Friends - Alternate Reality Ch. 56

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Ch 56--The One with Ross and Shelly Again.
1.8k words
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Part 56 of the 63 part series

Updated 06/11/2023
Created 06/22/2022
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Shelley called Ross the week following her defloration, "Hello, Professor Geller, it's Shelley."

Ross was truly glad to hear from her, "Shelley, how are you?"

Shelley said, "I'm good, and I think I'm ready to take the final steps."

Ross said, "That's great news, Shelley. We'll try to accommodate your schedule."

Shelley said, "It is I who should do the accommodating. The last time worked out well, so why don't you pick a day to get together after school?"

"Ummmm, let's see. Tomorrow is great. I'd like to make it five o'clock, because I don't want you out on the streets late at night."

"Five o'clock tomorrow. See ya'."

Ross caught her before she hung up, "Oh, wait! What kind of food would you like?"

Shelley didn't want to be a pain, so she said, "Oh, I like pretty much everything."

"Italian, it is."

Ross immediately phoned Rachel with the good news that he would be the first to enjoy Shelley sexually in one or more additional ways.

"Congratulations, Honey. You did such a good job popping her cherry that she came back for more. That says a lot. What are you going to do?"

"We didn't talk about that. We'll all find out together."

The next evening, Ross brought home an enormous amount of Italian food, and showered before five o'clock. Shelley arrived right on time, and looked happy and relaxed. They had a snack, some wine, and cheerfully went into the bedroom.

As Ross and Shelley stripped, Rachel asked, "Did you have anything in particular in mind for tonight, Shelley?"

"Um, I don't know. Can we start with the titty fuck?"

Ross said, "It would be my pleasure." He got the appropriate oil out of the nightstand. He got onto the bed on his knees. "Now, Shelley, just sit back against the headboard, and use this pillow for cushioning. Now, I'm going to oil you up. Your job is to push your boobs together tightly to keep my cock inside. I'll work it up and down. I'd like to come in your mouth."

"I don't think I'm ready for that. Can you just come on my chest?"

Ross said, "Sure. No problem." Ross and Rachel knew full well that Ross's ejaculation could not be confined to her chest, neat and tidy. Shelley was walking into a sperm storm. Ross straddled Shelley and pressed his cock to the space between her boobs. He nodded, and Shelley pushed her big tits together.

Ross sighed deeply. He pumped his cock up and down, inside the warm, slick home her breasts made for it. Ross said, "Tighter." He sped up his stroking. Again, he said, "Tighter." She did her best. He said, "Look up into my eyes." She did, and he felt a warm surge go through his body. He pumped harder than ever, and said, "I'm gonna come. Keep it up!" When he ejaculated, he pushed his cock upward and held it there. The head was almost touching her throat. He sprayed his cum into her throat and chin. She instinctively looked down, only to receive a blast of semen in her face, up her nose, and on her lips.

Ross finished coming, and pulled out. He said, "Oh, my God, Shelley. I didn't expect that. I'm sorry. That was unintentional."

Rachel gave Shelley a hand towel, and said, "You can go into the bathroom to clean up."

Once Shelley closed the bathroom door, Rachel and Ross stifled laughter. Rachel could barely speak, "Oh, the poor, innocent thing. I think that's nasal rape, Ross."

Ross said, "She's a quick study, Rachel. I think that'll be the only time I can fool her like that.

Once Shelley cleaned up and returned to bed, Rachel said, "Shelley, dear, the way to a man's heart is through a blowjob. Let's work into it slowly. This is honey. I'll smear it on him, and you lick it off. Ross and Shelley were in the same positions as before. Ross presented his sticky stick to her, and she delicately licked it. They gave her time to adjust. Rachel said, "Shelley, you have to lick harder than that. Make broad contact with your tongue. Here, try again."

Shelley did better this time. Rachel said, "That was just to familiarize yourself with him. Now, take him into your mouth. Remember, the cardinal rule is no teeth. Here's some more honey. Let's try." Shelley opened her mouth very wide, and Ross just stuck the end of his dick into hit. Rachel said, "Your lips form a seal around it, Shelly. You lick the underside of him with your tongue the whole time. When you've got that, you add sucking."

Ross said, "Keep your lips firmly on the cock, Shelley. There. Good! Now, the tongue." Shelley worked on these principles for several minutes. Ross said, "Ooh, that feels good, Shelley." When she began to tire, Ross said, "Shelley, I need release. How about another titfuck?"

Shelley said, "Okay, but I want to turn my face away when you come."

Ross said, "This time, lay flat on your back, with this pillow under your head, I'll do the moving. You just squeeze those knockers together tightly." He oiled her chest, climbed over her, and he laid his erection between her breasts. She pushed them together, and he started fucking them. He pumped very rapidly. Shelley figured that she saw the head of Ross's cock appear and then disappear approximately three times per second.

Ross worked her tits hard for several minutes. When he sensed his climax coming, he said, "I'm gonna come!" She turned her head severely to one side, and squeezed her eyes shut. He pumped violently right through his orgasm. Shots fell on her throat, the side of her face, and in her hair. Rachel could barely suppress a laugh. Shelley went into the bathroom to clean up, and she joined Rachel and Ross in the living room to finish dinner.

Rachel advised, "You can see why it's customary for the guy to spray his cum into the girl's mouth, like a blowjob. It's just so much neater and cleaner."

Shelley said, "The semen in the mouth thing is a hurdle for me, but I'll get it."

Rachel said, "You have to if you want to keep a man happy. Fact of life."

Shelley agreed to come again, two nights later. Ross told Rachel that he dearly wanted to fuck Shelley's pussy again. They formed a plan to make that happen. Once in the bedroom, Ross said to Shelley, "Just lie back, with your head on a pillow, raise your knees up, and spread your legs a little. Do you have orgasms from masturbating?"

Shelley said, barely audibly, "Yes."

Ross said, "Just wait. After you have an orgasm, I want to make love to you again, Shelley."

"Um, I guess so."

That was all the approval Ross needed. He dove into her muff, and sent her nearly into orbit in mere seconds. She tossed her head around, eyes bugging out, crying out incoherently. Ross grabbed her thighs to prevent her from dislodging him as she flailed about. After a few minutes, Shelley appeared to go into spasms, signaling her orgasm. After it ended, and she recovered sufficiently to speak, she said, "That's it. That's enough."

Ross swiftly lubed his erection, and mounted her before she could object. He tried to enter her as gently has he had the first time. She was more vocal this time, "Oh, no, don't. Professor Geller! No!" It was too late for no. He was already entering her, and nothing could stop him from spearing her and finishing. After he was most of the way in, she stopped protesting and just rode it out as best she could.

Ross churned his wang in Shelley's pussy for about a minute before coming explosively. He rocked her with his concluding thrusts. He pulled out, and chose to call it a night.

The following week, they scheduled Shelley to come Friday night, so that Ross would have plenty of time for what Rachel hoped would be his last meeting with her. First, they revisited Shelley's blowjob technique. It had improved enough that Ross came in Shelley's mouth. She was still poor at giving head, and she gagged and coughed up a lot of his sperm, but at least Ross went on record as her first.

While Shelley was in the bathroom, Ross said, "I want to complete this, Rachel. I want to be the first to have her in every way. She will have nothing new to offer any man, ever."

Since it was Friday night, Shelley drank liberally as they ate dinner. The plan was to get her dead drunk, and buttfuck her. That would be it for Ross and Shelley, as lovers. Rachel wanted this to end far more than Ross did. Rachel poured the booze into Shelley as fast as Shelley would swallow it. When Shelley had difficulty sitting upright, Ross and Rachel helped her into the bedroom. They removed her robe, lay her on her stomach on the bed, and let her rest. They slipped two pillows under her pelvis, and spread her legs a little.

Ross and Rachel had planned this carefully. The idea was to make it so quick and confusing that Ross could get his shot off before Shelley had time to object. It would be a challenge, because he had already come once that night. Ross lubricated himself, and delicately poured oil down Shelley's butt crack. Rachel sat on the bed, holding Shelley by the shoulders and talking to her. Rachel was tasked with distracting Shelley, and restraining her if she attempted to escape.

Rachel nodded to Ross. He spread her butt cheeks with his hands, put the tip of his dick into her anus, and pushed. Once established inside, he fell forward onto his outstretched arms, and put his weight behind his penetrating rod. Shelley looked about quickly, and asked, "What's going on?"

Rachel held Shelley's shoulders firmly, and said, "It's like a massage, Shelley. Ross is massaging you. It will feel nice. Just relax, dear."

Ross was all the way inside her ass, now. Nothing could dislodge him. He pounded her ass for a few minutes and gushed cum as a grand finale. He carefully pulled out. When Rachel and Ross released Shelley, she was confused, and staggered into the bathroom. Everything was normal when she emerged. Ross and Rachel were sipping wine in the living room. They invited Shelley to join them for dessert.

Shelley slumped into her seat. The shock of what Ross had done had sobered her up considerably. They poured coffee for her. She picked at her dessert. Finally, she said, "I'm going home," and went into the bedroom to dress.

When she came out, Shelley said, "I think this is over, guys. Bye." She wearily headed for the door. Ross was concerned that Shelley could not make it home safely. Rachel said, "Shelley, we'll go downstairs with you, and get you a cab, so you get home safe, okay?"

As the cab disappeared into the night, Ross said, "The perfect crime."

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