Friends - Alternate Reality Ch. 61

With Chapter 61, I have changed the style in response to feedback received. The chapter is much longer, and scenes are written with much more detail.

There were very few children or families in Chandler and Monica's apartment building. One reason for that was that all of the apartments had only a single bathroom. Another reason was that the building had been designed for adults only. Even though a subsequent state law prevented enforcement of that rule, the vibe of the place was still swinging singles and young couples.

The apartment on Chandler and Monica's floor formerly occupied by Terri was taken by a single mother named June. The daughter was eighteen, and smoking hot. Her body had the firmness of a girl, and the curves of a woman. Jenny was a senior in high school. She was a good kid, and her mother was appreciative of her daughter's conservative and studious nature. Jenny wanted to go to college, and major in business administration.

Jenny thought that Monica was probably the coolest and prettiest woman she knew. A great career, a great guy, a great face, and a great body. Jenny was attracted to Chandler primarily because he had somehow earned the love of Monica. Monica had long talks with Jenny about the business world, and Jenny came to see Chandler as almost a business superhero. Jenny needed to do a senior project about a real-life businessman. She asked Monica about it when they crossed paths in the laundry room. Monica said, "The perfect person for this, Jenny, is Chandler. He's on the fast track in a very hot profession. Data Analysis is lucrative, and a growing field."

Jenny asked, "Would you ask him if he would let me shadow him, Monica?"

Monica said, "No, you have to ask him yourself, but I can be there." The two women went back to Monica's apartment, where Chandler was watching TV. Monica asked Chandler to turn down the TV, and nodded to Jenny.

Jenny asked, hesitantly, "I need to do a project about a businessperson, and I was wondering if I could learn about what you do, Chandler."

Chandler tried to think of something he would like to do less. He saw Monica, standing behind Jenny, wearing an expression that told Chandler he'd better agree to Jenny's request. He said, "Yeah, I'd love to, Jenny."

Jenny was giddy with excitement. The three talked for a few minutes about what would be involved, and Jenny bounced out of the apartment with girlish enthusiasm. When Jenny was gone, Chandler cast a dour look Monica's way. She said, "I know, I know, Chandler. I think this is a mitzvah, a good deed." Chandler's expression did not change. She said, "Okay, I'll owe you." His expression still did not change. Monica rolled her eyes, began unbuttoning her blouse, and headed to the bedroom.

Jenny was pretty, with shoulder-length blonde hair, luminous skin, and a body that would not quit. She was tall and lean, with a narrow waist, flat stomach, and C-cup breasts. Jenny was also intelligent. Chandler took her to work, so she could shadow him. Beforehand, he asked Monica, "Please do me a favor, and try to get Jenny to tone down her look for my office, will you? I shudder when I see the things girls today are wearing."

Monica gave Chandler a knowing look. Monica took for granted that Chandler sometimes thought of Jenny, and even her mother, June, when he made love to her. Monica said, "We'll do our best, but remember that a high school girl like Jenny doesn't have anything that doesn't look sexy. Besides, she'd look sexy in anything.

June was a forty-year-old bombshell. She had short, curly reddish hair, very fair skin, and huge boobs. Her bosom was splendidly offset by her womanly hips. Her figure was that of a much younger woman. Chandler had, indeed, thought of both June and Jenny while he was in bed with Monica.

Chandler ended up having a fine time showing Jenny the ropes at his office. Her presence was warmly received by everyone, especially the straight men and lesbian women. A couple of the younger co-workers asked about Jenny's availability. Chandler didn't know what Jenny's availability actually was, but he claimed she had a boyfriend, just to simplify things. In fact, Jenny did not have a boyfriend, and was falling for Chandler.

Jenny called Chandler frequently about her project, and visited his apartment often. She looked at him in a certain way, and dressed even more alluringly than usual when they met at his place. Chandler had difficulty suppressing an erection when Jenny was around. Chandler was up front with Monica, "Honey, I think Jenny has a crush on me. She's been pretty provocative."

Monica sighed, "Sure, Chandler. She's a hot teenager, and everything she does seems like a flirtation. I wouldn't worry about it."

Chandler was deflated, until one evening, when Monica was out, Jenny came over to review the paper she was writing. Jenny was especially nervous that night, and Chandler soon found out why. At a seemingly random moment, when both their heads were down, close together, she kissed him on the lips. He sat up and looked at her, astonished. She kissed him again, this time with her lips slightly parted. Her did not return the kiss. Chandler said, "Jenny, you're a beautiful girl, but I am in a committed relationship."

Jenny almost cried, "Chandler, all the good men are taken. They guys in high school are idiots, and the older men are all spoken for. I want my first time to be special. Monica is lucky to have you, Chandler." Jenny gathered her things and left, crying and pouting.

When Monica got home, Chander excitedly told her what had transpired. Monica was shocked, "I love you, Chandler, but I never would have expected Jenny to make the first move. I think you did the right thing, telling her you're off limits, because you are off limits."

That weekend, Chandler, Monica, Ross and Rachel headed to Amish country for their monthly swapping weekend. As usual, they had adjoining rooms. One evening, when they were all in bed, Chandler talked to Rachel about Jenny. He said, "This girl, Jenny, I'm mentoring at Monica's insistence. Well, she kissed me, on the lips, twice, and told me how attractive I was. She implied that she wanted me to take her virginity. Monica thinks I'm imagining things, and I'm forbidden to do anything with Jenny, anyhow."

Rachel said, "Well, that's pretty tight, I think, but that sounds like Monica. Have you ever had a virgin?"

Chandler said, "No, of course not. Nobody ever liked me that much."

Rachel advised, "Don't pull that feeling-sorry-for-yourself crap with Monica. She would be very offended if she thought you were bitter about not being her first." Chandler pouted. Rachel continued, "Still, you have a point. I mean, Ross never had a virgin, either, but he's nailed two since he and I got together, and with my blessing."

Chandler sat up in bed, "What!? Ross has had two virgins while he was with you, and you approved of it?!" At breakfast, Chandler said, "Monica, did you know that, since he began seeing Rachel, Ross has had the pleasure of deflowering two girls?"

Monica pursed her lips, "Yes, I knew, Chandler. What's your point?"

Chandler was indignant, "I just feel a little envious. I've never had a virgin, and now a really hot one has chosen me to be her first, and I can't do anything about it."

Monica looked scathingly at Rachel, and said, "I had hoped you would not find out about Ross's experiences, Chandler. I guess I can't reasonably deny you. You have to make absolutely sure that Jenny does not get pregnant. Before you say anything to Jenny, let me find out what I can from her mother."

A few days later, Monica invited June over for coffee and dessert. Chandler was not home. As Monica served cake and poured coffee, she said, "June, your Jenny is such a stunner! I hope to have a daughter like her someday."

June smiled and said, "What about Chandler?"

Monica quipped, "Oh, Chandler would like to have a daughter like Jenny immediately, if you know what I mean!"

June laughed, and said, "Oh, I know! It's really hard having a pretty daughter. She's very mature for her age, but I am afraid she'll make wrong decisions when she goes off to college. That's why I have her on the pill, already."

Monica said, "I think that's only prudent, June. I'll be honest with you, June. Chandler thinks Jenny has a bit of a crush on him. I told him he was daydreaming, of course."

June said, "Actually, Monica, Chandler is probably right. She gushes about Chandler all the time. She actually said she wanted to marry a man like him. I guess she hasn't disguised her feelings from him."

Monica said, "Hmmm, no, I guess she hasn't. I tell you, June, I wish that I had met a man like Chandler when I was Jenny's age. I mean a man like the Chandler of today, not Chandler back then. I actually did know him then, and he was pretty immature."

June said, "I also hope she finds a guy like Chandler, Monica. What do we have to do to keep those two apart?"

Monica said, "I need to stay out of this discussion, June. I actually have more experience, romantically, than Chandler. Don't repeat this, but it's actually a LOT more experience. I won't deny him a once-in-a-lifetime experience. If you wish him to keep his hands off of Jenny, you have my blessing to speak to him about it."

June stared intently at Monica as she sipped her coffee slowly. She said, "You're saying I'd have to offer something of value to Chandler, to protect my daughter's virtue?"

Monica said, "I'm not saying anything, except that Jenny has a crush on Chandler, not me."

The pair ate cake in silence for a while, until Chandler came home from the gym. He wore athletic clothing that showed his physique to advantage. He excused himself to take a quick shower. While he was in the shower, Monica and June exchanged significant looks. June said, "Chandler is a very attractive man, Monica. I haven't had a man since my divorce, two years ago, but I can't imagine him being attracted to an older woman, like me. Not when he has you here."

Monica said, "That's the thing, June. I'm here. I'm here all the time. You are something new and different. Besides, any man would want you."

When Chandler emerged, wearing his silk robe, Monica said, "Come here, Chandler, so we can talk. June doesn't mind if you're in your robe, do you, June?"

June said, "Of course not."

Chandler joined them, and Monica rewarded him with a slice of cake. Jenny sized him up, and said, "Chandler, thank you for putting up with Jenny. I know she has a crush on you. It's obvious."

Chandler was astonished, "Uh, well, I don't know if she has a crush on me, June. She's a great girl. You should be proud."

June said, "I am proud. However, I was just telling Monica that I'd like Jenny to mature a little more before she gets romantically involved with anyone. I'd be terribly grateful to you if you would resist her advances, Chandler."

Chandler had a mouthful of cake. He looked from June to Monica and back, not sure what to say. Monica helped him, "I told June that you two should talk about an arrangement that would be mutually satisfying to both of you. I'll agree to whatever you two decide."

Chandler was cautious, "An arrangement that would ensure that I keep my hands off of Jenny?"

June sat up straight, which accentuated her splendid bust, "Yes, exactly. I know she wants you, Chandler. It's only natural that you would want her. I know that forbidding her to see you would only inflame her desire to do so. What do I have to do to keep you two apart?" She licked her lips slowly.

Chandler, dumbfounded, looked to Monica. Monica wagged her eyebrows at him, encouraging him to negotiate. He said, "Your daughter is an attractive young woman, June. On the other hand, you are a very attractive woman yourself...." He trailed off, needing to get one of the ladies to make an explicit proposition.

June said, "Thank you, Chandler. You are a very attractive man. Do you suppose an older woman, such as myself, might serve as a substitute, if you will, for a younger, forbidden fruit?"

Monica smiled at Chandler and raised her eyebrows. He said, "Why, yes, June, you are certainly attractive enough for any man. Of course, I have a very attractive woman, already."

Monica held his hand in hers, and said, "You have my permission to negotiate in good faith with June, Chandler."

June smiled, and said, "Good. Then, we have an understanding. When would be a good time to consummate our new relationship, Chandler? Jenny is at volleyball practice until about eight tonight."

Monica said, "Is right now okay with you, Chandler? You'd have all the time you need."

Chandler said, "Now would be good, I guess, as long as it's good with Monica."

June stood up, and smoothed her dress over her luscious body. She said, "Get some clothes on, Chandler, and come over to my place. I'll be waiting for you." She left with a little wiggle in her walk.

The moment June was out the door, Monica kissed Chandler on the lips, and said, "That's my gift to you, Chandler, to make up for some of the frustrations you've felt before. Go get ready, get over there, and enjoy yourself. I'll want to know everything, afterward."

Chandler dressed casually, kissed Monica as he passed her, and left the apartment. He knocked on June's door. In a moment, she answered, wearing the same dress as before, and waved him in. When he turned around, she planted a big, wet kiss on his lips, and said, "What are we waiting for?" She grabbed his semi-hard through his pants, and said, "Let's find a place for you to bury that thing!" She took his hand, and led him to her bedroom.

Chandler was lightly dressed. He kicked off his sandals, pulled his shirt over his head and dropped his pants. He stood before her in boxers. June approached, turned her back to him, proffering her zipper. He unzipped her dress. As she walked away, she peeled the dress off one shoulder, and then the other. She shook her body erotically, the dress fell to her feet, and she stepped out of it. June's back was white, smooth, and tapered to her narrow waist. June turned, and stood before him in bra and panties. Her body was dynamite. Huge tits, narrow waist, full hips, all topped with a big, sexy smile.

Chandler got an erection. He removed his boxers, carefully avoiding his throbbing cock. He walked to the head of the bed, turned down the sheets, and climbed into bed. June removed her bra, releasing her large, soft breasts. Her jugs were pendulous, but beautifully shaped. She had large, pink areolas. She pushed her panties down, and slipped under the sheets. Chandler noted that her trim pussy hair matched the reddish hair on her head. Monica had assured him that June dyed her hair, and Chandler was eager to report what he had seen. June either dyed her pubic hair to match, or she was a natural redhead.

June sat upright, against the headboard. Chandler rolled onto his side, took her nearest udder in his hand, and applied his mouth to the nipple. June gasped when he washed his tongue over the areola. She fingered her pussy while he ravished her breast. Chandler smeared his tongue and lips all over. He moved to the other breast, and gave it equal attention. June cooed, "Oh, Chandler, that's wonderful. You know how to handle boobs." Chandler responded by sucking as much of June's boob into his mouth as possible. She moaned contentedly.

June enjoyed the variety of moves that Chandler put on. He used the tip of his tongue delicately, then applied as much of the top surface as he could. He even used the extremely slick underside of his tongue on her nipple. Side-to-side, up-and-down, clockwise and counterclockwise, firm and soft, fast and slow. June groaned, "Oh, Monica, you lucky girl!"

Chandler got up on his knees, threw one leg over her, and straddled her hips. He bent at the waist, pushed his face between her boobs, and rolled his head around. They were so soft and juicy! He made her laugh by playfully motorboating them. Chandler used both hands to knead her breasts and squish them against his face. With his eyes closed, he pushed the breasts against his eyelids, relishing the warm, smooth surface. Then, he licked and sucked the nipples some more. June breathed in short gasps. She said, "Fuck me, Chandler. Please."

He gave each nipple one last kiss, and moved down. She slid down so she lay flat on the mattress, and spread her legs to admit him. He kneeled between her legs, and supported himself over her on his arms. They both paused to look into one another's eyes. June had amazing, light blue eyes. They both smiled. She took his erection in one hand and guided him to her juicy pussy. He knew he had done a good job on her breasts when he felt how moist her quim had become.

Chandler sighed when the tip of his cock nestled into the entrance to her vagina. He slid into her warm pussy smoothly. Chandler held his breath during his entry. The smooth, soft, warmth of her vagina addled his brain. His eyes first went down to see his dick disappearing into her red carpet. Then, his eyes crossed involuntarily. The last inch made him throw his head back, mouth open, eyes rolled up under his eyelids.

Chandler reached full penetration. He paused to catch his breath. He sighed, smiled kindly at her, and started to fuck. He was horny, not having had sex for nearly 48 hours. Impatient, he quickly reached high speed, banging his pelvis against hers. He breathed deeply, seeking to maintain the pace for a while. She made a small grunting sound each time he rammed his cock into her. Her breasts sloshed about in a fluid manner. He had seen this phenomenon in many porn films, but he had never before witnessed in person. The sight sent him over the edge.

With a strained noise, he grimaced, and increased his pace to ramming speed. Each thrust jolted her body, and her head moved in sharp jerks upon the pillow. Even though Chandler had only an average-sized penis, June bit her lower lip on the runup to his orgasm. She just needed to hold herself together for a few more moments. Both lovers were relieved when he delivered gobs of Chandler juice to her womb. Chandler's eyelids fluttered with the glorious release.

While his ejaculation died out, he breathed heavily to catch his breath, and continued to fuck her with slow, gentle strokes. He smiled at how squishy and moist he had made her pussy. After a few moments, she narrowed her eyes, and said, in a low, sultry voice, "You fucked me, Chandler. Mind if we trade places?"

He pulled out of her cunt, saying, "Not at all, June." He lay on his back, and adjusted a pillow comfortably under his head. She got to her knees and mounted him in much the same way as he had just done to her. On her knees, she lowered herself down. Mouth open, she let out a sexy, "Ahhhhhhhh." She settled gently onto his cock. She leaned over him, and held on to the headboard with both hands. With her eyes lightly closed, she wore a slight smile. She rode him expertly, grinding herself against him slowly. Chandler was pleased. He thought that June moved her hips much like a hula dancer. He made a mental note to tell Monica. He urged her, "That feels sooooo good, Monica!"

"June." She was not in the least offended.

"Excuse me. June. Ahhhh, nice!" Chandler closed his eyes for a few moments to savor the feel of her pussy gently stimulating his cock as she swirled her hips about.

June made soft moaning sounds that gradually increased in volume. Eyes closed, she was in a world of her own. She focused solely on her own pleasure. Her pendulous breasts hung down close enough that Chandler could stretch his neck upward and slurp the nipples occasionally. She was, he thought, a bit like a fisherman dangling an enticing bait to lure a fish to rise up and taste it. After several minutes of enjoyment for both of them, she tensed. She gripped the headboard more tightly, until her knuckles turned white. She let out guttural grunts, and shuddered several times. Her eyes were shut tight, and her brow was furrowed when she climaxed.