Anal Porn Stories
Page 307

Finally, My First Tranny!!!

I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty horney since my doctor is a female and I had a complete physical so she and her nurse were in the room with me. I got to the train station to go back to Willow Grove and was standing on the platform when I saw this beautiful brunette haired woman about 10 feet from me. She was wearing jeans, and a spagetti top shirt. I could see that she had a real nice pair of tits and my cock started to get hard in my jeans. Being horney and looking to get laid, I walked over to her and introduced myself. There w... Continue»
Posted by adw276 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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First gay sex

I met a guy on CL who was about 20 years older than I was. He was in his 40's and sent me pictures and had a fantastic, 7 inch cock. I told him I wanted my first time to be bareback, no interruption from a condom, as long as he pulled out and I wanted to makeout with a guy. We set up a time for me to go to his house. I was so nervous.

I pulled into his driveway and took a deep breath, 'this is it' i thought as I walked up to the door. He answered before I could even knock and it seemed like before the door was closed I was pushed up against the wall with his wet tongue in my mouth. I was p... Continue»
Posted by cosguy22 4 years ago  |  Categories: Anal, First Time, Gay Male  |  
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Blackmailed by Grandfather

Blackmailed by Grandfather

By billy69boy

During the summer, when we were young, our grandmother used to invite her many grandci1dren to stay over for a few nights. She would host two of us at a time. Her five grown chi1dren were all married and had several chi1dren of their own, so there were plenty of us to go around.

One summer, I was paired up with my cousin Cindy, who was a couple years younger than me. Cindy was a pretty little thing, blonde hair and blue eyes that always seemed to be hiding some secret mischief behind them. I didn't know the word back then, but I would call... Continue»
Posted by billy69boy 2 years ago  |  Categories: Anal, First Time, Taboo  |  
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My wife is going to dress me up as a woman then fu

I just turned my wife onto the idea of dressing me up in sexy women's outfits and putting makeup on me. I have wore her cloths with makeup before but I'm excited about getting her involved. I used a strap-on that she fucked me with that's bright pink and vibrates when i dress up without her knowing when she is at work. I get so turned on when wearing girls cloths and love anal toying a lot. So the other night i told my wife i keep having a reoccurring fantasy of dressing up as a girl and trying on her clothes and makeup. At first she was hesitant and said no but i explained that i would do an... Continue»
Posted by codemizer 4 years ago  |  Categories: Anal, Fetish, Gay Male  |  
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Oh, No! Oh, Yes! - Part 3

we met again Finally.


It's been over a year now since I accidentally sent my s****r-in-law the email that was

supposed to go to my wife. Who knew, as I sat there in a panic at the time wondering

what to do, that it would lead up to these encounters. So far my s****r-in-law and I have

been able to play together on two occasions since my initial accident of hitting the

send button. Since our last encounter our families did get together once but we were

unable to make anything happen. It was a quick visit and the timing of everything just

wasn't right. As usual we ne... Continue»
Posted by adel5000 4 years ago  |  Categories: Anal, Hardcore  |  
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my first tranny pt. 2

it hurt so bad but felt so damn good. I told her just to stay still so I can get use to it. get use to having a cock in my ass. that was a totally new feeling. it was something I always wanted to try. now I was.

she slowly started to move back & forth. not really pulling out, just enough to make me feel better about it. she was stroking my cock, which was rock hard. I could feel her balls on my ass. deep down i was freaking out. this is really happening. I knew that coming here I was going to fuck some ass. not get my ass fucked.

eventually, I got use to her cock in my ass & she was pu... Continue»
Posted by radec_24 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Black Man's White Pussyboy


Black Man's White Pussyboy

Story from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog.

I let Jay into the apartment. He was looking for a one bedroom,
furnished place and had called about my ad in the newspaper. I hoped to
rent this place quickly, then I would be full and could devote my time to
some maintenance and repairs rather than showing places. I looked at the
rental application he had filled out just a minute earlier. From the date
listed... Continue»
Posted by klammer 2 years ago  |  Categories: Anal, BDSM, Gay Male  |  
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Caught by the Neighbour

My story happened many years ago, when I was 16, I lived with
my mother and grandma as my dad left I was 7. My mother told
me that grandma and herself would be going away for a long
weekend on friday, great I thought, the whole house to myself
for4 days...
Friday came and it was a hot day, I raced home from school
in excitment of the 4 days i had ahead of me, as I got home mother
was just getting out of the shower, she is a good looking woman
aged 42, slim and 5'7 tall, grandma was in the kitchen all packed
and waiting to go. Grandma was 63 on the tubby side and 5'7
the same as mo... Continue»
Posted by roganjosh 2 years ago  |  Categories: Anal, Masturbation, Mature  |  
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Man and Wife WHORED out for CASH

My husband and I were really broke while we were looking for jobs and ever

penny counted! We had had several small jobs but we were starting a business

and could barely makes ends meet every month! I was a good looking girl and

had been told so by more than just a few guys and girls too and my husband was

good looking as well. Since we were married, we had been loyal to each other

and never ever cheated at all, much less been swingers!
One day, we had a ton of bills to pay and hardly any money at all. We were

desperate for cash and decided to palce an ad in a local
... Continue»
Posted by TampaHouseWives 2 years ago  |  Categories: Anal, Fetish, Taboo  |  
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My First Guy

Well this is a true story it happened to me about 22 years ago I was about 30 years old, had been experimenting with shemales but I meet this guy we'll call him Greg at a gay bar he was huge about 6' 8" tall with hugh arms big chest he probily weight in at about 280 lbs and small hips but with the best looking cock I'd ever seen on a guy it was at least 12" long, about 4" in diameter he was dress in short shorts and a t-shirt that he almost busted out of. His cock was almost showing out of the top of his shorts, my mouth was watering so bad I had to get a paper towel to catch my drewal. I walk... Continue»
Posted by rafael0058 5 years ago  |  Categories: Anal, First Time, Gay Male  |  
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A Father’s Dilemma!



My name is Rick and this is the story of helping my daughter to discover who she really is.
First a little background, my wife left me around eight years ago. This was just before my daughter, Rachel celebrated her ninth birthday. It was a painful experience for me as I was under the impression that our relationship was good. Unknown to me was the fact that my wife was actually very much a lesbian and had been since she was in high school. Please understand I am not opposed to women being lesbians. I believe that each person shou... Continue»
Posted by mooremike 1 year ago  |  Categories: Anal, Taboo  |  
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Step Jack Daddy: Part 5

Hey guys, sorry for not posting much, I will try to keep them up regularly now.

_______
Over the weekend, Jack and I we celebrated his promotion with a lot of sex. My poor pussy was extreamyly sore by Sunday night with all the pounding it received by Jack.
Jack was a machine. Fucked rough and my pussy loved it. Jack hated condoms so over the weekend we also got a shot for me, which would keep me in check for the next 3months. So we started fucking without anything between us. And hell the feeling of skin on skin... Gave me the hardest orgasms.

Monday, school started.. Jack had t... Continue»
Posted by Ashley1991 3 years ago  |  Categories: Anal, Hardcore, Taboo  |  
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A "striaght" boy's first time

There was a reason that gym was my favorite class of the day. It was because I loved checking out all of the hot guys' bodies, Seeing them remove their shirts to reveal their smooth rock hard abs. I wanted to lick them up and down. I had my eye on this one, however. His name was John, he was a senior like me, I would have done anything to get that dick in my mouth. I wanted him so bad but he was straight. That's how it always is, isn't it? You find a guy you really like, a guy you crush so hard over and then it turns out that they are straight. I was falling for him so hard but he would n... Continue»
Posted by bigboy2119 3 years ago  |  Categories: Anal, First Time, Gay Male  |  
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Maria Stephanos, News Anchor Fucking An Informant.

Maria Stephanos is driving to a seedy motel to meet an informant. She has never met him before but was told he has information for a story she is working on. She is nervous but it is ten o'clock in the morning so she feels a little better that it is in the daytime. She doesn't have to be at work until four o'clock for her six o'clock news broadcast.

Maria is a news anchor for Fox 25 News in Boston. She is 47 years old, married with two teenagers. She is wearing a tight black skirt, black high heeled shoes and a shiny satin black long sleeved blouse. She has bracelets on both wrists, long ea... Continue»
Posted by zombie100 2 years ago  |  Categories: Anal, Celebrities, Hardcore  |  
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MY MOTHER

Lily was raised by her single mom who was very well known as a sexy slut. She would go down to the local tavern where she was able to always bring home a man. When she got home they would fuck all night and she allowed the men anything they wanted. Lily would lay in bed and listen to them talk about fucking and sucking cock and fucking her mom's ass. Her mom would tell the man to fuck her hard and ram his cock in her cunt deep. She would yell "Yes. Fuck me harder. Ram that big cock in my cunt. I want more of that big cock." Also Lily would hear her mom tell him "Lick my pussy. That's it. Suck... Continue»
Posted by mymotherssextoy 2 years ago  |  Categories: Anal, Hardcore, Taboo  |  
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Workout

Several times a week I go to the health club for a mild workout. I often see a guy named Mike. We chat as we workout. Now I am a secret TS so I'm totally clean shaven but also lots of guys who are into working out are also. Anyhow Mike is a real hunk! As most guys do Mike will make an occasional joke about the size of his penis. The bulge I secretely glance at looks pretty good but real size hard to tell. So last week we were done together so we were showering & boy was he right about the size of his cock. So he caught me looking & said "see told you it is pretty big". I said "yes it ... Continue»
Posted by nyloned1 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Tell me a dirty story

I really missed Angela. Ever since she had gotten 'all grown up' (meaning 'turned 18') and moved into her own place, I hadn't seen her nearly as often as I used to. We were only one year apart and had grown up in a very close-knit f****y. We really were best friends. I was home alone on a Saturday night; I was bored. I hadn't talked to Angie in a few weeks, so I decided to give her a try and see if she was home. Doubtful on a Saturday night, that a girl as pretty as my little s****r Angie would be home alone, but I'd still give it a try. Angie was a real cutie; 5'8, long legs, long curly dark-... Continue»
Posted by vtevte 1 year ago  |  Categories: Anal, Hardcore, Taboo  |  
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Wanted to watch for his birthday

"My husband is a dirty little pervert!"

This was the thought that entered my head as his best friend pushed hard up into my pussy.

My husband, you see, has made a habit of befriending well hung friends (at the pool apparently but I think he finds them online) and then teasing me with the promise of sharing me with them. This has kept our sex life fresh and I know I am a lucky girl but trying to keep a straight face and a modest visage when fucking two guys is difficult if the other guy is always bigger than your husband. Our threesomes are always fun and it's not like we have done that... Continue»
Posted by mrshuggy 3 years ago  |  Categories: Anal, Group Sex, Voyeur  |  
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Wife tag teamed at party

It's been several months since the night my wife became the main attraction for two very horny and perverted young men that were attending the same party as my her. Let me give you some background of the events that lead up to the night my wife of 26 years was taken by two bold guys half her age. Carol, yes her real name had plans to stay at our friends acreage to attend a party as I was out of the country working at the time. Our friends have a beautiful place way out in the country and like to have large parties where there usually ends up being lots of drinking. Many of the guests take thei... Continue»
Posted by DD_Rules 2 months ago  |  Categories: Anal, Mature  |  
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holiday suprise

Got back from a sunny week in Fuerteventura yesterday. After a disapointing Christmas I was sorely looking forward to a week of peace in the sun.
Armed with books and an ipod I settled into a very nice hotel 95% full of Germans so chatting at the bar was stilted to say the least but friendly all the same.
I explored the nearby beaches and was stunned by the amount of naturists. All shapes, sizes and ages but mostly (very mostly) plump and mature. To be honest though my thoughts were that if they aren't embarressed then why should I be.
I settled down to my first naked sunbathe on day three ... Continue»
Posted by flashman1807 4 years ago  |  Categories: Anal, Mature, Voyeur  |  
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