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A whole weekend to himself Tony thought as he prepared himself in the shower. His wife and daughters had left hours ago and his wife had already confirmed their arrival at the health spa where they were visiting for some mother / daughter bonding time. "Whatever" laughed Tony to himself, what it meant was he had from now until Sunday evening in private, nearly 48 hours to do what he wished. Drying himself Tony looked in the mirror naked and studied what he saw. "Not bad for 45" he said out loud knowing he cut a distinguished figure which was still trim from working out regularly at the local gym.

Twisting one way then the other he looked, deciding that his chest and back hair weren't too much and the fuzz on his ass was OK as well. Hazel eyes and short dark cropped hair with perhaps a tinge of grey topped off his look. Tony tugged on his semi hard cock which twitched as he thought about his plans for later, then he knelt and reached into the very back of the drawer under the bed.

Tony opened the locked case and admired his secret selection of toys that his wife knew nothing about. Ever since his time with a very wild girlfriend in his youth Tony enjoyed anal stimulation. It was her that had introduced him to the pleasures of a dildo in his ass and had on occasions fucked him with a strap on. Tony knew his wife would not be interested as she wouldn't contemplate Tony touching her ass saying it was wrong, so heavens only knows what she would say if he mentioned his desires.

Tony spent a lot of time online chatting and playing and over the years he had drifted towards gay sites as although he didn't think he was gay the thought of being fucked was a huge turn on. He had never done anything offline as was too nervous to take the big step, but online he had masturbated himself to a climax and licked his hand clean of his own cum many times. When the right opportunity arose he would use the toys and sometimes even put on a cam show, though always careful to make sure his face was well out of shot.

It had been a while since he had performed and Tony selected the 8 inch dildo with the suction cup on the base. He loved that dildo as it was shaped like a man's cock with veins running down its length. Often he would fantasise that it was a real cock he was riding as he fucked himself to a climax. Grabbing the dildo, a large tub of gel and a towel Tony hummed happily as he set up the web cam and logged onto his favourite site. 'Tony/45/ married - wife doesn't know about my desire to be a bottom' Tony completed his profile and logged on. It wasn't long before the private messages started, he always liked to start with text chat before moving onto webcam once he was turned on.

The first conversation started with a message from a guy called Arthur, whose profile read '38 6'2" Brown hair brown eyes 8" uncut Gay Top - non scene love fucking tight asses

Arthur - "Hi how come your wife doesn't know?"

Tony typed "hi, don't think she would understand"

Arthur - "What you into?"

Tony thought for a moment before he typed "I love fucking my hairy ass with a dildo until I cum"

Arthur - "mmmmm sounds like fun, would love to replace your dildo with my cock and fuck you hard and deep."

Arthur - "what have you done offline?"

It was at this point Tony was never sure what to say as would sometimes say he was experienced and make up a fantasy life so they would cum together, tonight he decided to tell the truth and typed "never touched another man, don't think I am gay but like the thought of having my ass used which is why I use a dildo"

Tony stared at the screen as the words 'Chat closed' appeared, clearly his words had scared Arthur off.

Over the next hour Tony chatted to a variety of guys exchanging hot descriptions of sex and soon his cock was dripping and his ass twitching. He had moved around the variety of sites he knew and ended up on one that mixed text chat and web cam chat. A name appeared requesting a private chat, the name 'The Bronco Buster' made him laugh though the bio made his cock twitch. "Genuine UK gay top 35 clean discrete - I like to break in virgin ass and specialise in married men"

"Hi I am married and a virgin" Tony typed then sat back and waited for the reply.

"Hi back, you can call me Gary, so what have you done so far?"

They exchanged messages and Tony mentioned how he had been introduced into anal play, about his straight-laced wife and that he used a dildo even now.

"Good so far" Gary typed, "now I would like to see what my cock is going to get buried in so switch on your cam and I will do the same"

Tony clicked on the cam and began to grease the dildo while looking at the handsome man on the screen. While his image was of the gleaming dildo the other picture showed Gary had dark Mediterranean features with dark eyes, and he was clearly naked though with him sitting only his top half was visible. Gary smiled into the camera and spoke firmly and softly "let me see the ass that is going to take that dildo." Tony moved so that his ass was pointing as the cam, "cheeks apart" Gary ordered. Tony pulled his cheeks apart so his anal star was clearly showing; "nice" Gary murmured, "now prepare yourself."

Tony smeared gel on his fingers and pushed a finger deep into his ass moaning as it opened him. "Good boy" said Gary "and I think that hungry ass wants more." Tony introduced a second finger, twisting it deep as he prepared himself for the dildo. Tony looked at the screen and could see that Gary was clearly wanking himself under the desk. "Please may I see" moaned Tony as he worked a 3rd finger half in opening his ass further. "Soon" Gary laughed, "but first I want to see you fuck that married ass of yours with that dildo."

Tony needed no second invitation and holding it tightly eased himself onto the rubber cock groaning from the pain as his ass burned as he slowly pushed down letting the full 8 inches slide in. Such had been his concentration that he didn't notice Gary had stood and as the dildo bottomed out Tony found himself staring at the biggest cock he had ever seen outside of porn sites. "You like" Gary asked as he fisted himself slowly, pulling the foreskin back over the angry purple head.

"Fuck yes it's amazing" Tony moaned as he started to ride the dildo up and down.

"That's it ride that cock" Gary croaked as he watched Tony ride the dildo faster and faster. "I want to fuck you for real" Gary moaned as a pearl of pre cum appeared from the tip of his cock.

Tony's eyes were glued to that cock as he fucked the dildo and the taking a deep breath he gasped, "where do you live?" When Gary told him the name of the town Tony's heart started to pound, "oh my god you are only 15 minutes away."

"Can you accommodate" Gary asked as he worked his cock slowly at the cam. Tony told him he could and blurted out his address before he could change his mind then shivered with lust as he heard Gary say "I will be there soon, keep that hole open for me." The screen went dead and Tony gulped as he realised it was too late to back out now.

Tony heard the car pull up and opening the door a fraction saw Gary stride up the path almost running. He stepped into the hallway as Tony stepped back, still naked as per their conversation. "Good boy" Gary said as he moved forward to kiss Tony who recoiled. Gary laughed as Tony reddened, "sorry" Tony stammered," just I have never kissed another man, well not in a sexual way"

"Have you sucked cock?" Gary asked and as Tony shook his head no he went on "well we need to change that then, the kissing will come later." With those words he kicked off his shoes, pulled his shirt over his head before unzipping his jeans and stepping out of them. Tony started at the cock which although semi hard still seemed huge and cautiously reached out to touch it. He jumped as it twitched to his touch then started to swell and rise as Tony worked it with his hand. Without conscious thought he sank to his knees and opened his mouth to suck his first cock in the hallway of his own home.

"What should I do?" Tony stammered.

"Do to me what you wished your wife would do to you" Gary said as he stroked Tony's hair.

Tony found his jaw ached as he tried to open his mouth wide enough to take in the cock but he was determined. Sucking on the head he varied the amount of suction as well as the speed while at the same time working at the base of the shaft with one hand and caressing Gary's heavy balls and ass with the other. Tony felt Gary's cock grow harder and harder until finally he led Gary by his cock up stairs to his marital bedroom, "how do you want me" Tony stammered.

"On your back the first time" Gary commanded, "after you are broken in I will fuck you like a little bitch on all fours, but I want to see into your eyes as I enter you and pop your cherry."

Tony felt his ass twitch at the words and lay on the bed and relaxed as Gary lifted his legs high and apart. "You have taken the dildo out I see" murmured Gary, "no matter I think your hungry ass will soon be ready again."

Spreading gel on his fingers from the tube Tony had carefully laid out next to the towel he was laying on Gary pushed a thick finger into Tony's ass. Tony moaned loudly as it felt so different to his own fingers or the dildo and relaxing he felt Gary slowly finger fuck him as he bent and took his cock into his mouth. Gary worked on Tony's cock as he fingered Tony with first one then two fingers. By the time Gary introduced a third finger Tony was in heaven and squirming and writhing and couldn't stop the thick stream of cum he shot into Gary's mouth. Swallowing and sucking the last few drops Gary withdrew his fingers and lifting Tony's legs onto his shoulders said, "now I think you are ready to have your cherry popped for real."

Tony felt open and empty inside without the fingers and then he felt the pushing of the head of Gary's massive cock against his anal star. "Oh my fucking god it will never fit" Tony screamed as the head popped in sending stars into his brain.

"Just relax" Gary said as he slowly increased the pressure so pushing about half his cock inside Tony's ass.

"Fuck fuck fuck" was the only thing Tony could sob as the cock that felt bigger than anything before slid deeper.

"Good boy" said Gary as he pulled back a little before pushing further, each time he moved his cock in Tony would moan and writhe under him. Eventually Gary was buried fully to the hilt and held still, his cock fully in and looked into Tony's eyes. "So how does it feel to have 10 inches of cock in your ass?" Gary said softly.

"Fucking amazing" Tony murmured blinking away the tears and with that leaned up and kissed Gary on the mouth. As their tongues entwined Gary began to slowly fuck Tony with little movements so just an inch or two of his thick cock slid in and out.

Gary broke the kiss and looked down at Tony and asked softly, "do you want me to talk dirty to you?" Tony nodded enthusiastically, as it as like Gary had read his mind. "Good" said Gary as he moved upright to get better purchase, "I like to hear my married sluts moan and beg as I pound their slutty married holes." Gary began to fuck faster sending Tony into raptures, "I am going to fill you full of seed" Gary continued," then I am going to turn you over onto all fours and fuck you again and again."

"Oh fuck" Tony shouted loudly, as despite cumming not long before his cock spurted jets of sperm up between their bodies. His orgasm caused his anal muscles to contract and with a****l grunts Gary pumped hard and fast sending stream after stream of seed into Tony's ass as it gripped and milked him.

Gary collapsed into Tony's arms still impaled deep inside of him, until after a few minutes he slowly subsided and eventually slipped out. "Well that's your cherry well and truly popped." Gary laughed, "now let's have a shower. How long until you wife comes home? And is it ok for me to stay or do you want me to go?"

Tony glanced at the clock that was showing 2 o'clock in the morning. "She won't be home until Sunday around 3pm."

"Good" said Gary as he walked towards the shower, "once we are washed I want to see how much cum you can swallow. Then in the morning after I have fucked you on cam I might call up a few friends and have you gang banged. How does that sound?"

Tony felt weak at the knees at the thought but nodded eagerly as he followed Gary into the bathroom ready for his first belly full of someone else's cum.

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The first time I fucked a married woman was the most incredible experience of my life. She was in her mid 20's, about 5'6, 120lbs, Blonde that was married with the nicest pair of titties and juiciest cunt you can imagine. I am a 17 year old male thats 6'2 about 190lbs medium built and have a average size cock thats about 7 inches. When I first laid eyes on this woman I was struck by her beauty, she had curly blonde hair and was wearing a nice sun dress. It was in the afternoon when I was...

Erotic
4 years ago
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After a few months of being alone and satisfying myself with my hand, anal toys, and internet porn, I decided to place an online add and meet a few guys to service. It didn't take long before I had sucked a few guys and remembered how much I enjoyed it. It was clear that I loved having a cock in my mouth and having my ass played and now I wanted more. Just as I was craving a hung stud to come work me over, a hot top guy answered my ad who was just what I was looking for. His screen name was...

4 years ago
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On Becoming Miss Louisa Harper of New York and Newport 3

From 'The Autobiography of Miss Louisa Harper' ~ "Langdon Beech-Thorndyke III was 'a catch.' Mother and Father thought that he would be a perfect match for me. He was twenty three and I was fifteen. My parents hoped that we would become betrothed that summer and then a grandiose wedding would follow in three years after I turned eighteen. This was my sister's summer, though. Miranda would be married in August to a Vanderbilt cousin who she barely knew. The opulent affair...

4 years ago
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I married a few years out of college to a girl I met there. Last year I attended a conference in Chicago. I was staying in a nice hotel that had privileges to the adjoining fitness center. In between sessions, I headed over and lifted some weights before taking in the men's only sauna.I had only been in there for a few minutes before three guys came in and sat down on the benches. As the wooden benches were extremely hot, I noticed one guy sat over in the corner on his towel while the two older...

2 years ago
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I stood naked beside the bed. My hard cock jutted straight out from my body betraying my excitement. "I have never done this before," I said softly. "But it excites you doesn't it?""I guess so," I answered as my cheeks flushed red with embarrassment. "You guess so? It's a yes or no question. Does it excite you?""Yes," I replied honestly as I cast my eyes to the floor. "Yes what!""Yes master," I quickly corrected. My cock twitched as the words hit my ears. I had always been straight or maybe a...

4 years ago
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"So, what made you decide to post your ad online tonight?" he asked as I we walked down the hall of my apartment building."I don't know," I replied. "I guess I am just really horny and wanted to try something new."I knew, though, why I decided to post the ad that read "28 year old male looking to have sex with a man for the first time. Please, be open to fucking and being fucked." I have been playing around with anal play since my senior year of high school. I skipped school one day and decided...

4 years ago
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"Take off your clothes" he told me, and I nodded and began to strip. I was really nervous and horny. I was scared, too, but I was so excited! When I finished, I looked up at him, sitting there watching me. "Turn around and bend over, bitch!" he said, and I immediately did as he said. "Spread your ass cheeks and let me see what I'm going to be fucking." Reaching back, I spread my ass cheeks wide. I wet one finger in my mouth and rubbed it around my tight little asshole, letting it slip in up to...

3 years ago
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Training Milf Mom To Become A Naughty Bitch

Hi ISS readers! My name is Urvashi (20 years old). I have a boyfriend!. I love sex. I seem to have picked up this amazing passion from my naughty milf mom Urmila (43 years old), an insatiable woman. I helped her get better cocks inside her pussy, starting from this one! One lazy summer afternoon, my mom and I were lying on the bed. I was wearing a big cotton t-shirt that reached my thighs. Since my body is slim, a big cotton t-shirt is what I need to cover my curvy body when I am at home. My...

Lesbian
2 years ago
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Start Sucking His Black Cock Bitch Gay

It wouldn't stop. The impure thoughts wouldn't go away. Whenever he tried to ignore it, it always returned. It made him feel crazy in the head. He knew it was wrong, but his imagination continued to be more of an inconvenience in the real world.Scott had nothing to do on a Saturday morning. Betty , his wife, had already left the house to visit her friend's place. The twenty-nine-year-old husband was now alone in the master bedroom, and he wished that he would be somewhere else other than his...

4 years ago
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Ever since meeting the my lust for cock had become insatiable. I think back on that meeting with him and know that something in me had forever changed. No longer did I have the occasional thought about sucking a cock or maybe taking it in the ass. Cock, and the thought of serving powerful men was, and continues to be, on my mind most of the time. The memories of that day, how I became such a hungry slut, moaning like some whore and begging to be fucked, puts me into a constant state of...

2 years ago
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As the months went by, my cravings remained and I satisfied them from time to time by finding guys online who who wanted head. I would meet them or have them over and worship their cocks until they filled my mouth or covered my face with their cum. This would satisfy my hunger and sometimes weeks or months would pass before I would feel the need to suck another.During this time, I also met another girlfriend (yes, I'm totally Bi) who has no idea that I love pleasing men. As you can imagine,...

4 years ago
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My New Hobby Gay

Now, at this time in my life, I never even thought about the prospect of being with a man. I loved pussy, and pussy is all I ever wanted. Never in a million years would I consider being with a man, especially with our black cleaning man Marcus. Marcus grabbed my garbage and emptied it into his pale, dusted a few fixtures, and moped the floor. As he performed his errands we briefly talked, like we usually do, about cars, women, and what ever game was on that evening. I enjoyed watching him talk;...

3 years ago
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First Time Iam His Bitch Now Pt2 Gay

"Bitch!" he snapped back. "We're not done here yet! Now I want you to...""... to go stand in the shower," he commanded. "Don't turn on the water, leave the curtain open and wait for me."I had no idea why he wanted me in the shower without turning it on. Wouldn't he want me clean after what we had just done? But I wasn't about to ask questions. I was pretty much in his control and just obeyed.He walked into my bathroom. "Good, now stay in the tub and get on your knees." Again, I did as I was...

2 years ago
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On Becoming Miss Louisa Harper of New York and Newport 2

From 'The Autobiography of Miss Louisa Harper' ~ "Beauty comes from pain, Louisa. A proper young woman does not present herself unless she is properly coiffed, properly made-up, properly attired and wearing the proper accoutrements. That, Louisa, is what 'proper' means." Of course, I tried to argue. That is, after all, what an adolescent is supposed to do, but my mother would just purse her lips, shake her head in disgust and repeat that one sentence that she spoke most frequently...

4 years ago
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On Becoming Miss Louisa Harper of New York and Newport 6

From 'The Autobiography of Miss Louisa Harper of New York and Newport' ~ "The day of Miranda's wedding was cloudy and overcast, so perhaps Aunt Ada had been correct. Perhaps God would not waste a beautiful day on a wedding that would lead to a loveless marriage. Instead of using the vast tents that had been erected on the lawns at Golden Bluffs, everything was moved into our grand ballroom, which was large, but could not accommodate everyone who'd been invited. So, tables were also...

1 year ago
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Things have been weird this week. A girl asked me out for a date but I declined. I'm not entirely sure why, she just didn't seem like my type. The weird thing is that I've been crazy horny these days, jerking off daily. I'm also getting more into rougher porn; maybe it's just a phase. I haven't been out to the club since that fateful night. I swear it was all a bad dream, at least that's what I tell myself. Not going to the club makes meeting girls difficult... but then again, I haven't been...

3 years ago
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On Becoming Miss Louisa Harper of New York and Newport 5

From 'The Autobiography of Miss Louisa Harper' ~ "The week prior to Miranda's wedding was a hectic and crowded one at Golden Bluffs. All of our relations came to Newport for the event and many of them stayed with us. Unfortunately, we also had many friends and business associates staying as well, which did lead to some difficult choices. Father was a self-made man who had family he wanted in attendance, but they were from a lower rung of society. So, since the rooms were assigned to...

3 years ago
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Training my new slut fucktoy part 1

Victoria had just turned 18 and was still in high school. She was popular at 5' 1" with nice C cups a tight little petite 100 pound body complete with a hot sexy ass. She was dating the football quarterback Mike at her high school when we met. She started working at one of my favorite bars and we both knew there was a instant connection. After a few nights chatting after she got off work she started telling me about her sexual experiences. She had been fucked by her quarterback boyfriend...

2 years ago
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Willies New Bitch

Dressed in her best black lace lingerie, Kim Turner, a beautiful thirty one year old mother of two gripped the edge of the tab          ??????????????????????????? ?Willie?s New Bitch?  ???????????????????? A work of fiction for Adults by Taskmaster11????????????????????????????????????????? [email protected]??     ?????? ?????????????????????????????????????????????????A Prologue As always during the week, the husband was consumed by his usual deep sleep, but for his beautiful...

4 years ago
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My New Hobby Sucking BBC Gay

Now, at this time in my life, I never even thought about the prospect of being with a man. I loved pussy, and pussy is all I ever wanted. Never in a million years would I consider being with a man, especially with our black cleaning man Eddie. Eddie grabbed my garbage and emptied it into his pale, dusted a few fixtures, and moped the floor. As he performed his errands we briefly talked, like we usually do, about cars, women, and what ever game was on that evening. I enjoyed watching him talk;...

4 years ago
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Every Man Is A Little Bit Gay

gay first time – blow job – tied up – gay husband – bisexual male – bicurious male ‘They’re doing cookery classes down at the local college. I think I might give them a go,’ Trish said, looking up from reading the Evening Gazette, our local paper. ‘The last thing you need is cookery classes,’ I replied with some feeling. Trish is the best cook I’ve ever met, that’s one of the many reasons I married her. ‘I don’t need to learn how to boil an egg but they’re offering an advanced course on...

2 years ago
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Every Man Is A Little Bit Gay

gay first time – blow job – tied up – gay husband – bisexual male – bicurious male"They're doing cookery classes down at the local college. I think I might give them a go," Trish said, looking up from reading the Evening Gazette, our local paper."The last thing you need is cookery classes," I replied with some feeling. Trish is the best cook I've ever met; that's one of the many reasons I married her."I don't need to learn how to boil an egg but they're offering an advanced course on...

2 years ago
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My First Cock Now Swallow it Bitch Gay

I was eighteen. Long blonde hair, baby faced, cut build (I was in water polo), and tan. I had been browsing on a hook up website for a while. My parents were out of town for the weekend, and my girlfriend was at the beach with her friends till the next day. I figured today was the day. I went on the website and messaged a guy i was talking to. He was 25, white, brown hair, and had a nice face, but a slight beer belly. He said he could come over.After he said he was coming i quickly got in the...

2 years ago
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Turned into there Bitch PT2 Gay

It had been a couple of months since Ron and Gary moved in downstairs and turned me into their bitch. During that time, my ass and throat were open 24/7 for their cocks and they'd made steady use of both. I never had to go out cruising for sex, I could barely keep up with what I was getting.One morning, Ron told me to be ready at 9pm that night to go out, that they had a special surprise planned for me. Knowing how their evil minds worked, I spent the day with my stomach rolling and a constant...

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