Friends - Alternate Reality Ch. 22

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Ch 22--The One where Annie Spends the Night.
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Part 22 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Annie arrived at eight o'clock with a small bag. She hugged Rachel, then hugged Ross, held his face in her hands, and stretched upward to kiss him passionately. Rachel closed the door for discretion, and said, "Okay, you two. Annie needs to get settled, and then you can begin." Annie took a quick shower. Ross had already taken two. They ate some very good Chinese food, but Annie and Ross held back so as not to be too full for extreme sexual exertion.

Annie slapped down her Chinese, and said, "Ross, how do you wish to proceed?"

Ross was nonplussed, "Uh, um, I don't know." He looked to Rachel for guidance.

Rachel patted him on the cheek and said, "Oh, that is adorable, dear. I will help you nail my cousin." She sat back, and said, "Both of you come to the bedroom, where you will receive your assignments."

Annnie raised her hand like a schoolgirl, "Miss Greene, may I go to the little girl's room, please?"

"Yes, you may." Annie grabbed her bag and ran into the bathroom. Ross and Rachel went into the bedroom. Rachel said, "Undress, please." Ross was nude in moments. Rachel got undressed, but put on silk pajamas. This session was going to be all about Annie. Annie arrived, barefoot, and wearing a skimpy black negligee that made her sexuality explode into view. Her generous boobs hung out of the top, which barely concealed her nipples. She was hot.

Rachel said, "You two familiarize yourselves with one another." Annie and Ross met in the middle, and embraced. Ross put on hand on her breast, kneading it. Annie put one hand on his cock, and stroked it slowly. Their bodies pressed together, and they both wiggled against the other, relishing the sensations.

Rachel said, "Ross, peel that thing off her." He glanced at Rachel for validation. She nodded impatiently, and he stepped back. He reached out, pulled the tiny straps off her shoulders. The negligee hung on her breasts. He pulled down the negligee with both hands to expose her breasts, then her tummy, then her hips. The negligee landed on the floor around her feet. It was soon joined by her panties. Annie stepped out of the clothing, and they walked to opposite sides of the bed and climbed onto it.

Rachel directed, "Annie, here's the lube. I recommend that you oil him up, and yourself, if you know what's good for you." Annie filled her palm with lube and stroked Ross's cock lavishly. She put more lube on her fingers, and reached down to her pussy. She stroked her clitoris and worked lube into her vagina. She handed the bottle of lube back to Rachel, and stroked her clit some more.

Rachel said, "The first act is straight sex, missionary position. Do not hold back anything, Ross. You ready, Annie?" Annie nodded. She lay on her back in the center of the bed and assumed the "fuck me" position. She raised her knees up and opened them like a book.

Ross shuffled on his knees to get between her legs, and leaned over Annie with his arms extended, elbows locked, and hands next to her shoulders. For Rachel, he normally put his hands under her armpits, but Annie was shorter.

Annie was all smiles. Ross looked down. She was fully exposed. The target area was clear. He pointed his glistening cock to the hole, and gently inserted the head. Annie moaned, "Ahhhh." He looked into Annie's face, and pushed in further.

Rachel commanded, "Ross! Plunge that thing in there, and fuck her brains out." He was spurred to immediate action. He drove his cock hard, almost all the way in.

Annie howled, "Ohhhhh! Ohhhhhh! Ohhhhh!" One more shove, and he buried the whole thing.

Rachel said, "Now, fuck her, Ross! She's here for your pleasure. Do it." Annie grunted. Ross pumped his cock in and out of Annie's pussy with all the strength and agility at his disposal. He was already near climax, since he had not ejaculated in three days.

Ross shouted, "Ah! Ah! Ah! Ah!" as he hammered Annie. Annie had the wind almost knocked out of her with each thrust. Ross came. His fierce grimace and animalistic growl announced his orgasm. He injected a massive quantity of seed into her. He launched at least eight or ten spurts. Annie hung on for dear life.

Ross's ejaculation petered out. He pulled his dick out of Annie, and climbed off the bed. He stood next to Rachel, breathing hard from the extreme exertion. Annie rolled over on her side and drew her knees up into a fetal position, groaning. Rachel said, "Ross, honey, go rinse off. I'll scrape her off the mattress." Ross left, his erection leading the way. Rachel put her hand on Annie's shoulder, "Annie, are you all right?"

Annie said, "Yeah, I'm all right, you bitch. He almost cut me in half."

"Honey, you knew exactly what size his cock was."

"I know, I know. I'll be all right." With groans and whimpers, Annie stretched out and rolled onto her back. "What's next, Rachel?"

"Well, if you'd like a break, I think you two should pause for a snack before he does you again."

Annie put on a nightshirt, and Ross put on sweats, and the trio sat at the dining table and ate in silence for a while. They ate slowly, not wanting to feel too full. Rachel asked, "How are you feeling, Annie?"

Annie looked at Ross, "I'm great. It was a lot to handle, but I'll be fine."

Rachel asked, "How was she, Ross?"

Ever the gentleman, "She was very good. Not Rachel good, but very, very good."

Rachel asked, "What would you like to do next, Ross? Everything is on the table."

Ross looked at Annie, "I want to play with her boobs, and get a blowjob. Instead of deciding between the two, I think I'll have both."

Rachel said, "That can be arranged. All contestants to the arena, please." They returned to the bedroom, and Ross and Annie stripped. Rachel asked Ross, "How to you want her? On her knees or lying back in bed?"

"Definitely lying back in bed. I'm still too tired to stand."

Annie climbed into bed. Rachel gathered the pillows and made a sloping backstop for Annie to sit back against. Ross got on his knees, astride her hips, and presented his cock to Annie's mouth. She sucked on the head, and stroked the shaft with her hand. It was a slow start, but Ross forced himself to be patient. Annie started to bob her head a bit. She only got down about an inch below the head. The vast majority of Ross's cock was treated to a handjob only.

After a couple of minutes, Ross pushed his cock forward to get more of it into her mouth, but Annie tilted her head back an equal amount. Ross responded by holding her head with both hands and forcing his cock in another inch or so. He pistoned his cock in and out of the seal formed by her lips. He forced the action.

Soon, Ross had enough of himself in her mouth that she could no longer stroke the remainder with her hand. Ross urged her on, "Suck on it, Annie! Can you take more of it? Try to deepthroat me, Annie." Annie tried gamely to ingest Ross's full length, but she gagged with at least two inches remaining outside. Ross said, "Okay, just take what you can, and stroke it in and out."

Ross released Annie's head, and she did her best to move her head enough to satisfy him. Annie was no match for Rachel in the head department, but it still felt good. Ross left her to her own devices for a while. Long before he approached orgasm, Ross said, "Enough," and pulled his dick out of her mouth.

Ross declared, "Titfuck." A bottle of lubricant appeared before him in Rachel's hand. He spread it over her boobs and his cock, and handed the bottle back to Rachel. Ross pressed the underside of his cock against the gap between her breasts. Annie pushed her boobs together with her hands, engulfing his cock, except for the head, which remained visible just below her throat. He worked his cock up and down in long, deliberate strokes.

Annie did a good job of keeping his cock contained between her breasts. On the upstroke, the head of his penis poked out of the boobs and nearly touched her chin. She bent her head down, stuck out her tongue, and licked the tip of his cock each time it approached her lips. This was new to Ross. He enjoyed the fun of pushing his cock close enough for her to reach it.

With a little more force, he drove it almost to her lips, and she was able to lick the entire head. He said, "Tighter," and Annie pressed her boobs together harder. Ross sped up his thrusting, and he began to make squeaking sounds. He declared, "Suck the cum out." Annie nodded in understanding.

Ross gave a few more strokes, then pulled his cock all the way out of the tit tunnel, and pushed it into Annie's mouth. She sucked hard on the head, while furiously pumping the shaft. With the lube on his shaft, this felt superb to Ross, who rewarded Annie with four blasts of cum. She swallowed it, and stopped sucking. Ross said, "Yeah, good finish, Annie! Really good."

Ross fell back onto the bed with an enormous sigh. Rachel said, "I'll bring some wine." She reappeared in a few minutes with a bottle of white and three glasses. Rachel poured the first glass for Annie, who used it to wash down Ross's semen. Ross took the wine mainly because it was cold, and he was still perspiring from the effort he had put out. Rachel poured herself a glass, held it out, and said, "Here's to a great start to the weekend." The three clanked glasses and drank.

Rachel asked Ross, "Ross, honey, are you satisfied for a while?" He nodded wearily. "Well, then, let's get cleaned up and go into the living room to decompress a little." Ross took a shower and was out in the living room, wearing sweats, before the girls emerged from the bedroom. Annie wore her nightshirt. They all sat down.

Ross and Rachel cuddled on the loveseat. Rachel said, "You guys were great. An excellent performance by both of you."

Annie lay her head back, and said, "Rachel, this is supposed to be a threesome. You got the next one."

Rachel and Ross chuckled. Rachel teased, "A little too much for you, Annie?"

Annie said, "That was a very, very hard fuck. I'm beat."

Rachel clicked glasses with Ross, and said, "Congratulations, honey, you outlasted cousin Annie. And they said it couldn't be done." Annie laughed a little. "How are you, Ross? What would be yummy for Ross, right now?"

"Sleeeeeep."

Annie agreed, "Yes. Sleep."

Rachel said, "Fair enough. Ross in the middle, Annie on his right, me on his left, as always. Annie, you definitely need to rinse off. We'll have wine waiting in the bedroom." Annie staggered to the bathroom. Ross staggered to the bedroom. Rachel went to the linen closet for fresh sheets. Ross helped her change the sheets. He dropped onto the bed like a felled tree. Rachel handed him his wine glass. Rachel arranged the pillows, took off her pajamas, and slid in next to Ross.

Rachel asked, "What do you think, Ross?"

Ross said, "I am very glad we did this, Rachel. Thank you. And, it's not because of the sex. It's for the reason you insisted on it in the first place. This gives me my first yardstick against which to measure the woman I am with, and you come out far ahead. I have always known I was lucky to be with you, but this is next level."

Rachel asked, "Was she really that bad?"

"No! She wasn't bad. She was great. She wasn't you, though. It's not just the feelings I have for you, either. It's the sex. You're so much better!"

Rachel smiled, and said, "Mission accomplished."

Annie arrived, nude. She trudged to the bed, got in, and said, "Good night, all! Love you."

Rachel said, "Good night, honey. Great job."

Ross added, "Tasty. Very, very tasty, Annie. Good night."

Ross and Rachel lay back, Ross rolled on his side and spooned Rachel.

Rachel woke up first, thinking, "Ross must really have been worn out, not to be awake first." She went to the bathroom. When she returned, Ross was sleeping on his back. She gently uncovered Ross down to his thighs. He had an erection, so he must have been dreaming. She delicately took his cock into her mouth. She wanted to blow him a while before he came to full wakefulness.

He stirred when she began to tongue him. She took nearly all of him into her mouth and looked up at his face to see if he was waking up. She wanted to deepthroat him to underscore the fact that she could and Annie could not. She sucked softly for a short while, but his eyes soon opened and he groggily came to his senses.

The moment his eyes opened, Rachel went full throttle, sucking with all her might. She deepthroated him, and gazed into his eyes, for this was a huge turn-on for him. He ran his fingers through her hair affectionately. She sucked him for a while, and pulled her head off of him with a loud slurp.

Rachel moved up to snuggle with him. He stroked her back, and said, "You're everything to me, Rachel." She tensed up a bit. It had sounded like Ross would say, "I love you." Rachel knew that Ross had loved her for years, and that he was terribly sentimental. It must have been difficult for him to avoid saying it. She lay her head on his chest, and asked, "How'd you sleep?"

"Great, I guess. I hardly remember sleeping."

She jiggled him a bit, "You had some hard workouts last night."

He laughed, "That's true." He glanced to see that Annie was still asleep. "I think I found out what I needed to, Rachel. I've got the best girlfriend in the world."

"Well, Ross, you have to go through the whole weekend. If you don't need the validation, do it for the fun. We can't send her away early."

"I reluctantly agree."

Annie began to stir. She opened her eyes and moaned. She pulled the sheet over her head. Rachel said, "Ross, Annie is notoriously slow waking up. We'll need plenty of coffee." Ross and Rachel got up, put on some clothes, and went to the kitchen to make coffee and tea. Rachel took a steaming cup to Annie, who perked up just enough to drink some of it.

Ross and Rachel read the newspaper for a while, until Annie dragged herself out of the bedroom and to the bathroom. She came out a few minutes later, hair brushed, and dug into her bag for some clothes. When she returned, Ross said, "I think you two ladies deserve to be taken out to breakfast."

Annie asked, "I know I do. What of Rachel?"

Ross was quick to come to his girlfriend's defense, "Actually, Rachel gave me a very special wakeup call this morning. She did not speak, and for the very best of reasons."

Annie and Rachel debated what kind of breakfast they wanted. It finally came down to how much time they felt like devoting to pulling together a "look" from the wreckage of last night. They agreed to go to a simple deli, that nevertheless had great food. Ross made them Bloody Mary's in paper cups, that they drank on the way to the diner.

While they ate breakfast, Annie asked, "Have we got anything planned for today?"

Rachel said, "No, but I'd love to go shopping." Annie agreed. They would go back to Ross's, fix their faces, and shop till they dropped. Given the way the girls had been serving him, Ross felt obligated to accompany them. He had learned that hours of shopping could be tolerated if he brought his tablet and headphones with music, games and movies, and also made frequent detours to sporting goods or menswear.

They shopped for two hours, broke for lunch, shopped another two hours, had a snack, shopped another hour, and had an early dinner. Rachel pushed Annie to drink as much as she could get into her. Annie was theirs for the night already, so Ross wondered why she needed to be drunk.

They took a cab home, and Ross half carried Annie down the hall to his door. As they walked from the elevator, two of Ross's neighbors passed them in the hallway. Ross had the smoking hot Rachel, of course, plus an equally hot blonde slumped in his arms. That raised some eyebrows, and also raised Ross's reputation in the building.

Once inside, Rachel said, "You'd might as well lay her on the bed, Ross." He did so, and when he returned, he asked, "Why do you want her to be so drunk?"

Rachel answered, "Because, she probably would not consent to what you're going to do to her." Ross looked alarmed. Rachel embraced him, "Ross, you are going to let go all your inhibitions and enjoy that beautiful girl in there. You are going to fuck her in the ass. Not the way you do me, but all-out fun. Let it all go."

"I reluctantly agree."

They went into the bedroom and prepared the ceremonial sacrifice. Ross stripped. He and Rachel stripped Annie, who had been snoozing. Annie woke up enough to mumble incoherently. Rachel stacked two pillows in the center of the bed. They lay Annie atop the pillow, her ass high in the air. Rachel put on pajamas once again.

While Ross lubed his cock, Rachel soothed Annie and stroked her hair, "Annie, Ross is going to make love to you, okay? Do you consent to making love, dear?" Annie nodded. "Good. You just stay here with me and relax. Ross will do everything. He's ready now. Just relax." Ross was poised above Annie's asshole. He dripped lubricant onto it, and placed the head of his cock on the lips.

He gently pushed in. The intrusion woke Annie up quickly. She tried to turn to see what was going on behind her. Ross put his hand on her upper arms to pin her down. She babbled. He pushed in further, then rhythmically pumped it in and out like a piston. Annie complained, "No. It hurts. It hurts."

Rachel said, "Do it, Ross, before she rebels." Ross reared back and drove his cock in hard, up to the hilt.

Annie cried out, drunkenly, "Ow! Ow! Who's doing that? Stop it. Stop it." Ross thrust his hips against her buttocks hard for a couple of minutes before he came. He grunted with satisfaction with each dab of semen he left in her rectum. Annie pleaded, "Stop it. Stop it." Ross pulled out, slowly, as soon as he was finished.

Ross immediately dashed to the bathroom to shower. Rachel tried to console and revive Annie. Annie had stopped complaining soon after Ross withdrew his dick from her ass. Rachel said, "Here, honey, let's get off those pillows and lie down, okay?" As soon as Annie was able to drink it, Rachel poured more wine into her. Annie asked, "What happened?"

Rachel held a hand on Annie's forehead, and said, "Annie, Ross fucked you in the ass. It's all over, now. It's all over, and you are feeling much better."

Annie slurred her words, "Why did he do that?"

Rachel said, gently, "Annie, honey, you said he could, so he did. He did it because you wanted him to, but it's all over now, and you can rest."

Annie lay quietly for a while, then drifted off to sleep. Rachel and Ross spent some quiet time in the living room, toasting their success.

Annie slept through the night, but woke up with a headache. Rachel and Ross got as much water into her as possible, as well as a Bloody Mary and three aspirin. She felt a lot better by mid-morning, so they put on some nice clothes and went to brunch as a classy hotel. They toasted one another with champagne. The food greatly improved Annie's condition.

Annie asked, "Okay, what happened last night?"

Ross and Rachel looked at one another, and Rachel took up the tale. "Well, honey, you had a little too much to drink. When we got home, Ross wanted to buttfuck you. You didn't object, so he did. It didn't hurt, because Ross was careful. You woke up with a hangover."

"Rachel, my headache somehow extends to my ass. I've never had anyone that big in my ass before. I can't believe I agreed to that."

Ross said, "Well, Annie, now that we know, I won't do it again, okay?"

They lingered at brunch and got back to Ross's apartment at noon. They lounged about for a few hours, talking, making phone calls, and watching TV. A couple of hours before Annie had to leave for the train, Ross sat beside her on the couch, their sides touching, he put a long arm around her, and slipped his hand under her bouse and bra to cup her breast. She snuggled a bit closer to him.

Ross purred into her ear, "Annie, you are beautiful. You are the most beautiful girl I have ever been with. I want you, Annie. Please." Annie was a sucker for flattery. She nodded, and got up to head for the bedroom. Rachel followed Ross. Annie was in a pretty good mood, she started to strip Ross, and he her.

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