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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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Perspective: Jacob He pushed me onto the bed and our lips met. “Jacob,” he said, “I can’t believe…” His sentence turned into a moan as I began to pull off his clothes and explore his body. He didn’t need to finish the sentence. I knew roughly how he felt. I had moved into my first apartment three months ago, at the beginning of my second year of university. I wasn't the most prepared student, so as is typical I had left the house-hunting to the last minute. The friends I had made during my...

Gay
4 years ago
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A Train Ride to LoveChapter 7

(Secrets needing to be kept) "I can't make it on Thursday." "Oh! But why?" Sarah asked clearly disappointed. "I have to go away tomorrow and am not likely to be back until - Monday I would think." Sam kept his tone even despite the fact that he was seething. He had gone into work this morning full of enthusiasm, his night with Sarah, adding new life to him. Five minutes in Robert's office and he was spitting nails and seriously considering resigning his position. "I know you...

4 years ago
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On Top of a Mountain

They met on a mountain top. It was snowing heavily and it seemed they had both been stranded in the Restaurant. The last cable-car had already left and because of the weather, they were informed that there would not be another until the next day. Marion was a tall, well-built brunette, about 5’9”. She had silver-grey eyes with a twinkle. Her skin had a bronze hue and her mouth looked delectable. She was dressed in white ski pants and a shirt, covered with a red ski jacket, which could be seen...

3 years ago
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SWORN to SECRECY

Introduction: Enjoy. and Please Please Please Comment.. xo SWORN TO SECRECY She flipped through the papers of potential men. You are seriously not setting me up, with any of these men. She said displeased. Sitting back in her chair with a disgusted look to her face. Madison! Get real you are 35 and still single! I know I am your younger sister. But you need to make an effort if you dont want to be alone for the rest of your life Melanie spoke truthfully. Madison leaned forward and kept...

3 years ago
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My Mistress

Looking out my window, I saw the Cal-Trans truck parked along the curb. Swell, I thought to myself, another fine day with my street closed. But then, I noticed a lovely female worker who stepped out of a truck in front of my sidewalk. She was wearing the standard bright orange reflector safety vest over her blue jeans and a work shirt. Even from across my front yard I could see that she was stunning, with long beautiful brown hair and a gorgeous young face. All morning long, I peeked through my...

2 years ago
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Hard Luck Harlan Lawton Chapter 2 of 2

Sitting in a bar and crying in one's beer is a less than delightful way to live a life. That said, it is a primo way to think things over. So here was Jennifer allowing me, an old flame, an ex-husband, a complete loser the opportunity to get his rocks off, occasionally, and that for free! That there was a downside to that kind of favor does not seem to have occurred to her. My ego was crushed, but my balls were emptied out. My self-esteem, what little I’d had, was reduced to a vague mist in...

Cuckold
2 years ago
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Summer StormChapter 16

We moved to other locations that had us closer to each other and that provided better cover from stray bullets. While they had numbers, we knew the ground and had prepared our defenses. Their big SUV was stopped at the gate and it would be difficult to push it out of the way. They tried to start it but the starter motor just whirred without cranking it. I shot into the windshield seriously wounding or killing the man trying to start the engine. They wasted a lot of ammo on the snow and the...

1 year ago
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Halftime Stranger

It was a warm October night and I was at a college football game with a few buddies. Throughout the first half of the game, I looked to my right and there was this hot sexy bald guy 3 sections to my right. He had huge arms and was wearing a black wife-beater and jeans. We kept looking at each other and at each time, he would show that bright smile of his.At halftime, I went to the restroom and used one of the stalls, luckily I was the only one in the bathroom. As I opened the stall, he was...

4 years ago
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The Beginning

The evening was dark but I had a call from Billy. From this I got in my car and went over to his place. Anything sexual was the last thing on my mind, weird how things turn out. After chatting for some five minutes I noticed you were getting uncomfortable, a bit of wriggling going on, it didn’t cross my mind that it was a hard on until you looked up and said “it’s because you’re here”. Next thing I see is your cock out and you’re wanking, I just looked and was thinking I want a taste. I heard...

3 years ago
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The Omega TouchChapter 14 Purple Cows and Colored Pencils

Wednesday, July 15, 2009 7:15 PM “He needs to love you.” The ghost Tricia squatted on the bed, glowing, naked, translucent, and she looked at the real Tricia with an expression filled with love and concern. Her voice echoed as if spoken from a great distance through a long tunnel. “That is the answer to most of your questions,” she said. “He needs to love you.” “But...” Tricia began. She stared at the image. Her future self was beautiful, content, sexy, and energized. Her long ghostly...

3 years ago
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End of a Era Pt 01

copyright February/2011 Please consider reading the Trilogy of ‘The Trail West, Winterborn, and The Gathering to better understand how those characters and events flow into this story. Constructive critiques, comments, and emails are very welcome and much appreciated. If you like or even dislike the story, please take the time to let me know why. Thank you for reading and commenting on my work. I hope you enjoy the story. ********** Portland Oregon 1876 ‘State your name for the record...

2 years ago
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Lets Have a Threesome

It is a cold and blustery day and it is snowing out. I decide to call my friend Jayne and my friend Mark. They come over and we decide to watch a movie and have drinks. We put the movie in and start to watch it. About an hour later, we are all pretty drunk and feeling good. We start talking about things and we decide that we want to all get together and have a threesome. We all take each other clothes off slowly enjoying each others bodies, looking and dreaming of playing together. Mark...

1 year ago
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Nigger Life

I was sitting at a rundown bar, having a drink when she caught my eye. White girl, early 20’s, a little overweight, hanging out with another girl. Jen, as I later found out, was barefoot, with black heels on the floor next to her bar stool. I must have been daydreaming, staring at her feet as next thing I know, she walked up to me and said, “you have a problem, my feet hurt”. She was very rude, talking down to me, you could tell she had been drinking. I couldn’t help but look down at her...

3 years ago
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Soccer Mom

Part 1The day was a dark, soggy gray, with thick clouds and showers, as Linda Harmon carefully steered her Cadillac Escalade down the street. She had just dropped off her 10 year old step-son Luke and her 8 year old step-daughter Carrie at school. She saw the red light, and applied the brakes. While waiting out the light, her mind ran through what she had to do today. Stop by the bakers, order a birthday cake for Luke's 11th birthday party...then her train of thought was rudely interrupted by...

3 years ago
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My Stepdaughter and I p3

When I wrote p2 to this story I forgot to put p2 in the title but if you read the first part you will see that it takes up where the first part of this tory left off and sorry for the mess up, I will try to do better in the future. You may want to go back read the second part of this story if you haven't all ready read it. I do thank every one for their comments, and I do hope you injoy the story. Now for part 3.When my cock finally went soft and fell out of Joanne's pussy I sat up next to her...

2 years ago
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How I Became a Santa

Preface: Let me tell you a little about myself. I am now nearing 40 years old. I have been playing Santa for 23 years now, mostly for my own kids, although I have also been a department store Santa as well. My 3 kids are Anna age 11, Janet age 13, and Samantha age 14, she will be 15 in a couple of days. All three of them still believe in Santa, though Samantha is a little suspicious as to if there is actually a Santa or not. (Perhaps Santa will visit her this Christmas.) A thief: My job as...

3 years ago
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My Brother8217s Brother

Hello all, the readers of ISS. I am going to share with you a very recent experience I had with a Cuban boy; I fucked him over the last weekend. I am not going to burden you with the details of how I got him but only want to share with you his short story, how he discovered his elder brother being a cocksucker and a bottom boy too. I think it would be better if you heard the story from Alexandro Persilla (Alex) in his words and I hope you enjoy it as much as I did. I guess I was far hornier and...

Gay Male
4 years ago
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Neibhbour sexy biharen bhabhi

Hi me jagdish ek bar phir aap logo ki specially (bhabhi) ki sewa me phir se aa gaya. Lagta hai aap logo ko meri pahli kahani hot and sexy bhabhi pasand nahi aai. Es liye me aaj aap logo ke liye ek real story laya ho jo ki meri neighbour biharen bhabhi ki hai. Usko saarey gali waley muni ke naam se bolatey hai aur uskey tin bachchey bhi hai (27 yrs old lady) dekhney me wo saawli hai height 5:4” hai lekin uska figure bahut hi sexy hai 36-30-32 aur jab wo chalti hai to uski dono gand ek-2 kar ke...

4 years ago
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Jim The Cuckold Ch2

Dana arrived home well before Jim and quickly fell asleep. It had been years since she'd been sexually satisfied like she just had been. Perhaps, she pondered as she drifted off, the experience that night may have been the most satisfying of her whole life! *********************************************************** Jim drove home after his shower and went over what had transpired that night in his head. He got so horny thinking about Dana being fucked by Kyle, that he had to pull over and jerk...

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