Kyle's Big Dilemma

"I meant to tell you, Sis, - you sure do have nice legs." Kyle said, breathing hard with sexual excitement.

"Thank you, big brother! Coming from you, that's a wonderful compliment." Randi panted.

Randi quickly rolled Michaela's stockings down and off.

"You go first this time, Kyle," Michaela said, standing before him in her pretty lacy bra and panties.

Kyle unhooked her bra and watched her as she slid the straps down her arms, holding the cups to her breasts as she pulled her elbows free. Then she slowly let her bra fall forward to expose her pretty pink nipples and tossed her bra aside.

"Michaela, you're so beautiful," he exclaimed breathlessly.

Michaela unhooked Randi's bra and let her take it off to toss it aside.

"You think I'm beautiful? What do you think of these gorgeous breasts? " Michaela asked. "They're bigger than mine and look how pert her nipples look standing so tall! - Okay, your turn, Randi."

Randi smiled like she's collecting a lottery payment. She undid Kyle's belt, unbuttoned the top button, and tugged the zipper on the fly all the way down, all the while looking at Kyle and smiling. The pants slid down his legs then and she pulled them away, breathing hard as he stepped out of them. Randi stared at the bulge in the front of his cotton shorts then stood up slowly, hardly able to take her eyes away from the tantalizing sight of her brother's cock bulge.

"Are we going too fast for anyone?" Michaela asked them. "Anyone want to back out? If not, we'll do the last item followed by an embrace and a long kiss. Randi, would you like the honor of pulling Kyle's underwear off?"

Randi knelt in front of Kyle and slowly, ever so slowly, pulled the cotton shorts down Kyle's hips. Randi watched the pubic hair appear, then the base of Kyle's shaft, then more of the throbbing shaft, then suddenly the entire shaft sprung free and bounced before Randi's awe filled eyes. Randi gazed at the soft, light flesh colored, velvety head with just a trace of pre-cum in the small oblong hole at the tip. She stood and let Kyle take her into his arms tenderly to give her a long, sweet kiss on her trembling lips. Her hand went down to take hold of her newly won prize, Kyle's stiff, throbbing cock. They both enjoyed the kiss and embrace beyond which words could express. They came apart, breathing heavily with desire.

"Now, Kyle, why don't you remove Randi's panties?"

"Turn around, Sis," Kyle said softly.

Randi stood with her back toward him while he knelt and slowly pulled her pretty panties down her legs. He handed her the panties and stood up as she slowly turned around to face her brother.

"My god, Sis, you're gorgeous!" Kyle breathed out. "I must have been blind all these years!"

Kyle and Randi embraced and kissed again but this time with more passion and urgency boiling in their blood veins. Kyle's cock slid between Randi's thighs and rested against her pussy lips. They ground their hips against one another as they kissed and Randi became weak in her legs, moaning loudly as her hips gyrated against Kyle. She shuddered and trembled in an orgasm.

"I told you she was a sexual creature, Kyle," Michaela chuckled. "Now it's my turn. One of you take one side of my panties and the other one the other side and pull my panties down together."

Michaela turned her back to them and let them pull her panties off her. She turned and embraced Randi and gave her a hot kiss on the lips. Then she turned and embraced Kyle, kissing him with a dueling tongue. They ground their pelvises together hungrily. Michaela put her hand down to check out Kyle's erection. It was between seven and eight inches long she estimated and just thick enough to provide a good hand full. Not something to write home about but certainly not something to be ashamed of, she thought.

"Oh, Michaela, I want you so badly! I love you, I could never love anyone else the way I love you," Kyle panted with desire.

"Do you love Randi, Kyle?" Michaela asked.

"I've always loved Randi, she's my sister. I just found out tonight just how much I loved her," Kyle confessed. "But I still love you more, Michaela."

"Lay in the middle of the bed and show us how much you love us so we can believe you. You can start with me then show Randi how much you care about her. Alright?" Michaela requested.

Kyle got on the bed on his back and Randi and Michaela laid down on their backs beside him. He couldn't believe how lucky he was to have not one but two beautiful naked women with him, one on each side. He gasped when his sister, Randi, took hold of his cock and gently slid its head between her lips. He saw her take off her dark glasses to study his sturdy manhood with loving appreciation.

"Do you realize how long I've waited for this moment, Kyle? Now here it is, the fulfillment of a ten year long fantasy, thanks to Michaela. I believe I love her as much as I love you, Bro. Is that alright?"

"God, yeah, it's alright," he gasped. "I'm sorry I didn't know. Why didn't you make a move on me?"

"With my crooked eyes?" she scoffed. "I figured I was too ugly to compete with the cute girls you were going out with."

"Like who!" Kyle retorted.

"Like Arleen," was her reply.

"Ah, Arleen, the drama queen of the eleventh grade. Yeah, she was pleasant to look at, but snapped like a bear trap if I touched her legs anywhere above her knee. I did manage to get her to give me blow jobs but her teeth scratched my dick so bad I'd lose my hard-on! Yeah, tough competition there."

"Well, I wasn't there! How was I supposed to know?" Randi whined.

Michaela chuckled at the conversation the brother and sister were having. She leaned in and licked Kyle's cock up and down the sides. She was joined by Randi who licked the other side of Kyle's throbbing cock. Michaela backed away as Randi took the shaft into her mouth and put as much of it into her mouth as she could possibly get in it.

"Oh, god, Randi, you do that so well, a hundred times better than Arleen."

Michaela took his cock into her mouth when Randi went up to give Kyle a loving kiss. She savored Kyle's beautiful cock, enjoying his taste and texture immensely as she slowly bobbed her head up and down. She French kissed the seven inch dong like a dog licking a ham bone, her tongue making contact with every inch of the velvety shaft.

"Oh, Michaela, you do that so well, too!" Kyle gasped.

Randi popped Kyle's cock back into her mouth making sure her teeth didn't touch it and tried once again to see how far she could get it in. She watched Michaela gently sucking Randy's balls as she tried to swallow the whole shaft into her throat. Her heart pounded as she took her handsome brother's beautiful cock deep into her mouth.

"Kyle, your cock is so wonderful it makes me want to learn how to deep throat so I can get the whole thing into my mouth and throat!" Randi exclaimed.

"Oh, fuck, Sis, you can practice on me any time you want to!"

"So, what do you think about having sex with your sister now?" Michaela asked. "No more hang-ups about the sister thing?"

"No, she used to be my kid sister but now she's a gorgeous, sexy young woman who's hot for my cock!" Kyle answered. "How could I possibly have any hang-ups now?"

"Are you ready to fuck her then? I know she wants to fuck you, she told me so."

"I want to if it's okay with you," he answered. "I don't want to do anything to make you mad at me."

"I want you to, she needs you so badly," Michaela told him. But you'll have to take it slow at first 'til she gets stretched open some. She's really tight from lack of use. Let's get you lubed up and get her on top of you."

Michaela put her mouth on his throbbing cock again and released plenty of saliva on his cock for lubrication. She watched Randi straddle Kyle's hips to lower herself onto his waiting cock while she held the cock at the base to guide it home. She let out a sigh as she watched the cock enter Randi's vagina and slowly disappear into her tight love canal. She heard Randi start to cry softly, out of happiness more than anything. Michaela was so glad for her.

"Oh, god, I finally have your cock in my pussy, big brother. It feels as beautiful as I had imagined." Randi said while crying happily.

Randi had to stop and raise up a few times in the process to give her pussy a chance to secrete more lubrication for his cock to slide in further and further. Finally she could feel the cock deep inside her, touching her cervix causing her to shudder in a mini orgasm.

"Fuck me now, Bro. I've wanted you to fuck me for so long, now fuck me good and hard."

"Sis, are you on the pill?" he asked a little worried.

"No, Bro, I never was active enough to worry about it," she replied.

"Wait, I'll se if I can find something," Michaela said, looking in the night stand drawer. "Ah, Edwena planned ahead!"

Michaela handed Kyle a condom and some KY jelly. She watched him reluctantly pull out of Randi's sweet, tight pussy. Michaela took the condom and opened the package then used her mouth to put the condom on Kyle's hard cock. She applied some KY jelly over it and held it back in place for Randi to reclaim it in her wet, waiting pussy. Michaela noticed the cock slide in much easier this time due to the extra lubricant plus Randi's pussy had been stretched open a little the first time.

"Give the poor girl what she needs now. Fuck the shit out of her, Kyle," Michaela told him. "You can give her what I could never give her."

"Oh, yeah, please, Kyle. Please fuck the shit out of me," said Randi in a high voice full of emotion.

Randi began the rhythm and Kyle followed her lead, matching thrust for thrust. They worked so well in unison, Kyle's cock would slide from cock head to balls deep inside Randi's tight, wet, hot love canal and back again without a hitch. Randi shuddered in delightful orgasm after orgasm as they fucked.

"Damn, Bro, your cock feels so damn good I can't stop cumming," she said, panting with her head on his chest. "How about you doing Michaela for a bit while I rest?"

Kyle groaned when Randi moved off him and laid down beside him but moaned with pleasure when Michaela took Randi's place and slid his cock up in her juicy love canal. Kyle saw sparks because of the sensuous sensation.

"Oh, go slow, Michaela," he gasped. "I want to relish the feel of my cock in your pussy for the first time and remember our first fuck forever."

"I'll do my best but after watching you and Randi fuck, I'm so horny I just want to fuck you and get off!"

"Oh, Babe, do it. I'm with you all the way."

Michaela threw her best fuck on Kyle to give him something to remember, plus she wanted to remember it also. Michaela felt Kyle match her thrusts and hip movements expertly, adding a few moves of his own. She felt herself climbing higher and higher and knew her orgasm was going to be a big one. The feelings in her love canal were exquisite and Kyle's pubic hair rubbing against her clit felt super good. Michaela began to fuck with abandon as she climbed to the peak of Mount Orgasm. She thrust her pussy down on Kyle's cock trying to engulf it completely in her fuck hole. She heard Kyle breathing hard and grunting like he was getting close as well. Michaela climbed to the precipice and over the top. Her body shuddered and twitched.

"I'm cumming, Kyle! Don't stop, Baby, I'm cumming! Ah!"

Randi watched her brother thrust uncontrollably as Michaela leaned forward on Kyle's chest as she completed her orgasm. Randi knew Kyle's dam was about to burst and watched him intently as he thrust into Michaela.

"Oh, fuck, Michaela, I'm cumming! Yeah! Fuck! Yeah, ah, ah, ah!"

They laid coupled together, neither one wanting to move and kissed with a passion only lovers can share.

"God, watching the man I love fucking the woman I love is so hot I almost want to faint from the erotic overload," Randi said.

Michaela rolled off finally and Randi saw the proof of Kyle's orgasm pooled together in the reservoir of the condom. Randi removed the condom from her brother's cock and held it up to look at it. She smiled at the sizable amount of spunk then placed the condom in an empty ashtray on the night stand. She then took Kyle's cock to suck and clean the acrid spunk off. She didn't stop sucking when the cock was clean but kept it up until the cock was hard in her mouth once again. Randi reached in the night stand and pulled out another condom. She put the condom on Kyle's cock and caressed his balls gently.

"Now that you're hard again could you fuck me some more, Bro?"

Randi laid down on her back and spread her legs invitingly. Kyle got between her lovely legs and tapped on her clit with the head of his cock a few times. She was so wet from watching him and Michaela fucking he pushed his cock into her love hole with just a few gentle pushes this time.

"Ah, Kyle, you feel so fucking good, don't ever stop fucking me, okay? Even if you get married you just tell her you have to fuck me, too. If she don't like it, tell her, that's tough!"

Kyle chuckled at his sister's straight forwardness. He thrust his cock into her while looking into her eyes which were looking at him lovingly. Being on the top he could easily control the speed of their fucking. He greatly enjoyed the feel of his cock in her warm, wet love canal which clung to his velvety shaft like a suede glove.

"I'll never stop fucking you, Randi," Kyle said. "I don't think Michaela will mind it one bit."

Movement caught Michaela's eye and she turned to see Sylvia, Edwena and Eldon enter the room and stand quietly.

"What are you saying, Kyle?" Michaela said with a smile. "Did I say I was going to marry you?"

"Well, no, - but I was hoping you would someday," Kyle stammered.

"Well, you have to ask me to first!" Michaela scolded.

"I know. - Would you marry me if I asked you to?"

"Well, why don't you ask me?"

"Okay. Will you marry me, Michaela?"

"Yes, of course. But this has to go in the book of records."

"How's that?" he panted while plunging deeply into Randi.

"This has to be the first proposal made to a woman while the man was fucking another woman laying beside her."

The burst of laughter behind him was the first clue to Kyle that they were not alone. Kyle looked behind him to see the other three naked people standing there, watching him. He froze momentarily with his cock buried deep into his sister's cunt.

"Fuck me, Bro, I'm almost there!" Randi pleaded while smiling at Michaela.

"Oh, god, what am I gonna do with you two?!"

"I guess you'll have to keep on fucking both of us, stud," Michaela quipped.

Kyle resumed fucking Randi while trying to ignore everyone else. He couldn't ignore it when Michaela began to moan with pleasure as Eldon put his head between her legs to lick her pussy and suck on her throbbing clit. He glanced behind him to see the beautiful Edwena and even more beautiful Sylvia in a very erotic embrace.

"I feel it coming, Bro! I'm gonna cum big this time. I'm - cum - cum - Oh!"

"Oh, shit. Sis, it's a good thing I've got a rubber on! I'm gonna cum right in your tight little pussy! Uh! Uh! Oh, shit! Uh!

They shuddered together, locked in each others arms, until their orgasms left them well satisfied for the time being. Kyle pulled out of Randi and removed the condom. He placed it in the ashtray with the other one and sat back on the bed.

"If we lay cross wise on the bed all six of us would fit on it," Eldon suggested.

Eldon and Michaela got up to allow Kyle and Randi to lie cross wise on the bed. Kyle lay on his back between Randi and Michaela again. He looked down and saw Eldon's face between Michaela's thighs. He thought the guy must really know how to eat pussy judging from the sounds from Michaela's lips. He looked to the other side of him and saw the beautiful Sylvia on top of Randi, kissing her passionately. His thoughts were interrupted when Edwena laid her naked body down on top of him.

"Hey, Stud, any lead left in your pencil for me?" Edwena asked.

"Oh, heck yeah! I'd always have lead in my pencil for you." he answered.

Edwena took his cock in her mouth and began to suck him, making his cock stir back to life. It wasn't long before she had Kyle fully erect again and ready to do business. Edwena smiled at Eldon and pointed Kyle's cock at him, offering him a taste. She smiled as she watched Kyle's expression when he realized who had his cock in their mouth. She heard Kyle gasp as Eldon gave him an expert blow job, a look of disbelief on Kyle's face. Kyle wasn't at all turned of by another guy sucking his cock. In fact it felt so good and was such an erotic turn-on that Kyle was as aroused as he was at the start of the evening. Edwena smiled as Kyle laid his head back, enjoying what was happening to him. She looked over at Michaela who was watching Eldon, his head bobbing up and down on Kyle's shaft. Edwena finally pulled Eldon off Kyle's cock before it went too far.

"This is my load," she reminded him. "You'll have to get yours another time."

Kyle couldn't believe his eyes as he looked over and saw Sylvia's face between Randi's thighs. He knew the beautiful woman was licking Randi's pussy and let out a groan. Again his thoughts were disturbed when Edwena spun around and got him into a sixty-nine position. He had admired this woman with her clothes on so often at work, but now he got to look at her naked beauty up close and personal. She had a patch of coal black hair on her mound but her pussy lips were shaved or waxed baby-butt smooth. Kyle didn't hesitate to plant a kiss on her sexy pussy lips as she engulfed his cock in her mouth. Kyle felt someone gently caressing his ball sack but at this point couldn't care less who it was. Maybe it was Edwena who was expertly sucking his cock. Then again, maybe it wasn't. Oh, well, who cares, he thought, it felt good. He could tell the difference though between Edwena's blow job and Eldon's. Eldon was firmer and more demanding while Edwena's mouth is soft and gentle, more patient. Both feels good he decided. Soon Edwena spun around and kissed him.

"How about a nice, slow fuck now?" Edwena asked him.

"Sure, Darlin'," he smiled. "Let me get on top, I like it better that way."

As he got up to let Edwena lie down on the bed between Michaela and Randi, he looked at Eldon who was standing between Michaela's legs, stroking his cock. He checked it out and decided Eldon was about the same size as he is but it's hard to tell because Eldon's cock isn't straight, it curves off to the left a little bit Eldon noticed Kyle checking him out and stopped stroking to let Kyle have a good look. Kyle had never thought to touch another man's cock, especially a hard one, but he had the urge to reach over and touch the throbbing fuck stick attached to Eldon's pelvis. It felt pretty much the same as his own cock did except that he could only feel from the outside instead of from the inside as well as he did with his own. The one sided feel felt strange but erotic to have another throbbing cock in his hand. Kyle slid his hand up and down the curved shaft a couple of times then let go of it. It seemed to sway from side to side in protest of being abandoned. Maybe another time, Kyle thought but right now he had another iron in the fire: Edwena was waiting for him to fuck her. Always the gentleman Kyle wasn't about to deny a pretty lady her desires. Kyle slid his cock into Edwena's waiting love tunnel effortlessly and together they began a slow, sensuous mutual rocking of hips known as fucking.

She's one hot, sexy lady, Kyle. I'm glad I married her," Eldon smiled.

"Yeah," Kyle agreed. "Michaela is a beautiful, sexy girl, too. I'm glad I asked her to marry me."

Kyle was watching Eldon's cock slide slowly into Michaela's sweet pussy. The more he watched the more he could appreciate the older man's curved, circumcised cock. He wasn't jealous a bit, but felt glad because his sweet Michaela was able to get so much enjoyment from Eldon's cock. His wife, Edwena's, pussy was feeling so good he came back to pay attention to her. Her breasts were not excessively large but big enough to command attention. Her nipples were brown in color and made her breasts look like torpedoes. He looked over at Randi and Sylvia and saw Randi's face between Sylvia's thighs. Sylvia looked at him and smiled. A shiver went up his arms when he felt Sylvia pat him on his naked ass not far from his nut sack as he fucked Edwena. Sylvia, Michaela's mother, the woman whose beauty had seriously intimidated him so much was now naked beside him touching his naked ass. He was brought back to the present and was glad to hear Edwena moan as she climaxed and gushed her cum juices all over his throbbing cock which was about to cum as well.