The Debauching of Emily Ch. 02

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The debasement continues.
2.5k words
4.61
19.7k
1

Part 2 of the 3 part series

Updated 09/22/2022
Created 02/05/2011
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Three days after our awkward, exciting, successful attempt at sex Emily and I had lunch together. It was a different atmosphere now then before. It was much more comfortable and relaxed. But, the sexual tension had increased dramatically. Through lunch we both alluded to our first encounter. Finally, she just came out and admitted that she'd been sore as hell the last few days.

"Let me know when the pain subsides. I need you again." I said plaintively.

"I think I'll be ready until next week."

"Next week?!"

"Well," she said slowly, "I suppose it wasn't sooo baaad."

"Uh huh"

"Perhaps...tonight?"

"Aahhh! That's more like it!"

She giggled then leaned forward and kissed me.

That night we stayed in and enjoyed another night of good ol' American sex. The lights were dim. We were in her bed and I wasn't about to complain about the missionary position. Her big breasts were pressed against me and her hands grabbed my ass and pulled me in while I pulled out for another thrust. We both fucked to exhaustion.

By then it started getting cold. Football season was in full swing. She learned that I had to watch at least one game on Sunday. We were at my house. I sat on my sofa. The ends both had recliners. She laid her head on my lap and read a book. I rested a hand on her belly and we both enjoyed the afternoon.

The game was dull. Both teams played like they weren't wearing cups. I started to get a little mischievous and slid my hand between her legs. A few gentle caresses and her legs slowly slid open. I didn't say a word I just started gently rubbing the part of her pants where her pussy was. She continued to read but now with her legs apart.

The game continued. The end of the half approached with no score. By now Emily abandoned reading her book and let it fall to the ground. I continued to massage. I could hear her starting to pant.

"How long is this game going to continue," she pleaded.

"It's almost halftime."

"Halftime? How long does that last?"

"Long enough to bend you over and have my way with you," I said.

"Oh GOD!"

And with that she unbuttoned her pants. I slid my hand down and was warmly greeted by a wet pussy. She arched her back. I leaned down and kissed her. A warm, traditional kiss quickly degenerated into an animal French kiss with angry tongues lashing out at each other.

I reached up to feel her breasts. She quickly grabbed my hand and slid it back where it belonged. I sat up watching this beautiful women enjoy my petting. She unbuttoned her sweater exposing her breasts in a bra. I leaned forward and buried my head between her breasts and inhaled deeply. As I kissed those beautiful tits I slid two fingers in her hungry pussy. She moaned. Then I slid three fingers in and she moaned some more.

Finally and sat up again and enjoyed frigging my new girlfriend. She moaned and seethed with erotic pleasure. It was an amazing view.

I said, "Would you like to try a new position?"

"What?" I broke her concentration. "Oh. Yes!"

"Get naked," I commanded.

Soon we were both without clothes. Somebody scored a touchdown. Whatever. I rolled her over and had her lay face-down on the couch with her knees on the floor. I put one knee between her legs and used the other knee to gently force her legs apart. Emily gasped uncomfortably.

I took my rock hard dick and started to massage her clit. This had the desired effect and any discomfort she had with that position melted away.

"God, yes. Do it," she pleaded.

Not wanting to torture her too much I lined up my dick and slid it in. Soon I reached the back wall of the inside of her body. I slowly withdrew my cock and slid it back until it again pushed against the end. Each thrust was greeted with matching grunts from Emily. I ran my hands up and down her back then began to massage her shoulders. This allowed me to pull her back while I pushed forward. Each time I pressed against that wall and each time she grunted.

"I like pounding on you cervix," I groaned in a neanderthal tone.

"Oh god yes!"

"I'm gonna cum all over it!"

"yes. Yes! YES!!"

And with that I started thrusting harder and faster, my dick getting bigger and bigger. I was fucking the shit outta her! As I was enjoying the feelings in my dick and balls I looked down at her sweet ass. She had a great ass and I couldn't help but observe how tight it was. Clearly anal was something that she'd never tried before. Her little button was as tight as could be.

"Huh," I thought. "Her tight, little asshole isn't going to be that tight for long!"

I sucked on my thumb a little and then used it to massage her little ass button. Soon my balls took over. I grabbed both sides of her hips and thrust uncontrollably. I really kinda lost track of what I was doing. I came so hard that I fainted a little and fell over on top of her.

We laid there for a while until I regained consciousness. Finally I slid out of her, my goo gushing out of her well-fucked pussy. She rolled onto the sofa and I climbed on top of her kissing her breasts, neck, and mouth. She ran her hands through my hair.

"Did you like that position?" I whispered.

"Mmhmm," she purred. "What were you doing to me at the end there?"

"I was rubbing my thumb on your butt."

"Huh."

"Did you like it?"

"Yes. It felt good."

"Good."

"I've never had a man do that to me before."

"Huh."

"I hear the women at my office talk about stuff like that."

"Like what?" I asked as if I didn't know what she was talking about.

"Like, you know...The OTHER way..."

"Huh. What do you think about 'The OTHER way'?"

"Uhm. I don't know. I would have said, 'no, definitely not' before but that felt kind of good."

"Good. I'm glad you liked it. We can do more of that some time."

There was a pause. It wasn't a long pause but it was a pause. Clearly the wheels were turning in that pretty little head of hers. Was she thinking, "Hell yeah!" or was she thinking, "I can't imagine that I would ever agree to something like that."? Only time would tell and I knew that I had to play it juuusssst riiigghhtt.

Soon, we jumped up and took quick showers. I got back to the game and she assumed the same position as before and read her book. Quite a pleasant interlude.

A few days later I sent her a website that I thought she might like. "Anal Sex Yes" dot com. It gives good advice on how to do it the first time. I thought she'd like pointers. Step one: "Use lots of lube". Start with a vibrator etc etc.

"Man, this is gonna be great," I thought.

A few days later we had lunch again. I was really hoping she'd tell me she liked it. No mention of the website. No sexual innuendo either. that was unusual. She was affectionate but not terribly sexy. After lunch we were walking out of the restaurant when she mentioned, "Can you come over tonight? There's a good movie on tonight."

How could I resist?

Later that night I arrived to a half-schnockered woman who was half way through a bottle of red wine. She was in a little back nighty and high heels.

"Humh. I wonder what she wants?" I thought.

"Hiiiiii!" She slurred. The kiss was deep and slutty. This is gonna be good.

"I'vf binwaitin' furyou." More kisses and her ass was nice and tight.

It didn't take long for her to pull me upstairs. Man, she was ready.

"I want to try it...the OTHER way."

HOLY SHIT!

I practically ripped her clothes off. I pushed Emily on the bed and dove for her wet, drunk pussy. I licked her and slid three fingers into her. She just went with it and LOVED it. Her orgasm was EPIC! Wow. I hadn't seen anything like this before.

I flipped her over to fuck her from behind. Just then she reached into her nightstand drive and pulled out a vibrator, bottle of lube and a sly smile.

"I thought we could use these."

"Hell, yeah!"

I took control and pushed her onto the bed face down. She pushed up onto all fours and I positioned myself behind her. I couldn't wait to get into her waiting pussy. After the licking I gave her she was good and wet. I slid it without a problem.

"God, yes." she yelled.

I grabbed both hips and began to fuck her furiously. Just as things started to get good I opened the bottle of lube and dripped it onto her tight ass. Then I turned on her vibrator and laid it on her tight hole. There was a pause and then she moaned - a LOT!

"Yes. Oh, God. That's good."

"Yeah? You like it?"

"Hell yeah!"

I stroked and thrust and held the vibrator on her ass.

After a few minutes of that she said, "Put it in me."

I wasn't sure if I heard her right.

I lubed up the vibrator and pulled my dick out of her pussy. Twist and turn and push and it was IN!

"Oh GOD!"

I held it still while she got used to the sensation. I saw her grab the covers and clench her fists. She started making noises that I hadn't heard before.

I figured I'd slide my dick in her again. Wow. That was quite a sensation. The vibration went through her ass and into my rock-hard dick. She came like a freight train. Her screams were loud enough to wake the neighbors.

Soon she was instructing me to take it out. It slid out easily and she flopped flat on the bed, completely exhausted. I wasn't about to let this end here. I lubed up my dick and laid on top of her. Her legs were closed. I figured she'd be more comfortable for our first attempt if they were closed. I massaged her ass button with the head of my slick cock.

It didn't take long before Emily moaned, "God. Just do it."

I held myself up with one arm and lined my dick up with the other hand. I let my weight do all the work. Suddenly I felt her ass start to part and I eased up immediately. Once I cracked the seal I eased up on the pressure and let it slide all the way inside in one smooth plunge.

I held tight for a moment. No complaint and man, it felt great. I kissed the back of her neck and let her adjust to the new sensation. After a minute I asked, "How does it feel?"

There was complete silence. I eased my dick out again. The feeling of her ass clenching the entire length of my dick was too much to take. After I slid more than half way out, I eased it back in again.

This time there was an animal grunting sound coming from this lovely lady.

Again I asked, "How does it feel, baby?"

"Oh MY GOD!" she exclaimed, "It's amazing!"

It took all I had to keep from laughing. I had to bite my lip. "I'm glad you like it. Do you want more?"

"Yes! Stop talking and do it!"

"Do what?" I teased.

"Do it harder!"

"Tell me what you want me to do?" I was getting even harder with each command."

"Do IT! FUCK MY ASS!!!"

Well, there's a first. I wondered how far I could make her go. I started thrusting a little faster.

More grunts.

A little faster until I was at full speed ahead.

"Oh god! I feel like a whore!" she yelled.

"You ARE a whore. You're a DIRTY little whore. You're MY dirty little whore!"

"Yes! I want to be your dirty little whore!!"

Hearing that, feeling her tight, lubed ass, and seeing the look of extreme pleasure when she turned her head in my direction was just more than I could handle. It really did feel like my dick exploded. Her reaction was as if there had been an explosion actually occurring in her ass. Her orgasm happened about the same time mine did.

We were sweaty and exhausted. I thrust my cock in all the way for the last burst and fell on top of her. After we regained our composure I eased my dick out and walked to the shower - quite unsteady.

After a few minutes in the shower I heard the door open and she joined me.

We stood there in the hot shower kissing deep, passionate kisses. We retired back to bed and she rested her head on my shoulder. My right hand took the usual place at the base of her back and my left hand played with her hands.

"Wow. That was really something," she declared.

"Yeah. I loved it."

Then she looked at me and whispered, "I enjoyed being your dirty little whore."

"Hell yeah. That was fun. I need to pay you."

She hit me in mock surprise/disgust. We laid there some more enjoying the afterglow.

"Was that a fantasy you've had?"

"Yes," I said. "Was it a fantasy of yours?"

She didn't say a word but nodded her head coyly. I continued to stroke her ass.

"What other fantasies do you have?"

Silence.

"What do you think about when you're all alone with your vibrator?"

"Oh, I don't know. All SORTS of things."

"Well, you can tell me when you get comfortable. I'd like to fulfill your fantasies."

She giggled and ran her hand through my chest hair.

"I've never seen a porno movie before," she suddenly declared.

"Never? Not even part of one?"

"Uh uh."

"Would you like to watch one some time?"

"Sure. I think it would be interesting. Maybe the next time you come over you could bring one."

"No problem."

I felt my dick start to harden. Just about that time she saw the covers twitch and reached down to massage my balls.

"You're HARD!"

"Uh huh," I said slyly.

"Ooh, you DO like hearing about my fantasies, don't you?"

"Uh huh. See the effect it has on me?"

She stroked for a few moments then slid down and plunged her mouth down my length. There was no fooling around. She sucked and massaged deftly. I was impressed with how fast she learned.

It didn't take long. I felt the next gush of cum well up inside my balls. I arched my back and let loose.

"Oh HELL yeah!"

The burst made her choke a little but she took it like a champ and sucked out every last drop. I didn't even need to get a towel. We both started laughing as she slid up to resume her place in my arms.

I reached over and took my wallet from the night stand. I pulled out a twenty and handed it to her.

She laughed out loud and said, "I guess I really am a dirty little whore."

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2 Comments
AnonymousAnonymousabout 13 years ago
hell no!

Decent enough tale, but kindly find a substitute for 'Hell, yeah' please.

BarbaraBarbaraabout 13 years ago
Realistic, ironic genesis to all aspects of orgasmic conquest! Voted 5!

Loved the concluding $20-00 note! I might have enjoyed taking it up my back passage, gift wrapped around an air expanding dildo, to stretch my sphincter muscles until artificial lubrication wasn't needed anymore! I just let out the air, extract the dildo then invite my male lovers to take me anally! Most ladies prefer anal abuse to all other forms of penetration!

Cannot understand women that insist on vaginal sex, before considering the natural alternatives. Anal fisting is great, as long as finger jewellery is removed beforehand, just fulfilling and gratifying enough for any horny female in search of excitement I sleep better, feel hornier then literally beg for more hot male flesh deeply in my upper colon? A natural enema once daily, is always welcome in our house, male ejaculate hot and moist from my puckered rear bum's point of view! Hooked on Anal sex for ever!

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