First Experience With Older Man free porn video

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I remember my first time. I met a man about 20 years older than I was at a book store. As I got in my car he asked me for a lift and I said okay because I knew the neighborhood. As we drove back he reached his hand in my pants and started squeezing my balls. I told him to stop, and then he just started rubbing the head of my cock. I told him to knock it off. Once we got to his place he asked me in for a drink, I told him as long as he can control himself I can have a few beers.

We went up the stairs; he was behind me and kept commenting on my big ass. I asked him what do white guys know about ass, he laughed said I will show you. I told him just a beer or two then I have to get home to watch the game. He had a fully-stocked bar and asked if I wanted anything besides beer, I said a shot of volka would be nice. He said “Be a man” and poured me a double-shot. He turned on the tv and poured himself a shot as well. When I went to grab the remote he rubbed my ass, I told him once again to cool it.

The guy was old but he was fast, about 5’ 9’ bolding and around 275 lbs. I could see he was hard when he got up to pour me another double-shot hoping to loosen me up. He quickly sat down next to me on the sofa, his bulge was shooting out over his belly. He asked me if I wanted another shot, I told him I had to go to the bathroom to piss. When I came back he was on the sofa, naked from the waist down and on his 4th shot. He was hairy like a bear. His cock was hard, about 7 inches, thick and uncut. He said “I know you want it and I want to show you what this old white guy knows about ass, now bring that black ass over here!” I had another shot and walked over to him. Pull down your short he said while stroking, I said I have to go. Before I could turn, he grabbed my balls. I said “WAIT” if I give you a handjob can I just go, he said sure. He pulled down my shorts and underwear. He looked at my hard dick laughed and said you want me bitch. He told me to turn around and spread my cheeks, I listened and obeyed. He told me to bend over, I did as told. Then I felt a wet stubby finger go in my ass, I jumped and said handjob only and move away.

He said okay, when went to his bedroom and he got on his back and with his cock straight in the air. I laid next to him with my shirt still on and started stroking his cock. While jerking him I played with his balls and thought “Am I really doing this?!” He started pumping the harder I stroked him. He reached under and started stroking my cock, then he reached over my back and put his finger in my asshole. I did not fight him this time. I licked the tip of his cock and he said “Damn boy!” I continued to suck going lower and lower. And his finger when deeper and deeper. Then out of nowhere he grabbed my balls and said you are going to suck me until I pop, then I going to fuck your fat ass, now lick my ball boy. I licked his hairy balls, he tried to get 2 fingers in my asshole and I told him please use some lube…

I told him there is no way I can take that and I was….he just took his other hand and pushed my head down on his cock. As he is started jacking me again and told me to spread my legs wider so he could get a better grip. I spread my legs wider and he pumped my cock harder. I sucked and licked his fat cock, wow I tasted a bit of pre-cum! He jacked me so hard his fist actually slammed into my balls. I had to pause yelled “Don’t stop now boy I’m about to cum!” as he grabbed my balls for real and started to squeeze. I nervously caught my breath. I know if I did a good job he would let go of my sore nuts. His started moaning and pumped his cock in my mouth harder. His leg began to shake and his toes curled. He just yelled “No Shit” and that was it. Matt (if that was his real name) finally squirted. 1, 2, 3, 4 jets in my mouth. I swallowed half and the other half drooled out my mouth. Finally I was done. I looked outside and it was dark, I was thinking about driving home but I was still in no shape to drive. I asked Matt is I could sleep over and he looked at me with his semi-hard cock covered in spit and cum, pat me on the ass and said you know what it will cost you.

He went to the bathroom to wash off, reached in his dresser drawer and pulled out a skirt. I asked him what is that for, he told me to pull off my shirt. I did as told, then he reached back in the drawer and pulled out stockings, a plus-sized woman’s top, and a wig. “Put it on, all of it!” As I put on the stocking, skirt and wig; he just sat on the edge of the bed stroking himself back to a full erection. “You know what I want” You are a big gurl now. He stood behind me, I could feel his hard cock on my ass, he reached in front of me and started stroking my cock. He went lower and played with my balls. He told me he was sorry about abusing my balls but I had been frustrating him since we met. He spun me around kissed my neck and grabbed my ass cheeks firmly and said how much he wanted my ass. He pushed me on the bed face first, I knew what was about to happen and just tried to relax. I crawled on the bed, looked behind me and saw Matt was ready. His cock was pointing up like a rhino horn and just has big. I got on my knees and put my ass in the air. Matt said he needed to taste my ass first. He pushed up my short skirt, I tried to look back again and he said put your face in the pillow. First he tenderly licked my balls and stroked my cock. Then he spread my cheeks, I felt a wet tongue in my asshole, God I was in heaven. He asked me if I liked it I just moaned and said yes. I was so hard, he squirted some lube in his hand and started to stoke me again. I’m lying on the bed, face down, ass up with a tongue going from my hole to my balls and his fat sausage-like hands beating me off. I was just about to cum when he said…Not yet.

I felt him get off the bed, then I felt a liquid run between my ass crack, it was time. I told him to put some lube on his cock and more on my asshole. He asked if this enough as he jammed two fingers in my asshole. I jumped but I could not go far with his hand full of my balls again. “You are tight sugar” I asked Matt to be gentle to my asshole he just barked “Make that asshole wink baby” I winked my hole and he said I was ready. I felt the head of his cock begin to push in my ass I tried to pull away again and he just grabbed my hips like vise grips I could not get away. Inch by inch he went deep, I screamed in the pillow. OMG I cannot take this pain. Then he started pumping my asshole. He asked me if I was crying I said no but please hurry up and cum. He just gripped my hips tight them bang, bang, bang! I was not a virgin but I never had anything like this, never. “Oww baby you are hurting me” I was in so much pain I legs went straight. Matt moved from my hips to my shoulders. He took one hand and started stroking me and said this dick is mine. My ass was in pain and my cock wanted to cum. Pain and pleasure. Just as I was cumming he tore into my ass as hard as he could. I felt every twitch of his hard dick in my ass. He just laid there on top of me until his cock plopped out. I could feel its wetness on my balls. I looked at the clock it was almost 2am. Matt rolled of me, got up and smacked my ass. I stayed on the bed with cum, lube and other stuff leaking out my sore and damaged asshole. Matt laughed and said “Not bad for an old Pollock, now get your fat ass of my bed!” Evidently I did not move fast enough so Matt got a belt from his closet and I felt a sting across my ass. He took the pillow I had been screaming into and put it under my hips so my ass was back in the air. Wack, wack, wack, wack, “Didn’t I tell you to move your fat ass!” Wack, wack, wack! This time I cried as the belt went across my ass cheeks, my back and my balls.

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I've travelled almost my entire working life, mostly as a seafarer. Whilst I've had an amazing time, it meant that meeting - and keeping - someone special has been a real challenge. One of the ways that my wife and I have managed to keep our relationship fresh is through telling stories. It made the miles seem shorter, the separations easier.I hope you enjoy them as much as we have...I wasn't a very disciplined youth. To this day I have no real idea why I volunteered for the Army. When it came...

1 year ago
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Wingman

Ok, I admit it. I had found the perfect chick magnet. So what if it was just a CAT, yes a kitty cat. Well, not just any old cat. My cat loved walking on a leash. And it’s extremely friendly. It will let anyone pet it and would hop into your lap without a second thought. It was a very handsome chocolate point Siamese male. Today, I’m sitting at a shady picnic table at a nearby park. Right in line for the parade of young women headed for the beach. “Oh! Cute kitty! What’s its name?” as the...

2 years ago
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The Terrible Fate of the English Nobleman

         The Terrible Fate of the English Nobleman                        By Dr. Phil This is the story of an 18th century English nobleman living in the Caribbean. He is hated by a local pirate governor. The Englishman refuses to sell a small piece of land to the governor who has wanted it for a long time. The Englishman has been protected by his friendship with the captain of one of the pirate ships. Even the governor fears this ruthless captain. One day the pirate ship arrives in port with...

3 years ago
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Older Weman

As some people of Ukex know, i adore the more mature lady. I have a great sex life with my wife , but have to say that even though she was happy to do most things, she isn't a patch on some of the older ladies I have had sex with in the past few years.One of my lovers is a divorcee named Jean who is 64, and is a work colleague. Jean worked in the office, (still does in fact).We first had sex when I had been dropping her off home for a few weeks, and as a thank you she said that, if i didnt...

2 years ago
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My Pleasure Moments With Suman

By : Delhibiz Hi, this is Gautam from Delhi. I like the most the stories of ISS and reading them from long time. I am 28 years now and this story is 3 years back with one of my exclusive friend. However, she is not with me now and married to someone. Her name is Suman (name changed). We are of same age and worked in different firms in Delhi. During my official tour to Mumbai, we met each other and the story begun. Let me describe her about her physique.She is quite fair with some extra pounds...

2 years ago
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My first older man experience

I thought I would share details of my first experience with an older man. It was 5 years ago and I guess it was life changing, as ever since, older men have always been on my radar.I had known Simon all my life and still do. He and his wife of about 25 years or so (Jayne) are two of my mum’s closest friends. It was obvious that he began to look at me differently though after I headed for college, and things reached their peak on a weekend back at mum’s when she had organised one of those murder...

1 year ago
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Seducing a telephone repairman

I’ve had fantasies about the cable guy that I had once seduced. Jimmy and I unfortunately didn’t have video of it but he was able to take pictures of me taking his big black cock. I’ve recently had to go back to that picture set and loudly reminisce about it as Jimmy fucked me in bed one night. Ironically, a day came when we had trouble with our phone line and finally Jimmy placed a repair request order to fix the problem. When we were finally told what day the telephone repairman was coming to...

Erotic
1 year ago
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Robin and the Catwoman

“Oh my head.” Robin whispered as he stirred awake. It took a few moments for him to fully regain consciousness. His last memory was of chasing someone across the Gotham rooftops, now he was in someone’s apartment. “I’ve been captured!” He screamed in his mind as he suddenly realized he was under restraints. Taking a deep breath, he willed himself to think calmly, just as Batman as taught him. Take stock of the situation, then form a plan of action. The room was in semi-darkness, illuminated...

3 years ago
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In Praise of Older Women Part 5 Emancipation

Meg’s Tale      Both my lovers, Jack and Kate, had returned to their normal lives. My decisions now were made. I had decided to sell my house in the suburbs and move downtown into a condo.This would be another life change for me. Meg the suburbanite had resolved to become Meg the follower of new lifestyles which could not occur in the suburbs. I had spent my marriage in this house and the years where I had rebuilt myself into a new woman here. I was now ready to face the world and new...

MILF
4 years ago
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Ek Main Aur Ek Manu

Hello ma crazy reader my name z Siraz, siraz sidaqi. I was also a reader of ISS lyk you. Actually still I am while reading ol d stories on ISS. I used to thought about se fun in ma like and humesa hi mauke ki talash me rhta tha bt aisa lgta tha ki jaise upper wale ne ek mere hi liye koi mauka banaya hi nahin, isi tadap me aur us parwar digar se narajgi me meri jindagi bit rahi thi bt wo khte hai na, ki dhundho to khuda v mil Jata hai to baki ki kya majal bs usi tarz pe wakai wo din aa hi gaya...

4 years ago
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The Keyholder Pt 2

What was she doing playing chastity games with a twenty something guy? She knew it was crazy, yet Amy was smiling to herself as she stepped off the bus and walked quickly to the address that Ben had given her, a two bedroom apartment in an upmarket development. She hadn’t seen Ben since they’d made love at the hotel a week ago, but she could still remember the feel of his body and his freshly unlocked cock. She hadn’t belted him when they parted the next morning. This wasn’t because Ben didn’t...

BDSM
1 year ago
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The Keyholder

“Just that please,” Ben mumbled as he nervously placed the steel chastity cage and padlock on the counter. He was on his way back from drinks with the football team and the elation of winning combined with the alcohol had given him the courage to finally indulge one of his fantasies. Careful not to make too much eye contact, he glanced briefly at the woman behind the counter, who smiled kindly as she wrapped the cage for him and took the cash. He was now really starting to feel embarrassed,...

BDSM
3 years ago
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The Airman

The Airman?.. It?s strange how the mind can recall certain events with such clarity yet blot out others. It was as if my life began during the years of World War Two. I don?t recall much of anything prior. Of course, being raised and educated in an orphanage doesn?t highlight much. I do remember enlisting into the military at the earliest possible age, to be on my own. As a young airman in the Army Air Corp, I remember my last bombing mission and the ensuing events...

4 years ago
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How Do You Solve A Problem LikeMiss Manson

After her meeting with Ms. Storey that lunchtime and on hearing that the strict young deputy headmistress was going to allow Rebecca Mulligan to carry out her plan to deal with Miss Manson, the head of Music at St Katherine’s School did not hang around for long after the end of the school day. Once she had taken the full school orchestra for their after-school practice she returned to the Music office, packed her bag and hurried to her car. She arrived home just after 5 pm and decided that she...

Spanking
2 years ago
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The Older Woman Experience

My first story on here started with a great night spent with an older woman, when I was 27 and she was 39. But that wasn't my first (or my last) experience with an older woman. I think I'll save the biggest age gap story for another time, but it was around 2 years before my first night with Kim (see the first story if you haven't already!) that I had my first taste - quite literally - of a more mature woman. It clearly had an effect on me, because there have been a fair few occasions since when...

2 years ago
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TV Repairman

TV REPAIRMAN by kimmie oh The doorbell rang, and Billy padded barefoot over the hardwood floor of his apartment. He quickly checked his reflection in the mirror one last time. Then he took a deep breath, smiled, and opened the door. He felt a blast of January cold on his rather scantily clad body. In the vestibule stood a tall, good-looking older man in worn work clothes. The man gave Billy a quick once-over and Billy held his breath. He wondered if he had gone too far: the...

1 year ago
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My first sexual experience was with my older sister

I was just thinking back to my first sexual experience and thought it might be an interesting story to tell. I was in my room playing a video game. They were not as good back then as they are now. My sister, Donna, who was two years older than me came in and shut the door behind her. “Turn that off”, she said in sort of a commanding voice. I paused my game and looked at her. “What?”, I asked. We got along pretty well but I was annoyed that she had interrupted my game. “My...

4 years ago
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The Horseman

Once upon a time there was a princess. She was feeling very trapped in her kingdom so she wanted to take a ride. She summoned her horseman to take her on this ride. He was a loyal man and was willing to do anything her royalness asked of him. Because deep down inside he had serious feelings for her, But was afraid to show this because he was afraid that she did not feel the same way about him considering their positions in the social order as they were. He brought the horse around and helped...

3 years ago
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The Legend of the Dickless Horseman

 It was a dark and stormy night. I was reminded of that fact by a beagle glaring down at me, hunched over like a vulture, perched on the porch of my destination. I pulled my raspberry beret down snugly for protection from the bitter New York wind.I glanced at the decaying house before me. The years had not been kind. Whereas it once stood majestically on a hill radiating beauty now it was an eyesore; the real estate equivalent of Kathleen Turner. Still, it was precious to me. Full of wonderful...

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