A Surprising First Pt. 08

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Lori and Dee Go Anal.
2.9k words
4.39
22.3k
14

Part 8 of the 8 part series

Updated 06/07/2023
Created 02/21/2015
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Sorry I haven't been here to work on this series for a while. Too many things going on in real life. But I will try to finish it in the next few weeks.

*****

Following a long, hot, sexy shower, in which Dee and Lori washed each other's bodies sensually, they dried off and went into the kitchen, naked. Both were hungry and somewhat tired, but both were looking forward to another "lesson."

Dee checked the refrigerator for something light to eat. She decided on cheese, some fresh raw vegetables and crackers. Lori opened a bottle of white wine and poured them each a glass. She handed a glass to Dee.

"To new adventures," Lori said as she held her glass up.

"To incredible sex," Dee responded as she clinked Lori's glass.

"I like yours better," Lori said before taking a drink of the wine. "Let's eat and go back to bed. I've got more great sex to show you."

"I'll drink to that," Dee replied. And she did.

The women took their cheeses, vegetables (carrots, celery, broccoli) into the living room and sat next to each other on the couch as they ate. Neither seemed to be interested in food anymore. Dee was looking at Lori's perfect tits, thinking about how Lori's nipples responded to her touch.

Lori, on the other hand, was looking at Dee's pussy and thinking about the upcoming lesson. Dee was going to be introduced to anal sex tonight. Lori had a seven inch long, bullet shaped vibrator that was going to be Dee's first experience. If all went well, by morning Lori would be fucking Dee's ass with her strap-on. She was fully confident in her ability to show Dee how pleasureable it could be.

Within about 10 minutes both women had put their plates on the coffee table. They each still had their wine and touched glasses one more time. Lori leaned forward and kissed Dee, her tongue leisurely exploring Dee's mouth. Dee placed her right hand on Lori's face as she returned the kiss.

When the kiss broke, Lori suggested they get the wine and go back to the bedroom. Dee agreed.

They took their plates to the kitchen and Dee grabbed the bottle. "Lead the way, my lover and teacher," Dee said to Lori. She watched as Lori's gorgeous ass headed into the hallway. "I think I could fuck that," she thought. And fuck it she would.

When they got back to the bedroom Lori told Dee to get on the bed on her back. Dee set the bottle and her glass on the night stand and did as instructed. Lori disappeared into the living room for a moment and returned with her goodie bag.

"I'm going to introduce you to anal pleasure," she said. "And before we go to sleep you will have experienced an orgasm from anal penetration."

Dee felt like a bolt of electricity shot through her and exploded in her pussy. She became warm all over and suddenly the thought of having something pushed up her ass was no longer scary but exciting. She knew Lori would never hurt her. So it must be a good thing, right...?

"Don't worry," Lori assured her, as if reading her mind. "This is not going to hurt. I've been having anal sex since I was a teenager and I love it just as much as regular sex. Once your ass is broken in and you figure out how great it can feel, you are going to love it too."

Lori pulled the vibrator of choice from her bag. "After this week, not only will you be sharing your ass with me but with Steve and even with David. You're going to turn into an anal slut like me. I guarantee it."

Dee didn't know what to say. Lori's words were exciting her and her hand wandered mindlessly to her clit.

"Are you getting turned on, baby?" Lori asked when she noticed Dee slowly rubbing her clit.

"Oh yes..." Dee responded. "I need to cum again. You turn me on so much. I look forward to your lesson and my ass is already anticipating your touch."

Lori picked up a bottle of baby oil and poured some on her right hand and fingers. She got on the bed and crawled up between Dee's legs. Laying the oil and the vibrator aside, she told Dee to put her knees up and spread her legs. She moved Dee's hand away from her clit and Lori applied her tongue. As she did, she also began rubbing her oil covered fingers on and around Dee's anus.

"Oh my God, that feels good already," Dee moaned as Lori's middle finger gently probed Dee's sphincter. She pushed in slowly, just enough to make Dee squirm, then pulled back out. As much as she wanted to don the strap-on and have her way with Dee's sexy ass, she must take her time and break her in right. She would fuck Dee in the morning. And Dee would fuck her.

"Just relax and let me do what I do," Lori told Dee. "I'm just going to get your ass accustomed to being penetrated. I'll open you up slowly and it won't hurt at all. Then I'm going to fuck you with this." She held up the vibrator.

"Do you think something that big will go in my ass?" Dee asked incredulously.

"Baby, by the time I finish your lesson you'll be craving a large cock in your ass. And you'll be getting it before the week is over."

"Mmmmmmm," was all Dee could say in response, because just at that moment Lori pushed her middle finger slowly and deliberately into Dee's ass. She pulled out slowly, added a few more drops of oil, and pushed in again.

"How does that feel," she asked Dee.

"Surprisingly good," Dee responded. "I'm not sure why I never tried this before. Steve has wanted my ass since we were married but I always said no. The one time I said I'd try it he tried to put his cock in me and it hurt."

"It has to be done correctly," Lori told her. "Slow, steady, and working your way up to larger things is the best way to do it. By the time I get you stretched out that vibrator will feel like my finger."

"That sounds wonderful. If your vibrator feels anything like your finger I'm going to like it."

"Eve better," Lori told her. "You're going to cum hard."

Lori was now pushing her middle finger in and out of Dee's ass. Dee's anal opening was relaxing and it was time for a second finger. Lori drizzled a little more oil on her index finger and slowly introduced it into Dee's ass, alongside her middle one.

"Ooohhh..." A moan escaped Dee's lips. "That feels good. My pussy is getting wet."

"That's the idea," Lori said. "Soon I'm going to fuck you with my toy."

Dee shuddered. Lori's words were making her even wetter and she pushed three fingers into her own hot slit. Lori watched with interest. She was getting wet herself.

Lori got the baby oil once more and drizzled a little more on her ring finger. She slowly pushed all three of her fingers inside Dee's anus. This was the right size - nearly the exact size of her vibrator. She knew it wouldn't be long before she shoved the plastic sex toy inside Dee. It would be Dee's awakening to analy pleasure. And in the morning Lori would take Dee's virgin ass with her strap-on... if she could wait that long.

Lori began fucking Dee's ass with her three fingers. Dee was moaning and rubbing her pussy wildly. She obviously was loving this. "A quick study," Lori thought happily. This was going to work out well.

"OK, I think it's time," Lori said, slowing her movements and getting reaching for the vibrator.

"You're not going to stop, are you??" Dee was in full heat.

"Just changing over to the toy," Lori assured her. "You're really going to like this."

"I'm so fucking horny. I'm ready fow whatever you want to do to me," Dee responded.

"Patience, Lori..." Lori thought. She was tempted to strap on her fake cock and take Dee's ass properly. But she didn't want Dee to experience any pain or discomfort. Anything like that could turn her off to future anal exploration.

Lori lubed up the vibrator and slipped the tip of it into Dee, past her sphincter and about three inches inside.

"Mmmmmmmmmmmmmmmmm..." Dee let out a long, low moan. "That's incredible. I see what you mean. Are you going to fuck me?"

"Oh, yeah. I'm going to fuck you. And make you cum."

"Do it..." was Dee's response.

Lori pulled the vibrator nearly all the way out and applied more oil. Then she slid it in all the way, until the only part protruding was the half inch or so she was holdling on to. She pulled it out and pushed it back in, repeating it over and over as if she was fucking Dee.

Dee was responding physically. Lori could see it. She was playing with her clit, her eyes closed, her hips rising slightly off the mattress with each inward thrust.

After several minutes Lori couldn't take it anymore.

"Don't move," she instructed Dee. "I'll be right back."

Lori hurried into the living room leaving the vibrator buzzing in Dee's ass. Dee stopped rubbing her clit and followed Lori with her eyes. "Noooo... what are you up to?" she called after her.

Lori went to her bag and pulled out her strap-on. Dee was taking the vibrator so easily that Lori knew she could handle the phallus. And Lori needed to fuck Dee. Needed it like crazy. Her pussy was on fire and was dripping copiously. If she didn't attain release she was going to explode.

She inserted her end of the device into her hot, waiting pussy and cinched the straps. It hung in front of her at a 90 degree angle, appearing as a snake looking for its prey. Lori walked back into the bedroom. Dee was still on the bed in the same position, the vibrator audible from the doorway. Her fingers were still toying with her clit and she was watching, waiting for Lori's return.

"I can't wait until tomorrow," Lori said. "I need to do this now and you're ready. I have to fuck you and I have to fuck you now."

Dee stared at the flesh colored cock sticking out at least 7 inches from Lori's groin.

"Are you sure I'm ready for that?" she asked timidly.

"I'm sure," Lori replied. "How does that vibrator feel in your ass right now?"

"Heavenly," Dee said. "But..."

"Remember what I said - that I'd never hurt you?"

"Uh huh. But..."

"Trust me," Lori instructed. "I will go slow and easy and you will enjoy it. I promise."

Lori grasped the end of the vibrator and began working it in and out of Dee again.

"Oh, God... that's so good," Dee said, in spite of herself. "Can you make me feel that good with this?" She wrapped her hand around the fake cock.

"Watch and learn," Lori said with a wink.

Lori released the vibrator, leaving it buzzing in Dee's ass. She knelt between Dee's legs aned lined the phallus up with Dee's other opening. She slid it into Dee's warm, wet folds. The pressure inside her own pussy from the two ended strap-on was heavenly. But Lori couldn't afford to get carried away. She was getting it wet and slippery, that's all.

She pushed in and out of Dee a few times. Dee let out a long, low moan, obviously enjoying the double penetration. Abruptly, Lori pulled out and bent to remove the vibrator from Dee's ass.

She grabbed the bottle of lube and squirted some on her cock just for good measure.

"Pull your knees back," Lori instructed. Dee followed the order and pulled her knees toward her shoulders, raising her ass off the bed so Lori could get to it.

Lori squirted a slight amount of lube on Dee's very loose sphincter and lined up for entry. Dee started to tense up.

"Don't worry, baby," said Lori soothingly. "I'm going to go slow and be gentle. This is going to be even better than the vibe. I promise."

"OK," Dee responded. "I trust you. Take me as you will."

With that, Dee relaxed and Lori slowly introduced her plastic phallus into Dee's ass. The head slipped in easily. Dee gasped but it was in pleasure, not pain.

Lori pushed slowly, adding a little more lube as she did. "Her cock" was about halfway into Dee's rectum now and Dee was not complaining.

"How does that feel?" Lori asked.

"It... feels... great..." Dee panted. "Better... than... I... imagined..."

"We're still going to go slow until you're ready," Lori told her. She looked directly into Dee's eyes. "Then I'm going to fuck you until you cum."

"Oh God... I can't wait," Dee said. "I need to cum. I need to cum bad."

Lori took that as a sign and pushed further into Dee's ass. Finally she was at the hilt. Her pubis rested against Dee's beautiful, wet pussy lips. She pulled out slowly, about five inches, then pushed back in.

"Ohhhhh shiiiiiiiittttttt," came out of Dee in a whisper.

Lori pulled out again, drizzled more lube on her cock, the tossed the bottle aside. This was it.

She used her finger to rub the oil around the rubber cock then pushed it back in forcefully.

"Uuuunnnnnnnhhhhhhh," Dee said. "Fuck me! I'm ready. Fuck me hard and make me cum!"

Lori was happy to oblige. Her own pussy was screaming for release by now. She began thrusting into Dee in a rhythm, pushing in with long strokes and pulling out nearly all the way before plunging back in. Dee was taking it even better than Lori expected. She guessed that Dee's fear of anal sex was more about the taboo aspect of it than physical fear. But once she broke the lesbian boundary the taboos kind of went out the window.

She was into it now. She was fucking Dee hard, feeling the cock inside her own body stimulating her pussy and clit with each thrust. She wanted Dee to cum first. But then, she was going to explode in an orgasm that had been building all day.

"Are you going to cum, babe?" Lori asked.

"God, yes. Soon," Dee responded. "I never dreamed it could be this good!"

Her rate of breathing was increasing and her heart rate was through the ceiling. Dee was experiencing a sexual high that had eluded her for years - since she first fucked her husband.

Lori was getting close. "Dammit, Dee... cum. I might not be able to hold it," she thought.

"Cum for me, baby," Lori said. "Cum now." She bent and kissed Dee's lips before taking her right nipple in her mouth.

That did it for Dee. Whe Lori's mouth touched her nipple it was over.

"Oh my God...! I'm cumming, Lori! Oh, shit! Ooooohhhhhh! Oooohhhhhh! Oooohhhh mmmmmyyyyyyy Goooooddddddddd!"

Dee's body shook with the power of the orgasm that went through her. She had experienced powerful orgasms before - as recently as yesterday with Lori. But she had never experienced the power of what was going through her now.

She could feel her ass contracting around the fake cock. It should hurt but it was exquisite! The pleasure went from her ass to her pussy, up to her nipples and back to her pussy. She was overcome by pleasure and emotion and she grabbed Lori and pushed her tongue into Lori's mouth as deeply as it would go.

That set Lori off and her body also began convulse with pleasure.

"MMMMMmmmmmmm hmmmmmmmmmm,,,," Lori moaned into Dee's mouth as their tongues battled each other. It was good. So good...

Finally, after a very long period of pleasure, peak and coming down, Lori rested on Dee's chest. They were both breathing very hard and sweat coated their bodies.

"That was fucking amazing," Dee said. "I wish I'd done that 20 years ago! God damn...!"

"Told you," Lori said. "Always trust me, babe. I'll never steer you wrong."

"I want to fuck your ass now but I'm too fucking spent," Dee said.

"Tomorrow morning it's all yours," Lori assured her. "Let's rest now."

They laid there for several minutes and Lori said "Just think. Soon you'll not only have Steve fucking you like that but you might be fucking him in the ass as well."

"Do you think he'll go for it?" Dee asked.

"I think, once he gets to fuck your ass and then sees me and you fucking David's ass, he'll come around."

"You're going to let me fuck David's ass?"

"Of course," Lori said. "The whole idea of this is to get all four of us fucking each other and enjoying great sex forever."

"Me... fucking Steve's ass... That would be the hottest thing ever."

"Just wait until the guys fuck each other. That'll be hot too," Lori told her.

"Steve will never go for that," Dee said.

"Maybe. But you just never know what could happen. Before this week you never thought you'd ever take a cock up your ass. Now look at you."

Dee smiled. "I guess I'm as ass slut now. But that's OK. I love it!

"And I love you," Lori said, kissing her sweetly. "On Saturday night all of us are going to love each other in a way that will blow the boys' minds. They're never going to be the same."

"Neither am I," Dee said quietly. "Neither am I..."

*****

To be continued - sooner this time, I hope.

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Sunnydaze361Sunnydaze361almost 2 years ago

Simply the best! I have read the story before and had to start over again! It’s been a while since Part 8 but it one of the best stories here!

AnonymousAnonymousabout 8 years ago

I can't wait for the rest of the story.

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