My First Anal free porn video

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My sexual appetite has always been strong. Being bisexual, I easily transition from men to women and back again. Years ago, I had an incredibly adventurous sexual relationship with an equally adventurous woman. She was game for most anything I wanted. We explored anal, bondage, sex toys, and even threesomes, both MMF and MFF (another story). However, my sexual desires were stronger than hers as I have a strong desire for homosexual sex.

I had an apartment of my own, but slept most nights at her place. One night after sex I wanted more, but she was too tired. I decided I would find some hard dick. At that time in my life I didn't have a "go to" fuck buddy and took my chances at adult bookstores, known glory holes, or popular gay cruising spots. The pussy was great, but I hadn't had raw mano y mano sex in some time. We had our usual apres sex cigarette and I told her I was going to stay at my place that night, as I had to do laundry before work in the morning. She was fine with that. My plan was to cruise Washington Park, a popular gay cruising spot on Capitol Hill in Denver. I lived in the Capitol Hill area and it was on my way home.

I drove into "Wash Park" and steered towards the popular cruising area, parked my car, and shut off the headlights. With my seat reclined and my window down, I pulled my cock out of my pants and waited. Sometimes another car will approach, other times a man will walk from the wooded area and approach. Tonight it would be a man approaching my car on foot from out of the darkness. I was stroking my cock as he casually walked by and glanced in my window. He passed by, and in my mirror I saw him turn around and walk closer by the side of my car. He stopped, leaned down, and watched me fondling my hard cock. I looked up and asked him,

"Want to get in?"

Without a word, he walked around to the passenger side and climbed in. I reached over and rubbed my hand over the growing bulge in his jeans. I could feel his cock hardening through the fabric. His cock continued to swell in his jeans as I caressed it. I leaned in closer and with my left hand I unfastened his pants. After unbuckling his pants and pulling down his zipper, I put my mouth on the bulge straining against his underwear. My mouth against his thick cock and the musky odor of his jockey shorts were making my cock throb. I pulled the waistband down so I could free his stiff rod and take it in my mouth. He pushed the back of my head down on his fuck stick and lifted his hips and buried my face in his crotch. His cock was thick and I gagged as I struggled to break free of his grasp. He kept his grip on my head and thrust his hips upward, forcing his cock deeper into my mouth and down my throat. I wasn't accustomed to this type of aggression and was struggling to breathe as I gagged on his thick rod , my throat slime coating his cock. He finally let up and I lifted off his dick, and with saliva running down my chin I gasped for air. His cock was average in length but it was by far the thickest I had ever had in my mouth. I had to stretch my mouth to accommodate his girth. My middle finger and thumb didn't touch as I gripped his cock and brought it to my mouth to suck his knob. His cock wasn't much longer than mine, about six and a half to seven inches, but the girth was way bigger. I am six inches around and my fingers barely touch when I am stroking, he had to be seven inches or more.

"I live two blocks from here," he said, "let's go to my place where it's safer."

I quickly agreed as I wanted to experience more of his giant cock. He directed me to his apartment which, as it turned out, was right around the corner from of mine. His cock was still out as we drove and I kept glancing over at it as he stroked it. My cock was throbbing at the sight of his fat, veiny meat stick. He told me his name was Kent and then went on to tell me he was going to make me his bitch tonight. I wasn't sure what he meant by that and I was beginning to have second thoughts. When we got to his place he got out of the car with his cock still out of his pants and headed upstairs to his place. A man was coming out of the apartment building as we were approaching. He greeted Kent, looked down at his exposed organ and then looked at me and smiled.

We entered his apartment and I dropped to my knees and began sucking his cock bringing it back to it's full erect glory almost immediately. Crowning his veiny shaft was a fat, bulbous mushroom head and I worked my mouth around his cockhead and flicked my tongue around his piss hole. He ordered me to get undressed and lay on the couch. He was quite dominating, something I hadn't experienced before, but I did as I was told, He climbed on top of me and put his cock in my face. I took it in my mouth and began to suck his head while stroking his hardened shaft.

Kent reached down, grabbed his thick cock by the base and forcefully slapped my cheeks and forehead with it. My face was wet with my saliva and his pre-cum. Still holding it by the base, he fed it into my mouth and I stretched my mouth as he leaned over me and pumped his cock in and out of my mouth. He was pumping fast and shoving it in deeper with each thrust. It was getting more difficult to catch my breath as he fucked my mouth and I started gagging and spitting up throat slime. With both hands I pushed him away from me to keep from throwing up. I love sucking cock, but this was getting a little rough for me.

He got up and told me he wanted to fuck my ass. While curious about it, I had never taken a cock anally and told him so.

"Yeah, that's what they all say.", he said.

I told him I'd like to try it, but reiterated it would be my first time. I don't think he believed me. He left the room and came back with some lubricant. Laying on my back he had me pull my legs up and expose my virgin ass to him. He told me the lube had lidocaine in it and would numb my ass. He applied it to my ass and I felt him put his finger in my sphincter and work it around. It was quite pleasurable. He then greased his fuck stick, got between my legs and pressed his fat head against my mancunt. He was pressing hard, but he couldn't get it inside me. He told me to relax, but I was instinctively tensing up. I didn't know how to relax my asshole. He had me get on the floor on all fours and he knelt behind me. With his cock firmly against my rectum he told me to push out like I was taking a dump as he pushed in. With that, I felt his massive head push into my rectum and pop my cherry. I let out a loud yelp, it hurt like a motherfucker I begged him to take it slow and easy.

With his head firmly embedded in my ass he pushed me down on my stomach and rammed his cock all the way in with a single thrust. The pain was excruciating, it felt like I had a red hot poker in my ass. I was focused on the pain and at this point I wasn't sexually aroused, my cock was flaccid. He was thrusting in an out of my ass at a furious pace and I was moaning and grunting in pain with each thrust.

I began feeling lightheaded as though I was going to pass out and the experience soon turned surreal. With each hit on my prostate I was feeling a tingling sensation in the head of my cock. It was a weird combination of pleasure and pain. I reached underneath and took my cock in hand and felt pre-cum flooding out of the head. Kent slowed his pace while still burying the entire length of his cock in me and I felt my dick hardening. The pain was only minor now and my cock was fully erect. I had my hand wrapped around my cockhead and it rolled easily in my fist with the generous coating of pre-cum.

Kent pulled me up to my knees and with his cock buried deep in my ass, rolled me over on my side, lifted my leg over his head and was now between my legs with me on my back. He was fucking me in a steady in and out motion and with my legs held up and apart he was achieving greater penetration. I could tell he was bigger in girth at the base of his cock and with each entry I could feel my asshole being stretched to it's absolute limits. He put both his hands in the crook of my legs behind my knees and lifted my ass higher and began the furious pace he had begun when I was on my stomach. Fucking me while laying on my back he was able to connect with my prostate more forcefully and the sensation in my dickhead was intensified. In no time I was spurting hot cum all over my chest and stomach. He increased his thrusting and was plowing my ass like a piston. The force of his thrust was painful and suddenly, he jammed his cock as far as he could and I could feel it pulsing deep in my ass as he pumped his load in me. His cock throbbed for what seemed like an eternity. After it stopped, Kent pulled out to just the head and then drove three more hard and deep thrust into my wet fuckhole. I gasped with each thrust.

He pulled his cock out, got up, and said, "Get dressed, time to go home, faggot."

I got up on my knees and struggled to get to my feet. My ass was hurting like hell. When I got up I looked over at him and thick cum and strings of pre-cum we dripping from his cock. He was no longer fully erect, but his cock was still thick as it was retreating into it's flaccid state. I took it in my hand and caressed it. I wanted to suck it clean, but was wary of taking it in my mouth after being in my ass. I opted out.

Walking back to my car was difficult. I was painfully aware I had been fucked in the ass, and fucked hard. I had mixed feelings about trying it again. I could feel the mixture of cum and lube between my cheeks. I needed a hot shower. I went into the bathroom at home and got undressed. When I took my underwear off I noticed a pink and white mixture in the crotch. I grabbed some toilet paper and wiped my ass and it was tender to the touch. Looking at the toilet paper I saw red spots mixed with cum. blood. Kent had literally ripped my ass open. I was now concerned about what damage I may have done. I went on to bed and when I awoke the next morning, my ass was still quite sore. I went in the bathroom and dabbed it with some toilet paper and saw I was still spotting. Shit.

Speaking of shit, I had to go. My bowel movement burned like fire and there was blood in my stool. I was beginning to think I may need medical attention and even more concerned with how I would explain it. I was genuinely scared and called in sick and just laid in bed all day. The day after that the pain was subsiding and there were no visible signs of bleeding. It was a good five days before my ass was feeling normal again.

I waited another three years before having anal sex again. This time I made sure he had an average cock that was average in girth and not so bulbous. It was much more pleasurable and I now engage in anal on a regular basis. Bigger is not necessarily better, fellas.

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We see anal videos popping up all over. The common belief is that women hate anal and it find it nasty and disgusting besides painful and torturous. That's what makes these videos so popular. The truth my friends is something different.Few years ago I had my first anal with a young, 20 something girl. She hated it. She cried out loud and in our 6 month relationship we only did it twice.I broke up and got involved with another girl, a young school teacher who was addicted to sex but she didn't...

2 years ago
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Fucked my crush in Manali

Hi, readers. Your Milf Lover is back with a new story. This is also a real story. This happened after I lost my virginity to my aunt. I got more confidence to have sex with other girls. So let’s get to the story. This is the story of me getting lucky with my female best friend’s older sister. She had always been my crush since my school days. She was 4 years older than me. So the story starts when I receive a call from my friend one day. Me: Hi, what’s up! Friend: Hello, nothing much. I want...

2 years ago
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Sg Fuck buddy getting analed

I met Ling on the chatrooms last time when it was still popular. Wasn't the #sex rooms, but the non-sexual kinds. Used to chat about normal mundane stuff, never really cared if she was a 'real girl' or some guy pretending to be one, until one day she said something like 'I hate my breasts, they are too big'I was abit cautious and asked 'why? how big are they?'"I've big C cups, maybe Ds. I can't do all kinds of sports with them"This piqued my interest, so I started veering my conversations...

3 years ago
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But You Can Do Me Anally

But You Can Do Me Anally “But you can do me anally” was what I heard her say. I also heard the part about, “I’m a virgin and I’m going to stay that way. I’m saving myself for my future husband…but you can do me anally…I don’t mind.” Then she hung the phone up. That came from my thirteen-year-old sister Carrie as I entered the living room. I startled her. Carrie turned around so fast that I thought that she would loose her head. She turned bright red and said, “Oh thank God. I...

3 years ago
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Hailey Tries Anal

I sat at my desk doing homework and staring out my bedroom window hoping my boyfriend Mr. Chapman would get home soon. He’d been working a lot lately and as a result, we had seen little of each other. As a police officer, I knew his schedule was weird and I didn’t want to smother him or anything, but as his girlfriend, I worried about the late nights and wanted him to be safe and snuggling with me every night. Living with my parents threw a wrench in that particular fantasy, but I wanted it all...

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2 years ago
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Talking Dirty Pt 2 Anal

Two days after the Night (or, as Max calls it, “the night I sexually blossomed.” Ugh.), Max left town for the week to visit an old friend of his from college all the way over in Chicago. I won’t lie; it sucked. That Night (yes, we gave it a capital N) with him was amazing. It was a whirlwind of pleasure.And now he was leaving me.Okay, that sounded really overly dramatic, but you get the point.So after dropping him off at the airport, I drove back to my apartment. Ever since we started dating,...

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3 years ago
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Training Her For Double Anal

We were training her ass for double anal sex, or at least that was the plan. We had already had success taking her virginity; opening up her pussy to a dildo, then to my dick, then to double vaginal, and even some anal. We had talked about fisting, along with other things that were pure fantasy. Like, what monster would you fuck? (her answer: a werewolf)... But after our success with letting two men in her pussy, she became intrigued at the idea of doing the same with her ass. She agreed to let...

2 years ago
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My first anal

Preamble: This is the story of the first time I did anal. I wrote it on vacation at my parent's house, got a little carried away reliving the experience in my mind, and got very excited ... so sorry it is so long. I got so excited that I actually soaked through my panties my sweat pants. I have posted a pic of me after writing this story, wetness and all, and a pic of the guy from the story (well, at least his cock, which took alot to talk him into letting me take it). My First Anal:I was...

3 years ago
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His First Anal

His First AnalBy: Londeaaz Chohan Hazel’s pussy was still tingling from the fullness and the depth of penetration. All the toys she had ever used, never made this far into her cunt or stretched her this wide. She looked down at her red, puffy slit, still moist because of sharing sex with her man. Her clitoris stood firm from its sheath and begging for more attention.After resting few minutes, she had taken Mason’s semi stiff cock once again in her hand for stroking. Her kitty was sore and...

1 year ago
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BimBim Anal

Everyone loves anal sex these days, right? Well, if you have not experimented on it yet, I suggest you do your research and try it. However, if you are still hesitant or do not know where to go first, I have a recommendation. Well, on BimBim.com, there are dozens of ladies who love shoving everything from fingers to all manner of sex toys into their individual tuchus’ for your viewing pleasure. Also, as we will see, there are even more reasons besides that to consider looking up this site and...

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1 year ago
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NaughtyBlog Anal

Ages ago, I reviewed NaughtyBlog.com, which I must say is one of the better porn blogs that I have read. It is not quite as good as my own, of course, but it does have a certain level of charm. Unfortunately, in my initial overview, I had pretty much nothing about good things to comment on Naughty Blog.But I realized when writing that I will have to revisit this site to go into different aspects in an appropriate amount of depth. So, to do this adult-oriented blog justice, I’m going to do a...

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1 year ago
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iWank Anal

Everybody loves fucking pussy. It was purpose-built for cock, crafted by millions of years of evolution. It is a master of stroking every drop of cum out of a cock for reproduction. Men have been trying to replicate its glory since the penis came into existence. First, we tried a pile of wet leaves, and slowly we worked our way up to polymer plastics and rubbers installed inside a flashlight-like plastic outer coating. We have even installed them in things like my TSRPV2 (Tesla Sex Robot...

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2 years ago
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Erica Ranch Wife pt 4 her first anal

Introduction: After some hesitation , Erica finally tries anal Erica was pretty adventurous during our playtime. She had made suggestions about anal sex and offered none of the upturned-nose type behavior some people have with it. She had taken a rather vigorous anal fingering and had no problem with analingus when I performed it on her. In fact, she had motioned my head towards her butt,when I ate her out on several occasions. She was concerned about cleanliness and seemed pretty aware of...

4 years ago
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Mias first anal

Alex drove Mia home. She got out of the car and came around to his window for a quick kiss. Alex handed her a small package and told her to open it when she was alone. Burning with curiosity she hurried inside and ran into her room, shutting and locking the door behind her. She ripped open the package and found a short note from Alex at the top, which she immediately read. ‘Put it in and leave in. I’ll pick you up around three tomorrow.’ That was all the note said. Impatiently, she tipped...

2 years ago
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Virtually Anal

I really wanted to experience anal sex. It wasn’t something that my wife was comfortable with, though, I must admit, the rest of our sex life was pretty damn good. The closer I got to fifty, the more I was drawn towards the need to experience it. I really wanted to see my cock disappear inside some lovely woman’s arse, and for her to encourage the act. I also knew that I couldn’t cheat on my wife, not with another woman, not without her agreement anyway. Fortunately, I am well off. At forty...

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4 years ago
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How I Learned to Love Anal

Like most women, I always wondered why men were so interested in anal sex. Why would you want to put your cock in that hole when there is a perfectly good, silky smooth pussy right next door? Well this is how I came to love anal sex....Before I was married, most men I dated would ask me for anal sex and I always turned them down. To me, my ass was for one purpose and that wasn't very sexy! There would be times when a man would go down on me and would put a finger in there and it actually felt...

3 years ago
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Mias first anal

Alex drove Mia home. She got out of the car and came around to his window for a quick kiss. Alex handed her a small package and told her to open it when she was alone. Burning with curiosity she hurried inside and ran into her room, shutting and locking the door behind her. She ripped open the package and found a short note from Alex at the top, which she immediately read. "Put it in and leave in. I'll pick you up around three tomorrow." That was all the note said. Impatiently, she tipped the...

3 years ago
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Ive Never Been One For Anal

I have never been one for anal. I have always felt my ass was too tight and it seemed dirty. But oh, how I am now a fan of getting a little dirty. My boyfriend has always wanted to do my tight ass, but I never even wanted to see what it would feel like. I have always been the one fucking his ass. I purchased some Thai beads for him as I knew it was a fantasy for him to have his ass screwed and I loved to push my dildo’s inside him. Almost two years into our relationship I found out that anal...

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1 year ago
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Amber Gets Anal

Amber stood nervously before the apartment door. She had just moved to Chicago from a small town in Indiana little less than a year ago and her new group of friends had been frequently telling her over the last few weeks that they had a tradition whenever someone in their group turned twenty one. They wouldn’t give any details and only laughed mischievously when she asked about it. Tonight was Amber’s twenty-first birthday, and even though she had her reservations about their...

1 year ago
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RARBG Anal

Women are like bowling balls. They have three holes, and each is equally important. Yes, some men only use two, so they can throw those super curveballs, but do you know what we call those guys? Fags. They are the type of dudes to base their personalities on the fact they wear shorts all winter. A real man makes use of all three holes. To waste any god’s creation is the greatest sin against the sex gods, and therefore, the porn gods. They have a very tight relationship.Each hole has its...

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1 year ago
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Adult Empire Anal

If you haven't picked up on it yet, I fuck a lot. I fuck multiple times a day, every day. My cock is a blue-collar laborer. It punches into work every day, excited for what the shift may bring. You never know what could happen. Will we be fucking big-titted milfs? Or perhaps some petite teens are on the menu. And let's not forget about the National Albanian midget gymnast team. Those bitches are flexible.Full-Time Fuck CareerIt can be tough to find time to work when I have so much fucking to...

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2 years ago
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First Time Anal

She was always so quiet and reserved when I met her but my sometimes awkward desires would get to her even if it were something she'd already said she'd never do. I got her into oral sex with a little patience and care, and showing to her how wonderful it could feel, as well as shaving her pubes; more than her usual trimming, anyway. She's still as quiet as when I met her, but definitely much more open minded. It all comes down to how you do it. You don't need to 'blackmail' or 'bargain' with...

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