Friends - Alternate Reality Ch. 55

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Ch 55--The One with Ross and Shelley.
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Part 55 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Ross taught two classes at NYU. One was an undergraduate introduction to paleontology, and the other was an advanced undergraduate course focusing on the fossilization process. All the students in the fossilization class were hopeful of becoming professional paleontologists. One girl, named Shelley, was an outstanding candidate, who also made eyes at Professor Geller.

Shelly had china white skin, long dark hair with bangs, and a voluptuous body. Shelley rocked the "hot librarian" look. She wore oversized glasses, tied her hair back, and usually wore bulky knit sweaters. She was five-eight, with a tiny waist, and huge knockers that no sweater could conceal. She was a knockout. Ross always imagined Shelly shedding her sweater, shaking out her pony tail, and peeling off her eyeglasses as she slinked toward him.

Shelley aced the fossilization class in the fall semester. On the first day of the spring semester, she came to see Ross. Ross welcomed her into his office, "Shelley! There's my superstar. Here, have a seat."

Shelley said, "Thank you, Professor Geller. I was so happy with my grade in your class. It was the perfect Christmas present."

"You earned it, Shelley, and please keep me in mind if you need a letter of recommendation. I'll also keep an eye out for internships and other opportunities for you."

Shelley blushed, "Thank you, Professor. I was hoping you would say that. I also came to you seeking your advice on something that isn't strictly academic." She glanced over her shoulder at the open door. Ross got up and shut the door.

Shelley took a deep breath, and blurted out, "I want to lose my virginity."

Ross was taken aback. He was at a loss for words for several moments. Finally, he sputtered, "Um, I see. That's a big moment in anyone's life, Shelley."

"I want it to be you."

"Uhhh, that's very flattering, Shelley. Why me?"

Shelley went into debate mode, "Professor Geller, you are the most complete man I know, excepting only my father. You are young, yet mature, handsome, experienced, worldly, and you have a smoking hot girlfriend." Shelley gestured to the eight-by-ten of Rachel that sat on Ross's desk. "You'd be perfect for me. You could show me the ropes, and go back to your girlfriend, no questions asked."

Ross tensed, "That whole girlfriend thing is kind of a big factor in my decision-making, Shelley."

Shelley was supremely confident. She picked up Ross's phone off the desk, handed it to him, and said, "Call her, please. I'd like to talk to her, woman to woman. Her name is Rachel, isn't it?"

"Uh, yes, but she may not want to hear what you have to say."

Shelley waved her hand, "I've thought this through, sir. If she says no, I'm just a crazy kid making a crank call. You can say you threw me out of your office. If she says yes, then you and I are both winners, aren't we?"

Ross couldn't see a flaw in Shelley's reasoning. His pants began to stir, thinking that there might just be a chance of pulling this off. He dialed Rachel at work.

"Rachel, can you talk privately for a few minutes?"

"Sure, Ross. Let me close my door." Ross heard the sound of a door closing. "Shoot."

"Rachel, I have a student here named Shelley. She is a star student. She got an A-plus in my advanced class last semester. She came to me for advice. Apparently, it's something that requires a woman's touch. Could you please talk to her for a moment?"

"Yeah, sure."

Ross handed the phone to Shelley, who said, "Rachel? Hello, my name is Shelley. I won't waste any of your time or Professor Geller's time. I am a graduating senior. To put it bluntly, I don't want to graduate college a virgin. Professor Geller is the ideal man for the job, in my opinion. I could explain my reasoning ad nauseum, but you know him even better than I. I hope you will allow him to help me in this matter."

There was a pause. Rachel said, "Shelley, please put Professor Geller on." Shelley handed Ross the phone, and shrugged.

"Rachel?"

"Ross, this better not be some kind of joke."

Ross was insistent, "It's completely sincere on Shelley's part, Rachel. She is mature beyond her years. I think she means what she says, incredible as it may sound."

Rachel asked, "What do you want to do?"

Ross didn't know what to say, so he stumbled, "Oh, uh...well, I don't know...."

"I get it, Ross. You want to. Nothing scandalous in that." Rachel lowered her voice so Shelley would not be able to overhear, "Yes or no. Is she good looking?"

"Yes, yes, yes!"

"I think you should do it, Ross. She doesn't want anything from you but sex. This sounds like low hanging fruit. Maybe you should have her come to our place. It could be any time after work, or any time this weekend. We could talk it over, and, maybe, you dine on cherry pie!" Rachel hung up.

Ross cleared his throat, "Ahem, she wants you to come over for a chat, Shelley. We could do it any night after five, or this weekend. We could order some pizza, and think this through."

"I'm ready tonight."

Ross wrote on a notepad, and said, "Here's the address, and my phone number. It's about a half block south of the L line station. Be there around six, please. What kind of pizza do you like?"

"Vegetarian."

"Good! I'll see you then."

Ross had trouble keeping his erection at bay for the remainder of the afternoon. He was so nervous that he left early, arrived home by five, and took two showers. He ordered pizza. Rachel came home around 5:30, and sensed at once what was going on. She said, "Ooh, Ross, I see you're just out of the shower, and highly agitated. You're like a kid on Christmas morning, or Hannukah morning, if you will. I can't wait to see what this little morsel looks like.

"She's got a very intellectual vibe, but underneath, I think she is probably gorgeous."

The doorbell rang. Rachel was closest, and opened the door. It was Shelley. Rachel invited her in, and gave Ross a scolding look. Shelley was transformed. Her hair was down, falling luxuriously over her shoulder. No eyeglasses. She wore knits, but it was a chic, thin, stylish knit suit. It showed off her bombshell figure without revealing anything.

Ross said, "You look so different, Shelley!"

Shelley said, "I tone it down for school. I figure this is a special occasion."

Rachel said, "Sit down, Shelley. May I ask how old you are?"

"I'm twenty-one."

Rachel was serious, "You're contemplating taking a serious step. Are you sure you're ready?"

"Quite sure. I want to get this over with, and get on with my life. My status has become a distraction, and I don't want to waste any more mental energy on it. I'm sure."

Ross asked, "Would you like some wine, or a beer, Shelley?"

Shelley said, "Ooh, wine, please, Professor Geller. I could use something to calm myself down. Also, as an anesthetic."

Rachel said, "One thing you certainly got right, Shelley, is your choice of Ross. He is the perfect man for this."

Shelley said, "There's an old saying, 'If you have to swallow a frog, don't look at it for very long.' That's how I feel about all the anticipation for this event."

Rachel laughed, "That is a great saying, and I know exactly what you mean."

Ross brought three glasses of white wine. Rachel raised her glass, and Shelley drank half her glass in one gulp.

The doorbell rang. The pizza arrived. Ross said, "Okay, ladies, are we eating with our fingers tonight?"

Rachel shook her head, "We're both wearing nice clothes, here, Ross. Plates, knives, forks, and napkins, please." While Ross was fetching the gear, Rachel leaned forward, and spoke privately with Shelley, "Shelley, I think how you are handling this is terribly exciting. You show a lot of maturity and self-awareness. I think you should get with Ross."

"I want to. Tonight, if possible."

Rachel said, "Let me surprise him with it, okay?"

Ross served the pizza. They ate, and drank wine. Shelley was drinking more than Ross and Rachel combined. Understandable. After a piece or two, Rachel announced, "Ross, we ladies have decided that you and Shelley should retire to the bedroom and solve her little problem for her."

Ross nearly gagged on his pizza, "Great! I mean, I respect your choices, ladies."

Rachel asked Shelley, "Shelley, would you feel more comfortable if I were present in the room with you and Ross?"

Shelley was taken by surprise, "Um, I hadn't thought of that. I think it might give me more confidence if you were there, Rachel." Shelley finished her wine, and Ross poured another glass for her.

Rachel stood, "You don't want to fill up on pizza beforehand. We can return to dinner later. Shall we?" She led the way to the master bedroom. Rachel had considered consigning Ross and Shelley to the guest room, but decided that the master was fine, considering all the other things that had transpired in there.

Shelley gulped down her wine as she stood. She asked, "Could I have more wine, please? I'm nervous." Ross opened another bottle of white, and brought it into the bedroom. Rachel sat in a chair a few feet from the bed, and tried to be inconspicuous. Ross looked to Rachel for leadership, and she pantomimed removing clothing. Ross poured Shelley another glass of wine. As she drank, he went to the far side of the bed, and began to undress slowly. He unbuttoned his shirt, removed it, and kicked off his house slippers. Shelley finished her glass of wine. She looked across at Ross. He asked, "Would you like me help you undress, Shelley?"

She said, "No, I can do it." Shelley removed her top, revealing a D cup bra that struggled to restrain two world class knockers. She looked tentatively at Ross, who responded by removing his pants. His erection was prominent in his boxers. He removed them carefully, and slipped into bed, covering himself with a sheet up to his waist.

Shelley answered by slipping off her skirt and shoes. She wiggled out of her pantyhose. She had a pretty hairy muff, which was a stark contrast to Rachel's nearly hairless pussy. Finally, Shelley unhooked her bra behind her back and let it fall. Her breasts were fantastic. Ross felt his cock throb as a direct result of seeing them.

Ross pulled the sheet down on Shelley's side of the bed to invite her in. She shakily got in, and pulled the sheet up to her chest. Ross said, gently, "Shelley, why don't you lie on your stomach for a bit, and I will give you a backrub. It will make us both more comfortable."

Shelley lay on her stomach. Rachel got massage oil out of the nightstand, and handed it to Ross. He pulled the sheet down, exposing Shelley to her thighs, and straddled her thighs on his knees. He squirted some oil into his palm, and warmed it in his hands before spreading it over Shelley's bare back. When Ross bent over to reach up to Shelley's shoulders, his cock grazed her bottom. Ross said, "The trick is to warm the oil in your hands before applying it. Rachel found that out the hard way!" They all chuckled, and Shelley relaxed a little.

Shelley moaned, "Oh, God, that feels so good! Oh, Professor Geller, where have you been all my life?"

Ross gave a skilled, erotic backrub. When he thought the time was right, he, slipped his hands under her sides and cradled her breasts. He made little circles with his hands, massaging them. Shelley was silent. Ross re-oiled his hands. He placed one hand on the small of her back, and slipped the other under her pelvis, in search of her clitoris. Shelley flinched when he approached her pussy, but he got to her love button and massaged it gently.

Shelly could not help but to make soft cooing sounds. She was getting turned on. Ross caressed her expertly. Shelly was so stimulated that she rose up on her elbows, and looked over her shoulder at Ross. He smiled at her devilishly, and continued to work her clit. He almost whispered, "Are you ready?"

She did not answer, but she rolled onto her back, and put her legs on either side of Ross. He gently lifted her knees up, and oiled his cock heavily. Ross felt that he might spray his cum all over Shelley at any moment. He prayed he could hold out long enough to enter her. He planted his hands on either side of her chest, and bent down to kiss her lightly on the nose, which made her smile.

Now for the coup de grace. Ross wiggled his cock into her slit, finding her vagina. He gently pushed in. His cock head slipped in with no difficulty. Her expression had not changed. Good! He glided into her pussy, inch by inch, as slowly as he could force himself to go. After he was halfway in, Shelley's brow furrowed, and she looked uncomfortable for the first time. Ross had momentum now, and the irresistible urge to bury his dick in this chick and inseminate her.

As he approached full insertion, Shelley made a little, pained sound. When he bottomed out, he came immediately. Ross blasted round after round of cream into Shelley's untouched womanhood. He cried out, "Oh, God! Oh, God! Uh! Uh! Uh! Oh, Goddddd!" It was one of the longest-lasting climaxes of Ross's life. He held himself mostly still, for her sake. The hold that her pussy had on him provided all the stimulation he needed.

Shelley made uncomfortable grunts, which Ross ignored. He pulled out a couple of inches, and glided back in. He worked his manhood in and out smoothly. He relished the feel of his cockhead sliding along Shelley's intimate anatomy, back and forth, back and forth. He got more and more excited, and sped up his pumping action. When he came for the second time, he gave Shelley the first hard thrusts of her new sex life. Each thrust yielded a substantial grunt from Shelley.

When his second orgasm died out, Ross felt sated. He pulled his dick out slowly, and lay on his side beside her. There were no tears on her face. He asked, "Shelley, how are you?"

Shelley said, "I'm all right. It hurt a bit, but I'm all right." She pulled the sheet up over her chest for modesty. She asked, "May I use the bathroom?"

Rachel met Shelley with a robe as she climbed out of bed. Shelley disappeared into the bathroom. Rachel climbed onto the bed, and gave Ross a high five, "Congratulations, honey. You nailed that puppy! Twice, if I'm not mistaken. How was she?"

"Fucking great! That is, great fucking! Rachel, I need to say that I'd love to give Shelley some lessons, if she's willing, and, of course, if you're willing."

"That'd be fine. I'd want to limit it to you being her first blowjob, first titfuck, first buttfuck. I really don't want you in a relationship, Ross. We'll see what we can do."

Shelley came out of the bathroom, wearing the robe. Rachel asked, "How are you, Shelley? Would you like to have some more pizza and wine, dear? You can get dressed, take a shower, or anything you like."

Shelley said, "Um, I think I'll get dressed, and see." She gathered her clothes and retreated to the bathroom. Ross got dressed, and she and Rachel took the wine back out to the living room to wait for Shelley. In a few minutes, Shelley came out of the bedroom, clothed, and sat down on the couch. Ross poured her more wine, which she drank even faster than she did when she was a virgin.

Rachel said, "I can microwave the pizza, Shelley, if you like."

Shelley said, "Yes, thank you." While Rachel was in the kitchen, Shelley spoke in low tones to Ross, "Tell me about it, Professor Geller. How was it, honestly?"

Ross said, "It was fantastic, Shelley. You are a sexy woman. I know a sexy woman when I see one, and I know a good lover when I lay with one, and you are both."

Shelley asked, "What now?"

Ross said, "Let's talk about that with Rachel." Rachel passed around warmed-up pizza. "Rachel, what now?"

Rachel said, "Shelley, Ross had a great time in there, naturally. There are many other firsts for you to check off, and I think Ross is the guy to do it. I think you two should get together like this a few more times. That way, Shelley can go into any relationship without fear."

Shelley said, "Speaking of fear, is Professor Geller well-endowed?"

Rachel cringed a little, "You noticed that, did you? Yes, he's bigger than average, but the important thing is he is a gentleman who knows how to use it."

Shelley asked, "What other firsts were you thinking of?"

Rachel said, "Well, oral sex, both you on Ross and Ross on you. There's titfucking, for which you are eminently qualified. That is fun and painless. I also recommend you getting in your first anal, Shelley. So many girls have horror stories about that. That's a big ol' bullfrog you'd best swallow sooner rather than later. Ross is the man, I can assure you."

Shelley said, "I'll think about all that. I have a lot to process, right now. Do you mind if I take some pizza home?"

Shelley left in good spirits with a whole pizza.

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