Friends - Alternate Reality Ch. 17

As their relationship progressed, there grew an unspoken tension between Monica and Chandler about when, where, how, and by whom they should openly declare their love for each other. Chandler was understandably gun-shy about saying "I love you" to Monica because he had done so once, with humiliating results.

On the other hand, it somehow seemed more customary for the man to say it first. Men normally asked women out, and proposed marriage. Why should they not be the first to take the intermediate step of saying "I love you?" Chandler thought this convention unfair, given the beating he had taken when he had done precisely that. It seemed the women were to decide when each step should be taken, and it was for men to guess the time, and suffer the consequences if they mis-timed.

Monica found Chandler to be predictable and easily manipulated. She had engineered their first date and first kiss perfectly, and was confident of doing the same with Chandler's "I love you." He was clearly ready to say it. Monica wanted to make it, too, a moment to remember. She arranged a special dinner celebrating Chandler's birthday. The dinner occurred one week prior to his actual birthday, which fell on a Saturday, and would be celebrated with a party for friends and family.

Monica chose a very romantic, elite restaurant for dinner. She arranged for a specific table, which was both private and against one of the windows. The restaurant was nearly a thousand feet in the air, and the views were endless. The couple had a superb dinner, with wine. They often reached across the table to hold hands. By candlelight, Monica was breathtaking. Monica wanted Chandler to say the three little words after dinner and before dessert. She thought that eating dessert would be extra fun after the mutual declarations of love.

After ordering dessert, Monica reached across the table to hold Chandler's hand. She took his hand in both of hers, and said, "Chandler, you are everything to me, now. Tell me exactly what you are feeling at this moment."

Chandler was trapped. What could he say but "I love you?" He thought to himself, "If it doesn't work this time, it's on her!" He paused for dramatic effect, and said, "I love you."

Monica gave a happy cringe, and said, "I love you, too."

Chandler broke into a huge smile of relief and happiness. They grinned like fools during dessert. They shared bites of their desserts, making messes of their faces and laughing. The foreshadowing of the wedding cake sharing was obvious to them both, but neither mentioned it. That was another milestone for another day.

Monica began planning, for a distant date, Chandler's marriage proposal. Chandler felt that a great weight had been lifted from his shoulders. Both took for granted that this night would be heavy on sex. Rachel was at Ross's for the night. They began kissing and disrobing at the front door to Monica's apartment and all the way to her bed.

They had developed a routine that worked well for them, which was similar to their first night together. First, Monica gave Chandler a quick blowjob, being careful not to make him climax. Second, Chandler went down on Monica, bringing her to orgasm and thoroughly lubricating her vagina. Third, Chandler mounted Monica and came in her pussy. Fourth, Monica rode Chandler and, most often, had another orgasm. Fifth, Monica would blow Chandler, usually drawing a second orgasm from him.

Monica said, playfully, "This is such a special night, I think we should mix things up." Chandler registered his assent with the simultaneous raising of eyebrows and penis. She grabbed the lube, climbed into bed, and sat back against the headboard. She poured some oil across her chest. Chander walked on his knees to her, straddled her, and spread the oil around. At the same time, Monica heavily oiled Chandler's cock.

Monica pushed her boobs together to create the love tunnel. Chandler inserted his cock in the bottom and slid it through until the tip showed above Monica's breasts. He thrust with vigor, and urged, "Tighter." Monica squished her boobs together as tightly as she comfortably could. She added to his thrusts by working her boobs downward on his upward stroke, and vice versa.

Monica added a layer of stimulation by looking up at him and smiling. Chandler moaned as he stroked. Monica then put the finishing touch on the boob job by coaxing him, "Fuck my tits. Fuck my tits! FUCK MY TITS! You wanna come in my mouth, baby?" Chandler nodded, dripping perspiration from his forehead onto her chest. "Come, baby, and I'll swallow it. I want to swallow your cum! Titfuck me and come in my mouth. I'll suck it out of you and swallow it for dessert!"

That was the last straw, Chandler pulled his cock from between her tits and pushed it toward her mouth. He used both hands on the back of her head to encourage her to ingest his cock. She inhaled his cock and sucked with all her might. She worked her way down to the base of his shaft. Inside her mouth, she worked her tongue on the underside of his penis. He vocalized, "Ah! Ah! Ahh! Ahhhh! AHHHHH!" announcing his ejaculation. Monica knew very well when he came because she felt spurts of semen shooting past her uvula and down her throat.

She pulled her head back, wiping his cock with her lips and tongue to clean off all of the semen. She swallowed, then deepthroated him and repeated the cleansing cycle three times. She let his cock slip from between her lips, looked up at him, and gulped hard. She washed it down with wine. She wiped her mouth with the back of her hand, and cried, "Happy birthday, Chandler!"

He said, "Thank you! What's next?"

She moved down the bed, and said, "You lie back and recuperate. I'll handle everything." She straddled his hips, and lowered herself onto his cock. She moved carefully, for she had not used lubricant on her pussy, and she had sucked off most of the lubricant from his shaft. Once she had herself impaled as deeply as she could, she leaned forward to kiss him.

Monica rose back up, and commenced a complex dance. She twitched, twisted, and rotated her hips. Then, she arched her back and ground her clitoris against him forcefully. Now, she groaned. After a minute of that, she was ready to come. She thrust her hips forward fast and hard. When she climaxed, she dropped her head and groaned extravagantly.

Finished, Monica raised her head, tossed her hair back, and gave him a big smile. She said, "We can flip over any time, dear." She continued to massage his dick with her pussy.

Eventually, he said, "Now." In this instance, she dismounted to make the switch. She lay on her back, knees bent sharply. He got into position, and she spread her legs wide for him, Chander dove in with gusto. Monica yelped at his abrupt entry, but this was his birthday sex, and she got into the spirit of things. She massaged his prong with her vaginal muscles as best she could. It wasn't nearly a vise, but Chandler could certainly feel her clamping down on his cock. He found this highly erotic, not so much from the sensation but more from the fact that this beautiful woman would do that just to make him happy.

Chandler slammed his cock into her hard. She let out a little gasp with each impact. He focused on his breathing in order to maintain the torrid pace of his thrusts. It took several minutes of exertion for him to bring about his second orgasm. He said, "Here I come!"

Monica answered with "Yes! Fuck me! Fuck me hard! Harder! Ram it home, darling! I love you!" During her rant, he dispensed his cum. For a second orgasm, it was superb. Chandler fell over on his side, then rolled onto his back. They held hands, lying side-by-side. After a while, Monica rolled onto her side, facing him, and said, "Happy birthday, my love. Is there anything else I can do for you right now? Anything at all?"

Chandler shook his head, fully content. He rolled his head toward her, and said, "I love you, Monica."

"I love you, Chandler. Tell me what I can do to make your birthday celebration special. I know you're probably done for the evening, but you have a week to indulge. Anything."

He grinned. She sensed something. She asked, "There is something! What is it? You can ask for anything at all during birthday week. If you ask, you might get it. If you don't ask, you can't get it."

He turned on his side, facing her. "There is something guys talk about all the time, that I have never tried. I never trusted anyone enough to ask, much less do it."

She said, "Ah, if it's what I think it is, I've never done it either." They had a brief staring contest. She broke the spell, "Anal?"

"Yes. What do you think?"

She said, "Anytime this week. I suggest you not wait until your birthday party, because I'll be very busy and we may both be too tired or drunk."

"Thank you. I look forward to it, but I am nervous. You?"

She shrugged, "Oh, I'm not nervous. Between the two of us, I think we can figure it out. It'll be fun!" She had estimated that his cock was not as thick as certain things she had passed, so it shouldn't hurt any more than they did.

He said, "How about Friday night? Or will you be too busy with party preparations?"

"Friday night it is. I have all day Saturday to prep for the party. I can get you a new bottle of lube for your birthday!"

Monica confirmed that Rachel would be spending Friday night at Ross's. She did a little research into the best lubes for anal sex, finding little of value. Just for fun, she did wrap up a big bottle of lubricant for Chandler to open and use on her on Friday night. For his part, Chandler had a tough time concentrating at work all week, anticipating the big event.

Chandler dearly hoped that Monica could tolerate it or perhaps even enjoy it. If he liked it, he wanted her to like it, also. He did some research himself. On Friday night, they met for dinner immediately after work, and got home early. Monica excused herself to use the bathroom. When she was done, Chandler took his turn. When he was done, the door to Monica's room was open.

He went to the doorway, and his jaw dropped. The room was well lit with candles, and Monica stood radiant in a black negligee. She helped Chandler off with his clothes, but before she would let him strip off the negligee, she presented him the phallic birthday gift. Chandler opened it, expecting lubricant, and getting exactly that.

Chandler slid the tiny straps off Monica's shoulders, and the entire negligee fell to the floor like a feather. Monica climbed into bed, arranged a couple of pillows in the center of the bed, and lay face down, with her pelvis on the pillows. Her derriere was raised enticingly.

Chandler opened the lube, splashed it on his cock, and climbed up behind her. He gently pushed her knees apart and kneeled between her legs. Hovering over her, he guided his cock to her anus, which looked perfectly clean and pink. It was not at all ugly or disgusting, he found. He put the head of his penis into the opening gently. He asked, "Okay?"

"Yeah, just do it. I'm fine."

Chandler pushed gently, backed off a bit, and pushed again. In this incremental manner, he worked his way in. She gasped with each movement. When his groin touched her buttocks, he pushed some more, flattening her buttocks, and gaining another inch of depth. He said, "I'm in. How are you?"

Monica was feeling some strain, but not too bad. She said, "I'm fine. Happy birthday! Do your thing."

Chandler delicately withdrew about an inch and re-inserted. He repeated the action. The feeling was exquisite, different than a vagina. It would be nice to have both, for variety. He suddenly realized he forgot his special surprise for Monica.

He took his right hand off the bed, resting his torso solely on his left arm. He slid his hand between Monica's groin and the pillow, and sought out her clitoris. When he found it, Monica cried, "Ohhhhh!" He jiggled the clit, and she moaned continuously. It was difficult to stroke his cock in and out of her ass and finger her clitoris simultaneously. It was like rubbing your belly with one hand and tapping your head with the other. Chandler clumsily alternated between the clitoris and the anus with only a little overlap.

When Chandler felt his climax approaching, he buried his cock as deep as it would go, and focused only on bringing her off. The continuous stimulation got her moist and feeling great. After a few minutes, she bawled, "Oh, God! I'm coming! Ooooooh! Ugh!" He felt her stiffen and shudder. He returned to working his cock in and out, and ejaculated in her ass as gently as he could. He had worked hard to make it pleasurable for her, in hopes of enjoying anal more often.

Chandler extracted his cock as gently as if he were disarming a bomb. He climbed out of bed. She said, "Shower." Chandler headed for the bathroom with Monica a few seconds behind. They washed very thoroughly in very hot water. Once they were clean, Chandler held her and said, "Thank you for my birthday present. I loved it, and I love you."

She kissed him, "I love you. It wasn't too bad for me. I never expected to come in that situation. Well done!"

"I guess that makes you anal retentive." Monica gave him a sour look. Seriously, he asked, "What's the verdict?"

She pondered for a moment, "On special occasions. How's that?"

"Great! Your birthday is just around the corner."

She said, "Uh, I think that's supposed to be a special occasion for me."

As they toweled off, Monica confided, "I never told you about Ross and Rachel, and how they do what we just did. Ross didn't tell you, did he?" Chandler shook his head. "Well, it can be described as harmless role-playing, or as violent anal rape, depending on your gender." Chandler looked incredulous.

She continued, "Rachel is using it as assertiveness training for Ross. She doesn't consent, but she doesn't fight him, either. He has to take it, if he wants it. I accidentally saw him pounding her in the ass, and it was a little on the rough side, but it didn't hurt her, and it's even fun for her."

Chandler marveled, "Wow! I cannot, by any stretch of the imagination, picture Ross Geller forcing himself on a woman."

"Remember, Chandler, she not only gave him permission, she tantalized him into doing it. It wouldn't hold up in court."

Chandler said, "I'm happy with our method, if you are."

"Absolutely. There's lots of other kinds of role-playing we can do." Chandler's eyebrows went skyward.