Friends - Alternate Reality Ch. 16

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Ch 16--The One with Ross and Annie.
3.2k words
3.22
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Part 16 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Rachel's cousin, Annie, was coming to town to visit. Ross and Annie already knew each other a bit. Annie was 24, two years younger than Rachel, and four years younger than Ross. She was blonde, very pretty, and flighty. Annie and Rachel were devoted to one another, in spite of having had their differences over the years. The Greene clan was generally supportive and conscientious, so all of them got along well.

Annie had gone to college mainly to avoid having to get a job. She had bounced around to various jobs, and numerous relationships. Her parents still supported her, financially, to a great degree. Their hope was that Annie would marry some guy wealthy enough to take over the payments on her.

Annie and Rachel had shared Rachel's bed on previous visits, but Ross had a nice sofa bed in his living room. It was decided that Ross and Rachel would occupy his bedroom, and Annie would sleep in the living room. When Annie arrived at Rachel's apartment, Ross was there. Everyone greeted one another warmly, especially Joey, who had aggressively pursued Annie in the past, without success. Later, Rachel and Ross took Annie to Ross's. His apartment was exceptionally spacious and well-appointed. The three stayed up late, reminiscing and gossiping.

When they were alone in their bedroom, Ross quietly asked Rachel, "Did you notice anything odd about Annie's behavior tonight?"

"No odder than usual. Why?"

Ross said, "I think she was coming on to me, just a little bit."

Rachel laughed out loud, "Oh, Ross, you poor thing! I adore you, but Annie sets her sights pretty high, dear."

Ross was hurt, "You think she's out of my league?"

"Ross, you are the most important thing in my life, dear, but even I'm out of your league."

Ross challenged her, "Put your money where your mouth is, Rachel. If Annie comes on to me, I can do with her whatever she has in mind. No consequences."

Rachel said, "I agree. Just don't make a fool of yourself trying to make that happen."

"Fine."

The next morning, Saturday, Ross woke up earlier than Rachel, as usual. He went to the kitchen to make coffee and tea. He was nude, with a morning erection. Annie woke up and stared at him. She got a good, all-around look at Ross. When he realized she was there, Ross ran to the bedroom and put some sweats on. He came out, and closed the bedroom door behind him. Embarrassed, he said, "Annie, I apologize for that. I am sooooo sorry. I completely forgot that we had a houseguest. Please forgive me."

Annie was having fun with it, "There is nothing to apologize for, Ross. I enjoyed the view. I got a good, long look. A long look. Loooooong."

Ross was astonished at her daring. His first thought was that he wished Rachel was here to witness Annie's flattery. For that matter, he wished everyone he knew was here to witness it. He played it cool, "Did you sleep well, Annie?"

She said, "Yes, but probably not as well as you and Rachel. She's a lucky girl."

Ross ran with it, "Yes! Yes, she is a lucky girl, but every time I say it out loud, people laugh. Thank you for having the discernment to say it."

Annie flirted, "Tell me, Ross. What is it like between you two? Are you a hot couple?"

"Um, I'd like to think so. Things between us are amazing, Annie. We have real chemistry. I've never been this happy in my whole life." Annie batted her eyelashes. Ross said, "Hey, I'll make some coffee."

Annie wore pajamas. She followed him to the kitchen, and sidled up to Ross. She stood next to him as he made coffee, leaning so that their arms touched firmly. Ross knew that this was intentional on her part, thinking, "Damn, Rachel really needs to see this!" Ross tried to break the tension, "So, Annie, are you seeing anyone?"

Annie squirmed a bit, rubbing against Ross very deliberately. Ross thought, "Okay, maybe it's best Rachel doesn't see this."

Annie said, "Oh, no. I date, but not a lot, and no one special guy."

Ross knew that Annie's idea of dating "not a lot" could encompass almost anything. Annie was only about five foot three, so Ross towered over her. She reminded him of a teddy bear; little, adorable, warm, soft. Ross turned a bit toward Annie, and she pressed herself against his arm as he rotated. She ended up resting her breast against his arm. Annie was curvy, and had C-cup breasts, which looked huge on her frame. Ross thought, "Those are some fuckable tits."

Just then, Rachel's voice intruded, "Good morning, everyone. How did you guys sleep?" Ross startled dramatically when he heard her. She came into the kitchen, and he greeted her with a kiss. She did not seem to have noticed the interaction between Ross and Annie. Annie excused herself to use the bathroom. Just in case Rachel had seen, Ross covered his tracks by saying, scornfully, "Rachel, did you see that?"

"See what, Ross?"

"Uh, Annie rubbing up against me. A little too close for comfort, Rachel."

Rachel waved a hand, "Oh, she's like that with everyone. She's an incorrigible flirt. Trust me, you haven't got a shot."

Ross was desperate to make Rachel see what he saw, "Rachel, you should have seen what happened earlier. She was telling my how lucky you were to have me."

"Well, that was a very sweet thing for her to say. I agree. I am lucky." She kissed him.

"You don't understand, Rachel. I forgot that she was here, and I came out of the bedroom completely nude. She saw ev-er-y-thing. She just watched me until I noticed she was there. She was checking me out."

Rachel giggled uncontrollably, "Ross, how could you? So, she got a good view, huh? That is hilarious."

Ross felt like Marco Polo, a man trying to convince a skeptical world that what he had witnessed was genuine, "Rachel, after I put on sweats, I came out again, and she made a big deal of how she got a long look. She said it like, 'a loooooooooong look.' It was very forward."

Rachel said, "Dear Ross, she is a flirt, a hussy, and a prankster. She's not into you. If she is, you have my permission to go for it." Rachel poured herself a cup. "Thank you for the coffee, dear. Now, I think we should go out to breakfast, where we can make plans for the day. I have that damned baby shower this afternoon, so you will have to entertain Annie for a few hours."

Ross was alarmed, "Do you think it's a good idea to leave the two of us alone together?"

Rachel guffawed, and nearly shot coffee out her nose. "Oh, get over yourself, Ross. This has been fun, but any more and it will just be sad."

Ross felt certain that Annie's continued flirting was more than just habitual. They spent the morning shopping. Ross had learned that his opinion on any outfits the girls tried on would be worse than useless. He amused himself listening to music with his headphones, and by hanging out in the men's department.

The trio made it back to Ross's apartment in time for Rachel to change for the baby shower. She left in a hurry, bearing a frilly gift. Ross saw her to the door, and kissed her goodbye. When Ross closed the door and turned around, Annie was standing a few feet away, with a devilish look on her face. It was a look of determination. She walked slowly up to Ross, swinging her hips provocatively.

Annie did not stop advancing until their bodies were touching. In particular, her breasts pressed lightly against his midsection. She looked up at him, and licked her lips. She took him by the hand and they sat on the sofa, facing one another. Annie held one of his hands.

Ross ventured, "You are a flirt, Annie."

She said, "Yes, I'm a flirt, but this isn't flirting, Ross." She leaned forward, put a and on the back of his neck, pulled his head down, and kissed him on the lips.

Stunned, Ross said, "My God, I was right, after all. Rachel said that you were just flirting out of habit. I told her it was more than that."

Annie said, "It is more than that, Ross. I haven't had a man in a while, Ross, and I think Rachel should be willing to share."

Ross said, "Uh, I don't think Rachel is that generous. She did tell me that, if you really were into me, I had carte blanche to do whatever."

Annie's eyes went wide, "She actually gave you permission to be with me!? Ooh, let's go." Anne ran her hands under his shirt and up his chest. He had changed into a t-shirt and sweat pants. Ross had had two Bloody Mary's at breakfast, and three beers after they got home from shopping, so he was a little buzzed. His reactions were slow, but he stood up and shed himself of her hands, saying, "I'm not going to endanger my relationship with Rachel, Annie. Not for you, or for anyone."

Annie stood, and walked to the kitchen, saying, "Whatever you say, Ross." She brought back two beers for them. They sat down again, clinked bottles, and drank. Ross felt that the danger had passed, and that he was safe. When he had finished his beer, Annie said, "Ross, Rachel told me something. She said she wished she had my boobs, so you could titty fuck her. Do you enjoy doing that, Ross?"

Ross was wary, "I am perfectly happy with Rachel. She is beautiful, in every way."

Annie pressed, "Do you enjoy titty fucking, Ross?"

"I have, in the past, but that is over. I'm with Rachel now, and she is beautiful."

Annie said, "Ross, she is beautiful, but she is not every thing to every man. She said she wanted you to have a pair like mine to fuck. She gave you permission to do it, for God's sake! What else do you need?"

Annie's argument sounded compelling to Ross. Rachel had told him herself that she wished she had boobs big enough to titfuck. She had said, more than once, that he had free rein to do anything that Annie was willing to do. Also, she had repeatedly belittled him, dismissing him as too undesirable to attract Annie.

Annie was wearing a red tank top and black slacks. In one smooth motion, she pulled the top over her head and off. Her bra was black. It was lacy, it showed considerable cleavage, and it hooked in the front. To Ross, a bra that hooked in the front was a sexy come-on. He had considered asking Rachel to start wearing them. Now, Annie's perfect breasts called out for attention.

She leaned toward him, pushing her chest out, and said, "Unclasp me, Ross. You can just look at them, if you want." Ross stared at her cleavage, but said and did nothing. Annie slowly unclasped the bra herself. She did not open up the bra, but left the cups dangling precariously upon her breasts. It was dead sexy. She whispered, "Touch them. Go ahead. I want you to. Open up my bra, and feel them. It's not cheating. Besides, Rachel gave you permission to do anything with me. Do it."

Ross reached out, took the cups in his fingers, and spread them out, revealing Annie's spectacular chest. As he tucked the cups away, she leaned further into him, causing his hands to graze her breasts. "Touch me, Ross. I'm all yours. Do it." He fondled her breasts, then massaged them, then squeezed them.

Annie removed her bra entirely, and reached for something in her bag. It was a fancy bottle of lubricant. She said, "Ross, rub this on my chest, please. Come now, be a gentleman." She took his palm and poured oil into it, then drew it to her breast. Soon, Ross was rubbing oil onto her chest, relishing the slippery, squishy feel of her boobs.

Annie reached into his sweatpants and grasped his cock. She would not let it go. The feeling of her hand on him was too much for Ross to bear. He stood and shed his pants and shirt. He was nude, with an erection, and Annie's hand clasping him. She oiled her hand and stroked his pecker with it. She lay back, reclining against the arm of the sofa, drawing Ross with her.

He kneeled on the sofa, and leaned forward. She took her hand off his cock, and pushed her breasts together with both hands. She jiggled her boobs a bit to entice Ross to apply his cock to them. He inserted his cock between her breasts. Annie worked her boobs up and down on his cock, squeezing him tightly between them. Ross moaned, and reciprocated by sliding his cock up and down her chest.

She urged him, "Come on, Ross, do it! Fuck my titties! Fuck my titties!"

The encouragement acted powerfully on Ross, who intensified his stroking until he cried, "I'm gonna come!" She bent her head down, resting her chin on her throat. His cock pointed to her mouth. She opened her mouth to receive his seed. Grunting and moaning, he fired generous jets of cum into her face. She took one on her nose and forehead, another mostly in her mouth, and the final one on her chin.

The moment Ross climaxed, he came to his senses. He was horrified at what he had done, and terrified of the consequences. He drew back from her, picked up his clothes, and disappeared into his bedroom. Annie spit most of the semen that had landed in her mouth onto her chest. She went to the bathroom to wash his cum off. She came out a few minutes later, and put her bra and top back on. She went to the kitchen to mix a pitcher of martinis.

Ross peeped out of his room. He was dressed as before. Not seeing Annie, he dashed for the bathroom. Annie took the pitcher and the glasses, placed them on the coffee table, and sat on the sofa. Minutes passed before Ross emerged. Annie waved him down, "Ross, come over here. Let's have a drink, and talk."

He said, "I can't believe I did that."

She consoled him, "Ross, I can't believe you didn't do more. My advances have always been well received, until now." She pouted. He sat down, and she handed him his drink. "Ross, you were a little drunk, you had permission, I invited you, and all you did was touch me. No oral, no intercourse. It wasn't even really sex. I think we should just forget it ever happened, all right?"

Ross jumped at the rationalizations, "Yes! It was just a mistake. It wasn't really sex."

Annie clinked glasses with him, and Ross downed the martini quickly. She poured him another. She handed it to him, "Drink this one a little slower, please." He took the drink, and sipped it.

Annie said, "I have a story for you, Ross. When I was a freshman in college, and Rachel was a junior, she stole my boyfriend." Ross looked startled. "It's true. Well, he was more of a potential boyfriend, but I had my eye on him first, and she ended up dating him instead. So, turnabout is fair play. What we did here today is nothing compared to what they must have done."

"I never heard that story."

Annie said, "Well, I'm not surprised Rachel didn't tell you, or anyone. The point is, I just got a little bit of revenge on Rachel. You didn't cheat on her. You never penetrated me. You did something with me that you can't do with Rachel. Oh, and by the way, she gave you permission to do it! It can be our little secret."

"Yes. I like the secrecy aspect."

When Rachel returned from the baby shower, Ross had Chinese food laid out for them. He even put on slacks and a nice shirt. He felt guilty, but he didn't want to go overboard and give himself away. Rachel went to the bathroom, and kept her clothes on, since both Annie and Ross were well dressed. They sat down to eat. Rachel asked, "Well, what did you two do all afternoon?"

Ross had a prepared statement, "In addition to getting the Chinese, I did some reading, and Annie and I talked quite a bit. I'm afraid to say we also drank quite a bit."

Rachel asked, "Is that why you're not having wine? How much did you drink?"

Ross said, "After you left, Annie plied me with martinis, and I drank them just to be polite. She's really good at making martinis, by the way."

Annie smiled and shrugged at the compliment. Rachel said, "Annie and I have gotten drunk together many times. Annie, what did you do?"

Annie said, "I made some phone calls, and tried to get Ross drunk."

Rachel chided him, "Well, Ross, I hope you don't have a hangover tomorrow."

Annie grew more mischievous, "Rachel, you will be pleased to know that I went after Ross hard, but he would not yield. He's crazy about some other girl." Annie raised her glass to Rachel.

"Oh, that's sweet, Annie. Ross, what feminine wiles did Annie entice you with?"

Ross cleared his throat, and said, "I'd rather not say, Rachel. You know how sexually aggressive she can be. Almost a predator."

Annie said, "Well, if Ross won't tell you, I will. I thought I would tempt him with my boobs. It's the only thing I can offer that compares with what he gets at home."

Rachel pooh-poohed her, "Oh, puh-lease. You are smoking hot, Annie, and you know it. Isn't she, Ross?"

"No comment."

Rachel gave a querulous look, "What exactly happened here this afternoon? Annie tempted Ross with her boobs. What else? And I haven't forgotten that I gave Ross permission to do anything Annie was up for."

Ross said, "She really came on to me, Rachel."

Annie said, "Do you forgive me, cousin?"

Rachel said, "I forgive you. Ross, I hereby order you never to be alone with Annie again. I also remember that you didn't want to be left alone with her today."

Now, Annie was indignant. She put her hands on her hips and scolded Ross, "What's that supposed to mean!?"

Ross turned to Annie, "It means, Annie, that you are such a vixen that I didn't want to risk temptation." He turned to Rachel, "And I never will again."

Rachel said, "Okay, I absolve you both of your sins, if any. We carry on with a clean slate from right now."

Later, when they were alone, Rachel put her arms atop Ross's shoulders, and said, "I didn't want to embarrass Annie, but I must ask one question. Is there any risk of a sexually-transmitted disease? You know, Annie is highly sexually active."

Ross reassured her, "On my word of honor, there is no chance of an STD, or a pregnancy. And, my condom supply is untouched."

Rachel kissed him, and said, "I am so glad we don't need to use those things. I didn't realize how much they kill the mood. I suppose it's okay to keep some on hand. I won't count them, though."

"I appreciate your trust."

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BrianMurphyBrianMurphyalmost 2 years agoAuthor

Dear Anonymous:

Chapter 45.

I have all 50 chapters submitted, but they are publishing them at a rate of about one per day.

Brian Murphy

AnonymousAnonymousalmost 2 years ago

I've fairly enjoyed this, but when do we see the one with Monica and Ross? With maybe a bit of Rachel thrown in?

Dewey Cheatham

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