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It all began when Cindy stuck her finger up my ass. She was running her tongue lightly up and down the shaft of my cock, but paused for an instant to gauge my reaction. I moaned slightly, appreciatively. It felt good. She smiled and began slowly moving her finger in and out.

We were naked on her bed in her apartment on a Saturday morning, the sunlight streaming in through her bedroom windows. At first, I wasn't fully awake, although Cindy did a fine job of waking me up. She had started nibbling and nipping at my balls before moving up to my cock. And now she had a finger up my backside. I was awake and she had my full attention.

It wasn't the first time that a girlfriend had stuck a finger up my ass, but this was different. Cindy wasn't stopping at one. She began working a second finger inside me and then a third. She stopped and looked up at me as she slowly fucked me with her three fingers.

"How does this feel?"

"Hmm," I moaned to myself. "Feels wild. Strange. Really good." It felt so full and warm. "Don't stop."

"Oh no," she said smiling. "I am just getting started." With that she took my cock in her mouth and starting sucking in rhythm with her fingers pumping in my ass. I didn't last long. Between her mouth and her fingers, the orgasm was shattering.

She cuddled up next to me and began kissing my neck. Then she whispered, "Have you ever been fucked in the ass by a woman?"

I was startled, "Ah, no." I paused. "Nor by a man either."

She laughed. "That much I figured. You are too straight to swing both ways. Suggests a lack of imagination, you know."

It was my turn to laugh. So, I was too straight. Well, we are what we are. Cindy was bi and had broken up with a long-term girlfriend just before we met. She was my first bi girlfriend, or at least the first that I knew about.

I looked into her eyes, a lovely shade of hazel. They seemed to smile back at me.

"Well then, have you ever fantasized about a woman fucking you with a strap-on?"

Wow, I thought. "Can't say that I have. I know, a failure of imagination."

With that she rolled over on top of me, held me down by the shoulders and gave me a long and passionate kiss. Then she sat back, still holding down my shoulders. For her size, she seemed suddenly very strong. She had a wicked smile on her face and a wild look in her eyes.

"I really, really want to fuck you with my strap-on"

I wasn't sure what to a say, so I said the first thing that came to mind. "I didn't know that you had a strap-on"

"I have two," she said her smile growing wider. "Wanna see?"

"Sure," I replied, amazed how we just went from imminent sodomy to show-and-tell.

She hopped off me and went into her walk-in closet. In a few minutes she came out wearing a black harness and a not overly large dildo which was, somewhat incongruously, blue. She had a big smile on her face and wiggled her hips, making the rubber cock swing back and forth.

"This was in the last of the stuff I picked up from Nina's. What do you think?"

What did I think? I wasn't sure what to think. I knew that she had gotten the last of her things from her girlfriend's apartment, but had no idea that sex toys were in the box. Clearly I still had much to learn about Cindy.

She stood there, beautifully naked, except for the harness and the swinging blue rubber cock. The goofy grin on her face made it all seem playful and silly. Kind of sexy. Then again, the cock felt more than a little threatening, especially given its intended destination.

Could I handle it? Physically? Emotionally? Would it be liberating or emasculating? Was my masculinity all that fragile that it could be shattered by a blue rubber cock? Should I grab my clothes and run for the door or bend over and submit?

As I was considering my options, I realized that my cock was voting in the affirmative. Given that I had cum just a few minutes before, the erection was impressive. Perhaps, I was overthinking the situation. Best to go with my gut, or in this case, the guidance provided by my cock.

"I think you look very sexy," I finally replied.

"So can I fuck you?" she asked, putting an extra emphasis on the hard percussive "f" of fuck. It was both a question and a challenge.

I took a deep breath and said, "Sure."

She raised an eyebrow and stepped next the bed, holding the rubber dildo so that it was pointing straight at me, inches from my face. Then in a tone I didn't expect she barked, "Suck my cock, boy!"

I started to suggest that that wasn't really necessary, but, as I opened my mouth to speak, she shoved the blue dildo down my throat. She grabbed the back of my head with her other hand and pulled me forward.

The dildo wasn't that long, but I gagged as it hit the back of my throat. My eyes started to water and I jerked my head back against her hand. She pulled the cock back but kept fucking my face. Now that I could breathe, I started to get in the rhythm and began to move my head to meet the cock, taking it deep, but not enough to gag. She moved her hand from the back of my head to caress my cheek and said softly, "Good boy. Suck that cock."

I am not sure how long she fucked my face, but I sort of slipped into the surreal vision of a blue rubber cock being shoved down my throat while watching Cindy's breasts bounce slightly as she thrust her hips toward my face. Then suddenly, she stopped.

"You're a good little cocksucker, now aren't you?" she said with a evil grin. "Get on your hands and knees. Now we'll have some real fun."

I did as she directed, got on my hands and knees on the bed. I wasn't sure what to expect. Given how rough she was fucking my face, would she come at my ass like a battering ram?

Instead, she walked away to the bathroom. I heard water running and soon she was back with a warm washcloth which she rubbed against my ass.

"Gotta have you kissing sweet," she purred. She got up on the bed and leaned forward, kissing and licking my backside. She ran her tongue up and down my perineum, licking my scrotum and then flicking across my asshole. Then she sank her tongue in my ass, fluttering around and then stabbing in and out like a tiny cock. It felt warm, exciting and relaxing at the same time.

I heard her squirt lube and felt the cool wetness as she worked one lubricated finger into my ass, and then another and another. She slowly finger fucked me as I groaned happily.

"If you like my fingers, you are going to love my cock." She gave my ass a hard swat pulling me out of my revery.

"OK, roll over on your back, ass on the edge of the bed, a pillow under your hips. I want to see the look in your eyes as I fuck you."

I got in position. My knees were spread, my asshole slightly elevated. I have never felt so exposed and vulnerable. She stepped up between my legs. Her eyes seemed to burn with raw lust.

I felt the cock press against my asshole. Rather than ramming it in, as she had my mouth, she was very gentle, easing her way in the puckered gateway. The blue cock was much bigger than her fingers, but slid in smoothly. I closed my eyes and gasped at the blend of sensations - pressure but not pain, a sense of complete surrender, of submission, and the simple joy of losing control.

She began to move in and out, slowly at first, but then fast and faster. Soon she was fucking me hard, slapping my ass with her hips as she drove the cock into me, then pulling most of the way out before slamming back again. The strap-on jabbed hard across my prostate creating a feeling that was brand new - intense, and pleasurable yet almost painful.

It was overwhelming, too much and not enough. I couldn't take it and I wanted more. I found myself croaking, "Fuck me, Cindy. Fuck me." And she did. Harder and harder.

Cindy slid one hand down the top of the harness and rubbed her clitoris. "Jerk-off," she commanded. "I want to see you come."

The sensation of having my ass pounded by the strap-on merged into the sensations as I jerked my cock to life. The stimulation of my prostate as the dildo slammed into it were as powerful as the pleasure from my hand jerking the shaft and glans. I watched as Cindy grew closer and closer toward her own orgasm.

Suddenly, if was all too much and I came. Cum splattered on my belly as the world seemed to explode. Cindy kept driving into me with a manic frenzy, until she opened her mouth in a silent scream and her whole body began to shake. She slumped forward slightly with the strap-on still buried inside me. In a few minutes, she stood again and pulled out. I felt oddly empty.

She took off the harness, dropped it on the floor and climbed onto the bed. I was still gasping for breath. She cuddled next to me.

"So how was it?"

"Amazing." I ran my fingers though her hair. "Can we do that again?"

"Sure." she relied. "Next time, maybe I'll use the bigger dildo."

"Oh no," I said, feigning horror. "Let's practice more with the blue one. That one is big enough. I won't be surprised if my ass is plenty sore tomorrow."

"Maybe so. Will it have been worth it?"

"Absolutely," I replied.

I turned and kissed her, then whispered in her ear, "You can fuck me in the ass any time, my love."

She gave me a wicked smile. "An offer I shall not refuse."

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The wonderful thing about long lasting friendships is that they often create strange, but very interesting combinations of people. In a small group of friends, who have known each other for years, where the need to hide uncomfortable truths or embarrassing facts should no longer be present, where the need to impress and excel at things should no longer be needed, where genuine friendship should allow everyone to be who they really are, the question still remains – do we ever really reach a...

3 years ago
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Dream Fantasy 2

Dream Fantasy 2 By Paul G Jutras "Hello? Hello?" Jason said into the phone. "Can you hear me?" In a pink sailor top, pink ankle length skirt, white bobby socks and black Mary Janes, Paul sat on the floor, on his knees. Tears ran down his face as he cradled the phone in his pink polished hands. He closed his eyes as he listened to Jason's voice. "Hey, what's wrong?" Jason asked to the sound of silence. "Don't ask," Paul said, crossing his arms under his breasts forms. "Mom and...

4 years ago
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Cassie

Introduction: sorry about the story set up, I don't like giant walls of text. “Knock it off already.” Cassie had the remote control firmly entrenched in her hand and was doing her best to keep it out of reach. The TV was stuck on basketball, which sucked. I knew that there had to be some combination of leverage and brute force that would cause my sister’s fingers to open and let me gain command of the remote. Getting up and walking to the TV was simply out of the question.“Knock what off?,” I...

3 years ago
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Aggy Book 1Chapter 47

"Can I help you?" Angie turned to a red haired woman about her age. 'Deity. Who is she? The way she holds herself;' "The lounge? I was told ... directed to the lounge. I believe there is be a confidential discussion and I have yet to complete my business." "I'm Sally McGraw, dogsbody and general factotum, the lounge is over here. Coffee?" "Angie Merton. Thank you. Both please before you ask. Have you any idea how long they'll be?" Sally shook her head, returned to her office...

4 years ago
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The Great Eviction Event Unfolds Chapter 3

Jesse-2: Friday, December 12, 2014, 7:21 pm, PST Jesse roused, shaking his head. According to his watch, it was 7:21 pm. Looking about, he recognized the back yard and crashed Orange Line bus. The damaged shed had collapsed completely onto the objects inside while he slept. No--he’d passed out. Digging out his iPhone, he checked for phone calls or text. Nothing but annoying automatic notifications. He called Carolyn again. “Sweetie, it’s me again,” he said to her voice mail. “Call me as...

2 years ago
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Taking over the Hudson Family 1 by 1 part six

I laid their looking up at the ceiling for what felt like hours. I had not been able to sleep after what had happened last night. I was still reliving fucking my best friends father in front of her and her brother while they fucked in front of us. It all seemed like some kind of dream. Never though in my wildest dreams would I have been able to dream any of this up. I rolled over to my side thinking that would help me fall asleep but I had no luck. It did not help that Carrie was taking up...

3 years ago
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Earths CoreChapter 16 Invitation For A Fight

Clergyman raised an inviting hand toward the fat middle age man and smiled. "You look like a good proficient fellow". It was hard to say if he was mocking the man or recognize something in him, which to everyone else but the fat man seemed very unlikely. "Haha ... See, son, among all the people here, it is your father that a professional fighter deemed a worthy opponent". The fat man told to the boy beside him who also shared a proud smile of been the son of the only man Clergyman called...

3 years ago
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A Lucky Brother In Ottawa

The name is Clarence Pierre Romans, and I’m a gentleman with a story to share with you. A tale of self-exploration and sensuality, if you will. Presently, I’m studying business administration at Carleton University in the City of Ottawa, Province of Ontario. I have lived here since early 2010. I’m originally from the City of Brockton, Massachusetts. I was born there to a Haitian mother and Puerto Rican father. I consider myself African-American, though I’m obviously biracial. I stand six feet...

3 years ago
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Losing My Virginity To An InLaw

I’ve been sexually active for as long as I can remember. The first memories I have of other c***dren my age are those of a sexual nature and I suppose is the reason why I am such a sexaholic these days. For the sake of sharing with you my personal experience, let me tell you how I came to realize the beauty of a naked girl’s body at an early age.When all of this started I was very young, too young to know about right and wrong and too old to be content with things the way they are. I was...

3 years ago
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His First Sex Toy Part I

This story is the first of two told from two perspectives, of a guy and girl's first experiences with a sex toy. I felt best to separate for those who didn't want to read the other side.*A knock at the door brought the Delivery Guy, whereupon Steve opened it and signed for the parcel. He took it into his apartment and placed it on the table. The anticipation of opening it made him feel young once more, like a child at Christmas.The packaging was discreet, but inside contained a special item...

Toys
4 years ago
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Hookahed

Koontz was a useless decadent fat fuck, Bachman decided as he slipped out of his room in the dark hours of the morning. How the greasy slab of lard had ever gained control over the west side was a mystery to him. Well it wouldn't be a mystery for long, Bachman thought as he checked the corridor outside. It was empty. Bachman wasn't surprised. Security was a joke. He hadn't seen a guard since he'd left his car and been shown into the building. At the door he'd been greeted by Koontz...

4 years ago
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Stepdaughter Jenny longs for it

I’m looking for a guy who likes to fuck from the backside. my asshole is perfect for a pounding. Come onand give me a good hard beating. Please help if you can!if you Real Then Contact Me Now :www.miamalkova.websiteIt had all started in her stepfather's bed. Pretty little 18-year-old Jenny had begun to kiss her way down her stepfather Mitch's hairy chest, slowly, inch by hairy inch, adoring the taut skin and musky smell rising from his groin. Mitch lay motionless as his ultimate fantasy grew...

2 years ago
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A naughty late night burglar at home

I parked at our driveway that late evening, feeling very tired. I was hoping my loving hubby would be there; but our house looked dark and empty. I walked into the leaving room and turned a light on.I just wanted to enjoy a quick warm shower and drag my nice hubby to our marital bed; since I was also horny besides tired and needed a good sexual relief. My loving Victor would give it to me.As I looked inside, I gasped in shock and surprise; as I saw a naked man sitting on a chair, his head...

4 years ago
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Dominating Victoria

Not everyone in the yacht was a celebrity, some of them were just stunning models, plucked from their previous existence by the owner of the boat, one of the wealthiest men in the world. All of the women on board would qualify for Playboy and in fact many of them had. There were only a few men, the billionaire himself, a couple of the senior executives from his companies and a few random celebs who knew the billionaire from the parties he threw and were there to enjoy his largesse. Music blared...

4 years ago
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Himura BattousaiChapter 3 Descendant of Tokyo Samurai Myoujin Yahiko

The day after Kenshin defeated the Sword-bearing Police, rumors flew and people gathered in the Kamiya Kasshin dojo. Kaoru: Wow, there's more than fifteen people here! The Kamiya Kasshin school is revived! Kenshin: This isn't good. Kaoru: Huh? Kenshin: Excuse me, everyone. I'm not originally from this school, and I'm not taking any pupils, so if you came because you saw the disturbance yesterday, I'm sorry, but please leave. (Kaoru stands staring at an empty yard.) Kenshin: Well,...

3 years ago
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ANNIEpart 1 THE HEN NIGHT

The girls were in a man free zone in the large club room: men were not allowed in on hen nights. The crooner and the blue comedian had done their acts and now the male stripper held centre stage. he was blonde and muscular with a six pack and with a tanned body devoid of hair. Annie and her three companions where sat at a front table not sure if the huge bulge in his posing pouch was genuine. Annie was the bride-to-be, her companions her bride's maids. Annie was tipsy and enjoying herself...

Straight Sex
4 years ago
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It just happened

Oh, Brother what have I done!A year into transition I wanted to pay a visit to my sister in the city and while there meet with the brother I barely knew. I left home when he was seven any only saw him maybe twice thereafter.I decided to see my brother first as he lived just off the main highway on the way to my sisters.He spotted me in the driveway and ran up to open my door. A gentleman I thought.Once inside he offered me a glass of wine and grabbed a beer for himself.We did the standard chit...

3 years ago
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Edge of MadnessChapter 5

She walked though the door and saw her husband sitting in his favorite chair watching t.v. He wore a scowl on his face. Not a good sign, she thought. She'd try and be cheerful though, maybe that would change his mood. "Hi honey!" she called out to him as she walked into the parlor. He saw her holding her picnic basket and beach bag and noticed her cheeks all ruddy. "And where the hell have you been? I've been sitting here for over an hour. I'm tired and I'm hungry!" he growled at...

3 years ago
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Christmas With The Family

Christmas With The Family   An Original Work by Donato, Copyright 2007       Harry and Todd had been friends since grade school and now were freshmen at the same college, State University. It was almost Christmas and Todd had invited Harry to stay with he and his family as Harry's folks had been called out of town on a family emergency. It was the first time Harry was not to see his folks over Christmas and he was really down in the...

Mature
2 years ago
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Susan and Jason Naked In SchoolChapter 1 Monday

SUSAN I was so preoccupied with being nude the first day that all other thoughts were pushed out and I couldn’t even concentrate on school work. Everything went by in a blur until after first period. First period social studies didn’t last long but this was only because of the time we spent in the principal’s office getting naked. Harriet, John and I missed the majority of this class. This was expected of first day Program attendees. However, I was wondering about poor Jay. He didn’t have...

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