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Category: Anal Sex
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I love my wife, and I would never cheat on her. Usually, when someone makes such a bold statement, the word ‘but’ follows and we hear how this is not always the case. I suppose my story is no different. Kelly and I have been together since high school. I thought back then it was a love that would always last. Ten years later, it was still the case. Kelly had been out of town for three weeks now, acting as a consultant for a company in California.

Kelly had never been away from me this long before, and I was still trying to get used to the idea of her being gone for long periods of time while she forayed into the world of consulting to see if that is what she wanted to do.

Kelly was my wife and my life, but here it was a Saturday night and I was online with Claire, who I met in a chat room last week. We had been instant messaging for awhile tonight. The mysteriousness on the internet and the sexiness of Claire’s words usually get me turned on quickly, so I had already unzipped my pants to allow my penis to have access through my fly to open air, not letting it be constricted by my tight jeans. When we met last week, Claire and I began with brief chi chat on our lives, two lonely people with husbands and wives traveling. But soon things quickly progressed to topics of sex and what the other was interested in. We would describe what are fantasies were. Claire was describing one of hers to me now.

“I love anal, Jeff. My husband doesn’t know. In fact, I don’t know if he would go there. When he is gone on trips, I like to take my favorite tiny vibrator and tease my ass. Usually right at the opening, exciting my nerves, causing my hairs to stand on end. Then I allow the vibrator in, rotating the vibrator to make sure the vibrating tip does circles inside me.”

“I once mentioned anal sex to my wife. She was not up for that either. A couple of times I have tried slipping a finger in her ass. She has squirmed with what I think is pleasure but quickly taps me on the arm to tell me no.”

This talk had my penis quite erect and I looked down at it poking through my boxers and out the fly in my jeans. There was also a large bubble of pre cum forming at the head.

Claire was now describing her dream anal sex scenario. As I read her fantasy as she typed, I gave my dick a squeeze and watched as more precum pulsed out of my tip and began to leak down my shaft. I used my fingers to stop the cum in its path and used it to lube the entire helmet of my member. I twirled my sticky fingers around, stroking the underside of my cock to make my penis even more erect and sensitive. Once my precum was spread around, I applied my entire fist and began to stroke. As I stroked from base to head, more precum managed to escape. I ran my palm over it, lubing myself further and began stroking myself furiously while I read Claire’s words on having a penis pumping inside her ass. As Claire described being slapped as she tightened her ass around her mans cock to man him cum, I shot a load of my own onto the monitor. I cleaned up with a kleenex and described to Claire how her story had turned me on. As I explained to her what I had done, Claire had an orgasm of her own. We said good night and said we would have to share more in the future.

I would talk to Claire two or three times a week. Usually late at night when the loneliness hit the most for both of us. Claire would never come up during my nightly talks with Kelly when she asked what I was up to. Instead we would talk on how much we missed each other. Kelly and I would be having an anniversary next week.

“The job won’t be done until the day after sweetie. I’ll be back Friday.”

“You know what this means, I’ll have to cancel reservations at Oranges”

“Oranges, oh I love Oranges.”

“I love you.”

“I love you too, Jeff.”

We hung up. I was sad that Kelly wouldn’t be back in time for our anniversary. However, I was excited that she would be back soon.

On Monday, before Kelly’s return, I found Claire online and told her the great news.

“My wife is coming back this week.”

“Making it back in for the anniversary then?”

“No, she’ll still miss that. Which reminds me I’ll have to cancel reservations for Oranges, that’s her favorite restaurant.”

“We have an Oranges here, they have the best chicken breast.”

“That’s what my wife always gets at Oranges. I didn’t know Oranges was a chain.”

It was here that we realized that we were both in the same town. Claire and I had grown close; it seemed ridiculous to waste such good reservations and asked Claire to meet me at Oranges on Thursday night. We had provided the other with such good company, dinner would not be a goodbye because Kelly was coming home, but a dinner to celebrate a new friendship that we would have to continue whenever the other’s spouse was on travel. Claire described herself so I would recognize her and we agreed to meet at eight.

Thursday arrived. I took a nice long shower and dressed in a nice black collared shirt and khaki slacks and went off early to Oranges. I grabbed a seat and told the restaurant hostess my wife would be joining me shortly.

Ten minutes later I saw the hostess walking towards my table with a stunning, tall, red head behind her. I stood and gave her a hug as we met and the hostess helped her to her seat.

“I’ll be back with another glass of wine and the meal will be ready shortly,” the hostess said as she left to grab a wineglass.

“I hope you don’t mind if I ordered for us ahead of time. I hear they have the best chicken.”

“You heard huh,” Claire said with a laugh.

The hostess returned with a glass for Claire and poured her a healthy amount from the bottle tableside. Shortly the food came. Both the chicken breast and the steak were good. We couldn’t help but share our meals. We topped off the evening with conversation over a slice of apple pie for two. Throughout the evening, Claire and I expanded on our lives, what we hadn’t already known based on our internet chats. Over pie, our talk again diverted towards thoughts of sex. I told Claire about my first time with Kelly in high school occurring in a faculty office on the weekend. Claire was interested to know more, as well as to share more of her own stories. After settling the check, I was led by Claire to the hotel bar across the street for more drinks. Claire shared her first time with her husband. During her story I couldn’t help but stare at her blue eyes and imagine being her husband in her story. When Claire finished the climax of her story, she stared back at me.

Neither one of us spoke for quite awhile, just staring at each other.

“I have a room upstairs,” Claire spoke first.

“A night of more firsts.”

Claire led me to her room on the eighth floor. She swiped the card to gain access. As soon as we entered I grabbed Claire’s hand and walked her over to the bed. I sat on the edge of the bed while Claire stood over me. I reached behind her and unzipped her dark blue dress. My hands slid up her arms and grabbed the straps and slid them off her shoulders. As the dress slid off Claire, she stepped out of it, standing in her bra and panties, she then pushed me so my feet were on the floor but my back sprawled on the bed. She leaned over and we shared our first kiss. Her lips were so moist. She tasted so sweet. I did not get to taste her much more. Her head slid down, her hands running down my chest, over my hardening crotch, down my legs, she untied my shoes and took them of. She slowly took of my socks and while kneeling at my feet, took off her heels as well. Her hands followed a path back up my legs, traced a path over my zipper and began to work on my belt buckle. She unbuckled and unzipped my pants and pulled them down my ankles and off my feet. She again rose, allowing her hands to follow a path up my legs, over my boxers, across my erection, on up to my chest where she leaned over me again allowing our lips to touch.

Our kiss was longer this time, allowing our tongues to meet. Her long red hair fell over my face as my tongue danced with hers. My hands went through her hair down her back and unhooked the strap of her bra. Her bra fell to my chest. I continued to run my hands down her back over her ass and down her legs to my knees where they straddled my hips. Claire pushed back and let the bra straps slip over her elbows and threw it to the floor to join her dress and my pants. As our kiss ended, I was now free to see her breasts hanging over me. She had beautiful tits. I ran my hands back up her legs, over her waist, my fingers slightly over her back while my palms inched closer to her hanging breasts. I pressed my palms firmly as they pushed up her tits. I cupped my hands there as Claire leaned back and let out a sigh. Claire removed her knees from their place around my hips and stood up, grabbing my hands and pulling me up with her. As I stood, she grabbed my shirt around my waist and lifted it up over my head. We kissed again as she placed her hands over my chest. Her hands ran down my chest as mine ran down her back as we both tried to simultaneously take off the others underwear. Seeing the futility in trying to do so simultaneously, I let Claire hook my boxer strap with her thumbs and slide down my body as she pulled the boxers off my feet. She slowly and seductively slid back up, running her fingernails over my legs and thighs on her way back up. My fingers were now in her elastic and slowly pulled her black panties down, slowly revealing her trimmed patch of black pubic hair, sliding the material over her mound revealing her pussy lips. I slid the panties down her legs and off her feet. And returned, sliding my hand over her mound. As my fingers touched her clit on the way up her waist, she let out a yelp.

We kissed again as Claire pushed me back onto the bed. Our hands explored each other’s naked bodies. With my head near the headboard, Claire turned around and shoved her pussy into my face. I pulled her ass into me and put my nose in her pussy while my lips wrapped around her clit. Claire wrapped her hands around my erect cock and made long paths with her tongue up and down my dick. Pulling her butt further down on my face, my tongue traced a path past her clit down the crease of her pussy and continued on where I wanted to go and began to toy with the opening of her ass. As soon as my tongue found her anal entrance, Claire gave out a scream and thrust her ass further at me signaling me to proceed.

Claire began to deep throat my cock now, taking in my entire length as my tongue began to swirl all around her ass. I became bolder and ran my tongue into her opening. Twirling as I entered, I dove an inch into her ass. Claire began to stroke my cock faster, and I took this as a signal to thrust my tongue deeper and faster in her ass. My fingers also began to furiously rub her clit and explore her pussy walls as Claire’s nails teased my balls.

Claire removed her lips from my cock long enough to shout, “God, Jeff your tongue in my ass feels so good, fuck me now.”

Claire waddled to the edge of the bed, still on her hands and knees and thrust her ass in the air. I slid my legs out from under her and stroked my cock as I guided the tip over her clit to her pussy lips and slipped my engorged cock into her pussy. I began thrusting very wildly. Claire began moaning but then quickly shouted for me to stop.

“Check the drawer, Jeff. Fuck me now.”

“I opened the drawer to the night stand and pulled out some lubricant. I knew what Claire wanted. I applied a liberal amount to her asshole. I positioned my cock head on her ass and slowly pushed. Her ass was not going to easily take something of my size. I added more lube and slowly pushed until my cock slid inside of her. Without thrusting, I just pushed until my entire cock was in her knowing she could take my entire length before I began to fuck her. I felt as her ass was clenching around my cock. It felt so good to have my cock in such a tight space. I slowly began to rock my dick in and out of her. Claire leaned up, reaching her arms around to grab my back and slid them down to grasp my ass and helped me thrust deeper. Her hands were now signaling my speed, and she wanted me to pump her ass faster. I began to fuck her harder than I was her pussy. Her hands returned to the bed to grip. Her head fell to the sheets as she pushed her ass further onto my cock. Her other hand went to her pussy and began writhing away to bring herself to orgasm. I grabbed a hold of her waist to thrust her on my dick further. I even began to slap her ass. This sent her crazy as she moaned my name into the bed sheets. My hands went down her back and grabbed a hold of her red hair. I began to pull as my dick penetrated her ass. She began to slap her own ass as I pulled harder on her hair. Her red wig came off and I threw it to the ground and grabbed her natural blonde hair and pulled it over her back.

She began to breathe more sporadically. I let go of her hair, wrapped my arms around her waist to pull her onto my cock further, and then began to rub her clit as my cock moved in and out faster. I inserted a finger into her pussy and began to curl my finger inside her over her g-spot. She began to come. Her pussy walls collapsed on my finger and her ass convulsed over my cock. Her muscles clenched and her ass began to put lots of pressure on my dick. The contractions caused me to ejaculate. Hot bursts of my cum went deep into her ass. She was moaning and I was grunting as I thrusted my penis deeper as I continued to cum, releasing spurt after spurt. Her juices escaped her pussy and I felt them run down my leg. I slowed my pumps and my penis slid out of her ass. I inserted it into her pussy to collect her juices on my cock. I put a hand to my cock and brought the fingers to my tongue tasting her juices. As I collapsed on top of her, I let her taste my fingers as well. We spent the next few minutes tasting the juices from her pussy, my cock and her ass. I ran my juice-covered hands over her tits and through her gorgeous blonde hair.

When we were done tasting, we laid in each other’s arms in bliss.

“Happy anniversary, Jeff.”

“Happy anniversary, Kelly.”

“Thanks for following through with my fantasy.”

“You know I love you and will try anything with you. And you, anal sex, huh?”

“Well, Claire made it sound so fun.”

We fell asleep in each other’s arms and went home the next morning. I was glad to have Kelly home from work, but knew if she took another consulting job, I would not need to worry. Ours was a love to last forever.

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