Anal Porn Stories
Page 8

GETTING BEVERLY'S FIST

Beverly was my girlfriend we had been dating for a little while and I had her over for the weekend we had a nice day shopping and stuff but then we came home and she said she wanted to have sex...I was totally up for it but she had that look in her eye that night like she wanted to do something nasty to me she got me naked and got me on the bed “I'm going to stretch out your asshole for you!” She stated “Get on your hands and knees!” She commanded I obeyed I was a little nervous as to what she might do but also a little excited too she got some k-y lube from the nightstand the stuff I use when... Continue»
Posted by laceysgirl 21 days ago  |  Categories: Anal, Fetish, First Time  |  
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My First Time as Sara... Pt. 05

crossdresser – sissy – lingerie – anal – trap – oral – transexual – stockings – coquette – sissy boi

I've become Sara now for just about a year. One year of exploring deeply who I was, my past, my history and who I've become at this moment.

I was no longer just John, the meek man who was dumped by his fiancé for not being man enough. That skin was shed. Instead I became Sara. I became empowered and in charge of my life. It was as if panties and heels, cute girl next door dresses and sultry and sexy lingerie gave me a sense of empowerment.

I also had Steve with me the entire way. He be... Continue»
Posted by naughty_bi_interest 21 days ago  |  Categories: Anal, Fetish, Shemales  |  
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Not So Sweet Caroline

A part of me was wondering how I got there but most of me was at her attention.

I lay there in her bed nude, my swollen cock throbbing with every heart beat. My arms were tied to the bed at the wrist. My legs tied at the ankles. I am a strong man but she had overpowered me. I couldn’t have been her strength alone there is no way. Still I lay there completely at her mercy no way to wiggle free.

She just stood there contemplating her next move. You could see the satisfaction in her eyes as she had beaten in her game of chess. The only thing she was wearing was her glasses, the same glasses... Continue»
Posted by jhoney67 21 days ago  |  Categories: Anal, BDSM, Fetish  |  
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The Health Teacher

These stories are somewhat true and all names used are altered to preserve privacy. This is a continuation from "The Math Teacher" so check that out as well! ;)

Months had passed since the incident with Ms. Brisk and we had a sex buddy kind of relationship. We'd meet up whenever she felt the urge for a good fuck and I was never one to turn down a woman's request. Everything was fine until had to go to college. I finished my freshman year with relative ease and when I returned home, I found that she was actually dating someone while I was away. I wasn't mad though frankly. I was somewhat rel... Continue»
Posted by cjosh10 21 days ago  |  Categories: Anal, Hardcore, Mature  |  
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Taking care of my sick sweetheart

This happened quite some time ago, back when I was still a teenager in school, right smack in the middle of that golden age where you'd still be exploring your own personality, but absolutely couldn't wait to start exploring another person's body all at the same time. This other person, let's call her Annette, had been in my life for a few months already up to this point. From that first feeble, trembling kiss shortly after we met, we had lost enough of our shyness to finally dare touch each other a little more.

She lived in an apartment building in a relatively small city. When her parents... Continue»
Posted by MickeyD87 22 days ago  |  Categories: Anal, Fetish, First Time  |  
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"Do you feel like taking my cock...

…up your ass?"

I've already fucked her to one orgasm, with her lying on her back, legs spread wide open, me pounding into her cunt. But I haven't cum yet and I desperately need to. I think about having her turn over and get up on all fours so I can fuck her doggystyle, but I crave the feeling of something tighter around my cock. I haven't fucked her in the ass for at least a couple of months. I’m overdue for a bit of buggery, and I suspect that she is, too.

She gives a sharp intake of breath. I know I’ve touched a nerve by bringing up something that she really wants but is too shy to ask... Continue»
Posted by jakew51 22 days ago  |  Categories: Anal, Hardcore, Mature  |  
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Surprise Surprise part 2

We'd been fucking for hours and I'd lost count of the number of times I'd cum and which holes I'd filled with my cum. Her arse, pussy and mouth had each received at least one load and she hadn't cleaned up at all yet. Her lower region was covered with cum and despite working the load I'd shot all over her face into her mouth with her fingers her face still glistened from the earlier facial she had happily received. It was a huge load that had shot onto her pretty face and naturally some had ran down her chin and onto her pert little tits but after so much intense fucking it had long since disa... Continue»
Posted by heyheymymy1984 22 days ago  |  Categories: Anal, Group Sex, Mature  |  
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CD Waitress 4

I didn't know our destination, but we took a slow walk down from the peninsula to the edge of town and strolled along the shops looking in the windows. Several couples passed us, and I could see the men checking me out in the reflections of the glass windows.The local youths were more obvious, and a few made comments just loud enough to be heard, and I knew they would love to feel me up and get into my panties. Other girls regarded me as one of their own, and apprised me quickly as they wandered past. As a loner all of my life, this new acceptance, even desirability, thrilled me.A lingerie sho... Continue»
Posted by satinexinhose 22 days ago  |  Categories: Anal, Group Sex, Taboo  |  
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My First Time as Sara... Pt. 04


crossdressing – oral – crossdresser – heels – lingerie – fantasy – stockings – trap – anal – sissy

I love being Sara and everything it has awakened in me. In the months since I have been with Steve and becoming Sara, I have slowly shredded away my old self like a snake looses its skin. The only time I even dress up as John is when I'm at work. Even then, I have a little bit of Sara with me by either wearing panties and sometimes pantyhose under my khaki pants.

In the months as Sara, I've amassed a collection of clothes and slowly my closet was less John and more Sara. Skirts, bl... Continue»
Posted by naughty_bi_interest 22 days ago  |  Categories: Anal, Fetish, Shemales  |  
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A Latina babe with a surprise

A Latina babe with a surprise

That Winter we had escaped from the New York`s cold weather and had gone for a week to Miami.
My sweet Ana was so horny during these days… On the fourth night, after dinner outside in a nice restaurant, she suggested to go down to the hotel bar and pick up somebody to enjoy a good time for the rest of the night…

We decided finally to go out from our hotel and we ended in a nice pub just a few blocks away from there.
A nice brunette girl, Latino type, started a conversation with Ana.
My wife tried to speak in Spanish with her, but the girl said she only ... Continue»
Posted by Anitaslut44 23 days ago  |  Categories: Anal, Mature, Shemales  |  
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GloryHole experience

I entered through the rear door to the bookstore. It was nearest to the video booths. I knew it pretty well. I stopped by every time I was in this part of Texas. I was already wearing my bodyshaper and stockings under my street clothes. I had came in and purchased twenty dollars of tokens a few minutes earlier. I was clutching my oversize purse that contained my heels, dress, red wig, makeup condoms lube etc. This ABS had a restroom in the booth area. I loved that. I went directly to the restroom. It had 2 stalls and a urinal. No one was in there which surprised me as the lot seemed to be quit... Continue»
Posted by proudman2 23 days ago  |  Categories: Anal, Group Sex, Shemales  |  
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Train Journey -Part I

Hi All,

A bit about myself, i am a bisexual male living in north india and i like to crossdress when am alone or traveling alone. I have to travel a lot for work to various places all over the country and i CD whenever i travel alone and have had a lot of fun with guys and girls.

Well as it happens i had to go for some work for a few days in orissa and my office booked me on the rajdhani 1st class. The train was at around 4 30pm. As i always do on long work trips before going to the train station i went to my regular lingerie shop( the owner knows am a CD, buts another story) and bought... Continue»
Posted by hornyboyind 23 days ago  |  Categories: Anal, Gay Male, Shemales  |  
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Gangbang at Ricks part 5

Gangbang at Ricks part5

All of us left when we got up, I counted Heads (cock heads lol) still 8 nice size, and Kim n Me us Sissy's woke up first, i told her meet me in the shower, we can have fun cleaning each other for the rest of the day. trying not to wake them all up, but i had a big problem Nicks big soft cock head was still in me all night, it's going to get messy, his and Don's loads in my belly, Kim grab that big butt plug try to pull nick out of me, she knew pulled it did a good job pluging back up. she giggled ... Continue»
Posted by mrheat22 23 days ago  |  Categories: Anal, Gay Male, Shemales  |  
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Why my neighbor had to lick my black ass....

I lived in an apartment in my early 20's in a neighborhood you could call up and coming. The neighbor to my left (upstairs apartments) had a bit of a past that I didn't know about until she jumped to the wrong conclusion...

Julie is white...late 20's...with a cute face...and big ass.....We had lived near each other for about 6 months and bantered before that day, but nothing over the top....She was the apartment complex d**g dealer and I knew that......

On Saturdays at 1000 AM, her ex husband came to pick up their little boy Tyler. On one Saturday, "Sam", the ex-husband, parked in my vis... Continue»
Posted by ChocFantasy 23 days ago  |  Categories: Anal, Fetish, Interracial Sex  |  
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The Math Teacher

This story is somewhat true. Names used in story are fake for privacy. I had just graduated high school and I had got a call from my Math teacher, Ms. Brisk, that I had left somethings in her classroom and that if I didn't come to get them that they'd be thrown away. I hated Ms. Brisk's class to be honest. She was always so annoying and got on everyone's case. She did have a fairly nice body though. She was in her late 30s with brown skin. She rarely wore bras so you could visibly see her nipples through her tops and can tell that there was some sag in her D-cup breasts. Her ass, however, was ... Continue»
Posted by cjosh10 23 days ago  |  Categories: Anal, First Time, Mature  |  
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Mr. Vibrator for Pookie

Mr. Vibrator for Pookie

Pookie sat near the end of the sofa. His clothes and book bag with his sheet music were on the other end. He was nearly naked. The only thing he was wearing were the red and white socks that he loved so well. They started high up on his calves and ended over the toes on his dainty feet.

He had his pretty legs spread really wide with his right leg over the armrest. He was very relaxed; he had been in this position a number of times and loved it. Mr. Jamison had told him that after another lesson today with Mr. Vibrator, he had a wonderful surprise for him. ... Continue»
Posted by tankengine123 23 days ago  |  Categories: Anal, First Time, Taboo  |  
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Jacki's Journey into Sissyhood Pt. 02

sissy – pussy – oral – strap on – anal – plug - cum – mistress

I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm d****d across my shoulders and the large cock poking at my backside. I tried to slowly slide out from under Steve's arm, only to have him pull me closer and kiss my shoulder. "Good morning Jacki," Steve said sl**pily as he yawned.

I took my free hand and grasped his erection, and laughed," It seems this guy has been up for a while now."

He chuckled back, "Yeah, well who can blame him h... Continue»
Posted by naughty_bi_interest 23 days ago  |  Categories: Anal, Fetish, Shemales  |  
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Pretending to be Straight - First time!

When I was 29, I was using one of those dating apps where you can choose whether you want to see women or men in your search list. One day, feeling slightly bi-curious, I decided to change my profile to say that I'm heterosexual, just to see whether any women would actually write to me. Interestingly, I didn't get any messages from women, but got a number of messages from both "straight" and gay guys, who wanted to experiment with me. It felt incredibly exciting talking to those guys.

One guy in particular was very very cute, 20 year old University student, quite short, slim, pretty face w... Continue»
Posted by incantation 23 days ago  |  Categories: Anal, First Time, Gay Male  |  
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My First Time as Sara... Pt. 03

crossdresser – oral – sissy – lingerie – stockings – tranny – crossdressing – anal

I've been with Steve for a couple of months and to say I've been happier than at any time in my life would be a gross understatement. Being with Steve has been an awakening. I'm no longer afraid of life. I was shy and timid as John. I didn't make decisions. I didn't take the lead in anything and was easily bullied. My ex fiancé was the worse bully.

As Sara I came to understand a few things. I am starting to understand the power that woman have. I'm beginning to grasp the sway a woman can have when ... Continue»
Posted by naughty_bi_interest 23 days ago  |  Categories: Anal, Fetish, Shemales  |  
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Great Surprise

The story starts with an exhausting day of work. After a long day of work, I walk into the house looking for a relaxing shower and a cool drink. My fiance leads me into the living room and asks me to lay down for a massage. As she is giving me the massage, she whispers into my ear "I have a surprise for you tonight, so I want you to take your time in the shower and get cleaned up well" in a sassy tone that told me that I will enjoy this surprise to the fullest. Thrilled by this; I bite my tongue trying not to ask what the surprise is, so as not to ruin it.

So after a nice long rub down, she... Continue»
Posted by XXXNoBounds 23 days ago  |  Categories: Anal, First Time, Hardcore  |  
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