Unexpected First Anal (M2M) free porn video

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I was in Boston for business and went to a local adult bookstore to score some action. Unfortunately, there were only a few people there. I decided to look around at the movies that were available to see if something would be good to take back to the hotel room. I started in the straight videos but soon moved to the bi-vids. After looking at a few movies and deciding against them, I heard a voice say “you know the real thing is better than the movies”. I looked up a little embarrassed to see this huge guy standing next to me. He was in his mid-40s and had to be about 6-4 tall and well over 300lbs – most of it muscle.

He and I exchanged a few words and then he asked if I wanted to join him for a beer at the bar across the street. My heart raced with anticipation, as this guy was quite good looking and from the bulge in his jeans was well hung. At the bar, it was a little awkward at first talking he introduced him self as Cory and I in turn introduced myself. We soon found a common interest in football. I learned he was a NFL lineman for a few years for the Tamba Bay Bucs but had to retire early because of injury issues. After a while the topic turned to our wives and sex. Then he asked if I had been with a guy before. I hesitated but he said it was ok he had been with a few. I fessed up that I had sucked a 3 guys off. Soon, he invited me back to his hotel room and I accepted.

We walked up to the Hyatt and through the lobby. I was a bit self-conscious as thinking everyone was watching me knowing I was going to suck a guy’s cock. We went up to his suite and he started to undress. I followed and undressed, uncovering my fit 6-2, 180lb body. He moaned as he commented he liked what he saw and he appreciated my hairy body and average size cock. I looked at his amazing physique, and it was clear he still lifted weights. My eyes dropped to his semi-hard dick. It was dark and hairy and already pretty thick. Cory tuned in some porn on the TV and we laid in bed. All of a sudden he leaded over and forcefully started to kiss me. Although not my thing, because of his dominate attitude I kissed him back.

He leaned back and pulled me over to his chest. I sucked both of his nipples and then he pushed my head down to his cock. I rubbed his cock and licked it. It was only 6.5 inches long but it grew very thick. So think I could just get my had around it. I licked up and down his shaft and sucked his balls. We shifted positions. I got on the my knees on the floor and he stood in front of me. I returned to licking his shaft and he said “open wide and stick it in your mouth”. Man was we thick! I had to stretch my jaws just to get it into my mouth. My jaw was uncomfortably stretched and I could only get about 3 inches in my mouth. I only was blowing him for about 30 seconds, and he said “oh fuck I am going to cum”. He pushed my head down as he arrived at his climax. It was all I could do not gag as he started to cum.

As he came, he held my head on his dick shooting wad after wad of cum, flooding my mouth. I tried to swallow but the girth of his cock made it difficult and most of the cum ran down my chin and neck on to my chin. As his orgasm subsided he pulled out of my mouth. Almost apologetically, he told me he did not get blown that often and thus he came quite quickly. Frankly, I was fine with him cumming quickly, because my jaw hurt.

Cory proceeded to pull my cum covered body up on the bed and bent over taking my rock hard cock in his mouth. MMMM.. He was masterful at sucking cock and soon I was approaching the point of no-return. He pulled my dick out of his warm mouth and stroked it with his strong right hand. Within in seconds I was reaching my climax. Cory loosened his grip on my rock hard cock delaying my release by a few seconds. I screamed as I shot a huge load over my belly. Cory squeezed the remaining drops of cum from hard dick and then proceeded to rub his and my cum into my hairy chest. He collapsed beside me on the bed as we both caught our breath.

I guess he saw the disappointment in my face that everything happened so fast. We had only been in his room about 15 minutes. He told me to stay, and that he would be ready for round two in a little while. . We watched an NBA game for a hour the Cory turned the porn channel back on, signaling his readiness for round two. I reached down and started to massage his cock and he reached over and stroked me back to full mast. He then asked if I ever had anal sex with a man. I told him no, I had not. He said he wanted to take my anal virginity. I was nervous and truthfully scared, especially because of the thickness of his cock. So, I declined his offer

He then asked if I had ever had my ass eaten by a guy, and said no, but I would probably enjoy that. He piled up a few pillows on the bed and had me lay over top of them. My ass was in the air, and my head in a curled up blanket. Corry, then spread my cheeks and I felt his tongue start at the top of my crack and trace down to my asshole. He circled my asshole and the feeling was exquisite. He reached under me and massaged my dick. Soon he was sticking his tongue in my asshole. Hmmmm. I was loving the feeling. Cory moved his hand from my dick, leaving it aching for pleasure and started playing rubbing my asshole with a finger. He gently worked his finger into me over the next minute and I started to push up to take his finger deeper. His finger did hurt a little but I soon started to push back on it help make it feel better. Cory, keeping the finger in my asshole, reached over and got something out of the top drawer of the nightstand. I felt a cool wet sensation and figured he was lubing my asshole. As he pushed his finger it worked the lube, I started to groan my approbal. His finger was getting me horny and I was waiting for him to ask. Soon Cory asked if I had changed my mind about getting fucked in the ass? I did not answer. And he said I will take that as a YES. I still did not say anything as I was still scared of this thickness stretching my ass.

Cory applied a little more lube to my ass and then pulled out his finger. Cory told me to reach back and spread my cheeks and as I did I knew there was no turning back. He positioned his big headed dick at my tight opening, gently rubbing my outer anus. It felt really good and I relaxed a bit succumbing to the idea I was going to the idea that I was going get fucked for my first time. Cory started to push his dick in until it met the resistance of my inner ring of muscles. He paused and moved back out then slowly pushed into the head back in, but did not stop . The pressure on my anus ws intense and then I felt my ass give way and his thick dick head popped into my ass!. Immediately, I grabbed the sheets, and screamed “Damn”. Cory immediately pushed my hips down with this hands trapping me as I tried to pull away. I struggled but he continued to penetrate me deeper with each small stoke. “Fuck, Fuck, Fuck” I kept saying. He kept me trapped and proceeded to fuck me very slowly with long deep strokes. My asshole felt stretched to the limit as he kept fucking me. Cory told me that my ass was fucking tight and it was making his dick feel really good. I thought that is nice because my ass fucking in pain. Cory told me to stop resisting and relax. I kept grabbing the sheets, but did try to relax a little. He started to ease up on the pressure on my back and his idck started to slide more easily in and out of my rear. He kept saying “damn this feels great” as he fucked my tight hole. The pain subsided just a touch and my cursing turned to just grunts as he picked up the pace a bit. I could really fell him deep inside of me and as he was now going balls deep on every stroke. After about 5 minutes or so, he slowly pulled out. He had me turn over, and positioned me on my back with my butt raised in the air on top of the pillows. He squirted a bit more lube on his dick and got ready to mount me again. He put my legs up over his shoulders and positioned his hard cock at my sore rosebud. Cory told me to look at him and I opened my eyes and looked into his. He looked at me very intently as he pushed back into me. I again grunted and cursed, but this time the pain was a bit more tolerable but the fuck was every bit as intense. Within two strokes he was back at fucking me slowly but deeply. In this position his dick inside of me felt good although my anus still hurt from being stretched. He had me start to stroke myself. The feeling of my hand on my dick and his cock inside of me was incredibly intense. I guess this is what is meant by “hurt so good.” My painfully stretched ass and the pleasurable sensations from deep within where combining to really bring me close to cumming. Sensing my arousal, he told me to stop jerking for a while – that he did not want me to cum just yet. Cory then started to fuck me really hard. Yes, the pleasure turned back to a bit of discomfort from the hard fucking, but I was somehow enjoying it. I was saying fuck my ass, fuck my ass you stud. Cory’s breathing started to speed up and as I looked at him I could see his chest get red. He urgently told me “now, jerk now.” I reached down and rubbed my cock. Cory was approaching orgasm and so was I, Cory pushed deeply with all his weight and groaned. This started my orgasm. As he shot his come deep into my ass I could feel my ass contract around his cock as I shot my cum on my tummy. Both of our orgasms lasted an very long time.

As Cory, collapsed he pulled out of me. I reached around and felt my sore asshole and it was partially gaped from the intense fucking I just had. Cory told me to rub the cum into my chest which I willingly complied. As I turned to my side, and rolled off the pillows I could feel some of his cum run out of my asshole. We rested for a bit, then he told me to get dressed and leave. I was not allowed to wash up. As I walked from his room, through the lobby and out to my hotel 4 blocks away, I could feel cum leak from ass, and could smell cum on my chest. This was my first true walk of shame, and I wonder how many people realized what I just did.

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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...

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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...

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A WellLived Life Book 9 AnalaChapter 8 A New Semester and a New Job Part III

January, 1984, Chicago, Illinois “OK, now that we’ve made love, talk to me more about Becky,” I said to Anala. “What I was trying to tell you was that denying your feelings, and refusing to address the issue with the girls closest to you, is not healthy. Is there anyone else that you are literally afraid of being with? And forget your mom for the moment.” “Nobody that I can think of, excluding my mom. I’m not sure that I’m afraid, but I’ll concede that for the sake of the...

3 years ago
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A WellLived Life Book 9 AnalaChapter 36 Corrections

May, 1984, Chicago, Illinois Bethany and I said our goodbyes and I walked her out to her car. We kissed before she got into her car, and after she drove off, and I went back inside. My housemates were filtering out, along with my friends, and the house would soon be empty. I let Kara and Jackie know that I was going to pick up Anala. They disappeared together, and I headed out to my car to drive to Bridgeport. Other than a brief greeting, and a question about her final project, Anala and I...

1 year ago
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LiveJasmin Anal

LiveJasmin has been at the forefront of the live streaming smut business since the beginning of time, or so I’m told. They’re a reputable company, and they pride themselves on being classy and dignified. They’ve got a certain air of decency and elegance, and I like that about them. I can respect that. There’s nothing wrong with trying to be tasteful with your smut. I can appreciate a classy lady just as much as I can appreciate a total cumslut. That being said, I think LiveJasmin’s Anal section...

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1 year ago
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Flirt4Free Anal

What’s better than hot anal porn videos? That’s right, hot anal live streams are. Not to hate on regular porn videos, but live content will always be better because of the added intimacy – you can tip the girls, chat with them, buy them gifts, and even pay them to act out your anal fantasies. Well, if you enjoy this kind of content as much as I do, I recommend that you check out Flirt4Free.com/Anal.Flirt4Free is a fantastic and popular cam website in general, but their anal section is even...

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2 years ago
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A WellLived Life Book 9 AnalaChapter 38 Analysis Again

May, 1984, Chicago, Illinois I didn’t return Becky’s call; I called Jackie instead. I told her about what had happened with the phone message. “Let me get this straight. You didn’t make love with Penny, but you realized she’s the antidote to Becky?” “Yes. I thought about Penny so much, and was so focused on her, that Becky didn’t even cross my mind, and when I heard Becky’s phone message, I was annoyed, not because I’d missed lunch with her, but because I simply didn’t want anything to do...

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A WellLived Life Book 9 AnalaChapter 24 Everything Changes

April, 1984, Chicago, Illinois On Saturday morning, after a night of passion which had lasted until after 3:00am, Anala and I slept in. I’d called Sensei Jim earlier in the week to let him know that I was going to stop attending for a time. He’d pressed me hard not to stop, but I simply didn’t have the time, at least until the end of the semester. I’d promised to reevaluate the situation at the end of the summer, but I knew what the conclusion would most likely be. Because we slept late, I...

2 years ago
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A WellLived Life Book 9 AnalaChapter 25 The Big C

April, 1984, Chicago, Illinois My plans to get my schoolwork out of the way for Joyce’s visit hit a roadblock when I arrived home on Monday. I had a message on my answering machine from the union electrician. His brief message said that there were some changes and additions they wanted, and he asked me to call right away. I sighed and dialed the number he’d left. We spent twenty minutes discussing the changes, and I made copious notes. I looked at my calendar, checked my syllabi, and told...

1 year ago
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Streamate Anal

Anal has been a huge part of the content we consume on premium and tube sites every day. The genre is prevalent, and everybody loves seeing a babe taking cock up her ass. But do you know what’s better than recorded anal scenes? You guessed it right, anal live streams are. For the better part of the decade, I have been providing folks with the best sources of smut for their various kinky fap sessions. I have searched far and wide for all kinds of fetish content, so you can trust me when I say I...

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First time with an anal plug

I've always enjoyed ‘first time’ stories, so I thought for my first story I would tell one about one of my best first time experiences.This isn't my first anal experience though… that happened long before (and I may tell that story someday too if this gets a good response from people). I had tried other anal toys before this, some of them were my own creation, but they were all fairly thin and small mainly just to get to my prostate for direct stimulation and that was it. This short story is...

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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...

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...

4 years ago
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Our First Anal Adventure

Zee had very conflicted feelings about anal sex. The first time I asked her if she was into it, she replied "That part of me is an exit. Just an exit." I thought that was the end of it.Every so often, though, she'd bring it up. Usually it was in relation to her part-time job as a cam model. I didn't tell you that? Well, don't judge me, OK? There were always members asking her to do anal. I don't blame them for asking, either.I always said that Zee's ass was perfect for doggy style. It was also...

4 years ago
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First time anal

Hi guys, I have never written here before, but I would like to use this as a diary entry. This is the story of how I had my first anal experience this week.It was a normal Sunday afternoon, I was in bed with my girlfriend and we watched a series. When we kissed, I slowly took her shirt off. She has a great figure, is slim, nice breasts (B-Cup) and has blonde hair and a beautiful face. First I kissed her breasts, then her belly and in the meantime I took off her pants. I moved my tongue further...

3 years ago
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original anal sex diaries2009

My sex diary-The anal-slut chroniclesJan 1st 2009 This is my own story, written in my own words with absolute honesty, without bending the truth or any other bullshit designed to simply grab peoples attention in order to get them to read this, because to put it simply… I couldn’t give a fuck who read’s it. This is simply my transition from a heterosexual 25 year old lad, into a bi-sexual, submissive, anal-loving whore, starting today, with twelve months worth of entries (or so I...

1 year ago
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How to Receive Anal Sex Male Part 2

This is my follow up piece on how to receive anal sex. In this segment, I want to share more logistical ideas, tips, and experiences in receiving anal sex that can help the reader learn about potential unknown facts that I may not have shared in my first writing. As I try to think back on my sexual experiences, I have estimated to have had sex with probably 30-35 women, I have blown over 100 guys, and taken as many as 50-60 dicks in my ass. I have lots of experience and want to help you if you...

4 years ago
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How to Receive Anal Sex Male Part 2

This is my follow up piece on how to receive anal sex. In this segment, I want to share more logistical ideas, tips, and experiences in receiving anal sex that can help the reader learn about potential unknown facts that I may not have shared in my first writing. As I try to think back on my sexual experiences, I have estimated to have had sex with probably 30-35 women, I have blown over 100 guys, and taken as many as 50-60 dicks in my ass. I have lots of experience and want to help you if you...

4 years ago
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Violets Anal Training

Author: Powerone Title: Violets Anal Training Summary: Violet is subjected to anal and sphincter training so she will beprepared for anal sex. Keywords: M/F, anal, humil, reluc, mdom, span Copyright 2003 by Powerone.  The author may be contacted at [email protected] Violets Anal Training     Michael sat in the chair as she entered.  Poweronehad described her perfectly, long black hair, green eyes, pale skin, very smallhands and fingers, DD breasts and small hips .  She had a gothic...

4 years ago
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6 Benefits Of Anal Sex

According to a 2012 study by Indiana University, more people are having anal sex. While the 1990s only saw roughly one-quarter to one-third of men and women having tried anal, by 2009 that percentage had jumped to 40 to 45 percent. But while that may the case, anal sex is still, as Salon reported in 2012 "Science’s Last Taboo.” We know that some people are having it, but it’s not very likely that people are willing to talk about it. Somewhere between the poop rumors and the embarrassment of...

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