Friends - Alternate Reality Ch. 62

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Ch. 62 - The One Where Chandler Takes Sisters.
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Part 62 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Once or twice a week, Chandler fucked Jenny. Chandler had to guard against tipping June off. Nobody would ever believe that Chandler did not lust after Jenny. If he never went to June for relief, she would get suspicious. He also grew more ambitious, sexually. He called June, and said, "It's Chandler. I was just thinking about you. When are you available?"

The very next day, Chandler went to June's apartment and worked her over harder than ever before.

Afterward, Chandler lay on his side, resting on one elbow, and had a serious talk with June. He began, "That was great, June, as always. We need to talk, though." June's face went serious. He said, "I have stayed away from Jenny, but if she is determined to see me, she can find a way. Plus, she is friends with Monica. Anyway, she is really coming on to me, hard. I can have her anytime I want, June. I'm certain of it." June looked at him, tensely. He said, "I am therefore raising the price of my forbearance." June nodded slowly, acknowledging the truth of what Chandler had said. He continued, "When your sister visits, I want both of you."

June sat bolt upright, shocked, "Are you out of your fucking mind, Chandler? My sister?"

He said, calmly, "Better your sister than your daughter. A beautiful, innocent young woman, of legal age, wants me. That's a lot to say no to, June. My compensation must be commensurate." Then, in a more collaborative tone, he said, "June, you told me about your sister. She's single, not seeing anyone steadily, and she's much more adventurous than you. I've seen the photos," he gestured to a cluster of family photos on her dresser, "she's hot, like you. Make it happen, or I will open up Jenny. I can't stop thinking about being her first. Taking your daughter's virginity would be the pinnacle of my sexual career, June. It's only natural that I should want to do it."

June hissed, "You bastard!" She picked up her phone, dialed, and Chandler heard her say, "April, it's me.... I told you about that guy I've been seeing casually.... Yeah, that's right. Well, I want to get a little more, shall we say, adventurous, and I really truly would love to have you involved, April.... Yes.... Yes, that's right. I know you'd like making love with this guy, and it would be great fun with both of us at once, don't you think? Uh-huh, uh-huh, yes.... We'll talk more, all right? Love you.... Bye."

June hung up, and said, "Wipe that smirk off your face, Chandler, you got what you wanted."

Chandler said, "June, we both got what we wanted."

June asked, irritably, "Tell me the truth, Chandler. Do you think of Jenny while you're fucking me?"

Chandler answered honestly, "No! You're too new to me. I'm never bored with you. I occasionally think about Jenny when I pork Monica." This gave June some gratification.

April was three years younger than June. She was quite pretty. She had blondish hair, but she was a bit shorter than June, and had only D-cup breasts. Large breasts ran in the family. April had been divorced for several years, and had made herself popular on the Chicago dating circuit. April was coming for a long weekend visit. Chandler talked strategy with Monica, "Where do we do this? You're here, and Jenny is there. No privacy."

Monica frowned, "Hmm. I don't want to leave for the weekend, but I can be gone for some stretches of it. When I'm gone, you can do them here, in the guest bedroom. If you do them in our bedroom, June will know that I either know already, or will soon find out. I think maybe you spend Saturday in a hotel room with them. You can also do them at June's place, if Jenny will be out of the apartment, or here, if I am."

Chandler held her hands, "Monica, I love you so, so much."

Monica said, "I love you, too, Chandler, but don't think you won't pay for this."

Chandler laughed, "Oh, I know I will. I'm running up a huge tab!"

On Friday evening, June introduced her sister to Monica and Chandler, "Monica, Chandler, this is my kid sister, April." She thought, "Your husband is already drooling over her, Monica."

Monica was enthusiastic, "Great to meet you, April. Welcome to New York." She thought, "Another whore. Miss April and Miss June are going to get little Jenny's sloppy seconds."

April gushed, "Great to me you both!" She thought, "Your husband wants me. I can tell. He won't want to go back to you after I'm done with him."

June and April told Jenny that they would be shopping Saturday afternoon and evening. They met Chandler at the Provincial Hotel. It was a nice place. When Chandler ushered them into the room, they found champagne chilling. Chandler had had to swallow hard to muster the courage to order champagne for three, but the maître d' didn't react. He had probably heard it all in his years of experience.

April walked directly up to Chandler, wrapped her arms around him, and gave him a passionate open-mouthed kiss. June had never kissed Chandler on the lips. Managing to free himself, Chandler asked, "Champagne, ladies?" He opened the bottle, and poured three glasses. April made a toast, "To dangerous liaisons!" She drank the whole glass on one draught. Chandler barely sipped his. He didn't want to blunt his sexual powers with alcohol. Monica had agreed to grant him a three-day rest prior to his outing with the sisters. Chandler was raring to go.

June and April fell into a giggling, drunken, sisters' slumber party mode. Chandler undressed as they drank glass after glass of champagne. He was in his boxers before either woman undid her first button. June noticed Chandler and nearly laughed champagne out her nose. She cried, "Oh, right! We came here on a mission." She and April set down their flutes and began to undress. Chandler called down for another bottle of champagne.

Chandler gallantly assisted the sisters in disrobing, giving the occasional grope, lick or kiss. June said, "Watch this, sis!" as she pulled Chandler's boxers down. April nodded approvingly at his erection.

Chandler narrowed his eyed, rubbed his hands together devilishly, and said, "Why don't you two ladies lie down and get comfortable? I'll take good care of you both." The sisters looked at one another with exaggerated smiles, and climbed onto the bed. They lay side-by-side, their heads on pillows. Chandler came to the foot of the bed, and slowly crawled up to June's feet.

June spread her legs to give Chandler a good look at her quim, and said, "Oh, yeah, baby! This is the stuff!" Grinning, Chandler pressed his face into her trim muff and flicked his tongue over her clitoris rapidly. June's mouth and eyes flew open. She reached out to grab April's hands, and squeezed it so tight that it hurt April. When June recovered the power of speech, she croaked, "Oh, God, April, wait until you experience this!"

June writhed in ecstasy for a few minutes, until April said, "My turn! My turn!" Chandler pulled his face off of June. He grinned evilly, and crawled between April's shapely legs. His mouth and chin vanished into her muff, which was not nearly as blonde as the hair on her head. Chandler gave her a full-speed, high-powered introduction. Without hesitating or warming up, he swirled his tongue over her clit rapidly, with plenty of saliva for lubrication. April was stunned into silence. She involuntarily put one hand on the back of Chandler's head, and closed her legs around his ears.

Chandler kept up with the tonguing while he separated April's thighs with his arms, giving himself room to work. Gripping her thighs to immobilize them, Chandler worked hard for a few minutes. He wanted to impress the new girl. He was rewarded with staccato grunts, and the feel of April's hands clawing at his hair. She writhed erotically, froze stiff, and released into a limp pile. One down, one to go.

Filled with pride at his skillful handling of April, Chandler returned to finish off June. He licked, sucked, kissed and nibbled his heart out. June made small motions with her hips, which did not dislodge Chandler. She cried, "I'm coming! I'm coming! I'm coming!" When her orgasm came over her, she moaned, "Ohhhh! Ohhhhh! Ohhhhh!" June began to laugh uncontrollably, and said, "Stop! Stop, Chandler, please!" He kept up the cunnilingus to torture her for a little while, just to prove who was in control.

Finished with June, Chandler bounded up, out of bed, and said, "I'll be right back, ladies!" He ran to the bathroom to rinse his mouth and clean up his face.

Just then, there was a knock at the door, and a voice said, "Room Service."

Chandler hurried to the door, opened it just a crack, and returned with a fresh bottle of champagne. He refilled the girls' glasses, and served them in bed. That was the end of the first bottle, so he immediately opened the second. In Chandler's mind, he had already paid his sexual dues. The remainder of the night would be for him. He assumed that the women would have to be drunk if he were to achieve his loftiest goal of going 'round-the-world on both sisters.

The girls toasted one another repeatedly, and their glasses were empty. Chandler re-filled them. He stood next to the bed, looming over April and admiring her body. She was thirty-seven, but looked thirty. Laughing along with the sisters, he sneakily kneeled between April's legs, raised her knees up a bit, and stretched over her, his torso supported by his arms. Her pussy was sopping wet. Chandler, smiling like a used-car salesman, entered her. She noticed the intrusion, and looked down as if surprised by this turn of events. She slurred, "Hey, fella, whatcha doin"?

June said, "You're getting fucked, April. That's what we came here for."

April said, "Oh, yeah," and lay back on the pillow. By now, Chandler was inside her and fucking vigorously. He stared at her tits, wobbling beneath him, and thrust hard. He pulled out his dick at least halfway, and plunged it all the way in with force. He repeated this action rapid-fire for some fifty strokes before he could hold out no longer. He arched his back, grimaced, and pumped semen into April. He felt the flow of semen through his cock and into her cunt. April was happily oblivious. He completed his ejaculation, and continued to bang her without pause.

Chandler now noticed that June was gone. In a moment, she reappeared, standing at April's side, and refilling her champagne glass. He said, "Okay, June, you're next." Startled into action, June scurried around the bed and back to her supine position. Chandler stopped thrusting, and pulled his wet dick out of April's abused pussy. April toasted him unsteadily, "Fuck her brains out, boy!" and drank.

Chandler nearly jumped onto June. She took his slippery cock in her hand and stuffed it into her vagina. Once he was established inside her, she watched him with detachment, while she sipped her champagne. He humped her almost as hard as he had done April. Chandler had no intention of coming inside June this day. This might be his only shot at the delicious April, and he wanted all his seed to end up inside her.

Chandler was tiring, so he slowed his pace. He pulled all but the head of his cock out of June, and slid it back in with deliberation. He smiled at the sensation of his cock sliding along her tunnel, long and slow. Chandler perspired. Sweat dripped off his nose and onto June's chest. His legs were leaving wet spots on the sheets. It was time for him to fake his orgasm. He continued to thrust at the same slow pace, but he rammed it in much harder. He groaned, stiffened, and his whole body shook. Finally, he dropped his head, as if exhausted. June said, "That's my boy!" She was completely fooled.

Chandler dismounted June and stood beside the bed, saying, "I need to rinse off, ladies. Would you care to join me?"

The sisters looked at each other, shook their heads, and April said, "Hurry back!"

Chandler took a cold shower. He didn't soap up. He merely wanted to cool down and rinse off the sweat, semen and pussy juice. He needed to be fresh for his next effort. After just a couple of minutes, he turned off the shower. He toweled off quickly, and headed back out. His cock had wilted a bit in the shower, but it sprang back to life at the sight of the two sisters. They lay on their sides, facing one another. June and April caressed one another's breasts with intense curiosity. June has told Chandler that she and April had never made out, and he still believed that to be true. He was witnessing their first incestuous exploration.

He approached, and climbed onto the foot of the bed. Shuffling on his knees, she moved between the women, and said, "My turn, ladies. I need you both to sit upright, okay? He assisted April in sitting up. He placed a pillow behind her back, and another behind June's. Chandler shuffled up nearly to the headboard, threw one leg over April's chest, and settled down with his dick pointing straight at her red lips.

June taunted, "Looks like you've got a job to do, girlie."

April nodded, opened her mouth, and licked the underside of the cockhead. Chandler struggled not to drive it to the back of her throat. He pushed forward just a fraction of an inch. April got the hint, and put her lips around his cock. He pushed forward another fraction of an inch. She began to suck. She tongued his cock, and gradually took more of it in. She used her hand to stroke the base of his cock, while sucking the other half. It felt pretty good, not great.

Chandler pushed his cock in and out a little bit to supplement her mouth action. He said, "Suck it, April. Suck it. C'mon, now, suck. Give me a little more tongue." She responded positively. She shifted into a higher gear, jacking him off rapidly with her hand, sucking harder, and working her tongue all over his cock. Now, she was giving good head. Chandler said, "June, your little sister knows how to suck cock, after all."

June was dismissive, "April always brags about giving great head. I think I do it better." With her mouth full, April was only able to shake her head slightly, and grunt an opposing opinion.

Chandler ran with it, "April, show your sister that you are the blowjob champion." April was able to step up her game just slightly. Chandler felt his climax approach, and he said, "You're almost there, April! Just a little longer." She kept up the pace, and, in a minute, Chandler cheered, "Yes! Yes! That's it! Here it comes." He grunted with each burst of semen he fired down April's gullet, "Ugh! Ugh! Ugh! Ugh! Ugh!"

Chandler left his cock in April's mouth for a short while, before pulling away from her face. She fought to swallow Chandler's load, and recover her breath. Meanwhile, Chandler moved over to June, and positioned himself in front of her. June said, confidently, "Let's show her how it's done, honey." She opened her mouth wide. He inserted his penis. She closed her mouth around it and sucked like the wind. When air leaked into her mouth through the seal her lips made on his cock, it made a squeaking sound. The air was being drawn in by the force of the partial vacuum she maintained inside.

June bobbed her head back and forth with a vengeance. Vengeance, indeed. June was motivated by her rivalry with her little sister. Chandler felt as if the skin on his penis might tear away like tissue. Her tongue maintained a furious pace on his cock. Chandler quickly realized that he was going to come in June's mouth. She was giving him such good head that he didn't mind. June sucked the third load of cum out of him in record time. He jolted a couple of times when his orgasm came. Two little spurts, but, damn, they felt great!

After June cleaned off his cock with her mouth, she boasted, "There! I win!"

April pouted. Chandler wanted to lighten the mood and lower April's inhibitions, so he brought the champagne bottle over. He filled April's glass twice, and June's glass once. April excused herself to use the bathroom. Once April was out of the room, June said, "I was better, wasn't I?"

Chandler said, in low voice, "Yes you were, by a mile, but I don't want to offend your sister." June was disconsolate. Chandler sought to recruit her to his campaign to complete the trifecta with April. He said, "Would you like me to take April down a peg, June?" June nodded vigorously. Chandler said, almost in a whisper, "Let's get her drunk, and I'll fuck her in the ass, okay?"

June was thrilled, "Yeah! Let's do it! She hates anal!"

When April returned to the room, June got out of bed and refilled April's glass. April was drunk by now. There was about a third of a bottle remaining. June looked at the level of fluid, and then at Chandler, nodding. He nodded in return. They silently agreed that the remaining champagne would be enough to render April incapable of resisting. April cooperated by drinking champagne as fast as June poured it for her.

With less than a glassful of champagne remaining in the bottle, April belched a couple of times. Her head wobbled like it was on a spring. Chandler and June pulled April down the bed so that she could lay flat on her back. April closed her eyes as if to sleep. Working together, June and Chandler rolled April onto her stomach. Chandler lifted April by the hips, and motioned for June to place a couple of pillows under her sister.

Chandler clambered off the bed, retrieved his jacket, and pulled out a small bottle of lubricant. Returning to the foot of the bed, he pulled April's legs apart and got on his knees just below her pretty ass. Chandler hastily oiled his cock, and dribbled lubricant generously into her ass-crack. June stood by, hopping up and down and clapping silently in excitement. As much as June and April loved one another, they did have a friendly rivalry.

Chandler used his hands to spread April's cheeks apart. Taking aim at her pink anus, he planted his cockhead into it. Positioning himself over April, Chandler took a deep breath, pursed his lips, and thrust with all his might. He put every ounce of his weight behind the drive. April suddenly woke up and yelped. She looked about in confusion. Chandler was in to the hilt with that single thrust. He wasted no time pounding his hips down onto her ass. The pair bounced on the mattress.

Chandler had never really let himself go with anal. He was always afraid of hurting his partner, or, worse, displeasing her. In this instance, he felt the potential consequences were negligible, and he pounded April's ass as he had always longed to pound an ass. Grunting loudly with each thrust, Chandler compressed April's ass with every impact. She mumbled incoherent protests, which he and June ignored.

Chandler was terrifically turned on by his aggressive buttfucking of this beautiful woman. He came in a remarkably short time. He shortened his stroke, and sped it up, to deliver his few remaining sperm. Winded, he paused to catch his breath. After a few moments, he pulled his cock out in one quick motion, which drew another helpless yelp from April.

Sweating profusely, Chandler got off the bed, onto his feet, and staggered to the shower. This time, he used lots of soap and hot water, and took his time. Wearily, he wrapped a towel around his waist and stumbled out of the bathroom. June was waiting for him. She said, "My turn," and entered the shower. Chandler slowly gathered his clothing and dressed himself. He paced slowly about the room for a while, watching the inert April. He called room service for a pot of coffee. By the time he hung up, June was stepping out of the shower.

Chandler said, "I ordered coffee. For April. Do you think we can bring her around and get her home?"

June put a hand to her forehead, as if she had a headache, and said, "Oh, yes. I've seen her worse than this, plenty of times. It's still afternoon. We'll be home at a reasonable hour. You'd better go."

Chandler paused. He and June had never kissed, and never would, but he said, sincerely, "Thank you for this, June. Really."

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