Taking the Big Step

As a female this story makes me nervous about its content, not because of the subject matter, but because I have no idea if I have got the actions and feelings right. I would love to get any feedback but especially from any gay or bi male readers as to if it works or not. If it doesn't work I apologise but hope you enjoy.

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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 animal 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 tea time."

"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 mates 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.