Friends - Alternate Reality Ch. 21

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Ch 21--The One where Ross Reveals His History.
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Part 21 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Two months into their relationship, Rachel grew curious about Ross's past. She had attended Ross and Carol's wedding, and was eye-witness to their marriage and divorce. She had no visibility into his college years, and very little into the two years since his divorce. They had not delved into one another's sexual histories, except to declare themselves free of disease and Rachel protected against pregnancy.

They were watching a movie in which one character had married young, and later regretted not having had broader experience with the opposite sex. Rachel paused the movie, and asked Ross, straight out, "Do you ever wish you had more experience with women? I mean, more different women, when you were young?"

Ross was wary, "Well, no. I am happy with what I have."

"Bullshit, Ross! You must have had stretches when you wished you had a woman."

Ross tread carefully, "Of course, after I hit puberty, I was desperate for girls, and it was years until I got one." He looked at Rachel uncertainly, "The truth is, Carol was my first."

Rachel's jaw dropped, "She was not!"

"Yes, she was, and thank you for ridiculing me about a sensitive subject."

Rachel held Ross's arm, and backpedaled, "Oh, Ross, I didn't mean it that way. It must have been hard growing up, with high school and college, the way boys are. You must have some regrets, dear."

"I think I wouldn't have a problem with my dating history if Carol had not turned out to be a lesbian. Rachel, do not belittle me for this."

Rachel shook her head, "Oh, no, dear, no."

"Rachel, you were my second."

Rachel's face bore a look of paralyzing shock. She could not move or speak for several moments. She whispered, "Ross, is that true?" He nodded. "I didn't know, Ross. Oh, that is so sweet and precious, but the last two years must have been hell."

Ross did not meet her eye, "It was hell. Here I was, friends with a beautiful woman who I loved, but could not touch." He looked at her with a trace of anguish.

Rachel kissed him, and declared, "Ross, I don't want you going through life wondering 'What if?' I think you should sow some wild oats."

Ross knit his brow, "You want me to date other women?"

"No, I would be jealous if you dated other women. I want you to fuck other women. Just sex. Get it out of your system."

Ross said, "Rachel, what would that do to our relationship? My time with you has been the happiest of my life. I won't trade that for anything."

Rachel explained, "Well, without getting specific, I think you know I have had it pretty easy on the dating scene. I grabbed you only after I realized I never wanted a another shallow, temporary relationship. You are a real man, Ross. I know you're a one-woman man. I'm not afraid. I think the gulf between our backgrounds, especially since I have been your one and only straight lover, is liable to gnaw at you for the duration of our relationship. Aren't you even a little envious?"

Ross was apologetic, "I suppose so, in some ways, just like I've been envious of Joey."

Rachel took Ross's hands in hers, "Ross, I haven't been bothered by what transpired between you and Annie. Not at all. I basically let it happen. Tell me, really, what happened."

Ross was ashamed, "She bared her breasts to me. Then, she put her hand down my pants and grabbed my cock. I was a little drunk. She wouldn't let go. I succumbed. I fucked her tits. That's the truth, the whole truth, and nothing but the truth, Rachel. I swear."

Rachel chuckled, "It's all right, Ross! I knew something happened. This is minor. I'll tell you what, Ross, you can have Annie. All of her. Wouldn't you like that?"

Ross narrowed his eyes in suspicion, "Is this a trap?"

"No! No, silly. I am sincere. Annie would be a great choice for this project. I can think of one or two others...."

Ross said, "I don't know what to say, Rachel. This is unbelievable. I can't believe this is happening."

Rachel kissed him, "Everything will be all right, Ross, I promise. I just think that Carol was a gaping hole, no pun intended, in your life story. Your first love, your first marriage, and the only other woman you've been with. You need to wipe the slate clean, Ross. Get the taste of defeat out of your mouth. You need some big wins, you deserve them, and I'm going to give them to you."

Ross cautioned, "I want you to sleep on this, Rachel, before we do anything."

"Oh, I will. Tell me, Ross, would you be open to a three-way? I mean, us and another woman?"

Ross said, "That's a common fantasy for all men. That's all I'll say."

Rachel said, "Now I will insist that you not hold what I'm about to say against me." He nodded. "In such a three-way, if the other woman wants some girl-on-girl action, would that be a problem for you?"

Ross answered immediately, "No, no, God, no! As long as you're faithful to me otherwise, a threesome would be great, with another woman."

"You know Cindy from my office, right?"

Ross put his hand to his chin and said, "Cindy...Cindy. I'm not sure."

Rachel gently slapped his hand away from his chin, "Oh, Bullshit! You know her. She has bleach blonde hair and huge tits. You have probably jacked off, thinking about her."

"No comment."

"Well, Ross, she happens to be a free-wheeler, and bisexual. I'm pretty sure I could get her, but you might have to share me, just a little. You wouldn't have to share me with Annie because we're both straight."

Ross said, "If you are sure about this, you make it happen. I don't need anyone but you, Rachel, but, yes, I do regret my history before we got together."

Rachel knew that the promiscuous Annie had been in group sex situations before, particularly when she was younger. Rachel also knew that Annie was only promiscuous compared to Rachel. She was not a whore, just more active than Rachel. Rachel called Annie in Connecticut, "Annie! Rachel. I have a question for you. Would you like to meet a tall, handsome, intelligent guy who is an absolute sweetheart?"

Annie said, "You know that's not my type, Rachel. I eat those guys for lunch."

Rachel said, "It's Ross, and you've already had him for lunch."

Annie was astonished, "First of all, no comment on lunch. Second, are you two okay? Are you trying to get rid of Ross?"

"No, no, no, no. Ross deserves a little treat, and he's never had a three-way, so it'd be my special gift to him."

Annie was as wary as Ross had been, "Is this a trick? Or a joke? If it is, it's not funny."

Rachel said, "I know Ross titfucked you, Annie. It's okay. I'd like him to have the complete meal. It would be great for his self-confidence, Annie."

"I'm all over Ross, Rachel. I mean, for a one-nighter. Long-term, he's not my type."

Rachel said, "Perfect! We're available. How about you?"

"Hmmmm, how about this weekend?"

"Excellent! Your place or his?"

"Ross's place, of course. My place is so shitty, I'd be embarrassed. I can take the train down Friday evening, and come back Sunday evening. That gives us one day and two nights to set Ross on fire!"

"Okay! Talk soon. Love you."

"Love you, and love Ross!"

Rachel wanted to deliver exciting news in person. Ross stopped by Rachel's apartment for a quickie on Tuesday. After he ate her out and fucked her, as he was getting dressed, she asked, "Ross, you don't have anything planned for this weekend, do you?"

"Nope."

"Well good. My cousin, Annie, is coming Friday night and leaving Sunday night. We plan to stay at your place, in your bed, all three of us."

Ross was frozen in stunned silence. Rachel said, "It's true. You have almost two days and nights to live out every fantasy you've ever had about Annie. And don't tell me you haven't fantasized about her, Ross. I figure you should not screw me for the rest of the week, so you've got plenty of jizz for Annie."

"I reluctantly accept your terms."

Ross was so excited about his three-way weekend that he was frantic all week. He cleaned, bought flowers, arranged special surprises, and stroked himself while thinking about the bodacious little powerhouse named Annie. Short and curvy. A totally different look than his beloved Rachel, or than his ex, Carol.

On Friday evening, Rachel appeared at Ross's apartment. She said, "Ross, you are as excited as a five-year-old on Christmas Eve. Excuse me, Hannukah Eve. Annie is on her way. You'll be unwrapping your present soon."

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