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Sarah - Part Five

Sarah teaches me about anal sex
I returned from my holiday vacation the day after Christmas, eager to see Sarah. As I neared the house, I was happy to see her car and only her car in the driveway.

Inside, Sarah was sitting in my favorite leather chair wearing jeans and a sweatshirt, with bare feet, listening to music and drawing on her sketch pad. I had mentioned that Sarah was an artist, and there on her pad in pencil was a drawing of a life sized cock.

“Anyone I know?” I asked.

“You know whose dick this is!” she responded coyly.

We hugged and talked about our holiday experiences for a while. I went upstairs to unpack my things. When I came downstairs, Sarah had left the house.

I made myself some coffee and read the newspaper.

Sarah was gone about an hour. On her return, she simply said “hi” and went to her room.

I read the paper for a while, then shut off the reading light and closed my eyes.

I heard Sarah’s door open.

She was straddling me in the chair before I could even move. Totally naked, she grabbed my head and gave me on of those slobbering, open mouth, tongue sucking kisses that goes right to the core of your body and starts the blood pumping and the heart beating.

“I was only gone for five days, but I really missed this!” she said.

“Are you hard?”

“Yes I am,” I responded.

“Take it out. I want to play with it so bad!”

Sarah stood up, displaying her beautiful body. I undid my pants and pulled them off and Sarah grabbed my stiff shaft with both hands and made love to my cock.

Sucking, licking, stroking, running her fingers over the swollen head, she had me at the edge in minutes.

I, too, had not cum for five days, so Sarah’s blow job did not last long.

I told her that I was going to cum. All she did was sit back and stroke my manhood with both hands until I moaned loudly, arched my back, and shot long, high, thick lines of cum into the air. Most of it landed on her arms and hands; some on her shoulder and hair; the rest on the arms of the chair.

“I love how much you cum!” she said with a smile, still stroking hot goo out of my cock.

Sarah licked me clean, licked cum off her arms and hands, and went to the bathroom for a towel to wipe the rest off her shoulders and hair.

There is something very erotic, sensual and personal about watching a woman eat cum when it is your cum.

When Sarah returned, she was holding something behind her back as she climbed on me again.

“Want to see something?”


Sarah held up a bottle of K-Y lubricant, a large bottle.

“We’ve got almost a week together without our housemates being around. It’s time you learned about anal sex!”

Sarah began by explaining how to prepare a lady for anal sex. It was like a kindergarten teacher trying to teach the ABC’s to a toddler.

The lady should be turned on and willing; she should be prepared by playing with her asshole, and inserting things (a finger, a small thin dildo, etc.). If it is her first time, you need to go slow and use lots of lubrication. Once the lady can accept a finger in her ass, insert two fingers and gradually increase the size of what goes into her ass, until her sphincter muscle is relaxed and she is ready and willing for you to insert your cock.

Sarah, in her eagerness to get right to some anal play, left out certain key points that an anal virgin like me should know; even when the lady is relaxed, if it is here first time, her asshole will likely shut closed when you try and insert your cock. Anal insertion requires the guy to push the head of his cock against her hole, while the lady pushes back. When the head of your cock gets into her ass, you need to go slow and use plenty of lubrication. While you are slowly inching your cock into her ass, her sphincter muscle will close and clamp down on your cock, which is not a good feeling. Finally, once you are into her ass, you need to go slow for a while, even with experienced ladies, as there may be some initial pain and/or discomfort.

Sarah liked doggie while being fucked in the ass, but when it was time for her to cum, she greatly preferred to be on her back with her legs bent up and a cock in her ass, so she could rub her clit and make herself cum. A lady could also lie on her side with her legs bent, start out lying on her back, bent over something (like a chair or table or kitchen counter), or sit on top of the guy and control the depth of his cock and the speed of his insertion.

Whatever the position, it should be the lady’s choice.

Sarah preferred no condom, but that should be the guy’s choice.

Anal wasn’t something that should be done all the time; once a week for some women may be just fine. For others, it might be once a month or a longer period of time. Let the lady decide, it’s her ass that has to take your cock.

Anal can be a very pleasant experience and both partners may reach new levels of passion. Both must keep in mind that too much, too fast and too hard, may hurt or cause injury.

Sarah then told me her “golden rule” of anal sex that she was to repeat many times over the years.

“Too much lubrication is never enough.”

Having a naked lady straddling you on a chair, sticking her tongue down your throat, while at the same time explaining the procedures and wonders of anal sex, and how much she likes it, has a way of making a guy very hard.

I had greatly enjoyed the intensity and pleasure of my previous orgasm, and, as usual, I’d gone soft afterwards. Now I was hard again, with my swollen shaft rising between Sarah’s legs.

We kissed for a few minutes and I licked and sucked on her nipples, eliciting low, sensual moans from Sarah for my efforts.

Sarah laid back a little so I could play with her nipples, pinching pulling and tweaking them, the way she liked it.

She stroked my cock with both hands, looking at it while she stroked, and making drops of pre-cum emerge from the tip and run down over her fingers.

She kissed me long and hard again.

“Put your finger in my ass!” she directed as she unlocked her lips from mine.

I reached behind her and rubbed the tip of my finger on her asshole. There was a wonderful moment of pleasure as Sarah’s mouth opened and she loudly moaned.

“God, that feels good!” she moaned as she kissed me some more.

I inserted the tip of my finger.

“Uuuunnnnngggghhhhhh!” was her grateful response.

I slid my finger in up to the knuckle.

Sarah pulled me close, buried her head on my shoulder and made noises that I had not heard before.

I had learned something new that moment: inserting a finger into a lady’s asshole can cause her go limp with pleasure and make her want to fuck your brains out.

Better yet, the more I slid my finger in and out of her ass, the hotter and more turned Sarah became.

We could have stayed right in the chair, me fingering Sarah’s ass, and Sarah straddling my lap, leaning into me and enjoying the feeling, moaning softly into my ear.

But education and experience were on her agenda, and Sarah was turned on and in need of some attention.

Sarah grabbed my arm as she moved off of my lap and led me to her bed.

I removed my shirt and lay on my back, my manhood pointing up at the ceiling.

Sarah climbed on top of me and while holding my shaft on one hand, positioned the head at her wet slit and slid my cock into her love hole. She put the palms of her hands on my chest and rode my cock for the next ten minutes.

“Let me do all the work!” she instructed.

“Fuck that feels good!”

“You have a great cock!”

Sarah turned around with her back facing me and placing her hands on my legs just below my knees, she rode me again, this time letting me see my cock being swallowed by her cunt.

Clearly in control of our lovemaking at this point, Sarah moved off my cock and positioned herself on her hands and knees.

“Fuck me doggie!”

Doggie is a wonderful position. I love the look of a woman’s back, hips and ass. I can hold onto her hips to get the leverage I need to slam my cock into her slit and I can reach around and play with her clit or nipples. I also can grab a clump of hair and pull her head back, riding her; and, I can lean forward and whisper dirty things in her ear.

“Put your finger in my ass!” Sarah directed.

I learned that afternoon that it’s easier to put your thumb in a lady’s ass while fucking her doggie, than to contort one’s hand to get a finger in. A thumb is also thicker.

Length is not important. The pleasure nerves in a woman asshole are only about two inches inside her hole. In anal, girth trumps length for pleasure, but length, absent great girth, is easier to insert.

Holding Sarah’s hair, listening to her telling me to fuck her harder and faster and desperately trying to control my own need to cum, I slid my thumb into Sarah’s ass and listened to her moans of pleasure.

“Oh yeah!”

“Fuck, yes!”

“Do both faster!”

I drove my thumb into her asshole, while I slammed my cock into her love hole. The reaction was wonderful. Sarah looked back at me with trembling lips, and a slight smile, nodding her approval.

Sarah enjoyed the double penetration for a few more minutes and then fell forward and rolled over.

“It’s time for you to lose your virginity!”

She opened the spout on the K-Y bottle and dribbled lube all over my hard cock, rubbing it and down the shaft. She handed the bottle to me, got on her hands and knees and directed me to pour lube on her asshole.

I did, and it ran down her hole and down the side of her pussy lips, to the inside of her thigh.

“You know what to do. Just go slow, but push.”

Her small, cute, puckered asshole was about to meet a big, thick hard cock.

I was nervous and apprehensive, but inched up behind her, holding my oily shaft in the palm of my hand.

I quickly learned another thing about anal sex. When she’s on her hands and knees, her asshole is higher than her love hole!

Kneeling behind her, I am at just the right height to be able to slide my cock into her pussy. Now I had to find a way to raise myself up a few inches to get level with her asshole.

“This can be done,” I thought to myself.

A combination of Sarah putting her head down on the pillow rather than staying on her extended arms, and my getting up on one knee, and I was able to place the tip of my cock on her closed hole.

Anal sex is not as easy as it appears to be.

Given, I had a larger cock than most guys and Sarah was looser and more relaxed than most ladies might be. Still, I pushed hard and Sarah pushed back, but my swollen head was not making any headway.

“Push harder!” Sarah said calmly.

I did, and slowly, the head of my cock slid into Sarah’s ass. When it did, Sarah barked out orders.


“Put more oil on your cock!”

“Go slow!”

“Push some more!”

I dribbled more lube on my shaft and up at her asshole and pushed another half inch of stiff cock into Sarah’s ass.


“Put more lube on your cock!”

Each time we made some progress, we stopped and lubed. Eventually, my entire shaft was in Sarah’s ass.

“Now, slide your cock out a little, slowly, and then slide it back in!”

Still a little apprehensive, I followed her directions, not wanting to hurt her.

After several minutes, however, I was sliding my cock almost all the way out and then all the way in, and I could begin to feel Sarah’s sphincter relaxing around my shaft.

“You can go faster!” she told me.

Finally, after about a half hour of slow, steady effort, I was fucking Sarah in the ass for the first time. My first time!

Slowly, Sarah began to moan and tell me that it felt good.

Her asshole was tight, and her muscle gripped my dick hard.

Sarah was rubbing her clit and yelling out instructions between her moans of pleasure.



“Fuck me in the ass!”

She rubbed her clit furiously as I slid my cock into her hole as fast as I could. Sarah’s moans and noises had now combined into one long, deep, low moan.

“Fuck yes!”

“Fuck yes!”

Without alerting me, Sarah suddenly moved forward, causing my cock to slip out of her ass.

My first thought was that I had hurt her. But before I could say anything, she rolled onto her back and bent her legs back, her knees up by her ears.

I stared in amazement at the gaping hole that was once her puckered asshole.

“Fuck me in the ass!” she yelled.

While I had been startled by the size of her gaping asshole, Sarah’s command brought me back to the moment.

My cock slid into her ass easily this time, and there were no worries about my having to get up on one knee. I could fuck her ass now, just as I could fuck her pussy.

“Go faster!” Sarah commanded, now out of breath.

“Fuck! Faster! Harder!

“Fuck my ass!”

“Give me your cock!”

Sarah rubbed her pussy and clit in a fast, circular motion.

“Oh, God! Oh God!”

“I’m going to cum! Don’t stop!”

“Faster! Faster! Fuck my ass!”

Sarah had that look of pain on her face, a grimace with her teeth clenched. It was an, “I’m almost there look” and “I just need a little more,” look.

I was bracing myself with my arms and doing the best that I could to slide my cock into her asshole as fast and as hard as I could.

Sweat was dripping off my nose onto her tits and I, too, was out of breath. 

“Oh, God! Oh, God! I’m going to cum. I’m going to cum!” She yelled, running her words together in one long sentence.

Sarah worked her fingers relentlessly all over her wet clit. She rammed her fingers into her pussy, causing pussy juice to fly out in all directions. She hammered and pounded her pussy with her hand, but it was not pain she was feeling.

She yelled at me to fuck her ass.

Then it came. Anal fucking is hard work. But seeing Sarah’s orgasm, hearing the sounds she was making and knowing that I helped to give her this pleasure that raced through every fiber of her body, made it all worthwhile.

Her body contorted and shook so much that I had a hard time keeping my cock in her ass. And her orgasm lasted far longer than any I had seen before.

There were no words, only a continuous “Uuuuunnnnngggghhh”, as she violently arched her back and neck, her eyes rolled back into her head and saliva ran from the corners of her mouth.

When she finally settled down, she whispered, out of breath, that I should not stop, that I should continue to slowly fuck her ass.

I did as I was asked, and Sarah just laid there, pulling on her nipples and moaning.

She reached down with her hands and slowly rubbed her pussy.

"I’m going to cum again,” she said, this time with a lot less urgency. A statement, rather than a cry.

“I’m going to cum again.”

She rubbed both hands over her sopping wet pussy and stared at me with half-closed, sensuous, erotic, eyes.

“You’re going to make me cum again,” she said, almost crying.

Her head and back arched back again, there was a noticeable ripple that ran through down her stomach to her pussy, and she moaned, long and low.

“Yes! Yes! Yes!” she cried, as her body jerked and shook.

And then there was silence.

Sarah lay there, breathing heavy, moaning softly, her eyes closed. Beads of sweat on her forehead and chest, and my hard cock still in her ass.

I started to slide my cock out of her hole.

“No. Don’t take your cock out yet.”

She lay like that for minutes, enjoying the aftermath of her second orgasm, while I left my cock in her ass, slowly sliding it in and out.

Sarah reached forward with her arm and placed her palm of my chest, a signal to remove my cock.

When I did, I was again amazed at the size of the opening that was her asshole. Then suddenly, like her asshole was winking at me, it closed. In a way, I was relieved that her hole was okay.

“Cum on me! Cum all over me!" she whimpered.

I stroke my lubed cock while Sarah encouraged me to cum for her.

As I reached the point of no return, I was overcome by the intensity of the feeling. I know I yelled, I think several times. I know that I shot long ribbons of cum and I know that the feeling was intensely pleasurable.

Long strips of cum ran from Sarah’s stomach, across her tits, on her face and up into her hair. Gobs of cum also ran down the head board of her bed and I had even hit the wall over the headboard.

I collapsed next to Sarah. She pulled a bed sheet up to her chin. I snuggled in close to her body. She said nothing. I said nothing. I could feel cum continuing to ooze out of my limp cock.

I had experienced my first anal sex and loved every minute of it.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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