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This story, and the one's that follow, have a grain of real life experiences in them, but I've elaborated on them significanty so they really are little more than fiction. But I hope you enjoy reading them.

The usual warnings apply. This story involves sex between consenting adults. If you're not over 18 or it is i*****l to read this where you live, then please do not continue any further. You have been warned.

Fisting. The word alone seems to instantly divide gay men into two camps. Those who do or are interested and those who don't. Some simply aren't interested and leave it at that. But others take a highly negative and critical view of those who do. I'm not sure how or why this attitude came about but I suspect it is due to a view of fisting as inherently linked with an image of big hairy men in leather who swear, curse and spit at each other. Hands are rammed in arses in scenes that are almost bordering on psychotic. I've been fisted many times and none of my experiences fit with those I've seen on screen. This is my story.

Firstly a little about myself. I'm in my early 40s. I'm white, slim build, with a little chest hair which I usually shave off. I work out several times a week, a mixture of cardio and weights. I'm lean but not thin. I have some muscles but no-one would call me muscular. My cock is cut and an average six inches. I'm average height, about 5'7". I have relatively small hands although I didn't see how advantageous that would be if one got into fisting.

I'm not entirely sure how my interest in fisting began. I knew what fisting was, but the one time I had seen it on a video, it seemed so extreme and the actors so unlike myself, that it never seemed an option worth exploring.

When I was in my late 30s, my boyfriend at the time and I enjoyed using dildos. One was at the upper end of the human spectrum but none were outrageously enormous. Given we were both versatile and loved to switch roles, especially with dildos, we always douched as it made for some lengthy and fun sessions.

It all began during one session about five years ago. He'd already fucked me with his 7" uncut dick and I was now fucking Ed with a mid-sized dildo. Ed was also white, and a similar age, but was little taller and stockier. He had a bit of hair on his chest, but nothing extreme. I was lying next to him, facing him, my right hand between his legs and moving the dildo in and out of his arse. We were kissing passionately, our tongues dancing in each other's mouth, as I fucked him.

His arse had really loosened up and he just writhed in ecstasy when I would pull the dildo almost completely out and then push it back in. Sometimes, I would tease his hole with the tip of the dildo, he arse lips almost pouting to get it back in and then, just as suddenly, shove it back in.

After quite a while, I pulled the dildo out and set it aside and gently caressed his hole with my fingers.

"You want me to finger your arse babe?"

"Oh yeah," he replied. "Play with my hole."

I started teasing his hole and his arse with my fingers. This wasn't really unusual either as we'd finger fucked each other many times, although never with more than three fingers.

It's one of the quirks of nature that if you've had your arse stretched and you put something much smaller in, like a finger, the arse forms back around it, but not tightly. The sensations for the guy being fingered are always delightful.

"Oh Jim, that's fantastic," he gasped as my middle finger effortlessly slid in and out of his arse.

I began feeling inside him, enjoying the warmth and softness of his rectum. I quickly found his prostate gland and gave it a good massage. "Oh man, that's so good," he sighed. He was writhing about, enjoying the sensations emanating from his arse. Soon the solitary finger was joined by a second and then a third.

I kept probing his hole with my fingers and he urged me to push harder and faster. I don't know why, but I added in my little finger to the three others already stretching his hole. The addition of the extra finger caused his eyes widen and his head arched back. "Oh, yeah, stretch my hole," he said with a lusty grin on his face.

"You like your hole stretched boy?" I said with a smirk. We'd been together for a while and such silly fantasy talk was common in our sex life.

"Oh yeah, my arse is yours. Give me more."

And more was what he got as I added my thumb to the mix.

"Oh fuck man that's fantastic."

But instead of the vigorous finger fucking of before, I slowed down the pace and just applied more pressure, going a little deeper every time.

Ed was really getting into it. When he urged me to put lube on my hand, and took a couple of good snorts of poppers, I knew we had both crossed the line from finger fucking to fisting.

My hand kept moving in. I had just about reached the widest point when Ed suddenly looked worried.

"Are you ok, babe? Do you want me to stop?"

"I'm not sure. It feels so intense. I'm just not sure it will go."

"Take some really deep hits of the poppers, let go of your dick and just relax."

Neither of us realised it at the time, but that was the key. Because Ed was still stroking his cock, he was u*********sly tightening his hole.

I eased up just slightly, poured heaps more lube on my hand while he took a deep snort in each nostril and let go of his dick. I resumed the pressure and quickly reached the widest point again.

Ed u*********sly started tensing again. When he realised this he relaxed, breathed out slowly and that's when it happened. My hand slid inside. His arse lips were now around my wrist.

I've never seen anyone's eyes go so wide. "Oh fuckin hell Jim, I, I, I don't believe it, you're inside me," he stuttered, overcome with emotion.

He then looked worried. "Oh Jim, I can't take it, you need to pull it out." He was beginning to panic.

"Just relax sweetie, you'll be ok. I'm not going to make any sudden moves."

He calmed down and I began to slowly move my hand inside him, forming a fist. The waves of sensations were soon driving Ed nuts. At times he was almost babbling, he was enjoying himself so much. "Oh, fuckin hell, Ed, seeing your arse stretched around my wrist is so fuckin hot. It's so soft and beautiful inside you."

Having my hand inside him was amazing. I could sense his heart beating and felt his pulse around my wrist. The texture of the lining of his arse, was silky soft. My fingers had never felt anything quite like it before.

His dick, which had gone soft as I initially entered him, was now as hard as wood. He began stroking himself, his head rolling from side to side, as waves of sensations cascaded over this body. It didn't take long before he orgasmed again. "Oh fuck Jim, I'm going to cum," he gasped. "Go for it baby, shoot your load while my hand is up your arse."

Those words pushed him over the edge and he shot line after line of cum over his chest. Jim had never been a strong cummer, usually his cum almost dribbled out of his dick. But this time, he not only kept cumming but the force saw several shots land on his chest and one hit him on the lips, which he eagerly lapped up. "Oh man, oh fuck, oh wow," he cried, almost incomprehensibly.

When he calmed down, he realised my hand was still in his arse and he suddenly looked worried. "Don't worry, honey. Just stay relaxed and I'll slowly pull it out."

Watching his hole stretch again as I pulled out was mind blowing. "Oh man, that's amazing sight seeing your hole stretch." No sooner than it was out than I grabbed my cock and began stroking it, shooting a massive load all over Ed's chest. He greedily scooped it up and ate it all.

Exhausted, I lay down on top of him and we began to passionately kiss again. After a few minutes, I rolled off him and we lay side by side looking at each other. We were both smiling so much.

"I love you so much Jim," Ed said. "It was just so amazing, nothing has made me feel like that before. I can't wait until I get my hand inside your arse."

"Me too," I replied, although secretly I wasn't so sure. My hands were relatively small - Ed's were massive by comparison. It had been an effort to get my hand inside Ed - I couldn't imagine how his hand would ever get inside me.

But then the story of my first fist, is for another time.

Well, what did you think? It's my first story.

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The call started and I first saw her beautiful smile as she says “Hi Daddy”. He spaghetti strap top was falling off her shoulders as she tried to readjust the, I immediately realized she had gotten started before calling me. She sat the phone down on a table and tried to adjust it so the majority of the room was visible to me. The quality of the call was superb, I could see everything clearly, everything including the two black men sitting on the bed behind her. I could also hear well enough as...

2 years ago
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strooder had a huge wanking session over me

strooderHey. Ive just had a huge wanking session over you. I was reading your post about the messages NYNASTYGUIDO sent you and it got me thinking how amazing you would look if you were pregnant. Just imagine how your tits would swell up and develop big milky pregnancy nipples. Your legs and ass would become bigger and your belly would become huge, and you would be so horny with all those hormones.Im just imagining you now, how sexy you would look with extra big curves, how you could sit on me...

4 years ago
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ISS Reader And Me Having Sex

Hi to all single ladies and girls in Bangalore. This is one of the best experiences I have ever had in recent times. I’m a 25-year-old working, fun-loving guy. This started when one of the ISS readers texted me on hangouts. She introduced herself as Neelu, 27-year-old working professional. She occasionally reads on ISS whenever she is little high over weekends. She started telling me about my previous story which she felt is quite good. She was asking me if it was real, how was the experience,...

1 year ago
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MILs first anal

Not much has changed in my relationship with my MIL. We still have make love to each other several times a month, but she never seems to amaze me. The sex is great and she really knows how to use her body to please her lover. Just when I thought things could not get any better she dropped another bombshell on me. We were just laying in bed together, she was stroking my cock and I was enjoying a mouth full of tit, when she told me a story that happened when she was married to my father in law....

Erotic
2 years ago
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My Favourite Fantasy

It's 6am and my husband has just gone to work, I'm trying to have a lie-in, but it's so warm and sticky I'm having trouble sleeping, even with the window wide open, and I keep waking up!I feel a weight on my legs, and I think I've rolled the duvet into a big ball again, I try to move to straighten it out, and find I can't!Confused I open my eyes and see you there grinning! We've been talking online and on the phone for quite some time, and we've exchanged photos, so I know exactly who you are!...

2 years ago
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One Day only

Sliding my hands down my body, I feel the beginnings of a slight tremble. Do I have time? A quick glance at my watch confirms that I do, but should I? Why not. Feeling the slow pathway my fingers take to strip my body of all clothing, throwing them on a chair behind me, I laugh for the freedom. Everything but the polished black stilettos, they can stay. Standing there in front of the full length mirror, twisting and turning, studying my figure. "Not bad." I’m not bad at all, for a mother of...

Oral Sex
3 years ago
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Business Trip With Seema 8211 My PA Part 1

Hello ISS readers, here I am yet again with yet another fictional story. This one is about Sanjay who is a male of 38 years. Sanjay was a CEO in a reputed pharma company he deserved the position. Seema a 32 years married woman was his personal assistant for 3 years now. Seema was an attractive looking woman standing almost 5’9” slim and sexy body she was a fair looking beautiful woman. Sanjay too was a handsome looking man with a gym body they both had quite an understanding as a...

1 year ago
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ExxxtraSmall Jade Amber Vagina Volleyball

Jade Amber was itching to show her stepdad her volleyball skills. Stepdad was more focused on football playoffs, but figured he might as well spend some time with his needy yet petite stepdaughter. Before they could even get into ball handling, Jade was handling her stepdads balls and cock in her mouth. We are unsure how this proceeded to sex so quickly, but we are sure glad it did. Watching tiny Jade bounce on that stiff cock was more amazing than watching the regional college volleyball...

xmoviesforyou
3 years ago
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Jasons Quest for Incest Earned Moms Respect

Together, Angelina and Jason was a single mom family. Her marriage broke up five years ago and she managed to hold her own in the male dominated financial industry. This meant that she was smart and tough. She had hoped for a new husband but that had slipped her by, year after year. She was now 38. Even as her old sexual partners among her colleagues and friends drifted away from her, Angelina still managed to bed one of the young subordinates in her company. Her son Jason did well in...

3 years ago
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Why boyfriends should never complain

Willie Long guided his big rig around yet another curve in the California back road. He had picked up a load in Napa and was on his way to Chicago. Originally hailing from Georgia, Willie had been trucking since the mid 'eighties, spending most of that time on long hauls. He was unmarried and enjoyed the long rides and the varying scenery. He had seen many things over the years and had found himself in many situations. Because of that, he had learned to keep his eyes open while on the road...

First Time
4 years ago
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Alien

Pete was concerned. He nibbled on a nail and paced the little bedroom while looking down at the sleeping woman on the bed. She hadn’t moved in hours but her breathing was steady and she didn’t seem to have a fever. He had found her in the woods three days earlier and carried her all the way back to his cabin. It had been hard work since she was heavier than she looked.He figured her to be around five feet eight inches, she was quite tall and, without sounding too perverted, she had a killer...

Monster Sex
3 years ago
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College Sex with John

My last account was an introduction to me, Tom, my girlfriend Mary, her roomie, Karen, and Karen's boyfriend, John. I had switched universities my senior year (from the BigTen to the MVC), and ran into Mary, a girl I had gone to prep-school with 3 years before. She was very athletic, tall, very trim, short dark red hair, porcelain skin, small-tited, acrobatic in bed, and an incredible lover. She loved everything about sex (like me), the smells, tastes, and textures. She truly got off on my very...

Bisexual
2 years ago
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The Thief of the RoseChapter 12

Aaron met Reg in the dining hall early the next morning. After breakfast and settling up with Miss Sara, they gathered their things, saddled their horses and, after squaring accounts with the Sorcerer's Guild and retrieving the gold pieces, were off for Realto. Aaron intended to spend one day in Realto to say goodbye and make sure that Master Weaver was dealt with and then leave for Aithen. He was thinking of asking Reg to just stay at the duchy while he returned to the Capital when his...

4 years ago
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Loving AmyChapter 19

As they walked through the lobby every eye again followed her. She didn't notice as she saw no one but her husband. In their room she walked into his arms and kissed her. His hand went to her zipper and pulled it down. She took a step back and smiled at him. "Would you like to unwrap the package?" He pulled her dress off of her shoulders and, with a shrug, she caused it to fall to the floor at her feet. He unhooked her lacy bra and it fell to the floor with the dress. She reached for...

3 years ago
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Yuis Awakening Part 14

On Yui's return from her latest trip to Thailand, she and Emi wasted no time in catching up on each others' lustful fantasies. Yui related her night of lesbian orgy with the Australian woman and local girls, and Emi explained that she had spent most of the last few days at the studio, in front of her mirrors, loving herself.Now, the two girls were hitting the town, once more going to Bar Hers for cocktails. Once inside, they settled into a booth and snuggled closely in the semi-privacy. Indeed,...

2 years ago
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Monkey WrenchChapter 14

My bedroom was a couple of degrees warmer than the box. It was almost stifling. I tried kicking away my comforter, pleading for a breeze to sweep in from my open window. I woke up feeling sweaty and gross. I stretched and swung my legs out of my bed. My door flung inward. Zoë rushed into my room. “What’s going on, honey?” Dad’s voice chased my sister into the room. “I, uh, I didn’t do my homework and Dean did. I gotta copy it before I go to class,” She announced and closed the door. Brazen....

3 years ago
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My Dearest Darling VirginiaChapter 12

In the middle of Bibbidy Bobbidy Boo, Detective Lands called and asked Brad and me to come down to the station to sign our statements. Brad drove and we got there around one. Afterwards, Brad wanted to go check on his grandmother. When we got to the nursing home, we were met in the front hall of the lock-down area by Ethel Smith who was worried about missing her train. A petite ninety year-old with lots of vigor, her only health issue was the advancing dementia that left her confused. Brad...

3 years ago
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A Vacation REality

I was busy getting packed for our annual summer trip. We were going to Chicago this year, because my dad had to do some work before we could do much actual vacationing. I was upset and did not want to go on this trip because my cousin was not allowed to come with me. We usually spend every moment we can together, and in past years we have been able to vacation together as well, but not this year thanks to dad’s business. Just the night before, my cousin and I took our masturbation session...

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