Friends - Alternate Reality Ch. 26

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Ch 26--The One where Joey Dates Chandler's Ex.
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Part 26 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Joey suddenly realized that his roommate's new relationship with Monica, which Chandler and Joey both hoped would become permanent, opened up romantic options for him. Although Chandler was never a lady's man, he had dated some pretty girls. Some pretty hot girls. Some he had slept with, some not. Either way, Joey figured that they were all now fair game for him. Joey mentioned it to Chandler, "Hey, I was thinking that, since you're with Monica now, I can date any of your exes."

Chandler froze. He was unable to think of a credible reason to prohibit Joey from dating any former girlfriends, "Well, I guess so, but I don't think you'd really like any of them."

This was an unexpected and unpleasant development. Joey was definitely a lady's man. He tended to very short-term relationships, usually one-nighters, with women who ran the gamut. Joey's conquests might be promiscuous, chaste, intelligent, dumb, rich, poor, cute, pretty, beautiful or gorgeous.

Chander and Ross had agonized many times when Joey brought home a beautiful, educated, classy woman who was drawn to Joey only by his good looks and streetwise vibe. Some of them would have been perfect mates for Chandler or Ross, but sleeping with Joey voided their warranty, so to speak.

Joey's first target, predictably, was Janice. Chandler had had exactly four dates with her, and no sex. She was pretty, with short brown hair. Janice was tall. In heels or boots she looked taller than either Joey or Chandler. She intentionally wore tall shoes to gain a height advantage. She was an Archaeologist. She studied building and construction sites around New York City, looking for, identifying, and classifying human remains and artifacts. She was quick-witted, and both Ross and Chandler had longed for her.

To Chandler's horror, a matter of hours after Joey had asked for Janice's number, Joey reported that they had a date for Saturday night. Chandler spent the night in the apartment of an even more attractive woman across the hall. Around ten o'clock, Chandler had to go back to his apartment to get something, and he saw Joey's door closed, with a necktie hanging from the doorknob.

Joey and Chandler had separate bedrooms, and there was no chance of Chandler going into Joey's room, but Joey still put out the traditional "Do not disturb" sign anyway. There were faint noises. Chandler got what he needed and retreated to Monica's place. Monica was on the couch, reading. Chandler sat beside her, took her hand, and said, "I feel the need to talk. Is now okay?

Monica closed her book, "Sure. What's up?"

Chandler looked straight ahead, "I know I'm being ridiculous. I have a gorgeous woman that I'm crazy about—that'd be you—and yet I'm ruminating over a woman I never even held in my arms. Joey had a date with that girl I dated, Janice. Remember her?"

Monica said, "Oh, yes. She was cute. I thought you two would work out."

That stung, "Well, I hoped that we would, too. Four dates, and we never got intimate. Now, on her first date with Joey, they're already in bed across the hall. It's humiliating."

Monica took his hand, "Chandler, there's a Sheryl Crow lyric 'It's not having what you want, it's wanting what you've got.' We're together. False modesty aside, you won! You win at life! You got the better girl, and you got her forever."

Monica and Chandler had never formally discussed the long-term future. Chandler said, "You saying 'forever' is the most beautiful sound I've ever heard." They kissed slowly. He said, "Numbers 55 and 58 are waiting for us in there." They went, hand-in-hand, into her bedroom.

The next morning, Chandler woke up before Monica. He stumbled out to the kitchen to start the coffee. He noticed the little whiteboard now read "6." "When the hell did she update that?" Monica came out of the bedroom wearing a very thick and fluffy terry robe. Chandler thought, "She rolls out of bed looking gorgeous!"

They kissed. He poured her a cup of coffee, and she set about cooking breakfast. He sat at the kitchen table with the Wall Street Journal. Whenever she could turn away from the stove, she paged through that damned Kama Sutra. She said, "Well, the very next position, Chandler, is Number 59, 'The Nirvana.' It's just missionary style with the woman's leg on the inside and the man's on the outside."

"Lemme see that." Chandler saw at a glance the problem with "The Nirvana." It called for a man with a long dick, and Chandler's was not long, certainly not long enough. He said, "I know that looks like an easy position, Monica, but there's something we need to talk about. Ahem. Many of the positions in here, including Number 59, require that the man be exceptionally endowed. I won't be able to do them with you, and that would be disappointing for you, and embarrassing for me."

Monica was taken aback, "Oh, baby, how could I have been so insensitive?" She went to him, kneeled beside his chair, and put her hands on his leg. "Chandler, I'm going to tell you a secret. Everyone I have told about our sex life has heard the same thing. I told them the God's honest truth. Your endowment is perfect for me. Just right. If those positions don't suit us, then we won't try them, ever again. We can rip the pages out of the book. You remember Number 10, "The Toronaga'?"

"Timonaga."

"In the Timonaga, you went too deep and it hurt. If you were any larger, our sex life would not be as good."

Chandler kissed her, "Thank you, Monica, I feel so much better. I love you."

"I love you, too."

They ate Monica's delicious breakfast. Monica continued to examine the book. With only a few positions remaining, she said, "How about this one, honey? It's number 100, 'The Right Angle," and I'm sure we could do it if we find the right piece of furniture. Here, look."

She passed him the book, and he was encouraged by what he saw. It was a position prominent in many movies, both porn and mainstream. She woman lies on a table with her butt at the edge. The man stands on the floor and they do what comes naturally.

Monica swept some of the dishes aside, and sat on the edge of the dining table. Chandler said, "Too high, unless I stand on a box or something."

Monica said, "The drafting table!" Monica's share of the home office space was dominated by a huge drafting table that she got at a flea market. The table was extremely large, heavy and strong. It was also a couple inches lower than most tables. Monica closed the blinds, because the table sat before a large window that looked into the building next door. Monica sat on the table. Chandler moved between her legs, and it looked like there would be a perfect alignment between his penis and her vagina.

Monica yelled, "Hot dog!" as she ran into the bedroom. She returned with pillows and lube. She set them both on the drafting table. She returned to their bedroom and closed the door behind her. In two minutes, Monica sashayed out wearing a black negligee. It was one of Chandler's favorites. Tiny spaghetti straps strained to hold up her breasts, of which only the lower half were concealed.

Chandler had already felt stirring under his robe when they were scouting for locations to execute Number 100. Now, he was inflating rapidly. He removed his robe. Monica slowly dropped to her knees and suggestively held her mouth slightly open and her tongue out. That alone was sufficient to get Chandler hard, but he never missed an opportunity to see Monica's lovely face with his prong inserted into it.

Chandler stepped up to Monica and lay his dick on her tongue. She slurped and licked noisily to get it all wet, then sucked the outer half of his shaft. He held her head in his hands and gently pumped his hips, swishing his cock in and out of her mouth.

After a very short time, he stepped back and held out his hand to assist her to her feet. He greatly enjoyed sliding one strap off her shoulder and mauling the exposed breast with his mouth. He gave the other breast equivalent attention, and pulled her negligee down around her feet. She hopped up onto the drafting table and scooted over to lay upon the pillows with her head elevated and her butt partially overhanging the edge.

Chandler felt a huge upwelling of love for this woman. She created this moment for his pleasure and, more importantly, his happiness. He lubed his cock and stuck the head into her vagina. He pulled it out, and re-lubed the head. He inserted it all the way this time, but slowly. Monica looked down at the juncture between their bodies and licked her lips. She moaned, "That's just right. Drill me with that thing!" Chandler needed no further encouragement. He thrust forcefully, exposing at least half his cock each time, before plunging it in again.

Monica groaned, "Hammer it in! Bang me!" Chandler's hips were a blur, and he strained to keep his breath. She urged, "Fuck me, darling! Fuck me! Plant your seed, my beloved. Fill me with your cum. Fuck me! Fuck me! Fuck me!" Chandler's moans evolved into a rough growl. He transferred his seed in several pulses, each punctuating a very hard thrust.

When he was finally sated, Chandler stepped back. Monica reached for some tissue, and put her hand over her pussy to prevent Chandler's semen from dripping onto the floor. She ran awkwardly to the bathroom. The sight of his woman desperately trying to contain his cum in her pussy was warmly erotic to Chandler.

After a few minutes, Monica emerged from the bathroom wearing only a towel. She updated the whiteboard to "7." She came to Chandler, and stood on her tip toes to whisper into his ear, "What am I to do with you, Chandler? You pour so much cum into me that it overflows. I love that." Chandler had never felt so manly.

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