Friends - Alternate Reality Ch. 14

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Ch 14--The One with Monica and Chandler's First Time.
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Part 14 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Monica was between relationships, and growing envious of Ross and Rachel's deepening relationship. She had been in a very serious relationship lasting a year. The couple had decided it was going nowhere because she wanted children and he did not. They were wise enough to know that there was no compromise that could solve that dilemma. Either you had a kid, or you didn't.

Chandler wanted children. He had much to offer. He was good looking, two years older than Monica, smart, witty in the childish manner of straight men, and a good person. Monica had known him since she was sixteen. Ross probably knew Chandler better than anyone other than Chandler himself. Chandler had been Ross's best man at his ill-fated wedding with Carol. Ross openly declared that Chandler would be his best man again, should he re-marry. Monica's mind wandered to Chandler's male endowment, and what it might look like.

Monica realized with a shock that she had begun thinking of Chandler as a romantic prospect. Her jaw dropped when she admitted to herself that she had set her sights on Chandler as a boyfriend, lover, and husband. Monica stood up, and paced about her living room, coping with this sudden insight. It made so much sense. Chandler was husband material. Not flashy, not overtly sexy, not a bad boy, but a solid, upstanding man. A real man. Monica said to herself, "You've finally grown up, Monica."

For the first time in her life, Monica saw her future stretching out before her with perfect clarity. She and Chandler would share their lives, have children, grow old, and die together. Chandler was not the divorcing kind. Monica was determined that she would not be, either.

It was impossible to imagine either of them being unfaithful. Monica thought, wryly, "Unless, of course, Taylor Swift sets her sights on Chandler Bing. Oh, my God, by name will be Monica Bing! We'll be the Bings. My child will be little baby Bing!" Monica tried to tell herself that she was being shallow and childish, worrying about the sound of Chandler's name, "You cannot allow that to be a deal-breaker, Mrs. Bing."

Monica considered Chandler, and how to manage the next steps in their love-of-a-lifetime. Chandler was like Ross in many ways. They were both nerdy and intellectual. Neither was terribly successful with women. Either would make a perfect husband and father. Monica knew for certain that Chandler wasn't seeing anyone right now. In fact, he had been complaining about his desperate quest to find a woman for months, if not years.

Monica thought, "Chandler doesn't know it yet, but I am the only woman he is going to be with for the rest of his life." Put that way, it didn't sound appealing for Chandler, but Monica was a beautiful woman. She had no doubt in her mind that Chandler was already in love with her.

How to break the news to him? "Hi, Chandler, I'm the next, and only, woman you will ever have. Welcome aboard!" No, she needed to draw things out a little, almost like a normal romance between people who have just met. She had to manipulate him into courting her. Easy.

Monica picked up her phone and called Chandler's phone. "Hey, Chandler, are you home?" He was. "I've got some fettucine alfredo over here, if you want some." He did. "Great. See you in a few."

The next question is whether Joey was home, as well. Monica had to take that chance, since inviting only Chandler would make her intentions obvious. After a few moments, Chandler walked in...alone. Monica asked, "Where's Joey?"

Chandler answered, with disgust, "Out on a date." Joey did great with women.

She invited Chandler to sit at the kitchen table. She poured white wine for two, and set about re-heating the fettucine, which was from the day before. She inquired, "How about you, Chandler? What's upcoming on your social calendar?"

He moped, "Oh, nothing. I have a family wedding here in town Saturday after next."

She asked, "You don't have a date to the prom?"

He chuckled, "No. It's pretty tough to take someone you hardly know to a family wedding."

"Maybe you'll meet someone there. Weddings are great for matchmaking."

He said, "Well, half the people will be related to me, anyway."

She said, "I love going to weddings. Dancing, the food, the cake. It's great fun!"

Chandler was looking at Monica. She smiled sheepishly and fussed over the fettucine. He ventured, "If you like weddings, you could come with me."

She put her hands on her hips, as if astonished, "Oh, that's a great idea. I would love that. Thank you."

She served him the fettucine. He tasted it and raved, "Oh, my God, Monica, you are such a great cook! This is delicious. You should get into catering, because this is better than anything I have ever had at a wedding."

"Why thank you, Chandler Bing." They ate in silence for a bit, then she said, "Oh, that reminds me, I am dying to see the new James Bond movie. If you take me to the wedding, I'll take you to the movie...."

Chandler said, "That'd be great. Let's see if we can work out a time with the gang." Monica was deflated. He was just like Ross, so honest and direct. He naively thought that others were the same way, and he therefore could not take a hint. The following Friday, when Monica knew that everyone else had plans, she called Chandler, and said, "The Bond flick is showing at nine. Wanna go?"

"Sure, but Joey is on a date."

Monica said, "Phoebe, Ross and Rachel are busy too, so it'd just be us."

"Oh, okay. You hungry?"

"Yes!"

They went for pizza before the movie. James Bond offered something for both of them, with their widely divergent tastes in film. Monica had decided to inform Chandler that they were a couple with a romantic first kiss. She was eager to make this, the last first kiss for both of them, something they could remember fondly forever. Friday night proved to be foggy. There were no expansive views upon which to gaze.

There followed eight days of scheduling conflicts and work crises, so Monica and Chandler's second date was his family wedding. Monica had met scarcely anyone in Chandler's family. They, of course, were agog at the stunner that Chandler had shown up with. When Monica went to the lady's room, Chandler was beset by relatives who wanted to know how long they had been dating, were they serious, and what sort of bet she had lost to get stuck with Chandler as a date.

Monica was an excellent dancer. Chandler was mediocre at best, but always game, which was the most important thing to Monica. They did a lot of dancing. On every slow song, they held each other a tiny bit closer than they had previously.

The reception venue had a spectacular view, and the weather was, at long last, cooperating. They stepped out to admire the view. Monica held Chandler's hand as they walked out. Looking out, Monica put her arm around Chandler's waist. He turned to her, she turned to him, and they shared a lingering, closed-mouth kiss. Monica thought, "Perfect. This will make a great story for our grandkids."

Monica and Chandler had a great time at the wedding. Arriving back at their building, they held hands in the elevator, and on the walk to their respective doors. They kissed lightly, and Chandler, with characteristic candor, asked, "Was this our first date?"

"This was our second date."

From then on, Monica and Chandler had dinner together almost every night. Monica told Rachel that she was seeing Chandler the first week, and told Ross and Phoebe the second week. Monica and Chandler spent many hours talking about their values and expectations. They were confirming that they were a good match. They were still at the kissing and necking stage when they told Joey in week three.

Now that their circle of friends was up to speed, it seemed to Monica a good time to make love for the first time. On a Saturday night, when Rachel was staying at Ross's, Monica made a romantic dinner. They ate by candlelight, not saying much. After dinner, Monica stood, took Chandler's hand and gently drew him toward her bedroom.

Even though Rachel was not expected that night, Monica closed her bedroom door for thoroughness. She lit candles, some of which were scented. Chandler chose to defer to another time the revelation that he hated scented candles. Chandler began to disrobe while Monica was lighting the candles, mainly because it felt awkward to stand there doing nothing. They stripped on opposite sides of the bed, and got in together.

Monica took for granted that their lovemaking session would begin with mutual oral sex. There was a bit of awkwardness when he didn't take the hint and go down. Instead, he manually stimulated her pussy. Going with the flow, Monica helped by pouring oil into his palm and hers. They gave each other manual foreplay for a while. Monica coached him, "Yes. Yes. Focus on the clit. Just the clit. Oh, yeah! How does this feel?"

Chandler was about to climax from Monica's hand job. He said, "Too good. Stop, before I explode. Let me focus on you." Monica lay back and spread her knees. Chandler was now able to position himself in an ergonomically efficient manner.

Monica coached him further, "Get some more oil on your hands. Good. Try to slip a finger inside. Gently!" Monica made a mental note to have Chandler trim his fingernails. Monica estimated Chandler to have an average-sized endowment, which was fine with her. Anything larger would be painful. When she reckoned she was lubricated sufficiently, she said, "Now."

Chandler climbed over her and between her legs. She guided him with one hand. Chandler entered her slowly and smoothly. She cooed, "Yes. Yes. Good. Gently. Good." Once she felt his groin against hers, she knew he was in as deep as he could go. She smiled up at him, and said, "Do it. Enjoy yourself, sweetie." Chandler smiled back, and enjoyed himself by stroking his dick in and out rapidly. His eyes rolled up into his head, giving him a ghoulish appearance that amused Monica. He closed his eyes tightly, and an anguished look grew on his face.

Monica knew he was coming when he emitted a series of strangled squeaks. She happily cheered him on, "That's it. Do it! Do it! Do it! Yes!" Chandler off-loaded a large volume of semen. When his orgasm ended, he dropped his head, letting it hang limp above her. She reached up to place her hands atop his shoulders. When he returned to the land of the living, he opened his eyes to see her smiling up at him. She asked, "Are you back?"

He nodded, and croaked, "Yes." They both laughed softly. He backed down and out of her. She reached to her nightstand and took a fistful of tissues. She brought her knees up and applied the tissues to her pussy, which was dripping white Chandler-ade. Monica discretely closed the tissues between her legs, and gathered a wad of tissues to hand to Chandler, who wiped off his dick. Ever the neat-freak, Monica produced a tiny wastebasket for the used tissues, and then set it back on the floor next to the nightstand.

They caught their breath and relaxed a bit, smiling and gazing at one another's nude forms. Chandler's form was very respectable. Monica's was bombshell gorgeous. They kissed a few times. She said, "I forgot to bring the wine."

He said, "I'll get it."

"Bring the bottle and the glasses."

After Chandler's return, they toasted one another with a clink of glasses, and drank. Monica asked, "Do you want to shower before we continue? I wouldn't mind a little wash and brush up. We could do it separately or together. Your choice."

"Uhhhh, together?"

Monica laughed, and bounced out of bed. She put on a bathrobe, and handed Chandler a matching one. Chandler wondered how many other lovers had worn this same robe. Knowing Monica, it had been thoroughly cleaned and sanitized. They hadn't used a condom because they had previously discussed the reproductive and STD risk with one another, concluding that there was no credible threat of pox or pregnancy.

Monica led Chandler by the hand to the bathroom. The shower was a shower-tub combination. It offered enough room for the two of them, but only one could be under the spray at a time. They giggled as they worked to coordinate their movements so that neither grew cold.

Monica, true to form, had a special body wash. It felt as if it wasn't there, yet cleaned and refreshed everything it touched. They found that they could both be mostly covered by the shower if they embraced tightly beneath it. They kissed deeply.

Monica said, "I need privacy for a few minutes. How about you?"

"I'm good."

"Then, go back to bed and warm up a spot for me." They kissed some more, then toweled off. Chandler set out across the apartment. Monica closed the bathroom door, and took her special device from the lower cabinet, and got back in the tub. She stopped up the drain, turned on the water to begin filling the tub. Once there were a few inches of water, she used the device to clean out her vagina. It produced a gentle jet of water. It only took a minute to wash away any trace of fluids, whether hers or Chandler's. She drained the tub, dried off again, and set everything back in its place. She wore her bathrobe to return to her room.

Chandler lay in bed, his back propped up by pillows, covered by a sheet. With a naughty look, she discarded her robe and slid into bed beside him. After a bit of kissing, she drifted downward. His cock was semi-erect.

Monica applied her lips and tongue to it, and it quickly hardened. After she thoroughly kissed and licked every bit of it, she took the head between her lips and started sucking. She worked her head up and down, taking more of him in with each downward stroke. She caressed the underside of his cock with her tongue.

Monica had no trouble deep-throating Chandler. Once her lips reached the root of his manhood, she began making long strokes, up and down. With each cycle, she went from deepthroating to having only the head in her mouth. Her cheeks were hollowed inward due to the suction she generated. Chandler moaned helplessly, watching her with burgeoning affection.

When he squeaked, "I'm gonna come!" she deepthroated him and kept him entirely in her mouth. He spurted semen into the back of her throat. Throughout his orgasm, she sucked hard and swept his cock with her tongue. She swallowed the last drop, and pulled her face off of his groin, using her lips like a squeegee to clean him off.

It was the best head Chandler had ever had, by far. He wanted to kiss her in thanks, but he did not want to kiss the mouth that had just ingested his semen. Monica was sensitive to this natural aversion. She rinsed and gargled with wine, and swallowed the wine. Chandler was still reluctant, but it was clear that Monica now considered her mouth kissable, and he didn't dare complain. He kissed her, open-mouthed, and tasted--wine.

Now came the moment that Chandler had been dreading. He had hoped that it would not arise on their first lovemaking session. Monica lay down with her head slightly propped up by pillow, and smiled excitedly. She obviously expected Chandler to reciprocate with cunnilingus. Chandler had never performed cunnilingus. He told her, gently, "Monica, I need your help with this one. I'm nervous. I've never done this before."

Monica allowed her jaw to drop for a few moments. She recovered quickly, and implored, "Oh, that's all right, sweetie. You don't have to do it if you don't want to."

"Oh, no! I want to, I'm just nervous about the taste. I mean, what if I, you know...."

Monica understood that Chandler was afraid of gagging or vomiting. She kissed him lightly, and said, "I have our solution. I'll be right back." She dashed out of the room, and returned moments later with a small mixing bowl covered with plastic wrap. She peeled off the covering and said, "Fresh whipped cream. I made it for dessert, and I guess this qualifies." She got into bed and dipped her finger in the fluffy cream and fed a bit to Chandler. "Now, you can go at your own pace, dear. You can just slurp up the cream if you like."

Chandler timidly said, "That's not the cream I'm worried about."

Understanding broke over Monica's face, "Oh! Oh, I see! You don't have to worry, dear. I used my private time in the bathroom to thoroughly clean myself, inside and out. I have a special device for that. I've never been cleaner, sweetie." She ducked her head down to look up into his eyes, "Is that all right for you? If it's not, we can do other things."

"Give me the cream." Chandler dropped down to her nether region. She spread her legs to present herself to him. He applied at thick coating of cream to her entire pussy region.

She giggled, "That tickles. Now just lick it off."

Chandler swallowed hard, and dove in bravely. He licked and slurped all over. It tasted like whipped cream. By the time he got down to touching living tissue, he had the confidence to continue. Monica said, "That's good, honey. Now just lick the clit with the tip of your tongue." Chandler did as he was told. Monica moaned, "Oh, yeah. Oh, yeah. Oh, yeaaaahhhhhhhhh."

Chandler lifted his head from her muff and asked, "Shouldn't I be doing other things with other parts of you?"

Monica laid one hand atop his head, and said, "No. Not for me. Nothing else matters. Just flick your tongue over that button, and I'll go crazy. The faster, the better." When Chandler reached for more cream, Monica admonished, "Only put it on the top there, by the clitoris. That's all there is to it."

Chandler said, "Okay, I'm going in." He worked exclusively on the clitoris, and Monica now put both hands on his head, running her fingers through his hair. She moaned louder and louder, until she began to chant, "Yes. Yes. Yes. Yes! Yes! Yes!! Yes!! YES! YES! YES! YESSSSSSS!"

Chandler struggled to maintain contact between his tongue and her clit while she writhed about in ecstasy. He was helped by her hands, with which she pushed his face firmly into her muff. Suddenly, she pushed his head away, and said, gratefully, "That's all, sweetie. Great job!" Chandler got to his knees in the bed, and wiped his mouth with his hand. Monica suggested, "Sweetie, you can rinse with some wine, or go the bathroom to brush your teeth, or use mouthwash."

He said, "I need the bathroom anyway. Back soon!" Monica lay back in the warm afterglow of her orgasm. She thought, "This is going to work. He's a quick learner, and very eager. We're going to be great in the bedroom together. Another box checked, Mr. Bing!" She laughed at the inadvertent pun, "Another box, indeed."

When Chandler returned, Monica greeted him with warm kisses and kind words. She invited him to spend the night, to which he happily agreed. He dressed quickly and ran across the hall to get his toothbrush and a few other things.

Upon his return, Chandler eagerly explored Monica's body with his eyes, his hands, and his mouth. There had been so many questions, stolen glimpses, and fantasies over the years. Now, she was a reality, and he had cleared the first hurdle.

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