Anal Porn Stories
Page 300

An On-line Sissy Lives Her Dream

(Dedicated to a hot little sissy here on xhamster, Sluttish, whose looks and fantasies inspired this story. Her fantasy name is April. That’s where this story starts.)

It started innocuously enough with what seemed like a harmless exchange of private messages on a friends-based porn site. A person identifying as a male sent a note to a young sissy whose profile expressed some fantasies about being made into a full-time sissy, perhaps involving some f***ed feminization and even surgical “enhancements.” The young sissy, April, responded openly and eagerly, and the conversation developed into ... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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Earning It

I walked in the guys locker room at 4:30 knowing this was my only chance to win. I had just celebrated my 18th birthday three days before. My name is Cheryl and at 5’11” and 142 pounds, I am the queen of the volleyball court. District player of the year, All-State and recruited by dozens of colleges. But that’s not why people came to see me play. My body is perfect and those tight and tiny uniforms show it off perfectly. That’s why they come to see me. When I crouch to prepare for a serve, dads hold there breath. I wear my shorts one size too small and when I bend down, the spandex crawls de... Continue»
Posted by crickettwriter 4 years ago  |  Categories: Anal, First Time, Group Sex  |  
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My New Friend

It had been a very busy week and I needed to relax for the evening. It was Friday night and Keith had invited me to a party at his apartment. Just a few friends he said, a few drinks, finger food and music. It sounded very inviting so I decided to go. Keith and I had once had a relationship, but once it ended we became good friends so I was looking forward to seeing him. Life had been a bit lonely since I split up with Don. Don and I had been together when ever he could get away from his wife for about two years. Last month he was transferred to another division of his company so we had to say... Continue»
Posted by kbking70 3 years ago  |  Categories: Anal, First Time, Gay Male  |  
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AMAZING THREESOME SEX

It was a Thursday evening and the couple that I meet at a park in there town. I traveled there to meet them and was extremely nervous about the meeting. Since I am new to the lifestyle and especially have never done a threesome. when they arrived ,we walked through the part and talked for awhile and made sure there was a comfort zone for both parties. Since we did get along so well we decided to go back to their place. we had a bite to eat and a few drinks and talked for awhile to try and ease the tension. We were talking about the waterbed they had and was invited to go lay on it since I have... Continue»
Posted by fukkerguy 3 years ago  |  Categories: Anal, First Time, Group Sex  |  
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A Dogging Tale

It was a Wednesday evening and everything had been planned. I had made contact with an English MILF in a private advert, and her name was Vanessa.

According to her advert she was 46years old and a bit of an exhibitionist.

Given our similar interests we had agreed to meet in a local park/common and I had arrived and parked up in the gravelled parking area which was extremely secluded from the main woodland area. I locked up and switched my car lights off and was now waiting under a large oak tree.

Darkness has fallen and it was now 9PM which was the time we had agreed to meet. In the ... Continue»
Posted by mercedes7 2 years ago  |  Categories: Anal, Fetish, Mature  |  
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The Saleswoman

Well I have always had a fantasy of a saleswoman coming to my door, wearing high heels, sexy stockings, a tight skirt and low cut blouse. She knocks at the door and I invite here in. I let her start her pitch but soon interrupt her by asking "Did it hurt? When you fell from heaven?" for which I get a smile. I the ask "If I told you that you had a great body, would you hold it against me?" at which she laughs some more. I then say "nice outfit, it would look even better on my bedroom floor". The saleswoman then gets up.

I think I have pushed it too far but she walks over, bends down so I ca... Continue»
Posted by fatman26s 2 years ago  |  Categories: Anal, Hardcore  |  
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A night at Eugene'...

My c***d hood friend, Eugene and, I had been best friends since I can remember..When ever our folks were out of town we would stay at each others home. Upon one occasion, both our folks were traveling to a nearby town for a basketball game.

Eugene' b*****r, Wayne, was to watch over us. Wayne took this time to invite a few of his football team mates over. About seven o'clock the three of them arrived and Wayne preceded to get Eugene and I ready for bed, in about an hour we were in bed. Out side a strong storm had begin with lightening and thunder.

Eugene and I pulled the covers over ou... Continue»
Posted by d4david 1 year ago  |  Categories: Anal, Gay Male, Hardcore  |  
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The rent collection (STORY)

It was a squalid home, very little furniture it was poorly lit too, a few weeks ago she had been finally cut off the electric, she only had candles for lighting and a small wood burning fire in the living room used for heating and cooking, the clothes she wore left little to the imagination and they were dirty, dishevelled and too be honest pretty scant too, to save money she had been making them do, what little left of them there were.
Suddenly there was a loud knock at the door, she froze in the dimly lit room, she could hear her heart beat as she held her breathe, then it knocked again. “H... Continue»
Posted by bristim 3 years ago  |  Categories: Anal, Hardcore  |  
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Me and my wife

One of mine and my wife’s favorite things to do to get in the mood and enjoy a good night of lovemaking is to sit in our hot tub and thentransition into a full body massage. Let me clarify, I love to massage my wife. It’s her favorite and most relaxing thing in the world, and it’s great foreplay too. Over our 3 years of marriage, I have found that it pleases her greatly, and it gets us both hot in the process. It’s the buildup that is enjoyable and always ends with some hot sex usually right there on the table or the floor in front of the fireplace.

Our evening starts with us climbing in th... Continue»
Posted by satyajeet 1 year ago  |  Categories: Anal, Fetish, Mature  |  
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My Friend Sue

Sue and I were neighbours that occasionally bumped into each other in the village. One day Sue invited me back to her house for a cup of coffee. As we sat on the sofa together I got the distinct feeling that she fancied me. I brushed away the thought until she said "do you think me tits are too big?"
I couldn't believe my luck!

"I suppose its possible" I said, feeling my 8" cock growing harder In my boxer shorts.

“Why don't you show me what they look like?" I said adventurously.

Sue pulled her shirt up and revealed her huge beautiful knoc... Continue»
Posted by barrios 6 years ago  |  Categories: Anal, BDSM, Hardcore  |  
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My Other Daughter Part 5

I knew it was not going to be long before Ally showed up at my door again. However, with a friend in tow was not expected.
I had been home about an hour and finally relaxing with everyone out of town for a few days when a knock came.
"Come in" I shouted.
"Hi daddy. I hope you don't mind that I came over" Ally purred.
"Oh this this is my friend Cara."
I said hello to Cara but my eyes were glued to her body. She stood about 4'11" and maybe wieghed 105 with a 34-28-36 figure. It was further accented by the almost see through summer dress.
All excused herself while I got some drinks out an... Continue»
Posted by IndieMe 3 years ago  |  Categories: Anal, Fetish, Group Sex  |  
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Shower fuck.

A few months back, my boyfriend and I went on a weekend getaway to the beach. I always get a little frisky when traveling, but this was my first trip with my new boyfriend and I knew I was in store for a lot time on my knees sucking cock and getting my ass plowed. I was feeling particularly hot and bothered and I could tell by Joe's hard-on bulging in his pants during the car ride, that he was too.

I met Joe online, but we're a good fit. He works in insurance and would be totally boring if it wasn't for his huge cock. Joe acts straight, but once he's in the mood to fuck all he wants to do h... Continue»
Posted by BearCubaDub 1 year ago  |  Categories: Anal, Gay Male  |  
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toy time

This takes place 5 yrs after the last story.

Which is 6mths ago. All my stories are true.


I'd been looking forward to Friday all week, not because it's the end of the week, but because I had a annual leave day off work. I woke up nice and early so I could drop my girlfriend at work. After that the day was mine until I had to pick her up again at 5pm...

I rushed home, took a shower, had a smoke and then got out the toys....3 butt plugs in increasing sizes, a cock ring, a inflatable vibrating butt plug and a 8" black suction cup dildo....mmmm my mouth was watering. 

I lived up a... Continue»
Posted by bangoskank2 2 years ago  |  Categories: Anal, First Time, Gay Male  |  
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1st time double penetration

Time for my yearly check up with Dr. Woods. I love my doctor, I have been seeing him for several years. There has never been anything sexual with us, but I have caught him staring at me at times. Any woman would know how that is when a man looks at them a certain way. I also know any woman would love to be his patient! He is 6 foot 2, brown eyes, and silky wavy brown hair that you would love to just run your fingers through! Muscular with 6-pack abs. I’ve heard many women talk about him, but none I knew conquered him yet.
This appointment was going to be different; I was making my husband go ... Continue»
Posted by Ch3rryLove 1 year ago  |  Categories: Anal, First Time  |  
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Poker game (Public Sex - 1st Part)

Last three months I have been playing poker online and winning serious amount of money. Still I did not have feeling about playing live, so I decided to participate in i*****l poker game.

After two hours, I lost money, but leader in game offered to me loan. I accepted it, without knowing that I will have to give him back in next 5 days. Pure me, I lost all money after some time and now I was in bigger problem - I had to pay loan in 5 days.

Next morning, without smile on my face, I sat down on computer and visited my favorite web for online dating. Usually, I am getting lot of messages, b... Continue»
Posted by hotsandra94 1 year ago  |  Categories: Anal, Hardcore, Voyeur  |  
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An Adventure...

I was home alone and very horny, decided to check out some male sites and see what was going on. I found a site that would let you register for free, so I signed up and started to surf.

I came upon an ad that was close to the campus, the ad read "want to have some fun call (7**)***-***9..." Using my throw away I called and a very pleasant voice answered I explained that i found the number on a web site and asked if he placed it there, his answer '...yes, are you interested and want to have fun...' I answered in the affirmative and he continued.

'...Come to 7468 El---- Blvd. unit 237, ... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Gay Male, Hardcore  |  
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First time Oral!

Back several years ago I had a gay friend named Barry. He was a sweet guy and fun to hang out with. We would do the gay bars in my town about every weekend. Barry ended up meeting and dating an older man named Larry.. Larry was quite well off and had a huge house on the edge of the city.
We all became fast friends with the owners of one of the bars. Gary was telling us one night that he had hired a new DJ.. A straight guy name Jodie. He assured me that he was an amazing looking guy. He was due in town that coming Thursday. The only thing was that the landlady at the apartment he was going t... Continue»
Posted by dripinwet 3 years ago  |  Categories: Anal, First Time  |  
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Hot Horse Ride - # 4

Naughty Nikita needed more merry sexy experiences after I rode her so hotly.
Her horny sexy stallion showed his interest, smelling the feromones from her blond furry fanny. Her sexy smells brought me back to lusty life as well.

While she gazed in amazement at that growing member, I told my nubile lovely looking cutie to get on all fours and arch her spine on offer and open up.
She sweetly obied my orders and expected hornily me to enter her hottest hole.

I didn´t dare to disappoint my merry mare and took her anal cherry as first.
Our moans magnified by the heavy breathing of the stall... Continue»
Posted by petdyke 4 years ago  |  Categories: Anal, BDSM, First Time  |  
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my first time

I placed an add in Craigslist in my area describing that I was a very curious closet CD looking for my first experience. After MANY replies (all of them were either from freak-kind of guys, or someone that quit right away), I got in contact with a guy that seemed to be the right one. I was interested in meeting in the woods in one of the many parks around this area and he agreed on that (after we exchange some pics to “known each other” a little and be OK with what we were looking for).

I arrived in my truck to this very isolated area and I saw a single vehicle parked there (was very nic... Continue»
Posted by pamcdnc69 3 years ago  |  Categories: Anal, Fetish, First Time  |  
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Hunting Cougars

Hunting Cougars

We had got naked and we sat on the bed. She slowly crawled away from me, looking back over her shoulder making mewing noises like a big cat. Her pussy sliding between her legs giving me a fabulous view of her womanhood. I crawled over the bed towards her and grabbed her hips, there was a little giggle from her, I don’t think she really wanted to get away...
I slowly was kissing her cute ass and asked her what she would like me to do next...
She answered “Fuck me like a big cat!”
I knelt up behind her, and slowly rubbed her clit with my cock, slowly feeling the soft sl... Continue»
Posted by paddy57 3 years ago  |  Categories: Anal, Hardcore  |  
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