Friends - Alternate Reality Ch. 24

Rachel and Cindy worked in different departments at the clothing company. Cindy was an administrative assistant, with an outgoing, even loud, personality. Rachel considered Cindy to be an ideal candidate for Ross to experience. She was full-figured, but not flabby. She carried her weight well, much of it in her bosom. She had a pixie face and a pixie haircut, which was always colored, often pink or blue. Her look and demeanor, while not classical, was often described as "sexy."

At twenty-three, Cindy claimed to be highly experienced sexually. She openly bragged that she was bi-sexual. She also said that she generally preferred men, but that she was always open to encounters with women. Rachel had noted that, while Cindy was very forthcoming about her own sex life, she never identified or exposed any of her partners. Perfect.

Cindy liked Rachel, and often came by Rachel's office to visit. When Cindy stopped by to say hello, one day, Rachel asked, "So Cindy, are you seeing anyone right now?"

"I am seeing anyone now, but no one in particular. Do you have someone for me?"

Rachel said, "Close the door. You remember my boyfriend, Ross?"

Cindy licked her lips and said, "Mmmm-hmmm, yes."

"Well, Ross certainly remembers you. You and I are different types, and I think he craves a little variety." Rachel let that hang out there.

Cindy looked Rachel in the eye for a moment, and said, "I would love to get to know Ross socially, Rachel, if that's what you're driving at." Rachel nodded solemnly. "Tell me more about Ross in the bedroom."

Rachel made the sales pitch, "Well, he's kinda big, you know?" Rachel nodded as if she did, in fact, know. "He is athletic, and he knows how to do it. All of it. I just want to offer him a little variety."

Cindy asked, "Is this a package deal? Would you be on the table?"

"I would be there. I might be on the table, if absolutely necessary."

Cindy said, "Let's do it. Call me after work. Bye."

After work that night, Rachel called Cindy on her personal phone, "Cindy, it's me, Rachel, the woman who is offering up her boyfriend."

Cindy said, "Rachel, let's do this. When and where?"

Rachel said, "First, the ground rules. Both Ross and I were tested at the beginning of our relationship and have been monogamous since then," Rachel discounted the encounter with Annie as harmless, "but, from what you say, Ross would have to wrap up."

"Yes, that's my rule generally. Except for head. I'll do that raw. The condom is to protect Ross, not me."

"Excellent. What's your availability this weekend?"

"I'm free Friday night. Name a time and place."

Rachel said, "Ross has a nice apartment. Friday night?"

"I'll be there." Rachel gave Cindy Ross's address and phone number, and settled the logistical details. Ross sat next to Rachel on the couch, listening and biting his lip.

Rachel said, "It's all set. You have to wear condoms, except for her blowjobs."

Ross furrowed his brow, "You know you can transmit disease through oral, right?"

"Yes, but the condoms are to protect you, not her. I explained that you are clean."

Ross said, "Good. I've never gotten a blowjob with a condom on, and I never want to."

Rachel said, "This is Monday. You should be celibate Wednesday and Thursday, so you've got tonight and tomorrow night."

"Okay, let's do tonight and tomorrow night, and then I'll see you at my place on Friday."

The next day, at work, Rachel asked Cindy, "What would you like for dinner, Friday night?"

Cindy grinned and said, "I was thinking a nice Italian restaurant," clearly indicating she wished to be wined and dined. Rachel and Ross knew the perfect place, just two blocks from the apartment. The trio met up at the restaurant at seven o'clock. Rachel wanted to eat early since the primary purpose of the night was sex.

Cindy had changed from her not-so-conservative work clothes into a black dress with a plunging neckline that displayed much of her abundant cleavage. They shared a bottle of chianti. "Shared" was a relative term, because Rachel drank two glasses, Ross sipped a quarter glass, and Cindy guzzled the remainder.

Cindy was uncharacteristically edgy and nervous. She seemed to be drinking to calm herself. During dinner, Rachel grew concerned, "Cindy, is everything all right? Do you feel okay? We can do this another night, if you prefer."

Cindy began cry, and said, "I'm so sorry, Rachel and Ross. I don't know what to say."

Ross, said, soothingly, "It's all right, Cindy. I'll tell you what, why don't we finish dinner? After, if you like, we all go to my place, and just sit around talking. Nothing more. Would that make you more comfortable?"

Cindy blew her nose into a tissue, "Oh, Ross, you are such a sweetheart. That would be good." The remainder of the meal was easier. Cindy settled down. Rachel and Cindy debated whether to indulge in dessert.

Ross said, "Why don't you each pick something to go? You can have it tonight or tomorrow." The girls agreed, and they set off for Ross's apartment in good spirits.

As Rachel showed her around, Cindy raved, "You have an amazing place, Ross! And it's so well decorated. Did you help him decorate, Rachel?"

Rachel admitted, "No, no, I'm no decorator. Ross did this himself. He has excellent taste." Ross arrived with wine. Rachel and Ross sat, with Rachel leaning heavily on Ross. Cindy sat on the other sofa. Cindy drank almost a full glass of wine right away. Rachel cautioned, "Cindy, take it easy. Tell us how you are feeling, and what you're thinking."

Cindy began to tear up, and Rachel set a box of tissue on the coffee table in front of her. Cindy said, "I know I talk a good game, but I'm not as slutty as I say I am. I don't let guys take advantage of me. I am proud to say that, at least. I've never done a threesome, Rachel."

Rachel said, "Well, that's all right, Cindy. You can be selective if you want. That's a good thing, in this day and age. I'm not bi, anyway, Cindy, so it doesn't need to be a threesome."

Ross offered, "Cindy, let's just talk this out, okay? Rachel and I respect your choices, Cindy. We haven't been playing the field, and certainly not when it comes to group sex. That's normal for us, so don't be embarrassed if you live that way, too."

Cindy sniffled, "Oh, Ross, Rachel is so lucky to have you." Rachel smiled and kissed Ross on the cheek. "I wish I could find a guy like you."

Rachel said, "Ross is a great guy, but he's not the only one. Do you know when I started my relationship with Ross? It was after I decided I wanted a real man, a man I could count on, a man brave enough to be sensitive, and a man who wanted a life partner." Ross pursed his lips, and leaned his head against Rachel's.

Cindy was touched, "So sweet! Why would you share him?"

Rachel looked to Ross, he nodded, and she explained, "Well, frankly, Ross was married for years, so I have more experience romantically than he. I think he needs to sow some wild oats, or else he'll be jealous, or wonder if he should have played the field more before settling down. It's that simple. Sharing him is not going to be our lifestyle."

Cindy sat up straight, "Guys, let's do this. Can I have more wine, please?" Ross and Rachel looked at one another again. Cindy was not noticeably drunk yet, so they shrugged. Ross rose, filled her wine glass halfway, and sat down next to her.

Ross asked, "May I touch you, Cindy?"

She said, firmly, "Yes." He reached across her, placed his hand on the space between her breasts, and slid his hand over her breast, under her clothing. She turned her face to his, and he kissed her on the cheek. He rolled her breast around. He couldn't get his large hand completely around it.

Cindy was built unlike any woman Ross had ever been with, which is why Rachel selected her for this event. Cindy purred, and Ross moved her dress aside to expose first one breast, and then the other. She was responsive, so Rachel said, softly, "Let's move this into the bedroom. I'll get the wine."

Rachel picked up their glasses, and carried them to the bedroom, following Cindy and Ross. Rachel set down the wine, and lit some candles, while Cindy and Ross sat on the bed. He tried to unclasp her dress behind her neck, but had difficulty. Cindy and Ross both laughed. He figured it out, and her dress dropped to her waist.

Cindy's breasts were bounteous and beautifully shaped. Ross noted that they were perfectly symmetrical, which was a particular fetish of his. Ross was highly motivated to have this woman, and he would do almost anything to make that happen. He stood, and took Cindy's hand as she stood. Ross stripped while Cindy wriggled out of her dress and removed her shoes and hose.

When Ross dropped his pants and shorts, his cock sprung out of its confinement. It looked as if it should be accompanied by a comical "boingggg!" sound, and all three smiled at the sight. Cindy couldn't take her eyes off it, and impulsively reached for her wine glass and drank it all down. Rachel and Ross exchanged glances. Rachel reassured Cindy, "Ross is very gentle, Cindy, and we have lubricant, plus the condom. It will be nice, I promise. Why don't you get into bed, dear?"

Cindy tentatively climbed onto the bed, and sat at its center, her legs extended to her side and her torso propped up on her arm. She looked sexy. Rachel produced a condom. She and Ross had never used one together. Rachel was accustomed to putting on condoms with her mouth alone. Performing this trick, however, would remind Ross that she had more numerous lovers, all of whom needed to be separated from her by a layer of latex.

Rachel turned to Cindy, "Do you know how to put on a condom with just your mouth?" Much to Rachel's relief, Cindy nodded. Rachel's special talent would remain her secret. Cindy reached out for the condom and scooted to the edge of the bed, in front of Ross. Cindy opened the condom, took it out, placed it carefully on the tip of Ross's penis, and puckered up.

Cindy applied her pucker to the condom, pinched her lips tightly, and moved her head forward slowly. The condom unrolled, propelled by her lips. Ross had heard of this technique, but had never experienced it. He watched Cindy work with intense pleasure. As the condom wound down on his long cock, Cindy's lips lost their purchase. A couple of times, she had to pull back a little and reset her lips.

After the condom was on, Cindy backed away, and lay on her back, down the center of the bed. She arranged a pillow under her head. By silent agreement, Ross and Cindy would start out in the missionary position. This would relieve Cindy of responsibility for handling Ross's cock. Rachel swiped lubricant on Ross. Oil dripped down the condom and over his balls.

Ross lay on the bed beside Cindy. Rachel handed Ross the lube, and he applied some to Cindy's slit. He jiggled her clitoris, which caused her eyes to roll up into her head. She moaned, and gripped the sheets hard in her fists. Ross alternated between her clitoris and her vagina. When he thought she was ready, he returned the lube to Rachel.

Ross climbed between Cindy's legs, smiling greedily. He had rarely been as turned on as he was with this enticingly tentative and bountiful woman. Ross placed the tip of his cock carefully, and entered her. She gasped. He struggled to be patient. He slid into her in a few long strokes. She made anguished sounds, but did not cry out. He remained buried inside her for a few moments, allowing her time to adjust to his size. He watched her face. She relaxed a bit, nodded, and said, breathlessly, "Okay."

Ross was already near climax. He pulled out a couple of inches and slid it back in. Cindy's face, and the sounds she made, told him that she was uncomfortable. He could no longer restrain himself. He pumped his cock in and out of her, with a travel of several inches on each stroke. She groaned at moderate volume. He vocalized, "Ah! Ah! Ah! AH! AH!! AH!!!" Ultimately, he grimaced fiercely and filled the condom to overflowing.

Ross imagined that his cum squeezed out around his cock, and formed a thin ring around the junction of his cock and her vaginal entrance. He delivered many strokes after he finished coming. He was tempted to continue fucking her. Instead, he pulled his cock out, rose up on his knees, and noticed that he was wearing a condom. He had completely forgotten the condom. The condom was full of semen. Some juice leaked out by the rim, much as he had pictured it doing in her vagina.

Ross clamped his hand around the base of his cock to hold the juice inside the condom. He scrambled off the bed. Rachel pulled a sheet over Cindy's nude form. Rachel then pulled the condom off of Ross, using her fingers like a squeegee to contain all the semen inside. She handed Ross a few wet wipes. While he wiped his cock clean, she tied a knot in the condom and dropped it into the wastebasket.

Rachel and Ross turned their attention to Cindy. She was sitting up, holding the sheet over her breasts, and smiling. Rachel passed Cindy a glass of wine, and asked, "How are you, honey?"

Cindy sipped some wine, and said, "I'm okay. It was—big, but I'm okay." She drank more wine.

Ross said, almost apologetically, "Ladies, I'm afraid that I am so turned on right now that I have a powerful urge to mate immediately." He directed his next comment to Cindy, "I saved up for tonight, so I am reallllly horny."

Rachel and Cindy looked to one another. Cindy said, "I think I need a little break, Ross, unless you want head."

Ross said, "I want more than that, Cindy. I want to fuck your tits, and come in your mouth."

Cindy was a trooper, saying, "That's good for me." When Ross moved to get back in bed, Cindy held up her hand to stop him, "I have a technique I use for this, Ross. Is it okay if I try it now?"

Ross said, eagerly, "Yes! Yes, that would be great!"

Cindy slid to the edge of the bed, near Ross, dragging pillows behind her. Rachel stepped aside to give her room. Cindy stacked two pillows on the floor, and kneeled on them. She looked at Ross, and slipped another pillow under her knees. Satisfied that she had properly adjusted for the difference in height between her and Ross, she reached to Rachel for the lubricant. Cindy poured some on each breast and in the canyon between them. She spread it around the midline of her chest.

Cindy looked at Ross's erect cock, and nodded. Ross stepped toward her, and pressed his cock against her chest. It felt really good. Cindy gathered her huge tits in her hands, and pressed them together, making Ross's cock disappear entirely. Her boobs flowed and bulged out around her fingers and hands. The sight was powerfully erotic for Ross.

Before he could begin fucking Cindy's tits, she did something that Ross had seen often in porn, and had many times masturbated to. While Ross remained still, she worked her tits up and down, and bent her knees, hips and back in unison, to give her a longer stroke. She was able to expose nearly all of his prick when she rose up. On the down stroke, she drove the rod up her chest until her boobs molded around the root and the head nearly touched her chin.

Ross felt a rare, mind-blowing sensation. Her tits were fucking his cock. He moaned and grunted helplessly under her command. Rachel felt a tinge of jealousy because her own B cups were not sufficient to fully wrap Ross's cock. She shook her head in wonder at what she saw. Cindy was proud of her ability, and she smiled broadly.

When Cindy looked up, into Ross's eyes, he melted. It was one of the prettiest sights he had ever seen. Ross was grateful that he had already come once, because he would have blown his load in seconds if this was his first time of the night. He cheered her on, "Yeah. Yeah! Yeah!!"

Cindy looked up at him with a smile, and said, "Fuck my tits, Ross! Fuck my tits!" Ross sighed deeply. It took a couple of minutes of sustained effort for Cindy to bring Ross to the point at which he could feel his orgasm in the distance.

Rachel felt some renewed jealousy when Ross spoke to Cindy so softly that Rachel could barely hear him. Rachel felt that Ross was thereby communicating privately with Cindy. Ross and Rachel had agreed that private communication with any other lover was strictly off limits, for both of them. Ross almost whispered, "Talk to me."

Cindy obliged by looking up and begging, "Come in my mouth, please. Come in my mouth, Ross! Fuck my tits, and come in my mouth. I'll swallow it all, Ross. I'll suck the cum out of your dick, Ross. Fuck my tits! Come in my mouth!" Her pleas drove him to the edge of orgasm. He pulled his prick out of its warm, soft home between her breasts, and presented it to Cindy's mouth.

Cindy pumped his shaft with her fist, and sucked on the head. In this case, the technique mattered little because Ross was already on the verge of coming. When he ejaculated, he demanded, "Suck! Suck! Suck! Suck!" She took it all and swallowed a few times to get it all down. Before Cindy had a chance to detach, he said, "Keep on sucking for a bit, Cindy." She looked up at him, took her hand off his cock, and blew him with just her mouth.

She, too, was no match for Rachel in the blowjob department. Nevertheless, it felt really good. He said, "Take it as deep as you can." She got about two-thirds of his rod into her mouth before she began to gag. Her gag reflex closed her mouth and throat around his cock spasmodically. Although her gagging signaled the limit of how much of him she could swallow, it felt amazing.

Ross urged, "Keep trying to deepthroat. That feels great!" He relaxed to enjoy the sucking and gagging for a while. Only when he sensed that Cindy was tiring did he say, "That's good," and pull out. Ross took a step back, and exulted, "That was excellent! Outstanding!" Cindy smiled happily, and Rachel smiled weakly.

Ross said, "Let me jump in the shower. I'll only be a minute." He may have taken all of two minutes, for he returned, clean as a whistle, before Rachel and Cindy had their robes on. Ross was nude, his cock long, but hanging downward. Rachel helped him on with his robe. Ross said, "Do you guys want to go out into the living room for a while?

Cindy said, "Yes, but I'd like to shower first."

They left the bedroom. Cindy diverted to the bathroom, and Rachel and Ross conferred. Rachel asked, "Do you want me to ask her to stay the night, Ross?"

Rachel was a tiny bit disappointed when he said, "Yes." She was pleased, however, with his reasoning, "She doesn't give good head, and I've had her tits, but I would like to just fuck her pussy once more. Is that okay with you?"

Rachel said, "Sure. I would remind you that you could probably fuck her in the ass. If necessary, we could finish getting her drunk right now, and you could do it tonight."

Ross shrugged a bit, and said, "Nah, I think one more time in her pussy is all I want. I came so fast the first time that I really never got to settle down and experience it."

Rachel felt relieved and reassured that Cindy's radically different body held no fascination for Ross. When Cindy came out of the shower, Rachel said, "Cindy, would like to spend the night? I have everything you would need."

Cindy smiled meekly, and said, "Actually, I packed my toothbrush and a fresh pair of panties, just in case. I have plans later in the morning tomorrow, though."

Rachel and Ross were delighted to hear it, but did not show it. Rachel said, "Oh, we do, too. We do, too. Will you at least have time to go out to breakfast?"

"Sure! Uh, Ross, are we going to, you know, tonight?"

Ross said, "I'm done for the night, if you are okay with that. Tomorrow morning, I expect to feel differently."

Cindy asked, "Good. Any idea what you might want when you wake up?"

Ross leaned in, and spoke gently, "Well, to be honest, Cindy, you had me so hot that I finished very early our first time, you know."