Kyle's Big Dilemma

* All characters, places, events and information given in this story is fictitious. Any resemblance to persons living or dead is coincidental.

* All characters are 18 or over.

* Constructive criticism is greatly appreciated but flaming, insulting comments will be deleted. Thanks.

* This story contains incest, group sex, male bisexuality and female bisexuality. If you're squeamish about any of those subjects, please be forewarned.

* Thanks to CKite for feedback that gave me an idea used in this story.

***

Kyle closed his little lunchroom promptly at two o-clock and drove the familiar quick route home. If asked how his day went at work, he'd say 'okay' though he couldn't remember a single thing about it to save his soul. His mind was occupied the whole time about his sister, Randi, and the girl he wanted to date, Michaela. (Kyle and Michaela, while on their first date, found Randi on top of the high bridge and were afraid she was planning to jump in the river. Michaela let the twenty year old Randi stay the night with her so she could help the distraught young woman. Unbeknown to Kyle, Michaela seduced Randi to prove to her she wasn't ugly because of a crooked eye that she was ashamed of.) The handsome twenty-two year old parked his convertible in the driveway and walked with an eager stride into the house.

"Hi, Kyle," Randi greeted him cheerfully.

"Hi, Sis," he replied. "You're looking bright and cheery today. How'd it go last night with Michaela?"

Randi was sitting on the sofa looking prettier than he'd ever seen her before. Randi was nearly twenty-one and appeared to be happier and more relaxed than he'd seen her in years. Kyle decided to sit beside her and talk with her. He still felt concern about his younger sister and he wanted to make sure she was okay emotionally after the ordeal the night before. It was a scary situation for everyone concerned.

"I had so much fun with Michaela, Kyle. We talked a lot and I promised her I'd never do anything to hurt myself, but I wasn't going to jump off the bridge. I know everyone thinks so, but I wasn't!"

"Well you sure scared the shit out of everyone, running off like that and me and Michaela finding you on top of that bridge late last night."

"Oh, I'm sorry, Kyle," she apologized. "I just wanted to do some thinking and wanted to be alone for awhile. It won't happen again."

"You seem different today, not as depressed and as indifferent like you normally were.

"Oh, Kyle, I really am different thanks to Michaela!"

"Wow! You two really hit it off, ay??" Kyle exclaimed. "It must have been some sleepover. You really like her, huh?"

"Oh, yeah! She and I became instant best friends! I like Michaela so much."

"Well, I like her a lot, too, in fact, I think I love her, but I doubt she'll go out with me again after the way our first date went."

"Hi, Kyle," Michaela, an eighteen year old light blond Swedish girl with a cute Swedish accent said from behind him.

Kyle spun around in surprise, not believing his ears.

"Michaela! What - how long have you been here?" he grinned, happy to see her. "Man, what a surprise!"

Michaela sat beside him, sandwiching him between her and Randi.

"I brought Randi home about thirty minutes ago, long enough to hear everything you said," she smiled. "And, yes, I'll go out with you again. - But there might be a condition after last night."

"A condition? Oh?" he replied quizzically. "And what would that be?"

"You might have to date both of us," Michaela replied point blank. "What do you think about dating two girls at once?"

"What?!!! Guys don't date their sister! That's crazy," Kyle scoffed.

Michaela noticed Randi crawling back into her shell full of depression and hopelessness. Michaela found out during the sleepover that Randi was in lust with her brother and wanted him to have sex with her. Because of Randi's unstable mental condition at this point, Michaela agreed to let her be there if and when Michaela had sex with her brother, Kyle. She wanted to fuck him too. Lust for her brother, Kyle, plus anguish over her crooked eye was unbearable for her.

"You won't be dating just your sister, you'll be dating me and taking your sister along with us. If you don't, then I'll just have to date her myself!"

Kyle looked at her with an expressionless stare, his mind working overtime to figure it all out. He looked at Randi a bit, then back at Michaela.

"What happened last night? Are you telling me you're a lesbian or something? What are you trying to tell me?!" he finally managed to squeak out.

"I like you a lot, Kyle. No, I'm not a lesbian, but in all fairness to you I need to tell you right up front before we date and become close, I'm bisexual, Kyle."

Kyle looked deep into Michaela's eyes as if he were trying to hypnotize her. Slowly his lips began to curl up at the corners and he took on a mischievous little grin.

"So, last night, you and Randi -? Well I'll be dog gone!" he chuckled. "The girl I hoped to make my girlfriend has become my sister's girlfriend."

"Yes, Randi and I had sex last night, Kyle. Your sister is not a mechanical object. She's a warm, loving, sexy young woman who has needs too, just like you do. See how happy she is today? Some of those needs of hers have been met but there's still more, Kyle. I'll let her talk to you about that and I hope you'll be sensitive enough to listen to what she has to tell you."

"So, isn't it a little bit weird to take your sister on a date with you so she can have sex with your girlfriend, too?"

"Yeah, that would be a little bit kinky, but you're not fully understanding what I'm saying," Michaela said patiently.

They had to put their conversation on hold when their younger brother, Bobby, came into the house through the back door. He went into the kitchen to get a drink of water. He's a good looking young man of eighteen but not quite as handsome as his older brother, Kyle.

"I talked to my friend, Edwena, and she invited us over to her house for a little party tonight if you feel like taking us, Kyle."

Bobby walked up and, like all little brothers, was all ears.

"You guys are going to a party tonight?" he asked.

"Yeah," Randi stated. "You have a date tonight, don't you?"

"I'm going to the movies with Geri Ann," he answered. "You have fun tonight, Sis."

"Thanks, Bobby. I plan to," she smiled.

Bobby went back outside and dove into the pool.

"Alright, we'll give it a try," Kyle smiled. "I guess being alone on a date with Michaela is out of the question for now. But at least it's a date"

Michaela stood close to him and softly said, "I guarantee you you'll not mind it one bit, Kyle."

Kyle was not a virgin and, in fact, had sex quite a bit in the last four years of his active sex life. It was usually in the back seat of his car parked on Overlook Mountain and a strictly one on one situation. He was totally unprepared for Michaela who constantly kept him guessing. All he could do was smile and let her kiss him quickly on his lips.

"Okay," he finally replied. "I want to go out with you so bad I guess I'm willing to do most anything. Gee, I must be going crazy!"

"Randi, put on those dark glasses we bought you this morning," Michaela requested.

Randi got the dark glasses out of her purse and put them on.

"It's dark in here," Randi chuckled.

"You look like a blind girl now," Michaela said. "You can walk around in public now while holding my arm or your brother's arm and no one will raise an eyebrow. They're used to seeing blind people holding other people's arm while being guided around."

"You're so cunning, Michaela!" Randi exclaimed. "Why don't we take a swim in the pool this afternoon then go out for dinner? I'm sure the chef here could recommend a good restaurant for us."

"That sounds good to me," Kyle smiled. "It's a date!"

*

"Dang, Sis! You look pretty hot for a blind girl," Kyle said, looking the dark haired beauty up and down in her tight fitting bright red dress. "Every brick is in the right place, too, as far as I can tell."

"Thanks, Bro," Randi smiled. "You're looking handsome in your sports jacket there, son."

Michaela stood and smiled at them. In her dark green, short dress and long, light blond hair she was no less than hot in anybody's book. They were standing in the foyer of the Gardenia restaurant and were attracting many appreciative glances. A waitress came to lead them to their table and Michaela could hear a few low wolf whistles as she followed Randi and Kyle to their table. Randi giggled when she heard the whistles.

"Three steaks medium well done and a bottle of red wine," Kyle ordered.

"Chianti?" the waitress asked.

"That'll be fine." As the waitress left he leaned in and said in a low voice, "Dang, did you hear the wolf whistles? You should have seen the jealous stares I got from some guys. This dating two beautiful women is not so bad after all."

"Do you really think Randi is a beautiful woman?" Michaela smiled.

"Hell yes!" he replied. "Beautiful and sexy."

"You should tell her that more often. All women want to hear that as often as they can."

"Yeah, I love to hear it," Randi agreed. "It makes me tingle all over."

"Especially in one particular spot," Michaela quipped.

"Yeah!" Randi cheered, causing people to look at her.

Kyle cleared his throat nervously and said, "Well, being brother and sister, I don't see where that's of any use at all."

"Oh, - and who says so?!" Michaela said with a daring look in her eye.

Once again Kyle was surprised by Michaela's comment, not knowing exactly what she meant. Was she saying it was okay for a brother and sister to have sex?! Nah! It must be her cute little Swedish accent that makes him misunderstand her.

"Well, brother and sister just can't do those things," he squirmed.

"Statistics show that forty percent of siblings experiment sexually, mostly before the legal age of consent. They can't know for sure because most people refuse to talk about it. Here you are, two adults above the legal age and able to decide for yourselves whether you should do it or not. Why let others make that decision for you?"

"Kyle, I don't know any other way to say it so I'll just say it. I have wanted to have sex with you since puberty," Randi said softly.

"That is one of the things that caused her depression and strange behavior. She felt evil for having desire for her older brother but she just couldn't help herself," Michaela explained. "Haven't you noticed she never had many friends, especially boyfriends? She had to turn to someone."

"Damn, I was so busy dating all the girls at school that I never noticed my sister, Randi! Dang, Randi, I don't know what to say."

Kyle remained silent through dinner as the blocks of realization and understanding fell into place. After dinner and over their last glass of wine, the bottle being empty, he decided to speak again.

"Look, I'm not very smart but I catch on quick," he said. "I'll try and see what I can do. Randi is a beautiful and desirable young woman but I may have trouble with the sister thing. I'll do my best though, understand?"

"Have I ever told you how wonderful I think you are?" Michaela said.

"Yes, but tell me again. I think I need further convincing," Kyle quipped.

*

Kyle, Michaela, Randi, Edwena and Eldon were sitting around the living room, drinking champagne and talking about light stuff. Edwena thought about flashing her pussy at Kyle but decided not to start the night off so suddenly. Instead she put on some romantic dance music on the stereo. There must have been speakers all over because the room was filled with beautiful, romantic music.

"How about dancing with me, Kyle?" she asked.

"Sure," he said, standing and taking Edwena in his arms.

Michaela noticed how good a dancer Kyle was.

Edwena's husband, Eldon, came over to Randi and asked her to dance with him. Both he and Edwena were completely filled in by Michaela about Randi and her circumstances and they were going to do everything to facilitate the proceedings. Eldon took her tenderly in his arms and spoke a few quiet words to her while dancing. Soon Randi laid her head on his shoulder and he began to cup her butt cheeks in his hands. Michaela smiled, knowing what a delight those wonderful globes were to hold, but Kyle was staring at them in awe when he got the chance.

"Your sister is such a beautiful girl, don't you think, Kyle?" Edwena asked him.

"She's gorgeous," Kyle exclaimed.

"She's sexy too. Just look how they're dancing," she continued.

"Yeah, she sure is. - but he's your husband!" Kyle added.

"Oh, it's alright, we're both secure in our relationship. We don't get jealous of one another. - You can dance with me like that if you want to. Do you like dirty dancing?"

"Yeah, but Michaela -"

"Oh, she won't mind. She and I are good friends!"

Kyle gave in and put his hands down on Edwena's hips, inching them toward her luscious butt cheeks. Edwena took his hands and placed them square on her ass cheeks and pulled into him close. He looked at Michaela nervously but she was only smiling at him.

"Michaela tells me you think I have nice legs. Does my thigh feel good between your legs?"

"Ah, - yeah, it does," he squirmed.

"Your leg feels good between my thighs, too. Do you know what it's doing to me?"

"Yeah, the same thing you're doing to me," he gasped.

"That's right. Hey, why don't you dance with Michaela while I cut in and dance with Randi?" she suggested.

Just then the doorbell rang. Edwena excused herself and went to answer it. Michaela stood and took Edwena's place and began dirty dancing with Kyle. As Kyle held her tight and danced close with her, he thrust his leg between hers and began dancing very dirty. Their dancing was so racy that, if they had been naked, they would be having sex.

"Hey, everyone!" Edwena exclaimed. "Look who's here!"

Kyle jumped back from Michaela like he had received an electrical shock and stared open mouthed. The poor guy was almost going into cardiac arrest when his eyes feasted on the beautiful Sylvia Swenson, Michaela's mother, looking more gorgeous than ever. She was forty but she looked not one day older than thirty.

"Hello, Kyle," Sylvia smiled at him. "Please, don't let me interrupt your dancing. You two make the cutest couple."

Eldon walked up and took Sylvia in his arms and started dancing with her without even asking. Kyle saw Edwena start dancing with Randi so he resumed dancing with Michaela, though not quite as racy now.

"Your mother is alright with us dancing so close together?" Kyle whispered to Michaela.

"Of course," Michaela replied. "She understands, she's a woman too, you know. Where do you think I came from?"

Kyle pulled Michaela in tight and went back to dirty dancing. Needless to say, the feel of Michaela's lithe, luscious body pressed against him plus the sight of the dirty dancing going on around him gave him a raging hard-on. He beheld Sylvia as she danced with Eldon and felt envy for the man. How he wished it was him dancing with Sylvia. He kissed Michaela's neck in apology for his thoughts about her mother, though she didn't know about them. He looked at Eldon and had to admire the man. He was a good ten years older than Kyle but his handsome features, suave manner and confident comfort level in every situation made him easy to like.

"I need some more champagne!" Edwena said as the song ended and a commercial began.

Eldon filled everyone's glass, finishing the bottle of champagne. "To us," he said, raising his glass.

They each finished their drink, doing more giggling than talking. The wine earlier and now the champagne left Michaela, Randi and Kyle a bit tipsy and daring. Michaela stood with her arms hanging on Kyle's neck. She left Randi room to put her arms around Kyle's waist and kiss his cheek.

"Michaela, why don't you show Kyle and Randi to our guest room while we entertain Sylvia in our bedroom for a while?" Eldon suggested.

Eldon walked away with a hand on Edwena's ass and a hand on Sylvia's ass, squeezing each one firmly and caressing them both. When the trio got to the stairs, Eldon left no doubt as to the purpose of them going up stairs by lifting Edwena's skirt to expose her bare ass cheeks and giving them a couple of love smacks while smiling at Kyle.

"Damn! He's going to fuck both of 'em?" he asked quietly.

"Sure," Michaela answered. "Momma has a threesome with them every so often. She was here last night if you recall."

"Fuck! How did that happen?" Kyle asked in amazement.

"Actually it started right after I started working with Edwena. She was afraid her marriage to Eldon was headed for the rocks so I volunteered to help her save her marriage. To make a very long story much shorter, Edwena and I ended up in bed together for her first time while Eldon was out of town on business. Edwena thought he was fucking his secretary and wanted to confront him. Well, when he got back we cajoled him into admitting he was bisexual. Since Edwena was as guilty as he was, they could get a divorce and share time with their son or allow each other to have their little bisexual flings and stay together. They made the later choice which has turned out very well. Don't you think so?"

"They have a son?!" Kyle asked in surprise.

"Yes. He's at his grandparents now so we can have our party tonight."

"Ow, fuck, my head hurts," Kyle moaned. "It's gonna take me a while to assimilate all that shit. Boy, you get the job done when you put your mind to it, don't you! Edwena and Eldon, bisexual? And they have a kid?""

"Oh, come on now," Michaela chided. "If people like sex, they like sex. We shouldn't put restrictions on it."

"So, let me get this straight," Kyle mused. Eldon is bisexual and has sex with other guys. You, Edwena and Randi are bisexual because you have sex with each other."

"That's right," Michaela said.

"That makes you the odd man standing," Randi quipped.

"So, come on, let's go to the guest room and discover how much fun we can have together," Michaela suggested. "Nobody will have to do something they don't want to do, so relax."

Michaela led the way upstairs to the guest room. Once inside the room, Michaela pushed the door closed not bothering to lock it.

"Now, the first thing we should do is help each other undress," Michaela said. "We'll alternate directions with each piece of clothing until everyone is undressed. Okay?"

Michaela helped Kyle take his shoes off, Kyle helped Randi take her shoes off and Randi helped Michaela take her shoes off.

"Now we switch directions," Michaela said.

Kyle nervously pulled the zipper to Michaela's dress down and helped her out of her garment. Michaela then helped Randi out of her dress. Randi, feeling a little bit shy, helped Kyle off with his socks but she couldn't stop staring at the bulge in the front of his jeans caused by his swollen, throbbing cock.

"Change direction again."

Michaela pulled Kyle's shirt out of his pants and helped him off with it. Kyle looked Randi up and down as she stood before him in stay-up stockings, panties and matching bra. He nervously knelt down and rolled the stay-up stocking down her lovely left leg.

"There," he said proudly.

"No, hunt-uh, Bro, I took both your socks off, now you have to take off both my stockings!"

"Oh, alright," he mumbled.

He rolled the other stocking down and off her other leg and handed it to her. He noticed a fragrant aroma of a woman's vulva wet with excitement coming from her as he stood up. Yeah, Randi was trembling with nervousness but Kyle's heart was beating so hard you could take his pulse by watching his temples.