Anal With Ashley free porn video

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Ashley and I wanted each other the very moment we met, but our friendship got in the way.


Right after I married Sharon, we moved into a large apartment complex and became good friends with our neighbors, Jim and Ashley.
Ashley was a hot brunette, had a great body, and wore her long hair up in a sexy ponytail most of the time. I was dying to grab that ponytail and kiss her, but because the four of us were such good friends, I didn’t dare jeopardize our friendship by doing something so forward.
The four of us got together every weekend at the large community swimming pool in the summer and would barbeque hotdogs and burgers for dinner. The whole time I would be having fantasies about Ashley. I wanted to get her into bed so badly that I had a boner all the time she was around. And her flirtatious smiles didn’t help. I got the impression that she also wanted me.
Jim and I were always talking about our sex lives. He’d tell me how good Ashley was in bed, and I’d tell him how good Sharon was in bed. He told me that Ashley wouldn’t let him cum in her mouth, and I’d tell him that Sharon loved it when I shot off in her mouth. That made him insanely jealous and confessed that he’d like to get a blowjob from Sharon.
Then I said, “Maybe we should think about wife-swapping for a night.”
“You think Sharon and Ashley would do that?”
“I don’t know. Why don’t you talk to Ashley and I’ll talk to Sharon?”
“Oh, I don’t know. Ashley will get pissed.”
“Why do you think that?”
“She’s just so strait-laced. She’d never agree.”
“Then I guess that’s that.”
“Yeah. But I know that Ashley wants to try anal sex.”
“Really!” My cock jumped to attention with the thought of fucking Ashley’s virgin ass.
“Yeah, but I don’t want to.”
“You don’t? Then tell her that I’d love to.”
“You want to have anal sex with Ashley?”
“Of course! I’ve never tried it before either.”
“Mmm. Do you think Sharon would suck me off?”
“I think she would. She loves giving head and swallowing everything.”
“Oh damn!” Jim said as he rubbed the boner that had grown in his pants.
- - - - -
The following weekend, we planned to get together at our apartment. Sharon was still in the shower when Ashley knocked on our door.
“Hey, gorgeous! Where’s Jim?”
“He’s running late. Can I come in?”
“Sure!” I said as Ashley slipped in.
I saw my opportunity, so I grabbed Ashley around the waist and gave her a French kiss that she’d never forget. And to my pleasant surprise, she kissed me back. I grabbed her ponytail in one hand, pulled her head back, and kissed her on the neck and shoulders.
“Mmm, Bill. Jim said that you want to have anal sex with me,” she whispered.
“I do,” I replied as I pushed my leg between hers so she could feel my hard-on.
“Maybe I can talk to Sharon about wife-swapping.”
"That would be great because I really want to get you into bed."
Just then Jim knocked on the door and ended my arousing discussion with Ashley.
“Hey, Jim! Come in. Sharon is running late.”
“That’s okay. I need to talk to you anyway.”
“Okay. Why don’t we step outside?”
Once outside, I asked, “What’s up?”
“Ashley wants you to fuck her ass,” Jim whispered.
Trying to be surprised, I responded, “You’re joking!”
“Nope. But she’ll agree to only that. Nothing else.”
“I’m good with that,” I said, although I planned a lot more than anal sex with Ashley. I would have her in bed all night and would have plenty of time to do a lot with her.
- - - - -
Jim pulled me aside later and whispered, “Guess what? Ashley talked to Sharon and she agreed to wife-swapping if, IF we only do oral sex.”
“Well, you and I know that Ashley wants more than that.”
“I know. But now we have a go-ahead to wife-swap tonight.”
“Tonight?”
“Yep.”
“Wow! They’re eager to do this!”
“Yep.”
- - - - -
Three hours later, I had Ashley in bed and was pushing my nine-inch cock into her ass. I had it about halfway in when she looked back at me and wanted to stop. But I continued.
She groaned loudly as I pushed it all the way in.
“Bill. Pull it out. It hurts.”
“Shh. Just relax and enjoy it.”
So, she laid down and screamed as I continued to thrust into her tight ass.
Ashley’s virgin ass felt much better than I’d ever dreamed it would. And watching her ponytail swing around as I thrust into her, was very arousing. I knew that I would cum soon, so I began to increase my pace, slamming my stomach against Ashley’s ass with each thrust.
After several minutes, Ashley settled down and seemed to like it and was enjoying my hard cock in her ass. She reached back and spread her ass cheeks. That’s when I rammed hard into her and let my cock explode, spurting hard shots of cum into her ass.
“Oh god. I can feel you cumming! Your cock is jerking and I can feel your sperm shooting into me.”
“Does it feel good?”
“Yes! It feels better than I thought it would. I want to do this all night.”
“I want a blowjob, Ashley.”
“We didn’t agree to that, Bill. Just anal sex.”
“I know, but no one but you and I will know. So, I’ll go wash up and you can suck me off.”
“Well, okay, but you can not cum in my mouth. I’ve never done that and don’t want to!”
“Okay,” I replied, but fully intended to shoot off in Ashley’s mouth; even in her throat if she could take it.
- - - - -
When I returned to bed, Ashley took her turn in the bathroom. When she came out, she said, “Wow, Bill. You must have cum a quart of sperm in my ass! It just kept running out!”
“Well, that’s because your tight ass felt so good.”
Ashley crawled on top of me as our nude bodies touched. We kissed and fondled for a few minutes until my cock was hard and sticking up between her legs.
“Mmm. I wish you could put that inside me.”
“Then why don’t I?”
“No! I could get pregnant. Besides, we didn’t agree to that.”
Then I quickly rolled her over, straddled her chest, and said, “We didn’t agree to oral sex either, but I’m about to fuck your mouth.” Then I grabbed her wrists and pinned them to the bed.
“Okay, but remember what I said. Do not cum in my mouth.”
“I remember,” I said as Ashley opened her mouth and I pushed my cock almost down her throat.
“Agh!” she gagged and turned her head so that my cock slipped out. “Don’t do that, Bill. I’ll choke on that big thing!”
“That’s what a good blowjob entails…taking it down your throat until I shoot off. Then my cum will go straight into your stomach.”
“No way! I won’t do that.”
“Oh, come on. Just try it. When you gag it squeezes my cock and feels so good!” I said as I pushed my cock back into Ashley’s mouth. I intended to fuck her virgin throat whether she was expecting it or not.
I fucked her mouth for a few wonderful minutes, then as I leaned forward, I felt her throat open. That was my chance! So, I pushed my entire nine inches down Ashley’s throat until her nose was pressing against my stomach.
“Agh! Agh! Agh!” she gagged repeatedly and struggled to push me away.
But by then I was too close. Two more of her gags and my cock started to spurt cum into her stomach. She coughed and gagged, but with my stomach pressing on her face, she couldn’t get away. She had to take my cum until my balls were drained.
When I pulled out, Ashley coughed several times and said, “You son-of-a-bitch! You came in my mouth! AND you almost choked me in the process!”
“No. I came in your throat and my cum went straight into your stomach. Surely you felt it going down!”
“Well, I almost choked.”
“No. You just thought you were going to choke. But you didn’t, did you?”
“Well. No.”
“Good. Now come here and cuddle with me.”
“Why don’t we sixty-nine first. I want to have an orgasm with your cock in my mouth.”
“Mmm! that’s a wonderful idea,” I replied as Ashley turned around and I got into position over her. I knew that I probably couldn’t cum again. I’d cum twice already. But when I felt Ashley suck my flaccid cock into her warm mouth, I thought, “Maybe I can cum again! And if I do, it’s going to be in her mouth.”
I pushed my face between her legs and went to work on her clit. She moaned and thrust her crotch up to give me full access.
And within a few minutes, Ashley groaned and clamped her legs on my head as an intense orgasm ravished her body. As it continued, her legs began to quiver, and she was sucking my cock down her throat. Ashley was having a massive orgasm and was doing everything she could to make it last.
And her tight throat engulfing my cock was affecting that she was not prepared for. Just as my cock began to spurt, Ashley quickly tried to push it from her mouth. Then to my surprise, she stopped and kept sucking to get every drop of cum that my overworked balls could provide. When they were drained, she immediately swallowed everything, then sucked my cock for more.
We were both exhausted, so we cuddled and went to sleep. Ashley had taken my cock down her throat and I’d filled her tummy with cum. And I’d fucked her ass and she liked it, even though it was painful at first. The only thing remaining was for me to fuck her and I had a plan for that in the morning.
- - - - -
The next morning, I woke up, got the K-Y jelly, and put my plan into action.
“Mmm! Do you want my ass again?” Ashley whispered sleepily.
“Once is not enough, Ashley,” I replied as I smeared some K-Y on her butt hole and all the way down to her clit, where I stopped to rub it.
“Mmm, Bill. You’re getting me aroused.”
“That’s the idea,” I said as I began to rack my cock up and down from her butt to her clit. As I continued, Ashley began to moan and arch her back. It was time.
So, I put my arm around her, grabbed one of her ample breasts, and rammed my cock into her pussy.
“Whoa! Bill! Not there! You’re supposed to be in my ass!”
“I want to fuck you, Ashley. I always have.”
“No, Bill. We’re not supposed to!”
“Shh. Just enjoy my cock,” I whispered in her ear as I began to fuck her harder.
“Mmm, Bill. This is not right.”
“You love my cock inside you, don’t you Ashley?”
She finally gave in and said, “Yes. You feel so good inside me. I’ve had fantasies about you fucking me.”
“I thought so,” I whispered in her ear. “I just knew you’d be a good fuck.”
“Oh god. I’m going to cum!” Ashley whispered as she pushed back as I thrust into her.
Ashley had another intense orgasm, making her legs quiver and making her moan loudly. When it was over, she said, “Let me turn over so I can wrap my legs around you. That’s what I’ve dreamed about.”
For the next hour, I fucked gorgeous Ashley with her legs wrapped tightly around my waist. She had four intense orgasms ravish her body and was about to collapse when I began to shoot off.
“Mmm. You’re cumming inside me,” she whispered, then dropped her legs to the bed. “I’ve never been fucked so good before, Bill. You are amazing.”
Ashley was almost asleep before I finished cumming. So, while I was still hard, I continued to fuck her sleeping body. But I eventually rolled beside her and went to sleep as well.
- - - - -
Ashley and I began an affair that lasts until today. Once or twice a month, on a Saturday morning, we check into a small motel somewhere and fuck our brains out. She has come to love deep throat and loves to feel my sperm surging down her gullet. And we always end our meeting with a good session of anal sex.

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**This is my first story so feedback would be nice please. ** Some Information About the Characters: Juan- I was in 9th grade and I was 15 at the time. I was 5' 6" and had brown hair. My eyes were brown. I had a nice tan because I was part Hispanic. I wasn't build but I wasn't fat either. I was pretty much an average teenager. My penis was about 7 inches. Ashley Mathias- She was my English teacher. I don't know how long she had been teaching, but I knew she was probably in her...

3 years ago
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My Niece Jehna and her friend Ashley

This story is about my niece Jehna and one of her friends Ashley they are both 18 it came about when I was visiting my sisterr while I was looking for work and I had to stay with my sister as I lived in GA and she lived in FL. My sister had just moved into a 1 bedroom apt and it was fine with me on the sofa and the arrangement was working until her daughter Jehna who just turned 18 5’7 about 120lbs and nice 36c breasts broke up with her boyfriend and needed a place to stay so she also moved in...

Incest
4 years ago
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Saving Lindy Ashley

CHAPTER 1 Bo Short (Bo being short for Bob which was short for Robert) went into the bar. He’d been told to meet Charlie and Eddie Hooker there because a well-paying job was on offer. The brother’s Sergeant at Arms, a beefy guy called Herb, frisked Bo and the guy said through broken teeth, ‘Go to them. They’re behind me.’ The bar was half-full of guys who looked like crims and all the women looked like sluts, as women tend to do when they slouch in bars or show their panties sitting on...

3 years ago
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The Corseting of Ashley

The Corseting of Ashley By Ashley Another True Memoir Exploits, Humiliations, and Embarrassing Moments of Ashley It was a beautiful, sunny day in the nation's capital. For a road warrior, which is what we road weary types like to call ourselves, this was the beginning of a glorious mini- vacation. One of the benefits of flying very frequently is the chance, on occasion, to fly the significant other to where you are instead of making the usual trip home. Waking up in the...

3 years ago
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My cousin Ashley

Amazing how some things happen so overwhelmingly fast yet you can’t really forget a second of that brief moment, to this day, I haven’t had a thought that can override that of the first time me and my cousin Ash (Ashley) got to know just how much fun can two cousins have on a stormy Florida day. Well, it all started one morning of autumn, it was a Sunday, I recall; My cousin’s Teri, Ash and Alec were to visit us and stay until dinner time; Ash was sprung 18, same as me, and we...

4 years ago
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Building a CAP Based FutureChapter 9 Forever Ashley

My three morning classes were quiet. The teachers seemed a bit distracted, and the students just wanted to whisper about the President's announcement. Most students were speculating on the special show to be on television in two weeks. No one seemed to have a clear idea of what to expect. I stayed silent as the others continued to gossip. It was not due to a lack of interest in the possibilities. My issue was that I wanted to have facts rather than rumor, and other than Jessica, there was...

3 years ago
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Enter Ashley

Her body lay on the floor coated with body fluids, littered with numerous condoms, welts, and open wounds. Standing over her I listened to the music of her raspy shallow breathing, pain-filled groans, and the wet slapping sound her left hand made as it jerked involuntarily in a puddle of filth. Ashley's long brown hair now sticky, slimy, and knotted was pasted against her neck, face, scalp, and the floor. The horrible stench only added to the beauty of this scene, but could not be recorded...

2 years ago
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The three Ashleys

I have been working with the Ashley’s for a while. There are three of them, all sexy and very hot in their own way, and all about the same age, 25. I will call them by their biggest feature which sets them apart. There is Blond Ashley, very hot with dirty blond hair. Medium sized breasts and a great ass. Tall Ashley is a brunette and over 6 foot tall, and when she wears heals she is often taller that I am. Beautiful dark eyes and a quick smile. She has a nice rack that stand proud and her...

3 years ago
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Manali Ko Naye Dost Se Chudwaya 8211 Part I

Manali bohut cute ladki hai,sab uspe fida the.Wo bohut slim aur sexy bhi hai,par wo bohut conservative thi.usne mere sath bhi kabhi sex,yeha tak kiss bhi nahin kiya.Mai usse bohut pyar karta tha,mai bhi bohut conservative tha.mai kabhi usko kisi or ke sath sex karwane ki baat kabhi sapno mein bhi soch nehin sak ta tha.yeh tak usse sex karne ki khayal kabhi mere demag mein aaya nehin.Humare bech kabhi sex ko leke baat tak bhi nahin hoti thi.Par ekdin jab mai cricket practice se ghar wapas aa...

3 years ago
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Anal With Ahsan

By : Kalsoom Hi readers, this is Kalsoom again with many thanks to the readers for their richly response to my previous stories. Those who want to read the previous ones, may contact me at this story is to narrate my further experiences with Ahsan whom I kept meeting at Sameena’s house. In the beginning I feared about the pregnancy but Sameena and Ahsan were experts in this field so they kept providing me contraceptives and I was safe from any kind of fear. But this use of contraceptives and...

2 years ago
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Anal Fisting Guide

HOW TO FIST OR PLAY LARGE, ANALLYI get asked quite often how to “stretch” or train oneself to take larger toys and fists. I normally say the boiled down, simplified version of… “It is just a matter of relaxation, muscle control, plenty of lube, along with time and determination, and caution to do it right, at your body’s own pace.” This is the unabridged and detailed description that I have compiled from several sources over the years, so that I could have it in one place.Putting things in your...

1 year ago
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Anal Vids

Anal Vids are arguably one of the main reasons the Internet was invented. I know that sounds like some butthole-loving pervert talk, but hear me out. Even though people don’t like to talk about it in polite company, dirty movies have built and shaped the Internet. Buttfucking used to be considered more of a kink than a traditional sex act, but these days it’s become pretty normalized for your girlfriend to ask for a finger in the pooper when she’s drunk. Through the magic of the global web,...

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4 years ago
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Anal Sex with your Friend Always be Clear

"I don't know about this honey. I mean I know you have always been keen on anal sex.""And I know you think Faith is sexy, but do you really think she would be up for a threesome with us? I mean just cos you have always perved over her body and particularly her tight muscular ass. And I know I told you, in confidence, about my suspicions that there might be a kinky side to her.""But do you really want me to call her and ask if she would be up for anal fuck with you, and tell her that you want me...

2 years ago
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Anal Sex With My Wife

This is my first sex story on ISS but, i have read a lot of ISS and i find it very good collection on this site. I am 30 year of age and my wife age is 28 and we got married two year back. First of all i will describe myself and my wife. I am skiny guy with 5.4 feet and my wife is of perfect figure 32, 27, 32 with 5.2 feet. She has got very good boob and structure of ass is awesome. When she wear tight night dress i always dream to stick inside her ass We got married and we had a lot of naught...

4 years ago
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Anal Beth

I had known Beth for only a few months. She was pretty by anyone’s standards, with nice legs, a firm behind, and somewhat small breasts (I believe bite-sized is the term they are commonly called) with bigger than average nipples. We didn’t make it until our fourth or fifth date, and I can’t say that the sex was spectacular. Don’t get me wrong, it was good, but until we went to a hunting lodge one weekend with Joan and Bill, two close friends, our sexual adventures were quite ordinary. We all...

4 years ago
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Anal Threesome Part Three

They were in Claire's room, or rather what used to be her room. Now, it was slept in by all of them nearly every night, and the huge King sized bed was frequently put to the test with regards to the durability of it's bed springs. Kath lay on her side, wearing nothing but a pair of white-ankle length socks, propped up on her left elbow whilst her right arm draped elegantly along the contours of her right side. Her body was small, slim and firm, round little titties and a perfectly sculpted...

1 year ago
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Anal Mom

AnalMom! Let me give you two simple words that will put all kinds of dirty thoughts into your head immediately: Anal Mom. Goddamn, the two concepts go together like carrots and peas or big shafts and tight holes. Lead with that, and you’re going to have to really fuck things up to lose your audience. Anal sex and MILFs are just two of the most popular subgenres of smut, so combining the two should be a recipe for almost certain success. A site with the simple motto “Moms Do Anal On Video” is...

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3 years ago
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Anal Pleasure for Him and Her

It started years ago, when I was in my early teens. One night I was lying on my side running my hands over my ass and in the crack and over my anus. I always was repulsed by the thought of male anal sex or even exploration that could lead to it, but curiosity got the best of me. I had taken a shower so my anus was clean, and I started prodding it with my finger. I had heard of rim jobs and a friend of mine said his girlfriend gave him one once and said it was awesome. But as my anus was dry...

3 years ago
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Anal Beth

I had known Beth for only a few months. She was pretty by anyone's standards, with nice legs, a firm behind, and somewhat small breasts (I believe bite-sized is the term they are commonly called) with bigger than average nipples. We didn't make it until our fourth or fifth date, and I can't say that the sex was spectacular. Don't get me wrong, it was good, but until we went to a hunting lodge one weekend with Joan and Bill, two close friends, our sexual adventures were quite ordinary.We all...

4 years ago
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Anal With My Best Friends Girl

Why was my best friend telling me this? God, why couldn't he keep his mouth shut?I sat back against the hood of his car and sipped on a beer. On Javier's front lawn was a grill and flames were shooting up from the charcoal we'd just lit. We were both nineteen. I don't remember how the topic got started, but the sentence I've committed to memory was:"She really wants me to fuck her in the ass. Last night was like the hundredth time she'd asked me. She's been bugging me a lot about it lately."...

3 years ago
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Anal Addict

My brother, Brian, is 4 years older than me, and if I can remember right this happened one Saturday morning. I got up around 9 and as far as I knew, I was home alone. I didn't mind walking around in my little halter top night shirt and panties. By the way I am 5' 2" 90 pounds, short reddish brown hair and green eyes. I've got a small chest but I am happy with my looks. Anyway, I thought my brother was at football practice, my mom at work and my dad was gone for the weekend. I went down the...

2 years ago
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Anal Week

Anal WeekKathryn could feel her period was approaching. She tingled with excitement because she knew what that meant. It meant her man would have no choice in the matter he would have to fuck her arse. She cheekily rang Brad and declared her "friend" had arrived and with feigned sadness said her cunt was out of action for a few days. Brad's sadness was equally insincere. "You know what that means? You can only fuck me me up my arse!" she intoned. Brad grinned as he said "well you know I can't...

3 years ago
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Anal Sex with my Girlfriends Anorexic Grandd

I had been dating my girlfriend for a decade. We met when I was 40 and she was 55. A notable age difference but we had had an instant attraction at first glance. She was a well-kept woman of Hispanic descent with a gorgeous face with full, plush lips, still pert, uplifting tits and an ass that you could bounce a quarter off of. On our very first date I had sodomized her tight, well-oiled asshole for hours thanks to a little blue pill. I have been gaping that elastic hole daily to the size of a...

2 years ago
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Anal sex and breaking up

N. hadn’t just broken my hymen… he had breached a dam…. and released another aspect of my sexuality.I took every opportunity to fuck him and opportunities were abundant. He had taken a leave of absence from work prior to moving to Australia…and I was just waiting for university to start to move to my parents in Brussels. We fucked everyday….and several times a day. We were literally going through the Kamasutra…experiencing new positions…inventing some of our own. We fucked everywhere…in his...

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