'anal sex' stories

Microscopic Transsexuality

Lily's first plastic cock adventure.

Microscopic Sexuality and Lily's Plastic Cock Lily had been told that there was something 'masculine' about her desire. She often thought about what this meant. In an age where we are all over the idea of 'essentialising' and attributing certain traits exclusively to men or to women, is there a sound basis for saying that certain desires belong to a certain gender? Also, much of modern...

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Pegged by My Wife

A married couple discovers the joy of pegging.

I don't know when I first got interested in pegging specifically but I've enjoyed various toys in my ass for as long as I've been sexually active. The first time I tried a toy in my ass while I was jerking off I was maybe 21. I came so hard I couldn't believe it and from that moment on I was hooked. When my wife and I first started dating I kept quiet about my little fetish but eventually it came...

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An Anal Attentive Boss

He gives his attractive older boss when she craves.

THE WORKPLACE AFFAIR BEGINS My eyes opened slightly as I slowly work up. I was in an unfamiliar bed with unfamiliar surroundings. Everything that happened came back to me and I thought that this time I had really fucked up. My boss, Eleanor Watkins, had had too much to drink the night before and I brought her home. My only intention was to get her home safely as she had been in no condition...

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What are You Doing?

My girlfriend's first anal experience.

I groaned and rolled over in my bed. The dim light coming in through the curtains told me I had slept a little later than usual as I sighed and pulled the blankets closer. I felt my girlfriend shift slightly next to me, her naked ass pressing against the side of my leg. Memories of last night began drifting back to my mind through the fog of morning. We'd been out with friends in the city, a...

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Mommy, I Love Ya Ch. 03

A family that fucks together stays together.

A brief recap, incase you have not read the first two chapters. Wilson Butterworth III, started an incestuous relationship with his mother. He has penetrated the vagina of his sister Naomi. His Mom keeps referring to Wilson's father being killed by an "IUD' in Iraq. Actually a roadside bomb is known as a "IED". His Dad's personal effects, returned to the family by the military, included his...

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"Me-Too-- Fuck You!"

A real bad cop is finally caught by me-too females.

title- "ME--TOO, FUCK YOU" content- ANGRY LAPD COP CONFESSES ABUSIVE SEXUAL BEHAVIOR NOTE- This story contains abusive sexual practices that have been revealed and identified by the Me-Too Movement. If such details tough for you to handle, I sugest you skip this story? The truth may set you free but there is always a price to pay after learning the truth. ALSO, this story was...

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My Mom's New Husband Ch. 03

A day at the gym gets strange then a swim changes everything.

Summer seemed to drag on as the days slowed and the sun intensified and the heat from inside me raged on. I was now fully aware that I had an alter-personality submerged inside, a man that only one person on earth new about. And he was taking full advantage of it. My step dad held some sort of spell over me that I couldn't quite crack. My mom's job made it so I went days and weeks...

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Icky Vicky Roberts

Headmaster makes young man his toy.

Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story has been edited by myself, utilizing Microsoft Spell-check. You have been forewarned; expect to find mistakes. .* Stephen Hebert looked out the window at the courtyard of the Academy. From his third story window, he had an unobstructed view of the entire...

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The Comfort Girl Ch. 03

Evelyn Gets Between the Brothers.

If you make it to the end, please vote and/or comment. I love hearing from you. * Evelyn awoke writhing. Her limbs tangled in bed sheets. Another wet drag of a tongue on her pussy made her eyes spring open wide. She saw Wesley's head between her supple, sensitive skin, suckling at her core. God, this must be some kind of hell. His hair tickled her inner thighs as he continued his...

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Icky Little Vicky

First date ends up with fat girl on her knees.

Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story has been edited by myself, utilizing Microsoft Spell-check. You have been forewarned; expect to find mistakes. .* Tori Long flipped the switch that turned off the numbered sign of her register. The customer continued to unload her grocery cart, unaware...

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A Game of Basketball Pt. 08

A Funeral and a Dance.

If you couldn't tell, this is part 8 of an ongoing series. The story contains a male 18 year old topping a transgender 18 year old girl. You did read that correctly. This story contains anal. If you don't like that, don't read it. It is a really emotion heavy chapter. And really long. Hope you enjoy. * After The Santa Barbara Tournament After we got home I went straight to...

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Tablet Master Ch. 05

Pseudo Master.

Pseudo Master Everyone but Wasp, the Captain and the dying seaman had cleared the room. Shadyss was still covered in blood after ripping that seaman's head off, but she couldn't care less as she placed her forefinger on the dying seaman's forehead before reciting an incantation. The tip of her finger produced a faint green light that engulfed his body, glowing brighter at the back of his...

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Coming home after a business trip.

Note: This is the last chapter in the trilogy starting with Worth Every Yen and continued in A Few Yen More. It will not make sense without having read those first. * The alarm on my phone wakes me far too early to a room that's still dark. I turn my head to the left, then the right, hearing the bones in my neck pop. The noise seems loud to me, but it is not enough to cause either...

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Confluence of 3 Stories

3 life stories end and begin anew inside Annette.

Beauty lies in the eyes of the beholder. What one finds pretty may not be of so much appeal to another and vice versa. Some objects and some people on the other hand are liked by most people who set their eyes on them. Annette was that kind of pretty which most men couldn't take their eyes off. Annette entered her two bedroom apartment and kicked off her running shoes. She took off the...

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The Monday Night Club Ch. 03

Toby and I spend some time...

When I saw Toby at school the next afternoon, he walked up and gave me a quick shoulder/side hug. "How are you, man?" he said, quietly. "Horny as hell," I confessed. "Can't think about anything else... I'm not gonna make it to the weekend. Can we get together at your house before then?" I knew his mother was gone a lot, traveling for her job, so it was a good bet to ask. His face...

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Gay Students at Private School Ch. 04

Cody and Dougie become femboys. Dougie gets a new lover.

SATURDAY AND A NEW ADVENTURE Cody and Dougie had been instructed to come to the Principal's home right after breakfast on Saturday. They did as they were told leaving Jeremy and Ronnie to entertain each other. When they arrived at the house, they were greeted by the wives Jamie and Samantha. The two were dressed in miniskirts, thigh high hose and see-through blouses. It was amazing how much...

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The Flash of an Affair Pt. 02

It's all over but the shouting.

Emily stopped as she entered bedroom and gasped as she heard the sounds of the shower. She noticed the two suitcases open and full of clothing. He was still here!! Her heart leapt in her chest. She moved through the bedroom and into the bathroom. She said a quick prayer of thanks and moved to reclaim her husband and her marriage. Henry stepped back from the water and reached for the shampoo,...

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Hellish Retribution Ch. 02

Marcus finds help, and Elise learns of Wilkins' intentions.

"Officer Bates, please! My daughter is in danger!" "Dammit Richardson, I told you I can't help you!" Outside of the police station stood Marcus Richardson, engaged in a heated argument with an older man. Just two hours ago, he and his daughter Elise were lured into the ruins of the old demonology lab where he used to work and ambushed by one of his old coworkers, Russell Wilkins....

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The Monday Night Club Ch. 02

I get to know some school-friends better...

As Ricky was starting to slip out of me, I noticed a slim black guy standing a few feet behind him. "Hey, Emil, how you doin', my man?" he said. "Toby?! What the fuck?!" I answered in shock. "I didn't see you here before! Wow..." "I just got here; had to work late... Glad I haven't missed you , though, man. Mind if I take this dance, Ricky?" Toby was of east African...

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The Snowstorm

Mary's found in a snowstorm by three men who warm her up.

Consciousness came back to Mary slowly, her mind still hazy as her eye fluttered open. She moaned softly and winced as the light seemed too bright, then gasped in pain as the nerve endings in her body began shooting bolts of pain through her. Her head began pounding, only the worst hangover she'd ever had coming even close to this feeling. "I think she's waking up", she heard a voice say. It...

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The Monday Night Club Ch. 01

Abduction, Initiation, Education...

I guess you'd say I was a nerd in high school-- neither athletic enough to run with the jocks nor cool enough to belong to the 'in' crowd. My few friends were on the outside of things, too, it seemed. A kid down the street had showed me how to jerk off sometime in the seventh grade, and I escaped to that fantasy world at least once a day after discovering it: Everyone willingly cooperated...

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Ballet School Ch. 07

Chris Explores New Limits.

Chapter Seven-Atlas and Friends He told me to take a couple of days to rest and heal. The next thing we do, will blow your mind. He approached me after I was done training a couple of days later and asked me how I was. The day after our marathon sex session, I was in pain. My ass was sore and I felt bruised all over. I went to classes and back home straight to bed and slept right...

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Trevor's Dad

Broken in by a man's man.

I was always secretly fascinated with men. I am a man, so you could say there should be no surprises to be had, but of course everyone is different. We all have a penis and testicles. We all masturbate, and when we do, we produce something that goes by the glorious colloquial name of spunk. Technically semen. But spunk is dirtier. Naughtier. Semen is for impregnating women. Spunk is for fun....

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The First Time

Judy pegs Jed for the first time.

She was working the dildo in my mouth like it was her real cock and she could feel all of the moves and thrusts. Her body moved like this was natural for her to be shoving a cock in a man's throat. She coached me at times by telling me to move faster or slower. At times, she grabbed me by my ears and would make thrusts, in and out, just like she wanted so that she could control the feeling and...

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Au Restaurant Ris de Veau

A threesome enjoys more than just the gourmet meal.

Chapter 1 - Friday Dinner Date Friday night is date night and at least twice a month, we go to a nice restaurant on a double-date with our close friends Fred and Barb. Tonight, we had 8:00 dinner reservations at my favorite French restaurant, Ris de Veau, named after their signature sweetbreads dish, my favorite meal. It had been a hard week, closing out the second quarter at the Bank,...

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Destinee and Destiny Ch. 01.3-4

Destiny's story and Siblings finally come together.

I just want to thank you all for hanging in there with me so far. This is the true meat of this novel, and I poured everything I could into it, so I hope you enjoy! Also, I wanted to take a second to thank everyone who has favorited and taken the time to comment on this: _Anonymous user with 'my 2 cents' -- I know the chapters took a different pace then I led up to, but that's what I was...

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Blackmailed Bride Ch. 13

Brooke loses her anal virginity and not to Tanner.

This chapter contains oral and anal sex in addition to vaginal intercourse, nudity in artistic posing, some lesbian touching between lovers and non consent/reluctance. If you don't like those things, don't read more. You were warned. A reminder that in this fantasy world, STD's don't exist so the only consequence of unprotected sex would be pregnancy if other methods were not used. *...

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My Sissy Wife Pt. 03

Continuing, the morning after our anniversary.

Continued from where we left off in part 2. For everyone who read this and liked it, favorited it, left a comment, or sent me a message: thank you, you inspire me to keep writing. If there's anything you'd like to see here, or questions in general, please don't hesitate to reach out. Peace! * Somewhere in the night I must've rolled off you, I woke up before morning light once...

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The Slumber Party Ch. 15

Jessica meets Robert, and they click immediately.

Jessica loved her job. There was something so heartwarming about teaching elementary school. She was usually in charge of third- and fourth-graders, and she thought that was just the perfect age: young enough that they still respected adult authority and hadn't descended into the depths of teenage hooliganism, but old enough that they were starting to become rational creatures. And they were...

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In Your Care

Man and transgender woman meet, slowly fall for each other.

I sighed as I agreed to work overtime on Friday. Why not? I didn't have a date, hadn't had one in over a year. It seemed to be an escalating cycle: since I didn't have dates, I was focusing more on my work, and that led me to do things like take extra hours, which left me less time to be social. Well, at least the money was good. I decided I would need to break the cycle. On Saturday I would...

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