "Well anyway, I'm sure Tom's cock must be bigger than this little old thing." she said with a grin.
"Oh yeah! He's much bigger!" the redhead agreed, closing his eyes again.
She held the four inch dildo touching it to the boy's lips and watched them part to accept its tip. For some reason it turned her on to no end. She moved it in and out, thrilled to see him giving it head. "Here, you take it," she commanded and he took it from her. He continued the dildo's in and out movement himself.
The young woman picked up the container and sat up cross-legged on the bed next to her brother's nicely rounded ass. He was lost in images of his friend's cock. She saw him begin to grind his hips as he fucked the comforter. Again she couldn't help but think he looked like a slender young girl laying there naked.
Using her middle finger, she took a generous scoop of greasy lube from the container. Setting the container aside, she placed the tip of the lubed finger against the pinkish puckered hole which was her brother's anus. She half expected he would orgasm immediately again, but all that came out him was a sigh of pleasure. As she teased the ring of his sphincter spreading the Vaseline liberally, his sigh turned to a moan.
The moan became a groan as Diane pressed the tip of her middle finger into the tight ring. The young man's hips thrust against the bed in an attempt to escape the intrusion, but she persisted. She didn't press it in further, but she wasn't about to give up on her brother's training so quickly. It was up to her to get him ready.
She held her finger steady until his groans subsided, then eased it in slowly to the first knuckle. The movement brought another groan, so she withdrew her fingertip slightly. The groan changed to a moan. Back in went her finger, then out again, over and over.